WO2007029018A1 - Process for producing dioleyl palmitoyl glyceride - Google Patents
Process for producing dioleyl palmitoyl glyceride Download PDFInfo
- Publication number
- WO2007029018A1 WO2007029018A1 PCT/GB2006/003343 GB2006003343W WO2007029018A1 WO 2007029018 A1 WO2007029018 A1 WO 2007029018A1 GB 2006003343 W GB2006003343 W GB 2006003343W WO 2007029018 A1 WO2007029018 A1 WO 2007029018A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- palm oil
- process according
- glyceride
- weight
- stearin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 62
- 230000008569 process Effects 0.000 title claims abstract description 54
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 claims abstract description 87
- 239000000203 mixture Substances 0.000 claims abstract description 67
- 235000019482 Palm oil Nutrition 0.000 claims abstract description 55
- 239000002540 palm oil Substances 0.000 claims abstract description 55
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 27
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims abstract description 22
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims abstract description 22
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims abstract description 22
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000005642 Oleic acid Substances 0.000 claims abstract description 22
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims abstract description 22
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 16
- 239000011630 iodine Substances 0.000 claims abstract description 16
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- -1 glyceride ester Chemical class 0.000 claims abstract description 5
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 44
- 125000005456 glyceride group Chemical group 0.000 claims description 41
- 238000005194 fractionation Methods 0.000 claims description 23
- 235000021314 Palmitic acid Nutrition 0.000 claims description 15
- 150000003626 triacylglycerols Chemical class 0.000 claims description 15
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 238000004061 bleaching Methods 0.000 claims description 6
- 235000019486 Sunflower oil Nutrition 0.000 claims description 5
- 239000002600 sunflower oil Substances 0.000 claims description 5
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 5
- 239000008158 vegetable oil Substances 0.000 claims description 5
- 239000003346 palm kernel oil Substances 0.000 claims description 4
- 235000019865 palm kernel oil Nutrition 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 3
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 2
- 239000003549 soybean oil Substances 0.000 claims description 2
- 235000012424 soybean oil Nutrition 0.000 claims description 2
- 125000005313 fatty acid group Chemical group 0.000 claims 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 abstract 1
- 239000003925 fat Substances 0.000 description 47
- 235000019197 fats Nutrition 0.000 description 47
- 150000004665 fatty acids Chemical class 0.000 description 25
- 235000021313 oleic acid Nutrition 0.000 description 20
- 235000014113 dietary fatty acids Nutrition 0.000 description 16
- 229930195729 fatty acid Natural products 0.000 description 16
- 239000000194 fatty acid Substances 0.000 description 16
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 12
- 108090000790 Enzymes Proteins 0.000 description 11
- 102000004190 Enzymes Human genes 0.000 description 11
- 235000020256 human milk Nutrition 0.000 description 9
- 210000004251 human milk Anatomy 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
- 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 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 108090001060 Lipase Proteins 0.000 description 6
- 102000004882 Lipase Human genes 0.000 description 6
- 239000004367 Lipase Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229940088598 enzyme Drugs 0.000 description 6
- 229940040461 lipase Drugs 0.000 description 6
- 235000019421 lipase Nutrition 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 150000004670 unsaturated fatty acids Chemical group 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 235000021588 free fatty acids Nutrition 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 235000013336 milk Nutrition 0.000 description 4
- 239000008267 milk Substances 0.000 description 4
- 210000004080 milk Anatomy 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 235000008452 baby food Nutrition 0.000 description 3
- 239000011942 biocatalyst Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 235000005911 diet Nutrition 0.000 description 3
- 230000000378 dietary effect Effects 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 235000021243 milk fat Nutrition 0.000 description 3
- 235000016709 nutrition Nutrition 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 208000016444 Benign adult familial myoclonic epilepsy Diseases 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
- 108010048733 Lipozyme Proteins 0.000 description 2
- 241000235403 Rhizomucor miehei Species 0.000 description 2
- 241000303962 Rhizopus delemar Species 0.000 description 2
- 240000005384 Rhizopus oryzae Species 0.000 description 2
- 235000013752 Rhizopus oryzae Nutrition 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 208000016427 familial adult myoclonic epilepsy Diseases 0.000 description 2
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 2
- 125000001924 fatty-acyl group Chemical group 0.000 description 2
- ZGNITFSDLCMLGI-UHFFFAOYSA-N flubendiamide Chemical compound CC1=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C1NC(=O)C1=CC=CC(I)=C1C(=O)NC(C)(C)CS(C)(=O)=O ZGNITFSDLCMLGI-UHFFFAOYSA-N 0.000 description 2
- 235000019860 lauric fat Nutrition 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
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 description 2
- PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 102000019280 Pancreatic lipases Human genes 0.000 description 1
- 108050006759 Pancreatic lipases Proteins 0.000 description 1
- 241000282849 Ruminantia Species 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 238000003965 capillary gas chromatography Methods 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 235000019621 digestibility Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 235000019211 fat replacer Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940057917 medium chain triglycerides Drugs 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 150000002943 palmitic acids Chemical class 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940116369 pancreatic lipase Drugs 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- NWOPIWLNGYLZCJ-UHFFFAOYSA-M sodium;(3-hexadecanoyloxy-2-hydroxypropyl) hydrogen phosphate Chemical compound [Na+].CCCCCCCCCCCCCCCC(=O)OCC(O)COP(O)([O-])=O NWOPIWLNGYLZCJ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960001947 tripalmitin Drugs 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 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
- C11C3/08—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with fatty acids
-
- 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
Definitions
- This invention relates to a process.
- the invention relates to a process for the production of the triglyceride l,3-dioleoyl-2-palmitoyl glyceride (also referred to as OPO).
- Triglycerides are important components of many products, especially food products.
- the triglyceride l,3-dioleoyl-2-palmitoyl glyceride is an important glyceride component of human milk fat.
- Fat compositions containing similar amounts of the principal fatty acids found in human milk fat may be derived from oils and fats of vegetable origin. However, there remains a significant difference in composition between milk replacement fats, derived from natural sources, and that of human milk fat. This difference arises because most glycerides of vegetable origin are unsaturated in the 2- position. In contrast, a substantial amount of palmitic acid occupies the 2-position of glycerides in human milk fat.
- EP-A-0209327 discloses milk replacement fat compositions comprising the triglyceride l,3-dioleoyl-2-palmitoyl glyceride (OPO).
- these fat compositions can be obtained by subjecting fatty mixtures comprising glycerides consisting substantially of more saturated 2-palmitoyl glycerides to a rearrangement catalyst, such as a lipase, which is regiospecific in activity in the 1- and 3 -positions of the glycerides.
- a rearrangement catalyst such as a lipase
- Enzymatic processes of this kind are also described in GB 1577933.
- unsaturated fatty acid residues may be introduced into the 1- and 3-positions of the 2-palmitoyl glycerides by exchange with unsaturated free fatty acids or their alkyl esters.
- WO 2005/036987 discloses a process for producing a fat base by reacting a palmitic rich oil with unsaturated fatty acids such as oleic acid.
- the total palmitic acid residue content of the fat base is at most 38% and at least 60% of the fatty acid moieties are in the 2- position of the glyceride backbone.
- a related disclosure can be found in WO 2005/037373, filed on the same day.
- a process for producing OPO is also disclosed in US 5,658,768.
- the process involves a further enzymic conversion to reduce the level of unsaturates in the composition.
- EP-A-0882797 describes a process for producing ABA triglycerides using a 1,3- specific enzyme, under controlled conditions of water activity.
- the present invention provides a process for the production of a composition comprising l,3-dioleyl-2-palmitoyl glyceride (OPO), wherein the process comprises subjecting a palm oil stearin, with an iodine value (IV) between about 2 and about 12 to enzymic transesterification, with oleic acid or a non-glyceride ester thereof (such as an alkyl ester of oleic acid with an alcohol having from 1 to 6 carbon atoms).
- a palm oil stearin with an iodine value (IV) between about 2 and about 12 to enzymic transesterification
- oleic acid or a non-glyceride ester thereof such as an alkyl ester of oleic acid with an alcohol having from 1 to 6 carbon atoms.
- the process of the invention comprises:
- the process of the invention aims to increase the amount of OPO formed in the product of the process.
- a further aim of the process is an increase in the nutritional quality of the product.
- Iodine value is determined according to standard methods known in the art (e.g., ASTM D5554-95 (2001)).
