Quick Search
Butanone oxime (MEKO) is obtained by the reaction of butanone and hydroxylamine hydrochloride.
Butanone oxime (MEKO) can also be synthesized by the reaction between butanone and hydroxylamine sulfate.
Butanone oxime (MEKO), also known as methyl ethyl ketoxime, is an organic compound with the chemical formula C₄H₉NO.
CAS Number: 96-29-7
Molecular Formula: C4H9NO
Molecular Weight: 87.12
EINECS Number: 406-930-7
Synonyms: 2-Butanone oxime, 2-Butanone, oxime, 2-butanona, oxima, 4-01-00-03250 (Beilstein Handbook Reference), 96-29-7, BRN 1698241, Butanone oxime, Butanone oxime; (Ethyl methyl ketoxime), C4-H9-N-O, C4H9NO, CCRIS 1382, EC 202-496-6, EINECS 202-496-6, Ethyl methyl ketone oxime, Ethyl methyl ketoxime, Ethyl-methylketonoxim, Ethyl-methylketonoxim [Czech], HSDB 8043, MEK-oxime, MEKO, Methyl ethyl ketone oxime, Methyl ethyl ketoxime, NA1993, NSC 442, Skino #2, Troykyd anti-skin B, UN1993, UNII-51YGE935U9, USAF AM-3, USAF EK-906, (2E)-2-Butanone oxime;2-Butoxime;Aron M 1;Butan-2-one, oxime;butan-2-oneoxime;Butanoxime;ethylmethylcetoxime;Ethyl-methylketonoxim
Butanone oxime (MEKO) is derived from butanone (methyl ethyl ketone, MEK) by replacing one of the carbonyl oxygen atoms with an oxime (-C=NOH) functional group.
Butanone oxime (MEKO) is sensitive to heat.
Has exploded at least twice when heated in the presence of acidic impurities.
Mixtures with strong acids may explode. Reacts with sulfuric acid to form an explosive product .
Butanone oxime (MEKO) is the organic compound with the formula C2H5C(NOH)CH3.
This colourless liquid is the oxime derivative of methyl ethyl ketone.
Butanone 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.
It is particularly used in alkyd paints. Butanone oxime (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, Butanone oxime (MEKO) evaporates, thereby allowing the drying process to proceed. Other antiskinning agents have been used, including phenolic antioxidants (E.G butylated hydroxytoluene), but these tend to yellow the paint.
This oxime is also used in some types of RTV silicones.
Butanone oxime (MEKO) synonymous with 2-Butanone Oxime, is a clear, colorless liquid that is 99.5% pure.
It is primarily used as an anti-skinning agent in paint.
Butanone oxime (MEKO) has additional uses in the production of silicone adhesive products.
Butanone oxime (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).
Butanone oxime (MEKO) is a high production volume (HPV) chemical produced at over one million pounds annually.
AdvanSix has established a provisional occupational exposure limit of 3 ppm (10 mg/m3) for an 8-hour timeweighted average and a short-term exposure limit of 10 ppm for use in worksite safety programs.
Butanone oxime (MEKO) is a clear, colorless, combustible liquid.
Butanone oxime (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.
Butanone oxime (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.
Butanone oxime (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. Please see the Safety Data Sheet (SDS) for additional information.
MEKO is rapidly metabolized and eliminated from the body. MEKO does not cause harmful effects on reproduction or development.
Male rodents developed liver tumors when repeatedly exposed during their lifetime to high concentrations of Butanone oxime (MEKO).
These tumors developed late in life and did not affect survival.
Butanone oxime (MEKO) is not genotoxic, pointing to a threshold mechanism for cancer development (i.e., a “safe level” below which cancer will not occur: a level well above typical exposures).
Therefore, the human risk of cancer is low.
Butanone oxime (MEKO) has low toxicity to aquatic organisms, upon either single or repeated exposure.
Butanone oxime (MEKO) has minimal potential to accumulate in the bodies of humans or animals.
Butanone oxime (MEKO) is readily biodegradable and will not persist in the environment.
Butanone oxime (MEKO) can cause irritation to the skin, eyes, and respiratory system. Prolonged exposure may affect the liver and kidneys.
It is regulated in many regions due to its classification as a suspected carcinogen.
Use in well-ventilated areas with protective equipment, including gloves and eye protection.
Butanone oxime (MEKO) is primarily used in alkyd resin-based paints as an anti-skinning agent.
Butanone oxime (MEKO) prevents the surface of the paint from forming a hard, undesirable film during storage by reacting with oxygen.
