Morpholine is a colorless organic compound with the chemical formula O(CH2CH2)2NH, which has heterocycle features of both amine and ether functional groups.
Morpholine and its derivatives have been used as rubber additives, corrosion inhibitors, solvents, optical brighteners, antioxidants, and in manufacturing a range of drugs and herbicides.
Morpholine is a versatile intermediate with a weak, ammonia- or fish-like odor and various applications.
Morpholine is used as an essential building block mainly in rubber, water treatment, optical brighteners, pharma, agro-industry, and solvent for the fiber industry.
Morpholine is a highly versatile chemical used extensively as a corrosion inhibitor in steam boiler systems and as an intermediate in manufacturing products used as optical brighteners, textile lubricants, softening agents, adjuvants, antioxidants, plasticizers, and viscosity improvers.
ATAMAN has many morpholine derivatives used in diverse markets, such as electronics, printing dyes, pharmaceuticals, urethane catalysts, and textile solvents.
Morpholine and derivatives may be used as an accelerator/catalyst in epoxy formulations or as catalyst/initiator in UV-curable acrylic-based systems for coatings and adhesives.
Morpholine is a Solvent with good solubility power, high polarity, and low molecular weight.
Morpholine is readily biodegradable and with good human health and ecotoxic profile to be used in the EC Emulsifiable concentrate in the Agrochemicals as an alternative to NMP
EC / List no.: 203-815-1
CAS no.: 110-91-8
Mol. formula: C4H9NO
Properties of Morpholine
Chemical formula: C4H9NO
Molar mass: 87.122 g·mol−1
Appearance: Colorless liquid
Odor: Weak ammonia-like or fish-like
Density: 1.007 g/cm3
Melting point: −5 °C (23 °F; 268 K)
Boiling point: 129 °C (264 °F; 402 K)
Solubility in water: miscible
Vapor pressure: 6 mmHg (20 °C)
Acidity (pKa):8.36 (of conjugate acid)
Magnetic susceptibility (χ): -55.0·10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards: Flammable, Corrosive
Morpholine | Boiler Corrosion Inhibitor
Morpholine, an organic compound with both amine and ether groups, is obtained by dehydrating diethanolamine with sulphuric acid.
Morpholine can be adapted to many different activities for many critical applications.
Some of its different adaptations can be seen in the following applications.
Morpholine is an intermediate in producing rubber chemicals, even as optical brighteners.
Morpholine is an effective corrosion inhibitor in steam boiler systems.
Morpholine is also employed in pharma chemicals and antioxidants for lubricating oils.
Morpholines can be used as emulsifiers in wax and polish processing industries.
Morpholine is an excellent pH adjuster, which is very effective for nuclear power plants.
Morpholine can also be used as an ingredient in fungicides and bactericides.
Key Features and Benefits of Morpholine:
Prevents stress cracking corrosion
Reduces blow-down requirement
Does not add TDS of the water
Returns to the feed line with the condensate return, so raise the feed water pH.
Saves power & downtime
Versatile applications
Application Areas of Morpholine
Rubber Chemicals
Delayed action accelerator
Catalysts
Temperature-sensitive polymerization inhibitor
Gelling agent
Optical Brighteners
Stabler than chlorine bleaches
Pharma Chemicals
Morpholine derivatives as analgesics and anesthetics
Choleretics, antispasmodics, analeptics, antimalarials
Processing Industries
Processing Industries (Non-food)
Water Treatment
Corrosion Inhibitors
Neutralizing Amine
Antioxidants
Separating Agents
Wax Emulsifier
Self-polishing waxes and polishes
Surface tension depressor
Scrubbing organic sulfur compounds from fuel gas
Purification procedures
Biocide
Bacteriostatic/ bactericidal properties
Anti-fungal
Emulsifier
Agrochemicals
EC Emulsifiable concentrate
Morpholine is used in steam-generating-boiler systems plants to prevent internal corrosion of condensate return lines.
Replacement costs for underground steam/condensate systems are high.
A high cost is associated with reduced efficiency while systems are corroding.
Neutralizing amine morpholine plays a significant role in the curtailment of condensate corrosion.
Morpholine is a neutralizing amine to give the most economical and effective results in different systems.
Neutralizing Amine Chemistry
Several different neutralizing amine components are typically used in the treatment of boiler feedwater and/or condensate.
Neutralizing amines have different chemical properties, and it is essential to understand the differences to apply the correct components.
Neutralizing amines typically applied in power plant systems are cyclohexylamine (CHA), methoxypropylamine (MPA), monoethanolamine (ETA), and morpholine.
Neutralizing amines are weak bases that are typically classified in terms of their "neutralizing capacity," "basicity," and "distribution ratio."
The neutralizing capacity measures how much amine it takes to neutralize a given acid.
Usually, it is expressed as the ppm of CO2 (or carbonic acid) neutralized per ppm of neutralizing amine.
Once the acid has been neutralized, each amine has a different ability to boost pH, which is accomplished by the hydrolysis of the amine to form hydroxyl (OH-) ions.
The distribution ratio refers to the volatility of the amine, which is one factor that helps determine how each amine component will partition between the liquid and steam phases. The distribution ratio of a particular amine also influences how much amine is recycled throughout the system, and how many amines will be lost from the system via boiler blowdown and steam venting.
