DE2627430C3 - Verfahren zur Herstellung von beta- Methylthiopropionaldehyd - Google Patents
Verfahren zur Herstellung von beta- MethylthiopropionaldehydInfo
- Publication number
- DE2627430C3 DE2627430C3 DE2627430A DE2627430A DE2627430C3 DE 2627430 C3 DE2627430 C3 DE 2627430C3 DE 2627430 A DE2627430 A DE 2627430A DE 2627430 A DE2627430 A DE 2627430A DE 2627430 C3 DE2627430 C3 DE 2627430C3
- Authority
- DE
- Germany
- Prior art keywords
- mtpa
- acrolein
- reaction
- methylthiopropionaldehyde
- methyl mercaptan
- 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
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 3
- QYYAEQQRMTZUPJ-UHFFFAOYSA-N butanethial Chemical compound CCCC=S QYYAEQQRMTZUPJ-UHFFFAOYSA-N 0.000 title 1
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 48
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 24
- 238000010521 absorption reaction Methods 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 230000003197 catalytic effect Effects 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- JJYKJUXBWFATTE-UHFFFAOYSA-N mosher's acid Chemical compound COC(C(O)=O)(C(F)(F)F)C1=CC=CC=C1 JJYKJUXBWFATTE-UHFFFAOYSA-N 0.000 description 46
- 101000841267 Homo sapiens Long chain 3-hydroxyacyl-CoA dehydrogenase Proteins 0.000 description 41
- 102100029107 Long chain 3-hydroxyacyl-CoA dehydrogenase Human genes 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000007789 gas Substances 0.000 description 16
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000003990 capacitor Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 2
- AVBGNFCMKJOFIN-UHFFFAOYSA-N triethylammonium acetate Chemical compound CC(O)=O.CCN(CC)CC AVBGNFCMKJOFIN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 208000005156 Dehydration Diseases 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- 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
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7520183A FR2314917A1 (fr) | 1975-06-20 | 1975-06-20 | Procede de fabrication de l'aldehyde beta-methylthiopropionique |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2627430A1 DE2627430A1 (de) | 1976-12-23 |
| DE2627430B2 DE2627430B2 (de) | 1977-07-21 |
| DE2627430C3 true DE2627430C3 (de) | 1985-01-10 |
Family
ID=9157148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2627430A Expired DE2627430C3 (de) | 1975-06-20 | 1976-06-18 | Verfahren zur Herstellung von beta- Methylthiopropionaldehyd |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4225516A (en:Method) |
| JP (1) | JPS523013A (en:Method) |
| BE (1) | BE843077A (en:Method) |
| BR (1) | BR7603949A (en:Method) |
| CA (1) | CA1069536A (en:Method) |
| CH (1) | CH610882A5 (en:Method) |
| DE (1) | DE2627430C3 (en:Method) |
| ES (1) | ES448918A1 (en:Method) |
| FR (1) | FR2314917A1 (en:Method) |
| GB (1) | GB1510256A (en:Method) |
| IT (1) | IT1061767B (en:Method) |
| MX (1) | MX144160A (en:Method) |
| NL (1) | NL184517C (en:Method) |
| SE (1) | SE431089B (en:Method) |
| SU (1) | SU691086A3 (en:Method) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2460925A1 (fr) * | 1979-07-10 | 1981-01-30 | Rhone Poulenc Ind | Procede de preparation directe d'aldehyde beta-methylthiopropionique |
| US4331682A (en) * | 1980-03-14 | 1982-05-25 | Ciba-Geigy Corporation | Cyclopropanecarboxylic acid-α-haloethynyl-m-phenoxybenzyl esters and their use for combating insect pests |
| JPS5970827U (ja) * | 1982-11-02 | 1984-05-14 | 株式会社神崎高級工機製作所 | 自走式作業車の車速変速装置 |
| ES2020535B3 (es) * | 1986-10-28 | 1991-08-16 | Atochem North America Inc (A Pennsylvania Corp ) | Preparacion de 3-alquiltio aldehidos. |
| JPH03106372U (en:Method) * | 1990-02-21 | 1991-11-01 | ||
| US5352837A (en) * | 1993-06-08 | 1994-10-04 | Novus International, Inc. | Process for the preparation of 3-(methylthio)propanal |
| US5925794A (en) * | 1993-06-08 | 1999-07-20 | Novus International, Inc. | Process for the preparation of 3-(methylthio)propanal |
| US5637766A (en) * | 1993-06-08 | 1997-06-10 | Novus International, Inc. | Process for the preparation of 3-(methylthio) propanal |
| US5905171A (en) * | 1995-06-22 | 1999-05-18 | Novus International, Inc. | Process for the preparation of 3-(methylthio)propanal |
| AU699841B2 (en) * | 1994-07-11 | 1998-12-17 | Novus International Inc | Process for the preparation of 3-(methylthio)propanal |
| AR002174A1 (es) * | 1995-06-07 | 1998-01-07 | Novus Int Inc | Proceso para la preparacion de 3-(metiltio)propanal y 2-hidroxi-4-metiltio) butanonitrilo |
| US5663409A (en) * | 1995-06-07 | 1997-09-02 | Novus International, Inc. | Process for the preparation of 3-(methylthio) propanal and 2-hydroxy-4-(methylthio) butanenitrile |
| FR2735989B1 (fr) * | 1995-06-29 | 1997-08-14 | Rhone Poulenc Nutrition Animal | Procede et installation de purification d'un flux gazeux contenant de l'acroleine |
| US5825369A (en) * | 1996-01-16 | 1998-10-20 | International Business Machines Corporation | Compression of simple geometric models using spanning trees |
| AU2594797A (en) * | 1996-04-01 | 1997-10-22 | Jonathan Lester Brockwell | Processes for the manufacture of methylmercaptopropanal |
| FR2758459B1 (fr) * | 1997-01-17 | 1999-05-07 | Pharma Pass | Composition pharmaceutique de fenofibrate presentant une biodisponibilite elevee et son procede de preparation |
| FR2835831B1 (fr) * | 2002-02-12 | 2006-09-01 | Aventis Animal Nutrition Sa | Procede de purification de l'acroleine |
| JP4186572B2 (ja) * | 2002-09-27 | 2008-11-26 | 住友化学株式会社 | ３−メチルチオプロパナールの製造方法 |
| EP1413573A1 (en) * | 2002-10-24 | 2004-04-28 | Adisseo France S.A.S. | Process for the production of 3-methylthiopropanal |
| DE102004038053A1 (de) | 2004-08-05 | 2006-04-27 | Degussa Ag | Verfahren zur Herstellung von 3-(Methylthio)propanal |
| FR2938535B1 (fr) | 2008-11-20 | 2012-08-17 | Arkema France | Procede de fabrication de methylmercaptopropionaldehyde et de methionine a partir de matieres renouvelables |
| DE102010064250A1 (de) * | 2010-12-28 | 2012-06-28 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Methylmercaptopropionaldehyd |
| CN102633698B (zh) * | 2012-04-28 | 2014-07-30 | 重庆紫光天化蛋氨酸有限责任公司 | 甲硫醇和丙烯醛合成的粗甲硫基代丙醛的处理方法和系统 |
| EP2679579A1 (de) | 2012-06-27 | 2014-01-01 | Evonik Industries AG | Integriertes Verfahren zur Herstellung von Acrolein und 3-Methylmercaptopropionaldehyd |
| CN102796030A (zh) * | 2012-08-31 | 2012-11-28 | 重庆紫光天化蛋氨酸有限责任公司 | 由甲硫醇和丙烯醛液液反应制备3-甲硫基丙醛的方法及装置 |
| WO2016031396A1 (ja) * | 2014-08-28 | 2016-03-03 | 富士フイルム株式会社 | 加飾材付き基材、加飾層形成用転写材料、タッチパネル、及び、情報表示装置 |
| EP3205643A1 (de) | 2016-02-15 | 2017-08-16 | Evonik Degussa GmbH | Verfahren zur herstellung von 3-methylthiopropionaldehyd |
| CN111116437B (zh) * | 2018-11-01 | 2021-02-05 | 山东新和成氨基酸有限公司 | 制备2-羟基-4-甲硫基丁酸及其中间体的方法和装置 |
