Quick Search
Butanone, also known as methyl ethyl ketone (MEK), is an organic compound with the formula CH3C(O)CH2CH3.
This colourless liquid methyl ethyl ketone has a sharp, sweet odor reminiscent of acetone.
Methyl ethyl ketone is produced industrially on a large scale, but occurs in nature only in trace amounts.
CAS: 78-93-3
MF: C4H8O
MW: 72.11
EINECS: 201-159-0
Methyl ethyl ketone is partially soluble in water, and is commonly used as an industrial solvent.
Methyl ethyl ketone is an isomer of another solvent, tetrahydrofuran.
Methyl ethyl ketone is a stable, highly flammable chemical.
Methyl ethyl ketone is incompatible with oxidising agents, bases, and strong reducing agents.
Methyl ethyl ketone is a colourless liquid with a sharp, sweet odour.
Methyl ethyl ketone is produced in large quantities.
Methyl ethyl ketone is used as a solvent and nearly half of its use is in paints and other coatings because it will quickly evaporate into the air and Methyl ethyl ketone dissolves many substances.
Methyl ethyl ketone is also used in glues and as a cleaning agent.
Methyl ethyl ketone (MEK) is a colourless liquid with a sweet and sharp odour.
Methyl ethyl ketone is soluble in alcohol, ether, acetone benzene, and water.
Methyl ethyl ketone is a solvent often found in mixtures with acetone, ethyl acetate, n-hexane, toluene, or alcohols.
Methyl ethyl ketone has applications in the surface coating industry and in the de-waxing of lubricating oils.
Methyl ethyl ketone is used in the manufacture of colourless synthetic resins, artificial leather, rubbers, lacquers, varnishes, and glues.
A Methyl ethyl ketone that is a four-carbon ketone carrying a single keto- group at position C2.
Reported found as an impurity among products from the dry distillation of wood and in the oil (extracted with ether) of black tea; Methyl ethyl ketone is also present in coffee, cheese, bread, some citrus oils and some other natural products (grape, raspberry).
A colorless volatile liquid ketone.
Methyl ethyl ketone is manufactured by the oxidation of butane and used as a solvent.
Methyl ethyl ketone is used as a solvent for lacquers, adhesives, cleaning materials to be electroplated, degreasing, rubber and rubber cement, printing inks, and paints, wood stains and varnishes, paint removers, in cleaning solutions, as a catalyst, and as a carrier.
Methyl ethyl ketone will exist as a gas if released to the atmosphere.
Methyl ethyl ketone dissolves when mixed with water.
In the air Methyl ethyl ketone quickly is reacted into other chemicals, in the water and soil bacteria break it down.
Methyl ethyl ketone has slight acute (short-term) toxicity on aquatic life.
IMethyl ethyl ketone has slight chronic (long-term) toxicity to aquatic life.
Chronic and acute effects on plants, birds or land animals have not been determined.
Methyl ethyl ketone is not expected to bioaccumulate.
Industrial emissions of methyl ethyl ketone can produce elevated, but still low level concentrations in the atmosphere around the source.
Because of its short life expectancy in the atmosphere methyl ethyl ketone is expected to be confined to the local area within which it is emitted.
Since Methyl ethyl ketone does not bind to soil well, methyl ethyl ketone that makes its way into the ground may move through the ground and enter groundwater (bore water).
Because methyl ethyl ketone is used in many consumer products, including tobacco smoke, short-term indoor concentrations may be elevated above the levels considered safe for workers.
Methyl ethyl ketone enters the air during production, use and transporting it.
In the air sunlight will break Methyl ethyl ketone down into other chemicals in a day or less.
It dissolves when mixed with water.
In water Methyl ethyl ketone will be broken down into other chemicals in about two weeks.
In the soil and water, bacteria will break Methyl ethyl ketone down.
Methyl ethyl ketone does not deposit on the bottom of rivers or lakes.
Methyl ethyl ketone (MEK) is an industrial hydrocarbon solvent used in the manufacture of many products, including pesticides and pharmaceuticals.
