ja307612b_si_001.pdf (770.14 kB)
Synthesis of p‑Xylene from Ethylene
journal contribution
posted on 2012-09-26, 00:00 authored by Thomas
W. Lyons, Damien Guironnet, Michael Findlater, Maurice BrookhartAs oil supplies dwindle, there is a growing need to develop
new
routes to chemical intermediates that utilize alternative feedstocks.
We report here a synthesis of para-xylene, one of
the highest volume chemicals derived from petroleum, using only ethylene
as a feedstock. Ethylene is an attractive alternative feedstock, as
it can be derived from renewable biomass resources or harnessed from
large domestic shale gas deposits. The synthesis relies on the conversion
of hexene (from trimerization of ethylene) to 2,4-hexadiene followed
by a Diels–Alder reaction with ethylene to form 3,6-dimethylcyclohexene.
This monoene is readily dehydrogenated to para-xylene
uncontaminated by the ortho and meta isomers. We report here a selective synthesis of para-xylene, uncontaminated by the ortho or meta isomers, using ethylene as the sole feedstock.