Methods, artificial plant oil compositions, uses and infant formula

Abstract

A method for increasing the palmitic acid content in a starting vegetable oil composition is disclosed. The invention also relates to a synthetic vegetable oil composition having palmitic acid in the triglycerides at a weight of 20% to 60% by weight relative to the total weight of fatty acids in the triglycerides of the synthetic vegetable oil composition, wherein the synthetic vegetable oil composition is not derived from palm oil, palm kernel oil, or oils derived therefrom. The invention further relates to the use of the synthetic vegetable oil composition and infant formula foods comprising the synthetic vegetable oil composition.

Description

Technical Field

[0001] This invention relates to a method for increasing the amount of palmitic acid present in the triglycerides of a vegetable oil composition, thereby creating a vegetable oil composition in which the amount of palmitic acid present in the triglycerides is increased. The invention further relates to the use of the created vegetable oil composition and infant formula containing the created vegetable oil composition. Background Technology

[0002] It is known that certain types of highly fractionated palm stearin, as disclosed in, for example, EP1928990B1, EP3583857A1, EP0209327B1, and WO2005 / 036987, are used to produce products with high palmitic acid content (especially at the sn2- position) for use in mimicking human milk, particularly for infant nutrition. The advantage of using expensive hard palm stearin is that it is a way to ensure a high palmitic acid content in the starting oil.

[0003] EP2173197A2 discloses a method for producing randomized palm oil stearin with reduced levels of dialkyl ketones (DAKs) from 1 to 140 ppm. This method includes a step of chemically transesterifying the palm oil stearin in the presence of a transesterification catalyst, wherein the amount of catalyst is selected to reduce the level of unwanted DAKs. In fact, conventional chemical transesterification forms DAKs that are unsuitable for inclusion in, for example, infant formula.

[0004] Alternatively, one approach to producing vegetable oil compositions with high palmitic acid content (particularly present at the sn2- position) is to perform at least one enzymatic transesterification and optionally one physical transesterification on a starting vegetable oil (such as palm oil or palm kernel oil) with high palmitic acid content. However, the use of palm oil or palm kernel oil has disadvantages, particularly the potential negative environmental impacts. Summary of the Invention

[0005] For some infant formulas, a high content of palmitic acid at the sn2- position of the triglycerides in vegetable oils is not required. The inventors have recognized that infant formulas in which the triglycerides of vegetable oils contain fatty acids with a statistically significant distribution at the sn1, sn2, and sn3 positions of the glycerol backbone provide positive nutritional effects. The inventors have also recognized that no optimized and reliable method has yet been disclosed for manufacturing such vegetable oils.

[0006] Therefore, the main objective of this invention is to provide a method that is an improvement over the methods mentioned above in many respects, including providing an efficient and alternative route for enriching the palmitic acid content of vegetable oils, particularly from vegetable oils that do not contain palm oil, palm kernel oil and oils derived therefrom.

[0007] Another object of the present invention is to provide a method for utilizing palmitic acid in raw vegetable oils as much as possible. Another object of the present invention is to provide a method for producing vegetable oil compositions that meet the nutritional needs of infants and young children.

[0008] Another object of the present invention is to reduce or completely eliminate the use of palm-derived components (particularly palm oil and its fractions) as a source of palmitic acid for use in infant formula. A further object of the present invention is to achieve flexibility in the source of palmitic acid, thereby becoming less dependent on the availability of palm oil or its palmitic acid-rich fractions.

[0009] The present invention also relates to a synthetic vegetable oil composition having palmitic acid in triglycerides at a weight of 20% to 60% relative to the total weight of fatty acids in the triglycerides of the synthetic vegetable oil composition, such as 25% to 60% relative to the total weight of fatty acids in the triglycerides, such as 25% to 55% relative to the total weight of fatty acids in the triglycerides, such as 30% to 55% relative to the total weight of fatty acids in the triglycerides, such as 35% to 50% relative to the total weight of palmitic acid in the triglycerides, such as 35% to 45% relative to the total weight of palmitic acid in the vegetable oil composition, wherein the proportion of palmitic acid at the sn2- position is in the range of 25% to 35%.

