CA1297822C - Hydrolysis of fats - Google Patents
Hydrolysis of fatsInfo
- Publication number
- CA1297822C CA1297822C CA000528151A CA528151A CA1297822C CA 1297822 C CA1297822 C CA 1297822C CA 000528151 A CA000528151 A CA 000528151A CA 528151 A CA528151 A CA 528151A CA 1297822 C CA1297822 C CA 1297822C
- Authority
- CA
- Canada
- Prior art keywords
- lipase
- fats
- water
- diaphragm
- vessel
- 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
- 239000003925 fat Substances 0.000 title claims abstract description 104
- 238000006460 hydrolysis reaction Methods 0.000 title claims abstract description 48
- 230000007062 hydrolysis Effects 0.000 title claims abstract description 47
- 108090001060 Lipase Proteins 0.000 claims abstract description 206
- 239000004367 Lipase Substances 0.000 claims abstract description 206
- 102000004882 Lipase Human genes 0.000 claims abstract description 205
- 235000019421 lipase Nutrition 0.000 claims abstract description 204
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 93
- 229910001868 water Inorganic materials 0.000 claims abstract description 93
- 229920000642 polymer Polymers 0.000 claims abstract description 76
- 238000000034 method Methods 0.000 claims abstract description 75
- 230000008569 process Effects 0.000 claims abstract description 59
- 239000007788 liquid Substances 0.000 claims abstract description 40
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 30
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 230000000694 effects Effects 0.000 claims abstract description 28
- 238000001179 sorption measurement Methods 0.000 claims abstract description 25
- 239000000835 fiber Substances 0.000 claims abstract description 23
- 239000007864 aqueous solution Substances 0.000 claims abstract description 19
- 239000002245 particle Substances 0.000 claims abstract description 17
- 230000003647 oxidation Effects 0.000 claims abstract description 16
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 16
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 15
- 229920000831 ionic polymer Polymers 0.000 claims abstract description 15
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 15
- 239000000725 suspension Substances 0.000 claims abstract description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 72
- 239000012071 phase Substances 0.000 claims description 57
- 239000000047 product Substances 0.000 claims description 33
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 32
- 239000000194 fatty acid Substances 0.000 claims description 32
- 229930195729 fatty acid Natural products 0.000 claims description 32
- 150000004665 fatty acids Chemical class 0.000 claims description 31
- 239000011148 porous material Substances 0.000 claims description 28
- 239000000843 powder Substances 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 239000000243 solution Substances 0.000 claims description 22
- 238000011010 flushing procedure Methods 0.000 claims description 16
- 230000001413 cellular effect Effects 0.000 claims description 15
- 238000009736 wetting Methods 0.000 claims description 15
- 239000004744 fabric Substances 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 13
- 239000008346 aqueous phase Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 230000003301 hydrolyzing effect Effects 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 239000007791 liquid phase Substances 0.000 claims description 7
- 238000011144 upstream manufacturing Methods 0.000 claims description 7
- 238000002203 pretreatment Methods 0.000 claims description 6
- 239000011800 void material Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 3
- 230000014759 maintenance of location Effects 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 238000002791 soaking Methods 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 230000000630 rising effect Effects 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 abstract description 8
- 239000012429 reaction media Substances 0.000 abstract description 4
- 229940040461 lipase Drugs 0.000 description 160
- 235000019197 fats Nutrition 0.000 description 66
- 210000000188 diaphragm Anatomy 0.000 description 37
- 238000006243 chemical reaction Methods 0.000 description 21
- 108090000790 Enzymes Proteins 0.000 description 19
- 102000004190 Enzymes Human genes 0.000 description 19
