Methods of processing an oil composition

Abstract

Disclosed herein are methods of processing an oil composition. The oil composition comprises: 40-100 wt% oil, 0-20 wt% ethanol and 0-25 wt% water. The oil comprises 95-99 wt% triacylglycerides, 1-5 wt% diacylglycerides, and less than 1 wt% monoacylglycerides. The methods disclosed herein may comprise adding water and a base to the oil composition or adding water and an enzyme to the oil composition. Such methods comprise hydrolysing at least some of the diacylglycerides and / or triacylglycerides to obtain an oil comprising at least 10 wt% monoacylglycerides and / or at least 10 wt% diacylglycerides. The methods disclosed herein may comprise adding ethanol and a base to the oil composition. Such methods comprise transesterification of at least some of the monoacylglycerides, diacylglycerides and / or triacylglycerides to obtain an oil comprising at least 20 wt% fatty acid ethyl esters (FAEE). Also provided herein are products obtainable by the disclosed methods.

Description

[0001] METHODS OF PROCESSING AN OIL COMPOSITION

[0002] Technical Field

[0003] The present invention relates to a method of processing an oil composition.

[0004] Background

[0005] Triacylglycerides (also known as triglycerides) are commonly found in plant and animal fats. They comprise three fatty acid chains and a glycerol backbone, with each fatty acid chain attached to glycerol via an ester bond. Derivatives of triacylglycerides where only one or two of the glycerol hydroxyl groups are esterified are monoacylglycerides and diacylglycerides respectively. Triacylglycerides can be transesterified with alcohols to afford the corresponding fatty acid alkyl esters, or hydrolysed to afford the corresponding free fatty acid, in either case liberating the corresponding hydroxyl group of the glycerol. Products derived from triacylglycerides find utility in a range of applications.

[0006] Monoacylglycerides (MAGs) and diacylglycerides (DAGs) are generally of interest for their emulsification properties and find various applications in food, pharmaceutical, and cosmetic industries. These highly regulated industries require products that meet stringent technical standards. MAGs and DAGs can be made by removing fatty acid chains from triglycerides through processes such as hydrolysis and glycerolysis or other transesterification reactions. These reactions can be chemically catalysed using base catalysts or enzymatically catalysed using enzymes such as lipases, or by combining chemical and enzymatic methods.

[0007] Fatty acid methyl and ethyl esters (FAMEs and FAEEs, respectively) can be used as components in biodiesel. More recently, FAEEs have become favoured, in part due to the possibility of using bioderived ethanol (also known as “bioethanol”) in their production. FAEEs can be made by transesterification of fatty acid esters such as monoacylglycerides, diacylglycerides and triacylglycerides. This process typically involves reaction with methanol or ethanol in the presence of a base. WO 2009006317 Al relates to methods of processing a composition comprising triglycerides to produce ethyl esters of polyunsaturated fatty acids from the triglycerides.

[0008] Fats and oils are abundant and naturally-occurring. They are often discharged as waste from large-scale processes such as those found in the food industry.

[0009] Chemical processing of natural, bioderived resources into pure products is often challenging, due to the presence of impurities and variable quality. This means that they often require energy- and resource-intensive processes involving significant purification to obtain products that meet technical requirements.

[0010] Summary

[0011] According to a first aspect of the present invention, there is provided a method of processing an oil composition, wherein the oil composition comprises:

[0012] 40-100 wt % oil

[0013] 0-20 wt% ethanol;

[0014] 0-25 wt% water; and wherein the oil comprises:

[0015] 95-99 wt% triacylglycerides;

[0016] 1-5 wt% diacylglycerides; and less than 1 wt% monoacylglycerides; and wherein the method comprises:

[0017] (i) adding water and a base to the oil composition; hydrolysing at least some of the diacylglycerides and / or triacylglycerides to obtain an oil comprising: at least 10 wt % monoacylglycerides; and / or at least 10 wt% diacylglycerides; or

[0018] (ii) adding ethanol and a base to the oil composition; transesterification of at least some of the monoacylglycerides, diacylglycerides and / or triacylglycerides to obtain an oil comprising: at least 20 wt% fatty acid ethyl esters (FAEE); or

[0019] (iii) adding water and an enzyme to the oil composition; hydrolysing at least some of the diacylglycerides and / or triacylglycerides to obtain an oil comprising: at least 10 wt % monoacylglycerides; and / or at least 10 wt% diacylglycerides.

[0020] In some examples of the first aspect, the oil composition is a blended oil composition. In some such examples, the method comprises: adding ethanol and a base to the blended oil composition; transesterification of at least some of the monoacylglycerides, diacylglycerides and / or triacylglycerides to obtain an oil comprising: at least 20 wt% fatty acid ethyl esters (FAEE).

[0021] A second aspect of the present invention provides methods of obtaining an oil composition according to the first aspect from a plant source through an ethanol extraction process comprising mixing plant-based flour or flakes with ethanol and separating the oil composition from the flour or flakes.

[0022] A third aspect of the present invention provides a method of purifying the oil composition prior to step (i), (ii) or (iii) of the first aspect to remove one or more impurities including ash, protein, free fatty acids, phospholipids, waxes, carbohydrates, water and / or ethanol.

[0023] A fourth aspect of the present invention provides a method of processing an oil composition further comprising one or more purification steps after step (i), (ii) or (iii) of the first aspect.

[0024] A fifth aspect of the present invention provides oil obtainable by any of the first, second, third or fourth aspects. A sixth aspect of the present invention provides food, cosmetic or pharmaceutical products comprising the oil according to the fifth aspect.

[0025] A seventh aspect of the present invention provides monoacylglycerides and / or diacylglycerides and / or triacylglycerides obtainable by any of the first, second, third or fourth aspects.

[0026] An eighth aspect of the present invention provides a method of blending the oil obtainable by the fifth aspect or the monoacylglycerides and / or diacylglycerides and / or triacylglycerides obtainable by the seventh aspect with at least one fat and / or at least one oil.

[0027] A ninth aspect of the present invention provides products comprising monoacylglycerides and / or diacylglycerides according to the seventh aspect.

[0028] A tenth aspect of the present invention provides fatty acid ethyl esters obtainable by any of the first, second, third or fourth aspects.

[0029] An eleventh aspect of the present invention provides a method of synthesising structured lipids from monoacylglycerides, diacylglycerides, triacylglycerides, free fatty acids and / or fatty acid ethyl esters obtainable by any of the first, second, third or fourth aspects.

[0030] A twelfth aspect of the present invention provides structured lipids obtainable by the eleventh aspect.

[0031] A thirteenth aspect of the present invention provides biodiesel comprising fatty acid ethyl esters according to the tenth aspect.

[0032] Further features and advantages of the invention will become apparent from the following description of embodiments of the invention, given by way of example only, which is made with reference to the accompanying drawings. Brief Description of the Drawings

[0033] Figure 1 (background) shows a block diagram of one embodiment of a system for generating chickpea protein concentrate.

[0034] Figure 2 (background) shows a flowchart of one embodiment of a method for generating chickpea concentrate.

[0035] Figure 3 (background) shows one exemplary embodiment of a system for generating chickpea protein concentrate.

[0036] Figure 4 (background) shows a block diagram of a de-oiling processor prior to protein extraction.

[0037] Figure 5 (background) shows a block diagram of one embodiment of a de-oiling processor.

[0038] Figure 6 (background) shows a block diagram of another embodiment of a deoiling processor.

[0039] Figure 7 (background) shows a block diagram of one embodiment of an ethanol recycling loop for use in conjunction with the de-oiling processor.

[0040] Figure 8 shows a block diagram of an embodiment of a process for purifying an oil composition.

[0041] Figure 9 shows a block diagram of an embodiment of a process for purifying an oil composition by refining-bleaching-deodorising (RBD).

[0042] Figure 10 shows a block diagram of an embodiment of a method of processing an oil composition.

[0043] Abbreviations MAG = monoacylglyceride

[0044] DAG = diacylglyceride

[0045] TAG = triacylglyceride

[0046] FAME = fatty acid methyl ester

[0047] FAEE = fatty acid ethyl ester

[0048] FFA = free fatty acid

[0049] RBD = refining-bleaching-deodorising

[0050] Detailed Description

[0051] In an embodiment, there is provided a method of processing an oil composition to obtain products including MAGs, DAGs and FAEEs. The method comprises processing an oil composition through hydrolysis or transesterification reactions.

[0052] In some embodiments, the method comprises: (i) obtaining a crude oil composition from a plant source; (ii) blending the crude oil composition with other fats or oils; (iii) purifying the crude oil composition to remove impurities; (iv) hydrolysis or transesterification; (v) purifying the products; (vi) blending with other fats and / or oils. It will be understood that, in its simplest form, the method disclosed herein comprises step (iv) above only, and that each of the steps (i), (ii), (iii), (v) and / or (vi) may be omitted or included as desired. For example, oils comprising triglycerides can be found in many sources other than plants, and therefore step (i) can be omitted. In some embodiments, the oil composition subjected to steps (iii) or (iv) may be a blend of more than one oil composition, and therefore step (ii) can be suitably included or omitted. In some embodiments, the oil composition may be used as obtained in step (i) or step (ii) without further purification, and therefore step (iii) can be omitted. In some embodiments, the products obtained in step (iv) are not purified, and therefore step (v) can be omitted. In some embodiments, step (v) is omitted and the oil obtained after step (iv) may be blended with other fats and / or oils. In some embodiments, step (v) is included and purified products may be blended with other fats and / or oils. Further details and advantages of the various steps (i)-(vi) are disclosed herein. The Oil Composition

[0053] The oil composition comprises oil and, optionally, one or more additional components. The oil composition comprises 40-100 wt% oil, 0-20 wt% ethanol and 0- 25 wt% water. In some embodiments, the oil composition comprises 40-99.8 wt% oil, 0.1-20 wt% ethanol and 0.1-25 wt% water. In some embodiments, the oil composition comprises 40-100 wt% oil, 0-15 wt% ethanol and 0-25 wt% water. In some embodiments, the oil composition comprises 40-99.8 wt% oil, 0.1-15 wt% ethanol and 0.1-25 wt% water. These oil compositions are expressed relative to total oil composition (rather than the amount of oil comprising monoacylglycerides, diacylglycerides and triacylglycerides).

