Process for preparing a triglyceride composition

Abstract

The invention relates to a process for preparing a triglyceride composition comprising SOS triglycerides, wherein S represents stearic acid residues and O represents oleic acid residues. The process involves the steps of mixing a first triglyceride feed composition with a high oleic acid content with a fatty acid or fatty acid aliphatic alcohol ester composition and reacting the obtained mixture in the presence of an sn-1,3-specific lipase. The obtained first product composition is distilled to remove the fatty acids and / or fatty acid aliphatic alcohol esters. The process is repeated a second time by reacting the distilled first product composition with a second fatty acid or fatty acid aliphatic alcohol ester composition in the presence of an sn-1,3-specific lipase. Finally, the obtained second product composition is then distilled to remove fatty acids and / or fatty acid aliphatic alcohol esters. The resulting triglyceride composition can be used as a cocoa butter equivalent in the manufacture of a chocolate or chocolate-like product.

Description

[0001] PROCESS FOR PREPARING A TRIGLYCERIDE COMPOSITION

[0002] FIELD OF THE INVENTION

[0003] This invention relates to a process for preparing a triglyceride composition comprising SOS triglycerides. The preparation of SOS rich triglyceride compositions is of particular relevance in the production for cocoa butter equivalents or other confectionary products.

[0004] BACKGROUND OF THE INVENTION

[0005] Triglycerides comprise three fatty acid residues bonded to a glycerol backbone. Their structure can be described using "sn" notation, which stands for stereospecific numbering. In a Fischer projection of a natural L-glycerol derivative, the secondary hydroxyl group is shown to the left of C-2; the carbon atom above this then becomes C-1 and that below becomes C-3. The prefix “sn” is placed before the stem name of the compound.

[0006] H

[0007] H-C-OOCR’ position so-1

[0008] R OO-C-H position sn~2

[0009] I

[0010] H-C-OOCR"' position sn-3

[0011] H

[0012] Fischer projection of a natural L-glycerol derivative.

[0013] The physical properties of a triglyceride are determined by the nature of the fatty acid residues and their positions on the glycerol backbone. It can therefore be desirable to alter the type and position of fatty acid residues in vegetable oils to attain desired physical properties.

[0014] Triglyceride compositions which have a high SOS (stearic-oleic-stearic or 1 ,3-distearoyl 2-oleoyl) triglyceride content (wherein S represents stearic acid (C18:0) residues and O represents oleic acid (C18:1 ) residues) are particularly commercially valuable products. SOS triglycerides are present at a high level in cocoa butter and contribute to the characteristic physical properties of chocolate such as its firmness and “snap” when bitten, and its rapid melting at mouth temperature, which provides a smooth, creamy consistency during eating. Accordingly, triglyceride compositions which have a high SOS triglyceride content can be useful as cocoa butter equivalents or components thereof.

[0015] Enzymatic transesterification for producing symmetric mono-unsaturated triglycerides is well known within the prior art. Existing technologies generally involve a process where a starting oil that is rich in triolein (OOO) is mixed with fatty acids or fatty acid esters (such as methyl stearate). The blend is then processed using an sn-1 ,3-specific lipase which introduces stearic acid onto the triglyceride at the 1 and 3 positions, thereby converting 000 triglycerides into SOS triglycerides. Typically, the triglyceride composition that is obtained in the reaction then has to undergo further processing to both concentrate the SOS content of the oil and to remove undesired triglycerides which will negatively impact the functionality of the final triglyceride composition. Normally, this is done by subjecting the resulting SOS-rich triglyceride composition to a distillation process followed by one or two fractionation step(s). However, fractionation generally involves large facilities and high costs.

[0016] For instance, EP 2251428 A1 describes a process for preparing a triglyceride composition comprising from 50 to 80% by weight SOS and from 5 to 20% SOO, which comprises reacting triolein with stearic acid in the presence of a 1 ,3-specific lipase from Rhizopus oryzae to form interesterified glycerides. The interesterified glycerides are then fractionated, which provides a product having a high SOS content, but produces a side-stream that needs to be handled.

[0017] The SOS triglyceride content of the reaction product can be increased by providing a greater amount of fatty acid or fatty acid ester in the reaction mixture, which drives the equilibrium of the reaction towards the production of SOS triglycerides.

[0018] However, the use of a high ratio of the amount of fatty acid ester to the amount of oil necessitates the removal of large amounts of excess fatty acid ester and may result in an increased content of SSS triglycerides and SSO triglycerides. Both SSS and SSO triglycerides negatively affect the crystallization of the produced SOS-rich triglyceride composition. SSS triglycerides can be removed by fractionation to increase the SOS content of the product, but it is not possible to remove the SSO triglycerides from the obtained triglyceride composition and high amounts of SSO can render the product useless. US 6,090,598 describes a process in which the concentration of the desired triglyceride species can be increased without fractionation, by carrying out distillation of the product of an interesterification reaction in such a manner that only fatty acids and / or their esters liberated from triglycerides due to interesterification which have boiling points lower than that of the feedstock fatty acid or fatty acid ester are distilled off, while preventing distillation of the feedstock fatty acid or fatty acid ester. The concentration of the desired triglyceride species can then be increased by subjecting the product to further enzymatic interesterification. Whilst this process provides triglyceride products having an increased concentration of desired triglyceride species, it can only be used when the boiling point of the fatty or fatty acid ester that is liberated from the triglyceride in the interesterification reaction is lower than the boiling point of the feedstock fatty acid or fatty acid ester.

[0019] Accordingly, the process is not useful for obtaining compositions rich in SOS triglycerides from compositions rich in OOO triglycerides, because oleic acid liberated during an interesterification reaction cannot be effectively distilled off while preventing the distillation of stearic acid.

[0020] Thus, it is desirable to control processes for producing triglyceride compositions such that the different fatty acid residues are selectively attached at different positions on the glycerol backbone. Especially, it is desirable to obtain triglyceride compositions which are rich in SOS triglycerides, these being valuable commercial products which may be used alone or in combination with other triglycerides as a cocoa butter equivalent (CBE). Moreover, there remains a need to provide processes for the production of compositions sufficiently rich in SOS triglycerides, such that a fractionation step is not required to provide a further increase in SOS content following the transesterification reaction. Furthermore, it would be desirable to provide such processes whilst limiting the amount of side streams which require further processing. Furthermore, it would be desirable to provide a process which is not restricted to the use of starting materials in which the fatty acid or fatty acid ester liberated from the triglyceride starting material has a lower boiling point than the fatty acid or fatty acid ester feedstock.

