NZ724761B2 - Fatty acid composition and use thereof - Google Patents

Fatty acid composition and use thereof Download PDF

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Publication number
NZ724761B2
NZ724761B2 NZ724761A NZ72476115A NZ724761B2 NZ 724761 B2 NZ724761 B2 NZ 724761B2 NZ 724761 A NZ724761 A NZ 724761A NZ 72476115 A NZ72476115 A NZ 72476115A NZ 724761 B2 NZ724761 B2 NZ 724761B2
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New Zealand
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weight
acid
composition
fatty acids
fatty acid
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NZ724761A
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NZ724761A (en
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Krishnadath Bhaggan
Jun Ma
Zand Imro T
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Bunge Loders Croklaan Bv
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Priority claimed from PCT/EP2015/057073 external-priority patent/WO2015150405A1/en
Publication of NZ724761A publication Critical patent/NZ724761A/en
Publication of NZ724761B2 publication Critical patent/NZ724761B2/en

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    • 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
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/065—Microorganisms
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • 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
    • C11B1/00—Production of fats or fatty oils from raw materials
    • C11B1/02—Pretreatment
    • C11B1/025—Pretreatment by enzymes or microorganisms, living or dead
    • 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
    • C11B3/00—Refining fats or fatty oils
    • C11B3/003—Refining fats or fatty oils by enzymes or microorganisms, living or dead
    • 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
    • C11B3/00—Refining fats or fatty oils
    • C11B3/12—Refining fats or fatty oils by distillation

Abstract

fatty acid composition comprises: greater than 60% by weight stearic acid; from 3 to 30 % by weight oleic acid; and less than 10% by weight palmitic acid. The composition may be used in the preparation of a triglyceride.

Description

FATTY ACID COMPOSITION AND USE THEREOF This invention relates to a fatty acid composition, to a process for producing the composition and to the use of the composition in the preparation of triglycerides.
Triglyceride fats and oils are important components of many edible products. Fats and oils used in the food industry are frequently provided from vegetable sources such as sunflower and palm. Triglyceridefats can also be produced by the reaction of fats and oils with fatty acids; this allows the physical properties of the triglycerides, suCh as hardness and melting point, to be controlled. For example, the hydrogenation of oils to convert unsaturated fatty acids to saturated fatty acids, which can lead to the formation of unwanted trans fatty acids, can be avoided by transesterifying the oil with a satUrated fatty acid so as to introduce ted fatty acids into the triglyceride.
Stearic acid occurs in many animal and vegetable fats and oils, but it is more abundant in animal fat than vegetable fat. The exceptions are cocoa , shea butter and some other vegetable oil sources such as mango , sal and illipe, where the stearic acid content (as a triglyceride) is typically 28 to 45 %. See: http://en.wikipedia.org/wiki/Stearic_acid. Stearic acid can be prepared by treating these fats and oils with water at a high pressure and temperature, leading to the hydrolysis of triglycerides. The ing mixture is then distilled.
US 2589148 describes the separation of mixtures of fatty acids obtained by the hydrolysis of natural fats and oils. relates to a method of hydrolyzing a glycerol fatty acid ester—containing composition, such as a fat and/or an oil, to produce fatty acids having a low proportion of trans fatty acids.
EP-A—1001007 ns concentrates of shea sterols in ides with more than 12.5 weight % shea sterols, their preparation by enzymic hydrolysis of ides in shea oils or fractions f and the application of the concentrates in aerated food ts.
According to the present invention, there is provided a fatty acid composition sing: (i) greater than 60% by weight stearic acid; (ii) from 3% to 30%by weight oleic acid; and (iii) less than 10% by weight palmitic acid.
The term fatty acid, as used herein, refers to straight chain saturated or unsaturated ding mono-, di- and poly- unsaturated) carboxylic acids having from 12 to 22 carbon atoms. The term fat refers generally to compositions that n a mixture of fatty acid glycerides.
Also provided by the invention is a process for producing the fatty acid composition of the invention, comprising the enzymic hydrolysis of a triglyceride.
In another aspect, the invention provides the use of a composition of the invention in the preparation of a triglyceride.
Further provided by the invention is a method for the preparation of a first triglyceride comprising an enzymic acidolysis reaction between: a fat with at least 30% by weight of oleic acid in the 2- (Le, sn-2) on based on total C12 to 022 fatty acids at the 2- position; and the fatty acid composition of the invention.
