PRODUCTS

METHYL ETHYL KETONE

Methyl ethyl ketone, also known as methyl ethyl ketone (MEK),[a] is an organic compound with the formula CH3C(O)CH2CH3. This colourless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts.[7] It is partially soluble in water, and is commonly used as an industrial solvent.[8] It is an isomer of another solvent, tetrahydrofuran.

CAS No.: 78-93-3
EC No.: 201-159-0

Synonyms:
METHYL ETHYL KETONE; methyl ethyl ketone; METİL ETİL KETON; metil etil keton; 2-Butanone; Ethyl methyl ketone[2]; Ethylmethylketone; Methyl ethyl ketone (MEK; deprecated[2]); Methylpropanone; Methylacetone; 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-; METHYL ETHYL KETONE; methyl ethyl ketone; METİL ETİL KETON; metil etil keton; METHYL ETHYL KETONE; methyl ethyl ketone; METİL ETİL KETON; metil etil keton; Ethyl methyl cetone; MEK; Ketone, ethyl methyl; Metiletilchetone; Metyloetyloketon; ethylmethyl ketone; Metyl ethyl ketone; RCRA waste number U159; Caswell No. 569; Butanone 2 [French]; Butanon; Oxobutane; Methylethylketon; Ethylmethylketon [Dutch]; Metiletilcetona [Spanish]; METHYL ETHYL KETONE; methyl ethyl ketone; METİL ETİL KETON; metil etil keton; METHYL ETHYL KETONE; methyl ethyl ketone; METİL ETİL KETON; metil etil keton; Metyloetyloketon [Polish]; UNII-6PT9KLV9IO; 2-butanon; Aethylmethylketon [German]; Ethylmethylcetone [French]; Metiletilchetone [Italian]; methyl ethylketone; methyl-ethyl ketone; Ethyl methyl cetone [French]; HSDB 99; FEMA No. 2170; CCRIS 2051; AI3-07540 (USDA); METHYL ETHYL KETONE; methyl ethyl ketone; METİL ETİL KETON; metil etil keton; METHYL ETHYL KETONE; methyl ethyl ketone; METİL ETİL KETON; metil etil keton; EINECS 201-159-0; UN1193; 6PT9KLV9IO; C2H5COCH3; RCRA waste no. U159; EPA Pesticide Chemical Code 044103; AI3-07540; CHEBI:28398; MFCD00011648; 2-Butanone, ACS reagent; methylacetone; Metiletilcetona; 2-Butanone, 99+%, extra pure; 2-Butanone, 99.7%, for HPLC; Ethylmethylcetone; METHYL ETHYL KETONE; methyl ethyl ketone; METİL ETİL KETON; metil etil keton; METHYL ETHYL KETONE; methyl ethyl ketone; METİL ETİL KETON; metil etil keton; 2-Butanone, 99+%, for spectroscopy; 2-Butanone, ACS reagent, >=99.0%; methyl(ethyl) ketone; 2-Butanone, 99.5%, Extra Dry, AcroSeal(R); 2-Butanone, 99+%, for electronic use (MOS), residue free; n-butanone; 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; METHYL ETHYL KETONE; methyl ethyl ketone; METİL ETİL KETON; metil etil keton; METHYL ETHYL KETONE; methyl ethyl ketone; METİL ETİL KETON; metil etil keton; 2-Butanone, ACS grade; 2-Butanone, HPLC Grade; DSSTox_CID_1516; EC 201-159-0; DSSTox_RID_76193; DSSTox_GSID_21516; ghl.PD_Mitscher_leg0.417; ASTM-D740; KSC377S9D; C[CH]C(C)=O; CHEMBL15849; [C]C(=O)CC; 2-Butanone, analytical standard; 2-Butanone, LR, >=99%; DTXSID3021516; CTK2H7991; Methyl Ethyl Ketone - Mil Spec; Methyl ethyl ketone, ACS reagent; METHYL ETHYL KETONE; methyl ethyl ketone; METİL ETİL KETON; metil etil keton; METHYL ETHYL KETONE; methyl ethyl ketone; METİL ETİL KETON; metil etil keton; C(C(=O)C)[C]; ZINC901514; 2-Butanone, AR, >=99.5%; 2-Butanone, technical grade, 99%; Tox21_200041; BBL011450; LMFA12000043; STL146562; 2-Butanone, natural, >=99%, FG; AKOS000118991; 2-Butanone, for HPLC, >=99.7%; LS-1761; MCULE-8276670748; Methyl Ethyl Ketone Reagent Grade ACS; UN 1193; 2-Butanone, puriss., >=99% (GC); 2-Butanone, ReagentPlus(R), >=99%; CAS-78-93-3; KS-000011C7; 2-Butanone, >=99.5%, FCC, FG; METHYL ETHYL KETONE; methyl ethyl ketone; METİL ETİL KETON; metil etil keton; METHYL ETHYL KETONE; methyl ethyl ketone; METİL ETİL KETON; metil etil keton; 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; 5793-EP2270114A1; 5793-EP2280005A1; METHYL ETHYL KETONE; methyl ethyl ketone; METİL ETİL KETON; metil etil keton; 5793-EP2281817A1; 5793-EP2289879A1; 5793-EP2289884A1; 5793-EP2289897A1; 5793-EP2292601A1; 5793-EP2292602A1; 5793-EP2293650A1; METHYL ETHYL KETONE; methyl ethyl ketone; METİL ETİL KETON; metil etil keton; 5793-EP2298739A1; 5793-EP2298746A1; 5793-EP2298771A2; 5793-EP2298772A1; 5793-EP2301922A1; 5793-EP2305658A1; 5793-EP2305667A2; METHYL ETHYL KETONE; methyl ethyl ketone; METİL ETİL KETON; metil etil keton; 5793-EP2308839A1; METHYL ETHYL KETONE; methyl ethyl ketone; METİL ETİL KETON; metil etil keton; 5793-EP2371805A1; C02845; 15136-EP2270004A1; 15136-EP2270114A1; 2-Butanone, HPLC grade, for HPLC, >=99.5%; A839534; Q372291; METHYL ETHYL KETONE; methyl ethyl ketone; METİL ETİL KETON; metil etil keton; 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; methyl ethyl ketone; METİL ETİL KETON; metil etil keton; METHYL ETHYL KETONE; methyl ethyl ketone; METİL ETİL KETON; metil etil keton; Ethyl methyl ketone or methyl ethyl ketone [UN1193] [Flammable liquid]; Methyl ethyl ketone, United States Pharmacopeia (USP) Reference Standard; METHYL ETHYL KETONE; methyl ethyl ketone; METİL ETİL KETON; metil etil keton; 2-Butanone solution, certified reference material, 2000 mug/mL in methanol: water (9:1); Methyl Ethyl Ketone, Pharmaceutical Secondary Standard; Certified Reference Material; METHYL ETHYL KETONE; methyl ethyl ketone; METİL ETİL KETON; metil etil keton

