2,3-Butanediol

changed changed 477210239 2,3-Butanediol 2,3-Butanediol.png skin-invert-image 120px 2,3-butanediol Butane-2,3-diol 2,3-Butylene glycolPseudobutylene glycol2,3-DihydroxybutaneButan-2,3-diolDiethanolJuly 2018 & Bis-ethanol correct chemspider 257 correct CAS 513-85-9 correct CAS 19132-06-0 (2S,3S)-(+) correct CAS 24347-58-8 (2R,3R)-(−) correct CAS 5341-95-7 (2R,3S) correct FDA 45427ZB5IJ correct FDA 7E9UXG71S1 (2S,3S)-(+) correct FDA OR02B2286A (2R,3R)-(−) correct FDA F5IA8X9O8M (2R,3S) 262 2312529 CC(C(C)O)O 208-173-6 changed EBI 62064 1S/C4H10O2/c1-3(5)4(2)6/h3-6H,1-2H3 OWBTYPJTUOEWEK-UHFFFAOYSA-N 4 10 2 Colorless liquid odorless 0.987 g/mL 19 177 Miscible Soluble in alcohol, ketones, ether other solvents 1.4366 0.23 hPa (20 °C) 14.9 −0.92 −544.8 kJ/mol 213.0 J/K mol 5462 mg/kg (rat, oral) 1 1 0 85 402 1,4-Butanediol1,3-Butanediol 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.Boutron P Cryoprotection of red blood cells by a 2,3-butanediol containing mainly the levo and dextro isomers Cryobiology 29 3 1992 347–358 10.1016/0011-2240(92)90036-2 1499320Wang Y, Tao F, Xu P Glycerol dehydrogenase plays a dual role in glycerol metabolism and 2,3-butanediol formation in Klebsiella pneumoniae Journal of Biological Chemistry 289 9 2014 6080–6090 10.1074/jbc.M113.525535 http://www.jbc.org/content/289/9/6080.long 3937674 24429283 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. 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. 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 10.1002/bit.260310413 18584617 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. 3,5-dinitrobenzoic acid Combined Chemical Dictionary Chapman and Hall/CRC Press 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."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.Dai Jian-Ying Zhao Pan Cheng Xiao-Long Xiu Zhi-Long Enhanced Production of 2,3-Butanediol from Sugarcane Molasses Applied Biochemistry and Biotechnology 175 6 2015 3014–3024 0273-2289 10.1007/s12010-015-1481-x 25586489 11287904 Fermentative production of 2,3-butanediol from carbohydrates involves a network of biochemical reactions that can be manipulated to maximize production.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 10.1002/bit.260260603 18553372 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."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):Nikitina Maria A. Ivanova Irina I. 2016-02-23 Conversion of 2,3-Butanediol over Phosphate Catalysts ChemCatChem en 8 7 1346–1353 10.1002/cctc.201501399 102135312 1867-3880 (CH3CHOH)2 → CH3C(O)CH2CH3 + H2O It can also undergo deoxydehydration to form butene: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 10.1002/cctc.201700301 99415384 1867-3880 (CH3CHOH)2 + 2 H2 → C4H8 + 2 H2O References Category:Alkanediols Category:Vicinal diols Category:Butane