GB810501A - Improvements relating to the carboxymethylation of primary and secondary amines - Google Patents

Improvements relating to the carboxymethylation of primary and secondary amines

Info

Publication number
GB810501A
GB810501A GB15768/56A GB1576856A GB810501A GB 810501 A GB810501 A GB 810501A GB 15768/56 A GB15768/56 A GB 15768/56A GB 1576856 A GB1576856 A GB 1576856A GB 810501 A GB810501 A GB 810501A
Authority
GB
United Kingdom
Prior art keywords
acid
glycine
amino
primary
secondary amines
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
GB15768/56A
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.)
Novartis AG
Original Assignee
JR Geigy 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 JR Geigy AG filed Critical JR Geigy AG
Publication of GB810501A publication Critical patent/GB810501A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
    • C07C255/25—Aminoacetonitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
    • C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C07C229/16—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids
    • 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
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C237/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms

Landscapes

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

Abstract

Primary and secondary amines are carboxymethylated by adding an aqueous solution of glycollonitrile to an aqueous solution of the amine at a pH of at least 12 and maintaining the mixture at a temperature between 85 DEG C. and the boiling point at a pressure of 1-5 inches of mercury. Examples show the production of ethylene diamine tetracetic acid from ethylene diamine, N-dodecyl-iminodiacetic acid and N-dodecyl-glycine from dodecylamine, N:N - di - hydroxyethyl - glycine from diethanolamine and iminodiacetic acid and nitrilotriacetic acid from glycine. The required pH is produced by addition of a base, e.g. sodium, potassium, calcium, barium or lithium hydroxide or tetra - ethanolammonium hydroxide, and the product may be obtained as a salt with the base, or as the free acid after acidification. The process may also be applied to ethylamine, chlorethylamine, butylamine, cyclohexylamine, propylene diamine, diethylene triamine, triethylene tetramine, piperazine, amino-propionic acid, amino-isovaleric acid and amino-phenylpropionic acid.
GB15768/56A 1955-05-23 1956-05-22 Improvements relating to the carboxymethylation of primary and secondary amines Expired GB810501A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US810501XA 1955-05-23 1955-05-23

Publications (1)

Publication Number Publication Date
GB810501A true GB810501A (en) 1959-03-18

Family

ID=22161794

Family Applications (1)

Application Number Title Priority Date Filing Date
GB15768/56A Expired GB810501A (en) 1955-05-23 1956-05-22 Improvements relating to the carboxymethylation of primary and secondary amines

Country Status (1)

Country Link
GB (1) GB810501A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CZ297932B6 (en) * 2004-09-01 2007-05-02 Azacycles S. R. O. Process for preparing N-carboxymethylated amines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CZ297932B6 (en) * 2004-09-01 2007-05-02 Azacycles S. R. O. Process for preparing N-carboxymethylated amines

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