GB468375A - Improvements in the manufacture and production of partially hydrogenated compounds containing several nuclei - Google Patents
Improvements in the manufacture and production of partially hydrogenated compounds containing several nucleiInfo
- Publication number
- GB468375A GB468375A GB5436A GB5436A GB468375A GB 468375 A GB468375 A GB 468375A GB 5436 A GB5436 A GB 5436A GB 5436 A GB5436 A GB 5436A GB 468375 A GB468375 A GB 468375A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nickel
- hydroxy
- compounds
- treating
- naphthol
- 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Abstract
Partially hydrogenated hydroxy compounds are manufactured by treating aromatic or heterocyclic monohydroxy compounds, containing at least two nuclei which are joined together directly and which may contain other substituents in addition to the hydroxy group, in alkaline solution with hydrogen under increased pressure, e.g. above 25 atmospheres, preferably at 100--250 atmospheres, in the presence of hydrogenation catalysts, preferably at elevated temperatures, e.g. 70--150 DEG C., whereby hydrogenation takes place in the nucleus not containing the hydroxy group, and in some cases also partially in the nucleus containing the hydroxy group. The process is applicable to the hydrogenation of monohydroxy compounds of the naphthalene series, e.g. a - and b -naphthol, hydroxynaphthoic acids and their amides, e.g. anilides, toluidides or xylidides, and similar hydroxy compounds of anthracene, phenanthrene, diphenyl, diphenylene oxide, quinoline and carbazole, and also phenylpyrazolones, which are capable of reacting as hydroxy compounds. The reaction is effected by bringing the hydroxy compound into aqueous or alcoholic alkaline solution, adding a hydrogenation catalyst, e.g. a nickel, nickel-chromium or nickel-cobalt catalyst, which may be distributed on a carrier, and treating with hydrogen under pressure, e.g. in a rotary or stirring autoclave. In examples, the following hydrogenations are carried out in the presence of a nickel-chromium catalyst prepared by drying an aqueous mixture of nickel carbonate and chromic acid and treating with nitrogen at 300 DEG C. and then with hydrogen at 350 DEG C.; (1) 2 : 3-hydroxynaphthoic acid to its 5 : 6 : 7 :-8-tetrahydro derivative; (2) 2 : 3-hydroxynaphthoic acid anilide to its 5 : 6 : 7 : 8-tetrahydro derivative; (3) 1-phenyl-3-methyl-5-pyrazolone to the corresponding 1-cyclohexyl compound. Reference is also made to the production of 2-hydroxy-5 : 6 : 7 : 8-tetrahydronaphthalene from b -naphthol. Azo dyes; azo dyes forming upon the material.--The alkaline solution of 5 : 6 : 7 : 8-tetrahydro-2 : 3-hydroxynaphthoic acid anilide yields a brown dyestuff by coupling in substance or on the fibre with diazo compounds, e.g. with diazotized p-nitraniline.ALSO:Aromatic or heterocyclic monohydroxy compounds containing at least two nuclei joined together directly, e.g. monohydroxy compounds of the naphthalene series such as a - and b -naphthol, hydroxynaphthoic acids and their amides, e.g. anilides, toluidides or xylidides, similar hydroxy compounds of anthracene, phenanthrene, diphenyl, diphenylene oxide, quinoline and carbazole, and also phenylpyrazolones, which are capable of reacting as hydroxy compounds, are partially hydrogenated, in the nucleus not containing the hydroxy group, and in some cases also partially in the nucleus containing the hydroxy group, by treating them in alkaline solution with hydrogen under increased pressure, e.g. above 25 atmospheres, preferably at 100--250 atmospheres, in the presence of hydrogenation catalysts, e.g. a nickel, nickel-chromium or nickel-cobalt catalyst, preferably at elevated temperatures, e.g. 70--150 DEG C. In examples, the following hydrogenations are effected in the presence of a nickel-chromium catalyst prepared by drying an aqueous mixture of nickel carbonate and chromic acid and treating with nitrogen at 300 DEG C. and then with hydrogen at 350 DEG C.: (1) 2 : 3-hydroxynaphthoic acid to its 5 : 6 : 7 : 8-tetrahydro derivative; (2) 2 : 3-hydroxynaphthoic acid anilide to its 5 : 6 : 7 : 8-tetrahydro derivative; (3) 1-phenyl-3-methyl-5-pyrazolone to the corresponding 1-cyclohexyl compound. Reference is also made to the production of 2-hydroxy-5 : 6 : 7 : 8-tetrahydronaphthalene from b -naphthol.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB5436A GB468375A (en) | 1936-01-01 | 1936-01-01 | Improvements in the manufacture and production of partially hydrogenated compounds containing several nuclei |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB5436A GB468375A (en) | 1936-01-01 | 1936-01-01 | Improvements in the manufacture and production of partially hydrogenated compounds containing several nuclei |
Publications (1)
Publication Number | Publication Date |
---|---|
GB468375A true GB468375A (en) | 1937-07-01 |
Family
ID=9697580
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB5436A Expired GB468375A (en) | 1936-01-01 | 1936-01-01 | Improvements in the manufacture and production of partially hydrogenated compounds containing several nuclei |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB468375A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2553532A (en) * | 1947-03-22 | 1951-05-15 | Upjohn Co | Tetrahydronaphthols |
-
1936
- 1936-01-01 GB GB5436A patent/GB468375A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2553532A (en) * | 1947-03-22 | 1951-05-15 | Upjohn Co | Tetrahydronaphthols |
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