WO2014016245A1 - Random intraesterification - Google Patents
Random intraesterification Download PDFInfo
- Publication number
- WO2014016245A1 WO2014016245A1 PCT/EP2013/065408 EP2013065408W WO2014016245A1 WO 2014016245 A1 WO2014016245 A1 WO 2014016245A1 EP 2013065408 W EP2013065408 W EP 2013065408W WO 2014016245 A1 WO2014016245 A1 WO 2014016245A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- fat
- oil
- triglycerides
- saturated
- unsaturated
- Prior art date
Links
- 239000003921 oil Substances 0.000 claims abstract description 55
- 235000019198 oils Nutrition 0.000 claims abstract description 54
- 150000003626 triacylglycerols Chemical class 0.000 claims abstract description 50
- 238000000034 method Methods 0.000 claims abstract description 36
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 29
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 27
- 239000000194 fatty acid Substances 0.000 claims abstract description 27
- 229930195729 fatty acid Natural products 0.000 claims abstract description 27
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 26
- 230000008569 process Effects 0.000 claims abstract description 24
- 239000007787 solid Substances 0.000 claims abstract description 21
- 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 abstract description 19
- 235000012343 cottonseed oil Nutrition 0.000 claims abstract description 6
- 235000019486 Sunflower oil Nutrition 0.000 claims abstract description 5
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims abstract description 5
- 239000003549 soybean oil Substances 0.000 claims abstract description 5
- 235000012424 soybean oil Nutrition 0.000 claims abstract description 5
- 239000002600 sunflower oil Substances 0.000 claims abstract description 5
- 235000019484 Rapeseed oil Nutrition 0.000 claims abstract description 4
- 239000002385 cottonseed oil Substances 0.000 claims abstract description 4
- 235000019197 fats Nutrition 0.000 claims description 74
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 10
- 235000013305 food Nutrition 0.000 claims description 8
- 235000013310 margarine Nutrition 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000008162 cooking oil Substances 0.000 claims description 5
- 230000002255 enzymatic effect Effects 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 3
- 235000009508 confectionery Nutrition 0.000 claims description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 3
- 239000003925 fat Substances 0.000 abstract description 73
- 229920006395 saturated elastomer Polymers 0.000 description 16
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 239000007788 liquid Substances 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 235000021313 oleic acid Nutrition 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
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 5
- 239000005642 Oleic acid Substances 0.000 description 5
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 5
- 235000021355 Stearic acid Nutrition 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- 208000024172 Cardiovascular disease Diseases 0.000 description 3
- 238000008214 LDL Cholesterol Methods 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000009884 interesterification Methods 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
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 240000002791 Brassica napus Species 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 241000208818 Helianthus Species 0.000 description 2
- 235000003222 Helianthus annuus Nutrition 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- -1 but not limited to Chemical class 0.000 description 2
- 239000012159 carrier gas 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
- 238000004587 chromatography analysis Methods 0.000 description 2
- 235000019875 cocoa butter alternative Nutrition 0.000 description 2
- 239000008157 edible vegetable oil Substances 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 235000020778 linoleic acid Nutrition 0.000 description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 2
- 239000003264 margarine Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 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
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002314 glycerols Chemical group 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002889 oleic acids Chemical class 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
- 230000008092 positive effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000001304 sample melting Methods 0.000 description 1
- 235000021003 saturated fats Nutrition 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000002316 solid fats Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 238000009482 thermal adhesion granulation Methods 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 235000021081 unsaturated fats Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
-
- 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
Definitions
- the present invention relates to the process of intraesterification of fats.
- one or more types of triglycerides are modified by redistribution of the fatty acids between the triglycerides.
- Some food products such as margarine, spreads, coatings, fillings, and cooking oils, require specific properties such as spreadability, firmness, plasticity, mouthfeel and the release of flavour.
- Natural vegetable fats or oils used for food products often do not have these properties and require modification before they can be used.
- the main processes used for modification of fats or oils are fractionation, hydrogenation, and interesterification . These processes are known in the art and are, for instance, described in "Food Fats and Oils", Ninth Edition; Institute of Shortening and Edible Oils.
- Fractionation is the process in which the liquid and solid constituents of a fat or oil are separated and relies on the differences in melting points.
