Diisobutene Explained

Diisobutene 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 . The process also leads to some triisobutenes and tetraisobutenes.[1]

align="center" colspan="5" Diisobutene isomers
StructureCH2=C(CH3)-CH2C(CH3)3(CH3)2C=CHC(CH3)3
Systematic name2,4,4-Trimethyl-1-pentene2,4,4-Trimethyl-2-pentene
CAS number[107-39-1][107-40-4]
Density0.7150 g/mL0.7218 g/mL
Melting point-93.5 °C-106.3 °C
Boiling point101.4 °C104.9 °C

Applications

These compounds are used as precursors to isononylol and octylphenols by hydroformylation/hydrogenation and phenol alkylation, respectively. Both are precursors to plasticizers.[2] The isononylol is a precursor to 3,5,5-trimethylhexyl acetate, a commercial fragrance.[3] Diisobutenes were once of interest as components for automotive fuels.

Notes and References

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