A process for producing a vegetable oil composition in which at least 50% of the palmitic acids in the triglycerides of the vegetable oil composition are present at the sn2 position

Abstract

An efficient process is provided for producing a final vegetable oil composition in which at least 50% of the palmitic acids in the triglycerides of the final vegetable oil composition are present at the sn2 position. [Solution] A process is disclosed that includes the steps of providing a starting vegetable oil composition containing palmitic acid in triglycerides, performing an enzymatic interesterification process, and using excess free fatty acids and / or their non-glyceride esters obtained during the process and recycling them back into the process, wherein at least 70% by weight of the total amount of palmitic acid in the starting vegetable oil composition is present in the final vegetable oil composition. Also disclosed are vegetable oil compositions obtainable by the disclosed process, uses of the vegetable oil compositions in the manufacture of infant formula, and infant formulas comprising the vegetable oil compositions.

Description

[Technical Field]

[0001] Technical field of the invention The present invention relates to a process for making a final vegetable oil composition, wherein at least 50% of the palmitic acids in the triglycerides of the final vegetable oil composition are present in the sn2 position. The present invention further relates to vegetable oil compositions, as disclosed herein, wherein at least 50% of the palmitic acids in the triglycerides of the vegetable oil composition are present in the sn2 position, uses of vegetable oil compositions, wherein at least 50% of the palmitic acids in the triglycerides of the vegetable oil composition are present in the sn2 position, obtainable by the process disclosed herein, and to infant formulas comprising a vegetable oil composition, wherein at least 50% of the palmitic acids in the triglycerides of the vegetable oil composition are present in the sn2 position. [Background technology]

[0002] Background of the Invention The "traditional" process for producing a product with a high amount of palmitic acid (P) at the sn2 position, e.g., OPO (where O is oleic acid), is to use certain highly fractionated palm stearins, as disclosed, for example, in EP 1928990 B1, EP 3583857 A1, EP 0209327 B1, and WO 2005 / 036987. The advantage of using hard palm stearins is that this approach ensures a high content of palmitic acid in the starting oil. This, in turn, ensures a higher content of sn2 palmitic acid in the enzymatic interesterification, which is important for obtaining a purer OPO product. The disadvantage is that the hard palm stearins used as starting materials must undergo several processing steps to obtain the desired iodine value (IV) and sn2 palmitic acid content. Therefore, it is not only a labor-intensive and expensive starting material; it is also problematic when it is desired to use a scarce raw material, such as organic palm oil. When a scarce raw material, such as organic palm oil, is used, it is desirable to utilize as much palmitic acid as possible in the starting material. When fractionating hard palm stearin, the desired triglyceride is PPP. That is, all triglycerides present as POP and POO are undesirable and therefore are largely removed. All palmitic acid present in these triglycerides is lost, thus resulting in suboptimal utilization of palmitic acid in the starting material.

[0003] Therefore, a primary object of the present invention is to provide an efficient and alternative approach to producing vegetable oil compositions in which a high amount of palmitic acid is present at the sn2 position.

[0004] Another object of the present invention is to provide a method for utilizing as much palmitic acid as possible in the starting material. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] EP1928990 B1 [Patent Document 2] EP3583857 A1 [Patent Document 3] EP0209327B1 [Patent Document 4] WO2005 / 036987 Summary of the Invention

[0006] The present invention relates to a process for making a final vegetable oil composition in which at least 50% of the palmitic acid in the triglycerides of the final vegetable oil composition is present in the sn2 position, the process comprising the steps of providing a starting vegetable oil composition comprising palmitic acid in triglycerides, performing an enzymatic interesterification process, and using excess free fatty acids and / or non-glyceride esters obtained during the process and recycling them back into the process, wherein at least 70% by weight of the total amount of palmitic acid in the starting vegetable oil composition is present in the final vegetable oil composition.

[0007] This process makes it possible to obtain a vegetable oil composition in which a large amount of palmitic acid is present at the sn2 position out of the total palmitic acid in the triglycerides of the vegetable oil composition.

[0008] The present process efficiently utilizes palmitic acid in the starting oil composition, which is particularly advantageous when the starting oil composition is one that is in limited supply, such as organic palm oil. Thus, the present process takes into account limited supply and price. In the present process, at least 70 wt. % of the total amount of palmitic acid in the starting vegetable oil composition is present in the final vegetable oil composition.

[0009] The present invention also relates to a vegetable oil composition obtainable by the process according to the present invention, wherein at least 50% of the palmitic acids in the triglycerides of the vegetable oil composition are present in the sn2 position.

[0010] The present invention further relates to the use of a vegetable oil composition according to the present invention, wherein at least 50% of the palmitic acids in the triglycerides of the vegetable oil composition are present at the sn2 position, in the manufacture of infant formula or plant-based food. Plant-based food is intended to mean a food based primarily on plant-derived ingredients. The presence of trace amounts of non-plant-derived ingredients is permitted. In one embodiment, the plant-based food is made entirely from plant-derived ingredients and therefore does not contain animal-derived ingredients. An example of a plant-based food is a milk-free infant food.

[0011] The present invention also includes an infant formula comprising 15% to 100% by weight of a vegetable oil composition according to the present invention, in which at least 50% of the palmitic acids in the triglycerides of the vegetable oil composition are present at the sn2 position. [The present invention 1001] 1. A process for producing a final vegetable oil composition in which at least 50% of the palmitic acid in the triglycerides of the final vegetable oil composition is present in the sn2 position, the process comprising the steps of providing a starting vegetable oil composition comprising palmitic acid in triglycerides, performing an enzymatic interesterification process, and using excess free fatty acids and / or their non-glyceride esters obtained during the process and recycling them back into the process, wherein at least 70% by weight of the total amount of palmitic acid in the starting vegetable oil composition is present in the final vegetable oil composition. [The present invention 1002] (I) carrying out a hydrolysis or alcoholysis process and further carrying out distillation, thereby obtaining at least a palmitic acid-rich fraction; (II) carrying out esterification of glycerol with the palmitic acid-rich fraction to obtain a vegetable oil enriched in at least PPP TAGs; (III) subjecting the PPP TAG-rich vegetable oil to an enzymatic interesterification process with a fatty acid composition, thereby obtaining a crude vegetable oil blend; (IV) separating the crude vegetable oil blend to obtain a mixture of excess free fatty acids and / or their non-glyceride esters and the final vegetable oil composition in which palmitic acid is present in the sn2 position; (V) using the excess mixture of free fatty acids and / or their non-glyceride esters obtained during the process and recycling it back into the process. The process of the present invention 1001 further comprises: [The present invention 1003] The process of claim 1002, wherein the fatty acid composition of step (III) is a fatty acid composition enriched in C18 fatty acids and / or their non-glyceride esters. [The present invention 1004] Step (I) (Ia) subjecting the starting vegetable oil composition to a hydrolysis or alcoholysis process to obtain glycerol and free fatty acids and / or their non-glyceride esters; (Ib) separating the free fatty acids and / or non-glyceride esters thereof from the glycerol and water / alcohol to obtain a mixture of free fatty acids and / or non-glyceride esters thereof; (Ic) subjecting the mixture of free fatty acids and / or their non-glyceride esters to a distillation process to obtain a C18 fatty acid-rich fraction and a palmitic acid-rich fraction. The process of the present invention 1002 or 1003, comprising: [The present invention 1005] Step (III) (IIIa) subjecting the PPP TAG-rich vegetable oil obtained in step (II) to a distillation and / or neutralization process to remove excess free fatty acids and / or their non-glyceride esters, thereby obtaining a vegetable oil composition in which 63% to 97% by weight of the total triglycerides are tripalmitin TAG; (IIIb) mixing the obtained vegetable oil composition, in which 63% by weight to 97% by weight of the total triglycerides are tripalmitin TAG, with a fatty acid composition rich in C18 fatty acids and / or their non-glyceride esters to obtain a first mixture; (IIIc) subjecting the first mixture from step (IIIb) to an enzymatic interesterification process using one or more 1,3-specific enzymes, thereby obtaining a crude vegetable oil blend. Any of the processes 1002 to 1004 of the present invention, comprising: [The present invention 1006] Any of the aforementioned processes of the present invention, wherein the starting vegetable oil composition comprises 80% or less by weight of palmitic acid in triglycerides compared to the total weight of fatty acids in triglycerides. [The present invention 1007] 1006. The process of any of claims 1004 to 1006, wherein the step of using excess free fatty acids and / or non-glyceride esters thereof obtained during the process and recycling them back into the process comprises using the mixture of excess free fatty acids and / or non-glyceride esters thereof obtained from step (IV) and feeding them into the mixture of step (Ic). [The present invention 1008] Any of the processes of claims 1002 to 1007, further comprising the step of dividing the mixture of excess free fatty acids and / or their non-glyceride esters from step (IV) by a distillation process, thereby obtaining a palmitic acid (P, C16:0)-rich fraction and a C18 fatty acid-rich fraction, and using at least a portion of the palmitic acid-rich fraction in step (II). [The present invention 1009] The process of claim 1008, further comprising a distillation process for said C18 fatty acid-rich fraction and using at least a portion of said C18 fatty acid-rich fraction in step (IIIb). [The present invention 1010] 1009. The process of any of claims 1005 to 1009, wherein the C18 fatty acid enriched fraction from step (Ic) is used in step (IIIb). [The present invention 1011] The process of any of claims 1004 to 1010, further comprising the steps of separating the glycerol and water / alcohol from step (Ib) and using the glycerol obtained in said step in the esterification step (II). [The present invention 1012] The process of any of claims 1005 to 1011, further comprising the step of using excess free fatty acids and / or non-glyceride esters thereof obtained from step (IIIa) and feeding them to an esterification step (II). [The present invention 1013] Any of the preceding processes of the present invention, wherein no chemical catalyst is used in any of the process steps. [The present invention 1014] Any of the above-described processes of the present invention, wherein the starting vegetable oil composition has an iodine value of at least 15, such as at least 20, for example at least 25, such as at least 30, for example at least 35, such as at least 40, for example at least 45, such as at least 50, for example at least 55, or such as at least 60. [The present invention 1015] A vegetable oil composition obtainable by any of the processes of the present invention, wherein at least 50% of the palmitic acids in the triglycerides of the vegetable oil composition are present at the sn2 position. [The present invention 1016] Use of a vegetable oil composition of the present invention 1015, in which at least 50% of the palmitic acid in the triglycerides of the vegetable oil composition is present at the sn2 position, in the production of infant formula or plant-based food. [The present invention 1017] An infant formula comprising 15% to 100% by weight of a vegetable oil composition in which at least 50% of palmitic acid out of all palmitic acids in the triglycerides of the vegetable oil composition is present at the sn2 position. [Brief explanation of the drawings]

[0012] [Figure 1] 1 shows TAG production over time using the PPP of Example 2. [Figure 2] 1 shows TAG production over time using the PPP of Example 3. [Figure 3] 1 shows TAG production over time using POST IV 13 from Example 4. [Figure 4]1 shows a flowchart of a process according to one aspect of the present disclosure. [Figure 5] 1 shows a flowchart of a process according to one aspect of the present disclosure. DETAILED DESCRIPTION OF THE INVENTION

[0013] definition Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. Terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the relevant art, and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.

[0014] As used herein, the term "vegetable" is understood to be derived from a plant or a single-cell organism. Thus, a vegetable oil or vegetable triglyceride should be understood as a vegetable oil or vegetable triglyceride even if all fatty acids used to obtain the triglyceride or oil are derived from a plant or a single-cell organism.

[0015] Saturated fatty acids are chains of carbon atoms connected by single bonds, with the maximum number of hydrogen atoms attached to each carbon atom in the chain. Unsaturated fatty acids are chains of carbon atoms connected by single bonds and a variable number of double bonds, with incompletely attached hydrogen atoms. Unsaturated fatty acids can exist in two forms: cis and trans. The double bond can have one of two possible configurations: trans or cis. In the trans configuration (trans fatty acids), the carbon chain extends from opposite sides of the double bond, while in the cis configuration (cis fatty acids), the carbon chain extends from the same side of the double bond.

[0016] Use of the nomenclature CX means that the fatty acid contains X carbon atoms, for example, a C14 fatty acid has 14 carbon atoms and a C8 fatty acid has 8 carbon atoms.

[0017] The use of the nomenclature CX:Y means that the fatty acid contains X carbon atoms and Y double bonds, for example, a C14:0 fatty acid has 14 carbon atoms and 0 double bonds, and a C18:1 fatty acid has 18 carbon atoms and 1 double bond.

[0018] As used herein, "C18" includes C18:0, which is stearic acid (St), C18:1, which is oleic acid (O), C18:2, which is linoleic acid (Li or L), and C18:3, which is linolenic acid (Ln). Thus, "fatty acid compositions rich in C18 fatty acids and / or their non-glyceride esters" and "fractions rich in C18 fatty acids" also include one or more of stearic acid, oleic acid, linoleic acid, and linolenic acid.

[0019] A palmitic acid (C16:0) enriched fraction means that at least 85% by weight of the fraction is palmitic acid.

[0020] By C18 enriched fraction it is meant that at least 70% by weight of the fraction is C18.

[0021] Fractional distillation refers to the separation of fatty acids based on their boiling points. For a detailed description of fractional distillation, see Steven C. Cermak, Roque L. Evangelista and James A. Kenar (2012). Distillation of Natural Fatty Acids and Their Chemical Derivatives, Distillation - Advances from modeling to Applications, Dr. Sina Zereshki (Ed.), ISBN: 978-953-51-0428-5.

[0022] As used herein, "%" or "percentage" relates to weight percentage, i.e., wt% or wt.-%, unless otherwise indicated.

[0023] As used herein, "oil" and "fat" are used interchangeably unless otherwise specified.

[0024] As used herein, "vegetable oil" and "vegetable fat" are used interchangeably unless otherwise specified.

[0025] As used herein, the term "single-cell oil" refers to oil derived from oleaginous microorganisms, which are species of yeast, mold (fungi), bacteria, and microalgae. These single-cell oils are produced intracellularly, mostly in the stationary growth phase, under specific growth conditions (e.g., nitrogen-limiting conditions with an excess of carbon sources). Examples of oleaginous microorganisms include, but are not limited to, Mortierella alpineea, Yarrowia lipolytica, Schizochytrium, Nannochloropsis, Chlorella, Crypthecodinium cohnii, and Shewanella.

[0026] Food is a product intended for human consumption.

[0027] Plant-based food refers to food that is primarily based on plant-derived ingredients. Trace amounts of non-plant-derived ingredients are permitted. In one embodiment, the plant-based food is made entirely from plant-derived ingredients and therefore does not contain animal-derived ingredients. An example of a plant-based food is milk-free infant food.

[0028] As used herein, triglyceride composition, oil, or fat refer to the same thing, and it should be understood that the majority of the composition is triglycerides, although other acylglycerols such as monoglycerides and diglycerides may be present.

[0029] The terms "comprising," "to comprise," or "contains" should be interpreted as specifying the presence of stated parts, steps, features, or ingredients, but not excluding the presence of one or more additional parts, steps, features, or ingredients.

[0030] As used herein, the term "and / or" shall mean inclusive ("and") and exclusive ("or"), i.e., "A and / or B" shall mean "A only, or B only, or both A and B."

[0031] Detailed Description of the Invention A description herein of an aspect or embodiment of the invention using terms such as "comprising," "having," "including," or "containing" in reference to an element is intended to provide support for similar aspects or embodiments of the invention that "consist," "consist essentially of," or "substantially comprise" that particular element, unless otherwise stated or clearly contradicted by context; for example, a composition described herein as comprising a particular element should be understood to also describe a composition consisting of that element, unless otherwise stated or clearly contradicted by context. It will be further understood that the terms "comprises," "comprising," "includes," and / or "including," as used herein, specify the presence of stated features, integers, steps, operations, elements, and / or components, but do not exclude the presence or addition of one or more other features, integers, steps, operations, elements, components, and / or groups thereof.

[0032] Any and all examples provided herein, or the use of exemplary language (e.g., "such as"), are intended merely to further clarify the invention and do not limit the scope of the invention unless otherwise recited in the claims. No language in the specification should be construed as indicating any non-claimed element as essential to the practice of the invention.

[0033] The present invention relates to a process for making a final vegetable oil composition in which at least 50% of the palmitic acid in the triglycerides of the final vegetable oil composition is present in the sn2 position, the process comprising the steps of providing a starting vegetable oil composition comprising palmitic acid in triglycerides, carrying out an enzymatic interesterification process, and using excess free fatty acids and / or their non-glyceride esters obtained during the process and recycling them back into the process, wherein at least 70% by weight of the total amount of palmitic acid in the starting vegetable oil composition is present in the final vegetable oil composition.

[0034] Generally, triglycerides use the "sn" designation, which stands for stereospecific numbering. In the Fischer projection of natural L-glycerol derivatives, the secondary hydroxyl group is shown to the left of C-2; the carbon atom above that is then C-1, and the carbon atom below is C-3. The prefix "sn" is placed before the stem name of the compound.

[0035] sn1 / sn2 / sn3: TIFF2026012865000002.tif34128

[0036] The process results in an increase in the sn2 palmitic acid compared to the starting vegetable oil composition, i.e., the content of palmitic acid at the sn2 position (the middle position of the triglyceride) in the triglycerides of the final vegetable oil composition is increased when compared to the content of palmitic acid at the same position in the starting vegetable oil composition.

[0037] In one or more embodiments, the process can be run several times (e.g., 4, 5, 6, 7, or 8 cycles) so that the excess free fatty acids and / or non-glyceride esters thereof obtained during the process can be recycled back into the process several times, i.e., excess free fatty acids and / or non-glyceride esters thereof obtained during a previous run are used in a current run, thereby providing new excess free fatty acids and / or non-glyceride esters thereof for use in a next run, and so on.

[0038] By using the excess free fatty acids and / or their non-glyceride esters obtained during the process and recycling them back into the process, at least any unreacted palmitic acid remaining from one process cycle can be reused in the same process starting with a new amount of starting vegetable oil composition. That is, the palmitic acid-rich fraction obtained in a previous run is used in a current run, thereby providing a new palmitic acid-rich fraction for use in the next run, and so on. Thus, although palmitic acid is found in nature as a limited source, the present process ensures that the amount of palmitic acid wasted during the process is minimized, as the excess palmitic acid continues to be recycled into the process.

[0039] In one or more embodiments, the fatty acid non-glyceride esters are selected from methyl esters, ethyl esters, or combinations thereof.

