ChemicalBook--->CAS DataBase List--->78-93-3

78-93-3

78-93-3 Structure

78-93-3 Structure
IdentificationMore
[Name]

2-Butanone
[CAS]

78-93-3
[Synonyms]

2-BUTANONE
BUTANONE
BUTANONE, 2-
ETHYL METHYL KETONE
FEMA 2170
MEK
METHYL ETHYL KETONE
2-butanal
2-Butanon
2-butanone (MEK
2-butanone (MEK)
2-Butanone(MEK)
2-Ketobutane
2-Oxobutane
3-Butanone
Acetone, methyl-
Aethylmethylketon
ai3-07540(usda)
Butan-2-one
Butanon
[EINECS(EC#)]

201-159-0
[Molecular Formula]

C4H8O
[MDL Number]

MFCD00011648
[Molecular Weight]

72.11
[MOL File]

78-93-3.mol
Chemical PropertiesBack Directory
[Description]

2-Butanone is a stable, highly flammable chemical. It is incompatible with oxidising agents, bases, and strong reducing agents. It is a colourless liquid with a sharp, sweet odour. 2-Butanone is produced in large quantities. It 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 it dissolves many substances. It is also used in glues and as a cleaning agent.
[Appearance]

MEK is a clear, colorless liquid. Fragrant, mint-like, moderately sharp odor.
[Melting point ]

-87 °C (lit.)
[Boiling point ]

80 °C (lit.)
[density ]

0.806
[vapor density ]

2.49 (vs air)
[vapor pressure ]

71 mm Hg ( 20 °C)
[FEMA ]

2170
[refractive index ]

n20/D 1.379(lit.)
[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
[form ]

Solution
[pka]

14.7 (quoted, Riddick et al., 1986)
[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
[Stability:]

Stable. Highly flammable. Incompatible with oxidizing agents, bases, strong reducing agents. Protect from moisture.
[explosive limit]

1.8-11.5%(V)
[Odor Threshold]

0.44ppm
[Odor Type]

ethereal
[Water Solubility ]

290 g/L (20 ºC)
[JECFA Number]

278
[Merck ]

14,6072
[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)
[Dielectric constant]

18.5(20℃)
[Exposure limits]

TLV-TWA, PEL 590 mg/m3 (200 ppm) (ACGIH, OSHA); STEL 885 mg/m3 (300 ppm) (ACGIH); IDLH 3000 ppm (NIOSH).
[LogP]

0.3 at 40℃
[CAS DataBase Reference]

78-93-3(CAS DataBase Reference)
[NIST Chemistry Reference]

2-Butanone(78-93-3)
[EPA Substance Registry System]

78-93-3(EPA Substance)
Hazard InformationBack Directory
[Chemical Properties]

2-Butanone is a stable, highly flammable chemical. It is incompatible with oxidizing agents, bases, and strong reducing agents. It is a colorless liquid with a sharp, sweet odor. 2-Butanone is produced in large quantities. It is used as a solvent and nearly half of its use is in paints and other coatings because it quickly evaporates into the air and it dissolves many substances. It is also used in glues and as a cleaning agent.
[General Description]

A light-yellow colored liquid with a pleasant odor. Less dense than water. Flash point below 141°F. Contact may irritate or cause burns.
[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.
[Air & Water Reactions]

Highly flammable. Slightly soluble in water.
[Hazard]

Flammable, dangerous fire risk. Toxic by ingestion.
[Health Hazard]

May cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
[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.
[Potential Exposure]

MEK is used as a solvent in nitrocellulose coating and vinyl film manufacture; in smokeless powder manufacture; in cements and adhesives and in the dewaxing of lubricating oils. It is also an intermediate in drug manufacture
[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.
[First aid]

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.
[Shipping]

UN1193 Methyl ethyl ketone or Ethyl methyl ketone, Hazard Class: 3; Labels: 3-Flammable liquid.
[Incompatibilities]

May form explosive mixture with air. Violent reaction with strong oxidizers, amines, ammonia, inorganic acids; caustics, isocyanates, pyridines. Incompatible with potassium tert-butoxide, 2-propanol, chlorosulfonic acid; oleum. Attacks some plastics. Ketones are incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, nitrated amines, azo, diazo, azido compounds, carbamates, organic cyanates
[Waste Disposal]

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform to EPA regulations governing storage, transportation, treatment, and waste disposal. Incineration
[Physical properties]

