ES2149689B1 - PROCEDURE FOR THE SELECTIVE OBTAINING OF 12-HYDROXI-9-CIS-OCTADECENOATE OF 1-GLYCERILE USING IMMOBILIZED LIPASSES AS A CATALYST. - Google Patents
PROCEDURE FOR THE SELECTIVE OBTAINING OF 12-HYDROXI-9-CIS-OCTADECENOATE OF 1-GLYCERILE USING IMMOBILIZED LIPASSES AS A CATALYST.Info
- Publication number
- ES2149689B1 ES2149689B1 ES9800944A ES9800944A ES2149689B1 ES 2149689 B1 ES2149689 B1 ES 2149689B1 ES 9800944 A ES9800944 A ES 9800944A ES 9800944 A ES9800944 A ES 9800944A ES 2149689 B1 ES2149689 B1 ES 2149689B1
- Authority
- ES
- Spain
- Prior art keywords
- immobilized
- catalyst
- cis
- octadecenoate
- procedure
- 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 - Fee Related
Links
- 239000003054 catalyst Substances 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 3
- 102000004882 Lipase Human genes 0.000 abstract 4
- 108090001060 Lipase Proteins 0.000 abstract 4
- 239000004367 Lipase Substances 0.000 abstract 4
- 235000019421 lipase Nutrition 0.000 abstract 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 2
- 241001661345 Moesziomyces antarcticus Species 0.000 abstract 2
- 238000005886 esterification reaction Methods 0.000 abstract 2
- 230000002538 fungal effect Effects 0.000 abstract 2
- 239000011148 porous material Substances 0.000 abstract 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 abstract 1
- 241000235395 Mucor Species 0.000 abstract 1
- 229920006397 acrylic thermoplastic Polymers 0.000 abstract 1
- 239000003463 adsorbent Substances 0.000 abstract 1
- 125000000129 anionic group Chemical group 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 235000011187 glycerol Nutrition 0.000 abstract 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 abstract 1
- 229960003656 ricinoleic acid Drugs 0.000 abstract 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 abstract 1
- 241000894007 species Species 0.000 abstract 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Procedimiento para la obtención selectiva de 12-hidroxi-9-cis-octadecenoato de 1-glicerilo utilizando lipasas inmovilizadas como catalizador. La esterificación selectiva del ácido ricinoleico (12-hidroxi-9-cis-octadecenoico) y la glicerina se realiza mediante el empleo como catalizador, de lipasas inmovilizadas en resinas de intercambio aniónico o acrílicas porosas u otras que confieran al catalizador obtenido un diámetro de poro entre 50 y 400 {Ao , y una superficie específica entre 10 y 150 m{sup,2 /gr. Las lipasas empleadas provienen de las especies fúngicas Mucor miehi y Candida antarctica. La reacción de esterificación se realiza a presiones comprendidas entre la atmosférica y 1 mm de Hg., a una temperatura comprendida entre 20 y 90ºC. Los mejores rendimientos y selectividades se obtuvieron utilizando una lipasa de la especie fúngica de Candida antarctica inmovilizado en un adsorbente polimérico con un diámetro de poro de 180{Ao y una superficie específica de 95 m{sup,2 /gr., a la temperatura de 78,3 ºC y 60 mm de Hg de presión. Es de destacar que mediante el procedimiento objeto de esta invención se obtiene mayoritariamente el monoglicérido y específicamente el isómero cis.Procedure for the selective obtaining of 1-glyceryl 12-hydroxy-9-cis-octadecenoate using immobilized lipases as a catalyst. Selective esterification of ricinoleic acid (12-hydroxy-9-cis-octadecenoic acid) and glycerin is carried out by using as a catalyst, lipases immobilized in anionic exchange resins or porous acrylics or others that confer to the catalyst obtained a pore diameter between 50 and 400 {Ao, and a specific surface between 10 and 150 m {sup, 2 / gr. The lipases used come from the fungal species Mucor miehi and Candida antarctica. The esterification reaction is carried out at pressures between atmospheric and 1 mm Hg., At a temperature between 20 and 90 ° C. The best yields and selectivities were obtained using a lipase of the fungal species of Candida antarctica immobilized in a polymeric adsorbent with a pore diameter of 180 {Ao and a specific surface area of 95 m {sup, 2 / gr., At the temperature of 78.3 ° C and 60 mm Hg pressure. It is noteworthy that the monoglyceride and specifically the cis isomer is obtained by means of the process object of this invention.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES9800944A ES2149689B1 (en) | 1998-05-05 | 1998-05-05 | PROCEDURE FOR THE SELECTIVE OBTAINING OF 12-HYDROXI-9-CIS-OCTADECENOATE OF 1-GLYCERILE USING IMMOBILIZED LIPASSES AS A CATALYST. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES9800944A ES2149689B1 (en) | 1998-05-05 | 1998-05-05 | PROCEDURE FOR THE SELECTIVE OBTAINING OF 12-HYDROXI-9-CIS-OCTADECENOATE OF 1-GLYCERILE USING IMMOBILIZED LIPASSES AS A CATALYST. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2149689A1 ES2149689A1 (en) | 2000-11-01 |
| ES2149689B1 true ES2149689B1 (en) | 2001-04-01 |
Family
ID=8303687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES9800944A Expired - Fee Related ES2149689B1 (en) | 1998-05-05 | 1998-05-05 | PROCEDURE FOR THE SELECTIVE OBTAINING OF 12-HYDROXI-9-CIS-OCTADECENOATE OF 1-GLYCERILE USING IMMOBILIZED LIPASSES AS A CATALYST. |
Country Status (1)
| Country | Link |
|---|---|
| ES (1) | ES2149689B1 (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3854042T2 (en) * | 1987-12-09 | 1995-11-16 | Kao Corp., Tokio/Tokyo | Immobilized enzyme and esterification and intermediate esterification with the same. |
| DK306189D0 (en) * | 1989-06-21 | 1989-06-21 | Novo Nordisk As | IMMOBILIZED LIPASE PREPARATION AND ITS USE FOR ESTER SYNTHESIS |
-
1998
- 1998-05-05 ES ES9800944A patent/ES2149689B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES2149689A1 (en) | 2000-11-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EC2A | Search report published |
Date of ref document: 20001101 Kind code of ref document: A1 Effective date: 20001101 |
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| FD2A | Announcement of lapse in spain |
Effective date: 20180824 |