[0021] SUMMARY OF THE INVENTION

[0022] The inventors have found that it is possible to increase the concentration of SOS triglycerides provided in an enzymatic transesterification process, without the need to fractionate the product to further increase the SOS content of the product. By using the process of the invention, the inventors have found that the concentration of SOS triglycerides in the product can surprisingly be increased sufficiently to avoid the need for a fractionation step to concentrate the SOS content, whilst still limiting the amount of side streams which require further processing. As will be readily appreciated, such fractionation process are energy-demanding and some such as solvent fractionation require the use of potentially hazardous and environmentally challenging solvents. Thus avoiding the use of such a process is both energy efficient and cuts down on the need for, for example, washing steps which reduces the need for water usage and accordingly wastewater production. Moreover, the process of the invention is not restricted to the use of starting materials in which the fatty acid or fatty acid ester liberated from the triglyceride starting material has a lower boiling point than the fatty acid or fatty acid ester feedstock. Thus, the process of the invention can utilise a triglyceride feed composition that is rich in oleic acid residues to produce a composition that is rich in SOS triglycerides, in spite of the fact that oleic and stearic acid have essentially the same boiling point.

[0023] Accordingly, the invention provides a process for preparing a triglyceride composition comprising SOS triglycerides, wherein S represents stearic acid (C18:0) residues and O represents oleic acid (C18:1 ) residues, said process comprising: a) providing a first triglyceride feed composition, wherein the first triglyceride feed composition comprises at least 60% oleic acid fatty acid residues, by weight of the total C6-C24 fatty acid residues of the first triglyceride feed composition, and further wherein the first triglyceride feed composition has an oleic acid content in the sn-2 position of at least 65% by weight of the total sn-2 C6-C24 fatty acid residues of the first triglyceride feed composition; b) introducing into the first triglyceride feed composition a first fatty acid / fatty acid aliphatic alcohol ester composition to form a first reaction mixture, and reacting the first reaction mixture in the presence of an sn-1 ,3-specific lipase to produce a first product composition, wherein the first fatty acid / fatty acid aliphatic alcohol ester composition comprises at least 80% by weight of stearic acid, and / or an aliphatic alcohol ester thereof ; c) distilling the first product composition to remove fatty acids and / or aliphatic alcohol esters of fatty acids from the composition to produce a second triglyceride feed composition; d) introducing a second fatty acid / fatty acid aliphatic alcohol ester composition into the second triglyceride feed composition to form a second reaction mixture, and reacting the second reaction mixture in the presence of an sn-1 ,3-specific lipase to produce a second product composition, wherein the second fatty acid / fatty acid aliphatic alcohol ester composition comprises at least 80% by weight of stearic acid, and / or an aliphatic alcohol ester thereof; and e) distilling the second product composition to remove fatty acids and / or aliphatic alcohol esters of fatty acids from the second product composition, and optionally further comprising: f) introducing a third fatty acid / fatty acid aliphatic alcohol ester composition into the second product composition to form a third reaction mixture and reacting the third reaction mixture in the presence of an sn-1 ,3-specific lipase to produce a third product composition, wherein the third fatty acid / fatty acid aliphatic alcohol ester composition comprises at least 80% by weight of stearic acid, and / or an aliphatic alcohol ester thereof ; and g) distilling the third product composition to remove fatty acids, and / or aliphatic alcohol esters of fatty acids from the third product composition; wherein the ratio of the total amount of the first, second and, where present, third fatty acid / fatty acid aliphatic alcohol ester compositions to the amount of first triglyceride feed composition provided in step a) is 2:1 to 6:1 by weight.

[0024] By distilling the first product composition to remove fatty acids and / or aliphatic alcohol esters of fatty acids from the composition to produce a second triglyceride feed composition and then introducing a second fatty acid / fatty acid aliphatic alcohol ester composition comprising at least 80% by weight of stearic acid, and / or an aliphatic alcohol ester thereof, before a second reaction step, it has been found that the SOS triglyceride content of the product can be increased relative to known processes. Surprisingly, the inventors have found that, by using the process of the invention, an SOS content can be obtained that is sufficiently high to avoid the need for a costly fractionation step intended to increase the SOS triglyceride content of the product. Moreover, this is achieved without the need to use a high excess of fatty acid or fatty acid aliphatic alcohol ester which creates undesirable side reactions and side streams which are complicated to manage. Such high excesses of fatty acid or fatty acid aliphatic alcohol ester (for example 10:1) result in large volumes of side streams which themselves must be processed, for example by way of distillation, hydrogenation and bleaching which processes are energy intensive, require specific equipment and use unnecessary amounts of water. Therefore, ability to avoid such excesses is important from a sustainability and energy reduction point of view.

[0025] Accordingly, the process preferably does not comprise a fractionation step in which the SOS triglyceride content of the first, second and / or third product composition is increased by more than 5% by weight relative to the SOS triglyceride content of the product composition before the fractionation.

[0026] The resulting triglyceride composition can be used as a cocoa butter equivalent in the manufacture of a chocolate or chocolate-like product.

[0027] DETAILED DESCRIPTION OF THE INVENTION

[0028] As described above, the invention is directed to a process for preparing a triglyceride composition comprising SOS triglycerides, wherein S represents stearic acid (C18:0) residues and O represents oleic acid (C18:1 ) residues, said process comprising: a) providing a first triglyceride feed composition, wherein the first triglyceride feed composition comprises at least 60% oleic acid fatty acid residues by weight of the total C6- C24 fatty acid residues of the first triglyceride feed composition, and further wherein the first triglyceride feed composition has an oleic acid content in the sn-2 position of at least 65% by weight of the total sn-2 C6-C24 fatty acid residues of the first triglyceride feed composition; b) introducing into the first triglyceride feed composition a first fatty acid / fatty acid aliphatic alcohol ester composition to form a first reaction mixture, and reacting the first reaction mixture in the presence of an sn-1 ,3-specific lipase to produce a first product composition, wherein the first fatty acid / fatty acid aliphatic alcohol ester composition comprises at least 80% by weight of stearic acid, and / or an aliphatic alcohol ester thereof ; c) distilling the first product composition to remove fatty acids and / or aliphatic alcohol esters of fatty acids from the composition to produce a second triglyceride feed composition; d) introducing a second fatty acid / fatty acid aliphatic alcohol ester composition into the second triglyceride feed composition to form a second reaction mixture, and reacting the second reaction mixture in the presence of an sn-1 ,3-specific lipase to produce a second product composition, wherein the second fatty acid / fatty acid aliphatic alcohol ester composition comprises at least 80% by weight of stearic acid, and / or an aliphatic alcohol ester thereof; and e) distilling the second product composition to remove fatty acids and / or aliphatic alcohol esters of fatty acids from the second product composition, and optionally further comprising: f) introducing a third fatty acid / fatty acid aliphatic alcohol ester composition into the second product composition to form a third reaction mixture and reacting the third reaction mixture in the presence of an sn-1 ,3-specif ic lipase to produce a third product composition , wherein the third fatty acid / fatty acid aliphatic alcohol ester composition comprises at least 80% by weight of stearic acid, and / or an aliphatic alcohol ester thereof ; and g) distilling the third product composition to remove fatty acids, and / or aliphatic alcohol esters of fatty acids from the third product composition; wherein the ratio of the total amount of the first, second and, where present, third fatty acid / fatty acid aliphatic alcohol ester compositions to the amount of first triglyceride feed composition provided in step a) is 2:1 to 6:1 by weight.

