The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Date of Patent:
Jul. 17, 2018

Filed:

Dec. 11, 2014
Applicant:

Archer Daniels Midland Company, Decatur, IL (US);

Inventors:

Kenneth Stensrud, Decatur, IL (US);

Erik Hagberg, Decatur, IL (US);

Erin Rockafellow, Decatur, IL (US);

Assignee:

Archer Daniels Midland Company, Decatur, IL (US);

Attorney:
Primary Examiner:
Int. Cl.
CPC ...
C07D 493/00 (2006.01); C07D 493/04 (2006.01);
U.S. Cl.
CPC ...
C07D 493/04 (2013.01);
Abstract

A method for acid-catalyzed acylation of an isohexide is described. The method involves a reaction of an isohexide and an excess of carboxylic acid in the presence of a Lewis acid or a Brnsted acid catalyst. One or more Lewis acid or Brnsted acid can facilitate conversion of isohexides to their corresponding mono and diesters with a pronounced greater regio-selectivity of exo-OH over endo-OH of the isohexide in the product. Particular catalytic acid species include zirconium chloride (ZrCl) and phosphonic acid (HPO), which manifest a ratio of exo:endo regioselectivity of about 5.0≠3:1 and about 4.00.3:1, respectively.


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