JPS58159456A - メチルメルカプタンの製造方法 - Google Patents
メチルメルカプタンの製造方法Info
- Publication number
- JPS58159456A JPS58159456A JP57043428A JP4342882A JPS58159456A JP S58159456 A JPS58159456 A JP S58159456A JP 57043428 A JP57043428 A JP 57043428A JP 4342882 A JP4342882 A JP 4342882A JP S58159456 A JPS58159456 A JP S58159456A
- Authority
- JP
- Japan
- Prior art keywords
- methanol
- reaction
- reactor
- catalyst
- activated alumina
- 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
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 title claims abstract description 71
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 132
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims abstract description 78
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 52
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims abstract description 52
- 238000006243 chemical reaction Methods 0.000 claims abstract description 48
- 239000003054 catalyst Substances 0.000 claims abstract description 42
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 13
- AAQNGTNRWPXMPB-UHFFFAOYSA-N dipotassium;dioxido(dioxo)tungsten Chemical compound [K+].[K+].[O-][W]([O-])(=O)=O AAQNGTNRWPXMPB-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000006227 byproduct Substances 0.000 claims abstract description 7
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 229910052980 cadmium sulfide Inorganic materials 0.000 claims description 4
- 238000010574 gas phase reaction Methods 0.000 claims description 2
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 claims description 2
- WUPHOULIZUERAE-UHFFFAOYSA-N 3-(oxolan-2-yl)propanoic acid Chemical compound OC(=O)CCC1CCCO1 WUPHOULIZUERAE-UHFFFAOYSA-N 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 229930182817 methionine Natural products 0.000 abstract description 2
- 239000012808 vapor phase Substances 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 9
- 239000007789 gas Substances 0.000 description 7
- 239000011261 inert gas Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- 244000233967 Anethum sowa Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical group S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57043428A JPS58159456A (ja) | 1982-03-17 | 1982-03-17 | メチルメルカプタンの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57043428A JPS58159456A (ja) | 1982-03-17 | 1982-03-17 | メチルメルカプタンの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58159456A true JPS58159456A (ja) | 1983-09-21 |
| JPH0323541B2 JPH0323541B2 (enrdf_load_stackoverflow) | 1991-03-29 |
Family
ID=12663421
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57043428A Granted JPS58159456A (ja) | 1982-03-17 | 1982-03-17 | メチルメルカプタンの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58159456A (enrdf_load_stackoverflow) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63119452A (ja) * | 1986-09-11 | 1988-05-24 | ソシエテ ナショナル エルフ アキテーヌ（プロデュクション） | 触媒を用いてチオエーテルからメルカプタンを製造する方法 |
| US5026915A (en) * | 1985-05-13 | 1991-06-25 | Atochem North America, Inc. | Process for the manufacture of dialkyl disulfides |
| EP0706998A1 (en) * | 1994-10-11 | 1996-04-17 | Elf Atochem North America, Inc. | Process for the manufacture of high purity linear c4+ alkyl mercaptans |
| CN1090532C (zh) * | 1996-09-26 | 2002-09-11 | 底古萨股份公司 | 催化剂、其制备方法和在合成甲硫醇中的应用 |
| JP2007515416A (ja) * | 2003-12-18 | 2007-06-14 | デグサ ゲーエムベーハー | メチルメルカプタンを反応ガス混合物から分離する方法 |
| DE102007007458A1 (de) | 2007-02-15 | 2008-08-21 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Methylmercaptan aus Dialkylsulfiden und Dialkylpolysulfiden |
| JP2009542754A (ja) * | 2006-07-13 | 2009-12-03 | エボニック デグサ ゲーエムベーハー | 複数帯域の固定床反応器における、アルキルメルカプタンの製造方法 |
| JP2010502440A (ja) * | 2006-09-11 | 2010-01-28 | エボニック デグサ ゲーエムベーハー | Ｍｏ含有触媒、製造方法およびメチルメルカプタンの製造方法 |
| CN102658183A (zh) * | 2012-04-28 | 2012-09-12 | 重庆紫光天化蛋氨酸有限责任公司 | 催化甲硫醚与硫化氢合成甲硫醇的催化剂及其制备方法和应用 |