[0054] In some embodiments, the oil composition further comprises one or more additional components. The oil composition may further comprise one or more of ash, protein, free fatty acids, phospholipids, waxes and / or carbohydrates. In some embodiments, the oil composition comprises 40-100 wt% oil, 0-20 wt% ethanol and 0- 25 wt% water, 0-15 wt% carbohydrates, 0-7 wt% protein and 0-5 wt% ash. In some embodiments, the oil composition comprises 40-99.8 wt% oil, 0.1-20 wt% ethanol and 0.1-25 wt% water, 0-15 wt% carbohydrates, 0-7 wt% protein and 0-5 wt% ash. In some embodiments, the oil composition comprises 40-100 wt% oil, 0-15 wt% ethanol and 0- 25 wt% water, 0-15 wt% carbohydrates, 0-7 wt% protein and 0-5 wt% ash. In some embodiments, the oil composition comprises 40-99.8 wt% oil, 0.1-15 wt% ethanol and 0.1-25 wt% water, 0-15 wt% carbohydrates, 0-7 wt% protein and 0-5 wt% ash.

[0055] The oil comprises monoacylglycerides, diacylglycerides and / or triacylglycerides and can be obtained from a variety of sources. It is well known that plant and animal fats comprise said components. The oil comprises 90-100 wt% triacylglycerides; 0-10 wt% diacylglycerides; and less than 5 wt% monoacyl glycerides. In some embodiments, the oil comprises 95-99 wt% triacylglycerides; 1-5 wt% diacylglycerides; and less than 1 wt% monoacylglycerides. In some embodiments, the oil comprises less than 1 wt% free fatty acids, or 0.01-0.1 wt%. These compositions of the oil are expressed relative to the total amount of oil comprising monoacylglycerides, diacylglycerides and triacylglycerides (rather than the total oil composition).

[0056] In some embodiments, the oil composition comprises about 47 wt% oil, 13.5 wt% ethanol and 22 wt% water. In an embodiment, the oil composition comprises about 47 wt % oil, 13.5 wt% ethanol, 22 wt% water, 11 wt% carbohydrates, 4 wt% protein and 3 wt% ash.

[0057] In some embodiments, the oil composition comprises 95-99 wt% oil and 1 wt% ethanol. In such embodiments, the total amount of water, ash, protein and carbohydrates in the oil composition is 0-4 wt%. In some embodiments, the oil composition comprises about 100 wt% oil, or consists of oil.

[0058] It will be understood that the components (and their relative quantities) in the oil composition will vary dependent on the source and that the method of hydrolysis or transesterification is suitable for use on any of the oil compositions defined above, irrespective of the source.

[0059] Oil compositions disclosed herein comprise oil (comprising MAG, DAG and TAG) and optional further components. A waste product from a process could be an oil composition according to the present disclosure, if the waste product comprises oil (comprising MAG, DAG and TAG) and, optionally, further components as defined herein. It may be possible to use the method of processing an oil composition disclosed herein to upcycle an oil composition which is a waste product. For example, it may be possible to upcycle such an oil composition into products such as MAG, DAG and FAEE.

[0060] Obtaining an Oil Composition

[0061] An oil composition derived from a plant source may also be referred to herein as a “crude oil composition”. The term crude oil composition will be used to refer to an oil composition directly obtained from a source by extraction. The oil composition may be a crude or purified oil. As will be discussed in further detail later, a purified oil may be a crude oil composition that has been subjected to additional purification prior to hydrolysis or transesterification. In some embodiments, the crude oil composition is not subjected to additional purification prior to hydrolysis or transesterification, and therefore in these embodiments the terms “crude oil composition” and “oil composition” may be used interchangeably.

[0062] In some embodiments, the crude oil composition is obtained from a plant source. In some embodiments, the crude oil composition is obtained from a plant source which is chickpea, soy and / or lupin. In one such embodiment, the crude oil composition is obtained from a plant source which is chickpea. Methods of obtaining crude oil compositions from plant sources may include solvent extraction which separates oil from the other components in the plant source. Suitable solvents may include hexane and ethanol.

[0063] In some embodiments, a crude oil composition is obtained from a plant source by: mixing the plant source with ethanol (e.g. in a mixer); separating the crude oil composition from other components in the source (e.g. in a separator). Crude oil compositions obtained by this method comprise oil and ethanol. In some embodiments, the plant source is a plant-based flour. The flour may be chickpea-based flour, soybased flour or lupin-based flour. Separators suitable for use in this process include a disk-stack centrifuge, a decanter centrifuge, a 3 -phase cream separator and a countercurrent extraction unit.

[0064] A process involving isolation of protein from a plant source could also produce (as a byproduct) an oil composition as defined herein. It may be possible to use the method of processing disclosed herein to upcycle such oil compositions into products such as MAG, DAG and FAEE.

[0065] In some embodiments, a crude oil composition is obtained from a plant source by: (i) mixing plant-based flour or flakes with water and a base to generate an initial alkalized slurry comprising a starch precipitate and a protein-rich stream; (ii) separating the precipitate from the protein-rich stream. In some embodiments, the pH is adjusted to between 8-11 in step (i) by addition of the base. In some embodiments, the separator used in step (ii) is a disk-stack centrifuge or a decanter centrifuge.

[0066] In some embodiments, the process includes obtaining a flour or flakes from a plant source prior to mixing with water and a base. The flour or flakes are obtained by removing the shells and cortexes from the source and then milling into flour or flakes. Removal of the shells and cortexes can be done, for example, in a decortication device. Milling into flour or flakes can be done, for example, in a miller or a flaker.

[0067] In some embodiments, the protein-rich stream from step (ii) above is further separated into a crude oil composition and a de-oiled protein rich stream. In some embodiments, the separator used for this purpose is a disc-stack centrifuge or a 3-phase cream separator.

[0068] In some embodiments, the plant-based flour or flakes is de-oiled prior to mixing with base and water (i.e. prior to step (i) and (ii) above). This process generates a crude oil composition and a de-oiled flour or flakes. The plant-based flour or flakes is mixed with ethanol and the crude oil composition is then separated from the flour. In some embodiments, a de-oiling processor is used to de-oil the flour. The de-oiling processor can comprise: a mixer and a separator or as single device that does both mixing and separation. In some embodiments, the de-oiling processor further comprises a decortication device and a miller to generate the flour or flakes from the source prior to mixing and separation. In some embodiments, the mixer may be an immersion or ethanol-wetting tank. The ethanol may be pure ethanol or ethanol mixed with other liquids. In some embodiments, the ethanol is mixed with water. In some embodiments, the separator is a decanter centrifuge. For example, a counter-current extraction unit.

[0069] Optionally, this process further comprises: reducing the ethanol and / or water content of the crude oil composition by any suitable technique, for example, by evaporation. In some embodiments, a distillation column is used to remove ethanol from the crude oil composition. In some embodiments, the crude oil composition further comprises sugar and water and a separator can be used to separate the oil from the sugar and water. In some embodiments, the separator used for this purpose is a disk-stack centrifuge.

[0070] The following embodiments further illustrate how a crude oil composition may be obtained. These processes are described in, for example, US patent US10182590B2, herein incorporated by reference in its entirety.

[0071] FIG. 1 illustrates a system 100 including a first mixer 102, a first separator 104, a second separator 106 and a second mixer 108. The system further includes a third separator 110, a wash station 112, a third mixer 114, a homogenizer 116, a pasteurizer 118, a vacuum evaporator 120 and a dryer 122.

[0072] FIG. 1 illustrates one embodiment of a process flow operation for generating the chickpea concentrate. The process flow operation includes a separator 106 that generates a crude oil composition via a deoiling process.

[0073] The first mixer 102 receives flour, water and a base. In one embodiment, the flour is chickpea flour, but it is recognized that other suitable types of flour may be utilized. In this step, via the mixer, the flour is hydrated and there is a pH shift to solubilize the protein a solid-liquid extraction.

[0074] It is within the scope of the present invention that varying types of chickpea flour or the protein-based input ingredient(s) may be utilized, where the process described herein may be modified to account for such variations in the mixer 102 input. For example, the chick-pea flour may be a de-oiled flour, such that further processing operations described below for performing de-oiling operations may be omitted. For example, the flour may be pre-treated with a hexane extraction process, or other process to modify or adjust the physical composition of the flour, for example, as described in further detail in FIGS. 4-6 below. In one embodiment, in the mixer 102, hydration of the flour includes water ratio ranges between 5-12: 1 depending on equipment and desired purity of end product. While varying ranges may be utilized, this embodiment includes a low-end ratio is found to be 4: 1, with a high-end ratio dependent upon capacity of drying operations noted below. In one embodiment, operational temperature range is between 4-60 °C depending on embodiment of final product attribute, including generating a pH between 8-11. The mixer 102, in this embodiment, operates using low shear conditions. Similarly, this embodiment uses a reaction time between 30-60 min depending on holding conditions. The pressure in the mixer 102 is at or near atmospheric pressure.

[0075] It is noted that the above ranges and conditions, as well as ranges, conditions and values noted within the present specification, are exemplary in nature of the various embodiments. The ranges and conditions are not limiting of the disclosed invention, wherein operations aspects outside the noted ranges may be utilized in the protein extraction process, as recognized by one skilled in the art.

[0076] Based on the mixing operations, the mixer outputs an initial alkalized slurry. The initial alkalized slurry is then transported to the first separator 104. As described in further detail below, the initial alkalized slurry may be transported using a low sheer pump, but it is recognized that any suitable pump may be utilized.

[0077] The first separator 104 separates the initial alkalized slurry into a starch precipitate and a solubilized protein rich steam. The separator 104, in one embodiment, is a decanter centrifuge. The starch precipitate is extracted and in one embodiment can be discarded. The solubilized protein rich stream is further processed to a second separator 106.

[0078] In one embodiment, solubilized protein rich stream may be transferred to the separator 106 using a low-sheer pump, but any other suitable pump may be utilized.

[0079] The solubilized protein rich stream is separated using, in one embodiment, with the separator 106 being a disk-stack centrifuge to remove a crude oil composition. The centrifuge output includes a crude oil composition and a de-oiled solubilized protein rich stream. The crude oil composition may be processed by the method of processing an oil composition disclosed herein.

[0080] FIG. 2 illustrates one embodiment of a flowchart of steps of a method for generating a chickpea concentrate. The method described herein may be performed using the system 100 of FIG. 1, whereas it is recognized that the steps may be performed using any other suitable machine or apparatus for performing the described operation.

[0081] A first step, step 200, is generating an initial alkalized slurry by combining flour, water and base. As described above, the flour is a chickpea-based flour.

[0082] In one embodiment, instead of chickpea flour feed stock, wet-milled white chickpeas can be used and fed directly to the wet process. In another embodiment, an air classified protein concentrate can be used. It is recognized that various other embodiments exist such that based on preceding processing conditions, a chickpea flour-type input in some manner or another, is fed into the system.

[0083] A next step, step 202, is generating a solubilized rich protein stream by separating the initial alkalized slurry. This step may be performed using a separator, wherein in one embodiment the step includes the removal of a starch precipitate from the slurry.

[0084] A next step, 204, is generating a de-oiled solubilized rich protein stream by separating the solubilized rich protein stream. This step may be performing using a separator, including generating a crude oil composition as well as the de-oiled solubilized rich protein stream. The crude oil composition may be processed by the method of processing an oil composition disclosed herein.

[0085] FIG. 3 illustrates a processing flowchart of part of a chickpea protein extraction process. While noted with exemplary values, the embodiment of FIG. 3, including the exemplary values, are not limiting in nature as varying processing values may be readily utilized, as recognized by one skilled in the art. The process begins in FIG. 3, wherein 1000 kg Chickpea flour 402 is liquefied with 5000 kg water 404 using a liquefier 406. The combined slurry enters a first reaction tank 408 in which the pH is adjusted to 11 using aqueous sodium hydroxide 410, temperature at 55 °C and held under low shear conditions for approximately 75 minutes. Using the first decanter 412, approximately 1300 kg of wet starch 414 is then extracted and the protein rich liquid is passed through a 3-phase cream separator 416. This cream separator extracts approximately 230 kg of a crude oil composition 418. The crude oil composition 418 may be processed by the method of processing an oil composition disclosed herein.

[0086] FIG. 4 illustrates one embodiment of another technique for generating plantbased protein extraction by de-oiling the material prior to the protein extraction process. The elements of FIG. 4 provide for pre-processing of the flour, as illustrated in FIG. 1, but include the removal of oil, sugars and other organics within the flour.

[0087] The embodiment of FIG. 4 includes a de-oiling processor 502, as described in further detail in FIG. 5. The de-oiling processor receives the food element from which the protein is extracted. In the exemplary embodiments of FIGS. 4 and 5, the food source is chickpeas, but any other suitable type of food source may be utilized. Other suitable food sources include soy and lupin. Via the de-oiling process, the processor 502 generates de-oiled flour 504.

[0088] The embodiment of FIG. 4 includes a de-oiling processor 502, as described in further detail in FIG. 5. The de-oiling processor receives the food element from which the protein is extracted. In the exemplary embodiments of FIGS. 4 and 5, the food source is chickpeas, but any other suitable type of food source may be utilized. Via the de-oiling process, the processor 502 generates de-oiled flour 504.

[0089] FIG. 5 illustrates one embodiment of the de-oiling processor 502 of FIG. 4. In the exemplary embodiment, the de-oiling is performed using a decortication device 510, a milling or roller-flaker 512, a mixer 514, decanter centrifuge 516 and a dryer 518. The decortication device 510, mixer 514, decanter centrifuge 516 and dryer 518 may be any suitable device operative to perform the processing operations described herein, as recognized by one skilled in the art. The milling / roller-flaker 512 represents one of several varying embodiments operative within the present system. The device 512 may be a roller mill / flaker that is operative to process the decorticated chickpeas and generate flakes. The device 512 may, in another embodiment, be a flour mill operative to mill flour instead of flakes.

[0090] The decortication device 510 receives the chickpeas, which can be provided raw. The device 510 operates to remove the cortexes from the chickpea, removing the outer hull and exposing the protein-rich insides. The device 510 generates cortex waste 522, which can be discarded. The device 510 further outputs the chickpeas having the shells or cortexes removed to the milling / roller-flaker device 512.

[0091] The milling / roller-flaker device 512 operates to mill the chickpeas into a milled or flour feedstock. In one embodiment, instead of being milled to a particular powder, the device 512 may flake the chickpeas to a designated flake size, such as in one exemplary embodiment having flakes in the range of 0.25 mm to 0.4 mm, but such range is not limiting in nature. Whether the device 512 is a flaker or a miller, the output 526 still includes its oil. As noted herein, the flake ranges of 0.25 mm to 0.4 mm are exemplary ranges, but not express limiting ranges. It is recognized that smaller flake size may be utilized up until the flakes have a powder consistency. It is further recognized that larger flakes may be utilized where larger flakes may require further processing for efficient de-oiling.

[0092] As part of the de-oiling process, the mixer 514 therein mixes the flour 526 with ethyl alcohol 528, more commonly referred to as ethanol. The mixture of the ethanol with the flour provides for removal of the oil from the flour in accordance with known oil-extraction techniques. The mixer 514 may be an immersion or ethanol-wetting tank, which may include a mixing element to saturate the flour with ethanol. It is recognized that one embodiment uses pure ethanol herein, but other variations of ethanol may be utilized including ethanol mixed with other liquids, including have a water concentration or other mixture recognized by one skilled in the art, including for example ethanol recovered from a recycling loop as described below in FIG. 7.

[0093] The mixer 514 output is a mixture 530 of the flour and ethanol. The decanter centrifuge 516 receives the mixture 530 and therein extracts crude oil composition 532, consistent of ethyl alcohol with oils, sugar and other organics absorbed therein. The crude oil composition 532 may be processed by the method of processing an oil composition disclosed herein. The extractor 516 additionally generates the de-oiled flour 534 with remaining ethanol. In this embodiment, the flour mixture 534 is a wet mixture, which is then provided to the dryer 518.

[0094] FIG. 6 illustrates another embodiment of the de-oiling processor 502. This embodiment includes the decortication device 510, milling / roller-flaker 512 and dryer 518, but instead uses a counter-current extraction unit 540. By way of example, the unit 540 may be a Crown Countercurrent solvent extraction unit, manufactured by Crown Ironworks, Roseville, Minn.

[0095] Similar to the operations of FIG. 5, the decortication device 510 generates waste 522, as well as the input to the milling / roller-flaker 512. Depending on whether the device 512 is a roller miller / flaker or a flour mill, the output is either flakes or flour, having oil contained therein.

[0096] In this embodiment, the counter-current extraction unit 540 receives the flake / flour plus oil mixture 526. Performing operations consistent with countercurrent extraction, the device 540 therein generates two outputs. Crude oil composition 532 is the first output stream and de-oiled flour with ethanol 534 is the second stream. The crude oil composition 532 may be processed by the method of processing an oil composition disclosed herein. The above embodiment is described with chickpeas, but is also operable on other members of legume family, as well as any suitable feedstock having an oil content. FIG. 7 illustrates one embodiment of an ethanol recycling loop usable with the processor 502 of FIGS. 4-6. The recycling loop receives the crude oil composition 532, consisting of oil extracted from the material, ethanol and sugar. A distillation column 560 separates the input 532 into azeotropic ethanol 562 and an oil composition, sugar and other organics 564. In one embodiment, molecular sieves may be used to extract water from the ethanol 566. Such ethanol can then be recycled back to the mixer 528 of FIG. 5 and / or the countercurrent extraction unit 540 of FIG. 6. The crude oil composition 532 may be processed by the method of processing an oil composition disclosed herein. Removing ethanol from the crude oil composition 532 using the distillation column 560 is an example of purification of an oil composition that may be carried out prior to hydrolysis or transesterification. Methods of purifying an oil composition prior to hydrolysis or transesterification are discussed in more detail in the next section.

[0097] In FIG. 7, a mixer 568 receives both the oil composition and sugar 564 as well as water 570. A disc stack centrifuge 572 receives the mixture and output oil composition 574 and sugar and water mixture 576. Oil composition 574 may be processed by the method of processing an oil composition disclosed herein. Removing sugar and water from the oil composition using the disc stack centrifuge 572 is an example of purification of an oil composition that may be carried out prior to hydrolysis or transesterification. Methods of purifying an oil composition prior to hydrolysis or transesterification are discussed in more detail in the next section.

[0098] Purification of Oil Compositions

[0099] The oil composition subjected to hydrolysis or transesterification may be a crude oil composition directly obtained from plants. In some embodiments, the oil composition may be a crude oil composition that has been purified to remove one or more impurities. Impurities include ash, protein, free fatty acids, phospholipids, waxes, carbohydrates, water and / or ethanol. The crude oil composition (i.e. the purified oil composition) may be purified to reduce the ethanol content to less than 10 wt%, or less than 5 wt%, or less than 2 wt%, or less than 1 wt%. The crude oil composition may be purified such that it is substantially free of ethanol.

[0100] Suitable techniques for purifying the crude oil composition include solvent extraction oven drying, vacuum drying, distillation washing, agitation, degumming, deacidification, centrifugation, bleaching, deodorising and / or clarifying. These techniques will be known to those skilled in the art. For example, solvent extraction may be liquid-liquid extraction using organic solvents. Suitable solvents include hexane and ethanol, methanol, heptane, butane and ethyl acetate. In some embodiments, it may be extraction using supercritical CO2. Oven or vacuum drying may be used to reduce ethanol content by evaporation. Washing with water may be used to remove water- soluble impurities. Degumming involves the removal of water, carbohydrates and proteins. Deacidification removes fatty acids, phospholipids, pigments and waxes. The addition of bases, such as NaOH, neutralises these components causing them to precipitate. The precipitate can they be separated by any suitable method, for example, filtration. Centrifugation may be used to separate the oil from wash water and / or insoluble matter, such as ash. Bleaching may be used to remove “off-coloured” pigment components by adding clay to absorb the pigments. The clay can then be separated by any suitable method, for example, filtration. Deodorising is used to remove less stable compounds that have unusual odours or tastes. Clarifying refers to removal of solid components, for example, using a decanter.

