WO1998015640A1 - Procedimiento de preparacion selectiva de derivados de monosacaridos y polioles parcialmente acilados - Google Patents
Procedimiento de preparacion selectiva de derivados de monosacaridos y polioles parcialmente acilados Download PDFInfo
- Publication number
- WO1998015640A1 WO1998015640A1 PCT/ES1997/000240 ES9700240W WO9815640A1 WO 1998015640 A1 WO1998015640 A1 WO 1998015640A1 ES 9700240 W ES9700240 W ES 9700240W WO 9815640 A1 WO9815640 A1 WO 9815640A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- fatty acids
- polyols
- monosaccharides
- derivatives
- lipases
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 38
- 229920005862 polyol Chemical class 0.000 title claims abstract description 15
- 150000003077 polyols Chemical class 0.000 title claims abstract description 15
- 150000002772 monosaccharides Chemical class 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims description 8
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 17
- 229930195729 fatty acid Natural products 0.000 claims abstract description 17
- 239000000194 fatty acid Substances 0.000 claims abstract description 17
- 150000004665 fatty acids Chemical group 0.000 claims abstract description 17
- 239000004367 Lipase Substances 0.000 claims abstract description 10
- 102000004882 Lipase Human genes 0.000 claims abstract description 10
- 108090001060 Lipase Proteins 0.000 claims abstract description 10
- 235000019421 lipase Nutrition 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 235000000346 sugar Nutrition 0.000 claims description 7
- 239000012429 reaction media Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- 241000235403 Rhizomucor miehei Species 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 241001661345 Moesziomyces antarcticus Species 0.000 claims 1
- 230000002255 enzymatic effect Effects 0.000 abstract description 12
- 239000003054 catalyst Substances 0.000 abstract description 4
- 239000000654 additive Substances 0.000 abstract description 3
- 239000002537 cosmetic Substances 0.000 abstract description 3
- 235000013305 food Nutrition 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 230000008719 thickening Effects 0.000 abstract description 2
- 231100000167 toxic agent Toxicity 0.000 abstract description 2
- 239000003440 toxic substance Substances 0.000 abstract description 2
- 230000000887 hydrating effect Effects 0.000 abstract 1
- 239000002736 nonionic surfactant Substances 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 11
- 102000004190 Enzymes Human genes 0.000 description 9
- 108090000790 Enzymes Proteins 0.000 description 9
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 8
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 8
- 239000000600 sorbitol Substances 0.000 description 8
- 239000005639 Lauric acid Substances 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 5
- 239000008103 glucose Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000006911 enzymatic reaction Methods 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- HVCOBJNICQPDBP-UHFFFAOYSA-N 3-[3-[3,5-dihydroxy-6-methyl-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxydecanoyloxy]decanoic acid;hydrate Chemical compound O.OC1C(OC(CC(=O)OC(CCCCCCC)CC(O)=O)CCCCCCC)OC(C)C(O)C1OC1C(O)C(O)C(O)C(C)O1 HVCOBJNICQPDBP-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229930186217 Glycolipid Natural products 0.000 description 3
- FTCGZXFZNUEELT-BURFUSLBSA-N [(2r,3r,4s,5r)-2,3,4,5-tetrahydroxy-6-oxohexyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O FTCGZXFZNUEELT-BURFUSLBSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001311 chemical methods and process Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 235000014593 oils and fats Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000011942 biocatalyst Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000007385 chemical modification Methods 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000004668 long chain fatty acids Chemical class 0.000 description 2
- 230000003020 moisturizing effect Effects 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 241001133760 Acoelorraphe Species 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- -1 morning Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/02—Monosaccharides
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/62—Carboxylic acid esters
Definitions
- the invention falls within the food, pharmaceutical, cosmetic and chemical sectors.
- the products obtained are excellent non-ionic, biocompatible and biodegradable surfactants, used as additives for their emulsifying, unctuous, thickening and moisturizing character.