- Hydrogenation is a chemical reaction commonly used to convert unsaturated fatty acids to saturated fatty acids. Apart from converting liquid oils to semi-solids and/or solids, hydrogenation also increases the oxidative and thermal stability of the fat or oil. Hydrogenation can be partial or complete. Partial hydrogenation results in oils and soft solid fats and is often used in the production of cooking oils and margarines. A major disadvantage of partial hydrogenation is that it results in high levels of trans-isomers which have been implicated in cardiovascular disease.
- interesterification two or more desired oils or fats are blended and the fatty acids are redistributed between the triglycerides of these oils or fats.
- the selection and proportions of oil or fat types for in the reaction mixture determines the properties of the resulting oil or fat.
- Interesterification can be performed by chemical or enzymatic processes. In chemical interesterification two or more desired oils are blended, dried and a catalyst such as sodium methoxide is added. This process results in the random distribution of the fatty acids across the glycerol backbones of the triglycerides.
- Enzymatic esterification involves the random or position-specific redistribution of fatty acids by using an enzyme.
- the present inventors have applied the random redistribution of fatty acids with only one fat type, or one single fat type, instead of two or more fat types.
- the process in which only one fat type is used is herein
- Intraesterification This process can be applied to relatively new modified oils like high stearic high oleic oils in which a significant amount of saturated- unsaturated-unsaturated (SUU) type triglycerides is present.
- SAU saturated- unsaturated-unsaturated
- SUS saturated-unsaturated-saturated
- SSU saturated-saturated-unsaturated
- SSS saturated-saturated-saturated
- the invention thus provides a method for modifying one or more types of triglycerides in a fat or oil
- a single fat or oil selected from the group consisting of high stearic high oleic sunflower oil, high stearic high oleic soybean oil, high stearic high oleic rapeseed oil, high stearic high oleic cottonseed oil, palm olein and shea olein to an intraesterification process in which the fatty acids of the triglycerides of said fat are randomly redistributed between the triglycerides to obtain a fat with a modified solid fat content (SFC) profile and/or to obtain a fat with an increased melting point.
- SFC solid fat content
- SUS Triglycerides The differences between both types of SUS Triglycerides are melting behavior and oxidative stability.
- SOS type saturate-Oleic-saturate
- SOS type has melting points above 34°C. This fact conferes them very special characteristics depending on their relative concentration in the matrix (commercial fats and oils) in which they are present.
- concentration is high (about 80 %) , as in cocoa butter, the fat is brittle at room temperature and melts completely in the mouth (body temperature) , which are the highly appreciated characteristics of chocolate and cocoa butter alternatives.
- the concentration When the concentration is still significant (about 35 %) , they can be used as structuring fats i.e. in margarines and spreads. This means the capacity of retaining very high amounts of liquid oils in a special crystal network, that conferes these kind of products the
- the resulting SUS concentration increases to relative lower levels than those needed for cocoa butter alternatives or structuring fats.
- the change in SFC profile or melting behavior is enough in order to use this randomized fats in margarine, fillings and bakery applications .
- oxidative stability Another important characteristic is the oxidative stability. This is because the oxidation rate of linoleic acid (the main one in most of the liquid regular seedoils) is 40 times faster than oleic acid. This means that
- a third significant point is when S (saturate fatty acid) is stearic acid and U is oleic acid, (this is valid for high stearic high oleic oils and fractions but not for palm oleins in which the main S is palmitic acid) .
- Stearic acid is the only saturated fatty acid with the ability of generating solid or semisolid fats that is not considered harmful from a nutritional point of view because it has a neutral behavior regarding LDL cholesterol ("bad cholesterol") .
- a high concentration of oleic acid (a stable unsaturated) has a positive effect in lowering LDL cholesterol.
- the HSHO oils high stearic high oleic oils
- oleins are a good alternative to trans fats and other saturates (like palm oil and
- high stearic high oleic oils and fractions preferably used in the present invention (coming from modified traditional crops like sunflower, rapeseed, soybean, cottonseed) being originated from annual crops are more sustainable than tropical fats, specially because of the clearing of rainforest that takes place in the main palm oil producing countries, with very deleterious effect on environment .
- solid fat content (SFC) of fats and/or oils can be modified by the process of
- the invention resides in applying the
- SUS Saturated-unsaturated-saturated
- triglycerides in high stearic high oleic (HSHO) sunflower or high stearic high oleic (HSHO) soybean oils have a higher melting point than SUU type ( saturated-unsaturated- unsaturated) .
- SUU type saturated-unsaturated- unsaturated
- a fat or “one fat” as used herein is intended to refer to one oil or fat type, or single oil or fat type and not to a combination of different oil or fat types .
- Fats consist of a wide group of compounds that are generally soluble in organic solvents and generally
- fats are triglycerides, triesters of glycerol and any of several fatty acids.
- fat or “fats” is intended to refer to a mixture of triglycerides.
- triglyceride also referred to as TG, triacylglycerol , TAG, or triacylglyceride
- TG triacylglycerol
- TAG triacylglyceride
- the fatty acids in a fat can be any fatty acid.
- a fatty acid is a carboxylic acid with a long
- oils oils. In this application the terms fat and oil can be used interchangeably.
- fat refers to a mixture of triglycerides.
- triglycerides may comprise one or more types of
- triglycerides include for instance unsaturated-unsaturatedunsaturated (UUU) , saturated- unsaturated-unsaturated (SUU), unsaturated-saturated- unsaturated (USU) , unsaturated-unsaturated-saturated (UUS), saturated-saturated-unsaturated (SSU), saturated- unsaturated-saturated (SUS), unsaturated-saturated-saturated (USS), and saturated-saturated-saturated (SSS).
- UUU unsaturated-unsaturatedunsaturated
- SUU saturated- unsaturated-unsaturated
- USU unsaturated-saturated- unsaturated
- SSU saturated-saturated-unsaturated
- SUS saturated- unsaturated-saturated-saturated
- USS unsaturated-saturated-saturated
- SSSS saturated-saturated-saturated
- oil oil
- fat fat
- lipid lipid
- the words “oil” and “fat” are used interchangeably herein.
- the fat type can be obtained from any source.
- the fat is obtained from a vegetable source, including, but not limited to the following seed varieties: HSHO soybean, HSHO rapeseed, HSHO sunflower seed, HSHO cottonseed, palm and shea fruits.
- a vegetable source including, but not limited to the following seed varieties: HSHO soybean, HSHO rapeseed, HSHO sunflower seed, HSHO cottonseed, palm and shea fruits.
- the method of the present invention is particular suitable for fat types which comprise stearic acids and/or oleic acids, such as, but not limited to, high stearic high oleic (HSHO) sunflower oil, high stearic high oleic (HSHO) soybean oil, high stearic high oleic rapeseed oil, and high stearic high oleic (HSHO) cottonseed oil.
- HSHO high stearic high oleic
- HSHO high stearic high oleic
- soybean oil high stearic high oleic rapeseed oil
- HSHO high stearic high oleic
- the solid fat content (SFC) of the present fat type is changed by switching saturated- unsaturated-unsaturated (SUU) type triglycerides into saturated-unsaturated-saturated (SUS) type triglycerides, saturated-saturated-unsaturated (SSU) type triglycerides and/or saturated-saturated-saturated (SSS) type
- Intraesterification refers to the process in which fatty acids are redistributed between the triglycerides of only one fat type. The process of
- intraesterifying triglycerides of the present invention is performed by chemical reactions or by enzymatic processes with non specific 1,3 enzymes.
- Chemical reactions generally involve catalysis by sodium methoxide as described in
- the present randomly redistribution is carried out by a temperature within the range of 60 to 90 °C, preferably 75 to 85 °C, in the
- the present process provides an efficient method for intraesterification, of single fats resulting in a fat with an increased solid fat content (SFC) profile, when compared to the untreated singe fats .
- SFC solid fat content
- the present randomly redistribution is carried out by enzymatic processes.
- intraesterified product can be predicted by means of
- the level of one or more types of triglycerides of said fat has been modified by intraesterifying the fatty acids to obtain a random redistribution of the fatty acids between the triglycerides.
- saturated-unsaturated-saturated (SUS) type, saturated- saturated-unsaturated (SSU), and/or saturated- saturatedsaturated (SSS) type triglycerides in said fat is increased, changed, altered or modified as compared to the level of saturated-unsaturated-saturated (SUS) type, saturated-saturated-unsaturated (SSU), and/or saturated- saturated-saturated (SSS) type triglycerides in a fat that has not been modified.
- the fat obtained by the method of the present invention can be used in food applications, including, but not limited to, margarines, spreads, confectionery products and cooking oils.
- the fat produced by the method of the present invention can also be used as a third component to decrease the amount of structuring fat used in a blend.
- Figure 1 shows a predictive equation for random intraesterification.
- FIG. 2 shows the solid fat content of HSHO oils and oleins by NMR before and after the randomization.