The invention also provides a method for the preparation of a second triglyceride sing an enzymic acidolysis reaction between: a fat with at least 50% by weight of C12-C22 saturated-fatty acids in the 2- position based on total C12 to C22 fatty acids at the 2— position; anda second fatty acid composition obtainable by the process of the invention and sing greater than 63% by weight oleic acid, greater than 4% by weight linoleic acid and greater than 2% by weight stearic acid.
It has been found that compositions of the invention are particularly suitable for the ion of cerides (e.g., the first triglyceride) that can act as cocoa butter equivalents. They can form a cocoa butter equivalent that exhibits a cloSely similar g profile to cocoa butter.
The fatty acid ition of the invention ses at least 85 % by weight free fatty acids, more preferably at least 90 % by weight free fatty acids, such as at least 95 % by weight free fatty acids. The balance of the composition typically includes minor components such as glycerides.
The fatty acid composition is preferably non-hydrogenated i.e., the composition will not have been subjected to a hydrogenation step during its production from its natural source e.g., as a vegetable oil. The trans fatty acid t of the fatty acid composition is therefore typically less than 1 % by weight, more preferably less than 0.5 % by weight.
The fatty acid itions of the invention comprise greater than 60% by weight stearic acid. Preferably, the compositions comprise from 60 % to 80 % by weight stearic acid, more preferably from 61 to 75 % by weight stearic acid, such as from 62 to 72 % by - weight stearic acid.
The fatty acid compositions of the invention comprise from 3 % to 30 % by weight oleic acid, preferably from 10 to 29 % by weight oleic acid, such as from 15 to 28 % by weight oleic acid.
The fatty acid compositions of the invention comprise less than 10% by weight palmitic acid, preferably from 2 to 7 % by weight palmitic acid, such as from 4 to 6 % by weight palmitic acid. ‘ Preferably, the fatty acid compositions Comprise from 1 to 5 % by weight linoleic acid, such as from 2 to 4 % by weight linoleic acid. ably, the fatty acid compositions se from 1 to 3 % by Weight arachidic acid, such as from 1 to 2 % by weight arachidic acid.
A preferred fatty acid composition of the ion comprises from 60 % to 80 % by weight stearic acid, from 10 to 30 % by weight oleic acid, from 2 to 7 % by weight palmitic acid, from 1 to 5 % by weight linoleic acid, and from 1 to 3 % by weight arachidic acid.
The fatty acid composition of the invention is preferably obtainable from shea butter or its fractions, more preferably shea olein. Most preferably, the content of stearic acid in the shea olein is from 20 to 40 % by weight based on total fatty acids present and the content of oleic acid is from 45 to 65 % by weight based on total fatty acids present. will be appreciated that when referring to the shea olein, the fatty acid t refers fatty acids ing those bound in glycerides.
The process of the invention for producing the fatty acid composition of the invention comprises the enzymic hydrolysis of a triglyceride.
Preferably, the process of the invention also produces a second fatty acid composition comprising greater than 63% by weight oleic acid, greater than 4% by weight linoleic acid and greater than 2% by weight stearic acid.
More preferably, the second fatty acid composition comprises from 63 to 80 % by weight oleic acid, from 5 to 20 % by weight linoleic acid and from 5 to 20 % by weight stearic acid.
The second fatty acid composition comprises at least 90 % by weight free fatty acids, more preferably at least 95 % by weight free fatty acids, such as at least 98 % by weight free fatty acids. The balance of the composition typically includes minor components such as glycerides.
The second fatty acid ition preferably comprises from 65 to 75 % by weight oleic acid, such as from 66 to 70 % by weight oleic acid.
Preferably, the second fatty acid composition comprises from 5 to 15 % by weight linoleic acid, such as from 8 to 12 % linoleic acid.
The second fatty acid ition preferably ses from 5 to 20 % by weight stearic acid, such as from 8 to 15 % by weight stearic acid.
The second fatty acid composition may also comprise from 1 to 10 % by weight palmitic acid, more preferably from 4 to 8 % by weight ic acid.
The second fatty acid composition typically comprises from 0.5 to 2 % by weight of arachidonic acid.
A preferred second fatty acid composition comprises from 63 to 75 % by weight oleic acid, from 5 to 15 % by weight linoleic acid, from 5 to 20 % by weight stearic acid, from 1 to 10 % by weight palmitic acid, and from 0.5 to 2 % by weight of arachidonic acid.