While neutralizing amine chemistry may appear relatively straightforward, it is pretty complex. For example, the distribution ratio for a given amine is a function of pressure, temperature, and pH. This means if you feed more or less neutralizing amine in a given system and affect the pH, the distribution of the amine between the liquid and steam phases will change as well.
In addition, neutralization chemistry is based on the equilibrium chemistry of weak acids and weak bases.
Multiple neutralizing amine and acid components are present in many cases, so it becomes even more challenging to predict the amine distribution and pH profile across the system without using sophisticated computerized modeling techniques or performing extensive empirical in-plant analyses.
The thermal stability of the neutralizing amine must also be considered when designing a treatment program to control FAC. Most amines degrade to some degree in an aqueous, alkaline, high-temperature environment to form carbon dioxide, organic acids, and ammonia. Morpholine, CHA, ETA, and MPA are the most thermally stable amines routinely employed in high-pressure power plant applications.
Morpholine is a neutralizing amine that prevents carbonic acid corrosion in plant or refinery steam condensate systems.
Morpholine is an organic chemical compound with the formula O(CH2CH2)2NH.
This heterocycle features both amine and ether functional groups. Because of the amine, morpholine is a base; its conjugate acid is called morpholinium.
For example, neutralizing morpholine with hydrochloric acid makes the salt morpholinium chloride.
Applications
Rubber Chemicals
The effective use of morpholine is an intermediate in producing delayed-action rubber accelerators.
Accelerators are added to rubber before fabrication to increase the rate of vulcanization.
Morpholine-based delayed-action accelerators are usually made by reacting morpholine with 2-mercaptobenzothiazole.
Corrosion Inhibitors
Morpholine is widely used as a neutralizing amine in combating carbonic acid corrosion in condensate return lines of steam boiler systems.
Morpholine volatilizes with the steam from the boiler. It condenses when the steam does, thereby protecting the lines, which otherwise would be subjected to corrosion by the carbonic acid in the steam condensate. Morpholine vapors protect silver and other metals against corrosion and tarnish by acid fumes, such as sulfur dioxide and hydrogen sulfide.
Morpholine is a component of a corrosion inhibitor system that prevents the decomposition of a chlorinated hydrocarbon in a composition containing the chlorinated hydrocarbon and a large amount of water. Using low levels of morpholine can avoid the corrosion of metal aerosol containers and valves.
Catalysts
Morpholine has been employed as a catalyst for condensing aldehydes and ketones, which contain active methyl or methylene groups. The condensates may be hydrogenated to polyhydroxy compounds, which can be sulfated to form surface-active agents. Morpholine has also been used as a gelling agent in preparing alumina catalysts to treat hydrocarbons.
Catalysts of a fine particle size suitable for solid fluidized techniques result from this procedure.
Separating Agents
Morpholine's physical and chemical properties make it useful in various purification procedures.
Marked differences in the solubility of the methyl amines in morpholine have led to a convenient extractive method for separating these volatile amines.
Adding morpholine to styrene-containing hydrocarbon mixtures makes isolating substantially pure styrene by azeotropic distillation possible.
Morpholine is the preferred amine in an oil-amine mixture for scrubbing organic sulfur compounds from fuel gas.
Morpholine is also used in the purification of acetylene and certain olefins.
Optical Brighteners
Morpholine is an essential intermediate in the manufacture of optical brighteners.
Optical brighteners are employed by the soap and detergent industry in compounding detergents.
The diamino stilbene triazine type brightener with morpholine as a substituent on one of the triazine rings is particularly effective on cellulosic.
Having more excellent stability to chlorine bleaches than other brighteners, they are particularly suitable for home laundry detergents.
Emulsion polymerization agent
Small quantities of morpholine are used in the emulsion polymerization of monomers, such as butadiene and isoprene, as well as their copolymerization with styrene, acrylonitrile, and the like.
Polymerization inhibitor
Morpholine has been used as a temperature-sensitive polymerization inhibitor.
Small amounts permit complete impregnation of porous materials with molten vinyl pyrrole-type monomers just above their melting points but still allow complete polymerization at slightly higher temperatures.
Agriculture
As a fruit coating
Morpholine is used as a chemical emulsifier in the process of waxing fruit.
Naturally, fruits make waxes to protect against insects and fungal contamination, but this can be lost as the fruit is cleaned.
A small amount of new wax is applied to replace it. Morpholine is used as an emulsifier and solubility aid for shellac and as a wax for fruit coating.
The European Union has forbidden the use of morpholine in fruit coating.
As a component in fungicides
Morpholine derivatives used as agricultural fungicides in cereals are known as ergosterol biosynthesis inhibitors.
Industrial applications
Morpholine is a common additive, in parts per million concentrations, for pH adjustment in fossil fuel and nuclear power plant steam systems.
Morpholine is used because its volatility is about the same as water. Once it is added to the water, its concentration becomes evenly distributed in both the water and steam phases.
Its pH-adjusting qualities then become distributed throughout the steam plant to provide corrosion protection.
Morpholine is often used in conjunction with low concentrations of hydrazine or ammonia to provide a comprehensive all-volatile treatment chemistry for corrosion protection for the steam systems of such plants.
Morpholine decomposes reasonably slowly without oxygen at these steam systems' high temperatures and pressures.
