Fusel alcohols including isobutanol are grain fermentation byproducts. Therefore, trace amounts of isobutanol may be present in many alcoholic beverages.
The reaction is catalyzed by cobalt or rhodium complexes. The resulting aldehydes are hydrogenated to the alcohols, which are then separated. In Reppe carbonylation, the same products are obtained, but the hydrogenation is effected by the water-gas shift reaction.[5]
E. coli as well as several other organisms has been genetically modified to produce C4 alcohols from glucose, including isobutanol, 1-butanol, 2-methyl-1-butanol, 3-methyl-1-butanol, and 2-phenylethanol. The host's highly active amino acid biosynthetic pathway is shifted to alcohol production. α-Ketoisovalerate, derived from valine, is prone to decarboxylation to give isobutyraldehyde, which is susceptible to reduction to the alcohol:[7]
(CH3)2CHC(O)CO2H → (CH3)2CHCHO + CO2
(CH3)2CHCHO + NADH + H+ → (CH3)2CHCH2OH + NAD+
Applicationsedit
The uses of isobutanol and 1-Butanol are similar. They are often used interchangeably. The main applications are as varnishes and precursors to esters, which are useful solvents, e.g. isobutyl acetate. Isobutyl esters of phthalic, adipic, and related dicarboxylic acids are common plasticizers.[5] Isobutanol is also a component of some biofuels.[8]
Safety and regulationedit
Isobutanol is one of the least toxic of the butanols with an LD50 of 2460 mg/kg (rat, oral).[5]
^Carlini, Carlo; Flego, Cristina; Marchionna, Mario (2004-09-01). "Guerbet condensation of methanol with n-propanol to isobutyl alcohol over heterogeneous copper chromite/Mg–Al mixed oxides catalysts". Molecular Catalysis. 220 (2): 215–220. doi:10.1016/j.molcata.2004.05.034. The synthesis of isobutyl alcohol from methanol (MeOH) and n-propanol (PrOH) through the Guerbet condensation has been studied [. . .] using catalytic system of copper chromite and Mg-Al mixed oxides.
^Atsumi, Shota; Hanai, Taizo; Liao, James C. (January 2008). "Non-fermentative pathways for synthesis of branched-chain higher alcohols as biofuels". Nature. 451 (7174): 86–89. Bibcode:2008Natur.451...86A. doi:10.1038/nature06450. PMID 18172501. S2CID 4413113.
^Peralta-Yahya, Pamela P.; Zhang, Fuzhong; del Cardayre, Stephen B.; Keasling, Jay D. (15 August 2012). "Microbial engineering for the production of advanced biofuels". Nature. 488 (7411): 320–328. Bibcode:2012Natur.488..320P. doi:10.1038/nature11478. PMID 22895337. S2CID 4423203.
isobutanol, iupac, nomenclature, methylpropan, organic, compound, with, formula, 2chch2oh, sometimes, represented, buoh, this, colorless, flammable, liquid, with, characteristic, smell, mainly, used, solvent, either, directly, esters, isomers, butanol, butanol. Isobutanol IUPAC nomenclature 2 methylpropan 1 ol is an organic compound with the formula CH3 2CHCH2OH sometimes represented as i BuOH This colorless flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters Its isomers are 1 butanol 2 butanol and tert butanol all of which are important industrially 5 Isobutanol 2 Methyl propan 1 ol Names Preferred IUPAC name 2 Methylpropan 1 ol Other names Isobutyl alcoholIBA2 Methyl 1 propanol2 Methylpropyl alcoholIsopropylcarbinol Identifiers CAS Number 78 83 1 Y 3D model JSmol Interactive image Beilstein Reference 1730878 ChEBI CHEBI 46645 Y ChEMBL ChEMBL269630 Y ChemSpider 6312 Y ECHA InfoCard 100 001 044 EC Number 201 148 0 Gmelin Reference 49282 KEGG C14710 Y PubChem CID 6560 RTECS number NP9625000 UNII 56F9Z98TEM Y UN number 1212 CompTox Dashboard EPA DTXSID0021759 InChI InChI 1S C4H10O c1 4 2 3 5 h4 5H 3H2 1 2H3 YKey ZXEKIIBDNHEJCQ UHFFFAOYSA N YInChI 1 C4H10O c1 4 2 3 5 h4 5H 3H2 1 2H3 SMILES CC C CO Properties 3 Chemical formula C4H10O Molar mass 74 122 g mol Appearance Colorless liquid Odor sweet musty 1 Density 0 802 g cm3 liquid Melting point 108 C 162 F 165 K Boiling point 107 89 C 226 20 F 381 04 K Solubility in water 8 7 mL 100 mL 2 log P 0 8 Vapor pressure 9 mmHg 20 C 1 Refractive index nD 1 3959 Viscosity 3 95 cP at 20 C Hazards 3 GHS labelling Pictograms Signal word Danger Hazard statements H226 H315 H318 H335 H336 Precautionary statements P210 P233 P240 P241 P242 P243 P261 P264 P271 P280 P302 P352 P303 P361 P353 P304 P340 P305 P351 P338 P310 P312 P321 P332 P313 P362 P370 P378 P403 P233 P403 P235 P405 P501 NFPA 704 fire diamond 130 Flash point 28 C 82 F 301 K Autoignitiontemperature 415 C 779 F 688 K Explosive limits 1 7 10 9 Lethal dose or concentration LD LC LDLo