[0010] This article discloses, in its first aspect, a method for increasing the palmitic acid content of a starting vegetable oil composition, wherein the method comprises the following steps:

[0011] A) A starting vegetable oil composition is provided, comprising less than 35% by weight, such as less than 30% by weight, such as less than 25% by weight, such as less than 20% by weight, such as less than 15% by weight, or such as less than 10% by weight of C16:O-fatty acids in triglycerides relative to the total weight of fatty acids in the starting vegetable oil composition; said starting vegetable oil composition is non-palm oil;

[0012] B) Subjecting the starting vegetable oil composition to a hydrolysis or alcoholysis process to form glycerol, free fatty acids and / or their non-glycerol esters;

[0013] C). Distill the free fatty acids and / or their non-glycerides obtained in step B) to obtain at least one fatty acid composition rich in palmitic acid;

[0014] D) Esterification of glycerol with the fatty acid composition rich in palmitic acid and / or its non-glycerides, and optionally with a supplementary fatty acid composition, to form a crude vegetable oil blend;

[0015] E). Separate the crude vegetable oil blend to obtain a mixture of residual reactants and an artificial vegetable oil composition.

[0016] Without being bound by any theoretical constraints, the method described above allows for the efficient increase of palmitic acid content in starting vegetable oil compositions. This method is advantageous because it efficiently utilizes palmitic acid in the starting vegetable oil composition, especially when the starting vegetable oil composition has a low palmitic acid content. A resulting synthetic vegetable oil composition is provided that can be used for infant nutrition.

[0017] Non-palm oil is an oil not selected from palm oil, palm kernel oil, oils derived therefrom, any combination thereof, or any of their derivative fractions. Although palm oil is the most well-known vegetable oil containing high levels of palmitic acid (C16:0 fatty acid residues), other vegetable oils may also contain palmitic acid, but typically in lower abundance.

[0018] In step A, the starting oil is selected from non-palm sources and may be a single oil or oil fraction, or a blend of non-palm oils. The starting oil may contain oil recycled from later steps of the method. Fatty acids may be present as triglycerides, diglycerides, monoglycerides, and free fatty acids.

[0019] In step B, when alcoholysis is used, fatty acids are removed from glycerol to obtain free fatty acids and / or alcohol esters.

[0020] In step C, the hydrolyzed oil is fractionated by distillation, and the fraction rich in palmitic acid is selected to continue the process. If the previous step was alcoholysis, the fatty acids can be distilled as free fatty acids or as alcohol esters. Other major fractions may include, for example, glycerol, as well as fatty acid fractions with reduced amounts of palmitic acid.

[0021] In step D, fatty acids react with glycerol, preferably in excess to ensure that the majority of the fatty acids are in triglycerides. If necessary, fatty acids from other sources can be added to the reaction mixture. This is a random reaction process, resulting in a statistically significant distribution of fatty acids on glycerol.

[0022] In step E, unreacted fatty acids and glycerol are separated from the regenerated oil, which mainly contains triglycerides. The mixture of residual reactants can be recycled back into the method.

[0023] Although the above method does not include an expensive additional 1,3-selective enzymatic process, it can still efficiently obtain large quantities of triglycerides with palmitic acid at the sn2- position.

[0024] This document discloses, in a second aspect, a synthetic vegetable oil composition having 25 to 35% by weight palmitic acid (C16:0) present at the sn2-position in the total palmitic acid of the triglycerides in the synthetic vegetable oil composition, the composition having palmitic acid in the triglycerides in the amount of 20% to 60% by weight relative to the total weight of fatty acids in the triglycerides in the synthetic vegetable oil composition, the synthetic vegetable oil composition not being derived from palm oil, palm kernel oil or oils derived therefrom, wherein the proportion of palmitic acid at the sn2-position in the total palmitic acid of the triglycerides in the vegetable oil composition is in the range of 25% to 35%.

[0025] The use of the artificial vegetable oil composition in the manufacture of infant formula is disclosed in a third aspect of this document.

[0026] The use of the artificial vegetable oil composition in the manufacture of plant-based food products is disclosed in the fourth aspect of this document.

[0027] This document discloses, in its fifth aspect, an infant formula food comprising 5% to 100% by weight of the aforementioned artificial vegetable oil composition.

[0028] definition

[0029] As used herein, the term "vegetable" should be understood as originating from plants or single-celled organisms. Therefore, if all fatty acids used to obtain the triglycerides or oils are of plant or single-celled origin, then vegetable oils or vegetable triglycerides should still be understood as vegetable oils or vegetable triglycerides.

