PRODUCTS

METHYL ETHYL KETONE

Synonyms:METHYL ETHYL KETONE; METİL ETİL KETON; Ethyl Méthyl Cétone; Butanone ; 78-93-3; Methylethyl ketone; Meetco; Methyl acetone; Methylethylketone; 3-Methyl ethyl ketone; MEK; 2-butanon; Aethylmethylketon

Methyl ethyl ketone is a manufactured chemical but it is also present in the environment from natural sources. It is a colorless liquid with a sharp, sweet odor.

CAS No: 78-93-3
EINECS No: 201-159-0

Synonyms:
METHYL ETHYL KETONE ; METHYL ETHYL KETON; METHYL ETHYL KETHONE; METHYL ETHYL KETHON; Butanone ; Metil etil keton; Methil etil keton; 2-Methyl ethyl ketone; METHYL ETHYL KETONE; Butanone; Butan-2-one; Methyl ethyl ketone; Ethyl ethyl ketone; 78-93-3; Methylethyl ketone; Meetco; Methyl acetone; Methylethylketone; 3-Methyl ethyl ketone; Ethylmethylketon; ethylmethylketone; Aethylmethylketon; Methyl ethyl ketone 2; Acetone, methyl-; Ethyl methyl cetone; MEK; Ketone, ethyl methyl; Metiletilchetone; Metyloetyloketon; ethylmethyl ketone; Metyl ethyl ketone; RCRA waste number U159; Caswell No. 569; Methyl ethyl ketone 2 [French]; Butanon; Oxobutane; Methylethylketon; Ethylmethylketon [Dutch]; Metiletilcetona [Spanish]; Metyloetyloketon [Polish]; UNII-6PT9KLV9IO; 2-butanon; Aethylmethylketon [German]; Ethylmethylcetone [French]; Metiletilchetone [Italian]; methyl ethylketone; METHYL ETHYL KETONE ; METHYL ETHYL KETON; METHYL ETHYL KETHONE; METHYL ETHYL KETHON; Butanone ; Metil etil keton; Methil etil keton; 2-Methyl ethyl ketone; METHYL ETHYL KETONE; Butanone; Butan-2-one; Methyl ethyl ketone; Ethyl ethyl ketone; 78-93-3; Methylethyl ketone; Meetco; Methyl acetone; Methylethylketone; 3-Methyl ethyl ketone; Ethylmethylketon; ethylmethylketone; Aethylmethylketon; Methyl ethyl ketone 2; Acetone, methyl-; Ethyl methyl cetone; MEK; Ketone, ethyl methyl; Metiletilchetone; Metyloetyloketon; ethylmethyl ketone; Metyl ethyl ketone; RCRA waste number U159; Caswell No. 569; Methyl ethyl ketone 2 [French]; Butanon; Oxobutane; Methylethylketon; Ethylmethylketon [Dutch]; Metiletilcetona [Spanish]; Metyloetyloketon [Polish]; UNII-6PT9KLV9IO; 2-butanon; Aethylmethylketon [German]; Ethylmethylcetone [French]; Metiletilchetone [Italian]; methyl ethylketone; methyl-ethyl ketone; Ethyl methyl cetone [French]; METHYL ETHYL KETONE ; METHYL ETHYL KETON; METHYL ETHYL KETHONE; METHYL ETHYL KETHON; BUTANONE ; METİL ETİL KETON; METHİL ETİL KETON; 2-METHYL ETHYL KETONE; METHYL ETHYL KETONE; BUTANONE; BUTAN-2-ONE; METHYL ETHYL KETONE; ETHYL ETHYL KETONE; 78-93-3; METHYLETHYL KETONE; MEETCO; METHYL ACETONE; METHYLETHYLKETONE; 3-METHYL ETHYL KETONE; ETHYLMETHYLKETON; ETHYLMETHYLKETONE; AETHYLMETHYLKETON; METHYL ETHYL KETONE 2; ACETONE, METHYL-; ETHYL METHYL CETONE; MEK; KETONE, ETHYL METHYL; METİLETİLCHETONE; METYLOETYLOKETON; ETHYLMETHYL KETONE; METYL ETHYL KETONE; RCRA WASTE NUMBER U159; CASWELL NO. 569; METHYL ETHYL KETONE 2 [FRENCH]; BUTANON; OXOBUTANE; METHYLETHYLKETON; ETHYLMETHYLKETON [DUTCH]; METİLETİLCETONA [SPANİSH]; METYLOETYLOKETON [POLİSH]; UNII-6PT9KLV9IO; 2-BUTANON; AETHYLMETHYLKETON [GERMAN]; ETHYLMETHYLCETONE [FRENCH]; METİLETİLCHETONE [ITALİAN]; METHYL ETHYLKETONE; METHYL-ETHYL KETONE; ETHYL METHYL CETONE [FRENCH]; METHYL ETHYL KETONE ; METHYL ETHYL KETON; METHYL ETHYL KETHONE; METHYL ETHYL KETHON; Butanone ; Metil etil keton; Methil etil keton; 2-Methyl ethyl ketone; METHYL ETHYL KETONE; butanone; butan-2-one; methyl ethyl ketone; ethyl ethyl ketone; 78-93-3; methylethyl ketone; meetco; methyl acetone; methylethylketone; 3-methyl ethyl ketone; ethylmethylketon; ethylmethylketone; aethylmethylketon; methyl ethyl ketone 2; acetone, methyl-; ethyl methyl cetone; mek; ketone, ethyl methyl; metiletilchetone; metyloetyloketon; ethylmethyl ketone; metyl ethyl ketone; rcra waste number u159; caswell no. 569; methyl ethyl ketone 2 [french]; butanon; oxobutane; methylethylketon; ethylmethylketon [dutch]; metiletilcetona [spanish]; metyloetyloketon [polish]; unıı-6pt9klv9ıo; 2-butanon; aethylmethylketon [german]; ethylmethylcetone [french]; Metiletilchetone [Italian]; methyl ethylketone; methyl-ethyl ketone; Ethyl methyl cetone [French]; methyl-ethyl ketone; Ethyl methyl cetone [French]; METHYL ETHYL KETONE ; METHYL ETHYL KETON; METHYL ETHYL KETHONE; METHYL ETHYL KETHON; Butanone ; Metil etil keton; Methil etil keton; 2-Methyl ethyl ketone; METHYL ETHYL KETONE; Butanone; Butan-2-one; Methyl ethyl ketone; Ethyl ethyl ketone; ethyl methyl; metiletilchetone ;METİL ETİL KETON

