METHYL ETHYL KETOXIME


Methyl Ethyl Ketoxime = MEKO = Methyl ethyl ketone oxime = MEK-oxime = ketoxime = 2-Butanone, oxime
CAS Number: 96-29-7 


Antiskinning compound for oxidatively drying coating

Methyl Ethyl Ketoxime is an organic substance which is added to a paint to inhibit the reaction of the drier with (atmospheric) oxygen by binding the oxygen or by complexing of the drier metal.

Methylethyl ketone oxime is the organic compound with the formula C2H5C(NOH)CH3. Methyl ethyl ketoxime (MEKO) is a high-efficiency anti-skinning agent used for air-drying paints, inks and coatings. It is also used to improve the shelf life of silicone adhesives and sealants, and the functionality of polyurethane coatings. It is also widely used as an isocyanate-blocking agent in priming automobiles (electrodeposition coating) for paint jobs and as a curing agent for silicon rubber due to its outstanding water and heat resistance.


- MEKO is a Urethane blocking agent for coating applications.
- Methyl Ethyl Ketoxime can be used as Anti-skinning agent in paints (Alkyd based systems)
- MEKO is an Oxygen scavenger in boiler water treatment.
- MEKO can be used to produce oxime derivatives for other industrial applications


Butanone oxime 
2-Butanone, oxime 
Butan-2-one oxime 
2-Butanonoxime 
Methyl ethyl ketone oxime 
Methyl ethyl ketoxime 
Oxime 2-butanone 

Methylethyl ketone oxime is the organic compound with the formula C₂H₅CCH₃. This colourless liquid is the oxime derivative of methyl ethyl ketone. MEKO, as it is called in the paint industry, is used to suppress "skinning" of paints: the formation of a skin on paint before it is used.
Methyl Ethyl Ketoxime is an essential chemical used as an anti-skinning agent in paints and lacquers. This product can be used as an urethane blocking agent for coating applications which include powder coatings, automotive coatings, and coatings on plastic, textiles and general industrial metal.


Methylethyl ketone oxime is the organic compound with the formula C2H5C(NOH)CH3. This colourless liquid is the oxime derivative of methyl ethyl ketone. MEKO, as it is called in the paint industry, is used to suppress "skinning" of paints: the formation of a skin on paint before it is used. MEKO functions by binding the drying agents, metal salts that catalyze the oxidative crosslinking of drying oils. Once the paint is applied to a surface, MEKO evaporates, thereby allowing the drying process to proceed. Other antiskinning agents have been used, including phenol-based antioxidants, but these tend to yellow the paint.[1] Butanone oxime is also used in some types of RTV silicones.

Preferred IUPAC name
(2E)-N-Hydroxybutan-2-imine
Other names
MEKO, 2-Butanone oxime
Identifiers
CAS Number: 96-29-7 


Without the use of suitable additives alkyd based paints will form skins in the paint tin which need to be carefully removed prior to use. Traditionally the paint industry has used a slow evaporating solvent called Methyl Ethyl Ketoxime to prevent skins forming in the paint can.

The MEKO additive is added in very small proportions to the paint typically less than 0.5%.

MEKO is primarily used as an anti-skinning agent for oil and latex paints and coatings. Methyl Ethyl Ketoxime is also widely used as an isocyanate-blocking agent in priming automobiles for paint jobs and as a curing agent for silicon rubber due to its outstanding water and heat resistance.


Methylethyl ketone oxime is the organic compound with the formula C2H5C(NOH)CH3. MEKO is the oxime derivative of methyl ethyl ketone.

Application & Usage of MEK OXIME:
MEKO, as it is called in the paint industry, is used to suppress "skinning" of paints: the formation of a skin on paint before it is used.
MEK-oxime Prevents skinning in alkyd based systems.
MEK-oxime blocks urethanes in coating applications which include powder coatings

Methyl ethyl ketone oxime is the organic compound, is the oxime derivative of methyl ethyl ketone. 
Methyl ethyl ketone oxime works by binding the drying agents where metal salts that catalyze the oxidative crosslinking of drying oils. The methylethyl ketone oxime evaporates when the paint is applied thereby allowing the drying process to proceed.

In the paint industry, MEKO is used to suppress the skinning of paints. The methylethyl ketone oxime is a popular anti-skinning agent, used to suppress the formation of a skin on the paint before it is used. This anti-skinning agent is widely used as an isocyanate-blocking agent and primarily used for oil and latex paints and coatings.