The process of the invention preferably comprises: a) hydrolyzing a fat comprising at least 20% stearic acid based on the weight of the fatty acids present in the fat; b) distillation of the product of step a); and c) fractionation of the product of step b).
A particularly preferred process of the invention comprises: a) hydrolyzing a fat comprising at least 20% stearic acid based on the weight of the fatty acids present in the fat; b) distillation of the product of step a); and c) fractionation of the product of step b), wherein the fractionation in c) es: a first fatty acid Composition comprising greater than 60% by weight stearic acid, from 3% to 30% by weight oleic acid and less than 10% by weight palmitic acid; and a second fatty acid composition comprising greater than 63% by weight oleic acid, r than 4% by weightlinoleic acid and r than 2% by weight stearic acid.
Even more preferably, the proCess comprises: , a) hydrolyzing a fat comprising at least 20% stearic acid based on the weight of the fatty acids present in the fat; b) distillation of the product of step a); and ’c) fractionation of the product of step b), wherein the fractionation in c) produces: a first fatty acid composition comprising from 60 2.0 % to 80 % by weight stearic acid, from 10 to 30 % by weight oleic acid, from 2 to 7 % by weight palmitic acid, from 1 to 5 "/0be weight ic acid, and from '1 to 3 % by weight arachidic acid; and a second fatty acid ition cOmprises from 63 to 75 % by weight oleic acid, from 5 to 15 % by weight ic acid, from 5 to 20 % by weight stearic acid, from 1 to 10 % by weight palmitic acid, and from 0.5 to 2 % by weight of arachidonic acid.
The hydrolysis in a) preferably involves the hydrolysis of the fat to release at least 50 % by weight of the fatty acids that are present in glycerides in the fat as free fatty acids.
Preferably, at least 60 % by weight of the fatty acids in the fat are released, more preferably at least 70 % by weight, such as at least 75 % by .
The ysis in a) can be carried out chemically or enzymicaily. The hydrolysis in a) is preferably carried out using one or more lipase enzymes. The enzyme or mixture of enzymes is non-specific to aliow for hydrolysis at the 1-, 2- and 3— positions in the giyceride. 2015/057073 Preferably, the hydrolysis in a) is carried out in the presence of water, more preferably in an amount of from 1 to 50 % by weight. The hydrolysis is typically carried out at a temperature of from 20 to 60 °C for from 1 hour up to about 30 hours.
The fat used in step a) is ably shea butter and/or a fraction thereof, more preferably Shea olein. When shea olein is used, the content of stearic acid in the shea olein is ably from 20 to 40 % by weight based on total fatty acids present and the content of oleic acid is from 45 to 65 % by Weight based on total fatty acids present. Again, it will be iated that when referring to the shea olein, the fatty acid content refers to fatty acids including thoSe bound in glycerides.
The t obtained in a) is typically extracted from the reaction mixture (for example, by removal of the aqueous phase) and ally dried- This product is distilled in b), for example by short path distillation, in order to te free fatty acids from any unhydrolysed glycerides. The free fatty acids are collected as the distillate. Suitable distillation conditions are a temperature of 180 to 220 °C and a pressure of from 1 x 10'? to 10 x10‘3mbar.
The product of b) is fractionated in c). Fractionation can be wet or dry and is preferably dry (i.e., without added solvent). Fractionation is preferably carried out at a temperature in the range of from 30 to 45 °C. The cooling rate is preferably from 3 to 6 °C per hour, more preferably followed by a holding time of from 5 to 10 hours. The fractionation in c) forms a stearin fraction that is the first fatty acid fraction of the invention and an olein fraction that is the second fatty acid fraction of the invention. The first and second fatty acid fractions are then separated, for example by filter pressing.
The first and second fatty acid compositions of the invention may be used in the preparation of triglycerides.
The invention provides a method for the preparation of a first triglyceride sing an enzymic acidolysis reaction between: a fat with at least 30% by weight of oleic acid in the 2- position based on total 012 to C22 fatty acids at the 2- position; and the fatty acid composition of the invention.
Preferably, the fat with at least 30% by weight of oleic acid in the 2- on based on total C12 to C22 fatty acids at the 2- on is a palm mid-fraction. The weight ratio of the fat to the fatty acid composition is preferably in the range of from 2:1 to 1:2, more preferably from 1.221 to 121.2.