[0029] The first triglyceride feed composition which is provided in step a) and used in the process of the invention is an oil which should have a fatty acid composition with a relatively high level of oleic acid. The fatty acid composition of an oil or fat can be determined by a gas chromatographic analysis of the methyl ester derivatives, prepared by transesterification. The technique of gas-liquid chromatography (GLC), also referred to as gas chromatography (GC), is a form of partition chromatography in which the mobile phase is a gas and the stationary phase is a liquid. The sample is volatilised during injection and an equilibrium is formed between the gas phase and the liquid phase, which is fixed at the inner wall of the column. When the sample contains different components, they diffuse into the liquid phase to varying degrees according to their individual equilibrium constant, and so travel down the column at different rates. This results in different retention times, and thus a physical separation. The separated components emerge from the end of the column exhibiting peaks of concentration, ideally with a Gaussian distribution. These peaks are detected by the Flame Ionization Detector (FID), which converts the concentration of the component in the gas phase into an electrical signal, which is amplified and passed to a continuous recorder, so that the progress of the separation can be monitored and quantified. A suitable method is IUPAC method 2.304. The first triglyceride feed composition which is provided in step a) used as a reactant for the transesterification should comprise at least 60% oleic acid (C18:1) fatty acid residues, by weight of the total C6-C24 fatty acid residues of the first triglyceride feed composition. Preferably, the first triglyceride feed composition comprises at least 65% oleic acid (C18:1) fatty acid residues, more preferably at least 75% oleic acid (C18:1) fatty acid residues, and most preferably at least 80% oleic acid (C18:1 ) fatty acid residues, by weight of the total C6-C24 fatty acid residues of the first triglyceride feed composition. One advantageous feature of the invention is that vegetable oils which have a high level of oleic acid not only in the sn-2 position, but also in the sn-1 and sn-3 positions, can be used in the process for preparing a triglyceride composition comprising SOS triglycerides, which may not be possible when using known processes which require selective distillation of fatty acid residues that are liberated from the triglyceride starting material.

[0030] Since the process of the invention involves the use of an sn-1 ,3-specific lipase, in order to provide a composition having a high content of SOS triglycerides, it is necessary that the first triglyceride feed composition already has a high level of oleic acid residues at the sn-2 position. Accordingly, the first triglyceride feed composition should have an oleic acid content in the sn-2 position of at least 65% by weight of the total sn-2 C6-C24 fatty acid residues of the first triglyceride feed composition. Preferably, the first triglyceride feed composition has an oleic acid content in the sn-2 position of at least 70%, more preferably at least 75%, even more preferably at least 80%, and most preferably at least 85% by weight of the total sn-2 C6-C24 fatty acid residues of the first triglyceride feed composition.

[0031] The oleic acid content at the sn-2 position of a triglyceride composition can be determined by a method which involves scission of the fatty acids at the sn-1 and sn-3 positions using a pancreatic lipase enzyme followed by isolation of the resulting sn-2 monoacylglycerols (MAG) using TLC or NPLC and finally fatty acid methyl ester analysis by gas chromatography. A suitable method is IUPAC Official Method 2.210: "Determination of fatty acids in the 2-position in the triglycerides of oils and fats”, seventh ed., Standard Methods for the Analysis of Oils, Fats and Derivatives, Blackwell, Oxford, 1992. The first triglyceride feed composition preferably comprises one or more vegetable oils. In some embodiments, the first triglyceride feed composition comprises high oleic sunflower oil, triolein, shea olein, high oleic safflower oil, or any mixture thereof. Preferably, the first triglyceride feed composition is high oleic sunflower oil, triolein, shea olein, high oleic safflower oil, or any mixture thereof. These oils are particularly suitable, because they have a high oleic acid content and relatively low cost. More preferably, the first triglyceride composition comprises or consists essentially of high oleic sunflower oil. A particular advantage with the use of high oleic sunflower oil is that it is a non-tropical oil and so readily available in high-use markets such as Europe and North America. As will be appreciated, this has significant benefits in terms of energy reduction in transport, CO2 emission reduction and sustainability.

[0032] Step b) of the process of the invention comprises introducing into the first triglyceride feed composition a first fatty acid / fatty acid aliphatic alcohol ester composition. This composition provides stearic acid residues which are necessary for the production of SOS triglycerides and, accordingly, it is important that the content of stearic acid, and / or an aliphatic alcohol ester thereof , is sufficiently high. In particular, the first fatty acid / fatty acid aliphatic alcohol ester composition should comprise at least 80% by weight of stearic acid, and / or an aliphatic alcohol ester thereof. Preferably, the first fatty acid / fatty acid aliphatic alcohol ester composition comprises at least 85% by weight, more preferably at least 90% by weight, and most preferably at least 95% by weight of stearic acid, and / or an aliphatic alcohol ester thereof .

[0033] The use of an aliphatic alcohol ester of stearic acid is advantageous, because these esters have lower melting points than stearic acid itself. This enables lower temperatures to be used in the reaction, which improves enzyme stability, whilst avoiding unwanted crystallization during processing. Thus, preferably, the first fatty acid / fatty acid aliphatic alcohol ester composition comprises at least 80% by weight, more preferably at least 85% by weight, even more preferably at least 90% by weight, and most preferably at least 95% by weight of an aliphatic alcohol ester of stearic acid. Preferably, the aliphatic alcohol ester of stearic acid is a C1-C4 alkyl ester of stearic acid or a mixture thereof. Most preferably, aliphatic alcohol ester of stearic acid is selected from the group consisting of methyl stearate, ethyl stearate and mixtures thereof. The aliphatic alcohol ester of stearic acid may be used in mixture with stearic acid as a free fatty acid. However, preferably the amount of stearic acid present is less than 10% by weight, more preferably less than 8% by weight, even more preferably less than 6% by weight and most preferably less than 4% by weight. A particular advantage with the use of aliphatic alcohol esters of stearic acid, for example methyl stearate, is that it can be obtained from non-tropical oils such as rapeseed oil with advantages similar to those discussed above for sunflower oil. Yet a further advantage is that such aliphatic alcohol esters are known waste products from other processes, for example biofuel production, and therefore help facilitate recycling of waste products and the formation of a circular economy for fats and oils.

[0034] One advantage of the process of the invention is that a product having a high SOS triglyceride content can be produced without using large amounts of fatty acid or fatty acid ester to drive the reaction, which can result in large amounts of undesirable side streams which have to be processed. Accordingly, the ratio of the first fatty acid / fatty acid aliphatic alcohol ester composition introduced in step b) to the first triglyceride feed composition provided in step a) is preferably from 1 :1 to 3:1 by weight, more preferably from 1 :1 to 2.5:1 by weight, even more preferably from 1 :1 to 2:1 by weight, and most preferably from 1.1 :1 to 1.9:1 by weight.