- 239000004743 Polypropylene Substances 0.000 description 19
- 229940088598 enzyme Drugs 0.000 description 19
- 229920001155 polypropylene Polymers 0.000 description 18
- 239000003921 oil Substances 0.000 description 16
- 235000019198 oils Nutrition 0.000 description 16
- 229960005150 glycerol Drugs 0.000 description 15
- 239000000758 substrate Substances 0.000 description 15
- 235000011187 glycerol Nutrition 0.000 description 14
- 229920001903 high density polyethylene Polymers 0.000 description 14
- 239000004700 high-density polyethylene Substances 0.000 description 14
- 239000004006 olive oil Substances 0.000 description 13
- 235000008390 olive oil Nutrition 0.000 description 13
- -1 iodopropyl Chemical class 0.000 description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 230000002255 enzymatic effect Effects 0.000 description 7
- 239000000872 buffer Substances 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 6
- 108010093096 Immobilized Enzymes Proteins 0.000 description 5
- 241000179532 [Candida] cylindracea Species 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000004677 Nylon Substances 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 125000005456 glyceride group Chemical group 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229920001778 nylon Polymers 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000004416 thermosoftening plastic Substances 0.000 description 4
- FWEOQOXTVHGIFQ-UHFFFAOYSA-N 8-anilinonaphthalene-1-sulfonic acid Chemical compound C=12C(S(=O)(=O)O)=CC=CC2=CC=CC=1NC1=CC=CC=C1 FWEOQOXTVHGIFQ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920003182 Surlyn® Polymers 0.000 description 3
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000005484 gravity Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 229940041669 mercury Drugs 0.000 description 3
- 210000003739 neck Anatomy 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- 239000001488 sodium phosphate Substances 0.000 description 3
- 229910000162 sodium phosphate Inorganic materials 0.000 description 3
- 235000011008 sodium phosphates Nutrition 0.000 description 3
- 235000011150 stannous chloride Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- 150000003626 triacylglycerols Chemical class 0.000 description 3
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010016825 Flushing Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 240000002129 Malva sylvestris Species 0.000 description 2
- 235000006770 Malva sylvestris Nutrition 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- 102000019280 Pancreatic lipases Human genes 0.000 description 2
- 108050006759 Pancreatic lipases Proteins 0.000 description 2
- 229920005372 Plexiglas® Polymers 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- UYXTWWCETRIEDR-UHFFFAOYSA-N Tributyrin Chemical compound CCCC(=O)OCC(OC(=O)CCC)COC(=O)CCC UYXTWWCETRIEDR-UHFFFAOYSA-N 0.000 description 2
- 229920006243 acrylic copolymer Polymers 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 235000013351 cheese Nutrition 0.000 description 2
- 230000002844 continuous effect Effects 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 235000019626 lipase activity Nutrition 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000012982 microporous membrane Substances 0.000 description 2
- 229940116369 pancreatic lipase Drugs 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- LBCHYKTUUMRFHG-UHFFFAOYSA-N 3,5-diphenyl-7-oxabicyclo[2.2.1]hepta-1(6),2,4-triene Chemical compound C=1C(C=2C=CC=CC=2)=C2OC=1C=C2C1=CC=CC=C1 LBCHYKTUUMRFHG-UHFFFAOYSA-N 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920013683 Celanese Polymers 0.000 description 1
- 244000138502 Chenopodium bonus henricus Species 0.000 description 1
- 235000008645 Chenopodium bonus henricus Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000222175 Diutina rugosa Species 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 102000029813 Gastric triacylglycerol lipase Human genes 0.000 description 1
- 241000159512 Geotrichum Species 0.000 description 1
- SHGAZHPCJJPHSC-NUEINMDLSA-N Isotretinoin Chemical group OC(=O)C=C(C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-NUEINMDLSA-N 0.000 description 1
- 235000019687 Lamb Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 241000235403 Rhizomucor miehei Species 0.000 description 1
