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  19132-06-0 (2S,3S)-(+)  24347-58-8 (2R,3R)-(-) 5341-95-7 (2R,3S) | |
| 3D model (Jmol) | Interactive image |
| ChEBI | CHEBI:62064 |
| ChemSpider | 257 |
| ECHA InfoCard | 100.007.431 |
| EC Number | 208-173-6 |
| 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 |
| Refractive index (nD) |
1.4366 |
| Thermochemistry | |
| 213.0 J/K mol | |
| Std enthalpy of formation (ΔfH |
-544.8 kJ/mol |
| Hazards | |
| EU classification (DSD) |
Flammable (F) |
| R-phrases | R11 |
| S-phrases | (S2) S7 S16 |
| NFPA 704 | |
| Flash point | 85 °C (185 °F; 358 K) |
| 402 °C (756 °F; 675 K) | |
| Lethal dose or concentration (LD, LC): | |
| LD50 (median dose) |
5462 mg/kg (rat, oral) |
| Related compounds | |
| Related butanediols |
1,4-Butanediol 1,3-Butanediol |
| 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 | |
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) and one is a meso compound.[2][3] 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
- ↑ 2,3-Butanediol at SigmaAldrich
- ↑ 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.
- ↑ 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. - 1 2 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
- ↑ "3,5-dinitrobenzoic acid". Combined Chemical Dictionary. Chapman and Hall/CRC Press. 2007.
- ↑ "Fermentation Derived 2,3-Butanediol", by Marcio Voloch et al. in Comprehensive Biotechnology, Pergamon Press Ltd., England Vol 2, Section 3, p. 933 (1986).
7. C. De Mas, N. B. Jansen, G. T. Tsao (1988). "Production of optically active 2,3-butanediol by Bacillus polymyxa." Biotechnol. Bioeng. 31(4): 366-77.