CA1120499A - Process for the manufacture of methyl mercaptan from carbon oxides - Google Patents
Process for the manufacture of methyl mercaptan from carbon oxidesInfo
- Publication number
- CA1120499A CA1120499A CA000322731A CA322731A CA1120499A CA 1120499 A CA1120499 A CA 1120499A CA 000322731 A CA000322731 A CA 000322731A CA 322731 A CA322731 A CA 322731A CA 1120499 A CA1120499 A CA 1120499A
- Authority
- CA
- Canada
- Prior art keywords
- sulfide
- oxide
- hydrogen
- reactor
- 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
Links
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 238000000034 method Methods 0.000 title claims abstract description 52
- 229910002090 carbon oxide Inorganic materials 0.000 title claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 title claims description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 53
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 36
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims abstract description 33
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims abstract description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052751 metal Inorganic materials 0.000 claims abstract description 10
- 239000002184 metal Substances 0.000 claims abstract description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 9
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 8
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052804 chromium Inorganic materials 0.000 claims abstract description 7
- 239000011651 chromium Substances 0.000 claims abstract description 7
- -1 alkali metal inorganic base Chemical class 0.000 claims abstract description 6
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 6
- 239000010941 cobalt Substances 0.000 claims abstract description 6
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052742 iron Inorganic materials 0.000 claims abstract description 5
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052750 molybdenum Inorganic materials 0.000 claims abstract description 3
- 239000011733 molybdenum Substances 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 42
- 239000000376 reactant Substances 0.000 claims description 20
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 13
- 239000006227 byproduct Substances 0.000 claims description 11
- 238000005984 hydrogenation reaction Methods 0.000 claims description 10
- 150000001340 alkali metals Chemical class 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 229910052792 caesium Inorganic materials 0.000 claims description 7
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 7
- 229910052976 metal sulfide Inorganic materials 0.000 claims description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 239000001569 carbon dioxide Substances 0.000 claims description 4
- 150000007529 inorganic bases Chemical class 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 239000011949 solid catalyst Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 229910044991 metal oxide Inorganic materials 0.000 claims description 3
- 150000004706 metal oxides Chemical class 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- 229910052701 rubidium Inorganic materials 0.000 claims description 3
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims description 3
- QTNDMWXOEPGHBT-UHFFFAOYSA-N dicesium;sulfide Chemical class [S-2].[Cs+].[Cs+] QTNDMWXOEPGHBT-UHFFFAOYSA-N 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 claims description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 2
- PTISTKLWEJDJID-UHFFFAOYSA-N sulfanylidenemolybdenum Chemical class [Mo]=S PTISTKLWEJDJID-UHFFFAOYSA-N 0.000 claims description 2
- 239000012071 phase Substances 0.000 claims 2
- WWNBZGLDODTKEM-UHFFFAOYSA-N sulfanylidenenickel Chemical compound [Ni]=S WWNBZGLDODTKEM-UHFFFAOYSA-N 0.000 claims 2
- 150000004763 sulfides Chemical class 0.000 claims 2
- 239000012808 vapor phase Substances 0.000 claims 2
- 229910052977 alkali metal sulfide Inorganic materials 0.000 claims 1
- 150000002816 nickel compounds Chemical class 0.000 claims 1
- 239000007790 solid phase Substances 0.000 claims 1
- JQOAZIZLIIOXEW-UHFFFAOYSA-N zinc;chromium(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Cr+3].[Cr+3].[Zn+2] JQOAZIZLIIOXEW-UHFFFAOYSA-N 0.000 claims 1
- 239000007787 solid Substances 0.000 abstract description 2
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 16
- 239000007789 gas Substances 0.000 description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 15
- 229910002091 carbon monoxide Inorganic materials 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 7
- 229910052593 corundum Inorganic materials 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 229910001845 yogo sapphire Inorganic materials 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 150000003568 thioethers Chemical class 0.000 description 4