Organic synthesis
Morpholine undergoes most chemical reactions typical for other secondary amines. However, the presence of the ether oxygen withdraws electron density from the nitrogen, rendering it less nucleophilic (and less basic) than structurally similar secondary amines such as piperidine. For this reason, it forms a stable chloramine.[9]
It is commonly used to generate enamines.
Morpholine is widely used in organic synthesis. For example, it is a building block in preparing the antibiotic linezolid, the anticancer agent gefitinib (Iressa), and the analgesic dextromoramide.
In research and industry, morpholine's low cost and polarity lead to its everyday use as a solvent for chemical reactions.
How Morpholine is manufactured:
Three methods of producing morpholine have been described:
a) Reductive ammoniation of diethylene glycol and hydrogen. Possible catalysts include copper, nickel, cobalt, chromium, molybdenum, manganese, platinum, palladium, rhodium and ruthenium. Morpholine is recovered by fractional distillation
b) Dehydration of diethanolamine with a strong acid such as oleum, concentrated sulfuric acid, or hydrochloric acid.
The acid is neutralized by adding an alkali to give the free base of morpholine.
Morpholine is recovered by extraction using an organic solvent or concentrated aqueous alkali followed by distillation.
c) Heating bis(chloroethyl)ether and anhydrous ammonia in a closed vessel.
After venting the excess ammonia, the product is filtered from ammonium chloride, and purified morpholine is obtained by distillation.
Preferred IUPAC name
Morpholine[2]
Other names
Diethylenimide oxide
1,4-Oxazinane
Tetrahydro-1,4-oxazine
Diethylene imidoxide
Diethylene oximide
Tetrahydro-p-oxazine
Identifiers
CAS Number
110-91-8 check
MORPHOLINE
110-91-8
1-Oxa-4-azacyclohexane
Tetrahydro-1,4-oxazine
Diethylene oximide
Diethylenimide oxide
Diethyleneimide oxide
Diethylene imidoxide
Drewamine
Tetrahydro-2H-1,4-oxazine
Tetrahydro-p-oxazine
p-Isoxazine, tetrahydro-
Tetrahydro-1,4-isoxazine
morpholin
BASF 238
Caswell No. 584
2H-1,4-Oxazine, tetrahydro-
4H-1,4-Oxazine, tetrahydro-
Morpholine, 4-soya alkyl derivs.
NSC 9376
138048-80-3
MFCD00005972
N-Vinylbenzylmorpholine-divinylbenzene Copolymer
C4H9NO
Tetrahydro-4H-1-4-oxazine
8B2ZCK305O
CHEBI:34856
NSC-9376
DSSTox_CID_5688
DSSTox_RID_77880
DSSTox_GSID_25688
CAS-110-91-8
CCRIS 2482
HSDB 102
MORPHOLINE,REAG
Tetrahydro-p-isoxazine
MORPHOLINE, PRACT
EINECS 203-815-1
UN2054
EPA Pesticide Chemical Code 054701
BRN 0102549
morphline
UNII-8B2ZCK305O
morpho line
morpholine-
AI3-01231
6LR
4H-1, tetrahydro-
MORPHOLINE [MI]
Morpholine [UN2054] [Flammable liquid]
Morpholine Reagent Grade
MORPHOLINE [FCC]
MORPHOLINE [HSDB]
MORPHOLINE [IARC]
MORPHOLINE [INCI]
Morpholine on Rasta Resin
WLN: T6M DOTJ
EC 203-815-1
NCIMech_000154
Tetrahydro-1, 4-isoxazine
NCIOpen2_007748
Oprea1_317540
Tetryhydro-2H-1,4-oxazine
Tetrahydro-4H-1,4-Oxazine
4-27-00-00015 (Beilstein Handbook Reference)
BIDD:ER0297
Morpholine, analytical standard
CHEMBL276518
DTXSID2025688
NSC9376
AMY22834
BCP24054
STR00194
ZINC1699948
Tox21_202450
Tox21_303240
STL182843
AKOS000118829
Morpholine, ACS reagent, >=99.0%
Morpholine, ReagentPlus(R), >=99%
DB13669
NA 2054
UN 2054
NCGC00249227-01
NCGC00256942-01
NCGC00259999-01
61791-40-0
Morpholine, p.a., ACS reagent, 99.0%
DB-030063
Morpholine [UN2054] [Flammable liquid]
FT-0628993
M0465
EN300-18064
Morpholine purified by distillation from glass
Morpholine, purified by redistillation, >=99.5%
Q410243
J-522715
1-Oxa-4-azacyclohexane ; Tetrahydro-2H-1,4-oxazine
F2190-0339
Morpholine, polymer-bound, 200-400 mesh, extent of labeling: 2.75-3.25 mmol/g loading, 1 % cross-linked
ScavengePore(TM) phenethyl morpholine, macroporous, 40-70 mesh, extent of labeling: 0.7-1.5 mmol/g loading
StratoSpheres(TM) PL-MPH resin, 50-100 mesh, extent of labeling: 3.0-4.0 mmol/g loading, 1 % cross-linked
102549 [Beilstein]
110-91-8 [RN]
203-815-1 [EINECS]
8B2ZCK305O
MFCD00005972 [MDL number]
Morfolina [Italian]
Morfolina [Portuguese]
Morpholin [German] [ACD/IUPAC Name]
Morpholine [ACD/Index Name] [ACD/IUPAC Name] [Wiki]
