NL8600148A - Werkwijze voor het bereiden van glyceriden in aanwezigheid van lipasen. - Google Patents
Werkwijze voor het bereiden van glyceriden in aanwezigheid van lipasen. Download PDFInfo
- Publication number
- NL8600148A NL8600148A NL8600148A NL8600148A NL8600148A NL 8600148 A NL8600148 A NL 8600148A NL 8600148 A NL8600148 A NL 8600148A NL 8600148 A NL8600148 A NL 8600148A NL 8600148 A NL8600148 A NL 8600148A
- Authority
- NL
- Netherlands
- Prior art keywords
- fatty acid
- lipase
- process according
- ester
- glycerol
- Prior art date
Links
- 102000004882 Lipase Human genes 0.000 title claims description 72
- 108090001060 Lipase Proteins 0.000 title claims description 72
- 239000004367 Lipase Substances 0.000 title claims description 64
- 238000000034 method Methods 0.000 title claims description 42
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 108
- 239000000194 fatty acid Substances 0.000 claims description 71
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 68
- 229930195729 fatty acid Natural products 0.000 claims description 68
- 235000019421 lipase Nutrition 0.000 claims description 63
- 150000004665 fatty acids Chemical class 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 25
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 22
- 241001507683 Penicillium aurantiogriseum Species 0.000 claims description 18
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 claims description 17
- 239000007858 starting material Substances 0.000 claims description 16
- -1 fatty acid ester Chemical class 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 102000017055 Lipoprotein Lipase Human genes 0.000 claims description 10
- 108010013563 Lipoprotein Lipase Proteins 0.000 claims description 10
- 102000005398 Monoacylglycerol Lipase Human genes 0.000 claims description 10
- 108020002334 Monoacylglycerol lipase Proteins 0.000 claims description 10
- 150000003626 triacylglycerols Chemical class 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 230000003301 hydrolyzing effect Effects 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 5
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 5
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 5
- 238000004587 chromatography analysis Methods 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 235000003441 saturated fatty acids Nutrition 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229920001567 vinyl ester resin Polymers 0.000 claims 2
- 125000005456 glyceride group Chemical group 0.000 description 55
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 35
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 16
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 15
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 15
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 15
- 239000005642 Oleic acid Substances 0.000 description 15
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 15
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical class CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 5
- 241000228143 Penicillium Species 0.000 description 5
- 239000004599 antimicrobial Substances 0.000 description 5
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- CMDXMIHZUJPRHG-UHFFFAOYSA-N ethenyl decanoate Chemical compound CCCCCCCCCC(=O)OC=C CMDXMIHZUJPRHG-UHFFFAOYSA-N 0.000 description 3
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 3
- UJRIYYLGNDXVTA-UHFFFAOYSA-N ethenyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OC=C UJRIYYLGNDXVTA-UHFFFAOYSA-N 0.000 description 3
- AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000000199 molecular distillation Methods 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 2
- 229920002271 DEAE-Sepharose Polymers 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 235000020778 linoleic acid Nutrition 0.000 description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 2
- 229960004488 linolenic acid Drugs 0.000 description 2
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- AFSHUZFNMVJNKX-CLFAGFIQSA-N 1,2-dioleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCC\C=C/CCCCCCCC AFSHUZFNMVJNKX-CLFAGFIQSA-N 0.000 description 1
- DRAWQKGUORNASA-CLFAGFIQSA-N 1,3-dioleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)COC(=O)CCCCCCC\C=C/CCCCCCCC DRAWQKGUORNASA-CLFAGFIQSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- DRAWQKGUORNASA-UHFFFAOYSA-N Anticancer Glycerol Ester PMV70P691-119 Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCC=CCCCCCCCC DRAWQKGUORNASA-UHFFFAOYSA-N 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 238000001162 G-test Methods 0.000 description 1
- 108700016170 Glycerol kinases Proteins 0.000 description 1
- 102000057621 Glycerol kinases Human genes 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 description 1
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-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
- 238000005273 aeration Methods 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 108010054790 glycerol-3-phosphate oxidase Proteins 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 229940117972 triolein Drugs 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 210000001835 viscera Anatomy 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6458—Glycerides by transesterification, e.g. interesterification, ester interchange, alcoholysis or acidolysis
-
- 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
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/02—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/06—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with glycerol
-
- 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
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6472—Glycerides containing polyunsaturated fatty acid [PUFA] residues, i.e. having two or more double bonds in their backbone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2154685 | 1985-02-06 | ||
| JP60021546A JPS61181390A (ja) | 1985-02-06 | 1985-02-06 | 酵素によるグリセライドの製造法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8600148A true NL8600148A (nl) | 1986-09-01 |
Family
ID=12057981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8600148A NL8600148A (nl) | 1985-02-06 | 1986-01-23 | Werkwijze voor het bereiden van glyceriden in aanwezigheid van lipasen. |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0191217B2 (enExample) |
| JP (1) | JPS61181390A (enExample) |
| KR (1) | KR930009511B1 (enExample) |
| DE (1) | DE3561892D1 (enExample) |
| ES (1) | ES8701832A1 (enExample) |
| NL (1) | NL8600148A (enExample) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63296698A (ja) * | 1987-05-29 | 1988-12-02 | Lion Corp | 高純度モノグリセリドの連続製造方法 |
| DE3854664T2 (de) * | 1987-10-14 | 1996-05-02 | Kao Corp | Verfahren zur Herstellung eines Polyol-Fettsäureesters und dadurch erhaltene Glyceridmischung. |
| DE3743824C2 (de) * | 1987-12-23 | 1997-03-06 | Hoechst Ag | Verfahren zur enzymatischen Racematspaltung von racemischen Alkoholen mit/in Vinylestern durch Umesterung |
| US5316927A (en) * | 1988-10-04 | 1994-05-31 | Opta Food Ingredients, Inc. | Production of monoglycerides by enzymatic transesterification |
| EP0407959A3 (en) * | 1989-07-11 | 1992-01-02 | Lion Corporation | Process for producing polyol fatty acid monoesters |
| DE3928383C1 (enExample) * | 1989-08-28 | 1991-01-24 | Henkel Kgaa, 4000 Duesseldorf, De | |
| DE3928382A1 (de) * | 1989-08-28 | 1991-03-07 | Henkel Kgaa | Verfahren zur herstellung reiner monoglyceride |
| US5677160A (en) * | 1989-10-30 | 1997-10-14 | Henkel Corporation | Fat splitting process |
| US5142072A (en) * | 1989-12-19 | 1992-08-25 | The Procter & Gamble Company | Selective esterification of long chain fatty acid monoglycerides with medium chain fatty acid anhydrides |
| US5188858A (en) * | 1991-01-18 | 1993-02-23 | The Procter & Gamble Company | Propylene glycol diesters of medium chain and long chain saturated fatty acids useful as reduced calorie cocoa butter substitutes and hard butters |
| DK166650B1 (da) * | 1991-03-15 | 1993-06-28 | Aarhus Oliefabrik As | Fedtbaser samt anvendelse af disse i kosmetiske og farmaceutiske emulsionsprodukter |
| WO1996038534A1 (en) * | 1995-05-31 | 1996-12-05 | Henkel Corporation | Improved fat splitting process |
| US6936289B2 (en) | 1995-06-07 | 2005-08-30 | Danisco A/S | Method of improving the properties of a flour dough, a flour dough improving composition and improved food products |
| ATE280221T1 (de) | 1997-04-09 | 2004-11-15 | Danisco | Verwendung von lipase zur verbesserung von teigen und backwaren |
| US6261812B1 (en) * | 1997-08-18 | 2001-07-17 | Kao Corporation | Process for producing diglycerides |
| US6025348A (en) * | 1998-04-30 | 2000-02-15 | Kao Corporation | Oil and fat composition containing phytosterol |
| JP3720194B2 (ja) * | 1998-07-09 | 2005-11-24 | 花王株式会社 | 部分グリセリドの製造法 |
| DE69904941T3 (de) | 1998-07-21 | 2008-01-31 | Danisco A/S | Lebensmittel |
| US6068997A (en) * | 1999-03-01 | 2000-05-30 | Kemin Industries, Inc. | Method for the conversion of lecithin into lysolecithin |
| KR100385625B1 (ko) * | 2000-08-08 | 2003-05-27 | 일신유화주식회사 | 고순도 디글리세리드의 분리 및 정제방법 |
| KR20020048464A (ko) * | 2000-12-16 | 2002-06-24 | 정대원 | 효소를 이용한 모노글리세리드의 선택적 제조방법 |
| CA2444960C (en) | 2001-05-18 | 2011-08-09 | Danisco A/S | Method of improving dough and bread quality |
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| US20050196766A1 (en) | 2003-12-24 | 2005-09-08 | Soe Jorn B. | Proteins |
| DE602004030000D1 (de) | 2003-01-17 | 2010-12-23 | Danisco | Verfahren zur in-situ-herstellung eines emulgators in einem nahrungsmittel |
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| BRPI0404595A (pt) * | 2004-10-26 | 2006-06-13 | Natura Cosmeticos Sa | nanoemulsão óleo-em-água, composição cosmética e produto cosmético compreendendo a mesma, processo para preparação da dita nanoemulsão |
| CA2599653A1 (en) | 2005-03-10 | 2006-09-21 | 3M Innovative Properties Company | Methods of reducing microbial contamination |
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| BRPI0608691A2 (pt) | 2005-03-10 | 2010-12-07 | 3M Innovative Properties Company | composição antimicrobiana, e, métodos para matar ou inativar microorganismos em tecido da mucosa de um mamìfero, para tratar uma lesão ou ferimento infectado, para descolonização de microorganismos, para proporcionar eficácia antimicrobiana residual sobre uma superfìcie e para tratar uma condição |
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| AU2007344910B2 (en) | 2007-01-25 | 2013-03-28 | Dupont Nutrition Biosciences Aps | Production of a lipid acyltransferase from transformed Bacillus licheniformis cells |
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| FR2945180B1 (fr) | 2009-05-07 | 2013-02-22 | Arjowiggins Security | Support d'information presentant des proprietes antivirales et son procede de fabrication |
| FR2967074B1 (fr) * | 2010-11-08 | 2013-06-28 | Arjowiggins Security | Compositions fluides aptes a former un revetement presentant des proprietes antivirales |
| CN104131045A (zh) * | 2014-08-08 | 2014-11-05 | 江西华敏粮油有限公司 | 一种甘油二酯的制备方法 |
| CA3102464C (en) * | 2018-06-05 | 2023-09-05 | Dsm Ip Assets B.V. | Process for the production of diglycerides |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5723535A (en) * | 1980-07-17 | 1982-02-06 | Sumitomo Metal Ind Ltd | Control process of raw material yard facility |
-
1985
- 1985-02-06 JP JP60021546A patent/JPS61181390A/ja active Granted
- 1985-08-14 EP EP85305796A patent/EP0191217B2/en not_active Expired - Lifetime
- 1985-08-14 DE DE8585305796T patent/DE3561892D1/de not_active Expired
- 1985-08-20 ES ES547036A patent/ES8701832A1/es not_active Expired
-
1986
- 1986-01-18 KR KR1019860000282A patent/KR930009511B1/ko not_active Expired - Fee Related
- 1986-01-23 NL NL8600148A patent/NL8600148A/nl active Search and Examination
Also Published As
| Publication number | Publication date |
|---|---|
| EP0191217B2 (en) | 1992-02-19 |
| ES8701832A1 (es) | 1986-12-01 |
| KR860006548A (ko) | 1986-09-13 |
| JPS61181390A (ja) | 1986-08-14 |
| KR930009511B1 (ko) | 1993-10-06 |
| EP0191217B1 (en) | 1988-03-16 |
| DE3561892D1 (en) | 1988-04-21 |
| JPH0412112B2 (enExample) | 1992-03-03 |
| EP0191217A1 (en) | 1986-08-20 |
| ES547036A0 (es) | 1986-12-01 |
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