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 PDFInfo
- 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
- Authority
- FR
- France
- Prior art keywords
- selenated
- hmsebn
- methylthiobutyronitrile
- hydroxy
- applications
- 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.)
- Active
Links
- VWWOJJANXYSACS-UHFFFAOYSA-N 2-hydroxy-4-methylsulfanylbutanenitrile Chemical compound CSCCC(O)C#N VWWOJJANXYSACS-UHFFFAOYSA-N 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 3
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 abstract 4
- CLUWOWRTHNNBBU-UHFFFAOYSA-N 3-methylthiopropanal Chemical compound CSCCC=O CLUWOWRTHNNBBU-UHFFFAOYSA-N 0.000 abstract 3
- 239000012429 reaction media Substances 0.000 abstract 3
- 150000001299 aldehydes Chemical class 0.000 abstract 1
Classifications
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- 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
Landscapes
- 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.
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 |
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 |
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 |
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 |
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 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR2102123 | 2021-03-04 | ||
FR2102123A FR3120367B1 (fr) | 2021-03-04 | 2021-03-04 | Procédé de préparation du 2-hydroxy-4-méthylthiobutyronitrile ou de son équivalent sélénié et applications |
Publications (2)
Publication Number | Publication Date |
---|---|
FR3120367A1 FR3120367A1 (fr) | 2022-09-09 |
FR3120367B1 true FR3120367B1 (fr) | 2024-02-16 |
Family
ID=76159506
Family Applications (1)
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) |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MY109603A (en) * | 1992-05-21 | 1997-03-31 | Daicel Chem | Process for producing 2-hydroxy-4-methylthiobutanoic acid |
PT832062E (pt) | 1995-06-07 | 2002-03-28 | Novus Int Inc | Processo de hidrolise continuo para preparacao de acido 2-hidroxi-4-metiltiobutanoico ou seus sais |
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 |
MX341595B (es) | 2011-02-23 | 2016-08-26 | Evonik Degussa Gmbh | Metodo para producir 2-hidroxi-4-(metiltio)butironitrilo a partir de 3-(metiltio)propanal y cianuro de hidrogeno. |
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 |
-
2021
- 2021-03-04 FR FR2102123A patent/FR3120367B1/fr active Active
-
2022
- 2022-03-04 KR KR1020237030084A patent/KR20230148825A/ko unknown
- 2022-03-04 US US18/280,388 patent/US20240076267A1/en active Pending
- 2022-03-04 JP JP2023553011A patent/JP2024509428A/ja active Pending
- 2022-03-04 CN CN202280018560.2A patent/CN117043139A/zh active Pending
- 2022-03-04 TW TW111108007A patent/TW202302531A/zh unknown
- 2022-03-04 WO PCT/FR2022/050388 patent/WO2022185018A1/fr active Application Filing
- 2022-03-04 EP EP22712964.0A patent/EP4301729A1/fr active Pending
Also Published As
Publication number | Publication date |
---|---|
FR3120367A1 (fr) | 2022-09-09 |
JP2024509428A (ja) | 2024-03-01 |
CN117043139A (zh) | 2023-11-10 |
US20240076267A1 (en) | 2024-03-07 |
KR20230148825A (ko) | 2023-10-25 |
EP4301729A1 (fr) | 2024-01-10 |
WO2022185018A1 (fr) | 2022-09-09 |
TW202302531A (zh) | 2023-01-16 |
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PLFP | Fee payment |
Year of fee payment: 2 |
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Effective date: 20220909 |
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