- 240000005384 Rhizopus oryzae Species 0.000 description 1
- 235000013752 Rhizopus oryzae Nutrition 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 238000011021 bench scale process Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 108010091264 gastric triacylglycerol lipase Proteins 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N linoleic acid group Chemical group C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 230000002366 lipolytic effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 210000004379 membrane Anatomy 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000005373 porous glass Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- ZNZJJSYHZBXQSM-UHFFFAOYSA-N propane-2,2-diamine Chemical compound CC(C)(N)N ZNZJJSYHZBXQSM-UHFFFAOYSA-N 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012064 sodium phosphate buffer Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005314 unsaturated fatty acid group Chemical group 0.000 description 1
Classifications
-
- 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
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
- C11C1/04—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis
- C11C1/045—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis using enzymes or microorganisms, living or dead
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
- C12N11/02—Enzymes or microbial cells immobilised on or in an organic carrier
- C12N11/08—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a synthetic polymer
- C12N11/082—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a synthetic polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
- C12N11/02—Enzymes or microbial cells immobilised on or in an organic carrier
- C12N11/08—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a synthetic polymer
- C12N11/089—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a synthetic polymer obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C12N11/096—Polyesters; Polyamides
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Microbiology (AREA)
- Zoology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/823,114 US4629742A (en) | 1986-01-27 | 1986-01-27 | Hydrolysis of fats |
| US823,114 | 1986-01-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1297822C true CA1297822C (en) | 1992-03-24 |
Family
ID=25237837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000528151A Expired - Fee Related CA1297822C (en) | 1986-01-27 | 1987-01-26 | Hydrolysis of fats |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4629742A (enExample) |
| EP (1) | EP0232933B2 (enExample) |
| JP (1) | JPS62179388A (enExample) |
| AT (1) | ATE74966T1 (enExample) |
| CA (1) | CA1297822C (enExample) |
| DE (1) | DE3778176D1 (enExample) |
| ES (1) | ES2032431T5 (enExample) |
| GR (2) | GR3005178T3 (enExample) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8600245D0 (en) * | 1986-01-07 | 1986-02-12 | Shell Int Research | Preparation of 2-arylpropionic acids |
| US4678580A (en) * | 1986-01-27 | 1987-07-07 | Akzo America Inc. | Hydrolysis of fats |
| IN171359B (enExample) * | 1986-09-17 | 1992-09-19 | Colgate Palmolive Co | |
| ATE131206T1 (de) * | 1987-10-13 | 1995-12-15 | Lubrizol Corp | Verfahren zur herstellung von hochreiner ölsäure durch hydrolyse von sonnenblumenkernöl. |
| DE3737335A1 (de) * | 1987-11-04 | 1989-05-18 | Basf Ag | Verfahren zur herstellung eines biokatalysators und dessen verwendung zur razematspaltung |
| GB8729889D0 (en) * | 1987-12-22 | 1988-02-03 | Unilever Plc | Bio-catalysts support systems |
| GB8729890D0 (en) * | 1987-12-22 | 1988-02-03 | Unilever Plc | Improvements in & relating to fat processes |
| DE3819467A1 (de) * | 1988-06-08 | 1989-12-14 | Basf Ag | Verfahren zur herstellung eines biokatalysators und dessen verwendung zur razematspaltung |
| DK111589D0 (da) * | 1989-03-08 | 1989-03-08 | Novo Industri As | Fat hydrolysis process |
| FR2647807A1 (fr) * | 1989-06-01 | 1990-12-07 | Elf Aquitaine | Catalyseur enzymatique pour l'hydrolyse ou la synthese de la liaison ester |
| DK306189D0 (da) * | 1989-06-21 | 1989-06-21 | Novo Nordisk As | Immobiliseret lipasepraeparat og anvendelse deraf til estersyntese |
| WO1991006661A1 (en) * | 1989-11-03 | 1991-05-16 | Opta Food Ingredients, Inc. | Lipase-catalyzed in situ generation of mono- and di-glycerides |
