US3852350A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process of preparing amides
Assignee: Goodyear Tire and Rubber Co
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Filing: 1972-09-05
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Granted: 1974-12-03
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Expires: 1992-09-05
Abstract
Abstract Amides are prepared by reacting an aromatic amine with an acid chloride in the presence of a neutralizing agent and a catalytic amount of a strongly basic tertiary amine; for example, N-(4anilinophenyl) methacrylamide prepared by reacting paminodiphenylamine with methacryloyl chloride in the presence of sodium carbonate and triethylamine.
Inventors
- 👤 F Wilson
- 👤 T Slam
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 19:20
CPC Classifications
C; C07; C07C; C07C231/00
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
126 words
A PROCESS OF PREPARING AN AMIDE BY REACTING AN AROMATIC AMINE WITH AN ACID CHLORIDE IN AN APROTIC SOLVENT SOLUTION THEREOF IN THE PRESENCE OF AN INORGANIC NEUTRALIZING AGENT AND A CATALYTIC AMOUNT OF A TERTIARY AMINE, WHEREIN THE AROMATIC AMINE, NEUTRALIZING AGENT AND TERTIARY AMINE ARE COMBINED IN THE APROTIC SOLVENT, SAID COMBINATION THEN BEING COMBINED WITH THE ACID CHLORIDE AT A TEMPERATURE OF LESS THAN 50*C., AND THE REACTION OCCURRING AT A TEMPERATURE OF LESS THAN 50*C., WHEREIN AT LEAST ONE MOLE EQUIVALENT OF THE NEUTRALIZING AGENT IS USED PER MOLE OF AROMATIC AMINE AND WHEREIN THE CATALYTIC AMOUNT OF THE TERTIARY AMINE IS 0.0033 MOLE TO 0.20 MOLE PER MOLE OF AROMATIC AMINE AND WHEREIN THE AROMATIC AMINE HAS THE FOLLOWING STRUCTURAL FORMULA
Claim 2
Dependent Claim
126 words
A PROCESS OF PREPARING AN AMIDE BY REACTING AN AROMATIC AMINE WITH AN ACID CHLORIDE IN AN APROTIC SOLVENT SOLUTION THEREOF IN THE PRESENCE OF AN INORGANIC NEUTRALIZING AGENT AND A CATALYTIC AMOUNT OF A TERTIARY AMINE, WHEREIN THE AROMATIC AMINE, NEUTRALIZING AGENT AND TERTIARY AMINE ARE COMBINED IN THE APROTIC SOLVENT, SAID COMBINATION THEN BEING COMBINED WITH THE ACID CHLORIDE AT A TEMPERATURE OF LESS THAN 50*C., AND THE REACTION OCCURRING AT A TEMPERATURE OF LESS THAN 50*C., WHEREIN AT LEAST ONE MOLE EQUIVALENT OF THE NEUTRALIZING AGENT IS USED PER MOLE OF AROMATIC AMINE AND WHEREIN THE CATALYTIC AMOUNT OF THE TERTIARY AMINE IS 0.0033 MOLE TO 0.20 MOLE PER MOLE OF AROMATIC AMINE AND WHEREIN THE AROMATIC AMINE HAS THE FOLLOWING STRUCTURAL FORMULA
Claim 3
Dependent Claim
21 words
The process according to claim 1 wherein at least one mole of acid chloride is added per mole of aromatic amine.
Claim 4
Dependent Claim
22 words
The process according to claim 2 wherein at least two molar equivalents of neutralizing agent are added per mole of aromatic amine.
Claim 5
Dependent Claim
16 words
The process according to claim 3 wherein the catalyst level is from 0.033 to 0.04 mole.
Claim 6
Dependent Claim
14 words
The process according to claim 3 wherein R18 is hydrogen and R3 is phenyl.
Claim 7
Dependent Claim
23 words
The process according to claim 3 wherein the tertiary amine is selected from the group consisting of N,N''-dimethylaniline, triisopropanol amine, N,N,N'',N''-tetramethylethylenediamine and triethylamine.
Claim 8
Dependent Claim
29 words
The process according to claim 3 wherein the aromatic amine is p-aminodiphenyl amine and the acid chloride is selected from the group consisting of acryloyl chloride and methacryloyl chloride.
Claim 9
Dependent Claim
13 words
The process according to claim 7 wherein the neutralizing agent is sodium carbonate.
Claim 10
Dependent Claim
33 words
The process according to claim 8 wherein when the acid chloride is acryloyl chloride the tertiary amine is triisopropanol amine and when the acid chloride is methacryloyl chloride, the tertiary amine is N,N''-dimethylaniline.
Claim 11
Dependent Claim
26 words
The process according to claim 3 wherein the acid chloride is methacryloyl chloride, and is added at a temperature of from 0* C. to 30* C.
Claim 12
Dependent Claim
40 words
The process according to claim 3 wherein when the acid chloride is acryloyl chloride and is added at a temperature of -10* C. to 15* C. and held at -10* C. to 15* C. until the reaction is substantially complete.
References Cited (Backward Citations)
US3658769A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1977-12-02 | 1978-06-03 | 1978-12-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1981-12-02 | 1982-06-03 | 1982-12-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1985-12-02 | 1986-06-03 | 1986-12-03 | $7700.00 | Window Closed / Lapsed |