An effective skinning agent can alleviate the difficulty of skinning. The methylethyl ketone oxime (MEKO) is used as a skinning agent in paint, it reduces skinning of paint by binding the drying agents where metal salts that catalyze the oxidative crosslinking of drying oils. Once the paint is applied the methyl ethyl ketone oxime evaporates, thereby allowing the drying process to proceed.


APPLICATION OF MEKO IN WATER TREATMENT
Methyl ethyl ketoxime (MEKO) is well known as an oxygen scavenger and metal passivator in boilers.
For more than a decade, MEKO has proven effective in suppressing dissolved oxygen throughout the utility steam cycle. The protective film formed appears to be less susceptible to flow assisted corrosion than the magnetite film formed with most of the other scavengers. This results in reduced metal oxide transport into the boiler and reduced metal oxide deposition in the boiler.
At elevated dosages, MEKO contributes to removal of oxides from the boiler. This can extend the time between chemical cleaning, reducing overall costs and extending boiler life expectancy. The use of MEKO does not adversely effect the cycle chemistry or the performance of ion exchange type condensate polishers.


Chemical Name: Methyl ethyl ketoxime
Synonyms: 2-Butoxime; 2-Butanonoxim; Methyl ethyl ketone oxime; Ethyl methyl;2-Butanone Oxime; MEKO;MethylEthyl Ketoxime; MethylEthyl Ketone Oxime; Diacetylmonoxime
ketoxime; MEK-oxime; MEKO
MEKO is primarily used as an anti-skinning agent for oil and latex paints and coatings. 
Methyl Ethyl Ketoxime is also widely used as an isocyanate-blocking agent in priming automobiles (electrodeposition coating) for paint jobs and as a curing agent for silicon rubber due to its outstanding water and heat resistance.

Application:
1. Methyl Ethyl Ketoxime is a kind of oil-based coating antioxidant, used for anti-skinning treatment during the storage and transportation of a variety of oil-based paint, alkyd paint, epoxy ester paint and etc. Mainly used as an anti-skinning agent and viscidity stabilizer for alkyd resin coating. 
As an anti-skinning agent, this product is recommended to be added in the amount of 0.1-0.3% after a test to determine the best usage and dosage.
2. Methyl Ethyl Ketoxime of high purity can be used in the synthesis of silicone cross-linking agent, silicon curing agent and isocyanate sealant
3. Methyl Ethyl Ketoxime can be used in offset printing ink and other industries, and used as corrosion inhibitor in industrial boiler or water treatment system.
4. IMethyl Ethyl Ketoxime can also be used as wood preservative and pharmaceutical intermediate for alum and magnesium removal and etc.
5. Methyl Ethyl Ketoxime can be used to produce high purity hydroxylamine sulfate, hydroxylamine hydrochloride and etc.

Without the use of suitable additives alkyd based paints will form skins in the paint tin which need to be carefully removed prior to use. 
Traditionally the paint industry has used a slow evaporating solvent called Methyl Ethyl Ketoxime to prevent skins forming in the paint can.

Methyl ethyl ketoxime (MEKO) is a high-efficiency anti-skinning agent used for air-drying paints, inks and coatings.
Methyl Ethyl Ketoxime is also used to improve the shelf life of silicone adhesives and sealants, and the functionality of polyurethane coatings.
MEKO is produced to meet the low moisture and high assay standards that formulators require

CAS Number: 96-29-7
CAS Name: 2-Butanone oxime
EC (EINECS) Number: 202-496-6
• Methyl ethyl ketoxime (MEKO) is an essential chemical used as an anti-skinning agent in paints and lacquers, as a blocking-agent for isocyanate in polyurethanes, and in the manufacture ofoxime silanes (that are used as crosslinkers for silicone sealants).
• MEKO is a High Production Volume (HPV) chemical produced at over 1,000,000 pounds annually. 
• MEKO is a clear, colorless combustible liquid.
• MEKO is severely irritating to eyes. If it gets into the eyes, immediately flush with plenty of water and seek medical attention to avoid serious damage.  
MEKO is moderately toxic in the unlikely event of ingestion. 
Ingesting or breathing high concentrations may cause harmful, but reversible, effects on the blood (anemia) and inhalation can irritate nasal passages.
MEKO is slightly irritating to skin, and can be absorbed through the skin to cause harmful effects on the blood and nervous system. 
Getting MEKO on the skin may cause an allergic response in certain individuals.
• MEKO is rapidly metabolized and eliminated from the body. MEKO does not cause harmful effects on reproduction or development.
• MEKO has minimal potential to accumulate in the bodies of humans or animals. It is readily biodegradable and will not persist in the environment.