2-Butanone 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). It is incompatible with oxidizing agents, bases, and strong reducing agents. It is a colorless liquid with a sharp, sweet odor. 2-Butanone is produced in large quantities. It is used as a solvent and nearly half of its use is in paints and other coatings because it quickly evaporates into the air and it dissolves many substances. It is also used in glues and as a cleaning agent.
[Occurrence]

Reported found as an impurity among products from the dry distillation of wood and in the oil (extracted with ether) of black tea; it is also present in coffee, cheese, bread, some citrus oils and some other natural products (grape, raspberry).
[Uses]

2-Butanone 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.
[Uses]

MEK is used as a solvent for various coating systems, for example, vinyl, adhesives, nitrocellulose, and acrylic coatings. It is used in paint removers, lacquers, varnishes, spray paints, sealers, glues, magnetic tapes, printing inks, resins, rosins, cleaning solutions, and for polymerization. It is found in other consumer products, for example, household and hobby cements, and wood-filling products. MEK 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. It is an extraction solvent in the processing of foodstuffs and food ingredients. MEK can also be used to sterilize surgical and dental equipment.
In addition to its manufacture, environmental sources of MEK include exhaust from jet and internal combustion engines, and industrial activities such as gasification of coal. It is found in substantial amounts in tobacco smoke. MEK is produced biologically and has been identified as a product of microbial metabolism. It has also been found in plants, insect pheromones, and animal tissues, and MEK is probably a minor product of normal mammalian metabolism. It is stable under ordinary conditions but can form peroxides on prolonged storage; these may be explosive.
[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. It 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.It is used in themanufacture of smokeless powder and colorless synthetic resins, as a solvent, and insurface coating. It is also used as a flavoringsubstance in food.
[Definition]

A colorless volatile liquid ketone. It is manufactured by the oxidation of butane and used as a solvent.
[Definition]

ChEBI: A dialkyl ketone that is a four-carbon ketone carrying a single keto- group at position C-2.
[Preparation]

By catalytic dehydrogenation of secondary butyl alcohol; by dehydration of butane-2,3-diol by refluxing with 25% aqueous H2SO4. Industrially, it 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.
[Production Methods]

Methyl ethyl ketone is commercially manufactured from nbutene in a metal-catalyzed hydrogenation reaction that proceeds through the intermediate formation of 2-butanol . A second method of synthesis involves the liquid- phase oxidation of n-butane with the formation of acetic acid as a coproduct.
[Taste threshold values]

Taste characteristics at 5 ppm: chemical-like and slightly fruity green.
[Flammability and Explosibility]

Methyl ethyl ketone is extremely flammable (NFPA rating = 3), and its vapor can travel a considerable distance to an ignition source and "flash back." MEK vapor forms explosive mixtures with air at concentrations of 1.9 to 11% (by volume). Carbon dioxide or dry chemical extinguishers should be used for MEK fires.
[Chemical Reactivity]

Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
[Pharmacology]

Anticonvulsant activity was demonstrated in rats given orally a dose of 805 mg MEK/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, MEK 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 MEK (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 MEK may help to explain the marked enhancement of neurotoxicity that is observed with combined MBK/MEK exposures (Hetland et al. 1976).
[Carcinogenicity]

Although MEK has not been specifically examined in a rodent 2-year bioassay, there is little to suggest that the material is carcinogenic. When used as a delivery vehicle in a dermal carcinogenicity bioassay for organic sulfur compounds, Horton et al. found that the application of benzyl disulfide or phenylbenzylthiophene in a 25–29% solution of MEK in dodecylbenzene together failed to increase the incidence of benign skin papillomas in male C3H/HeJmice. The mice used in the experiments were treated twice a week for 52 weeks with the MEKcontaining test solution.
[Source]

Improper disposal of cleaning fluids, adhesives, paints, and lacquers, and laboratory solvent. Leaches from PVC cement used to join tubing (Wang and Bricker, 1979). Also present in cigarette smoke (500 ppm) and exhaust from gasoline-powered engines (<0.1–2.6 ppm) (Verschueren, 1983).
Gas-phase tailpipe emission rates from California Phase II reformulated gasoline-powered automobiles with and without catalytic converters were 0.47 and 32 mg/km, respectively (Schauer et al., 2002).
Schauer et al. (2001) measured organic compound emission rates for volatile organic compounds, gas-phase semi-volatile organic compounds, and particle phase organic compounds from the residential (fireplace) combustion of pine, oak, and eucalyptus. The gas-phase emission rates of 2-butanone were 215 mg/kg of pine burned, 115 mg/kg of oak burned, and 77 mg/kg of eucalyptus burned.
[Environmental Fate]

