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 acidInfo
- 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
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.
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)
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 |
-
1953
- 1953-02-23 GB GB4963/53A patent/GB741739A/en not_active Expired
-
1954
- 1954-02-11 ES ES0213620A patent/ES213620A1/en not_active Expired
Cited By (31)
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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