- the TAG composition of the different stearin fractions was determined by GC using an Agilent 6890 gas chromatograph (Palo Alto, CA) equipped with a Quadrex
- Aluminium-Clad 40065HT (30 m length, 0.25 mm i.d., 0.1 pm film thickness (Woodbridge, CT, USA) and a flame ionization detector. Hydrogen was used as the carrier gas at a linear rate of 50 cm/ s and split ratio 1:80.
- the injector and detector temperatures were 360 and 370°C respectively, the oven temperature was 335°C, and a head pressure gradient from 100 to 180 kPa was applied.
- the relative response of the FID was corrected according to the method of Carelli and Cert 1993 (Comparative study of the determination of triacylglycerols in vegetable oils using chromatographic techniques. J. Chromatogr .630 , 213-222).
- Fatty acids were analyzed as their methyl esters in a similar chromatograph but equipped with a Supelco SP- 2380 fused silica capillary column (30 m length; 0.25 mm i.d.; 0.20 pm film thickness: Bellefonte, PA).
- the analysis conditions were carrier gas (hydrogen) flow at 28 cm « s-l, detector and injector temperature were 200°C, whereas oven temperature was kept at 170°C.
- Example 2 Two more trials were performed as described in Example 2, specifically one additional trial for the olein and 2 additional trials for the oil) .
- the solid fat content (SFC) of the HSHO oil, HSHO olein fraction and the intraesterified products of examples 2 and 3 were determined using NMR. (Nuclear magnetic
- Figure 2 shows that the solid fat content of the random intraesterified products of example 2 and 3 is modified compared with the solid fat content of the original HSHO oil and HSHO olein fraction, becoming suitable to be used in some confectionery fillings and as part of the fat phase of margarines and spreads.
- EXAMPLE 5
- the melting point of the HSHO oil, HSHO olein fraction and random intraesterified products of examples 2 and 3 was determined using standard techniques.
- Table 2 shows that the melting point of the random intraesterified HSHO oil and HSHO olein fraction are
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Zoology (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)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Edible Oils And Fats (AREA)
- Fats And Perfumes (AREA)
- Confectionery (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
RU2015105746A RU2668269C2 (en) | 2012-07-24 | 2013-07-22 | Random intraesterification |
US14/414,692 US11414624B2 (en) | 2012-07-24 | 2013-07-22 | Random intraesterification |
IN481DEN2015 IN2015DN00481A (en) | 2012-07-24 | 2013-07-22 | |
UAA201501567A UA115066C2 (en) | 2012-07-24 | 2013-07-22 | Random intraesterification |
BR112015001326A BR112015001326B8 (en) | 2012-07-24 | 2013-07-22 | METHOD FOR MODIFYING ONE OR MORE TYPES OF TRIGLYCERIDES INTO A FAT OR OIL, TRIGLYCERIDE, FAT AND THEIR USE |
EP13753284.2A EP2880142B1 (en) | 2012-07-24 | 2013-07-22 | Random intraesterification |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EPPCT/EP2012/064546 | 2012-07-24 | ||
EP2012064546 | 2012-07-24 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2014016245A1 true WO2014016245A1 (en) | 2014-01-30 |
WO2014016245A4 WO2014016245A4 (en) | 2014-03-27 |
Family
ID=49036557
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2013/065408 WO2014016245A1 (en) | 2012-07-24 | 2013-07-22 | Random intraesterification |
Country Status (9)
Country | Link |
---|---|
US (1) | US11414624B2 (en) |
EP (1) | EP2880142B1 (en) |
AR (1) | AR091872A1 (en) |
BR (1) | BR112015001326B8 (en) |
HU (1) | HUE038364T2 (en) |
IN (1) | IN2015DN00481A (en) |
RU (1) | RU2668269C2 (en) |
UA (1) | UA115066C2 (en) |
WO (1) | WO2014016245A1 (en) |
Cited By (5)
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 |
WO2017042149A1 (en) * | 2015-09-07 | 2017-03-16 | Fuji Oil Europe | Fat compositions |
WO2017055102A1 (en) * | 2015-09-29 | 2017-04-06 | Loders Croklaan B.V. | Temperature tolerant chocolate spread or filling and method of preparation |
