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2,3-Butanediol

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2,3-Butanediol
2,3-butanediol
Names
Preferred IUPAC name Butane-2,3-diol
Other names 2,3-Butylene glycol
Pseudobutylene glycol
2,3-Dihydroxybutane
Butan-2,3-diol
Diethanol & Bis-ethanol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.431 Edit this at Wikidata
EC Number
  • 208-173-6
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H10O2/c1-3(5)4(2)6/h3-6H,1-2H3Key: OWBTYPJTUOEWEK-UHFFFAOYSA-N
SMILES
  • CC(C(C)O)O
Properties
Chemical formula C4H10O2
Molar mass 90.122 g·mol
Appearance Colorless 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 in other solvents 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
Heat capacity (C) 213.0 J/K mol
Std enthalpy of
formation (ΔfH298) 		-544.8 kJ/mol
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1 1 0
Flash point 85 °C (185 °F; 358 K)
Autoignition
temperature 		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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

2,3-Butanediol is the organic compound with the formula (CH3CHOH)2. It is classified as a vic-diol (glycol). It exists as three stereoisomers, a chiral pair and the meso isomer. All are colorless liquids. Applications include 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. 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-epoxybutane:

(CH3CH)2O + H2O → CH3(CHOH)2CH3

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".

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.

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. It can be derived from the fermentation of sugarcane molasses.

Fermentative production of 2,3-butanediol from carbohydrates involves a network of biochemical reactions that can be manipulated to maximize production.

2,3-butanediol has been proposed as a rocket fuel that could be created on Mars by means of cyanobacteria and E. coli, shipped from Earth, working on resources available at the surface of Mars.

2,3-Butanediol has been detected, in peppers, grape wine, anatidaes.

Reactions

2,3-Butanediol undergo dehydration to form butanone (methyl ethyl ketone):

(CH3CHOH)2 → CH3C(O)CH2CH3 + H2O

It can also undergo deoxydehydration to form butene:

(CH3CHOH)2 + 2 H2 → C4H8 + 2 H2O

References

  1. 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. doi:10.1016/0011-2240(92)90036-2. PMID 1499320.
  2. 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.
  3. ^ 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
  4. C. De Mas; N. B. Jansen; G. T. Tsao (1988). "Production of optically active 2,3-butanediol by Bacillus polymyxa". Biotechnol. Bioeng. 31 (4): 366–377. doi:10.1002/bit.260310413. PMID 18584617. S2CID 36530193.
  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).
  7. Dai, Jian-Ying; Zhao, Pan; Cheng, Xiao-Long; Xiu, Zhi-Long (2015). "Enhanced Production of 2,3-Butanediol from Sugarcane Molasses". Applied Biochemistry and Biotechnology. 175 (6): 3014–3024. doi:10.1007/s12010-015-1481-x. ISSN 0273-2289. PMID 25586489. S2CID 11287904.
  8. Jansen, Norman B.; Flickinger, Michael C.; Tsao, George T. (1984). "Application of bioenergetics to modelling the microbial conversion of D-xylose to 2,3-butanediol". Biotechnol Bioeng. 26 (6): 573–582. doi:10.1002/bit.260260603. PMID 18553372. S2CID 22878894.
  9. "Rocket fuel made on Mars could propel astronauts back to Earth", Design Products & Applications, accessed 6 December 2021.
  10. Nikitina, Maria A.; Ivanova, Irina I. (2016-02-23). "Conversion of 2,3-Butanediol over Phosphate Catalysts". ChemCatChem. 8 (7): 1346–1353. doi:10.1002/cctc.201501399. ISSN 1867-3880. S2CID 102135312.
  11. Kwok, Kelvin Mingyao; Choong, Catherine Kai Shin; Ong, Daniel Sze Wei; Ng, Joy Chun Qi; Gwie, Chuandayani Gunawan; Chen, Luwei; Borgna, Armando (2017-06-07). "Hydrogen-Free Gas-Phase Deoxydehydration of 2,3-Butanediol to Butene on Silica-Supported Vanadium Catalysts". ChemCatChem. 9 (13): 2443–2447. doi:10.1002/cctc.201700301. ISSN 1867-3880. S2CID 99415384.
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