[0040] In one or more embodiments, the process further comprises the steps of: (I) carrying out a hydrolysis or alcoholysis process and further carrying out distillation, thereby obtaining at least a palmitic acid-rich fraction; (II) carrying out esterification of glycerol with the palmitic acid-rich fraction to obtain a vegetable oil enriched in at least PPP TAGs; (III) subjecting the PPP TAG-rich vegetable oil to an enzymatic interesterification process with a fatty acid composition, thereby obtaining a crude vegetable oil blend; (IV) separating the crude vegetable oil blend to obtain a mixture of excess free fatty acids and / or their non-glyceride esters and a final vegetable oil composition in which palmitic acid is present in the sn2 position; (V) Using the excess mixture of free fatty acids and / or their non-glyceride esters obtained during the process and recycling it back into the process.

[0041] In one or more embodiments, the fatty acid composition of step (III) is a fatty acid composition enriched in C18 fatty acids and / or their non-glyceride esters.

[0042] In one or more embodiments, step (I) comprises the following steps: (Ia) subjecting the starting vegetable oil composition to a hydrolysis or alcoholysis process to obtain glycerol and free fatty acids and / or their non-glyceride esters; (Ib) separating the free fatty acids and / or their non-glyceride esters from the glycerol and water / alcohol to obtain a mixture of free fatty acids and / or their non-glyceride esters; (Ic) subjecting the mixture of free fatty acids and / or their non-glyceride esters to a distillation process to obtain a fraction rich in C18 fatty acids and a fraction rich in palmitic acid.

[0043] Glycerol and water / alcohol means glycerol and water if a hydrolysis process is carried out in step (Ia), and glycerol and alcohol if an alcoholysis process is carried out in step (Ia).

[0044] In one or more embodiments, the hydrolysis in step (Ia) can be carried out at high pressure and high temperature in a countercurrent reactor. Oil is fed near the bottom of the reactor, and water is fed near the top of the reactor. Due to the difference in density, water is transported downward in the reactor, while oil tends to move upward. Hydrolysis occurs during contact between the water phase and the oil phase, forming fatty acids and glycerol. Glycerol is discharged from the bottom of the reactor along with excess water, and fatty acids are discharged from the top of the reactor. The glycerol can be reused in the process after the water is removed. After the hydrolysis step, the hydrolyzed fatty acids can be purified by distillation.

[0045] In one or more embodiments, the esterification in step (II) comprises the following steps: (a) blending glycerol with a palmitic acid-rich fraction to obtain a blend; (b) heating the admixture under reduced pressure for a predetermined period of time; (c) heating the admixture to a further increased temperature for a predetermined period of time as compared to step (b), while simultaneously further reducing the pressure; (d) maintaining the admixture at the temperature and pressure of step (c) for a predetermined period of time.

[0046] In one or more embodiments of the esterification in step (II), steps (b) and (c) are combined into one step by continuously heating the mixed admixture of glycerol and fatty acids to a desired temperature under reduced pressure for a predetermined period of time.

[0047] In one or more embodiments of the esterification in step (II), step (c) comprises two steps: (c1) reducing the pressure compared to step (b) for a predetermined period of time, and (c2) increasing the temperature under the reduced pressure of step (c1) for a predetermined period of time.

[0048] In one or more embodiments of the esterification in step (II), step (c1) and step (c2) are carried out sequentially in that order.

[0049] In one or more embodiments of the esterification in step (II), steps (c1) and (c2) are reversed.

[0050] In one or more embodiments of the esterification in step (II), the glycerol and palmitic acid-rich fraction of step (a) are mixed in a ratio of 1:3.125 or up to 1:10 (moles of glycerol:moles of free fatty acids and / or their non-glyceride esters) to obtain a blend.

[0051] In one or more embodiments of the esterification in step (II), the step of combining glycerol with the palmitic acid-rich fraction to obtain an admixture (step (a)) is carried out in a vessel. The vessel can be any vessel suitable for carrying out a chemical reaction. Such a vessel can be, for example, but is not limited to, a flask, a tank, a tube, a laboratory flask, a round-bottom flask, a three-neck flask, a two-neck flask, a single-neck flask, a glass flask, or a metal flask. The reaction can be carried out with or without agitation, such as stirring.

[0052] In one or more embodiments of the esterification in step (II), a condenser is used. The condenser is heated to a temperature of 40°C to 150°C, for example, 50°C to 90°C, or for example, 65°C to 90°C. This temperature of the condenser depends on the size and surface area of ​​the condenser, and it is important to use a temperature at which the water evaporates and most of the glycerol condenses to avoid excessive loss of glycerol. Methods for adjusting this will be known to those skilled in the art.

[0053] In one or more embodiments of the esterification in step (II), the admixture is heated in step (b) to a temperature in the range of 140° C. to 180° C. In one or more embodiments of the process, the admixture is heated in step (b) to a temperature in the range of 160° C. to 170° C.

[0054] In one or more embodiments of the esterification in step (II), the reduced pressure in step (b) is in the range of 150 mbar to 400 mbar, for example in the range of 175 mbar to 250 mbar.

[0055] In one or more embodiments of the esterification in step (II), the predetermined period of time in step (b) is in the range of 15 minutes to 5 hours, for example in the range of 30 minutes to 4 hours.

[0056] In one or more embodiments of the esterification in step (II), the predetermined period of time in step (b) is at least 15 minutes, such as at least 20 minutes, for example at least 30 minutes, such as at least 1 hour, for example at least 2 hours, such as at least 3 hours.

[0057] In one or more embodiments of the esterification in step (II), the temperature in step (c) is in the range of 180°C to 250°C, for example in the range of 210°C to 230°C.

[0058] In one or more embodiments of the esterification in step (II), the admixture in step (c) is heated to at least 160°C.

[0059] In one or more embodiments of the esterification in step (II), the admixture in step (c) is heated to a maximum of 230° C. In one or more embodiments, the admixture in step (c) is heated to a maximum of 240° C.

[0060] The temperature is gradually increased when proceeding from step (b) to step (c). In one or more embodiments, the temperature is increased from about 170° C. in step (b) to about 210° C. in step (c).

[0061] In one or more embodiments of the esterification in step (II), the pressure in step (c) is in the range of 10 mbar to 400 mbar, such as in the range of 20 mbar to 250 mbar, for example in the range of 30 mbar to 150 mbar, such as in the range of 30 mbar to 90 mbar, or such as in the range of 30 mbar to 40 mbar.

[0062] The pressure is gradually reduced when proceeding from step (b) to step (c). In one or more embodiments, the pressure is reduced from about 200 mbar in step (b) to about 30 mbar in step (c).

[0063] In one or more embodiments of the esterification in step (II), the predetermined period of time in step (c) is in the range of 15 minutes to 5 hours, for example in the range of 30 minutes to 4 hours.

[0064] In one or more embodiments of the esterification in step (II), the predetermined period of time in step (c) is at least 15 minutes, such as at least 20 minutes, such as at least 30 minutes, such as at least 1 hour, or such as at least 2 hours.

[0065] In one or more embodiments of the esterification in step (II), a catalyst is added in step (a). The catalyst can be any catalyst known to be useful in esterification processes. In one or more embodiments, the catalyst is an organic catalyst. In one or more embodiments, zinc oxide is used as a catalyst. Thus, in one or more embodiments of this process, zinc oxide (ZnO) is added as a catalyst in step (a). As known to those skilled in the art, the predetermined time in step (d) will be reduced if a catalyst is used.

[0066] In one or more embodiments, step (III) comprises the steps of: (IIIa) subjecting the PPP TAG-rich vegetable oil obtained in step (II) to a distillation and / or neutralization process to remove excess free fatty acids and / or their non-glyceride esters, thereby obtaining a vegetable oil composition in which 63% to 97% by weight of the total triglycerides are tripalmitin TAG; (IIIb) mixing the obtained vegetable oil composition, in which 63% by weight to 97% by weight of the total triglycerides are tripalmitin TAG, with a fatty acid composition rich in C18 fatty acids and / or their non-glyceride esters to obtain a first mixture; (IIIc) subjecting the first mixture from step (IIIb) to an enzymatic interesterification process using one or more 1,3-specific enzymes, thereby obtaining a crude vegetable oil blend.

[0067] In one or more embodiments, the distillation in step (IIIa) is physical scouring. In one or more embodiments, the distillation is carried out at a temperature of at least 160°C, optionally under reduced pressure. In one or more embodiments, the distillation is carried out at a temperature of at least 190°C under reduced pressure. In one or more embodiments, the distillation is carried out at a temperature of 220°C to 260°C under reduced pressure, for example, at about 240°C under reduced pressure. This is standard condition for distillation processes known to those skilled in the art. In one embodiment, chemical scouring can be used instead of physical scouring, in which case the temperature change to about 100°C would be known to those skilled in the art.

[0068] In one or more embodiments, the one or more 1,3-specific enzymes can be 1,3-specific lipases (i.e., lipases specific for sn1 and sn3 positions), which reduce the content of palmitic acid at the outer positions of triglycerides, thereby increasing the ratio of palmitic acid at the sn2 position to the total palmitic acid content in triglycerides.

[0069] In one or more embodiments, using the excess free fatty acids and / or non-glyceride esters thereof obtained during the process and recycling them back into the process comprises using the mixture of excess free fatty acids and / or non-glyceride esters thereof obtained from step (IV) and feeding them to the mixture of step (Ic).

[0070] In one or more embodiments, the process further comprises dividing the mixture of excess free fatty acids and / or their non-glyceride esters from step (IV) by a distillation process, thereby obtaining a palmitic acid (P, C16:0)-rich fraction and a C18 fatty acid-rich fraction, and using at least a portion of the palmitic acid-rich fraction in step (II).

[0071] By recovering the mixture of excess free fatty acids and / or their non-glyceride esters and separating them by a distillation process, thereby obtaining a palmitic acid (P, C16:0)-rich fraction and a C18 fatty acid-rich fraction, at least the unreacted palmitic acid remaining from the process can be reused in a process starting with a new amount of starting vegetable oil composition. This allows the palmitic acid-rich fraction obtained in a previous run to be used in the current run, thereby obtaining a new palmitic acid-rich fraction for use in the next run, and so on. That is, although palmitic acid is found in nature as a limited source, the present process continues to reuse the excess palmitic acid back into the process, ensuring that the amount of palmitic acid wasted during the process is minimized.

[0072] In one or more embodiments, the process further comprises a distillation process of the fraction enriched in C18 fatty acids, and using at least a portion of the fraction enriched in C18 fatty acids in step (IIIb).

[0073] In one or more embodiments, the C18 fatty acid-rich fraction from step (Ic) is used in step (IIIb). Thus, in one or more embodiments, all of the obtained fraction is reused in the process, so there are no unused fractions.

[0074] When the starting vegetable oil composition is split, palmitic acid is the primary product, but the resulting C18 fatty acids and glycerol are also, in one or more embodiments, refined and fed back into the process, thereby creating an efficient process from a raw material standpoint while preserving the origin of the starting oil composition.

[0075] In one or more embodiments, the process further comprises separating the glycerol and water / alcohol from step (Ib) and using the glycerol obtained in said step in the esterification step (II).

[0076] In one or more embodiments, the process further comprises using excess free fatty acids and / or non-glyceride esters thereof obtained from step (IIIa) and further feeding them to the esterification step (II).

[0077] In one or more embodiments, the process further comprises bleaching and / or neutralizing the product obtained in the distillation and / or neutralization process of step (IIIa).

[0078] In one or more embodiments, the process further comprises bleaching and / or neutralizing and / or deodorizing the final vegetable oil composition obtained from the separation of step (IV).

[0079] In one or more embodiments, the vegetable oil composition obtained after step (IIIa) has between 70% and 97% tripalmitin TAG by weight of total triglycerides, e.g., between 85% and 97% tripalmitin TAG by weight of total triglycerides.

[0080] In one or more embodiments, the proportion of palmitic acid at the sn2 position in the triglycerides of the vegetable oil composition obtained after step (IIIa) is in the range of 85% to 99%.

[0081] In one or more embodiments, the vegetable oil composition obtained after step (IIIa) has an amount of diglycerides and / or monoglycerides of 6% or less, such as 3% or less, or such as 2% or less, relative to the total weight of the vegetable oil composition. In one or more embodiments, the vegetable oil composition obtained after step (IIIa) has an amount of diglycerides and / or monoglycerides in the range of 0% to 6% relative to the total weight of the vegetable oil composition, such as in the range of 0.5% to 5% relative to the total weight of the vegetable oil composition, such as in the range of 0.5% to 4%, such as in the range of 0.5% to 3%, such as in the range of 0.5% to 3%, or such as in the range of 0.5% to 2%.

[0082] In one or more embodiments, the proportion of sn2 palmitic acid in the total palmitic acid in the triglycerides of the final vegetable oil composition is 52% or more, such as 55% or more, such as 60% or more, or such as 70% or more. In one or more embodiments, the proportion of sn2 palmitic acid in the total palmitic acid in the triglycerides of the final vegetable oil composition is in the range of 52% to 80%, such as in the range of 52% to 75%, such as in the range of 52% to 70%, or such as in the range of 55% to 70%.

[0083] In one or more embodiments, the final vegetable oil composition comprises 30% to 60% by weight, such as 30% to 50% by weight, such as 35% to 45% by weight, or such as 40% to 45% by weight, of palmitic acid in triglycerides relative to the total weight of fatty acids in the triglycerides in the final vegetable oil composition. In one or more embodiments, the final vegetable oil composition comprises at least 30% by weight, such as at least 35% by weight, or such as at least 40% by weight, of palmitic acid in triglycerides relative to the total weight of fatty acids in the triglycerides in the final vegetable oil composition.

[0084] In one or more embodiments, the ratio of oleic acid to linoleic acid (oleic acid:linoleic acid) in the triglycerides of the final vegetable oil composition is in the range of 10:1 to 1:2, such as in the range of 5:1 to 1:1.

[0085] In one or more embodiments, 40% or more of the triglycerides in the final vegetable oil composition are of the OPO, OPL, and / or LPL type.

[0086] In one or more embodiments, 40% or more of the triglycerides in the final vegetable oil composition are of the OPO type.

[0087] In one or more embodiments, at least 75% by weight of the total amount of palmitic acid in the starting vegetable oil composition is present in the final vegetable oil composition, e.g., at least 80% by weight, such as at least 90% by weight, or such as at least 95% by weight of the total amount of palmitic acid in the starting vegetable oil composition is present in the final vegetable oil composition.

[0088] In one or more embodiments, no chemical catalysts are used in any of the steps of the process. By avoiding the use of chemical catalysts, the process is simpler and, if an organic starting vegetable oil composition is used, the final vegetable oil composition can remain organic.

[0089] In one or more embodiments, the enzymes used are non-genetically modified enzymes, which are enzymes made without the use of genetically modified organism (GMO) technology.

[0090] In one or more embodiments, no organic solvents are used in any of the steps of the process.

[0091] The process, which does not use chemical catalysts and non-GMO-produced enzymes (e.g., lipases) in any of the steps, and furthermore does not use organic solvents, should help ensure that the final vegetable oil composition, when starting from an organically certified starting oil composition, is made under organic rules and regulations, thus making the final product organically certified.

[0092] In one or more embodiments, the starting vegetable oil composition comprises 80% or less by weight of palmitic acid in triglycerides compared to the total weight of fatty acids in the triglycerides.

[0093] In one or more embodiments, the starting vegetable oil composition comprises at least 9% palmitic acid in triglycerides relative to the total weight of fatty acids in the triglycerides, such as at least 15%, for example at least 25%, for example at least 35%, such as at least 40%, for example at least 50%, or such as at least 60% palmitic acid.

[0094] In one or more embodiments, the starting vegetable oil composition comprises palmitic acid in triglycerides in the range of 9% to 80%, such as in the range of 15% to 80%, for example in the range of 20% to 80%, such as in the range of 30% to 80%, for example in the range of 30% to 75%, or such as in the range of 30% to 70%, relative to the total weight of fatty acids in the triglycerides.

[0095] In one or more embodiments, the starting vegetable oil composition has an iodine value of at least 15, such as at least 20, for example at least 25, such as at least 30, for example at least 35, such as at least 40, for example at least 45, such as at least 50, for example at least 55, or such as at least 60.

[0096] In one or more embodiments, the starting vegetable oil composition has an iodine value of at least 70, such as at least 80, such as at least 90, such as at least 100, such as at least 110, such as at least 120, or such as at least 130.

[0097] In one or more embodiments, the starting vegetable oil composition has an iodine value of 140 or less, such as 130 or less, such as 120 or less, or such as 110 or less.

[0098] In one or more embodiments, the starting vegetable oil composition has an iodine value of 100 or less, such as 90 or less, such as 80 or less, or such as 70 or less.

[0099] In one or more embodiments, the starting vegetable oil composition has an iodine value in the range of 15-140, such as in the range of 30-70, or such as in the range of 30-55.

[0100] Since palmitic acid is a rare source material, especially when organic variants are required, it would be highly advantageous to start with a starting oil with a lower palmitic acid content than, for example, palm stearin, which has a low iodine value of 12. This would result in a more economical process. Previous teachings have shown that to produce vegetable fats with a high content of sn2 palmitic acid, the starting material for the process should be selected as hard as possible from palm stearin (e.g., palm stearin with a low iodine value (less than 12)), since this equates to more palmitic acid, especially more sn2 palmitic acid, in the starting composition. In contrast, the present invention allows for the creation of a balanced process for producing vegetable oil compositions with a high content of sn2 palmitic acid, even when starting from other starting materials, such as palm fractions with a higher iodine value.

[0101] In one embodiment, the process disclosed herein begins with, as a starting oil, a palm fraction having an iodine value of at least 15. The palm fraction is then converted into a highly pure vegetable oil rich in PPP TAGs.

[0102] The process is therefore a more efficient process that allows for the use of cheaper, less processed starting materials while still achieving a high yield and purity of the final product.

[0103] Because organic palm oil is not widely available, palmitic acid is a scarce raw material, especially if it is to be an organic variant, but the present process makes it possible to utilize almost all of the palmitic acid present in the starting oil, with almost no palmitic acid being wasted during the process.

[0104] In one or more embodiments, the starting vegetable oil composition is derived from one of the following sources: palm oil or a fraction or derivative thereof, palm kernel oil, corn oil, single stage dry fractionated palm stearin, rice bran oil, peanut oil, coconut oil, soybean oil, cotton oil, or a combination thereof.

[0105] In one or more embodiments, the starting vegetable oil composition is certified organic.

[0106] In one or more embodiments, the starting plant oil composition is not derived from a unicellular organism.

[0107] In one or more embodiments, the excess free fatty acid and / or non-glyceride ester thereof is excess free fatty acid.

[0108] 4 and 5 show a flow chart of one embodiment of the process disclosed herein.

[0109] Also disclosed herein is a process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAGs) are tripalmitic (PPP) TAGs, wherein the process utilizes at least 70% of the palmitic acid (P, C16:0) present in the starting vegetable oil composition, and the process comprises: providing a starting vegetable oil composition comprising 80% or less palmitic acid triglycerides relative to the total weight of fatty acids in the triglycerides; subjecting the starting vegetable oil composition to a hydrolysis or alcoholysis process to obtain glycerol and free fatty acids and / or their non-glyceride esters; - separating the free fatty acids and / or their non-glyceride esters from the glycerol and water / alcohol to obtain a mixture of free fatty acids and / or their non-glyceride esters; subjecting the mixture of free fatty acids and / or their non-glyceride esters to a distillation process to obtain a C18 fatty acid-rich fraction and a palmitic acid-rich fraction; esterifying glycerol with the palmitic acid-rich fraction from the previous step to obtain a mixture of excess free fatty acids and / or their non-glyceride esters and a vegetable oil enriched in PPP TAGs; The PPP TAG-rich vegetable oil obtained in the previous step is subjected to a distillation and / or neutralization process to remove excess free fatty acids and / or their non-glyceride esters. thereby obtaining a vegetable oil composition in which 63% to 97% by weight of the total triglycerides are tripalmitin TAG.

[0110] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAGs) are tripalmitin (PPP) TAGs, no chemical catalyst is used in any of the steps of the process.

[0111] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAGs) are tripalmitic (PPP) TAGs, the process utilizes at least 75% of the palmitic acid present in the starting vegetable oil composition, such as at least 80%, such as at least 85%, or such as at least 90% of the palmitic acid present in the starting vegetable oil composition.

[0112] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAGs) are tripalmitin (PPP) TAGs, the esterification comprises the following steps: (a) blending glycerol with a palmitic acid-rich fraction to obtain a blend; (b) heating the admixture under reduced pressure for a predetermined period of time; (c) further increasing the temperature and heating the admixture for a predetermined period of time compared to step (b), while simultaneously further reducing the pressure; (d) maintaining the admixture at the temperature and pressure of step (c) for a predetermined period of time.

[0113] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAGs) are tripalmitin (PPP) TAGs, the esterification comprises combining steps (b) and (c) into one step by continuously heating the combined admixture of glycerol and fatty acids to a desired temperature under reduced pressure for a predetermined period of time.

[0114] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAGs) are tripalmitin (PPP) TAGs, the esterification includes step (c) comprising two steps: (c1) reducing the pressure compared to step (b) for a predetermined period of time; and (c2) increasing the temperature under the reduced pressure of step (c1) for a predetermined period of time.

[0115] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAGs) are tripalmitin (PPP) TAGs, the esterification comprises steps (c1) and (c2) being performed sequentially in that order. In one or more embodiments, steps (c1) and (c2) are reversed.

[0116] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAGs) are tripalmitic (PPP) TAGs, the esterification comprises mixing the glycerol and palmitic acid-rich fraction of step (a) in a ratio of 1:3.125 or up to 1:10 (moles of glycerol:moles of free fatty acids and / or their non-glyceride esters) to obtain an admixture.

[0117] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAGs) are tripalmitin (PPP) TAGs, the esterification includes blending glycerol with the palmitic acid-rich fraction to obtain a blend (step (a)), which is carried out in a vessel. The vessel can be any vessel suitable for carrying out a chemical reaction. Such a vessel can be, for example, but is not limited to, a flask, a tank, a tube, a laboratory flask, a round-bottom flask, a three-neck flask, a two-neck flask, a single-neck flask, a glass flask, or a metal flask. The reaction can be carried out with or without agitation, such as stirring.

[0118] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAGs) are tripalmitin (PPP) TAGs, the esterification involves the use of a condenser. The condenser is heated to a temperature of 40°C to 150°C, e.g., 50°C to 90°C, or e.g., 65°C to 90°C. The condenser temperature depends on the size and surface area of ​​the condenser, and it is important to use a temperature at which the water evaporates and most of the glycerol condenses to avoid excessive glycerol loss. Methods for adjusting this will be known to those skilled in the art.

[0119] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAGs) are tripalmitin (PPP) TAGs, the esterification comprises heating the admixture in step (b) to a temperature in the range of 140° C. to 180° C. In one or more embodiments of the process, the admixture in step (b) is heated to a temperature in the range of 160° C. to 170° C.

[0120] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAGs) are tripalmitin (PPP) TAGs, the esterification comprises a reduced pressure in step (b) in the range of 150 mbar to 400 mbar, for example, in the range of 175 mbar to 250 mbar.

[0121] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAGs) are tripalmitin (PPP) TAGs, the esterification comprises a predetermined period of time in step (b) ranging from 15 minutes to 5 hours, for example, ranging from 30 minutes to 4 hours.

[0122] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAGs) are tripalmitin (PPP) TAGs, the esterification comprises the predetermined period of time in step (b) being at least 15 minutes, such as at least 20 minutes, for example at least 30 minutes, such as at least 1 hour, for example at least 2 hours, for example at least 3 hours.

[0123] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAGs) are tripalmitin (PPP) TAGs, the esterification comprises a temperature in step (c) ranging from 180°C to 250°C, e.g., from 210°C to 230°C.

[0124] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAGs) are tripalmitin (PPP) TAGs, the esterification comprises heating the admixture in step (c) to at least 160°C.

[0125] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAG) are tripalmitin (PPP) TAG, the esterification comprises heating the admixture in step (c) to a maximum of 230°C. In one or more embodiments, the admixture in step (c) is heated to a maximum of 240°C. When proceeding from step (b) to step (c), the temperature is gradually increased. In one or more embodiments, the temperature is increased from about 170°C in step (b) to about 210°C in step (c).

[0126] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAGs) are tripalmitin (PPP) TAGs, the esterification comprises a pressure in step (c) ranging from 10 mbar to 400 mbar, e.g., from 20 mbar to 250 mbar, e.g., from 30 mbar to 150 mbar, e.g., from 30 mbar to 90 mbar, or e.g., from 30 mbar to 40 mbar. Proceeding from step (b) to step (c), the pressure is gradually reduced. In one or more embodiments, the pressure is reduced from about 200 mbar in step (b) to about 30 mbar in step (c).

[0127] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAGs) are tripalmitin (PPP) TAGs, the esterification comprises a predetermined period of time in step (c) ranging from 15 minutes to 5 hours, for example, ranging from 30 minutes to 4 hours.

[0128] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAGs) are tripalmitin (PPP) TAGs, the esterification comprises the predetermined period of time in step (c) being at least 15 minutes, such as at least 20 minutes, such as at least 30 minutes, such as at least 1 hour, or such as at least 2 hours.

[0129] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAG) are tripalmitin (PPP) TAG, the esterification includes adding a catalyst in step (a). The catalyst can be any catalyst known to be useful in esterification processes. In one or more embodiments, the catalyst is an organic catalyst. In one or more embodiments, zinc oxide is used as the catalyst. Thus, in one or more embodiments of this process, zinc oxide (ZnO) is added as a catalyst in step (a). As known to those skilled in the art, the predetermined time in step (d) will be reduced if a catalyst is used.

[0130] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAGs) are tripalmitin (PPP) TAGs, the process comprises: mixing the obtained vegetable oil composition, in which 63% to 97% by weight of the total triglycerides are tripalmitin TAG, with a fatty acid composition rich in C18 fatty acids and / or their non-glyceride esters to obtain a first mixture; subjecting the first mixture from the previous step to an enzymatic interesterification process using one or more 1,3-specific enzymes, thereby obtaining a crude vegetable oil blend; Separating the crude vegetable oil blend obtained in the previous step to obtain a mixture of excess free fatty acids and / or their non-glyceride esters. to obtain a final vegetable oil composition in which palmitic acid is present at the sn2 position.

[0131] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAGs) are tripalmitin (PPP) TAGs, the enzymatic interesterification process is carried out by adding one or more 1,3-specific enzymes to the first mixture or by pumping the first mixture through a column containing one or more 1,3-specific enzymes. In one or more embodiments, the temperature of the enzymatic interesterification process is in the range of 40°C to 75°C, such as in the range of 50°C to 70°C, or such as in the range of 55°C to 65°C.

[0132] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAGs) are tripalmitin (PPP) TAGs, a separation step is performed on the resulting crude vegetable oil blend by a distillation and / or neutralization process to remove excess free fatty acids and / or their non-glyceride esters.

[0133] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAGs) are tripalmitin (PPP) TAGs, the step of subjecting the resulting PPP TAG-rich vegetable oil to a distillation and / or neutralization process to remove excess free fatty acids and / or their non-glyceride esters is physical degumming. In one or more embodiments, the distillation is carried out at a temperature of at least 160°C, optionally under reduced pressure. In one or more embodiments, the distillation is carried out at a temperature of at least 190°C under reduced pressure. In one or more embodiments, the distillation is carried out at a temperature of 220°C to 260°C under reduced pressure, for example, at about 240°C under reduced pressure. These are standard conditions for distillation processes known to those skilled in the art. In one embodiment, chemical degumming can be used instead of physical degumming, in which case the temperature change to about 100°C would be known to those skilled in the art.

[0134] In one or more embodiments of the process for making a vegetable oil composition in which 63% to 97% by weight of the total triglycerides (TAG) are tripalmitin (PPP) TAG, the hydrolysis step can be carried out in a countercurrent reactor at high pressure and temperature. After water is removed, the glycerol can be reused in the process. After the hydrolysis step, the hydrolyzed fatty acids can be purified by distillation.

[0135] The present disclosure also includes a vegetable oil composition obtainable by the processes disclosed herein, wherein at least 50% of the palmitic acids in the triglycerides of the vegetable oil composition are present at the sn2 position.

[0136] Also disclosed are vegetable oil compositions wherein at least 50% of the palmitic acids in the triglycerides of the vegetable oil composition are present in the sn2 position.