After application, it evaporates, ensuring proper curing and film formation.
Acts as a blocking agent for isocyanates.
This blocking prevents premature reactions and allows controlled curing at elevated temperatures, leading to better final properties of polyurethane materials.
Helps stabilize formulations and improve shelf life.
Butanone oxime (MEKO) is used to synthesize other oxime compounds in the pharmaceutical, agricultural, and specialty chemical industries.
Common in manufacturing settings for paints, coatings, and adhesives.
Butanone oxime (MEKO)indirect exposure through residual amounts in painted surfaces or cured materials.
Melting point: -30 °C
Boiling point: 59-60 °C15 mm Hg(lit.)
Density: 0.924 g/mL at 25 °C(lit.)
vapor density: 3 (vs air)
vapor pressure: <8 mm Hg ( 20 °C)
refractive index: n20/D 1.442(lit.)
Flash point: 140 °F
solubility: water: soluble100g/L at 25°C
form: Liquid
pka: pK1:12.45 (25°C)
color: Clear colorless to pale yellow
Water Solubility: 114 g/L (20 ºC)
BRN: 1698241
Dielectric constant: 3.4（20℃）
Stability: Stable. Combustible. Incompatible with strong oxidizing agents. May react with strong acids to form an explosive material.
InChIKey: WHIVNJATOVLWBW-SNAWJCMRSA-N
LogP: 0.63 at 25℃
Butanone oxime (MEKO) knows as a novel oxygen scavenger is disclosed in the U.S. and patented by Drew Chemical Company in 1984.
Butanone oxime (MEKO) 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.
Oxygen scavenging performance: oxime compound is an organic compound with an oxime group.
Butanone oxime (MEKO)s are currently used for boiler shutdown protection and oxygen mainly acetaldehyde oxime, dimethyl ketone oxime (acetone oxime) and methyl ethyl ketone oxime.
Butanone oxime (MEKO)s 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.
Butanone oxime (MEKO) 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.
Volatile: the volatile degree of oxime compounds is higher than that of hydrazine, DEHA, morpholine, cyclohexylamine, etc.
Butanone oxime (MEKO) 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.
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.
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.
Butanone oxime (MEKO) 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.
A screening assessment on butanone oxime was published in 2010 as part of Batch 7 of the Challenge under the Chemicals Management Plan.
In that screening assessment, butanone oxime was identified as a potential concern to human health based on a comparison of levels to which Canadians may be exposed to butanone oxime and levels associated with health effects.
The primary identified exposure to butanone oxime was from the inhalation of indoor air during and immediately following the application of interior alkyd paints and coating products available to consumers, while important identified health effects in animal studies included potential carcinogenicity, adverse effects on organs, and adverse effects on nose tissue.
Can cause irritation to the respiratory tract.
High exposure levels may lead to dizziness or headaches.
Butanone oxime (MEKO) prolonged exposure may result in irritation or dermatitis.
Butanone oxime (MEKO) can cause irritation or redness.
Potential carcinogen based on animal studies. Chronic exposure may damage the liver or kidneys.
Butanone oxime (MEKO) has moderate volatility and solubility, meaning it can evaporate into the air or dissolve in water, potentially impacting the environment.
Butanone oxime (MEKO) is considered toxic to aquatic life.
Proper disposal is necessary to prevent contamination.
Occupational exposure limits (OELs) are established in some jurisdictions to minimize risks.
Uses:
Butanone oxime (MEKO) is mainly used as anti-skinning agent and silicon curing agent for alkyd resin coatings.
Butanone oxime (MEKO) is used as an antioxidant to prevent skin formation, which is better than butyraldehyde oxime and cyclohexanone oxime.
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.
Butanone oxime (MEKO) was employed as reagent and solvent in the syntheses of ketoimine and 2,4-dipyridyl-1,3,5-triazapentadiene palladium(II) complexes.
Butanone oxime (MEKO) was also used in the synthesis of novel acetaldiimine cobalt complex, [CoI2{((CH3CH2)(CH3)C=NO)2C(CH3)2}].
Butanone oxime (MEKO) is used primarily as an antiskinning agent in alkyd coating resins.
Butanone oxime (MEKO) is used in the following products: coating products.
Butanone oxime (MEKO) is used in the following areas: building & construction work.
Butanone oxime (MEKO) is used for the manufacture of: wood and wood products, pulp, paper and paper products, plastic products, fabricated metal products, electrical, electronic and optical equipment, machinery and vehicles and furniture.
Other release to the environment of Butanone oxime (MEKO) is likely to occur from: indoor use as processing aid and outdoor use as processing aid.
