Difference between revisions of "Isobutanol"

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|  ImageName1 = Isobutanol
 
|  ImageName1 = Isobutanol
 
|  IUPACName = 2-Methylpropan-1-ol
 
|  IUPACName = 2-Methylpropan-1-ol
−
|  OtherNames = Isobutyl alcohol, IBA,<br /> 2-methylpropyl alcohol
+
|  OtherNames = Isobutyl alcohol, IBA,<br/>2-Methylpropyl alcohol
 
| Section1 = {{Chembox Identifiers
 
| Section1 = {{Chembox Identifiers
 
|  SMILES = CC(C)CO
 
|  SMILES = CC(C)CO
 
|  CASNo = 78-83-1
 
|  CASNo = 78-83-1
 
|    CASNo_Ref = {{cascite}}
 
|    CASNo_Ref = {{cascite}}
 +
|  RTECS = NP9625000
 +
|  ChemSpiderID = 6312
 +
|  InChI = 1/C4H10O/c1-4(2)3-5/h4-5H,3H2,1-2H3
 +
|  StdInChI = 1S/C4H10O/c1-4(2)3-5/h4-5H,3H2,1-2H3
 +
|  InChIKey = ZXEKIIBDNHEJCQ-UHFFFAOYAQ
 +
|  StdInChIKey = ZXEKIIBDNHEJCQ-UHFFFAOYSA-N
 +
|  EC-number = 201-148-0
 
|  RTECS = NP9625000
 
|  RTECS = NP9625000
 
   }}
 
   }}
 
| Section2 = {{Chembox Properties
 
| Section2 = {{Chembox Properties
 +
|  Reference = <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 = 74.12 g/mol
+
|  MolarMass = 74.122 g/mol
−
|  Appearance = Colorless liquid
+
|  Appearance = colorless liquid
−
|  Density = 0.802 g/cm³, liquid
+
|  Density = 0.802 g/cm<sup>3</sup>, liquid
−
|  Solubility = Limited solubility
+
|  Solubility = limited solubility
 
|  MeltingPt = -108 °C (165 K)
 
|  MeltingPt = -108 °C (165 K)
 
|  BoilingPt = 108 °C (381 K)
 
|  BoilingPt = 108 °C (381 K)
 
|  pKa =
 
|  pKa =
−
|  Viscosity = 3.95 [[centipoise]] at 20[[Celsius|°C]]
+
|  Viscosity = 3.95 cP at 20 ºC
 +
|   RefractIndex = 1.3959
 +
|  LogP = 0.8
 
   }}
 
   }}
−
| Section3 = {{Chembox Structure
+
| Section7 = {{Chembox Hazards
−
|  Dipole =
+
|  Reference = <ref name="ICSC"/><ref>{{CLP Regulation|index=603-108-00-1|page=493}}</ref><ref>{{PGCH-ref|0352|name=Isobutyl alcohol}}.</ref>
 +
|  ExternalMSDS = {{ICSC-small|01|13}}
 +
|  EUIndex = 603-108-00-1
 +
|  GHSPictograms = {{GHS02|Flam. Liq. 3}}{{GHS05|STOT SE 3}}{{GHS07|Skin Irrit. 2; Eye Dam. 1}}
 +
|  GHSSignalWord = DANGER
 +
|  HPhrases = {{H-phrases|226|335|315|318|336}}
 +
|  FlashPt = 28 °C (82 ºF)
 +
|  Autoignition = 415 ºC (779 ºF)
 +
|  ExploLimits = 1.7–10.9%
 +
|  PEL = 100 ppm TWA
 +
|  IDLH = 1600 ppm
 
   }}
 
   }}
−
| Section7 = {{Chembox Hazards
 
−
|  ExternalMSDS = [http://ptcl.chem.ox.ac.uk/MSDS/IS/isobutyl_alcohol.html External MSDS]
 