Morpholine [French] [ACD/Index Name] [ACD/IUPAC Name]
QD6475000
Tetrahydro-1,4-oxazine
UNII:8B2ZCK305O
Морфолин [Russian]
モルホリン [Japanese]
吗啉 [Chinese]
吗啡啉 [Chinese]
(2H9)Morpholine [ACD/IUPAC Name]
1,4-Oxazinane
134071-14-0 [RN]
138048-80-3 [RN]
175591-17-0 [RN]
1-Oxa-4-azacyclohexane
203578-31-8 [RN]
2H-1,4-Oxazine, tetrahydro-
4-27-00-00015 (Beilstein Handbook Reference) [Beilstein]
4H-1,4-Oxazine, tetrahydro-
Diethylene imidoxide
Diethylene oximide
Diethyleneimide oxide
diethylenimide oxide
Drewamine
Morpholine purified by distillation from glass
Morpholine-d8
N-Vinylbenzylmorpholine-divinylbenzene Copolymer
Oprea1_317540
p-Isoxazine, tetrahydro-
ST5213815
STR00194
T6M DOTJ [WLN]
Tetrahydro-1, 4-isoxazine
Tetrahydro-1,4-isoxazine
Tetrahydro-2H-1,4-oxazine
Tetrahydro-4H-1,4-Oxazine
Tetrahydro-4H-1-4-oxazine
Tetrahydro-P-isoxazine
Tetrahydro-p-oxazine
Tetryhydro-2H-1,4-oxazine
UN 2054
UNII-8B2ZCK305O
WLN: T6M DOTJ
Translated names
morfoliin (et)
Morfoliini (fi)
morfolin (cs)
morfolin (hr)
morfolin (hu)
morfolin (no)
morfolin (sl)
morfolin (sv)
morfolina (es)
morfolina (it)
morfolina (pl)
morfolina (pt)
morfolina (ro)
morfolinas (lt)
morfoline (nl)
morfolín (sk)
morfolīns (lv)
morpholin (da)
Morpholin (de)
morpholine (fr)
tetrahidro-1,4-oxazina (es)
tetrahydro-1,4-oksazyna (pl)
μορφολίν (el)
мoрфолин (bg)
CAS names
Morpholine
IUPAC names
2-chloro-1-morpholin-4-ylethanone
4H-1,4-Oxazine, tetrahydro-
Morpholin
MORPHOLINE
Morpholine
morpholine
Morpholine
morpholine
MORPHOLINE-2,2,3,3,5,5,6,6-D8 (D, 98%)
tetrahydro 1.4 oxazine
Tetrahydro-1,4-oxazine
Tetrahydro-2H-1,4-oxazine
Tetraidro-1,4-ossazina
Trade names
1-Oxa-4-azacyclohexane
2H-1,4-Oxazine, tetrahydro-
4H-1,4-Oxazine, tetrahydro-
BASF 238
Diethylene imidoxide
Diethylene oximide
Diethylenimide oxide
Drewamine
Morpholin
Morpholine (8CI, 9CI)
p-Isoxazine, tetrahydro-
Tetrahydro-1,4-oxazine
Tetrahydro-2H-1,4-oxazine
Tetrahydro-p-oxazine
Morpholine is an organic chemical compound having the chemical formula O(CH2CH2)2NH. Morpholine is used as a boiler water treatment additive in steam systems of power plants and refineries. Morpholine is an organic chemical compound that is used as a corrosion inhibitor and additive and is used to synthesize other chemicals. The molecular formula of Morpholine is C4H9NO.
Morpholine is a heterocyclic chemical compound that has amine and ether functional groups. Morpholine is a base due to the presence of an amine. Morpholine is colorless and free of suspended matter. Morpholine is commonly used as a solvent in organic synthesis, reactions, and chemical industry research due to its low cost and polarity.
This heterocycle features both amine and ether functional groups. Because of the amine, morpholine is a base; its conjugate acid is called morpholinium. For example, treating morpholine with hydrochloric acid makes the salt morpholinium chloride.
The naming of morpholine is attributed to Ludwig Knorr, who incorrectly believed it to be part of the structure of morphine.
Morpholine appears as a colorless liquid with a fishlike odor. Flashpoint 100°F. Corrosive to tissue. Less dense than water and soluble in water. Vapors heavier than air. Used to make other chemicals, as a corrosion inhibitor, and in detergents.
Morpholine is a saturated organic heteromonocyclic parent and a member of morpholines.
Morpholine is an important building block for rubber chemicals and has many applications in other industries.
It is used as an intermediate for water treatment, the production of pharmaceutical and agricultural products, and optical brighteners.
Morpholine (1,4-tetrahydro-oxazine) is a simple heterocyclic compound that has great industrial importance and a wide range of applications. This chemical compound and its derivatives have been used as rubber additives, corrosion inhibitors, solvents, optical brighteners, antioxidants and in the manufacture of a range of drugs and herbicides.
Morpholine is an organic chemical compound having the chemical formula O(CH2CH2)2NH. Morpholine is a colorless liquid with a weak, ammonia- or fish-like odor.
