FR2486527A1 - Procede de preparation de n-cyclohexylbenzothiazole-2-sulfenamide - Google Patents
Procede de preparation de n-cyclohexylbenzothiazole-2-sulfenamide Download PDFInfo
- Publication number
- FR2486527A1 FR2486527A1 FR8113528A FR8113528A FR2486527A1 FR 2486527 A1 FR2486527 A1 FR 2486527A1 FR 8113528 A FR8113528 A FR 8113528A FR 8113528 A FR8113528 A FR 8113528A FR 2486527 A1 FR2486527 A1 FR 2486527A1
- Authority
- FR
- France
- Prior art keywords
- cyclohexylamine
- mercaptobenzothiazole
- sulfenamide
- reaction
- cyclohexylbenzothiazole
- 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
- 238000000034 method Methods 0.000 title claims abstract description 25
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 title claims abstract description 4
- 238000002360 preparation method Methods 0.000 title description 7
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 claims abstract description 33
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims abstract description 30
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 230000003647 oxidation Effects 0.000 claims abstract description 7
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 7
- 230000001590 oxidative effect Effects 0.000 claims abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000011593 sulfur Substances 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 239000012043 crude product Substances 0.000 claims abstract description 4
- 239000006227 byproduct Substances 0.000 claims abstract description 3
- 238000001914 filtration Methods 0.000 claims abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 9
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 150000001412 amines Chemical class 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
- 238000004519 manufacturing process Methods 0.000 claims description 2
- IGWFHAFFBQEUIX-UHFFFAOYSA-N 2-sulfanyl-1,2-benzothiazine Chemical compound C1=CC=C2C=CN(S)SC2=C1 IGWFHAFFBQEUIX-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 230000005587 bubbling Effects 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-M thiosalicylate(1-) Chemical compound [O-]C(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-M 0.000 claims 1
- 150000003946 cyclohexylamines Chemical class 0.000 abstract description 6
- 239000012266 salt solution Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 14
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 8
- 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
- 150000003839 salts Chemical class 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KLEUYJCQHIYGMQ-UHFFFAOYSA-N 3-cyclohexyl-2h-1,3-benzothiazole Chemical compound C1SC2=CC=CC=C2N1C1CCCCC1 KLEUYJCQHIYGMQ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- RMVRSNDYEFQCLF-UHFFFAOYSA-N phenyl mercaptan Natural products SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XHRCFGDFESIFRG-UHFFFAOYSA-N 2-chloro-n-ethyl-n-[(2-methylphenyl)methyl]ethanamine Chemical compound ClCCN(CC)CC1=CC=CC=C1C XHRCFGDFESIFRG-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-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
- 241001676573 Minium Species 0.000 description 1
- PKEQGLNTIMPZAI-UHFFFAOYSA-N SC=1SC2=C(N1)C=CC=C2.[Ca] Chemical compound SC=1SC2=C(N1)C=CC=C2.[Ca] PKEQGLNTIMPZAI-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- -1 amine salt Chemical class 0.000 description 1
- 229940043430 calcium compound Drugs 0.000 description 1
- 150000001674 calcium compounds Chemical class 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000013040 rubber vulcanization Methods 0.000 description 1
- GPNLWUFFWOYKLP-UHFFFAOYSA-N s-(1,3-benzothiazol-2-yl)thiohydroxylamine Chemical compound C1=CC=C2SC(SN)=NC2=C1 GPNLWUFFWOYKLP-UHFFFAOYSA-N 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
- 239000000725 suspension Substances 0.000 description 1
- 239000002699 waste material Substances 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)
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 (2)
| Publication Number | Publication Date |
|---|---|
| FR2486527A1 true FR2486527A1 (fr) | 1982-01-15 |
| FR2486527B3 FR2486527B3 (enrdf_load_stackoverflow) | 1983-05-13 |
Family
ID=5392615
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8113528A Granted FR2486527A1 (fr) | 1980-07-09 | 1981-07-09 | Procede de preparation de n-cyclohexylbenzothiazole-2-sulfenamide |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE889546A (enrdf_load_stackoverflow) |
| CH (1) | CH648028A5 (enrdf_load_stackoverflow) |
| CS (1) | CS215179B1 (enrdf_load_stackoverflow) |
| DE (1) | DE3127193A1 (enrdf_load_stackoverflow) |
| ES (1) | ES8203868A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2486527A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2080294B (enrdf_load_stackoverflow) |
| IT (1) | IT8122813A0 (enrdf_load_stackoverflow) |
| YU (1) | YU41459B (enrdf_load_stackoverflow) |
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 BE BE0/205344A patent/BE889546A/fr not_active IP Right Cessation
- 1981-07-08 GB GB8121021A patent/GB2080294B/en not_active Expired
- 1981-07-08 ES ES503774A patent/ES8203868A1/es not_active Expired
- 1981-07-08 IT IT8122813A patent/IT8122813A0/it unknown
- 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 |
|---|---|
| BE889546A (fr) | 1981-11-03 |
| FR2486527B3 (enrdf_load_stackoverflow) | 1983-05-13 |
| DE3127193A1 (de) | 1982-05-19 |
| YU41459B (en) | 1987-06-30 |
| ES503774A0 (es) | 1982-04-01 |
| CH648028A5 (de) | 1985-02-28 |
| YU169481A (en) | 1983-06-30 |
| GB2080294A (en) | 1982-02-03 |
| ES8203868A1 (es) | 1982-04-01 |
| GB2080294B (en) | 1985-05-09 |
| IT8122813A0 (it) | 1981-07-08 |
| CS215179B1 (en) | 1982-07-30 |
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