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AssigneeArcher Daniels Midland Company
InventorsStephen Howard, Alexandra Sanborn
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Described herein are improved methods for the preparation of 5- and 6-membered cyclic mono and diesters of sugar alcohols and anhydrosugar alcohols by reaction with an organic acid RCOOH over a solid acidic substrate. The process is adaptable to a continuous process for simultaneously making and separating the cyclic esters from the sugar alcohols and anhydrosugar alcohols under mild conditions using the solid acid substrate as both the catalyst and a chromatographic bed for separation. The reactions are performed at mild temperatures of 70° C. to 100° C. and the formation of the cyclic esters is nearly quantitative. Also described is a method for making 5- and 6-membered cyclic mono and diesters of sugar alcohols and anhydrosugar alcohols using microwave irradiation in the presence of the organic acid.
A method of preparing cyclic esters from 5 or 6 carbon compounds comprising, contacting a column bed containing a solid acid catalyst with at least one starting 5 or 6 carbon compound selected from the group consisting of a sugar alcohol, a monoanhydrosugar alcohol, and a dianhydrosugar alcohol in the presence of an organic acid in a single step reaction under a single set of reaction conditions for a time sufficient to form at least one of a cyclic monoester and cyclic diester derivative of at least one of the monoanhydrosugar alcohol and a dianhydrosugar alcohol.
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