- Lipases are the hydrolytic enzymes that best catalyze the processes in which long fatty acids are involved. These form covalent bonds with alcohols in poorly hydrated media. They are biocatalysts of great industrial interest for their versatility, and availability. In addition the lipases are biodegradable. When there are several hydroxyl groups in the same molecule, lipases allow long synthetic routes (with protection / deprotection stages) to be replaced by an enzymatic stage due to their great regioselectivity. This increases yields and reduces the cost of the process itself, and that of waste treatment [Biocatalysts for Industry (1991) Plenum Press, N.Y.Ed.J. Dordick], compared to that of an alternative chemical process. In addition the chemo- and cnantiosclivity of lipases can lead to very competitive synthetic processes.
- More than 80% of the global surfactants market are molecules formed by the condensation between polyols or monosaccharides and long-chain fatty acids (glycerides, spanes, tweens, etc.). Sorbitan derivatives esterified with long chain fatty acids are biocompatible glycolipid surfactants widely used in different types of industries.
- the esterified sorbitan derivatives are commercially called Spanes. They have a Very lipophilic character, and they are precursors of the Tweenes. Currently Tweens and Spanes are prepared industrially by non - enzymatically to 180-150 C. Surfactants gluco- and glycolipid are additives used in cosmetic and pharmaceutical, for their different properties (moisturizing power, lubricant, etc.). Many of these emulsifiers, which in themselves are biocompatible, present problems for use in certain applications (ie food sector). The problems are inherent in the traditional chemical method of preparation. The presence of certain synthetic agents in chemical processes of preparation or purification of feed additive constitutes one of the drawbacks of the preparation methods used. The selective obtaining of emulsifiers by enzymes can solve this problem. European and American laws consider substances produced or modified by enzymes "natural".
- glycolipid surfactants derived from monosaccharides and polyols has been studied in the literature, where yields are not high [Khaled, N., Montet, D.Pina, M. and Graille, J. Biotech.Let., 13, 167-172 (1991) and Schlotterbeck, A. Lang, S., Wray, V. and Wagner, F. Biotechnol.Lett. 15, 61-64 (1993)] and / or require previous non-enzymatic stages [Fregapane, G., Samcy, DB and Vulfson, EN Enz.Microb.Technol.
- the present invention provides an enzymatic method of selective synthesis of esters of partially acylated polyols and monosaccharides with fatty acids in practically anhydrous media. It allows to obtain total or practically quantitative yields in a single stage.
- the invention relates to the highly selective enzymatic production of monosaccharides and mono- and / or disubstituted polyols with fatty acids.
- the procedure is based on the simple mixture of the polyol or monosaccharide with the fatty acid, the addition of the solvent, and uses lipases that allow them to be obtained collectively without catalysts or toxic agents.
- the process requires the continuous withdrawal of the water produced during it.
- Synthesized surfactants have a higher biodegradability than ethoxylated alkylphenols frequently used in detergents for washing machines, etc.
- Lipases can act with pure fatty acids and also with mixtures of these from natural oils and fats (olive, coconut, palm, etc).
- the European Union has large surpluses of oils and fats.
- the inimization of waste and the recovery of by-products (oils and fats), their revaluation and recycling in the industry, is one of the priority objectives at European level and others.
- the invention is applicable to linear polyols such as sorbitol.
- Monosaccharides such as glucose, fructose, mannose etc. are also selectively transformed.
- the galactose reaction has lower selectivity, obtaining a greater mixture of mono and diesters.
- the patented process allows different fatty acids of variable chain length to be used, preferably from C8 to C22.
- the acid chain can be saturated or unsaturated, linear or branched (i.c. octanoic acid, hexadecanoic acid, oleic acid, etc.). It is also possible to use a mixture of fatty acids (i.e. industrial acids from coconut, soy, corn, cottonseed, etc.). The direct use of ethyl esters of fatty acids is much less effective in these processes.
- the process can be catalyzed by yeast lipolic enzymes or animal, plant, bacterial or fungal origin. This can be in native form, immobilized on an inert support and / or chemically modified, or it can be obtained by genetic engineering. Thus, good yields have been found with immobilized lipases from Antarctic Candida (Novozim
- the process can be carried out in different solvents or relatively polar organic media in order to at least partially solubilize the polyol (or sugar), preferably those of low boiling point to facilitate its elimination.
- the solvent and reactants must have a low aqueous content, preferably less than 5% w / w and more preferably in the range 0.01 to 1% w / w.
- the concentration of fatty acid should be greater than 100 mM and be in a molar excess of at least 1.5 times with respect to sugar.
- the process can be carried out continuously and in a stirred tank.
- the amount of enzyme needed depends on the specific activity of the enzyme preparation used.
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Microbiology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/269,997 US6200784B1 (en) | 1996-10-04 | 1997-10-01 | Process for the selective preparation of derivatives of monosaccharides and polyols which are partially acylated |
BR9712201-7A BR9712201A (pt) | 1996-10-04 | 1997-10-01 | Processo para preparação seletiva de monossacarìdio parcialmente acilado e derivados de poliol linear |
DK97942040T DK0945516T3 (da) | 1996-10-04 | 1997-10-01 | Fremgangsmåde til selektiv fremstilling af delvis acylerede derivater af monosaccharider og polyoler |
AU43856/97A AU4385697A (en) | 1996-10-04 | 1997-10-01 | Process for the selective preparation of derivatives of monosaccharides and polyols which are partially acylated |
ES97942040T ES2196365T3 (es) | 1996-10-04 | 1997-10-01 | Procedimiento de preparacion selectiva de derivados parcialmente acilados de monosacaridos y de polioles. |
EP97942040A EP0945516B1 (en) | 1996-10-04 | 1997-10-01 | Process for the selective preparation of partially acylated derivatives of monosaccharides and polyols |
AT97942040T ATE236265T1 (de) | 1996-10-04 | 1997-10-01 | Verfarhren zur herstellung von teilweise acylierten derivativen von monosacchariden und polyolen |
DE69720514T DE69720514T2 (de) | 1996-10-04 | 1997-10-01 | Verfarhren zur herstellung von teilweise acylierten derivativen von monosacchariden und polyolen |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ESP9602091 | 1996-10-04 | ||
ES09602091A ES2114506B1 (es) | 1996-10-04 | 1996-10-04 | Procedimiento de preparacion selectiva de derivados de monosacaridos y polioles parcialmente acilados. |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998015640A1 true WO1998015640A1 (es) | 1998-04-16 |
Family
ID=8296229
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/ES1997/000240 WO1998015640A1 (es) | 1996-10-04 | 1997-10-01 | Procedimiento de preparacion selectiva de derivados de monosacaridos y polioles parcialmente acilados |
Country Status (10)
Country | Link |
---|---|
US (1) | US6200784B1 (es) |
EP (1) | EP0945516B1 (es) |
AT (1) | ATE236265T1 (es) |
AU (1) | AU4385697A (es) |
BR (1) | BR9712201A (es) |
DE (1) | DE69720514T2 (es) |
DK (1) | DK0945516T3 (es) |
ES (2) | ES2114506B1 (es) |
PT (1) | PT945516E (es) |
WO (1) | WO1998015640A1 (es) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2827192B1 (fr) * | 2001-07-13 | 2004-06-04 | Cognis France Sa | Preparations contenant des agents tensio-actifs non ioniques comme agents d'extraction |
US8652064B2 (en) * | 2008-09-30 | 2014-02-18 | Covidien Lp | Sampling circuit for measuring analytes |
WO2011014653A2 (en) * | 2009-07-29 | 2011-02-03 | The Research Foundation Of The City University Of New York | Methods for thickening hydrophobic liquids with amphiphilic esters |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS62195292A (ja) * | 1986-02-21 | 1987-08-28 | Dai Ichi Kogyo Seiyaku Co Ltd | リパ−ゼを用いる脂肪酸エステルの製法 |
JPS62289190A (ja) * | 1986-06-05 | 1987-12-16 | Dai Ichi Kogyo Seiyaku Co Ltd | リパ−ゼを用いる脂肪酸エステルの製法 |
EP0274798A2 (en) * | 1986-12-19 | 1988-07-20 | Unilever N.V. | Process for the preparation of esters |
EP0506159A1 (en) * | 1991-03-19 | 1992-09-30 | Unichema Chemie B.V. | Esterification process |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6138062A (ja) | 1984-07-30 | 1986-02-24 | ナショナル住宅産業株式会社 | 床構造 |
GB8806691D0 (en) | 1988-03-21 | 1988-04-20 | Cerestar Holding Bv | Surface active compounds & process for their preparation |
FR2652587B1 (fr) | 1989-10-03 | 1992-01-31 | Pernod Ricard | Procede de synthese du cis-3-hexene-1-ol a partir d'acide gras insature. |
US5508182A (en) * | 1991-02-13 | 1996-04-16 | Schneider; Manfred P. | Esterification of hydrophilic polyols by adsorption onto a solid support and employing a substrate-immiscible solvent |
-
1996
- 1996-10-04 ES ES09602091A patent/ES2114506B1/es not_active Expired - Lifetime
-
1997
- 1997-10-01 PT PT97942040T patent/PT945516E/pt unknown
- 1997-10-01 BR BR9712201-7A patent/BR9712201A/pt not_active Application Discontinuation
- 1997-10-01 US US09/269,997 patent/US6200784B1/en not_active Expired - Fee Related
- 1997-10-01 EP EP97942040A patent/EP0945516B1/en not_active Expired - Lifetime
- 1997-10-01 AU AU43856/97A patent/AU4385697A/en not_active Abandoned
- 1997-10-01 WO PCT/ES1997/000240 patent/WO1998015640A1/es active IP Right Grant
- 1997-10-01 ES ES97942040T patent/ES2196365T3/es not_active Expired - Lifetime
- 1997-10-01 DK DK97942040T patent/DK0945516T3/da active
- 1997-10-01 DE DE69720514T patent/DE69720514T2/de not_active Expired - Fee Related
- 1997-10-01 AT AT97942040T patent/ATE236265T1/de not_active IP Right Cessation
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS62195292A (ja) * | 1986-02-21 | 1987-08-28 | Dai Ichi Kogyo Seiyaku Co Ltd | リパ−ゼを用いる脂肪酸エステルの製法 |
JPS62289190A (ja) * | 1986-06-05 | 1987-12-16 | Dai Ichi Kogyo Seiyaku Co Ltd | リパ−ゼを用いる脂肪酸エステルの製法 |
EP0274798A2 (en) * | 1986-12-19 | 1988-07-20 | Unilever N.V. | Process for the preparation of esters |
EP0506159A1 (en) * | 1991-03-19 | 1992-09-30 | Unichema Chemie B.V. | Esterification process |
Non-Patent Citations (2)
Title |
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DATABASE WPI Week 8805, Derwent World Patents Index; AN 1988-031288 * |
DATABASE WPI Week 9210, Derwent World Patents Index; AN 1987-280944 * |
Also Published As
Publication number | Publication date |
---|---|
EP0945516B1 (en) | 2003-04-02 |
ES2114506A1 (es) | 1998-05-16 |
ATE236265T1 (de) | 2003-04-15 |
EP0945516A1 (en) | 1999-09-29 |
DK0945516T3 (da) | 2003-07-21 |
DE69720514D1 (de) | 2003-05-08 |
ES2114506B1 (es) | 1999-02-01 |
AU4385697A (en) | 1998-05-05 |
US6200784B1 (en) | 2001-03-13 |
PT945516E (pt) | 2003-08-29 |
ES2196365T3 (es) | 2003-12-16 |
BR9712201A (pt) | 2002-05-21 |
DE69720514T2 (de) | 2004-03-04 |
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