[0030] As used herein, the term "oil" refers to glycerides of fats and oils containing fatty acyl groups and does not imply any specific melting point. The term "fat" is used synonymously with "oil" in this document.

[0031] The nomenclature CX indicates that the fatty acid contains X carbon atoms. For example, C14-fatty acids have 14 carbon atoms, while C16-fatty acids have 16 carbon atoms.

[0032] The nomenclature CX:Y indicates that the fatty acid contains X carbon atoms and Y double bonds. For example, C14:0 fatty acid has 14 carbon atoms and 0 double bonds, while C18:1 fatty acid has 18 carbon atoms and 1 double bond.

[0033] Triglycerides are typically labeled using the "sn" designation, which stands for stereospecific number. In the Fische projection of natural L-glycerol derivatives, the secondary hydroxyl group appears to the left of the C-2 carbon atom; then the carbon atom above it becomes C-1 and the carbon atom below it becomes C-3. The prefix 'sn' is placed before the main name of the compound.

[0034] Sn1 / sn2 / sn3:

[0035]

[0036] As used herein, unless otherwise specified, “%” or “percentage” refers to weight percentage (i.e., weight % or wt%).

[0037] As used in this article, the term "fatty acid" encompasses both free fatty acids and fatty acid residues in triglycerides.

[0038] As used herein, the expression "oils derived therefrom" encompasses any processed oil, that is, oil that has undergone a certain process. For example, this term includes any fraction of oil, that is, oil that has undergone fractionation.

[0039] As used herein, the expressions “fatty acid composition rich in…” or “enriched fraction” refer to a fatty acid composition rich in a specific fatty acid. This expression includes fatty acid compositions that have undergone enrichment of one or more fatty acids, i.e., “enriched fatty acid composition” or “enriched fraction”.

[0040] Various methods can be used to separate FFA into fractions with the desired composition, including but not limited to fractionation, FFA classification, and SPD (short-path distillation). SPD treatment will be described in detail in the section on SPD.

[0041] Fractionation is described in the literature, and C16 FFA enriched fractions can be obtained with a purity of 90% or higher. See, for example, Bailey's industrial oil and fats products, Vol. 2, 4th edition, a Wiley Interscience publication, Chapter 6. See further, R. Berger and W. Pherson, J. Am. Oil Chemists' Soc, vol. 56 (1979). See also RH Potts and FB white, J. Am. Oil Chemists' Soc, vol. 30, No. 2, (1953). And further, see Distillation – Advances from modelling to application, Chapter 5, 2012, published by InTech, ISBN 978-953-51-0428-5.

[0042] FFA classification is described, for example, in JAOCS, Vol. 61, No. 2, pp. 219-222 (1984) and JAOCS, Vol. 75, Chapter 10, pp. 1403-1409 (1998). Detailed Implementation

[0043] In describing the following embodiments, the present invention envisions all possible combinations and arrangements of the following embodiments with the aspects disclosed above.

[0044] This invention relates to a method for increasing the palmitic acid content in a starting vegetable oil composition, wherein the method comprises the following steps:

[0045] A) A starting vegetable oil composition is provided, comprising palmitic acid in triglycerides at a weight of less than 35%, such as less than 30%, such as less than 25%, such as less than 20%, such as less than 20% by weight relative to the total weight of fatty acids in the triglycerides of the starting vegetable oil composition; said starting vegetable oil composition is not selected from: palm oil, palm kernel oil, oils derived therefrom, and any combination thereof;

[0046] B) Subjecting the starting vegetable oil composition to a hydrolysis or alcoholysis process to form glycerol, free fatty acids and / or their non-glycerol esters;

[0047] C). Distill the free fatty acids and / or their non-glycerides obtained in step B) to obtain at least one fatty acid composition rich in C16:O-fatty acids;

[0048] D) Esterification of glycerol, the fatty acid composition rich in C16:O-fatty acids and / or their non-glycerides, and optionally a supplementary fatty acid composition, to form a crude vegetable oil blend;

[0049] E). Separate the crude vegetable oil blend to obtain a mixture of residual reactants and an artificial vegetable oil composition.

