2,3-Butanediol

2,3-Butanediol
Names
IUPAC name
Butane-2,3-diol
Other names
2,3-Butylene glycol
Dimethylene glycol
2,3-Dihydroxybutane
Butan-2,3-diol
Identifiers
513-85-9 
ChEBI CHEBI:62064 
ChemSpider 257 Yes
EC number 208-173-6
Jmol-3D images Image
PubChem 262
Properties
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)
miscible
Solubility soluble in alcohol, ketones, ether
log P -0.92
Vapor pressure 0.23 hPa (20 °C)
Acidity (pKa) 14.9
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
1
1
0
Flash point 85 °C (185 °F; 358 K)
402 °C (756 °F; 675 K)
5462 mg/kg (rat, oral)
Related compounds
Related butanediols
 1,4-Butanediol
1,3-Butanediol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

2,3-Butanediol is a organic compound with the formula is (CH3)2(CHOH)2.[1] 2,3-Butanediol has three stereoisomers, all of which are colorless, viscous liquids. Butanediols have applications as precursors to various plastics and pesticides.

Isomerism

Of the three stereoisomers, two are enantiomers (levo- and dextro-2,3-butanediol).[2][3] The three stereoisomers consist of two enantiomers and one meso compound. The enantiomeric pair have (2R, 3R) and (2S, 3S) configurations at carbons 2 and 3, while the meso compound has configuration (2R, 3S) (or equivalently (2S, 3R)).

Industrial production and uses

2,3-Butanediol is prepared by hydrolysis of 2,3-butene oxide:[4]

(CH3CH)2O + H2O → (CH3)2(CHOH)2

The isomer distribution depends on the stereochemistry of the epoxide.

The meso isomer is used to combine with naphthalene-1,5-diisocyanate. The resulting polyurethane is called "Vulkollan)".[4]

Biological production

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.[5]

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.[6]

References

  1. ↑ 2,3-Butanediol at SigmaAldrich
  2. ↑ Boutron P (1992). "Cryoprotection of red blood cells by a 2,3-butanediol containing mainly the levo and dextro isomers". CRYOBIOLOGY 29 (3): 347–358. PMID 1499320.
  3. ↑ Wang Y, Tao F, Xu P (2014). "Glycerol dehydrogenase plays a dual role in glycerol metabolism and 2,3-butanediol formation in Klebsiella pneumoniae". Journal of Biological Chemistry 289 (9): 6080–6090. doi:10.1074/jbc.M113.525535. PMC 3937674. PMID 24429283.
  4. ↑ 4.0 4.1 Heinz Gräfje, Wolfgang Körnig, Hans-Martin Weitz, Wolfgang Reiß, Guido Steffan, Herbert Diehl, Horst Bosche, Kurt Schneider and Heinz Kieczka "Butanediols, Butenediol, and Butynediol" in Ullmann's Encyclopedia of Industrial Chemistry, 2000, Wiley-VCH, Weinheim. doi:10.1002/14356007.a04_455
  5. ↑ "3,5-dinitrobenzoic acid". Combined Chemical Dictionary. Chapman and Hall/CRC Press. 2007.
  6. ↑ "Fermentation Derived 2,3-Butanediol", by Marcio Voloch et al. in Comprehensive Biotechnology, Pergamon Press Ltd., England Vol 2, Section 3, p. 933 (1986).