KEY WORDS:
MORPHOLINE, 110-91-8, 1-Oxa-4-azacyclohexane, Tetrahydro-1-4-oxazine, Diethylene oximide, Diethylenimide oxide, Diethyleneimide oxide, Diethylene imidoxide, Drewamine, Tetrahydro-2H-1-4-oxazine
PRODUCT USE
Solvent for resins, waxes, casein, and dyes. Morpholine fatty acid salts are used as surface active agents and emulsifiers.
Other morpholine compounds are used as corrosion inhibitors, antioxidants, and plasticizers.
Morpholine compounds are also used as viscosity improvers, insecticides, fungicides, herbicides, local anesthetics, and antiseptics. Morpholine has a volatility similar to water.
It is, therefore, widely used as a neutralizing amine in combating carbonic acid corrosion in condensate return lines in steam boiler systems, aqueous
hydraulic liquids, and similar systems. Morpholine vapors protect silver and other metals against corrosion and tarnish by acid fumes such as
SO2 and H2S. Corrosion of metal aerosol containers and valves can also be prevented by using low levels of morpholine. Morpholine is
effective in hydraulic system fluids based on glycols, where various metals are in contact with the fluid simultaneously.
Morpholine derivatives have been used as corrosion inhibitors in mineral lubricating oil, turbine oils, for protecting storage tanks, pipes, and other devices used in handling petroleum distillates, and for inhibiting the corrosive action of grease-proof paper on steel and other metals Intermediate
SYNONYMS
C4-H9-O-N, C4-H9-O-N, OCH2-CH2-NHCH2-CH2, "diethyleneimide oxide", "diethylene imideoxide", "diethylene oximide", "diethylenimide
oxide", Drewamine, "p-isoxamine, tetrahydro-", "p-isoxamine, tetrahydro-", 1-oxa-4-azacyclohexane, 1-oxa-4-azacyclohexane, "2H-1,
4-oxazine, tetrahydro-", "2H-1, 4-oxazine, tetrahydro-", "4H-1, 4-oxazine, tetrahydro-", "4H-1, 4-oxazine, tetrahydro-", "tetrahydro-1,
4-isoxazine", "tetrahydro-1, 4-isoxazine", tetrahydro-p-oxazine, tetrahydro-p-oxazine, "tetrahydro-2H-1, 4-oxazine", "tetrahydro-2H-1,
4-oxazine", "BASF 238"
CAS Number: 110-91-8;EINECS 263-172-8; IUPAC name: Morpholine. Other names:Diethylenimide oxide; 1,4-Oxazinane; Tetrahydro-1,4-oxazine; Diethylene imidoxide; Diethylene oximide; Tetrahydro-p-oxazine
Synonyms & Trade Names: Diethylene imidoxide, Diethylene oximide, Tetrahydro-1,4-oxazine, Tetrahydro-p-oxazine
Chemical formula: C4H9NO
Molar mass: 87.122 g·mol−1
Appearance:Colorless liquid
Odor: Weak ammonia-like or fish-like
Density: 1.007 g/cm3
Melting point: −5 °C (23 °F; 268 K)
Boiling point: 129 °C (264 °F; 402 K)
Solubility in water: miscible
Vapor pressure: 6 mmHg (20 °C)
Acidity (pKa):8.36 (of conjugate acid)
Magnetic susceptibility (χ): -55.0·10−6 cm3/mol
Main hazards: Flammable, Corrosive
Odor: characteristic
Use: Due to morpholine's chemical stability and similar volatility to water, it makes an excellent corrosion inhibitor for steam boilers and water treatment systems.
Morpholine is a common emulsifier in fruit waxes to protect against fungal and insect contamination. Morpholine can be used as a pH modifier for fossil and nuclear fuels, in rubber accelerants, as a descaling agent, antiseptic, textile printing and dyeing agent, antioxidant, deodorizer, and in medicines and pesticides.
Applications: Corrosion inhibitor in steam condensate ( Boiler), Optical brighteners, pharmaceuticals.
Morpholine is an organic chemical compound used as a corrosion inhibitor and additive to synthesize other chemicals. The molecular formula of Morpholine is C4H9NO. Morpholine is a heterocyclic chemical compound that has amine and ether functional groups. Morpholine is a base due to the presence of an amine. Morpholine is colorless and free of suspended matter. Morpholine is commonly used as a solvent in organic synthesis, reactions, and chemical industry research due to its low cost and polarity.
APPLICATIONS
1. ADDITIVES AND CATALYSTS
Morpholine is an additive for adjusting pH in nuclear power plant steam systems and fossil fuels. Morpholine is also used for corrosion protection of boiler water stream systems in chemical plants. Morpholine is used for the preparation of alumina catalysts. They are prepared as a gelling agent for the treatment of hydrocarbons.
2. ORGANIC SYNTHESIS
Morpholine is commonly used for the synthesis of enamines. It is an essential ingredient to produce linezolid, an antibiotic for treating infections caused by gram-positive bacteria. It is also used in gefitinib, a cancer drug. Morpholine is also used in the analgesic dextromoramide. Morpholine salts such as morpholine hydrochloride are used for the organic synthesis of intermediates.
3. AGRICULTURE
Morpholine in the form of a chemical emulsifier, is used for the protection of fruits. This is achieved through waxing, which applies a wax layer onto the fruits. This coating protects fruits from insects and fungal infestation. Ergosterol biosynthesis inhibitors are the derivatives of morpholine, which are used as fungicides in cereals. Some morpholine-based fungicides used on cereal crops are amorolfine, fenpropimorph, and trimorph.
