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Biomass‐Based and Oxidant‐Free Preparation of Hydroquinone from Quinic Acid
Author(s) -
Assoah Benedicta,
Veiros Luis F.,
Afonso Carlos A. M.,
Candeias Nuno R.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600616
Subject(s) - chemistry , quinic acid , hydroquinone , organic chemistry , yield (engineering) , catalysis , toluene , decarbonylation , materials science , metallurgy
A biomass‐based route to the preparation of hydroquinone starting from the renewable starting material quinic acid is described. Amberlyst‐15 in the dry form promoted the one‐step formation of hydroquinone from quinic acid in toluene without any oxidants or metal catalysts in 72 % yield. Several acidic polymer‐based resins and organic acids as promoters as well as a variety of reaction conditions were screened including temperature, concentration and low‐ and high‐boiling‐point solvents. A 1:4 (w/w) ratio of quinic acid/Amberlyst‐15 was determined to be optimal to promote hydroquinone formation with only traces of a dimeric side‐product. A mechanism has been proposed based on the decarbonylation of protonated quino‐1,5‐lactone that is supported by experimental and computational calculation data.