GB844031A - A method of preparing 10-aminodecanoic acid and esters thereof - Google Patents

A method of preparing 10-aminodecanoic acid and esters thereof

Info

Publication number
GB844031A
GB844031A GB37717/58A GB3771758A GB844031A GB 844031 A GB844031 A GB 844031A GB 37717/58 A GB37717/58 A GB 37717/58A GB 3771758 A GB3771758 A GB 3771758A GB 844031 A GB844031 A GB 844031A
Authority
GB
United Kingdom
Prior art keywords
acid
ester
octadiene
nona
dicyano
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
GB37717/58A
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.)
Montedison SpA
Original Assignee
Montedison SpA
Montecatini Societa Generale per lIndustria Mineraria e Chimica SpA
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 Montedison SpA, Montecatini Societa Generale per lIndustria Mineraria e Chimica SpA filed Critical Montedison SpA
Publication of GB844031A publication Critical patent/GB844031A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C229/08—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 hydrogen atoms
    • 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
    • C07C227/04—Formation of amino groups in compounds containing carboxyl 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
    • C07C229/30—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 unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • 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
    • C07C255/19—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton
    • 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
    • C07C255/23—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same unsaturated acyclic carbon skeleton

Landscapes

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

Abstract

Some polyamide is obtained when 10-aminodexanoic acid methyl ester is distilled. The monomeric ester is obtained by esterifying 1, 8-diazano-2, 6-octadiene with methanol, and hydrogenating the resulting methyl ester of a -cyano-nona-3, 7-dienoic acid in the presence of ammonia and Raney nickel.ALSO:The invention comprises the alkyl esters of 9-cyano-nona-3,7-dienoic acid; and the preparations of 10-aminodecanoic acid and alkyl esters thereof by esterifying 1,8-dicyano-2,6-octadiene with an alkanol to obtain an alkyl ester of 9-cyanonona-3,7-dienoic acid, and hydrogenating the latter catalytically to obtain an alkyl ester of 10-aminodecanoic acid; and if desired hydrolysing the ester to form the free acid or a salt thereof. The hydrogenation may be effected in a single stage, e.g. in the presence of Raney nickel and ammonia or sodium hydroxide at 20-150 DEG C. and 1-20 atmospheres; or in two stages, the double bonds first being hydrogenated, e.g. by using palladium, and the nitrile group then being hydrogenated, e.g. in the presence of an Ni/Cr catalyst and an alkali. In the esterification of the dicyano-octadiene some diester ROOC(CH2CH =CHCH2)2COOR is formed, and can be converted to sebacic diester and sebacic acid.
GB37717/58A 1957-11-28 1958-11-24 A method of preparing 10-aminodecanoic acid and esters thereof Expired GB844031A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT844031X 1957-11-28

Publications (1)

Publication Number Publication Date
GB844031A true GB844031A (en) 1960-08-10

Family

ID=11325092

Family Applications (1)

Application Number Title Priority Date Filing Date
GB37717/58A Expired GB844031A (en) 1957-11-28 1958-11-24 A method of preparing 10-aminodecanoic acid and esters thereof

Country Status (1)

Country Link
GB (1) GB844031A (en)

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