CS215179B1 - Method of making the n-cyclohexybenzthiazol-2-sulphenamide - Google Patents
Method of making the n-cyclohexybenzthiazol-2-sulphenamide Download PDFInfo
- Publication number
- CS215179B1 CS215179B1 CS804887A CS488780A CS215179B1 CS 215179 B1 CS215179 B1 CS 215179B1 CS 804887 A CS804887 A CS 804887A CS 488780 A CS488780 A CS 488780A CS 215179 B1 CS215179 B1 CS 215179B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- mercaptobenzothiazole
- cyclohexylamine
- sulfenamide
- salt
- product
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 19
- 239000005708 Sodium hypochlorite Substances 0.000 claims abstract description 10
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
- 230000003647 oxidation Effects 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- RZJAGVAZCIMIJP-UHFFFAOYSA-N 5-amino-2-(4-aminophenyl)benzenethiol Chemical compound SC1=C(C=CC(=C1)N)C1=CC=C(N)C=C1 RZJAGVAZCIMIJP-UHFFFAOYSA-N 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- GJEAMHAFPYZYDE-UHFFFAOYSA-N [C].[S] Chemical compound [C].[S] GJEAMHAFPYZYDE-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000011261 inert gas Substances 0.000 claims 1
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 abstract description 29
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 8
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 abstract description 5
- 150000003946 cyclohexylamines Chemical class 0.000 abstract description 4
- 239000007800 oxidant agent Substances 0.000 abstract description 4
- 229940054266 2-mercaptobenzothiazole Drugs 0.000 abstract 3
- 239000005864 Sulphur Substances 0.000 abstract 1
- 239000012043 crude product Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 238000004073 vulcanization Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 8
- 239000000243 solution Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 159000000007 calcium salts Chemical class 0.000 description 3
- -1 amine salt Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- BNOMVHZDJIXZAA-UHFFFAOYSA-N 2-methylhexan-1-amine Chemical class CCCCC(C)CN BNOMVHZDJIXZAA-UHFFFAOYSA-N 0.000 description 1
- XTDMOBIAHSICBE-UHFFFAOYSA-N 3h-1,3-benzothiazole-2-thione;cyclohexanamine Chemical compound NC1CCCCC1.C1=CC=C2SC(S)=NC2=C1 XTDMOBIAHSICBE-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 150000001669 calcium Chemical class 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229940043430 calcium compound Drugs 0.000 description 1
- 150000001674 calcium compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000008237 rinsing water Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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
- C07D277/70—Sulfur atoms
- C07D277/76—Sulfur atoms attached to a second hetero atom
- C07D277/80—Sulfur atoms attached to a second hetero atom to a nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS804887A CS215179B1 (en) | 1980-07-09 | 1980-07-09 | Method of making the n-cyclohexybenzthiazol-2-sulphenamide |
| CH4463/81A CH648028A5 (de) | 1980-07-09 | 1981-07-07 | Verfahren zur herstellung von n-cyclohexylbenzothiazol-2-sulfenamid. |
| IT8122813A IT8122813A0 (it) | 1980-07-09 | 1981-07-08 | Procedimento di preparazione di n-cicloesilbenzotiazol-2-solfenammi de. |
| GB8121021A GB2080294B (en) | 1980-07-09 | 1981-07-08 | Method for the production of n-cyclohexylbenzothiazole-2-sulfenamide |
| BE0/205344A BE889546A (fr) | 1980-07-09 | 1981-07-08 | Procede de preparation de n-cyclohexylbenzothiazole-2-sulfenamide |
| ES503774A ES8203868A1 (es) | 1980-07-09 | 1981-07-08 | Procedimiento de preparacion de n-ciclohexilbenzotiazol-2- sulfenamida |
| DE19813127193 DE3127193A1 (de) | 1980-07-09 | 1981-07-09 | Verfahren zur herstellung von n-cyclohexylbenzothiazol-2-sulfenamid |
| YU1694/81A YU41459B (en) | 1980-07-09 | 1981-07-09 | Process for producing n-cyclohexyl benzothiazole -2- sulfene - amides |
| FR8113528A FR2486527A1 (fr) | 1980-07-09 | 1981-07-09 | Procede de preparation de n-cyclohexylbenzothiazole-2-sulfenamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS804887A CS215179B1 (en) | 1980-07-09 | 1980-07-09 | Method of making the n-cyclohexybenzthiazol-2-sulphenamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS215179B1 true CS215179B1 (en) | 1982-07-30 |
Family
ID=5392615
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS804887A CS215179B1 (en) | 1980-07-09 | 1980-07-09 | Method of making the n-cyclohexybenzthiazol-2-sulphenamide |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE889546A (es) |
