CA1069536A - Procede de fabrication de l'aldehyde beta-methylthiopropionique - Google Patents
Procede de fabrication de l'aldehyde beta-methylthiopropioniqueInfo
- Publication number
- CA1069536A CA1069536A CA255,246A CA255246A CA1069536A CA 1069536 A CA1069536 A CA 1069536A CA 255246 A CA255246 A CA 255246A CA 1069536 A CA1069536 A CA 1069536A
- Authority
- CA
- Canada
- Prior art keywords
- reaction
- beta
- aldehyde
- amtp
- acrolein
- 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 abstract description 22
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title description 2
- 238000002360 preparation method Methods 0.000 title description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims abstract description 47
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims abstract description 25
- 238000010521 absorption reaction Methods 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 229910001868 water Inorganic materials 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 7
- 230000003197 catalytic effect Effects 0.000 claims abstract description 7
- 230000003647 oxidation Effects 0.000 claims abstract description 7
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 7
- 239000008246 gaseous mixture Substances 0.000 claims abstract 3
- 239000012429 reaction media Substances 0.000 claims description 9
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
- 238000000605 extraction Methods 0.000 abstract description 2
- KQEIJFWAXDQUPR-UHFFFAOYSA-N 2,4-diaminophenol;hydron;dichloride Chemical compound Cl.Cl.NC1=CC=C(O)C(N)=C1 KQEIJFWAXDQUPR-UHFFFAOYSA-N 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 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 2
- 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
- 230000015556 catabolic process Effects 0.000 description 2
- 210000001072 colon Anatomy 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 2
- 229940093635 tributyl phosphate Drugs 0.000 description 2
- 239000005745 Captan Substances 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 241000219422 Urtica Species 0.000 description 1
- 235000009108 Urtica dioica Nutrition 0.000 description 1
- KYKQHSMYWLWROM-UHFFFAOYSA-N ac1l4yjn Chemical compound [Hg].[Hg] KYKQHSMYWLWROM-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000001816 cooling 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
- 235000013305 food Nutrition 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- -1 methyl- Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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 (1)
| Publication Number | Publication Date |
|---|---|
| CA1069536A true CA1069536A (fr) | 1980-01-08 |
Family
ID=9157148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA255,246A Expired CA1069536A (fr) | 1975-06-20 | 1976-06-18 | Procede de fabrication de l'aldehyde beta-methylthiopropionique |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4225516A (instruction) |
| JP (1) | JPS523013A (instruction) |
| BE (1) | BE843077A (instruction) |
| BR (1) | BR7603949A (instruction) |
| CA (1) | CA1069536A (instruction) |
| CH (1) | CH610882A5 (instruction) |
| DE (1) | DE2627430C3 (instruction) |
| ES (1) | ES448918A1 (instruction) |
| FR (1) | FR2314917A1 (instruction) |
| GB (1) | GB1510256A (instruction) |
| IT (1) | IT1061767B (instruction) |
| MX (1) | MX144160A (instruction) |
| NL (1) | NL184517C (instruction) |
| SE (1) | SE431089B (instruction) |
| SU (1) | SU691086A3 (instruction) |
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 |
| EP0273101B1 (en) * | 1986-10-28 | 1991-01-30 | ATOCHEM NORTH AMERICA, INC. (a Pennsylvania corp.) | Preparation of 3-(alkylthio) aldehydes |
| JPH03106372U (instruction) * | 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 |
| 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 |
| US5925794A (en) * | 1993-06-08 | 1999-07-20 | Novus International, Inc. | Process for the preparation of 3-(methylthio)propanal |
| WO1996001810A1 (en) * | 1994-07-11 | 1996-01-25 | 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 |
| US6057481A (en) * | 1996-04-01 | 2000-05-02 | Union Carbide Chemicals & Plastics Technology Corporation | 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 |
| US3529940A (en) * | 1966-04-25 | 1970-09-22 | Sumitomo Chemical Co | Apparatus for two-stage production of beta-methylmercaptopropionaldehyde |
| GB1150252A (en) * | 1966-04-25 | 1969-04-30 | Sumitomo Chemical Co | Improvements relating to the production of beta-Methylmercaptopropionaldehyde |
| GB1166961A (en) * | 1966-04-30 | 1969-10-15 | Sumitomo Chemical Co | Process for Producing beta-Methylmercaptopropionaldehyde |
| 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 (instruction) * | 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 US US05/696,432 patent/US4225516A/en not_active Expired - Lifetime
- 1976-06-15 SU SU762370202A patent/SU691086A3/ru active
- 1976-06-16 JP JP51070901A patent/JPS523013A/ja active Granted
- 1976-06-16 MX MX165165A patent/MX144160A/es unknown
- 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 CA CA255,246A patent/CA1069536A/fr not_active Expired
- 1976-06-18 BR BR7603949A patent/BR7603949A/pt unknown
- 1976-06-18 CH CH783176A patent/CH610882A5/xx not_active IP Right Cessation
- 1976-06-18 DE DE2627430A patent/DE2627430C3/de not_active Expired
- 1976-06-18 IT IT50004/76A patent/IT1061767B/it active
- 1976-06-18 GB GB25461/76A patent/GB1510256A/en not_active Expired
- 1976-06-18 SE SE7607035A patent/SE431089B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2627430C3 (de) | 1985-01-10 |
| ES448918A1 (es) | 1977-07-01 |
| DE2627430B2 (de) | 1977-07-21 |
| NL7606580A (nl) | 1976-12-22 |
| CH610882A5 (instruction) | 1979-05-15 |
| BE843077A (fr) | 1976-12-17 |
| NL184517C (nl) | 1989-08-16 |
| IT1061767B (it) | 1983-04-30 |
| MX144160A (es) | 1981-09-08 |
| JPS57317B2 (instruction) | 1982-01-06 |
| FR2314917B1 (instruction) | 1977-12-02 |
| JPS523013A (en) | 1977-01-11 |
| FR2314917A1 (fr) | 1977-01-14 |
| SE431089B (sv) | 1984-01-16 |
| SU691086A3 (ru) | 1979-10-05 |
| NL184517B (nl) | 1989-03-16 |
| GB1510256A (en) | 1978-05-10 |
| SE7607035L (sv) | 1976-12-21 |
| BR7603949A (pt) | 1977-03-22 |
| DE2627430A1 (de) | 1976-12-23 |
| US4225516A (en) | 1980-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |