CN101812004B - 3-(甲硫基)丙醛和2-羟基-4-(甲硫基)丁腈的制备方法 - Google Patents
3-(甲硫基)丙醛和2-羟基-4-(甲硫基)丁腈的制备方法 Download PDFInfo
- Publication number
- CN101812004B CN101812004B CN2010101447601A CN201010144760A CN101812004B CN 101812004 B CN101812004 B CN 101812004B CN 2010101447601 A CN2010101447601 A CN 2010101447601A CN 201010144760 A CN201010144760 A CN 201010144760A CN 101812004 B CN101812004 B CN 101812004B
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- Prior art keywords
- mmp
- methylthio group
- reaction
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- reaction medium
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- Expired - Fee Related
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- 238000000034 method Methods 0.000 title claims abstract description 30
- CZUGFKJYCPYHHV-UHFFFAOYSA-N 3-methylthiopropanol Chemical compound CSCCCO CZUGFKJYCPYHHV-UHFFFAOYSA-N 0.000 title 1
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims abstract description 37
- 239000003054 catalyst Substances 0.000 claims description 29
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 26
- 239000012429 reaction media Substances 0.000 claims description 21
- 239000004793 Polystyrene Substances 0.000 claims description 12
- 229920005989 resin Polymers 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 12
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 6
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- -1 dimethyl aminoethyl Chemical group 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000005826 halohydrocarbons Chemical class 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000000025 natural resin Substances 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 229920003002 synthetic resin Polymers 0.000 claims description 2
- 239000000057 synthetic resin Substances 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 abstract description 66
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract description 26
- CLUWOWRTHNNBBU-UHFFFAOYSA-N 3-methylthiopropanal Chemical compound CSCCC=O CLUWOWRTHNNBBU-UHFFFAOYSA-N 0.000 abstract 2
- VWWOJJANXYSACS-UHFFFAOYSA-N 2-hydroxy-4-methylsulfanylbutanenitrile Chemical compound CSCCC(O)C#N VWWOJJANXYSACS-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 41
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 229960004452 methionine Drugs 0.000 description 10
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 9
- 229930182817 methionine Natural products 0.000 description 9
- 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 description 9
- 230000004044 response Effects 0.000 description 9
- 230000008961 swelling Effects 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229920005990 polystyrene resin Polymers 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000009466 transformation Effects 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 238000006555 catalytic reaction Methods 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- HBAHZZVIEFRTEY-UHFFFAOYSA-N 2-heptylcyclohex-2-en-1-one Chemical compound CCCCCCCC1=CCCCC1=O HBAHZZVIEFRTEY-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- 229920001367 Merrifield resin Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PICCHNWCTUUCAQ-UHFFFAOYSA-N 2-hydroxypentanethioic s-acid Chemical compound CCCC(O)C(O)=S PICCHNWCTUUCAQ-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical group OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- FFEARJCKVFRZRR-UHFFFAOYSA-N L-Methionine Natural products CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 1
