Methyl ethyl ketone
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| Names | |||
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Preferred IUPAC name
Butan-2-one
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| Other names
Ethyl methyl ketone
Methyl ethyl ketone (deprecated) MEK 2-Butanone Methylpropanone Ethylmethylketone Methylacetone |
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| Identifiers | |||
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3D model (Jmol)
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| 741880 | |||
| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.001.054 | ||
| 25656 | |||
| KEGG | |||
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PubChem CID
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| RTECS number | EL6475000 | ||
| UNII | |||
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| Properties | |||
| C4H8O | |||
| Molar mass | 72.11 g·mol−1 | ||
| Appearance | Colorless liquid | ||
| Odor | mint or acetone-like | ||
| Density | 0.8050 g/mL | ||
| Melting point | −86 °C (−123 °F; 187 K) | ||
| Boiling point | 79.64 °C (175.35 °F; 352.79 K) | ||
| 27.5 g/100 mL | |||
| Vapor pressure | 78 mmHg (20°C) | ||
| Acidity (pKa) | 14.7 | ||
| -45.58·10−6 cm3/mol | |||
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Refractive index (nD)
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1.37880 | ||
| Viscosity | 0.43 cP | ||
| Structure | |||
| 2.76 D | |||
| Hazards | |||
| Safety data sheet | See: data page | ||
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EU classification (DSD)
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Flammable (F) Irritant (Xi) |
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| R-phrases | R11 R36 R66 R67 | ||
| S-phrases | (S2) S9 S16 | ||
| NFPA 704 | |||
| Flash point | −9 °C (16 °F; 264 K) | ||
| 505 °C (941 °F; 778 K) | |||
| Explosive limits | 1.4%-11.4% | ||
| Lethal dose or concentration (LD, LC): | |||
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LD50 (median dose)
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2737 mg/kg (oral, rat) 4050 mg/kg (oral, mouse) |
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LC50 (median concentration)
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12667 ppm (mammal) 13333 ppm (mouse, 2 hr) 7833 ppm (rat, 8 hr) |
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| US health exposure limits (NIOSH): | |||
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PEL (Permissible)
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TWA 200 ppm (590 mg/m3) | ||
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REL (Recommended)
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TWA 200 ppm (590 mg/m3) ST 300 ppm (885 mg/m3) | ||
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IDLH (Immediate danger)
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3000 ppm | ||
| Related compounds | |||
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Related Ketones
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Acetone; 3-pentanone; 3-Methylbutanone | ||
| Supplementary data page | |||
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Refractive index (n), Dielectric constant (εr), etc. |
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Thermodynamic
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Phase behaviour solid–liquid–gas |
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| UV, IR, NMR, MS | |||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |||
Butanone, also known as methyl ethyl ketone (MEK), is an organic compound with the formula CH3C(O)CH2CH3. This colorless liquid ketone has a sharp, sweet odor reminiscent of butterscotch and acetone. It is produced industrially on a large scale, and also occurs in trace amounts in nature. It is soluble in water and is commonly used as an industrial solvent.
Butanone may be produced by oxidation of 2-butanol. The dehydrogenation of 2-butanol using a catalyst is catalyzed by copper, zinc, or bronze:
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.
Both liquid-phase oxidation of heavy naphtha and the Fischer-Tropsch reaction produce mixed oxygenate streams, from which 2-butanone is extracted by fractionation.
Butanone is biosynthesized by some trees and found in some fruits and vegetables in small amounts. It is released to the air from car and truck exhausts.
Butanone 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 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. Butanone is also used in dry erase markers as the solvent of the erasable dye.
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Wikipedia