| CH (1) | CH648028A5 (es) |
| CS (1) | CS215179B1 (es) |
| DE (1) | DE3127193A1 (es) |
| ES (1) | ES8203868A1 (es) |
| FR (1) | FR2486527A1 (es) |
| GB (1) | GB2080294B (es) |
| IT (1) | IT8122813A0 (es) |
| YU (1) | YU41459B (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3325724A1 (de) * | 1983-07-16 | 1985-01-24 | Akzo Gmbh, 5600 Wuppertal | Verfahren zur herstellung von thiazolyl-2-sulfenamiden |
| GB8725334D0 (en) * | 1987-10-29 | 1987-12-02 | Monsanto Europe Sa | Preparation of benzothiazole-2-sulphenamides |
| US5436346A (en) * | 1991-12-21 | 1995-07-25 | Akzo Nobel N.V. | Process for the preparation of benzothiazolyl-2-sulphenamides |
| DE10307138A1 (de) * | 2003-02-20 | 2004-09-02 | Bayer Ag | Verfahren zur Herstellung von Lagerstabilen Benzthiazolylsulfenamiden |
| CN102863402A (zh) * | 2012-09-25 | 2013-01-09 | 科迈化工股份有限公司 | 促进剂cbs制备方法 |
| CN106432135A (zh) * | 2016-09-30 | 2017-02-22 | 王显权 | N‑环己基‑2‑苯并噻唑次磺酰胺的生产方法 |
| CN110523332B (zh) * | 2019-09-16 | 2021-07-02 | 山东尚舜化工有限公司 | 一种连续生产硫化促进剂cbs的设备及方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE615580C (de) * | 1933-04-14 | 1935-07-08 | I G Farbenindustrie Akt Ges | Verfahren zur Herstellung von Sulfenamiden sekundaerer Amine |
| FR852118A (fr) * | 1938-03-25 | 1940-01-24 | Ici Ltd | Procédé de fabrication et application de nouveaux dérivés du mercaptobenzthiazol |
| GB655668A (en) * | 1940-07-26 | 1951-08-01 | Monsanto Chemicals | Improvements in or relating to methods of making sulphenamides |
| BE754504A (fr) * | 1969-08-08 | 1971-02-08 | Bayer Ag | Procede pour la preparation de benzothiazylsulfenamides |
-
1980
- 1980-07-09 CS CS804887A patent/CS215179B1/cs unknown
-
1981
- 1981-07-07 CH CH4463/81A patent/CH648028A5/de not_active IP Right Cessation
- 1981-07-08 IT IT8122813A patent/IT8122813A0/it unknown
- 1981-07-08 GB GB8121021A patent/GB2080294B/en not_active Expired
- 1981-07-08 BE BE0/205344A patent/BE889546A/fr not_active IP Right Cessation
- 1981-07-08 ES ES503774A patent/ES8203868A1/es not_active Expired
- 1981-07-09 FR FR8113528A patent/FR2486527A1/fr active Granted
- 1981-07-09 DE DE19813127193 patent/DE3127193A1/de not_active Ceased
- 1981-07-09 YU YU1694/81A patent/YU41459B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH648028A5 (de) | 1985-02-28 |
| BE889546A (fr) | 1981-11-03 |
| ES503774A0 (es) | 1982-04-01 |
| FR2486527A1 (fr) | 1982-01-15 |
| GB2080294B (en) | 1985-05-09 |
| YU41459B (en) | 1987-06-30 |
| FR2486527B3 (es) | 1983-05-13 |
| GB2080294A (en) | 1982-02-03 |
| ES8203868A1 (es) | 1982-04-01 |
| DE3127193A1 (de) | 1982-05-19 |
| IT8122813A0 (it) | 1981-07-08 |
| YU169481A (en) | 1983-06-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CS215179B1 (en) | Method of making the n-cyclohexybenzthiazol-2-sulphenamide | |
| JP5102493B2 (ja) | ２−メルカプトベンゾチアゾールを得る方法 | |
| US3840591A (en) | Process for the production of p-nitrotoluene-2-sulfonic acid | |
| CA1173461A (en) | Process for producing 2-mercaptoethylamine hydrohalides | |
| US5367082A (en) | Process for the preparation of 2-mercaptobenzothiazole | |
| US4061646A (en) | Process for purification of crude 2-mercaptobenzothiazole | |
| JPS6019770A (ja) | カルベンダジムの製造の際の副生成物の割合を減少させる方法 | |
| JPS61115075A (ja) | 貯蔵可能なベンズチアゾールスルフエンアミド類の製造方法 | |
| US3974170A (en) | Preparation of 2-mercaptoazoles | |
| US3681371A (en) | Process for purification of crude 2-mercaptobenzothiazole | |
| US4374247A (en) | Process for preparing 2,2-disubstituted thiazolidines | |
| US4677209A (en) | Process for the preparation of 2-mercaptobenzoxazoles | |
| US4192804A (en) | Process for the purification of mercaptobenzothiazole | |
| US3842098A (en) | Production of 2-mercaptobenzimidazole by reacting o-phenylene diamine and carbon disulfide | |
| PH26962A (en) | Process for direct isolation of captopril | |
| JPH035394B2 (es) | ||
| JPS636545B2 (es) | ||
| JPS5858348B2 (ja) | 粗２−メルカプト．ベンゾ．チアゾ−ルの精製方法 | |
| US2772279A (en) | Preparation of sulfenamides | |
| SK53493A3 (en) | Method of production of n-cyclohexylbenzothiazole-2-sulfenamide | |
| US3931321A (en) | Process for the preparation of O-aminothiophenols | |
| CS221042B1 (en) | Method of cleaning the 2-mercaptobenzthiazole | |
| US2423310A (en) | Manufacture of thiuram disulfides | |
| SK280366B6 (sk) | Spôsob výroby n-cyklohexylbenzotiazolyl-2-sulfénam | |
| JPH0380785B2 (es) |