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 colourless flammable gas.
|Preferred IUPAC name
3D model (JSmol)
In Liquefied petroleum gas: 1075
CompTox Dashboard (EPA)
|Molar mass||56.106 g/mol|
|Density||0.5879 g/cm3, liquid|
|Melting point||−140.3 °C (−220.5 °F; 132.8 K)|
|Boiling point||−6.9 °C (19.6 °F; 266.2 K)|
|GHS signal word||DANGER|
|P210, P377, P381, P403|
|Flash point||flammable gas|
|465 °C (869 °F; 738 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
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 (similarly, isobutylene can be dimerized to diisobutylene (DIB), then hydrogenated to make isooctane). Isobutylene is also used in the production of methacrolein. Polymerization of isobutylene produces butyl rubber (polyisobutylene or PIB). Antioxidants such as butylated hydroxytoluene (BHT) and butylated hydroxyanisole (BHA) are produced by Friedel-Crafts alkylation of phenols using isobutylene.
Polymer and chemical grade isobutylene is typically obtained by dehydrating tertiary butyl alcohol (TBA) or catalytic dehydrogenation of isobutane (Catofin or similar processes). Gasoline oxygenates MTBE and ETBE are produced by reacting methanol or ethanol with isobutylene contained in butene streams from olefin steam crackers or refineries, or with isobutylene from dehydrated TBA. Isobutylene is not isolated from the olefin or refinery butene stream before the reaction as separating the ethers from the remaining butenes is simpler. Isobutylene can also be produced in high purities by "back-cracking" MTBE or ETBE at high temperatures and then separating the isobutylene by distillation from the much higher boiling resulting alcohols.
- (CH3)3C-CH=C(CH3)2 + CH2=CH2 → (CH3)3C-CH=CH2 + (CH3)2C=CH2
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.
- The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.), Merck, 1989, ISBN 091191028X, 5024.
- Isobutene, International Chemical Safety Card 1027, Geneva: International Programme on Chemical Safety, April 2000
- Olah, George A.; Molnár, Árpád, Hydrocarbon Chemistry, Wiley-Interscience, ISBN 978-0-471-41782-8.
- Lionel Delaude, Alfred F. Noels. "Metathesis". Kirk-Othmer Encyclopedia of Chemical Technology. Wiley.CS1 maint: Uses authors parameter (link)