JPS5928482A - 油脂類のエステル交換反応方法 - Google Patents
油脂類のエステル交換反応方法Info
- Publication number
- JPS5928482A JPS5928482A JP57136476A JP13647682A JPS5928482A JP S5928482 A JPS5928482 A JP S5928482A JP 57136476 A JP57136476 A JP 57136476A JP 13647682 A JP13647682 A JP 13647682A JP S5928482 A JPS5928482 A JP S5928482A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- oil
- ester interchange
- water
- transesterification
- 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.)
- Granted
Links
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 69
- 238000000034 method Methods 0.000 title claims abstract description 16
- 150000002148 esters Chemical class 0.000 title abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 102000004190 Enzymes Human genes 0.000 claims abstract description 24
- 108090000790 Enzymes Proteins 0.000 claims abstract description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims abstract description 6
- 238000002425 crystallisation Methods 0.000 claims abstract description 5
- 230000008025 crystallization Effects 0.000 claims abstract description 5
- 239000000741 silica gel Substances 0.000 claims abstract description 5
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 claims abstract description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000010457 zeolite Substances 0.000 claims abstract description 3
- 238000005809 transesterification reaction Methods 0.000 claims description 31
- 230000000694 effects Effects 0.000 claims description 14
- 235000014593 oils and fats Nutrition 0.000 claims description 14
- 150000004706 metal oxides Chemical class 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 4
- 244000228088 Cola acuminata Species 0.000 claims description 2
- 235000010205 Cola acuminata Nutrition 0.000 claims description 2
- 235000015438 Cola nitida Nutrition 0.000 claims description 2
- 239000004575 stone Substances 0.000 claims description 2
- 150000003463 sulfur Chemical class 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 239000000758 substrate Substances 0.000 abstract description 12
- 239000006227 byproduct Substances 0.000 abstract description 11
- 239000007795 chemical reaction product Substances 0.000 abstract description 9
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 9
- 239000000194 fatty acid Substances 0.000 abstract description 9
- 229930195729 fatty acid Natural products 0.000 abstract description 9
- 150000004665 fatty acids Chemical class 0.000 abstract description 9
- 239000011541 reaction mixture Substances 0.000 abstract description 2
- 230000002745 absorbent Effects 0.000 abstract 1
- 239000002250 absorbent Substances 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 239000010440 gypsum Substances 0.000 abstract 1
- 229910052602 gypsum Inorganic materials 0.000 abstract 1
- 239000010446 mirabilite Substances 0.000 abstract 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 abstract 1
- 229940088598 enzyme Drugs 0.000 description 20
- 239000003921 oil Substances 0.000 description 20
- 235000019198 oils Nutrition 0.000 description 20
- 239000003925 fat Substances 0.000 description 15
- 235000019197 fats Nutrition 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 9
- 102000004882 Lipase Human genes 0.000 description 6
- 108090001060 Lipase Proteins 0.000 description 6
- 125000005456 glyceride group Chemical group 0.000 description 6
- 239000004367 Lipase Substances 0.000 description 5
- 235000014121 butter Nutrition 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 235000019421 lipase Nutrition 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 241000235527 Rhizopus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 239000004006 olive oil Substances 0.000 description 3
- 235000008390 olive oil Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-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
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 description 2
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- -1 diglyceride (DG) Chemical compound 0.000 description 2