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 229910000480 nickel oxide Inorganic materials 0.000 description 3
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 3
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 238000011017 operating method Methods 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 229960003975 potassium Drugs 0.000 description 2
- 235000007686 potassium Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000006052 feed supplement Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000011819 refractory material Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/04—Mixing
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/20—Sulfiding
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88343878A | 1978-03-06 | 1978-03-06 | |
| US883,438 | 1978-03-06 | ||
| US1197779A | 1979-02-14 | 1979-02-14 | |
| US011,977 | 1979-02-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1120499A true CA1120499A (en) | 1982-03-23 |
Family
ID=26683002
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000322731A Expired CA1120499A (en) | 1978-03-06 | 1979-03-05 | Process for the manufacture of methyl mercaptan from carbon oxides |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS54135715A (nl) |
| AR (1) | AR222991A1 (nl) |
| BR (1) | BR7901361A (nl) |
| CA (1) | CA1120499A (nl) |
| DE (1) | DE2908668A1 (nl) |
| ES (1) | ES478320A1 (nl) |
| FR (1) | FR2419281A1 (nl) |
| GB (1) | GB2016468B (nl) |
| IT (1) | IT1114467B (nl) |
| MX (1) | MX151167A (nl) |
| NL (1) | NL190447C (nl) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4449006A (en) * | 1982-09-29 | 1984-05-15 | Pennwalt Corporation | Preparation of methyl mercaptan from carbon oxides |
| US4536492A (en) * | 1982-09-29 | 1985-08-20 | Pennwalt Corporation | Catalyst for the preparation of methyl mercaptan from carbon oxides |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4491639A (en) * | 1982-09-30 | 1985-01-01 | Gas Research Institute | Methods of making high activity transition metal catalysts |
| WO2005040082A2 (en) * | 2003-10-10 | 2005-05-06 | Degussa Ag | Process for the manufacture of methylmercaptan |
| CN101143329A (zh) * | 2006-09-11 | 2008-03-19 | 德古萨股份公司 | Mo-O-K基催化剂、其制备方法及其在甲硫醇合成中的应用 |
| EP1982764A1 (en) * | 2007-04-17 | 2008-10-22 | Evonik Degussa GmbH | Catalyst for the preparation of methyl mercaptan |
| DE102007024576A1 (de) * | 2007-05-25 | 2009-05-20 | Evonik Degussa Gmbh | Verfahren zur kontinuierlichen Herstellung von Methylmercaptan aus kohlenstoff- und wasserstoffhaltigen Verbindungen |
| FR2937566B1 (fr) | 2008-10-24 | 2014-07-18 | Arkema France | Catalyseur d'hydrogenation, notamment de sulfure de carbone |
| DE102009027837A1 (de) * | 2009-07-20 | 2011-01-27 | Evonik Degussa Gmbh | Verfahren zur kontinuierlichen Herstellung von Methylmercaptan aus kohlenstoffhaltigen Verbindungen, Schwefel und Wasserstoff |
| CN109195948B (zh) | 2016-05-31 | 2021-05-11 | 诺华丝国际股份有限公司 | 由二甲基硫醚生产甲基硫醇的方法 |
| CN114849693A (zh) * | 2022-06-17 | 2022-08-05 | 黄河三角洲京博化工研究院有限公司 | 一种用于合成甲硫醇的催化剂、制备方法及应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3070632A (en) * | 1959-12-21 | 1962-12-25 | Pennsalt Chemicals Corp | Process for preparation of methyl mercaptan |
-
1979
- 1979-03-01 GB GB7907182A patent/GB2016468B/en not_active Expired
- 1979-03-05 CA CA000322731A patent/CA1120499A/en not_active Expired
- 1979-03-05 IT IT48218/79A patent/IT1114467B/it active
- 1979-03-05 NL NLAANVRAGE7901730,A patent/NL190447C/nl not_active IP Right Cessation
- 1979-03-05 MX MX176799A patent/MX151167A/es unknown
- 1979-03-06 ES ES478320A patent/ES478320A1/es not_active Expired
- 1979-03-06 FR FR7905762A patent/FR2419281A1/fr active Granted
- 1979-03-06 DE DE2908668A patent/DE2908668A1/de active Granted
- 1979-03-06 AR AR275717A patent/AR222991A1/es active
- 1979-03-06 JP JP2519279A patent/JPS54135715A/ja active Granted
- 1979-03-06 BR BR7901361A patent/BR7901361A/pt unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4449006A (en) * | 1982-09-29 | 1984-05-15 | Pennwalt Corporation | Preparation of methyl mercaptan from carbon oxides |
| US4536492A (en) * | 1982-09-29 | 1985-08-20 | Pennwalt Corporation | Catalyst for the preparation of methyl mercaptan from carbon oxides |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2908668A1 (de) | 1979-09-20 |
| JPS6312866B2 (nl) | 1988-03-23 |
| DE2908668C2 (nl) | 1992-10-29 |
| NL7901730A (nl) | 1979-09-10 |
| MX151167A (es) | 1984-10-08 |
| JPS54135715A (en) | 1979-10-22 |
| AR222991A1 (es) | 1981-07-15 |
| BR7901361A (pt) | 1979-10-02 |
| IT7948218A0 (it) | 1979-03-05 |
| FR2419281B1 (nl) | 1984-06-22 |
| GB2016468A (en) | 1979-09-26 |
| IT1114467B (it) | 1986-01-27 |
| ES478320A1 (es) | 1980-01-16 |
| NL190447B (nl) | 1993-10-01 |
| GB2016468B (en) | 1982-09-15 |
| FR2419281A1 (fr) | 1979-10-05 |
| NL190447C (nl) | 1994-03-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |