| Revision as of 16:58, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits Saving copy of the {{chembox}} taken from revid 389514462 of page 2,3-Butanediol for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 00:43, 12 July 2024 edit حسن علي البط (talk | contribs)Extended confirmed users, Pending changes reviewers19,940 edits added Category:Butane using HotCat |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 372005776 |
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| verifiedrevid = 477210239 |
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| Name = 2,3-Butanediol |
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| Name = 2,3-Butanediol |
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| ImageFile = 2,3-Butanediol.png |
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| ImageFile = 2,3-Butanediol.png |
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| ImageSize=150px |
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| ImageSize=120px |
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| ImageName = 2,3-butanediol |
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| ImageName = 2,3-butanediol |
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| IUPACName = Butane-2,3-diol |
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| PIN = Butane-2,3-diol |
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| OtherNames = 2,3-Butylene glycol<br />Dimethylene glycol<br />2,3-Dihydroxybutane<br />Butan-2,3-diol |
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| OtherNames = 2,3-Butylene glycol<br />Pseudobutylene glycol<br />2,3-Dihydroxybutane<br />Butan-2,3-diol<br>Diethanol{{citation needed|date=July 2018}} & Bis-ethanol |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 257 |
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| ChemSpiderID = 257 |
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| CASNo_Ref = {{cascite}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 513-85-9 |
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| CASNo = 513-85-9 |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| PubChem= 262 |
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| SMILES = CC(C(C)O)O |
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| CASNo1 = 19132-06-0 |
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| CASNo1_Comment = (2''S'',3''S'')-(+) |
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| CASNo2_Ref = {{cascite|correct|CAS}} |
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| CASNo2 = 24347-58-8 |
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| CASNo2_Comment = (2''R'',3''R'')-(−) |
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| CASNo3_Ref = {{cascite|correct|CAS}} |
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| CASNo3 = 5341-95-7 |
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| CASNo3_Comment = (2''R'',3''S'') |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 45427ZB5IJ |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII1 = 7E9UXG71S1 |
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| UNII1_Comment = (2''S'',3''S'')-(+) |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| UNII2 = OR02B2286A |
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| UNII2_Comment = (2''R'',3''R'')-(−) |
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| UNII3_Ref = {{fdacite|correct|FDA}} |
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| UNII3 = F5IA8X9O8M |
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| UNII3_Comment = (2''R'',3''S'') |
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| PubChem= 262 |
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| ChEMBL = 2312529 |
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| SMILES = CC(C(C)O)O |
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| EINECS = 208-173-6 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 62064 |
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| InChI = 1S/C4H10O2/c1-3(5)4(2)6/h3-6H,1-2H3 |
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| InChIKey = OWBTYPJTUOEWEK-UHFFFAOYSA-N |
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}} |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>4</sub>H<sub>10</sub>O<sub>2</sub> |
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| C = 4 | H = 10 | O = 2 |
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| Appearance = Colorless liquid |
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| MolarMass = 90.121 g/mol |
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| Density = 0.987 g/mL |
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| Odor = odorless |
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| Density = 0.987 g/mL |
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| MeltingPt = |
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| MeltingPtC = 19 |
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| BoilingPtC = 177 |
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| BoilingPtC = 177 |
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| Solubility = Miscible |
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| SolubleOther = Soluble in ], ]s, ] |
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| Solvent = other solvents |
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| RefractIndex = 1.4366 |
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| VaporPressure = 0.23 hPa (20 °C) |
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| pKa = 14.9 |
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| LogP = -0.92 |
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}} |
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| Section4 = {{Chembox Thermochemistry |
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| DeltaHf = -544.8 kJ/mol |
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| HeatCapacity = 213.0 J/K mol |
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| Section7 = {{Chembox Hazards |
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| Section7 = {{Chembox Hazards |