Butanone oxime (MEKO) is used in the following products: coating products and polymers.
Release to the environment of Butanone oxime (MEKO) can occur from industrial use: formulation of mixtures.
Butanone oxime (MEKO) is used in the following products: coating products.
Butanone oxime (MEKO) has an industrial use resulting in manufacture of another substance (use of intermediates).
Butanone oxime (MEKO) is used in the following areas: formulation of mixtures and/or re-packaging.
Butanone oxime (MEKO) is used for the manufacture of: chemicals.
Release to the environment of Butanone oxime (MEKO) can occur from industrial use: in processing aids at industrial sites, as an intermediate step in further manufacturing of another substance (use of intermediates), as processing aid, manufacturing of the substance and formulation of mixtures.
Widely used in alkyd paints to prevent the formation of skin on the paint surface during storage.
Butanone oxime (MEKO) is used in polyurethane production to block isocyanates, which helps in controlled polymer reactions.
A precursor for producing other chemical compounds in the pharmaceutical, agrochemical, and coatings industries.
Butanone oxime (MEKO) is widely used as an anti-skinning agent in alkyd resin-based paints and coatings.
When paints are stored in sealed containers, exposure to oxygen can cause a hardened film (or "skin") to form on the surface, which can make the paint unusable or difficult to apply.
Butanone oxime (MEKO) reacts with oxygen in the paint, effectively preventing this skin formation and ensuring that the paint remains in a usable condition for longer periods.
In the production of polyurethane materials, Butanone oxime (MEKO) acts as a blocking agent for isocyanates.
Isocyanates are highly reactive chemicals that need to be controlled to prevent premature reactions during the manufacturing process.
Butanone oxime (MEKO) temporarily "blocks" the isocyanates, ensuring they only react under specific conditions, such as elevated temperatures during curing.
This control improves the quality and consistency of the final polyurethane products, which are used in foams, adhesives, and coatings.
Butanone oxime (MEKO) is used to stabilize adhesive and sealant formulations, particularly in solvent-based systems.
Its inclusion helps to prevent unwanted chemical reactions during storage, extending the shelf life of these products.
Additionally, Butanone oxime (MEKO) ensures that the adhesives retain their bonding properties and do not degrade before application.
Butanone oxime (MEKO) is used as a precursor in the synthesis of various oxime compounds.
These oximes find applications in the pharmaceutical industry for drug production, in the agricultural sector for making pesticides and herbicides, and in specialty chemicals for niche industrial applications.
Similar to its role in paints, Butanone oxime (MEKO) prevents the formation of an unwanted skin or film on printing inks, particularly those used in high-speed printing presses.
This ensures consistent ink flow and prevents clogs or interruptions during the printing process.
Butanone oxime (MEKO) is sometimes included in anti-corrosion formulations, where it helps stabilize the chemical composition of the coatings and enhances their durability by preventing unwanted reactions that could compromise performance.
Butanone oxime (MEKO) is occasionally used in laboratories as a reagent or chemical stabilizer in experimental setups that involve reactive substances.
Butanone oxime (MEKO)s ability to temporarily block or stabilize reactive groups makes it a versatile tool in research and development.
Butanone oxime (MEKO) serves as an anti-skinning agent in solvent-based paints, varnishes, and lacquers.
When paint is exposed to air during storage, oxidation can occur, forming an undesirable, hardened "skin" on the surface.
Butanone oxime (MEKO) prevents this by reacting with oxygen, delaying or stopping the oxidative polymerization process.
Butanone oxime (MEKO) ensures that the paint remains smooth, easy to stir, and ready for application, even after prolonged storage, reducing waste and improving product quality.
In marine and industrial coatings, Butanone oxime (MEKO) helps maintain uniformity in highly durable and protective coatings used on ships, pipelines, and industrial machinery, where consistent film formation is critical.
In the manufacturing of polyurethane products, Butanone oxime (MEKO) is a critical blocking agent for isocyanates.
Isocyanates are key components in polyurethane, but their high reactivity makes them prone to unwanted premature reactions during processing.
Butanone oxime (MEKO) temporarily "blocks" the reactive sites of isocyanates, rendering them inactive until the curing stage when heat is applied.
This allows manufacturers to produce stable, storable prepolymers that can be activated later during the final production of foams, elastomers, coatings, or adhesives.
Butanone oxime (MEKO)’s blocking ability enables more precise control over the curing process, resulting in high-performance materials with tailored properties for automotive, aerospace, and construction applications.