[0050] The method of the present invention yields an artificial vegetable oil composition with an increased palmitic acid content compared to the starting vegetable oil composition.

[0051] In one or more embodiments, the method includes increasing the amount of palmitic acid present at the sn2-position in the total palmitic acid in the triglycerides of the synthetic vegetable oil composition. It is believed that the method results in an increase in palmitic acid at the sn2-position compared to the starting vegetable oil composition, meaning that the amount of palmitic acid at the sn2-position (i.e., the middle position on the triglyceride) in the resulting vegetable oil composition is greater (when compared to the amount of palmitic acid at the same position in the starting vegetable oil composition).

[0052] In one or more embodiments, the starting vegetable oil composition contains less than 20% by weight of palmitic acid in the triglycerides (relative to the total weight of fatty acids in the triglycerides).

[0053] In one or more embodiments, the starting vegetable oil composition contains less than 35% by weight, such as less than 30% by weight, such as less than 25% by weight, such as less than 20% by weight, or such as less than 15% by weight, of palmitic acid in triglycerides (relative to the total weight of fatty acids in triglycerides).

[0054] In one or more embodiments, the starting vegetable oil composition contains at least 1% by weight of palmitic acid in the triglycerides (relative to the total weight of fatty acids in the triglycerides).

[0055] In one or more embodiments, the starting vegetable oil composition comprises 2 to 12% by weight of palmitic acid in triglycerides (relative to the total weight of fatty acids in triglycerides).

[0056] In one or more embodiments, the starting vegetable oil composition is selected from the group consisting of sunflower oil, rapeseed oil, canola oil, coconut oil, rice bran oil, safflower oil, corn oil, high-oleic sunflower oil, high-oleic rapeseed oil, shea butter, soybean oil, oils derived therefrom, and any combination and / or blend thereof.

[0057] In one or more embodiments, the starting vegetable oil composition does not contain pequi oil, sea buckthorn oil, cherry seed oil (also known as phulwara oil), palash seed oil, oils derived therefrom, or any combination thereof.

[0058] In one or more embodiments, the starting vegetable oil composition does not contain hydrogenated oil.

[0059] In one or more embodiments, the starting vegetable oil composition has an iodine value of at least 6, preferably at least 8, more preferably at least 15, such as at least 20, such as at least 25, such as at least 30, such as at least 35, such as at least 40, such as at least 45, such as at least 50, such as at least 55, or such as at least 60.

[0060] In one or more embodiments, the iodine value of the starting vegetable oil composition is below 160, such as below 150, such as below 140, or such as below 130.

[0061] It is highly advantageous to utilize starting vegetable oil compositions with a lower palmitic acid content and, for example, a low iodine value of 12 than palm stearin, because palmitic acid is a difficult-to-obtain source material, especially if an organic variant is required. This allows for a more economical approach.

[0062] Hydrolysis or alcoholysis can be carried out in a countercurrent reaction column under high pressure and high temperature. Oil is fed from the bottom of the column, and water or alcohol is fed from the top. Due to the density difference, water or alcohol will flow downwards through the column, while oil will strive to flow upwards. During the contact between the water or alcohol phase and the oil, hydrolysis occurs, forming fatty acids and glycerol. Glycerol will exit the column at the bottom along with excess water or alcohol, while fatty acids will exit at the top. Glycerol can be reused in the process after the water or alcohol has been removed.

[0063] In one or more embodiments, in step B), the temperature is 200 to 270°C, preferably 200 to 260°C, and more preferably 200 to 240°C.

[0064] In one or more embodiments, in step B), the pressure is 30 to 60 bar, preferably 45 to 55 bar.

[0065] In one or more embodiments, in step B), the free fatty acid comprises palmitic acid and C18-fatty acid, and / or its non-glycerides. The C18-fatty acid may comprise C18:0-fatty acid, C18:1-fatty acid, C18:2-fatty acid, and / or C18:3-fatty acid.

[0066] In another embodiment, the free fatty acids comprise palmitic acid and lauric acid (C12:0) and / or their non-glycerides. This can be the case, for example, when the starting oil is lauric oil or its blends or fractions (such as coconut oil).

[0067] In one or more embodiments, step B) further includes separating the free fatty acid and / or its non-glycerol esters from the glycerol and any water / alcohol.

