WO2014126454A1 - A process for producing high oleic content liquid palm oil fraction - Google Patents

A process for producing high oleic content liquid palm oil fraction Download PDF

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Publication number
WO2014126454A1
WO2014126454A1 PCT/MY2014/000015 MY2014000015W WO2014126454A1 WO 2014126454 A1 WO2014126454 A1 WO 2014126454A1 MY 2014000015 W MY2014000015 W MY 2014000015W WO 2014126454 A1 WO2014126454 A1 WO 2014126454A1
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Prior art keywords
palm oil
triacylglycerols
directed
palmitic
fraction
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PCT/MY2014/000015
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French (fr)
Inventor
Noor Lida Habi MAT DIAN
Miskandar MAT SAHRI
Chin Ping Tan
Oi Ming Lai
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Malaysian Palm Oil Board
Universiti Putra Malaysia
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Publication of WO2014126454A1 publication Critical patent/WO2014126454A1/en

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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
    • C11B7/0075—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of melting or solidifying points
    • 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
    • A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
    • A23D9/04—Working-up
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • 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

Definitions

  • the present invention relates to a process for producing high oleic content liquid pa!m oil fraction.
  • High oleic oils are currently touted to be the healthiest edible fat in the human diet. High concentrations of oleic acid lowers blood cholesterol levels and raise the good high density lipoprotein (HDL) cholesterol while lowering the bad low density lipoprotein (LDL) cholesterols levels.
  • HDL high density lipoprotein
  • LDL bad low density lipoprotein
  • Palm oil (PO) is a balanced oil with equal parts of saturated (SAFA) and unsaturated fatty acids.
  • SAFA saturated
  • unsaturated fatty acids SFA
  • the liquid fraction of PO presents a limitation as it contains high level of SAFA. Palm olein containing high SAFA content increases the possibility of turning into solid under cold temperature, thus making it functionally less desirable.
  • oil with high SAFA content is nutritionally undesirable as SAFAs may cause health implications.
  • the content of unsaturated fatty acids (USAFA), especially oleic acid content of palm oil and palm oil olein must be increased.
  • the present invention is directed to a process for producing highly unsaturated palm oil fraction employing the principle of catalyst-directed interesterification of palm oil.
  • the present invention relates to a process for producing high oleic content liquid palm oil fraction wherein the process includes:
  • substantially moisture-free palm oil i. subjecting substantially moisture-free palm oil to a temperature ranging from 75°C to 85°C for a period of 30 to 45 minutes resulting in molten palm oil;
  • step (i) lowering the temperature in step (i) to a range of 55°C to 70°C;
  • step (iii) subjecting the oil-catalyst mixture obtained in step (iii) to react at directed interesterification temperature of 20°C to 55°C for a period of 5 to 48 hours;
  • step (vi) purifying the catalyst-free directed interesterified palm oil obtained in step (vi);
  • step (viii) subjecting the purified directed interesterified palm oil obtained in step (vii) to a a temperature ranging from 65°C to 85°C;
  • step (viii) crystallizing the molten directed interesterified palm oil obtained in step (viii) to form high oleic content liquid palm olein and high palmitic content solid stearin fractions at a temperature range of 5°C to 30°C;
  • step (ix) separating the high palmitic content stearin solid crystals obtained in step (ix) at a temperature range of 5°C to 30°C, resulting in high oleic content liquid palm oil fraction.
  • an object of the present invention is to provide a process of restructuring of fatty acids on triacylglycerol molecules of palm oil to produce highly unsaturated palm oil fraction in a form of liquid which has high iodine value and high in oleic acid.
  • the restructuring of fatty acids on triacylglycerol molecules of palm oil involves rearranging fatty acids on triacylglycerol molecules of palm oil by way of directed interesterification. The directed interesterification is described herein.
  • the directed interesterification is catalyzed by an enzyme, namely lipase, whereby reaction is directed towards temperatures below melting point of the highest melting point triacylglycerols to allow crystallization and exclusion of the triacylglycerols from the reaction until all that is left behind is a liquid phase rich in low melting triacylglycerols, which in turn is rich in unsaturated fatty acids.
  • an enzyme namely lipase
  • the present invention is described herein.
  • the process begins by subjecting substantially moisture-free palm oil to a temperature ranging from 75°C to 85°C resulting in molten oil, preferably at 80°C for 30 to 45 minutes, under vacuum, in a stirred vessel.
