KR20140050082A - 단일불포화지방산 또는 에스테르로부터 오메가-아미노산 또는 에스테르를 합성하는 방법 - Google Patents
단일불포화지방산 또는 에스테르로부터 오메가-아미노산 또는 에스테르를 합성하는 방법 Download PDFInfo
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- KR20140050082A KR20140050082A KR1020147005099A KR20147005099A KR20140050082A KR 20140050082 A KR20140050082 A KR 20140050082A KR 1020147005099 A KR1020147005099 A KR 1020147005099A KR 20147005099 A KR20147005099 A KR 20147005099A KR 20140050082 A KR20140050082 A KR 20140050082A
- Authority
- KR
- South Korea
- Prior art keywords
- acid
- ester
- formula
- nitrile
- reaction
- 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.)
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- 238000000034 method Methods 0.000 title claims abstract description 32
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- 238000006243 chemical reaction Methods 0.000 claims abstract description 51
- -1 nitrile compound Chemical class 0.000 claims abstract description 26
- 230000008569 process Effects 0.000 claims abstract description 17
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims abstract description 7
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims abstract description 6
- 239000003054 catalyst Substances 0.000 claims description 29
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- 239000003925 fat Substances 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- LQJBNNIYVWPHFW-QXMHVHEDSA-N gadoleic acid Chemical compound CCCCCCCCCC\C=C/CCCCCCCC(O)=O LQJBNNIYVWPHFW-QXMHVHEDSA-N 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000011984 grubbs catalyst Substances 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000003622 immobilized catalyst Substances 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 238000006140 methanolysis reaction Methods 0.000 description 1
- SBIGSHCJXYGFMX-UHFFFAOYSA-N methyl dec-9-enoate Chemical compound COC(=O)CCCCCCCC=C SBIGSHCJXYGFMX-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- KISVAASFGZJBCY-UHFFFAOYSA-N methyl undecenate Chemical compound COC(=O)CCCCCCCCC=C KISVAASFGZJBCY-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical group [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- UIAMCVSNZQYIQS-KTKRTIGZSA-N oleonitrile Chemical compound CCCCCCCC\C=C/CCCCCCCC#N UIAMCVSNZQYIQS-KTKRTIGZSA-N 0.000 description 1
- 238000006385 ozonation reaction Methods 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000005538 phosphinite group Chemical group 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical group C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- XPQPWPZFBULGKT-UHFFFAOYSA-N undecanoic acid methyl ester Natural products CCCCCCCCCCC(=O)OC XPQPWPZFBULGKT-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1157020 | 2011-08-01 | ||
| FR1157020A FR2978764B1 (fr) | 2011-08-01 | 2011-08-01 | Procede de synthese d'un omega-aminoacide ou ester a partir d'un acide ou ester gras mono-insature |
| PCT/FR2012/051770 WO2013017782A1 (fr) | 2011-08-01 | 2012-07-26 | Procede de synthese d'un omega-aminoacide ou ester a partir d'un acide ou ester gras mono-insature |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20140050082A true KR20140050082A (ko) | 2014-04-28 |
Family
ID=46639637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020147005099A Withdrawn KR20140050082A (ko) | 2011-08-01 | 2012-07-26 | 단일불포화지방산 또는 에스테르로부터 오메가-아미노산 또는 에스테르를 합성하는 방법 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8884041B2 (enExample) |
| EP (1) | EP2739603B1 (enExample) |
| JP (1) | JP5981542B2 (enExample) |
| KR (1) | KR20140050082A (enExample) |
| CN (1) | CN103842331B (enExample) |
| AR (1) | AR087404A1 (enExample) |
| BR (1) | BR112014002065A2 (enExample) |
