GB408676A - The manufacture of symmetrically substituted azobenzene compounds - Google Patents
The manufacture of symmetrically substituted azobenzene compoundsInfo
- Publication number
- GB408676A GB408676A GB28770/32A GB2877032A GB408676A GB 408676 A GB408676 A GB 408676A GB 28770/32 A GB28770/32 A GB 28770/32A GB 2877032 A GB2877032 A GB 2877032A GB 408676 A GB408676 A GB 408676A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hours
- acid
- mixture
- sodium salt
- azo
- 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
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical class C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- 159000000000 sodium salts Chemical class 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 239000000706 filtrate Substances 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 2
- GNTARUIZNIWBCN-UHFFFAOYSA-N 2-chloro-5-nitrobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1Cl GNTARUIZNIWBCN-UHFFFAOYSA-N 0.000 abstract 1
- QUEKGYQTRJVEQC-UHFFFAOYSA-N 2516-96-3 Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1Cl QUEKGYQTRJVEQC-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- 239000005749 Copper compound Substances 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- -1 azo compound Chemical class 0.000 abstract 1
- 239000000987 azo dye Substances 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000001880 copper compounds Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Abstract
Azo dyes and intermediates.--Symmetrically substituted azobenzene derivatives, which are dyestuffs or are intermediates for the preparation of azo dyestuffs, are obtained by reducing in an alkaline medium a 1-nitro-4-halogenbenzene-3-sulphonic or carboxylic acid to the corresponding 4 : 4<1>-dihalogenazobenzene-3 : 3<1>-disulphonic or dicarboxylic acid and replacing the halogen atoms by amino or hydroxy groups by known methods. Alternatively, the reduction may be carried further to produce the hydrazo compounds which are then oxidized to the azo compounds before replacing the halogen atoms. The following examples are specified. (1) 5-Nitro-2-chlorobenzoic acid is dissolved in caustic soda solution and zinc dust is slowly stirred in while keeping the temperature below 50 DEG C., the mixture being then heated during 2 hours to 90 DEG C. and maintained at this temperature for 8 hours; the mixture is then filtered hot and the sodium salt of 4 : 4<1>-dichloroazobenzene-3 : 3<1>-dicarboxylic acid is salted out from the filtrate and is heated under pressure for about 10 hours at 150 DEG C. with caustic soda solution containing some copper powder or a suitable copper compound; the excess of alkali is then neutralized and the sodium salt of 4 : 4<1>-dihydroxyazobenzene-3 : 3<1>-dicarboxylic acid is salted out. (2) 5-Nitro-2-chlorobenzenesulphonic acid is dissolved in aqueous ammonia, zinc dust is added while keeping the temperature below 60 DEG C. and the mixture is heated during 2 hours to 90 DEG C.; the mixture is then filtered, air is blown into the filtrate to oxidize the 4 : 4<1>-dichlorohydrazobenzene-3 : 3<1>-disulphonic acid and the sodium salt of the azo compound is salted out; this product is heated under pressure for 8 hours at 160 DEG C. with aqueous ammonia, whereupon the excess of ammonia is driven off and the sodium salt of 4 : 4<1>-diaminoazobenzene-3 : 3<1>-disulphonic acid is salted out. The Specification as open to inspection under Sect. 91 comprises also the production of similar symmetrical azo compounds in which the benzene nuclei are further substituted, e.g. by alkyl. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE408676X | 1931-10-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB408676A true GB408676A (en) | 1934-04-16 |
Family
ID=6422324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28770/32A Expired GB408676A (en) | 1931-10-17 | 1932-10-14 | The manufacture of symmetrically substituted azobenzene compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB408676A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0036636A1 (en) * | 1980-03-26 | 1981-09-30 | Pharmacia Ab | A method and intermediates for preparing 3,3'-azo-bis-(6-hydroxy benzoic acid) |
| EP0036637A1 (en) * | 1980-03-26 | 1981-09-30 | Pharmacia Ab | Use of 3,3'-azo-bis-(6-hydroxy benzoic acid) as a drug and pharmaceutical compositions containing the same |
| FR2500824A1 (en) * | 1981-03-02 | 1982-09-03 | Searle & Co | 5,5'-AZOBIS-SALICYLIC ACID AND ITS USEFUL SALTS, IN PARTICULAR FOR THE TREATMENT OF INFLAMMATORY DISEASES OF THE INTESTINE |
| EP0066861A1 (en) * | 1981-06-08 | 1982-12-15 | Pharmacia Ab | Dianionic 5,5'-azobis-salicylic-acid composition |
-
1932
- 1932-10-14 GB GB28770/32A patent/GB408676A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0036636A1 (en) * | 1980-03-26 | 1981-09-30 | Pharmacia Ab | A method and intermediates for preparing 3,3'-azo-bis-(6-hydroxy benzoic acid) |
| EP0036637A1 (en) * | 1980-03-26 | 1981-09-30 | Pharmacia Ab | Use of 3,3'-azo-bis-(6-hydroxy benzoic acid) as a drug and pharmaceutical compositions containing the same |
| FR2500824A1 (en) * | 1981-03-02 | 1982-09-03 | Searle & Co | 5,5'-AZOBIS-SALICYLIC ACID AND ITS USEFUL SALTS, IN PARTICULAR FOR THE TREATMENT OF INFLAMMATORY DISEASES OF THE INTESTINE |
| JPS57144219A (en) * | 1981-03-02 | 1982-09-06 | Searle & Co | Azobissalicylic acid and salts thereof and medicinal composition containing them |
| EP0066861A1 (en) * | 1981-06-08 | 1982-12-15 | Pharmacia Ab | Dianionic 5,5'-azobis-salicylic-acid composition |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2094224A (en) | Pyrene 3, 5, 8, 10-tetra-sulphonic acid and derivatives thereof | |
| GB408676A (en) | The manufacture of symmetrically substituted azobenzene compounds | |
| US2681926A (en) | Dichlorodiaminostilbenedisulfonic acids | |
| US3008950A (en) | Red monoazo-dyestuffs | |
| US2778815A (en) | Process for the production of aromatic omicron-hydroxydiazo compounds | |
| US1987538A (en) | Water-soluble anthraquinone dyestuffs and process for making same | |
| US1959461A (en) | Symmetrically substituted azobenzene compounds | |
| US2120814A (en) | Azo dyestuffs | |
| US2175815A (en) | Copper complex compounds of disazo dyestuffs of the stilbene series | |
| US1857244A (en) | New monoazodyestuffs | |
| US2714588A (en) | Copper-containing disazo dyestuffs | |
| US2139325A (en) | Manufacture of 4-amino-azo-benzene-4'-sulphonic acid | |
| US3471469A (en) | Water-soluble monoazo-pyrazolone dyestuffs | |
| US2050913A (en) | Azo-dyestuffs and process of making same | |
| US1059670A (en) | Dye. | |
| US1149231A (en) | Yellow chrome-mordant dyestuffs and process of making same. | |
| US1879240A (en) | Azo dyestuffs | |
| US628025A (en) | Blue-black wool-dye and process of making same. | |
| US1012853A (en) | Dye. | |
| US1962226A (en) | Azo dyes, and method for their preparation | |
| DE632083C (en) | Process for the production of acidic dyes of the anthraquinone series | |
| US2031634A (en) | Water soluble diazoimino compounds | |
| US2122127A (en) | Ortho-hydroxyazo dyes and process for manufacturing the same | |
| US464775A (en) | Ors to tfie farbenfabrikek | |
| US1498913A (en) | Vat dyes of the thioindigo series and process of making same |