  • the temperature was then lowered to a range from 55°C to 70°C, preferably at 60°C.
  • a concentration load of 2% to 15% (w/w), preferably 10% (w/w), of catalyst, an enzyme, a lipase, specific or non-specific, was added into the molten oil and allowed to react for 30 to 90 minutes.
  • the reaction temperature was then again lowered to the directed interesterification temperature range of 20°C to 55°C, preferably at 25°C to 30°C, for a period of 5 to 48 hours, preferably at 10-20 hours.
  • the reaction was stopped immediately, for example, by rapidly heating the reaction mixture at a temperature ranging from 75°C to 85°C, preferably at 80°C, and then followed by filtration, preferably but not limiting to vacuum filtration, for removal of enzyme to obtain enzyme-free directed interesterified palm oil.
  • the enzyme-free directed interesterified palm oil was then purified, preferably by way of short path distillation or other means of purification.
  • the enzyme-free directed interesterified palm oil was subjected to melting at temperature ranging from 65°C to 85°C, preferably at 75°C, to ensure that all fat crystals in liquid form before proceeding to crystallization.
  • crystallization was conducted at a temperature ranging from 10°C to 30°C, preferably at 20 to 25°C, together with slow agitation for several hours and followed by vacuum filtration, or other separation method, to separate the liquid high oleic content olein fraction from the high palmitic content stearin crystals.
  • a catalyst into a moisture-free palm oil can be carried out at selected directed interesterification temperature range at of 20°C to 55°C, preferably at 25to 30°C, for 5 to 48 hours, preferably at 10 to 20 hours.
  • Triacylglycerols composition (w/w %) of directed interesterified palm oil (reaction temperature of 30°C, reaction time of 18 hours, and 10% enzyme load) as compared to refined, bleached and deodorized palm oil.
  • TAG triacylglycerol
  • RBD refined, bleached and deodorized
  • OLL TAG containing one oleic and two linoleic fatty acids
  • OLO TAG containing one linoleic and two oleic fatty acids
  • PPP TAG containing three palmitic fatty acids
  • PPS TAG containing two palmitic and one stearic fatty acids
  • PLL TAG containing one palmitic and two linoleic fatty acids
  • PLO TAG containing one palmitic, one oleic and one linoleic fatty acids
  • POO TAG containing one palmitic and two oleic fatty acids
  • PLP TAG containing one linoleic and two palmitic fatty acids
  • POP TAG containing one oleic and two palmitic fatty acids
  • TAG TAG containing one oleic, one palmitic and one stearic fatty acids
  • RBD refined, bleached and deodorized
  • MONO monounsaturated fatty acid
  • POLY polyunsaturated fatty acid
  • RBD refined, bleached and deodorized
  • Triacylglycerols composition of olein fraction (w/w %) of enzymatic directed interesterified palm oil (reaction temperature of 30°C, reaction time of 18 hours, and 10% enzyme load) fractionated at 10°C as compared to refined, bleached and deodorized palm olein, fractionated from refined, bleached and deodorized palm oil
  • TAG triacylglycerol
  • RBD refined, bleached and deodorized
  • OLL TAG containing one oleic and two linoleic fatty acids
  • OLO TAG containing one linoleic and two oleic fatty acids
  • PPP TAG containing three palmitic fatty acids
  • PPS TAG containing two palmitic and one stearic fatty acids
  • PLL TAG containing one palmitic and two linoleic fatty acids
  • PLO TAG containing one palmitic, one oleic and one linoleic fatty acids
  • PLP TAG containing one linoleic and two palmitic fatty acids
  • POP TAG containing one oleic and two palmitic fatty acids
  • TAG TAG containing one oleic, one palmitic and one stearic fatty acids
  • the high oleic olein fraction obtained by a combination of the enzymatic directed interesterification of palm oil, and crystallization and fractionation of the enzymatic directed interesterified palm oil at the temperatures of 5 to 30°C is suitable to be used as frying oil or as a salad oil or other food preparation or formulations which require the usage of liquid oils.
  • the high palmitic solid and hard stearin fraction obtained by a combination of the enzymatic directed interesterification of palm oil, and crystallization and fractionation of the enzymatic directed interesterified palm oil is suitable to be used as a component for interesterified fat for usage as a base fat for low saturated fatty acids solid fat formulations, or other usage that requires the incorporation of hard fats.
