Browse history interactively

Page 1

Page 1Revision 1

Page 2

Page 2Revision 2

← Previous editContent deleted Content addedVisualWikitext

Revision as of 14:44, 9 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').← Previous edit		Latest revision as of 01:08, 19 October 2024 edit undoД.Ильин (talk | contribs)Extended confirmed users652 edits img
(159 intermediate revisions by 88 users not shown)
Line 1:		Line 1:
	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 407859916
			| verifiedrevid = 443881102
	| Name = Isobutanol
	| ImageFileL1 = Isobutanol.png		| Name = Isobutanol (2-Methyl-propan-1-ol)
			| ImageFile = Isobutanol.svg
	| ImageSizeL1 = 150px
			| ImageSize = 200
	| ImageNameL1 = Isobutanol
			| ImageName = Skeletal formula of isobutanol
	| ImageFileR1 = Isobutanol-3D-vdW.png
			| ImageFile1 = Isobutanol-3D-balls.png
	| ImageSizeR1 = 100px
			| ImageSize1 = 200
	| ImageNameR1 = Isobutanol
			| ImageName1 = Ball-and-stick model of isobutanol
	| IUPACName = 2-Methylpropan-1-ol
			| ImageFile2 = Isobutanol.jpg
	| OtherNames = Isobutyl alcohol, IBA, 2-methylpropyl alcohol
			| ImageSize2 = 200px
	| Section1 = {{Chembox Identifiers
			| PIN = 2-Methylpropan-1-ol
	| UNII_Ref = {{fdacite|correct|FDA}}
			| OtherNames = Isobutyl alcohol<br />IBA<br />2-Methyl-1-propanol<br />2-Methylpropyl alcohol<br />Isopropylcarbinol
			|Section1={{Chembox Identifiers
			| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 56F9Z98TEM		| UNII = 56F9Z98TEM
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = C14710		| KEGG = C14710
	| InChI = 1/C4H10O/c1-4(2)3-5/h4-5H,3H2,1-2H3		| InChI = 1/C4H10O/c1-4(2)3-5/h4-5H,3H2,1-2H3
	| PubChem = 6560		| PubChem = 6560
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 269630		| ChEMBL = 269630
Line 24:		Line 27:
	| StdInChIKey = ZXEKIIBDNHEJCQ-UHFFFAOYSA-N		| StdInChIKey = ZXEKIIBDNHEJCQ-UHFFFAOYSA-N
	| CASNo = 78-83-1		| CASNo = 78-83-1
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| EC-number = 201-148-0		| EC_number = 201-148-0
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 6312		| ChemSpiderID = 6312
	| RTECS = NP9625000		| RTECS = NP9625000
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 46645
			| ChEBI = 46645
			| Gmelin = 49282
			| UNNumber = 1212
			| Beilstein = 1730878
	| SMILES = CC(C)CO		| SMILES = CC(C)CO
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Reference = <ref name="ICSC">{{ICSC-ref|01|13|name=Isobutanol|date=April 2005}}.</ref>		| Properties_ref = <ref name="ICSC">{{ICSC-ref|01|13|name=Isobutanol|date=April 2005}}.</ref>
	| Formula = C<sub>4</sub>H<sub>10</sub>O		| Formula = C<sub>4</sub>H<sub>10</sub>O
	| MolarMass = 74.122 g/mol		| MolarMass = 74.122 g/mol
	| Appearance = Colorless liquid		| Appearance = Colorless liquid
			| Odor = sweet, musty<ref name=PGCH/>
	| Density = 0.802 g/cm<sup>3</sup>, liquid
