WO2012050422A1 - Process for production of diacylglycerol-enriched oil or fat - Google Patents
Process for production of diacylglycerol-enriched oil or fat Download PDFInfo
- Publication number
- WO2012050422A1 WO2012050422A1 PCT/MY2011/000187 MY2011000187W WO2012050422A1 WO 2012050422 A1 WO2012050422 A1 WO 2012050422A1 MY 2011000187 W MY2011000187 W MY 2011000187W WO 2012050422 A1 WO2012050422 A1 WO 2012050422A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oil
- glycerol
- reaction mixture
- process according
- weight
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 78
- 150000001982 diacylglycerols Chemical class 0.000 title abstract description 37
- 238000004519 manufacturing process Methods 0.000 title description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 127
- 239000011541 reaction mixture Substances 0.000 claims abstract description 53
- 108090001060 Lipase Proteins 0.000 claims abstract description 50
- 102000004882 Lipase Human genes 0.000 claims abstract description 50
- 239000004367 Lipase Substances 0.000 claims abstract description 50
- 235000019421 lipase Nutrition 0.000 claims abstract description 50
- 238000002360 preparation method Methods 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000006227 byproduct Substances 0.000 claims abstract description 12
- 239000000463 material Substances 0.000 claims abstract description 5
- 239000003921 oil Substances 0.000 claims description 57
- 235000019198 oils Nutrition 0.000 claims description 57
- 239000003925 fat Substances 0.000 claims description 47
- 235000019197 fats Nutrition 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 24
- 235000021588 free fatty acids Nutrition 0.000 claims description 18
- 150000002759 monoacylglycerols Chemical class 0.000 claims description 16
- CMDGQTVYVAKDNA-UHFFFAOYSA-N propane-1,2,3-triol;hydrate Chemical compound O.OCC(O)CO CMDGQTVYVAKDNA-UHFFFAOYSA-N 0.000 claims description 16
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 9
- 239000012052 hydrophilic carrier Substances 0.000 claims description 6
- 230000018044 dehydration Effects 0.000 claims description 5
- 238000006297 dehydration reaction Methods 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000010775 animal oil Substances 0.000 claims description 3
- 239000008158 vegetable oil Substances 0.000 claims description 3
- 241000228212 Aspergillus Species 0.000 claims description 2
- 241000228245 Aspergillus niger Species 0.000 claims description 2
- 241000235395 Mucor Species 0.000 claims description 2
- 241000498617 Mucor javanicus Species 0.000 claims description 2
- 241000235403 Rhizomucor miehei Species 0.000 claims description 2
- 241000235527 Rhizopus Species 0.000 claims description 2
- 241000303962 Rhizopus delemar Species 0.000 claims description 2
- 241000235545 Rhizopus niveus Species 0.000 claims description 2
- 240000005384 Rhizopus oryzae Species 0.000 claims description 2
- 230000003100 immobilizing effect Effects 0.000 claims description 2
- 244000005700 microbiome Species 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 230000003393 splenic effect Effects 0.000 claims 1
- 235000019871 vegetable fat Nutrition 0.000 claims 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 13
- 108010048733 Lipozyme Proteins 0.000 description 10
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 description 10
- 150000003626 triacylglycerols Chemical class 0.000 description 5
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 239000008157 edible vegetable oil Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 230000002779 inactivation Effects 0.000 description 3
- 239000010466 nut oil Substances 0.000 description 3
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- CNVZJPUDSLNTQU-SEYXRHQNSA-N petroselinic acid Chemical compound CCCCCCCCCCC\C=C/CCCCC(O)=O CNVZJPUDSLNTQU-SEYXRHQNSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- GWHCXVQVJPWHRF-KTKRTIGZSA-N (15Z)-tetracosenoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O GWHCXVQVJPWHRF-KTKRTIGZSA-N 0.000 description 1
- YUFFSWGQGVEMMI-JLNKQSITSA-N (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O YUFFSWGQGVEMMI-JLNKQSITSA-N 0.000 description 1
