UA78613C2 - A process for the production of 3-methylthiopropanal and a process for the production of 2-hydroxy-4-(methylthio)butanenitrile - Google Patents
A process for the production of 3-methylthiopropanal and a process for the production of 2-hydroxy-4-(methylthio)butanenitrile Download PDFInfo
- Publication number
- UA78613C2 UA78613C2 UAA200504636A UA2005004636A UA78613C2 UA 78613 C2 UA78613 C2 UA 78613C2 UA A200504636 A UAA200504636 A UA A200504636A UA 2005004636 A UA2005004636 A UA 2005004636A UA 78613 C2 UA78613 C2 UA 78613C2
- Authority
- UA
- Ukraine
- Prior art keywords
- catalyst
- reaction
- differs
- mtra
- acrolein
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 41
- 238000004519 manufacturing process Methods 0.000 title abstract description 7
- CLUWOWRTHNNBBU-UHFFFAOYSA-N 3-methylthiopropanal Chemical compound CSCCC=O CLUWOWRTHNNBBU-UHFFFAOYSA-N 0.000 title abstract description 4
- VWWOJJANXYSACS-UHFFFAOYSA-N 2-hydroxy-4-methylsulfanylbutanenitrile Chemical compound CSCCC(O)C#N VWWOJJANXYSACS-UHFFFAOYSA-N 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims abstract description 76
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims abstract description 62
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims abstract description 61
- 150000007530 organic bases Chemical class 0.000 claims abstract description 17
- 239000012429 reaction media Substances 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims description 52
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
- 150000007524 organic acids Chemical class 0.000 claims description 11
- 235000011054 acetic acid Nutrition 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical group CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- JGSIAOZAXBWRFO-UHFFFAOYSA-N 3-methylsulfanyl-1-phenyl-4,5-dihydrobenzo[g]indazole Chemical compound C1CC2=CC=CC=C2C2=C1C(SC)=NN2C1=CC=CC=C1 JGSIAOZAXBWRFO-UHFFFAOYSA-N 0.000 claims 2
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 claims 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 22
- 229930182817 methionine Natural products 0.000 description 14
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 238000003860 storage Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000007259 addition reaction Methods 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 239000007809 chemical reaction catalyst Substances 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- -1 acetic acid Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- BPSNETAIJADFTO-UHFFFAOYSA-N 2-pyridinylacetic acid Chemical compound OC(=O)CC1=CC=CC=N1 BPSNETAIJADFTO-UHFFFAOYSA-N 0.000 description 2
- SFWWGMKXCYLZEG-UHFFFAOYSA-N 3-methylmorpholine Chemical compound CC1COCCN1 SFWWGMKXCYLZEG-UHFFFAOYSA-N 0.000 description 2
- CZUGFKJYCPYHHV-UHFFFAOYSA-N 3-methylthiopropanol Chemical compound CSCCCO CZUGFKJYCPYHHV-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000004312 hexamethylene tetramine Substances 0.000 description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 2
- 229940091173 hydantoin Drugs 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- ZHHJVIJTVGDMMV-UHFFFAOYSA-N 2-(3-methylmorpholin-4-yl)acetic acid Chemical compound CC1COCCN1CC(O)=O ZHHJVIJTVGDMMV-UHFFFAOYSA-N 0.000 description 1
