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Methyl Ethyl Ketoxime is the organic compound with the formula C2H5C(NOH)CH3. This colourless liquid is the oxime derivative of methyl ethyl ketone. Methyl Ethyl Ketoxime, as it is called in the paint industry, is used to suppress the "skinning" of paints: the formation of a skin on the paint before it is used. Methyl Ethyl Ketoxime functions by binding the drying agents, metal salts that catalyze the oxidative crosslinking of drying oils. Once the paint is applied to a surface, Methyl Ethyl Ketoxime evaporates, thereby allowing the drying process to proceed. Other anti skinning 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.
CAS NO: 96-29-7
EC NUMBER: 202-496-6
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
A mixture of: butan-2-one oxime; syn-O,O'-di(butan-2-one oxime)diethoxysilane
N-(butan-2-ylidene)hydroxylamine bis(Z)-(butan-2-ylidene)amino diethyl silicate
reaction mass of: butan-2-one oxime
syn-O,O'-di(butan-2-one oxime)diethoxysilane
SYNONYMS:
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; SKINO 2; MEK oxime; ethylmethyl-ketoxime; methylethyl ketoxime,methylethylketone oxime; ACMC-1BQBU; CHEMBL3181847; DTXSID1021821; Tox21_201706; Tox21_300162; ANW-40802; AKOS017263158; ZINC242701543; NCGC00254161-01; NCGC00259255-01; B0688; FT-0611623; 103055-EP2275407A1; 103055-EP2301918A1; (2E)-2-Butanone oxime; 2-Butoxime; Aron M 1; Butan-2-one, oxime; butan-2-oneoxime; Butanoxime; ethylmethylcetoxime; Ethyl-methylketonoxim; MEK-Oxime; methylethylcetoxime; methylethylketoxime(meko); Pentan-2-one,oxime; SKINO; SKINO 2; Skino No. 2; skino#2; Troykyd anti-skin B; troykydanti-skinb; USAF AM-3; USAF DO-44; USAFEK-906; usafam-3; usafek-906; 2-BUTANONE OXIME; 2-BUTANONOXIME; MEKO; METHYL ETHYL KETONE OXIME; METHYL ETHYL KETOXIME; BUTANONE OXIME; Ethyl methyl ketone oxime; ETHYL METHYL KETOXIME; 2-BUTANONE OXIME, 99%, MIXTURE OF SYN AN D ANTI; 2-Butanone Oxime、Methyl Ethyl Ketoxime; 2-Butanoneoxime,99%; Etylmethylketoxime; Methylethylketoxim; 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; Exkin 2; Ethylmethylketonoxime; Ethyl Methyl Ketoxime Methyl Ethyl Ketoxime; (E)-butan-2-one oxiMe; 2-Butanone Oxime >; 2-Butanone oxime fandachem
Consumer Uses
Methyl Ethyl Ketoxime is used in the following products: coating products.
Another release to the environment of Methyl Ethyl Ketoxime is likely to occur from: indoor use as a processing aid and outdoor use as a processing aid.
Widespread uses by professional workers
Methyl Ethyl Ketoxime is used in the following products: coating products. Another release to the environment of Methyl Ethyl Ketoxime is likely to occur from: indoor use as a processing aid and outdoor use as a processing aid.
Formulation or re-packing
Methyl Ethyl Ketoxime is used in the following products: coating products and polymers.
Release to the environment of Methyl Ethyl Ketoxime can occur from industrial use: formulation of mixtures.
Uses at industrial sites
Methyl Ethyl Ketoxime is used in the following products: coating products.
Methyl Ethyl Ketoxime has an industrial use resulting in the manufacture of another substance (use of intermediates).
Methyl Ethyl Ketoxime is used in the following areas: formulation of mixtures and/or re-packaging.
Methyl Ethyl Ketoxime is used for the manufacture of chemicals.
Release to the environment of Methyl Ethyl Ketoxime can occur from industrial use: in processing aids at industrial sites, as an intermediate step in further manufacturing of another substance (use of intermediates), manufacturing of the substance, formulation of mixtures and as a processing aid.