[0101] The degumming process may include the addition of additives. Suitable additives include phosphoric acid, citric acid and phospholipid enzymes, such as phospholipases. For example, phospholipases break down phospholipids, making them more water soluble. These additives increase the water-solubility of the water-soluble impurities present in the crude oil composition to improve their extraction when the oil is washed with water. The addition of enzymes has been found to reduce the viscosity of the water phase. Water-soluble impurities in the crude oil composition include colloidal substances such as proteins. One of the disadvantages of purifying the crude oil composition by washing with water is that some of the oil is lost during separation of the purified oil and the wash water. The inclusion of these additives can lead to improved oil yield after purification of the crude oil composition. In some embodiments, the addition of citric acid and phospholipid enzymes in combination can improve the oil yield yet further compared with a single additive alone. However, in some examples, the amount of ethanol present in the crude oil composition may lead to denaturation of the enzymes, so enzymes may not always be suitable. The greatest improvement in oil yield through addition of citric acid and phospholipid enzymes in combination is achieved when the ethanol content of the crude oil composition is between 0-15 wt%, or 0-13 wt%, or less than 3 wt%. The ethanol content could be reduced to this level by any suitable method prior to the addition of enzymes during the water wash.

[0102] It has also been found that washing with water followed by centrifugation can lead to satisfactory purification of crude oil compositions. The washing process includes: (i) adding water; (ii) agitating the crude oil composition for a period of time; (iii) centrifugation to separate the oil and water. Repeating this process can improve the removal of impurities further. In some examples, hot water is used and / or the oil-water mixture is heated to improve dissolution of water-soluble impurities. In some embodiments, the crude oil composition is purified by: (i) adding water; (ii) maintaining the temperature at 80 °C for 30 min with agitation; (iii) centrifugation to separate the oil composition and water; (iv) adding further water; (v) agitation at room temperature for 5 minutes; (vi) centrifugation to separate the oil composition and water. It is possible to achieve satisfactory purification using steps (i)-(iii) only. Variations of this process (temperature, time, ratio of oil to water used) will be obvious to the skilled person and can be used to obtain various oil compositions comprising between 95-99 wt% oil and 1% ethanol, with the remaining 0-4 wt% comprising ash, carbohydrate, protein and water. For example, steps (i)-(iii) can be used to reduce the ethanol content of the oil to less than 1.5 wt%. Advantageously, carrying out steps (i)-(vi) can reduce the ethanol content of the oil to less than 0.3 wt% and / or less than 1 wt% ash, carbohydrate, protein and water.

[0103] In some examples, the crude oil composition is purified by refining-bleaching- deodorising (RBD), a common technique for oil purification which will be well-known to those skilled in the art. When RBD is used to purify the crude oil composition, the resulting oil composition can be said to be substantially-free of impurities, such that it comprises about 100% oil. In some embodiments, the RBD process comprises degumming, deacidification, centrifugation, bleaching and deodorising.

[0104] Method of Processing an Oil Composition

[0105] Also disclosed herein is a method of processing an oil composition. The oil composition comprises: 40-100 wt % oil; 0-20 wt% ethanol; 0-25 wt% water. In some embodiments, the oil composition comprises: 47-100 wt % oil; 0-20 wt% ethanol; 0-22 wt% water; 0-15 wt% carbohydrate; 0-7 wt% protein and 0-5 wt% ash. These oil compositions are expressed relative to total oil composition (rather than the amount of oil comprising monoacylglycerides, diacylglycerides and triacylglycerides).

[0106] The method of processing an oil composition can be used to synthesise monoacylglycerides, diacylgycerides and / or fatty acid ethyl esters (FAEE). In some embodiments, the method comprises: (i) adding water and a base to the oil composition; hydrolysing at least some of the diacylglycerides and triacylglycerides to obtain an oil comprising: at least 10 wt% monoacylglycerides; and / or at least 1-90 wt% diacylglycerides; or the method comprises: (ii) adding ethanol and a base to the oil composition; transesterification of at least some of the monoacylglycerides, diacylglycerides and / or triacylglycerides to obtain an oil comprising: at least 20 wt% fatty acid ethyl esters (FAEE). These product compositions are expressed relative to the total amount of oil comprising monoacylglycerides, diacylglycerides and triacylglycerides (rather than the total oil composition).

[0107] In some embodiments, the method comprises: adding water and an enzyme to the oil composition; hydrolysing at least some of the diacylglycerides and triacylglycerides to obtain an oil comprising: at least 10 wt % monoacylglycerides; and / or at least 10 wt% diacylglycerides. These product compositions are expressed relative to the total amount of oil comprising monoacylglycerides, diacylglycerides and triacylglycerides (rather than the total oil composition). Synthesis of Monoacylglycerides and Diacylglycerides

[0108] In some embodiments, the method of processing an oil composition comprises adding water and a base to the oil composition, or the method comprises adding water and an enzyme to the oil composition; and hydrolysing at least some of the diacylglycerides and / or triacylglycerides to obtain an oil comprising at least 10 wt% monoacylglycerides; and / or at least 10 wt% diacylglycerides. In these embodiments, the method can be used to synthesise monoacylglycerides and / or diacylglycerides.

[0109] Triacylglycerides comprise three fatty acid chains and a glycerol backbone, with each fatty acid chain attached to glycerol via an ester bond. Hydrolysis can be used cleave the ester bonds, leading to diacylglycerides, monoacylglycerides or free glycerol depending on the degree of hydrolysis of the triacylglycerides. The overall reaction consists of a series of equilibria between TAG, DAG, MAG and free glycerol:

[0110] TAG DAG MAG free glycerol

[0111] This aspect of the method comprises addition of water (and a base or enzyme) to the oil composition. In order to hydrolyse TAGs to an equivalent molar quantity of DAGs, a molar ratio of at least 1 :1 of water:TAG is required. In order to hydrolyse TAGs to an equivalent molar quantity of MAGs, a molar ratio of at least 2: 1 of water:TAG is required. It will be understood that different ratios can be used. A molecular weight of the oil can be calculated, for example, based on the fatty acid profile of the MAG, DAG and TAG. The fatty acid profile may be determined by any suitable method, such as gas chromatography. The molecular weight of the oil can be used to determine suitable weight ratios of water and ethanol. For example, an oil of the present invention may have a molecular weight of 875 gmol'1. Such an oil would require approximately 18 g of water per 875 g of oil for a 1: 1 molar ratio of water to oil, or 36 g of water per 875 g of oil for a 2: 1 molar ratio.

[0112] In embodiments including addition of a base, the base may catalyse the reaction. For example, the base may be an inorganic base such as a group (I) or group (II) metal hydroxide. In some embodiments the base is NaOH, KOH, sodium methoxide (CHsONa), sodium ethoxide (C^HsONa) or Ca(OH)2. In some embodiments, the base is Ca(OH)2.

[0113] The method comprises hydrolysing at least some of the diacylglycerides and / or triacyl glycerides in the oil. The extent of hydrolysis can be controlled through selection of reaction parameters such as time, temperature and stoichiometry to achieve the desired product. For example, longer reaction times may yield an oil composition that is higher in MAG. Intermediate reaction times may yield a composition that is higher in DAG compared with longer reaction times. The reaction time should be selected as a compromise wherein sufficient TAG conversion is achieved without significant complete hydrolysis to free glycerol. In some examples, reaction parameters can be selected to obtain a mix of monoacylglycerols and diacylglycerols.

[0114] These reactions typically require high temperatures. For example, the reaction temperature is between 220 to 260 °C.

[0115] When the method of processing an oil composition comprises adding water and an enzyme to the oil composition and hydrolysing at least some of the diacylglycerides and / or triacylglycerides, the oil composition may be any of the oil compositions defined herein. Ethanol can inhibit enzyme activity, for example, by denaturation. In some embodiments, when an enzyme is used, the oil composition comprises 0-15 wt% ethanol, or 0-10 wt% ethanol, or 0-5 wt%, or 0-3 wt%, or 0-1 wt%, or is substantially free or free of ethanol.

[0116] In some embodiments, when an enzyme is used, the oil composition comprises 40-100 wt% oil, 0-15 wt% ethanol and 0-25 wt% water, 0-15 wt% carbohydrates, 0-7 wt% protein and 0-5 wt% ash. In some embodiments, the oil composition comprises 40-99.8 wt% oil, 0.1-15 wt% ethanol and 0.1-25 wt% water, 0-15 wt% carbohydrates, 0-7 wt% protein and 0-5 wt% ash. In some embodiments, the oil composition comprises about 47 wt% oil, 13.5 wt% ethanol and 22 wt% water. In some embodiments, when an enzyme is used, the oil composition comprises 95-99 wt% oil and 1 wt% ethanol. In such embodiments, the total amount of water, ash, protein and carbohydrates in the oil composition is 0-4 wt%. In some embodiments, when an enzyme is used, the oil composition comprises about 100 wt% oil, or consists of oil.

[0117] In some embodiments, the enzyme is a lipase enzyme. In some embodiments, the enzyme may be a powder enzyme or an immobilised enzyme. For example, a powder lipase or an immobilized lipase. In some embodiments, the enzyme is a powder lipase. Suitable lipase enzymes include those extracted from Candida rugosa. Rhyzopus oryzae or Rhizomucor miehei. For example, powder enzymes available commercially include Amano AY and Amano G available from Amano Enzyme and Lipomod34MDP and Lipomod 767P available from Biocatalysts. For example, immobilised enzymes available commercially include Lipozyme 435 and Lipozyme TL IM from Novozymes.

[0118] When enzymes are used, it may be advantageous to control the temperature and pH, for example, to a temperature and pH which results in optimum enzymatic activity. In some embodiments, the temperature is in the range 40-70 °C. In some embodiments, the pH is 5-9. In some embodiments, the enzyme is an immobilised enzyme and a higher temperature may be used. In some embodiments, the amount of enzyme added is 2-10 wt% relative to the amount of oil (i.e. the oil comprising MAG, DAG and TAG) present in the oil composition. In some embodiments, the amount of enzyme added is about 3 wt%.

[0119] After hydrolysis of at least some of the diacylglycerides and / or triacylglycerides, an oil is obtained comprising at least 10 wt % monoacylglycerides; and / or at least 10 wt% diacylglycerides. In some embodiments, after hydrolysis the oil comprises at least 1 wt%, or at least 20 wt%, or at least 25 wt%, or at least 30 wt% diacylglycerides. In some embodiments, the oil comprises at least 10 wt%, or at least 40 wt%, or at least 70 wt%, or at least 90 wt% monoacylglycerides. After hydrolysis, the oil may comprise residual triacylglycerides. These TAGs may be the same or different to those present before hydrolysis, for example, due to interesterification to rearrange the fatty acid positions. In some embodiments, after hydrolysis the oil comprises at least 10 wt% monoacylglycerides and / or at least 10 wt% diacylglycerides, and further comprises triacylglycerides. In some embodiments, after hydrolysis the oil comprises less than 70 wt%, or less than 20 wt%, or less than 2 wt% triacylglycerides. In some embodiments, the oil is substantially free of triacylglycerides.

