TY - DATA T1 - Synthesis of p‑Xylene from Ethylene PY - 2012/09/26 AU - Thomas W. Lyons AU - Damien Guironnet AU - Michael Findlater AU - Maurice Brookhart UR - https://acs.figshare.com/articles/journal_contribution/Synthesis_of_i_p_i_Xylene_from_Ethylene/2483440 DO - 10.1021/ja307612b.s001 L4 - https://ndownloader.figshare.com/files/4126213 KW - shale gas deposits KW - alternative KW - feedstock KW - ethylene KW - meta isomers KW - chemical KW - EthyleneAs oil supplies KW - synthesis KW - uncontaminated KW - ortho N2 - 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. ER -