JPH0440995B2 - - Google Patents
Info
- Publication number
- JPH0440995B2 JPH0440995B2 JP61071915A JP7191586A JPH0440995B2 JP H0440995 B2 JPH0440995 B2 JP H0440995B2 JP 61071915 A JP61071915 A JP 61071915A JP 7191586 A JP7191586 A JP 7191586A JP H0440995 B2 JPH0440995 B2 JP H0440995B2
- Authority
- JP
- Japan
- Prior art keywords
- lipase
- reaction
- fats
- oils
- fat
- 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 - Lifetime
Links
- 235000019197 fats Nutrition 0.000 claims description 60
- 108090001060 Lipase Proteins 0.000 claims description 53
- 239000004367 Lipase Substances 0.000 claims description 53
- 102000004882 Lipase Human genes 0.000 claims description 53
- 235000019421 lipase Nutrition 0.000 claims description 53
- 238000006460 hydrolysis reaction Methods 0.000 claims description 35
- 238000005809 transesterification reaction Methods 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 25
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- 235000019879 cocoa butter substitute Nutrition 0.000 claims description 13
- 230000007062 hydrolysis Effects 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 10
- 150000004665 fatty acids Chemical class 0.000 claims description 10
- 229930195729 fatty acid Natural products 0.000 claims description 9
- 239000000194 fatty acid Substances 0.000 claims description 9
- 235000021588 free fatty acids Nutrition 0.000 claims description 7
- 125000005456 glyceride group Chemical group 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- -1 alcohol ester Chemical class 0.000 claims description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 2
- 239000005642 Oleic acid Substances 0.000 claims description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- 235000003441 saturated fatty acids Nutrition 0.000 claims 1
- 150000004671 saturated fatty acids Chemical class 0.000 claims 1
- 125000005457 triglyceride group Chemical group 0.000 claims 1
- 239000003925 fat Substances 0.000 description 56
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 55
- 229940040461 lipase Drugs 0.000 description 49
- 239000003921 oil Substances 0.000 description 49
- 235000019198 oils Nutrition 0.000 description 48
- 238000000034 method Methods 0.000 description 21
- 239000000047 product Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 235000019482 Palm oil Nutrition 0.000 description 10
- 239000002540 palm oil Substances 0.000 description 10
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 8
- 235000021355 Stearic acid Nutrition 0.000 description 7
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 7
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 7
- 230000008707 rearrangement Effects 0.000 description 7
- 239000008117 stearic acid Substances 0.000 description 7
- 235000014593 oils and fats Nutrition 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 4
- 241001135917 Vitellaria paradoxa Species 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 239000002808 molecular sieve Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 229940057910 shea butter Drugs 0.000 description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- 241000498617 Mucor javanicus Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000007853 buffer solution Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000005313 fatty acid group Chemical group 0.000 description 3
- 239000004006 olive oil Substances 0.000 description 3
- 235000008390 olive oil Nutrition 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000007039 two-step reaction Methods 0.000 description 2
- RBLADLVPSYELCA-IKPAITLHSA-N 1,3-bis(octadecanoyloxy)propan-2-yl (9z)-octadec-9-enoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC RBLADLVPSYELCA-IKPAITLHSA-N 0.000 description 1
- FDCOHGHEADZEGF-QPLCGJKRSA-N 1,3-dipalmitoyl-2-oleoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC FDCOHGHEADZEGF-QPLCGJKRSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000235395 Mucor Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 102000019280 Pancreatic lipases Human genes 0.000 description 1
- 108050006759 Pancreatic lipases Proteins 0.000 description 1
- 241000235527 Rhizopus Species 0.000 description 1
- 241000303962 Rhizopus delemar Species 0.000 description 1
- 241000235528 Rhizopus microsporus var. chinensis Species 0.000 description 1
- 240000005384 Rhizopus oryzae Species 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 description 1
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 1
- 241000179532 [Candida] cylindracea Species 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 235000019869 fractionated palm oil Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 230000002366 lipolytic effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 229940116369 pancreatic lipase Drugs 0.000 description 1
- 229920001282 polysaccharide Chemical class 0.000 description 1
- 239000005017 polysaccharide Chemical class 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 235000009566 rice Nutrition 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
- 108010079522 solysime Proteins 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 108010072641 thermostable lipase Proteins 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 229940117972 triolein Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Landscapes
- Edible Oils And Fats (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Confectionery (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61071915A JPS62228290A (ja) | 1986-03-29 | 1986-03-29 | カカオバタ−代用脂の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61071915A JPS62228290A (ja) | 1986-03-29 | 1986-03-29 | カカオバタ−代用脂の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62228290A JPS62228290A (ja) | 1987-10-07 |
| JPH0440995B2 true JPH0440995B2 (de) | 1992-07-06 |
Family
ID=13474309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61071915A Granted JPS62228290A (ja) | 1986-03-29 | 1986-03-29 | カカオバタ−代用脂の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62228290A (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR200480826Y1 (ko) * | 2016-01-07 | 2016-07-11 | 이희우 | 제단용 꽃 장식대 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69322974D1 (de) * | 1992-10-29 | 1999-02-18 | Loders Croklaan Bv | Enzymatisches triglycerid-umsetzverfahren |
| JP3388838B2 (ja) * | 1993-11-18 | 2003-03-24 | 旭電化工業株式会社 | 製菓用油脂組成物の製造方法 |
| EP0882797B1 (de) * | 1997-06-04 | 2003-07-16 | Loders Croklaan B.V. | Herstellung von symmetrischen Triglyceriden aba |
| JP4530311B2 (ja) * | 2000-07-13 | 2010-08-25 | 日本水産株式会社 | リパーゼを用いたグリセライドの製造方法 |
| KR101070791B1 (ko) * | 2008-11-07 | 2011-10-07 | 씨제이제일제당 (주) | 효소적 에스테르 교환 반응으로 제조된 코코아 버터 대용 유지 및 그 제조방법 |
| JP2013507117A (ja) * | 2009-12-04 | 2013-03-04 | シージェイ チェイルジェダング コーポレイション | チョコレート及び製菓用の油脂組成物 |
| JP6390255B2 (ja) * | 2014-08-07 | 2018-09-19 | 横浜ゴム株式会社 | ゴム組成物および空気入りタイヤ |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60203196A (ja) * | 1984-03-26 | 1985-10-14 | Asahi Denka Kogyo Kk | リパ−ゼによる油脂類のエステル交換反応方法 |
| JPS60213196A (ja) * | 1984-03-16 | 1985-10-25 | ジーイーシー プレッシー テレコミュニケーションズ リミテッド | デイジタル線路終端装置コマンド・インターフエース |
-
1986
- 1986-03-29 JP JP61071915A patent/JPS62228290A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60213196A (ja) * | 1984-03-16 | 1985-10-25 | ジーイーシー プレッシー テレコミュニケーションズ リミテッド | デイジタル線路終端装置コマンド・インターフエース |
| JPS60203196A (ja) * | 1984-03-26 | 1985-10-14 | Asahi Denka Kogyo Kk | リパ−ゼによる油脂類のエステル交換反応方法 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR200480826Y1 (ko) * | 2016-01-07 | 2016-07-11 | 이희우 | 제단용 꽃 장식대 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62228290A (ja) | 1987-10-07 |
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