ES2693607T3 - Procedimiento para la separación de metilmercaptano a partir de mezclas de reacción gaseosas - Google Patents
Procedimiento para la separación de metilmercaptano a partir de mezclas de reacción gaseosas Download PDFInfo
- Publication number
- ES2693607T3 ES2693607T3 ES04803357.5T ES04803357T ES2693607T3 ES 2693607 T3 ES2693607 T3 ES 2693607T3 ES 04803357 T ES04803357 T ES 04803357T ES 2693607 T3 ES2693607 T3 ES 2693607T3
- Authority
- ES
- Spain
- Prior art keywords
- mmp
- methylmercaptan
- methyl mercaptan
- reaction
- reaction mixture
- 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
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 title claims abstract description 97
- 238000000034 method Methods 0.000 title claims abstract description 27
- 239000011541 reaction mixture Substances 0.000 title claims abstract description 18
- 238000000926 separation method Methods 0.000 title claims abstract description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 54
- CLUWOWRTHNNBBU-UHFFFAOYSA-N 3-methylthiopropanal Chemical compound CSCCC=O CLUWOWRTHNNBBU-UHFFFAOYSA-N 0.000 claims abstract description 30
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 20
- 238000004821 distillation Methods 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000003555 thioacetals Chemical class 0.000 claims abstract description 8
- 230000003197 catalytic effect Effects 0.000 claims abstract description 5
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000001569 carbon dioxide Substances 0.000 claims description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 11
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 6
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229930182817 methionine Natural products 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- -1 MMP aldehyde Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- IWLYFBGNNDXONS-UHFFFAOYSA-N 2-hydroxy-2-sulfanylpentanoic acid Chemical compound CCCC(O)(S)C(O)=O IWLYFBGNNDXONS-UHFFFAOYSA-N 0.000 description 1
- CQSQMXIROIYTLO-UHFFFAOYSA-N 2-methylpropanethial Chemical compound CC(C)C=S CQSQMXIROIYTLO-UHFFFAOYSA-N 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- AAQNGTNRWPXMPB-UHFFFAOYSA-N dipotassium;dioxido(dioxo)tungsten Chemical compound [K+].[K+].[O-][W]([O-])(=O)=O AAQNGTNRWPXMPB-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000002828 fuel tank Substances 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000001451 organic peroxides Chemical class 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
- 239000002243 precursor Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000012808 vapor phase Substances 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
-
- 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
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/26—Separation; Purification; Stabilisation; Use of additives
- C07C319/28—Separation; Purification
-
- 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
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10359636A DE10359636A1 (de) | 2003-12-18 | 2003-12-18 | Verfahren zur Abtrennung von Methylmercaptan aus Reaktionsgemischen |
| DE10359636 | 2003-12-18 | ||
| PCT/EP2004/013565 WO2005058809A1 (en) | 2003-12-18 | 2004-11-30 | Method for the separation of methyl mercaptan from reaction gas mixtures |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2693607T3 true ES2693607T3 (es) | 2018-12-12 |
Family
ID=34672899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES04803357.5T Expired - Lifetime ES2693607T3 (es) | 2003-12-18 | 2004-11-30 | Procedimiento para la separación de metilmercaptano a partir de mezclas de reacción gaseosas |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7199270B2 (enExample) |
| EP (1) | EP1694639B1 (enExample) |
| JP (1) | JP4886520B2 (enExample) |
| KR (1) | KR101139206B1 (enExample) |
