2,3-Butanediol
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477210239
| Name = 2,3-Butanediol
| ImageFile = 2,3-Butanediol.png
| ImageSize=120px
| ImageName = 2,3-butanediol
| PIN = Butane-2,3-diol
| OtherNames = 2,3-Butylene glycol
Pseudobutylene glycol
2,3-Dihydroxybutane
Butan-2,3-diol
Diethanol{{citation needed|date=July 2018}} & Bis-ethanol
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 257
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 513-85-9
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo1 = 19132-06-0
| CASNo1_Comment = (2S,3S)-(+)
| CASNo2_Ref = {{cascite|correct|CAS}}
| CASNo2 = 24347-58-8
| CASNo2_Comment = (2R,3R)-(−)
| CASNo3_Ref = {{cascite|correct|CAS}}
| CASNo3 = 5341-95-7
| CASNo3_Comment = (2R,3S)
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 45427ZB5IJ
| UNII1_Ref = {{fdacite|correct|FDA}}
| UNII1 = 7E9UXG71S1
| UNII1_Comment = (2S,3S)-(+)
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = OR02B2286A
| UNII2_Comment = (2R,3R)-(−)
| UNII3_Ref = {{fdacite|correct|FDA}}
| UNII3 = F5IA8X9O8M
| UNII3_Comment = (2R,3S)
| PubChem= 262
| ChEMBL = 2312529
| SMILES = CC(C(C)O)O
| EINECS = 208-173-6
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 62064
| InChI = 1S/C4H10O2/c1-3(5)4(2)6/h3-6H,1-2H3
| InChIKey = OWBTYPJTUOEWEK-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C = 4 | H = 10 | O = 2
| Appearance = Colorless liquid
| Odor = odorless
| Density = 0.987 g/mL
| MeltingPtC = 19
| BoilingPtC = 177
| Solubility = Miscible
| SolubleOther = Soluble in alcohol, ketones, ether
| Solvent = other solvents
| RefractIndex = 1.4366
| VaporPressure = 0.23 hPa (20 °C)
| pKa = 14.9
| LogP = −0.92
}}
| Section4 = {{Chembox Thermochemistry
| DeltaHf = −544.8 kJ/mol
| HeatCapacity = 213.0 J/K mol
}}
| Section7 = {{Chembox Hazards
| LD50 = 5462 mg/kg (rat, oral)
| NFPA-H = 1 | NFPA-F = 1 | NFPA-R = 0
| FlashPtC = 85
| AutoignitionPtC = 402
}}
| Section8 = {{Chembox Related
| OtherFunction = 1,4-Butanediol
1,3-Butanediol
| OtherFunction_label =butanediols
}}
}}
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.{{cite journal | author=Boutron P | title=Cryoprotection of red blood cells by a 2,3-butanediol containing mainly the levo and dextro isomers | journal= Cryobiology | volume=29 | issue=3 | year=1992 | pages=347–358 | doi=10.1016/0011-2240(92)90036-2 | pmid=1499320}}{{cite journal |vauthors=Wang Y, Tao F, Xu P | title=Glycerol dehydrogenase plays a dual role in glycerol metabolism and 2,3-butanediol formation in Klebsiella pneumoniae | journal= Journal of Biological Chemistry | volume=289 | issue=9 | year=2014 | pages=6080–6090 | doi=10.1074/jbc.M113.525535 | url=http://www.jbc.org/content/289/9/6080.long | pmc=3937674 | pmid=24429283| doi-access=free }} 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: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}}
:(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.{{Cite journal | author1 = C. De Mas| author2 =N. B. Jansen| author3 = G. T. Tsao | date = 1988 | title = Production of optically active 2,3-butanediol by Bacillus polymyxa | journal = Biotechnol. Bioeng. | volume = 31 | issue = 4 | pages = 366–377| doi =10.1002/bit.260310413| pmid =18584617| s2cid =36530193}} 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.{{cite encyclopedia
| title = 3,5-dinitrobenzoic acid
| encyclopedia = Combined Chemical Dictionary
| publisher = Chapman and Hall/CRC Press
| year = 2007 }}
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.[https://www.msu.edu/~narayan/2-3-Butanediol.pdf "Fermentation Derived 2,3-Butanediol"], by Marcio Voloch et al. in Comprehensive Biotechnology, Pergamon Press Ltd., England Vol 2, Section 3, p. 933 (1986). It can be derived from the fermentation of sugarcane molasses.{{cite journal|last1=Dai|first1=Jian-Ying|last2=Zhao|first2=Pan|last3=Cheng|first3=Xiao-Long|last4=Xiu|first4=Zhi-Long|title=Enhanced Production of 2,3-Butanediol from Sugarcane Molasses|journal=Applied Biochemistry and Biotechnology |volume=175 |issue=6 |year=2015 |pages=3014–3024 |issn=0273-2289 |doi=10.1007/s12010-015-1481-x|pmid=25586489|s2cid=11287904}}
Fermentative production of 2,3-butanediol from carbohydrates involves a network of biochemical reactions that can be manipulated to maximize production.{{Cite journal|last1=Jansen|first1=Norman B.|last2=Flickinger|first2=Michael C.|last3=Tsao|first3=George T.|date=1984|title=Application of bioenergetics to modelling the microbial conversion of D-xylose to 2,3-butanediol|journal=Biotechnol Bioeng|volume=26|issue=6|pages=573–582|doi=10.1002/bit.260260603|pmid=18553372|s2cid=22878894}}
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.[https://www.dpaonthenet.net/article/188369/ "Rocket fuel made on Mars could propel astronauts back to Earth", Design Products & Applications], accessed 6 December 2021.
2,3-Butanediol has been detected, in peppers, grape wine, anatidaes.
Reactions
2,3-Butanediol undergo dehydration to form butanone (methyl ethyl ketone):{{Cite journal|last1=Nikitina|first1=Maria A.|last2=Ivanova|first2=Irina I.|date=2016-02-23|title=Conversion of 2,3-Butanediol over Phosphate Catalysts|journal=ChemCatChem|language=en|volume=8|issue=7|pages=1346–1353|doi=10.1002/cctc.201501399|s2cid=102135312|issn=1867-3880}}
:(CH3CHOH)2 → CH3C(O)CH2CH3 + H2O
It can also undergo deoxydehydration to form butene:{{Cite journal|last1=Kwok|first1=Kelvin Mingyao|last2=Choong|first2=Catherine Kai Shin|last3=Ong|first3=Daniel Sze Wei|last4=Ng|first4=Joy Chun Qi|last5=Gwie|first5=Chuandayani Gunawan|last6=Chen|first6=Luwei|last7=Borgna|first7=Armando|date=2017-06-07|title=Hydrogen-Free Gas-Phase Deoxydehydration of 2,3-Butanediol to Butene on Silica-Supported Vanadium Catalysts|journal=ChemCatChem|volume=9|issue=13|pages=2443–2447|doi=10.1002/cctc.201700301|s2cid=99415384|issn=1867-3880}}
:(CH3CHOH)2 + 2 H2 → C4H8 + 2 H2O