METHYL ETHYL KETONE

Methyl ethyl ketone
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MEK[1]
Skeletal formula of Methyl ethyl ketone
Ball-and-stick model of Methyl ethyl ketone
Space-filling model of Methyl ethyl ketone
methyl ethyl ketone
Names
Preferred IUPAC name
Butan-2-one[2]
Other names
2-Methyl ethyl ketone
Ethyl methyl ketone[2]
Ethylmethylketone
Methyl ethyl ketone (MEK; deprecated[2])
Methylpropanone
Methylacetone
Identifiers
CAS Number
78-93-3 check
3D model (JSmol)
Interactive image
Interactive image
Beilstein Reference   741880
ChEBI
CHEBI:28398 check
ChEMBL
ChEMBL15849 check
ChemSpider
6321 check
ECHA InfoCard   100.001.054 Edit this at Wikidata
Gmelin Reference   25656
KEGG
C02845 check
PubChem CID
6569
RTECS number
EL6475000
UNII
6PT9KLV9IO check
CompTox Dashboard (EPA)
DTXSID3021516 Edit this at Wikidata
InChI[show]
SMILES[show]
Properties
Chemical formula   C4H8O
Molar mass   72.107 g·mol−1
Appearance   Colorless liquid
Odor   Mint or acetone-like[3]
Density   0.8050 g/mL
Melting point   −86 °C (−123 °F; 187 K)
Boiling point   79.64 °C (175.35 °F; 352.79 K)
Solubility in water   27.5 g/100 mL
log P   0.37[4]
Vapor pressure   78 mmHg (20 °C)[3]
Acidity (pKa)   14.7
Magnetic susceptibility (χ)   −45.58·10−6 cm3/mol
Refractive index (nD)   1.37880
Viscosity   0.43 cP
Structure
Dipole moment   2.76 D
Hazards
Safety data sheet   See: data page
Safety Data Sheet
GHS pictograms   GHS02: FlammableGHS07: Harmful[5]
GHS Signal word   Danger[5]
GHS hazard statements   H225, H319, H336[5]
GHS precautionary statements   P233, P210, P280, P240, P241, P243, P242, P264, P261, P271, P370+378, P303+361+353, P305+351+338, P337+313, P304+340, P312, P403+235, P501, P403+233, P405[5]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
310
Flash point   −9 °C (16 °F; 264 K)
Autoignition
temperature   505 °C (941 °F; 778 K)
Explosive limits   1.4–11.4%[3]
Lethal dose or concentration (LD, LC):
LD50 (median dose)
2737 mg/kg (oral, rat)
4050 mg/kg (oral, mouse)[6]
LC50 (median concentration)
12667 ppm (mammal)
13333 ppm (mouse, 2 hr)
7833 ppm (rat, 8 hr)[6]
NIOSH (US health exposure limits):
PEL (Permissible)   TWA 200 ppm (590 mg/m3)[3]
REL (Recommended)   TWA 200 ppm (590 mg/m3) ST 300 ppm (885 mg/m3)[3]
IDLH (Immediate danger)   3000 ppm[3]
Related compounds
Related ketones   Acetone; 3-pentanone; 3-methylMethyl ethyl ketone
Supplementary data page
Structure and
properties   Refractive index (n),
Dielectric constant (εr), etc.
Thermodynamic
data   Phase behaviour
solid–liquid–gas
Spectral data   UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Methyl ethyl ketone, also known as methyl ethyl ketone (MEK),[a] is an organic compound with the formula CH3C(O)CH2CH3. This colourless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts.[7] It is partially soluble in water, and is commonly used as an industrial solvent.[8] It is an isomer of another solvent, tetrahydrofuran.