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| EUClass = Flammable ('''F''') |
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| LD50 = 5462 mg/kg (rat, oral) |
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| NFPA-H = 1 | NFPA-F = 1 | NFPA-R = 0 |
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| LD50 = 5462 mg/kg |
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| NFPA-F = 3 |
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| FlashPtC = 85 |
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| AutoignitionPtC = 402 |
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| RPhrases = {{R11}} |
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| SPhrases = {{S2}} {{S7}} {{S16}} |
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}} |
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| Section8 = {{Chembox Related |
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| Section8 = {{Chembox Related |
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| OtherFunctn = ]<br>] |
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| OtherFunction = ]<br>] |
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| Function =]s |
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| OtherFunction_label =]s |
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'''2,3-Butanediol''' is the ] with the formula (CH<sub>3</sub>CHOH)<sub>2</sub>. It is classified as a ''vic''-diol (]). It exists as three stereoisomers, a ] pair and the meso isomer. All are colorless liquids. Applications include precursors to various plastics and pesticides. |
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==Isomerism== |
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Of the three ]s, two are ]s (levo- and dextro-2,3-butanediol) and one is a ].<ref name="pmid1499320">{{cite journal | author=Boutron P | title=Cryoprotection of red blood cells by a 2,3-butanediol containing mainly the levo and dextro isomers | journal= ] | volume=29 | issue=3 | year=1992 | pages=347–358 | doi=10.1016/0011-2240(92)90036-2 | pmid=1499320}}</ref><ref name="pmid24429283">{{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= ] | 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 }}</ref> The enantiomeric pair have (2''R'', 3''R'') and (2''S'', 3''S'') configurations at carbons 2 and 3, while the meso compound has configuration (2''R'', 3''S'') or, equivalently, (2''S'', 3''R''). |
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==Industrial production and uses== |
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2,3-Butanediol is prepared by ] of ]:<ref name="Ullmann">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}}</ref> |
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:(CH<sub>3</sub>CH)<sub>2</sub>O + H<sub>2</sub>O → CH<sub>3</sub>(CHOH)<sub>2</sub>CH<sub>3</sub> |
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The isomer distribution depends on the stereochemistry of the ]. |
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The meso isomer is used to combine with naphthalene-1,5-diisocyanate. The resulting ] is called "Vulkollan".<ref name="Ullmann"/> |
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==Biological production== |
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The (2''R'',3''R'')-] of 2,3-butanediol is produced by a variety of ]s in a process known as ].<ref>{{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}}</ref> It is found naturally in ], in the roots of '']'', ], and in rotten ]s. It is used in the resolution of ] compounds in ].<ref>{{cite encyclopedia |
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| title = 3,5-dinitrobenzoic acid |
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| encyclopedia = Combined Chemical Dictionary |
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| publisher = ]/] |
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| year = 2007 }}</ref> |
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During ] research was done towards producing 2,3-butanediol by fermentation in order to produce ], the ] of the ] used in a leading type of ].<ref>, by Marcio Voloch et al. in ''Comprehensive Biotechnology'', Pergamon Press Ltd., England Vol 2, Section 3, p. 933 (1986).</ref> It can be derived from the fermentation of ] ].<ref name="DaiZhao2015">{{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}}</ref> |
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Fermentative production of 2,3-butanediol from ]s involves a network of biochemical reactions that can be manipulated to maximize production.<ref>{{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}}</ref> |
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2,3-butanediol has been proposed as a ] that could be created on ] by means of ] and '']'', shipped from Earth, working on resources available at the surface of Mars.<ref>, accessed 6 December 2021.</ref> |
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2,3-Butanediol has been detected, in peppers, grape wine, anatidaes. |
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== Reactions == |
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2,3-Butanediol undergo dehydration to form ] (methyl ethyl ketone):<ref>{{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}}</ref> |
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:(CH<sub>3</sub>CHOH)<sub>2</sub> → CH<sub>3</sub>C(O)CH<sub>2</sub>CH<sub>3</sub> + H<sub>2</sub>O |
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It can also undergo ] to form ]:<ref>{{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}}</ref> |
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:(CH<sub>3</sub>CHOH)<sub>2</sub> + 2 H<sub>2</sub> → C<sub>4</sub>H<sub>8</sub> + 2 H<sub>2</sub>O |
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==References== |
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<references/> |
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{{DEFAULTSORT:Butanediol, 2, 3-}} |
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] |
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] |