			| Density = 0.802 g/cm<sup>3</sup>, liquid
	| Solubility = 9.5 mL/100 mL<ref>{{cite web | url = http://www.chemicalland21.com/petrochemical/ISO-BUTANOL.htm | title = Iso-butanol | publisher = ChemicalLand21}}</ref>
			| Solubility = 8.7 mL/100 mL<ref>{{cite web | url = http://www.chemicalland21.com/petrochemical/ISO-BUTANOL.htm | title = Iso-butanol | publisher = ChemicalLand21}}</ref>
	| MeltingPtC = -101.9
	| BoilingPtC = 107.89		| MeltingPtC = -108
	| pKa =		| BoilingPtC = 107.89
	| Viscosity = 3.95 cP at 20 ºC		| pKa =
			| Viscosity = 3.95 cP at 20 °C
	| RefractIndex = 1.3959		| RefractIndex = 1.3959
	| LogP = 0.8		| LogP = 0.8
			| VaporPressure = 9 mmHg (20°C)<ref name=PGCH/>
	}}		}}
	| Section7 = {{Chembox Hazards		|Section7={{Chembox Hazards
	| Reference = <ref name="ICSC"/>		| Hazards_ref = <ref name="ICSC"/>
	| ExternalMSDS =		| ExternalSDS =
			| GHSPictograms = {{GHS02}}{{GHS07}}
	| EUIndex = 603-108-00-1
			| GHSSignalWord = Danger
	| EUClass = Irritant ('''Xi''')
			| HPhrases = {{H-phrases|226|315|318|335|336}}
	| RPhrases = {{R10}} {{R37/38}} {{R41}}, {{R67}}
			| PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|271|280|302+352|303+361+353|304+340|305+351+338|310|312|321|332+313|362|370+378|403+233|403+235|405|501}}
	| SPhrases = {{S2}} {{S7/9}} {{S13}} {{S26}} {{S37/39}} {{S46}}
	| NFPA-H = 1		| NFPA-H = 1
	| NFPA-F = 3		| NFPA-F = 3
	| NFPA-R = 0		| NFPA-R = 0
	| FlashPt = 28 °C (82 ºF)		| FlashPtC = 28
	| Autoignition = 415 ºC (779 ºF)		| AutoignitionPtC = 415
	| ExploLimits = 1.7–10.9%		| ExploLimits = 1.7–10.9%
			| IDLH = 1600 ppm<ref name=PGCH>{{PGCH|0352}}</ref>
			| REL = TWA 50 ppm (150 mg/m<sup>3</sup>)<ref name=PGCH/>
			| PEL = TWA 100 ppm (300 mg/m<sup>3</sup>)<ref name=PGCH/>
			| LDLo = 3750 mg/kg (rabbit, oral)<br/>2460 mg/kg (rat, oral)<ref>{{IDLH|78831|Isobutyl alcohol}}</ref>
	}}		}}
	| Section8 = {{Chembox Related		|Section8={{Chembox Related
	| OtherFunctn = ]<br/>]<br/>]		| OtherFunction = ]<br/>]<br/>]
	| Function = ]s		| OtherFunction_label = ]s
	| OtherCpds = ]<br/>]		| OtherCompounds = ]<br/>]
	}}		}}
	}}		}}
	'''Isobutanol''' (]: '''2-methylpropan-1-ol''') is an ] with the formula (CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>OH. This colorless, flammable liquid with a characteristic smell is mainly used as a solvent. Its ]s include ], ], and ], all of which are more important industrially.		'''Isobutanol''' (]: '''2-methylpropan-1-ol''') is an ] with the ] (CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>OH (sometimes ] as '''''i''-BuOH'''). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its ]s are ], ], and ], all of which are important industrially.<ref name=Ullmann/>
			==Occurrence==
			]s including isobutanol are grain fermentation byproducts. Therefore, trace amounts of isobutanol may be present in ].
