SEBACIC ACID


Sebacic acid is a naturally occurring dicarboxylic acid with the formula (CH2)8(CO2H)2. 
It is a white flake or powdered solid. 
Sebaceus is Latin for tallow candle, sebum is Latin for tallow, and refers to its use in the manufacture of candles. 
Sebacic acid is a derivative of castor oil.

In the industrial setting, sebacic acid and its homologues such as azelaic acid can be used as a monomer for nylon 610, plasticizers, lubricants, hydraulic fluids, cosmetics, candles, etc.

Production
Sebacic acid is produced from castor oil by cleavage of ricinoleic acid, which is obtained from castor oil. 
Octanol is a byproduct.

It can also be obtained from decalin via the tertiary hydroperoxide, which gives cyclodecenone, a precursor to sebacic acid


Sebacic Acid is used in the manufacture of Nylon 6-10 and it is also used as a corrosion inhibitor in metalworking fluids and as a complexing agent in greases. 
Sebacic Acid can also be found in plasticizers, lubricants, hydraulic fluids, cosmetics, and candle manufacturing.

sebacic acid is used in several commercial antifreezes 

Sebacic acid is a dicarboxylic acid that occurs naturally and found in powdered crystal and white flake form which is derived from castor oil. 
Derivatives of this acid includes Dibutyl Sebacate, Diisopropyl sebacate, Dimethyl Sebacate, Disodium sebacate, and Dioctyl Sebacate. 
It has wide application as monomer in lubricants, textiles, cosmetics, candles and hydraulic fluids production. 
Moreover, this product is extensively used as a chemical intermediate in painting materials, antiseptics and aromatics manufacturing.

Sebacic acid is powdered crystal or white flake which is obtained from castor oil by utilizing sulfuric acid with catalysts including phenol & zinc oxide and sodium hydroxide. 
Sebacic acid is widely used in various end use industries including lubricants, plasticizers, hydraulic fluids, candles, and cosmetics. 
Market growth of sebacic acid is backed upon increasing lubricants demand in automotive and industrial sector. 
Downstream potential of sebacic acid includes dibutyl sebacate, dioctyl sebacate, dimethyl sebacate, diisopropyl sebacate, and disodium sebacate. 
These are used in several sectors including polymers and cosmetics. Growing cosmetics sector growth owing to increasing personal grooming trends may propel product demand.
 

Sebacic acid is used for making high performance engine oil and lubricants, adhesives, engine coolants, bio-degradable packaging, sub-sea pipe/cable coatings, aerospace polymers, anti-corrosion applications and bio-plastics

SEBACIC ACID
Sebacic Acid is made from castor oil and belongs to the homologous series of dicarboxylic acids. 
It is used as source material for various products. 

 Sebacic acid is a dicarboxylic acid, which is a powdered crystal or white flake in its pure form.  
Sebacic acid is a non-hazardous acid and it is extensively used in the manufacturing of bio-polyamides. 
Sebacic acid is provides various advantages such as adaptability and hydrophobicity among others make it ideal for a wide range of applications. 
The major applications of the sebacic acid include plasticizers, solvents, adhesives, personal care & cosmetics, and textiles. 
The growing usage in end-use industries coupled with the growing inclination towards personal care and healthcare products are the major factors driving the global sebacic acid market. 
Sebacic acid is also used as feedstock for the production of sebacate diesters, which, in turn, are used in lubricants and greases. 
Moreover, the growing demand for automotive, pharmaceuticals, construction, and packaging industry is further expected to fuel the growth of the market.  
Furthermore, sebacic acid is also used in the manufacturing of PVC coatings with enhanced temperature resistive abilities.  
However, the presence of substitutes such as adipic acid, azelaic acid, and others are some of the major factors restraining the growth of the market. 
The growing application of sebacic acid as a feedstock for bio-based polymers is a major opportunity in the market. 
These bio-based polymers produced from sebacic acid exhibits superior qualities such as excellent flexibility and durability among others.


The growing urbanization and industrial development in the developing economies are the major factors driving the growth of the sebacic acid market. 
Moreover, adoption rate in the paints and coatings industry along with the growing demand for cosmetic & personal products is expected to have a positive impact on the growth of the market. 
Furthermore, with the increasing investment in the building & construction sector, the demand for adhesives and paints & coatings is growing substantially. 
This, in turn, is driving the growth of the sebacic acid market. 
Moreover, growing applications of PVC coatings are expected to boost the market in the region. 
The growing investment in the retail sector has made the availability of cosmetics and personal care products easier, which is fuelling the market growth further.


The global sebacic acid market is segmented into application and region.  
On the basis of the application, the global sebacic acid market is segmented into personal care & cosmetics, lubricants, greases, plasticizers, solvents, adhesives, chemical intermediates, paints and coatings, textiles, candles, and hydraulic fluids among others.

INDUSTRIES
The best known application of sebacic acid is the production of polyamides. In addition, it is used as a crosslinker in the adhesives industry, as a plasticizer in the plastics industry, as a component of lubricants and as an extender in packaging films.

 Description :
Sebacic acid, dicarboxylic acid with 10 carbons, is a product of vegetal origin, processed from castor oil
Can be used :
- To produce polymers such as polyamides, co-polyamides, co-polyesters, polyester polyols, bioplastics, etc.
- To produce esters which are widely used as plasticizers in industrial applications (lubricants, plastics), in cosmetics, etc.
- As a corrosion inhibitor (widely used under the form of a salt) in coolant application,
- As a buffering ingredient in cosmetic.

Sebacic acid is a dicarboxylic acid based on renewable castor oil.

Sebacic acid is a white flake, crystal powder or granular and belongs to the group of dicarboxylic acids. 
Its salts and esters are referred as sebacates The reaction with hexamethylene diamine creates a polyamide, called nylon 6.10. 
The sebacic acid is mainly used as raw material for the production of lubricants and coolants, but also for the production of antifreeze and plasticizers.

Nowadays biobased polymers contain sometimes sebacic acid as well.

Examples of applications

Sebacic acid is mainly used in the production of lubricants and greases, coolants, antifreeze, coatings, plasticizers, polyamides and polyesters.


Sebacic acid is a dicarboxylic acid, which is a powdered crystal or white flake in its pure form.  
Sebacic acid is a non-hazardous acid and it is extensively used in the manufacturing of bio-polyamides. 
Sebacic acid is provides various advantages such as adaptability and hydrophobicity among others make it ideal for a wide range of applications. 
The major applications of the sebacic acid include plasticizers, solvents, adhesives, personal care & cosmetics, and textiles. 
The growing usage in end-use industries coupled with the growing inclination towards personal care and healthcare products are the major factors driving the global sebacic acid market. 
Sebacic acid is also used as feedstock for the production of sebacate diesters, which, in turn, are used in lubricants and greases. 
Moreover, the growing demand for automotive, pharmaceuticals, construction, and packaging industry is further expected to fuel the growth of the market.  
Furthermore, sebacic acid is also used in the manufacturing of PVC coatings with enhanced temperature resistive abilities.  
However, the presence of substitutes such as adipic acid, azelaic acid, and others are some of the major factors restraining the growth of the market. 
The growing application of sebacic acid as a feedstock for bio-based polymers is a major opportunity in the market. 
These bio-based polymers produced from sebacic acid exhibits superior qualities such as excellent flexibility and durability among others.


Synonyms     
1,10-decanedioic acid    
1,8-dicarboxyoctane    
Decanedioic acid    
Sebacic acid    
SEBACIC ACID    
Sebacinsäure 

IUPAC name
Decanedioic acid
Other names
1,8-Octanedicarboxylic acid
Identifiers
CAS Number    
111-20-6 check

Chemical formula: C10H18O4
Molar mass: 202.250 g·mol−1
Density: 1.209 g/cm3
Melting point: 131 to 134.5 °C 
Boiling point: 294.4 °C at 100 mmHg
Solubility in water: 0.25 g/L
Acidity (pKa): 4.720, 5.450

Chemical Safety    
Irritant

Laboratory Chemical Safety Summary (LCSS) Datasheet
Molecular Formula    C10H18O4 or HOOC(CH2)8COOH
Synonyms    
sebacic acid

DECANEDIOIC ACID
111-20-6
1,10-Decanedioic acid


Molecular Weight    
202.25 g/mol


An α,ω-dicarboxylic acid that is the 1,8-dicarboxy derivative of octane.

Sebacic acid is a white granular powder. 
Melting point 153°F. 
Slightly soluble in water. 
Sublimes slowly at 750 mm Hg when heated to melting point.

Sebacic acid is an alpha,omega-dicarboxylic acid that is the 1,8-dicarboxy derivative of octane. 
It has a role as a human metabolite and a plant metabolite. 
It is a conjugate acid of a sebacate(2-) and a sebacate. 
It derives from a hydride of a decane.

sebacic acid
DECANEDIOIC ACID
111-20-6
1,10-Decanedioic acid
1,8-Octanedicarboxylic acid
Sebacic acids
Decanedicarboxylic acid
n-Decanedioic acid
Sebacinsaure
sebacate
Acide sebacique
Sebacinsaeure
USAF HC-1
Ipomic acid
Sebacinsaure [German]
Seracic acid
Decanedioic acid, homopolymer
Acide sebacique [French]
UNII-97AN39ICTC
NSC 19492
SebacicAcid
1,8-dicarboxyoctane
CCRIS 2290
NSC19492
EINECS 203-845-5
MFCD00004440
BRN 1210591
97AN39ICTC
AI3-09127
26776-29-4
CHEBI:41865
Sebacic acid, 98%
DSSTox_CID_6867
DSSTox_RID_78231
DSSTox_GSID_26867
CAS-111-20-6
Polysebacic polyanhydride
n-Decanedioate
Iponic acid
4-oxodecanedioate
sebacic acid group
1,10-Decanedioate
Sebacic acid, 94%
Sebacic acid, 99%
Dicarboxylic acid C10
1,8-Octanedicarboxylate
ACMC-1C1QX
WLN: QV8VQ
EC 203-845-5
SCHEMBL3977
NCIOpen2_008624
4-02-00-02078 (Beilstein Handbook Reference)
KSC176K6J
octane-1,8-dicarboxylic acid
ARONIS24100
Decanedioic acid 111-20-6
CHEMBL1232164
DTXSID7026867
CTK0H6564
KS-00000UFN

Sebacic acid market is bifurcated on the basis of application as plasticizers, lubricants, solvents, adhesives, and chemical intermediates. 
Plasticizers including dibutyl sebacate, dioctyl sebacate, diethyl sebacate, and sebacic acid dihydrazide are widely used in alkyd resin, polyvinyl chloride, polyamide molding resins, and polyester resin. 
The product is used for manufacturing dibutyl sebacate which is a bio-based dibutyl ester of the sebacic acid. 
It is a specialty plasticizer which provides superior low temperature and excellent compatibility characteristics to various polymers.