Manufacture
Release to the environment of Methyl Ethyl Ketoxime can occur from industrial use: manufacturing of the substance.
USE AREAS
General adhesives and binding agents for a variety of uses
Relating to agriculture, including the raising and farming of animals and growing of crops
Products used on crops, or related to the growing of crops
Related to fruit crops, or the processing or preserving of fruit
General adhesives and binding agents for a variety of uses
Promoting absorption of moisture
To prevent the formation of skin
Subcategory of apparel, including gloves
Components of automobiles (e.g. gaskets, cavity seals, bearings, gears), accessories such as batteries or safety accessories, etc
Binding agents, used in paint, sand, etc
Various types of paint for various uses, modifiers included when more information is known
Buffer or pH regulating agent,
Related to the building or repair of ships, pleasure boats, or sporting boats
Bricks or related to bricklaying/masonry
Flooring materials (carpets, wood, vinyl flooring), or related to flooring such as wax or polish for floors
Related to heating, such as heating systems, heating fuels, fireplaces, furnaces, radiators, boilers, etc
Plumbing, plumbing tools
Materials used in the building process, such as flooring, insulation, caulk, tile, wood, glass, etc.
Fillers for paints, textiles, plastics, etc
Flooring materials (carpets, wood, vinyl flooring), or related to flooring such as wax or polish for floors
Insulating materials to protect from noise, cold, etc (such as used in homes or buildings), insulating materials related to electricity
Caulk, mortar, or putty compounds
Wall construction materials, or wall coverings
Catalyst, more information not known
Detergents with a wide variety of applications; modifiers included when known
Drug product, or related to the manufacturing of drugs; modified by veterinary, animal, or pet if indicated by the source
Desiccators, siccatives, drying agents
Insulating materials to protect from noise, cold, etc (such as used in homes or buildings), insulating materials related to electricity
Includes antifoaming agents, coagulating agents, dispersion agents, emulsifiers, flotation agents, foaming agents, viscosity adjusters, etc
General flavouring agents used in foods, including condiments and seasonings
General fuels, fuel additives, motor/automotive fuels
Related to the activity of hunting
Impregnation materials and impregnation agents for various products (wood, oils, grease, paper)
Leather products, and products/chemicals used in the process of tanning and dressing leather
Related to the manufacturing of pulp or paper products, or paper products in general
Textiles used for clothing or furniture upholstery, processes related to textiles (e.g.
Industrial fluids such as hydraulic fluids, lubricating agents, functional fluids, etc
Related to electrical work (such as wiring of a building), electric current insulation materials, or other electrical components
Industry Uses
Adhesives and sealant chemicals
Paint additives and coating additives not described by other categories
Solvents (which become part of product formulation or mixture)
Surface active agents
Consumer Uses
Adhesives and sealants
Paints and coatings
Industry Processing Sectors for Manufacturing
Adhesive manufacturing
All other basic organic chemical manufacturing
Construction
Paint and coating manufacturing
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 blunt protective effects. In Europe and other developed countries it has been widely applied, and in China it is also successfully developed in the nineties and has been successful in the 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 wide temperature and pressure ranges, oximes has good oxygen-scavenging performance. The optimum temperature range is 138~336 ℃, and the 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, the 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
Colourless 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 in alkyd paint anti-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.
Preparation
With suitable precautions, to 1 litre of sodium hydroxylamine disulfonate solution from Preparation 2-1 (approx. 1.2 miles) is added 72 gm (1 mole) of methyl ethyl ketone. The mixture is warmed to 70°C. Then the reaction flask is wrapped with insulation and allowed to cool slowly for 12 hr.
After neutralization with 48% sodium hydroxide solution, the oxime is extracted from the reaction mixture with benzene. The benzene solution is distilled fractionally. The product distils between 152° and 154°C; yield, 65 gm (75%).
Production method
It is derived from Acetone and hydroxylamine hydrochloride. The reaction can also be made from butanone and hydroxylamine sulfate.
Methyl Ethyl Ketoxime is an organic substance that 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.
Methyl ethyl 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.