[0035] The first triglyceride feed composition and the first fatty acid / fatty acid aliphatic alcohol ester composition together form a first reaction mixture. Step b) of the process of the invention comprises reacting the first reaction mixture in the presence of an sn-1 , 3- specific lipase to produce a first product composition. This enzyme effects transesterification at the sn-1 and sn-3 positions of the triglyceride, thus replacing fatty acid residues at these positions in the first triglyceride feed composition with stearic acid residues from the first fatty acid / fatty acid aliphatic alcohol ester composition. Preferably, the sn-1 ,3-specific lipase is a microbial lipase, for example a bacterial or fungal lipase. More preferably, the sn-1 ,3-specific lipase is derived from a fungal species, especially the species Rhizopus oryzae, Thermomyces lanuginosus, or Rhizomucor miehei.

[0036] Lipases derived from these species have been found to be particularly suitable for the process of the invention in terms of specificity, reaction rate and robustness. Most preferably, the sn-1 ,3-specific lipase is derived from Rhizopus oryzae. Preferably, the sn-1 ,3-specific lipase is immobilised on a support. The immobilization of enzymes on supports is well known in the art, and immobilized sn-1 ,3-specific lipases are commercially available from various suppliers. Immobilization of sn-1 ,3-specific lipases on support materials has been found to improve enzyme performance, thus providing higher levels of SOS triglycerides. A variety of support materials are known, such as various polymers and silica. In an embodiment of the invention, the support material on which the sn-1 ,3-specific lipase is immobilized is hydrophobic. One particularly useful enzyme is immobilized Lipase DF “Amano” IM from Rhizopus oryzae (available from Amano Enzyme).

[0037] The reaction of step b) is preferably carried out in the presence of water. The presence of water increases the activity of sn-1 ,3-specific lipase, thus promoting the formation of SOS triglycerides. However, when the level of water is too high, undesirable by-products such as diacylglycerols and SSO triglycerides can be formed. Accordingly, the first reaction mixture preferably comprises water, preferably in an amount of 0.001-1 % by weight, more preferably in an amount of 0.005-0.5% by weight, even more preferably in an amount of 0.01-0.1 % by weight, most preferably in an amount of 0.015-0.05% by weight, based on the total weight of the first reaction mixture.

[0038] To promote the stability of the sn-1 ,3-specific lipase the first reaction mixture preferably has a pH in the range 5 to 7.5, more preferably in the range 6 to 7.

[0039] In step b) of the process, the reaction mixture is preferably heated to a temperature in the in the range 40-70°C, more preferably in the range 45-65°C, and most preferably in the range 50-60°C. The temperature for the reaction is chosen so as to be high enough to provide good enzyme activity and thus a high level of SOS triglycerides, whilst also being low enough to maintain a high enzyme lifetime and thus process economy.

[0040] The product of the enzymatic transesterification process of step b) is referred to herein as the first product composition. The first product composition preferably has an SOS triglyceride content in the range 25-45% by weight, more preferably 28-42% by weight, based on the total weight of triglycerides in the composition.

[0041] The first product composition obtained in step b) is distilled in step c) to remove fatty acids and / or aliphatic alcohol esters of fatty acids from the composition, to produce a second triglyceride feed composition. Distillation can be carried out by conventional methods. In this distillation process, both stearic acid and oleic acid residues are removed. The removal of these fatty acid residues allows control over content of fatty acids and / or aliphatic alcohol esters of fatty acids in the second reaction mixture. Preferably, the distillation step c) removes at least 60% by weight, more preferably at least 70% by weight, even more preferably at least 80% by weight, and still more preferably at least 90% by weight of the fatty acids and / or aliphatic alcohol esters of fatty acids that are present in the first product composition. Most preferably, distillation step c) removes essentially all of the fatty acids and / or aliphatic alcohol esters of fatty acids that are present in the first product composition.

[0042] In step d) of the process of the invention, a second fatty acid / fatty acid aliphatic alcohol ester composition is introduced into the second triglyceride feed composition to form a second reaction mixture, and the second reaction mixture is reacted in the presence of an sn-1 ,3-specific lipase to produce a second product composition. The second fatty acid / fatty acid aliphatic alcohol ester composition provides further stearic acid residues for the production of SOS triglyceride and, accordingly, it is important that the content of stearic acid, and / or an aliphatic alcohol ester thereof , is sufficiently high. In particular, the second fatty acid / fatty acid aliphatic alcohol ester composition should comprise at least 80% by weight of stearic acid, and / or an aliphatic alcohol ester thereof . Preferably, the second fatty acid / fatty acid aliphatic alcohol ester composition comprises at least 85% by weight, more preferably at least 90% by weight, and most preferably at least 95% by weight of stearic acid, and / or an aliphatic alcohol ester thereof .

[0043] The second fatty acid / fatty acid aliphatic alcohol ester composition comprises at least 80% by weight, preferably at least 85% by weight, more preferably at least 90% by weight, and most preferably at least 95% by weight of an aliphatic alcohol ester of stearic acid. Preferably, the aliphatic alcohol ester of stearic acid is a C1-C4 alkyl ester of stearic acid or a mixture thereof. Most preferably, aliphatic alcohol ester of stearic acid is selected from the group consisting of methyl stearate, ethyl stearate and mixtures thereof. The aliphatic alcohol ester of stearic acid may be used in mixture with stearic acid as a free fatty acid. However, preferably the amount of stearic acid present is less than 10% by weight, more preferably less than 8% by weight, even more preferably less than 6% by weight and most preferably less than 4% by weight.

[0044] One advantage of the process of the invention is that a product having a high SOS triglyceride content can be produced without using large amounts of fatty acid or fatty acid ester to drive the reaction, which can result in large amounts of undesirable side streams which have to be processed. Accordingly, the ratio of the second fatty acid / fatty acid aliphatic alcohol ester composition introduced in step d) to the first triglyceride feed composition provided in step a) is preferably from 1 :1 to 3:1 by weight, more preferably from 1 :1 to 2.5:1 by weight, even more preferably from 1 :1 to 2:1 by weight, and most preferably from 1.1 :1 to 1.9:1 by weight. As noted above, the use of such relatively small amounts of fatty acid / fatty acid alcohol ester, provides numerous advantages not least due to a reduction in the amount of material to be processed, unwanted side steams and associated processing.

[0045] The preferred reaction conditions for the reaction of step d) are the same as those set out above for the reaction of step b), including with respect to the sn-1 ,3-specific lipase, the presence and amount of water, the pH of the reaction mixture, and the temperature to which the reaction mixture is heated.

[0046] The SOS triglyceride content of the second product composition can be controlled by adjusting the ratios of the first fatty acid / fatty acid aliphatic alcohol ester composition introduced in step b) and the second fatty acid / fatty acid aliphatic alcohol ester composition introduced in step d) to the first triglyceride feed composition provided in step a). Preferably the second product composition has an SOS triglyceride content in the range 55-75% by weight, preferably 60-75% by weight, more preferably 65-75% by weight, based on the total weight of triglycerides in the composition. The SOS triglyceride content is considered before any optional fractionation step as discussed below.

