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RU2002124569A - METHODINE PRODUCTION METHOD - Google Patents

METHODINE PRODUCTION METHOD

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Publication number
RU2002124569A
RU2002124569A RU2002124569/04A RU2002124569A RU2002124569A RU 2002124569 A RU2002124569 A RU 2002124569A RU 2002124569/04 A RU2002124569/04 A RU 2002124569/04A RU 2002124569 A RU2002124569 A RU 2002124569A RU 2002124569 A RU2002124569 A RU 2002124569A
Authority
RU
Russia
Prior art keywords
ammonia
catalyst
methionine
preceding paragraphs
ketone
Prior art date
Application number
RU2002124569/04A
Other languages
Russian (ru)
Other versions
RU2265593C2 (en
Inventor
Эрве ПОНСЕБЛАН (FR)
Эрве Понсеблан
Жан-Кристоф РОССИ (FR)
Жан-Кристоф РОССИ
Филипп ЛАВАЛЬ (FR)
Филипп Лаваль
Жорж ГРО (FR)
Жорж Гро
Original Assignee
Авентис Анималь Нютрисьон С.А. (Fr)
Авентис Анималь Нютрисьон С.А.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from PCT/EP2000/001529 external-priority patent/WO2001060789A1/en
Application filed by Авентис Анималь Нютрисьон С.А. (Fr), Авентис Анималь Нютрисьон С.А. filed Critical Авентис Анималь Нютрисьон С.А. (Fr)
Publication of RU2002124569A publication Critical patent/RU2002124569A/en
Application granted granted Critical
Publication of RU2265593C2 publication Critical patent/RU2265593C2/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups

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)

Abstract

A process for the production of methionine which comprises (a) a first step of contacting hydroxymethylthiobutyronitrile with ammonia or a solution of ammonia to produce a product comprising 2-amino methylthiobutyronitrile, (b) a second step of removing any excess ammonia or solution of ammonia from the product, (c) a third step of reacting the 2-amino methylthiobutyronitrile with a ketone and an alkali metal hydroxide to produce a product stream comprising methionine amide and an alkali metal salt of methionine, (d) a fourth step of removing any unreacted ketone and excess ammonia from the product stream, (e) a fifth step of contacting the treated product stream of step (d) with an ion exchange resin, to carry out an exchange process of the alkali metal on the resin, thereby liberating free methionine, (f) a sixth step of hydrolising the methionine amide in the presence of a catalyst comprising titanium to produce ammonium methioninate, and (g) a seventh step of liberating methionine from ammonium methioninate.

Claims (19)

