CA2065088A1 - Method of preparing 4-aminodiphenylamine - Google Patents
Method of preparing 4-aminodiphenylamineInfo
- Publication number
- CA2065088A1 CA2065088A1 CA002065088A CA2065088A CA2065088A1 CA 2065088 A1 CA2065088 A1 CA 2065088A1 CA 002065088 A CA002065088 A CA 002065088A CA 2065088 A CA2065088 A CA 2065088A CA 2065088 A1 CA2065088 A1 CA 2065088A1
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- substituted derivatives
- alkyl
- derivatives
- adpa
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 2
- OIJHFHYPXWSVPF-UHFFFAOYSA-N para-Nitrosodiphenylamine Chemical compound C1=CC(N=O)=CC=C1NC1=CC=CC=C1 OIJHFHYPXWSVPF-UHFFFAOYSA-N 0.000 abstract 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 abstract 1
- XXYMSQQCBUKFHE-UHFFFAOYSA-N 4-nitro-n-phenylaniline Chemical class C1=CC([N+](=O)[O-])=CC=C1NC1=CC=CC=C1 XXYMSQQCBUKFHE-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 150000003863 ammonium salts Chemical group 0.000 abstract 1
- 150000001448 anilines Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A method of producing 4-ADPA is disclosed wherein aniline or substituted aniline derivatives and nitrobenzene are reacted under suitable conditions to produce 4-nitrodiphrenylamine ar substituted derivatives thereof and/or 4-nitrosodiphenylamine or substituted derivatives thereof and/or their salts, either or both of which are subsequently reduced to produce 4-ADPA or substituted derivatives thereof. The 4-ADPA or substituted derivatives thereof can be reductively alkylated to produce p-phenylenediamine products or substituted derivatives thereof which are useful as antiozonants. A second embodiment of the invention is the tetrasubstituted ammonium salts or alkyl substituted diammonium salts of 4-nitrodiphenylamine, 4-nitrosodiphenylamine and the substituted derivatives thereof wherein each substituent of the tetrasubstituted ammonium ion is independently selected from the group consisting of alkyl, aryl and arylalkyl groups and each alkyl substituent of the alkyl substituted diammonium salt is independently selected.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1992/002232 WO1993000324A1 (en) | 1991-06-21 | 1992-03-27 | Method of preparing 4-aminodiphenylamine |
| USPCT/US92/02232 | 1992-03-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2065088A1 true CA2065088A1 (en) | 1993-09-28 |
| CA2065088C CA2065088C (en) | 2001-06-12 |
Family
ID=22230904
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002065088A Expired - Lifetime CA2065088C (en) | 1992-03-27 | 1992-04-03 | Method of preparing 4-aminodiphenylamine |
Country Status (2)
| Country | Link |
|---|---|
| CA (1) | CA2065088C (en) |
| TW (1) | TW379210B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9938217B2 (en) | 2016-07-01 | 2018-04-10 | Res Usa, Llc | Fluidized bed membrane reactor |
| US9981896B2 (en) | 2016-07-01 | 2018-05-29 | Res Usa, Llc | Conversion of methane to dimethyl ether |
| US10189763B2 (en) | 2016-07-01 | 2019-01-29 | Res Usa, Llc | Reduction of greenhouse gas emission |
| CN112439454A (en) * | 2019-09-05 | 2021-03-05 | 中石化南京化工研究院有限公司 | RT base condensation catalyst and preparation method thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116095890A (en) * | 2023-01-13 | 2023-05-09 | 北京六合宁远医药科技股份有限公司 | Synthetic method containing trifluoromethyl indazole boronic acid |
-
1992
- 1992-04-03 CA CA002065088A patent/CA2065088C/en not_active Expired - Lifetime
- 1992-04-08 TW TW081102690A patent/TW379210B/en active
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9938217B2 (en) | 2016-07-01 | 2018-04-10 | Res Usa, Llc | Fluidized bed membrane reactor |
| US9981896B2 (en) | 2016-07-01 | 2018-05-29 | Res Usa, Llc | Conversion of methane to dimethyl ether |
| US10189763B2 (en) | 2016-07-01 | 2019-01-29 | Res Usa, Llc | Reduction of greenhouse gas emission |
| CN112439454A (en) * | 2019-09-05 | 2021-03-05 | 中石化南京化工研究院有限公司 | RT base condensation catalyst and preparation method thereof |
| CN112439454B (en) * | 2019-09-05 | 2023-04-07 | 中国石油化工股份有限公司 | RT base condensation catalyst and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2065088C (en) | 2001-06-12 |
| TW379210B (en) | 2000-01-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 20120403 |