CA1292242C - Procede catalytique de production de mercaptans a partir de thioethers - Google Patents
Procede catalytique de production de mercaptans a partir de thioethersInfo
- Publication number
- CA1292242C CA1292242C CA000546729A CA546729A CA1292242C CA 1292242 C CA1292242 C CA 1292242C CA 000546729 A CA000546729 A CA 000546729A CA 546729 A CA546729 A CA 546729A CA 1292242 C CA1292242 C CA 1292242C
- Authority
- CA
- Canada
- Prior art keywords
- thioether
- laughed
- mercaptan
- character
- catalyst
- 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
- 150000003568 thioethers Chemical class 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims abstract description 33
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
- 230000003197 catalytic effect Effects 0.000 title claims abstract description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 239000003377 acid catalyst Substances 0.000 claims abstract 4
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 8
- 150000001336 alkenes Chemical class 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 5
- -1 etheroxide Chemical class 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 150000002500 ions Chemical group 0.000 claims description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 239000010457 zeolite Substances 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 2
- 150000003457 sulfones Chemical group 0.000 claims description 2
- 150000003462 sulfoxides Chemical group 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 229910021536 Zeolite Inorganic materials 0.000 claims 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000000101 thioether group Chemical group 0.000 claims 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 description 6
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 4
- 229920001429 chelating resin Polymers 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 4
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 3
- 229940069096 dodecene Drugs 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- ZRKMQKLGEQPLNS-UHFFFAOYSA-N 1-Pentanethiol Chemical compound CCCCCS ZRKMQKLGEQPLNS-UHFFFAOYSA-N 0.000 description 2
- 102100038916 Caspase-5 Human genes 0.000 description 2
- 101100112336 Homo sapiens CASP5 gene Proteins 0.000 description 2
- 101100273286 Mus musculus Casp4 gene Proteins 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 2
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- IUDGNRWYNOEIKF-UHFFFAOYSA-N 11-bromo-undecanoic acid Chemical compound OC(=O)CCCCCCCCCCBr IUDGNRWYNOEIKF-UHFFFAOYSA-N 0.000 description 1
- HTIRHQRTDBPHNZ-UHFFFAOYSA-N Dibutyl sulfide Chemical compound CCCCSCCCC HTIRHQRTDBPHNZ-UHFFFAOYSA-N 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N Na2O Inorganic materials [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 239000012445 acidic reagent Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- DXHPZXWIPWDXHJ-UHFFFAOYSA-N carbon monosulfide Chemical compound [S+]#[C-] DXHPZXWIPWDXHJ-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical class OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material 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
- 239000000203 mixture Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/02—Thiols having mercapto groups bound to acyclic carbon atoms
- C07C321/04—Thiols having mercapto groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
- C07C319/06—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols from sulfides, hydropolysulfides or polysulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/18—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by addition of thiols to unsaturated compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/02—Thiols having mercapto groups bound to acyclic carbon atoms
- C07C321/06—Thiols having mercapto groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8612690A FR2603889B1 (fr) | 1986-09-11 | 1986-09-11 | Procede catalytique de production de mercaptans a partir de thioethers |
| FR8612690 | 1986-09-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1292242C true CA1292242C (fr) | 1991-11-19 |
Family