- the quality of the OPO composition can be determined from the carbon number of the constituent triglycerides in the composition.
- the reactant glyceride for the process is PPP, having a carbon number of 48 (C48), the product OPO has a carbon number of 52 and OPP and 000 have carbon numbers of 50 and 54, respectively. It is desirable to minimise the 000, PPP and OPP levels in the product, whilst maximising the amount of OPO.
- the presence of palmitoyl groups (i.e., palmitic acid residues) in the 2- position of the glyceride is particularly important.
- the quality of the product can be expressed by multiplying the amount of triglycerides other than C54 i.e, (100 — 54) by the ratio of total (C48 + C50 + C52) to ((3 X C48) + (2 X C50) + (C52)), which includes a factor for the number of pahnitoyl residues in the triglyceride, and/or by the amount of palmitic acid residues in the 2- position of the glyceride.
- composition or fraction produced by the process of the invention preferably has a value for the ratio:
- a suitable source of tripalmitoyl glyceride (PPP) for use in the process of the invention is palm oil stearin.
- Palm oil typically contains up to 12% by weight trisaturated acid glycerides including tripalmitoyl glyceride (PPP; also referred to as tripalmitin).
- Palm oil stearin may contain 4 parts tripahnitin and 1 part of symmetrical disaturated triglycerides, by weight.
- the palm oil stearin used in part (i) of the process is provided by fractionating palm oil or a derivative thereof.
- the palm oil stearin preferably has a palmitic acid content of at least 60% by weight, more preferably at least 70% by weight, such as at least 75%, at least 80% or at least 85% by weight e.g., at least 90% by weight, based on the total fatty acid residue content.
- the palm oil stearin used in step (i) of the process of the present invention may be obtained from solvent (wet) fractionation, Lanza fractionation, or dry fractionation of palm oil, such as multi-stage counter current dry fractionation of palm oil.
- the palm oil can be crude palm oil, refined palm oil, fractions of palm oil (e.g., obtained by dry fractionation), other derivatives of palm oil, or mixtures thereof.
- the palm oil stearin used in step (i), preferably comprises 2-palmitoyl glycerides, typically in an amount of greater than 50% by weight, such as greater than 55% by weight or greater than 60% by weight.
- the palm oil stearin has an iodine value (IV) of between about 2 and about 12, preferably between about 4 and about 11, more preferably between about 6 and about 11, such as from about 8 to about 10.
- the palm oil stearin is typically refined in optional step (ii), which preferably involves bleaching and deodorising.
- the bleaching of the palm oil stearin in the process of the invention is performed above 95 0 C, more preferably above 100 0 C (such as at from 105 0 C to 12O 0 C).
- volatile impurities are removed from the palm oil stearin to yield deodorised palm oil stearin, typically at temperatures above 200 0 C.
- the impurities removed in the deodorising step commonly include free fatty acids, aldehydes, ketones, alcohols and other hydrocarbon impurities.
- the bleaching and deodorising are performed under standard conditions known in the art and may be carried out in a single process step or two or more process steps.
- the steps may be carried out at reduced pressures (e.g., 10 mm Hg or below), wherein the palm oil stearin is contacted with steam to help vaporise the impurities.
- Bleaching and deodorising the palm oil stearin may help to improve the yield of the process.
- stearin includes a triglyceride mixture or fat blend from which at least 10% by weight of the lower melting constituents have been removed by some kind of fractionation, e.g., dry fractionation, Lanza fractionation or solvent fractionation.
- olein refers to a triglyceride mixture or fat blend from which at least 10% by weight of the higher melting constituents have been removed by some kind of fractionation, e.g., dry fractionation, Lanza fractionation or solvent fractionation.
- fatty acid, fatty acyl groups, and related terms used herein refer to saturated or unsaturated, straight chain carboxylic acids having from 4 to 24 carbon atoms, preferably from 12 to 22 carbon atoms.
- Unsaturated acids may comprise one, two, or more double bonds, preferably one or two double bonds.
- alkyl refers to straight chain or branched saturated hydrocarbons having from 1 to 6 carbon atoms.
- the enzymic transesterification according to the process of the present invention ⁇ is preferably carried out using a 1,3 specific lipase as a biocatalyst.
