GB727465A - Di-alkyl substituted alkylene polyamino acetic acids - Google Patents

Di-alkyl substituted alkylene polyamino acetic acids

Info

Publication number
GB727465A
GB727465A GB13806/51A GB1380651A GB727465A GB 727465 A GB727465 A GB 727465A GB 13806/51 A GB13806/51 A GB 13806/51A GB 1380651 A GB1380651 A GB 1380651A GB 727465 A GB727465 A GB 727465A
Authority
GB
United Kingdom
Prior art keywords
ethylene diamine
diamine
diacetic acid
carboxymethylating
trimethylene
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
GB13806/51A
Inventor
Frederick Charles Bersworth
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.)
Dow Chemical Co
Original Assignee
Dow Chemical Co
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 Dow Chemical Co filed Critical Dow Chemical Co
Priority to GB13806/51A priority Critical patent/GB727465A/en
Publication of GB727465A publication Critical patent/GB727465A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton

Landscapes

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

Abstract

The invention comprises compounds of the general formula <FORM:0727465/IV (b)/1> in which R is an alkyl group containing from 1 to 6 carbon atoms; M is H, NH4, K, Na or amine; n is 0, 1 or 2 and Alkylene is ethylene, propylene, butylene or trimethylene. They may be prepared by carboxymethylating an alkyl substituted alkylene polyamine of formula <FORM:0727465/IV (b)/2> to replace the remaining amino hydrogens by acetic acid groups, preferably by treating it in alkaline pH solution with alkali metal cyanide and formaldehyde and hydrolysing the product. With di- and poly-valent metal bases the acids form "chelate" compounds, e.g. <FORM:0727465/IV (b)/3> with calcium hydroxide and a similar compound with ferric hydroxide. In the examples: (a) N,N1-diethyl ethylene diamine diacetic acid is obtained by carboxymethylating N,N1-dimethyl ethylene diamine with alkali metal cyanide and formaldehyde followed by acidification; (b) N,N1-diethyl ethylene diamine diacetic acid is obtained as in (a) by using N,N1-diethyl ethylene diamine instead of the di-methyl diamine; (c) N,N1-di-isopropyl ethylene diamine diacetic acid is obtained by similarly carboxymethylating didiisopropyl ethylene diamine; (d) N,N1-dihexyl ethylene diamine diacetic acid is obtained by similarly carboxymethylating N,N1 - dihexyl ethylene diamine; and (e) N,N1 - dibutyl ethylene diamine diacetic acid is obtained by treating an alkaline solution of N,N1-dibutyl ethylene diamine with hydrocyanic acid and formaldehyde, followed by acidifying. Dialkyl derivatives of the following amines may also be used as starting materials: propylene diamine, butylene diamine, trimethylene diamine, diethylene triamine, dipropylene triamine, dibutylene triamine, di-(trimethylene) triamine, triethylene tetramine, tripropylene tetramine, tributylene tetramine and tri-(trimethylene) tetramine. The alkyl groups would replace one hydrogen atom in each of the two terminal amino groups. Specification 600,629 and U.S.A. Specification 2,387,735 are referred to.
GB13806/51A 1951-06-11 1951-06-11 Di-alkyl substituted alkylene polyamino acetic acids Expired GB727465A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB13806/51A GB727465A (en) 1951-06-11 1951-06-11 Di-alkyl substituted alkylene polyamino acetic acids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB13806/51A GB727465A (en) 1951-06-11 1951-06-11 Di-alkyl substituted alkylene polyamino acetic acids

Publications (1)

Publication Number Publication Date
GB727465A true GB727465A (en) 1955-04-06

Family

ID=10029732

Family Applications (1)

Application Number Title Priority Date Filing Date
GB13806/51A Expired GB727465A (en) 1951-06-11 1951-06-11 Di-alkyl substituted alkylene polyamino acetic acids

Country Status (1)

Country Link
GB (1) GB727465A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5010191A (en) * 1985-08-19 1991-04-23 The Regents Of The University Of California Imaging agents for in vivo magnetic resonance and scintigraphic imaging

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5010191A (en) * 1985-08-19 1991-04-23 The Regents Of The University Of California Imaging agents for in vivo magnetic resonance and scintigraphic imaging

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