US4443623A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Preparation of predominately methyl acrylamidoglycolate methyl ether in a normally liquid product
Assignee: Wyeth Holdings LLC
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Filing: 1982-05-12
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Granted: 1984-04-17
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Expires: 2002-05-12
Abstract
Abstract Reaction of glyoxylic acid with a C 3 to C 6 alcohol capable of forming an azeotrope with water to form the C 3 to C 6 alkyl glyoxylate or alkyl glyoxylate alkyl hemiacetal, reacting the intermediate with acrylamide and optionally with a C 3 to C 6 alcohol to form the C 3 to C 6 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.
Inventors
- 👤 James M. Photis
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 13:50
CPC Classifications
C; C07; C07C; C07C233/00; C07C233/01; C07C233/45
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
168 words
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 C 3 to C 6 alkyl acrylamido glycolate C 3 to C 6 alkyl ether, C 3 to C 6 alkyl acrylamidoglycolate methyl ether, and methyl acrylamidoglycolate C 3 to C 6 alkyl ether to provide a non-viscous liquid, which comprises reacting glyoxylic acid with a C 3 to C 6 alcohol under conditions which lead to azeotropic removal of water to provide C 3 to C 6 alkyl glyoxylate alkyl hemiacetal, reacting said C 3 to C 6 alkyl glyoxylate alkyl hemiacetal with an acrylamide while removing volatiles therefrom to provide C 3 to C 6 alkyl acrylamidoglycolate and reacting said C 3 to C 6 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.
Claim 2
Dependent Claim
168 words
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 C 3 to C 6 alkyl acrylamido glycolate C 3 to C 6 alkyl ether, C 3 to C 6 alkyl acrylamidoglycolate methyl ether, and methyl acrylamidoglycolate C 3 to C 6 alkyl ether to provide a non-viscous liquid, which comprises reacting glyoxylic acid with a C 3 to C 6 alcohol under conditions which lead to azeotropic removal of water to provide C 3 to C 6 alkyl glyoxylate alkyl hemiacetal, reacting said C 3 to C 6 alkyl glyoxylate alkyl hemiacetal with an acrylamide while removing volatiles therefrom to provide C 3 to C 6 alkyl acrylamidoglycolate and reacting said C 3 to C 6 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.
Claim 3
Dependent Claim
10 words
The process of claim 1 wherein said acrylamide is methacrylamide.
Claim 4
Dependent Claim
15 words
The process of claim 1 wherein said C 3 to C 6 alcohol is butanol.
Claim 5
Dependent Claim
12 words
The process of claim 1 wherein said transesterification/etherification catalyst is sulfuric acid.
Claim 6
Dependent Claim
212 words
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 C 3 to C 6 alkyl acrylamidoglycolate C 3 to C 6 alkyl ether, C 3 to C 6 alkyl acrylamidoglycolate methyl ether, and methyl acrylamidoglycolate C 3 to C 6 alkyl ether to provide a non-viscous liquid, which comprises reacting glyoxylic acid with a C 3 to C 6 alcohol under conditions which lead to azeotropic removal of water to provide C 3 to C 6 alkyl hemiacetal, reacting said C 3 to C 6 alkyl alyoxylate alkyl hemiacetal with an acrylamide while removing volatiles thereform to provide C 3 to C 6 alkyl acrylamidoglycolate, reacting said C 3 to C 6 alkyl acrylamidoglycolate with a C 3 to C 6 alcohol in the presence of an etherification catalyst under conditions which lead to the azeotropic removal of water to provide a C 3 to C 6 alkyl acrylamidoglycolate alkyl ether and then reacting said C 3 to C 6 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.
Claim 7
Dependent Claim
212 words
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 C 3 to C 6 alkyl acrylamidoglycolate C 3 to C 6 alkyl ether, C 3 to C 6 alkyl acrylamidoglycolate methyl ether, and methyl acrylamidoglycolate C 3 to C 6 alkyl ether to provide a non-viscous liquid, which comprises reacting glyoxylic acid with a C 3 to C 6 alcohol under conditions which lead to azeotropic removal of water to provide C 3 to C 6 alkyl hemiacetal, reacting said C 3 to C 6 alkyl alyoxylate alkyl hemiacetal with an acrylamide while removing volatiles thereform to provide C 3 to C 6 alkyl acrylamidoglycolate, reacting said C 3 to C 6 alkyl acrylamidoglycolate with a C 3 to C 6 alcohol in the presence of an etherification catalyst under conditions which lead to the azeotropic removal of water to provide a C 3 to C 6 alkyl acrylamidoglycolate alkyl ether and then reacting said C 3 to C 6 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.
Claim 8
Dependent Claim
10 words
The process of claim 5 wherein said acrylamide is methacrylamide.
Claim 9
Dependent Claim
15 words
The process of claim 5 wherein said C 3 to C 6 alcohol is butanol.
Claim 10
Dependent Claim
16 words
The process of claim 5, wherein said etherification catalyst and said transesterification/transetherification catalyst are sulfuric acid.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1987-04-17 | 1987-10-17 | 1988-04-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-04-17 | 1991-10-17 | 1992-04-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-04-17 | 1995-10-17 | 1996-04-17 | $7700.00 | Window Closed / Lapsed |