[0047] The second product composition obtained in step d) is distilled in step e) to remove fatty acids and / or aliphatic alcohol esters of fatty acids from the composition. Distillation can be carried out by conventional methods. In this distillation process, both stearic acid and oleic acid residues are removed. Preferably, the distillation step e) removes at least 60% by weight, more preferably at least 70% by weight, even more preferably at least 80% by weight, and still more preferably at least 90% by weight of the fatty acids and / or aliphatic alcohol esters of fatty acids that are present in the second product composition. Most preferably, distillation step e) removes essentially all of the fatty acids and / or aliphatic alcohol esters of fatty acids that are present in the second product composition.

[0048] Removal of fatty acids and / or aliphatic alcohol esters of fatty acids from the second product composition provides a commercially useful triglyceride composition.

[0049] Alternatively, the removal of fatty acids and / or aliphatic alcohol esters of fatty acids from the second product composition provides control over content of fatty acids and / or aliphatic alcohol esters of fatty acids in further reaction step f), as discussed below.

[0050] In some embodiments, it may be desirable to carry out a further transesterification step using the second product composition (after distillation step e)) as a feedstock. This may be useful, forinstance, to provide a product composition which has a particularly high level of SOS triglycerides, orwhere it is desired to keep the amount of fatty acid and / or aliphatic alcohol ester of fatty acid that is used to a minimum. Accordingly, in some embodiments, the process further comprises: f) introducing a third fatty acid / fatty acid aliphatic alcohol ester composition into the second product composition to form a third reaction mixture and reacting the third reaction mixture in the presence of an sn-1 ,3-specif ic lipase to produce a third product composition , wherein the third fatty acid / fatty acid aliphatic alcohol ester composition comprises at least 80% by weight of stearic acid, and / or an aliphatic alcohol ester thereof ; and g) distilling the third product composition to remove fatty acids, and / or aliphatic alcohol esters of fatty acids from the third product composition.

[0051] In step f), a third fatty acid / fatty acid aliphatic alcohol ester composition is introduced into the second product composition to form a third reaction mixture, and the third reaction mixture is reacted in the presence of an sn-1 ,3-specific lipase to produce a third product composition. The third fatty acid / fatty acid aliphatic alcohol ester composition provides further stearic acid residues for the production of SOS triglyceride and, accordingly, it is important that the content of stearic acid, and / or an aliphatic alcohol ester thereof , is sufficiently high. In particular, the third fatty acid / fatty acid aliphatic alcohol ester composition should comprise at least 80% by weight of stearic acid, and / or an aliphatic alcohol ester thereof. Preferably, the third fatty acid / fatty acid aliphatic alcohol ester composition comprises at least 85% by weight, more preferably at least 90% by weight, and most preferably at least 95% by weight of stearic acid, and / or an aliphatic alcohol ester thereof.

[0052] The third fatty acid / fatty acid aliphatic alcohol ester composition comprises at least 80% by weight, preferably at least 85% by weight, more preferably at least 90% by weight, and most preferably at least 95% by weight of an aliphatic alcohol ester of stearic acid. Preferably, the aliphatic alcohol ester of stearic acid is a C1-C4 alkyl ester of stearic acid or a mixture thereof. Most preferably, the aliphatic alcohol ester of stearic acid is selected from the group consisting of methyl stearate, ethyl stearate and mixtures thereof. The aliphatic alcohol ester of stearic acid may be used in mixture with stearic acid as a free fatty acid. However, preferably the amount of stearic acid present is less than 10% by weight, more preferably less than 8% by weight, even more preferably less than 6% by weight and most preferably less than 4% by weight.

[0053] As noted above, optional steps f) and g) are useful for further reducing the overall amount of fatty acid and / or aliphatic alcohol ester of fatty acid that is used in the process. The ratio of the third fatty acid / fatty acid aliphatic alcohol ester composition introduced in step f) to the first triglyceride feed composition provided in step a) is preferably from 1 :1 to 3:1 by weight, more preferably from 1 :1 to 2.5:1 by weight, even more preferably from 1 :1 to 2:1 by weight, and most preferably from 1.1 :1 to 1.9:1 by weight.

[0054] The preferred reaction conditions for the reaction of step f) are the same as those set out above for the reaction of step b), including with respect to the sn-1 ,3-specific lipase, the presence and amount of water, the pH of the reaction mixture, and the temperature to which the reaction mixture is heated.

[0055] The SOS triglyceride content of the third product composition can be controlled by adjusting the ratios of the first fatty acid / fatty acid aliphatic alcohol ester composition introduced in step b), the second fatty acid / fatty acid aliphatic alcohol ester composition introduced in step d), and the third fatty acid / fatty acid aliphatic alcohol ester composition introduced in step f) to the first triglyceride feed composition provided in step a). Preferably the third product composition has an SOS triglyceride content in the range 55-75% by weight, preferably 60-75% by weight, more preferably 65-75% by weight, based on the total weight of triglycerides in the composition. The SOS triglyceride content is considered before any optional fractionation step as discussed below. The third product composition obtained in step f) is distilled in step g) to remove fatty acids and / or aliphatic alcohol esters of fatty acids from the third product composition. Again, distillation can be carried out by conventional methods. In this distillation process, both stearic acid and oleic acid residues are removed. Preferably, the distillation step g) removes at least 60% by weight, more preferably at least 70% by weight, even more preferably at least 80% by weight, and still more preferably at least 90% by weight of the fatty acids and / or aliphatic alcohol esters of fatty acids that are present in the first product composition. Most preferably, distillation step g) removes essentially all of the fatty acids and / or aliphatic alcohol esters of fatty acids that are present in the first product composition. Removal of fatty acids and / or aliphatic alcohol esters of fatty acids from the third product composition provides a commercially useful triglyceride composition.

[0056] If desired, further enzymatic transesterification and distillation steps may be carried out using the third and subsequent product compositions as a feedstock for reaction with further fatty acid / fatty acid aliphatic alcohol ester compositions.

[0057] Overall, one advantage of the process of the invention is that a product having a high SOS triglyceride content can be produced without using large amounts of fatty acid or fatty acid ester to drive the reaction, which can result in large amounts of undesirable side streams which have to be processed, as well as undesirable by-products. Accordingly, the ratio of the total amount of the first, second and, where present, third fatty acid / fatty acid aliphatic alcohol ester compositions to the amount of first triglyceride feed composition provided in step a) is from 2:1 to 6:1 , preferably from 2.2:1 to 5:1 , more preferably from 2.4:1 to 4:1 , and most preferably from 2.5:1 to 3.5:1 by weight.

[0058] The process of enzymatic transesterification can result in the production of some SSS triglycerides. If the content of SSS triglycerides is too high (e.g. above 3% of the composition by weight based on total triglycerides), then this can have a negative impact in the viscosity of the product. Accordingly, it can be of value to remove at least some of the SSS triglycerides in a simple fractionation step (“detopping”), where the SSS triglyceride content of the product is significantly reduced, without any significant increase in the SOS triglyceride content of the product. Accordingly, the process of the invention may further comprise fractionating the second product composition or the third product composition to remove a solid fraction comprising SSS triglycerides and optionally diacylglycerols, wherein the fractionation:

[0059] (a) decreases the SSS triglyceride content of the product composition by at least 30% by weight relative to the SSS triglyceride content of the product composition before the fractionation; and

[0060] (b) does not increase the SOS triglyceride content of the product composition by more than 5% by weight relative to the SOS triglyceride content of the product composition before the fractionation, preferably wherein the fractionation does not increase the SOS triglyceride content of the product composition by more than 3% by weight relative to the SOS triglyceride content of the product composition before the fractionation.