[0137] In one or more embodiments of the vegetable oil composition, the proportion of sn2 palmitic acid in the total palmitic acid in the vegetable oil composition is 52% or more, such as 55% or more, such as 60% or more, or for example, more than 70%. In one or more embodiments of the vegetable oil composition, the proportion of sn2 palmitic acid in the total palmitic acid in the vegetable oil composition is in the range of 52% to 80%, such as in the range of 52% to 75%, such as in the range of 52% to 70%, or for example, in the range of 55% to 70%.

[0138] In one or more embodiments, the vegetable oil composition comprises 30% to 60% by weight, such as 30% to 50% by weight, such as 35% to 45% by weight, or such as 40% to 45% by weight, of palmitic acid in triglycerides relative to the total weight of fatty acids in the vegetable oil composition. In one or more embodiments, the vegetable oil composition comprises at least 30% by weight, such as at least 35% by weight, or such as at least 40% by weight, of palmitic acid in triglycerides relative to the total weight of fatty acids in the vegetable oil composition.

[0139] In one or more embodiments of the vegetable oil composition, the ratio of oleic acid to linoleic acid (oleic acid:linoleic acid) in the triglycerides of the vegetable oil composition is in the range of 10:1 to 1:2, for example, in the range of 5:1 to 1:1.

[0140] In one or more embodiments of the vegetable oil composition, 40% or more of the triglycerides in the final vegetable oil composition are of the OPO, OPL, and / or LPL type.

[0141] In one or more embodiments, 40% or more of the triglycerides in the final vegetable oil composition are of the OPO type.

[0142] Also disclosed herein is the use of a vegetable oil composition according to the present disclosure, wherein at least 50% of the palmitic acids in the triglycerides of the vegetable oil composition are present in the sn2 position, in the manufacture of infant formula.

[0143] Also disclosed herein is the use of a vegetable oil composition according to the present disclosure, wherein at least 50% of the palmitic acid in the triglycerides of the vegetable oil composition is present at the sn2 position, in the production of a plant-based food product.

[0144] Further disclosed is an infant formula comprising 15% to 100% by weight of a vegetable oil composition according to the present disclosure, wherein at least 50% of the palmitic acids in the triglycerides of the vegetable oil composition are present at the sn2 position.

[0145] In one or more embodiments, an infant formula comprising 20% ​​to 90% by weight, such as 20% to 80% by weight, or such as 20% to 70% by weight, of a vegetable oil composition, wherein at least 50% of the palmitic acids in the vegetable oil composition are present at the sn2 position, of the total palmitic acids.

[0146] When describing embodiments, not all possible combinations and permutations of embodiments are explicitly described. Nevertheless, the mere fact that certain measures are recited in mutually different dependent claims or described in different embodiments does not indicate that combinations of these measures cannot be used to advantage. The present invention contemplates all possible combinations and permutations of the described embodiments.

[0147] The present invention is further illustrated by the following examples, which should not be construed as limiting the scope of protection. [Example]

[0148] Example 1 - Preparation of PPP TAG (PPP) enriched oil from palm fraction Various oils containing palmitic acid can be used as the starting oil composition. For this example, three different palm fractions were used: palm stearin, palm oil, and palm olein. Table 1 shows the compositions of the three oils.

[0149] (Table 1) TIFF2026012865000003.tif35128 * Analysis according to IUPAC 2.205 ** Analysis according to IUPAC 2.304

[0150] The palm fraction is separated into free fatty acids (FFA), water, and glycerol via standard countercurrent hydrolysis under high pressure and excess water. The FFA fraction is transferred to a distillation unit, where the FFA is separated (split) into a palmitic acid-rich fraction (P-rich fraction) and an oleic acid-rich fraction (O-rich fraction), respectively. The resulting fractions have the compositions shown in Tables 2a, 2b, and 2c below.

[0151] Those skilled in the art will know that the characteristics of the stripping column, the temperature applied, and the reflux will determine the splitting of the different fatty acids. In these cases, about 6% of the residual palmitic acid was found in the oleic acid-rich fraction. In principle, the amount of palmitic acid found in the C18 stream could be reduced at the expense of a smaller capacity for the distillation column.

[0152] (Table 2a) (Palm oil) TIFF2026012865000004.tif40128

[0153] (Table 2b) (Palm stearin) TIFF2026012865000005.tif40128

[0154] (Table 2c) (Palm olein) TIFF2026012865000006.tif34128 * Analysis according to IUPAC 2.304

[0155] Glycerol and free fatty acids were then mixed in a reaction vessel in a 1:4 weight ratio (33% free fatty acid excess). The free fatty acids in this example contained 98% by weight C16:0, 1% by weight C18:1, and 1% fatty acids that were not C:16 or C18:1 (the starting oil was palm oil; see Table 2a). The reaction vessel was equipped with a vacuum inlet, a cold trap, and a condenser heated to 70°C. The reaction mixture was heated to 150°C under reduced pressure (200 mbar) over approximately 20 minutes. The pressure was gradually reduced to 33 mbar over 30-60 minutes, while the temperature was gradually increased to 210°C. After reaching the final reaction temperature, the reaction mixture was left under these conditions for 5 hours. The resulting crude oil was then distilled under reduced pressure at 240°C to remove excess free fatty acids, yielding a PPP TAG-rich oil consisting of 97.9% TAG, 1.3% DAG, and 0.4% FFA, as shown in Table 3 below.

[0156] Table 3 shows the composition of PPP TAG (also known simply as PPP or tripalmitin)-rich oil. TIFF2026012865000007.tif44128 * Analyzed using IUPAC 2.304 ** Diglycerides and monoglycerides are given as % of acylglycerols and were analyzed by AOCS Cd 11d-96 *** Analysis according to IUPAC 2.323 **** Analysis according to IUPAC 2.201

[0157] The resulting PPP TAG-rich oil had 98% P(sn2), compared to 14% for palm oil with an IV of 52 and 40% for palm stearin with an IV of 34.

[0158] Example 2 - Enzymatic interesterification of PPP TAG (tripalmitin, PPP) enriched oil with a composition of free fatty acids enriched in C18 fatty acids (1:2 w / w ratio) First, 3.95 kg of raw material mixture was prepared by mixing tripalmitin (1.3 kg) and free fatty acids rich in C18 fatty acids (2.65 kg) in a weight ratio of 1:2.

[0159] The composition of the utilized PPP and free fatty acids rich in C18 fatty acids is shown in Table 4.

[0160] (Table 4) TIFF2026012865000008.tif61128 * Analysis using IUPAC 2.304 ** Analysis according to IUPAC 2.323

[0161] This mixture was reacted by feeding it to a column containing 10 g of 1,3-specific lipase DF IM (Amano Japan) at 60°C at a flow rate of 40 g / h, corresponding to 4 g oil / 1 g enzyme / h. After approximately 95 hours (just over 4 days), the reaction was stopped. During the reaction, samples were taken to monitor the enzyme activity and product quality over time (see Figure 1).

[0162] After partitioning the formed TAG and excess free fatty acids, the resulting composition is obtained (shown in Table 5 below).

[0163] (Table 5) TIFF2026012865000009.tif39128 * Analysis according to IUPAC 2.323

[0164] C52 can be considered a measure of OPO, OPL, LPL, etc., and C50 is an intermediate product (such as PPO or PPL).

[0165] Table 6 below shows the fatty acid composition of the product made from PPP and free fatty acids enriched in C18 fatty acids, and the fatty acid mixture after distillation from TAG.

[0166] (Table 6) TIFF2026012865000010.tif29128 * Analysis using IUPAC 2.304

[0167] Example 3 - Enzymatic interesterification of PPP TAG (tripalmitin, PPP) enriched oil with a composition of free fatty acids enriched in C18 fatty acids (1:4 w / w ratio) This example was carried out under exactly the same conditions as Example 2, with the only difference being that the ratio of PPP to fatty acids rich in C18 fatty acids was 1:4 by weight, rather than 1:2 as in Example 2. Samples were taken during the reaction to monitor the enzyme activity and product quality over time (see Figure 2). This results in a product with a higher amount of sn2 palmitate relative to the total palmitate present. The amount of C52 formed is significantly higher, with an average P(sn2) / total P of 68%.

[0168] Example 4 - Comparative Example: Enzymatic Interesterification of Palm Oil Stearin (POST) with an Iodine Value (IV) of 13 and a Composition of Free Fatty Acids Rich in C18 Fatty Acids The exact same process as in Example 2 is carried out, only this time the starting material is palm oil stearin (POST) with an iodine value (IV) of 13 (POST IV 13). The composition of the utilized POST IV 13 and free fatty acids rich in C18 fatty acids used in this example are shown in Table 4 of Example 2. This should be viewed as an example of the situation in today's process where oil rich in PPP TAGs is not available.

[0169] First, 3.95 kg of a raw material mixture was prepared by mixing palm stearin IV 13 (1.3 kg) with free fatty acids rich in C18 fatty acids (2.65 kg) in a 1:2 weight ratio. This mixture was fed to a column containing 10 g of 1,3-specific lipase DF IM (Amano Japan) at 60 °C at a flow rate of 40 g / h, corresponding to 4 g oil / 1 g enzyme / h. After approximately 95 h (just over 4 days), the reaction was stopped. During the reaction, samples were taken to monitor enzyme activity and product quality over time (see Figure 3). C52 can be considered a measure of OPO, OPL, LPL, etc., while C50 is an intermediate product (PPO, PPL, etc.). As more oil passes through the enzyme, enzyme activity decreases, resulting in a decrease in the formation of C52 and an increase in the formation of C50.

