US4193937A
Expired / Lapsed
US
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Process for preparing 3-chloro- and 3,5-dichloro-anilines
Assignee: Bayer AG
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Filing: 1978-09-15
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Granted: 1980-03-18
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Expires: 1998-09-15
Abstract
Abstract Analines, meta-substituted by chlorine are prepared by reacting chloro-anilines having the formula ##STR1## wherein X 1 and X 2 are the same or different and represent chlorine, hydrogen or optionally substituted alkyl, aryl, aralkyl, alkoxy or aralkoxy, with one of the radicals X 1 or X 2 representing chlorine when 3-chloroanilines are being prepared and X 1 and X 2 representing chlorine when 3,5-dichloroanilines are being prepared and R 1 , R 2 and R 3 are the same or different and represent chlorine, hydrogen or optionally substituted alkyl, aryl, aralkyl, alkoxy or aralkoxy, with at least one of the radicals R 1 , R 2 or R 3 representing chlorine with hydrogen in solution in a neutral or acid medium in the presence of noble metals which are in the elementary form or in the form of compounds and are optionally applied to supports, and in the presence of sulfur or sulfur compounds at elevated temperatures and under pressure.
Inventors
- 👤 Karlfried Wedemeyer
- 👤 Wolfgang Kiel
- 👤 Werner Evertz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 11:37
CPC Classifications
B; B01; B01J; B01J23/00; B01J23/38; B01J23/40; B01J37/00; B01J37/02; B01J37/03; B01J37/031
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
185 words
Process for preparing anilines meta-substituted by chlorine which comprises reacting chloroanilines having the formula ##STR7## wherein X 1 and X 2 are the same or different and represent chlorine, hydrogen or optionally substituted alkyl, aryl, aralkyl, alkoxy or aralkoxy, with one of the radicals X 1 or X 2 representing chlorine when 3-chloroanilines are being prepared and X 1 and X 2 representing chlorine when 3,5-dichloroanilines are being prepared and R 1 , R 2 and R 3 are the same or different and represent chlorine, hydrogen or optionally substituted alkyl, aryl, aralkyl, alkoxy or aralkoxy, with at least one of the radicals R 1 , R 2 or R 3 representing chlorine, with hydrogen in solution in an acid medium in the presence of noble metals which are in the elementary form or in the form of compounds and are optionally applied to supports, and in the presence of sulfur or sulfur compounds at elevated temperatures and under pressure, said chloroaniline being introduced into a reaction vessel and the pH of the contents thereof being adjusted to less than 6.5 before addition of hydrogen.
Claim 2
Dependent Claim
185 words
Process for preparing anilines meta-substituted by chlorine which comprises reacting chloroanilines having the formula ##STR7## wherein X 1 and X 2 are the same or different and represent chlorine, hydrogen or optionally substituted alkyl, aryl, aralkyl, alkoxy or aralkoxy, with one of the radicals X 1 or X 2 representing chlorine when 3-chloroanilines are being prepared and X 1 and X 2 representing chlorine when 3,5-dichloroanilines are being prepared and R 1 , R 2 and R 3 are the same or different and represent chlorine, hydrogen or optionally substituted alkyl, aryl, aralkyl, alkoxy or aralkoxy, with at least one of the radicals R 1 , R 2 or R 3 representing chlorine, with hydrogen in solution in an acid medium in the presence of noble metals which are in the elementary form or in the form of compounds and are optionally applied to supports, and in the presence of sulfur or sulfur compounds at elevated temperatures and under pressure, said chloroaniline being introduced into a reaction vessel and the pH of the contents thereof being adjusted to less than 6.5 before addition of hydrogen.
Claim 3
Dependent Claim
14 words
Process of claim 1 carried out at temperatures of from 150° to 350° C.
Claim 4
Dependent Claim
14 words
Process of claim 1 carried out at temperatures of from 180° to 270° C.
Claim 5
Dependent Claim
17 words
Process of claim 1 carried out at a hydrogen pressure of from 20 to 200 atmospheres gauge.
Claim 6
Dependent Claim
17 words
Process of claim 1 carried out at a hydrogen pressure of from 60 to 120 atmospheres gauge.
Claim 7
Dependent Claim
101 words
Process of claim 1 wherein the chloroanilines have the formula ##STR8## wherein X 3 and X 4 are the same or different and represent chlorine or hydrogen, with one of the radicals X 3 or X 4 representing chlorine when 3-chloroanilines are being prepared and X 3 and X 4 representing chlorine when 3,5-dichloroanilines are being prepared, and R 7 , R 8 and R 9 are the same or different and represent chlorine, hydrogen, the methyl or phenyl group or the radicals ##STR9## with at least one of the radicals R 7 , R 8 or R 9 representing chlorine.
Claim 8
Dependent Claim
27 words
Process of claim 1 wherein the noble metals used are elements of group VIII of the periodic table, in the elementary form or as oxides or sulfides.