- 229930195722 L-methionine Natural products 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- KZVNBJZCTXLJIK-UHFFFAOYSA-N [Hg].CS Chemical compound [Hg].CS KZVNBJZCTXLJIK-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- NWFNSTOSIVLCJA-UHFFFAOYSA-L copper;diacetate;hydrate Chemical compound O.[Cu+2].CC([O-])=O.CC([O-])=O NWFNSTOSIVLCJA-UHFFFAOYSA-L 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000009666 routine test Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003555 thioacetals Chemical class 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 235000019160 vitamin B3 Nutrition 0.000 description 1
- 239000011708 vitamin B3 Substances 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
Images
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
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (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 |
|---|---|---|---|
| DE102004038053.8 | 2004-08-05 | ||
| DE102004038053A DE102004038053A1 (de) | 2004-08-05 | 2004-08-05 | Verfahren zur Herstellung von 3-(Methylthio)propanal |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2005800265919A Division CN101031542B (zh) | 2004-08-05 | 2005-07-14 | 3-(甲硫基)丙醛和2-羟基-4-(甲硫基)丁腈的制备方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101812004A CN101812004A (zh) | 2010-08-25 |
| CN101812004B true CN101812004B (zh) | 2012-09-19 |
Family
ID=35149290
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010101447601A Expired - Fee Related CN101812004B (zh) | 2004-08-05 | 2005-07-14 | 3-(甲硫基)丙醛和2-羟基-4-(甲硫基)丁腈的制备方法 |
| CN2005800265919A Expired - Fee Related CN101031542B (zh) | 2004-08-05 | 2005-07-14 | 3-(甲硫基)丙醛和2-羟基-4-(甲硫基)丁腈的制备方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2005800265919A Expired - Fee Related CN101031542B (zh) | 2004-08-05 | 2005-07-14 | 3-(甲硫基)丙醛和2-羟基-4-(甲硫基)丁腈的制备方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7119233B2 (https=) |
| EP (2) | EP1778631B1 (https=) |
| JP (2) | JP4773441B2 (https=) |
| CN (2) | CN101812004B (https=) |
| BR (1) | BRPI0513072A (https=) |
| CA (1) | CA2573047A1 (https=) |
| DE (1) | DE102004038053A1 (https=) |
| ES (2) | ES2667220T3 (https=) |
| MX (1) | MX2007000345A (https=) |
| RU (1) | RU2383531C2 (https=) |
| WO (1) | WO2006015684A2 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005003990A1 (de) * | 2005-01-28 | 2006-08-03 | Degussa Ag | Herstellung von 3-(Alkylthio)propanal |
| 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 |
| FR2966456B1 (fr) * | 2010-10-26 | 2013-03-15 | Adisseo France Sas | Procede d'obtention d'acroleine par deshydratation catalytique de glycerol ou de glycerine |
| EP2468383A1 (de) * | 2010-12-22 | 2012-06-27 | Evonik Degussa GmbH | Verfahren zur thermischen Nachverbrennung von Abgasen aus der Acrolein- und aus der Blausäureherstellung |
| MY174539A (en) | 2011-02-23 | 2020-04-24 | Evonik Degussa Gmbh | Method for producing 2-hydroxy-4-(methylthio)butanenitrile from 3-(methylthio)propanal and hydrogen cyanide |
| SG192908A1 (en) | 2011-02-23 | 2013-09-30 | Evonik Degussa Gmbh | Storage-stable 2-hydroxy-4-(methylthio) butyric acid nitrile |
| WO2014195157A1 (de) | 2013-06-03 | 2014-12-11 | Evonik Degussa Gmbh | Verfahren zur herstellung von acrolein |
| CN107417570B (zh) * | 2017-09-14 | 2020-04-14 | 哈尔滨理工大学 | 利用丙酮氰醇制备α-羟基腈的方法 |
| 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 |
| CN109651215B (zh) * | 2019-02-14 | 2023-12-22 | 天宝动物营养科技股份有限公司 | 一种2-羟基-4-甲硫基丁腈的连续制备工艺和装置 |
| CN121794383A (zh) | 2023-07-17 | 2026-04-03 | 摩珈生物科技有限公司 | 通过3-甲硫基丙醛与c1来源的甲酰辅酶a缩合生产蛋氨酸 |
| CN119912370B (zh) * | 2025-04-03 | 2025-08-05 | 山东新和成氨基酸有限公司 | 一种2-羟基-4-甲硫基丁腈的制备方法及反应装置 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2542768A (en) * | 1945-10-24 | 1951-02-20 | Du Pont | Hydroxy-methylmercaptobutyronitrile |