4. RUBBER INDUSTRY
Morpholine is widely used as an intermediate in the rubber industry to produce rubber vulcanization accelerators such as DTOS, MDS, and NOBS. Over 50% of the demand for morpholine is from rubber vulcanization accelerators, and about 30% is used for NOBS.
5. METAL CORROSION INHIBITORS
Morpholine is a corrosion inhibitor for metals such as copper, iron, lead, zinc, and others. It is widely used in automobiles, mechanical instruments, and medical equipment. In its gas-liquid state, Morpholine has lower toxicity towards the environment when compared to its forerunners like cyclohexylamine and dicyclohexylamine nitrite.
6. MANUFACTURING
Morpholine manufactures paper, glass, soap, detergent, dye, and synthetic fiber. It is used to manufacture analysis reagents for nitrogen determination.
Morpholine also finds applications in pharmaceuticals, tanning, textiles, household care, and ceramics industries.
SCOPE
In recent times, drug discovery efforts have unveiled numerous interesting morpholine-based compounds. There is still much to be explored regarding the synthesis of drugs and intermediates. With technological advancement, morpholine will find more applications in various industries.
Uses
Industrial applications: Morpholine is a common additive, in parts per million concentrations, for pH adjustment in fossil fuel and nuclear power plant steam systems. Morpholine is used because its volatility is about the same as water. Once it is added to the water, its concentration becomes distributed relatively evenly in both the water and steam phases. Its pH-adjusting qualities then become distributed throughout the steam plant to provide corrosion protection. Morpholine is often used in conjunction with low concentrations of hydrazine or ammonia to give a comprehensive all-volatile treatment chemistry for corrosion protection for the steam systems of such plants.
Morpholine decomposes reasonably slowly without oxygen at these steam systems' high temperatures and pressures.
Organic synthesis
Morpholine undergoes most chemical reactions typical for other secondary amines. However, the presence of the ether oxygen withdraws electron density from the nitrogen, rendering it less nucleophilic (and less basic) than structurally similar secondary amines such as piperidine. For this reason, it forms a stable chloramine.
It is commonly used to generate enamines.
Morpholine is widely used in organic synthesis. For example, it is a building block in preparing the antibiotic linezolid, the anticancer agent gefitinib (Iressa), and the analgesic dextromoramide.
In research and industry, morpholine's low cost and polarity lead to its everyday use as a solvent for chemical reactions.
Agriculture
As a fruit coating
Morpholine is used as a chemical emulsifier in the process of waxing fruit. Naturally, fruits make waxes to protect against insects and fungal contamination, but this can be lost as the fruit is cleaned. A small amount of new wax is applied to replace it. Morpholine is used as an emulsifier and solubility aid for shellac and as a wax for fruit coating. The European Union has forbidden the use of morpholine in fruit coating.
As a component in fungicides
Morpholine derivatives used as agricultural fungicides in cereals are known as ergosterol biosynthesis inhibitors.
Description
This compound belongs to the class of organic compounds known as morpholines. These organic compounds contain a morpholine moiety, consisting of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively.
Kingdom: Organic compounds
Super Class: Organoheterocyclic compounds
Class: Oxazinanes
Sub Class: Morpholines
Direct Parent: Morpholines
Alternative Parents: Oxacyclic compounds / Dialkylamines / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents: Aliphatic heteromonocyclic compound / Amine / Azacycle / Dialkyl ether / Ether / Hydrocarbon derivative / Morpholine / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound
Molecular Framework: Aliphatic heteromonocyclic compounds
External Descriptors: morpholines, saturated organic heteromonocyclic parent (CHEBI:34856)
Morpholine is a pale hygroscopic liquid with the chemical formula of O(CH2CH2)2NH, free of foreign matter. It bears its characteristic amine odor that is detectable above 0.1 ppm concentration in boiler feed. It is a widely used neutralizing amine in combating carbonic acid corrosion in condensate return lines of steam boiler systems. It volatilizes and condenses with the steam from the boilers, thereby affording protection to the lines, which otherwise would be subjected to corrosion from the carbonic acid present in the steam condensate. Its vapors protect silver and other metals against corrosion and tarnishing by acrid fumes, such as sulfur dioxide and hydrogen sulfide.
Morpholine is used as a boiler water treatment additive in steam systems of power plants and refineries. It forms an even wax-like coating as morpholine oleate. It prevents the decomposition of a chlorinated hydrocarbon in a composition containing the chlorinated hydrocarbon and a large amount of water. It is often used in conjunction with low concentrations of hydrazine or ammonia to provide a comprehensive all-volatile boiler water treatment chemistry for corrosion protection for the steam systems of such plants. Morpholine decomposes reasonably slowly without oxygen at the high temperatures and pressures in these steam systems.
Because its volatility is the same as water, upon addition to water, its concentration becomes distributed relatively evenly in both the water and steam phases. Its pH-adjusting qualities become more dispersed throughout the steam plant to provide corrosion protection.