Sebacic acid market growth will be supported by consumer inclination towards bio lubricant over conventional owing to low CO emission and stringent environmental policies. 
Lubricants application accounted market size over 120 million in 2018.  
Sebacic acid is used as additives for low temperature lubricants at high altitudes.  
Additionally, investments in automotive industry to develop high-performance fuel-efficient vehicles along with rise in consumer spending will stimulate product utilization.
 

Global lubricant industry growth will witness significant gains and rise over USD 180 billion at the end of 2024. 
Sebacic acid due to excellent lubricity, low temperature fluidity, high flash points, and higher thermal stability is widely used for manufacturing lubricants for automotive and aerospace sector. 
The product is also used as raw material to produce sebacate diesters such as DOS and DBS which in turn used in lubricants or complexed greases. 
Market growth is attributed to growing air travel and automotive industry globally.
 

Application
Sebacic acid has been used in the synthesis of:
• biodegradable and elastomeric polyesters [poly(glycerol sebacate)]
• novel bio-nylon, PA5.10[2]
• novel temperature-response hydrogel based on poly(ether-ester anhydride) nanoparticle for drug-delivery applications

Sebacic acid is normally made from castor oil, which is essentially glyceryl ricinoleate. 
The castor oil is treated with caustic soda at high temperature, for example 250 °C, so that saponification, leading to the formation of ricinoleic acid, is followed by a reaction giving sebacic acid and octan-2-ol

Aliphatic Polyamides
ProfessorMarianne Gilbert, in Brydson's Plastics Materials (Eighth Edition), 2017

18.2.3 Sebacic Acid and Azelaic Acid
Sebacic acid is normally made from castor oil, which is essentially glyceryl ricinoleate. 
The castor oil is treated with caustic soda at high temperature, for example 250 °C, so that saponification, leading to the formation of ricinoleic acid, is followed by a reaction giving sebacic acid and octan-2-ol:


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Because of the by-products formed, the yield of sebacic acid is necessarily low, and in practice, yields of 50–55% (based on the castor oil) are considered to be good.

Sebacic acid may also be produced by an electrooxidation process developed by Asahi Chemical Industry in Japan (Yamataka et al., 1979), and also piloted by BASF in Germany. 
It produces high purity sebacic acid from readily available adipic acid. The process consists of three steps. Adipic acid is partially esterified to the monomethyl adipate. 
Electrolysis of the potassium salt of monomethyl adipate in a mixture of methanol and water gives dimethyl sebacate. The last step is the hydrolysis of dimethyl sebacate to sebacic acid.
Overall yields are reported to be about 85% (Castor Oil, 2015).

Sebacic acid is used for PA610.

Polyamide 1010 is the polycondensation product of 1,10-decamethylene diamine and 1,10-decanedioic acid (sebacic acid)


Sebacic acid (13) (Fig. 4.3), a naturally occurring fatty acid, is reported to increase insulin-dependent glucose uptake by L6 skeletal muscle cells up to 1.7-fold in a dose-dependent manner 

Sebacic acid is a natural C10 liquid fatty acid, directly produced from castor oil. Our decanedioic acid has a high quality, a secure supply chain, and a natural origin. 

High purity
100% of vegetal origin
Linear chain
Granules or powder forms
High reactivity to produce a wide range of esters

 Sebacic acid offers a competitve solution in many applications:


To produce polymers
In industry: to produce plasticizers, lubricants, and corrosion retardants
In cosmetics: as buffering ingredient or as a chemical intermediate to produce a wide range of esters

Sebacic acid can be used directly in cosmetics formulation as a pH corrector (buffering). 
In this case, the main applications are skin care (mainly face/neck care), and color cosmetics.

The sebacic acid is also widely used as a synthesis intermediate to produce sebacates esters such as DIPS or DIS (diisopropyl sebacate), DOS (diethylhexyl sebacate), DES (diethyl sebacate) and DBS (dibutyl sebacate).


These sebacate are used as: emollient, solvent, plasticizer, masking (reducing or inhibiting the basic odour of the product), film forming, hair or skin conditioning. 
Generally, sebacate esters are claimed to enable a good penetration, give a non-oily and silky skin feel. 
These esters are also recognized to be good pigment dispersant (DOS), be good sun protection factor (SPF) booster (DIPS blended), and prevent whitening in antiperspirant (DIPS).


The sebacic acid (DC 10), is widely used to produce a various range of plastics, and brings to those plastics a bio-based part.

DC 10 provides a good compromise in term of properties: better than those given by adipic acid and very close to those allowed by dodecanedioic acid or by azelaic acid.


The most famous application of sebacic acid in the plastics world is the manufacture of polyamides (PA 6.10, PA 4.10, PA 10.10, etc). 
Compared to diacids with a lower carbon atom number (eg: adipic acid), the Sebacic acid provides better flexibility, ductility, hydrophobicity, and lower melting temperature.


The other types of plastics where sebacic acid is used are copolyamides, polyesters, copolyesters, alkyd resins, polyester, polyols, polyurethanes, etc.


Sebacic acid is widely used to produce a salt derivative, the (di)sodium sebacate, which is a corrosion inhibitor. 
The main application of this salt is coolant (anti-freeze) fluids for aircraft, automotive and truck engines.


Sebacic acid is also a raw material to produce sebacate diesters (DOS, DBS, …), used in complexed greases or lubricants. 
Generally, diesters are used as base oils for high performance lubricants (automotive, aerospace turbines, high reliability industrial hydraulics and compressor systems).

Moreover, sebacates have enhanced viscosity and excellent lubricity when compared with adipates.

These diesters offer major advantages (compared to mineral oils):


High viscosity index   
Low temperature fluidity
Low pour points 
Low volatility
High flash points
Low peroxide value
Good additive response     
High thermal stability
Overall excellent lubricity   
Oxidation resistance 
Low coking characteristics

 


1,10-decanedioic acid
111-20-6 [RN]
1210591 [Beilstein]
203-845-5 [EINECS]
Acide sebacique [French]
Acide sébacique [French] [ACD/IUPAC Name]
Decanedioic acid [ACD/Index Name]
MFCD00004440 [MDL number]
Sebacic acid [ACD/IUPAC Name] [Wiki]
Sebacinsaure [German]
Sebacinsäure [German] [ACD/IUPAC Name]
VS0875000
Ipomic acid
Seracic acid
[111-20-6]
1, 10-Decanedioic acid
1,10-Decanedicarboxylic acid
1,10-Decanedioic-2,2,9,9-d4 Acid
1,8-dicarboxyoctane
1,8-Octanedicarboxylic acid
1,8-Octanedicarboxylic acid (Decanedioic acid)
26776-29-4 [RN]
32734-00-2 [RN]
339080-77-2 [RN]
4-02-00-02078 [Beilstein]
4-02-00-02078 (Beilstein Handbook Reference) [Beilstein]
5505-62-4 [RN]
693-23-2 [RN]
72162-23-3 [RN]
73351-71-0 [RN]
Acide sebacique
CHEBI:41865
CORFREE M1
Decandioic acid, Octane-1,8-dicarboxylic acid
Decanedicarboxylic acid
decanedioate
decanedioicacid
EINECS 203-845-5
http:////www.amadischem.com/proen/517165/
http://en.atomaxchem.com/111-20-6.html
http://www.hmdb.ca/metabolites/HMDB0000792
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:41865
NCGC00164361-01
N-DECANEDIOIC ACID
Octane-1,8-dicarboxylic acid
sebacic acid 94%
sebacic acid 98%
sebacic acid, 98%
sebacic acid, 98+%
sebacic acid, reagent
SEBACIC ACID|DECANEDIOIC ACID
SEBACIC ACID-C-D16
sebacicacid
Sebacins??ure
Sebacinsaeure
Sebacinsaure
Sebacinsaure [German]
WLN: QV8VQ

Microbial production of sebacic acid from a renewable source: production, purification, and polymerization†    
Woo-Young Jeon,‡a   Min-Jeong Jang,‡b   Gyu-Yeon Park,‡ab   Hye-Jeong Lee,a   Sung-Hwa Seo,a   Hee-Suk Lee,a   Changpyo Han,a   Heeun Kwon,a   Ho-Chang Lee,c   Jong-Hwa Lee,c   Yong-Taek Hwang,d   Myung-Ock Lee,d   Jeong-Gyu Lee,e   Hong-Weon Lee*ab  and  Jung-Oh Ahn ORCID logo *ab  
 Author affiliations
Abstract
Sebacic acid (SA) is an aliphatic ten-carbon dicarboxylic acid (1,10-decanedioic acid) with a variety of industrial applications, including the production of plasticizers, lubricants, cosmetics, and plastics. 
Currently, SA is produced exclusively from alkaline pyrolysis of castor oil. 
Herein, we present an environmentally friendly green route of SA production from plant oil-derived sources by microbial ω-oxidation. 
We genetically engineered β-oxidation-blocked diploid yeast Candida tropicalis, and created an effective microbial cell factory with an increase of 46% in SA production by overexpression of genes involved in ω-oxidation of hydrocarbons compared to the original strain. 
A biotransformation process of SA production from decanoic acid methyl ester was developed to overcome the challenges of high-density cell culture, substrate feed, substrate/intermediate toxicity, and foam generation. 
Fed-batch production of engineered C. tropicalis resulted in a molar yield of above 98%, a productivity of 0.57 g L−1 h−1, and a final titre of 98.3 g L−1 in a 5-litre fermenter and the results were successfully reproduced using a larger scale 50-litre fermenter. 
The produced SAs were successfully purified to >99.8% using acid precipitation and recrystallization. 
Finally, bio-nylon 610 was successfully synthesized by polymerization of the purified SA with hexamethylenediamine and showed thermal properties very similar to those of commercially available nylon 610. 
The processes developed and described in this study can be employed to produce and isolate SA for the synthesis of bio-nylons, using environmentally friendly procedures based on microbial biotransformation with potential industrial applications.


