2,3-Butanediol

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2,3-Butanediol
2,3-butanediol
Identifiers
CAS number 513-85-9 YesY
PubChem 262
ChemSpider 257 YesY
EC number 208-173-6
ChEBI CHEBI:62064 N
Jmol-3D images Image 1
Properties
Molecular formula C4H10O2
Molar mass 90.121 g/mol
Appearance nearly colorless solid or liquid
Odor odorless
Density 0.987 g/mL
Melting point 19 °C (66 °F; 292 K)
Boiling point 177 °C (351 °F; 450 K)
Solubility in water miscible
Solubility soluble in alcohol, ketones, ether
log P -0.92
Vapor pressure 0.23 hPa (20 °C)
Acidity (pKa) 14.9
Refractive index (nD) 1.4366
Thermochemistry
Specific
heat capacity
C
213.0 J/K mol
Std enthalpy of
formation
ΔfHo298
-544.8 kJ/mol
Hazards
EU classification Flammable (F)
R-phrases R11
S-phrases (S2) S7 S16
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil 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 85 °C (185 °F; 358 K)
LD50 5462 mg/kg (rat, oral)
Related compounds
Related butanediols 1,4-Butanediol
1,3-Butanediol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

2,3-Butanediol is a chemical compound composed of carbon, hydrogen, and oxygen. Its formula is C4H10O2. It is one of the constitutional isomers of butanediol.[1]

Uses and manufacturing[edit]

The (2R,3R)-stereoisomer of 2,3-butanediol is produced by a variety of microorganisms in a process known as butanediol fermentation. It is found naturally in cocoa butter, in the roots of Ruta graveolens, sweet corn, and in rotten mussels. It is used in the resolution of carbonyl compounds in gas chromatography.[2]

History[edit]

During World War II research was done towards producing 2,3-butanediol by fermentation in order to produce 1,3-butadiene, the monomer of the polybutadiene used in a leading type of synthetic rubber.[3]

References[edit]

  1. ^ 2,3-Butanediol at SigmaAldrich
  2. ^ "3,5-dinitrobenzoic acid". Combined Chemical Dictionary. Chapman and Hall/CRC Press. 2007. 
  3. ^ "Fermentation Derived 2,3-Butanediol", by Marcio Voloch et al. in Comprehensive Biotechnology, Pergamon Press Ltd., England Vol 2, Section 3, p. 933 (1986).