Hexadiene

1,5-Hexadiene

1,5-Hexadiene

Chemical compound

1,5-Hexadiene is the organic compound with the formula (CH2)2(CH=CH2)2. It is a colorless, volatile liquid. It is used as a crosslinking agent and precursor to a variety of other compounds.

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Synthesis

1,5-Hexadiene is produced commercially by the ethenolysis of 1,5-cyclooctadiene:[1]

(CH2CH=CHCH2)2 + 2 CH2=CH2 → 2 (CH2)2CH=CH2

The catalyst is derived from Re2O7 on alumina.

A laboratory-scale preparation involves reductive coupling of allyl chloride using magnesium:[2]

2 ClCH2CH=CH2 + Mg → (CH2)2(CH=CH2)2 + MgCl2

References

  1. [1]
    Lionel Delaude; Alfred F. Noels (2005). "Metathesis". Kirk-Othmer Encyclopedia of Chemical Technology. Weinheim: Wiley-VCH. doi:10.1002/0471238961.metanoel.a01. ISBN 9780471484943.
  2. [2]
    Amos Turk; Henry Chanan (1947). "Biallyl". Org. Synth. 27: 7. doi:10.15227/orgsyn.027.0007.
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