Key Features & Benefits of Morpholine:
Prevents corrosion due to stress cracking
Reduces blow-down requirement
Compatible with other boiler water treatment chemicals
Returns to the feed line with the condensate return, so raise the feed water pH
Corrosion of metal aerosol containers and valves can be prevented by using low levels of morpholine. It increases the pH of boiler water to protect the boiler against corrosion. Due to its amine-based formulation, it does not add salt to the boiler and hence does not contribute to the TDS, which results in reduced blow down and fuel savings. Morpholine can be used in all types, sizes, and pressure of boilers.
ATAMAN KIMYA provides high-quality Morpholine for boiler water treatment globally.
www.atamankimya.com
Morpholine, an organic compound with both amine and ether groups, is obtained by dehydrating diethanolamine with sulphuric acid. Morpholine can be adapted to many different activities for many important applications. Some of its different adaptations can be seen in the following applications. It functions as an intermediate in the production of rubber chemicals, even as optical brighteners. It acts as an effective corrosion inhibitor in steam boiler systems. Morpholines can utilize as pharma chemicals and antioxidants for lubricating oils.
Morpholines can be used as emulsifiers in wax and polishes processing industries.
Morpholine is a very good pH adjuster and very effective for nuclear power plants. One more reason for it to be used is that it rates vaporization, which is quite similar to water; so what happens is when it is added to water, it disperses accordingly in water in both of its liquid and vapor phases. It can also be used as an ingredient in fungicides and bactericides.
Key Features and Benefits
Prevents stress cracking corrosion
Reduces blow-down requirement
Returns to the feed line with the condensate return so raise the feed water pH.
Saves power & downtime
Compatible with other treatment chemicals
Versatile applications
Physicochemical Data
Properties: Typical Value
Form: Clear liquid
Appearance: Colourless
Odour: Amine like
Assay as Morpholine:99.0% min.
Solubility: Completely soluble in water
Application Areas
Rubber Chemicals: Delayed action accelerator
Catalysts: Temperature-sensitive polymerization inhibitor
Gelling agent
Optical Brighteners
Stabler than chlorine bleaches
Pharma Chemicals: Morpholine derivatives as analgesics and anesthetics
Choleretics, antispasmodics, analeptics, antimalarials
Corrosion Inhibitors:Neutralizing Amine
Antioxidants
Separating Agents: Wax Emulsifier
Self-polishing waxes and polishes: Surface tension depressor
Scrubbing organic sulfur compounds from fuel gas
Purification procedures
Biocide
Bacteriostatic/ bactericidal properties
Anti-fungal
Processing Industries
Processing Industries (Non-food)
Water Treatment
Handling Measures and Precautions: DG Cargo. Morpholine is hazardous in nature. Proper human safety products such as splash goggles, lab coat, dust and vapour respirator, NIOSH approved gloves and boots should be worn while handling and applying chemicals. Splashes on the skin should be washed off with water immediately. In case of splashing into the eyes, flush them with fresh water and obtain medical attention. Should not be injected. Kindly refer SDS for more details.
Storage
Morpholine should be stored in original vented containers, away from heat, direct sunlight and combustibles. Store in a cool and dry place. Kindly refer SDS for details.
1-Oxa-4-azacyclohexane
2H-1,4-Oxazine, tetrahydro-
4H-1,4-Oxazine, tetrahydro-
BASF 238
Diethylene imidoxide
Diethylene oximide
Diethyleneimide oxide
Diethylenimide oxide
Drewamine
Morpholine
MORPHOLINE
p-Isoxazine, tetrahydro-
Tetrahydro-1,4-isoxazine
Tetrahydro-1,4-oxazine
Tetrahydro-2H-1,4-oxazine
Tetrahydro-p-oxazine
MORPHOLINE
Morfolin
110-91-8
1-Oxa-4-azacyclohexane
Tetrahydro-1,4-oxazine
Diethylene oximide
Diethylenimide oxide
Diethyleneimide oxide
Drewamine
Diethylene imidoxide
morpholin
Tetrahydro-2H-1,4-oxazine
Tetrahydro-p-oxazine
p-Isoxazine, tetrahydro-
Tetrahydro-1,4-isoxazine
BASF 238
Caswell No. 584
Morpholine, 4-soya alkyl derivs.