[0068] In one or more embodiments, the method further includes using the glycerol obtained in step B) for esterification step D).

[0069] In one or more embodiments, in step C), a fatty acid composition rich in lauric acid and / or a fatty acid composition rich in C18-fatty acids and / or their non-glycerides are also obtained.

[0070] In one or more embodiments, after step C), the fatty acid composition rich in palmitic acid and / or its non-glycerides comprises at least 30% by weight palmitic acid, such as at least 35% by weight C16:O-fatty acid, for example at least 40% by weight palmitic acid, preferably at least 50% by weight C16:O-fatty acid, more preferably at least 75% by weight palmitic acid, preferably 85% to 97% by weight C16:O-fatty acid, and for example 90% to 99% by weight palmitic acid. Without being bound by any theory, it is believed that a very pure fraction of palmitic acid is obtained due to distillation step C).

[0071] In one or more embodiments, the supplementary fatty acid composition of step D) is a fatty acid composition rich in C18-fatty acids and / or their non-glycerides.

[0072] In one or more embodiments, the method includes using the fatty acid composition rich in C18-fatty acids and / or their non-glycerides obtained in step C) in the esterification step D).

[0073] In one or more embodiments, the esterification in step D) includes the following sub-steps:

[0074] i) Blending a fatty acid composition rich in palmitic acid and / or its non-glycerides, optionally a supplemental fatty acid composition, with glycerol to form a glycerol and free fatty acid blend;

[0075] ii) Heat the blend under reduced pressure for a period of time;

[0076] iii) Further increase the temperature and heat the blend for a period of time, while reducing the pressure relative to step ii);

[0077] iv) The blend is held at the temperature and pressure of step iii) for a period of time.

[0078] In one or more embodiments of the esterification in step D), the step of blending glycerol with the palmitic acid-rich fraction to obtain the blend (step i) is carried out in a container. The container can be any container suitable for carrying out the chemical reaction. Such a container can be, for example (but not limited to), a flask, can, tube, laboratory flask, round-bottom flask, three-necked flask, two-necked flask, single-necked flask, glass flask, or metal flask. The reaction can be carried out with or without stirring (such as agitation).

[0079] In one or more embodiments of the esterification in step D), a condenser is used. The condenser is heated to a temperature of 40°C to 150°C, such as 50°C to 90°C, or such as 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 water evaporates while the majority of the glycerol is condensed to avoid excessive loss of glycerol.

[0080] In one or more embodiments of esterification in step D), the pressure reduction in step ii) is in the range of 150 mbar to 400 mbar, or such as in the range of 175 mbar to 250 mbar.

[0081] In one or more embodiments of the esterification in step D), steps ii) and iii) are combined into one step by continuously heating the glycerol and fatty acid composition to the desired temperature under reduced pressure for a period of time.

[0082] In one or more embodiments of esterification in step D), step iii) comprises two steps: iii1) reducing the pressure (compared to step ii) over a period of time; and iii2) increasing the temperature at the reduced pressure in step iii1) over a period of time.

[0083] In one or more embodiments of esterification in step D), steps iii1) and iii2) are performed sequentially in this order.

[0084] In one or more embodiments of esterification in step D), steps iii1) and iii2) are reversed.

[0085] In one or more embodiments, the blend in step ii) is heated to at least 140 °C. In one or more embodiments, the blend in step ii) is heated to a maximum of 240 °C. Preferably, the blend is heated at a temperature of 160 to 220 °C, and advantageously at 180 to 200 °C.

[0086] In one or more embodiments of esterification in step D), the pressure reduction in step ii) is in the range of 150 mbar to 400 mbar, or such as in the range of 175 mbar to 250 mbar.

[0087] In one or more embodiments of esterification in step D), the time period in step ii) is in the range of 15 minutes to 5 hours, or such as in the range of 30 minutes to 4 hours.

[0088] In one or more embodiments of esterification in step D), the time period in step ii) is at least 15 minutes, such as at least 20 minutes, such as at least 30 minutes, such as at least 1 hour, such as at least 2 hours, or such as at least 3 hours.

[0089] In one or more embodiments of esterification in step D), the temperature in step iii) is in the range of 180 °C to 250 °C, or such as in the range of 210 °C to 230 °C.

[0090] In one or more embodiments of the esterification in step D), the blend in step iii) is heated to at least 160 °C.

