GB1177154A - Production of 12-Aminododecanoic Acid or Alkali Metal Salts thereof - Google Patents
Production of 12-Aminododecanoic Acid or Alkali Metal Salts thereofInfo
- Publication number
- GB1177154A GB1177154A GB3285767A GB3285767A GB1177154A GB 1177154 A GB1177154 A GB 1177154A GB 3285767 A GB3285767 A GB 3285767A GB 3285767 A GB3285767 A GB 3285767A GB 1177154 A GB1177154 A GB 1177154A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- catalysts
- raney
- cobalt
- hydrogenation
- 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
- PBLZLIFKVPJDCO-UHFFFAOYSA-N 12-aminododecanoic acid Chemical compound NCCCCCCCCCCCC(O)=O PBLZLIFKVPJDCO-UHFFFAOYSA-N 0.000 title abstract 6
- -1 Alkali Metal Salts Chemical class 0.000 title abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 title abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- RAFOGKOTRLOFKP-UHFFFAOYSA-N 12-amino-12-oxododecanoic acid Chemical compound NC(=O)CCCCCCCCCCC(O)=O RAFOGKOTRLOFKP-UHFFFAOYSA-N 0.000 abstract 2
- 239000007868 Raney catalyst Substances 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 229910017052 cobalt Inorganic materials 0.000 abstract 2
- 239000010941 cobalt Substances 0.000 abstract 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 229910000428 cobalt oxide Inorganic materials 0.000 abstract 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 229910000510 noble metal Inorganic materials 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 238000005979 thermal decomposition reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,177,154. 12-Aminododecanoic acid. BP CHEMICALS (U.K.) Ltd. 8 July, 1968 [18 July, 1967], No. 32857/67. Heading C2C. 12-Aminododecanoic acid is prepared by catalytic hydrogenation of 11-cyanoindecanoic acid or its 11-carbamoylundecanoic acid, alkali metal salts. Mixtures of the cyano acid with 11-carbamoylundecanoic acid that result from the thermal decomposition of 1,1<SP>1</SP>-peroxydicyclohexylamine at 300-1000‹ C. are suitable starting materials. Preferred hydrogenation catalysts are those containing a Group VIII metal, e.g. Raney nickel, Raney cobalt, cobalt oxide admixed with phosphate, and platinum on carbon, and preferred solvents are aqueous acetic acid and (for Raney catalysts) lower alkanols, especially a mixture of n-propanol and aqueous ammonia. The hydrogenation is normally carried out at 50-60‹ C. under 60-80 atmospheres using noble metal catalysts, or at 10-200‹ C. and between 1 and 300 atmospheres with cobalt or nickel catalysts. Traces of 12,12<SP>1</SP>-imino bis-(dodecanoic acid) are formed as by-product.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3285767A GB1177154A (en) | 1967-07-18 | 1967-07-18 | Production of 12-Aminododecanoic Acid or Alkali Metal Salts thereof |
| DE19681768946 DE1768946A1 (en) | 1967-07-18 | 1968-07-16 | Process for the preparation of 12-aminododecanoic acid or its alkali salts |
| FR1574471D FR1574471A (en) | 1967-07-18 | 1968-07-17 | |
| NL6810075A NL6810075A (en) | 1967-07-18 | 1968-07-17 | |
| BE718262D BE718262A (en) | 1967-07-18 | 1968-07-18 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3285767A GB1177154A (en) | 1967-07-18 | 1967-07-18 | Production of 12-Aminododecanoic Acid or Alkali Metal Salts thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1177154A true GB1177154A (en) | 1970-01-07 |
Family
ID=10345052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3285767A Expired GB1177154A (en) | 1967-07-18 | 1967-07-18 | Production of 12-Aminododecanoic Acid or Alkali Metal Salts thereof |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE718262A (en) |
| DE (1) | DE1768946A1 (en) |
| FR (1) | FR1574471A (en) |
| GB (1) | GB1177154A (en) |
| NL (1) | NL6810075A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011138051A1 (en) | 2010-05-07 | 2011-11-10 | Arkema France | Process for preparing saturated amino acids or saturated amino esters comprising a metathesis step |
| WO2014072641A1 (en) | 2012-11-09 | 2014-05-15 | Arkema France | Selective extraction of an omega-functionalised acid after oxidative cleavage of an unsaturated fatty acid and derivatives |
| US9790168B2 (en) | 2013-02-08 | 2017-10-17 | Arkema France | Method of synthesising amino acid by metathesis, hydrolysis, then hydrogenation |
| CN107445850A (en) * | 2017-08-09 | 2017-12-08 | 无锡殷达尼龙有限公司 | A kind of preparation method of 12 aminoundecane-earboxylic acid |
| CN116783156A (en) * | 2021-02-02 | 2023-09-19 | 阿科玛法国公司 | Ammonolysis method of bromoalkanoic acid |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5434307A (en) * | 1993-05-21 | 1995-07-18 | Howard University | Synthesis of 12-oxododecanoic acid oxime from vernolic acid |
-
1967
- 1967-07-18 GB GB3285767A patent/GB1177154A/en not_active Expired
-
1968
- 1968-07-16 DE DE19681768946 patent/DE1768946A1/en active Pending
- 1968-07-17 NL NL6810075A patent/NL6810075A/xx unknown
- 1968-07-17 FR FR1574471D patent/FR1574471A/fr not_active Expired
- 1968-07-18 BE BE718262D patent/BE718262A/xx unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011138051A1 (en) | 2010-05-07 | 2011-11-10 | Arkema France | Process for preparing saturated amino acids or saturated amino esters comprising a metathesis step |
| WO2014072641A1 (en) | 2012-11-09 | 2014-05-15 | Arkema France | Selective extraction of an omega-functionalised acid after oxidative cleavage of an unsaturated fatty acid and derivatives |
| US9790168B2 (en) | 2013-02-08 | 2017-10-17 | Arkema France | Method of synthesising amino acid by metathesis, hydrolysis, then hydrogenation |
| CN107445850A (en) * | 2017-08-09 | 2017-12-08 | 无锡殷达尼龙有限公司 | A kind of preparation method of 12 aminoundecane-earboxylic acid |
| CN116783156A (en) * | 2021-02-02 | 2023-09-19 | 阿科玛法国公司 | Ammonolysis method of bromoalkanoic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| BE718262A (en) | 1969-01-20 |
| NL6810075A (en) | 1969-01-21 |
| FR1574471A (en) | 1969-07-11 |
| DE1768946A1 (en) | 1972-02-24 |
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