DK2877034T3 - 1,3-specifik intra-esterificering - Google Patents
1,3-specifik intra-esterificering Download PDFInfo
- Publication number
- DK2877034T3 DK2877034T3 DK13741714.3T DK13741714T DK2877034T3 DK 2877034 T3 DK2877034 T3 DK 2877034T3 DK 13741714 T DK13741714 T DK 13741714T DK 2877034 T3 DK2877034 T3 DK 2877034T3
- Authority
- DK
- Denmark
- Prior art keywords
- oil
- fraction
- sus
- olein
- selective
- Prior art date
Links
- 238000005886 esterification reaction Methods 0.000 title claims 4
- 239000003921 oil Substances 0.000 claims description 115
- 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 claims description 69
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 claims description 67
- 238000000034 method Methods 0.000 claims description 50
- 238000005194 fractionation Methods 0.000 claims description 26
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 20
- 230000002255 enzymatic effect Effects 0.000 claims description 12
- 230000035484 reaction time Effects 0.000 claims description 12
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 10
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 10
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 10
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000005642 Oleic acid Substances 0.000 claims description 10
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 10
- 235000013310 margarine Nutrition 0.000 claims description 8
- 108090001060 Lipase Proteins 0.000 claims description 7
- 102000004882 Lipase Human genes 0.000 claims description 7
- 239000004367 Lipase Substances 0.000 claims description 6
- 235000019421 lipase Nutrition 0.000 claims description 6
- 239000003264 margarine Substances 0.000 claims description 6
- 239000008162 cooking oil Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 4
- 235000020238 sunflower seed Nutrition 0.000 claims description 4
- 241000208818 Helianthus Species 0.000 claims description 2
- 235000003222 Helianthus annuus Nutrition 0.000 claims description 2
- 241000235403 Rhizomucor miehei Species 0.000 claims description 2
- 241000223257 Thermomyces Species 0.000 claims description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims 4
- 150000001336 alkenes Chemical class 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 235000019198 oils Nutrition 0.000 description 101
- 239000003925 fat Substances 0.000 description 34
- 235000019197 fats Nutrition 0.000 description 34
- 150000003626 triacylglycerols Chemical class 0.000 description 32
- 108090000790 Enzymes Proteins 0.000 description 23
- 102000004190 Enzymes Human genes 0.000 description 23
- 235000014113 dietary fatty acids Nutrition 0.000 description 19
- 229930195729 fatty acid Natural products 0.000 description 19
- 239000000194 fatty acid Substances 0.000 description 19
- 150000004665 fatty acids Chemical class 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- 239000007788 liquid Substances 0.000 description 10
- 235000019486 Sunflower oil Nutrition 0.000 description 9
- 239000002600 sunflower oil Substances 0.000 description 9
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 235000013305 food Nutrition 0.000 description 6
- 238000009482 thermal adhesion granulation Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 238000009884 interesterification Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000004671 saturated fatty acids Chemical class 0.000 description 4
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 4
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 4
- 208000024172 Cardiovascular disease Diseases 0.000 description 3
- 238000008214 LDL Cholesterol Methods 0.000 description 3
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 239000008157 edible vegetable oil Substances 0.000 description 3
- 235000020778 linoleic acid Nutrition 0.000 description 3
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 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
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- RBLADLVPSYELCA-UHFFFAOYSA-N (Z)-Glycerol 1,3-dioctadecanoate 2-9-octadecenoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC RBLADLVPSYELCA-UHFFFAOYSA-N 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 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000019871 vegetable fat Nutrition 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
- 108010048733 Lipozyme Proteins 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009885 chemical interesterification Methods 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 235000019875 cocoa butter alternative Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000009886 enzymatic interesterification Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- MVLVMROFTAUDAG-UHFFFAOYSA-N ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC MVLVMROFTAUDAG-UHFFFAOYSA-N 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 150000002314 glycerols Chemical group 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000019629 palatability Nutrition 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000021003 saturated fats Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 235000021081 unsaturated fats Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings or cooking oils characterised by the production or working-up
- A23D9/04—Working-up
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/003—Compositions other than spreads
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/02—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by the production or working-up
- A23D7/04—Working-up
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6458—Glycerides by transesterification, e.g. interesterification, ester interchange, alcoholysis or acidolysis
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Edible Oils And Fats (AREA)
- Fats And Perfumes (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Claims (9)
1. Fremgangsmåde til forøgelse af SUS-indholdet i en olie eller i en oleinfrakti-on, hvilken fremgangsmåde omfatter at udføre en 1,3-selektiv enzymatisk intra-esterificering på en naturlig startolie eller en oleinfraktion, der er fremstillet deraf, hvor forholdet mellem SUS og SUU er mindst 1 : 1,5 og SSS-indholdet er lavt, især tæt på 0 %, hvor den naturlige startolie eller oleinfraktionen er en solsikkeolie med højt stearin-indhold og højt olein-indhold (HSHO) der er ekstraheret af solsikkefrø og ikke blandet med andre olier.