[0091] In one or more embodiments of the esterification in step D), the blend in step iii) is heated to a maximum of 230 °C. In one or more embodiments, the blend in step c) is heated to a maximum of 250 °C.

[0092] As we proceed from step ii) to step iii), the temperature gradually increases. In one or more embodiments, the temperature increases from about 170 °C in step b) to about 210 °C in step c).

[0093] In one or more embodiments of esterification in step D), the pressure in step iii) is in the range of 10 mbar to 400 mbar, such as in the range of 20 mbar to 250 mbar, such as 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.

[0094] As the process proceeds from step ii) to step iii), the pressure gradually decreases. In one or more embodiments, the pressure decreases from approximately 200 mbar in step ii) to approximately 30 mbar in step iii).

[0095] In one or more embodiments of esterification in step D), the time period in step iii) is in the range of 15 minutes to 5 hours, or such as in the range of 30 minutes to 4 hours.

[0096] In one or more embodiments of esterification in step D), the time period in step iii) 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.

[0097] In one or more embodiments, during the esterification step D), the distribution of fatty acids at the sn1, sn2, and sn3 positions of the glycerol backbone exhibits a statistical distribution. Without being bound by any theory, this statistical distribution of fatty acids at the sn1, sn2, and sn3 positions of the glycerol backbone is achieved during the esterification step. Therefore, the triglyceride profile of the esterified fatty acid blend can be calculated based on its fatty acid composition using probability laws. Esterification should be understood as the process of combining a fatty acid moiety with an alcohol (particularly glycerol) to form a triglyceride. The fatty acid moiety can be understood as free fatty acids, fatty acid esters, fatty acid anhydrides, activated fatty acids, and / or the fatty acyl moiety of fatty acids.

[0098] In one or more embodiments, the method includes an additional step of utilizing residual reactants obtained during the method and recycling them back into the method.

[0099] In one or more embodiments, the step of utilizing and recycling the residual reactants obtained during the method back into the method includes: using a mixture of the residual reactants obtained from step E) and providing it to the esterification step D).

[0100] In one or more embodiments, in step E), the residual reactants include any free fatty acids and / or their non-glycerol esters, monoglycerides, glycerol, and / or water that did not react in esterification step D). In one or more embodiments, water is continuously removed during step D) to shift the reaction equilibrium toward esterification.

[0101] In one or more embodiments, the method can be run multiple times (e.g., 2, 3, 4, 5, 6, 7, 8 or more cycles) such that free fatty acids and / or their non-glycerides, monoglycerides, and glycerol that did not react during the method can be recycled back into the method multiple times. That is, free fatty acids and / or their non-glycerides, monoglycerides, and glycerol that did not react in the previous run are used in the current run, thereby obtaining new excess free fatty acids and / or their non-glycerides for use in subsequent runs, and so on.

[0102] By utilizing unreacted free fatty acids and / or their non-glycerides, monoglycerides, and glycerol during the process and recycling them back to step D), at least the unreacted palmitic acid remaining from a process cycle can be reused in the same process starting with a new amount of starting vegetable oil composition. This means that at least the palmitic acid-rich fraction obtained in the previous run is used in the current run, thereby obtaining a new palmitic acid-rich fraction for use in subsequent runs, and so on. Therefore, since palmitic acid is found to be a finite resource in nature, the method of the present invention ensures that the amount of palmitic acid wasted during the process is minimized because it keeps excess palmitic acid reused in the process.

[0103] In one or more embodiments, the separation in step E) is achieved by distillation.

[0104] In one or more embodiments, the distillation in step C) and / or step E) is fractionation.

[0105] In one or more embodiments, the distillation step is physical refining. Distillation is carried out at a temperature of at least 160 °C under reduced pressure at a level of 0.2 mbar to 200 mbar, such as 0.2 to 100 mbar, such as 1 to 100 mbar, such as 1 to 10 mbar (depending on temperature). In one or more embodiments, distillation is carried out at a temperature of at least 190 °C under reduced pressure. In one or more embodiments, distillation is carried out at a temperature of 220 °C to 260 °C under reduced pressure, such as at about 240 °C under reduced pressure. In one embodiment, chemical refining may be used instead of physical refining in step E), and those skilled in the art will know that changing the temperature to about 100 °C is acceptable.

