Preparation of predominately methyl acrylamidoglycolate methyl ether in a normally liquid product
First Claim
1. A process for preparing methyl acrylamidoglycolate methyl ether in non-viscous liquid form comprising a major proportion of methyl acrylamidoglycolate methyl ether and a sufficient quantity of at least one of C3 to C6 alkyl acrylamido glycolate C3 to C6 alkyl ether, C3 to C6 alkyl acrylamidoglycolate methyl ether, and methyl acrylamidoglycolate C3 to C6 alkyl ether to provide a non-viscous liquid, which comprises reacting glyoxylic acid with a C3 to C6 alcohol under conditions which lead to azeotropic removal of water to provide C3 to C6 alkyl glyoxylate alkyl hemiacetal, reacting said C3 to C6 alkyl glyoxylate alkyl hemiacetal with an acrylamide while removing volatiles therefrom to provide C3 to C6 alkyl acrylamidoglycolate and reacting said C3 to C6 alkyl acrylamidoglycolate with methanol at elevated temperature in the presence of a transesterification/etherification catalyst while removing water and volatiles therefrom to provide said methyl acrylamidoglycolate methyl ether in non-viscous liquid form.
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Abstract
Reaction of glyoxylic acid with a C3 to C6 alcohol capable of forming an azeotrope with water to form the C3 to C6 alkyl glyoxylate or alkyl glyoxylate alkyl hemiacetal, reacting the intermediate with acrylamide and optionally with a C3 to C6 alcohol to form the C3 to C6 alkyl acrylamidoglycolate or alkyl acrylamidoglycolate alkyl ether in essentially polymer free form which are readily converted by transesterification/etherification or transesterification/transetherification with methanol into predominately methyl acrylamidoglycolate methyl ether preferably in liquid form.
17 Citations
8 Claims
- 1. A process for preparing methyl acrylamidoglycolate methyl ether in non-viscous liquid form comprising a major proportion of methyl acrylamidoglycolate methyl ether and a sufficient quantity of at least one of C3 to C6 alkyl acrylamido glycolate C3 to C6 alkyl ether, C3 to C6 alkyl acrylamidoglycolate methyl ether, and methyl acrylamidoglycolate C3 to C6 alkyl ether to provide a non-viscous liquid, which comprises reacting glyoxylic acid with a C3 to C6 alcohol under conditions which lead to azeotropic removal of water to provide C3 to C6 alkyl glyoxylate alkyl hemiacetal, reacting said C3 to C6 alkyl glyoxylate alkyl hemiacetal with an acrylamide while removing volatiles therefrom to provide C3 to C6 alkyl acrylamidoglycolate and reacting said C3 to C6 alkyl acrylamidoglycolate with methanol at elevated temperature in the presence of a transesterification/etherification catalyst while removing water and volatiles therefrom to provide said methyl acrylamidoglycolate methyl ether in non-viscous liquid form.
- 5. A process for preparing methyl acrylamidoglycolate methyl ether in non-viscous liquid form comprising a major proportion of methyl acrylamidoglycolate methyl ether and a sufficient quantity of at least one of C3 to C6 alkyl acrylamidoglycolate C3 to C6 alkyl ether, C3 to C6 alkyl acrylamidoglycolate methyl ether, and methyl acrylamidoglycolate C3 to C6 alkyl ether to provide a non-viscous liquid, which comprises reacting glyoxylic acid with a C3 to C6 alcohol under conditions which lead to azeotropic removal of water to provide C3 to C6 alkyl hemiacetal, reacting said C3 to C6 alkyl alyoxylate alkyl hemiacetal with an acrylamide while removing volatiles thereform to provide C3 to C6 alkyl acrylamidoglycolate, reacting said C3 to C6 alkyl acrylamidoglycolate with a C3 to C6 alcohol in the presence of an etherification catalyst under conditions which lead to the azeotropic removal of water to provide a C3 to C6 alkyl acrylamidoglycolate alkyl ether and then reacting said C3 to C6 alkyl acrylamidoglycolate alkyl ether with methanol at elevated temperature in the presence of a transesterification/transetherification catalyst while removing volatiles therefrom to provide said methyl acrylamidoglycolate methyl ether in non-viscous liquid form.
Specification
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- Resources
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Current AssigneeAmerican Colloid Company (Minerals Technologies Incorporated)
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Original AssigneeAmerican Colloid Company (Minerals Technologies Incorporated)
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InventorsPhotis, James M.
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Primary Examiner(s)Shippen, Michael L.
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Application NumberUS06/377,505Time in Patent Office706 DaysField of Search560/170, 560/186US Class Current560/170CPC Class CodesC07C 233/45 having the nitrogen atom of...