Contents
1   Production
2   Applications
2.1   As a solvent
2.2   As a plastic welding agent
2.3   Other uses
3   Safety
3.1   Flammability
3.2   Health effects
3.3   Regulation
4   See also
5   Notes
6   References
7   External links
Production
Methyl ethyl ketone may be produced by oxidation of 2-butanol. The dehydrogenation of 2-butanol using a catalyst is catalyzed by copper, zinc, or bronze:

CH3CH(OH)CH2CH3 → CH3C(O)CH2CH3 + H2
This 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.[7] The cumene process can be modified to produce phenol and a mixture of acetone and Methyl ethyl ketone instead of only phenol and acetone in the original.[9]

Both liquid-phase oxidation of heavy naphtha and the Fischer-Tropsch reaction produce mixed oxygenate streams, from which 2-Methyl ethyl ketone is extracted by fractionation.[10]

Applications
As a solvent
Methyl ethyl ketone is an effective and common solvent[8] and is used in processes involving gums, resins, cellulose acetate and nitrocellulose coatings and in vinyl films.[11] For this reason it 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. It has similar solvent properties to acetone but boils at a higher temperature and has a significantly slower evaporation rate.[12] Unlike acetone, it forms an azeotrope with water,[13][14] 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 a plastic welding agent
As Methyl ethyl ketone dissolves polystyrene and many other plastics, it is sold as "model cement" for use in connecting parts of scale model kits. Though often considered an adhesive, it is actually functioning as a welding agent in this context.

Other uses
Methyl ethyl ketone is the precursor to methyl ethyl ketone peroxide, which is a catalyst for some polymerization reactions such as crosslinking of unsaturated polyester resins. Dimethylglyoxime can be prepared from Methyl ethyl ketone first by reaction with ethyl nitrite to give diacetyl monoxime followed by conversion to the dioxime:[15]

Preparation of dimethylglyoxime.png
In the Peroxide process on producing hydrazine, the starting chemical ammonia is bonded to Methyl ethyl ketone, oxidized by hydrogen peroxide, bonded to another ammonia molecule.

Pechiney-Ugine-Kuhlmann process.png
In the final step of the process, a hydrolysis produces the desired product hydrazine and regenerates the Methyl ethyl ketone.

Me(Et)C=NN=C(Et)Me + 2 H2O → 2 Me(Et)C=O + N2H4
Safety
Flammability
Methyl ethyl ketone can react with most oxidizing materials, and can produce fires.[8] It is moderately explosive, requiring only a small flame or spark to cause a vigorous reaction.[8] Methyl ethyl ketone fires should be extinguished with carbon dioxide, dry agents, or alcohol-resistant foam.[8] Concentrations in the air high enough to be flammable are intolerable to humans due to the irritating nature of the vapor.[12]

