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METHYL ETHYL KETOXIME









Methyl Ethyl Ketoxime (MEKO)
Product Stewardship Summary of ATAMAN KIMYA 2021

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. 
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.

Application:
1. This product 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. This product of high purity can be used in the synthesis of silicone cross-linking agent, silicon curing agent and isocyanate sealant
3. This product can be used in offset printing ink and other industries, and used as corrosion inhibitor in industrial boiler or water treatment system.
4. It can also be used as wood preservative and pharmaceutical intermediate for alum and magnesium removal and etc.
5. It 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.
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

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.


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

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