The method is typically carried out using a lipase, preferably a 1,3 specific . A small amount of water is preferably present, such as in an amount of from 0.05 to 5 % by weight of the reaction mixture.
Excess'fatty acids may be removed from the triglyceride by distillation, for example short path distillation.
The product of the enzymic acidolysis reaction, optionally after any distillation, is preferably fractionated. Fractionation may be wet or dry but is preferably solvent (i.e., wet) fractionation, more preferably in the presenCe of acetone. The fractionatibn is ably carried out to provide the first triglyceride asa mid—fraction. A first solvent fractionation is carried out, preferably at a temperature of from 5 to 15 °C, solids are removed and the olein (liquid, supernatant fraction) is collected. A second fractionation of this olein fraction is d out, preferably at a temperature in the range of from 15 to °C such as from 20 to 25 °C, and a stearin on is collected as the triglyceride product. The yield of the final ceride after fractionation is preferably from 40 to 70 % by , more ably from 50 to 65 % by weight. The first triglyceride may be used as a cocoa butter equivalent i.e., as a substitute for cocoa butter or as an additive to cocoa butter. For example, the first triglyceride may be used in a tionery coating, bar orifilling, e.g., together with components such as sugar and/or cocoa powder.
Also provided by the invention is a method for the preparation of a second triglyceride comprising an enzymic acidolysis reaction between: a fat with at least 20-40% by weight of 2 saturated fatty acids in the 2- position based on total C12 to 022 fatty acids at the 2- position; and a second fatty acid composition comprising greater than 63 % by weight oleic acid, greater than 4 % by weight linoleic acid and greater than 2 % by weight stearic acid.
The second triglyceride produced from the second fatty acid composition preferably comprises 1,3-dioleoylpalmitoyl glyceride (OPO).
The fat with at least 20-40% by weight of C12-022 saturated fatty acids in the 2- position based on total C12 to C22 fatty acids at the 2— position ably has at least 50% palmitic acid at the 2- on based on total fatty acids at the 2- position. It will be WO 50405 iated that the palmitic acid present in the fat is bound in glycerides, including triglycerides. A red fat having at least 20—40%% by weight of 012-022 saturated fatty acids in the 2- position based on total C12 to C22 fatty acids at the 2- position is palm oil stearin.
The method comprising the c acidolysis reaction between the fat and the second fatty acid composition may becarried out as described in . Thus, the method may be carried out in the ce of an , preferably a 1,3 specific lipase. Under the influence of the 1,3 lipase, oleoyl residues are introduced into the 1- and 3- positions of the triglyceride by ge with the fatty acid es of the triglyceride. The 2-palmitoyl triglycerides modified in this way may be separated from the reaction mixture. The reaction in the process of the present invention selectively exchanges palmitic acid with oleic acid on the sition rather than the 2-position.
The transesterification reaction is performed to reach or approach equilibrium at a conversion ratio to 1,3—dioleoyl 2—palmitoyl glyceride Of a minimum of 50 %, preferably at least 60 %, most preferably at least 70 % by moles based on the starting triglyceride.
Preferably, palm oil stearin is, for example, mixed with the Second fatty acid composition at a weight ratio of palm oil stearin to oleic acid of preferably from 0.1:1 to 2:1, more preferably from 0.4:1 to 12:1, even more preferably from 0.4:1 to 1:1, most preferably from 121.1 to 1:2 on a weight basis.' The reaction is preferably carried out at a temperature from 30°C to 90°C, preferably from 50°C to 80°C, such as around 60°C to 70°C, and may be conducted batchwise or in continuous fashion, with or without a water- immiscible organic solvent. Before the reaction, 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 de/emar, from Amano Enzyme lnc., Japan) or lised concentrates of Rhizomucor miehei yme RM M from Novozymes, k). The product obtained is ably subjected to a further step in which it is purified. In order to separate the fatty acids and eSters from the product triglyceride fraction, the composition (optionally after further ent, such as isolation of the fat phase) may be distilled at low pressure (< 10 mbar) and elevated temperatures (>200 °C).
After distillation of the composition, the triglyceride fraction is preferably fractionated to recover the CPO-containing glyceride. This can be done using solvent onation or dry fractionation, using a single, two-step or multi-step fractionation technique, but is preferably carried out using single step dry fractionation. Fractionation preferably tripalmitins down to a level of less than 15 weight %, more removes the unconverted preferably less than 10 weight "/0, most preferably less than 8 weight %. The product is typically fully refined to remove all remaining fatty acids and inants to produce a refined OPO fraction. Fractionation preferably comprises a hold temperature in the formed during onation is preferably separated range of from 37 to 47°C. The stearin from the olein by tion, for example by filter pressing. The yield of the desired olein is preferably in the range of from 70 to 95 % by weight. - The method may comprise one or more additional steps of further purifying the product with respect to 1,3-dioleoyl 2—palmitoyl glyceride.
The second triglyceride that is produced by the process of the present invention may least comprise OPO glycerides preferably in an amount of at least 10 % by weight or at 20% by weight. The balance typically comprises other 0 triglycerides. used, for example, as a fat component in an infant The second triglyceride may be formula.
The listing or discussion of an apparently prior-published document in this ication should not necessarily be taken as an ledgement that the document is part of the state of the art or is common general knowledge.
Preferences and options for a given aspect, embodiment, feature or parameter of the invention should, unless the context indicates othenNise, be regarded as having been disclosed in ation with any and all preferences and options for all other aspects, embodiments, features and ters of the invention. For example, the preferred features of the first and second fatty acid compositions may be applied to the process the invention and the methods of the invention for producing the first and second triglycerides.
The following non-limiting es illustrate the invention and do not limit its scope any way. In the examples and throughout this specification, all percentages, parts and ratios are by weight unless indicated othenlvise. For example, percentages by weight of fatty acids in the first and second fatty acid compositions are based on the the percentage of the respective free fatty acid in the total weight of the composition.
EXAMPLES Shea olein was fully hydrolyzed enzymatically. The reaction was catalyzed by a mixture of lipases, Lipase Amano G and Lipase Amano AY.
About 4 kg of shea olein was mixed with 1.2 kg of demineralized water (30% wt) and the mixture was stirred at 40°C until a homogeneous emulsion was obtained. To this emulsion‘was added 2 gram of Lipase Amano AY and 1.6 gram of Lipase Amano G and the mixture was stirred for an additional 24 hours at 4050. After this, the reaction was Stopped by heating the reaction mixture to 80°C and ng‘at this temperature for at least 30 min. Thereafter the stirring was stopped, settled down and the water phase was removed. The free fatty acid containing product was washed with 1.0 kg hot ralized water and dried under vacuum. Thedried fatty acid containing t was led in order to Separate the free fatty acids from the unhydrolyzed glycerides by means of short path distillation at a temperature of about 195°C and a pressure of about 4 x 10‘3 mbar. The free fatty acids were collected as distillate. The fatty acid composition of the products is given in Table 1. 2015/057073 Table 1. Fatty acid composition of shea olein and fractions of shea olein after enzymatic hydrolysis and distillation N4:.co 'to 09AM .09 —\l\) .01 4:. 01 00 .p. 01DJ 00 Ac’ 00 miss” -f>-\l . .0940 .b IF.- Hm 3 o .p o w $.09 A\l.f-nmm oo‘1 mono Plato—A m_\.
In this and other tables, Cx:y refers to a fatty acid having x carbon atoms and y double bonds; 0 refers to cis fatty acids; levels determined by GC-FAME Example 2 The distillate obtained in Example 1 was dry-fractionated using a lab-scale crystallizer.
To achieve a workable amount, several batches were produced. The fraction was performed at three different temperatures in the range of from 30°C to 45°C.
About 500 gram of the distillate was put in the crystallizer and heated to 70°C in order to erase any crystal memory. After this the oil was cooled to 40-35°C at a cooling rate of about 4.3-5°C /hour.
After this the obtained slurry was stabilized at the final temperature for about 7 hours and the formed crystals were separated from the olein fraction by using a lab-scale filter press. The pressing program used was as s: increase of pressure from O to 24 bar in 6 hours and then squeezing at 24 bar for 6 hours.
High c acid n fractions were obtained cts 1a, 1b, 10 of the invention) and high oleic acid olein fractions were obtained (Products 2a, 2b, 20). See Table 2.
Table 2. Dry fractionation of shea fatty acids obtained via enzymatic ysis of shea olein and lation. Fractionation was performed at different temperatures.
