JPS6251593B2 - - Google Patents

Info

Publication number: JPS6251593B2
Authority: JP; Japan
Prior art keywords: reaction; lipase; acid value; oil; glycerin
Prior art date: 1985-05-08
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

Application number

JP60097639A

Other languages

English (en)

Japanese (ja)

Other versions

JPS61257192A (ja

Inventor

Yoshiji Kosugi

Noboru Tomizuka

Hideo Suzuki

Hisao Igusa

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

National Institute of Advanced Industrial Science and Technology AIST

Original Assignee

Agency of Industrial Science and Technology

Priority date (The priority date 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 date listed.)

1985-05-08

Filing date

1985-05-08

Publication date

1987-10-30

1985-05-08 Application filed by Agency of Industrial Science and Technology filed Critical Agency of Industrial Science and Technology

1985-05-08 Priority to JP60097639A priority Critical patent/JPS61257192A/ja

1986-11-14 Publication of JPS61257192A publication Critical patent/JPS61257192A/ja

1987-10-30 Publication of JPS6251593B2 publication Critical patent/JPS6251593B2/ja

Status Granted legal-status Critical Current

Links

PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 74
238000006243 chemical reaction Methods 0.000 claims description 68
239000002253 acid Substances 0.000 claims description 58
108090001060 Lipase Proteins 0.000 claims description 51
102000004882 Lipase Human genes 0.000 claims description 51
239000004367 Lipase Substances 0.000 claims description 48
235000019421 lipase Nutrition 0.000 claims description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 40
235000011187 glycerol Nutrition 0.000 claims description 37
LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 22
238000004519 manufacturing process Methods 0.000 claims description 7
239000003921 oil Substances 0.000 description 45
235000019198 oils Nutrition 0.000 description 45
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
238000005809 transesterification reaction Methods 0.000 description 16
230000007423 decrease Effects 0.000 description 15
238000000034 method Methods 0.000 description 14
150000002148 esters Chemical class 0.000 description 13
238000003786 synthesis reaction Methods 0.000 description 12
230000015572 biosynthetic process Effects 0.000 description 11
235000014113 dietary fatty acids Nutrition 0.000 description 10
239000000194 fatty acid Substances 0.000 description 10
229930195729 fatty acid Natural products 0.000 description 10
150000004665 fatty acids Chemical class 0.000 description 10
108090000790 Enzymes Proteins 0.000 description 9
102000004190 Enzymes Human genes 0.000 description 9
235000019774 Rice Bran oil Nutrition 0.000 description 8
235000021588 free fatty acids Nutrition 0.000 description 8
239000008165 rice bran oil Substances 0.000 description 8
OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 7
230000000694 effects Effects 0.000 description 7
239000003925 fat Substances 0.000 description 7
238000010701 ester synthesis reaction Methods 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
229920001467 poly(styrenesulfonates) Polymers 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
241000233866 Fungi Species 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
230000003301 hydrolyzing effect Effects 0.000 description 5
239000002994 raw material Substances 0.000 description 5
241000894006 Bacteria Species 0.000 description 4
241000588881 Chromobacterium Species 0.000 description 4
108010093096 Immobilized Enzymes Proteins 0.000 description 4
241000235395 Mucor Species 0.000 description 4
241000589516 Pseudomonas Species 0.000 description 4
230000009471 action Effects 0.000 description 4
230000008901 benefit Effects 0.000 description 4
239000000969 carrier Substances 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
125000005456 glyceride group Chemical group 0.000 description 4
239000000203 mixture Substances 0.000 description 4
238000000926 separation method Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
208000005156 Dehydration Diseases 0.000 description 3
SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 3
241000235527 Rhizopus Species 0.000 description 3
241000235545 Rhizopus niveus Species 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
230000003247 decreasing effect Effects 0.000 description 3
230000018044 dehydration Effects 0.000 description 3
238000006297 dehydration reaction Methods 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
235000019626 lipase activity Nutrition 0.000 description 3
150000003626 triacylglycerols Chemical class 0.000 description 3
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 3
108010015598 Chromobacterium viscosum lipase Proteins 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
235000008331 Pinus X rigitaeda Nutrition 0.000 description 2
235000011613 Pinus brutia Nutrition 0.000 description 2
241000018646 Pinus brutia Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
239000011324 bead Substances 0.000 description 2
-1 diglyceride Chemical compound 0.000 description 2
235000013305 food Nutrition 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
230000003100 immobilizing effect Effects 0.000 description 2
239000012528 membrane Substances 0.000 description 2
244000005700 microbiome Species 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000000344 soap Substances 0.000 description 2
229930003799 tocopherol Natural products 0.000 description 2
239000011732 tocopherol Substances 0.000 description 2
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
235000019482 Palm oil Nutrition 0.000 description 1
241000589540 Pseudomonas fluorescens Species 0.000 description 1
101000966371 Rhizopus niveus Lipase Proteins 0.000 description 1
229930182558 Sterol Natural products 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000003957 anion exchange resin Substances 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
238000002306 biochemical method Methods 0.000 description 1
229920001222 biopolymer Polymers 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000000919 ceramic Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000013329 compounding Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000011437 continuous method Methods 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
239000010779 crude oil Substances 0.000 description 1
GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
239000008157 edible vegetable oil Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
150000004676 glycans Chemical class 0.000 description 1
230000005484 gravity Effects 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000000691 measurement method Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000000199 molecular distillation Methods 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
239000002540 palm oil Substances 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
230000008569 process Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229920002379 silicone rubber Polymers 0.000 description 1
239000004945 silicone rubber Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
235000003702 sterols Nutrition 0.000 description 1
150000003432 sterols Chemical class 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
229960001295 tocopherol Drugs 0.000 description 1
235000010384 tocopherol Nutrition 0.000 description 1
235000019149 tocopherols Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000000341 volatile oil Substances 0.000 description 1
230000004580 weight loss Effects 0.000 description 1
GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1

Landscapes

Preparation Of Compounds By Using Micro-Organisms (AREA)

JP60097639A 1985-05-08 1985-05-08 モノグリセライド高含有物の製造法 Granted JPS61257192A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP60097639A JPS61257192A (ja)	1985-05-08	1985-05-08	モノグリセライド高含有物の製造法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP60097639A JPS61257192A (ja)	1985-05-08	1985-05-08	モノグリセライド高含有物の製造法

Publications (2)

Publication Number	Publication Date
JPS61257192A JPS61257192A (ja)	1986-11-14
JPS6251593B2 true JPS6251593B2 (fr)	1987-10-30

Family

ID=14197702

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP60097639A Granted JPS61257192A (ja)	1985-05-08	1985-05-08	モノグリセライド高含有物の製造法

Country Status (1)

Country	Link
JP (1)	JPS61257192A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0665311B2 (ja) *	1987-09-09	1994-08-24	花王株式会社	ジグリセリドの製造法
US5288619A (en) *	1989-12-18	1994-02-22	Kraft General Foods, Inc.	Enzymatic method for preparing transesterified oils
CN103074164B (zh) *	2013-01-11	2014-07-30	江南大学	一种固定化脂肪酶催化法制备月桂酸单甘油酯的方法

1985
- 1985-05-08 JP JP60097639A patent/JPS61257192A/ja active Granted

Also Published As

Publication number	Publication date
JPS61257192A (ja)	1986-11-14

Legal Events

Date	Code	Title	Description
2004-08-24	R250	Receipt of annual fees	Free format text: JAPANESE INTERMEDIATE CODE: R250
2005-05-08	EXPY	Cancellation because of completion of term

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JP4849967B2 (ja)	2012-01-11	脂肪酸類の製造方法
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JP2983655B2 (ja)	1999-11-29	ジグリセリドの製造法
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KR20080056154A (ko)	2008-06-20	고정화 리파아제를 사용하는 효소가수분해법 공정 및고온고압가수분해법 공정을 포함하는 유지로부터의지방산류 제조를 위한 2-단계 과정
JP3509124B2 (ja)	2004-03-22	固定化リパーゼを用いた油脂類のエステル交換方法
JPH0528114B2 (fr)	1993-04-23
JP2778135B2 (ja)	1998-07-23	リパーゼ固定化酵素剤の調製方法
JP2676470B2 (ja)	1997-11-17	固定化リパーゼ、その製造方法及び該リパーゼを用いた油脂類のエステル交換方法
JPH05268952A (ja)	1993-10-19	リパーゼ剤の調製法
JP2570774B2 (ja)	1997-01-16	油脂の改質法
JPH0582197B2 (fr)	1993-11-17
JPH09296197A (ja)	1997-11-18	油脂の脱水、精製法
JPS63240790A (ja)	1988-10-06	高分子量リパ−ゼによる対称型トリグリセリドの製造法
JPS63254989A (ja)	1988-10-21	トリパルミトレイルグリセライドの製造方法