DE945927C - Process for the production of glutamic acid - Google Patents

Process for the production of glutamic acid

Info

Publication number
DE945927C
DE945927C DEF14057A DEF0014057A DE945927C DE 945927 C DE945927 C DE 945927C DE F14057 A DEF14057 A DE F14057A DE F0014057 A DEF0014057 A DE F0014057A DE 945927 C DE945927 C DE 945927C
Authority
DE
Germany
Prior art keywords
ester
glutamic acid
production
rooc
acylaminomalone
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.)
Expired
Application number
DEF14057A
Other languages
German (de)
Inventor
Dr Rer Nat Heinrich Hellmann
Dipl-Chem Franz Lingens
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.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Priority to DEF14057A priority Critical patent/DE945927C/en
Application granted granted Critical
Publication of DE945927C publication Critical patent/DE945927C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof

Description

Verfahren zur Herstellung von Glutaminsäure Es wurde eine Glutaminsäure-Synthese beschrieben (Hoppe-Seylers, Zeitschr. f. physiol. Chem. 287 [I95I], 235), welche in einer Kondensation von Malonester und Piperidinomethylformamino-malonester (I) in siedendem Xylol unter der katalytischen Wirkung von Natriumhydroxyd bei nachfolgender Hydrolyse besteht. COOR COOR ROOC Cm, 0 I ROOC ROOC + /NCH2CNHCHO ROOC CHCHlCNHCHO ROOC ROOC f COOR COOR (I) (11) Hydrolyse Hydrolyse) HOOCCH2CH!CHCOOH I NH2 Es wurde nan gefunden, daß man diese Synthese vereinfachen kann und zu reineren Produkten kommt, wenn man ein Gemisch aus Malonester, Formaldehyd und einem Acylaminomalonester in einem inerten Lösungsmittel, z. B. Xylol mit katalytischen Mengen von Alkalihydroxyd erhitzt. Hierbei entsteht ebenfalls zunächst - Methylen-malonester-acylaminomalonester (II), der dann zur Glutaminsäure abgebaut wird. COOR ROOCCH2 -> \ - cH,o + HC-NH-Acyl (II ROOC COOR Beispiel 4,3 g (0,02 Mol) Acetaminomalbnsäurediäthylester, 5,2 g (0,03 Mol) Malonsäurediäthylester und o,g g (ozon Mol) Paraformaldehyd werden in 20 ccm Xylol mit katalytischen Mengen von gepulvertem Natriumhydroxyd 5 Stunden auf 1000 erhitzt. Nach dem Erkalten wird vom Natriumhydroxyd abfiltriert und das Lösungsmittel im Vakuum abdestilliert. Aus dem zurückbleibenden' hellgelben Öl kristallisiert beim Stehenlassen im Eisschrank der Methylen-malonsäurediäthylester- acetaminomalonsäurediäthylester, Cl? H27 O9 N, welcher nach Umkristallisieren aus verdünntem Methanol bei 58" schmilzt. Der Tetrasarbonsäureester wird als Kristallisat,-oder einfacher in Form des erhaltenen gelbstichigen Öles, durch 8stündiges Kochen in konzenftierter Salzsäure verseift und gleichzeitig decarboxyliert; die farblose Lösung wird im Vakuum eingeengt. Bei o°-wird mit Chlorwasserstoff gesättigt, wobei Glutaniinsäurehydrochlorid ausfällt.Process for the preparation of glutamic acid A glutamic acid synthesis has been described (Hoppe-Seylers, Zeitschr. F. Physiol. Chem. 287 [1951], 235), which results in a condensation of malonic ester and piperidinomethylformamino-malonic ester (I) in boiling xylene the catalytic effect of sodium hydroxide in subsequent hydrolysis exists. COOR COOR ROOC Cm, 0 I ROOC ROOC + / NCH2CNHCHO ROOC CHCHlCNHCHO ROOC ROOC f COOR COOR (I) (11) hydrolysis Hydrolysis) HOOCCH2CH! CHCOOH I. NH2 It has been found nan that this synthesis can be simplified and purer products are obtained if a mixture of malonic ester, formaldehyde and an acylaminomalone ester in an inert solvent, e.g. B. xylene heated with catalytic amounts of alkali hydroxide. This also initially produces - methylene malonic ester acylaminomalone ester (II), which is then broken down into glutamic acid. COOR ROOCCH2 -> \ - cH, o + HC-NH-acyl (II ROOC COOR Example 4.3 g (0.02 mol) of diethyl acetaminomalate, 5.2 g (0.03 mol) of diethyl malonate and 0.2 g (ozone mol) of paraformaldehyde are heated to 1000 for 5 hours in 20 cc of xylene with catalytic amounts of powdered sodium hydroxide. After cooling, the sodium hydroxide is filtered off and the solvent is distilled off in vacuo. The methylene-malonic acid diethyl ester-acetaminomalonic acid diethyl ester, Cl? H27 O9 N, which melts at 58 "after recrystallization from dilute methanol. The tetrasarboxylic acid ester is saponified as crystals, or more simply in the form of the yellowish oil obtained, by boiling for 8 hours in concentrated hydrochloric acid and at the same time decarboxylated; the colorless solution is concentrated in vacuo. At 0 ° it is saturated with hydrogen chloride, whereby glutaniic acid hydrochloride precipitates.

Wegen der größeren Reinheit des erfindungsgemäß erhaltenen Produktes erübrigt sich jedoch meist die Reinigung mittels Kohle. Because of the greater purity of the product obtained according to the invention however, cleaning with charcoal is usually unnecessary.

Claims (2)

PATENTANSPRÜCHE: I. Verfahren zur Herstellung von Glutaminsäure, dadurch gekennzeichnet, daß man ein Gemisch aus Malonester, Formaldehyd und einem Acylaminomalonester in einem inerten Lösungsmittel mit katalytischen Mengen von - Alkalihydroxyd erhitzt und den entstandenen Methylen malonester-acylaminomalonester mit konzentrierter Salzsäure kocht. PATENT CLAIMS: I. Process for the production of glutamic acid, characterized in that a mixture of malonic ester, formaldehyde and one Acylaminomalone ester in an inert solvent with catalytic amounts of - Heated alkali hydroxide and the resulting methylene malonic ester-acylaminomalone ester boils with concentrated hydrochloric acid. 2. Verfahren nach Anspruch I, dadurch gekennzeichnet, daß man als inertes Lösungsmittel Xylol - verwendet. 2. The method according to claim I, characterized in that as inert solvent xylene - used.
DEF14057A 1954-03-02 1954-03-02 Process for the production of glutamic acid Expired DE945927C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF14057A DE945927C (en) 1954-03-02 1954-03-02 Process for the production of glutamic acid

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF14057A DE945927C (en) 1954-03-02 1954-03-02 Process for the production of glutamic acid

Publications (1)

Publication Number Publication Date
DE945927C true DE945927C (en) 1956-07-19

Family

ID=7087478

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF14057A Expired DE945927C (en) 1954-03-02 1954-03-02 Process for the production of glutamic acid

Country Status (1)

Country Link
DE (1) DE945927C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1169448B (en) * 1960-03-26 1964-05-06 Bayer Ag Process for performing asymmetrical three-carbon condensations

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1169448B (en) * 1960-03-26 1964-05-06 Bayer Ag Process for performing asymmetrical three-carbon condensations

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