JPS597156A - １−アミノベンゼン−２−スルホル酸類の製造方法 - Google Patents
１−アミノベンゼン−２−スルホル酸類の製造方法Info
- Publication number
- JPS597156A JPS597156A JP58113004A JP11300483A JPS597156A JP S597156 A JPS597156 A JP S597156A JP 58113004 A JP58113004 A JP 58113004A JP 11300483 A JP11300483 A JP 11300483A JP S597156 A JPS597156 A JP S597156A
- Authority
- JP
- Japan
- Prior art keywords
- oxidation
- carried out
- formula
- aqueous
- hydrogen peroxide
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000002253 acid Substances 0.000 title description 2
- 150000007513 acids Chemical class 0.000 title description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 20
- 230000003647 oxidation Effects 0.000 claims description 15
- 238000007254 oxidation reaction Methods 0.000 claims description 15
- -1 alkali metal cation Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 239000002609 medium Substances 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture 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
- 239000007800 oxidant agent Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 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
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229950000244 sulfanilic acid Drugs 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- YYYOQURZQWIILK-UHFFFAOYSA-N 2-[(2-aminophenyl)disulfanyl]aniline Chemical compound NC1=CC=CC=C1SSC1=CC=CC=C1N YYYOQURZQWIILK-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-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- ZCXGMSGCBDSEOY-UHFFFAOYSA-N 2-benzothiazolsulfonic acid Chemical group C1=CC=C2SC(S(=O)(=O)O)=NC2=C1 ZCXGMSGCBDSEOY-UHFFFAOYSA-N 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
- FQBAMYDJEQUGNV-UHFFFAOYSA-N 2-methoxybenzenesulfonic acid Chemical compound COC1=CC=CC=C1S(O)(=O)=O FQBAMYDJEQUGNV-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000001218 Thorium Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 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
- 230000015572 biosynthetic process Effects 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
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000007788 liquid 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
- 125000005342 perphosphate group Chemical group 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
- 239000002244 precipitate Substances 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
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823224155 DE3224155A1 (de) | 1982-06-29 | 1982-06-29 | Verfahren zur herstellung von 1-aminobenzol-2-sulfonsaeuren |
| DE3224155.0 | 1982-06-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS597156A true JPS597156A (ja) | 1984-01-14 |
| JPH0377183B2 JPH0377183B2 (enExample) | 1991-12-09 |
Family
ID=6167083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58113004A Granted 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 |
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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015020961A (ja) * | 2013-07-17 | 2015-02-02 | 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、アレーンスルホン酸の製法及びビナフチルジスルホン酸 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015020961A (ja) * | 2013-07-17 | 2015-02-02 | 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、アレーンスルホン酸の製法及びビナフチルジスルホン酸 |
Also Published As
| Publication number | Publication date |
|---|---|
| US4548761A (en) | 1985-10-22 |
| EP0101806A1 (de) | 1984-03-07 |
| DE3365128D1 (en) | 1986-09-11 |
| DE3224155A1 (de) | 1983-12-29 |
| JPH0377183B2 (enExample) | 1991-12-09 |
| IN159836B (enExample) | 1987-06-06 |
| EP0101806B1 (de) | 1986-08-06 |
| BR8303440A (pt) | 1985-02-12 |
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