1. Способ получения метионина, включающий (а) гидролиз метионинамида в присутствии катализатора, содержащего титан, с получением метионината аммония, причем указанный катализатор имеет пористость от 5 до 1000 нм, суммарный объем пор от 0,2 до 0,55 см3/г и площадь поверхности от 30 до 150 м2/г, и (b) вторую стадию рекуперации метионина из соли, метионината аммония, путем удаления аммиака.1. A method of producing methionine, comprising (a) hydrolysis of methioninamide in the presence of a catalyst containing titanium, to obtain ammonium methioninate, said catalyst having a porosity of 5 to 1000 nm, a total pore volume of 0.2 to 0.55 cm 3 / g and a surface area of 30 to 150 m 2 / g, and (b) a second step for recovering methionine from the salt, ammonium methionate, by removing ammonia. 2. Способ по п.1, в котором катализатор имеет распределение размеров макропор от 5 до 100 нм и от 20 до 1000 нм.2. The method according to claim 1, in which the catalyst has a macropore size distribution of from 5 to 100 nm and from 20 to 1000 nm. 3. Способ по п.1 или 2, в котором общий объем пор равен от 0,25 до 0, 45 см3/г.3. The method according to claim 1 or 2, in which the total pore volume is from 0.25 to 0.45 cm 3 / g. 4. Способ по любому из предшествующих пунктов, в котором площадь поверхности равна от 40 до 120 м2/г.4. The method according to any one of the preceding paragraphs, wherein the surface area is from 40 to 120 m 2 / g. 5. Способ по любому из предшествующих пунктов, в котором диаметр катализатора равен от 0,05 до 2 мм.5. The method according to any one of the preceding paragraphs, in which the diameter of the catalyst is from 0.05 to 2 mm. 6. Способ по любому из предшествующих пунктов, в котором катализатор содержит TiO2, Ti-W, Ti-Mo, Ti-Si-W, Ti-Nb-Mo, Ti-Zr, Ti-Al, Ti-Cr, Ti-Zn и Ti-V или их смесь.6. The method according to any one of the preceding paragraphs, in which the catalyst contains TiO 2 , Ti-W, Ti-Mo, Ti-Si-W, Ti-Nb-Mo, Ti-Zr, Ti-Al, Ti-Cr, Ti Zn and Ti-V or a mixture thereof. 7. Способ по п.6, в котором катализатор содержит TiO2.7. The method according to claim 6, in which the catalyst contains TiO 2 . 8. Способ по любому из предшествующих пунктов, в котором катализатор присутствует в количестве от 0,1 до 2 г катализатора на грамм амида.8. The method according to any one of the preceding paragraphs, in which the catalyst is present in an amount of from 0.1 to 2 g of catalyst per gram of amide. 9. Способ по любому из предшествующих пунктов, в котором амид присутствует в количестве от 0,01 до 2 моль/кг.9. The method according to any one of the preceding paragraphs, in which the amide is present in an amount of from 0.01 to 2 mol / kg 10. Способ по любому из предшествующих пунктов, в котором гидролиз осуществляют при температуре от 50 до 150°С.10. The method according to any one of the preceding paragraphs, in which the hydrolysis is carried out at a temperature of from 50 to 150 ° C. 11. Способ по любому из предшествующих пунктов, в котором гидролиз осуществляют при давлении от 1 до 10 бар.11. The method according to any one of the preceding paragraphs, in which the hydrolysis is carried out at a pressure of from 1 to 10 bar. 12. Способ по любому из предшествующих пунктов, в котором аммиак удаляют отгонкой.12. The method according to any one of the preceding paragraphs, in which ammonia is removed by distillation. 13. Способ получения метионина, пригодный для промышленного применения и включающий (a) введение 2-гидрокси-4-метилтиобутаннитрила в контакт с аммиаком или содержащим аммиак раствором для получения первого продукта, содержащего 2-амино-4-метилтиобутаннитрил, (b) осуществление взаимодействия 2-амино-4-метилтиобутаннитрила с кетоном и гидроксидом щелочного металла с образованием второго продукта, содержащего метионинамид, (c) удаление не прореагировавшего кетона, аммиака и воды из второго потока продукта, (d) гидролиз метионинамида в присутствии катализатора, включающего титан, с получением третьего потока продукта, содержащего метионинат аммония, причем указанный катализатор имеет пористость от 5 до 1000 нм, суммарный объем пор от 0,2 до 0,55 см3/г, и площадь поверхности от 30 до 150 м2/г и (е) высвобождение метионина из соли, метионината аммония.13. A method of producing methionine suitable for industrial use, comprising (a) contacting 2-hydroxy-4-methylthiobutannitrile with ammonia or an ammonia-containing solution to produce a first product containing 2-amino-4-methylthiobutanenitrile, (b) reacting 2-amino-4-methylthiobutannitrile with a ketone and alkali metal hydroxide to form a second product containing methioninamide, (c) removing unreacted ketone, ammonia and water from the second product stream, (d) hydrolysis of methioninamide in the presence of and a catalyst comprising titanium, to obtain a third product stream containing ammonium methioninate, said catalyst having a porosity of 5 to 1000 nm, a total pore volume of 0.2 to 0.55 cm 3 / g, and a surface area of 30 to 150 m 2 / g; and (e) release of methionine from a salt, ammonium methioninate. 14. Способ по п.13, в котором метионинамид вводят в контакт с кислотной смолой перед гидролизом.14. The method of claim 13, wherein the methioninamide is contacted with the acidic resin before hydrolysis. 15. Способ по п.13, в котором метионин, полученный на стадии (е) вводят в контакт с кислотной смолой.15. The method according to item 13, in which the methionine obtained in stage (e) is contacted with an acidic resin. 16. Способ по любому из пп.13-15, в котором непрореагировавшие и/или регенерированные аммиак, кетон и воду отправляют в секцию регенерации, и аммиак отделяют от воды и кетона.16. The method according to any of paragraphs.13-15, in which unreacted and / or regenerated ammonia, ketone and water are sent to the regeneration section, and ammonia is separated from water and ketone. 17. Способ по п.16, в котором разделение осуществляют путем абсорбции и перегонки.17. The method according to clause 16, in which the separation is carried out by absorption and distillation. 18. Способ по п.16 или 17, в котором выделенный аммиак возвращают на повторную переработку в реактор для синтеза аминонитрила.18. The method according to clause 16 or 17, in which the separated ammonia is returned for recycling to the reactor for the synthesis of aminonitrile. 19. Способ по любому из пп.16-18, в котором отделенные кетон и воду возвращают на повторную переработку в реактор для синтеза аминоамида.19. The method according to any one of claims 16-18, wherein the separated ketone and water are returned for recycling to the aminoamide synthesis reactor.
RU2002124569/04A 2000-02-15 2001-02-14 Method for preparing methionine RU2265593C2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
PCT/EP2000/001529 WO2001060789A1 (en) 2000-02-15 2000-02-15 Process for the production of methionine
EPPCT/EP00/01528 2000-02-15
EPPCT/EP00/01529 2000-02-15
PCT/EP2000/001528 WO2001060788A1 (en) 2000-02-15 2000-02-15 Process for the production of methionine

