DE102005016369A1 - Verfahren zur kontinuierlichen Herstellung von Methylmercaptan - Google Patents
Verfahren zur kontinuierlichen Herstellung von Methylmercaptan Download PDFInfo
- Publication number
- DE102005016369A1 DE102005016369A1 DE102005016369A DE102005016369A DE102005016369A1 DE 102005016369 A1 DE102005016369 A1 DE 102005016369A1 DE 102005016369 A DE102005016369 A DE 102005016369A DE 102005016369 A DE102005016369 A DE 102005016369A DE 102005016369 A1 DE102005016369 A1 DE 102005016369A1
- Authority
- DE
- Germany
- Prior art keywords
- methanol
- catalyst
- zones
- process according
- hydrogen sulfide
- 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.)
- Withdrawn
Links
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 title claims abstract description 65
- 238000000034 method Methods 0.000 title claims abstract description 45
- 238000010924 continuous production Methods 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 175
- 239000003054 catalyst Substances 0.000 claims abstract description 68
- 239000007789 gas Substances 0.000 claims abstract description 56
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 37
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims abstract description 33
- 239000000376 reactant Substances 0.000 claims abstract description 14
- 239000007788 liquid Substances 0.000 claims description 13
- 238000002156 mixing Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 239000008246 gaseous mixture Substances 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 229910052792 caesium Inorganic materials 0.000 claims description 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 2
- 238000009827 uniform distribution Methods 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 28
- 238000002360 preparation method Methods 0.000 abstract description 9
- 239000000047 product Substances 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 10
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000000926 separation method 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
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
Classifications
-
- 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
- C07C319/08—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by replacement of hydroxy groups or etherified or esterified hydroxy groups
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)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005016369A DE102005016369A1 (de) | 2005-04-09 | 2005-04-09 | Verfahren zur kontinuierlichen Herstellung von Methylmercaptan |
| PCT/EP2006/060403 WO2006108737A1 (de) | 2005-04-09 | 2006-03-02 | Verfahren zur kontinuierlichen herstellung von methylmercaptan |
| CN2006800115329A CN101155778B (zh) | 2005-04-09 | 2006-03-02 | 甲硫醇的连续制备方法 |
| CA002604083A CA2604083A1 (en) | 2005-04-09 | 2006-03-02 | Method for the continuous production of methyl mercaptan |
| JP2008504720A JP5237789B2 (ja) | 2005-04-09 | 2006-03-02 | メチルメルカプタンを連続的に製造する方法 |
| ES06708606T ES2387037T3 (es) | 2005-04-09 | 2006-03-02 | Procedimiento para la preparación continua de metilmercaptano |
| BRPI0607785-4A BRPI0607785A2 (pt) | 2005-04-09 | 2006-03-02 | processo para a produção contìnua de metilmercaptano |
| MX2007012405A MX2007012405A (es) | 2005-04-09 | 2006-03-02 | Metodo para la produccion continua de metilmercaptano. |
| RU2007141136/04A RU2374226C2 (ru) | 2005-04-09 | 2006-03-02 | Способ непрерывного получения метилмеркаптана |
| EP06708606A EP1871740B1 (de) | 2005-04-09 | 2006-03-02 | Verfahren zur kontinuierlichen herstellung von methylmercaptan |
| US11/278,894 US7368611B2 (en) | 2005-04-09 | 2006-04-06 | Process for the continuous production of methylmercaptan |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005016369A DE102005016369A1 (de) | 2005-04-09 | 2005-04-09 | Verfahren zur kontinuierlichen Herstellung von Methylmercaptan |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102005016369A1 true DE102005016369A1 (de) | 2006-10-12 |
Family
ID=36754581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102005016369A Withdrawn DE102005016369A1 (de) | 2005-04-09 | 2005-04-09 | Verfahren zur kontinuierlichen Herstellung von Methylmercaptan |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7368611B2 (enExample) |
| EP (1) | EP1871740B1 (enExample) |
| JP (1) | JP5237789B2 (enExample) |
| CN (1) | CN101155778B (enExample) |
| BR (1) | BRPI0607785A2 (enExample) |
| CA (1) | CA2604083A1 (enExample) |
| DE (1) | DE102005016369A1 (enExample) |
| ES (1) | ES2387037T3 (enExample) |
| MX (1) | MX2007012405A (enExample) |
| RU (1) | RU2374226C2 (enExample) |
| WO (1) | WO2006108737A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004037739A1 (de) * | 2004-08-04 | 2006-03-16 | Degussa Ag | Wolframat enthaltende Katalysatoren zur Synthese von Alkylmercaptan und Verfahren zu ihrer Herstellung |
