2-Butanone CAS 78-93-3
Introduction：Basic information about 2-Butanone CAS 78-93-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
2-Butanone Basic information
| Product Name: | 2-Butanone |
| Synonyms: | 2-Butanone,99%;2-Butanone,97%;MEK = 2-BUTANONE;METHYL ETHYL KETONE (MEK)(BUTANONE);2-Butanone, extra pure, 99+%;2-Butanone, for spectroscopy, 99+%;2-Butanone, residue free, for electronic use, 99+%;METHYL ETHYL KETONE DISTILLED IN GLASS |
| CAS: | 78-93-3 |
| MF: | C4H8O |
| MW: | 72.11 |
| EINECS: | 201-159-0 |
| Product Categories: | Catalyst, Miscellaneous Reagents;Analytical Reagents;Analytical/Chromatography;CHROMASOLV for HPLC;Chromatography Reagents &HPLC &HPLC Grade Solvents (CHROMASOLV);HPLC/UHPLC Solvents (CHROMASOLV);UHPLC Solvents (CHROMASOLV);A-B;Analytical Reagents for General Use;Multi-Compendial;Puriss p.a.;Puriss p.a. ACS;Organics;Analytical Chemistry;Solvents for HPLC & Spectrophotometry;Solvents for Spectrophotometry;ACS and Reagent Grade Solvents;ACS Grade;ACS Grade Solvents;Amber Glass Bottles;Carbon Steel Flex-Spout Cans;Semi-Bulk Solvents;Solvent Bottles;Solvent by Application;Solvent Packaging Options;Solvents;fine chemicals |
| Mol File: | 78-93-3.mol |
2-Butanone 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 | n |
| 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 |
| Relative polarity | 0.327 |
| PH | pH(1+4, 25℃):6.0～7.0 |
| Odor | Sweet/sharp odor detectable at 2 to 85 ppm (mean = 16 ppm) |
| Odor Threshold | 0.44ppm |
| Odor Type | ethereal |
| explosive limit | 1.8-11.5%(V) |
| 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 etal., 2002) |
| Exposure limits | TLV-TWA, PEL 590 mg/m3 (200 ppm)(ACGIH, OSHA); STEL 885 mg/m3(300 ppm) (ACGIH); IDLH 3000 ppm(NIOSH). |
| Dielectric constant | 18.5（20℃） |
| Stability: | Stable. Highly flammable. Incompatible with oxidizing agents, bases, strong reducing agents. Protect from moisture. |
| Cosmetics Ingredients Functions | PERFUMING SOLVENT |
| InChI | 1S/C4H8O/c1-3-4(2)5/h3H2,1-2H3 |
| InChIKey | ZWEHNKRNPOVVGH-UHFFFAOYSA-N |
| SMILES | CC(CC)=O |
| LogP | 0.3 at 40℃ |
| Surface tension | 23.69mN/m at 298.15K |
| CAS DataBase Reference | 78-93-3(CAS DataBase Reference) |
| NIST Chemistry Reference | 2-Butanone(78-93-3) |
| EPA Substance Registry System | Methyl ethyl ketone (78-93-3) |
| ECETOC JACC REPORT | 2-Butanone (78-93-3) |
Safety Information
| Hazard Codes | F,Xi,T |
| Risk Statements | 11-36-66-67-39/23/24/25-23/24/25 |
| Safety Statements | 9-16-45-36/37 |
| RIDADR | UN 1193 3/PG 2 |
| OEB | A |
| OEL | TWA: 200 ppm (590 mg/m3), STEL: 300 ppm (885 mg/m3) |
| WGK Germany | 1 |
| RTECS | EL6475000 |
| Autoignition Temperature | 516 °C |
| TSCA | TSCA listed |
| HazardClass | 3 |
| PackingGroup | II |
| HS Code | 29141200 |
| Storage Class | 3 - Flammable liquids |
| Hazard Classifications | Eye Irrit. 2 Flam. Liq. 2 STOT SE 3 |
| Hazardous Substances Data | 78-93-3(Hazardous Substances Data) |
| Toxicity | LD50 orally in rats: 6.86 ml/kg (Smyth) |
| IDLA | 3,000 ppm |
| 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 useis in paints and other coatings because it will quickly evaporate into the air and it dissolvesmany substances. It is also used in glues and as a cleaning agent. |
| Chemical Properties | Methyl ethyl ketone (MEK) is a colorless liquid with an odor that has been described as moderately sharp, fragrant, peppermint, or acetone like. It 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). |
| 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 withether) of black tea; it is also present in coffee, cheese, bread, some citrus oils and some other natural products (grape, raspberry). |
| 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. |
