GB741739A - 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
GB741739A
GB741739A GB4963/53A GB496353A GB741739A GB 741739 A GB741739 A GB 741739A GB 4963/53 A GB4963/53 A GB 4963/53A GB 496353 A GB496353 A GB 496353A GB 741739 A GB741739 A GB 741739A
Authority
GB
United Kingdom
Prior art keywords
acid
nitrile
semi
acids
pelargonic
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
GB4963/53A
Inventor
Albert Stanley Carpenter
Frank Reeder
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
Priority to GB4963/53A priority Critical patent/GB741739A/en
Priority to ES0213620A priority patent/ES213620A1/en
Publication of GB741739A publication Critical patent/GB741739A/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
    • C07C253/00—Preparation of carboxylic acid nitriles
    • 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

Landscapes

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

Abstract

o -Amino nonanoic acid is prepared by reacting an unsaturated acid occurring naturally in vegetable oils and having the general formula R-CH = CH(CH2)7COOH, wherein R is an aliphatic monovalent radical, with ammonia to form the corresponding nitrile of the acid, oxidising the nitrile to form azelaic acid seminitrile CN.(CH2)7COOH, together with an acid R.COOH as by-product, either by reacting the nitrile with ozone with concurrent treatment with water or by reacting the nitrile with ozone, subsequently decomposing the resulting ozonide of the acid nitrile with water to form a mixture of acids and aldehydes and oxidizing the aldehyde portion thereof to the corresponding acids, and hydrogenating the semi-nitrile in the presence of a hydrogenation catalyst to the desired amino-nonanoic acid. In examples (1) oleic acid is heated with ammonia at about 300 DEG C. and the resulting nitrile ozonized in ethyl chloride at -40 DEG C.; the oleonitrile ozonide is refluxed with water, excess sodium carbonate added and the aqueous layer containing the sodium salts of pelargonic acid and azelaic acid semi-nitrile separated from the insoluble pelargonic aldehyde and o -cyanooctanol which are oxidized with oxygen at 120-140 DEG C. in presence of ferric oxide and the product extracted with aqueous sodium carbonate to provide another solution of sodium salts of the acids; the two solutions are acidified and the liberated pelargonic acid and azelaic acid semi-nitrile separated; the nitrile is hydrogenated in alcoholic solution to aminononanoic acid under pressure in presence of ammonia and a Raney nickel catalyst; (2) oleonitrile is produced as in (1) and ozonized in aqueous ethyl acetate at 70 DEG C.; pelargonic acid and azelaic acid semi-nitrile are recovered from the product and the latter hydrogenated as in (1). In place of oleic acid, there may be used ricinoleic, linoleic and linolenic acids. According to the Provisional Specification, R is any monovalent radical.
GB4963/53A 1953-02-23 1953-02-23 Improvements in and relating to the production of omega-amino nonanoic acid Expired GB741739A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB4963/53A GB741739A (en) 1953-02-23 1953-02-23 Improvements in and relating to the production of omega-amino nonanoic acid
ES0213620A ES213620A1 (en) 1953-02-23 1954-02-11 Improvements in and relating to the production of omega-amino nonanoic acid

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4963/53A GB741739A (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
GB741739A true GB741739A (en) 1955-12-14

Family

ID=9787189

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4963/53A Expired GB741739A (en) 1953-02-23 1953-02-23 Improvements in and relating to the production of omega-amino nonanoic acid

Country Status (2)

Country Link
ES (1) ES213620A1 (en)
GB (1) GB741739A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2865937A (en) * 1956-03-06 1958-12-23 Welsbach Corp Processes for the production of dibasic and monobasic acids
US3126410A (en) * 1964-03-24 Certificate of correction
US3206503A (en) * 1962-06-13 1965-09-14 Koppers Co Inc Norcamphoric acid manufacture
WO2010055273A1 (en) 2008-11-17 2010-05-20 Arkema France Method for the synthesis of an omega-amino acid or ester starting from a monounsaturated fatty acid or ester
FR2941694A1 (en) * 2009-02-05 2010-08-06 Arkema France PROCESS FOR SYNTHESIZING AN OMEGA-AMINOACIDE OR ESTERING FROM A MONO-UNSATURATED FATTY ACID OR ESTER
FR2970252A1 (en) * 2011-01-10 2012-07-13 Arkema France PROCESS FOR PRODUCING NITRILE-FATTY ACID COMPOUNDS
WO2013011226A1 (en) * 2011-07-19 2013-01-24 Arkema France Process for synthesizing omega-functionalized acids from fatty acids or fatty esters
WO2013017782A1 (en) 2011-08-01 2013-02-07 Arkema France Method for synthesizing an omega-amino acid or ester from a monounsaturated fatty acid or ester
WO2013079849A1 (en) * 2011-12-01 2013-06-06 Arkema France Method for cleaving unsaturated fatty chains
WO2014122410A2 (en) 2013-02-08 2014-08-14 Arkema France Combined synthesis of a nitrile-ester/acid and of a diester/diacid