| DE2320544C2 (de) | 1973-04-21 | 1975-06-05 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Verfahren zur Herstellung von 3-Methylmercaptopropionaldehyd |
| FR2314917A1 (fr) | 1975-06-20 | 1977-01-14 | Rhone Poulenc Ind | Procede de fabrication de l'aldehyde beta-methylthiopropionique |
| DE2623285C3 (de) | 1976-05-25 | 1980-10-02 | Gebrueder Grau Und Co Kg Chem. Fabrik, 7070 Schwaebisch Gmuend | Riechstoffkomposition |
| FR2460925A1 (fr) | 1979-07-10 | 1981-01-30 | Rhone Poulenc Ind | Procede de preparation directe d'aldehyde beta-methylthiopropionique |
| FR2480925A1 (fr) | 1980-04-22 | 1981-10-23 | Electricite De France | Echangeur thermique modulaire |
| US4440676A (en) | 1981-12-24 | 1984-04-03 | The British Petroleum Company P.L.C. | Process for the production of a dipeptide, a polypeptide or a protein |
| 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 |
| US5905171A (en) | 1995-06-22 | 1999-05-18 | Novus International, Inc. | Process for the preparation of 3-(methylthio)propanal |
| US5352837A (en) | 1993-06-08 | 1994-10-04 | 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 |
| 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 |
| DE69722195T2 (de) * | 1996-04-01 | 2004-04-01 | Union Carbide Chemicals & Plastics Technology Corp., Danbury | Verfahren zur herstellung von methylmercatopropanal |
| JP4517486B2 (ja) * | 2000-09-25 | 2010-08-04 | 住友化学株式会社 | ２−ヒドロキシ−４−メチルチオブタンニトリルの製造方法 |
| WO2003009936A2 (en) * | 2001-07-23 | 2003-02-06 | Andrew Bruce Holmes | Palladium-catalysed carbon-carbon bond forming reactions in compressed carbon dioxide |
| 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 |
-
2004
- 2004-08-05 DE DE102004038053A patent/DE102004038053A1/de not_active Ceased
-
2005
- 2005-07-14 MX MX2007000345A patent/MX2007000345A/es active IP Right Grant
- 2005-07-14 CN CN2010101447601A patent/CN101812004B/zh not_active Expired - Fee Related
- 2005-07-14 RU RU2007108071/04A patent/RU2383531C2/ru not_active IP Right Cessation
- 2005-07-14 JP JP2007524209A patent/JP4773441B2/ja not_active Expired - Fee Related
- 2005-07-14 BR BRPI0513072-7A patent/BRPI0513072A/pt not_active Application Discontinuation
- 2005-07-14 EP EP05775924.3A patent/EP1778631B1/de not_active Expired - Lifetime
- 2005-07-14 CA CA002573047A patent/CA2573047A1/en not_active Abandoned
- 2005-07-14 ES ES15186588.8T patent/ES2667220T3/es not_active Expired - Lifetime
- 2005-07-14 EP EP15186588.8A patent/EP2987785B1/de not_active Expired - Lifetime
- 2005-07-14 ES ES05775924.3T patent/ES2560447T3/es not_active Expired - Lifetime
- 2005-07-14 WO PCT/EP2005/007666 patent/WO2006015684A2/de not_active Ceased
- 2005-07-14 CN CN2005800265919A patent/CN101031542B/zh not_active Expired - Fee Related
- 2005-08-05 US US11/198,609 patent/US7119233B2/en not_active Expired - Lifetime
-
2011
- 2011-03-24 JP JP2011066503A patent/JP5306402B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2573047A1 (en) | 2006-02-16 |
| CN101812004A (zh) | 2010-08-25 |
| JP2011132256A (ja) | 2011-07-07 |
| CN101031542A (zh) | 2007-09-05 |
| WO2006015684A3 (de) | 2006-08-03 |
| MX2007000345A (es) | 2007-03-07 |
| CN101031542B (zh) | 2010-05-12 |
| DE102004038053A1 (de) | 2006-04-27 |
| JP2008508330A (ja) | 2008-03-21 |
| ES2667220T3 (es) | 2018-05-10 |
| RU2007108071A (ru) | 2008-09-20 |
| EP2987785B1 (de) | 2018-03-14 |
| US7119233B2 (en) | 2006-10-10 |
| RU2383531C2 (ru) | 2010-03-10 |
| JP5306402B2 (ja) | 2013-10-02 |
| EP1778631A2 (de) | 2007-05-02 |
| BRPI0513072A (pt) | 2008-04-22 |
| US20060030739A1 (en) | 2006-02-09 |
| JP4773441B2 (ja) | 2011-09-14 |
| EP1778631B1 (de) | 2015-11-18 |
| WO2006015684A2 (de) | 2006-02-16 |
| EP2987785A1 (de) | 2016-02-24 |
| ES2560447T3 (es) | 2016-02-19 |
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