JPH0310617B2 - - Google Patents
Info
- Publication number
- JPH0310617B2 JPH0310617B2 JP57057485A JP5748582A JPH0310617B2 JP H0310617 B2 JPH0310617 B2 JP H0310617B2 JP 57057485 A JP57057485 A JP 57057485A JP 5748582 A JP5748582 A JP 5748582A JP H0310617 B2 JPH0310617 B2 JP H0310617B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- hydroxyethyl
- sulfone
- parts
- 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.)
- Expired - Lifetime
Links
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 31
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- PWHHOXIZSHCFSH-UHFFFAOYSA-N 2-(2-hydroxy-2-nitro-2-phenylethyl)sulfanyl-1-nitro-1-phenylethanol Chemical compound C=1C=CC=CC=1C([N+]([O-])=O)(O)CSCC(O)([N+]([O-])=O)C1=CC=CC=C1 PWHHOXIZSHCFSH-UHFFFAOYSA-N 0.000 claims description 6
- 239000012736 aqueous medium Substances 0.000 claims description 2
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 claims 1
- 125000002560 nitrile group Chemical group 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000000034 method Methods 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- -1 sulfuric acid ester Chemical class 0.000 description 12
- 238000007254 oxidation reaction Methods 0.000 description 11
- 150000003457 sulfones Chemical class 0.000 description 10
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- TWROWYXNCKRGSE-UHFFFAOYSA-N [N+](=O)([O-])C(CS(=O)(=O)CC([N+](=O)[O-])(C1=CC=CC=C1)O)(O)C1=CC=CC=C1 Chemical compound [N+](=O)([O-])C(CS(=O)(=O)CC([N+](=O)[O-])(C1=CC=CC=C1)O)(O)C1=CC=CC=C1 TWROWYXNCKRGSE-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 150000002825 nitriles Chemical class 0.000 description 6
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 230000001590 oxidative effect Effects 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 239000011733 molybdenum Substances 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 235000010265 sodium sulphite Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 3
- 150000003462 sulfoxides Chemical class 0.000 description 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 3
- 229910052721 tungsten Inorganic materials 0.000 description 3
- 239000010937 tungsten Substances 0.000 description 3
- 229910052720 vanadium Inorganic materials 0.000 description 3
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 3
- VKPQLZPZPYQFOK-UHFFFAOYSA-N 2-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=CC=C1S(Cl)(=O)=O VKPQLZPZPYQFOK-UHFFFAOYSA-N 0.000 description 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- MYPTVBMGGUVBLK-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C=CC=C1)C(CSCC(C1=C(C=CC=C1)[N+](=O)[O-])O)O Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)C(CSCC(C1=C(C=CC=C1)[N+](=O)[O-])O)O MYPTVBMGGUVBLK-UHFFFAOYSA-N 0.000 description 2
- WDJLDRBCOKVKBE-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=C(C=C1)C(CSCC(C1=CC=C(C=C1)[N+](=O)[O-])O)O Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)C(CSCC(C1=CC=C(C=C1)[N+](=O)[O-])O)O WDJLDRBCOKVKBE-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- BDZBTWJKEAVPTC-UHFFFAOYSA-N 1-(3-aminophenyl)-2-[2-(3-aminophenyl)-2-hydroxyethyl]sulfonylethanol Chemical compound NC1=CC=CC(C(O)CS(=O)(=O)CC(O)C=2C=C(N)C=CC=2)=C1 BDZBTWJKEAVPTC-UHFFFAOYSA-N 0.000 description 1
- UXXFFFKLKFFDHH-UHFFFAOYSA-N 2-(2-hydroxy-2-phenylethyl)sulfanyl-1-phenylethanol Chemical compound C=1C=CC=CC=1C(O)CSCC(O)C1=CC=CC=C1 UXXFFFKLKFFDHH-UHFFFAOYSA-N 0.000 description 1