[0061] The percentage change in SSS triglyceride content and SOS triglyceride content is considered relative to the amount of these triglycerides present in the product composition before fractionation. For instance, a decrease in the SSS triglyceride content of the product composition from 5% by weight based on total triglycerides to 2% by weight based on total triglycerides is considered to be a 60% decrease in the SSS triglyceride content of the product composition.

[0062] The fractionation process described above can be carried out using a standard dry fractionation process. For instance, the product composition can be heated to ensure that the composition is melted and then cooled to selectively crystallize the SSS triglycerides. The composition can then be filtered to remove a solid fraction comprising SSS triglycerides. The remaining product composition (the liquid fraction) can then be used as a cocoa butter equivalent or a component thereof.

[0063] Solvent fractionation is often used to increase the SOS triglyceride content of a product. Solvent fractionation can effectively separate SOS triglycerides from other triglycerides formed such as SSS, SOO and 000 triglycerides to produce good quality products, but the cost for building the equipment for this process is high, and the use of solvents can create safety and customer acceptance issues. From a energy reduction, waster usage and sustainability point of view, there are clear benefits to avoiding such fractionation processes. Dry fractionation is a more economically feasible alternative, but not as efficient in the separation of SOS triglycerides from other triglycerides formed. This results in the need for product to be recirculated, which adds to process costs. More recirculation also means more formation of by-products and therefore also a decreased overall yield. More than one fractionation step may be needed to achieve the desired quality. Accordingly, both types of fractionation are complex and costly process steps which affect the process economy, as well as being energy intensive. One advantage of the process of the invention is that, whilst a simple fractionation process may be useful to remove excess SSS triglycerides, it is possible to dispense with more complex fractionation processes which are used to significantly increase the SOS triglyceride content of the product. Accordingly, the process of the invention preferably does not comprise a fractionation step in which the SOS triglyceride content of the first, second and / or third product composition is increased by more than 5% by weight relative to the SOS triglyceride content of the product composition before the fractionation. More preferably, the process does not comprise a fractionation step in which the SOS triglyceride content of the product composition is increased by more than 3% by weight relative to the SOS triglyceride content of the product composition before the fractionation.

[0064] It is also preferred that the process does not comprise a solvent fractionation step.

[0065] In products which are intended foruse as cocoa butter equivalents, or components thereof, it is desirable to keep the SSO triglyceride content low, and the ratio of SOS triglycerides to SSO triglycerides high. The process of the invention can provide products with a high ratio of SOS triglycerides to SSO triglycerides. Thus, in some embodiments of the invention, the second product composition, or where present the third product composition , has a weight ratio of SOS triglycerides to SSO triglycerides of at least 40:1 , preferably at least 50:1 , more preferably at least 60:1 , even more preferably at least 70:1 and most preferably at least 80:1. These ratios are based on the product composition before any optional fractionation step as discussed above.

[0066] In some embodiments, the fatty acids and / or aliphatic alcohol esters of fatty acids removed in step c), e) and / or g) are hydrogenated and introduced as the first, second and / or third fatty acid / fatty acid aliphatic alcohol ester composition, or a component thereof, in step b), d) and / or f). In this way, the amount of side streams can be reduced. The fatty acids and / or aliphatic alcohol esters of fatty acids removed in step c), e) and / or g) may be bleached prior to being introduced in step b), d) and / or f). Bleaching may be carried out before or after hydrogenation. The bleaching removes impurities and secures a better enzymatic lifetime and hence a more efficient transesterification. The transesterification steps of the process may be carried out as a batch process, a fed- batch process, or a continuous process. In a batch process, reactants are mixed in one reactor for a certain reaction time until desired yield of product is produced, and the enzymes are filtered off. In a fed-batch process, the reactants are added to the batch reactor not all at once, but little at a time. In a continuous process, the enzymes are fixed in a packed bed reactor, reactants are pumped through the reactor, and a product stream is drawn off from the reactor. In a continuous process, the flow rate of the feed ( / .e. the first, second or third reaction mixture) through the reactor is preferably in the range 0.5 to 14, more preferably 2 to 10, and most preferably 4 to 8 g feed / g enzyme / h. Continuous processes have been found to be advantageous for simpler recycling of fatty acid esters and fatty acids and reduced migration of acyl groups within the triglycerides. Accordingly, in preferred embodiments of the invention, steps b) and d) are performed as continuous processes. When present, step f) is preferably performed as a continuous process.

[0067] As noted above, the products of the processes of the invention are useful as cocoa butter equivalents, or components thereof. Accordingly, in some embodiments, the process of the invention further comprises using the triglyceride composition comprising SOS triglycerides as a cocoa butter equivalent or a component thereof in the manufacture of a chocolate or chocolate-like product.

[0068] EXAMPLES

[0069] In the following Examples, enzymatic transesterification in a continuous process set-up is used to produce a composition comprising SOS triglycerides from a feed composition containing High Oleic Sunflower Oil (HOSO) as the first triglyceride feed composition and methyl stearate (MeSt) as the fatty acid / fatty acid aliphatic alcohol ester composition. All experiments were performed with two enzymatic columns connected in a series for each transesterification step, each of which were packed with 7 g of immobilized Lipase DF “Amano” IM from Rhizopus oryzae. When multiple transesterification steps were used in a process (Examples 2-5) each transesterification step involved the use of two columns, serially connected, packed with 7 g of immobilised enzymes each. E.g. in Example 2, which includes two transesterification steps, this involves the use of 4 separate columns, each packed with 7 g of enzyme. Example 1 (Comparative Example)

[0070] In this experiment a MeSt / HOSO ratio of 3:1 by weight is utilised for the reaction mixture, which is subjected to a single enzymatic transesterification step. This means that the reaction mixture is run through two enzymatic columns, serially connected, one time. Excess fatty acids and aliphatic alcohol esters of fatty acids are then removed by distillation and the finished product is analysed.

[0071] Example 2

[0072] In this experiment a MeSt / HOSO ratio of 1 .5:1 by weight is utilised for the first reaction mixture, which is run through two enzymatic columns, serially connected, once (Step b)). Then, fatty acids and aliphatic alcohol esters of fatty acids are removed by distillation. Further MeSt and water are then added to provide a second reaction mixture, wherein the ratio of the further MeSt to the HOSO provided for the first reaction is 1 .5:1 by weight. The second reaction mixture is then processed through two new enzymatic columns, serially connected (Step d)). The excess fatty acids and aliphatic alcohol esters of fatty acids are removed by distillation and the finished product is analysed.