  • the enzymatic directed interesterified palm oil is a fat containing low and high melting fractions, wherein the low melting fraction consists, high oleic olein, mainly of triunsaturated triacylglycero!s and diunsaturated-monosaturated triacylglycerols and the high melting fraction, the high palmitic stearin, consists mainly of trisaturated and disaturated-monounsaturated triacylglycerols.
  • the enzymatic directed interesterified palm oil may also contain a significant amount of diacylglycerols and monoacylglycerols of up to 50% by weight depending on the reaction time of up to 48 hours.
  • the enzymatic directed interesterified palm oil comprises of 20-35% by weight triunsaturated triacylglycerols, 30-40% by weight trisaturated triacylglycerols, 20-30% by weight diunsaturated-monosaturated triacylglycerols, and 15-25% by weight disaturated-monosaturated triacylglycerols, wherein the triunsaturated triacylglycerols further comprise of OLO, OOL, OLL, LLO and OOO triacylglycerols, the trisaturated triacylglycerols comprise of PPP and PPS triacylglycerols, the diunsaturated-monosaturated triacylglycerols further comprise of POO and PLO triacylglycerols, and the disaturated-monosaturated triacylglycerols further comprise of POP triacylglycerols.
  • the liquid olein fraction obtained from crystallization and fractionation of the enzymatic directed interesterified palm oil comprises of 55-65% by weight monounsaturated fatty acid (Oleic acid, C18:1), 10-15% by weight polyunsaturated fatty acid (Linoleic acid, C18:2) and 20-30% by weight saturated (Palmitic acid, C16:0; Stearic acid, C18:0) fatty acids content.
  • the liquid olein fraction has an iodine value of 75 to 95, depending on the crystallization and fractionation temperatures of the enzymatic directed interesterified palm oil, for example, 5 to 30°C, and may also consists of 20-40% diacylglycerols.
  • the solid stearin fraction obtained from crystallization and fractionation of the enzymatic directed interesterified palm oil, has an iodine value 10-25 and melting point of 55-65°C, comprises of 65-90% saturated fatty acids and 10- 35% monounsaturated fatty acid wherein the saturated fatty acids further comprises of palmitic acid, C 6:0 and stearic acid, C18:0, and wherein the monounsaturated fatty acids further comprises oleic acid, C 8:1.
  • the solid stearin fraction comprises of 65-95% trisaturated triacylglycerols and 5-35% disaturated-monounsaturated triacylglycerols, depending on the crystallization and fractionation temperatures of the enzymatic directed interesterified palm oil, that are 5-30°C

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Abstract

A process for producing high oleic content liquid palm oil fraction wherein the process includes subjecting substantially moisture-free palm oil to heat resulting in molten palm oil, lowering the temperature adding catalyst into the molten palm oil to initiate directed interesterification reaction, subjecting the oil-catalyst mixture to react at directed interesterification temperature, deactivating the catalyst, removing the catalyst from the directed interesterified palm oil, purifying the catalyst-free directed interesterified palm oil, subjecting the purified directed interesterified palm oil, crystallizing the molten directed interesteritified palm oil form high oleic content liquid palm olein and high palmitic content solid stearin fractions and separating the high palmitic content stearin solid crystals resulting in high oleic content liquid palm oil fraction.

Description

A PROCESS FOR PRODUCING HIGH OLEIC CONTENT LIQUID PALM OIL
FRACTION
FIELD OF INVENTION
The present invention relates to a process for producing high oleic content liquid pa!m oil fraction.
BACKGROUND OF INVENTION
High oleic oils are currently touted to be the healthiest edible fat in the human diet. High concentrations of oleic acid lowers blood cholesterol levels and raise the good high density lipoprotein (HDL) cholesterol while lowering the bad low density lipoprotein (LDL) cholesterols levels.
Palm oil (PO) is a balanced oil with equal parts of saturated (SAFA) and unsaturated fatty acids. With current consumer preference for low SAFA fat products, even palm olein (POo), the liquid fraction of PO presents a limitation as it contains high level of SAFA. Palm olein containing high SAFA content increases the possibility of turning into solid under cold temperature, thus making it functionally less desirable. Furthermore, oil with high SAFA content is nutritionally undesirable as SAFAs may cause health implications. To improve the nutritional and functional properties, the content of unsaturated fatty acids (USAFA), especially oleic acid content of palm oil and palm oil olein must be increased.