Butanone oxime (MEKO) plays a role in stabilizing solvent-based adhesives and sealants:
It prevents the adhesives from curing prematurely, extending their shelf life and ensuring they retain their intended bonding properties.
Butanone oxime (MEKO) is especially important in applications requiring precision bonding for construction, woodworking, or electronics, where improper curing could lead to material failure.
Butanone oxime (MEKO) serves as a precursor for synthesizing various oxime compounds:
Butanone oxime (MEKO) is used to produce intermediates for drugs and therapeutic agents.
Certain oxime derivatives are known for their roles in antibiotics, antiviral agents, and enzyme inhibitors.
Butanone oxime (MEKO) is used to create pesticide and herbicide intermediates, contributing to the development of compounds that protect crops from pests and improve agricultural yield.
Butanone oxime (MEKO) is an important component in developing custom-made chemical compounds for niche industrial purposes, including complex polymers and catalysts.
In printing inks, Butanone oxime (MEKO) acts as an anti-skinning agent, similar to its role in paints:
It ensures that the inks remain free-flowing and do not form a dried layer, particularly during high-speed printing operations.
This is crucial for industries like packaging, publishing, and textiles, where uninterrupted printing and consistent ink quality are essential.
Butanone oxime (MEKO) stabilizes the chemical composition of the coating, preventing reactions that could degrade its effectiveness.
These coatings are often used in environments exposed to harsh conditions, such as bridges, industrial plants, and offshore structures, where MEKO helps enhance durability and longevity.
Butanone oxime (MEKO) is used in wood finishing products such as stains, varnishes, and protective coatings:
It ensures even curing and prevents skin formation, resulting in a smooth, polished finish on wooden furniture and surfaces.
This makes it highly valued in high-quality woodworking and furniture manufacturing.
In laboratories, Butanone oxime (MEKO) is used as a reagent or stabilizer for studying reaction mechanisms and stabilizing reactive compounds:
It plays a role in experimental research, especially in organic chemistry, where oxime compounds are studied for their reactivity and potential applications.
It is used in paints and coatings specifically designed for vehicle exteriors, ensuring smooth application and protection against wear and environmental damage.
Butanone oxime (MEKO) is also utilized in the production of polyurethane foams used in car interiors, helping manufacturers achieve desired properties such as flexibility, strength, and thermal resistance.
Butanone oxime (MEKO) is used in high-performance materials required for aerospace and defense industries:
Its ability to block isocyanates is crucial in creating polyurethane-based coatings and composites that withstand extreme temperatures, high stress, and corrosive environments.
Residual amounts may be present in paints, varnishes, and adhesives used in homes or businesses, though regulations often limit its concentration due to toxicity concerns.
Butanone oxime (MEKO)s role in maintaining product stability ensures a longer shelf life for many consumer-grade materials.
Safety Profile:
Butanone oxime (MEKO) is classified as a suspected carcinogen, based on animal studies that showed an increased risk of liver tumors in long-term exposure scenarios.
While the direct risk to humans remains under investigation, many regulatory agencies advise caution in handling and prolonged exposure.
Repeated or prolonged exposure to MEKO, especially via inhalation, has been shown to cause liver and kidney damage in animal studies.
These effects are believed to result from the compound's metabolism and its impact on cellular processes in these organs.
Butanone oxime (MEKO) has the potential to cause skin sensitization, meaning repeated contact can lead to an allergic reaction, characterized by itching, redness, and swelling, even at lower concentrations over time.
Poison by intraperitoneal route.
Moderately toxic by subcutaneous route.
May explode if heated. Reacts with sulfuric acid to form an explosive product.
When heated to decomposition it emits toxic fumes of NOX.
Inhaling Butanone oxime (MEKO) vapors can irritate the respiratory tract, leading to symptoms such as coughing, shortness of breath, dizziness, or headaches.
Prolonged exposure to high concentrations may result in more severe respiratory discomfort and, in some cases, nausea or drowsiness.
Direct contact with Butanone oxime (MEKO) can cause irritation, leading to redness, itching, or dryness of the skin.
Prolonged or repeated exposure may result in dermatitis, which is characterized by inflammation and cracking of the skin.
Butanone oxime (MEKO) is an irritant to the eyes, and splashes can cause redness, watering, and discomfort.
Prolonged exposure or large quantities may lead to more severe irritation, potentially requiring medical attention.
Accidental ingestion of Butanone oxime (MEKO) can cause gastrointestinal discomfort, such as nausea, vomiting, or abdominal pain.
Although rare, ingestion of larger amounts may affect internal organs and require emergency medical care.