[0170] Comparing the results from the two enzymatic transesterification reactions, it can be seen that the utilization of tripalmitin made via the esterification process gives a higher quality product as measured by significantly higher amounts of sn2 palmitic acid compared to standard palm stearin (72% vs. 93% - see Table 8), and the concentration of OPO in the product made using the PPP starting material is higher compared to the palm stearin starting material.

[0171] From Table 4, it is clear that the PPP TAG (PPP)-rich oil produced had a high yield of palmitic acid (98%), with the amount of PPP obtained approaching 95% (compared to 62% for POST IV 13), making it an excellent starting point for creating oil compositions with high amounts of palmitic acid present at the sn2 position, such as OPO.

[0172] Conclusions from the above examples Table 7 shows a comparison of the products before and after enzymatic interesterification.

[0173] Table 7 shows TAG before and after enzymatic interesterification. TIFF2026012865000011.tif44148 * Analysis according to IUPAC 2.323 ** The % sn2 C16:0 of ​​total C16:0 is calculated as 100 / 3 × (sn2 C16:0 as determined by IUPAC 2.210) / (C16:0 as determined by IUPAC 2.304). The denominator 3 is due to the fact that there are three positions in a triglyceride. *** The analysis can be performed by any known method by a commercial laboratory.

[0174] Table 8 shows the different fatty acid contents at the sn-2 position in both the starting oil material and the resulting product for POST IV 13 and PPP. TIFF2026012865000012.tif41145 *The fatty acid composition at the sn2 position is given as the % of fatty acid residues at the sn2 position and analyzed by IUPAC 2.210.

[0175] It is clear from Tables 7 and 8 that the resulting PPP contains much more palmitic acid at the sn2 position than the POST IV 13 reference. This should therefore be a better starting point for making oil compositions with high amounts of palmitic acid present at the sn2 position, such as OPO. In fact, this is true. Looking at the ratio of OPO to its asymmetric counterpart POO (or OOP), it is clear that the ratio is much higher (more than three times) when starting with PPP (see Table 7).

[0176] Example 5 Starting with 10 kg of palm oil (containing 42% palmitic acid), a palmitic acid-rich fraction is obtained with a 40% yield (Example 1). A 33% excess of palmitic acid is then reacted with glycerol to obtain PPP triglycerides (Example 1). Of the starting palmitic acid (42%), 29% is present in PPP (a 10% excess remains for the next cycle). Enzymatic interesterification is then carried out using PPP as the starting material (Example 2). The resulting OPO-rich oil contains 52% palmitic acid, equal to 15% of the starting palmitic acid (14% remains for the next cycle). Thus, in the first cycle, 15% / 42% = 36% of the palmitic acid from the starting palm oil is recovered in the product, and (10% + 14%) / 42% = 57% is recycled to the next cycle (resulting in a 7% loss of palmitic acid). This process is then repeated with the recovered palmitic acid, and in the next cycle, an additional 21% of the palmitic acid from the starting palm oil is recovered, resulting in a recovery of 36% + 21% = 57% of the starting palm oil. The table below shows the percentage of palmitic acid recovered in the first four cycles. Figure 5 shows the initial process for obtaining the required free fatty acids, while Figure 4 shows the process for recycling the palmitic acid.

[0177] TIFF2026012865000013.tif38128

[0178] The cumulative amount of palmitic acid in the product compared to the amount present in the starting oil depends on several factors, among them: - If the loss of palmitic acid during distillation is reduced, the amount of palmitic acid recovered per cycle increases. - If purer OPO is made, there will be less palmitic acid in the OPO product, resulting in lower palmitic acid recovery per cycle.

[0179] The invention is further described in the following non-limiting sections.

[0180] 1. A process for making a final vegetable oil composition in which at least 50% of the palmitic acid in the triglycerides of the final vegetable oil composition is present in the sn2 position, the process comprising the steps of providing a starting vegetable oil composition comprising palmitic acid in triglycerides, carrying out an enzymatic interesterification process, and using excess free fatty acids and / or their non-glyceride esters obtained during the process and recycling them back into the process, wherein at least 70% by weight of the total amount of palmitic acid in the starting vegetable oil composition is present in the final vegetable oil composition.

[0181] 2. (I) carrying out a hydrolysis or alcoholysis process and then carrying out distillation, thereby obtaining at least a palmitic acid-rich fraction; (II) carrying out esterification of glycerol with the palmitic acid-rich fraction to obtain a vegetable oil enriched in at least PPP TAGs; (III) subjecting the PPP TAG-rich vegetable oil to an enzymatic interesterification process with a fatty acid composition, thereby obtaining a crude vegetable oil blend; (IV) separating the crude vegetable oil blend to obtain a mixture of excess free fatty acids and / or their non-glyceride esters and the final vegetable oil composition in which palmitic acid is present in the sn2 position; (V) using the excess mixture of free fatty acids and / or their non-glyceride esters obtained during the process and recycling it back into the process. Item 1, further comprising the process.

[0182] 3. The process according to item 2, wherein the fatty acid composition in step (III) is a fatty acid composition rich in C18 fatty acids and / or their non-glyceride esters.

[0183] 4. Step (I) (Ia) subjecting the starting vegetable oil composition to a hydrolysis or alcoholysis process to obtain glycerol and free fatty acids and / or their non-glyceride esters; (Ib) separating the free fatty acids and / or non-glyceride esters thereof from the glycerol and water / alcohol to obtain a mixture of free fatty acids and / or non-glyceride esters thereof; (Ic) subjecting the mixture of free fatty acids and / or their non-glyceride esters to a distillation process to obtain a C18 fatty acid-rich fraction and a palmitic acid-rich fraction. Item 4. The process according to item 2 or 3, comprising:

[0184] 5. Step (III) (IIIa) subjecting the PPP TAG-rich vegetable oil obtained in step (II) to a distillation and / or neutralization process to remove excess free fatty acids and / or their non-glyceride esters, thereby obtaining a vegetable oil composition in which 63% to 97% by weight of the total triglycerides are tripalmitin TAG; (IIIb) mixing the obtained vegetable oil composition, in which 63% by weight to 97% by weight of the total triglycerides are tripalmitin TAG, with a fatty acid composition rich in C18 fatty acids and / or their non-glyceride esters to obtain a first mixture; (IIIc) subjecting the first mixture from step (IIIb) to an enzymatic interesterification process using one or more 1,3-specific enzymes, thereby obtaining a crude vegetable oil blend. Item 5. The process according to any one of Items 2 to 4, comprising:

[0185] 6. The process of any preceding paragraph, wherein the starting vegetable oil composition comprises 80% or less by weight of palmitic acid in triglycerides compared to the total weight of fatty acids in triglycerides.

[0186] 7. The process according to any one of items 4 to 6, wherein the step of using excess free fatty acids and / or non-glyceride esters thereof obtained during the process and recycling them back into the process comprises using the mixture of excess free fatty acids and / or non-glyceride esters thereof obtained from step (IV) and feeding them to the mixture in step (Ic).

[0187] 8. The process according to any one of items 2 to 7, further comprising the step of dividing the mixture of excess free fatty acids and / or their non-glyceride esters from step (IV) by a distillation process, thereby obtaining a palmitic acid (P, C16:0)-rich fraction and a C18 fatty acid-rich fraction, and using at least a portion of the palmitic acid-rich fraction in step (II).

[0188] 9. The process according to item 8, further comprising a distillation process for the fraction rich in C18 fatty acids and using at least a portion of the fraction rich in C18 fatty acids in step (IIIb).

[0189] 10. The process according to any one of items 5 to 9, wherein the fraction enriched in C18 fatty acids from step (Ic) is used in step (IIIb).

[0190] 11. The process according to any one of items 4 to 10, further comprising the steps of separating glycerol and water / alcohol from step (Ib) and using the glycerol obtained in said step in the esterification step (II).

[0191] 12. The process according to any one of items 5 to 11, further comprising the step of using excess free fatty acids and / or non-glyceride esters thereof obtained from step (IIIa) and supplying them to esterification step (II).

[0192] 13. The process according to any one of paragraphs 5 to 12, further comprising bleaching and / or neutralizing the product obtained in the distillation and / or neutralization process of step (IIIa).

[0193] 14. The process according to any one of items 2 to 13, further comprising bleaching and / or neutralizing and / or deodorizing the final vegetable oil composition obtained in the separation of step (IV).

[0194] 15. The process according to any one of paragraphs 5 to 14, wherein the vegetable oil composition obtained after step (IIIa) has 70% to 97% by weight of tripalmitin TAG of total triglycerides, for example, 85% to 97% by weight of tripalmitin TAG of total triglycerides.

[0195] 16. The process according to any one of items 5 to 15, wherein the proportion of palmitic acid at the sn2 position of all fatty acids in the triglycerides of the vegetable oil composition obtained after step (IIIa) is in the range of 85% to 99%.

[0196] 17. The process according to any one of paragraphs 5 to 16, wherein the vegetable oil composition obtained after step (IIIa) has an amount of diglycerides and / or monoglycerides of 6% or less, such as 3% or less, or such as 2% or less, relative to the total weight of the vegetable oil composition.

[0197] 18. A process according to any preceding paragraph, wherein the proportion of sn2 palmitic acid in the total palmitic acid in the triglycerides of the final vegetable oil composition is 52% or more, such as 55% or more, such as 60% or more, or such as 70% or more.