Accordingly, a need exists for a process for producing high oleic content liquid palm oil fraction.
SUMMARY OF INVENTION
The present invention is directed to a process for producing highly unsaturated palm oil fraction employing the principle of catalyst-directed interesterification of palm oil.
More particularly, the present invention relates to a process for producing high oleic content liquid palm oil fraction wherein the process includes:
i. subjecting substantially moisture-free palm oil to a temperature ranging from 75°C to 85°C for a period of 30 to 45 minutes resulting in molten palm oil;
ii. lowering the temperature in step (i) to a range of 55°C to 70°C;
iii. adding a catalyst into the molten palm oil to initiate directed interesterification reaction at a range of 55°C to 70°C for a period of 30 to 90 minutes;
iv. subjecting the oil-catalyst mixture obtained in step (iii) to react at directed interesterification temperature of 20°C to 55°C for a period of 5 to 48 hours;
v. deactivating the catalyst;
vi. removing the catalyst from the directed interesterified palm oil;
vii. purifying the catalyst-free directed interesterified palm oil obtained in step (vi);
viii. subjecting the purified directed interesterified palm oil obtained in step (vii) to a a temperature ranging from 65°C to 85°C;
ix. crystallizing the molten directed interesterified palm oil obtained in step (viii) to form high oleic content liquid palm olein and high palmitic content solid stearin fractions at a temperature range of 5°C to 30°C; and
x. separating the high palmitic content stearin solid crystals obtained in step (ix) at a temperature range of 5°C to 30°C, resulting in high oleic content liquid palm oil fraction. DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
It should be noted that the following detailed description is directed to a process for producing highly unsaturated palm oil fraction. More particularly, an object of the present invention is to provide a process of restructuring of fatty acids on triacylglycerol molecules of palm oil to produce highly unsaturated palm oil fraction in a form of liquid which has high iodine value and high in oleic acid. The restructuring of fatty acids on triacylglycerol molecules of palm oil involves rearranging fatty acids on triacylglycerol molecules of palm oil by way of directed interesterification. The directed interesterification is described herein. The directed interesterification is catalyzed by an enzyme, namely lipase, whereby reaction is directed towards temperatures below melting point of the highest melting point triacylglycerols to allow crystallization and exclusion of the triacylglycerols from the reaction until all that is left behind is a liquid phase rich in low melting triacylglycerols, which in turn is rich in unsaturated fatty acids.
The present invention is described herein. The process begins by subjecting substantially moisture-free palm oil to a temperature ranging from 75°C to 85°C resulting in molten oil, preferably at 80°C for 30 to 45 minutes, under vacuum, in a stirred vessel. The temperature was then lowered to a range from 55°C to 70°C, preferably at 60°C. Next, a concentration load of 2% to 15% (w/w), preferably 10% (w/w), of catalyst, an enzyme, a lipase, specific or non-specific, was added into the molten oil and allowed to react for 30 to 90 minutes. The reaction temperature was then again lowered to the directed interesterification temperature range of 20°C to 55°C, preferably at 25°C to 30°C, for a period of 5 to 48 hours, preferably at 10-20 hours. When desired reaction time is achieved, the reaction was stopped immediately, for example, by rapidly heating the reaction mixture at a temperature ranging from 75°C to 85°C, preferably at 80°C, and then followed by filtration, preferably but not limiting to vacuum filtration, for removal of enzyme to obtain enzyme-free directed interesterified palm oil. Typically, the enzyme-free directed interesterified palm oil was then purified, preferably by way of short path distillation or other means of purification. Then, the enzyme-free directed interesterified palm oil was subjected to melting at temperature ranging from 65°C to 85°C, preferably at 75°C, to ensure that all fat crystals in liquid form before proceeding to crystallization. Lastly, crystallization was conducted at a temperature ranging from 10°C to 30°C, preferably at 20 to 25°C, together with slow agitation for several hours and followed by vacuum filtration, or other separation method, to separate the liquid high oleic content olein fraction from the high palmitic content stearin crystals.
Alternatively, the addition of a catalyst into a moisture-free palm oil can be carried out at selected directed interesterification temperature range at of 20°C to 55°C, preferably at 25to 30°C, for 5 to 48 hours, preferably at 10 to 20 hours.
