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Synthesis of p-xylene from ethylene.

Journal of the American Chemical Society (2012-09-01)
Thomas W Lyons, Damien Guironnet, Michael Findlater, Maurice Brookhart
ABSTRACT

As 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.

MATERIALS
Product Number
Brand
Product Description

Supelco
p-Xylene, analytical standard
Pricing and availability is not currently available.
Sigma-Aldrich
p-Xylene, puriss. p.a., ≥99.0% (GC)
Pricing and availability is not currently available.
Sigma-Aldrich
p-Xylene, ReagentPlus®, 99%
Pricing and availability is not currently available.
Sigma-Aldrich
p-Xylene, suitable for HPLC, ≥99%
Pricing and availability is not currently available.
Supelco
p-Xylene, Pharmaceutical Secondary Standard; Certified Reference Material
Pricing and availability is not currently available.
Sigma-Aldrich
p-Xylene, anhydrous, ≥99%
Pricing and availability is not currently available.
Sigma-Aldrich
p-Xylene, SAJ first grade, ≥99.0%
Pricing and availability is not currently available.