US4172948A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Preparation of diphenylmethane mono and dicarbamates and polymethylene polyphenyl carbamates
Assignee: Atlantic Richfield Co
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Filing: 1979-01-24
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Granted: 1979-10-30
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Expires: 1999-01-24
Abstract
Abstract Diphenylmethane mono and dicarbamates and polymethylene polyphenyl carbamate homologs and derivatives of these compounds are prepared by employing a superatmospheric pressure of anhydrous hydrogen chloride to catalytically rearrange an (alkoxycarbonyl)phenylaminomethylphenyl compound having the general formula <IMAGE> INCLUDING THE HIGHER HOMOLOGS OF SUCH COMPOUNDS, WHEREIN X, Y AND Z, WHICH ARE DIFFERENT ON THE RING, ARE AN ALKYL GROUP HAVING FROM 1 TO 3 CARBON ATOMS, AN -NHCOOR, -CH2ArNHCOOR or -N(COOR)CH2Ar group; x, y and z may also be at least one hydrogen; R is a 1 to 3 carbon atom alkyl group and Ar is phenyl which may be substituted with a 1 to 3 carbon atom alkyl group.
Inventors
- 👤 Edward T. Shawl
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 16:24
CPC Classifications
C; C07; C07C; C07C271/00; C07C271/06
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
167 words
A process for the preparation of a diphenylmethane mono and dicarbamate and polymethylene polyphenyl carbamate homologs and derivatives which comprises reacting under substantially anhydrous conditions, (alkoxycarbonyl)phenylaminomethylphenyl compound having the formula ##STR9## and the higher homologs of said compounds, wherein x, y and z, which are different on the ring are an alkyl group of from 1 to 3 carbon atoms, an --NHCOOR, --CH 2 ArNHCOOR or --N(COOR)CH 2 Ar group, R is a 1 to 3 carbon alkyl group and Ar is phenyl which may be substituted with an alkyl group of from 1 to 3 carbon atoms; x, y and z may also be at least one hydrogen; at a temperature in the range of from about 35° C. to 170° C. in the presence of an effective amount of an anhydrous hydrogen chloride catalyst at a pressure of from about 50 psig to 600 psig to rearrange the (alkoxycarbonyl)phenylaminomethylphenyl compounds to the mono and dicarbamates and polymethylene polyphenylcarbamates and derivatives and recovering the desired carbamate.
Claim 2
Dependent Claim
167 words
A process for the preparation of a diphenylmethane mono and dicarbamate and polymethylene polyphenyl carbamate homologs and derivatives which comprises reacting under substantially anhydrous conditions, (alkoxycarbonyl)phenylaminomethylphenyl compound having the formula ##STR9## and the higher homologs of said compounds, wherein x, y and z, which are different on the ring are an alkyl group of from 1 to 3 carbon atoms, an --NHCOOR, --CH 2 ArNHCOOR or --N(COOR)CH 2 Ar group, R is a 1 to 3 carbon alkyl group and Ar is phenyl which may be substituted with an alkyl group of from 1 to 3 carbon atoms; x, y and z may also be at least one hydrogen; at a temperature in the range of from about 35° C. to 170° C. in the presence of an effective amount of an anhydrous hydrogen chloride catalyst at a pressure of from about 50 psig to 600 psig to rearrange the (alkoxycarbonyl)phenylaminomethylphenyl compounds to the mono and dicarbamates and polymethylene polyphenylcarbamates and derivatives and recovering the desired carbamate.
Claim 3
Dependent Claim
33 words
A process according to claim 1 wherein the (alkoxycarbonyl)phenylaminomethylphenyl compound is derived from the condensation reaction of an N-aryl carbamic acid ester with a carbonyl compound in the presence of an acid solution.
Claim 4
Dependent Claim
13 words
A process according to claim 2 wherein the N-arylcarbamic acid ester is ethylphenylcarbamate.
Claim 5
Dependent Claim
12 words
A process according to claim 2 wherein the carbonyl compound is formaldehyde.
Claim 6
Dependent Claim
20 words
A process according to claim 1 wherein the (alkoxycarbonyl)phenylaminomethylphenyl compound is the ethyl ester of 2-[(ethoxycarbonyl)phenylaminomethyl]-phenylcarbamic acid or 4-[(ethoxycarbonyl)phenylaminomethyl]phenylcarbamic acid.
Claim 7
Dependent Claim
26 words
A process according to claim 1 wherein the reaction is carried out at a temperature in the range of from about 50° C. to 130° C.
Claim 8
Dependent Claim
24 words
A process according to claim 1 wherein the anhydrous hydrogen chloride is employed at a pressure of from about 75 psig to 250 psig.
Claim 9
Dependent Claim
45 words
A process according to claim 1 wherein the reaction is carried out in the presence of a solvent selected from the group consisting of nitrated and halogenated hydrocarbons having up to 12 carbon atoms, and alkanes and substituted alkanes having up to 16 carbon atoms.
Claim 10
Dependent Claim
14 words
A process according to claim 8 wherein the solvent is nitrobenzene, nitrotoluene or dichlorobenzene.
Claim 11
Dependent Claim
11 words
A process according to claim 9 wherein the solvent is nitrobenzene.
Claim 12
Dependent Claim
82 words
A process for the preparation of a diphenylmethane dicarbamate, diethyl ester, which comprises reacting the ethyl ester of 2-[(ethoxycarbonyl)phenylaminomethyl]phenylcarbamic acid or 4-[(ethoxycarbonyl)phenylaminomethyl]phenylcarbamic acid derived from the condensation reaction of ethylphenylcarbamate with a carbonyl compound in the presence of an aqueous acid solution, at a temperature in the range of from about 50° C. to 130° C. in the presence of an anhydrous hydrogen chloride catalyst at a pressure of from about 75 psig to 250 psig and recovering the desired diphenylmethane dicarbamate.
Claim 13
Dependent Claim
82 words
A process for the preparation of a diphenylmethane dicarbamate, diethyl ester, which comprises reacting the ethyl ester of 2-[(ethoxycarbonyl)phenylaminomethyl]phenylcarbamic acid or 4-[(ethoxycarbonyl)phenylaminomethyl]phenylcarbamic acid derived from the condensation reaction of ethylphenylcarbamate with a carbonyl compound in the presence of an aqueous acid solution, at a temperature in the range of from about 50° C. to 130° C. in the presence of an anhydrous hydrogen chloride catalyst at a pressure of from about 75 psig to 250 psig and recovering the desired diphenylmethane dicarbamate.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-10-29 | 1983-04-30 | 1983-10-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-10-29 | 1987-04-30 | 1987-10-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-10-29 | 1991-04-30 | 1991-10-30 | $7700.00 | Window Closed / Lapsed |