- ONFOSYPQQXJWGS-UHFFFAOYSA-N 2-hydroxy-4-(methylthio)butanoic acid Chemical compound CSCCC(O)C(O)=O ONFOSYPQQXJWGS-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007333 cyanation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- 239000003797 essential amino acid Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000006052 feed supplement Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07C319/14—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
-
- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP20020356211 EP1413573A1 (en) | 2002-10-24 | 2002-10-24 | Process for the production of 3-methylthiopropanal |
| PCT/IB2003/004557 WO2004037774A1 (en) | 2002-10-24 | 2003-10-14 | Process for the production of 3-methylthiopropanal |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA78613C2 true UA78613C2 (en) | 2007-04-10 |
Family
ID=32050124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UAA200504636A UA78613C2 (en) | 2002-10-24 | 2003-10-14 | A process for the production of 3-methylthiopropanal and a process for the production of 2-hydroxy-4-(methylthio)butanenitrile |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US7256315B2 (zh) |
| EP (2) | EP1413573A1 (zh) |
| JP (1) | JP4521277B2 (zh) |
| KR (1) | KR100984125B1 (zh) |
| CN (1) | CN1277816C (zh) |
| AR (1) | AR041714A1 (zh) |
| AT (1) | ATE371642T1 (zh) |
| AU (1) | AU2003267771A1 (zh) |
| BR (1) | BR0315385A (zh) |
| CA (1) | CA2495746A1 (zh) |
| DE (1) | DE60316011T2 (zh) |
| ES (1) | ES2291662T3 (zh) |
| MX (1) | MXPA05004158A (zh) |
| MY (1) | MY134665A (zh) |
| NO (1) | NO20052471L (zh) |
| PL (1) | PL375101A1 (zh) |
| RU (1) | RU2336266C2 (zh) |
| TW (1) | TWI319391B (zh) |
| UA (1) | UA78613C2 (zh) |
| WO (1) | WO2004037774A1 (zh) |
| ZA (1) | ZA200501389B (zh) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1925612A4 (en) * | 2005-09-12 | 2009-07-01 | Sumitomo Chemical Co | PROCESS FOR PREPARING 4- (METHYLTHIO) BUTANE-1,2-DIOL |
| DE102008042932A1 (de) * | 2008-10-17 | 2010-04-22 | Evonik Degussa Gmbh | Herstellung und Verwendung von Methionylmethionin als Futtermitteladditiv für Fische und Krustentiere |
| FR2938535B1 (fr) | 2008-11-20 | 2012-08-17 | Arkema France | Procede de fabrication de methylmercaptopropionaldehyde et de methionine a partir de matieres renouvelables |
| JP5182199B2 (ja) * | 2009-04-06 | 2013-04-10 | 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 |
| JP5182198B2 (ja) * | 2009-04-06 | 2013-04-10 | 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 |
| JP5402864B2 (ja) * | 2010-07-20 | 2014-01-29 | 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 |
| CN109160893A (zh) * | 2018-10-15 | 2019-01-08 | 禄丰天宝磷化工有限公司 | 一种甲硒基丙醛的制备方法 |
| 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 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2427582A (en) * | 1944-09-27 | 1947-09-16 | Du Pont | Beta (acylthio) aldehydes and ketones and their preparation |
| US2776996A (en) * | 1955-12-22 | 1957-01-08 | Du Pont | Manufacture of beta-methylmercaptopropionaldehyde |
| FR2314917A1 (fr) * | 1975-06-20 | 1977-01-14 | Rhone Poulenc Ind | Procede de fabrication de l'aldehyde beta-methylthiopropionique |
| JPS57197262A (en) * | 1981-05-29 | 1982-12-03 | Res Dev Corp Of Japan | Production of optically active beta-arylthio or alkylthioketone |