| US5395629A (en) * | 1992-11-12 | 1995-03-07 | Nestec S.A. | Preparation of butterfat and vegetable butter substitutes |
| JPH08511159A (ja) * | 1993-05-20 | 1996-11-26 | ロダース・クロックラーン・ビー・ブイ | 固定化リパーゼ |
| WO1995033047A1 (en) * | 1994-05-26 | 1995-12-07 | Novo Nordisk A/S | Method for reusing a carrier for lipase immobilization |
| US5583162A (en) * | 1994-06-06 | 1996-12-10 | Biopore Corporation | Polymeric microbeads and method of preparation |
| EP0835304A1 (en) * | 1995-06-27 | 1998-04-15 | Unilever N.V. | Immobilized enzyme and its use for the processing of triglyceride oils |
| JPH09296197A (ja) * | 1996-04-22 | 1997-11-18 | Novo Nordisk As | 油脂の脱水、精製法 |
| US6048908A (en) * | 1997-06-27 | 2000-04-11 | Biopore Corporation | Hydrophilic polymeric material |
| DE19931847A1 (de) | 1999-07-09 | 2001-01-11 | Basf Ag | Immobilisierte Lipase |
| BR0303436A (pt) * | 2002-09-06 | 2004-09-08 | Kao Corp | Processo de regenaração de enzima imobilizada |
| JP4849967B2 (ja) * | 2005-06-21 | 2012-01-11 | 花王株式会社 | 脂肪酸類の製造方法 |
| KR101294474B1 (ko) * | 2005-10-05 | 2013-08-07 | 카오카부시키가이샤 | 고정화 효소를 이용한 유용 물질의 제조 방법 |
| EP1840203A1 (en) * | 2006-03-31 | 2007-10-03 | Cargill, Inc. | Enzymatic modification in a continuously regenerated packed bed column |
| UA97127C2 (uk) | 2006-12-06 | 2012-01-10 | Бандж Ойлз, Инк. | Спосіб безперервної ферментативної обробки композиції, що містить ліпід, та система для його здійснення |
| US8252560B2 (en) * | 2006-12-15 | 2012-08-28 | Kao Corporation | Process for producing useful substance with immobilized enzyme |
| JP4915732B2 (ja) * | 2006-12-15 | 2012-04-11 | 花王株式会社 | 固定化酵素を用いた有用物質の製造方法 |
| US8889373B2 (en) | 2010-08-12 | 2014-11-18 | Eastman Chemical Company | Enzyme catalyst immobilized on porous fluoropolymer support |
| BR112014018682A8 (pt) * | 2012-01-30 | 2017-07-11 | Mallinath Lali Arvind | Processo para produção de ácidos graxos, sn-regio mono-acilglicerol (mag), sn- regio diacil-gliceróis (dag) e glicerol; e processo para produção de ácidos graxos e glicerol |
| IL313986B1 (en) | 2012-02-17 | 2026-05-01 | Alcresta Inc | Methods, compositions and devices for supplying dietary fatty acid needs |
| CA2836956C (en) | 2012-12-19 | 2020-07-21 | Potters Industries, Llc | Method and system for marking a transportation corridor |
| EP3502247B1 (en) | 2014-05-20 | 2025-11-19 | Bunge Loders Croklaan B.V. | Process for immobilization of a lipase |
| US10258590B2 (en) | 2015-10-14 | 2019-04-16 | Alcresta Therapeutics, Inc. | Enteral feeding device and related methods of use |
| US11045396B2 (en) | 2017-08-17 | 2021-06-29 | Alcresta Therapeutics, Inc. | Devices and methods for the supplementation of a nutritional formula |
| CA3253720A1 (en) | 2022-04-20 | 2023-10-26 | Novozymes A/S | PROCESS FOR PRODUCING FREE FATTY ACIDS |
| DE202022105549U1 (de) | 2022-09-30 | 2024-02-08 | Emsland-Stärke Gesellschaft mit beschränkter Haftung | Natives funktionales Kartoffelprotein |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL51672A0 (en) * | 1976-04-05 | 1977-05-31 | Miles Lab | Process and apparatus for carrying out enzymatic reactions in serially connected reactors |
-
1986
- 1986-01-27 US US06/823,114 patent/US4629742A/en not_active Expired - Lifetime
-
1987
- 1987-01-21 ES ES87200089T patent/ES2032431T5/es not_active Expired - Lifetime
- 1987-01-21 AT AT87200089T patent/ATE74966T1/de not_active IP Right Cessation
- 1987-01-21 EP EP87200089A patent/EP0232933B2/en not_active Expired - Lifetime
- 1987-01-21 DE DE8787200089T patent/DE3778176D1/de not_active Expired - Lifetime
- 1987-01-23 JP JP62012598A patent/JPS62179388A/ja active Granted
- 1987-01-26 CA CA000528151A patent/CA1297822C/en not_active Expired - Fee Related
-
1992
- 1992-07-15 GR GR920401524T patent/GR3005178T3/el unknown
-
1995
- 1995-03-01 GR GR950400443T patent/GR3015235T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE74966T1 (de) | 1992-05-15 |
| JPS62179388A (ja) | 1987-08-06 |
| JPH053274B2 (enExample) | 1993-01-14 |
| EP0232933A1 (en) | 1987-08-19 |
| GR3015235T3 (en) | 1995-06-30 |
| EP0232933B1 (en) | 1992-04-15 |
| GR3005178T3 (en) | 1993-05-24 |
| ES2032431T3 (es) | 1993-02-16 |
| EP0232933B2 (en) | 1994-12-07 |
| DE3778176D1 (de) | 1992-05-21 |
| ES2032431T5 (es) | 1995-08-16 |
| US4629742A (en) | 1986-12-16 |
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