| CN (1) | CN100516036C (enExample) |
| BR (1) | BRPI0417700A (enExample) |
| DE (1) | DE10359636A1 (enExample) |
| ES (1) | ES2693607T3 (enExample) |
| RU (1) | RU2361859C2 (enExample) |
| WO (1) | WO2005058809A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011093839A (ja) * | 2009-10-29 | 2011-05-12 | Sumitomo Chemical Co Ltd | ３−メチルチオプロパナールの製造方法 |
| DE102010064250A1 (de) * | 2010-12-28 | 2012-06-28 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Methylmercaptopropionaldehyd |
| KR101911563B1 (ko) | 2011-02-23 | 2018-10-24 | 에보니크 데구사 게엠베하 | 3-(메틸티오)프로판알 및 시안화수소로부터 2-히드록시-4-(메틸티오)부탄니트릴을 제조하는 방법 |
| DE102011081828A1 (de) | 2011-08-30 | 2013-02-28 | Evonik Degussa Gmbh | Verfahren zur Umsetzung von Methylmercaptopropionaldehyd aus Roh-Acrolein und Roh-Methylmercaptan |
| BR112014003602B1 (pt) | 2011-08-30 | 2021-05-18 | Evonik Operations Gmbh | sistema de reação e método para produção contínua de um sal de metionina |
| CN105080174B (zh) * | 2015-08-25 | 2017-03-22 | 成都德美工程技术有限公司 | 二甲亚砜生产尾气的处理方法及装置 |
| CN114181125A (zh) * | 2021-12-10 | 2022-03-15 | 宁夏紫光天化蛋氨酸有限责任公司 | 甲硫醇的分离方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2626282A (en) * | 1949-10-05 | 1953-01-20 | Standard Oil Dev Co | Vapor phase production of betamethylmercaptopropionaldehyde |
| FR1520328A (fr) | 1966-04-25 | 1968-04-05 | Sumitomo Chemical Co | Procédé de fabrication du beta-méthylmercaptopropionaldéhyde en deux étapes |
| YU32920B (en) | 1966-04-25 | 1975-12-31 | Sumitomo Co Ltd | Postupak za proizvodnju -metilmerkaptopropionaldehida od akroleina i metilmerkaptana |
| BE697818A (enExample) * | 1966-04-30 | 1967-10-02 | ||
| NL132124C (enExample) * | 1966-09-02 | |||
| DE1768826B1 (de) | 1968-07-04 | 1971-08-26 | Degussa | Verfahren zur Gewinnung von niederen aliphatischen Mercaptanen |
| DE2320544C2 (de) | 1973-04-21 | 1975-06-05 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Verfahren zur Herstellung von 3-Methylmercaptopropionaldehyd |
| 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 |
| US5905171A (en) * | 1995-06-22 | 1999-05-18 | Novus International, Inc. | Process for the preparation of 3-(methylthio)propanal |
| DE19654516C1 (de) * | 1996-12-27 | 1998-10-01 | Degussa | Verfahren zur Auftrennung des Produktgasgemisches der katalytischen Synthese von Methylmercaptan |
| DE19654515C1 (de) * | 1996-12-27 | 1998-10-01 | Degussa | Verfahren zur kontinuierlichen Herstellung von Methylmercaptan |
-
2003
- 2003-12-18 DE DE10359636A patent/DE10359636A1/de not_active Withdrawn
-
2004
- 2004-11-30 CN CNB2004800373143A patent/CN100516036C/zh not_active Expired - Fee Related
- 2004-11-30 KR KR1020067012050A patent/KR101139206B1/ko not_active Expired - Fee Related
- 2004-11-30 RU RU2006125513/04A patent/RU2361859C2/ru active
- 2004-11-30 JP JP2006544258A patent/JP4886520B2/ja not_active Expired - Fee Related
- 2004-11-30 WO PCT/EP2004/013565 patent/WO2005058809A1/en not_active Ceased
- 2004-11-30 ES ES04803357.5T patent/ES2693607T3/es not_active Expired - Lifetime
- 2004-11-30 EP EP04803357.5A patent/EP1694639B1/en not_active Expired - Lifetime
- 2004-11-30 BR BRPI0417700-2A patent/BRPI0417700A/pt not_active IP Right Cessation
- 2004-12-17 US US11/016,130 patent/US7199270B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1694639B1 (en) | 2018-08-22 |
| KR101139206B1 (ko) | 2012-04-26 |
| US7199270B2 (en) | 2007-04-03 |
| WO2005058809A1 (en) | 2005-06-30 |
| DE10359636A1 (de) | 2005-07-28 |
| EP1694639A1 (en) | 2006-08-30 |
| KR20060125809A (ko) | 2006-12-06 |
| RU2361859C2 (ru) | 2009-07-20 |
| JP2007515416A (ja) | 2007-06-14 |
| RU2006125513A (ru) | 2008-01-27 |
| BRPI0417700A (pt) | 2007-03-20 |
| CN1894207A (zh) | 2007-01-10 |
| US20050137426A1 (en) | 2005-06-23 |
| CN100516036C (zh) | 2009-07-22 |
| JP4886520B2 (ja) | 2012-02-29 |
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