ES213621A1 - Improvements in and relating to the production of omega-amino nonanoic acid - Google Patents

Improvements in and relating to the production of omega-amino nonanoic acid

Info

Publication number
ES213621A1
ES213621A1 ES0213621A ES213621A ES213621A1 ES 213621 A1 ES213621 A1 ES 213621A1 ES 0213621 A ES0213621 A ES 0213621A ES 213621 A ES213621 A ES 213621A ES 213621 A1 ES213621 A1 ES 213621A1
Authority
ES
Spain
Prior art keywords
acid
semi
azelaic
aldehyde
amino
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
ES0213621A
Other languages
Spanish (es)
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.)
Akzo Nobel UK PLC
Original Assignee
Courtaulds PLC
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 Courtaulds PLC filed Critical Courtaulds PLC
Publication of ES213621A1 publication Critical patent/ES213621A1/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
    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/126—Acids containing more than four carbon atoms

Landscapes

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

Abstract

o -Amino nonanoic acid is prepared by subjecting an unsaturated acid occurring naturally in vegetable oils and having the formula R-CH=CH(CH2)7COOH, R being an aliphatic monovalent radical, to oxidative cleavage to form azelaic semi-aldehyde OHC-(CH2)7COOH, together with a further aldehyde RCHO as byproduct, the oxidative cleavage being effected either by reacting the acid with hydrogen peroxide to form a corresponding dihydroxy substituted acid and oxidizing this acid to form the aldehydes or by reacting the acid with ozone to form an ozonide which is subjected to hydrolysis or catalytic hydrogenation to form the aldehydes, and then either reacting the azelaic semi-aldehyde with hydroxylamine to form azelaic semi-aldoxime and hydrogenating the aldoxime in the presence of a hydrogenation catalyst to the desired amino-nonanoic acid or hydrogenating the azelaic semi-aldehyde in the presence of ammonia and a hydrogenation catalyst to the same amino acid. In a modification of the process, esters of the aminononanoic acid are prepared following the same sequence of reactions and either starting with an ester of the original unsaturated acid or esterifying one of the intermediate products which contains an esterifiable carboxylic group, for example, the azelaic semi-aldehyde or dihydroxy acid. In examples: (1) oleic acid in dry ethanol is treated with ozonized oxygen and the resulting solution of ozonide is hydrogenated in presence of palladium on calcium carbonate as catalyst the aldehyde mixture formed is reacted with hydroxylamine hydrochloride in presence of excess sodium acetate and the solution refluxed after removal of solvent, pelargonic aldoxime is precipitated by excess of aqueous sodium carbonate and thereafter azelaic semi-aldoxime is precipitated on acidification the azelaic semi-aldoxime is hydrogenated in ethanolic solution in presence of ammonia and a Raney nickel catalyst and the ammonium salt of the desired amino-nonanoic acid recovered from the product and converted into the free amino-acid the aldehydic products of the oxidative cleavage may be separated before the oxime-formation step by distillation or the semi-carbazone method (2) oleic acid is hydroxylated with hydrogen peroxide and acetic acid, and the resulting 9 : 10-dihydroxy stearic acid recovered and converted to its ethyl ester the ester is oxidized in dry benzene with lead tetra-acetate and the so-obtained pelargonic aldehyde and the ethyl ester of azelaic semi-aldehyde recovered by distillation the ethyl ester is converted into its oxime which is hydrogenated as in (1) to yield ethyl 9-amino nonanoate (3) as in (2), the ethyl ester of the azelaic semi-aldehyde being hydrogenated in ethanolic solution in presence of ammonia and Raney nickel to form ethyl amino nonanoate. Reference is also made to linoleic and ricinoleic acids and their esters. According to the Provisional Specification, R is any monovalent radical.
ES0213621A 1953-02-23 1954-02-11 Improvements in and relating to the production of omega-amino nonanoic acid Expired ES213621A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4964/53A GB743491A (en) 1953-02-23 1953-02-23 Improvements in and relating to the production of omega-amino nonanoic acid

Publications (1)

Publication Number Publication Date
ES213621A1 true ES213621A1 (en) 1955-04-16

Family

ID=9787212

Family Applications (1)

Application Number Title Priority Date Filing Date
ES0213621A Expired ES213621A1 (en) 1953-02-23 1954-02-11 Improvements in and relating to the production of omega-amino nonanoic acid

Country Status (2)

Country Link
ES (1) ES213621A1 (en)
GB (1) GB743491A (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2933696B1 (en) 2008-07-10 2010-08-20 Arkema France PROCESS FOR THE SYNTHESIS OF OMEGA-AMINOALCANOIC ACIDS OR THEIR ESTERS FROM NATURAL FATTY ACIDS
FR2933695B1 (en) 2008-07-10 2010-08-20 Arkema France PROCESS FOR THE SYNTHESIS OF AMINO-9-NONANOIC ACID OR ESTERS THEREOF FROM UNSATURATED NATURAL FATTY ACIDS.
FR2941694B1 (en) 2009-02-05 2011-02-11 Arkema France PROCESS FOR SYNTHESIZING AN OMEGA-AMINOACIDE OR ESTERING FROM A MONO-UNSATURATED FATTY ACID OR ESTER
FR2970252B1 (en) 2011-01-10 2013-11-15 Arkema France PROCESS FOR PRODUCING NITRILE-FATTY ACID COMPOUNDS
KR101969185B1 (en) 2011-07-08 2019-04-15 디에스엠 아이피 어셋츠 비.브이. Preparation of nitrile compounds
FR2978147B1 (en) 2011-07-19 2015-01-09 Arkema France PROCESS FOR SYNTHESIZING OMEGA-FUNCTIONALIZED ACIDS FROM HYDROXYLIC ACIDS OR FATTY ESTERS
FR2983477B1 (en) * 2011-12-01 2013-12-27 Arkema France PROCESS FOR CUTTING UNSATURATED FAT CHANNELS
FR3001966A1 (en) 2013-02-08 2014-08-15 Arkema France CONJUGATED SYNTHESIS OF A NITRILE-ESTER / ACID AND A DIESTER / DIACIDE

Also Published As

Publication number Publication date
GB743491A (en) 1956-01-18

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