[0073] The total weight ratio of MeSt to HOSO in this process is 3:1. Example 3

[0074] In this experiment a MeSt / HOSO ratio of 1 .5:1 by weight is utilised for the first reaction mixture, which is run through two enzymatic columns, serially connected, once (Step b)). Then, fatty acids and aliphatic alcohol esters of fatty acids are removed by distillation. Further MeSt and water are then added to provide a second reaction mixture, wherein the ratio of the further MeSt to the HOSO provided for the first reaction is 1 :1 by weight. The second reaction mixture is then processed through two new enzymatic columns, serially connected (Step d)). Fatty acids and aliphatic alcohol esters of fatty acids are removed by distillation and the finished product is analysed.

[0075] The total weight ratio of MeSt to HOSO in this process is 2.5:1 .

[0076] Example 4

[0077] In this experiment a MeSt / HOSO ratio of 1 .5:1 by weight is utilised for the first reaction mixture, which is run through two enzymatic columns, serially connected, once (Step b)). Then, fatty acids and aliphatic alcohol esters of fatty acids are removed by distillation. Further MeSt and water are then added to provide a second reaction mixture, wherein the ratio of the further MeSt to the HOSO provided for the first reaction is 2:1 by weight. The second reaction mixture is then processed through two new enzymatic columns, serially connected (Step d)). Fatty acids and aliphatic alcohol esters of fatty acids are removed by distillation and the finished product is analysed. The total weight ratio of MeSt to HOSO in this process is 3.5:1.

[0078] Example 5

[0079] In this experiment a MeSt / HOSO ratio of 1 :1 by weight is utilised for the first reaction mixture, which is run through two enzymatic columns, serially connected, once (Step b)). Then, fatty acids and aliphatic alcohol esters of fatty acids are removed by distillation. Further MeSt and water are then added to provide a second reaction mixture, wherein the ratio of the further MeSt to the HOSO provided for the first reaction is 1 :1 by weight. The second reaction mixture is then processed through two new enzymatic columns, serially connected (Step d)). Fatty acids and aliphatic alcohol esters of fatty acids are again removed by distillation. Further MeSt and water are then added to provide a third reaction mixture, wherein the ratio of the further MeSt to the HOSO provided for the first reaction is 1 :1 by weight. The third reaction mixture is then processed through two new enzymatic columns, serially connected (Step f)). Fatty acids and aliphatic alcohol esters of fatty acids are removed by distillation and the finished product is analysed.

[0080] The total weight ratio of MeSt to HOSO in this process is 3:1.

[0081] Summary of Results The table below summarises the results of Examples 1-5:

[0082] The examples show that there are significant technical advantages associated with the process of the invention as represented by Examples 2-5, as compared with known processes as represented by Example 1. In particular, a comparison of Examples 1 and 2 shows that, by distilling the first product composition to remove fatty acids and / or aliphatic alcohol esters of fatty acids from the composition and then introducing a second fatty acid / fatty acid aliphatic alcohol ester composition (here further MeSt), before a second reaction step, the SOS triglyceride content of the product can be increased, without the need to increase the overall amount of MeSt that is used. A comparison of Example 3 with Example 1 demonstrates that, surprisingly, by use of the process of the invention, the SOS triglyceride content of the product can be maintained, or even increased, whilst reducing the total amount of MeSt that is used. Example 4 demonstrates that the process of the invention can be used to obtain triglyceride compositions which have a very high content of SOS triglycerides. Example 5 demonstrates that the SOS triglyceride content of the triglyceride compositions produced according to the process of the invention can be further increased, while still limiting the use of fatty acid or fatty acid ester, by the use of a further transesterification step f) with subsequent distillation. In each of Examples 2-5, the SOS content of the product is sufficiently high such that the need to further increase the SOS content using fractionation is avoided.

[0083] Example 6

[0084] If the SSS triglyceride content of a product composition becomes too high, it can have a negative impact on the viscosity of the product. Therefore, it can be of value to remove a part of the SSS in a fractionation step (“de-topping”), where the SSS triglyceride content is significantly reduced.

[0085] Such a process was performed on the product from Example 5 after removing fatty acids and aliphatic alcohol esters of fatty acids by distillation. The process was performed using a DeSmet L-Frac crystallizer and an associated filter. The following temperature profile was used:

[0086] The composition was first heated to 70°C where it was kept for 2.5 hours. Then the composition was cooled from 70°C to 36.5°C in two hours and subsequently kept isothermally at 36.5°C for 1 .25 hours before pumping the resulting slurry to the filter. All temperatures are given as the temperature of the water jacket on the L-Frac.

[0087] When pumping the slurry to the filter, the solid fat content of the slurry was measured as 4% using an Oxford Instruments MQC+ bench-top NMR and the temperature of the composition was 37.1 °C. The filtration was carried out by pumping the composition to the filter, gradually increasing the pressure in the crystallizer for 20 minutes until a pressure of 2 bar(g) was reached. Then the connection between the crystallizer and the filter was sealed off and the filter pressure was gradually increased to 25 bar(g) over a span of two hours. The pressure was subsequently released, and the filter cake could be removed from the filter. The remaining product (the liquid fraction) was then analysed and the results are indicated in the table below:

[0088] This example shows that it is possible to perform a simple “de-topping” of the product composition, where the amount of SSS triglyceride is significantly reduced, while the amount of SOS in the product only changes slightly.

Claims

Claims1. A process for preparing a triglyceride composition comprising SOS triglycerides, wherein S represents stearic acid (C18:0) residues and O represents oleic acid (C18:1 ) residues, said process comprising: a) providing a first triglyceride feed composition, wherein the first triglyceride feed composition comprises at least 60% oleic acid fatty acid residues by weight of the total C6- C24 fatty acid residues of the first triglyceride feed composition, and further wherein the first triglyceride feed composition has an oleic acid content in the sn-2 position of at least 65% by weight of the total sn-2 C6-C24 fatty acid residues of the first triglyceride feed composition; b) introducing into the first triglyceride feed composition a first fatty acid / fatty acid aliphatic alcohol ester composition to form a first reaction mixture, and reacting the first reaction mixture in the presence of an sn-1 ,3-specific lipase to produce a first product composition, wherein the first fatty acid / fatty acid aliphatic alcohol ester composition comprises at least 80% by weight of stearic acid, and / or an aliphatic alcohol ester thereof ; c) distilling the first product composition to remove fatty acids and / or aliphatic alcohol esters of fatty acids from the composition to produce a second triglyceride feed composition; d) introducing a second fatty acid / fatty acid aliphatic alcohol ester composition into the second triglyceride feed composition to form a second reaction mixture, and reacting the second reaction mixture in the presence of an sn-1 ,3-specific lipase to produce a second product composition, wherein the second fatty acid / fatty acid aliphatic alcohol ester composition comprises at least 80% by weight of stearic acid, and / or an aliphatic alcohol ester thereof; and e) distilling the second product composition to remove fatty acids and / or aliphatic alcohol esters of fatty acids from the second product composition, and optionally further comprising: f) introducing a third fatty acid / fatty acid aliphatic alcohol ester composition into the second product composition to form a third reaction mixture and reacting the third reaction mixture in the presence of an sn-1 ,3-specific lipase to produce a third product composition, wherein the third fatty acid / fatty acid aliphatic alcohol ester composition comprises at least 80% by weight of stearic acid, and / or an aliphatic alcohol ester thereof ; and g) distilling the third product composition to remove fatty acids, and / or aliphaticalcohol esters of fatty acids from the third product composition; wherein the ratio of the total amount of the first, second and, where present, third fatty acid / fatty acid aliphatic alcohol ester compositions to the amount of first triglyceride feed composition provided in step a) is 2:1 to 6:1 by weight.

2. The process of claim 1 , wherein the first triglyceride feed composition comprises at least 70% oleic acid fatty acid residues, preferably at least 80% oleic acid fatty acid residues, by weight of the total C6-C24 fatty acid residues of the first triglyceride feed composition.

3. The process of any preceding claim, wherein the first triglyceride feed composition has an oleic acid content in the sn-2 position of at least 70%, preferably at least 75%, more preferably at least 80% and most preferably at least 85%, by weight of the total sn-2 C6- C24 fatty acid residues of the first triglyceride feed composition.

4. The process of any preceding claim, wherein the first triglyceride feed composition comprises high oleic sunflower oil, triolein, shea olein, high oleic safflower oil, or any mixture thereof, preferably wherein the first triglyceride feed composition is high oleic sunflower oil, triolein, shea olein, high oleic safflower oil, or any mixture thereof.

5. The process of any preceding claim, wherein the first, second, and / or third fatty acid / fatty acid aliphatic alcohol ester composition comprises at least 85% by weight, preferably at least 90% by weight, and more preferably at least 95% by weight, stearic acid, and / or an aliphatic alcohol ester thereof .

6. The process of any preceding claim, wherein the first, second, and / or third fatty acid / fatty acid aliphatic alcohol ester composition comprises at least 80% by weight of a C1-C4 alkyl ester of stearic acid, preferably selected from methyl stearate, ethyl stearate and mixtures thereof.

7. The process of any preceding claim, wherein in step b), step d), and / or step f) the sn-1 ,3-specific lipase is a microbial lipase, such as a bacterial lipase or a fungal lipase, optionally selected from Rhizopus oryzae, Thermomyces lanuginosus, and Rhizomucor miehei, preferably Rhizopus oryzae.

8. The process of any preceding claim, wherein the first product composition has an SOS triglyceride content in the range 25-45% by weight, preferably 28-42% by weight, based on the total weight of triglycerides in the composition.

9. The process of any preceding claim, wherein the second product composition and / or the third product composition has an SOS triglyceride content in the range 55-75% by weight, preferably 60-75% by weight, more preferably 65-75% by weight, based on the total weight of triglycerides in the composition.

10. The process of any preceding claim, wherein the ratio of the firstfatty acid / fatty acid aliphatic alcohol ester composition to the first triglyceride feed composition provided in step a) is from 1 :1 to 3:1 by weight, preferably from 1 :1 to 2.5:1 by weight, more preferably from 1 :1 to 2:1 by weight, and most preferably from 1.1 :1 to 1.9:1 by weight.11 . The process of any preceding claim, wherein the ratio of the second fatty acid / fatty acid aliphatic alcohol ester composition to the first triglyceride feed composition provided in step a) is from 1 :1 to 3:1 by weight, preferably from 1 :1 to 2.5:1 by weight, more preferably from 1 :1 to 2:1 by weight, and most preferably from 1.1 :1 to 1.9:1 by weight.

12. The process of any preceding claim, wherein the ratio of the third fatty acid / fatty acid aliphatic alcohol ester composition to the first triglyceride feed composition provided in step a) is from 1 :1 to 3:1 by weight, preferably from 1 :1 to 2.5:1 by weight, more preferably from 1 :1 to 2:1 by weight, and most preferably from 1.1 :1 to 1.9:1 by weight.

13. The process of any preceding claim, wherein the ratio of the total amount of the first, second and, where present, third fatty acid / fatty acid aliphatic alcohol ester compositions to the amount of first triglyceride feed composition provided in step a) is from 2.2:1 to 5:1 , preferably from 2.4:1 to 4:1 , more preferably from 2.5:1 to 3.5:1 by weight.

14. The process of any preceding claim, wherein in step b), step d) and / or step f), the reaction mixture is heated to a temperature in the range 40-70°C, preferably in the range 45-65°C, more preferably in the range 50-60°C.

15. The process of any preceding claim, wherein the first reaction mixture, second reaction mixture, and / or third reaction mixture has a pH in the range 5 to 7.5, preferably in the range 6 to 7.

16. The process of any preceding claim, wherein the first reaction mixture, second reaction mixture, and / or third reaction mixture comprises water, preferably in an amount of 0.001-1 % by weight, more preferably in an amount of 0.005-0.5% by weight, even more preferably in an amount of 0.01-0.1 % by weight, most preferably in an amount of 0.015- 0.05% by weight, based on the total weight of the reaction mixture.

17. The process of any preceding claim, further comprising fractionating the second product composition or the third product composition to remove a solid fraction comprising SSS triglycerides and optionally diacylglycerols, wherein the fractionation:(a) decreases the SSS triglyceride content of the product composition by at least 30% by weight relative to the SSS triglycerides content of the product composition before the fractionation; and(b) does not increase the SOS triglyceride content of the product composition by more than 5% by weight relative to the SOS triglyceride content of the product composition before the fractionation, preferably wherein the fractionation does not increase the SOS triglyceride content of the product composition by more than 3% by weight relative to the SOS triglyceride content of the product composition before the fractionation.

18. The process of any preceding claim, wherein the process does not comprise a fractionation step in which the SOS triglyceride content of the first, second and / or third product composition is increased by more than 5% by weight relative to the SOS triglyceride content of the product composition before the fractionation, preferably wherein the process does not comprise a fractionation step in which the SOS triglyceride content of the product composition is increased by more than 3% by weight relative to the SOS triglyceride content of the product composition before the fractionation.

19. The process of any preceding claim, wherein the fatty acids and / or aliphatic alcohol esters of fatty acids removed in step c), e) and / or g) are hydrogenated and introduced as the first, second and / or third fatty acid / fatty acid aliphatic alcohol ester composition, or a component thereof, in step b), d) and / or f).

20. The process of any preceding claim, wherein the second product composition, or where present the third product composition, has a weight ratio of SOS triglycerides to SSO triglycerides of at least 40:1 , preferably at least 50:1 , more preferably at least 60:1 , even more preferably at least 70:1 and most preferably at least 80:1.

21. The process of any preceding claim, wherein steps b) and d) are performed as continuous processes, optionally further wherein step f) is performed as a continuous process.

22. The process of any preceding claim, further comprising using the triglyceride composition comprising SOS triglycerides as a cocoa butter equivalent or a component thereof in the manufacture of a chocolate or chocolate-like product.

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