- the fatty acids on the 2-position of the triglycerides typically do not change (for example, less than 10% by moles of fatty acyl groups in the 2-position, more preferably less than 5%, such as less than 1%, change during the process).
- unsaturated fatty acid residues may be introduced into the 1- and 3 -positions of the 2-pahnitoyl glycerides by exchange with the fatty acid residues of other glycerides or more preferably by means of transesterification in the fatty mixture.
- Exchange preferably takes place between unsaturated free fatty acids, preferably oleic acid, or alkyl esters of oleic acid with alcohols having from 1 to 6 carbon atoms.
- the 2-palmitoyl glycerides modified in this way may be separated from the reaction mixture.
- the enzymic transesterification reaction in the process of the present invention selectively exchanges palmitic acid with oleic acid on the 1,3 -position rather than the 2-position.
- the transesterification reaction is typically performed to reach or approach equilibrium at a conversion ratio of a minimum of at least 50%, preferably at least 60%, most preferably at least 70%.
- the palm oil stearin is, for example, mixed with an oleic acid concentrate (comprising free oleic acid at a concentration of greater than 65% by weight, preferably greater than 70% by weight, most preferably greater than 75% by weight).
- the oleic acid may be provided as a mixture comprising oleic acid (preferably in an amount of greater than 65% by weight), linoleic acid and, optionally, one or more other fatty acids.
- the ratio of palm oil stearin to oleic acid concentrate is preferably from 0.1 : 1 to 2 : 1, more preferably from 0.4 : 1 to 1.2 : 1, even more preferably from 0.4 : 1 to 1 : 1, most preferably from 1:1.1 to 1:2 on a weight basis.
- the reaction is preferably carried out at a temperature of from 3O 0 C to 9O 0 C, preferably from 50 0 C to 8O 0 C, such as about 6O 0 C to 7O 0 C, and may be conducted batchwise or in continuous fashion, with or without a water-immiscible organic solvent.
- the humidity is preferably controlled to a water activity between 0.05 and 0.55, preferably between 0.1 and 0.5, depending on the type of biocatalyst enzyme system used.
- the reaction may be performed, for example, at 60°C in a stirred tank or in a packed bed reactor over biocatalysts, based on concentrates of Lipase D ⁇ Rhizopus oryzae, previously classified as Rhizopus delemar, from Amano Enzyme Inc., Japan) or immobilised concentrates of Rhizomucor miehei (Lipozyme RM IM from Novozymes A/S, Denmark).
- the transesterified mixture (optionally after further treatment, such as isolation of the fat phase) is preferably distilled. Distillation is preferably carried out at low pressure (e.g., lower than 10 mbar) and elevated temperatures (e.g., greater than 200°C) to remove the fatty acids from the product triglyceride fraction.
- the composition obtained in (iv) is preferably fractionated in (v) to recover an olein fraction (i.e., a lower melting fraction).
- an olein fraction i.e., a lower melting fraction.
- This can be done using solvent fractionation, Lanza fractionation or dry fractionation, using a single, two-step or multi-step fractionation technique, but is preferably carried out using single step dry fractionation.
- the olein can also be obtained by subjecting the transesterified mixture to multi-stage counter current dry fractionation. Fractionation of the triglyceride fraction removes the unconverted tripalmit ⁇ n (PPP) down to a level of less than 15 weight %, preferably less than 10 weight %, most preferably less than 8 weight %.
- the olein fraction, obtained after step (v) is typically further refined or purified to remove all remaining fatty acids and contaminants to produce a refined olein fraction.
- the process may optionally comprise further steps before, between or after (i) to (v), such as partial purification or enrichment of the products in the desired component(s).
- composition obtained after (iv) or the fraction comprising an increased amount of OPO glyceride obtained after (v) in the process of the invention preferably comprises at least 10% by weight OPO 5 more preferably at least 15%, even more preferably at least 20%, such as at least 25% or 30% or even 40% by weight OPO based on total glycerides in the fraction.
- the balance typically comprises other non-OPO triglycerides, and may further contain minor amounts of diglycerides and monoglycerides. Minor amounts of free fatty acids may also be present.
- the fraction is preferably a composition which comprises a mixture of triglycerides wherein different fatty acid residues, including unsaturated fatty acid residues, are randomly distributed between the 1- and 3-positions and at least half of the fatty acid residues in the 2-positions are Cl 6 and/or Cl 8 saturated, preferably consisting substantially of palmitic acid residues, in particular 60-90% by weight of the total 2-position fatty acids are preferably palmitic acid.