| DE102006032635A1 (de) * | 2006-07-13 | 2008-01-17 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Alkylmercaptanen in einem Mehrzonenfestbettreaktor |
| DE602006010705D1 (de) | 2006-09-15 | 2010-01-07 | Roche Diagnostics Gmbh | Biochemische Marker für akute Lungenembolie |
| US7645906B2 (en) * | 2007-03-27 | 2010-01-12 | Chevron Phillips Chemical Company Lp | Graded catalyst bed for methyl mercaptan synthesis |
| EP3034490A1 (en) * | 2014-12-19 | 2016-06-22 | Evonik Degussa GmbH | Process for the preparation of alkyl mercaptans |
| MY189842A (en) | 2016-05-31 | 2022-03-11 | Novus Int Inc | Process for producing methyl mercaptan from dimethyl sulfide |
| WO2019173208A1 (en) * | 2018-03-05 | 2019-09-12 | Chevron Phillips Chemical Company Lp | Synthesis of methyl ethyl sulfide and related production systems |
| CN108440353A (zh) * | 2018-04-25 | 2018-08-24 | 山东祥维斯生物科技股份有限公司 | 一种氯甲烷与硫化氢反应制备甲硫醇的方法 |
| KR102142355B1 (ko) | 2018-11-23 | 2020-08-07 | 한국화학연구원 | 촉매 비활성화 방지를 위한 다층의 촉매층 배열을 갖는 cdr 반응기 |
| CN114011343B (zh) * | 2021-12-01 | 2024-11-05 | 亳州聚识信息科技有限公司 | 一种甲硫醇制取设备 |
| WO2026071901A1 (ru) * | 2024-09-24 | 2026-04-02 | Акционерное общество "Специальное конструкторско-технологическое бюро "Катализатор" | Способ непрерывного получения метилмеркаптана |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2822400A (en) | 1955-06-22 | 1958-02-04 | American Oil Co | Methyl mercaptan production process |
| US3053902A (en) * | 1957-09-20 | 1962-09-11 | Union Oil Co | Preparation of mercaptans |
| DE1768826B1 (de) | 1968-07-04 | 1971-08-26 | Degussa | Verfahren zur Gewinnung von niederen aliphatischen Mercaptanen |
| FR2253013B1 (enExample) * | 1973-11-30 | 1980-01-04 | Rhone Progil | |
| FR2477538A2 (fr) | 1980-03-06 | 1981-09-11 | Rhone Poulenc Ind | Procede de preparation de methylmercaptan a partir d'hydrogene sulfure et de methanol |
| CN1023445C (zh) * | 1989-03-15 | 1994-01-12 | 中国石油化工总公司 | 可变床层总高度催化反应方法及其装置 |
| DE19639584A1 (de) * | 1996-09-26 | 1998-04-23 | Degussa | Katalysator, Verfahren zu seiner Herstellung und Verwendung zur Synthese von Methylmercaptan |
| DE19654515C1 (de) * | 1996-12-27 | 1998-10-01 | Degussa | Verfahren zur kontinuierlichen Herstellung von Methylmercaptan |
| DE19654516C1 (de) | 1996-12-27 | 1998-10-01 | Degussa | Verfahren zur Auftrennung des Produktgasgemisches der katalytischen Synthese von Methylmercaptan |
| RU2157366C1 (ru) * | 1999-03-10 | 2000-10-10 | Наумейко Анатолий Васильевич | Способ производства метилмеркаптана, способ получения катализатора для производства метилмеркаптана и способ получения сероводорода для производства метилмеркаптана |
| DE10338887A1 (de) * | 2003-08-23 | 2005-03-17 | Degussa Ag | Katalysator zur Synthese von Alkylmercaptan und Verfahren zu seiner Herstellung |
-
2005
- 2005-04-09 DE DE102005016369A patent/DE102005016369A1/de not_active Withdrawn
-
2006
- 2006-03-02 MX MX2007012405A patent/MX2007012405A/es active IP Right Grant
- 2006-03-02 ES ES06708606T patent/ES2387037T3/es not_active Expired - Lifetime
- 2006-03-02 EP EP06708606A patent/EP1871740B1/de not_active Expired - Lifetime
- 2006-03-02 RU RU2007141136/04A patent/RU2374226C2/ru active
- 2006-03-02 CA CA002604083A patent/CA2604083A1/en not_active Abandoned
- 2006-03-02 WO PCT/EP2006/060403 patent/WO2006108737A1/de not_active Ceased
- 2006-03-02 BR BRPI0607785-4A patent/BRPI0607785A2/pt not_active Application Discontinuation
- 2006-03-02 CN CN2006800115329A patent/CN101155778B/zh not_active Expired - Fee Related
- 2006-03-02 JP JP2008504720A patent/JP5237789B2/ja not_active Expired - Fee Related
- 2006-04-06 US US11/278,894 patent/US7368611B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| RU2007141136A (ru) | 2009-05-20 |
| ES2387037T3 (es) | 2012-09-12 |
| CA2604083A1 (en) | 2006-10-19 |
| JP5237789B2 (ja) | 2013-07-17 |
| MX2007012405A (es) | 2007-11-09 |
| EP1871740A1 (de) | 2008-01-02 |
| BRPI0607785A2 (pt) | 2009-06-13 |
| JP2008534645A (ja) | 2008-08-28 |
| WO2006108737A1 (de) | 2006-10-19 |
| CN101155778B (zh) | 2011-07-06 |
| RU2374226C2 (ru) | 2009-11-27 |
| EP1871740B1 (de) | 2012-05-16 |
| US20060229474A1 (en) | 2006-10-12 |
| CN101155778A (zh) | 2008-04-02 |
| US7368611B2 (en) | 2008-05-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: DEGUSSA GMBH, 40474 DUESSELDORF, DE |
|
| 8127 | New person/name/address of the applicant |
Owner name: EVONIK DEGUSSA GMBH, 40474 DUESSELDORF, DE |
|
| R012 | Request for examination validly filed |
Effective date: 20120121 |
|
| R119 | Application deemed withdrawn, or ip right lapsed, due to non-payment of renewal fee | ||
| R119 | Application deemed withdrawn, or ip right lapsed, due to non-payment of renewal fee |
Effective date: 20141101 |