Sebacic acid is a naturally occurring dicarboxylic acid with the formula (CH2)8(CO2H)2. 
It is a white flake or powdered solid. Sebaceus is Latin for tallow candle, sebum is Latin for tallow, and refers to its use in the manufacture of candles. 
Sebacic acid is a derivative of castor oil.In the industrial setting, sebacic acid and its homologues such as azelaic acid can be used as a monomer for nylon 610, plasticizers, lubricants, hydraulic fluids, cosmetics, candles, etc.
sebacic acid (CHEBI:41865) has parent hydride decane (CHEBI:41808)
sebacic acid (CHEBI:41865) has role human metabolite (CHEBI:77746)
sebacic acid (CHEBI:41865) has role plant metabolite (CHEBI:76924)
sebacic acid (CHEBI:41865) is a α,ω-dicarboxylic acid (CHEBI:28383)
sebacic acid (CHEBI:41865) is conjugate acid of sebacate (CHEBI:132954)
sebacic acid (CHEBI:41865) is conjugate acid of sebacate(2−) (CHEBI:76283)
3-hydroxysebacic acid (CHEBI:89182) has functional parent sebacic acid (CHEBI:41865)
decanedioyl-CoA (CHEBI:76345) has functional parent sebacic acid (CHEBI:41865)
sebacate (CHEBI:132954) is conjugate base of sebacic acid (CHEBI:41865)
sebacate(2−) (CHEBI:76283) is conjugate base of sebacic acid (CHEBI:41865)


Application

Plasticizers
Lubricants
Solvents
Adhesives
Chemical Intermediates
Others


Sebacic Acid
CAS: 111-20-6
In its purest form, Sebacic Acid is a powdered crystal or white flaky substance. 
It’s a naturally occurring dicarboxylic acid that is non-hazardous, though it can be vulnerable to flash ignition in its powder form. 
One of the most common uses for sebacic acid is in the manufacturing of candles. 
Sebacic acid also shows up in the industrial industry, being used as a monomer and intermediate for various products and materials.

What is Sebacic Acid? Where Does it Come From?

Sebacic acid is produced from castor oil. It’s mostly colorless but can be a light shade of yellow. 
It also has a mild odor to it, though nothing that stands out.

There are two ways that sebacic acid can be produced: castor oil and adipic acid. 
It’s far more common for sebacic acid to be derived from castor oil, as the process is green and cost effective. 
To make the sebacic acid, the castor oil is heated to high temperatures with alkali. 
The purity of the product is based on the type of reaction it has. 
Generally, modern conversion technology leads to a purer product.

Key Benefits of Sebacic Acid:

In cosmetic products, sebacic acid can act as a pH corrector. 
In plastics, sebacic acid can be used to provide better flexibility and lower melting temperature. 
For lubricants and anti-corrosion applications, sebacic acid is used to produce a salt derivative that can be used as a coolant for aircraft, automotive and truck engines.

Here are the attributes that make sebacic acid as flexible as it is.

Excellent lubricity

Low temperature fluidity

Higher thermal stability

High flash points

Low pour points

Common Uses for Sebacic Acid:

Sebaceus is Latin for tallow candle, and sebum is Latin for tallow. 
These terms refer to the use of sebacic acid in the manufacturing of candles. 
But as stated above, sebacic acid has a lot of uses for the industrial setting. 
Sebacic acid can be used as a monomer for nylon, lubricants, hydraulic fluids, cosmetics, plasticizers and more. 
It can also be used as an intermediate for antiseptics, aromatics and painting products.

ALSO KNOWN AS
Decanedioic acid; 1,8-Octanedicarboxylic acid


Use: Decanedioic acid isolated from the herbs of Piper cubeba. 
It is an intermediate of aromatics, antiseptics, and painting materials, also a cross-linking agent for epoxy resins

Use: In its purest form, Sebacic Acid is a powdered crystal or white flaky substance. 
It’s a naturally occurring dicarboxylic acid that is non-hazardous, though it can be vulnerable to flash ignition in its powder form. One of the most common uses for sebacic acid is in the manufacturing of candles. 
Sebacic acid also shows up in the industrial industry, being used as a monomer and intermediate for various products and materials.

Synonyms:
     decanedioic acid
1,10-    decanedioic acid
1,8-    dicarboxyoctane
     ipomic acid
1,8-    octanedicarboxylic acid
     sebacicacid
     seracic acid


SEBACIC ACID    
1,10-Decanedioic acid
1,8-Octanedicarboxylic acid
Decanedioic acid    
CAS #: 111-20-6
EC Number: 203-845-5


Sebacic acid
 Trade name
1,10-Decanedioic acid
1,8-Octanedicarboxylic acid
Decanedioic acid (9CI)
Decanedioic acid (9Cl)
SA
Sebacic acid
Sebacic acid (8CI)
Sebacic acid (8Cl)
Sebazinsaeure
n-Decanedioic acid
 Other identifiers
1,8-Octanedicarboxylic acid
(No other type specified)
Decanedioic acid
(IUPAC name)
decanedioic acid


Other names: Sebacic acid; Decanedicarboxylic acid; 1,10-Decanedioic acid; 1,8-Octanedicarboxylic acid; Seracic acid; USAF HC-1; n-Decanedioic acid; NSC 19492; Ipomic acid

Sebacinsäure

Sebacic acid is widely used in the preparation of sebacic acid esters, such as dibutyl sebacate, dioctyl sebacate, diisooctyl sebacate. 
These esters can be used as plasticizers for plastics and cold-resistant rubber, as well as for polyamide, polyurethane, alkyd resin, synthetic lubricating oil, lubricating oil additives, spices, coatings, cosmetics, etc. 
It can also be used as raw material for producing nylon 1010, nylon 910, nylon 810, nylon 610, nylon 9 and high temperature resistant lubricating oil diethylhexyl ester. 
It is also the raw material for the production of alkyd resins (used as surface coatings, plasticized nitrocellulose coatings, and urea resin varnishes) and polyurethane rubber, cellulose resins, vinyl resins, and synthetic rubber plasticizers, softeners, and solvents.

1. Sebacic acid can be used as cold plasticizer, nylon resins and other raw material.
2. It can be used as analytical reagents, etc.
3. Sebacic acid is mainly used as sebate plasticizer and nylon molding resin raw material, it is also used for high-temperature lubricant raw material. 
Its main product is methyl ester, isopropyl, butyl, octyl, nonyl phenyl ester and methyl ester, common ester is dibutyl sebacate and dioctyl sebacate. 
Sebacic acid plasticizers can be widely used in polyvinyl chloride, alkyd resins, polyester resins and polyamide molding resin due to its low toxicity and high temperature performance, so it is often used in the resin of some special purposes. 
Nylon molding resin which producted by sebacic acid has high toughness and low moisture absorption, it can also be processed into many special-purpose products. Sebacic acid is also rubber softener, surfactant, coating and fragrance raw materials.
4. Sebacic acid is used as GC Less tail agent, separation and analysis of fatty acids, it can be used to precipitate and quantitative determination of thorium, separation of thorium, cerium and other rare earth elements. 
Plasticizers, synthetic resins and synthetic fibers.

Production method    
It can be obtained by raw materials of natural castor oil or adipic acid monoester. 
Sebacic acid can be obtained by polymerization reaction with ethylene and carbon tetrachloride, but the world's industrial production of sebacic acid almost all use castor oil as raw material.
1. castor oil cracking process: under effect of alkali, castor oil is heated to proceed hydrolysis and generates sodium castor oil soap, then sulfuric acid is added to acidolysis and ricinoleic acid is obtained; 
in the presence of diluent cresol , alkali is added and it is heated to 260-280℃ to proceed splitting decomposition and generates sebacic acid and sodium bis octanol and hydrogen, lysate is diluted with water, heated and adding acid to neutralize, double salt is turned into monosodium salt; 
and then neutralized liquid after actived carbon decoloration is boiling and added acid, sebacic acid monosodium salt turns into sebacic acid and seeds out, after separation, drying can derive products. 
Material consumption fixed: castor oil (industrial) 2100kg/t, sulfuric acid (98%) 1600kg/t, caustic soda (95%) 1200kg/t, cresol (industrial) 100kg/t. 2.Oil n-decane fermentation method: n-decane is obtained by the separation of 200 # solvent oil or 166-182℃ fraction, sebacic acid is obtained by 19-2 Solutions Candida lipolytica fermentation.
2. New cyclopentanone method: palladium salt-copper or iron is as catalyst, in the solvent of ethanol, propanol or other alcohol, in the eased condition of low temperature of 40-60℃ and ordinary pressure, cyclopentene is oxidated by air to generate cyclopentanone, then it is obtained by oxidated of iron catalyst and titanium.

Sebacic acid, also known as 1, 10-decanedioic acid, belongs to aliphatic dibasic acid. 
Sebacic acid was present in the leaves of flue-cured tobacco, burley tobacco and aromatic tobacco. 
Sebacic acid was white crystal in flake form at room temperature. 
Slightly soluble in water, sebacic acid was insoluble in benzene, petroleum ether, carbon tetrachloride. 
In contrast, sebacic acid was soluble in ethanol and ethyl ether. Irritant to the eyes, respiratory system and skin irritation, sebacic acid oral harmful. 
However, sebacic acid was low toxic and flammable.

Sebacic acid is a dicarboxylic acid with structure (HOOC)(CH2)8(COOH), and is naturally occurring.
In its pure state it is a white flake or powdered crystal. 
The product is described as non-hazardous, though in its powdered form it can be prone to flash ignition (a typical risk in handling fine organic powders).
Sebaceus is Latin for tallow candle, sebum (tallow) is Latin for tallow, and refers to its use in the manufacture of candles. 
Sebacic acid is a derivative of castor oil, with the vast majority of world production occurring in China which annually exports over 20,000 metric tonnes, representing over 90 % of global trade of the product.
In the industrial setting, sebacic acid and its homologues such as azelaic acid can be used in plasticizers, lubricants, hydraulic fluids, cosmetics, candles, etc. 
Sebacic acid is also used as an intermediate for aromatics, antiseptics, and painting materials.


Decanedioic acid was named by Thenard LJ (1802) from the Latin sebaceus(tallow candle) or sebum (tallow) in reference to its use in the manufacture of candles. 
Thenard LJ isolated this compound from distillation products of beef tallow. 
In 1954, it was reported that it was produced in excess of 10,000 tons annually by alkali fission of castor oil. 
Sebacic acid and its derivatives, as azelaic acid, have a variety of industrial uses as plasticizers, lubricants, diffusion pump oils, cosmetics, candles, etc. 
It is also used in the synthesis of polyamide, as nylon, and of alkyd resins. 
An isomer, isosebacic acid, has several applications in the manufacture of vinyl resin plasticizers, extrusion plastics, adhesives, ester lubricants, polyesters, polyurethane resins and synthetic rubber.

Sebacic acid reacts exothermically to neutralize bases, both organic and inorganic. 
May react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. 
Can react with active metals to form gaseous hydrogen and a metal salt.
Such reactions are slow in the dry, but systems may absorb enough water from the air to allow corrosion of iron, steel, and aluminum parts and containers. 
Reacts slowly with cyanide salts to generate gaseous hydrogen cyanide. Reacts with solutions of cyanides to cause the release of gaseous hydrogen cyanide. 
May generate flammable and/or toxic gases and heat with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. 
May react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. 
Can be oxidized exothermically by strong oxidizing agents and reduced by strong reducing agents. 
May initiate polymerization reactions.


Purify sebacic acid via the disodium salt which, after crystallisation from boiling water (charcoal), is again converted to the free acid. 
The free acid is crystallised repeatedly from hot distilled water or from Me2CO/pet ether and dried under vacuum. [Beilstein 2 IV 2078.]


Sebacic acid has the maximum demand from the cosmetics industry as it finds applications in various formulations. 
It is a prominent ingredient in different products wherein it is used as a pH adjuster, firm filming agent, and fragrance enhancer. 
The rising popularity of social media is also boosting the growth of the cosmetics sector. 
Moreover, increased awareness about personal care products, especially in emerging regions, is likely to spur the segment growth.

Currently, the polymer manufacturing application segment accounts for the highest market share. 
The chemical is an integral component in the manufacturing of biodegradable plastics. 
The plastic ban in developing countries has also been regarded as a boon to the manufacturers of biodegradable polymers. 
The others segment includes paints and coatings and metalworking fluids. 
The product is used as a precursor in lubricants and paints owing to its oxidizing corrosion inhibition and filming properties.


The global sebacic acid market size was valued at USD 245.6 million in 2017. 
It is projected to expand further at a CAGR of 3.7% over the forecast period. 
Growing demand for biodegradable polymers due to their eco-friendly nature is expected to drive the global market. 
The demand for sebacic acid is also supported by favorable government regulations across the globe.

It is mainly derived from castor oil and is classified as a second-generation derivative. 
It accounts for a market share of about 27% in the gen II castor oil derivatives market. 
It is majorly used in the manufacturing of biodegradable plastics, and nylon 6.10, which have major applications in textiles, automotive, and packaging industries.

The U.S. market for the chemical is majorly driven by its use as a precursor to polymers and lubricants and growing demand in cosmetic products. 
Increasing population coupled with growing awareness about personal health and skin care products is augmenting the demand for good quality cosmetics. 
This, in turn, is boosting the market growth. Moreover, wide usage in several end-use industries, such as lubricants, paints, and adhesives, and polymers, is contributing to the product demand.

Emerging economies, such as China, India, Japan, and Brazil, are investing heavily in chemical production to fulfill the growing demand. 
This chemical is classified as non-toxic and non-hazardous substance by the ECHA and REACH and hence also provides easy, as well as affordable, trade between different regions. 
Growing urban population, majorly in China and India, has led to a rise in demand for cosmetic products. 
Governments in these regions have undertaken several initiatives to develop green chemicals that provide a faster yield of castor seeds.

Sebacic acid cost is heavily dependent on castor oil, the key raw material. 


Application Insights
Sebacic acid has the maximum demand from the cosmetics industry as it finds applications in various formulations. 
It is a prominent ingredient in different products wherein it is used as a pH adjuster, firm filming agent, and fragrance enhancer. 
The rising popularity of social media is also boosting the growth of the cosmetics sector. 
Moreover, increased awareness about personal care products, especially in emerging regions, is likely to spur the segment growth.

Currently, the polymer manufacturing application segment accounts for the highest market share. 
The chemical is an integral component in the manufacturing of biodegradable plastics. 
The plastic ban in developing countries has also been regarded as a boon to the manufacturers of biodegradable polymers. The others segment includes paints and coatings and metalworking fluids. 
The product is used as a precursor in lubricants and paints owing to its oxidizing corrosion inhibition and filming properties.


Global sebacic acid market

These properties have augmented the demand for it in major industries, such as automotive, aerospace, and construction. 
Increasing automobile production has boosted the market for paints and lubricants, in turn, driving the sebacic acid demand. Rapid urbanization, as well as industrialization, in the developing countries of Asia Pacific, have led to a rise in demand for metalworking chemicals containing sebacic acid.


The primary factor driving demand in North America is the broad product scope and extensive usage in end-use industries, such as automobiles, textiles, and cosmetics industries. 
Original Equipment Manufacturers (OEM’s) in the region are focusing on upgrading vehicles by providing additional coatings to the base paint. 
Sebacic acid is an important ingredient for these paints and coatings as it acts as a filming ingredient due to its excellent temperature resistance properties.

Application:
Polymers
Cosmetics
Lubricants
Others (Metal working, Paints & Coatings, etc.)


    
Sebacic acid;
Decanedioic acid


 FA  Fatty acids
  FA01 Fatty Acids and Conjugates
   FA0117 Dicarboxylic acids
    C08277  Decanedioic acid


sebacic acid is a C10 di-functional fatty acid with natural origin. It s in the form of white granular or powder. 

Method for preparing sebacic acid with ricinus oil compounds
Abstract
The invention discloses a method for preparing a sebacic acid from a castor oil compound. 
The method comprises the following steps that: pyrolysis of a castor oil compound, an isomerous carboxylic acid of a thinner, a high-temperature surface active agent for improving homogenization of a reaction mixture and/or high-temperature polymerization inhibitor for inhibiting polymerization of the castoroil compound at a high temperature is performed in a concentrated base solution to give initial pyrolysis product which is mixture of a decanedioic acid disodium salt, 10-hydroxydecanoic acid and a 10-formyldecanoic acid; the mixture is oxidized by a high-temperature strong base to give the decanedioic acid disodium salt. 
An end pyrolysis product is subjected to neutralization, separation of fatty acid, decolourization by macroporous resin, decolourization by active carbon, acidification, crystallization and recrystallization to produce an industrial sebacic acid and a fine sebacic acid. 
The method has the advantages of avoidance of pollution caused by phenol contained waste water generated by using a phenol contained thinner, more complete pyrolysis, improvement on yield of sebacic acid and purity of sebacic acid, and reduction in raw material consumption.

Sebacic Acid & it's Derivatives
Sebacic acid,sebacic acid diesters,Sebacic acid,monoester,Sebacic acid,solts,1,10-Decanediol
Products    Brand    Chemical name    Containers
(㎏)    Description and uses
Sebacic acid    Sebacic acid    Sebacic Acid
(1,10-Decanedioic Acid)    20
250
500    Nylon,Polyesters,Corrosion inhibitor
Sebacic acid diesters    DES    Diethyl Sebacate    16    Cosmetics,Pharmacy
DMS    Dimethyl Sebacate    190    Intermediotes
DOS    Dioctyl Sebacate    180    Plasticizers,Grease oil
DBS    Dibuthyl Sebacate    180    Plasticizers,Approved byFDA
DIPS    Diisopropyl Sebacate    16    Cosmetics,Pharmacy
Sebacic acid solts    Sebacic acid soda    Disodium Sebacate    10    Antifreeze,Corrosion inhibitor
1,10-Decanediol    1,10-Decanediol    1,10-Decanediol    20    Pharmacy,Perfume,Polyesters

Sebacic acid is a dicarboxylic acid obtained from the dry distillation of castor oil. 
It is derived from castor oil. 
Two molecules are needed to obtain a castor sebacic acid.

Castor oil is obtained from the fruit seed of castor (Ricinus communis L.) a large shrub that grows mainly in India, Brazil and China.

The seed has an oil content of 40-50%.

It is solid at room temperature and melts above 130 ° C.

Is in the form of white crystalline solid (powder or granules).

Growing demand for sebacic acid from automotive industry is one of the key factors for the growth of global sebacic acid market during forecast period.
Sebacic acid is used in the form of sebacate esters in automotive industries for manufacturing PVC films as it helps to provide properties such as low-temperature flexibility and crack resistance, which is anticipated to drive the growth of global sebacic acid market over the coming years.

In addition to this, several major automotive manufacturing companies are using sebacic acid as a coolant in automobiles which is projected to further spur the global sebacic acid market growth through 2025. 
However, the availability of various substitutes of sebacic acid like adipic acid, and azelaic acid for various applications is a factor that can act as major impediment to the global sebacic acid market during forecast period.
The global sebacic acid market is segmented based on source, application, region and company.
Based on application, the market can be segmented into personal care & cosmetics, lubricants & greases, metalworking fluids, plastics, polymers and others.

Among them, the personal care & cosmetics sector dominated the market until 2019 and is projected to maintain its lead over the forecast period as well. 
This growth is attributable to its use as a pH adjuster, firm filming agent, and fragrance enhancer in numerous products, which is likely to increase its demand in cosmetics industry, thereby boosting the growth of global sebacic acid market over the coming years.