2. Fremgangsmåden ifølge krav 1, hvor forholdet mellem SUS og SUU er i rækkefølge med forøget præference mindst 1 : 1,5, 1 : 2, 1 : 3,5, 1 : 5, 1 : 7,5, 1 :10, 1 : 15.
3. Fremgangsmåde til forøgelse af stearinudbyttet fra en startolie eller startole-infraktion ved fraktionering deraf, hvilken fremgangsmåde omfatter trinnene: a) eventuelt at fraktionere en startolie med et forhold mellem SUS og SUU på mindst 1 : 1,5 og et lavt SSS-indhold, især tæt på 0 %, for at opnå en stearinfraktion og en startoleinfraktion; b) at udføre fremgangsmåden ifølge krav 1 eller 2 på startolien eller startoleinfraktionen for at opnå 1,3-selektiv intra-esterificeret olie eller olein med et højere SUS-indhold end startolien eller startoleinfraktionen; c) at fraktionere den 1,3-selektive intra-esterificerede olie eller olein, der således opnås for at opnå en stearinfraktion og en oleinfraktion.
4. Fremgangsmåden ifølge krav 3, hvor tota I stearin ud byttet fra trin (a) og (c) til sammen er højere end stearinudbyttet efter fraktionering af startolien.
5. Fremgangsmåde ifølge et hvilket som helst af kravene 1-4, hvor den umættede U i SUS og/eller SUU er oliesyre.
6. Fremgangsmåde ifølge et hvilket som helst af kravene 1-5, hvor reaktionstiden for den 1,3-selektive enzymatiske intra-esterificering er mindst ca. 30 minutter, fortrinsvis mellem ca. 2 og 8 timer, mere fortrinsvis mellem ca. 2 og 6 timer, endnu mere foretrukket mellem ca. 2 og 4 timer og mest fortrinsvis ca. 4 timer.
7. Fremgangsmåde ifølge et hvilket som helst af kravene 1-6, hvor den 1,3-selektive enzymatiske intra-esterificering udføres under anvendelse af lipase-enzymer, især lipasen fra Rhizomucor miehei (RMIM) eller lipasen fra Thermo-myces lanuginosis (TLIM).
8. Stearinfraktion der kan opnås ved at udføre fremgangsmåden ifølge et hvilket som helst af kravene 3-7.
9. Anvendelse af stearinfraktionen ifølge krav 8 i margarine, smørepålæg, belægninger, fyldstoffer, stegeolierog madolie.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP2012064547 | 2012-07-24 | ||
| PCT/EP2013/065419 WO2014016250A1 (en) | 2012-07-24 | 2013-07-22 | 1,3-specific intraesterification |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2877034T3 true DK2877034T3 (da) | 2019-01-28 |
Family
ID=48875017
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK13741714.3T DK2877034T3 (da) | 2012-07-24 | 2013-07-22 | 1,3-specifik intra-esterificering |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9795152B2 (da) |
| EP (1) | EP2877034B1 (da) |
| JP (1) | JP6749761B2 (da) |
| AR (1) | AR091873A1 (da) |
| BR (1) | BR112015001616B8 (da) |
| DK (1) | DK2877034T3 (da) |
| ES (1) | ES2704278T3 (da) |
| HU (1) | HUE041320T2 (da) |
| IN (1) | IN2015DN00523A (da) |
| RU (1) | RU2635696C2 (da) |
| UA (1) | UA117348C2 (da) |
| WO (1) | WO2014016250A1 (da) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20170049121A1 (en) * | 2015-08-20 | 2017-02-23 | Bunge Oils, Inc. | High stearic high oleic shortening compositions and methods of making and using the same |
| MY206870A (en) * | 2018-09-14 | 2025-01-10 | Bunge Nvnyolajipari Zrtkruen Mukdo Rszvnytrsasg | Fat spread product, process for preparing the same, and its use as table spread or in bakery |
