GB803778A - Production of n-(hydrocarbon substituted) aminocarboxylic acids, their esters or salts - Google Patents

Production of n-(hydrocarbon substituted) aminocarboxylic acids, their esters or salts

Info

Publication number
GB803778A
GB803778A GB35716/56A GB3571656A GB803778A GB 803778 A GB803778 A GB 803778A GB 35716/56 A GB35716/56 A GB 35716/56A GB 3571656 A GB3571656 A GB 3571656A GB 803778 A GB803778 A GB 803778A
Authority
GB
United Kingdom
Prior art keywords
acids
esters
ethylene
acid
salts
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
GB35716/56A
Inventor
Walter Reppe
Nikolaus Von Kutepow
Heinz Hohenschutz
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.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik 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 BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Priority to GB35716/56A priority Critical patent/GB803778A/en
Publication of GB803778A publication Critical patent/GB803778A/en
Expired legal-status Critical Current

Links

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
    • C07C227/18—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 by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
    • 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
    • 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
    • C07C227/02—Formation of carboxyl groups in compounds containing amino groups, e.g. by oxidation of amino alcohols
    • 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
    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
    • C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
    • C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
    • 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
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines

Landscapes

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

Abstract

The invention comprises reacting an aminocarboxylic acid, its esters with a monohydric aliphatic, cycloaliphatic or araliphatic alcohol, or its salts with alkali or alkaline earth metals such compounds containing at least one hydrogen attached to nitrogen, with CO, an olefinic hydrocarbon and water at room temperature or above and increased pressure, in the presence of iron or cobalt carbonyl or carbonyl hydride or an ammonium or amine salt, especially tertiary ring-combined amine salts, of such carbonyl hydrides, to produce N-(hydrocarbon substituted) aminocarboxylic acids, esters or salts, the molar ratio of CO to olefine being 2:1 to 5:1, preferably 3:1. The preferred temperatures and pressures are 80-160 DEG C. and 5-500 atmospheres, more preferably 10-200 atmospheres, and the preferred catalyst is iron pentacarbonyl. Suitable amino carboxylic acids include aliphatic monobasic acids with 2 to 6 C atoms, such as glycocoll, a -alanine, serine, valine and leucine; aliphatic dibasic acids such as glutamic and aspartic acids; acids containing two amino groups, such as ornithine and lysine; heterocyclic acids such as proline and hydroxyproline; aromatic acids, such as aminobenzoic, N - methylaminobenzoic, N - ethylaminobenzoic and aminonaphthoic acids. Suitable olefinic hydrocarbons include open chain monounsaturated olefines such as ethylene, propylene, n-butylene, iso-butylene, octylene, dodecylene, octadecylene; cyclic olefines such as cyclohexene and cyclo-octene; araliphatic olefines such as styrene; and diolefines such as butadiene, isoprene, dimethylbutadiene, hexanediene-(2,5) and piperylene. The addition of solvents, such as alcohols, hydrocarbons, esters, lactams and carboxylic acid amides is advantageous; in particular when reacting aminocarboxylic acid esters, it is advantageous to use the alcohol which constitutes the alcoholic component of the esters. The reaction is preferably carried out at alkaline pH, but may be carried out at neutral or slightly acid pH; in this last case the use of formic acid is preferred. The process may be continuous or discontinuous. Examples describe the reaction of a -alanine with ethylene, leucine with ethylene, d,l-proline with ethylene, p-aminobenzoic acid ethyl ester with propylene, anthranilic acid with ethylene and 3-amino-2-naphthoic acid with ethylene. The products are N-substituted by a group containing one carbon atom more than the olefine.
GB35716/56A 1956-11-22 1956-11-22 Production of n-(hydrocarbon substituted) aminocarboxylic acids, their esters or salts Expired GB803778A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB35716/56A GB803778A (en) 1956-11-22 1956-11-22 Production of n-(hydrocarbon substituted) aminocarboxylic acids, their esters or salts

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB35716/56A GB803778A (en) 1956-11-22 1956-11-22 Production of n-(hydrocarbon substituted) aminocarboxylic acids, their esters or salts

Publications (1)

Publication Number Publication Date
GB803778A true GB803778A (en) 1958-10-29

Family

ID=10380788

Family Applications (1)

Application Number Title Priority Date Filing Date
GB35716/56A Expired GB803778A (en) 1956-11-22 1956-11-22 Production of n-(hydrocarbon substituted) aminocarboxylic acids, their esters or salts

Country Status (1)

Country Link
GB (1) GB803778A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108727209A (en) * 2018-06-20 2018-11-02 复旦大学 With N, the compound and preparation method thereof of N- dialkyl group leucine structures

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108727209A (en) * 2018-06-20 2018-11-02 复旦大学 With N, the compound and preparation method thereof of N- dialkyl group leucine structures

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