1,5-Hexadiene is the
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with the formula (CH)(CH=CH). It is a colorless, volatile liquid. It is used as a
crosslinking agent
In chemistry and biology a cross-link is a bond or a short sequence of bonds that links one polymer chain to another. These links may take the form of covalent bonds or ionic bonds and the polymers can be either synthetic polymers or natural ...
and precursor to a variety of other compounds.
Synthesis
1,5-Hexadiene is produced commercially by the
ethenolysis
In organic chemistry, ethenolysis is a chemical process in which internal olefins are degraded using ethylene () as the reagent. The reaction is an example of cross metathesis. The utility of the reaction is driven by the low cost of ethylene ...
of
1,5-cyclooctadiene
Cycloocta-1,5-diene is a cyclic hydrocarbon with the chemical formula , specifically .
There are three configurational isomers with this structure, that differ by the arrangement of the four CāC single bonds adjacent to the double bonds. Each ...
:
:(CHCH=CHCH) + 2 CH=CH ā 2 (CH)CH=CH
The catalyst is derived from
ReO on alumina.
A laboratory-scale preparation involves reductive coupling of
allyl chloride
Allyl chloride is the organic compound with the formula C H2=CHCH2 Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a ch ...
using magnesium:
:2 ClCHCH=CH + Mg ā (CH)(CH=CH) + MgCl
References
Alkadienes
Monomers
{{Hydrocarbons