| KR102172409B1 (ko) * | 2018-12-18 | 2020-11-02 | 충남대학교산학협력단 | 저소화성 유지 조성물 및 아실 마이그레이션 반응을 사용한 이의 제조방법 |
| US20230062018A1 (en) * | 2020-01-13 | 2023-03-02 | Archer Daniels Midland Company | Enzymatic intraesterification of non-tropical plant oil for structuring food spreads and margarine |
| AU2021253529A1 (en) | 2020-04-09 | 2022-09-08 | Société des Produits Nestlé S.A. | Method for manufacturing sn-2 palmitic triacylglycerols |
| CN115197784B (zh) * | 2022-07-08 | 2024-01-09 | 华南理工大学 | 一种猪油替代油脂及其制备方法与应用 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5288619A (en) * | 1989-12-18 | 1994-02-22 | Kraft General Foods, Inc. | Enzymatic method for preparing transesterified oils |
| US6022577A (en) * | 1990-12-07 | 2000-02-08 | Nabisco Technology Company | High stearic acid soybean oil blends |
| JPH06240290A (ja) * | 1993-02-16 | 1994-08-30 | Asahi Denka Kogyo Kk | 分別軟質油の加工方法 |
| JP3485522B2 (ja) | 2000-05-11 | 2004-01-13 | 日清オイリオ株式会社 | アイスコーティング用油脂組成物およびアイスコーティング用剤 |
| SK285334B6 (sk) | 2000-06-15 | 2006-11-03 | Unilever Nv | Spôsob prípravy triglyceridového tuku, spôsob prípravy tukovej fázy, potravinový výrobok s obsahom tukovej zmesi a použitie tukovej zmesi |
| UA92455C2 (ru) | 2003-11-14 | 2010-11-10 | Консехо Супериор Де Инвестигасионес Сьентификас | Масло, полученное из семян подсолнечника, с модифицированным распределением жирных кислот в молекуле триацилглицерина |
| AR061984A1 (es) * | 2006-07-14 | 2008-08-10 | Consejo Superior Investigacion | Aceites fraccionados liquidos y estables |
| KR20090031740A (ko) | 2006-07-19 | 2009-03-27 | 닛신 오일리오그룹 가부시키가이샤 | 초콜릿 제품에 적합한 하드버터의 제조방법 |
| TWI429400B (zh) | 2007-09-07 | 2014-03-11 | Nisshin Oillio Group Ltd | 硬奶油的製造方法 |
| KR101075559B1 (ko) * | 2009-09-28 | 2011-10-20 | 씨제이제일제당 (주) | 하드버터의 제조방법 |
-
2013
- 2013-07-22 BR BR112015001616A patent/BR112015001616B8/pt active IP Right Grant
- 2013-07-22 UA UAA201501568A patent/UA117348C2/uk unknown
- 2013-07-22 DK DK13741714.3T patent/DK2877034T3/da active
- 2013-07-22 EP EP13741714.3A patent/EP2877034B1/en active Active
- 2013-07-22 RU RU2015105971A patent/RU2635696C2/ru active
- 2013-07-22 HU HUE13741714A patent/HUE041320T2/hu unknown
- 2013-07-22 ES ES13741714T patent/ES2704278T3/es active Active
- 2013-07-22 WO PCT/EP2013/065419 patent/WO2014016250A1/en not_active Ceased
- 2013-07-22 JP JP2015523515A patent/JP6749761B2/ja active Active
- 2013-07-22 US US14/415,122 patent/US9795152B2/en active Active
- 2013-07-22 IN IN523DEN2015 patent/IN2015DN00523A/en unknown
- 2013-07-24 AR ARP130102617A patent/AR091873A1/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| JP2015522296A (ja) | 2015-08-06 |
| RU2015105971A (ru) | 2016-09-10 |
| RU2635696C2 (ru) | 2017-11-15 |
| BR112015001616A2 (pt) | 2017-07-04 |
| AR091873A1 (es) | 2015-03-04 |
| EP2877034B1 (en) | 2018-10-03 |
| US9795152B2 (en) | 2017-10-24 |
| US20150164101A1 (en) | 2015-06-18 |
| JP6749761B2 (ja) | 2020-09-02 |
| BR112015001616B1 (pt) | 2020-08-04 |
| IN2015DN00523A (da) | 2015-06-26 |
| BR112015001616B8 (pt) | 2022-10-18 |
| ES2704278T3 (es) | 2019-03-15 |
| EP2877034A1 (en) | 2015-06-03 |
| UA117348C2 (uk) | 2018-07-25 |
| HUE041320T2 (hu) | 2019-05-28 |
| WO2014016250A1 (en) | 2014-01-30 |
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