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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 catalyst

Info

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
Application number
FR7730699A
Other languages
French (fr)
Other versions
FR2405924B1 (en
Inventor
A Commeyras
J Taillades
L Mion
R Pascal
M Lasperas
Et A Rousset
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bpifrance Financement SA
Original Assignee
Agence National de Valorisation de la Recherche ANVAR
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
Application filed by Agence National de Valorisation de la Recherche ANVAR filed Critical Agence National de Valorisation de la Recherche ANVAR
Priority to FR7730699A priority Critical patent/FR2405924A1/en
Publication of FR2405924A1 publication Critical patent/FR2405924A1/en
Application granted granted Critical
Publication of FR2405924B1 publication Critical patent/FR2405924B1/fr
Granted legal-status Critical Current

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.
FR7730699A 1977-10-12 1977-10-12 Alpha-amino acid prodn. from amino nitrile - by single stage hydrolysis in presence of carbonyl catalyst Granted FR2405924A1 (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (8)

* Cited by examiner, † Cited by third party
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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