Methylethyl ketone oxime is the organic compound with the formula C2H5C(NOH)CH3. 
This colourless liquid is the oxime derivative of methyl ethyl ketone. 
MEKO, as it is called in the paint industry, is used to suppress "skinning" of paints: the formation of a skin on paint before it is used. 
MEKO functions by binding the drying agents, metal salts that catalyze the oxidative crosslinking of drying oils. 
Once the paint is applied to a surface, MEKO evaporates, thereby allowing the drying process to proceed.antiskinning agents have been used, including phenol-based antioxidants, but these tend to yellow the paint.
Butanone oxime is also used in some types of RTV silicones.

Colorless and pigmented oxidatively drying paints and coatings based on oxidatively drying oils, alkyd resins, epoxy esters and other oxidatively drying refined oils are known. 
These oils and binders crosslink oxidatively under the influence of oxygen (preferably atmospheric oxygen) by means of the addition of driers, such as metal carboxylates of transition metals; If this crosslinking takes place before the product is actually used, a solid barrier film, a skin, can form on the surface. Skin formation can occur in open or closed containers. 
This is highly undesirable and should therefore be avoided since it makes the paint more difficult to work with, and commonly interferes with the uniform distribution of the driers. The accumulation of the driers in the paint skin that forms can lead to considerable delays in the drying of the paint when it is applied.

Skinning of the paint film after application is also disadvantageous. Excessively rapid drying of the surface of the paint prevents the lower film layers from drying evenly because they are shielded from oxygen, which is prevented from sufficiently penetrating into and dispersing within the paint film. 
This can lead among other things to flow problems in the paint film, adhesion problems, or insufficiently hard films.
It is known to add organic substances to a paint that inhibit the reaction of the drier with (atmospheric) oxygen by binding the oxygen or by complexing of the drier metal.

Methyl ethyl ketoxime (MEKO) is a high-efficiency anti-skinning agent used for air-drying paints, inks and coatings.
It is also used to improve the shelf life of silicone adhesives and sealants, and the functionality of polyurethane coatings.
MEKO is produced to meet the low moisture and high assay standards that formulators require.

BENEFITS of our anti skinning product Methyl ethyl ketoxime (MEKO) include:
- Improved storage stability
- Prolonged open time of films


MEKO is used as an anti-skinning agent for various oil-based paints, alcohol acid paints and epoxy resin paints during storage and delivery. It can also be used as a silicone curing agent. Its main uses are anti-skinning and silicone curing for alcohol acid and resin coatings. As an anti-skin and anti-oxidation agent, the product provides better effect than Butyraldehyde oxime and cyclohexanone oxime. It can also be used for synthesis of aqueous polyurethane resin


Methyl ethyl ketoxime, have another name called Diacetylmonoxime (Methyl ethyl ketoxime or 2-butanon oxime, MEKO), it can be used as the linking agent raw material of silicon, also can be used as paint anti and boiler feed water oxygen scavenger, is a fine chemical product that industrial value is arranged very much.
At present, industrial production mainly adopts hydroxylamine assay both at home and abroad, i.e. methylethylketone and oxammonium hydrochloride or oxammonium sulfate reactioN

