Preparation of alkyl acrylamidoglycolates and their alkyl ethers

• US 4,760,168 A
• Filed: 02/20/1987
• Issued: 07/26/1988
• Est. Priority Date: 05/12/1982
• Status: Expired due to Term

• Current Assignee: American Cyanamid Co (Pfizer Inc.)
• Original Assignee: American Cyanamid Co (Pfizer Inc.)
• Inventors: Schirmann, Peter J.
• Primary Examiner(s): Shippen, Michael L.
• Application Number:
  US07/018,743
• Time in Patent Office: 522 Days
• Field of Search: 560/170
• US Class Current: 560/170
• CPC Class Codes: N/A

Abstract

Reaction of an acrylamide with an alkyl glyoxylate or an alkyl glyoxylate hemiacetal provides an alkyl acrylamidoglycolate which can readily be alkylated to provide the alkyl ether thereof.

Claims

1. A process for preparing an alkyl acrylamidoglycolate alkyl ether in solid form wherein the alkyl groups in the ester and ether functionalities are the same, which comprises reacting an acrylamide with an alkyl glyoxylate hemiacetal in essentially equal molar proportions at a temperature in the range of about 50°

C. to about 90°

C. in the presence of a polymerization inhibitor to yield an alkyl acrylamidoglycolate, reacting said alkyl acrylamidoglycolate in the presence of an etherification catalyst at reflux temperature with an excess of an alcohol selected from the group consisting of aliphatic and cycloaliphatic alcohols of 1-6 carbon atoms and 1,2-dihydroxy alcohols of 2-6 carbon atoms whose alkyl group is the same as the alkyl group in the ester functionality of said alkyl acrylamidoglycolate to yield said alkyl acrylamidoglycolate alkyl ether and removing the excess alcohol by distillation.

2. the process of claim 1 wherein the alkyl glyoxylate hemiacetal is selected from methyl glyoxylate methyl hemiacetal, ethyl glyoxylate ethyl hemiacetal and butyl glyoxylate butyl hemiacetal.