| CA (1) | CA2842750A1 (enExample) |
| FR (1) | FR2978764B1 (enExample) |
| PL (1) | PL2739603T3 (enExample) |
| WO (1) | WO2013017782A1 (enExample) |
| ZA (1) | ZA201400886B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3001964B1 (fr) | 2013-02-08 | 2015-02-20 | Arkema France | Synthese de compose insature ramifie par metathese croisee |
| FR3001966A1 (fr) * | 2013-02-08 | 2014-08-15 | Arkema France | Synthese conjuguee d'un nitrile- ester/acide et d'un diester/diacide |
| FR3001965B1 (fr) * | 2013-02-08 | 2015-02-20 | Arkema France | Procede de synthese d'aminoacide par metathese, hydrolyse puis hydrogenation |
| FR3002227B1 (fr) * | 2013-02-20 | 2021-10-01 | Arkema France | Procede de nitrilation en phase gaz et liquide gaz |
| FR3029203B1 (fr) * | 2014-11-27 | 2016-12-30 | Arkema France | Compositions elastomeres contenant au moins un plastifiant forme par un ester de diacide gras insature, de preference mono-insature |
| FR3041634B1 (fr) | 2015-09-30 | 2017-10-20 | Arkema France | Composition a base d'amino acide ou ester de qualite polymere et procedes d'obtention |
| US10774035B2 (en) | 2016-09-23 | 2020-09-15 | Umicore Ag & Co. Kg | Preparation of amino acids and amino acid derivatives |
| US20240132424A1 (en) * | 2021-02-11 | 2024-04-25 | Petróleo Brasileiro S.A. – Petrobras | Method for the coproduction of c10 to c13 olefins and esters from fatty acid methyl esters |
| IT202100022328A1 (it) * | 2021-08-25 | 2023-02-25 | Versalis Spa | Metodo per la preparazione di acidi ω-ammino-carbossilici e loro derivati. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB741739A (en) | 1953-02-23 | 1955-12-14 | Courtaulds Ltd | Improvements in and relating to the production of omega-amino nonanoic acid |
| FR2938533B1 (fr) | 2008-11-17 | 2010-11-19 | Arkema France | Procede de synthese d'un omega-aminoacide ou ester a partir d'un acide ou ester gras mono-insature |
| FR2959742B1 (fr) * | 2010-05-07 | 2012-08-24 | Arkema France | Procede de preparation d'amino-acides ou esters satures comprenant une etape de metathese |
-
2011
- 2011-08-01 FR FR1157020A patent/FR2978764B1/fr not_active Expired - Fee Related
-
2012
- 2012-07-26 KR KR1020147005099A patent/KR20140050082A/ko not_active Withdrawn
- 2012-07-26 WO PCT/FR2012/051770 patent/WO2013017782A1/fr not_active Ceased
- 2012-07-26 EP EP12744111.1A patent/EP2739603B1/fr not_active Not-in-force
- 2012-07-26 US US14/234,879 patent/US8884041B2/en not_active Expired - Fee Related
- 2012-07-26 BR BR112014002065A patent/BR112014002065A2/pt not_active IP Right Cessation
- 2012-07-26 CA CA2842750A patent/CA2842750A1/fr not_active Abandoned
- 2012-07-26 JP JP2014523363A patent/JP5981542B2/ja not_active Expired - Fee Related
- 2012-07-26 PL PL12744111T patent/PL2739603T3/pl unknown
- 2012-07-26 CN CN201280048363.1A patent/CN103842331B/zh not_active Expired - Fee Related
- 2012-08-01 AR ARP120102795A patent/AR087404A1/es active IP Right Grant
-
2014
- 2014-02-05 ZA ZA2014/00886A patent/ZA201400886B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2842750A1 (fr) | 2013-02-07 |
| FR2978764B1 (fr) | 2013-08-16 |
| BR112014002065A2 (pt) | 2017-02-21 |
| FR2978764A1 (fr) | 2013-02-08 |
| WO2013017782A1 (fr) | 2013-02-07 |
| ZA201400886B (en) | 2015-11-25 |
| JP2014524938A (ja) | 2014-09-25 |
| JP5981542B2 (ja) | 2016-08-31 |
| US20140187808A1 (en) | 2014-07-03 |
| EP2739603B1 (fr) | 2015-06-17 |
| CN103842331B (zh) | 2015-11-25 |
| US8884041B2 (en) | 2014-11-11 |
| EP2739603A1 (fr) | 2014-06-11 |
| CN103842331A (zh) | 2014-06-04 |
| AR087404A1 (es) | 2014-03-19 |
| PL2739603T3 (pl) | 2015-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20140226 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |