FR3120367B1 - Procédé de préparation du 2-hydroxy-4-méthylthiobutyronitrile ou de son équivalent sélénié et applications - Google Patents

Procédé de préparation du 2-hydroxy-4-méthylthiobutyronitrile ou de son équivalent sélénié et applications Download PDF

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Publication number
FR3120367B1
FR3120367B1 FR2102123A FR2102123A FR3120367B1 FR 3120367 B1 FR3120367 B1 FR 3120367B1 FR 2102123 A FR2102123 A FR 2102123A FR 2102123 A FR2102123 A FR 2102123A FR 3120367 B1 FR3120367 B1 FR 3120367B1
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FR
France
Prior art keywords
selenated
hmsebn
methylthiobutyronitrile
hydroxy
applications
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Active
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FR2102123A
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English (en)
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FR3120367A1 (fr
Inventor
Virginie Belliere-Baca
Aymeric Guinaudeau
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Adisseo France SAS
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Adisseo France SAS
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Priority to FR2102123A priority Critical patent/FR3120367B1/fr
Application filed by Adisseo France SAS filed Critical Adisseo France SAS
Priority to CN202280018560.2A priority patent/CN117043139A/zh
Priority to EP22712964.0A priority patent/EP4301729A1/fr
Priority to KR1020237030084A priority patent/KR20230148825A/ko
Priority to US18/280,388 priority patent/US20240076267A1/en
Priority to PCT/FR2022/050388 priority patent/WO2022185018A1/fr
Priority to JP2023553011A priority patent/JP2024509428A/ja
Priority to TW111108007A priority patent/TW202302531A/zh
Publication of FR3120367A1 publication Critical patent/FR3120367A1/fr
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Publication of FR3120367B1 publication Critical patent/FR3120367B1/fr
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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
    • C07C391/00—Compounds containing selenium
    • 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
    • C07C319/28—Separation; Purification
    • 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
    • C07C323/50—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 carboxyl groups bound to the same carbon skeleton
    • C07C323/51—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 carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/57—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 carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58—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 carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
    • 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
    • C07C323/50—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 carboxyl groups bound to the same carbon skeleton
    • C07C323/51—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 carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60—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 carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L’invention concerne un procédé de préparation du 2-hydroxy-4-méthylthiobutyronitrile (HMTBN) ou de son équivalent sélénié (HMSeBN) à partir d’acide cyanhydrique et de 3-méthylthiopropanal (MTP) ou de l’aldéhyde sélénié correspondant (MSeP) comprenant les étapes suivantes : on ajuste le rapport molaire de l’HCN au MTP ou au MSeP à une valeur supérieure ou égale à 1 et on ajuste et on maintient le pH à une valeur supérieure ou égale à 3,5, pour obtenir un milieu réactionnel dans lequel l’HMTBN ou le HMSeBN est formé, puis on abaisse le pH du milieu réactionnel à une valeur inférieure ou égale à 2,5 et on extrait l’HCN du milieu réactionnel, et on récupère l’HMTBN ou l’HMSeBN. L’invention concerne aussi les applications de ce procédé.
FR2102123A 2021-03-04 2021-03-04 Procédé de préparation du 2-hydroxy-4-méthylthiobutyronitrile ou de son équivalent sélénié et applications Active FR3120367B1 (fr)

Priority Applications (8)

Application Number Priority Date Filing Date Title
FR2102123A FR3120367B1 (fr) 2021-03-04 2021-03-04 Procédé de préparation du 2-hydroxy-4-méthylthiobutyronitrile ou de son équivalent sélénié et applications
EP22712964.0A EP4301729A1 (fr) 2021-03-04 2022-03-04 Procédé de préparation du 2-hydroxy-4-méthylthiobutyronitrile ou de son équivalent sélénié et applications
KR1020237030084A KR20230148825A (ko) 2021-03-04 2022-03-04 2-하이드록시-4-메틸티오부티로니트릴 또는 이의 셀레늄 등가물을 제조하는 방법 및 적용
US18/280,388 US20240076267A1 (en) 2021-03-04 2022-03-04 Method for preparing 2-hydroxy-4-methylthiobutyronitrile or the selenium equivalent thereof, and applications
CN202280018560.2A CN117043139A (zh) 2021-03-04 2022-03-04 制备2-羟基-4-甲硫基丁腈或其硒等价物的方法及其应用
PCT/FR2022/050388 WO2022185018A1 (fr) 2021-03-04 2022-03-04 Procédé de préparation du 2-hydroxy-4-méthylthiobutyronitrile ou de son équivalent sélénié et applications
JP2023553011A JP2024509428A (ja) 2021-03-04 2022-03-04 ２－ヒドロキシ－４－メチルチオブチロニトリル並びにそのセレン等価物の製造方法及び利用
TW111108007A TW202302531A (zh) 2021-03-04 2022-03-04 用於製備2-羥基-4-甲硫基丁腈或其硒等價體之方法及其等之應用技術

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR2102123A FR3120367B1 (fr) 2021-03-04 2021-03-04 Procédé de préparation du 2-hydroxy-4-méthylthiobutyronitrile ou de son équivalent sélénié et applications
FR2102123 2021-03-04

Publications (2)

Publication Number Publication Date
FR3120367A1 FR3120367A1 (fr) 2022-09-09
FR3120367B1 true FR3120367B1 (fr) 2024-02-16

Family

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Application Number Title Priority Date Filing Date
FR2102123A Active FR3120367B1 (fr) 2021-03-04 2021-03-04 Procédé de préparation du 2-hydroxy-4-méthylthiobutyronitrile ou de son équivalent sélénié et applications

Country Status (8)

Country Link
US (1) US20240076267A1 (fr)
EP (1) EP4301729A1 (fr)
JP (1) JP2024509428A (fr)
KR (1) KR20230148825A (fr)
CN (1) CN117043139A (fr)
FR (1) FR3120367B1 (fr)
TW (1) TW202302531A (fr)
WO (1) WO2022185018A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3163937A1 (fr) 2024-06-28 2026-01-02 Adisseo France S.A.S. Procédé de préparation du 3-méthylsélénopropanal

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
FR2733231B1 (fr) * 1995-04-24 1997-07-04 Rhone Poulenc Nutrition Animal Procede de condensation de l'acide cyanhydrique avec un aldehyde
MX9709477A (es) 1995-06-07 1998-02-28 Novus Int Inc Proceso continuo de hidrolisis para preparar acido 2-hidroxi-4-metiltiobutanoico o sales del mismo.
DE19547236A1 (de) 1995-12-18 1997-07-03 Degussa Verfahren zur Herstellung von D,L-Methionin oder dessen Salz
US6545179B2 (en) 2000-02-15 2003-04-08 Aventis Animal Nutrition, Sa Process for the production of methionine
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
FR2907785B1 (fr) * 2006-10-27 2009-01-16 Tetrahedron Sas Procede de preparation de l'acide 2-hydroxy-4-methylselenobutyrique, seul ou en melange avec son analogue soufre, ainsi que leurs utilisations en nutrition, en particulier en nutrition animale
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
JP6826012B2 (ja) * 2017-09-08 2021-02-03 住友化学株式会社 メチオニン及び／又は２−ヒドロキシ−４−（メチルチオ）ブタン酸の製造方法
CN109160894A (zh) * 2018-10-15 2019-01-08 禄丰天宝磷化工有限公司 一种环保清洁的dl-2-氨基-4-甲硒基丁酸生产工艺

Also Published As

Publication number Publication date
EP4301729A1 (fr) 2024-01-10
JP2024509428A (ja) 2024-03-01
CN117043139A (zh) 2023-11-10
US20240076267A1 (en) 2024-03-07
KR20230148825A (ko) 2023-10-25
TW202302531A (zh) 2023-01-16
WO2022185018A1 (fr) 2022-09-09
FR3120367A1 (fr) 2022-09-09

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