The following examples further illustrate but by no means limit the scope of present invention:
RESULTS Example 1
TABLE 1 : Triacylglycerols composition (w/w %) of directed interesterified palm oil (reaction temperature of 30°C, reaction time of 18 hours, and 10% enzyme load) as compared to refined, bleached and deodorized palm oil.
Figure imgf000006_0001
TAG: triacylglycerol
DIE: directed interesterified
RBD: refined, bleached and deodorized
U3: triunsaturated triacylglycerols
S3: trisaturated triacylglycerols
U2S: diunsaturated-monosaturated triacylglycerols
S2U: disaturated-monounsaturated triacylglycerols
O: Oleic acid L: Linoleic acid
P: Palmitic acid
S: Stearic acid
OLL: TAG containing one oleic and two linoleic fatty acids
OLO: TAG containing one linoleic and two oleic fatty acids
OOO: TAG containing three oleic fatty acids
PPP: TAG containing three palmitic fatty acids
PPS: TAG containing two palmitic and one stearic fatty acids
PLL: TAG containing one palmitic and two linoleic fatty acids
PLO: TAG containing one palmitic, one oleic and one linoleic fatty acids POO: TAG containing one palmitic and two oleic fatty acids
SOO: TAG containing one stearic and two oleic fatty acids
PLP: TAG containing one linoleic and two palmitic fatty acids
POP: TAG containing one oleic and two palmitic fatty acids
POS: TAG containing one oleic, one palmitic and one stearic fatty acids
Example 2
TABLE 2: Fatty acid composition of olein fraction (w/w %) of enzymatic directed interesterified palm oil (reaction temperature of 30°C, reaction time of 18 hours, and 10% enzyme load) fractionated at 5, 10 and 15°C as compared to the olein fraction of refined, bleached and deodorized palm oil.
Figure imgf000008_0001
DIE: directed interesterified
POo: palm olein
RBD: refined, bleached and deodorized
SAT: saturated fatty acid
MONO: monounsaturated fatty acid POLY: polyunsaturated fatty acid
La: Laurie acid
M: Myristic acid
O: Oleic acid
L: Linoleic acid
P: Palmitic acid
S: Stearic acid
Example 3
TABLE 3: Iodine value of olein and stearin fractions of enzymatic interesterified palm oil (reaction temperature of 30°C, reaction time of 18 hours, and 10% enzyme load) fractionated at 5, 10 and 15°C as compared to the olein and stearin fractions of refined bleached and deodorized palm oil.
Figure imgf000009_0001
DIE: directed interesterified
PO: palm oil
RBD: refined, bleached and deodorized
IV: iodine value Example 4
TABLE 4: Triacylglycerols composition of olein fraction (w/w %) of enzymatic directed interesterified palm oil (reaction temperature of 30°C, reaction time of 18 hours, and 10% enzyme load) fractionated at 10°C as compared to refined, bleached and deodorized palm olein, fractionated from refined, bleached and deodorized palm oil
Figure imgf000010_0001
PO: palm oil
POo: palm olein
IV: iodine value
TAG: triacylglycerol
DIE: directed interesterified
RBD: refined, bleached and deodorized
U3: triunsatu rated triacylglycerols
S3: triunsaturated triacylglycerols
U2S: diunsaturated-monosaturated triacylglycerols
S2U: disaturated-monounsaturated triacylglycerols O: Oleic acid
L: Linoleic acid
P: Palmitic acid
S: Stearic acid
OLL: TAG containing one oleic and two linoleic fatty acids
OLO: TAG containing one linoleic and two oleic fatty acids
OOO: TAG containing three oleic fatty acids
PPP: TAG containing three palmitic fatty acids
PPS: TAG containing two palmitic and one stearic fatty acids
PLL: TAG containing one palmitic and two linoleic fatty acids
PLO: TAG containing one palmitic, one oleic and one linoleic fatty acids
POO: TAG containing one palmitic and two oleic fatty acids
SOO: TAG containing one stearic and two oleic fatty acids
PLP: TAG containing one linoleic and two palmitic fatty acids
POP: TAG containing one oleic and two palmitic fatty acids
POS: TAG containing one oleic, one palmitic and one stearic fatty acids
The high oleic olein fraction obtained by a combination of the enzymatic directed interesterification of palm oil, and crystallization and fractionation of the enzymatic directed interesterified palm oil at the temperatures of 5 to 30°C is suitable to be used as frying oil or as a salad oil or other food preparation or formulations which require the usage of liquid oils. The high palmitic solid and hard stearin fraction obtained by a combination of the enzymatic directed interesterification of palm oil, and crystallization and fractionation of the enzymatic directed interesterified palm oil is suitable to be used as a component for interesterified fat for usage as a base fat for low saturated fatty acids solid fat formulations, or other usage that requires the incorporation of hard fats.