Oxime oxygen scavenger
Oxime compounds (dimethyl ketone oxime, methyl ethyl ketoxime (butanone oxime), acetaldehyde oxime) knows as a novel oxygen scavenger is disclosed in the U.S. and patented by Drew Chemical Company in 1984. 
It displays low toxicity, efficiency, fast-performance, and a blunt protective effects. 
In Europe and other developed countries it has been widely applied, and China it is also successfully developed in the nineties, and has been successful in promotion.
1. Oxygen scavenging performance: oxime compound is an organic compound with an oxime group. Oxime compounds are currently used for boiler shutdown protection and oxygen mainly acetaldehyde oxime, dimethyl ketone oxime (acetone oxime) and methyl ethyl ketone oxime. Oxime compounds have a strong reduction, easy to react with oxygen. When put in a wide temperature and pressure ranges, oximes has good oxygen scavenging performance. The optimum temperature range is 138~336 ℃, and pressure range is 0.3~13.7Mpa. According to comparative experiments, under the same conditions, the rate of oxygen and oxygen efficiency oximes is higher than that of hydrazine.
2. corrosion and passivation: oximes can restore high iron and copper oxide into suboxide, which can be a good solution in the steel magnetic oxide film formed on the surface of the metal surface passivation plays well, corrosion inhibition. Wherein dimethylketoximino is the best, using the minimum amount required. According to comparative experiments, oxime compounds having the same passivation, corrosion inhibition hydrazine, can significantly reduce the iron content in solution at high temperature and pressure conditions. The steel has a protective effect, among which the dimethylketoximino is best, which requires the least amount . Meanwhile, oxime compounds have cleaning actions to copper corrosion products deposited in the pipeline, economizer, etc., which is in the initial period of oximes. This is the reason why furnace copper water content is significantly higher.
3. Volatile: the volatile degree of oxime compounds is higher than that of hydrazine, DEHA, morpholine, cyclohexylamine, etc. It is close to the volatility of NH3. When the steam condenses, highly volatile oxygen scavenger will has a certain amount of condensation agent which is dissolved in water, therefore, helpful to protect the condensate system metal material.
4. decomposition: By experiments under the high temperature and pressure conditions, the decomposition products of oxime compound is NH3, N2, H2O, trace of acetic acid, formic acid produces, no adverse effects on water vapor system.
5. low toxicity: based on the data comparison of LD50, the LD50 for hydrazine is 290mg/kg, acetaldehyde oxime is 1900mg/kg, methyl ethyl ketone oxime is 2800mg/kg, dimethylket oximino 5500mg/kg. So the toxicity of hydrazine is very strong, and toxicity of oxime compound is very small. It belongs to low toxicity compounds. Test through the skin and mucous membrane contact with oxygen scavengers showed no significant oximes oxygen scavenger irritation and damage, but hydrazine causes damage of skin irritation, erosion, mucosal hyperemia.

Chemical Properties
Colorless oily liquid. Melting point-29.5 ℃. Boiling point 152-153 ℃, 59-60 ℃ (2kPa), the relative density is 0.9232 (20/4 ℃), and refractive index 1.4410. With alcohol, ether immiscibility, dissolved in 10 parts of water.
Uses
Mainly used inalkyd paintanti-skinningagentand siliconcuring agent.The product is used to prevent the use of the crust. It is better than butyraldehydeoxime, cyclohexanone oxime in effect.
Used in organic synthesis
For a variety of oil-based paint, alkyd paint, epoxy paint, such as esters during storage and transportation of anti-skinning process, also used as a curing agent silicon

96-29-7 
Name: Ethyl methyl ketone oxime
CAS: 96-29-7
Molecular Formula: C4H9NO
Molecular Weight: 87.1204

CAS 96-29-7 
Names and Identifiers

Name
Ethyl methyl ketone oxime

Synonyms    
2-Butanone oxime
2-butoxime
aron m 1
butanone oxime
ethyl methyl ketoxime
Methyl ethyl ketoxime
(2E)-butan-2-one oxime
(2Z)-butan-2-one oxime
CAS:96-29-7
EINECS    202-496-6

96-29-7 - Physico-chemical Properties
Molecular Formula:C4H9NO
Molar Mass:87.1204 g/mol
Density: 0.9g/cm3
Melting Point:-30℃
Boling Point:152.5°C at 760 mmHg
Flash Point:60°C
Solubility: 114 g/L (20℃)
Vapor Presure: 1.88mmHg at 25°C
Refractive Index:1.421
96-29-7 

Risk and Safety
Hazard Symbols    Xn - Harmful
Harmful
Risk Codes    
R21 - Harmful in contact with skin
R40 - Limited evidence of a carcinogenic effect
R41 - Risk of serious damage to eyes
R43 - May cause sensitization by skin contact

Safety Description    
S13 - Keep away from food, drink and animal foodstuffs.
S23 - Do not breathe vapour.
S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection.
UN IDs    UN 1993


CHEMICAL REACTIVITY
Reactive Group: –

Oximes
Reactivity Alerts: –

Highly Flammable
Decomposes at Elevated Temperatures (<120 deg. C)
Air and Water Reactions:-

Highly flammable.
Water
Reactivity Profile:-

MEKO is sensitive to heat.
Has exploded at least twice when heated in the presence of acidic impurities.
Reacts with oxidizing agents.
Mixtures with strong acids may explode.
Reacts with sulfuric acid to form an explosive product.
APPLICATIONS

Adhesives and sealant chemicals
Paint additives and coating additives not described by other categories
Solvents (which become part of product formulation or mixture
 

IN PAINT INDUSTRY
MEKO, as it is called in the paint industry, is used to suppress “skinning” of paints: the formation of a skin on paint before it is used, hence is a popular anti-skinning agent.

Skinning is the biggest nuisance in protective coatings. Skinning causes the avoidable waste of a costly coating material.
Paint containers are not always filled to the brim. So air present in a void reacts with the paint, thereby causing oxidation and polymerization of the coating at the air/paint interface. This results in formation of a solid skin during storage.
The lost of paint due to skinning is estimated to be as much as 3 to 5%. This not only worries the consumers but also the manufacturers when it comes to filling of small containers. The minute doze of an effective anti-skinning agent can alleviate the difficulty of skinning.

what is MEKO: Chemical property of MEKO which is useful in paint industry :-

MEKO functions by binding the drying agents, metal salts that catalyze the oxidative crosslinking of drying oils.

Once the paint is applied to a surface, MEKO evaporates, thereby allowing the drying process to proceed. Other antiskinning agents have been used, including phenol-based antioxidants, but these tend to yellow the paint.

 

HEALTH HAZARDS:-
Symptoms of exposure to this compound may include slight eye and skin irritation.
If gets absorbed through the skin can cause harmful effects on the blood and nervous system.
If inhaled in greater amounts can give rise to symptoms such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest may also develop.
It may interfere with alcohol metabolism resulting in the formation of acetaldehyde, blotchy red marks, red eyes, tiredness and visible veins.
FIRE HAZARDS:-
This chemical is combustible.
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon  A water spray may also be used.
ENVIRONMENTAL HAZARDS:-

MEKO has minimal potential to accumulate in the bodies of humans or animals. It is readily biodegradable and will not persist in the environment.
When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide and nitrogen oxides.


(2E)-N-Hydroxy-2-butanimin [German] [ACD/IUPAC Name]
(2E)-N-Hydroxy-2-butanimine [ACD/IUPAC Name]
(2E)-N-Hydroxy-2-butanimine [French] [ACD/IUPAC Name]
(2E)-N-Hydroxybutan-2-imine
10341-63-6 [RN]
2-BUTANONE OXIME
2-Butanone, oxime, (2E)- [ACD/Index Name]
96-29-7 [RN]
EL9275000
Methyl ethyl ketoxime
Methylethyl ketone oxime
MFCD00013935 [MDL number]
(2E)-butan-2-one oxime
(E)-N-(BUTAN-2-YLIDENE)HYDROXYLAMINE
(NE)-N-butan-2-ylidenehydroxylamine
(NZ)-N-butan-2-ylidenehydroxylamine
2-BUTA OXIME
2-Butanone oxime
2-Butanone oxime,C4H9NO,96-29-7
2-BUTANONE, OXIME, (E)-
2-Butanoneoxime
2-butoxime
Aron M 1
butan-2-one, oxime
Butanone oxime
Ethyl methyl ketone oxime
ETHYL METHYL KETOXIME
Ethyl-methylketonoxim
MEK-oxime
Methyl ethyl ketone oxime
Methylethylketoxime
N-Hydroxybutan-2-imine
Pentan-2-one,oxime
SKINO 2
Skino No. 2
Troykyd anti-skin B
丁酮肟

2-Butanone oxime
2-butanone oxime
2-butanone oxime; ethyl methyl ketoxime; ethyl methyl ketone oxime
A mixture of: butan-2-one oxime; syn-O,O'-di(butan-2-one oxime)diethoxysilane

Butanone oxime
Butanone oxime
butanone oxime
butanone oxime; ethyl methyl ketoxime; ethyl methyl ketone oxime; Ethyl methyl ketone oxime
ethyl methyl ketone oxime
Ethyl methyl ketoxime
ethyl methyl ketoxime
Ethyl-methylketonoxim
MEK-oxime
Methyl ethyl ketone oxime
Methyl ethyl ketoxime
Skino #2
Troykyd anti-skin B