Methyl ethyl ketone is also used in cosmetics and as a flavouring agent.
There are no published data regarding exposure to Methyl ethyl ketone during human pregnancy.
As with all chemicals, unnecessary exposure to Methyl ethyl ketone should be avoided during pregnancy.
However, where occupational exposure is unavoidable, adequate health and safety precautions should be taken to ensure that exposure is well within the recommended exposure limits and does not lead to maternal symptoms of toxicity.
Methyl ethyl ketone Chemical Properties
Melting point: -87 °C (lit.)
Boiling point: 80 °C (lit.)
Density: 0.805 g/mL at 25 °C (lit.)
Vapor density: 2.49 (vs air)
Vapor pressure: 71 mm Hg ( 20 °C)
Refractive index: n20/D 1.379(lit.)
FEMA: 2170 | 2-BUTANONE
Fp: 26 °F
Storage temp.: 2-8°C
Solubility: Miscible with acetone, ethanol, benzene, ether (U.S. EPA, 1985), and many other solvents, particularly ketones and aldehydes
pka: 14.7 (quoted, Riddick et al., 1986)
Form: Solution
Color: Colorless
Odor: Sweet/sharp odor detectable at 2 to 85 ppm (mean = 16 ppm)
PH: pH(1+4, 25℃):6.0～7.0
Relative polarity: 0.327
Explosive limit: 1.8-11.5%(V)
Odor Threshold: 0.44ppm
Water Solubility: 290 g/L (20 ºC)
Merck: 14,6072
JECFA Number: 278
BRN: 741880
Henry's Law Constant: 23.0 at 50.00 °C, 34.1 at 60.00 °C, 50.6 at 70.00 °C, 70.4 at 80.00 °C (headspace-GC, Hovorka et al., 2002)
Exposure limits: TLV-TWA, PEL 590 mg/m3 (200 ppm) (ACGIH, OSHA); STEL 885 mg/m3 (300 ppm) (ACGIH); IDLH 3000 ppm (NIOSH).
Stability: Stable. Highly flammable.
Incompatible with oxidizing agents, bases, strong reducing agents.
Protect from moisture.
LogP: 0.3 at 40℃
CAS DataBase Reference: 78-93-3(CAS DataBase Reference)
NIST Chemistry Reference: Methyl ethyl ketone(78-93-3)
EPA Substance Registry System: Methyl ethyl ketone (78-93-3)
Methyl ethyl ketone (MEK) is a colorless liquid with an odor that has been described as moderately sharp, fragrant, peppermint, or acetone like.
Methyl ethyl ketone soluble in water up to 28% by weight and is miscible with many other organic solvents.
The lower explosive limit is 1.4% and the upper explosive limit is 11.4%.
Methyl ethyl ketone may be incompatible with strong oxidizers, amines, ammonia, inorganic acids, caustics, isocyanates, and pyridines.
When used industrially, methyl ethyl ketone must be handled with caution, as it is a Class lB flammable liquid NIOSH (2010).
Methyl ethyl ketone is a flammable liquid.
Methyl ethyl ketone is partially soluble in water, and soluble in most other organic solvents.
Methyl ethyl ketone will float on water while it rapidly dissolves in it.
Methyl ethyl ketone is a clear, colorless, volatile, very flammable liquid with a sweet, mint or acetone-like odor.
Odor threshold concentration is 10.0 ppmv (Leonardos et al., 1969).
Experimentally determined detection and recognition odor threshold concentrations were 5.8 mg/m3 (2.0 ppmv) and 16 mg/m3 (5.4 ppmv), respectively (Hellman and Small, 1974).
Methyl ethyl ketone is incompatible with oxidizing agents, bases, and strong reducing agents.
Methyl ethyl ketone is a colorless liquid with a sharp, sweet odor.
Methyl ethyl ketone is produced in large quantities.
Methyl ethyl ketone is used as a solvent and nearly half of its use is in paints and other coatings because Methyl ethyl ketone quickly evaporates into the air and it dissolves many substances.