- QQLILYBIARWEIF-UHFFFAOYSA-N 2-(2-hydroxyethylsulfonyl)ethanol Chemical compound OCCS(=O)(=O)CCO QQLILYBIARWEIF-UHFFFAOYSA-N 0.000 description 1
- DFJSXKDFHPUCDP-UHFFFAOYSA-N 2-[2-hydroxy-2-(3-nitrophenyl)ethyl]sulfonyl-1-(3-nitrophenyl)ethanol Chemical compound C=1C=CC([N+]([O-])=O)=CC=1C(O)CS(=O)(=O)CC(O)C1=CC=CC([N+]([O-])=O)=C1 DFJSXKDFHPUCDP-UHFFFAOYSA-N 0.000 description 1
- KCMKIDORSDPITL-UHFFFAOYSA-N 2-acetamidobenzenesulfonic acid Chemical compound CC(=O)NC1=CC=CC=C1S(O)(=O)=O KCMKIDORSDPITL-UHFFFAOYSA-N 0.000 description 1
- FPPLREPCQJZDAQ-UHFFFAOYSA-N 2-methylpentanedinitrile Chemical compound N#CC(C)CCC#N FPPLREPCQJZDAQ-UHFFFAOYSA-N 0.000 description 1
- WPHUUIODWRNJLO-UHFFFAOYSA-N 2-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1S(Cl)(=O)=O WPHUUIODWRNJLO-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- MKVZBWHQISBPHT-UHFFFAOYSA-N OC(CS(=O)(=O)CC(O)C1=CC=C(C=C1)[N+]([O-])=O)C1=CC=C(C=C1)[N+]([O-])=O Chemical compound OC(CS(=O)(=O)CC(O)C1=CC=C(C=C1)[N+]([O-])=O)C1=CC=C(C=C1)[N+]([O-])=O MKVZBWHQISBPHT-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- ONFKRXFVLZDIDU-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C=CC=C1)C(CS(=O)(=O)CC(C1=C(C=CC=C1)[N+](=O)[O-])O)O Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)C(CS(=O)(=O)CC(C1=C(C=CC=C1)[N+](=O)[O-])O)O ONFKRXFVLZDIDU-UHFFFAOYSA-N 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- ZTOMUSMDRMJOTH-UHFFFAOYSA-N glutaronitrile Chemical compound N#CCCCC#N ZTOMUSMDRMJOTH-UHFFFAOYSA-N 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
- NLTVDSADVNSFTM-UHFFFAOYSA-N n-[2-(2-acetamido-2-hydroxy-2-phenylethyl)sulfonyl-1-hydroxy-1-phenylethyl]acetamide Chemical compound C=1C=CC=CC=1C(O)(NC(=O)C)CS(=O)(=O)CC(O)(NC(C)=O)C1=CC=CC=C1 NLTVDSADVNSFTM-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57057485A JPS58174353A (ja) | 1982-04-06 | 1982-04-06 | モノニトロフエニル−β−ヒドロキシエチルスルホンの製造法 |
| US06/477,443 US4612394A (en) | 1982-04-06 | 1983-03-21 | Process for producing aminophenyl-β-hydroxyethylsulfone |
| EP83301683A EP0092909B1 (en) | 1982-04-06 | 1983-03-25 | Process for producing aminophenyl-beta-hydroxyethylsulfone |
| DE8383301683T DE3373093D1 (en) | 1982-04-06 | 1983-03-25 | Process for producing aminophenyl-beta-hydroxyethylsulfone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57057485A JPS58174353A (ja) | 1982-04-06 | 1982-04-06 | モノニトロフエニル−β−ヒドロキシエチルスルホンの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58174353A JPS58174353A (ja) | 1983-10-13 |
| JPH0310617B2 true JPH0310617B2 (da) | 1991-02-14 |
Family
ID=13057009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57057485A Granted JPS58174353A (ja) | 1982-04-06 | 1982-04-06 | モノニトロフエニル−β−ヒドロキシエチルスルホンの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58174353A (da) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5757486A (en) * | 1980-09-24 | 1982-04-06 | Tokyo Shibaura Electric Co | Method of assembling high frequency induction furnace facility |
-
1982
- 1982-04-06 JP JP57057485A patent/JPS58174353A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5757486A (en) * | 1980-09-24 | 1982-04-06 | Tokyo Shibaura Electric Co | Method of assembling high frequency induction furnace facility |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58174353A (ja) | 1983-10-13 |
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