Translated names
2-butanonoksim; etylmetylketoksim (no)
butan-on-oxim; ethylmethylketoxim, ethyl(methyl)ketonoxim (cs)
butanon oksim; ethyl methyl ketoxime; ethyl methyl ketone oxime (sl)
butanon-oksim; etil-metil-ketoksim; etil-metil-keton-oksim (hr)
butanon-oxim; etil-metil-ketoxim; etil-metil-keton-oxim (hu)
butanon-oximă; etil-metilcetoximă; etil-metil-ceton-oximă; (ro)
butanona oksīms; etilmetilketoksīms; etilmetilketona oksīms (lv)
butanone-oxime; éthylméthylcétoxime; éthyl(méthyl)cétone-oxime (fr)
butanonioksiimi; etyylimetyyliketoksiimi; etyylimetyyliketonioksiimi (fi)
butanono oksimas; etilmetilketoksimas; etilmetilketono oksimas (lt)
butanonossima; etilmetilchetossima; etilmetilchetone ossima (it)
butanonoxim; ethylmethylketoxim; ethylmethylketonoxim (da)
Butanonoxim; Ethylmethylketoxim; Ethylmethylketonoxim (de)
butanonoxim; ethylmethylketoxim; ethylmethylketonoxim (nl)
butanonoxim; etylmetylketoxim; etylmetylketonoxim (sv)
Butanoonoksiim; etüülmetüülketoksiim; etüülmetüülketoonoksiim (et)
butanón-oxím; etyl(metyl)ketoxím; etyl(metyl)ketón-oxím (sk)
oksym butanonu; oksym ketonu etylowo-metylowego (pl)
ossimu tal-butanon; ketossimu tal-etil metil; ossimu tal-etil metil keton (mt)
oxima de butanona; cetoxima etílica e metílica; oxima de cetona etílica e metílica (pt)
Oxima de butanona; etil-metil-cetoxima; oxima de etil-metil-cetona (es)
οξίμη βουτανόνης· μεθυλαιθυλοκετοξίμη· οξίμη μεθυλαιθυλοκετόνης (el)
бутаноноксим; етилметилкетоксим; етилметилкетоноксим (bg)

CAS names
2-Butanone, oxime

IUPAC names
(2E)-butan-2-one oxime
(2E)-N-Hydroxy-2-butanimine
(NE)-N-butan-2-ylidenehydroxylamine
(NZ)-N-butan-2-ylidenehydroxylamine
2-Butanone Oxime
2-Butanone oxime
2-butanone oxime
2-Butanone oxime
2-butanone oxime; ethyl methyl ketoxime; ethyl methyl ketone oxime
2-butanone oxime; ethyl methyl ketoxime;ethyl methyl ketone oxime
2-Butanone, oxime
2-butanone, oxime
butan-2-one oxime
butan-2-one-oxime
Butanone oxime
butanone oxime
butanone oxime
Butanonoxim (Methyl ethyl ketoxim)
ethyl methyl ketone oxime
ethyl methyl ketoxime
ketoxime
MEKO
MEKO; butanone oxime; butan-2-one oxime; 2-butanone oxime
METHYL ETHYL KETONE OXIME
Methyl Ethyl Ketoxime
Methyl ethyl ketoxime
Methyl Ethyl Ketoxime
Methylethyl ketoxime
N-butan-2-ylidenehydroxylamine
tbc

Trade names
Antioxidant B
ANTIPELLE METILETILCHETOSSIMA
butanone oxime
Durham CA111
Exkin 2
MEKO
Methyl ethyl ketoxime
SKINO
(2E)-N-Hydroxy-2-butanimine
MEKO, 2-Butanone oxime
2-butanone oxime
MEKO
methylethyl ketoxime
2-BUTANONE OXIME
Methyl ethyl ketoxime
96-29-7
2-Butanone, oxime
Butanone oxime
Ethyl methyl ketoxime
Troykyd anti-skin B
Ethyl methyl ketone oxime
(E)-butan-2-one oxime
2-Butoxime
Methylethylketoxime
NSC 442
Pentan-2-one,oxime
Butan-2-one, oxime
Skino No. 2
CAS-96-29-7
Aron M 1
N-butan-2-ylidenehydroxylamine
SKINO 2
2-Butanone, oxime, (E)-
MEK oxime
ethylmethyl-ketoxime
methylethyl ketoxime
methylethylketone oxime
ACMC-1BQBU
2-Butanone, oxime, (Z)-


MEK-oxime
Butanone oxime
Methyl ethyl ketone oxime
2-BUTANONE OXIME
Ethyl methyl ketoxime
USAF EK-906
Ethyl-methylketonoxim
UNII-51YGE935U9
2-Butanone, oxime
Methyl ethyl ketoxime
51YGE935U9
Troykyd anti-skin B
Skino #2
USAF AM-3
WLN: QNUY2&1
Ethyl-methylketonoxim [Czech]
CCRIS 1382
96-29-7
NSC 442
EINECS 202-496-6
BRN 1698241


