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Synthesis of Isosorbide Esters from Sorbitol with Heterogeneous Catalysts
Author(s) -
Fraile José M.,
Saavedra Carlos J.
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201601866
Subject(s) - isosorbide , sorbitol , chemistry , yield (engineering) , catalysis , organic chemistry , acetic acid , sulfonic acid , solvent , alkyl , nuclear chemistry , materials science , metallurgy
Sulfonic solids of different nature (alkyl, aryl and perfluoroalkyl sulfonic) are able to catalyze the dehydration of sorbitol under solvent free conditions at moderate temperature (130 °C) under vacuum and the esterification of isosorbide with carboxylic acids, either acetic or octanoic acids. Yields around 80 % of isosorbide can be obtained from sorbitol with only 1 mol% catalyst after 24 h. Yields of dicarboxylates from isosorbide were in the range of 70–80 % for diacetate and up to 97 % for dioctanoate. The two‐step one‐pot process from sorbitol is highly efficient for isosorbide diacetate (up to 71 % yield), whereas the esterification with octanoic acid is more sensitive to the presence of by‐products (up to 57 % yield).