Diisobutene

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Diisobutene (also known as Diisobutylene) refers to a pair of organic compounds with the overall formula C8H16. The isomers have the same carbon skeleton but differ in the location of the C=C bond. Both are colorless liquids with very similar physical properties. These compounds arise via the acid catalyzed dimerization of isobutene, a reaction that proceeds via the carbocation (CH3)3C+. The process also leads to some triisobutenes and tetraisobutenes. [1]

Contents

Diisobutene isomers
Image 2,4,4-Trimethylpent-1-ene.svg 2,4,4-Trimethylpent-2-ene.svg
StructureCH2=C(CH3)-CH2C(CH3)3(CH3)2C=CHC(CH3)3
Systematic name 2,4,4-Trimethyl-1-pentene2,4,4-Trimethyl-2-pentene
CAS number [107-39-1][107-40-4]
Density 0.7150 g/mL0.7218 g/mL
Melting point -93.5 °C-106.3 °C
Boiling point 101.4 °C104.9 °C

Applications

Hydrogenation is performed at a significant scale to give isooctane, which is an important fuel additive. Diisobutene is used as precursors to isononylol and octylphenols by hydroformylation/hydrogenation and phenol alkylation, respectively. Both are precursors to plasticizers. [2] The isononylol (3,5,5-trimethyl-hexan-1-ol) is a precursor to 3,5,5-trimethylhexyl acetate, a commercial fragrance. [3] Diisobutenes were once of interest as components for automotive fuels.

See also

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References

  1. ↑ Schmidt, Roland; Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke, Hartmut (2014). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–74. doi:10.1002/14356007.a13_227.pub3. ISBN   978-3-527-30673-2.
  2. ↑ Geilen, Frank M.A.; Stochniol, Guido; Peitz, Stephan; Schulte-Koerne, Ekkehard (2014). "Butenes". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–13. doi:10.1002/14356007.a04_483.pub3. ISBN   978-3-527-30385-4.
  3. ↑ Panten, Johannes; Surburg, Horst (2015). "Flavors and Fragrances, 2. Aliphatic Compounds". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–55. doi:10.1002/14356007.t11_t01. ISBN   978-3-527-30673-2.
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