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US4133833A
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Production of N,N-di(ethyl)-meta-toluamide from meta-toluic acid by liquid phase catalytic reaction with diethylamine
Assignee: Vertellus Performance Materials Inc
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Filing: 1978-01-09
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Granted: 1979-01-09
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Expires: 1998-01-09
Abstract
Abstract Meta-toluic acid reacts with diethylamine in the liquid phase at elevated temperatures in the presence of a catalyst selected from the group consisting of titanium tetrachloride and certain organic titanates to form N,N-diethyl-meta-toluamide.
Inventors
- 👤 Ezekiel H. Hull
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 17:56
CPC Classifications
C; C07; C07C; C07C233/00; C07C233/01; C07C233/12
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
124 words
A process for the preparation of N,N-diethyl-meta-toluamide which comprises contacting meta-toluic acid with diethylamine in the liquid phase at a temperature of about 150° C. to 300° C. in the presence of a catalyst in the amount of about 0.0001 to 0.1 gram per gram of said meta-toluic acid, said catalyst being selected from the group consisting of titanium tetrachloride; Ti(OA) 4 wherein the four A moieties may be identical or not and each is selected from the group consisting of alkyl of from 3 to 18 carbon atoms; triethanolamine titanate chelates; titanium acetylacetonate chelates; tetraoctylene glycol titanate chelates; and titanium lactate ammonium salt chelates, and the water produced during said contacting being removed from said liquid phase during the course of said preparation.
Claim 2
Dependent Claim
124 words
A process for the preparation of N,N-diethyl-meta-toluamide which comprises contacting meta-toluic acid with diethylamine in the liquid phase at a temperature of about 150° C. to 300° C. in the presence of a catalyst in the amount of about 0.0001 to 0.1 gram per gram of said meta-toluic acid, said catalyst being selected from the group consisting of titanium tetrachloride; Ti(OA) 4 wherein the four A moieties may be identical or not and each is selected from the group consisting of alkyl of from 3 to 18 carbon atoms; triethanolamine titanate chelates; titanium acetylacetonate chelates; tetraoctylene glycol titanate chelates; and titanium lactate ammonium salt chelates, and the water produced during said contacting being removed from said liquid phase during the course of said preparation.
Claim 3
Dependent Claim
19 words
The process of claim 1 wherein said catalyst is Ti(OA) 4 wherein A is as defined in claim 1.
Claim 4
Dependent Claim
11 words
The process of claim 2 wherein said catalyst is tetra(n-butyl) titanate.
Claim 5
Dependent Claim
13 words
The process of claim 1 wherein said catalyst is a triethanolamine titanate chelate.
Claim 6
Dependent Claim
25 words
The process of claim 1 wherein said catalyst is present in an amount of about 0.001 to 0.02 gram per gram of said meta-toluic acid.
Claim 7
Dependent Claim
15 words
The process of claim 1 wherein said temperature is about 205° C. to 250° C.
Claim 8
Dependent Claim
21 words
The process of claim 1 wherein meta-toluic acid and diethylamine are contacted in a molar ratio of about 0.5:1 to 2:1.
Claim 9
Dependent Claim
41 words
The process of claim 1 wherein said temperature is about 205° C. to 250° C., said preparation is performed at reflux under about atmospheric pressure, and said water is removed from said liquid phase by azeotropic distillation with benzene or toluene.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-01-08 | 1982-07-10 | 1983-01-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-01-08 | 1986-07-10 | 1987-01-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-01-08 | 1990-07-10 | 1991-01-09 | $7700.00 | Window Closed / Lapsed |