Biological. Following a lag time of approximately 5 h, 2-butanone degraded in activated sludge (30 mg/L) at a rate constant ranging from 0.021 to 0.025/h (Urano and Kato, 1986).
Bridié et al. (1979) reported BOD and COD values of 2.03 and 2.31 g/g using filtered effluent from a biological sanitary waste treatment plant. These values were determined using a standard dilution method at 20 °C for a period of 5 d. The ThOD for 2-butanone is 2.44 g/g. Using the BOD technique to measure biodegradation, the mean 5-d BOD value (mM BOD/mM 2-butanone) and ThOD were 3.23 and 58.7%, respectively (Vaishnav et al., 1987).
Photolytic. Synthetic air containing gaseous nitrous acid and exposed to artificial sunlight (λ = 300–450 nm) photooxidized 2-butanone into peroxyacetyl nitrate and methyl nitrate (Cox et al., 1980). They reported a rate constant of 2.6 x 10-12 cm3/molecule?sec for the reaction of gaseous 2- butane with OH radicals based on a value of 8 x 10-12 cm3/molecule?sec for the reaction of ethylene with OH radicals.
The OH radical-initiated photooxidation of 2-butanone in a smog chamber produced peroxyacetyl nitrate and acetaldehyde (Cox et al., 1981). Reported rate constants for the reaction of 2-butanone with OH radicals in the atmosphere and in water are 1.15 x 10-13 and 1.50 x 10-13 cm3/molecule?sec, respectively (Wallington and Kurylo, 1987; Wallington et al., 1988a). The rate constant for the reaction of 2-butanone and OH radicals in the atmosphere at 300 K is 2.0 x 10-12 cm3/molecule?sec (Hendry and Kenley, 1979). Cox et al. (1981) reported a photooxidation half-life of 2.3 d for the reaction of 2-butanone and OH radicals in the atmosphere.
Chemical/Physical. 2-Butanone will not hydrolyze because it has no hydrolyzable functional group (Kollig, 1993).
Combustion in air will produce carbon monoxide (incomplete combustion), carbon dioxide, and water vapor.
At an influent concentration of 1.0 g/L, treatment with GAC resulted in an effluent concentration of 532 mg/L. The adsorbability of the carbon used was 94 mg/g carbon (Guisti et al., 1974).
[Toxicity evaluation]

There is very limited information on the mechanisms of toxicity of MEK. Relatively high-inhaled concentrations of 1475–29 500 mg m-3 (500–10 000 ppm) caused pulmonary vasoconstriction and hypertension in cats and dogs. There are several human case reports of neurological effects resulting from high exposure to MEK in combination with other solvents, and animal studies have confirmed synergism between MEK and ethyl n-butyl ketone, methyl n-butyl ketone, n-hexane, carbon tetrachloride, 2,5-hexanedione, and chloroform. The main target organs involved in toxicological interactions are the nervous system and liver, and the lung has also been mentioned.
Safety DataBack Directory
[Hazard Codes ]

F,Xi,T
[Risk Statements ]

R11:Highly Flammable.
R36:Irritating to the eyes.
R66:Repeated exposure may cause skin dryness or cracking.
R67:Vapors may cause drowsiness and dizziness.
R39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
[Safety Statements ]

S9:Keep container in a well-ventilated place .
S16:Keep away from sources of ignition-No smoking .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37:Wear suitable protective clothing and gloves .
[RIDADR ]

UN 1193 3/PG 2
[WGK Germany ]

1
[RTECS ]

EL6475000
[Autoignition Temperature]

516 °C
[TSCA ]

Yes
[HazardClass ]

3
[PackingGroup ]

II
[HS Code ]

29141200
[storage]

2-Butanone should be protected from moisture.
[Precautions]

2-Butanone vapor and air mixtures are explosive. It reacts violently with strong oxidants and inorganic acids causing fi re and explosion hazard.
[Safety Profile]