[0198] 19. The process of any preceding clause, wherein the final vegetable oil composition comprises 30% to 60% by weight, such as 30% to 50% by weight, such as 35% to 45% by weight, or such as 40% to 45% by weight, of palmitic acid in triglycerides relative to the total weight of fatty acids in triglycerides in the final vegetable oil composition.

[0199] 20. The process according to any of the preceding paragraphs, wherein the ratio of oleic acid to linoleic acid (oleic acid:linoleic acid) in the triglycerides of the final vegetable oil composition is in the range of 10:1 to 1:2, for example in the range of 5:1 to 1:1.

[0200] 21. The process of any preceding paragraph, wherein at least 75% by weight of the total amount of palmitic acid in the starting vegetable oil composition is present in the final vegetable oil composition, for example, at least 80%, such as at least 90%, or such as at least 95% by weight of the total amount of palmitic acid in the starting vegetable oil composition is present in the final vegetable oil composition.

[0201] 22. The process of any preceding paragraph, wherein no chemical catalyst is used in any of the process steps.

[0202] 23. The process of any preceding paragraph, wherein the enzyme used is a non-recombinant enzyme.

[0203] 24. The process of any preceding paragraph, wherein no organic solvents are used in any of the process steps.

[0204] 25. The process of any preceding paragraph, wherein the starting vegetable oil composition comprises at least 9% palmitic acid in triglycerides, such as at least 15%, for example at least 25%, for example at least 35%, for example at least 40%, for example at least 50%, or for example at least 60% palmitic acid, relative to the total weight of fatty acids in triglycerides.

[0205] 26. The process of any preceding paragraph, wherein the starting vegetable oil composition has an iodine value of at least 15, such as at least 20, for example at least 25, for example at least 30, for example at least 35, such as at least 40, for example at least 45, for example at least 50, for example at least 55, or such as at least 60.

[0206] 27. The process of any preceding paragraph, wherein the starting vegetable oil composition is derived from one of the following sources: palm oil or a fraction or derivative thereof, palm kernel oil, corn oil, primary dry fractionated palm stearin, rice bran oil, peanut oil, coconut oil, soybean oil, cotton oil, or a combination thereof.

[0207] 28. A vegetable oil composition obtainable by the process described in any of the preceding paragraphs, wherein at least 50% of the palmitic acids in the triglycerides of the vegetable oil composition are present at the sn2 position.

[0208] 29. A vegetable oil composition according to item 28, wherein the proportion of sn2-position palmitic acid in the total palmitic acid in the vegetable oil composition is 52% or more, for example 55% or more, for example 60% or more, or for example 70% or more.

[0209] 30. The vegetable oil composition according to either item 28 or 29, comprising 30% to 60% by weight, for example 30% to 50% by weight, for example 35% to 45% by weight, or for example 40% to 45% by weight of palmitic acid in triglycerides relative to the total weight of fatty acids in the triglycerides in the vegetable oil composition.

[0210] 31. The vegetable oil composition according to any one of items 28 to 30, wherein the ratio of oleic acid to linoleic acid (oleic acid:linoleic acid) in the triglycerides of the vegetable oil composition is in the range of 10:1 to 1:2, for example, in the range of 5:1 to 1:1.

[0211] 32. A vegetable oil composition, wherein at least 50% of the palmitic acids in the triglycerides of the vegetable oil composition are present at the sn2 position.

[0212] 33. The vegetable oil composition according to item 32, wherein the proportion of sn2 palmitic acid in the total palmitic acid in the vegetable oil composition is 52% or more, for example 55% or more, for example 60% or more, or for example 70% or more.

[0213] 34. The vegetable oil composition according to either item 32 or 33, comprising 30% to 60% by weight, for example 30% to 50% by weight, for example 35% to 45% by weight, or for example 40% to 45% by weight of palmitic acid in triglycerides relative to the total weight of fatty acids in the triglycerides in the vegetable oil composition.

[0214] 35. The vegetable oil composition according to any one of items 32 to 34, wherein the ratio of oleic acid to linoleic acid (oleic acid:linoleic acid) in the triglycerides of the vegetable oil composition is in the range of 10:1 to 1:2, for example, in the range of 5:1 to 1:1.

[0215] 36. Use of a vegetable oil composition according to any one of items 28 to 36 in the production of infant formula, wherein at least 50% of palmitic acid in the triglycerides of the vegetable oil composition is present at the sn2 position.

[0216] 37. Use of a vegetable oil composition according to any one of items 28 to 36 in the production of a plant-based food, wherein at least 50% of palmitic acid in the triglycerides of the vegetable oil composition is present at the sn2 position.

[0217] 38. An infant formula comprising 15% to 100% by weight of a vegetable oil composition in which at least 50% of all palmitic acids in the triglycerides of the vegetable oil composition are present at the sn2 position.

Claims

1. A process for producing a final vegetable oil composition in which at least 50% of the total palmitic acid in the triglycerides of the final vegetable oil composition is located at the sn2 position, A step of preparing a starting vegetable oil composition containing palmitic acid in triglycerides, The process of carrying out an enzymatic transesterification process, and A step of using the excess free fatty acids and / or their non-glyceride esters obtained during the process and returning them to the process for reuse, so that at least the unreacted palmitic acid remaining from the process can be reused in the same process starting with a new amount of the starting vegetable oil composition. Includes, A process in which at least 70% by weight of the total amount of palmitic acid in the starting vegetable oil composition is present in the final vegetable oil composition where at least 50% of the total palmitic acid in the triglycerides of the final vegetable oil composition is located at the sn2 position.

2. (I) A process of carrying out hydrolysis or alcoholization, followed by distillation, thereby obtaining a fraction rich in at least palmitic acid; (II) A step of esterifying glycerol with the palmitic acid-rich fraction to obtain a vegetable oil rich in at least PPP TAG; (III) A step of subjecting the PPP TAG-rich vegetable oil to an enzymatic transesterification process with a fatty acid composition to obtain a crude vegetable oil blend; (IV) Separating the crude vegetable oil mixture to obtain a mixture of excess free fatty acids and / or their non-glyceride esters and the final vegetable oil composition in which palmitic acid is present at the sn2 position; (V) A mixture of excess free fatty acids and / or their non-glyceride esters obtained during the process is used and returned to the process for reuse. The process according to claim 1, further comprising:

3. The process according to claim 2, wherein the fatty acid composition of step (III) is a fatty acid composition rich in C18 fatty acids and / or their non-glyceride esters.

4. Process (I) (Ia) A step of subjecting the starting vegetable oil composition to a hydrolysis or alcoholization process to obtain glycerol and free fatty acids and / or their non-glyceride esters; (Ib) A step of separating the free fatty acid and / or its non-glyceride ester from the glycerol and water / alcohol to obtain a mixture of the free fatty acid and / or its non-glyceride ester; (Ic) A distillation process is carried out on a mixture of free fatty acids and / or their non-glyceride esters to obtain a fraction rich in C18 fatty acids and a fraction rich in palmitic acid. The process according to claim 2 or 3, including the process described in claim 2 or 3.

5. Process (III) (IIIa) Distillation and / or neutralization processes are carried out on the PPP TAG-rich vegetable oil obtained in step (II) to remove excess free fatty acids and / or their non-glyceride esters; thereby obtaining a vegetable oil composition in which 63% to 97% by weight of the total triglycerides is tripalmitin TAG; (IIIb) A step to obtain a first mixture by mixing the obtained vegetable oil composition, in which 63% to 97% by weight of the total triglycerides is tripalmitin TAG, with a fatty acid composition rich in C18 fatty acids and / or their non-glyceride esters; (IIIc) The first mixture from step (IIIb) is subjected to an enzymatic transesterification process using one or more 1,3-specific enzymes, thereby obtaining a crude vegetable oil admixture. The process according to any one of claims 2 to 4, including the process described in any one of claims 2 to 4.

6. The process according to any one of claims 1 to 5, wherein the starting vegetable oil composition contains triglyceride palmitic acid in an amount of 80% by weight or less compared to the total weight of triglyceride fatty acids.

7. The process according to any one of claims 4 to 6, wherein the step of using the excess free fatty acids and / or their non-glyceride esters obtained in the process and returning them to the process for reuse includes using the mixture of excess free fatty acids and / or their non-glyceride esters obtained from step (IV) and supplying them to the mixture of step (Ic).

8. The process according to any one of claims 2 to 7, further comprising the step of separating the mixture of excess free fatty acids and / or their nonglyceride esters from step (IV) by a distillation process to obtain a fraction rich in palmitic acid (P,C16:0) and a fraction rich in C18 fatty acids, and using at least a portion of the palmitic acid-rich fraction in step (II).

9. The process according to claim 8, further comprising a distillation process for the C18 fatty acid-rich fraction and the use of the C18 fatty acid-rich fraction in at least a portion of the process (IIIb).

10. The process according to any one of claims 5 to 9, wherein the C18 fatty acid-rich fraction from step (Ic) is used in step (IIIb).

11. The process according to any one of claims 4 to 10, further comprising the steps of separating glycerol and water / alcohol from step (Ib), and using the glycerol obtained in step (II) in an esterification step.

12. The process according to any one of claims 5 to 11, further comprising using the excess free fatty acids and / or their non-glyceride esters obtained from step (IIIa) and further supplying them to step (II) of the esterification step.

13. The process according to any one of claims 1 to 12, wherein no chemical catalyst is used in any of the process steps.

14. The process according to any one of claims 1 to 13, wherein the starting vegetable oil composition has an iodine value of at least 15, at least 20, at least 25, at least 30, at least 35, at least 40, at least 45, at least 50, at least 55, or at least 60.

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