- TWSWSIQAPQLDBP-CGRWFSSPSA-N (7e,10e,13e,16e)-docosa-7,10,13,16-tetraenoic acid Chemical compound CCCCC\C=C\C\C=C\C\C=C\C\C=C\CCCCCC(O)=O TWSWSIQAPQLDBP-CGRWFSSPSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- OXEDXHIBHVMDST-UHFFFAOYSA-N 12Z-octadecenoic acid Natural products CCCCCC=CCCCCCCCCCCC(O)=O OXEDXHIBHVMDST-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- YWWVWXASSLXJHU-UHFFFAOYSA-N 9E-tetradecenoic acid Natural products CCCCC=CCCCCCCCC(O)=O YWWVWXASSLXJHU-UHFFFAOYSA-N 0.000 description 1
- 235000009434 Actinidia chinensis Nutrition 0.000 description 1
- 244000298697 Actinidia deliciosa Species 0.000 description 1
- 235000009436 Actinidia deliciosa Nutrition 0.000 description 1
- 235000003320 Adansonia digitata Nutrition 0.000 description 1
- 244000056971 Adansonia gregorii Species 0.000 description 1
- 235000003319 Adansonia gregorii Nutrition 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- 235000011437 Amygdalus communis Nutrition 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
- 244000226021 Anacardium occidentale Species 0.000 description 1
- 241001673904 Argania Species 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- 235000012284 Bertholletia excelsa Nutrition 0.000 description 1
- 244000205479 Bertholletia excelsa Species 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- 235000004936 Bromus mango Nutrition 0.000 description 1
- 241000589513 Burkholderia cepacia Species 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- 241000222175 Diutina rugosa Species 0.000 description 1
- 235000021294 Docosapentaenoic acid Nutrition 0.000 description 1
- 235000021292 Docosatetraenoic acid Nutrition 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- OPGOLNDOMSBSCW-CLNHMMGSSA-N Fursultiamine hydrochloride Chemical compound Cl.C1CCOC1CSSC(\CCO)=C(/C)N(C=O)CC1=CN=C(C)N=C1N OPGOLNDOMSBSCW-CLNHMMGSSA-N 0.000 description 1
- 235000003239 Guizotia abyssinica Nutrition 0.000 description 1
- 240000002795 Guizotia abyssinica Species 0.000 description 1
- 235000019487 Hazelnut oil Nutrition 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 235000018330 Macadamia integrifolia Nutrition 0.000 description 1
- 235000003800 Macadamia tetraphylla Nutrition 0.000 description 1
- 240000000912 Macadamia tetraphylla Species 0.000 description 1
- 235000014826 Mangifera indica Nutrition 0.000 description 1
- 240000007228 Mangifera indica Species 0.000 description 1
- 241001661345 Moesziomyces antarcticus Species 0.000 description 1
- 244000183331 Nephelium lappaceum Species 0.000 description 1
- XJXROGWVRIJYMO-SJDLZYGOSA-N Nervonic acid Natural products O=C(O)[C@@H](/C=C/CCCCCCCC)CCCCCCCCCCCC XJXROGWVRIJYMO-SJDLZYGOSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- 235000004347 Perilla Nutrition 0.000 description 1
- 244000124853 Perilla frutescens Species 0.000 description 1
- CNVZJPUDSLNTQU-UHFFFAOYSA-N Petroselaidic acid Natural products CCCCCCCCCCCC=CCCCCC(O)=O CNVZJPUDSLNTQU-UHFFFAOYSA-N 0.000 description 1
- 235000019497 Pistachio oil Nutrition 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 235000019774 Rice Bran oil Nutrition 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- 235000009184 Spondias indica Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 1
- 235000019498 Walnut oil Nutrition 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
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- TWSWSIQAPQLDBP-UHFFFAOYSA-N adrenic acid Natural products CCCCCC=CCC=CCC=CCC=CCCCCCC(O)=O TWSWSIQAPQLDBP-UHFFFAOYSA-N 0.000 description 1
- 238000005377 adsorption chromatography Methods 0.000 description 1
- 229940108929 alfalfa oil Drugs 0.000 description 1
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021302 avocado oil Nutrition 0.000 description 1
- 239000008163 avocado oil Substances 0.000 description 1
- 239000010480 babassu oil Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000010473 blackcurrant seed oil Substances 0.000 description 1
- 235000021324 borage oil Nutrition 0.000 description 1
- 239000010495 camellia oil Substances 0.000 description 1
- 235000019519 canola oil Nutrition 0.000 description 1
- 239000000828 canola oil Substances 0.000 description 1
- 235000013709 carrot oil Nutrition 0.000 description 1
- 235000020226 cashew nut Nutrition 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- GWHCXVQVJPWHRF-UHFFFAOYSA-N cis-tetracosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCCCCCC(O)=O GWHCXVQVJPWHRF-UHFFFAOYSA-N 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- HOBAELRKJCKHQD-QNEBEIHSSA-N dihomo-γ-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(O)=O HOBAELRKJCKHQD-QNEBEIHSSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 1
