GB808874A - Process for the preparation of substituted aminocarboxylic acid amides - Google Patents

Process for the preparation of substituted aminocarboxylic acid amides

Info

Publication number
GB808874A
GB808874A GB8556/57A GB855657A GB808874A GB 808874 A GB808874 A GB 808874A GB 8556/57 A GB8556/57 A GB 8556/57A GB 855657 A GB855657 A GB 855657A GB 808874 A GB808874 A GB 808874A
Authority
GB
United Kingdom
Prior art keywords
acid
amine
salt
dodecylamine
coconut oil
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
GB8556/57A
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.)
Boehme Fettchemie GmbH
Original Assignee
Boehme Fettchemie GmbH
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 Boehme Fettchemie GmbH filed Critical Boehme Fettchemie GmbH
Publication of GB808874A publication Critical patent/GB808874A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • 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
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • 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)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lubricants (AREA)

Abstract

The invention comprises a process for the preparation of substituted aminocarboxylic acid amides soluble or dispersible in water or of salts thereof, which consists in preparing a mono-amine salt from an aliphatic, cycloaliphatic or aliphatic-aromatic primary or secondary amine which contains in the molecule at least one lipophilic hydrocarbon residue of at least six carbon atoms, which residue may be interrupted by hetero atoms or may contain substituents, and a di- or poly-basic aminocarboxylic acid, removing the elements of water from the said amine salt and so obtaining a substituted aminocarboxylic acid amide, and, if desired, converting said amide into a salt thereof. The elements of water may be removed by dry-heating at above 100 DEG C., preferably at 180-200 DEG C., and may be effected under reduced pressure and/or in a current of nitrogen. Suitable amines are hexylamine, dodecylamine, oleylamine, octadecylamine, cyclohexylamine, alkylcyclohexyl primary amines (alkyl residues C3-C12), naphthenylamines, alkylphenyl primary amines (alkyl residues C3-C18), and amine mixtures such as coconut oil amine; also secondary amines such as methyloleylamine, ethyldodecylamine and didodecylamine. Suitable aminocarboxylic acids include nitrilotriacetic acid, ethylenediamine tetraacetic acid, hydroxyalkyliminodiacetic acids such as hydroxyethyliminodiacetic acid, and hydroxyethyl-ethylenediamine triacetic acid. The formation of the amine salts may be effected in aqueous solution or in organic solvents, or by melting the starting components together. The free carboxyl groups of the final products may be converted into salt groups in known manner, suitable salt-forming components being metals, such as sodium, potassium, magnesium, calcium and aluminium, ammonium and organic bases such as alkanolamines, pyridine and cyclohexylamine. In examples the reactants are (1) n-dodecylamine and hydroxythyliminodiacetic acid; (2) coconut oil amine and hydroxyethylimino diacetic acid; (3) dodecylamine and nitrolotriacetic acid; and (4) coconut oil amine and nitrilotriacetic acid, the sodium salts of the final products being prepared in each case.
GB8556/57A 1956-03-16 1957-03-15 Process for the preparation of substituted aminocarboxylic acid amides Expired GB808874A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE808874X 1956-03-16

Publications (1)

Publication Number Publication Date
GB808874A true GB808874A (en) 1959-02-11

Family

ID=6723182

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8556/57A Expired GB808874A (en) 1956-03-16 1957-03-15 Process for the preparation of substituted aminocarboxylic acid amides

Country Status (1)

Country Link
GB (1) GB808874A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3998967A (en) * 1973-12-12 1976-12-21 Stauffer Chemical Company Method of inhibiting the growth of bacteria and fungi with higher aliphatic amine salts of nitrilotriacetic acid
US4927279A (en) * 1984-03-14 1990-05-22 Morgan Ruth B Keyboards for homes
US10035970B2 (en) 2016-05-09 2018-07-31 Basf Se Friction-reducing compound, method of producing same, and lubricant composition

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3998967A (en) * 1973-12-12 1976-12-21 Stauffer Chemical Company Method of inhibiting the growth of bacteria and fungi with higher aliphatic amine salts of nitrilotriacetic acid
US4927279A (en) * 1984-03-14 1990-05-22 Morgan Ruth B Keyboards for homes
US10035970B2 (en) 2016-05-09 2018-07-31 Basf Se Friction-reducing compound, method of producing same, and lubricant composition

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