	==Production==		==Production==
	Isobutanol is produced by the ] of ]. Two methods are practiced industrially, ] is more common and generates a mixture of normal and ]s, which are ]d to the alcohols and then separated. Reppe carbonylation is also practiced.<ref>{{Ullmann | first1 = Heinz-Dieter | last1 = Hahn | first2 = Georg | last2 = Dämbkes | first3 = Norbert | last3 = Rupprich | title = Butanols|doi = 10.1002/14356007.a04_463}}.</ref>		Isobutanol is produced by the ] of ]. Two methods are practiced industrially, ] is more common and generates a mixture of ] and ]:
			:CH<sub>3</sub>CH=CH<sub>2</sub> + CO + H<sub>2</sub> → CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CHO
			The reaction is catalyzed by cobalt or rhodium complexes. The resulting aldehydes are ]d to the alcohols, which are then separated. In Reppe ], the same products are obtained, but the hydrogenation is effected by the ].<ref name=Ullmann>{{Ullmann | first1 = Heinz-Dieter | last1 = Hahn | first2 = Georg | last2 = Dämbkes | first3 = Norbert | last3 = Rupprich | title = Butanols|doi = 10.1002/14356007.a04_463|year=2005}}.</ref>
			===Laboratory synthesis===
	Isobutanol is also produced naturally during the fermentation of carbohydrates and may also be a byproduct of the decay process of organic matter.{{Fact|date=March 2009}} Isobutanol, along with other low molecular weight alcohols can also be produced by some engineered microorganisms such as ].<ref>{{Citation | doi = 10.1007/s00253-010-2522-6 | author = Smith, Kevin Michael; Cho, Kwang-Myung; Liao, James C. | title = Engineering Corynebacterium glutamicum for isobutanol production | journal = Applied Microbiology and Biotechnology | year = 2010 | volume = 87 | issue = 3 | pages = 1045–1055 | pmid = 20376637 | pmc = 2886118 | postscript = .}}</ref>
			] and ] can be reacted to produce isobutyl alcohol via ].<ref>{{cite journal
			|title=Guerbet condensation of methanol with n-propanol to isobutyl alcohol over heterogeneous copper chromite/Mg–Al mixed oxides catalysts
			|date=2004-09-01
			|journal=Molecular Catalysis
			|volume=220
			|issue=2
			|pages=215–220
			|quote=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.
			|doi=10.1016/j.molcata.2004.05.034
			|first1=Carlo|last1=Carlini
			|first2=Cristina|last2=Flego
			|first3=Mario|last3=Marchionna
			}}</ref>
			===Biosynthesis of isobutanol===
	Research done by ]'s BioEnergy Science Center (BESC) at ] for the first time produced isobutanol directly from cellulose. The team led by James Liao of the ] used the process of consolidated bioprocessing where ] ] directly converted ] to isobutanol.<ref>{{cite web |url=http://apps1.eere.energy.gov/news/progress_alerts.cfm/pa_id=497 |title=Energy Department Announces New Advance in Biofuel Technology |date=March 07, 2011 | publisher=United States Department of Energy |language=English |accessdate=March 07, 2011}}</ref><ref>{{cite web |url=http://aem.asm.org/cgi/content/abstract/AEM.02454-10v1?maxtoshow=&hits=10&RESULTFORMAT=&fulltext=isobutanol&searchid=1&FIRSTINDEX=0&resourcetype=HWCIT |title=Metabolic Engineering Of Clostridium Cellulolyticum For Isobutanol Production From Cellulose |author=Wendy Higashide, Yongchao Li, Yunfeng Yang, and James C. Liao |date=March 04, 2011 | publisher=American Society for Microbiology |language=English |accessdate=March 07, 2011}}</ref>
			{{main|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. α-], derived from ], is prone to decarboxylation to give ], which is susceptible to reduction to the alcohol:<ref name=":0">{{Cite journal|title = Non-fermentative pathways for synthesis of branched-chain higher alcohols as biofuels|journal = Nature|pages = 86–89|volume = 451|issue = 7174|doi = 10.1038/nature06450|first1 = Shota|last1 = Atsumi|first2 = Taizo|last2 = Hanai|first3 = James C.|last3 = Liao|pmid=18172501|date=January 2008|bibcode = 2008Natur.451...86A|s2cid = 4413113}}</ref>
			:(CH<sub>3</sub>)<sub>2</sub>CHC(O)CO<sub>2</sub>H → (CH<sub>3</sub>)<sub>2</sub>CHCHO + CO<sub>2</sub>
			:(CH<sub>3</sub>)<sub>2</sub>CHCHO + NADH + H<sup>+</sup> → (CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>OH + NAD<sup>+</sup>
	==Applications==		==Applications==
			The uses of isobutanol and ] are similar. They are often used interchangeably. The main applications are as varnishes and precursors to esters, which are useful solvents, e.g. ]. Isobutyl esters of phthalic, adipic, and related dicarboxylic acids are common ]s.<ref name=Ullmann/> Isobutanol is also a component of some ].<ref name="Nature Review">{{cite journal|last=Peralta-Yahya|first=Pamela P.|author2=Zhang, Fuzhong|author3=del Cardayre, Stephen B.|author4=Keasling, Jay D.|title=Microbial engineering for the production of advanced biofuels|journal=Nature|date=15 August 2012|volume=488|issue=7411|pages=320–328|doi=10.1038/nature11478|pmid=22895337|bibcode=2012Natur.488..320P|s2cid=4423203}}</ref>
	Isobutanol has a variety of technical and industrial applications:
	*feedstock in the manufacture of ], which is used in the production of ] and similar ]s, and in the food industry as a ]
	*precursor of derivative esters; ] ]s such as ] (DIBP) are used as plasticizer agents in plastics, rubbers, and other dispersions
	*paint solvent
	*varnish remover
	*ink ingredient
	*paint additive, to reduce ], improve brush flow, and retard formation of oil residues (''blush'') on painted surfaces
	*gasoline additive, to reduce ]
	*automotive polish additive
	*automotive paint cleaner additive
	*chemical extractant in production of organic compounds
	*mobile phase in ].
