Isobutylene

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 but not highly flammable.

Isobutylene
Ball-and-stick model of isobutylene
Space-filling model of isobutylene
Names
Preferred IUPAC name
2-Methylprop-1-ene
Other names
2-Methylpropene
Isobutene
γ-Butylene
2-Methylpropylene
Methylpropene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.697
EC Number
  • 204-066-3
RTECS number
  • UD0890000
UNII
UN number 1055
In Liquefied petroleum gas: 1075
Properties[1]
C4H8
Molar mass 56.106 g/mol
Appearance Colorless gas
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)
Insoluble
-44.4·10−6 cm3/mol
Hazards[2]
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H220
P210, P377, P381, P403
NFPA 704 (fire diamond)
Flammability code 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
4
1
0
Flash point flammable gas
465 °C (869 °F; 738 K)
Explosive limits 1.8–9.6%
Related compounds
Related butenes
 1-Butene
cis-2-Butene
trans-2-Butene
Related compounds
 Isobutane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Uses

Isobutylene is used as an intermediate in the production of a variety of products. By reaction with methanol and ethanol, it is a precursor to 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.

tert-Butylamine is produced commercially by amination of isobutylene using zeolite catalysts:[3]

NH3 + CH2=C(CH3)2 → H2NC(CH3)3

Manufacture

Polymer and chemical grade isobutylene is typically obtained by dehydrating tertiary butyl alcohol (TBA) or catalytic dehydrogenation of isobutane (Catofin or similar processes).[4] 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.

By-product

In the ethenolysis of diisobutylene to prepare neohexene, isobutylene is a byproduct:[5]

(CH3)3C-CH=C(CH3)2 + CH2=CH2 → (CH3)3C-CH=CH2 + (CH3)2C=CH2

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]

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See also

References
  1. The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.), Merck, 1989, ISBN 091191028X, 5024.
  2. Isobutene, International Chemical Safety Card 1027, Geneva: International Programme on Chemical Safety, April 2000
  3. Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2000). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001.
  4. Olah, George A.; Molnár, Árpád, Hydrocarbon Chemistry, Wiley-Interscience, ISBN 978-0-471-41782-8.
  5. Lionel Delaude, Alfred F. Noels. "Metathesis". Kirk-Othmer Encyclopedia of Chemical Technology. Wiley.CS1 maint: uses authors parameter (link)
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