GB743491A - 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
- GB743491A GB743491A GB4964/53A GB496453A GB743491A GB 743491 A GB743491 A GB 743491A GB 4964/53 A GB4964/53 A GB 4964/53A GB 496453 A GB496453 A GB 496453A GB 743491 A GB743491 A GB 743491A
- Authority
- GB
- United Kingdom
- 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
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.
Priority Applications (2)
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 |
ES0213621A ES213621A1 (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 |
---|---|---|---|
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 |
---|---|
GB743491A true GB743491A (en) | 1956-01-18 |
Family
ID=9787212
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4964/53A Expired GB743491A (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) | ES213621A1 (en) |
GB (1) | GB743491A (en) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
FR2970253A1 (en) * | 2011-01-10 | 2012-07-13 | Arkema France | PROCESS FOR PRODUCING NITRILE-FATTY ACID COMPOUNDS |
WO2013007634A1 (en) | 2011-07-08 | 2013-01-17 | Dsm Ip Assets B.V. | Preparation of nitrile compounds |
WO2013011226A1 (en) | 2011-07-19 | 2013-01-24 | Arkema France | Process for synthesizing omega-functionalized acids from fatty acids or fatty esters |
US8377661B2 (en) | 2008-07-10 | 2013-02-19 | Arkema France | Method for synthesising omega-amino-alkanoic acids or the esters thereof from natural fatty acids |
US8450509B2 (en) | 2008-07-10 | 2013-05-28 | Arkema France | Method for synthesising 9-aminononanoic acid or the esters thereof from natural unsaturated fatty acids |
WO2014122410A2 (en) | 2013-02-08 | 2014-08-14 | Arkema France | Combined synthesis of a nitrile-ester/acid and of a diester/diacid |
CN104093692A (en) * | 2011-12-01 | 2014-10-08 | 阿克马法国公司 | Method for cleaving unsaturated fatty chains |
-
1953
- 1953-02-23 GB GB4964/53A patent/GB743491A/en not_active Expired
-
1954
- 1954-02-11 ES ES0213621A patent/ES213621A1/en not_active Expired
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8377661B2 (en) | 2008-07-10 | 2013-02-19 | Arkema France | Method for synthesising omega-amino-alkanoic acids or the esters thereof from natural fatty acids |
US8450509B2 (en) | 2008-07-10 | 2013-05-28 | Arkema France | Method for synthesising 9-aminononanoic acid or the esters thereof from natural unsaturated fatty acids |
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 |
FR2970253A1 (en) * | 2011-01-10 | 2012-07-13 | Arkema France | PROCESS FOR PRODUCING NITRILE-FATTY ACID COMPOUNDS |
FR2970252A1 (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 |
WO2013007634A1 (en) | 2011-07-08 | 2013-01-17 | Dsm Ip Assets B.V. | Preparation of nitrile compounds |
WO2013011226A1 (en) | 2011-07-19 | 2013-01-24 | Arkema France | Process for synthesizing omega-functionalized acids from fatty acids or fatty esters |
CN104093692A (en) * | 2011-12-01 | 2014-10-08 | 阿克马法国公司 | 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 |
---|---|
ES213621A1 (en) | 1955-04-16 |
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