Distillate Stearin Stearin Stearin Compar- Olein Olein Product Product Product ative Product Product example anal sis C16:0 -=--_-:0.2 4. 7 4.5 C18“0 28.7 63.6 69.8 70.4 98.3 10.3 .1 20 19.8 -—-—112 C18:3 0.1 0.1 ' 0.1 0.1 6-6 6-6 020:0. 1.1 1.5 1. 5 1.5 0.8 .4 3.2 0.2 ' 0.2 * 0.5 C22:0 0.1 0.1 0.1 * 0.1 _ SAFA 36.1 705 76.6 76.8 99.8 17.7 166 216 16-1 66 616 PUFA 11.4 11.1 Example 3 Acidolysis of palm mid-faction was carried out with the shea stearic acid concentrate of Example 2. The acidolysis reaction was performed using a lab scale packed bed reactor (PBR).
About 1200 gram of hard palm mid-fraction was blended with 1200 gram of stearic acid concentrate from Example 2 (Product 10). To this blend, 0.15% (wt) demineralized water was added and the mixture was transferred to the feed vessel of the PBR equipment.
The PBR column was filled with 5 gram of lipase from Rhizopus oryzae immobilized on an Accurel support and the temperature was set at 70°C. The feed was passed through the column at an average flow rate of about 12.7 g/hours and the acidolyis on was monitored by measuring the level of 1,3-dipalmitoyl—2—oleoyl glyceride (POP) in the product. The excess of fatty acids in the interesterified product were led off by means of short path lation. The interesterified palm mid fraction (residue product obtained after lation) was solvent fractionated as follows in order to obtain the desired on meeting the required characteristics.
About 400 gram of the interesterified oil was dissolved in 2 kg of acetone at 50°C and was cooled down to 842°C and kept at this temperature for 30 min. After this, the , formed crystals were filtered off and the atant was heated up to 50°C and then cooled down to 20—24°C and kept at this temperature for 30 min. The formed crystals were filtered off and the solvent from the supernatant was evaporated that resulted in the main product. The l yield was about 57%, while the top stearin was about 10% and olein fraction about 33%. The analytiCal data for the products are contained in Table 3.
Table 3. Enzymatic cocoa butter analogue (eCCB) ed via ysis of palm mid- fraction With shea olein stearic acid concentrate followed by distillation and fractionation.
Interesterified'k eCCB mid ' mid— fraction . palm ' fraction L 0-2 0.1 o —_-m-—— —__3'__ —_n—0* :__:_08 _———__ SAFA 60.1 47.8 887 MUFA Total Trans Silver phase data HPLC* 830 j: . 3p|us double * * 0.6 * bond in the tri-l ceride Triglyceride composition Nil-_02 o 2 mil—___:— Iii-___- Ito-___- MLP 0.1 0-3 _— PPSt o-s - lira-___— PLP ___m- PLSt PLO 2 4.3 0.7 [- PLL on o [- StStSt StOSt Stoo 000 ___:- suo ___!- ow ___:- "___ AOSt ___mszeNzoNMR szewzsNMR___ szeNsowMR___— szewss NMR __- *S = saturated fatty acid; 0 = oleic acid; L= linoleic acid; ** Triglyceride ition MPP, etc, was determined by GC (ISO 23275) and es triglycerides having the same fatty acids in different positions e.g., MPP includes MPP and PMP; M, O, P, St, L and A refer to myristic, oleic, palmitic, stearic, linoleic and arachidic acids, respectively 826Nx refers to solid fat content determined according to 180 8291-1 (beta stabilized at 26°C) at X °C Figure 1 is a plot of % solids at temperatures 20, 25, 30 and 35 °C for fat blends sing 0-100% cocoa butter (CB) and 100-0% of the eCCB mic cocoa butter”) of Example 3 showing the compatibility of the enzymatic cocoa butter analogue with cocoa butter (CB).
Acidolysis of palm stearin was carried out with the shea oleic acid trate of Example 2. The acidolysis reaction was med using a lab scale packed bed reactor (PBR).
About 1290 gram of hard palm stearin with iodine value (IV) number of about 14 was blended with about1810 gram of oleic acid concentrate from Example 2 (Product 2a). To this blend, about 0.‘l5°/o (wt) demineralized water was added and the mixturewas transferred to the feed vessel of the PBR equipment. The PBR column was filled with 5 gram of lipase from Rhizopus oryzae lized on Accurel and the temperature Was set at 60°C. The feed was passed through the column at an average flow rate of about 12.7 g/hours and the acidolyis reaction was monitored by measuring the level ofcarbon number C48 in the product. The excess of fatty acids in the interesterified product were distilled off by means of short path distillation. The interesterified hard palm stearin (the residue of the product obtained after distillation) was dry fractionated as folloWs in order to’obtain the desired olein fraction g the required characteristics.