| US10577314B2 (en) | 2016-05-31 | 2020-03-03 | Novus International, Inc. | Process for producing methyl mercaptan from dimethyl sulfide |
| CN114478334A (zh) * | 2022-02-25 | 2022-05-13 | 新疆广汇陆友硫化工有限公司 | 一种甲硫醇硫化法生产二甲基二硫的方法 |
-
1982
- 1982-03-17 JP JP57043428A patent/JPS58159456A/ja active Granted
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5026915A (en) * | 1985-05-13 | 1991-06-25 | Atochem North America, Inc. | Process for the manufacture of dialkyl disulfides |
| JPS63119452A (ja) * | 1986-09-11 | 1988-05-24 | ソシエテ ナショナル エルフ アキテーヌ（プロデュクション） | 触媒を用いてチオエーテルからメルカプタンを製造する方法 |
| EP0706998A1 (en) * | 1994-10-11 | 1996-04-17 | Elf Atochem North America, Inc. | Process for the manufacture of high purity linear c4+ alkyl mercaptans |
| CN1090532C (zh) * | 1996-09-26 | 2002-09-11 | 底古萨股份公司 | 催化剂、其制备方法和在合成甲硫醇中的应用 |
| JP4886520B2 (ja) * | 2003-12-18 | 2012-02-29 | エボニック デグサ ゲーエムベーハー | メチルメルカプタンを反応ガス混合物から分離する方法 |
| JP2007515416A (ja) * | 2003-12-18 | 2007-06-14 | デグサ ゲーエムベーハー | メチルメルカプタンを反応ガス混合物から分離する方法 |
| JP2009542754A (ja) * | 2006-07-13 | 2009-12-03 | エボニック デグサ ゲーエムベーハー | 複数帯域の固定床反応器における、アルキルメルカプタンの製造方法 |
| JP2010502440A (ja) * | 2006-09-11 | 2010-01-28 | エボニック デグサ ゲーエムベーハー | Ｍｏ含有触媒、製造方法およびメチルメルカプタンの製造方法 |
| DE102007007458A1 (de) | 2007-02-15 | 2008-08-21 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Methylmercaptan aus Dialkylsulfiden und Dialkylpolysulfiden |
| US7576243B2 (en) | 2007-02-15 | 2009-08-18 | Evonik Degussa Gmbh | Process for preparing methyl mercaptan from dialkyl sulphides and dialkyl polysulphides |
| CN102658183A (zh) * | 2012-04-28 | 2012-09-12 | 重庆紫光天化蛋氨酸有限责任公司 | 催化甲硫醚与硫化氢合成甲硫醇的催化剂及其制备方法和应用 |
| US10577314B2 (en) | 2016-05-31 | 2020-03-03 | Novus International, Inc. | Process for producing methyl mercaptan from dimethyl sulfide |
| CN114478334A (zh) * | 2022-02-25 | 2022-05-13 | 新疆广汇陆友硫化工有限公司 | 一种甲硫醇硫化法生产二甲基二硫的方法 |
| CN114478334B (zh) * | 2022-02-25 | 2023-11-10 | 新疆广汇陆友硫化工有限公司 | 一种甲硫醇硫化法生产二甲基二硫的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0323541B2 (enrdf_load_stackoverflow) | 1991-03-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6143921A (en) | Method for producing vinyl acetate monomer from ethane or ethylene oxidation | |
| US7833929B2 (en) | Process for the manufacture of methylmercaptan | |
| EP0086822B1 (en) | Process for the production of methyl halides and methyl alcohol from methane | |
| NZ522267A (en) | Process for the production of vinyl acetate using palladium and/or nickel based metal complex as catalyst | |
| JPS58159456A (ja) | メチルメルカプタンの製造方法 | |
| EP3464239B1 (en) | Process for producing methyl mercaptan from dimethyl sulfide | |
| EP1212276B1 (en) | Sulfur containing promoter for alkanes oxidative dehydrogenation processes | |
| US4485079A (en) | Ammoxidation of methanol to produce hydrogen cyanide | |
| US4665242A (en) | Process for the production of methyl mercaptan from oxides of carbon | |
| EP0446869A1 (en) | Process for preparing 1,1,1-trifluorochloroethane and 1,1,1,2-tetrafluoroethane | |
| JP2963396B2 (ja) | メチルメルカプタンの製造法 | |
| US4449006A (en) | Preparation of methyl mercaptan from carbon oxides | |
| US4579976A (en) | Catalytic process for the preparation of trifluoroacetaldehyde | |
| US7211688B2 (en) | Process for the production of an alkenyl carboxylate or an alkyl carboxylate | |
| US20240025847A1 (en) | Method for preparing mercaptans by sulfhydrolysis of sulfides | |
| CA2655736A1 (en) | Method for producing alkylmercaptans in a multi-zone fixed-bed reactor | |
| US4536492A (en) | Catalyst for the preparation of methyl mercaptan from carbon oxides | |
| US4358622A (en) | Preparation of methacrolein and methacrylonitrile from tert-butyl alkanoates | |
| US4443383A (en) | Preparation of methacrolein and methacrylonitrile from tert-butyl alkanoates | |
| JPH08224478A (ja) | メタクロレインを調製するための触媒 | |
| JPS6249258B2 (enrdf_load_stackoverflow) |