Widely used for the production of a broad range of industrial products, such as plasticizers, candles, lubricants, hydraulic fluids and resins, sebacic acid has been in high demand over recent years. 
Currently, its synthesis mostly relies on castor oil, which is a bio-based, renewable raw material, as the substance is extracted from Ricinus communis’ seeds. 
This green aspect is one of the main reasons why sebacic acid production dominates castor oil’s industrial use, particularly in China - the second largest producer of this oil.

One of the most common synthetic routes to obtain sebacic acid involves the hydrolyzation of castor oil to obtain ricinoleic acid, which then undergoes an alkali fusion/cracking in the presence of phenol and sodium hydroxide (NaOH). 
Once sebacic acid is purified, the resulting wastewater contains large quantities of the initial phenolic compound used.

Being a contaminant, phenols should be removed from wastewater and properly disposed of. 
If the concentration of the organic compound is particularly high, the effluents are recalcitrant to conventional biological treatments in wastewater facilities. 
Therefore, it is important for production facilities to conduct phenol extraction activities prior to discharging the effluents. Furthermore, manufacturers should also look at methods to recover or recycle phenol in their processes.


Lubricity Characterizations of Sebacic Acid Based Ester
The current study aimed to evaluate the effect of long-chain and branch alcohol on lubricity of sebacic acid based ester. 
Since currently synthesis of a new lubricant to improve the lubricity properties and quality of lubricant is increasing, in this study, sebacic acid esters were synthesized by the conventional esterification method with some modification using sulfuric acid (SA) as catalyst. 
Twelve samples of sebacic acid esters with different chemical structures were synthesized including di-2-octyl sebacate, didecyl sebacate, di-2 ethylhexanol sebacate, di-2-ethylbutyl sebacate and dioleyl sebacate. These diesters were tested in terms of their suitability as lubricant. 
The results showed that the pour point, flash point and oxidation stability were affected by liner and branch of the alcohol used. 
Di-2-ethylbutyl sebacate (D2EBS) and di-2-ethylhexanol sebacate (D2EHS) showed very low pour point at -44°C and -60°C respectively, while the same carbon number of dihexyl sebacate (DHS) and dioctyl sebacate (DOS) recorded high pour point at 8°C and 15 °C respectively. 
These differences were due to the presence of the branching. DOS recorded the highest oxidative stability at 290°C. 
However, there was a slight negative effect of the branching on the flash point.


Sebacic acid is a widely used industrial intermediate, with an annual global demand of around 20,000 metric tons. 
In addition to its application in greases, sebacic acid is a key intermediate in engineering plastics, specialty adhesives and as a corrosion inhibitor in metalworking fluids and longlife antifreeze formulations.

Sebacic acid also is used to make disodium sebacate (DSS). DSS is approved for use in greases for incidental food contact under CFR 21.178.3570. 
Sebacate esters find application as low-temperature plasticizers, synlube base stocks, and in cosmetics as emollients and fragrance carriers. 
As with azeleate esters, the sebacate esters are frequently used as liquid proxies for the corresponding acid in making greases.

SHIFTING MARKETS

Both sebacic acid and azelaic acid are oleochemical derivatives. 
Azelaic acid is produced via the ozonolysis of oleic acid. The emergence of the biodiesel industry in North America, Europe and Asia has significantly increased the industrial demand for soy and corn oils, the principle sources of oleic acid. This has exerted upward price pressure on the key raw material for azelaic acid.

Sebacic acid is a castor oil derivative. It is produced via the cracking of ricinoleic acid, the primary fatty acid component of castor oil. In addition to being the raw material for sebacic acid, ricinoleic acid is an important raw material for the grease industry as it yields 12-hydroxystearic acid (12- HSA) upon hydrogenation.


Sebacic Acid-Powder is the result of a caustic fusion of castor oil.
Some major applications of Sebacic Acid are the manufacture of Nylon 6-10, a corrosion inhibitor in metalworking fluids, and a complexing agent in greases.

Tag: sebacic acid
Formulation 101: Lithium Complex Grease
Posted on October 15, 2018 - Product News

Lithium-Complex GreaseThe first use of grease dates back to ancient times, when man first used animal fats and vegetable oils to reduce friction. 
Analysis of these crude lubricants shows that lime was sometimes mixed in as a thickener, making this the first complex grease.

The science of lubricating technology has come a long way since ancient times. 
Simply put, lubricating grease is defined as a solid-to-semi fluid dispersion of a thickening agent in a liquid lubricant. 
Beyond that different ingredients can be added to impart special properties.

Traditionally, metallic soaps such as calcium stearate, sodium stearate, and lithium stearate are used as thickeners. 
Fatty acids such as lithium 12-hydroxystearate can also be used. 
Lithium greases are by far the most popular grease worldwide, because they have excellent heat tolerance like the sodium greases and the water resistance of calcium greases.

Lithium Complex greases first entered the market in 1962. 
According to NLGI International, Today Lithium Complex grease accounts for 42% of all North American Grease production. 
Lithium Complex Greases are favored over traditional Lithium greases because of their higher dropping points and improved heat resistance. 
They also work well in low temperatures.

A basic recipe for grease is below:

Thickener    10 – 15 %
Base Oil    80 – 90%
Performance Additives    5 – 10%
A tremendous amount of formulation science is put into achieving all the performance properties of a premium grease. 
Because greases are formulated for their intended applications, and the properties of the grease are very important, several laboratory tests are used to assess grease properties.

ATAMAN’s Grease Product Line
12‐Hydroxystearic Acid (12‐HSA)
Adipic Acid
Azelaic Acid
Boric Acid
Sebacic Acid
Dibutyl Sebacate (DBS)
Dimethyl Sebacate (DMS)
Dioctyl Sebacate (DOS)
Disodium Sebacate (DSS)
Lithium Hydroxide


Sebacic acid, also known as SBA, is a castor oil derivative which finds many industrial uses. 
It is used as a corrosion inhibitor in lubricants and metalworking fluids by forming a thin coating on the metal which restricts access by corrosive ions. 
Sebacic acid is used in the production of Nylon 6-10 and is a common carboxylic acid used in the manufacture of plasticizers. 
It also finds uses in hydraulic fluids, cosmetics and candles. 
Lithium hydroxystearate complex greases use dicarboxylic acids, such as sebacic acid, for unusual performance parameters. 
Producers of SBA include China, the world’s largest, India and the United States.

This invention relates to a metal corrosion inhibitor for use in aqueous solutions, and to antifreeze/coolant compositions containing such a corrosion inhibitor. 
More particularly, this invention relates to a corrosion inhibitor comprising a combination of monobasic acids or the alkali metal, ammonium, or amine salts of said acids and a hydrocarbyl triazole together with imidazole, and to antifreeze/coolant compositions containing the same.

[0002] Automobile engine cooling systems contain a variety of metals, including copper, solder, brass, steel, cast iron, aluminum, magnesium, and their alloys. 
The possibility of corrosive attack on such metals is high, due to the presence of various ions as well as the high temperatures, pressures, and flow rates found in such cooling systems. 
The presence of corrosion products within the cooling system can interfere with heat transfer from the engine combustion chambers, which may subsequently cause engine overheating and engine component failure due to excess metal temperatures. 
See generally Fay, R. H., "Antifreezes and Deicing Fluids," in Kirk-Othmer Encyclopedia of Chemical Technology (1978 ed.), vol. 3, pp. 79 - 95. 
It would therefore be generally advantageous if the formation of corrosion products within automobile cooling systems could be controlled or eliminated. 
It is one object of the instant invention to provide a corrosion inhibitor useful in the prevention and control of corrosion in automobile engine cooling systems containing various metals.

[0003] The trend towards improved fuel economy for automobiles has led to the increased use of aluminum and in some cases magnesium for engine and cooling system components. 
However, it has been found that pitting and crevice corrosion are particularly prevalent in aluminum-containing cooling systems. 
Many conventional corrosion inhibitor additives used in automobile cooling systems do not provide adequate protection against the pitting and crevice corrosion phenomena found with various aluminum and magnesium alloys. 
It would therefore be particularly advantageous if the pitting and crevice corrosion phenomena found in automobile cooling systems containing aluminum or magnesium alloys could be controlled or eliminated. 
It is another object of the instant invention to provide a corrosion inhibitor for use in automobile cooling systems which prevents or controls pitting and crevice corrosion of aluminum and magnesium metal surfaces.

[0004] Corrosion inhibitors employed in automobile antifreeze/coolant formulations are gradually depleted by use and the build-up of corrosion products in the cooling system. 
It would thus be advantageous if the build-up of corrosion products within the system and subsequent corrosion inhibitor depletion or degradation could be controlled or eliminated. 
It is a further object of the instant invention to provide a corrosion inhibitor which is less prone to depletion or degradation than traditional corrosion inhibitors used in antifreeze/coolant formulations.

[0005] It is well known that various monobasic acids as well as the salts of such acids are individually effective as corrosion inhibitors when employed in antifreeze/coolant formulations. 
For example, the use of sodium salts of various monobasic acids as mild steel corrosion inhibitors in aqueous solutions is disclosed in Hersch, P., et al., "An Experimental Survey Of Rust Preventives In Water - II. The Screening Of Organic Inhibitors," Journal of Applied Chemistry, vol. 11 (July, 1961), pp. 254-55. 
The use of a mixture of sodium sebacate (the sodium salt of sebacic acid) and benzotriazole as a useful corrosion inhibitor in engine coolants is disclosed in G. Butler & A.D. Mercer, "Inhibitor Formulations for Engine Coolants," British Corrosion Journal, vol. 12., no. 3 (1977), pp. 171-74.

[0006] Several U.S. and foreign patent references disclose the use of various monobasic acids, or the salts of such acids, as corrosion inhibitors for use in antifreeze/coolant compositions:
   US-A-4,342,596 discloses a corrosion inhibiting composition for metals comprising 5-20 parts of a C₈-C₂₀ aliphatic monobasic acid, 0.5-4 parts of a lubricant, 0.5-4.0 parts of an amino alkylalkanolamine, 10-35 parts of an aromatic mono- or polycarboxylic acid, and an amine used to form a water-soluble salt with the aromatic acid;
   US-A-3,573,225 discloses a corrosion inhibitor containing 50-100 parts of a salt of a C₆-C₁₈ saturated carboxylic acid, 20-200 parts of an alkali metal benzoate, and 1-50 parts of an alkanolamide selected from the reaction products of ethanolamines and a saturated C₆-C₁₈ fatty acid;
   GB-A-2,122,598 discloses a metal corrosion inhibitor which comprises at least one C₆-C₁₀ aliphatic carboxylic acid, at least one C₆-C₈ polyhydroxycarboxylic acid, and at least one aromatic monocarboxylic acid, in which each of the acids is present as a salt;
   US-A-4,759,864 discloses a corrosion-inhibited antifreeze concentrate formulation containing no phosphate, amine or nitrite consisting essentially of liquid alcohol freezing point depressant, a C₆-C₁₂ aliphatic monobasic acid, an alkali metal borate and a hydrocarbyl triazole.

[0007] US-A-4,647,392 discloses a corrosion inhibitor for use in antifreeze systems comprising the combination of a C₅-C₁₆ aliphatic monobasic acid, a C₅-C₁₆ hydrocarbyl dibasic acid and a hydrocarbyl triazole.

[0008] EP-A-0251480 discloses a corrosion inhibitor for use in antifreeze systems comprising the combination of a C₈-C₁₂ aliphatic monobasic acid, an alkylbenzoic acid, and a hydrocarbyl triazole.

[0009] The present invention is directed to a novel corrosion inhibitor composition for use in aqueous systems, an antifreeze/coolant concentrate containing the inhibitor composition and aqueous antifreeze/coolant compositions containing the inhibitor composition. 
It has been found that the components of the corrosion inhibitor composition have an improved corrosion inhibiting effect when used in antifreeze/coolant compositions.

[0010] The antifreeze concentrate comprises a water soluble liquid alcohol freezing point depressant and a corrosion inhibitor consisting of carboxylic acids or their salts and a triazole compound, wherein the concentrate contains 
1) from 0.1 to 15 weight percent, calculated as the free acid, of a C₅-C₁₆ aliphatic monobasic acid or the alkali metal, ammonium or amine salt thereof, 
2) from 0.1 to 0.5 weight percent of a hydrocarbyl triazole, and 
3) from 0.05 to 5 weight percent imidazole, said weight percentages being based on the amount of liquid alcohol present.

[0011] There is also provided a method of treating aqueous fluids containing a water soluble liquid alcohol freezing point depressant to reduce the corrosion of metals in contact with the fluid by the addition of carboxylic acids or their salts and a triazole compound as corrosion inhibitors, characterised in that 
1) from 0.1 to 15 weight percent, calculated as the free acid, of a C₅-C₁₆ aliphatic monobasic acid or the alkali metal, ammonium or amine salt thereof, 
2) from 0.1 to 0.5 weight percent of a hydrocarbyl triazole, and 
3) from 0.05 to 5 weight percent imidazole are incorporated into the fluid, said weight percentages being based on the amount of the liquid alcohol present.

[0012] The novel corrosion inhibitor of the instant invention comprises the combination of an aliphatic monobasic acid or the alkali metal, ammonium, or amine salt of said acid, a hydrocarbyl triazole and imidazole for use as a corrosion inhibitor in aqueous systems, particularly in automobile antifreeze/coolant compositions.

[0013] The aliphatic monobasic acid component of the above-described corrosion inhibitor may be any C₅-C₁₆ aliphatic monobasic acid or the alkali metal, ammonium, or amine salt of said acid, preferably at least one C₆-C₁₂ aliphatic monobasic acid or the alkali metal, ammonium, or amine salt of said acid. 
This would include one or more of the following acids or isomers thereof: 
heptanoic, octanoic, nonanoic, decanoic, undecanoic and dodecanoic, and mixtures thereof. 
Octanoic acid and 2-ethyl hexanoic acid are particularly preferred. 
Any alkali metal, ammonium, or amine can be used to form the monobasic acid salt; however, alkali metals are preferred. 
Sodium and potassium are the preferred alkali metals for use in forming the monobasic acid salt.

[0014] The hydrocarbyl triazole component of the above-described corrosion inhibitor is preferably an aromatic triazole or an alkyl-substituted aromatic triazole; for example, benzotriazole or tolyltriazole. 
The most preferred triazole for use is tolyltriazole. 
The hydrocarbyl triazole is employed at concentrations of about 0.1-0.5 wt. %, preferably about 0.1-0.3 wt.%. 
Hydrocarbyl triazoles are useful in improving the corrosion protection of copper and copper alloys.

[0015] Imidazole may be added at levels of from 0.05 to 5 weight percent, preferably from 0.1 to 1 weight percent, the weight percent being based on the amount of liquid alcohol present. 
Alkyl- or aryl-substituted imidazoles may also be used.

[0016] The above-described corrosion inhibitor mixture will most typically be employed in antifreeze formulations as coolants for internal combustion engines. 
Other applications may include hydraulic fluids, aqueous cutting oils, paints, soluble oils, metal cutting fluids, aircraft deicers, and greases. 
In these applications, the monobasic acid salts may be formed with metal hydroxides including sodium, potassium, lithium, barium, calcium, and magnesium.

[0017] The antifreeze formulations most commonly used include mixtures of water and water soluble liquid alcohol freezing point depressants such as glycol and glycol ethers. 
The glycol ethers which can be employed as major components in the present composition include glycols such as ethylene glycol, diethylene glycol, propylene glycol, and dipropylene glycol, and glycol monoethers such as the methyl, ethyl, propyl and butyl ethers of ethylene glycol, diethylene glycol, propylene glycol, and dipropylene glycol. 
Ethylene glycol is particularly preferred as the major antifreeze formulation component.

[0018] In one preferred embodiment of the instant invention, the above-described corrosion inhibitor is employed in admixture with an aqueous antifreeze/coolant solution comprising 10% to 90% by weight of water, preferably 25% to 50% by weight, a water soluble liquid alcohol freezing point depressant, preferably ethylene glycol.

[0019] It has been found that excellent pH control and buffer capacity near neutral pH is provided when using combinations of partly neutralised aliphatic acid corrosion inhibitors and imidazole. 
Reserve alkalinity, reserve acidity and pH are easily controlled by either modifying the amount of neutralisation of the acids and/or the imidazole content. 
The addition of imidazole assists in the pH control. 
Alkali metal hydroxides may be added to adjust the pH of the composition to the desired level. 
The formulations according to the present invention are simple to blend to a near neutral pH range, as is required in engine antifreeze systems.

[0020] Dibasic acids may be included in order to further improve corrosion protection, i.e. from 0.1 to 15 weight percent, calculated as the free acid of a C₅-C₁₆ hydrocarbyl dibasic acid or the salt thereof. 
The dibasic acid component of the above-described corrosion inhibitor may be any hydrocarbyl C₅-C₁₆ dibasic acid or the alkali metal, ammonium, or amine salt of said acid, preferably at least one C₈-C₁₂ hydrocarbyl dibasic acid or the alkali metal, ammonium, or amine salt of said acid. 
Included within this group are both aromatic and aliphatic C₅-C₁₆ dibasic acids and salts, preferably C₈-C₁₂ aliphatic dibasic acids and the alkali metal, ammonium, or amine salts of said acids. 
This would include one or more of the following acids: suberic, azelaic, sebacic, undecanedioic, dodecanedioic, the diacid of dicyclopentadiene (hereinafter referred to as DCPDDA), terephthalic, and mixtures thereof. 
Sebacic acid is particularly preferred. 
Any alkali metal, ammonium, or amine can be used to form the dibasic acid salt; however, alkali metals are preferred. 
Sodium and potassium are the preferred alkali metals for use in forming the dibasic acid salt. 
The combination of monobasic acid, dibasic acid, imidazole and hydrocarbyl triazole is particularly preferred.

[0021] One or more additional conventional corrosion inhibitors may also be employed in combination with the above-described corrosion inhibitor. 
Such conventional corrosion inhibitors may be employed at concentrations of 0.01-5.0 wt. %, and may be selected from the group comprising: alkali metal borates, alkali metal silicates, alkali metal benzoates, alkali metal nitrates, alkali metal nitrites, alkali metal molybdates, and hydrocarbyl thiazoles. 
The most preferred conventional corrosion inhibitors for use in combination with the novel corrosion inhibitor of the instant invention are hydrocarbyl triazoles, hydrocarbyl thiazoles, and sodium metasilicate pentahydrate. Organosilane stabilizers may also be employed in conjunction with the sodium metasilicate pentahydrate.

[0022] The method of this invention will be further illustrated by the following examples. 
In the following examples, all percents are weight percents unless otherwise specified.
EXAMPLES

[0023] A number of antifreeze concentrate formulations were prepared comprising a major amount of ethylene glycol (at least 93 wt%).
Example 1 (Comparative)

[0024] An antifreeze formulation was prepared comprising a major amount of ethylene glycol, 3.5% 2-ethylhexanoic acid, and 2% NaOH (50%) to modify the pH of the formulation to between 7.0 and 9.0.
Example 2 (Comparative)

[0025] An antifreeze formulation was prepared comprising a major amount of ethylene glycol, 0.2% tolytriazole, and 0.02% NaOH (50%) to modify the pH of the formulation to between 7.0 and 9.0.
Example 3 (Comparative)

[0026] An antifreeze formulation was prepared comprising a major amount of ethylene glycol, 0.2% tolytriazole, 3.5% 2-ethyl hexanoic acid, and 2% NaOH (50%) to modify the pH of the formulation to between 7.0 and 9.0.
Example 4 (Comparative)

[0027] An antifreeze formulation was prepared comprising a major amount of ethylene glycol, and 0.8% imidazole.
Example 5 (Invention)

[0028] An antifreeze formulation was prepared comprising a major amount of ethylene glycol, 0.2% tolytriazole, 3.5% 2-ethyl hexanoic acid, 0.1% imidazole, and 2% NaOH (50%) to modify the pH of the formulation to between 7.0 and 9.0.
Example 6 (Invention)

[0029] An antifreeze formulation was prepared comprising a major amount of ethylene glycol, 0.2% tolytriazole, 3.5% 2-ethyl hexanoic acid, 0.8% imidazole, and 1.75% NaOH (50%) to modify the pH of the formulation to between 7.0 and 9.0.
Example 7 (Comparative)