- 229940090949 docosahexaenoic acid Drugs 0.000 description 1
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 1
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 1
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 235000008524 evening primrose extract Nutrition 0.000 description 1
- 239000010475 evening primrose oil Substances 0.000 description 1
- 229940089020 evening primrose oil Drugs 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- LQJBNNIYVWPHFW-QXMHVHEDSA-N gadoleic acid Chemical compound CCCCCCCCCC\C=C/CCCCCCCC(O)=O LQJBNNIYVWPHFW-QXMHVHEDSA-N 0.000 description 1
- VZCCETWTMQHEPK-UHFFFAOYSA-N gamma-Linolensaeure Natural products CCCCCC=CCC=CCC=CCCCCC(O)=O VZCCETWTMQHEPK-UHFFFAOYSA-N 0.000 description 1
- VZCCETWTMQHEPK-QNEBEIHSSA-N gamma-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O VZCCETWTMQHEPK-QNEBEIHSSA-N 0.000 description 1
- 235000020664 gamma-linolenic acid Nutrition 0.000 description 1
- 229960002733 gamolenic acid Drugs 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 239000008169 grapeseed oil Substances 0.000 description 1
- 239000010468 hazelnut oil Substances 0.000 description 1
- 239000010460 hemp oil Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000010507 melon oil Substances 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 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
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000010471 pistachio oil Substances 0.000 description 1
- 229940082415 pistachio oil Drugs 0.000 description 1
- 239000010491 poppyseed oil Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000001944 prunus armeniaca kernel oil Substances 0.000 description 1
- 239000008171 pumpkin seed oil Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 235000007861 rambutan Nutrition 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000008165 rice bran oil Substances 0.000 description 1
- 239000010667 rosehip oil Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- JIWBIWFOSCKQMA-UHFFFAOYSA-N stearidonic acid Natural products CCC=CCC=CCC=CCC=CCCCCC(O)=O JIWBIWFOSCKQMA-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 239000003760 tallow Substances 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
- AQWHMKSIVLSRNY-UHFFFAOYSA-N trans-Octadec-5-ensaeure Natural products CCCCCCCCCCCCC=CCCCC(O)=O AQWHMKSIVLSRNY-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000008170 walnut oil Substances 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- DTOSIQBPPRVQHS-UHFFFAOYSA-N α-Linolenic acid Chemical compound CCC=CCC=CCC=CCCCCCCCC(O)=O DTOSIQBPPRVQHS-UHFFFAOYSA-N 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
-
- 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
- C11B3/003—Refining fats or fatty oils by 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
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/16—Hydrolases (3) acting on ester bonds (3.1)
- C12N9/18—Carboxylic ester hydrolases (3.1.1)
- C12N9/20—Triglyceride splitting, e.g. by means of lipase
-
- 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
Definitions
- the present invention relates to a process for producing diacylglycerol-enriched fat or oil. More particularly, the present invention relates to a process for producing a diacylglycerol-enriched fat or oil containing reduced amount of impurities.
- a fat or oil containing a high concentration of diacylglycerol (hereinafter is referred to as a "diacylglycerol-enriched fat or oil”) is known to have advantageous pharmacological properties such as a body fat burning action in the human body. Therefore diacylglycerol-enriched fat or oil has been widely used as an edible oil.
- diacylglycerol can be produced by several processes, including esterification; transesterification; glycerolysis; and partial hydrolysis. These processes may be carried out with the use of a chemical alkaline catalyst, or the like; or an fatty acid-reacting enzyme catalyst such as a lipase, or the like. From the viewpoints of product purity, consumer acceptance and energy consumption, the enzymatic process is more generally used.
- diacylglycerol-enriched fats or oils produced by such methods contain impurities, such as free fatty acids, monoacylglycerols and other components.