[0120] In some embodiments, the oil composition obtained after hydrolysis comprises further components. These further components may be the same as those present in the oil composition prior to hydrolysis. For example, the oil composition after hydrolysis can further comprise ash, protein, free fatty acids, phospholipids, waxes and / or carbohydrates. Examples of other further components that may be present in the oil composition include byproducts of the hydrolysis reaction such as free glycerol and free fatty acids. Free glycerol may be formed by hydrolysis of monoacylglycerides. It is possible to control the amount of hydrolysis of monoacylglycerides that occurs through selection of reaction parameters such as reaction time. It is desirable to minimise the amount of free glycerol produced, as this will have a negative impact on the overall diacylglyceride and / or monoacylglyceride yield of the process. In some embodiments, the amount of free glycerol present in the oil after hydrolysis is less than 5 wt%, or less than 2 wt%.

[0121] In some embodiments, after hydrolysis the oil comprises 1-90 wt%, 0-10 wt%, 15-25 wt%, 25-35 wt% or 20-30 wt% DAG. In some embodiments, after hydrolysis the oil comprises 10-99 wt%, 5-15 wt%, 45-55 wt%, 65-75 wt% or 85-95 wt% MAG. In some embodiments, after hydrolysis the oil comprises 1-90 wt% DAG and 10-99 wt% MAG. In some embodiments, after hydrolysis the oil comprises 15-25 wt% DAG and 5-15 wt% MAG. In some embodiments, after hydrolysis the oil comprises 25-35 wt% DAG and 45-55 wt% MAG. In some embodiments, after hydrolysis the oil comprises 20-30 wt% DAG and 65-75 wt% MAG. In some embodiments, after hydrolysis the oil comprises 0-10 wt% DAG and 85-95 wt% MAG. In some embodiments, after hydrolysis the oil comprises 65-75 wt% TAG, 15- 25 wt% DAG, 5-15 wt% MAG and 0-3 wt% free glycerol. In some embodiments, after hydrolysis the oil comprises 15-25 wt% TAG, 25-35 wt% DAG, 45-55 wt% MAG and 0-5 wt% free glycerol. In some embodiments, after hydrolysis the oil comprises 0-5 wt% TAG, 20-30 wt% DAG, 65-75 wt% MAG and 0-5 wt% free glycerol. In some embodiments, after hydrolysis the oil comprises 0-10 wt% DAG, 85-95 wt% MAG and 0-5 wt% free glycerol and is substantially free of TAG.

[0122] In some embodiments, after hydrolysis the oil comprises about 70 wt% TAG, about 20 wt% DAG, about 9 wt% MAG and less than about 1 wt% free glycerol. In some embodiments, after hydrolysis the oil comprises about 20 wt% TAG, about 30 wt% DAG, about 48 wt% MAG and less than about 2 wt% free glycerol. In some embodiments, after hydrolysis the oil comprises about 2 wt% TAG, about 25 wt% DAG, about 71 wt% MAG and less than about 2 wt% free glycerol. In some embodiments, after hydrolysis the oil comprises about 5 wt% DAG, about 93 wt% MAG and less than about 2 wt% free glycerol and is substantially free of TAG.

[0123] In some embodiments, the oil composition subjected to hydrolysis comprises about 100 wt% oil or consists of oil. In some embodiments, the oil composition is obtained by purifying a crude oil composition by refining-bleaching-deodorising (RBD), as described herein, to obtain an oil composition comprising about 100% oil or consisting of oil. In some embodiments, the RBD process comprises degumming, deacidification, centrifugation, bleaching and deodorising. After hydrolysis, the oil may be blended with at least one additional fat and / or at least one additional oil. Therefore, in some embodiments, the method comprises: (i) hydrolysis of an oil composition comprising about 100 wt% oil or consisting of oil; (ii) blending the oil obtained after hydrolysis with at least one additional fat and / or at least one additional oil. In some embodiments, the method comprises: (i) purification of a crude oil composition, wherein the purification comprises refining-bleaching-deodorisation; (ii) hydrolysis of an oil composition comprising about 100 wt% oil, or consisting of oil; (iii) blending the oil obtained after hydrolysis with at least one additional fat and / or at least one additional oil. In some embodiments, the at least one additional fat and / or at least one additional oil comprises about 100 wt% oil, or consists of oil, wherein the oil comprises greater than about 95 wt% triacylglycerides, or greater than 97 wt%, or greater than 98 wt%. In some embodiments, the at least one additional fat and / or at least one additional oil has been purified (prior to blending) by a purification process comprising refining, bleaching and deodorisation (RBD). In such embodiments, the additional fat and / or at least one additional oil comprises about 100 wt% oil, or consists of oil, wherein the oil comprises greater than about 95 wt% triacylglycerides, or greater than 97 wt%, or greater than 98 wt%. Suitable fats and / or oils include vegetable fats and oils, mediumchain triglyceride (MCT) oils, oils enriched with long-chain polyunsaturated fatty acids (LC-PUFAs), fish oils, marine oils, microbial oils, interesterified oils, coconut oil, structured lipids, olive oil and oils enriched in omega 6s. For example, vegetable oils may be high oleic canola, palm oil, and / or palm olein. In some such examples of these products, the monoacylglycerides and / or diacylglycerides may act as an emulsifier. Marine oils are oils from marine animals. Marine oils usually contain high levels of LC-PUFAs, like eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). Examples of marine oils include mackerel oil, fish oil and krill oil. Microbial oils are oils produced by microorganisms, such as arachidonic acid-rich single-cell oil (ARASCO) and docosahexaenoic acid-rich single-cell oil (DHASCO). ARASCO contains high levels of arachidonic acid and DHASCO contains high levels of docosahexaenoic acid.

[0124] In some embodiments, after hydrolysis of at least some of the diacylglycerides and / or triacylglycerides, an oil is obtained comprising at least 10 wt % monoacylglycerides; and / or at least 10 wt% diacylglycerides, and the method further comprises blending said oil with at least one additional fat and / or at least one additional oil. In some embodiments, after hydrolysis and prior to blending, the oil comprises at least 1 wt%, or at least 20 wt%, or at least 25 wt%, or at least 30 wt% diacylglycerides. In some embodiments, after hydrolysis and prior to blending, the oil comprises at least 10 wt%, or at least 40 wt%, or at least 70 wt%, or at least 90 wt% monoacylglycerides. In some embodiments, after hydrolysis the oil may comprise residual triacylglycerides, and the method further comprises blending said oil with at least one additional fat and / or at least one additional oil. These residual TAGs may be the same or different to those present before hydrolysis, for example, due to interesterification to rearrange the fatty acid positions. In some embodiments, after hydrolysis and prior to blending, the oil comprises at least 10 wt% monoacylglycerides and / or at least 10 wt% diacylglycerides, and further comprises triacylglycerides. In some embodiments, after hydrolysis and prior to blending, the oil comprises less than 70 wt%, or less than 20 wt%, or less than 2 wt% triacylglycerides. In some embodiments, after hydrolysis and prior to blending, the oil is substantially free of triacylglycerides.

[0125] In some embodiments, the oil composition obtained after hydrolysis comprises further components, and the method further comprises blending said oil with at least one additional fat and / or at least one additional oil. These further components may be the same as those present in the oil composition prior to hydrolysis. For example, the oil composition after hydrolysis can further comprise ash, protein, free fatty acids, phospholipids, waxes and / or carbohydrates. Examples of other further components that may be present in the oil composition include byproducts of the hydrolysis reaction such as free glycerol and free fatty acids. Free glycerol may be formed by hydrolysis of monoacylglycerides. It is possible to control the amount of hydrolysis of monoacylglycerides that occurs through selection of reaction parameters such as reaction time. It is desirable to minimise the amount of free glycerol produced, as this will have a negative impact on the overall diacylglyceride and / or monoacylglyceride yield of the process. In some embodiments, the amount of free glycerol present in the oil after hydrolysis and prior to blending is less than 5 wt%, or less than 2 wt%.

[0126] In some embodiments, after hydrolysis the oil comprises 1-90 wt%, 0-10 wt%, 15-25 wt%, 25-35 wt% or 20-30 wt% DAG, and the method further comprises blending said oil with at least one additional fat and / or at least one additional oil. In some embodiments, after hydrolysis the oil comprises 10-99 wt%, 5-15 wt%, 45-55 wt%, 65- 75 wt% or 85-95 wt% MAG, and the method further comprises blending said oil with at least one additional fat and / or at least one additional oil. In some embodiments, after hydrolysis the oil comprises 1-90 wt% DAG and 10-99 wt% MAG, and the method further comprises blending said oil with at least one additional fat and / or at least one additional oil. In some embodiments, after hydrolysis the oil comprises 15-25 wt% DAG and 5-15 wt% MAG, and the method further comprises blending said oil with at least one additional fat and / or at least one additional oil. In some embodiments, after hydrolysis the oil comprises 25-35 wt% DAG and 45-55 wt% MAG, and the method further comprises blending said oil with at least one additional fat and / or at least one additional oil. In some embodiments, after hydrolysis the oil comprises 20-30 wt% DAG and 65-75 wt% MAG, and the method further comprises blending said oil with at least one additional fat and / or at least one additional oil. In some embodiments, after hydrolysis the oil comprises 0-10 wt% DAG and 85-95 wt% MAG, and the method further comprises blending said oil with at least one additional fat and / or at least one additional oil.

[0127] In some embodiments, after hydrolysis the oil comprises 65-75 wt% TAG, 15- 25 wt% DAG, 5-15 wt% MAG and 0-3 wt% free glycerol, and the method further comprises blending said oil with at least one additional fat and / or at least one additional oil. In some embodiments, after hydrolysis the oil comprises 15-25 wt% TAG, 25-35 wt% DAG, 45-55 wt% MAG and 0-5 wt% free glycerol, and the method further comprises blending said oil with at least one additional fat and / or at least one additional oil. In some embodiments, after hydrolysis the oil comprises 0-5 wt% TAG, 20-30 wt% DAG, 65-75 wt% MAG and 0-5 wt% free glycerol, and the method further comprises blending said oil with at least one additional fat and / or at least one additional oil. In some embodiments, after hydrolysis the oil comprises 0-10 wt% DAG, 85-95 wt% MAG and 0-5 wt% free glycerol and is substantially free of TAG, and the method further comprises blending said oil with at least one additional fat and / or at least one additional oil.