Methyl ethyl ketone is also used in glues and as a cleaning agent.
Uses
Methyl ethyl ketone (2-butanone, ethyl methyl ketone, methyl acetone) is an organic solvent of relatively low toxicity, which is found in many applications.
Methyl ethyl ketone is used in industrial and commercial products as a solvent for adhesives, paints, and cleaning agents and as a de-waxing solvent.
A natural component of some foods, methyl ethyl ketone can be released into the environment by volcanoes and forest fires.
Methyl ethyl ketone is used in themanufacture of smokeless powder and colorless synthetic resins, as a solvent, and insurface coating.
Methyl ethyl ketone is also used as a flavoringsubstance in food.
Methyl ethyl ketone is used as a solvent for various coating systems, for example, vinyl, adhesives, nitrocellulose, and acrylic coatings.
Methyl ethyl ketone is used in paint removers, lacquers, varnishes, spray paints, sealers, glues, magnetic tapes, printing inks, resins, rosins, cleaning solutions, and for polymerization.
Methyl ethyl ketone is found in other consumer products, for example, household and hobby cements, and wood-filling products.
Methyl ethyl ketone is used in dewaxing lubricating oils, the degreasing of metals, in the production of synthetic leathers, transparent paper and aluminum foil, and as a chemical intermediate and catalyst.
Methyl ethyl ketone is an extraction solvent in the processing of foodstuffs and food ingredients.
Methyl ethyl ketone can also be used to sterilize surgical and dental equipment.
In addition to its manufacture, environmental sources of Methyl ethyl ketone include exhaust from jet and internal combustion engines, and industrial activities such as gasification of coal.
Methyl ethyl ketone is found in substantial amounts in tobacco smoke.
Methyl ethyl ketoneis produced biologically and has been identified as a product of microbial metabolism.
Methyl ethyl ketone has also been found in plants, insect pheromones, and animal tissues, and Methyl ethyl ketone is probably a minor product of normal mammalian metabolism.
Methyl ethyl ketone is stable under ordinary conditions but can form peroxides on prolonged storage; these may be explosive.
Methyl ethyl ketone is an eye irritant that has been used as a water soluble photoinitiator for the photopolymerization of methacrylic acid (MAA).
As solvent; in the surface coating industry; manufacture of smokeless powder; colorless synthetic resins.
Methyl ethyl ketone is an effective and common solvent and is used in processes involving gums, resins, cellulose acetate and nitrocellulose coatings and in vinyl films.
For this reason Methyl ethyl ketone finds use in the manufacture of plastics, textiles, in the production of paraffin wax, and in household products such as lacquer, varnishes, paint remover, a denaturing agent for denatured alcohol, glues, and as a cleaning agent.
Methyl ethyl ketone has similar solvent properties to acetone but boils at a higher temperature and has a significantly slower evaporation rate.
Unlike acetone, Methyl ethyl ketone forms an azeotrope with water, making it useful for azeotropic distillation of moisture in certain applications.
Methyl ethyl ketone is also used in dry erase markers as the solvent of the erasable dye.
As butanone dissolves polystyrene and many other plastics, Methyl ethyl ketone is sold as "model cement" for use in connecting parts of scale model kits.
Though often considered an adhesive, Methyl ethyl ketone is actually functioning as a welding agent in this context.
Preparation
By catalytic dehydrogenation of secondary butyl alcohol; by dehydration of butane-2,3-diol by refluxing with 25% aqueous H2SO4.
Industrially, Methyl ethyl ketone is also prepared by controlled oxidation of butane, by dry distillation of calcium acetate and calcium propionate, or by refluxing methyl acetoacetate and diluted H2SO4.
Reactivity Profile
Amines are chemical bases.
They neutralize acids to form salts plus water.
These acid-base reactions are exothermic.
The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base.
Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides.
Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat.
Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides.
They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.