Health effects
Methyl ethyl ketone is a constituent of tobacco smoke.[16] It is an irritant, causing irritation to the eyes and nose of humans.[12] Serious health effects in animals have been seen only at very high levels. These included skeletal birth defects and low birth weight in mice, when they inhaled it at the highest dose tested (3000 ppm for 7 hours/day).[17] There are no long-term studies with animals breathing or drinking it,[18] and no studies for carcinogenicity in animals breathing or drinking it.[19]:96 There is some evidence that Methyl ethyl ketone can potentiate the toxicity of other solvents, in contrast to the calculation of mixed solvent exposures by simple addition of exposures.[20]

As of 2010, some reviewers advised caution in using Methyl ethyl ketone because of reports of neuropsychological effects.[21]

Methyl ethyl ketone is listed as a Table II precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances.[22]

Regulation
Emission of Methyl ethyl ketone was regulated in the US as a hazardous air pollutant, because it is a volatile organic compound contributing to the formation of tropospheric (ground-level) ozone. In 2005, the US Environmental Protection Agency removed Methyl ethyl ketone from the list of hazardous air pollutants (HAPs).[23][24][25]

Methyl Ethyl Ketone (MEK)
Physical characteristic: Colorless Liquid
Chemical formula: C4H8O
Molecular weight: 72,11 g/mol
Type of packaging: Barrel / IBC / Tank
MEK is an active & organic solvent. It is in a clear, inflammable and liquid form. It is in the ketone groups. It has a high evaporation rate. It is one of the most widely used ketones in the industry.
Areas of usage:
It is used in organic synthesis reactions.
It is used in the sectors of paint, coating and detergent.

Methyl Ethyl Ketone is a liquid solvent used in surface coatings, adhesives, printing inks, chemical intermediates, magnetic tapes and lube oil dewaxing agents. Methyl Ethyl Ketone also is used as an extraction medium for fats, oils, waxes and resins. It is a highly efficient and versatile solvent for surface coatings. Because of its effectiveness as a solvent, Methyl Ethyl Ketone is especially valuable in formulating high solids coatings, which help to reduce emissions from coating operations. Methyl Ethyl Ketone is a natural component of many foods, including apple juice, beans, chicken, honey and a variety of cheeses. Synonyms for Methyl Ethyl Ketone are 2-butanone, ethyl methyl ketone, and methyl acetone.

Methyl Ethyl Ketone is a Food and Drug Administration (FDA)-approved indirect food additive for adhesives and polymers. The panel, with the U.S. EPA as the sponsoring organization, prepared the technical support documents for Methyl Ethyl Ketone under the International Council of Chemical Associations (ICCA) Voluntary High Production Volume (HPV) chemical review.

Methyl Ethyl Ketone Hazardous Air Pollutant Delisting

On December 19, 2005, EPA issued a final rule removing Methyl Ethyl Ketone from Section 112 (b) (1) of the Clean Air Act. Petitions to remove a substance from the HAP list are authorized under Section 112 (b) (3). EPA determined that ambient concentrations, bioaccumulation, or deposition of Methyl Ethyl Ketone may not reasonably be anticipated to cause adverse human health or environmental effects.

The panel's delisting petition presented extensive information on Methyl Ethyl Ketone's potential health and environmental effects, environmental releases, and resulting ambient air concentrations. Hazard information included in the petition illustrated Methyl Ethyl Ketone’s low acute and chronic toxicity and low environmental toxicity. Air dispersion modeling results showed that ambient concentrations of Methyl Ethyl Ketone, even at the highest fenceline levels are below levels of concern.

Methyl Ethyl Ketone EPCRA Section 313 Delisting

On June 30, 2005, EPA deleted Methyl Ethyl Ketone from its list of chemicals subject to reporting under Section 313 of the Emergency Planning and Community Right-to Know Act’s Toxic Release Inventory (TRI) and Section 6607 of the Pollution Prevention Act of 1990. Facilities are no longer required to report releases of and other waste management information on Methyl Ethyl Ketone. EPA’s final delisting rule is the result of a decision by the Court of Appeals of the District of Columbia Circuit, on an appeal filed by the panel, to overturn the District Court and direct EPA to delist Methyl Ethyl Ketone from the TRI.

Methyl Ethyl Ketone VCCEP Independent Review

On February 19, 2004, the panel participated in an independent review, coordinated by Toxicology Excellence for Risk Assessment (TERA), of Methyl Ethyl Ketone under EPA’s Voluntary Children’s Chemical Evaluation Program (VCCEP). The purpose of the review was to determine whether existing data are adequate to characterize the risks of Methyl Ethyl Ketone to children, and if not, to identify data needs. The panel’s submission to TERA included a quantitative risk characterization demonstrating that normally anticipated children’s exposures to Methyl Ethyl Ketone pose negligible adverse health risks and that no further data are needed to adequately characterize risk to children under the VCCEP program.