[0128] In some embodiments, after hydrolysis the oil comprises about 70 wt% TAG, about 20 wt% DAG, about 9 wt% MAG and less than about 1 wt% free glycerol, and the method further comprises blending said oil with at least one additional fat and / or at least one additional oil. In some embodiments, after hydrolysis the oil comprises about 20 wt% TAG, about 30 wt% DAG, about 48 wt% MAG and less than about 2 wt% free glycerol, and the method further comprises blending said oil with at least one additional fat and / or at least one additional oil. In some embodiments, after hydrolysis the oil comprises about 2 wt% TAG, about 25 wt% DAG, about 71 wt% MAG and less than about 2 wt% free glycerol, and the method further comprises blending said oil with at least one additional fat and / or at least one additional oil. In some embodiments, after hydrolysis the oil comprises about 5 wt% DAG, about 93 wt% MAG and less than about 2 wt% free glycerol and is substantially free of TAG, and the method further comprises blending said oil with at least one additional fat and / or at least one additional oil.

[0129] Products Comprising Monoacylglycerides and Diacylglycerides

[0130] Another aspect of the present invention is to produce products comprising monoacylglycerides and / diacylglycerides obtained via the disclosed method. For example, an emulsifier comprising monoacylglycerides and / or diacylglycerides. Other examples include food, cosmetic or pharmaceutical products comprising monoacylglycerides and / or diacylglycerides. In some examples, the products may be fats and / or oils comprising monoacylglycerides and / or diacylglycerides obtained via the disclosed method. In some examples, such products can be made by isolating monoacylglycerides and / or diacylglycerides obtained via the disclosed method, then blending said monoacylglycerides and / or diacylglycerides with at least one fat and / or at least one oil.

[0131] In some embodiments, the method comprises one or more purification steps after hydrolysis to obtain a purified fraction comprising monoacylglycerides and / or a purified fraction comprising diacylglycerides. In some such embodiments, the method further comprises blending a purified fraction comprising monoacylglycerides and / or a purified fraction comprising diacylglycerides with at least one fat and / or at least one oil.

[0132] Suitable fats and / or oils include vegetable fats and oils, medium-chain triglyceride (MCT) oils, oils enriched with long-chain polyunsaturated fatty acids (LC- PUFAs), fish oils, marine oils, microbial oils, interesterified oils, coconut oil, structured lipids, olive oil and oils enriched in omega 6s. For example, vegetable oils may be high oleic canola, palm oil, and / or palm olein. In some such examples of these products, the monoacylglycerides and / or diacylglycerides may act as an emulsifier. Marine oils are oils from marine animals. Marine oils usually contain high levels of LC-PUFAs, like eicosapentaenoic acid (EP A) and docosahexaenoic acid (DHA). Examples of marine oils include mackerel oil, fish oil and krill oil. Microbial oils are oils produced by microorganisms, such as arachidonic acid-rich single-cell oil (ARASCO) and docosahexaenoic acid-rich single-cell oil (DHASCO). ARASCO contains high levels of arachidonic acid and DHASCO contains high levels of docosahexaenoic acid.

[0133] Synthesis of Structured Lipids

[0134] Structured lipids are triacylglycerides with specific combinations of fatty acid chains, such as the type of fatty acid and the position on the glycerol backbone. For example, they may contain a high level of a particular fatty acid, such as oleic acid, for nutritional reasons. The fatty acid chains may be modified to alter the physical properties of the structured lipid, such as its melting point. For example, to obtain a structured lipid that is a solid at room temperature. Structured lipids can be synthesised from products of the method of processing an oil composition disclosed herein. In some embodiments, structured lipids may be synthesised from the reaction of a monoacylglyceride and a diacylglyceride to give a structured lipid (triacylglyceride) and glycerol. In some embodiments, structured lipids may be synthesised from free fatty acids and triacylglycerides, wherein at least some of the free fatty acids replace at least some of the fatty acid chains present in the triacylglyceride to alter the composition of fatty acid chains in the triacylglyceride.

[0135] In some embodiments, a catalyst may be used. Suitable catalysts for interesterification include chemical or enzyme catalysts. In some embodiments, the enzyme may be a free enzyme or an immobilised enzyme. In some embodiments, the enzyme is an immobilized enzyme. Any suitable immobilised enzyme may be used. For example, free enzymes may be immobilised by any suitable known method to produce an immobilised enzyme. In other examples, commercially available immobilized enzymes such as Novozymes TL IM and Novozymes 435 may be used. In some embodiments in which an enzyme is used, the enzyme may be a stereospecific enzyme.

[0136] Synthesis of Fatty Acid Ethyl Esters (FAEE)

[0137] In some embodiments, the method of processing an oil composition comprises adding ethanol and a base to the oil composition; and transesterification of at least some of the monoacylglycerides, diacylglycerides and / or triacylglycerides to obtain an oil comprising at least 20 wt% fatty acid ethyl esters (FAEE).

[0138] The method comprises addition of ethanol and a base to the oil composition. In order to achieve full conversion of TAGs to an equivalent molar quantity of FAEEs, a molar ratio of at least 3 : 1 of ethanol : TAG is required. It will be understood that different ratios can be used. In some examples, the ethanokTAG molar ratio is between 3 : 1 and 9: 1. In some embodiments, the ratio of ethanol to oil may be 2: 1 by weight. Advantageously the crude oil compositions obtained from the ethanol extraction processes described above comprise ethanol. This can reduce the volume of ethanol that needs to be added to achieve a given ratio of ethanol: oil. As discussed above, the skilled person is capable of converting from molar ratio to weight ratio based on the molecular weight of a given oil.

[0139] The base may catalyse the reaction. This base may be any common base. For example, the base may be an inorganic base such as a group (I) or group (II) metal hydroxide. In some embodiments the base is NaOH, KOH or Ca(OH)2. In some embodiments, the base is Ca(OH)2. In some embodiments, the base is a strong base such as sodium methoxide (CHsONa) or sodium ethoxide (C2HsONa).

[0140] The method comprises transesterification of at least some of the monoacylglycerides, diacylglycerides and / or triacylglycerides. The extent of transesterification can be controlled through selection of reaction parameters such as time, temperature and stoichiometry to achieve the desired conversion. After transesterification of at least some of the monoacylglycerides, diacylglycerides and / or triacylglycerides an oil is obtained comprising at least 20 wt% fatty acid ethyl esters (FAEE). In some embodiments, an oil is obtained comprising at least 40 wt%, or at least 60 wt%, or at least 80 wt%, or at least 90 wt%, or at least 95 wt%, or at least 99 wt% fatty acid ethyl esters (FAEE).

[0141] In some embodiments, the oil composition obtained after transesterification comprises further components. These further components may be the same as those present in the oil composition prior to transesterification. For example, the oil composition after transesterification can further comprise ash, protein, free fatty acids, phospholipids, waxes and / or carbohydrates. Examples of other further components that may be present in the oil composition include byproducts of the transesterification reaction such as free glycerol and unesterified free fatty acids.

[0142] In some embodiments, the oil composition may be blended prior to transesterification. Said blending comprises blending the oil composition with at least one additional oil composition to make a blended oil composition. Blended oil compositions may comprise a first oil composition, and one, two, three, four or more additional oil compositions. The first oil composition may be a crude or purified oil composition, as described above. In some examples, the first oil composition is blended with a second oil composition. In some examples, the first oil composition is blended with a second and a third oil composition. In some examples, a blended oil composition can be made by blending at least a first and a second oil composition in any suitable ratio.

[0143] The first oil composition comprises oil and, optionally, one or more additional components. The first oil composition comprises 40-100 wt% oil, 0-20 wt% ethanol and 0-25 wt% water. In some embodiments, the first oil composition comprises 40- 99.8 wt% oil, 0.1-20 wt% ethanol and 0.1-25 wt% water. In some embodiments, the first oil composition comprises 40-100 wt% oil, 0-15 wt% ethanol and 0-25 wt% water. In some embodiments, the first oil composition comprises 40-99.8 wt% oil, 0.1-15 wt% ethanol and 0.1-25 wt% water. These first oil compositions are expressed relative to total first oil composition (rather than the amount of oil comprising monoacylglycerides, diacylglycerides and triacylglycerides).

[0144] In some embodiments, the first oil composition further comprises one or more additional components. The first oil composition may further comprise one or more of ash, protein, free fatty acids, phospholipids, waxes and / or carbohydrates. In some embodiments, the first oil composition comprises 40-100 wt% oil, 0-20 wt% ethanol and 0-25 wt% water, 0-15 wt% carbohydrates, 0-7 wt% protein and 0-5 wt% ash. In some embodiments, the first oil composition comprises 40-99.8 wt% oil, 0.1-20 wt% ethanol and 0.1-25 wt% water, 0-15 wt% carbohydrates, 0-7 wt% protein and 0-5 wt% ash. In some embodiments, the first oil composition comprises 40-100 wt% oil, 0-15 wt% ethanol and 0-25 wt% water, 0-15 wt% carbohydrates, 0-7 wt% protein and 0-5 wt% ash. In some embodiments, the first oil composition comprises 40-99.8 wt% oil, 0.1-15 wt% ethanol and 0.1-25 wt% water, 0-15 wt% carbohydrates, 0-7 wt% protein and 0-5 wt% ash.

[0145] The oil in the first oil composition comprises 90-100 wt% triacylglycerides; 0- 10 wt% diacylglycerides; and less than 5 wt% monoacylglycerides. In some embodiments, the oil in the first oil composition comprises 95-99 wt% triacylglycerides; 1-5 wt% diacylglycerides; and less than 1 wt% monoacylglycerides. In some embodiments, the oil comprises less than 1 wt% free fatty acids, or 0.01-0.1 wt%. These compositions of the oil are expressed relative to the total amount of oil comprising monoacylglycerides, diacylglycerides and triacylglycerides (rather than the total first oil composition).

[0146] In some embodiments, the first oil composition comprises about 47 wt% oil, 13.5 wt% ethanol and 22 wt% water. In an embodiment, the first oil composition comprises about 47 wt % oil, 13.5 wt% ethanol, 22 wt% water, 11 wt% carbohydrates, 4 wt% protein and 3 wt% ash. In some embodiments, the first oil composition is obtained from a plant source. In some embodiments, the first oil composition is obtained from a plant source which is chickpea, soy and / or lupin. In one such embodiment, the first oil composition is obtained from a plant source which is chickpea. In some embodiments, the at least one additional oil composition comprises about 100 wt% oil, or consists of oil, wherein the oil comprises greater than about 95 wt% triacylglycerides, or greater than 97 wt%, or greater than 98 wt%. In some embodiments, the at least one additional oil composition has been purified (prior to blending) by a purification process comprising refining, bleaching and deodorisation (RBD). In such embodiments, the additional oil composition comprises about 100 wt% oil, or consists of oil, wherein the oil comprises greater than about 95 wt% triacylglycerides, or greater than 97 wt%, or greater than 98 wt%.

[0147] Suitable additional oil compositions for blending with a first oil composition include vegetable fats and oils, medium-chain triglyceride (MCT) oils, oils enriched with long-chain polyunsaturated fatty acids (LC-PUFAs), fish oils, marine oils, microbial oils, interesterified oils, coconut oil, structured lipids, olive oil and oils enriched in omega 6s. For example, vegetable oils may be high oleic canola oil, com oil, soybean oil, palm oil, and / or palm olein. Marine oils are oils from marine animals. Marine oils usually contain high levels of LC-PUFAs, like eicosapentaenoic acid (EP A) and docosahexaenoic acid (DHA). Examples of marine oils include mackerel oil, fish oil and krill oil. Microbial oils are oils produced by microorganisms, such as arachidonic acid-rich single-cell oil (ARASCO) and docosahexaenoic acid-rich singlecell oil (DHASCO). ARASCO contains high levels of arachidonic acid and DHASCO contains high levels of docosahexaenoic acid.

[0148] Purification of the Products

[0149] In some embodiments, the method further comprises one or more purification steps after the hydrolysis or transesterification reactions to increase the purity of the desired product. In some embodiments, the one or more purification steps is selected from centrifugation, crystallisation and / or distillation. After purification, at least one purified fraction is obtained. A purified fraction may comprise at least 90 wt% monoacylglycerides, at least 90 wt% diacylglycerides or at least 90 wt% FAEEs. If hydrolysis or transesterification proceeds to the extent that free glycerol is produced, free glycerol can be separated from the desired products using centrifugation. FAEE can be obtained by crystallisation. In some embodiments, low temperature crystallisation (also known as winterisation) may be used to separate FAEE from the remainder of the oil.

[0150] In some embodiments, the oil comprising monoacylglycerides and / or diacylglycerides can be purified using distillation. For example, when the oil comprises monoacylglycerides, a distillate comprising at least 90 wt% monoacylglycerides can be obtained by distillation. The distillate may comprise at least 90 wt% monoacylglycerides, or at least 95 wt%, or at least 99 wt%. When the oil comprises diacylglycerides, a distillate comprising at least 90 wt% diacylglycerides can be obtained by distillation. The distillate may comprise at least 90 wt% diacylglycerides, or at least 95 wt%, or at least 99 wt%. In some embodiments, the oil may comprise monoacylglycerides and diacylglycerides. In these embodiments, it is possible to obtain two separate distillates, one comprising at least 90 wt% monoacylglycerides and one comprising at least 90 wt% diacylglycerides. Advantageously, this permits the two products to be obtained from a single process.

[0151] As described earlier, in some embodiments, after hydrolysis the oil comprising monoacylglycerides and / or diacylglycerides further comprises residual triacylglycerides. In some such embodiments, the oil comprising monoacylglycerides and / or diacylglycerides, and further comprising residual triacylglycerides, can be purified using distillation. In some such embodiments, it is possible to obtain a distillate comprising at least 90 wt% monoacylglycerides and / or a distillate comprising at least 90 wt% diacylglycerides, as described above, and to obtain a residue after distillation comprising at least 90 wt% triacylglycerides. This residue after distillation may be considered a purified fraction comprising triacylglycerides. For example, the residue after distillation may be a purified fraction comprising at least 90 wt% triacylglycerides or at least 95 wt%, or at least 99 wt%. In some embodiments, the oils comprising monoacylglycerides, diacylglycerides and triacylglycerides may be separated into: a distillate comprising monoacylglycerides, a distillate comprising diacylglycerides and a residue comprising triacylglycerides.

[0152] In some embodiments, free glycerol is separated from the oil comprising monoacylglycerides and / or diacylglycerides using centrifugation in a first purification step, and then distillation is used to obtain a distillate comprising at least 90 wt% or at least 95 wt%, or at least 99 wt% monoacylglycerides and / or a distillate comprising at least 90 wt% or at least 95 wt%, or at least 99 wt% diacylglycerides. In some embodiments, free glycerol is separated from the oil comprising monoacylglycerides and / or diacylglycerides, and further comprising residual triacylglycerides, using centrifugation in a first purification step, and then distillation is used to obtain a distillate comprising at least 90 wt% monoacylglycerides, or at least 95 wt%, or at least 99 wt%, and / or a distillate comprising at least 90 wt% diacylglycerides, or at least 95 wt%, or at least 99 wt%, and / or a residue comprising at least 90 wt% triacylglycerides or at least 95 wt%, or at least 99 wt%.

[0153] In some embodiments, artificial or natural antioxidants may be added to at least one purified fraction comprising monoacylglycerides and / or at least one purified fraction comprising diacylglycerides and / or at least one purified fraction comprising triacylglycerides.

[0154] In some embodiments, at least one purified fraction comprising monoacylglycerides and / or at least one purified fraction comprising diacylglycerides and / or at least one purified fraction comprising triacylglycerides may be blended with at least one fat and / or at least one oil, and, optionally, artificial or natural antioxidants may be added. In some embodiments, the at least one fat and / or at least one oil comprises about 100 wt% oil, or consists of oil, wherein the oil comprises greater than about 95 wt% triacylglycerides, or greater than 97 wt%, or greater than 98 wt%. In some embodiments, the at least one fat and / or at least one oil has been purified (prior to blending) by a purification process comprising refining, bleaching and deodorisation (RBD). In such embodiments, the at least one fat and / or at least one oil comprises about 100 wt% oil, or consists of oil, wherein the oil comprises greater than about 95 wt% triacylglycerides, or greater than 97 wt%, or greater than 98 wt%.

[0155] In some embodiments, a purified fraction comprising at least 90 wt% monoacylglycerides, or at least 95 wt%, or at least 99 wt%, may be blended with at least one fat and / or at least one oil. In some embodiments, a purified fraction comprising at least 90 wt% diacylglycerides, or at least 95 wt%, or at least 99 wt%, may be blended with at least one fat and / or at least one oil. In some embodiments, a purified fraction comprising at least 90 wt% triacylglycerides, or at least 95 wt%, or at least 99 wt%, may be blended with at least one fat and / or at least one oil. Such blends comprise MAGs, DAGs and / or TAGs obtainable by the method of processing an oil composition disclosed herein. Additionally, such blends further comprise TAGs from the at least one fat and / or at least one oil. These blends may be subjected to the interesterification process described herein to interesterify said MAGs, DAGs and TAGs present in the blends. In some embodiments, after interesterification, artificial or natural antioxidants may be added.

[0156] In some embodiments, the ratio of MAGs, DAGs and / or TAGS to the at least one fat and / or at least one oil may be 1 : 1, 1 :2, 1 :3, 1:5, or 1 :7. In some embodiments, a catalyst may be used. Suitable catalysts for interesterification include chemical or enzyme catalysts. In some embodiments, the enzyme may be a free enzyme or an immobilised enzyme. In some embodiments, the enzyme is an immobilized enzyme. Any suitable immobilised enzyme may be used. For example, free enzymes may be immobilised by any suitable known method to produce an immobilised enzyme. In other examples, commercially available immobilized enzymes such as Novozymes TL IM and Novozymes 435 may be used. In some embodiments in which an enzyme is used, the enzyme may be a stereospecific enzyme.

[0157] In some embodiments, a purified fraction comprising at least 90 wt% monoacylglycerides, or at least 95 wt%, or at least 99 wt%, may be blended with at least one fat and / or at least one oil. Such blends comprise MAGs obtainable by the method of processing an oil composition disclosed herein and TAGs from the at least one fat and / or at least one oil. The blend may be subjected to interesterification to interesterify said MAGs and TAGs. In some such embodiments, interesterification comprises adding a catalyst.

[0158] In some embodiments, a purified fraction comprising at least 90 wt% diacylglycerides, or at least 95 wt%, or at least 99 wt%, may be blended with at least one fat and / or at least one oil. Such blends comprise DAGs obtainable by the method of processing an oil composition disclosed herein and TAGs from the at least one fat and / or at least one oil. The blend may be subjected to interesterification to interesterify said DAGs and TAGs. In some such embodiments, interesterification comprises adding a catalyst.

[0159] In some embodiments, a purified fraction comprising at least 90 wt% triacylglycerides, or at least 95 wt%, or at least 99 wt%, may be blended with at least one fat and / or at least one oil. In some embodiments, the at least one fat and / or at least one oil comprises about 100 wt% oil, or consists of oil, wherein the oil comprises greater than about 95 wt% triacylglycerides, or greater than 97 wt%, or greater than 98 wt%. In some embodiments, the at least one fat and / or at least one oil has been purified (prior to blending) by a purification process comprising refining, bleaching and deodorisation (RBD). In such embodiments, the fat and / or at least one oil comprises about 100 wt% oil, or consists of oil, wherein the oil comprises greater than about 95 wt% triacylglycerides, or greater than 97 wt%, or greater than 98 wt%. Such blends comprise TAGs obtainable by the method of processing an oil composition disclosed herein and TAGs from the at least one fat and / or at least one oil. The blend may be subjected to interesterification to interesterify said TAGs. In some such embodiments, interesterification comprises adding a catalyst.

[0160] Suitable fats and / or oils include vegetable fats and oils, medium-chain triglyceride (MCT) oils, oils enriched with long-chain polyunsaturated fatty acids (LC- PUFAs), fish oils, marine oils, microbial oils, interesterified oils, coconut oil, structured lipids, olive oil and oils enriched in omega 6s. For example, vegetable oils may be high oleic canola, palm oil, and / or palm olein. Marine oils are oils from marine animals. Marine oils usually contain high levels of LC-PUFAs, like eicosapentaenoic acid (EP A) and docosahexaenoic acid (DHA). Examples of marine oils include mackerel oil, fish oil and krill oil. Microbial oils are oils produced by microorganisms, such as arachidonic acid-rich single-cell oil (ARASCO) and docosahexaenoic acid-rich singlecell oil (DHASCO). ARASCO contains high levels of arachidonic acid and DHASCO contains high levels of docosahexaenoic acid.

[0161] In some embodiments, the fatty acid ethyl esters can be purified using distillation. For example, a distillate comprising at least 90 wt% FAEEs can be obtained by distillation. The distillate may comprise at least 90 wt% FAEEs, or at least 95 wt%, or at least 99 wt%. In some embodiments, free glycerol is separated from the oil comprising FAEEs using centrifugation in a first purification step, and then distillation is used to obtain a distillate comprising at least 90 wt% or at least 95 wt%, or at least 99 wt% FAEEs.

[0162] Advantageously, it is possible to obtain a purified fraction comprising at least 95 wt% FAEE. In some examples, the purified fraction comprises at least 96.5 wt% FAEE. At this or higher purity, the FAEEs are suitable for use in biodiesel and meet the requirements of the international standard for biodiesel EN14214.

[0163] Products Comprising Processed Oil

[0164] Another aspect of the present invention is to produce products comprising oil obtained via the method of processing an oil composition disclosed herein, such as the oil obtained after hydrolysis or transesterification. For example, food, cosmetic or pharmaceutical products comprising oil obtained via the method of processing an oil composition disclosed herein.

[0165] In some examples, the oil obtained via the method of processing an oil composition disclosed herein may be blended with at least one additional fat and / or at least one additional oil. In some embodiments described herein, an oil comprising monoacylglycerides and / or diacylglycerides is obtained after hydrolysis. The oil obtained in such embodiments may be blended with at least one additional fat and / or at least one additional oil. In some such embodiments, the monoacylglycerides and / or diacylglycerides may act as an emulsifier in the resulting fats and / or oils. Suitable additional fats and / or oils include vegetable fats and oils, medium-chain triglyceride (MCT) oils, oils enriched with long-chain polyunsaturated fatty acids (LC-PUFAs), fish oils, marine oils, microbial oils, interesterified oils, coconut oil, structured lipids, olive oil and oils enriched in omega 6s. For example, vegetable oils may be high oleic canola, palm oil, and / or palm olein. In some such examples of these products, the monoacylglycerides and / or diacylglycerides may act as an emulsifier. Marine oils are oils from marine animals. Marine oils usually contain high levels of LC-PUFAs, like eicosapentaenoic acid (EP A) and docosahexaenoic acid (DHA). Examples of marine oils include mackerel oil, fish oil and krill oil. Microbial oils are oils produced by microorganisms, such as arachidonic acid-rich single-cell oil (ARASCO) and docosahexaenoic acid-rich single-cell oil (DHASCO). ARASCO contains high levels of arachidonic acid and DHASCO contains high levels of docosahexaenoic acid.

[0166] The above embodiments are to be understood as illustrative examples of the invention. It is to be understood that any feature described in relation to any one embodiment may be used alone, or in combination with other features described, and may also be used in combination with one or more features of any other of the embodiments, or any combination of any other of the embodiments. Furthermore, equivalents and modifications not described above may also be employed without departing from the scope of the invention, which is defined in the accompanying claims.

Claims

CLAIMS1. A method of processing an oil composition: wherein the oil composition comprises:40-100 wt% oil;0-20 wt% ethanol;0-25 wt% water; and wherein the oil comprises:95-99 wt% triacylglycerides;1-5 wt% diacylglycerides; and less than 1 wt% monoacylglycerides; and wherein the method comprises:(i) adding water and a base to the oil composition; hydrolysing at least some of the diacylglycerides and / or triacylglycerides to obtain an oil comprising: at least 10 wt% monoacylglycerides; and / or at least 10 wt% diacylglycerides; or(ii) adding ethanol and a base to the oil composition; transesterification of at least some of the monoacylglycerides, diacylglycerides and / or triacylglycerides to obtain an oil comprising: at least 20 wt% fatty acid ethyl esters (FAEE) or(iii) adding water and an enzyme to the oil composition;hydrolysing at least some of the diacylglycerides and / or triacylglycerides to obtain an oil comprising: at least 10 wt% monoacylglycerides; and / or at least 10 wt% diacylglycerides.

2. The method of claim 1, wherein the oil obtained after step (i), (ii) or (iii) further comprises residual triacylglycerides.

3. The method of claim 1 or claim 2, wherein the oil composition is obtained from a plant source.

4. The method of claim 3, wherein the plant source is chickpea, soy or lupin.

5. The method of claim 3 or claim 4, wherein the oil composition is obtained from a plant source through an ethanol extraction process comprising: mixing plantbased flour or flakes with ethanol and separating the oil composition from the flour or flakes.

6. The method of claim 5, wherein the method further comprises generating the flour or flakes from the plant source prior to mixing with ethanol.

7. The method of any preceding claim, wherein the oil composition is purified prior to step (i), (ii) or (iii) to remove one or more impurities including ash, protein, free fatty acids, phospholipids, waxes, carbohydrates, water and / or ethanol.

8. The method of claim 7, wherein the purification includes one or more selected from solvent extraction, oven drying, vacuum drying, distillation, washing, agitation, degumming, deacidification, centrifugation, bleaching, deodorising and / or clarifying.

9. The method of claim 8, wherein the purification comprises: adding water to the oil composition; maintaining the temperature above room temperature with agitation; centrifugation to separate the oil composition and water; adding further water to the oil composition; agitation at room temperature; centrifugation to separate the oil composition and water.

10. The method of any preceding claim, wherein the oil composition is a blended oil composition.

11. The method of claim 10, wherein the blended oil composition comprises a first oil composition and one or more additional oil compositions selected from: vegetable fats, vegetable oils, medium-chain triglyceride (MCT) oils, oils enriched with long-chain polyunsaturated fatty acids (LC-PUFAs), fish oils, marine oils, microbial oils, interesterified oils, coconut oil, structured lipids, olive oil and oils enriched in omega 6s.

12. The method of claim 10 or claim 11, wherein the method comprises step (ii).

13. The method of any preceding claim, wherein the base is selected from KOH, NaOH, sodium methoxide (CHjONa), sodium ethoxide (C^HsONa) and Ca(OH)2.

14. The method of any preceding claim, wherein: the amount of water added in step (i) or (iii) results in a molar ratio of water to oil between 1 : 1 to 9: 1, or wherein the amount of ethanol added in step (ii) results in a molar ratio of ethanol to oil between 3 : 1 to 9: 1.

15. The method of any preceding claim, wherein the method further comprises one or more purification steps after step (i), (ii) or (iii).

16. The method of claim 15, wherein the one or more purification steps is selected from centrifugation, crystallisation and / or distillation.

17. The method of claim 15 or 16, wherein after the one or more purification steps, a purified fraction comprising more than 90 wt% monoacylglycerides is obtained.

18. The method of claim 15 or 16, wherein after the one or more purification steps, a purified fraction comprising more than 90 wt% diacylglycerides is obtained.

19. The method of claim 15 or 16, wherein after the one or more purification steps, a purified fraction comprising more than 90 wt% triacylglycerides is obtained.

20. The method of claim 14 or 15, wherein after the one or more purification steps, a purified fraction comprising more than 90 wt% fatty acid ethyl esters (FAEE) is obtained.

21. An oil obtainable by the method of any of claims 1-16.

22. The method of any of the preceding claims, wherein: the method comprises: step (i) or (iii); and the oil composition is purified prior to step (i) or (iii), said purification comprising refining, bleaching and deodorization (RBD); and / or the oil composition comprises about 100 wt% oil or consists of oil; and the method further comprises blending the oil obtained after step (i) or (iii) with at least one additional fat and / or at least one additional oil.

23. The method according to claim 22, wherein the at least one additional fat and / or at least one additional oil is selected from: vegetable fats, vegetable oils, medium-chain triglyceride (MCT) oils, oils enriched with long-chainpolyunsaturated fatty acids (LC-PUFAs), fish oils, marine oils, microbial oils, interesterified oils, coconut oil, structured lipids, olive oil and oils enriched in omega 6s.

24. The method of any one of claims 17 to 19, wherein: the method comprises step (i) or (iii); and the oil composition is purified prior to step (i) or (iii), said purification comprising refining, bleaching and deodorization (RBD); and / or the oil composition comprises about 100 wt% oil or consists of oil; and the method further comprises blending the purified fraction comprising monoacylglycerides and / or the purified fraction comprising diacylglycerides and / or the purified fraction comprising triacylglycerides with at least one fat and / or at least one oil.

25. The method according to claim 24, wherein the at least one fat and / or at least one oil is selected from: vegetable fats, vegetable oils, medium-chain triglyceride (MCT) oils, oils enriched with long-chain polyunsaturated fatty acids (LC-PUFAs), fish oils, marine oils, microbial oils, interesterified oils, coconut oil, structured lipids, olive oil and oils enriched in omega 6s.

26. A fat or oil obtainable by the method of any of claims 22 to 25.

27. The method of claim 24 or claim 25, further comprising interesterification of the monoacylglycerides, diacylglycerides and / or triacylglycerides from the purified fraction with the triacylglycerides from the at least one fat and / or at least one oil.

28. A food, cosmetic or pharmaceutical product comprising: an oil obtainable by the method of any of claims 1-16; and / ora fat obtainable by the method of any of claims 22 to 25; and / or an oil obtainable by the method of any of claims 22 to 25.

29. Monoacylglycerides and / or diacylglycerides and / or free fatty acids obtainable by the method of any of claims 1-20.

30. An emulsifier comprising monoacylglycerides and / or diacylglycerides obtainable by the method of any of claims 1-20.

31. A food, cosmetic or pharmaceutical product comprising monoacylglycerides and / or diacylglycerides obtainable by the method of any of claims 1-20.

32. Fatty acid ethyl esters obtainable by the method of any of claims 1-16 or 20.

33. A method of making structured lipids comprising interesterification of monoacylglycerides, diacylglycerides, triacylglycerides, free fatty acids and / or fatty acid ethyl esters obtainable by the method of any of claims 1-20.

34. Structured lipids obtainable by the method of claim 27 or claim 33.

35. A food, cosmetic or pharmaceutical product comprising structured lipids obtainable by the method of claim 27 or claim 33.

36. Biodiesel comprising fatty acid ethyl esters (FAEE) obtainable by the method of any of claims 1-16 or 20.

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