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p ‐Cymene as Solvent for Olefin Metathesis: Matching Efficiency and Sustainability
Author(s) -
Granato Artur V.,
Santos Alexandra G.,
dos Santos Eduardo N.
Publication year - 2017
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201700116
Subject(s) - metathesis , chemistry , solvent , grubbs' catalyst , salt metathesis reaction , ring opening metathesis polymerisation , organic chemistry , isomerization , yield (engineering) , toluene , olefin metathesis , polymerization , materials science , catalysis , polymer , metallurgy
Abstract The underexploited biorenewable p ‐cymene is employed as a solvent for the metathesis of various substrates. p ‐Cymene is a nontoxic compound that can be obtained in large amounts as a side product of the cellulose and citrus industry. For the cross‐metathesis of estragole with methyl acrylate, this solvent prevents the consecutive double‐bond isomerization of the product and affords the best yield of all solvents tested. Undesired consecutive isomerization is a major challenge for many substrates in olefin metathesis, including pharmaceutical precursors, and the use of p ‐cymene as a solvent may be a way to prevent it. This solvent results in a better metathesis performance than toluene for the three substrates tested in this work, matching its performance for two other substrates.