DE2202204C2 - Verfahren zur Herstellung von 2-Mercaptobenzimidazol - Google Patents
Verfahren zur Herstellung von 2-MercaptobenzimidazolInfo
- Publication number
- DE2202204C2 DE2202204C2 DE2202204A DE2202204A DE2202204C2 DE 2202204 C2 DE2202204 C2 DE 2202204C2 DE 2202204 A DE2202204 A DE 2202204A DE 2202204 A DE2202204 A DE 2202204A DE 2202204 C2 DE2202204 C2 DE 2202204C2
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- phenylenediamine
- mercaptobenzimidazole
- benzothiazole
- solvent
- 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
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims 2
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 title description 14
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 33
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 32
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 11
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 230000020477 pH reduction Effects 0.000 claims description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 1
- 238000001556 precipitation Methods 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 11
- 239000012535 impurity Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 238000006701 autoxidation reaction Methods 0.000 description 5
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 229940078552 o-xylene Drugs 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 230000010349 pulsation Effects 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- TUCSLJFYSQXGEV-UHFFFAOYSA-N 2-Butylbenzothiazole Chemical compound C1=CC=C2SC(CCCC)=NC2=C1 TUCSLJFYSQXGEV-UHFFFAOYSA-N 0.000 description 1
- CVULGJIRGZVJHQ-UHFFFAOYSA-N 2-ethylbenzothiazole Chemical compound C1=CC=C2SC(CC)=NC2=C1 CVULGJIRGZVJHQ-UHFFFAOYSA-N 0.000 description 1
- ZVTBXGSHAYDNOP-UHFFFAOYSA-N 2-propyl-1,3-benzothiazole Chemical compound C1=CC=C2SC(CCC)=NC2=C1 ZVTBXGSHAYDNOP-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- BNOODXBBXFZASF-UHFFFAOYSA-N [Na].[S] Chemical compound [Na].[S] BNOODXBBXFZASF-UHFFFAOYSA-N 0.000 description 1
- -1 alkali metal salt Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- LUJSWKPWNJSZAL-UHFFFAOYSA-L disodium dioxido-oxo-sulfanylidene-lambda6-sulfane sulfuric acid Chemical compound [Na+].[Na+].OS(O)(=O)=O.[O-]S([O-])(=O)=S LUJSWKPWNJSZAL-UHFFFAOYSA-L 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- HIZCIEIDIFGZSS-UHFFFAOYSA-L trithiocarbonate Chemical compound [S-]C([S-])=S HIZCIEIDIFGZSS-UHFFFAOYSA-L 0.000 description 1
- 239000012989 trithiocarbonate Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/28—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2202204A DE2202204C2 (de) | 1972-01-18 | 1972-01-18 | Verfahren zur Herstellung von 2-Mercaptobenzimidazol |
| US00323118A US3842098A (en) | 1972-01-18 | 1973-01-12 | Production of 2-mercaptobenzimidazole by reacting o-phenylene diamine and carbon disulfide |
| AU51115/73A AU465570B2 (en) | 1972-01-18 | 1973-01-15 | A process for the production of 2-mercaptobenzim-idazole |
| NL7300573A NL7300573A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-01-18 | 1973-01-15 | |
| BE794066D BE794066A (fr) | 1972-01-18 | 1973-01-15 | Procede de preparation de 2-mercapto-benzimidazol |
| CA161,391A CA1004678A (en) | 1972-01-18 | 1973-01-16 | Process for the production of 2-mercaptobenzimidazole |
| BR73343A BR7300343D0 (pt) | 1972-01-18 | 1973-01-16 | Processo para a fabricacao de 2-mercapto-benzimidazol |
| IT47707/73A IT976903B (it) | 1972-01-18 | 1973-01-16 | Procedimento per la produzione di 2 mercaptobenzimidazolo |
| CH58573A CH583709A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-01-18 | 1973-01-16 | |
| ES410701A ES410701A1 (es) | 1972-01-18 | 1973-01-17 | Procedimiento para la produccion de 2-mercaptobenzimidazol altamente puro. |