About 1000 gram of the interesterified oil was dry onated. The oil Was first heated to 70°C and then cooled down to 37 - 42°C as follows: from 70°C to 42 - 47°C and then - 47°C in about 2-5 hours, hold for 2-6 hours at 42 Cooled further to 37 — 42°C in 5-10 hours and hold at this temperature for about 5-10 hours.
The crystals formed were separated by using a lab scale filter press. The slurry was pressed using the following program: increase pressure from 0 — 24 bar in 60 min and ing at 24 bar for 30 min.
In this way, about 87% olein product was obtained. The analytical results are shown in table 4.
Table 4. Enzymatic interesterified palm n obtained via acidolysis containing 080 and 880 type of triglycerides.
Palm stearin Interesterififled Olein on Stearin Palm stearIn = product fraction _ Fractionation Temp IC)-_ 37-42' Viewm % __-o_— FAME composition C18:2cis _-_m--_€18scis -E-=C2021cis _-_“._—0.2 0.2 O. 1 c24:0 “HE-“m.
SAFA —___ MUFA 98 419 ——fi_-_PUFA 22 Silver phase HPLC

Claims (19)

1. A fatty acid composition comprising: (i) from 60 to 80 % by weight stearic acid; (ii) from 3 to 30% by weight oleic acid; and (iii) less than 10 % by weight ic acid.
2. The composition as claimed in Claim 1, wherein the fatty acids in the composition are drogenated.
3. The composition as claimed in Claim 1 or Claim 2, which comprises from 10 to 30 % by weight oleic acid.
4. The ition as claimed in any one of Claims 1 to 3, which comprises from 2 to 7 % by weight palmitic acid.
5. The composition as claimed in any one of Claims 1 to 4, which comprises from 1 to 5 % by weight linoleic acid.
6. The composition as claimed in any one of Claims 1 to 5, which comprises from 1 to 3 % by weight arachidic acid.
7. The composition as claimed in any one of Claims 1 to 6, which is obtained from shea olein.
8. A process for producing the fatty acid composition of any one of the preceding claims, comprising the enzymic hydrolysis of a triglyceride.
9. The process as claimed in Claim 8, which also produces a second fatty acid composition comprising greater than 63% by weight oleic acid, greater than 4% by weight linoleic acid and greater than 2% by weight stearic acid.
10. The process as claimed in Claim 9, wherein the second fatty acid composition ses from 63 to 80 % by weight oleic acid, from 5 to 20 % by weight linoleic acid and from 5 to 20 % by weight stearic acid.
11. The process as d in any one of Claims 8 to 10 comprising: a) hydrolyzing a fat comprising at least 20% stearic acid based on the weight of the fatty acids present in the fat; b) distillation of the product of step a); and c) fractionation of the product of step b).
12. The process as claimed in Claim 11, wherein the fat of step a) is shea butter and/or a fraction thereof.
13. Use of a composition as claimed in any one of Claims 1 to 7 in the preparation of a triglyceride.
14. Method for the ation of a triglyceride comprising an enzymic acidolysis reaction n: a fat with at least 30% by weight of oleic acid in the 2- position based on total C12 to C22 fatty acids at the 2- position; and the fatty acid composition of any one of Claims 1 to 7.
15. Method for the preparation of a triglyceride comprising an c acidolysis reaction between: a fat with at least 20-40% by weight of C12-C22 saturated fatty acids in 2- on based on total C12 to C22 fatty acids at the 2- position; and the second fatty acid ition as defined in Claim 9 or Claim 10.
16. The composition as claimed in any one of Claims 1 to 7, substantially as hereinbefore described with reference to any one of the examples.
17. The process as claimed in any one of Claims 8 to 12, substantially as hereinbefore described with reference to any one of the examples.
18. The use as claimed in Claim 13, substantially as hereinbefore described with reference to any one of the examples.
19. The method as claimed in Claim 14 or Claim 15, substantially as hereinbefore bed with reference to any one of the examples.
NZ724761A 2014-04-04 2015-03-31 Fatty acid composition and use thereof NZ724761B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP14163603 2014-04-04
EP14163603.5 2014-04-04
PCT/EP2015/057073 WO2015150405A1 (en) 2014-04-04 2015-03-31 Fatty acid composition and use thereof

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NZ724761B2 true NZ724761B2 (en) 2021-01-06

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