2H-1,4-Oxazine, tetrahydro-
4H-1,4-Oxazine, tetrahydro-
EINECS 203-815-1
UN2054
C4H9NO
EPA Pesticide Chemical Code 054701
BRN 0102549
Tetrahydro-4H-1-4-oxazine
61791-40-0
Morpholine [UN2054] [Flammable liquid]
Morpholine, 99+%, extra pure
CAS-110-91-8
MORPHOLINE,REAG
Tetrahydro-p-isoxazine
MORPHOLINE, PRACT
morphline
morpho line
morpholine-
EINECS 263-172-8
4H-1, tetrahydro-
PubChem15002
Morpholine
1,4$l^{2}-oxazinane
Tetrahydro-1, 4-isoxazine
Oprea1_317540
Tetryhydro-2H-1,4-oxazine
Tetrahydro-4H-1,4-Oxazine
4-27-00-00015 (Beilstein Handbook Reference)
Morpholine, analytical standard
morfoliin (et)
Morfoliini (fi)
morfolin (cs)
morfolin (hr)
morfolin (hu)
morfolin (no)
morfolin (sl)
morfolin (sv)
morfolina (es)
morfolina (it)
morfolina (pl)
morfolina (pt)
morfolina (ro)
morfolinas (lt)
morfoline (nl)
morfolín (sk)
morfolīns (lv)
morpholin (da)
Morpholin (de)
morpholine (fr)
morfolin (tr)
morfolin (türkçe)
tetrahidro-1,4-oxazina (es)
tetrahydro-1,4-oksazyna (pl)
μορφολίν (el)
мoрфолин (bg)
CAS names
Morpholine
IUPAC names
2-chloro-1-morpholin-4-ylethanone
4H-1,4-Oxazine, tetrahydro-
Morpholin
MORPHOLINE
Morpholine
morpholine
tetrahydro 1.4 oxazine
Tetrahydro-1,4-oxazine
Tetrahydro-2H-1,4-oxazine
Tetraidro-1,4-ossazina
Trade names
1-Oxa-4-azacyclohexane
2H-1,4-Oxazine, tetrahydro-
4H-1,4-Oxazine, tetrahydro-
BASF 238
Diethylene imidoxide
Diethylene oximide
Diethylenimide oxide
Drewamine
p-Isoxazine, tetrahydro-
Tetrahydro-1,4-oxazine
Tetrahydro-2H-1,4-oxazine
Tetrahydro-p-oxazine
102549 [Beilstein]
110-91-8 [RN]
203-815-1 [EINECS]
8B2ZCK305O
MFCD00005972 [MDL number]
Morfolina [Italian]
Morfolina [Portuguese]
Morpholin [German] [ACD/IUPAC Name]
Morpholine [ACD/Index Name] [ACD/IUPAC Name] [Wiki]
Morpholine [French] [ACD/Index Name] [ACD/IUPAC Name]
QD6475000
Tetrahydro-1,4-oxazine
UNII:8B2ZCK305O
Морфолин [Russian]
モルホリン [Chinese]
吗啉 [Chinese]
吗啡啉 [Chinese]
138048-80-3 [RN]
1-Oxa-4-azacyclohexane
2H-1,4-Oxazine, tetrahydro-
4-27-00-00015 (Beilstein Handbook Reference) [Beilstein]
4H-1,4-Oxazine, tetrahydro-
Diethylene imidoxide
Diethylene oximide
Diethyleneimide oxide
diethylenimide oxide
Drewamine
Morpholine-d8
N-Vinylbenzylmorpholine-divinylbenzene Copolymer
Oprea1_317540
p-Isoxazine, tetrahydro-
ST5213815
STR00194
T6M DOTJ [WLN]
Tetrahydro-1, 4-isoxazine
Tetrahydro-1,4-isoxazine
Tetrahydro-2H-1,4-oxazine
Tetrahydro-4H-1,4-Oxazine
Tetrahydro-4H-1-4-oxazine
Tetrahydro-P-isoxazine
Tetrahydro-p-oxazine
Tetryhydro-2H-1,4-oxazine
UN 2054
UNII-8B2ZCK305O
WLN: T6M DOTJ
Other identifiers
CAS number
1357848-50-0
CAS number
1357848-50-0
Deleted CAS number
147366-31-2
CAS number
147366-31-2
Deleted CAS number
613-028-00-9
Index Number
854893-20-2
CAS number
854893-20-2
Deleted CAS number
88542-81-8
CAS number
88542-81-8
Deleted CAS number
96122-95-1
CAS number
96122-95-1
Deleted CAS number
99108-56-2
CAS number
99108-56-2
Deleted CAS number
Morpholine is a heterocycle featured in numerous approved and experimental drugs as well as bioactive molecules. It is often employed in the field of medicinal chemistry for its advantageous physicochemical, biological, and metabolic properties, as well as its facile synthetic routes. The morpholine ring is a versatile and readily accessible synthetic building block, it is easily introduced as an amine reagent or can be built according to a variety of available synthetic methodologies. This versatile scaffold, appropriately substituted, possesses a wide range of biological activities. There are many examples of molecular targets of morpholine bioactive in which the significant contribution of the morpholine moiety has been demonstrated; it is an integral component of the pharmacophore for certain enzyme active‐site inhibitors whereas it bestows selective affinity for a wide range of receptors. A large body of in vivo studies has demonstrated morpholine's potential to not only increase potency but also provide compounds with desirable drug‐like properties and improved pharamacokinetics. In this review we describe the medicinal chemistry/pharmacological activity of morpholine derivatives on various therapeutically related molecular targets, attempting to highlight the importance of the morpholine ring in drug design and development as well as to justify its classification as a privileged structure.
Morpholine
Morpholine is a colorless, hygroscopic liquid with a characteristic amine-like odor. It is completely miscible with water and a large number of organic solvents, and is itself a solvent for a large variety of organic materials, including resins, dyes, waxes, shellac, and casein.
Molecular Formula : C4H9NO
Usage
Morpholine are mainly used to manufacture rubber accelerant (such as NOBS, OTOS and MDS), sulfuration agent (like DT-DM), cleanser, descaling agent, anti rust, anti-scorching agent, antiseptic, surfactant, textile printing & dyeing agent, optical bleaching agent, chemical plating bath, antioxidant, hydrolyzing agent, initiator, developer, fruit preserving agent, deodorizer, brightener and organic solvents. It is widely used in many industries such as medicine, pesticide, animal medicine, petroleum and extraction of coke aromatic hydrocarbon.