The enzymatic directed interesterified palm oil is a fat containing low and high melting fractions, wherein the low melting fraction consists, high oleic olein, mainly of triunsaturated triacylglycero!s and diunsaturated-monosaturated triacylglycerols and the high melting fraction, the high palmitic stearin, consists mainly of trisaturated and disaturated-monounsaturated triacylglycerols. The enzymatic directed interesterified palm oil may also contain a significant amount of diacylglycerols and monoacylglycerols of up to 50% by weight depending on the reaction time of up to 48 hours.
Further, the enzymatic directed interesterified palm oil comprises of 20-35% by weight triunsaturated triacylglycerols, 30-40% by weight trisaturated triacylglycerols, 20-30% by weight diunsaturated-monosaturated triacylglycerols, and 15-25% by weight disaturated-monosaturated triacylglycerols, wherein the triunsaturated triacylglycerols further comprise of OLO, OOL, OLL, LLO and OOO triacylglycerols, the trisaturated triacylglycerols comprise of PPP and PPS triacylglycerols, the diunsaturated-monosaturated triacylglycerols further comprise of POO and PLO triacylglycerols, and the disaturated-monosaturated triacylglycerols further comprise of POP triacylglycerols.
The liquid olein fraction obtained from crystallization and fractionation of the enzymatic directed interesterified palm oil (as mentioned above) comprises of 55-65% by weight monounsaturated fatty acid (Oleic acid, C18:1), 10-15% by weight polyunsaturated fatty acid (Linoleic acid, C18:2) and 20-30% by weight saturated (Palmitic acid, C16:0; Stearic acid, C18:0) fatty acids content.
Further, it comprises of 35-50% by weight triunsaturated triacylglycerols, 30- 40% by weight diunsaturated-monosaturated triacylglycerols and 10-15% by weight disaturated-monosaturated triacylglycerols. The liquid olein fraction has an iodine value of 75 to 95, depending on the crystallization and fractionation temperatures of the enzymatic directed interesterified palm oil, for example, 5 to 30°C, and may also consists of 20-40% diacylglycerols.
The solid stearin fraction, obtained from crystallization and fractionation of the enzymatic directed interesterified palm oil, has an iodine value 10-25 and melting point of 55-65°C, comprises of 65-90% saturated fatty acids and 10- 35% monounsaturated fatty acid wherein the saturated fatty acids further comprises of palmitic acid, C 6:0 and stearic acid, C18:0, and wherein the monounsaturated fatty acids further comprises oleic acid, C 8:1.
Further, the solid stearin fraction comprises of 65-95% trisaturated triacylglycerols and 5-35% disaturated-monounsaturated triacylglycerols, depending on the crystallization and fractionation temperatures of the enzymatic directed interesterified palm oil, that are 5-30°C
While several particularly preferred embodiments of the present invention have been described and illustrated, it should now be apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the present invention. Accordingly, the following claims are intended to embrace such changes, modifications and areas of application that are within the spirit and scope of the present invention.

Claims

A process for producing high oleic content liquid palm oil fraction wherein the process includes:
subjecting substantially moisture-free palm oil to a temperature ranging from 75°C to 85°C for a period of 30 to 45 minutes resulting in molten palm oil;
lowering the temperature in step (i) to a range of 55°C to 70°C;
adding a catalyst into the molten palm oil to initiate directed interesterification reaction at a range of 55°C to 70°C for a period of 30 to 90 minutes;
subjecting the oil-catalyst mixture obtained in step (iii) to react at directed interesterification temperature of 20°C to 55°C for a period of 5 to 48 hours;
deactivating the catalyst;
vi. removing the catalyst from the directed interesterified palm oil;
vii. purifying the catalyst-free directed interesterified palm oil obtained in step (vi);
viii. subjecting the purified directed interesterified palm oil obtained in step (vii) to a a temperature ranging from 65°C to 85°C;
ix. crystallizing the molten directed interesterified palm oil obtained in step (viii) to form high oleic content liquid palm olein and high palmitic content solid stearin fractions at a temperature range of 5°C to 30°C; and
x. separating the high palmitic stearin solid crystals obtained in step (ix) resulting in high oleic liquid palm oil fraction.
