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Methods of forming alpha, beta-unsaturated acids and esters

United States Patent

January 31, 2006
View the Complete Patent at the US Patent & Trademark Office
Pacific Northwest National Laboratory - Visit the Technology Commercialization Program Website
The invention includes a method of forming an alpha, beta-unsaturated compound. A carboxylic acid is mixed with an alpha-hydroxy acid or an alpha-hydroxy ester and is esterified to form an alpha-acyloxy derivative. The alpha-acyloxy derivative is transformed into an alpha, beta-unsaturated derivative. The invention additionally includes a process of forming an acrylate. Lactic acid or a lactic acid ester is reacted with a first portion of acetic acid in the presence of a first catalyst to produce the corresponding 2-acetoxy propionic acid or ester. A non-reacted portion of the acetic acid is recycled. The 2-acetoxy propionic acid or ester is transferred to a second vessel containing a second catalyst, and acetic acid is liberated from the 2-acetoxy propionic acid or ester to produce a corresponding acrylic acid or acrylate ester. The acid or ester is subsequently esterified by reaction with an alcohol to form a desired acrylate ester.
Lilga; Michael A. (Richland, WA), Werpy; Todd A. (W. Richland, WA), Holladay; Johnathan E. (Kennewick, WA)
Battelle Memorial Institute (Richland, WA)
10/ 315,404
December 9, 2002