FR2405924A1 - Alpha-amino acid prodn. from amino nitrile - by single stage hydrolysis in presence of carbonyl catalyst - Google Patents
Alpha-amino acid prodn. from amino nitrile - by single stage hydrolysis in presence of carbonyl catalystInfo
- Publication number
- FR2405924A1 FR2405924A1 FR7730699A FR7730699A FR2405924A1 FR 2405924 A1 FR2405924 A1 FR 2405924A1 FR 7730699 A FR7730699 A FR 7730699A FR 7730699 A FR7730699 A FR 7730699A FR 2405924 A1 FR2405924 A1 FR 2405924A1
- Authority
- FR
- France
- Prior art keywords
- alpha
- pref
- iii
- opt
- hydrolysis
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Prepn. of alpha-aminoacids (I) comprises catalytic hydrolysis of an alpha-aminonitrile (II) or its salts, in aq. soln. of >=1 carbonyl deriv. (III) as catalyst in the presence of OH ions. The concn. of OH ions is approx. equimolar to that of (II), and after reaction free (I) is extracted. Pref. (III) is 0.1-2, esp. 0.1-1 mole per mole (II) and the min. amt. of water is 1 mole per mole (II). Pref. the soln. is heated to 80 degrees C. (II) are esp. of formula RCH-(NH2)CN. (R is H, or opt. branched 1-12C hydrocarbyl opt. contg. >=1 heteroatom such as S, and opt. substd. by >=1 OH, NH2, COOH, phenyl, hydroxyphenyl, carboxamido, indolyl, iminazyl or guanidinyl, pref. at the end of the chain; R can also form with the alpha-N, a satd. heterocycle which can be substd. e.g. by OH). (I) are used in human and veterinary medicine, in nutrition and in soaps and cosmetics. Hydrolysis is in a single stage with no need to isolate the intermediate alpha-amino amide. (III) and the NH3 generated during hydrolysis can be recycled and conversions are almost quantitative. In an example, alanine was prepd. in 96.6% yield by hydrolysing alpha-aminopropionitrile hydrochloride in presence of acetone.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7730699A FR2405924A1 (en) | 1977-10-12 | 1977-10-12 | Alpha-amino acid prodn. from amino nitrile - by single stage hydrolysis in presence of carbonyl catalyst |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7730699A FR2405924A1 (en) | 1977-10-12 | 1977-10-12 | Alpha-amino acid prodn. from amino nitrile - by single stage hydrolysis in presence of carbonyl catalyst |
Publications (2)
Publication Number | Publication Date |
---|---|
FR2405924A1 true FR2405924A1 (en) | 1979-05-11 |
FR2405924B1 FR2405924B1 (en) | 1980-05-16 |
Family
ID=9196411
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR7730699A Granted FR2405924A1 (en) | 1977-10-12 | 1977-10-12 | Alpha-amino acid prodn. from amino nitrile - by single stage hydrolysis in presence of carbonyl catalyst |
Country Status (1)
Country | Link |
---|---|
FR (1) | FR2405924A1 (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2519973A1 (en) * | 1982-01-15 | 1983-07-22 | Centre Nat Rech Scient | PROCESS FOR THE CATALYTIC HYDROLYSIS OF AN ALPHA-AMINO-NITRILE IN THE HETEROGENEOUS PHASE, AND THE POLYMERIC RESINS WITH CATALYTIC ACTIVITY FOR THE IMPLEMENTATION OF THE PROCESS |
WO1994008957A1 (en) * | 1992-10-20 | 1994-04-28 | Degussa Aktiengesellschaft | Method for the continuous preparation of methionine or methionine derivatives |
EP3453701A1 (en) * | 2017-09-08 | 2019-03-13 | Sumitomo Chemical Company, Limited | Method for producing methionine and/or 2-hydroxy-4-(methylthio)butanoic acid |
CN111635330A (en) * | 2020-06-24 | 2020-09-08 | 江苏扬农化工集团有限公司 | Method for recycling reaction residues of key intermediate of hexamethylene diamine and co-producing carboxylic acid |
-
1977
- 1977-10-12 FR FR7730699A patent/FR2405924A1/en active Granted
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2519973A1 (en) * | 1982-01-15 | 1983-07-22 | Centre Nat Rech Scient | PROCESS FOR THE CATALYTIC HYDROLYSIS OF AN ALPHA-AMINO-NITRILE IN THE HETEROGENEOUS PHASE, AND THE POLYMERIC RESINS WITH CATALYTIC ACTIVITY FOR THE IMPLEMENTATION OF THE PROCESS |
EP0084470A1 (en) * | 1982-01-15 | 1983-07-27 | Etablissement Public dit: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS) | Catalytic hydrolysis process of an alpha-amino-nitrile in the heterogeneous phase, and catalytically active polymer resins for this process |
WO1994008957A1 (en) * | 1992-10-20 | 1994-04-28 | Degussa Aktiengesellschaft | Method for the continuous preparation of methionine or methionine derivatives |
US5672745A (en) * | 1992-10-20 | 1997-09-30 | Degussa Aktiengesellschaft | Method for the continuous preparation of methionine or methionine derivatives |
EP3453701A1 (en) * | 2017-09-08 | 2019-03-13 | Sumitomo Chemical Company, Limited | Method for producing methionine and/or 2-hydroxy-4-(methylthio)butanoic acid |
US10501409B2 (en) | 2017-09-08 | 2019-12-10 | Sumitomo Chemical Company, Limited | Method for producing methionine and/or 2-hydroxy-4-(methylthio) butanoic acid |
CN111635330A (en) * | 2020-06-24 | 2020-09-08 | 江苏扬农化工集团有限公司 | Method for recycling reaction residues of key intermediate of hexamethylene diamine and co-producing carboxylic acid |
CN111635330B (en) * | 2020-06-24 | 2023-01-24 | 江苏扬农化工集团有限公司 | Method for recycling reaction residues of key intermediate of hexamethylene diamine and co-producing carboxylic acid |
Also Published As
Publication number | Publication date |
---|---|
FR2405924B1 (en) | 1980-05-16 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
ST | Notification of lapse |