2. A process as claimed in claim 1 wherein step (i) is conducted at 80°C.
3. A process as claimed in claim 1 wherein step (ii) is conducted at 60°C.
4. A process as claimed in claim 1 wherein the catalyst in step (iii) is an enzyme.
5. A process as claimed in claim 4 wherein the enzyme is a lipase.
6. A process as claimed in claim 5 wherein the lipase is at a concentration load range of 2% to 15% (w/w).
7. A process as claimed in claim 6 wherein the lipase is at a concentration load 10% (w/w).
8. A process as claimed in claim 1 wherein step (iv) is conducted at a temperature ranging from 25°C to 30°C for of 10 to 20 hours.
9. A process as claimed in claim 1 wherein step (v) is conducted at a temperature ranging from 75°C to 85°C.
10. A process as claimed in claim 1 wherein step (vi) is conducted using separation method.
11. A process as claimed in claim 10 wherein the separation method is vacuum filtration.
12. A process as claimed in claim 1 wherein step (vii) is conducted using purification method.
13. A process as claimed in claim 12 wherein the purification method is short path distillation.
14. A process as claimed in claim 1 wherein step (x) is conducted using separation method.
15. A process as claimed in claim 15 wherein the separation method is vacuum filtration.
16. A high oleic content liquid palm olein fraction produced as claimed in claims 1 to 16.
17. A high oleic content liquid palm olein fraction as claimed in claim 17 having an iodine value of 75 to 95.
18. A high oleic content liquid palm olein fraction as claimed in claim 17 comprises of 55-65% by weight monounsaturated fatty acid, oleic, (C18:1), 10-15% by weight polyunsaturated fatty acid, linoleic (C18:2) and 20-30% by weight saturated palmitic (C16:0) and stearic (C18:0) acids.
19. A high oleic content liquid palm olein fraction as claimed in claim 17 comprises of 35-50% by weight triunsaturated triacylglycerols, 30-40% by weight diunsaturated-monosaturated triacylglycerols and 10-15% by weight disaturated-monosaturated triacylglycerols.
20. A high oleic content liquid palm olein fraction as claimed in claim 17 may consists of 20-40% by weight diacylglycerols.
21. A high palmitic content solid palm stearin fraction produced as claimed in claims 1 to 16.
22. A high palmitic content solid palm stearin fraction as claimed in claim 22 comprises of
65-90% by weight saturated fatty acids and 10-35% by weight monounsaturated fatty acids, wherein the saturated fatty acids further comprises of palmitic acid, C16:0 and stearic acid, C18:0, and
wherein the monounsaturated fatty acids further comprises of oleic acid, C18:1.
23. A high palmitic content solid palm stearin fraction as claimed in claim 22 comprises of 65-95% by weight trisaturated triacylglycerols and 5-35% by weight disaturated-monounsaturated triacylglycerols.
24. A high palmitic content solid palm stearin fraction as claimed in claim 22 having an iodine value of 10 to 25 and melting point of 55°C to 65°C.
25. A high palmitic content solid palm stearin fraction as claimed in claim 22 obtained during crystallization and fractionation temperatures of 5°C to 30°C.
26. Use of high oleic content liquid palm olein fraction as claimed in claims 17 to 21 as healthy frying oil or as salad oil, or other food preparation or formulations which require the usage of liquid oil.
27. Use of high palmitic solid palm stearin fraction as claimed in claims 22 to 26 as interesterified hard stock for the manufacture of trans free, low saturated fatty acid solid fat formulations, or other usage which requires the incorporation of hard fat.