EP3245876B1 (en) | 2016-05-16 | 2019-05-01 | Unigra' S.r.l. | Spreadable food composition |
WO2019166598A1 (en) | 2018-03-01 | 2019-09-06 | Bunge Növényolajipari Zártköruen Muködo Részvénytársaság | New high stearic oilseed stearin fat and process for its preparation |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2020053378A1 (en) | 2018-09-14 | 2020-03-19 | Bunge Növényolajipari Zártköruen Muködo Részvénytársaság | Fat spread product, process for preparing the same, and its use as table spread or in bakery |
CN115279876A (en) * | 2020-01-13 | 2022-11-01 | 阿彻丹尼尔斯米德兰公司 | Enzymatic lactonization of non-tropical vegetable oils for structuring food spreads and margarines |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6277433B1 (en) * | 1999-03-19 | 2001-08-21 | Loders Croklaan B.V. | Fat mixtures |
WO2006133124A1 (en) * | 2005-06-06 | 2006-12-14 | Aarhuskarlshamn Usa, Inc. | Low trans puff pastry composition, method of use and puff pastry products |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1577933A (en) * | 1976-02-11 | 1980-10-29 | Unilever Ltd | Fat process and composition |
EP1439758B1 (en) * | 2001-11-02 | 2009-03-18 | AarhusKarlshamn Denmark A/S | Non-lauric, non-trans, non-temper fat compositions |
AU2003248335B2 (en) * | 2002-02-28 | 2006-03-02 | Upfield Europe B.V. | Triglyceride fat suitable for spread manufacture |
AR061984A1 (en) * | 2006-07-14 | 2008-08-10 | Consejo Superior Investigacion | LIQUID AND STABLE FRACTIONED OILS |
MY158495A (en) * | 2008-04-24 | 2016-10-14 | Nisshin Oillio Group Ltd | Fat-and-oil composition, and oil-in water emulsified product containing the fat-and-oil composition |
-
2013
- 2013-07-22 BR BR112015001326A patent/BR112015001326B8/en active IP Right Grant
- 2013-07-22 IN IN481DEN2015 patent/IN2015DN00481A/en unknown
- 2013-07-22 UA UAA201501567A patent/UA115066C2/en unknown
- 2013-07-22 HU HUE13753284A patent/HUE038364T2/en unknown
- 2013-07-22 WO PCT/EP2013/065408 patent/WO2014016245A1/en active Application Filing
- 2013-07-22 US US14/414,692 patent/US11414624B2/en active Active
- 2013-07-22 RU RU2015105746A patent/RU2668269C2/en active
- 2013-07-22 EP EP13753284.2A patent/EP2880142B1/en active Active
- 2013-07-24 AR ARP130102616A patent/AR091872A1/en active IP Right Grant
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6277433B1 (en) * | 1999-03-19 | 2001-08-21 | Loders Croklaan B.V. | Fat mixtures |
WO2006133124A1 (en) * | 2005-06-06 | 2006-12-14 | Aarhuskarlshamn Usa, Inc. | Low trans puff pastry composition, method of use and puff pastry products |
Non-Patent Citations (4)
Title |
---|
"Food Fats and Oils", INSTITUTE OF SHORTENING AND EDIBLE OILS |
J. CHROMATOGR., vol. 630, pages 213 - 222 |
LIEN ET AL: "The role of fatty acid composition and positional distribution in fat absorption in infants", JOURNAL OF PEDIATRICS, MOSBY-YEAR BOOK, ST. LOUIS, MO, US, vol. 125, no. 5, 1 November 1994 (1994-11-01), pages S62 - S68, XP022291794, ISSN: 0022-3476, DOI: 10.1016/S0022-3476(06)80738-9 * |
NEFF, W.E., AND LIST, G. R.: "Oxidative stability of natural and randomized high-palmitic- and high-stearic-acid oils from genetically modified soybean varieties", JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY., vol. 76, no. 7, 1999, USAOCS PRESS, CHAMPAIGN, IL., pages 825 - 831, XP002717484, ISSN: 0003-021X * |
Cited By (8)
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 |
WO2017042149A1 (en) * | 2015-09-07 | 2017-03-16 | Fuji Oil Europe | Fat compositions |
WO2017055102A1 (en) * | 2015-09-29 | 2017-04-06 | Loders Croklaan B.V. | Temperature tolerant chocolate spread or filling and method of preparation |
CN108135196A (en) * | 2015-09-29 | 2018-06-08 | 荷兰洛德斯克罗科兰有限公司 | Temperature tolerance chocolate spread or filling and preparation method |
CN108135196B (en) * | 2015-09-29 | 2021-06-15 | 荷兰洛德斯克罗科兰有限公司 | Temperature-tolerant chocolate spread or filling and method of making |
EP3245876B1 (en) | 2016-05-16 | 2019-05-01 | Unigra' S.r.l. | Spreadable food composition |