| WO2022008505A1 (en) | 2020-07-08 | 2022-01-13 | Evonik Operations Gmbh | Process for preparing 3-methylthiopropionaldehyde |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2676190A (en) * | 1951-10-23 | 1954-04-20 | Du Pont | Process for the manufacture of beta-methylmercapto-propionaldehyde |
| US2776996A (en) * | 1955-12-22 | 1957-01-08 | Du Pont | Manufacture of beta-methylmercaptopropionaldehyde |
| YU32920B (en) * | 1966-04-25 | 1975-12-31 | Sumitomo Co Ltd | Postupak za proizvodnju -metilmerkaptopropionaldehida od akroleina i metilmerkaptana |
| US3529940A (en) * | 1966-04-25 | 1970-09-22 | Sumitomo Chemical Co | Apparatus for two-stage production of beta-methylmercaptopropionaldehyde |
| BE697818A (en:Method) * | 1966-04-30 | 1967-10-02 | ||
| US3555082A (en) * | 1966-12-15 | 1971-01-12 | Knapsack Ag | Process for isolating acrylic acid from the reaction gases obtained by oxidation of propylene or acrolein |
| ES357862A1 (es) * | 1967-10-13 | 1970-04-01 | Glanzstoff Ag | Procedimiento para la fabricacion de beta metilmecaptopro- pionaldehido. |
| NL6809647A (en:Method) * | 1968-07-09 | 1970-01-13 | ||
| DE2320544C2 (de) * | 1973-04-21 | 1975-06-05 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Verfahren zur Herstellung von 3-Methylmercaptopropionaldehyd |
-
1975
- 1975-06-20 FR FR7520183A patent/FR2314917A1/fr active Granted
-
1976
- 1976-06-15 SU SU762370202A patent/SU691086A3/ru active
- 1976-06-15 US US05/696,432 patent/US4225516A/en not_active Expired - Lifetime
- 1976-06-16 MX MX165165A patent/MX144160A/es unknown
- 1976-06-16 JP JP51070901A patent/JPS523013A/ja active Granted
- 1976-06-16 ES ES448918A patent/ES448918A1/es not_active Expired
- 1976-06-17 BE BE168033A patent/BE843077A/xx not_active IP Right Cessation
- 1976-06-17 NL NLAANVRAGE7606580,A patent/NL184517C/xx not_active IP Right Cessation
- 1976-06-18 CH CH783176A patent/CH610882A5/xx not_active IP Right Cessation
- 1976-06-18 BR BR7603949A patent/BR7603949A/pt unknown
- 1976-06-18 CA CA255,246A patent/CA1069536A/fr not_active Expired
- 1976-06-18 DE DE2627430A patent/DE2627430C3/de not_active Expired
- 1976-06-18 IT IT50004/76A patent/IT1061767B/it active
- 1976-06-18 SE SE7607035A patent/SE431089B/xx unknown
- 1976-06-18 GB GB25461/76A patent/GB1510256A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE7607035L (sv) | 1976-12-21 |
| NL184517B (nl) | 1989-03-16 |
| CA1069536A (fr) | 1980-01-08 |
| SE431089B (sv) | 1984-01-16 |
| FR2314917B1 (en:Method) | 1977-12-02 |
| JPS523013A (en) | 1977-01-11 |
| CH610882A5 (en:Method) | 1979-05-15 |
| SU691086A3 (ru) | 1979-10-05 |
| US4225516A (en) | 1980-09-30 |
| JPS57317B2 (en:Method) | 1982-01-06 |
| NL7606580A (nl) | 1976-12-22 |
| IT1061767B (it) | 1983-04-30 |
| DE2627430A1 (de) | 1976-12-23 |
| BR7603949A (pt) | 1977-03-22 |
| ES448918A1 (es) | 1977-07-01 |
| FR2314917A1 (fr) | 1977-01-14 |
| BE843077A (fr) | 1976-12-17 |
| NL184517C (nl) | 1989-08-16 |
| MX144160A (es) | 1981-09-08 |
| DE2627430B2 (de) | 1977-07-21 |
| GB1510256A (en) | 1978-05-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8281 | Inventor (new situation) |
Free format text: BIOLA, GEORGES, VENISSIEUX, FR KOMORN, YVES, LYON, FR LIMONGI, ERIC, VILLEURBANNE, FR |
|
| C3 | Grant after two publication steps (3rd publication) |