- all of the fatty acid residues, or virtually all (e.g., greater than 99% by weight), in the glycerides of the composition are even-numbered.
- the unsaturated fatty acid residues in the 1- and 3-positions preferably consist largely of oleic acid and linoleic acid.
- the compositions preferably includes at least as much (on a molar basis) of saturated fatty acid in the 2-position as in the 1- and 3-positions combined, more preferably up to twice as much (on a molar basis).
- the 1,3-positions include both unsaturated C18 and saturated C4 to C14 fatty acids.
- the proportion and type of these fatty acids may be determined in accordance with dietary and physical requirements of the composition required.
- milk replacement fats should be capable of emulsiftcation at blood heat in liquid feed and should therefore preferably be capable of being melted at this temperature (37 0 C).
- the melting point of fats is determined by their fatty acid composition, which may be selected accordingly. Fats with the correct fatty acid composition may be selected for use in the present invention, therefore, with a view to producing fat compositions with certain desired physical characteristics.
- compositions produced by the present invention are those comprising triglycerides having at least 40%, more preferably at least 45%, such as at least 50% by weight palmitic acid present in the 2-position of title glyceride, based on the weight of total fatty acid residues present. Additionally or alternatively, the compositions may comprise less than 8% by weight SSS glycerides (wherein S represents saturated fatty acid having at least 18 carbon atoms, preferably 18 carbon atoms) based on total weight of triglycerides, and at least 40% by weight oleic acid residues in the 1- and 3-positions, based on the weight of total fatty acid residues present.
- SSS glycerides wherein S represents saturated fatty acid having at least 18 carbon atoms, preferably 18 carbon atoms
- the fat composition produced by the process of the invention has palmitic acid groups at the 2- position of the glyceride (an "SN-2 value") in an amount of at least 50%, more preferably at least 52%, even more preferably at lerast 53%, such as at least 54% or at least 55% or at least 56%.
- An SN-2 value of x % means that of the total palmitic acid residues in the glyceride, x % (by weight or moles) are in the 2- position and (100 - x) % of the palmitic acid residues are distributed between the 1- and 3- positions of the glyceride. This value is preferably determined as described in the method set out in Example 2.
- composition obtained by the process of the present invention contains preferably less than 10% by weight 1,2,3-trisaturated glycerides, preferably less than 8% by weight 1,2,3-trisaturated glycerides.
- the invention may comprise an additional step of further purifying the product in OPO.
- the process of the present invention may, additionally or alternatively, comprise the further step (vi) of blending the OPO fraction with other fats and/or oils, preferably with at least one vegetable oil, to form a fat blend.
- Suitable fats are fats comprising: up to 40% by weight of medium-chain triglycerides; up to 30% by weight of lauric fats; up to 50% by weight of other vegetable fats; or up to 40wt % of butterfat; or fractions or mixtures of these fats.
- lauric fats preferably palm kernel oil
- lauric fats may be included in the compositions to provide blends aiming to match the compositions of milk fat or its melting characteristics
- vegetable oils such as sunflower oil, high oleic sunflower oil, palm kernel oil, rapeseed oil and soybean oil, coconut oil, high oleic safflower oil which have a high content of polyunsaturated fatty acid glycerides, which improve the dietary - benefit of the compositions, may be included.
- the compositions produced by the process of the invention preferably provide blends matching the composition of milk fat or its melting characteristics.
- the fat compositions or fat blends produced by the process of the invention are suitable for replacing at least a part of the fat in infant food formulations.
- the present invention also therefore provides for a method for the production of infant food compositions comprising fat, protein and carbohydrate components in the approximate relative weight proportions 2.5:1:5, wherein at least a part of the fat normally used in such formulations is replaced by the fat composition or fat blend made in accordance with the present invention. Dry formulations containing this mixture, together with additional components customary in such formulations, should be dispersed for use in sufficient water to produce an emulsion of approximately 3 1 A grams of fat per 100 ml of dispersion. Therefore, in another aspect, the invention provides a method of producing an infant food formulation by packaging and labelling the composition comprising OPO triglyceride obtained after step (v) or step (vi) of the process.