Health Hazard
Occupational workers are exposed to 2-butanone by breathing contaminated air in workplaces associated with the production or use of paints, glues, coatings, or cleaning agents.
Prolonged exposures to 2-butanone cause symptoms of poisoning such as cough, dizziness, drowsiness, headache, nausea, vomiting, dermatitis, irritation of the nose, throat, skin, and eyes and at very high levels cause drooping eyelids, uncoordinated muscle movements, loss of consciousness, and birth defects.
Chronic inhalation studies in animals have reported slight neurological, liver, kidney, and respiratory effects.
However, information on the chronic (long-term) effects of 2-butanone (methyl ethyl ketone) in humans is limited.
The acute toxicity of methyl ethyl ketone is low.
Exposure to high concentrations can cause headache, dizziness, drowsiness, vomiting, and numbness of the extremities.
Irritation of the eyes, nose, and throat can also occur.
Methyl ethyl ketone is considered to have adequate warning properties.
Repeated or prolonged skin exposure to methyl ethyl ketone can cause defatting of the skin, leading to cracking, secondary infection, and dermatitis.
This compound has not been found to be carcinogenic or to show reproductive or developmental toxicity in humans.
Methyl ethyl ketone has exhibited developmental toxicity in some animal tests.
Fire Hazard
Flammable/combustible material. May be ignited by heat, sparks or flames.
Vapors may form explosive mixtures with air.
Vapors may travel to source of ignition and flash back.
Most vapors are heavier than air.
They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers.
Runoff to sewer may create fire or explosion hazard.
Containers may explode when heated.
Many liquids are lighter than water.
Pharmacology
Anticonvulsant activity was demonstrated in rats given orally a dose of 805 mg Methyl ethyl ketone/kg, which significantly delayed the onset of isonicotinic acid hydrazide-induced convulsions and provided 60% protection against electroshock convulsions, but failed to protect against metrazole convulsions (Kohli, Kishor, Dua & Saxena, 1967).
Golubev (1969) reported that 0.25 M-MEK caused contraction of the rabbit pupil, and MEK and other volatile substances isolated from human urine and injected iv into rabbits damaged cerebral and coronary arteries and caused increased capillary permeability, but did not alter the blood-sugar level (Mabuchi, 1969).
In dogs, Methyl ethyl ketone caused vomiting, muscular debility and the formation of large quantities of urinary magnesium ammonium phosphate crystals (Verstraete, van der Stock & Mattheeuws, 1964).
Combined ip administration of MBK and Methyl ethyl ketone (1:3) to guinea-pigs increased the urinary excretion of the MBK metabolites 2-hexanol and 2,5-hexanedione (Couri, Abdel-Rahman & Hetland, 1976).
If the neurotoxic action of MBK is mediated by a metabolite, stimulation of MBK metabolism by simultaneous exposure to Methyl ethyl ketone may help to explain the marked enhancement of neurotoxicity that is observed with combined MBK/MEK exposures (Hetland et al. 1976).
Production
Butanone may be produced by oxidation of 2-butanol.
The dehydrogenation of Methyl ethyl ketone is catalysed by copper, zinc, or bronze:
CH3CH(OH)CH2CH3 → CH3C(O)CH2CH3 + H2
Methyl ethyl ketone is used to produce approximately 700 million kilograms yearly.
Other syntheses that have been examined but not implemented include Wacker oxidation of 2-butene and oxidation of isobutylbenzene, which is analogous to the industrial production of acetone.
The cumene process can be modified to produce phenol and a mixture of acetone and butanone instead of only phenol and acetone in the original.
Both liquid-phase oxidation of heavy naphtha and the Fischer–Tropsch reaction produce mixed oxygenate streams, from which Methyl ethyl ketone is extracted by fractionation.