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3126410A (en) * 1964-03-24 Certificate of correction
US2865937A (en) * 1956-03-06 1958-12-23 Welsbach Corp Processes for the production of dibasic and monobasic acids
US3206503A (en) * 1962-06-13 1965-09-14 Koppers Co Inc Norcamphoric acid manufacture
US20110224454A1 (en) * 2008-11-17 2011-09-15 Arkema France Method for the synthesis of an omega-amino acid or ester starting from a monounsaturated fatty acid or ester
WO2010055273A1 (en) 2008-11-17 2010-05-20 Arkema France Method for the synthesis of an omega-amino acid or ester starting from a monounsaturated fatty acid or ester
US8748651B2 (en) * 2008-11-17 2014-06-10 Arkema France Method for the synthesis of an omega-amino acid or ester starting from a monounsaturated fatty acid or ester
US20110300590A1 (en) * 2009-02-05 2011-12-08 Arkema France Method for Synthesizing an Omega-Amino Acid or Ester from a Monounsaturated Fatty Acid or Ester
KR101331741B1 (en) * 2009-02-05 2013-11-20 아르끄마 프랑스 Method for synthesizing an omega-amino acid or ester from a monounsaturated fatty acid or ester
JP2012516882A (en) * 2009-02-05 2012-07-26 アルケマ フランス Method for synthesizing omega-amino acids or esters from monounsaturated fatty acids or esters
CN102307848B (en) * 2009-02-05 2014-07-23 阿肯马法国公司 Method for synthesizing an omega-amino acid or ester from a monounsaturated fatty acid or ester
FR2941694A1 (en) * 2009-02-05 2010-08-06 Arkema France PROCESS FOR SYNTHESIZING AN OMEGA-AMINOACIDE OR ESTERING FROM A MONO-UNSATURATED FATTY ACID OR ESTER
WO2010089512A1 (en) 2009-02-05 2010-08-12 Arkema France Method for synthesizing an omega-amino acid or ester from a monounsaturated fatty acid or ester
US8697401B2 (en) 2009-02-05 2014-04-15 Arkema France Method for synthesizing an ω-amino acid or ester from a monounsaturated fatty acid or ester
FR2970252A1 (en) * 2011-01-10 2012-07-13 Arkema France PROCESS FOR PRODUCING NITRILE-FATTY ACID COMPOUNDS
FR2970253A1 (en) * 2011-01-10 2012-07-13 Arkema France PROCESS FOR PRODUCING NITRILE-FATTY ACID COMPOUNDS
WO2012095575A1 (en) 2011-01-10 2012-07-19 Arkema France Process for producing nitrile-fatty acid compounds
CN103814007A (en) * 2011-07-19 2014-05-21 阿克马法国公司 Process for synthesizing omega-functionalized acids from fatty acids or fatty esters
CN103814007B (en) * 2011-07-19 2016-07-06 阿克马法国公司 For the method being synthesized omega-functionalized acid by fatty acid or fatty ester
US20140148607A1 (en) * 2011-07-19 2014-05-29 Arkema France Process for Synthesizing Omega-Functionalized Acids from Fatty Acids or Fatty Esters
FR2978147A1 (en) * 2011-07-19 2013-01-25 Arkema France PROCESS FOR SYNTHESIZING OMEGA-FUNCTIONALIZED ACIDS FROM HYDROXYLIC ACIDS OR FATTY ESTERS
WO2013011226A1 (en) * 2011-07-19 2013-01-24 Arkema France Process for synthesizing omega-functionalized acids from fatty acids or fatty esters
US8927746B2 (en) 2011-07-19 2015-01-06 Arkema France Process for synthesizing omega-functionalized acids from fatty acids or fatty esters
US8884041B2 (en) 2011-08-01 2014-11-11 Arkema France Method for synthesizing an omega-amino acid or ester from a monounsaturated fatty acid or ester
WO2013017782A1 (en) 2011-08-01 2013-02-07 Arkema France Method for synthesizing an omega-amino acid or ester from a monounsaturated fatty acid or ester
US20140357880A1 (en) * 2011-12-01 2014-12-04 Arkema France Method for cleaving unsaturated fatty chains
CN104093692A (en) * 2011-12-01 2014-10-08 阿克马法国公司 Method for cleaving unsaturated fatty chains
FR2983477A1 (en) * 2011-12-01 2013-06-07 Arkema France PROCESS FOR CUTTING UNSATURATED FAT CHANNELS
US9035079B2 (en) * 2011-12-01 2015-05-19 Arkema France Method for cleaving unsaturated fatty chains
WO2013079849A1 (en) * 2011-12-01 2013-06-06 Arkema France Method for cleaving unsaturated fatty chains
WO2014122410A2 (en) 2013-02-08 2014-08-14 Arkema France Combined synthesis of a nitrile-ester/acid and of a diester/diacid
US9567293B2 (en) 2013-02-08 2017-02-14 Arkema France Combined synthesis of a nitrile-ester/acid and of a diester/diacid

Also Published As

Publication number Publication date
ES213620A1 (en) 1955-04-16

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