| Uses | MEK is used as a solvent for various coating systems, forexample, 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 otherconsumer products, for example, household and hobbycements, and wood-filling products. MEK is used in dewaxinglubricating oils, the degreasing of metals, in the production ofsynthetic leathers, transparent paper and aluminum foil, and asa chemical intermediate and catalyst. It is an extraction solventin the processing of foodstuffs and food ingredients. MEK canalso be used to sterilize surgical and dental equipment. In addition to its manufacture, environmental sources ofMEK include exhaust from jet and internal combustionengines, and industrial activities such as gasification of coal. Itis found in substantial amounts in tobacco smoke. MEK isproduced biologically and has been identified as a product ofmicrobial metabolism. It has also been found in plants, insectpheromones, and animal tissues, and MEK is probably a minorproduct of normal mammalian metabolism. It is stable underordinary conditions but can form peroxides on prolongedstorage; these may be explosive. |
| 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. |
| Definition | ChEBI: A dialkyl ketone that is a four-carbon ketone carrying a single keto- group at position C-2. |
| Production Methods | Methyl ethyl ketone is commercially manufactured from nbutenein a metal-catalyzed hydrogenation reaction thatproceeds through the intermediate formation of 2-butanol. A second method of synthesis involves the liquid-phase oxidation of n-butane with the formation of aceticacid as a coproduct. |
| Definition | A colorlessvolatile liquid ketone. It is manufacturedby the oxidation of butane and used as asolvent. |
| Preparation | By catalytic dehydrogenation of secondary butyl alcohol; by dehydration of butane-2,3-diol by refluxing with 25% aqueousH2SO4. Industrially, it is also prepared by controlled oxidation of butane, by dry distillation of calcium acetate and calciumpropionate, or by refluxing methyl acetoacetate and diluted H2SO4. |
| Taste threshold values | Taste characteristics at 5 ppm: chemical-like and slightly fruity green. |
| General Description | Methyl ethyl ketone (MEK) is a colourless liquid with a sweet and sharp odour. It is soluble in alcohol, ether, acetone benzene, and water. It is a solvent often found in mixtures with acetone, ethyl acetate, n-hexane, toluene, or alcohols. It has applications in the surface coating industry and in the de-waxing of lubricating oils. MEK is used in the manufacture of colourless synthetic resins, artificial leather, rubbers, lacquers, varnishes, and glues. |
| Air & Water Reactions | Highly flammable. Slightly soluble in water. |
| 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. |
| Hazard | Flammable, dangerous fire risk. Toxic byingestion. |
| 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. |
| Health Hazard | The acute toxicity of methyl ethyl ketone is low. Exposure to high concentrationscan cause headache, dizziness, drowsiness, vomiting, and numbness of theextremities. Irritation of the eyes, nose, and throat can also occur. Methyl ethylketone is considered to have adequate warning properties. Repeated or prolonged skin exposure to methyl ethyl ketone can cause defatting ofthe skin, leading to cracking, secondary infection, and dermatitis. This compoundhas not been found to be carcinogenic or to show reproductive or developmentaltoxicity in humans. Methyl ethyl ketone has exhibited developmental toxicity insome 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. |
| Flammability and Explosibility | Methyl ethyl ketone is extremely flammable (NFPA rating = 3), and its vapor cantravel a considerable distance to an ignition source and "flash back." MEK vaporforms 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). |
| 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. |
| Potential Exposure | MEK is used as a solvent in nitrocellulose coating and vinyl film manufacture; in smokelesspowder manufacture; in cements and adhesives and in thedewaxing of lubricating oils. It is also an intermediate indrug manufacture |
| First aid | If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seekmedical attention immediately. If this chemical contactsthe skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove fromexposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing hasstopped and CPR if heart action has stopped. Transferpromptly to a medical facility. When this chemical hasbeen swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. |