Moderately toxic by ingestion, skin contact, and intraperitoneal routes. Human systemic effects by inhalation: conjunctiva irritation and unspecified effects on the nose and respiratory system. An experimental teratogen. A strong irritant. Human eye irritation @ 350 ppm. Affects peripheral nervous system and central nervous system. Highly flammable liquid. Reaction with hydrogen peroxide + nitric acid forms a heatand shock-sensitive explosive product. Ignition on contact with potassium tert-butoxide. Mixture with 2- propanol will produce explosive peroxides during storage. Vigorous reaction with chloroform + alkali. Incompatible with chlorosulfonic acid, oleum. To fight fire, use alcohol foam, CO2, dry chemical. Used in production of drugs of abuse. When heated to decomposition it emits acrid smoke and fumes.
[Hazardous Substances Data]

78-93-3(Hazardous Substances Data)
[Toxicity]

LD50 orally in rats: 6.86 ml/kg (Smyth)
[IDLA]

3,000 ppm
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Methanol-->Hydrogen peroxide-->Zinc oxide-->Palladium chloride-->SULFATE STANDARD-->n-Butane-->Isobutylbenzene-->1-BUTENE-->2-Butanol-->Copper chromite-->CUPRIC CHLORIDE SOLUTION-->COPPER ALLOYS SET OF 5 DISCS (35 MM DIAM., 2 MM THICKNESS)-->ZINC-COPPER COUPLE-->Dehydrogenation catalyst
[Preparation Products]

2-PHENOXYACETAMIDINE HYDROCHLORIDE-->Alizapride-->3-Methylbenzofuran-2-carboxylic acid-->Benzofuran-2-carboxylic acid-->TERT-BUTYL 4-(AMINOMETHYL)PYRIDIN-2-YLCARBAMATE-->3-AMINO-5,6-DIMETHYL-3H-THIENO[2,3-D]PYRIMIDIN-4-ONE-->optical diskbase material modified PMMA copolymer-->2-Butanone peroxide-->1-(3-AMINO-BENZOFURAN-2-YL)-ETHANONE-->2-Benzofurancarboxylic acid ethyl ester-->5-METHOXYBENZOFURAN-2-BORONIC ACID-->(5,6-DIMETHYL-THIENO[2,3-D]PYRIMIDIN-4-YL)-HYDRAZINE-->2-IODO-ISONICOTINIC ACID-->(2-TERT-BUTOXYFORMAMIDO-PYRIDIN-4-YL)METHYL METHANESULFONATE-->3',4'-(DIOCTYLOXY)BENZALDEHYDE-->DL-Isoleucine-->Prothiofos-->Coumaphos-->SEC-BUTYLAMINE-->Industrial gear oil-->Saquinavir-->Dimethylglyoxime-->4-CHLORO-5,6-DIMETHYLTHIENO[2,3-D]PYRIMIDINE-->2,3-Pentanedione-->Industrial gear oil,weight load-->Xanthophyll-->5,6-DIMETHYLTHIENO[2,3-D]PYRIMIDIN-4(3H)-ONE-->TERT-BUTYL 4-(HYDROXYMETHYL)PYRIDIN-2-YLCARBAMATE-->ETHYL 2-AMINO-4,5-DIMETHYLTHIOPHENE-3-CARBOXYLATE-->ASTRAZON PINK FG-->Industrial gear oil,middle load-->2-(AMINOCARBONYL)NICOTINIC ACID-->2-AMINO-4,5-DIMETHYL-THIOPHENE-3-CARBONITRILE-->sec-Butylamine-->Mivacurium chloride-->Benomyl-->2,3-Butanedione monoxime-->Carboxymethoxylamine hemihydrochloride-->3-Methyl-1-pentyn-3-ol-->2,3-Dimethylindole
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

2-Butanone(78-93-3).msds
Spectrum DetailBack Directory
[Spectrum Detail]

2-Butanone(78-93-3)MS
2-Butanone(78-93-3)1HNMR
2-Butanone(78-93-3)13CNMR
2-Butanone(78-93-3)IR1
2-Butanone(78-93-3)IR2
2-Butanone(78-93-3)Raman
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

2-Butanone, for spectroscopy, 99+%(78-93-3)
[Alfa Aesar]

2-Butanone, HPLC Grade, 99.5+%(78-93-3)
[Sigma Aldrich]

78-93-3(sigmaaldrich)
78-93-3 suppliers list
Tags:78-93-3 Related Product Information
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