ID=9338842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000546729A Expired - Lifetime CA1292242C (fr) | 1986-09-11 | 1987-09-11 | Procede catalytique de production de mercaptans a partir de thioethers |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4927972A (en]) |
| EP (1) | EP0260185B1 (en]) |
| JP (1) | JPS63119452A (en]) |
| KR (1) | KR900008118B1 (en]) |
| CA (1) | CA1292242C (en]) |
| DE (1) | DE3766453D1 (en]) |
| ES (1) | ES2019652B3 (en]) |
| FR (1) | FR2603889B1 (en]) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5977125A (en) | 1994-10-31 | 1999-11-02 | Eisai Co., Ltd. | Mono-or polyenic carboxylic acid derivatives |
| JP3964478B2 (ja) | 1995-06-30 | 2007-08-22 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ヘテロ環含有カルボン酸誘導体及びそれを含有する医薬 |
| JP4959063B2 (ja) * | 2001-03-09 | 2012-06-20 | 和光純薬工業株式会社 | チオール化合物を含んでなる反応試薬 |
| FR2844726B1 (fr) * | 2002-09-25 | 2004-12-03 | Atofina | Procede catalytique de fabricaton de mercaptans a partir de thioethers |
| DE102007007458A1 (de) * | 2007-02-15 | 2008-08-21 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Methylmercaptan aus Dialkylsulfiden und Dialkylpolysulfiden |
| FR3002230B1 (fr) | 2013-02-15 | 2016-02-05 | Arkema France | Utilisation de mercapto-esters methyliques en tant qu'agents de transfert de chaine |
| FR3012449B1 (fr) | 2013-10-24 | 2015-10-30 | Arkema France | Procede de synthese d'un mercaptan par addition d'hydrogene sulfure sur une olefine |
| WO2021105376A1 (de) * | 2019-11-28 | 2021-06-03 | Saltigo Gmbh | Verbessertes verfahren zur herstellung von unsymmetrischen dialkylsulfiden |
| US11161810B1 (en) * | 2020-06-10 | 2021-11-02 | Arkema Inc. | Continuous photochemical production of high purity linear mercaptan and sulfide compositions |
| CN118084748B (zh) * | 2024-02-28 | 2024-10-15 | 淄博润祥工贸有限公司 | 一种叔十二碳硫醇及其制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2831031A (en) * | 1954-02-16 | 1958-04-15 | American Oil Co | Conversion of organic sulfur compounds |
| US3069472A (en) * | 1960-08-23 | 1962-12-18 | Pennsalt Chemical Corp | Novel process for preparation of mercaptans by catalytic cleavage of sulfides |
| US3376348A (en) * | 1964-02-12 | 1968-04-02 | Hooker Chemical Corp | Preparation of alkyl sulfides |
| JPS5246203B2 (en]) * | 1972-09-27 | 1977-11-22 | ||
| US4005149A (en) * | 1975-05-01 | 1977-01-25 | Phillips Petroleum Company | Mercaptans by hydrogen sulfide-cleavage of organic sulfides in presence of carbon disulfide |
| US4059636A (en) * | 1976-05-04 | 1977-11-22 | Phillips Petroleum Company | Mercaptans by catalytic cleavage of organic sulfides |
| US4102931A (en) * | 1977-05-17 | 1978-07-25 | Pennwalt Corporation | Manufacture of tertiary mercaptans using zeolite catalysts |
| US4278816A (en) * | 1977-08-26 | 1981-07-14 | Stauffer Chemical Company | Process for preparing phenols and thiophenols |
| JPS5515425A (en) * | 1978-07-17 | 1980-02-02 | Seitetsu Kagaku Co Ltd | Preparation of p-halogenothiophenol |
| US4313006A (en) * | 1980-09-03 | 1982-01-26 | Pennwalt Corporation | Process for converting dialkyl sulfides to alkyl mercaptans |
| JPS58159456A (ja) * | 1982-03-17 | 1983-09-21 | Seitetsu Kagaku Co Ltd | メチルメルカプタンの製造方法 |
| JPH075531A (ja) * | 1991-11-20 | 1995-01-10 | Gordon Williamson Stuart | 光反射装置 |
-
1986
- 1986-09-11 FR FR8612690A patent/FR2603889B1/fr not_active Expired
-
1987
- 1987-09-02 ES ES87401969T patent/ES2019652B3/es not_active Expired - Lifetime
- 1987-09-02 EP EP87401969A patent/EP0260185B1/fr not_active Expired - Lifetime
- 1987-09-02 DE DE8787401969T patent/DE3766453D1/de not_active Expired - Lifetime
- 1987-09-10 KR KR1019870010054A patent/KR900008118B1/ko not_active Expired
- 1987-09-11 CA CA000546729A patent/CA1292242C/fr not_active Expired - Lifetime
- 1987-09-11 JP JP62228203A patent/JPS63119452A/ja active Granted
-
1988
- 1988-12-12 US US07/284,767 patent/US4927972A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR900008118B1 (ko) | 1990-10-31 |
| US4927972A (en) | 1990-05-22 |
| ES2019652B3 (es) | 1991-07-01 |
| FR2603889A1 (fr) | 1988-03-18 |
| FR2603889B1 (fr) | 1989-05-05 |
| DE3766453D1 (de) | 1991-01-10 |
| EP0260185A1 (fr) | 1988-03-16 |
| KR880003905A (ko) | 1988-06-01 |
| JPH042587B2 (en]) | 1992-01-20 |
| EP0260185B1 (fr) | 1990-11-28 |
| JPS63119452A (ja) | 1988-05-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |