JP2012529907A - ハードバターの製造方法 - Google Patents
ハードバターの製造方法 Download PDFInfo
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- JP2012529907A JP2012529907A JP2012515958A JP2012515958A JP2012529907A JP 2012529907 A JP2012529907 A JP 2012529907A JP 2012515958 A JP2012515958 A JP 2012515958A JP 2012515958 A JP2012515958 A JP 2012515958A JP 2012529907 A JP2012529907 A JP 2012529907A
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- 235000014121 butter Nutrition 0.000 title claims abstract description 50
- 238000004519 manufacturing process Methods 0.000 title claims description 24
- 235000019197 fats Nutrition 0.000 claims abstract description 83
- 238000005194 fractionation Methods 0.000 claims abstract description 39
- 238000002844 melting Methods 0.000 claims abstract description 38
- 230000008018 melting Effects 0.000 claims abstract description 37
- 239000002904 solvent Substances 0.000 claims abstract description 34
- 108090000790 Enzymes Proteins 0.000 claims abstract description 18
- 102000004190 Enzymes Human genes 0.000 claims abstract description 18
- 239000002994 raw material Substances 0.000 claims abstract description 5
- 239000003921 oil Substances 0.000 claims description 85
- 235000019198 oils Nutrition 0.000 claims description 83
- 239000003925 fat Substances 0.000 claims description 82
- 238000000034 method Methods 0.000 claims description 45
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 34
- 244000299461 Theobroma cacao Species 0.000 claims description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 32
- 235000019219 chocolate Nutrition 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 15
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- MVLVMROFTAUDAG-UHFFFAOYSA-N ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC MVLVMROFTAUDAG-UHFFFAOYSA-N 0.000 claims description 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 6
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- 125000004494 ethyl ester group Chemical group 0.000 claims description 5
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- 239000002600 sunflower oil Substances 0.000 claims description 4
- 239000008158 vegetable oil Substances 0.000 claims description 4
- 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 claims description 3
- 235000019871 vegetable fat Nutrition 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
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005642 Oleic acid Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 2
- 235000014593 oils and fats Nutrition 0.000 claims description 2
- 150000002148 esters Chemical group 0.000 claims 2
- 238000005809 transesterification reaction Methods 0.000 abstract description 19
- 238000000926 separation method Methods 0.000 description 19
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- 150000003626 triacylglycerols Chemical class 0.000 description 10
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- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
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- 239000004615 ingredient Substances 0.000 description 6
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- 239000000047 product Substances 0.000 description 5
- 125000005457 triglyceride group Chemical group 0.000 description 5
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 4
- 235000009508 confectionery Nutrition 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 235000013373 food additive Nutrition 0.000 description 4
- 239000002778 food additive Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 108090001060 Lipase Proteins 0.000 description 3
- 239000004367 Lipase Substances 0.000 description 3
- 102000004882 Lipase Human genes 0.000 description 3
- 108010048733 Lipozyme Proteins 0.000 description 3
- 229940110456 cocoa butter Drugs 0.000 description 3
- 235000019868 cocoa butter Nutrition 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 235000019421 lipase Nutrition 0.000 description 3
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003507 refrigerant Substances 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 235000019220 whole milk chocolate Nutrition 0.000 description 3
- QXPXMOHHFYONAC-SGEDCAFJSA-N 1-(hexadecanoyloxy)-3-(octadecanoyloxy)propan-2-yl (9z)-octadec-9-enoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC QXPXMOHHFYONAC-SGEDCAFJSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000235403 Rhizomucor miehei Species 0.000 description 2
- 241000235527 Rhizopus Species 0.000 description 2
- 241000235545 Rhizopus niveus Species 0.000 description 2
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- 238000012545 processing Methods 0.000 description 2
- RYNHWWNZNIGDAQ-CDAVXRBQSA-N 1,2-Dioleoyl-3-stearoyl-rac-glycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC RYNHWWNZNIGDAQ-CDAVXRBQSA-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
- HUOSYVFXLJXXIK-LPPQCEDISA-N C(CCCCCCCCCCCCCCCCC)(=O)OCC(OC(CCCCCCC\C=C/CCCCCCCC)=O)COC(CCCCCCCCCCCCCCCCC)=O.C(CCCCCCCCCCCCCCCCC)(=O)OCC(OC(CCCCCCC\C=C/CCCCCCCC)=O)COC(CCCCCCCCCCCCCCCCC)=O Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)OCC(OC(CCCCCCC\C=C/CCCCCCCC)=O)COC(CCCCCCCCCCCCCCCCC)=O.C(CCCCCCCCCCCCCCCCC)(=O)OCC(OC(CCCCCCC\C=C/CCCCCCCC)=O)COC(CCCCCCCCCCCCCCCCC)=O HUOSYVFXLJXXIK-LPPQCEDISA-N 0.000 description 1
- 241000498617 Mucor javanicus Species 0.000 description 1
- 241000235402 Rhizomucor Species 0.000 description 1
- 241000303962 Rhizopus delemar Species 0.000 description 1
- 240000005384 Rhizopus oryzae Species 0.000 description 1
- 235000013752 Rhizopus oryzae 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
- -1 and for example Substances 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
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- 235000015895 biscuits Nutrition 0.000 description 1
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- 239000002537 cosmetic Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- JQOAQUXIUNVRQW-UHFFFAOYSA-N hexane Chemical compound CCCCCC.CCCCCC JQOAQUXIUNVRQW-UHFFFAOYSA-N 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000012360 testing method 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
Images
Classifications
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING OR TREATMENT THEREOF
- A23C15/00—Butter; Butter preparations; Making thereof
- A23C15/02—Making thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G1/00—Cocoa; Cocoa products, e.g. chocolate; Substitutes therefor
- A23G1/30—Cocoa products, e.g. chocolate; Substitutes therefor
- A23G1/32—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds
- A23G1/36—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds characterised by the fats used
- A23G1/38—Cocoa butter substitutes
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G1/00—Cocoa; Cocoa products, e.g. chocolate; Substitutes therefor
- A23G1/30—Cocoa products, e.g. chocolate; Substitutes therefor
- A23G1/32—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds
- A23G1/46—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds containing dairy products
-
- 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
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
- C11B7/0008—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents
- C11B7/0025—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents in solvents containing oxygen in their molecule
-
- 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
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
- C11B7/0083—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils with addition of auxiliary substances, e.g. cristallisation promotors, filter aids, melting point depressors
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Edible Oils And Fats (AREA)
- Confectionery (AREA)
- Fats And Perfumes (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
【選択図】図1
Description
ハイオレイックひまわり油とステアリン酸エチルエステル(Stearic ethyl ester)とをsn-1,3位に特異性を有する酵素であるLipozyme RMIM(immobilized sn-1,3-specific lipase from Rhizomucor miehei)(リゾムコール・ミーハイ由来のsn-1,3位に特異性を有する固定化リパーゼであるリポザイム RMIM)を用いてエステル交換反応させ、SOS含量が25w/w%以上になるようにした。合成された油脂を0.001mbar、230℃で蒸溜してエチルエステルを除去し、トリアシルグリセリド(Triacylglyceride:TAG)が98w/w%以上になるようにした。
上記実施例1と同様に、ハイオレイックひまわり油とステアリン酸エチルエステル(Stearic ethyl ester)をsn-1,3位に特異性を有する酵素であるLipozyme RMIM (immobilized sn-1,3-specific lipase from Rhizomucor miehei)を用いてエステル交換反応させ、SOS含量が25w/w%以上になるようにした。合成された油脂は0.001mbar、230℃で蒸溜し、エチルエステルを除去し、トリアシルグリセリド(Triacylglyceride:TAG)が98%以上になるようにした。