Claim 9
Dependent Claim
14 words
Process of claim 1 wherein palladium or platinum are used as the noble metal.
Claim 10
Dependent Claim
16 words
Process of claim 1 wherein the noble metals are used on a support of active charcoal.
Claim 11
Dependent Claim
16 words
Process of claim 1 wherein the reaction is carried out in the presence of elementary sulfur.
Claim 12
Dependent Claim
17 words
Process of claim 1 wherein the reaction is carried out in the presence of inorganic sulfur compounds.
Claim 13
Dependent Claim
17 words
Process of claim 1 wherein the reaction is carried out in the presence of monosulfides or polysulfides.
Claim 14
Dependent Claim
17 words
Process of claim 1 wherein the reaction is carried out in the presence of organic sulfur compounds.
Claim 15
Dependent Claim
16 words
Process of claim 1 wherein the reaction is carried out in the presence of carbon disulfide.
Claim 16
Dependent Claim
57 words
Process of claim 1 wherein the catalyst is prepared by suspending the noble metal applied to a support, or the noble metal compound, in the aqueous solution of a metal salt and precipitating the sparingly water-soluble metal sulfide onto the noble metal applied to a support, or the noble metal compound, by adding a water-soluble sulfide compound.
Claim 17
Dependent Claim
57 words
Process of claim 1 wherein the catalyst is prepared by suspending the noble metal applied to a support, or the noble metal compound, in the aqueous solution of a metal salt and precipitating the sparingly water-soluble metal polysulfide onto the noble metal applied to a support, or the noble metal compound, by adding a water-soluble polysulfide compound.
Claim 18
Dependent Claim
19 words
A process according to claim 1 wherein the pH is adjusted by introducing therein an inorganic or organic acid.
Claim 19
Dependent Claim
13 words
A process according to claim 17 wherein the acid is an inorganic acid.
Claim 20
Dependent Claim
16 words
A process according ro claim 18 wherein the inorganic acid is hydrochloric, sulfuric or phosphoric acid.
Claim 21
Dependent Claim
13 words
A process according to claim 17 wherein said acid is an organic acid.
Claim 22
Dependent Claim
15 words
A process according to claim 20 wherein the organic acid is acetic or propionic acid.
Claim 23
Dependent Claim
189 words
Process for preparing anilines meta-substituted by chlorine which comprises reacting chloroanilines having the formula ##STR10## wherein X 1 and X 2 are the same or different and represent chlorine, hydrogen or optionally substituted alkyl, aryl, aralkyl, alkoxy or aralkoxy, with one of the radicals X 1 or X 2 representing chlorine when 3-chloroanilines are being prepared and X 1 and X 2 representing chlorine when 3,5-dichloroanilines are being prepared and R 1 , R 2 and R 3 are the same or different and represent chlorine, hydrogen or optionally substituted alkyl, aryl, aralkyl, alkoxy or aralkoxy, with at least one of the radicals R 1 , R 2 or R 3 representing chlorine, with hydrogen in solution in a neutral or acid medium in the presence of noble metals which are in the elementary form or in the form of compounds and are optionally applied to supports, and in the presence of sulfur or sulfur compounds at elevated temperatures and under pressure, the hydrogen being introduced into a reaction vessel containing the chloroaniline and as the acid of the acid medium an organic acid, sulfuric acid or phosphoric acid.
Claim 24
Dependent Claim
189 words
Process for preparing anilines meta-substituted by chlorine which comprises reacting chloroanilines having the formula ##STR10## wherein X 1 and X 2 are the same or different and represent chlorine, hydrogen or optionally substituted alkyl, aryl, aralkyl, alkoxy or aralkoxy, with one of the radicals X 1 or X 2 representing chlorine when 3-chloroanilines are being prepared and X 1 and X 2 representing chlorine when 3,5-dichloroanilines are being prepared and R 1 , R 2 and R 3 are the same or different and represent chlorine, hydrogen or optionally substituted alkyl, aryl, aralkyl, alkoxy or aralkoxy, with at least one of the radicals R 1 , R 2 or R 3 representing chlorine, with hydrogen in solution in a neutral or acid medium in the presence of noble metals which are in the elementary form or in the form of compounds and are optionally applied to supports, and in the presence of sulfur or sulfur compounds at elevated temperatures and under pressure, the hydrogen being introduced into a reaction vessel containing the chloroaniline and as the acid of the acid medium an organic acid, sulfuric acid or phosphoric acid.
Claim 25
Dependent Claim
13 words
A process according to claim 22 wherein the acid is an organic acid.
Claim 26
Dependent Claim
14 words
A process according to claim 22 wherein the inorganic acid is sulfuric or phosphoric.
References Cited (Backward Citations)
US3912783A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-03-18 | 1983-09-17 | 1984-03-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-03-18 | 1987-09-17 | 1988-03-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-03-18 | 1991-09-17 | 1992-03-18 | $7700.00 | Window Closed / Lapsed |