Synonyms
2-Butanone
METHYL ETHYL KETONE
Butan-2-one
Butanone
78-93-3
Ethyl methyl ketone
Methylethyl ketone
Meetco
Methyl acetone
Methylethylketone
3-Butanone
Ethylmethylketon
ethylmethylketone
Aethylmethylketon
Butanone 2
Acetone, methyl-
MEK
Ethyl methyl cetone
Ketone, ethyl methyl
Metiletilchetone
Metyloetyloketon
2-butanon
ethylmethyl ketone
RCRA waste number U159
FEMA No. 2170
Oxobutane
Methylethylketon
methyl ethylketone
MFCD00011648
6PT9KLV9IO
2-Butanone, HPLC Grade
C2H5COCH3
CHEBI:28398
Metyl ethyl ketone
Caswell No. 569
Butanone 2 [French]
methylacetone
Metiletilcetona
Ethylmethylketon [Dutch]
Ethylmethylcetone
Metiletilcetona [Spanish]
Metyloetyloketon [Polish]
Aethylmethylketon [German]
Ethylmethylcetone [French]
Metiletilchetone [Italian]
2-Butanone, ACS reagent, >=99.0%
methyl-ethyl ketone
HSDB 99
Ethyl methyl cetone [French]
methyl(ethyl) ketone
CCRIS 2051
AI3-07540 (USDA)
EINECS 201-159-0
UNII-6PT9KLV9IO
UN1193
RCRA waste no. U159
EPA Pesticide Chemical Code 044103
n-butanone
AI3-07540
2-butanal
2-Oxobutane
ethyl methylketone
ethylmathyl ketone
methyl-ethylketone
methylethyl-ketone
butane-2-one
2 -butanone
2- butanone
butan-3-one
methyl etyl ketone
ethyl-methyl ketone
methyl ethyl cetone
methyl-ethyl-ketone
ethyl(methyl) ketone
Ketone, methyl ethyl
2-Butanone, ACS grade
DSSTox_CID_1516
MEK [INCI]
2-BUTANONE [FCC]
EC 201-159-0
2-BUTANONE [FHFI]
DSSTox_RID_76193
DSSTox_GSID_21516
ghl.PD_Mitscher_leg0.417
ASTM-D740
CHEMBL15849
2-Butanone, analytical standard
2-Butanone, LR, >=99%
DTXSID3021516
Methyl Ethyl Ketone - Mil Spec
METHYL ETHYL KETONE [II]
METHYL ETHYL KETONE [MI]
Methyl ethyl ketone, ACS reagent
ZINC901514
METHYL ETHYL KETONE [HSDB]
2-Butanone, AR, >=99.5%
METHYL ETHYL KETONE [VANDF]
2-Butanone, technical grade, 99%
METHYL ETHYL KETONE [MART.]
Tox21_200041
LMFA12000043
STL146562
2-Butanone, natural, >=99%, FG
METHYL ETHYL KETONE [USP-RS]
AKOS000118991
2-Butanone, for HPLC, >=99.7%
Methyl Ethyl Ketone Reagent Grade ACS
UN 1193
2-Butanone, puriss., >=99% (GC)
2-Butanone, ReagentPlus(R), >=99%
CAS-78-93-3
2-Butanone, >=99.5%, FCC, FG
NCGC00090973-01
NCGC00090973-02
NCGC00257595-01
BP-30009
2-Butanone 100 microg/mL in Acetonitrile
Ethyl methyl ketone or methyl ethyl ketone
2-Butanone, SAJ first grade, >=99.0%
2-Butanone, JIS special grade, >=99.0%
E0140
FT-0628728
C02845
2-Butanone, HPLC grade, for HPLC, >=99.5%
A839534
Q372291
2-Butanone, puriss., ACS reagent, reag. Ph. Eur., 99.5%
2-Butanone, 5000 mug/mL in methanol: water (9:1), analytical standard
2-Butanone, puriss. p.a., ACS reagent, reag. Ph. Eur., >=99.5% (GC)
Ethyl methyl ketone or methyl ethyl ketone [UN1193] [Flammable liquid]
Methyl ethyl ketone, United States Pharmacopeia (USP) Reference Standard
Methyl Ethyl Ketone, Pharmaceutical Secondary Standard; Certified Reference Material