- XIRNKXNNONJFQO-UHFFFAOYSA-N ethyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC XIRNKXNNONJFQO-UHFFFAOYSA-N 0.000 description 2
- MVLVMROFTAUDAG-UHFFFAOYSA-N ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC MVLVMROFTAUDAG-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 241000228212 Aspergillus Species 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000235395 Mucor Species 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 244000088415 Raphanus sativus Species 0.000 description 1
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 1
- 241001135917 Vitellaria paradoxa Species 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 239000010495 camellia oil Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000019879 cocoa butter substitute Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil 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
- 238000004332 deodorization Methods 0.000 description 1
- 229940079919 digestives enzyme preparation Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 1
- 229940067592 ethyl palmitate Drugs 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal 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
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940057910 shea butter Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 125000005457 triglyceride group Chemical group 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Fats And Perfumes (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57136476A JPS5928482A (ja) | 1982-08-05 | 1982-08-05 | 油脂類のエステル交換反応方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57136476A JPS5928482A (ja) | 1982-08-05 | 1982-08-05 | 油脂類のエステル交換反応方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5928482A true JPS5928482A (ja) | 1984-02-15 |
| JPH0412113B2 JPH0412113B2 (xx) | 1992-03-03 |
Family
ID=15176014
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57136476A Granted JPS5928482A (ja) | 1982-08-05 | 1982-08-05 | 油脂類のエステル交換反応方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5928482A (xx) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61291689A (ja) * | 1985-06-19 | 1986-12-22 | 日清製油株式会社 | 芳香を保持した改質油脂の製造法 |
| JPS6344892A (ja) * | 1986-08-13 | 1988-02-25 | Kao Corp | 油脂類のエステル交換反応方法 |
| US5017476A (en) * | 1988-05-06 | 1991-05-21 | Degussa Aktiengesellschaft | Method for the biocatalytic reaction of organic substances |
-
1982
- 1982-08-05 JP JP57136476A patent/JPS5928482A/ja active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61291689A (ja) * | 1985-06-19 | 1986-12-22 | 日清製油株式会社 | 芳香を保持した改質油脂の製造法 |
| JPS6344892A (ja) * | 1986-08-13 | 1988-02-25 | Kao Corp | 油脂類のエステル交換反応方法 |
| JPH0338837B2 (xx) * | 1986-08-13 | 1991-06-11 | Kao Corp | |
| US5017476A (en) * | 1988-05-06 | 1991-05-21 | Degussa Aktiengesellschaft | Method for the biocatalytic reaction of organic substances |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0412113B2 (xx) | 1992-03-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4268527A (en) | Method for producing cacao butter substitute | |
| EP0064855B1 (en) | Fat processing | |
| JP3720194B2 (ja) | 部分グリセリドの製造法 | |
| JP5216277B2 (ja) | 食用油脂の製造方法 | |
| IE44771B1 (en) | Fat process and composition | |
| JPS61181390A (ja) | 酵素によるグリセライドの製造法 | |
| RU2528954C2 (ru) | Способ производства триглицеридной композиции | |
| JPS6344892A (ja) | 油脂類のエステル交換反応方法 | |
| JPS63287492A (ja) | 油脂類のエステル交換反応方法 | |
| JPS5928482A (ja) | 油脂類のエステル交換反応方法 | |
| JPS61247390A (ja) | グリセリンおよび縮合されたグリセリンと脂肪酸との部分エステルの製法 | |
| CA2025124A1 (en) | Transesterification | |
| JP3785467B2 (ja) | 油脂組成物の製造方法 | |
| JP6557798B1 (ja) | 油脂の製造方法 | |
| JPH0327199B2 (xx) | ||
| JP2002088392A (ja) | 油脂類のエステル交換方法 | |
| JP4945838B2 (ja) | 油脂の製造方法 | |
| EP0084900B1 (en) | Margarine fat blend with a reduced tendency to sandiness and a process for reducing the development of sandiness in fat blends | |
| JPH07179882A (ja) | 耐冷凍性油脂およびその製造法 | |
| JPH0665310B2 (ja) | ジグリセリドの製造法 | |
| JPH0369516B2 (xx) | ||
| JPS60251891A (ja) | 油脂のエステル交換反応方法 | |
| JPH01104184A (ja) | 酵素によるエステル化方法 | |
| JPH0248233B2 (xx) | ||
| JP2024507454A (ja) | ｓｎ－２位パルミチン酸又はｓｎ－２位オレイン酸のいずれかが富化されたトリアシルグリセロールの製造方法 |