Product Identification:
Name:2-Butanone Oxime; MEKO;MethylEthyl Ketoxime;
MethylEthyl Ketone Oxime; Diacetylmonoxime
CAS No.: 96-29-7
Molecular Formula: C4H9NO
Molecular Weight: 87.12
EINECS No.: 202-496-6

Methyl ethyl ketoxime (MEKO) is an essential chemical used as an anti-skinning agent in paints and lacquers, as a blocking-agent for isocyanate in polyurethanes, and in the manufacture of oxime silanes (that are used as crosslinkers for silicone sealants). 


Application: Methyl ethyl ketoxime (MEKO) is an essential chemical used as an anti-skinning agent in paints and lacquers, as a blocking-agent for isocyanate in polyurethanes, and in the manufacture of oxime silanes (that are used as crosslinkers for silicone sealants).

2-BUTANONE OXIME

Methyl ethyl ketoxime

96-29-7

2-Butanone, oxime

N-butan-2-ylidenehydroxylamine

Ethyl methyl ketoxime

(E)-butan-2-one oxime

DSSTox_CID_1821

DSSTox_RID_76348

DSSTox_GSID_21821

2-Butoxime

Methylethylketoxime

Pentan-2-one,oxime

Butan-2-one, oxime

Skino No. 2

CAS-96-29-7

Aron M 1

SKINO 2

MEK oxime

ethylmethyl-ketoxime

methylethyl ketoxime

methylethylketone oxime

Methyl ethyl ketoxime is used as urethane blocking agent; it blocks urethane in coating applications which include power coatings, automotive coatings, coatings on plastic, textile, and general industrial metals. It is used as anti-skinning agent in paints and is used in water treatment. It is also used to produce oxime derivatives for other industrial applications. It is also a useful intermediates for the preparation of O-alkyd and O-acyl oximes, nitrones, amides, carbamates, O-silyl compounds and heterocyclic systems.

Antiskinning Agents in PAINTS and COATINGS
Alkyd paints undergo cross linking polymerization during storage stage forming a skin like polymeric surface at the top of the paint. 

The reason for this polymerization is the trapped oxygen and the catalytic action of cobalt driers.

The skinning as this phenomenon is named can be prevented only by eliminating the cause, in this case the oxygen or the cobalt drier activity. 

This can be achieved by using specific substances that either are free radical scavengers delaying the oxidation process or complexing driers deactivate temporally the cobalt ion. The ion stays free again after application of the paint and evaporation of the complexing agent.

Oxime is any compound with the general formula R\R'/C=N-OH, where R and R' are hydrogen atoms or organic groups. Oximes are condensation products of hydroxylamines with aldehydes (forming aldoxime), ketones (forming ketoxime), or quonone. Aldoximes exist only as a syn isomer. But benzaldoxime (aromatic aldoximes) exist in syn- and anti isomers: the syn form melts at 34C, antiisomeric form at 130 C; both forms are soluble in ethanol and ether. 

There are two geometrical isomer: syn and anti isomer (the term syn-anti isomerism is for stereoisomers by other atoms' unsaturated bond rather than carbon). Two isomers have very different properties. The conversion of oximes into corresponding amides, known as Beckmann rearrangement (usually using sulphuric acid as a catalyst), is used to make synthetic fiber monomers. Cyclhexanone oxime is converted into its isomer epsilon-caprolactam which is the raw material to make nylon-6. The amides obtained by Beckmann rearrangement can be converted into amines by hydrolysis, which are useful in the manufacture of dyes, plastics, synthetic fibres, and pharmaceuticals.
Oximes are used as a peel-preventing additive in paints and lacquers. It acts as an antioxidant against oxidative drying materials which forms sticky skin with air oxygen. The another effect of anti-skinning offers drying time delay which can be used in formulating paints.

Oximes are used as chemical building block for the synthesis of agrochemicals and pharmaceuticals. In medicine application, Oxime structure is effective in cholinesterase reactivators to treat the poisoning by organophosphates. Example of these drugs are pralidoxime, obidoximine, methoxime, asoxime, and trimedoxime. Oxime moiety is found in some cephalosporin antibiotics. Diacetyl monoxime is used as an inhibitor of ATP-sensitive potassium ion channels.