- impurities such as free fatty acids, monoacylglycerols and other components.
- WO2007/075079 titled “Process for the Production of Diacylglycerol” published on 5 July 2007 discloses a partial hydrolysis process for producing diacylglycerol by reacting triacyiglycerol with water, in the presence of a 1 ,3-position specific immobilized lipase. In this process, a precise control of water is required to obtain an optimal diacylglycerol yield. However, a relatively high amount of free fatty acids, in an amount of 30 to 35% by weight are also generated as by-products in the process. Removal of this high amount of by-products generated by this process is not cost effective. US Pat. No.
- the disclosed process needs to be conducted at a low temperature, in the range of 0 to 25°C, in order to allow crystallization of free fatty acids and monoacylglycerols to take place. Furthermore, the disclosed process also requires long reaction time, of about 10 to 200 hours. This leads to higher operating costs.
- WO03/029392 titled “Chemical Process for the Production of 1 ,3-diglyceride Oils", published on 10 April 2003 discloses a glycerolysis process for producing diacylglycerol by reacting triacylglycerol with glycerol in the presence of potassium acetate as a catalyst.
- this process requires high reaction temperatures, in the range of 190 to 240°C. Exposure of the reaction mixture to such elevated temperatures may encourage formation of other undesirable compounds.
- a process for producing a diacylglycerol-enriched fat or oil in accordance with this invention It is an advantage of a process in accordance with this invention that the process provides a diacylglycerol-enriched fat or oil obtained in accordance with the process of the invention has reduced amount of free fatty acids and monoacylglycerols.
- a second advantage of this invention is that the process allows glycerolysis reaction to occur without causing any inactivation of the immobilized lipase preparation by the glycerol itself.
- the process produces a diacylglycerol-enriched fat or. oil by adding glycerol to a reaction mixture containing a fat or oil and an immobilized lipase preparation at a rate of not more than 40 parts by weight of glycerol per 100 parts by weight of the immobilized lipase preparation per hour.
- the process is performed in the following manner. The process begins by charging a reaction chamber with a fat or oil and an immobilized lipase preparation to obtain a reaction mixture. Glycerol is then added to the reaction mixture at a rate of not more than 40 parts by weight of glycerol per 100 parts by weight of the immobilized lipase preparation per hour. Water in the reaction mixture is removed by a dehydration method. Unreacted materials and by-products contained in the reaction mixture after the reaction are then separated from the reaction mixture to obtain the desired diacylglycerol-enriched fat or oil.
- additional water is added to the reaction mixture.
- the additional water is pre- mixed with glycerol to obtain a glycerol-water mixture prior to adding the glycerol-water mixture to the reaction mixture at a rate of not more than 40 parts by weight of glycerol- water mixture per 100 parts by weight of the immobilized lipase preparation per hour.
- the additional water is added in an amount of at least 0.2 parts by weight to 100 parts by weight of the immobilized lipase preparation.
- glycerol is added to the reaction mixture is in an amount of not more than 15% by weight of the fat or oil.
- the by-products produced by the process include free fatty acids and monoacylglycerols.
- the total concentration of the free fatty acids and the monoacylglycerols in the reaction mixture after the glycerol is added is preferably not more than 15% by weight of the fat or oil.
- the concentration of the free fatty acids in the reaction mixture after the glycerol is added is more preferably not more than 10% by weight of the oil or fat.
- the immobilized lipase preparation is prepared by immobilizing the lipase on a hydrophilic carrier.
- Figure 1 is a graph showing time course of the diacylglycerol production from Examples 1 to 5 and Comparative Examples 1 to 5.
- the present invention provides a cost effective and environmentally less detrimental process for producing a diacylglycerol-enriched fat or oil which has an improved degree of purification as an edible oil while retaining the biologically advantageous components of the fat or oil used in the production of the fat or oil product.
- a process for producing a diacylglycerol-enriched fat or oil whereby glycerol is added to a reaction mixture containing a fat or oil and an immobilized lipase preparation at a rate of not more than 40 parts by weight of glycerol per 100 parts by weight of the immobilized lipase preparation per hour, to obtain a mixture comprising triacylglycerol, diacylglycerol, monoacylglycerol and free fatty acids.
- the glycerol is added to the reaction mixture at a rate of from 5 to 40 parts by weight of glycerol per 100 parts by weight of the immobilised lipase preparation per hour.
- the glycerol is added to the reaction mixture in a continuous or semi-continuous manner.
- the process comprises charging a reaction chamber with a fat or oil and an immobilized lipase preparation to obtain a reaction mixture.
- Glycerol is then added to the reaction mixture at a rate of not more than 40 parts by weight of glycerol per 100 parts by weight of the immobilized lipase preparation per hour.
- Glycerol is added to the reaction mixture in a controlled manner such that glycerolysis reaction can occur without causing any inactivation of the immobilised lipase preparation by the glycerol itself.
- the process in accordance with an embodiment of this invention also comprises removing water content in the reaction mixture by a dehydration method.
- the water in the reaction mixture is removed from the reaction chamber while glycerol is added to the reaction mixture.
- the water in the reaction mixture is removed after the glycerolysis reaction is completed. Unreacted materials and by-products contained in the reaction mixture after the glycerolysis reaction is completed are then separated from the reaction mixture to obtain the desired diacylglycerol-enriched fat or oil.
- fat or oil used in the process of the present invention include crude or refined vegetable oils and/or animal oils.
- the vegetable oils may include any one of or a mixture of two or more of the following oil: canola oil, coconut oil, corn oil, cottonseed oil, palm oil, palm kernel oil, peanut oil, rapeseed oil, safflower oil, soybean oil, sunflower oil, olive oil, rice bran oil, corn bran oil, borage oil, evening primrose oil, flaxseed oil, grape seed oil, linseed oil, argania oil alfalfa oil, almond seed oil, apricot kernel oil, avocado oil, babassu oil, baobab oil, blackcurrant seed oil, brazil nut oil, cocoa seed oil, camellia oil, carrot oil, cashew nut oil, hazelnut oil, hemp seed oil, kiwi seed oil, macadamia nut oil, mango seed oil, melon seed oil, niger seed oil, peach kernel oil, perilla oil, pistachi
- the Animal oils may include beef tallow, lard, and/or fish oil.
- the fat or oil used in the process may further be fat or oil obtained from the process of hardening, hydrogenation, transesterification, or randomisation, fractionation, distillation; and mixtures thereof.
- the processed fat and oil in accordance with this invention comprises C 2 -C 2 4 saturated or unsaturated fatty acids or mixtures thereof.
- Example of such fats or oils include acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, undecanoic acid, lauric acid, myristic acid, myristoleic acid, palmitic acid, palmitoleic acid, zoomaric acid, stearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, a- linolenic acid, ⁇ -linolenic acid, stearidonic acid, arachidic acid, arachidonic acid, gadoleic acid, arachic acid, dihomo-y-linolenic acid, eicosapentaenoic acid, behenic acid, erucic acid, adrenic acid, docosapentaenoic acid, docosahexaenoic acid, or nervonic acid.
- the immobilised lipase preparation used in the present invention preferably is a lipase having immobilised onto a hydrophilic carrier.
- the hydrophilic carrier preferably is a silica gel.
- the lipase used in the present invention can be a non-position specific lipase or a I mposition specific lipase.
- lipase examples include lipases derived from microorganisms of the genera Rhizopus, Aspergillus, Mucor, Candida and Pseudomonas, more specifically, lipases derived from Rhizopus delemar, Rhizopus japonicus, Rhizopus niveus, Aspergillus niger, Mucor javanicus, Mucor miehei, Candida rugosa, Candida antarctica, Pseudomonas cepacia and the like.
- the immobilised lipase preparation is obtained by immobilising a lipase in accordance with a publicly known method for immobilising an enzyme, preferably by means of adsorption and/or absorption.
- immobilised lipase preparations that can be used in the present invention include "Lipozyme TL IM” (trade name, product of Novozymes).
- the proportion of the total glycerol added to the reaction mixture is not particularly limited.
- the glycerolysis reaction is conducted in such a manner that the proportion of the total glycerol added to the reaction mixture is not more than 15% by weight of the fat or oil used in the process, preferably from 5 to 10% by weight of the fat or oil used in the process.
- the process in accordance with this invention can be conducted in the absence or presence of additional water other than the water contained in the immobilised lipase preparation and/or the raw materials.
- the glycerolysis reaction is conducted in the presence of additional water.
- the glycerol to be added to the reaction mixture is first pre-mixed with water to obtain a glycerol-water mixture.
- the resultant glycerol-water mixture is then added to the reaction mixture at a rate of not more than 40 parts by weight of glycerol-water mixture per 100 parts by weight of the immobilized lipase preparation per hour, preferably at a rate of from 5 to 40 parts by weight of glycerol-water mixture per 100 parts by weight of the immobilised lipase preparation per hour, to obtain a mixture comprising triacylglycerol, diacylglycerol, monoacylglycerol and free fatty acids.
- the glycerolysis reaction in the process of the present invention is conducted in such a manner that the amount of water present in the reaction mixture at any point of time of the reaction is not more than 10 parts by weight to 100 parts by weight of the immobilised lipase preparation, more preferably, in an amount from 0.2 to 2 parts by weight to 100 parts by weight of the immobilised lipase preparation.
- the amount of water in the reaction mixture may change. As the amount of water increases, excess water may be removed from the reaction chamber by any known dehydration methods. In one preferred embodiment of the invention, the excess water is removed from the reaction chamber by means of reducing the pressure in the reaction chamber.
- the process in accordance with this invention is conducted at a temperature within the operational temperature of the immobilised lipase preparation.
- the glycerolysis reaction is carried out at a temperature in the range of 50°C to 90°C, more preferably, in the range of 60°C to 80°C.
- the by-products generated by the process of the present invention include free fatty acids and monoacylglycerols. These by-products can be easily separated from triacylglycerol and diacylglycerol contained in the reaction mixture after the glycerolysis reaction is completed, using standard separation techniques. These techniques include deodorisation, steam distillation, molecular distillation, adsorption chromatography, and any combination thereof. However, one skilled in the art will recognise that other separation methods may be employed without departing from the invention.
- the content of free fatty acids and monoacylglycerols in the reaction mixture after the glycerolysis reaction is not more than 15% by weight of the fat or oil used in the process.
- the content of free fatty acids in the reaction mixture after the glycerolysis reaction is not more than 10% by weight of the fat or oil used in the process.
- the diacylglycerol-enriched fat or oil produced by the process of the present invention preferably contains diacylglycerol in an amount of 25 to 60% by weight of the fat or oil used in the process.
- a higher yield of diacylglycerol is obtained by the process of the present invention.
- a yield of 45 to 55% by weight of diacylglycerol is obtained.
- the process of the present invention produces a diacylglycerol-enriched fat or oil which has an improved degree of purification as an edible oil while retaining the biologically advantageous components of the fat or oil used in the process, as the amount of undesirable by-products generated by the process is reduced. This also makes the process of the present invention more cost effective as less time and steps are required to remove the undesirable by-products.
- the process of the present invention is also more cost effective in that the process uses relatively inexpensive fats or oils as the raw materials and relatively low-cost lipase preparation as the catalyst.
- the process of the present invention also allows one to control the amount of glycerol or glycerol-water mixture to be added to the reaction mixture to allow glycerolysis reaction to occur without causing any inactivation of the immobilized lipase preparation by the glycerol itself.
- a 500 ml flask was first charged with 100g of palm olein and 10g of Lipozyme TL IM. Thereafter, 8g of glycerol were mixed with 0.08 ml of water and the resultant glycerol- water mixture was added at a rate of 1.6g glycerol/hour. The reaction mixture was reacted at 70°C for 8 hours. During the course of the reaction, samples were taken from the reaction mixture at 1 hour interval. The samples were then analysed for free fatty acids, monoacylglycerols (MAG), diacylglycerols (DAG) and triacylglycerols (TAG) by using high performance liquid chromatography. The results are shown in Table 2.