Publications (2)

Publication Number Publication Date
RU2002124569A true RU2002124569A (en) 2004-01-10
RU2265593C2 RU2265593C2 (en) 2005-12-10

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
RU2002124569/04A RU2265593C2 (en) 2000-02-15 2001-02-14 Method for preparing methionine

Country Status (5)

Country Link
CN (1) CN1227223C (en)
AT (1) ATE358120T1 (en)
AU (1) AU4066401A (en)
RU (1) RU2265593C2 (en)
WO (1) WO2001060788A1 (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2919607B1 (en) * 2007-07-31 2012-10-12 Adisseo Ireland Ltd PROCESS FOR THE CATALYTIC CONVERSION OF 2-HYDROXY-4-METHYLTHIOBUTANENITRILE (HMTBN) TO 2-HYDROXY-4-METHYLTHIOBUTANAMIDE (HMTBM)
MY171361A (en) * 2011-08-30 2019-10-10 Evonik Operations Gmbh Method for producing a methionine salt
DE102011081828A1 (en) * 2011-08-30 2013-02-28 Evonik Degussa Gmbh Process for the reaction of methylmercaptopropionaldehyde from crude acrolein and crude methylmercaptan
JP2014108956A (en) * 2012-12-04 2014-06-12 Sumitomo Chemical Co Ltd Method of manufacturing methionine
CN103497133B (en) * 2013-10-24 2015-05-13 重庆紫光化工股份有限公司 Method for preparing N-methylol group-D,L-calcium methionine microelement chelates by means of saponification liquid produced through D,L- methionine
CN103641757B (en) * 2013-11-19 2016-03-30 重庆紫光化工股份有限公司 The preparation method of HMBC
EP3689851A1 (en) * 2019-02-04 2020-08-05 Evonik Operations GmbH Salt-free production of methionine from methionine nitrile
WO2020249495A1 (en) * 2019-06-13 2020-12-17 Evonik Operations Gmbh Process for the preparation of methionine
CN112979515A (en) * 2019-12-18 2021-06-18 重庆紫光化工股份有限公司 Method for preparing 2-amino-4-methylthiobutanamide
CN112979514A (en) * 2019-12-18 2021-06-18 重庆紫光化工股份有限公司 Method for preparing D, L-methionine from 2-hydroxy-4-methylthiobutyronitrile
US20250108359A1 (en) 2022-01-28 2025-04-03 Evonik Operations Gmbh Granular catalyst for the hydrolysis of amino nitriles and amino amides to amino acids or derivatives thereof

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0393753A (en) * 1989-09-04 1991-04-18 Sumitomo Chem Co Ltd Production of alpha-amino acid
DE4235295A1 (en) * 1992-10-20 1994-04-21 Degussa Continuously feasible process for the preparation of methionine or methionine derivatives
FR2772026A1 (en) * 1997-12-05 1999-06-11 Rhone Poulenc Nutrition Animal Preparation of methionine or its hydroxy analog using cation exchange resin

Also Published As

Publication number Publication date
AU4066401A (en) 2001-08-27
ATE358120T1 (en) 2007-04-15
CN1400966A (en) 2003-03-05
CN1227223C (en) 2005-11-16
RU2265593C2 (en) 2005-12-10
WO2001060788A1 (en) 2001-08-23

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Effective date: 20160215