- Methyl Ethyl Ketoxime is a Urethane blocking agent for coating applications.
- Methyl Ethyl Ketoxime can be used as an Anti-skinning agent in paints (Alkyd based systems)
- Methyl Ethyl Ketoxime is an Oxygen scavenger in boiler water treatment.
- Methyl Ethyl Ketoxime can be used to produce oxime derivatives for other industrial applications
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 from forming in the paint can.
The Methyl Ethyl Ketoxime additive is added in very small proportions to the paint typically less than 0.5%.
Methyl Ethyl Ketoxime 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.
Methyl ethyl ketone oxime is the organic compound with the formula C2H5C(NOH)CH3. Methyl Ethyl Ketoxime is the oxime derivative of methyl ethyl ketone.
Application & Usage of Methyl Ethyl Ketoxime:
Methyl Ethyl Ketoxime, as it is called in the paint industry, is used to suppress the "skinning" of paints: the formation of a skin on the paint before it is used.
Methyl Ethyl Ketoxime Prevents skinning in alkyd-based systems.
Methyl Ethyl Ketoxime 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 methyl ethyl ketone oxime evaporates when the paint is applied thereby allowing the drying process to proceed.
In the paint industry, Methyl Ethyl Ketoxime is used to suppress the skinning of paints. The methyl ethyl ketone oxime is a popular anti-skinning agent, used to suppress the formation of 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 methyl ethyl ketone oxime (MEKO) is used as a skinning agent in paint, it reduces skinning of paint by binding the drying agents where metal salts 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 METHYL ETHYL KETOXIME IN WATER TREATMENT
Methyl ethyl ketoxime (MEKO) is well known as an oxygen scavenger and metal passivator in boilers.
For more than a decade, Methyl Ethyl Ketoxime 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, Methyl Ethyl Ketoxime 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 Methyl Ethyl Ketoxime does not adversely affect the cycle chemistry or the performance of ion exchange type condensate polishers.
Methyl Ethyl Ketoxime 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 areas:
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 a corrosion inhibitor in industrial boiler or water treatment system.
4. Methyl Ethyl Ketoxime can also be used as a 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 from 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.
Methyl Ethyl Ketoxime is produced to meet the low moisture and high assay standards that formulators require
Methylethyl ketone oxime is the organic compound with the formula C2H5C(NOH)CH3.
This colourless liquid is the oxime derivative of methyl ethyl ketone.
Methyl Ethyl Ketoxime, as it is called in the paint industry, is used to suppress the "skinning" of paints: the formation of a skin on the paint before it is used.
Methyl Ethyl Ketoxime functions by binding the drying agents, metal salts that catalyze the oxidative crosslinking of drying oils.
Once the paint is applied to a surface, Methyl Ethyl Ketoxime evaporates, thereby allowing the drying process to proceed. anti skinning 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.
Colourless 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 the 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 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.
Methyl Ethyl Ketoxime is produced to meet the low moisture and high assay standards that formulators require.
Methyl Ethyl Ketoxime 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 a better effect than Butyraldehyde oxime and cyclohexanone oxime. It can also be used for the 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 feedwater 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
Application Areas
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
Methyl Ethyl Ketoxime, as it is called in the paint industry, is used to suppress “skinning” of paints: the formation of a skin on the 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 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 the formation of solid skin during storage.
The loss 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 the filling of small containers. The minute dose of an effective anti-skinning agent can alleviate the difficulty of skinning.
Methyl Ethyl Ketoxime functions by binding the drying agents, metal salts that catalyze the oxidative crosslinking of drying oils.
Once the paint is applied to a surface, Methyl Ethyl Ketoxime evaporates, thereby allowing the drying process to proceed. Other anti skinning agents have been used, including phenol-based antioxidants, but these tend to yellow the paint.
BENEFITS OF Methyl ethyl ketoxime (MEKO):
• Efficient oxygen scavenging
• Passivation of steel surfaces in pre-boiler, boiler and condensate areas
• Equally effective in both vapour 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) invented bulk storage containers
When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide and nitrogen oxides.