−
|  MainHazards = Flammable
 
−
|  NFPA-H = 1
 
−
|  NFPA-F = 3
 
−
|  NFPA-R =
 
−
|  FlashPt = 28 °C
 
−
|  RSPhrases = R: 10-20-22-36-37-38<br /> S: 7-16-24/25-26
 
−
  }}<!--
 
−
| [[Isobutanol chemdata supplement#Structure and properties|Structure and<br />properties]]
 
−
| [[Refractive index|''1.3959'']]
 
−
|-
 
−
| [[Isobutanol chemdata supplement#Thermodynamic properties|Thermodynamic<br />data]]
 
−
-->
 
 
| Section8 = {{Chembox Related
 
| Section8 = {{Chembox Related
−
|  Function = [[alcohol]]s
+
|  OtherFunctn = [[Butan-1-ol]]<br/>[[Sec-Butanol|''sec''-Butanol]]<br/>[[Tert-Butanol|''tert''-Butanol]]
−
|  OtherFunctn = [[Isopropyl alcohol]],<br />[[ethanol]], [[2-Butanol|2-butanol]]
+
|   Function = [[butanol]]s
−
|   OtherCpds = [[acetone]], [[propylene]], [[diisopropyl ether]]
+
|  OtherCpds = [[2,2-Dimethylpropan-1-ol]]
 
   }}
 
   }}
 
}}
 
}}
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Isobutanol is considered to be slightly toxic and it has been shown to cause [[liver]] damage in mice and humans. Ingestion may also lead to [[alcohol poisoning]].
 
Isobutanol is considered to be slightly toxic and it has been shown to cause [[liver]] damage in mice and humans. Ingestion may also lead to [[alcohol poisoning]].
  
−
In March 2009 the [[Canada]]ian government announced its ban of isobutanol in [[cosmetics]].<ref>''Cosmetic Chemicals Banned in Canada'' [[Chemical & Engineering News]], '''87''', 11 (16 March 2009), p. 38</ref>
+
In March 2009 the [[Canada|Canadian]] government announced its ban of isobutanol in [[cosmetics]].<ref>{{citation | title = Cosmetic Chemicals Banned in Canada | journal = Chem. Eng. News | volume = 87 | issue = 11 | date = 2009-03-16 | page = 38}}.</ref>
−
 
 
−
 
 
−
MSDS
 
−
http://www.jtbaker.com/msds/englishhtml/i7600.htm
 
  
 
==References==
 
==References==
 
{{reflist}}
 
{{reflist}}
−
*[http://www.inchem.org/documents/hsg/hsg/hsg009.htm Health and Safety Guide for Isobutanol]. [[World Health Organisation]], 1987. Last accessed [[October 5]], [[2005]].
 
  
 
==External links==
 
==External links==
 
{{Commons|Butanol}}
 
{{Commons|Butanol}}
 +
*{{ICSC|01|13}}
 +
*{{PGCH|0352}}
 
*{{EHC|65|name=Butanols: four isomers}}
 
*{{EHC|65|name=Butanols: four isomers}}
 +
*{{HSG|009|name=Isobutanol|number=9}}
 
* http://www.forbes.com/2008/03/19/innovation-ethanol-fuel-tech-innovation08-cx_wp_0319innovation.html
 
* http://www.forbes.com/2008/03/19/innovation-ethanol-fuel-tech-innovation08-cx_wp_0319innovation.html
  

Revision as of 08:59, 22 August 2009

Isobutanol
Isobutanol
Isobutanol
IUPAC name 2-Methylpropan-1-ol
Other names Isobutyl alcohol, IBA,
2-Methylpropyl alcohol
Identifiers
InChI InChI=1/C4H10O/c1-4(2)3-5/h4-5H,3H2,1-2H3
InChIKey ZXEKIIBDNHEJCQ-UHFFFAOYAQ
Standard InChI InChI=1S/C4H10O/c1-4(2)3-5/h4-5H,3H2,1-2H3
Standard InChIKey ZXEKIIBDNHEJCQ-UHFFFAOYSA-N
CAS number [78-83-1]
EC number 201-148-0
RTECS NP9625000
ChemSpider 6312
SMILES
Properties[1]
Chemical formula C4H10O
Molar mass 74.122 g/mol
Appearance colorless liquid
Density 0.802 g/cm3, liquid
Melting point