METHYL ETHYL KETONE

Computed Properties   HelpNew Window
Property Name   Property Value   Reference
Molecular Weight of Methyl ethyl ketone:    72.11 g/mol   Computed by PubChem 2.1 (PubChem release 2019.06.18)
XLogP3   0.3   Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Hydrogen Bond Donor Count of Methyl ethyl ketone:   0   Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Hydrogen Bond Acceptor Count of Methyl ethyl ketone:1   Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Rotatable Bond Count of Methyl ethyl ketone:   1   Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Exact Mass   72.057515 g/mol   Computed by PubChem 2.1 (PubChem release 2019.06.18)
Monoisotopic Mass of Methyl ethyl ketone:   72.057515 g/mol   Computed by PubChem 2.1 (PubChem release 2019.06.18)
Topological Polar Surface Area of Methyl ethyl ketone:   17.1 Å²   Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Heavy Atom Count of Methyl ethyl ketone:   5   Computed by PubChem
Formal Charge of Methyl ethyl ketone:   0   Computed by PubChem
Complexity of Methyl ethyl ketone:   38.9   Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Isotope Atom Count of Methyl ethyl ketone:   0   Computed by PubChem
Defined Atom Stereocenter Count of Methyl ethyl ketone:   0   Computed by PubChem
Undefined Atom Stereocenter Count of Methyl ethyl ketone:   0   Computed by PubChem
Defined Bond Stereocenter Count of Methyl ethyl ketone:   0   Computed by PubChem
Undefined Bond Stereocenter Count of Methyl ethyl ketone:   0   Computed by PubChem
Covalently-Bonded Unit Count of Methyl ethyl ketone:   1   Computed by PubChem
Compound Is Canonicalized of Methyl ethyl ketone:   Yes

Methyl ethyl ketone appears as colorless fairly volatile liquid with a pleasant pungent odor. Flash point 20°F. Vapors heavier than air. Does not react with water or many common materials. Stable in normal transportation. Irritates the nose, eyes, and throat. Combustion may produce toxic materials. Density 6.7 lb / gal. Used as a solvent, for making other chemicals, and for production of wax from petroleum.

CAMEO Chemicals
2-Methyl ethyl ketone is a manufactured chemical but it is also present in the environment from natural sources. It is a colorless liquid with a sharp, sweet odor. It is also known as methyl ethyl ketone (MEK). 2-Methyl ethyl ketone is produced in large quantities. 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. 2-Methyl ethyl ketone occurs as a natural product. It is made by some trees and found in some fruits and vegetables in small amounts. It is also released to the air from car and truck exhausts.