- the palm oil stearin was physically refined (bleached and deodorised). After refining, the palm oil stearin was mixed with an oleic acid concentrate (Cl 8:1 concentration > 75%). The ratio of palm oil stearin to oleic acid concentrate was between 1.2 to 2 on weight basis. The mixing ratio was determined by the activity of the enzymes, the quality of the palm oil stearin and the quality of the oleic acid (concentration of palmitic and oleic acids).
- the humidity was controlled carefully at a water activity between 0.1 and 0.5, depending on the type of biocatalyst enzyme system used.
- the reaction was performed at 6O 0 C in a stirred tank or in a packed bed reactor over biocatalysts, based on concentrates of Lipase D (Rhizopus oryzae, previously classified as Rhizopus delemar, from Amano Enzyme Inc., Japan) or immobilised concentrates of Rhizomucor miehei (Lipozyme RM IM from Novozymes AJS, Denmark).
- the enzymic transesterification reaction selectively exchanges palmitic acid with oleic acid on the 1,3 -position rather than the 2-position.
- the reaction was performed to reach an approach to equilibrium of a minimum of 70% exchange.
- the fatty acids were removed from the product triglyceride fraction by distillation at low pressure ( ⁇ 10 mbar) and elevated temperatures (>200°C).
- the triglyceride fraction was dry fractionated to remove the unconverted tri- pahnitines down to a level of maximum 6 weight %.
- the olein fraction was fully refined to remove all remaining fatty acids and contaminants to produce a refined OPO composition.
- the product after acidolysis had the following composition:
- the product was fractionated at about 35 0 C.
- the fractionated product had the following composition:
Abstract
Description
Claims
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008529693A JP5289051B2 (en) | 2005-09-08 | 2006-09-08 | Method for producing dioleoyl palmitoyl glyceride |
DK06779360.4T DK1928990T3 (en) | 2005-09-08 | 2006-09-08 | PROCEDURE FOR PREPARING DIOLEYL PALMITOYL Glyceride |
EP06779360.4A EP1928990B1 (en) | 2005-09-08 | 2006-09-08 | Process for producing dioleyl palmitoyl glyceride |
AU2006288937A AU2006288937B2 (en) | 2005-09-08 | 2006-09-08 | Process for producing dioleoyl palmitoyl glyceride |
BRPI0615859A BRPI0615859B1 (en) | 2005-09-08 | 2006-09-08 | process for producing a composition |
US11/991,610 US8153407B2 (en) | 2005-09-08 | 2006-09-08 | Process for producing a triglyceride |
KR1020087008417A KR101126305B1 (en) | 2005-09-08 | 2006-09-08 | Process for producing dioleoyl palmitoyl glyceride |
US13/550,352 USRE44719E1 (en) | 2005-09-08 | 2006-09-08 | Process for producing a triglyceride |
CN2006800330132A CN101258230B (en) | 2005-09-08 | 2006-09-08 | Process for producing dioleyl palmitoyl glyceride |
IL189920A IL189920A (en) | 2005-09-08 | 2008-03-04 | Process for producing dioleyl palmitoyl glyceride |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05255492.0 | 2005-09-08 | ||
EP05255492 | 2005-09-08 |
Publications (1)
Publication Number | Publication Date |
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WO2007029018A1 true WO2007029018A1 (en) | 2007-03-15 |
Family
ID=35519310
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB2006/003343 WO2007029018A1 (en) | 2005-09-08 | 2006-09-08 | Process for producing dioleyl palmitoyl glyceride |
Country Status (12)
Country | Link |
---|---|
US (2) | US8153407B2 (en) |
EP (1) | EP1928990B1 (en) |
JP (1) | JP5289051B2 (en) |
KR (1) | KR101126305B1 (en) |
CN (1) | CN101258230B (en) |
AU (1) | AU2006288937B2 (en) |
BR (1) | BRPI0615859B1 (en) |
DK (1) | DK1928990T3 (en) |
IL (1) | IL189920A (en) |
MY (1) | MY145320A (en) |
RU (1) | RU2422498C2 (en) |
WO (1) | WO2007029018A1 (en) |
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WO2009062663A3 (en) * | 2007-11-14 | 2009-11-12 | Lipid Nutrition B.V. | Infant formula composition |
WO2013068879A2 (en) | 2011-11-10 | 2013-05-16 | Pfizer Inc. | Infant formula with high sn-2 palmitate and oligofructose |
EP2636312A1 (en) * | 2012-03-08 | 2013-09-11 | IOI Lipid Enzymtec Sdn. Bhd. | Glyceride composition |
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WO2015014967A1 (en) * | 2013-08-01 | 2015-02-05 | Loders Croklaan B.V. | Glyceride composition |
EP2845490A1 (en) | 2013-09-05 | 2015-03-11 | Loders Croklaan B.V. | Fat composition for improved body fat distribution |
WO2017084241A1 (en) * | 2015-11-20 | 2017-05-26 | 中国农业科学院油料作物研究所 | Method for preparing 1,3-dioleoyl-2-palmitoylglycerol in a subcritical system |
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EP4204523A1 (en) * | 2020-08-31 | 2023-07-05 | AAK AB (publ) | A process for production of a vegetable oil composition having at least 50% palmitic acid present in the sn2-position out of total palmitic acid in the triglycerides of the vegetable oil composition |
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EP2115107B1 (en) | 2007-02-28 | 2018-04-11 | Loders Croklaan B.V. | Process for producing a glyceride composition |
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WO2009062663A3 (en) * | 2007-11-14 | 2009-11-12 | Lipid Nutrition B.V. | Infant formula composition |
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EP2636312A1 (en) * | 2012-03-08 | 2013-09-11 | IOI Lipid Enzymtec Sdn. Bhd. | Glyceride composition |
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EP3027063B1 (en) | 2013-08-01 | 2018-11-21 | Bunge Loders Croklaan B.V. | Opo glyceride composition |
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EP2845490A1 (en) | 2013-09-05 | 2015-03-11 | Loders Croklaan B.V. | Fat composition for improved body fat distribution |
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WO2017084241A1 (en) * | 2015-11-20 | 2017-05-26 | 中国农业科学院油料作物研究所 | Method for preparing 1,3-dioleoyl-2-palmitoylglycerol in a subcritical system |
US10590443B2 (en) | 2016-02-19 | 2020-03-17 | Fuji Oil Holdings Inc. | Method for producing multiple oil/fat compositions by complex transesterification reaction system |
US20210002681A1 (en) * | 2018-03-02 | 2021-01-07 | Fuji Oil Holdings Inc. | Production method for oil/fat composition rich in palmitic acid at position 2 |
CN110724715A (en) * | 2018-07-16 | 2020-01-24 | 浙江贝家生物科技有限公司 | Method for synthesizing 1, 3-dioleoyl-2-palmitic acid triglyceride composition by using non-localized enzyme |
CN110724715B (en) * | 2018-07-16 | 2021-07-20 | 浙江贝家生物科技有限公司 | Method for synthesizing 1, 3-dioleoyl-2-palmitic acid triglyceride composition by using non-localized enzyme |
WO2022008718A1 (en) | 2020-07-10 | 2022-01-13 | Bunge Loders Croklaan B.V. | Fat composition |
Also Published As
Publication number | Publication date |
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AU2006288937A1 (en) | 2007-03-15 |
JP5289051B2 (en) | 2013-09-11 |
DK1928990T3 (en) | 2017-05-01 |
MY145320A (en) | 2012-01-31 |
AU2006288937B2 (en) | 2010-08-26 |
JP2009507480A (en) | 2009-02-26 |
EP1928990A1 (en) | 2008-06-11 |
IL189920A (en) | 2013-06-27 |
RU2008113374A (en) | 2009-10-20 |
EP1928990B1 (en) | 2017-02-15 |
KR101126305B1 (en) | 2012-03-19 |
BRPI0615859A2 (en) | 2012-12-18 |
BRPI0615859B1 (en) | 2017-06-06 |
KR20080044337A (en) | 2008-05-20 |
US20090130728A1 (en) | 2009-05-21 |
CN101258230B (en) | 2012-11-21 |
USRE44719E1 (en) | 2014-01-21 |
RU2422498C2 (en) | 2011-06-27 |
US8153407B2 (en) | 2012-04-10 |
IL189920A0 (en) | 2008-08-07 |
CN101258230A (en) | 2008-09-03 |
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