-108 °C (165 K)

Boiling point

108 °C (381 K)

Solubility in water limited solubility
log P 0.8
Refractive index (nD) 1.3959
Viscosity 3.95 cP at 20 ºC
Hazards[1][2][3]
Material safety data sheet (MSDS) ICSC 0113
EU index number 603-108-00-1
GHS pictograms Flam. Liq. 3STOT SE 3Skin Irrit. 2; Eye Dam. 1
GHS signal word DANGER
GHS hazard statements H226, H335, H315, H318, H336
Flash point 28 °C (82 ºF)
Autoignition temp. 415 ºC (779 ºF)
Explosive limits 1.7–10.9%
PEL (U.S.) 100 ppm TWA
IDLH level 1600 ppm
Related compounds
Other butanols Butan-1-ol
sec-Butanol
tert-Butanol
Other compounds 2,2-Dimethylpropan-1-ol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol; also known as 2-methylpropyl alcohol, among other names) is a colorless, flammable, organic compound with a characteristic smell. Its isomers are n-butanol, 2-butanol, and tert-butanol. It is classified as an alcohol, and, as such, it is widely used as a solvent in chemical reactions, as well as being a useful starting material for organic synthesis.

Isobutanol is produced naturally during the fermentation of carbohydrates. It may also be a by-product of the decay process of organic matter.

Applications

  • feedstock in the manufacture of isobutyl acetate, which is used in the production of lacquer and similar coatings, and in the food industry as a flavouring agent
  • in the industrial synthesis of derivative esters; isobutyl esters such as diisobutyl phthalate (DIBP) are used as plasticizer agents in plastics, rubbers, and other dispersions
  • as paint solvent
  • as varnish remover
  • as ink
  • as paint additive, to reduce viscosity
  • as paint additive, to improve brush flow
  • as paint additive, to retard the formation of oil residues (blush) on painted surfaces
  • as gasoline additive, to reduce carburetor icing
  • as additive to automotive polish
  • as additive to automotive paint cleaner
  • as a chemical extractant in production of organic compounds
  • as a mobile phase in thin layer chromatography.

Future applications could serve as an eventual substitute to gasoline to fuel combustion engines and is being aggressively researched by companies such as Gevo for this use.

Safety

Isobutanol is a volatile, flammable liquid that should be stored and used in well-ventilated areas. It is moderately irritating to the skin and greatly irritating to the eyes, mucous membranes, and respiratory tract. Exposure to high concentrations of its vapour can cause temporary narcosis.

Isobutanol is considered to be slightly toxic and it has been shown to cause liver damage in mice and humans. Ingestion may also lead to alcohol poisoning.

In March 2009 the Canadian government announced its ban of isobutanol in cosmetics.[4]

References

  1. ↑ 1.0 1.1 Isobutanol; International Chemical Safety Card 0113; International Labour Organization: Geneva, April 2005, <http://www.inchem.org/documents/icsc/icsc/eics0113.htm>.
  2. ↑ Index no. 603-108-00-1 of Annex VI, Part 3, to Regulation (EC) No 1272/2008 of the European Parliament and of the Council of 16 December 2008 on classification, labelling and packaging of substances and mixtures, amending and repealing Directives 67/548/EEC and 1999/45/EC, and amending Regulation (EC) No 1907/2006. OJEU L353, 31.12.2008, pp 1–1355 at p 493.
  3. ↑ Isobutyl alcohol. In Pocket Guide to Chemical Hazards; U.S. Department of Health and Human Services (NIOSH) Publication No. 2005-149; Government Printing Office: Washington, DC, 2005. ISBN 9780160727511, <http://www.cdc.gov/niosh/npg/default.html>.
  4. ↑ Cosmetic Chemicals Banned in Canada. Chem. Eng. News 2009-03-16, 87 (11), 38.

External links

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