Diacetyl (dimethylglyoxal) reacts with hydroxylamine to produce diacetyldioxime (dimethylglyoxime). The characteristic property of oxime is the scavenging free radical and oxygen. Diacetyl oxime is used as a chelating agent. An application example is the spectrophotometric determination of Co(II), Fe(II), Ni(II), Pd(II) and Re(VII)1. Dimethylglyoxime reacts with a nickel salt in a green solution to generate a red colored insoluble tetradentate coordinate complex of nickel. It is used as a reagent for the colorimetric determination of urea and ureido compounds.

Oxime is used as a ligand in transition-metal complex catalyst chemistry. Oxime acts as an antioxidant, radical scavenger which find applications in textile, plastic, paint, detergent, and rubber industry.


Methyl ethyl ketoxime (MEKO) as CORROSION INHIBITOR IN WATER TREATMENT INDUSTRY:

Methyl Ethyl Ketoxime (MEKO) is one of the chemical oxygen scavengers that are commonly used for treatment of boiler systems. 
Corrosion and flow assisted corrosion (FAC) of condensers, feedwater heaters, feedwater piping and economizers result in forced outages, which cost the utility industry millions of dollars in maintenance. In many instances, they require the purchase or generation of power at elevated cost.

The accumulation of the products of corrosion in the generating tubes of steam generators also contributes to corrosion, and eventually these deposits must be removed through chemical cleaning.

Methyl ethyl ketoxime (MEKO) was first successfully introduced to the utility industry more than 10 years ago as a replacement for hydrazine. Initial work entailed monitoring dissolved oxygen in both the condensate pump discharge and deaerator outlet. At low ppb levels of MEKO, the dissolved oxygen levels in both streams were maintained or reduced. Users also noted a dramatic reduction in the quantities of metal oxides removed during the normal five-year operating cycle.

Subsequent applications at several stations demonstrated MEKO's ability to control dissolved oxygen, even under upset conditions. Also, the levels of iron and copper oxide corrosion products generated in the feedwater circuit reduced significantly.

This has been attributed to the change in oxide film morphology in the presence of MEKO. The oxide film generated tends toward g-iron oxide, which is more resistant to FAC than the magnetite film formed under the hydrazine regime.

Recently, rigorous testing also demonstrated that deposit weights can be reduced in the generating tubes of these high-pressure utility steam generators during normal operation. This allows the plant to extend the period of time between chemical cleaning and reduces the potential for corrosion of the boiler tubes because of metal oxide deposition and subsequent chemical cleaning.

This paper presents data on the impact of MEKO on dissolved oxygen control, reduction in the generation and transport of metal oxides in the condenser/feedwater circuits and deposit reduction in the steam generators. Also, the effects of MEKO on cation conductivity, organic acid generation and condensate polisher resin will also be addressed. Through the proper application of this oxygen scavenger/metal passivator, corrosion throughout the entire utility steam cycle can be reduced.

Corrosion and flow assisted corrosion (FAC) of condensers, feedwater heaters, feedwater piping and economizers result in forced outages, which cost the utility industry millions of dollars in maintenance. In many instances, they require the purchase or generation of power at elevated cost.

The accumulation of the products of corrosion in the generating tubes of steam generators also contributes to corrosion, and eventually these deposits must be removed through chemical cleaning.

BENEFITS OF Methyl ethyl ketoxime (MEKO):
• Efficient oxygen scavenging
• Passivation of steel surfaces in pre-boiler, boiler and condensate areas
• Equally effective in both vapor and liquid phases
• No secondary amines
• Easier to handle than hydrazine and hydroquinone
• Economical relative to other products, such as sodium erythorbate
• Compatible with other commonly used treatment chemicals
• Lower evaporative loss of actives than diethylhydroxylamine (DEHA) in vented bulk storage containers


MECHANISM: 
Methyl Ethyl Ketoxime (MEKO) reacts with dissolved oxygen in an aqueous system.
The reaction is virtually non-existent at room temperatures, but at elevated boiler conditions it is reported to react with oxygen.

MEKO is claimed to react with iron and copper oxides to produce passive protective oxides:

Because the reaction with oxygen is slow at low temperature, the reaction is probably also very slow under normal condensate temperature conditions.
MEKO will degrade under boiler conditions:

At 1800 psig MEKO will produce the same amount of ammonia that would be produced from an equivalent amount of nitrogen in the form of hydrazine.


 

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