CA1173460A - Process for the manufacture of 3,3'-dichloro-4,4'- diamino-biphenyl-dihydrochloride - Google Patents
Process for the manufacture of 3,3'-dichloro-4,4'- diamino-biphenyl-dihydrochlorideInfo
- Publication number
- CA1173460A CA1173460A CA000386089A CA386089A CA1173460A CA 1173460 A CA1173460 A CA 1173460A CA 000386089 A CA000386089 A CA 000386089A CA 386089 A CA386089 A CA 386089A CA 1173460 A CA1173460 A CA 1173460A
- Authority
- CA
- Canada
- Prior art keywords
- ion
- temperature
- chloride
- stoichiometric amount
- agent
- 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.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/09—Diamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Abstract of the disclosure:
The 3,3'-dichloro-4,4'-diamino-biphenyl sulfate obtained in the form of a sulfuric-acid-containing solution from the "benzidine rearrangement" can be converted with good yield to a very pure dihydrochloride by heating the nearly saturated aqueous solution of the sulfate to a temperature in the range of from above 100°C to reflux temperature while adding about 50 to about 70 %
of the stoichiometric amount of a chloride-ion-yielding agent, especially hydrochloric acid, subsequently cooling to a temperature in the range of from about 90 to below 100°C, adding further chloride-ion-yielding agent, and cooling to about room temperature. It is especially advantageous to add first the remaining stoichiometric amount of precipitating agent or a slight excess thereof in the temperature range of from about 90 to below 100°C, and a larger excess of up to about twice the stoichiometric amount at a later moment. The dihydrochloride obtained in a well crystallized form is advantageously washed with hydrochloric acid; filtrate and washing water can be easily worked up to hydrochloric and sulfuric acid, respectively. The product is obtained in such a pure state that it can be directly processed to dyeing agents.
The 3,3'-dichloro-4,4'-diamino-biphenyl sulfate obtained in the form of a sulfuric-acid-containing solution from the "benzidine rearrangement" can be converted with good yield to a very pure dihydrochloride by heating the nearly saturated aqueous solution of the sulfate to a temperature in the range of from above 100°C to reflux temperature while adding about 50 to about 70 %
of the stoichiometric amount of a chloride-ion-yielding agent, especially hydrochloric acid, subsequently cooling to a temperature in the range of from about 90 to below 100°C, adding further chloride-ion-yielding agent, and cooling to about room temperature. It is especially advantageous to add first the remaining stoichiometric amount of precipitating agent or a slight excess thereof in the temperature range of from about 90 to below 100°C, and a larger excess of up to about twice the stoichiometric amount at a later moment. The dihydrochloride obtained in a well crystallized form is advantageously washed with hydrochloric acid; filtrate and washing water can be easily worked up to hydrochloric and sulfuric acid, respectively. The product is obtained in such a pure state that it can be directly processed to dyeing agents.
Claims (6)
1. In a process for the manufacture of 3,3'-dichloro-4,4'-diamino-biphenyl-dihydrochloride from the aqueous, sulfuric-acid -containing solution of the sulfate by precipitation with a chloride-ion-yielding agent, isolation and washing of the precipitated product with an aqueous solution containing a chloride-ion-yielding agent the improvement comprising heating the nearly saturated aqueous solution of the sulfate to a temperature in the range of from above 100°C to reflux temperature while adding about 50 to about 70 % of the stoichiometric amount of chloride-ion-yielding agent, subsequently cooling to a temperature in the range of from about 90 to below 100°C, adding further chloride-ion-yielding agent, and cooling to about room temperature.
2. The process as claimed in Claim 1, wherein the chloride-ion-yielding agent is hydrochloric acid.
3. The process as claimed in Claim 1, which comprises adding about 65 % of the stoichiometric amount of chloride-ion-yielding agent in the temperature range of above 100°C to reflux temperature, and further chloride-ion-yielding agent up to about twice the stoichiometric amount in the temperature range of from about 90 to below 100°C.
4. The process as claimed in Claim 1, which comprises adding first the remaining stoichiometric amount of chloride-ion-yielding agent or a slight excess thereof in the temperature range of from about 90 to below 100°C, and a larger excess of said agent at a later moment.
5. The process as claimed in Claim 1, which comprises washing the precipitated dihydrochloride with aqueous hydrochloric acid.
6. The process as claimed in Claim 5, which comprises reusing the washing filtrate for a subsequent crystallization.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3035221.7 | 1980-09-08 | ||
| DE19803035221 DE3035221A1 (en) | 1980-09-18 | 1980-09-18 | METHOD FOR PRODUCING 3,3'-DICHLOR-4,4'-DIAMINO-BIPHENYL DIHYDROCHLORIDE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1173460A true CA1173460A (en) | 1984-08-28 |
Family
ID=6112279
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000386089A Expired CA1173460A (en) | 1980-09-18 | 1981-09-17 | Process for the manufacture of 3,3'-dichloro-4,4'- diamino-biphenyl-dihydrochloride |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0048679B1 (en) |
| JP (1) | JPS5781442A (en) |
| KR (1) | KR880000889B1 (en) |
| CA (1) | CA1173460A (en) |
| DE (2) | DE3035221A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109836337A (en) * | 2019-03-08 | 2019-06-04 | 陕西大生制药科技有限公司 | A kind of method of purification of diphenyl amine compound |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE547986C (en) * | 1928-12-18 | 1932-04-01 | I G Farbenindustrie Akt Ges | Process for the separation of mixtures of aromatic amines |
| US2839578A (en) * | 1954-02-24 | 1958-06-17 | Eastman Kodak Co | Treatment of aromatic amino compounds |
-
1980
- 1980-09-18 DE DE19803035221 patent/DE3035221A1/en not_active Withdrawn
-
1981
- 1981-09-12 EP EP81710044A patent/EP0048679B1/en not_active Expired
- 1981-09-12 DE DE8181710044T patent/DE3164439D1/en not_active Expired
- 1981-09-16 KR KR1019810003457A patent/KR880000889B1/en active
- 1981-09-16 JP JP56144832A patent/JPS5781442A/en active Granted
- 1981-09-17 CA CA000386089A patent/CA1173460A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109836337A (en) * | 2019-03-08 | 2019-06-04 | 陕西大生制药科技有限公司 | A kind of method of purification of diphenyl amine compound |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3164439D1 (en) | 1984-08-02 |
| JPS5781442A (en) | 1982-05-21 |
| JPH026342B2 (en) | 1990-02-08 |
| KR830007504A (en) | 1983-10-21 |
| DE3035221A1 (en) | 1982-05-06 |
| EP0048679A1 (en) | 1982-03-31 |
| KR880000889B1 (en) | 1988-05-30 |
| EP0048679B1 (en) | 1984-06-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |