CA2873378C - Lipase in short-chain esterification of fatty acids - Google Patents
Lipase in short-chain esterification of fatty acids Download PDFInfo
- Publication number
- CA2873378C CA2873378C CA2873378A CA2873378A CA2873378C CA 2873378 C CA2873378 C CA 2873378C CA 2873378 A CA2873378 A CA 2873378A CA 2873378 A CA2873378 A CA 2873378A CA 2873378 C CA2873378 C CA 2873378C
- Authority
- CA
- Canada
- Prior art keywords
- fatty acids
- fatty acid
- patatin
- methanol
- feed stock
- 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.)
- Active
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 102
- 239000000194 fatty acid Substances 0.000 title claims abstract description 102
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 102
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 78
- 108090001060 Lipase Proteins 0.000 title abstract description 26
- 102000004882 Lipase Human genes 0.000 title abstract description 26
- 239000004367 Lipase Substances 0.000 title abstract description 22
- 238000005886 esterification reaction Methods 0.000 title abstract description 18
- 235000019421 lipase Nutrition 0.000 title abstract description 17
- 230000032050 esterification Effects 0.000 title description 10
- 101710091688 Patatin Proteins 0.000 claims abstract description 63
- 238000000034 method Methods 0.000 claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 96
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 75
- 150000001298 alcohols Chemical class 0.000 claims description 29
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 15
- 150000004667 medium chain fatty acids Chemical class 0.000 claims description 8
- 150000004666 short chain fatty acids Chemical class 0.000 claims description 8
- 239000003225 biodiesel Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 125000004494 ethyl ester group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 244000061456 Solanum tuberosum Species 0.000 abstract description 26
- 235000002595 Solanum tuberosum Nutrition 0.000 abstract description 26
- 235000019626 lipase activity Nutrition 0.000 abstract description 4
- 235000012015 potatoes Nutrition 0.000 abstract 1
- 102000004169 proteins and genes Human genes 0.000 description 22
- 108090000623 proteins and genes Proteins 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000012429 reaction media Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 17
- 235000021588 free fatty acids Nutrition 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 150000003904 phospholipids Chemical class 0.000 description 14
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- 239000012535 impurity Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical class OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000005639 Lauric acid Substances 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 239000003463 adsorbent Substances 0.000 description 6
- 238000000855 fermentation Methods 0.000 description 6
- 230000004151 fermentation Effects 0.000 description 6
- 235000015203 fruit juice Nutrition 0.000 description 6
- 230000009257 reactivity Effects 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000003925 fat Substances 0.000 description 4
- 235000019197 fats Nutrition 0.000 description 4
- -1 fatty acid esters Chemical class 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 102000003886 Glycoproteins Human genes 0.000 description 3
- 108090000288 Glycoproteins Proteins 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 238000005377 adsorption chromatography Methods 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 150000004668 long chain fatty acids Chemical class 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 235000021391 short chain fatty acids Nutrition 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 230000002051 biphasic effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000011143 downstream manufacturing Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000005189 flocculation Methods 0.000 description 2
- 230000016615 flocculation Effects 0.000 description 2
- 229930008677 glyco alkaloid Natural products 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- JGHZJRVDZXSNKQ-UHFFFAOYSA-N methyl octanoate Chemical compound CCCCCCCC(=O)OC JGHZJRVDZXSNKQ-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 108091075678 patatin family Proteins 0.000 description 2
- 239000001814 pectin Substances 0.000 description 2
- 229920001277 pectin Polymers 0.000 description 2
- 235000010987 pectin Nutrition 0.000 description 2
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 150000004669 very long chain fatty acids Chemical class 0.000 description 2
- ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 208000016444 Benign adult familial myoclonic epilepsy Diseases 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 102000004157 Hydrolases Human genes 0.000 description 1
- 108090000604 Hydrolases Proteins 0.000 description 1
- 239000005641 Methyl octanoate Substances 0.000 description 1
- 108010084311 Novozyme 435 Proteins 0.000 description 1
- 102000015439 Phospholipases Human genes 0.000 description 1
- 108010064785 Phospholipases Proteins 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical class [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 1
- 229920002684 Sepharose Polymers 0.000 description 1
- 241000519995 Stachys sylvatica Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- SUHOQUVVVLNYQR-MRVPVSSYSA-N choline alfoscerate Chemical compound C[N+](C)(C)CCOP([O-])(=O)OC[C@H](O)CO SUHOQUVVVLNYQR-MRVPVSSYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 208000016427 familial adult myoclonic epilepsy Diseases 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 244000144992 flock Species 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 229960004956 glycerylphosphorylcholine Drugs 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000002366 lipolytic effect Effects 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002417 nutraceutical Substances 0.000 description 1
- 235000021436 nutraceutical agent Nutrition 0.000 description 1
- MYSFLUCHHGIXIT-UHFFFAOYSA-N octanoic acid;hydrate Chemical compound O.CCCCCCCC(O)=O MYSFLUCHHGIXIT-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- DVDUMIQZEUTAGK-UHFFFAOYSA-N p-nitrophenyl butyrate Chemical compound CCCC(=O)OC1=CC=C([N+]([O-])=O)C=C1 DVDUMIQZEUTAGK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING OR TREATMENT THEREOF
- A23C19/00—Cheese; Cheese preparations; Making thereof
- A23C19/06—Treating cheese curd after whey separation; Products obtained thereby
- A23C19/09—Other cheese preparations; Mixtures of cheese with other foodstuffs
- A23C19/0921—Addition, to cheese or curd, of minerals, including organic salts thereof, trace elements, amino acids, peptides, protein hydrolysates, nucleic acids, yeast extracts or autolysate, vitamins or derivatives of these compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING OR TREATMENT THEREOF
- A23C19/00—Cheese; Cheese preparations; Making thereof
- A23C19/02—Making cheese curd
- A23C19/04—Making cheese curd characterised by the use of specific enzymes of vegetable or animal origin
- A23C19/043—Enzymes other than proteolytic enzymes or milk clotting enzymes, e.g. lipase, lysosyme
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING OR TREATMENT THEREOF
- A23C19/00—Cheese; Cheese preparations; Making thereof
- A23C19/02—Making cheese curd
- A23C19/05—Treating milk before coagulation; Separating whey from curd
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING OR TREATMENT THEREOF
- A23C19/00—Cheese; Cheese preparations; Making thereof
- A23C19/06—Treating cheese curd after whey separation; Products obtained thereby
- A23C19/063—Addition of, or treatment with, enzymes or cell-free extracts of microorganisms
-
- 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
-
- 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
- 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
-
- 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
-
- 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
- C12P7/649—Biodiesel, i.e. fatty acid alkyl esters
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y301/00—Hydrolases acting on ester bonds (3.1)
- C12Y301/01—Carboxylic ester hydrolases (3.1.1)
- C12Y301/01003—Triacylglycerol lipase (3.1.1.3)
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Biotechnology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Nutrition Science (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Dairy Products (AREA)
- Seasonings (AREA)
- Fats And Perfumes (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Fruits And Vegetables (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12174894 | 2012-07-04 | ||
| EP12174894.1 | 2012-07-04 | ||
| PCT/NL2013/050489 WO2014007622A1 (en) | 2012-07-04 | 2013-07-03 | Lipase in short-chain esterification of fatty acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2873378A1 CA2873378A1 (en) | 2014-01-09 |
| CA2873378C true CA2873378C (en) | 2020-01-14 |
Family
ID=48833028
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2873378A Active CA2873378C (en) | 2012-07-04 | 2013-07-03 | Lipase in short-chain esterification of fatty acids |
| CA2873366A Active CA2873366C (en) | 2012-07-04 | 2013-07-03 | Methods using patatin |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2873366A Active CA2873366C (en) | 2012-07-04 | 2013-07-03 | Methods using patatin |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US20150189896A1 (enExample) |
| EP (2) | EP2870252B1 (enExample) |
| JP (2) | JP6230601B2 (enExample) |
| CN (2) | CN104428419A (enExample) |
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| WO2016067804A1 (ja) * | 2014-10-30 | 2016-05-06 | 不二製油グループ本社株式会社 | 長鎖多価不飽和脂肪酸含有油脂およびそれを含有する食品 |
| ES2747912T3 (es) | 2015-11-06 | 2020-03-12 | Cooperatie Avebe U A | Fermentación |
| EP3213638A1 (en) * | 2016-03-01 | 2017-09-06 | Coöperatie Avebe U.A. | Vegan cheese analogue |
| CA3237785A1 (en) | 2017-03-31 | 2018-10-04 | J.R. Simplot Company | Potato protein powders |
| EP3578630B1 (en) | 2018-06-04 | 2020-12-02 | The Procter & Gamble Company | Liquid detergent composition |
| AU2021316071B2 (en) * | 2020-07-30 | 2024-05-16 | Coöperatie Koninklijke Avebe U.A. | Patatin as binder in meat substitutes |
| EP3944769B1 (en) | 2020-07-30 | 2025-09-03 | Coöperatie Koninklijke Avebe U.A. | Patatin as binder in meat substitutes |
| JP2024508521A (ja) * | 2021-03-02 | 2024-02-27 | コオペラティ・コーニンクレッカ・アヴェベ・ユー・エイ | パタチン乳化結合剤 |
| EP4376623A1 (en) | 2021-07-29 | 2024-06-05 | Coöperatie Koninklijke Avebe U.A. | Patatin as binder in food products other than meat substitutes |
| WO2023080785A1 (en) | 2021-11-03 | 2023-05-11 | Coöperatie Koninklijke Avebe U.A. | Patatin inhibition |
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| US6398707B1 (en) | 2001-05-31 | 2002-06-04 | Wen-Teng Wu | Method of preparing lower alkyl fatty acids esters and in particular biodiesel |
| US7943360B2 (en) * | 2002-04-19 | 2011-05-17 | Verenium Corporation | Phospholipases, nucleic acids encoding them and methods for making and using them |
| US7226771B2 (en) * | 2002-04-19 | 2007-06-05 | Diversa Corporation | Phospholipases, nucleic acids encoding them and methods for making and using them |
| CA2515583C (en) * | 2003-03-07 | 2015-07-14 | Diversa Corporation | Hydrolases, nucleic acids encoding them and methods for making and using them |
| EP1920662A1 (en) | 2006-11-10 | 2008-05-14 | Coöperatie Avebe U.A. | Native potato protein isolates |
| US8486481B2 (en) * | 2006-11-10 | 2013-07-16 | Coöperatie Avebe U.A. | Glycoalkaloid removal |
| CA2716692A1 (en) * | 2008-02-29 | 2009-09-03 | Dsm Ip Assets B.V. | Lipases with high specificity towards short chain fatty acids and uses thereof |
| DK2406372T3 (da) * | 2009-03-10 | 2017-11-27 | Dsm Ip Assets Bv | Prægastrisk esterase og derivater deraf |
| JP2011148874A (ja) * | 2010-01-20 | 2011-08-04 | Daiki Axis:Kk | 脂肪酸アルキルエステルの製造方法とその製造装置 |
| JP5756972B2 (ja) * | 2010-02-24 | 2015-07-29 | 国立研究開発法人産業技術総合研究所 | バイオディーゼル燃料の製造方法及びバイオディーゼル燃料組成物 |
| US20110211679A1 (en) * | 2010-02-26 | 2011-09-01 | Vladimir Mezhibovsky | Voice Response Processing |
| CN102947456A (zh) | 2010-06-18 | 2013-02-27 | 布特马斯先进生物燃料有限责任公司 | 补充脂肪酸以改善醇产量 |
| AU2011268220B2 (en) * | 2010-06-18 | 2015-01-29 | Butamax(Tm) Advanced Biofuels Llc | Extraction solvents derived from oil for alcohol removal in extractive fermentation |
| JP5793288B2 (ja) * | 2010-09-30 | 2015-10-14 | 綱 秀 典 金 | バイオ石油燃料製造方法と、それに使用する触媒および製造システム |
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| MX357703B (es) | 2018-07-20 |
| JP2015521845A (ja) | 2015-08-03 |
| MX2014014866A (es) | 2015-04-08 |
| PL2870252T3 (pl) | 2020-07-13 |
| EA025269B9 (ru) | 2017-03-31 |
| EP2870253A1 (en) | 2015-05-13 |
| CN104428420B (zh) | 2018-06-01 |
| WO2014007622A1 (en) | 2014-01-09 |
| JP6231091B2 (ja) | 2017-11-15 |
| EA025269B1 (ru) | 2016-12-30 |
| BR112014032741B1 (pt) | 2022-01-25 |
| EA201491987A1 (ru) | 2015-06-30 |
| EP2870252B1 (en) | 2020-01-22 |
| WO2014007621A1 (en) | 2014-01-09 |
| CA2873378A1 (en) | 2014-01-09 |
| US20150140618A1 (en) | 2015-05-21 |
| EP2870252A1 (en) | 2015-05-13 |
| MX362234B (es) | 2019-01-09 |
| EA027459B1 (ru) | 2017-07-31 |
| CA2873366C (en) | 2021-06-15 |
| JP2015527060A (ja) | 2015-09-17 |
| US20150189896A1 (en) | 2015-07-09 |
| BR112014032171A2 (pt) | 2017-06-27 |
| EA201491986A1 (ru) | 2015-05-29 |
| MX2014014876A (es) | 2015-03-09 |
| DK2870252T3 (da) | 2020-03-16 |
| US10034485B2 (en) | 2018-07-31 |
| CN104428420A (zh) | 2015-03-18 |
| CN104428419A (zh) | 2015-03-18 |
| BR112014032741A2 (pt) | 2017-06-27 |
| CA2873366A1 (en) | 2014-01-09 |
| JP6230601B2 (ja) | 2017-11-15 |
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