[0030] An antifreeze formulation was prepared comprising a major amount of ethylene glycol, 3.5% sebacic acid, and 2.75% NaOH (50%) to modify the pH of the formulation to between 7.0 and 9.0.
Example 8 (Comparative)

[0031] An antifreeze formulation was prepared comprising a major amount of ethylene glycol, 0.2% tolytriazole, 3.5% sebacic acid, and 2.8% NaOH (50%) to modify the pH of the formulation to between 7.0 and 9.0.
Example 9 (Comparative)

[0032] An antifreeze formulation was prepared comprising a major amount of ethylene glycol, 0.2% tolytriazole, 3.5% sebacic acid, 0.5% imidazole, 2.53% NaOH (50%) to modify the pH of the formulation to between 7.0 and 9.0.
Example 10 (Comparative)

[0033] An antifreeze formulation was prepared comprising a major amount of ethylene glycol, 0.2% tolytriazole, 0.85% sebacic acid, 1.65% octanoic acid, and 1.55% NaOH (50%) to modify the pH of the formulation to between 7.0 and 9.0.
Example 11 (Invention)

[0034] An antifreeze formulation was prepared comprising a major amount of ethylene glycol, 0.2% tolytriazole, 0.85% sebacic acid, 1.65% octanoic acid, 0.5% imidazole, and 1.55% NaOH (50%) to modify the pH of the formulation to between 7.0 and 9.0.
Example 12 (Comparative)

[0035] An antifreeze formulation was prepared comprising a major amount of ethylene glycol, 3.5% hexanoic acid, and 2.13% NaOH (50%) to modify the pH of the formulation to between 7.0 and 9.0.
Example 13 (Invention)

[0036] An antifreeze formulation was prepared comprising a major amount of ethylene glycol, 0.2% tolytriazole, 3.5% hexanoic acid, 0.8% imidazole, and 1.76% NaOH (50%) to modify the pH of the formulation to between 7.0 and 9.0.
Example 14 (Comparative)

[0037] An antifreeze formulation was prepared comprising a major amount of ethylene glycol, 0.2% tolytriazole, 3.25% 2-ethyl hexanoic acid, 0.25% sebacic acid, and 2.07% NaOH (50%) to modify the pH of the formulation to between 7.0 and 9.0.
Example 15 (Comparative)

[0038] An antifreeze formulation was prepared comprising a major amount of ethylene glycol, 0.2% tolytriazole, 3.25% 2-ethyl hexanoic acid, 0. 25% sebacic acid, 1. 15% borax (10aq), and 2.07% NaOH (50%) to modify the pH of the formulation to between 7.0 and 9.0.
Example 16 (Invention)

[0039] An antifreeze formulation was prepared comprising a major amount of ethylene glycol, 0.2% tolytriazole, 3.25% 2-ethyl hexanoic acid, 0.25% sebacic acid, 0.8% imidazole, and 1.85% NaOH (50%) to modify the pH of the formulation to between 7.0 and 9.0.
Table I shows the results of dynamic high temperature corrosion tests carried out according to MTU for an aliphatic acid inhibitor formulation, without buffer, with borate and imidazole. Low corrosion rates are found for the buffer-free formulation and for the formulation containing imidazole as a buffer agent. 
High corrosion rates are found for the formulation containing borate. 
It can be seen that although borates may provide pH buffer capacity, corrosion protection of aluminium is affected.


RETURN TO ISSUEPREVARTICLENEXT
Production of Sebacic Acid Using Two-Phase Bipolar Membrane Electrodialysis
Fang Zhang, Chuanhui Huang, and Tongwen Xu*
Abstract
To produce a water-insoluble acid—sebacic acid—in an environmentally friendly manner, two-phase bipolar membrane electrodialysis (TPBMED) was proposed to convert sodium sebacate into sebacic acid in ethanol−water mixtures. 
The results indicated that BP-C configuration (BP, bipolar membrane; C, cation-exchange membrane) was better than the other configurations: BP-A (A, anion-exchange membrane), BP-A-C, and BP-A-A. 
In a TPBMED stack of BP-C configuration, the sodium sebacate could be totally transformed to sebacic acid with a current efficiency of 94% and energy consumption of 2.2 kW h kg−1. 
The process cost was estimated to be $0.57 kg−1. 
Nonetheless, to simultaneously dissolve sebacic sodium and sebacic acid, the ethanol content in the mixture was controlled at 60 v/v %, and the maximal concentration of sebacic acid produced was only 0.13 mol dm−3 due to the limit on solubility.

1,8-Octanedicarboxylic acid
Acide sebacique
Decanedicarboxylic acid
Decanedioic acid
n-Decanedioic acid
Sebacic acid
Sebacic acids
Sebacinsaure


Translated names
Decanedioic acid (9CI)
Registration dossier
Decanedioic acid (9Cl)
Registration dossier
SA
Registration dossier
Sebacic acid (8CI)
Registration dossier
Sebacic acid (8Cl)
Registration dossier
Sebazinsaeure


Sebacic acid, is widely used to produce a various range of Bio-Nylons and Bio-plastics. 

What is Sebacic Acid? 
It also has a role as a human metabolite, and is used as an intermediate for aromatics, antiseptics, and painting materials. 
Sebacic acid is produced from castor oil. 
Sebacic acid is mainly used in the production of lubricants and greases, coolants, antifreeze, coatings, plasticizers, polyamides and polyesters. 
Sebacic Acid and its derivatives such as azelaic acid have a variety of industrial uses as plasticizers, lubricants, hydraulic fluids, cosmetics, candles, etc. 

Market growth of sebacic acid is backed upon increasing lubricants demand in automotive and industrial sector. 

There are two ways that sebacic acid can be produced: castor oil and adipic acid. 
SEBACIC ACID reacts exothermically to neutralize bases, both organic and inorganic. 

These sebacate are used as emollient, masking (reducing or inhibiting the basic odour of the product), hair and skin conditioning. 

Dibutyl Sebacate (C18H34O4), also known as sebacic acid dibutyl ester, is used as a Some of the principal uses of sebacic acid include acting as an intermediate in nylon, synthetic resins and other plastics.

Sebacic acid is used as a corrosion inhibitor and also as a coolant fluid in automotive, aircraft, and truck engines. 
Sebacic acid is a derivative of castor oil. 
For lubricants and anti-corrosion applications, sebacic acid is used to produce a salt derivative that can be used as a coolant for aircraft, automotive and truck engines. 

Some of the derivatives of the sebacic acid are known to have various industrial uses as lubricants, plasticizers, cosmetics, hydraulic fluids, and candles amongst others. 

Sebacic acid is used for PA610. 

Sebacic acid along with its homologues such as azelaic acid is extensively used in a number of industrial applications in plasticizers, lubricants, hydraulic fluids, cosmetics, candles, etc. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners), outdoor use, indoor use in close systems with minimal release (e.g. Sebacic acid can be used as a monomer for nylon, lubricants, hydraulic fluids, cosmetics, plasticizers and more. 


Sebaceus is Latin for tallow candle, sebum is Latin for tallow, and refers to its use in the manufacture of candles. 
The last step is the hydrolysis of dimethyl sebacate to sebacic acid. 

The commercial application of sebacic acid are as follows: Sebacic acid is used in formulation as a pH corrector in Cosmetics and skin care. 
The official told Times of Oman, "Sebacic started operating its first phase last year and is one of the successful businesses in Duqm. 

The most famous application of sebacic acid in the plastics world is the manufacture of polyamides (PA 6.10, PA 4.10, PA 10.10, etc. 

It can also be used as an intermediate for antiseptics, aromatics and painting products. 

Sebacic Acid is an organic dicarboxylic acid. 
Sebacic Acid was named from the Latin sebaceus (tallow candle) or sebum (tallow) in reference to its use in the manufacture of candles. 

1,8-OCTANEDICARBOXYLIC ACID, DECANEDIOIC ACID, and SEBACIC ACID. Decanedioic Acid. 

Sebacic acid definition is - a crystalline dicarboxylic acid C10H18O4 used especially in the manufacture of synthetic resins. 

SEBACIC ACID reacts exothermically to neutralize bases, both organic and inorganic. 

Sebacate esters ensure good penetration to give a non-oily and silky skin. 

These terms refer to the use of sebacic acid in the manufacturing of candles. 

It provides better properties than those given by adipic acid or by azelaic acid. 


 Sebacic acid is widely used to produce corrosion inhibitor. 

It is usedin the synthesis of polyamide and alkyd resins. 


COOLANT MSDS FORMULATION 1: 
3. Composition / Information on ingredients
Chemical Name Other name CAS No. %
1) Ethylene Glycol 1,2-Ethanediol
1,2-Dihydroxyethane 107-21-1 88 ~ 95 %
2) Water Dihydrogen Oxide 7732-18-5 2 ~ 5 %
3) Sebacic Acid Decanedioic acid 111-20-6 Max 2 %
4) BUSINESS SECRET(S1) - - Max 4 %


FORMULATION 2: 
SECTION 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance / Mixture : Mixture
Hazardous components

Chemical name CAS-No. Classification Concentration (%)

ETHYLENE GLYCOL 107-21-1 
92.6533 %

DIETHYLENE GLYCOL 111-46-6 
4.6355 %

SEBACIC ACID 111-20-6 
2.6822 % 

SODIUM HYDROXIDE 1310-73-2 
1.3929 %

ETHYLENE GLYCOL 107-21-1 
>=90.00 - <=100.00

DIETHYLENE GLYCOL 111-46-6 
>=1.00 - < 5.00


Corrosion Inhibitor FORMULATION : 
3. COMPOSITION / INFORMATION ON INGREDIENTS
SUBSTANCES
See section below for composition of Mixtures
Mixtures
CAS No. %[weight] Name
149-57-5 10-30 2-ethylhexanoic acid
111-20-6 2-3 sebacic acid
29385-43-1 <1 tolyltriazone
3734-33-6 0.01 denatonium benzoate

Concentrated antifreeze / coolant with corrosion inhibitors FORMULATION: 
3. Composition/information on ingredients
Mixture
Chemical name Common name and synonyms CAS number Concentration (%)
Ethylene glycol Caustic soda 107-21-1 85.0 - 95.0
Sodium hydrate
soda lye

Disodium sebacate Sebacic acid, disodium salt 17265-14-4 1.0 - 4.0

Sodium benzoate 
Caustic soda 532-32-1 1.0 - 4.0
Sodium hydrate
soda lye

Sodium nitrate 
Nitrate of soda 7631-99-4 1.0 - 3.0
Sodium saltpeter

Sodium tolytriazole 1H-Benzotriazole, 4(or 5)-methyl-, 64665-57-2 0.2 - 0.5
sodium salt


The following precursor ingredients are present at very low levels (< 0.03%), or are no longer present, in the final product:
Sodium hydroxide Caustic soda 1310-73-2 1.0 - 2.0
Sodium hydrate
soda lye

Benzoic acid Benzenecarboxylic acid 65-85-0 2.0 - 3.0
Carboxybenzene

Sebacic acid Decanedioic acid 111-20-6 2.0 - 3.0


LUBRICANT & MWF
Metal working fluids & Lubricants are at the core of Magnum Int'l customer base.  
This is where we excel & our knowledge base and supply chain is dedicated to the ingredients required by your multifaceted industries.

Alcohols
Amines
Chelating Agents
Chlorinated Solvents
Glycol Ethers
Isopropanolamines
EP additives
 
Aliphatic
Aromatic
Vegetable Oils
Glycols
Ketones
Surfactants
Tall Oil & TOFA
 
Acids
Alkyl Alkonolamines
Glycerin
Dicarboxylic Acids
Isoparaffinic Solvents
Chlorinated Paraffins
Polyisobutenes


PRODUCTS DEDICATED TO MWF
2-Ethyl Hexanol
Dicyclohexylamine (DCHA)
​Dodecanedioic Acid (DDDA)
Ethanolamines
Methyldiethanolamine(MDEA)
Sebacic Acid
TOFA
 
Adipic Acid
Diglycolamine (DGA)
Dimethylamino Methylpropanol
(DMAMP)
Chlorinated Paraffins
Methoxypropylamine (MOPA)
Sulfurized Isobutylene (SIB)
Glycol Ethers
 
Aminoethylethanolamine
(AEEA)
Dimethylaminopropylmaine
(DMAPA)
Isopropanolamines
(MIPA, DIPA, TIPA)
Polybutenes
Sulfurized Olefins
Glycols
Vegetable oils:  Canola, Soybeen, Rapeseed, Safflower, Cottonseed and a variety of others.
Alkyl Alkonolaines:  MMEA, DMEA, DEEA, EMEA, EDEA, PMEA, DEIPA, DBPA, BMEA, BDEA


Lubricity Characterizations of Sebacic Acid Based Ester
Waled Abdo Ahmed1, Jumat Salimon2 and Mohd Ambar Yarmo3
School of Chemical Science and Food Technology, Faculty of Science and Technology UKM, Bangi 43600- Malaysia

Abstract— The current study aimed to evaluate the effect of long-chain and branch alcohol on lubricity of sebacic acid based ester.
Since currently synthesis of a new lubricant to improve the lubricity properties and quality of lubricant is increasing, in this study,sebacic acid esters were synthesized by the conventional esterification method with some modification using sulfuric acid (SA) as catalyst. 
Twelve samples of sebacic acid esters with different chemical structures were synthesized including di-2-octyl sebacate, didecyl sebacate, di-2 ethylhexanol sebacate, di-2-ethylbutyl sebacate and dioleyl sebacate. 
These diesters were tested in terms of their suitability as lubricant. 
The results showed that the pour point, flash point and oxidation stability were affected by liner and branch of the alcohol used. 
Di-2-ethylbutyl sebacate (D2EBS) and di-2-ethylhexanol sebacate (D2EHS) showed very low pour point at -44°C and -60°C respectively, while the same carbon number of dihexyl sebacate (DHS) and dioctyl sebacate (DOS) recorded high pour point at 8°C and 15 °C respectively. 
These differences were due to the presence of the branching. 
DOS recorded the highest oxidative stability at 290°C. 
However, there was a slight negative effect of the branching on the flash point.
Keywords— lubricity; Sebacic acid ester; pour point; flash point; viscosity index 

Sebacic acid is a chemical compound which is primarily derived from castor oil with two primary uses as a reactant with other chemicals to produce distinct chemical compounds or polymers or directly in formulated products such as a corrosion inhibitor in cutting and metal working fluids. 
Sebacic acid can be used directly in formulated products such as antifreeze coolants. 

As a fatty chemical, it coats exposed metals with a thin film that helps protect against oxygen and electrolytic corrosion. 
The sebacate esters are frequently used as liquid proxies for the corresponding acid in making greases. 
Sebacate esters compete with the chemical derivatives of adipic acid, azelaic acid, and dodecanedioic acid as plasticizers. 
Derivatives of sebacic acid can be used in the production of corrosion inhibitors.

Chemical Reaction And Yield %
The esterification reaction of sebacic acid and alcohol (1:2) mole ratio was done out according to routine method, through 4 h at the range of 100-130°C with some modification using nitrogen. 
H2SO4 was used as a catalyst.
Figure 1 shows the reaction procedure of sebacic acid and 2- ethyl-1-hexanol. 
The formed water through reaction was removed by dean stark method using toluene as a zoetrope.
After 4 h the reaction stopped and left for 2- 3 h to stable and cool, it was dissolved in 50ml of diethyl ether and put in
separating funnel, and then the mixture was washing using saturated NaHCO3 (10ml X 3) followed by 10 ml of saturated NaCl until the pH of organic layer was 7.

Fig. 1 Esterification reaction of sebacic acid and 2-ethyl-1-hexanol to form D2EHS. 


Sebacic acid derived from castor oil is an exceptional concoction with a wide variety of applications and benefits. 
It is utilized in the manufacturing bio-polyamides, conferring critical properties such as adaptability, solidness, hydrophobicity, and lower dissolving temperatures. 
In addition, it is utilized as polyesters, as its flexibility, chemical resistance, and strength supports the dibasic acid nature of sebacic acid. 
These polyesters are used in various coating applications such as coils, architectural, and high solids paints.

The growth of the global sebacic acid market is driven by wide variety of applications & bio-based nature of sebacic acid and low manufacturing cost. 
However, increase in health and environmental concerns is expected to hamper the market growth.

Sebacic Acid
Sebacic Acid Product Data Sheet
C10 dicarboxylic acid flake primarily used in the cosmetics, lubricants, plasticiser and chemical manufacturing industries and as an intermediate for alkyd resins.


Sebacic acid is a white or off-white, waxy compound derived from castor oil.
It is a dicarboxylic acid with a high melting point, which drives many of its applications. 
As stated earlier, it can be used either as a reactant, or directly in formulated products.
The use of sebacic acid as a reactant in making chemical compounds.

Sebacic acid may be polymerized to make nylon 6/10, which in turn is fabricated into products such as toothbrush bristles, fishing lines, and paper machine felts.
It also may be polymerized to produce polyester resins, coatings, and adhesives.

Sebacic acid may also be a reactant with various alcohols to produce sebacate esters.
These esters are used as plasticizers (which soften stiff plastics and resins) in polyvinyl chloride (PVC) films to provide low temperature flexibility and freedom from cracking


Sebacic acid is also used directly in formulated products such as antifreeze coolants, as corrosion inhibitors in cutting and metal-working fluids, and in other formulated products such as coatings, and lubricants

Sebacic acid is most often used as a raw material for making other chemicals and polyester resins

In theory, sebacic acid can be produced in a number of ways - including from petrochemical feedstocks - but the primary commercial route begins with castor oil. 
Castor oil is obtained from castorseed (sometimes called castor beans), the fruit of Ricinus communis, a subtropical shrub, by mechanical pressing and/or solvent extraction


Sebacic acid is made from the ricinoleic acid in castor oil. 
One of the manufacturing process challenges is how to deal with the other fatty acids and constituents contained in castor oil without losing their intrinsic value as potential by- or co-products


Sebacic acid is a saturated, straight-chain naturally occurring dicarboxylic acid with 10 carbon atoms. 
Sebacic acid is a normal urinary acid. 
In patients with multiple acyl-CoA-dehydrogenase deficiency (MADD) or glutaric aciduria type II (GAII) are a group of metabolic disorders due to deficiency of either electron transfer flavoprotein or electron transfer flavoprotein ubiquinone oxidoreductase, biochemical data shows an increase in urine sebacic acid excretion. 
Sebacic acid is a white flake or powdered crystal slightly soluble in water that has been proposed as an alternative energy substrate in total parenteral nutrition. 
Sebacic Acid was named from the Latin sebaceus (tallow candle) or sebum (tallow) in reference to its use in the manufacture of candles. 
Sebacic Acid and its derivatives such as azelaic acid have a variety of industrial uses as plasticizers, lubricants, hydraulic fluids, cosmetics, candles, etc. 
It is used in the synthesis of polyamide and alkyd resins. 
It is also used as an intermediate for aromatics, antiseptics and painting materials

1,10-Decanedioate
1,10-Decanedioic acid
1,8-Octanedicarboxylate
1,8-Octanedicarboxylic acid
4,7-Dioxosebacic acid
4-Oxodecanedioate
4-Oxodecanedioic acid
Acide sebacique
Decanedicarboxylic acid
Decanedioate

Sodium sebacate is obtained through alkaline division of ricinoleic acid/castor oil and is processed to create sebacic acid, with 2-octanol and heptane created as by-products. Sebacic acid is a starting material in the production of polyamides, particularly polyamide 6.10. 
It is also used as a plasticiser in the plastics industry and used in the synthetic resin and the lubricant industry.

Sebacic acid is a homogenous dicarboxylic acid and a derivative of castor oil. 
Sebacic acid are used for plasticizer for synthetic material and as intermediate for nylon.
Synonym: 1,8-Octanedicarboxylic Acid
CAS-No. 111-20-6
EINECS-No. 2038455
Uses/applications: Raw material for plasticizers (Sebacate), Synthetic resins, Polyamide, lubricants, etc.

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