- MAG monoacylglycerols
- DAG diacylglycerols
- TAG triacylglycerols
- a 500ml flask was first charged with 100g of palm olein and 10g of Lipozyme TL IM. Thereafter, 8g of glycerol were mixed with 0.08ml of water and the resultant glycerol- water mixture was added all at once at the start of the reaction. The reaction mixture was reacted at 70°C for 8 hours. During the course of the reaction, samples were taken from the reaction mixture at 1 hour interval. The samples were then analysed for free fatty acids, monoacylglycerols (MAG), diacylglycerols (DAG) and triacylglycerols (TAG) by using high performance liquid chromatography. The results are shown in Table 2. The amounts of glycerol and water in the glycerol-water mixture vary in Comparative Examples 1 to 5, as shown in Table 1.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Microbiology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Fats And Perfumes (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2013533787A JP5782130B2 (en) | 2010-10-12 | 2011-08-15 | Process for producing diacylglycerol-enriched oil or fat |
KR1020137011748A KR20130106851A (en) | 2010-10-12 | 2011-08-15 | Process for production of diacylglycerol-enriched oil or fat |
CN201180059908.4A CN103403173B (en) | 2010-10-12 | 2011-08-15 | Produce and be rich in the oil of DG or the method for fat |
HK14100412.4A HK1187375A1 (en) | 2010-10-12 | 2014-01-14 | Process for production of diacylglycerol-enriched oil or fat |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
MYPI2010004804A MY164377A (en) | 2010-10-12 | 2010-10-12 | Process for production of diacylgylcerol-enriched oil or fat |
MYPI2010004804 | 2010-10-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2012050422A1 true WO2012050422A1 (en) | 2012-04-19 |
Family
ID=44759744
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/MY2011/000187 WO2012050422A1 (en) | 2010-10-12 | 2011-08-15 | Process for production of diacylglycerol-enriched oil or fat |
Country Status (5)
Country | Link |
---|---|
JP (1) | JP5782130B2 (en) |
KR (1) | KR20130106851A (en) |
HK (1) | HK1187375A1 (en) |
MY (1) | MY164377A (en) |
WO (1) | WO2012050422A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103484507A (en) * | 2013-07-30 | 2014-01-01 | 贵州大学 | Fermentation production culture medium and culture method for aspergillus niger capable of selective synthesis of 1,3-diglyceride |
CN109239105A (en) * | 2018-09-19 | 2019-01-18 | 天津大学 | It is a kind of for identifying the millimeter wave method of glyceryl monooleate phase |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6337414B1 (en) | 1998-07-09 | 2002-01-08 | Kao Corporation | Process for producing partial glyceride |
WO2003029392A1 (en) | 2001-10-03 | 2003-04-10 | Archer-Daniels-Midland Company | Chemical process for the production of 1,3-diglyceride oils |
EP1717318A1 (en) * | 2005-04-28 | 2006-11-02 | Kao Corporation | Process for producing fat or oil |
EP1803819A2 (en) * | 2005-12-28 | 2007-07-04 | Universiti Putra Malaysia | Process for the production of diacylglycerol |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5072258B2 (en) * | 2005-04-28 | 2012-11-14 | 花王株式会社 | Oil and fat manufacturing method |
-
2010
- 2010-10-12 MY MYPI2010004804A patent/MY164377A/en unknown
-
2011
- 2011-08-15 JP JP2013533787A patent/JP5782130B2/en not_active Expired - Fee Related
- 2011-08-15 KR KR1020137011748A patent/KR20130106851A/en not_active Application Discontinuation
- 2011-08-15 WO PCT/MY2011/000187 patent/WO2012050422A1/en active Application Filing
-
2014
- 2014-01-14 HK HK14100412.4A patent/HK1187375A1/en not_active IP Right Cessation
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6337414B1 (en) | 1998-07-09 | 2002-01-08 | Kao Corporation | Process for producing partial glyceride |
WO2003029392A1 (en) | 2001-10-03 | 2003-04-10 | Archer-Daniels-Midland Company | Chemical process for the production of 1,3-diglyceride oils |
EP1717318A1 (en) * | 2005-04-28 | 2006-11-02 | Kao Corporation | Process for producing fat or oil |
EP1803819A2 (en) * | 2005-12-28 | 2007-07-04 | Universiti Putra Malaysia | Process for the production of diacylglycerol |
WO2007075079A1 (en) | 2005-12-28 | 2007-07-05 | Universiti Putra Malaysia | Process for the production of diacylglycerol |
Non-Patent Citations (3)
Title |
---|
