DE3224155A1 - Verfahren zur herstellung von 1-aminobenzol-2-sulfonsaeuren - Google Patents
Verfahren zur herstellung von 1-aminobenzol-2-sulfonsaeurenInfo
- Publication number
- DE3224155A1 DE3224155A1 DE19823224155 DE3224155A DE3224155A1 DE 3224155 A1 DE3224155 A1 DE 3224155A1 DE 19823224155 DE19823224155 DE 19823224155 DE 3224155 A DE3224155 A DE 3224155A DE 3224155 A1 DE3224155 A1 DE 3224155A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- oxidation
- aqueous
- oxidizes
- alkaline
- 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.)
- Withdrawn
Links
- 239000002253 acid Substances 0.000 title claims description 4
- 150000007513 acids Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 10
- 230000003647 oxidation Effects 0.000 claims description 10
- 238000007254 oxidation reaction Methods 0.000 claims description 10
- -1 alkali metal salts Chemical class 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 7
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical class NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 claims description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000002609 medium Substances 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YAQKYKGFPQPPQE-UHFFFAOYSA-N 2-methyl-6-nitro-1,3-benzothiazole Chemical compound C1=C([N+]([O-])=O)C=C2SC(C)=NC2=C1 YAQKYKGFPQPPQE-UHFFFAOYSA-N 0.000 description 2
- KZHGPDSVHSDCMX-UHFFFAOYSA-N 6-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=C2N=C(N)SC2=C1 KZHGPDSVHSDCMX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- UGDMYHVETQRVGB-UHFFFAOYSA-N 1,3-benzothiazole-6-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2N=CSC2=C1 UGDMYHVETQRVGB-UHFFFAOYSA-N 0.000 description 1
- KZKGEEGADAWJFS-UHFFFAOYSA-N 2-amino-5-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(N)C(S(O)(=O)=O)=C1 KZKGEEGADAWJFS-UHFFFAOYSA-N 0.000 description 1
- LTASFWDWBYFZQQ-UHFFFAOYSA-N 2-amino-5-nitrobenzenesulfonic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O LTASFWDWBYFZQQ-UHFFFAOYSA-N 0.000 description 1
- ZMCHBSMFKQYNKA-UHFFFAOYSA-M 2-aminobenzenesulfonate Chemical compound NC1=CC=CC=C1S([O-])(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-M 0.000 description 1
- BSQLQMLFTHJVKS-UHFFFAOYSA-N 2-chloro-1,3-benzothiazole Chemical compound C1=CC=C2SC(Cl)=NC2=C1 BSQLQMLFTHJVKS-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical class [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/16—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by oxidation of thiols, sulfides, hydropolysulfides, or polysulfides with formation of sulfo or halosulfonyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823224155 DE3224155A1 (de) | 1982-06-29 | 1982-06-29 | Verfahren zur herstellung von 1-aminobenzol-2-sulfonsaeuren |
| IN341/DEL/83A IN159836B (enExample) | 1982-06-29 | 1983-05-24 | |
| US06/502,077 US4548761A (en) | 1982-06-29 | 1983-06-08 | Process for the preparation of 1-aminobenzene-2-sulphonic acids |
| EP83105897A EP0101806B1 (de) | 1982-06-29 | 1983-06-16 | Verfahren zur Herstellung von 1-Aminobenzol-2-sulfonsäuren |
| DE8383105897T DE3365128D1 (en) | 1982-06-29 | 1983-06-16 | Process for preparing 2-amino-benzene sulphonic acids |
| JP58113004A JPS597156A (ja) | 1982-06-29 | 1983-06-24 | １−アミノベンゼン−２−スルホル酸類の製造方法 |
| BR8303440A BR8303440A (pt) | 1982-06-29 | 1983-06-28 | Processo para a preparacao de acidos 1-aminobenzeno-2-sulfonicos |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823224155 DE3224155A1 (de) | 1982-06-29 | 1982-06-29 | Verfahren zur herstellung von 1-aminobenzol-2-sulfonsaeuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3224155A1 true DE3224155A1 (de) | 1983-12-29 |
Family
ID=6167083
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823224155 Withdrawn DE3224155A1 (de) | 1982-06-29 | 1982-06-29 | Verfahren zur herstellung von 1-aminobenzol-2-sulfonsaeuren |
| DE8383105897T Expired DE3365128D1 (en) | 1982-06-29 | 1983-06-16 | Process for preparing 2-amino-benzene sulphonic acids |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8383105897T Expired DE3365128D1 (en) | 1982-06-29 | 1983-06-16 | Process for preparing 2-amino-benzene sulphonic acids |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4548761A (enExample) |
| EP (1) | EP0101806B1 (enExample) |
| JP (1) | JPS597156A (enExample) |
| BR (1) | BR8303440A (enExample) |
| DE (2) | DE3224155A1 (enExample) |
| IN (1) | IN159836B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6261111B2 (ja) * | 2013-07-17 | 2018-01-17 | 国立大学法人名古屋大学 | アレーンスルホンアミドの還元方法及びアレーンスルホン酸の製法 |
| CN104774165B (zh) * | 2015-03-16 | 2016-08-24 | 菏泽佳成化工有限公司 | 一种橡胶塑解剂dbd的绿色工业化制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2642458A (en) * | 1950-07-26 | 1953-06-16 | Monsanto Chemicals | Process of preparing 2-sulfobenzoic acid |
| US3038932A (en) * | 1958-07-02 | 1962-06-12 | American Cyanamid Co | Preparation of ortho-aminobenzenesulfonic acids |
| NL287952A (enExample) * | 1963-01-18 | |||
| US3670002A (en) * | 1970-02-20 | 1972-06-13 | Atlantic Richfield Co | Oxidation of thiols to thiolsulfonates and sulfonic acids |
| EP0025274A1 (en) * | 1979-08-20 | 1981-03-18 | Imperial Chemical Industries Plc | Preparation of aminosulphonic acids and their derivatives |
-
1982
- 1982-06-29 DE DE19823224155 patent/DE3224155A1/de not_active Withdrawn
-
1983
- 1983-05-24 IN IN341/DEL/83A patent/IN159836B/en unknown
- 1983-06-08 US US06/502,077 patent/US4548761A/en not_active Expired - Lifetime
- 1983-06-16 EP EP83105897A patent/EP0101806B1/de not_active Expired
- 1983-06-16 DE DE8383105897T patent/DE3365128D1/de not_active Expired
- 1983-06-24 JP JP58113004A patent/JPS597156A/ja active Granted
- 1983-06-28 BR BR8303440A patent/BR8303440A/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US4548761A (en) | 1985-10-22 |
| EP0101806A1 (de) | 1984-03-07 |
| JPS597156A (ja) | 1984-01-14 |
| DE3365128D1 (en) | 1986-09-11 |
| JPH0377183B2 (enExample) | 1991-12-09 |
| IN159836B (enExample) | 1987-06-06 |
| EP0101806B1 (de) | 1986-08-06 |
| BR8303440A (pt) | 1985-02-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |