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Butanone

Butanone
Skeletal formula of butanone
Ball-and-stick model of butanone
Space-filling model of butanone
methyl ethyl ketone
Names
Preferred IUPAC name
Butan-2-one
Other names
Ethyl methyl ketone
Methyl ethyl ketone (not recommended)
MEK
2-Butanone
Methylpropanone
Ethylmethylketone
Methylacetone
Identifiers
78-93-3 YesY
3D model (Jmol) Interactive image
Interactive image
741880
ChEBI CHEBI:28398 YesY
ChEMBL ChEMBL15849 YesY
ChemSpider 6321 YesY
ECHA InfoCard 100.001.054
25656
KEGG C02845 YesY
PubChem 6569
RTECS number EL6475000
UNII 6PT9KLV9IO YesY
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
1.37880
Viscosity 0.43 cP
Structure
2.76 D
Hazards
Safety data sheet See: data page
Flammable (F)
Irritant (Xi)
R-phrases R11 R36 R66 R67
S-phrases (S2) S9 S16
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
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):
LD50 (median dose)
2737 mg/kg (oral, rat)
4050 mg/kg (oral, mouse)
12667 ppm (mammal)
13333 ppm (mouse, 2 hr)
7833 ppm (rat, 8 hr)
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 200 ppm (590 mg/m3)
REL (Recommended)
TWA 200 ppm (590 mg/m3) ST 300 ppm (885 mg/m3)
IDLH (Immediate danger)
3000 ppm
Related compounds
Related Ketones
Acetone; 3-pentanone; 3-Methylbutanone
Supplementary data page
Refractive index (n),
Dielectric constantr), etc.
Thermodynamic
data
Phase behaviour
solid–liquid–gas
UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
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

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