lowest published 3750 mg kg rabbit oral 2460 mg kg rat oral 4 NIOSH US health exposure limits PEL Permissible TWA 100 ppm 300 mg m3 1 REL Recommended TWA 50 ppm 150 mg m3 1 IDLH Immediate danger 1600 ppm 1 Safety data sheet SDS ICSC 0113 Related compounds Related butanols 1 Butanolsec Butanoltert Butanol Related compounds IsobutyraldehydeIsobutyric acid Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Occurrence 2 Production 2 1 Laboratory synthesis 2 2 Biosynthesis of isobutanol 3 Applications 4 Safety and regulation 5 References 6 External linksOccurrence editFusel alcohols including isobutanol are grain fermentation byproducts Therefore trace amounts of isobutanol may be present in many alcoholic beverages Production editIsobutanol is produced by the carbonylation of propylene Two methods are practiced industrially hydroformylation is more common and generates a mixture of isobutyraldehyde and butyraldehyde CH3CH CH2 CO H2 CH3CH2CH2CHO The reaction is catalyzed by cobalt or rhodium complexes The resulting aldehydes are hydrogenated to the alcohols which are then separated In Reppe carbonylation the same products are obtained but the hydrogenation is effected by the water gas shift reaction 5 Laboratory synthesis edit Propanol and methanol can be reacted to produce isobutyl alcohol via Guerbet condensation 6 Biosynthesis of isobutanol edit Main article Butanol fuel E coli as well as several other organisms has been genetically modified to produce C4 alcohols from glucose including isobutanol 1 butanol 2 methyl 1 butanol 3 methyl 1 butanol and 2 phenylethanol The host s highly active amino acid biosynthetic pathway is shifted to alcohol production a Ketoisovalerate derived from valine is prone to decarboxylation to give isobutyraldehyde which is susceptible to reduction to the alcohol 7 CH3 2CHC O CO2H CH3 2CHCHO CO2 CH3 2CHCHO NADH H CH3 2CHCH2OH NAD Applications editThe uses of isobutanol and 1 Butanol are similar They are often used interchangeably The main applications are as varnishes and precursors to esters which are useful solvents e g isobutyl acetate Isobutyl esters of phthalic adipic and related dicarboxylic acids are common plasticizers 5 Isobutanol is also a component of some biofuels 8 Safety and regulation editIsobutanol is one of the least toxic of the butanols with an LD50 of 2460 mg kg rat oral 5 In March 2009 the Government of Canada announced a ban on isobutanol use in cosmetics 9 References edit a b c d e NIOSH Pocket Guide to Chemical Hazards 0352 National Institute for Occupational Safety and Health NIOSH Iso butanol ChemicalLand21 a b Isobutanol International Chemical Safety Card 0113 Geneva International Programme on Chemical Safety April 2005 Isobutyl alcohol Immediately Dangerous to Life or Health Concentrations IDLH National Institute for Occupational Safety and Health NIOSH a b c d Hahn Heinz Dieter Dambkes Georg Rupprich Norbert 2005 Butanols Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a04 463 ISBN 978 3527306732 Carlini Carlo Flego Cristina Marchionna Mario 2004 09 01 Guerbet condensation of methanol with n propanol to isobutyl alcohol over heterogeneous copper chromite Mg Al mixed oxides catalysts Molecular Catalysis 220 2 215 220 doi 10 1016 j molcata 2004 05 034 The synthesis of isobutyl alcohol from methanol MeOH and n propanol PrOH through the Guerbet condensation has been studied using catalytic system of copper chromite and Mg Al mixed oxides Atsumi Shota Hanai Taizo Liao James C January 2008 Non fermentative pathways for synthesis of branched chain higher alcohols as biofuels Nature 451 7174 86 89 Bibcode 2008Natur 451 86A doi 10 1038 nature06450 PMID 18172501 S2CID 4413113 Peralta Yahya Pamela P Zhang Fuzhong del Cardayre Stephen B Keasling Jay D 15 August 2012 Microbial engineering for the production of advanced biofuels Nature 488 7411 320 328 Bibcode 2012Natur 488 320P doi 10 1038 nature11478 PMID 22895337 S2CID 4423203 Cosmetic Chemicals Banned in Canada Chem Eng News 87 11 38 2009 03 16 External links edit nbsp Wikimedia Commons has media related to Isobutanol International Chemical Safety Card 0113 NIOSH Pocket Guide to Chemical Hazards 0352 National Institute for Occupational Safety and Health NIOSH IPCS Environmental Health Criteria 65 Butanols four isomers IPCS Health and Safety Guide 9 Isobutanol Retrieved from https en wikipedia org w index php title Isobutanol amp oldid 1216140559, wikipedia, wiki, book, books, library,