	Isobutanol could possibly serve as an alternative to gasoline to fuel combustion engines, and it is being produced by companies such as ].<ref>{{citation | first = William | last = Pentland | title = Beyond Ethanol | url = http://www.forbes.com/2008/03/19/innovation-ethanol-fuel-tech-innovation08-cx_wp_0319innovation.html | publisher = Forbes | date = 2008-03-20 | accessdate = 2009-08-31}}.</ref> A 1993 SAE technical paper addresses blending methanol, ethanol and isobutanol with unleaded gasoline for use as a motor fuel.<ref>sae.org/technical/papers/932953</ref> A similar mixture is being used by Dyson Racing in the 2010 ].<ref>www.dysonracing.com/company/news/article.php?news_id=1112</ref> Gevo acquired Agri-Energy's ], ethanol production facility to retrofit it to produce commercial quantities of isobutanol for motor fuel.<ref name=Wald>{{cite news|last=Wald|first=Matthew L.|title=Ethanol Plant Is Switching to Butanol|url=http://green.blogs.nytimes.com/2011/03/10/ethanol-plant-is-switching-to-butanol/?hp|accessdate=10 March 2011|newspaper=]|date=10 March 2011}}</ref>
	==Safety and regulation==		==Safety and regulation==
	Isobutanol is one of the least ] of the butanols with an {{LD50}} of 2460 mg/kg (rat, oral).		Isobutanol is one of the least ] of the butanols with an {{LD50}} of 2460&nbsp;mg/kg (rat, oral).<ref name=Ullmann/>
	In March 2009, the ] government announced a ban on isobutanol use in ].<ref>{{citation | title = Cosmetic Chemicals Banned in Canada | journal = Chem. Eng. News | volume = 87 | issue = 11 | date = 2009-03-16 | page = 38}}.</ref>		In March 2009, the ] announced a ban on isobutanol use in ].<ref>{{citation | title = Cosmetic Chemicals Banned in Canada | journal = Chem. Eng. News | volume = 87 | issue = 11 | date = 2009-03-16 | page = 38}}.</ref>
	==References==		==References==
	{{reflist}}		{{Reflist|35em}}
	==External links==		==External links==
	{{Commonscat|Isobutanol}}		{{Commons category|Isobutanol}}
	*{{ICSC|0113|01}}		* {{ICSC|0113|01}}
	*{{PGCH|0352}}		* {{PGCH|0352}}
	*{{EHC|65|name=Butanols: four isomers}}		* {{EHC|65|name=Butanols: four isomers}}
	*{{HSG|009|name=Isobutanol|number=9}}		* {{HSG|009|name=Isobutanol|number=9}}
			{{Alcohols}}
			{{Sedatives}}
			{{GABAAR PAMs}}
			{{Authority control}}
	{{alcohols}}
	]
	]		]
			]
			]
	]
			]
	]
	]		]
			]
	]
			]
	]
	]
	]
	]
	]
	]
	]
	]
	]