Isobutylene

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Isobutylene
IUPAC name

2-Methylpropene

Other names

Isobutene
γ-Butylene
2-Methylpropylene
Methylpropene
2-Methylprop-1-ene

Identifiers
CAS number 115-11-7 YesY
PubChem 8255
ChemSpider 7957 YesY
UNII QA2LMR467H YesY
EC number 204-066-3
UN number 1055
In Liquefied petroleum gas: 1075
RTECS number UD0890000
Jmol-3D images Image 1
Properties[1]
Molecular formula C4H8
Molar mass 56.11 g mol−1
Appearance Colorless gas
Density 0.5879 g/cm3, liquid
Melting point −140.3 °C
Boiling point −6.9 °C; 19.6 °F; 266.2 K
Solubility in water Insoluble
Hazards[2]
GHS pictograms
GHS signal word DANGER
GHS hazard statements H220
GHS precautionary statements P210, P377, P381, P403
EU Index 601-012-00-4
EU classification Extremely flammable (F+)
R-phrases R12
S-phrases (S2), S9, S16, S33
NFPA 704
4
1
0
Flash point flammable gas
Autoignition temperature 465 °C (869 °F)
Explosive limits 1.8–9.6%
Related compounds
Related butenes 1-Butene
cis-2-Butene
trans-2-Butene
Related compounds Isobutane
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Isobutylene (or 2-methylpropene) is a hydrocarbon of industrial significance. It is a four-carbon branched alkene (olefin), one of the four isomers of butylene. At standard temperature and pressure it is a colorless flammable gas.

Occurrence in nature

Isobutylene is a component of natural gas and crude oil found in porous rock formations in the upper strata of some areas of the Earth's crust.

Uses

Isobutylene is used as an intermediate in the production of a variety of products. It is reacted with methanol and ethanol in the manufacture of the gasoline oxygenates methyl tert-butyl ether (MTBE) and ethyl tert-butyl ether (ETBE), respectively. Alkylation with butane produces isooctane, another fuel additive. Isobutylene is also used in the production of methacrolein. Polymerization of isobutylene produces butyl rubber (polyisobutylene). Antioxidants such as butylated hydroxytoluene (BHT) and butylated hydroxyanisole (BHA) are produced by Friedel-Crafts alkylation of phenols using isobutylene.

Manufacture

Isobutylene can be isolated from refinery streams by reaction with sulfuric acid, but the most common industrial method for its production is by catalytic dehydrogenation of isobutane.[3] In the 1990s, the production of isobutylene increased dramatically as the demand for oxygenates such as MTBE grew.

Safety

Isobutylene is a highly flammable gas and presents an explosion danger. Usually stored as a compressed, liquefied gas, if released it may produce an oxygen-deficient atmosphere that presents an asphyxiation hazard.[2]

See also

References

  1. ↑ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.), Merck, 1989, ISBN 091191028X , 5024.
  2. ↑ 2.0 2.1 Isobutene, International Chemical Safety Card 1027, Geneva: International Programme on Chemical Safety, April 2000 
  3. ↑ Olah, George A.; Molnár, Árpád, Hydrocarbon Chemistry, Wiley-Interscience, ISBN 978-0-471-41782-8 .

External links

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