JANNI BROGAARD KRISTENSEN ET AL: "Diacylglycerol synthesis by enzymatic glycerolysis: Screening of commercially available lipases", JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY, vol. 82, no. 5, 1 May 2005 (2005-05-01), pages 329 - 334, XP055020135, ISSN: 0003-021X, DOI: 10.1007/s11746-005-1074-5 * |
KRISTENSEN J B ET AL: "Process optimization using response surface design and pilot plant production of dietary diacylglycerols by lipase-catalyzed glycerolysis", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 53, 5 August 2005 (2005-08-05), pages 7059 - 7066, XP002402019, ISSN: 0021-8561, DOI: 10.1021/JF0507745 * |
LO SEONG KOON LO: "Lipase-catalysed production and chemical composition of diacylglycerols from soybean oil deodoriser distillate", EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY, WILEY VCH VERLAG, WEINHEIM, DE, vol. 106, 1 January 2004 (2004-01-01), pages 218 - 224, XP002435250, ISSN: 1438-7697, DOI: 10.1002/EJLT.200300888 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103484507A (en) * | 2013-07-30 | 2014-01-01 | 贵州大学 | Fermentation production culture medium and culture method for aspergillus niger capable of selective synthesis of 1,3-diglyceride |
CN109239105A (en) * | 2018-09-19 | 2019-01-18 | 天津大学 | It is a kind of for identifying the millimeter wave method of glyceryl monooleate phase |
CN109239105B (en) * | 2018-09-19 | 2020-12-25 | 天津大学 | Millimeter wave method for identifying phase of glycerol monooleate |
Also Published As
Publication number | Publication date |
---|---|
JP5782130B2 (en) | 2015-09-24 |
MY164377A (en) | 2017-12-15 |
JP2013542727A (en) | 2013-11-28 |
HK1187375A1 (en) | 2014-04-04 |
KR20130106851A (en) | 2013-09-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US11781161B2 (en) | Enzymatic enrichment of n-3 fatty acids in the form of glycerides | |
EP1966387B1 (en) | Process for the production of diacylglycerol | |
US20220282290A1 (en) | Method for Synthesizing Diglyceride | |
CA2803477A1 (en) | Process for separating polyunsaturated fatty acids from long chain unsaturated or less saturated fatty acids | |
Wongsakul et al. | Synthesis of 2‐monoglycerides by alcoholysis of palm oil and tuna oil using immobilized lipases | |
EP2059132A1 (en) | Production of acylglycerol esters | |
WO2016136751A1 (en) | Production method for oil and fat | |
JP6715586B2 (en) | Method for producing highly unsaturated fatty acid | |
CN105754982B (en) | Immobilized lipase and method for producing immobilized lipase | |
WO2012050422A1 (en) | Process for production of diacylglycerol-enriched oil or fat | |
JP7365202B2 (en) | Method for producing fats and oils with high diacylglycerol content | |
JP6645804B2 (en) | Manufacturing method of structural fats and oils | |
JP7092460B2 (en) | Manufacturing method of structural fats and oils | |
US20120052538A1 (en) | Triglycerides with high content of unsaturated fatty acids | |
JP6818226B2 (en) | Oil and fat manufacturing method | |
JP6859212B2 (en) | Method for producing fats and oils containing high diacylglycerol | |
JP2019094445A (en) | Method for producing linseed oil | |
JP2018172517A (en) | Production method of fat and oil | |
US11771106B2 (en) | Oil composition with mono-acylglycerides | |
Shimada et al. | Application of multistep reactions with lipases to the oil and fat industry | |
US9896703B2 (en) | Method for producing transesterified fat and/or oil | |
JP2008220236A (en) | Method for producing middle-chain and long-chain fatty acid monoglyceride | |
CN103403173A (en) | Process for production of diacylglycerol-enriched oil or fat | |
WO2011075802A1 (en) | Production of diacylglycerols by lipase - catalyzed hydrolysis of palm oil |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 11764876 Country of ref document: EP Kind code of ref document: A1 |
|
DPE1 | Request for preliminary examination filed after expiration of 19th month from priority date (pct application filed from 20040101) | ||
ENP | Entry into the national phase |
Ref document number: 2013533787 Country of ref document: JP Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
ENP | Entry into the national phase |
Ref document number: 20137011748 Country of ref document: KR Kind code of ref document: A |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 11764876 Country of ref document: EP Kind code of ref document: A1 |