| ZA730356A ZA73356B (en) | 1972-01-18 | 1973-01-17 | A process for the production of 2-mercaptobenzoimidazole |
| GB257573A GB1413577A (en) | 1972-01-18 | 1973-01-18 | Process for the production of 2-mercapto benzimidazole |
| JP745073A JPS5442982B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-01-18 | 1973-01-18 | |
| AR246194A AR201482A1 (es) | 1972-01-18 | 1973-01-18 | Procedimiento para la produccion de 2-mercaptobenzimidazol altamente puro aplicable como medio protector contra el envejecimiento del caucho |
| FR7301794A FR2436141A1 (fr) | 1972-01-18 | 1973-01-18 | Procede de preparation de 2-mercaptobenzimidazol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2202204A DE2202204C2 (de) | 1972-01-18 | 1972-01-18 | Verfahren zur Herstellung von 2-Mercaptobenzimidazol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2202204A1 DE2202204A1 (de) | 1973-08-09 |
| DE2202204C2 true DE2202204C2 (de) | 1983-06-01 |
Family
ID=5833305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2202204A Expired DE2202204C2 (de) | 1972-01-18 | 1972-01-18 | Verfahren zur Herstellung von 2-Mercaptobenzimidazol |
Country Status (15)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3895025A (en) * | 1973-03-29 | 1975-07-15 | Du Pont | 2-Benzimidazolethiol preparation |
| US4172833A (en) * | 1978-03-20 | 1979-10-30 | R. T. Vanderbilt Company, Inc. | Process for preparation of 2-mercaptotoluimidazole and salts thereof |
| GB2036026A (en) * | 1978-05-17 | 1980-06-25 | Teijin Ltd | Hexahydronaphthoimidazothiazoles and process for preparing same |
| DE3008159A1 (de) * | 1980-03-04 | 1981-09-17 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 4- bzw. 5-methyl-2-mercaptobenzimidazol |
| US4335132A (en) * | 1980-12-29 | 1982-06-15 | Sterling Drug, Inc. | 5-(Py-Y)-1H-benzimidazol-2-ols and 5-(Py-Y-)-1H-benzimidazole-2-thiols |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR7303M (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1967-03-07 | 1969-09-29 |
-
1972
- 1972-01-18 DE DE2202204A patent/DE2202204C2/de not_active Expired
-
1973
- 1973-01-12 US US00323118A patent/US3842098A/en not_active Expired - Lifetime
- 1973-01-15 AU AU51115/73A patent/AU465570B2/en not_active Expired
- 1973-01-15 NL NL7300573A patent/NL7300573A/xx not_active Application Discontinuation
- 1973-01-15 BE BE794066D patent/BE794066A/xx not_active IP Right Cessation
- 1973-01-16 BR BR73343A patent/BR7300343D0/pt unknown
- 1973-01-16 IT IT47707/73A patent/IT976903B/it active
- 1973-01-16 CH CH58573A patent/CH583709A5/xx not_active IP Right Cessation
- 1973-01-16 CA CA161,391A patent/CA1004678A/en not_active Expired
- 1973-01-17 ES ES410701A patent/ES410701A1/es not_active Expired
- 1973-01-17 ZA ZA730356A patent/ZA73356B/xx unknown
- 1973-01-18 JP JP745073A patent/JPS5442982B2/ja not_active Expired
- 1973-01-18 FR FR7301794A patent/FR2436141A1/fr active Granted
- 1973-01-18 AR AR246194A patent/AR201482A1/es active
- 1973-01-18 GB GB257573A patent/GB1413577A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT976903B (it) | 1974-09-10 |
| GB1413577A (en) | 1975-11-12 |
| CA1004678A (en) | 1977-02-01 |
| ZA73356B (en) | 1973-10-31 |
| AU465570B2 (en) | 1975-10-02 |
| NL7300573A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-07-20 |
| CH583709A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-01-14 |
| FR2436141B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-04-30 |
| AR201482A1 (es) | 1975-03-21 |
| DE2202204A1 (de) | 1973-08-09 |
| JPS4878170A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-10-20 |
| BE794066A (fr) | 1973-07-16 |
| ES410701A1 (es) | 1976-01-01 |
| JPS5442982B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-12-17 |
| US3842098A (en) | 1974-10-15 |
| FR2436141A1 (fr) | 1980-04-11 |
| AU5111573A (en) | 1974-07-18 |
| BR7300343D0 (pt) | 1973-09-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |