US4381403A
Expired / Lapsed
US
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Process for the preparation of N-monosubstituted carbamic acid esters
Assignee: Lyondell Chemical Technology LP
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Filing: 1980-03-31
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Granted: 1983-04-26
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Expires: 2000-03-31
Abstract
Abstract A process for the preparation of N-monosubstituted carbamic acid esters by reacting an unsubstituted carbamic acid ester and an aromatic primary amine at a suitable pressure and reaction temperature in the presence of a monohydric aliphatic alcohol and preferably in the presence of a strongly basic tertiary amine as catalyst. Optionally an inert co-solvent in addition to the alcohol may be employed.
Inventors
- 👤 Samuel J. Falcone
- 👤 John J. McCoy
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 15:36
CPC Classifications
C; C07; C07C; C07C269/00; C07C269/04
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
160 words
A process for the preparation of an N-monosubstituted carbamic acid ester which comprises reacting an unsubstituted carbamic acid ester having the formula NH 2 CO 2 R wherein R is a straight or branched chain alkyl group containing from 1 to 10 carbon atoms, with an aromatic primary amine having the formula R'(NH 2 )n wherein R' is a substituted or unsubstituted aryl or aralkyl group containing one or more benzenoid rings which may be fused or joined by single valency bonds and n is an integer of 1 to 6, at a temperature in the range of from about 125° C. to 250° C. in the presence of a monohydric aliphatic alcohol having from 1 to 10 carbon atoms and a catalytic amount of from about 0.01 to 30 mole percent based on the aromatic primary amine employed of a tertiary amine which may be an aliphatic, cycloaliphatic, aryliphatic or aromatic amine containing from 1 to 18 carbon atoms.
Claim 2
Dependent Claim
160 words
A process for the preparation of an N-monosubstituted carbamic acid ester which comprises reacting an unsubstituted carbamic acid ester having the formula NH 2 CO 2 R wherein R is a straight or branched chain alkyl group containing from 1 to 10 carbon atoms, with an aromatic primary amine having the formula R'(NH 2 )n wherein R' is a substituted or unsubstituted aryl or aralkyl group containing one or more benzenoid rings which may be fused or joined by single valency bonds and n is an integer of 1 to 6, at a temperature in the range of from about 125° C. to 250° C. in the presence of a monohydric aliphatic alcohol having from 1 to 10 carbon atoms and a catalytic amount of from about 0.01 to 30 mole percent based on the aromatic primary amine employed of a tertiary amine which may be an aliphatic, cycloaliphatic, aryliphatic or aromatic amine containing from 1 to 18 carbon atoms.
Claim 3
Dependent Claim
23 words
A process according to claim 1 wherein the unsubstituted carbamic acid ester is selected from the group consisting of methylcarbamate, ethylcarbamate, and octylcarbamate.
Claim 4
Dependent Claim
15 words
A process according to claim 2 wherein the unsubstituted carbamic acid ester is ethyl carbamate.
Claim 5
Dependent Claim
23 words
A process according to claim 1 wherein the aromatic primary amine is selected from the group consisting of aniline, toluene diamines and naphthylamines.
Claim 6
Dependent Claim
13 words
A process according to claim 4 wherein the aromatic primary amine is aniline.
Claim 7
Dependent Claim
29 words
A process according to claim 1 wherein the reactant aromatic primary amine to unsubstituted carbamic acid ester is employed at a molar ratio of from about 10:1 to 0.1:1.
Claim 8
Dependent Claim
17 words
A process according to claim 6 wherein the molar ratio employed is from about 5:1 to 0.25:1.
Claim 9
Dependent Claim
30 words
A process according to claim 1 wherein the alcohol is employed at a molar ratio of from about 0.5:1 to 15:1 based on the amine or unsubstituted carbamic acid reactant.
Claim 10
Dependent Claim
23 words
A process according to claim 1 wherein the monohydric aliphatic alcohol is selected from the group consisting of methanol, ethanol, octanol and decanol.
Claim 11
Dependent Claim
11 words
A process according to claim 9 wherein the alcohol is ethanol.
Claim 12
Dependent Claim
11 words
A process according to claim 9 wherein the alcohol is methanol.
Claim 13
Dependent Claim
29 words
A process according to claim 1 wherein the tertiary amine is employed in a catalytic amount of from 0.1 to 20 mole percent of the aromatic primary amine employed.
Claim 14
Dependent Claim
24 words
A process according to claim 1 wherein the tertiary amine is selected from the group consisting of triethylamine, tri-n-propylamine, tri-n-octylamine, pyridine, 1,5-diazabicyclo[4.3.0]non-5-ene and 1,8-diazabicyclo[5.4.0]undec-7-ene.
Claim 15
Dependent Claim
12 words
A process according to claim 13 wherein the tertiary amine is triethylamine.
Claim 16
Dependent Claim
12 words
A process according to claim 13 wherein the tertiary amine is pyridine.
Claim 17
Dependent Claim
12 words
A process according to claim 13 wherein the tertiary amine is 1,8-diazabicyclo[5.4.0]undec-7-ene.
Claim 18
Dependent Claim
22 words
A process according to claim 1 wherein the reaction temperature is in the range of from about 175° C. to 225° C.
Claim 19
Dependent Claim
21 words
A process according to claim 1 wherein the reaction is carried out under a pressure of from 1 to 50 atmospheres.
Claim 20
Dependent Claim
24 words
A process according to claim 1 wherein the reaction is carried out in the presence of an inert solvent in addition to the alcohol.
Claim 21
Dependent Claim
58 words
A process for the preparation of ethylphenylcarbamate which comprises reacting ethylcarbamate with aniline at a temperature of from about 175° C. to 225° C. at a molar ratio of aniline to ethylcarbamate in the range of from 5:1 to 0.25:1 in the presence of ethyl alcohol and a catalytic amount of from 0.1 to 20 mole percent triethylamine.
Claim 22
Dependent Claim
58 words
A process for the preparation of ethylphenylcarbamate which comprises reacting ethylcarbamate with aniline at a temperature of from about 175° C. to 225° C. at a molar ratio of aniline to ethylcarbamate in the range of from 5:1 to 0.25:1 in the presence of ethyl alcohol and a catalytic amount of from 0.1 to 20 mole percent triethylamine.
Claim 23
Dependent Claim
19 words
A process according to claim 20 wherein the reaction is carried out in the presence of an inert solvent.
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) | 1986-04-25 | 1986-10-25 | 1987-04-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-04-25 | 1990-10-25 | 1991-04-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-04-25 | 1994-10-25 | 1995-04-26 | $7700.00 | Window Closed / Lapsed |