WO2019166598A1 (en) | 2018-03-01 | 2019-09-06 | Bunge Növényolajipari Zártköruen Muködo Részvénytársaság | New high stearic oilseed stearin fat and process for its preparation |
CN111935987A (en) * | 2018-03-01 | 2020-11-13 | 纳文尤拉吉帕瑞扎特克文两合供应公司 | Novel high stearic acid oilseed stearin fat and preparation method thereof |
Also Published As
Publication number | Publication date |
---|---|
HUE038364T2 (en) | 2018-10-29 |
EP2880142B1 (en) | 2018-04-11 |
US20150166932A1 (en) | 2015-06-18 |
AR091872A1 (en) | 2015-03-04 |
WO2014016245A4 (en) | 2014-03-27 |
RU2668269C2 (en) | 2018-09-28 |
BR112015001326B1 (en) | 2021-10-19 |
RU2015105746A (en) | 2016-09-10 |
IN2015DN00481A (en) | 2015-06-26 |
BR112015001326B8 (en) | 2022-10-18 |
EP2880142A1 (en) | 2015-06-10 |
US11414624B2 (en) | 2022-08-16 |
BR112015001326A2 (en) | 2017-07-04 |
UA115066C2 (en) | 2017-09-11 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US11414624B2 (en) | Random intraesterification | |
Oliveira et al. | Chemical interesterification of blends with palm stearin and patawa oil | |
KR101483336B1 (en) | Fat and method for producing fat | |
JP5421496B1 (en) | Oil and fat composition and plastic oil and fat composition | |
Shin et al. | Enzymatic interesterification of anhydrous butterfat with flaxseed oil and palm stearin to produce low-trans spreadable fat | |
EP2636313B1 (en) | Glyceride composition obtainable from shea oil | |
JPWO2010110260A1 (en) | Method for producing hard butter composition | |
EP2877034B1 (en) | 1,3-specific intraesterification | |
US20070148312A1 (en) | Non-hydrogenated vegetable oil based shortening containing an elevated diglyceride emulsifier composition | |
Verstringe et al. | Enzymatic and other modification techniques to produce cocoa butter alternatives | |
Shankar Shetty et al. | Plastic fats from sal, mango and palm oil by lipase catalyzed interesterification | |
Debnath et al. | Hydrodynamic, thermo-analytical and molecular structural investigations of enzyme interesterified oil and its thermo-oxidative stability by thermogravimetric analysis | |
Chu et al. | Physical and chemical properties of a lipase-transesterified palm stearin/palm kernel olein blend and its isopropanol-solid and high melting triacylglycerol fractions | |
JP5353349B2 (en) | Migration inhibitor additive | |
JP5830582B2 (en) | Fats and oils | |
Musavi et al. | Formulation of trans-free margarines using hydrogenated and interesterified palm olein | |
Lee et al. | Blending, hydrogenation, fractionation and interesterification processing | |
Huey et al. | Characterization of low saturation palm oil products after continuous enzymatic interesterification and dry fractionation | |
Xu et al. | Sheaolein-based cold-soluble powder fats with medium-and long-chain triacylglycerol: production via chemical interesterification using sheaolein and palm kernel stearin | |
JP2010081834A (en) | Method for producing hard butter composition | |
JP2023067821A (en) | Oil-and-fat composition | |
HITHAMANI et al. | Lipase-mediated interesterification of oils and fats for the preparation of bakery and confectionery fats | |
Alves et al. | Structuration of lipid bases zero-trans and palm oil-free for food applications | |
JP6777528B2 (en) | Oil composition | |
Marangoni et al. | Trends in Interesterification of Fats and Oils |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 13753284 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 14414692 Country of ref document: US |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2013753284 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: A201501567 Country of ref document: UA |
|
ENP | Entry into the national phase |
Ref document number: 2015105746 Country of ref document: RU Kind code of ref document: A |
|
REG | Reference to national code |
Ref country code: BR Ref legal event code: B01A Ref document number: 112015001326 Country of ref document: BR |
|
ENP | Entry into the national phase |
Ref document number: 112015001326 Country of ref document: BR Kind code of ref document: A2 Effective date: 20150121 |