CDC-ATSDR Toxic Substances Portal
Methyl ethyl ketone is used as a solvent. Acute (short-term) inhalation exposure to methyl ethyl ketone in humans results in irritation to the eyes, nose, and throat. Limited information is available on the chronic (long-term) effects of methyl ethyl ketone in humans. Chronic inhalation studies in animals have reported slight neurological, liver, kidney, and respiratory effects. No information is available on the developmental, reproductive, or carcinogenic effects of methyl ethyl ketone in humans. Developmental effects, including decreased fetal weight and fetal malformations, have been reported in mice and rats exposed to methyl ethyl ketone via inhalation and ingestion. EPA has classified methyl ethyl ketone as a Group D, not classifiable as to human carcinogenicity.

Methyl ethyl ketone

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 of Methyl ethyl ketone:
CAS Number of Methyl ethyl ketone:
78-93-3 ☑
3D model (JSmol)
Interactive image
Interactive image
Beilstein Reference   741880
ChEBI
CHEBI:28398 ☑
ChEMBL
ChEMBL15849 ☑
ChemSpider
6321 ☑
ECHA InfoCard   100.001.054
Gmelin Reference   25656
KEGG
C02845 ☑
PubChem CID
6569
RTECS number
EL6475000
UNII
6PT9KLV9IO ☑
CompTox Dashboard (EPA)
DTXSID3021516 Edit this at Wikidata
InChI[show]
SMILES[show]
Properties of Methyl ethyl ketone:
Chemical formula of Methyl ethyl ketone:   C4H8O
Molar mass of Methyl ethyl ketone:   72.107 g·mol−1
Appearance of Methyl ethyl ketone:   Colorless liquid
Odor of Methyl ethyl ketone:   Mint or acetone-like[3]
Density of Methyl ethyl ketone:   0.8050 g/mL
Melting point of Methyl ethyl ketone:   −86 °C (−123 °F; 187 K)
Boiling point of Methyl ethyl ketone:   79.64 °C (175.35 °F; 352.79 K)
Solubility of Methyl ethyl ketone: in water   27.5 g/100 mL
log P   0.37[4]
Vapor pressure of Methyl ethyl ketone:   78 mmHg (20 °C)[3]
Acidity of Methyl ethyl ketone:(pKa)   14.7
Magnetic susceptibility of Methyl ethyl ketone:(χ)   −45.58·10−6 cm3/mol
Refractive index of Methyl ethyl ketone: (nD)   1.37880
Viscosity of Methyl ethyl ketone:   0.43 cP
Structure of Methyl ethyl ketone:
Dipole moment of Methyl ethyl ketone:   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).
☑ verify (what is ☑☒ ?)
Infobox references
Methyl ethyl ketone, also known as methyl ethyl ketone (MEK),[a] is an organic compound with the formula CH3C(O)CH2CH3. This colorless liquid ketone has a sharp, sweet odor reminiscent of butterscotch and acetone[vague] Methyl ethyl ketone is produced industrially on a large scale, but occurs in nature only in trace amounts.[7]Methyl ethyl ketone is partially soluble in water, and is commonly used as an industrial solvent.[8] Methyl ethyl ketone is an isomer of another solvent, tetrahydrofuran.

Production of Methyl ethyl ketone:
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 of Methyl ethyl ketone
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 is a liquid solvent used in surface coatings, adhesives, printing inks, chemical intermediates, magnetic tapes and lube oil dewaxing agents. Methyl ethyl ketonealso 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 ketoneis especially valuable in formulating high solids coatings, which help to reduce emissions from coating operations. Methyl ethyl ketoneis a natural component of many foods, including apple juice, beans, chicken, honey and a variety of cheeses. Synonyms for Methyl ethyl ketoneare 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 ketoneunder 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 ketonefrom 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 ketonemay not reasonably be anticipated to cause adverse human health or environmental effects.

The panel's delisting petition presented extensive information on MEK's potential health and environmental effects, environmental releases, and resulting ambient air concentrations. Hazard information included in the petition illustrated MEK’s low acute and chronic toxicity and low environmental toxicity. Air dispersion modeling results showed that ambient concentrations of MEK, 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 ketonefrom 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 MEK. 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 ketonefrom 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 ketoneunder 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 ketoneto 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 ketonepose negligible adverse health risks and that no further data are needed to adequately characterize risk to children under the VCCEP program.

On April 19, 2004, TERA issued its report of the Methyl ethyl ketonepeer consultation meeting. In summary, panel members concluded that the Methyl ethyl ketonedata were adequate to characterize risks to children as outlined under the VCCEP program. No data needs were identified by any of the review committee members.

A manuscript “Methyl Ethyl Ketone Safety Characterization for Infants and Children: Assessment in the USEPA Voluntary Children’s Chemical Evaluation Program” describes the results of the TERA review and was published in Human and Ecological Risk Assessment 13: 747-772, 2007.