JPH0369516B2 - - Google Patents
Info
- Publication number
- JPH0369516B2 JPH0369516B2 JP55067555A JP6755580A JPH0369516B2 JP H0369516 B2 JPH0369516 B2 JP H0369516B2 JP 55067555 A JP55067555 A JP 55067555A JP 6755580 A JP6755580 A JP 6755580A JP H0369516 B2 JPH0369516 B2 JP H0369516B2
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- glyceride
- melting point
- separated
- mixture
- 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
Links
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 87
- 239000000194 fatty acid Substances 0.000 claims description 87
- 229930195729 fatty acid Natural products 0.000 claims description 87
- 150000004665 fatty acids Chemical class 0.000 claims description 64
- 239000000203 mixture Substances 0.000 claims description 33
- 235000014121 butter Nutrition 0.000 claims description 32
- 125000005456 glyceride group Chemical group 0.000 claims description 32
- 238000002844 melting Methods 0.000 claims description 31
- 230000008018 melting Effects 0.000 claims description 28
- 239000003921 oil Substances 0.000 claims description 28
- -1 fatty acid ester Chemical class 0.000 claims description 25
- 239000003925 fat Substances 0.000 claims description 23
- 235000019197 fats Nutrition 0.000 claims description 23
- 108090000790 Enzymes Proteins 0.000 claims description 19
- 102000004190 Enzymes Human genes 0.000 claims description 19
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 10
- 239000000376 reactant Substances 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000012545 processing Methods 0.000 claims description 6
- 150000003626 triacylglycerols Chemical class 0.000 claims description 4
- 125000005457 triglyceride group Chemical group 0.000 claims description 3
- 238000003672 processing method Methods 0.000 claims 2
- 235000019198 oils Nutrition 0.000 description 26
- 238000005809 transesterification reaction Methods 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 18
- 229940088598 enzyme Drugs 0.000 description 18
- 230000000694 effects Effects 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 12
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000002994 raw material Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 150000004702 methyl esters Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000005909 Kieselgur Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 5
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 5
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 5
- 108090001060 Lipase Proteins 0.000 description 5
- 239000004367 Lipase Substances 0.000 description 5
- 102000004882 Lipase Human genes 0.000 description 5
- 239000005642 Oleic acid Substances 0.000 description 5
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 5
- 235000021355 Stearic acid Nutrition 0.000 description 5
- 229940110456 cocoa butter Drugs 0.000 description 5
- 235000019868 cocoa butter Nutrition 0.000 description 5
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 5
- 238000005194 fractionation Methods 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 5
- 229940040461 lipase Drugs 0.000 description 5
- 235000019421 lipase Nutrition 0.000 description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 5
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 5
- 239000002957 persistent organic pollutant Substances 0.000 description 5
- 238000004904 shortening Methods 0.000 description 5
- 239000008117 stearic acid Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 4
- 238000004064 recycling Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 235000021314 Palmitic acid Nutrition 0.000 description 3
- 240000005384 Rhizopus oryzae Species 0.000 description 3
- 244000299461 Theobroma cacao Species 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000006911 enzymatic reaction Methods 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 241000235527 Rhizopus Species 0.000 description 2
- 235000019485 Safflower oil Nutrition 0.000 description 2
- 235000009470 Theobroma cacao Nutrition 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- MVLVMROFTAUDAG-UHFFFAOYSA-N ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC MVLVMROFTAUDAG-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 230000002366 lipolytic effect Effects 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 235000008390 olive oil Nutrition 0.000 description 2
- 229910001562 pearlite Inorganic materials 0.000 description 2
- 239000003813 safflower oil Substances 0.000 description 2
- 235000005713 safflower oil Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-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
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 235000004936 Bromus mango Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 244000241235 Citrullus lanatus Species 0.000 description 1
- 235000012828 Citrullus lanatus var citroides Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- FDCOHGHEADZEGF-OCEACIFDSA-N Glycerol 1,3-dihexadecanoate 2-(9Z-octadecenoate) Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C\CCCCCCCC FDCOHGHEADZEGF-OCEACIFDSA-N 0.000 description 1
- 240000007228 Mangifera indica Species 0.000 description 1
- 235000014826 Mangifera indica Nutrition 0.000 description 1
- 241001465754 Metazoa Species 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
- 235000019482 Palm oil Nutrition 0.000 description 1
- 102000019280 Pancreatic lipases Human genes 0.000 description 1
- 108050006759 Pancreatic lipases Proteins 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 241000235545 Rhizopus niveus Species 0.000 description 1
- 101000966371 Rhizopus niveus Lipase Proteins 0.000 description 1
- 235000009184 Spondias indica Nutrition 0.000 description 1
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 1
- 235000005767 Theobroma cacao ssp. sphaerocarpum 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
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 1
- 241001135917 Vitellaria paradoxa Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 235000001046 cacaotero Nutrition 0.000 description 1
- 239000010495 camellia oil Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000019879 cocoa butter substitute Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000009884 interesterification Methods 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 229940116369 pancreatic lipase Drugs 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229940057910 shea butter Drugs 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
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000005496 tempering Methods 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
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 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 |
|---|---|---|---|
| JP6755580A JPS56163196A (en) | 1980-05-20 | 1980-05-20 | Process of oil and grease |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6755580A JPS56163196A (en) | 1980-05-20 | 1980-05-20 | Process of oil and grease |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56163196A JPS56163196A (en) | 1981-12-15 |
| JPH0369516B2 true JPH0369516B2 (da) | 1991-11-01 |
Family
ID=13348318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6755580A Granted JPS56163196A (en) | 1980-05-20 | 1980-05-20 | Process of oil and grease |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56163196A (da) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009031680A1 (ja) | 2007-09-07 | 2009-03-12 | The Nisshin Oillio Group, Ltd. | 1,3-ジ飽和-2-不飽和トリグリセリドの分別方法 |
| WO2009031679A1 (ja) | 2007-09-07 | 2009-03-12 | The Nisshin Oillio Group, Ltd. | ハードバターの製造方法 |
| WO2010110260A1 (ja) | 2009-03-25 | 2010-09-30 | 不二製油株式会社 | ハードバター組成物の製造法 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0783718B2 (ja) * | 1986-05-21 | 1995-09-13 | 日清製油株式会社 | １，３−ジステアロ−２−オレインの製造法 |
| JP2715633B2 (ja) * | 1990-07-17 | 1998-02-18 | 鐘淵化学工業株式会社 | ファットブルーム耐性向上剤、及びこれを含有してなるハードバター、並びにそれらを用いたチョコレート類． |
| JP5008229B2 (ja) * | 2000-08-11 | 2012-08-22 | 株式会社Ａｄｅｋａ | 可塑性油脂組成物 |
-
1980
- 1980-05-20 JP JP6755580A patent/JPS56163196A/ja active Granted
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009031680A1 (ja) | 2007-09-07 | 2009-03-12 | The Nisshin Oillio Group, Ltd. | 1,3-ジ飽和-2-不飽和トリグリセリドの分別方法 |
| WO2009031679A1 (ja) | 2007-09-07 | 2009-03-12 | The Nisshin Oillio Group, Ltd. | ハードバターの製造方法 |
| EP2388307A1 (en) | 2007-09-07 | 2011-11-23 | The Nisshin OilliO Group, Ltd. | Fractionation method of 1,3-disaturated-2-unsaturated triglyceride |
| EP2388306A1 (en) | 2007-09-07 | 2011-11-23 | The Nisshin OilliO Group, Ltd. | Fractionation method of 1,3-disaturated-2-unsaturated triglyceride |
| EP2399977A1 (en) | 2007-09-07 | 2011-12-28 | The Nisshin OilliO Group, Ltd. | Fractionation method of 1,3-disaturated-2-unsaturated triglyceride |
| US8980346B2 (en) | 2007-09-07 | 2015-03-17 | The Nisshin Oillio Group, Ltd. | Process for preparing hard butter |
| WO2010110260A1 (ja) | 2009-03-25 | 2010-09-30 | 不二製油株式会社 | ハードバター組成物の製造法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56163196A (en) | 1981-12-15 |
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