| Carcinogenicity | Although MEK has not been specificallyexamined in a rodent 2-year bioassay, there is little tosuggest that the material is carcinogenic. When used as adelivery vehicle in a dermal carcinogenicity bioassay fororganic sulfur compounds, Horton et al. found that theapplication of benzyl disulfide or phenylbenzylthiophenein a 25–29% solution of MEK in dodecylbenzene togetherfailed to increase the incidence of benign skin papillomas inmale C3H/HeJmice. The mice used in the experimentswere treated twice a week for 52 weeks with the MEKcontainingtest solution. |
| Source | Improper disposal of cleaning fluids, adhesives, paints, and lacquers, and laboratorysolvent. Leaches from PVC cement used to join tubing (Wang and Bricker, 1979). Also present incigarette 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-poweredautomobiles with and without catalytic converters were 0.47 and 32 mg/km, respectively (Schaueret al., 2002). Schauer et al. (2001) measured organic compound emission rates for volatile organiccompounds, gas-phase semi-volatile organic compounds, and particle phase organic compoundsfrom the residential (fireplace) combustion of pine, oak, and eucalyptus. The gas-phase emissionrates of 2-butanone were 215 mg/kg of pine burned, 115 mg/kg of oak burned, and 77 mg/kg ofeucalyptus 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 effluentfrom a biological sanitary waste treatment plant. These values were determined using a standarddilution method at 20 °C for a period of 5 d. The ThOD for 2-butanone is 2.44 g/g. Using the BODtechnique to measure biodegradation, the mean 5-d BOD value (mM BOD/mM 2-butanone) andThOD 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 ofethylene with OH radicals. The OH radical-initiated photooxidation of 2-butanone in a smog chamber producedperoxyacetyl nitrate and acetaldehyde (Cox et al., 1981). Reported rate constants for the reactionof 2-butanone with OH radicals in the atmosphere and in water are 1.15 x 10-13 and 1.50 x 10-13cm3/molecule?sec, respectively (Wallington and Kurylo, 1987; Wallington et al., 1988a). The rateconstant for the reaction of 2-butanone and OH radicals in the atmosphere at 300 K is 2.0 x 10-12cm3/molecule?sec (Hendry and Kenley, 1979). Cox et al. (1981) reported a photooxidation half-lifeof 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 functionalgroup (Kollig, 1993). Combustion in air will produce carbon monoxide (incomplete combustion), carbon dioxide, andwater vapor. At an influent concentration of 1.0 g/L, treatment with GAC resulted in an effluentconcentration of 532 mg/L. The adsorbability of the carbon used was 94 mg/g carbon (Guisti etal., 1974). |
| storage | 2-Butanone should be protected from moisture. |
| Shipping | UN1193 Methyl ethyl ketone or Ethyl methylketone, Hazard Class: 3; Labels: 3-Flammable liquid. |
| Toxicity evaluation | There is very limited information on the mechanisms oftoxicity of MEK. Relatively high-inhaled concentrations of1475–29 500 mg m-3 (500–10 000 ppm) caused pulmonaryvasoconstriction and hypertension in cats and dogs. There areseveral human case reports of neurological effects resultingfrom high exposure to MEK in combination with othersolvents, and animal studies have confirmed synergismbetween 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 interactionsare the nervous system and liver, and the lung has alsobeen mentioned. |
| 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. Ketonesare incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keepaway from alkaline materials, strong bases, strong acids,oxoacids, epoxides, nitrated amines, azo, diazo, azido compounds, carbamates, organic cyanates |
| Toxics Screening Level | The current ITSL for Methyl Ethyl Ketone (also known as 2-butanone or MEK) is 5000 μg/m3, with 24 hr averaging time (AT). |
| Waste Disposal | Consult with environmentalregulatory agencies for guidance on acceptable disposalpractices. Generators of waste containing this contaminant(≥100 kg/mo) must conform to EPA regulations governingstorage, transportation, treatment, and waste disposal.Incineration |
| Precautions | 2-Butanone vapor and air mixtures are explosive. It reacts violently with strong oxidants and inorganic acids causing fi re and explosion hazard. |
2-Butanone Preparation Products And Raw materials
| 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 |