酵素エステル交換反応によってトリグリセリドの構造が変化するが、このトリグリセリドの構造が油脂の物理的、化学的特性を決定する。従って、上記実施例1で酵素エステル交換反応の前後の油脂に対して、HPLCを利用し油脂中のトリグリセリドの種類と含量を確認した。
OOO:トリオレイン(triolein)
SOO:1-ステアロイル-2,3-ジオレイルグリセリン(1-stearoyl-2,3-dioleoylglycerin)
SOS:1,3-ジステアロイル-2-オレオイルグリセリン(1,3-distearoyl-2-oleoylglycerin)
POS:1-パミトイル-2-オレイル-3-ステアロイルグリセリン(1-palmitoyl-2-oleoyl-3-stearoylglycerin)
上記実施例1で得られた固体相の中融点油脂に対して、核磁気共鳴を利用し、固体脂含量(Solid Fat Content:SFC)を分析した。固体脂含量分析のための核磁気共鳴分析条件を下記の表2に表した。
示差熱量計で溶剤分別の前後に対して溶融プロファイル(Melting Profile)を測定することができ、これで、高融点、低融点の分画が除去の可否が判る。実施例1のアセトン分別により最終的に得られた固体相の中融点油脂に対して、DSCプロファイルを測定した。
Claims (7)
- 原料油脂を溶剤に溶解させて油脂溶液を製造する工程と、
上記油脂溶液を10〜25℃に維持して高融点分画を結晶化して除去する工程と、
上記高融点分画が除去された油脂溶液を0〜15℃に維持して中融点分画を結晶化して得る工程とを含み、
溶剤分別法によって、トリグリセリド中に1,3-ジステアロイル-2-オレオイルグリセリン(SOS)を85w/w%以上含むSOSハードバターを製造することを特徴とするハードバターの製造方法。 - 上記原料油脂は、オレイン酸を80%以上含む植物性油脂とステアリン酸エチルエステルとをsn-1,3位に特異性を有する酵素を利用してエステル交換反応を施した後、エステルを除去してトリグリセリドにしたことを特徴とする請求項1に記載のハードバターの製造方法。
- 上記原料油脂は、ハイオレイックひまわり油であることを特徴とする請求項2に記載のハードバターの製造方法。
- 上記のエチルエステルの除去を、0.001〜0.1mbar、200〜250℃で行うことを特徴とする請求項2に記載のハードバターの製造方法。
- 上記溶剤は、ヘキサン、アセトン、メチルエチルケトン、エタノール、またはこれらの混合物であることを特徴とする請求項1に記載のハードバターの製造方法。
- 上記油脂溶液を製造する工程において、油脂溶液は、原料油脂を25w/w%以上含むように製造されることを特徴とする請求項1に記載のハードバターの製造方法。
- 請求項1〜6の何れか1項に記載のハードバターの製造方法により製造されるSOSハードバターを含むチョコレート類。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2009-0091779 | 2009-09-28 | ||
KR1020090091779A KR101075559B1 (ko) | 2009-09-28 | 2009-09-28 | 하드버터의 제조방법 |
PCT/KR2009/006249 WO2011037296A1 (ko) | 2009-09-28 | 2009-10-28 | 하드버터의 제조방법 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2012529907A true JP2012529907A (ja) | 2012-11-29 |
JP5589071B2 JP5589071B2 (ja) | 2014-09-10 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2012515958A Active JP5589071B2 (ja) | 2009-09-28 | 2009-10-28 | ハードバターの製造方法 |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP2484216A1 (ja) |
JP (1) | JP5589071B2 (ja) |
KR (1) | KR101075559B1 (ja) |
CN (1) | CN102548420A (ja) |
RU (1) | RU2511238C2 (ja) |
SG (1) | SG178826A1 (ja) |
WO (1) | WO2011037296A1 (ja) |
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US9795152B2 (en) | 2012-07-24 | 2017-10-24 | Advanta Holdings Bv | 1,3-specific intraesterification |
MY160097A (en) * | 2013-02-13 | 2017-02-28 | Malaysian Palm Oil Board | A process to produce high oleic liquid palm oil fraction |
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JPH061996A (ja) * | 1992-06-17 | 1994-01-11 | Asahi Denka Kogyo Kk | 油脂のエステル交換方法 |
JPH06327475A (ja) * | 1993-05-24 | 1994-11-29 | Nisshin Oil Mills Ltd:The | 固定化酵素の調製方法 |
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JPS5263206A (en) * | 1975-11-19 | 1977-05-25 | Fuji Oil Co Ltd | Fractionation of shea butter |
GB1562011A (en) * | 1977-01-20 | 1980-03-05 | Asahi Denka Kogyo Kk | Hard vegetable oil based butter |
ATE125426T1 (de) * | 1992-03-11 | 1995-08-15 | Loders Croklaan Bv | Verbesserte, auf triglycerid-additiven basierte schokoladezusammensetzungen. |
JPWO2006095505A1 (ja) * | 2005-03-08 | 2008-08-14 | 不二製油株式会社 | 耐熱性フィリング類及びその製造法 |
MY142954A (en) * | 2005-05-13 | 2011-01-31 | Nisshin Oillio Group Ltd | Intermolecular compounds of fatty acid triglycerides |
TWI429400B (zh) | 2007-09-07 | 2014-03-11 | Nisshin Oillio Group Ltd | 硬奶油的製造方法 |
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- 2009-10-28 RU RU2012102253/13A patent/RU2511238C2/ru active
- 2009-10-28 WO PCT/KR2009/006249 patent/WO2011037296A1/ko active Application Filing
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH061996A (ja) * | 1992-06-17 | 1994-01-11 | Asahi Denka Kogyo Kk | 油脂のエステル交換方法 |
JPH06327475A (ja) * | 1993-05-24 | 1994-11-29 | Nisshin Oil Mills Ltd:The | 固定化酵素の調製方法 |
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KR20110034295A (ko) | 2011-04-05 |
EP2484216A1 (en) | 2012-08-08 |
JP5589071B2 (ja) | 2014-09-10 |
RU2511238C2 (ru) | 2014-04-10 |
CN102548420A (zh) | 2012-07-04 |
WO2011037296A1 (ko) | 2011-03-31 |
SG178826A1 (en) | 2012-04-27 |
RU2012102253A (ru) | 2013-11-10 |
KR101075559B1 (ko) | 2011-10-20 |
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