JPS5811952B2 - メルカプトベンゾチアゾ−ルの精製法 - Google Patents
メルカプトベンゾチアゾ−ルの精製法Info
- Publication number
- JPS5811952B2 JPS5811952B2 JP53084511A JP8451178A JPS5811952B2 JP S5811952 B2 JPS5811952 B2 JP S5811952B2 JP 53084511 A JP53084511 A JP 53084511A JP 8451178 A JP8451178 A JP 8451178A JP S5811952 B2 JPS5811952 B2 JP S5811952B2
- Authority
- JP
- Japan
- Prior art keywords
- mercaptobenzothiazole
- carbon tetrachloride
- tetrachloroethylene
- purified
- crude product
- 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
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 title claims description 50
- 238000000034 method Methods 0.000 title claims description 27
- 238000000746 purification Methods 0.000 title description 9
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 32
- 229950011008 tetrachloroethylene Drugs 0.000 claims description 9
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 8
- 239000012043 crude product Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 2
- 238000005292 vacuum distillation Methods 0.000 claims 1
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 24
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 22
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 7
- 239000012535 impurity Substances 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 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
- 230000003647 oxidation Effects 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- QDTDFSFRIDFTCF-UHFFFAOYSA-N n-phenyl-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=CC=C2SC=1NC1=CC=CC=C1 QDTDFSFRIDFTCF-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005303 weighing Methods 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
- C07D277/72—2-Mercaptobenzothiazole
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 |
|---|---|---|---|
| FR7721437A FR2397409A1 (fr) | 1977-07-12 | 1977-07-12 | Procede de purification de mercaptobenzothiazole |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5419976A JPS5419976A (en) | 1979-02-15 |
| JPS5811952B2 true JPS5811952B2 (ja) | 1983-03-05 |
Family
ID=9193274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP53084511A Expired JPS5811952B2 (ja) | 1977-07-12 | 1978-07-11 | メルカプトベンゾチアゾ−ルの精製法 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4192804A (enExample) |
| EP (1) | EP0000464B1 (enExample) |
| JP (1) | JPS5811952B2 (enExample) |
| CA (1) | CA1097656A (enExample) |
| CS (1) | CS222268B2 (enExample) |
| DD (1) | DD137226A5 (enExample) |
| DE (1) | DE2860932D1 (enExample) |
| DK (1) | DK145821C (enExample) |
| ES (1) | ES471636A1 (enExample) |
| FR (1) | FR2397409A1 (enExample) |
| IE (1) | IE47028B1 (enExample) |
| IT (1) | IT1108498B (enExample) |
| SU (1) | SU818482A3 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2450828A1 (fr) | 1979-03-06 | 1980-10-03 | Ugine Kuhlmann | Procede de purification du mercaptobenzothiazole |
| FR2565977B1 (fr) * | 1984-06-15 | 1986-08-29 | Atochem | Procede de purification du mercaptobenzothiazole |
| DE3604705A1 (de) * | 1986-02-14 | 1987-08-27 | Bayer Antwerpen Nv | Verfahren zur aufarbeitung von 2-merkaptobenzthiazol enthaltenden teeren |
| FR2617479B1 (fr) * | 1987-07-03 | 1989-12-29 | Manuf Landaise Produits Ch | Procede de purification du mercaptobenzothiazole |
| ITMI20010473A1 (it) | 2001-03-07 | 2002-09-07 | Cooperativa Ct Ricerche Poly T | Fasi stazionarie chirali basate su derivati dell'acido 4-ammino-3,5-dinitrobenzoico |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3030373A (en) * | 1959-05-01 | 1962-04-17 | Monsanto Chemicals | Emulsion purification of mercaptobenzothiazole |
| BE791800A (fr) * | 1971-11-29 | 1973-05-23 | Sumitomo Chemical Co | Procede de preparation de 2-mercaptobenzothiazole |
-
1977
- 1977-07-12 FR FR7721437A patent/FR2397409A1/fr active Granted
-
1978
- 1978-06-27 CA CA306,303A patent/CA1097656A/fr not_active Expired
- 1978-07-03 DK DK300378A patent/DK145821C/da not_active IP Right Cessation
- 1978-07-03 DE DE7878400052T patent/DE2860932D1/de not_active Expired
- 1978-07-03 EP EP78400052A patent/EP0000464B1/fr not_active Expired
- 1978-07-06 US US05/922,417 patent/US4192804A/en not_active Expired - Lifetime
- 1978-07-11 IE IE1396/78A patent/IE47028B1/en unknown
- 1978-07-11 ES ES471636A patent/ES471636A1/es not_active Expired
- 1978-07-11 JP JP53084511A patent/JPS5811952B2/ja not_active Expired
- 1978-07-11 DD DD78206654A patent/DD137226A5/xx unknown
- 1978-07-12 SU SU782634049A patent/SU818482A3/ru active
- 1978-07-12 CS CS784667A patent/CS222268B2/cs unknown
- 1978-07-12 IT IT68641/78A patent/IT1108498B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| US4192804A (en) | 1980-03-11 |
| DK300378A (da) | 1979-01-13 |
| FR2397409B1 (enExample) | 1980-01-18 |
| JPS5419976A (en) | 1979-02-15 |
| EP0000464B1 (fr) | 1981-08-12 |
| FR2397409A1 (fr) | 1979-02-09 |
| IE781396L (en) | 1979-01-12 |
| DE2860932D1 (en) | 1981-11-12 |
| ES471636A1 (es) | 1979-02-01 |
| CS222268B2 (en) | 1983-06-24 |
| IE47028B1 (en) | 1983-11-30 |
| EP0000464A1 (fr) | 1979-01-24 |
| IT1108498B (it) | 1985-12-09 |
| DD137226A5 (de) | 1979-08-22 |
| IT7868641A0 (it) | 1978-07-12 |
| SU818482A3 (ru) | 1981-03-30 |
| DK145821C (da) | 1983-08-29 |
| CA1097656A (fr) | 1981-03-17 |
| DK145821B (da) | 1983-03-14 |
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