28. A process for producing an enzymatic directed interesterified palm oil high in triunsaturated and trisaturated triacylglycerols wherein the process includes:
i. subjecting substantially moisture-free palm oil to a temperature ranging from 75°C to 85°C for a period of 30 to 45 minutes resulting in molten palm oil; lowering the temperature in step (i) to a range of 55°C to 70°C;
adding a catalyst into the molten palm oil to initiate directed interesterification reaction at a range of 55°C to 70°C for a period of 30 to 90 minutes;
subjecting the oil-catalyst mixture obtained in step (iii) to react at directed interesterification temperature of 20°C to 55°C for a period of 5 to 48 hours;
deactivating the catalyst;
removing the catalyst from the directed interesterified palm oil;
purifying the catalyst-free directed interesterified palm oil obtained in step (vi).
29. An enzymatic directed interesterified palm oil as claimed in claim 29 wherein the enzymatic directed interesterified palm oil is a fat comprises of low and high melting fractions
wherein the low melting fraction consists mainly of triunsaturated triacylglycerols and diunsaturated-monosaturated triacylglycerols and the high melting fraction consists mainly of trisaturated and disaturated- monounsaturated triacylglycerols.
30. An enzymatic directed interesterified palm oil as claimed in claim 29 contains a significant amount of diacylglycerols and monoacylglycerols of up to 50% depending on the reaction time of up to 48 hours.
31 . An enzymatic directed interesterified palm oil as claimed in claim 29 comprises of
20-35% by weight triunsaturated triacylglycerols,
30-40% by weight trisaturated triacylglycerols,
20-30% by weight diunsaturated-monosaturated triacylglycerols, and 15-25% by weight disaturated-monosaturated triacylglycerols,
wherein the triunsaturated triacylglycerols further comprise of triacylglycerols containing one linoleic and two oleic fatty acids (OLO), wherein the trisaturated triacylglycerols further comprise of triaclyglycerols containing three palmitic fatty acids (PPP) and triaclyglycerols containing two palmitic and one stearic fatty acids (PPS), wherein the disaturated-monosaturated triacylglycerols further comprise of triaclyglycerols containing one palmitic and two oleic fatty acids (POO) and triaclyglycerols containing one palmitic, one oleic and one linoleic fatty acids (PLO), and
wherein the diunsaturated-monosaturated triacylglycerols further comprise of triaclyglycerols containing one oleic and two palmitic fatty acids (POP).
32. A process for producing a directed interesterified palm oil high content in triunsaturated and trisaturated triacylglycerols wherein the process includes:
i. subjecting substantially moisture-free palm oil to 80°C for a period of 30 to 45 minutes resulting in molten palm oil;
ii. lowering the temperature in step (i) to 60°C;
iii. adding 10% (w/w) lipase into the molten palm oil to initiate directed interesterification reaction at a range of 55°C to 70°C;
iv. subjecting the palm oil-lipase mixture obtained in step (iii) to react at directed interesterification temperature of 25°C to 35°C for a period of 10 to 20 hours;
v. deactivating the lipase at 80°C;
vi. removing the lipase from the directed interesterified palm oil;
vii. purifying the lipase-free directed interesterified palm oil obtained in step (vi).
PCT/MY2014/000015 2013-02-13 2014-02-13 A process for producing high oleic content liquid palm oil fraction WO2014126454A1 (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070160739A1 (en) * 2003-12-26 2007-07-12 Yuji Kuwabara Method of dry fractionation of fat or oil
US20090130728A1 (en) * 2005-09-08 2009-05-21 Erik Johannes Anton Schweitzer Process for Producing a Triglyceride
KR20110034295A (en) * 2009-09-28 2011-04-05 씨제이제일제당 (주) A process for preparing hard butter
US20120027912A1 (en) * 2009-03-25 2012-02-02 Nobuo Sagi Method for producing hard butter composition
US20120238770A1 (en) * 2009-12-04 2012-09-20 Archer Daniels Midland Company Glycidyl ester reduction in oil

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070160739A1 (en) * 2003-12-26 2007-07-12 Yuji Kuwabara Method of dry fractionation of fat or oil
US20090130728A1 (en) * 2005-09-08 2009-05-21 Erik Johannes Anton Schweitzer Process for Producing a Triglyceride
US20120027912A1 (en) * 2009-03-25 2012-02-02 Nobuo Sagi Method for producing hard butter composition
KR20110034295A (en) * 2009-09-28 2011-04-05 씨제이제일제당 (주) A process for preparing hard butter
US20120238770A1 (en) * 2009-12-04 2012-09-20 Archer Daniels Midland Company Glycidyl ester reduction in oil

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