| JP3219544B2 (ja) * | 1992-05-21 | 2001-10-15 | ダイセル化学工業株式会社 | ２−ヒドロキシ−４−メチルチオブタン酸の製造法 |
| MY109603A (en) * | 1992-05-21 | 1997-03-31 | Daicel Chem | Process for producing 2-hydroxy-4-methylthiobutanoic acid |
| US5637766A (en) * | 1993-06-08 | 1997-06-10 | Novus International, Inc. | Process for the preparation of 3-(methylthio) propanal |
| 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 |
| US5696282A (en) * | 1996-03-26 | 1997-12-09 | Phillips Petroleum Company | Process for producing organosulfur compounds |
-
2002
- 2002-10-24 EP EP20020356211 patent/EP1413573A1/en not_active Withdrawn
-
2003
- 2003-10-14 AT AT03748466T patent/ATE371642T1/de not_active IP Right Cessation
- 2003-10-14 BR BR0315385-1A patent/BR0315385A/pt not_active IP Right Cessation
- 2003-10-14 DE DE60316011T patent/DE60316011T2/de not_active Expired - Lifetime
- 2003-10-14 KR KR1020057007069A patent/KR100984125B1/ko active IP Right Grant
- 2003-10-14 JP JP2004546263A patent/JP4521277B2/ja not_active Expired - Fee Related
- 2003-10-14 CN CNB2003801015894A patent/CN1277816C/zh not_active Expired - Fee Related
- 2003-10-14 UA UAA200504636A patent/UA78613C2/uk unknown
- 2003-10-14 WO PCT/IB2003/004557 patent/WO2004037774A1/en active IP Right Grant
- 2003-10-14 ES ES03748466T patent/ES2291662T3/es not_active Expired - Lifetime
- 2003-10-14 US US10/524,548 patent/US7256315B2/en not_active Expired - Lifetime
- 2003-10-14 EP EP03748466A patent/EP1556343B1/en not_active Expired - Lifetime
- 2003-10-14 MX MXPA05004158A patent/MXPA05004158A/es not_active Application Discontinuation
- 2003-10-14 RU RU2005105040/04A patent/RU2336266C2/ru active
- 2003-10-14 CA CA002495746A patent/CA2495746A1/en not_active Abandoned
- 2003-10-14 PL PL03375101A patent/PL375101A1/xx not_active IP Right Cessation
- 2003-10-14 AU AU2003267771A patent/AU2003267771A1/en not_active Abandoned
- 2003-10-17 TW TW092128917A patent/TWI319391B/zh not_active IP Right Cessation
- 2003-10-20 MY MYPI20033986A patent/MY134665A/en unknown
- 2003-10-24 AR ARP030103885A patent/AR041714A1/es not_active Application Discontinuation
-
2005
- 2005-02-16 ZA ZA200501389A patent/ZA200501389B/en unknown
- 2005-05-23 NO NO20052471A patent/NO20052471L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NO20052471L (no) | 2005-07-25 |
| CN1705641A (zh) | 2005-12-07 |
| BR0315385A (pt) | 2005-08-23 |
| KR100984125B1 (ko) | 2010-09-28 |
| CA2495746A1 (en) | 2004-05-06 |
| EP1556343B1 (en) | 2007-08-29 |
| PL375101A1 (en) | 2005-11-14 |
| DE60316011D1 (de) | 2007-10-11 |
| ATE371642T1 (de) | 2007-09-15 |
| ZA200501389B (en) | 2006-07-26 |
| EP1556343A1 (en) | 2005-07-27 |
| TW200413299A (en) | 2004-08-01 |
| MY134665A (en) | 2007-12-31 |
| WO2004037774A1 (en) | 2004-05-06 |
| ES2291662T3 (es) | 2008-03-01 |
| KR20050067423A (ko) | 2005-07-01 |
| AU2003267771A1 (en) | 2004-05-13 |
| JP4521277B2 (ja) | 2010-08-11 |
| MXPA05004158A (es) | 2005-08-03 |
| RU2005105040A (ru) | 2005-10-27 |
| EP1413573A1 (en) | 2004-04-28 |
| TWI319391B (en) | 2010-01-11 |
| AR041714A1 (es) | 2005-05-26 |
| DE60316011T2 (de) | 2008-05-15 |
| US20050240048A1 (en) | 2005-10-27 |
| JP2006515834A (ja) | 2006-06-08 |
| NO20052471D0 (no) | 2005-05-23 |
| CN1277816C (zh) | 2006-10-04 |
| RU2336266C2 (ru) | 2008-10-20 |
| US7256315B2 (en) | 2007-08-14 |
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