[0106] In one or more embodiments, the method further includes neutralizing, bleaching, and / or deodorizing the artificial vegetable oil composition obtained from step E).

[0107] In one or more embodiments, the palmitic acid content in the artificial vegetable oil composition is more than twice that of the palmitic acid content in the starting vegetable oil composition.

[0108] In one or more embodiments, the palmitic acid content in the artificial vegetable oil composition is more than two and a half times higher than the palmitic acid content in the starting vegetable oil composition.

[0109] In one or more embodiments, no chemical catalyst is used in any step of the method. By avoiding the use of chemical catalysts, the method is simpler, and if an organic starting vegetable oil composition is used, the resulting synthetic vegetable oil composition can remain organic. Furthermore, no toxic byproducts, such as dialkyl ketones (DAKs), are produced. DAKs contain two alkyl chains derived from fatty acids; that is, they are ketones having straight-chain alkyl groups (C10-C24) and (C10-C24), wherein these alkyl groups may be the same or different.

[0110] In one or more embodiments, enzymes are not used in any step of the method.

[0111] In one or more embodiments, the method comprises a single esterification step (D).

[0112] The present invention also relates to an artificial vegetable oil composition having palmitic acid in triglycerides at a weight of 20% to 60% relative to the total weight of fatty acids in the triglycerides of the artificial vegetable oil composition, wherein the artificial vegetable oil composition is not derived from palm oil, palm kernel oil and oils derived therefrom.

[0113] In one or more embodiments, the proportion of palmitic acid at the sn2-position in the total palmitic acid in the triglycerides of the artificial vegetable oil composition is in the range of 30 to 35%, preferably, the palmitic acid present at the sn2-position (C16:0) in the total palmitic acid in the triglycerides of the artificial vegetable oil composition is 25 to 35% by weight.

[0114] In one or more embodiments, the proportion of palmitic acid at the sn2-position is 33% of the total C16:0-fatty acids in the triglycerides of the artificial vegetable oil composition.

[0115] In one or more embodiments, the artificial vegetable oil composition comprises 30% to 60% by weight (such as 35% to 60% and preferably 35% to 50%) of palmitic acid in triglycerides (relative to the total weight of fatty acids in the triglycerides of the artificial vegetable oil composition).

[0116] In one or more embodiments, the artificial vegetable oil composition contains less than 4% by weight, preferably less than 2% by weight, of palmitoleic acid (C16:1) present in the triglycerides (relative to the total weight of fatty acids in the triglycerides of the artificial vegetable oil composition).

[0117] In one or more embodiments, the artificial vegetable oil composition contains less than 10% by weight, preferably less than 8% by weight, and advantageously less than 6% by weight of linolenic acid (C18:3) present in triglycerides (relative to the total weight of fatty acids in the triglycerides of the artificial vegetable oil composition).

[0118] In one or more embodiments, the artificial vegetable oil composition contains less than 5% by weight, preferably less than 4% by weight, of stearic acid (C18:0) present in the triglycerides (relative to the total weight of fatty acids in the triglycerides of the artificial vegetable oil composition).

[0119] Alternatively, in one or more embodiments, the artificial vegetable oil composition comprises 5 to 25% by weight, preferably 8 to 20% by weight, and advantageously 10 to 20% by weight, of stearic acid (C18:0) present in the triglycerides (relative to the total weight of fatty acids in the triglycerides of the artificial vegetable oil composition). It is believed that artificial vegetable oil compositions having this stearic acid content provide a fatty acid composition close to that of human breast milk fat.

[0120] In one or more embodiments, the weight ratio of palmitic acid (C16:0) to stearic acid (C18:0) in the artificial vegetable oil composition is from 2:1 to 5:1, preferably from 2:1 to 4:1. The artificial vegetable oil composition preferably contains a higher amount of palmitic acid than stearic acid. This is advantageous from a nutritional point of view because the artificial vegetable oil composition having this weight ratio of palmitic acid (C16:0) to stearic acid (C18:0) mimics the ratio present in human breast milk fat.

[0121] In one or more embodiments, the artificial vegetable oil composition contains less than 5% by weight, preferably less than 3% by weight, of C20 to C24 fatty acids present in triglycerides (relative to the total weight of fatty acids in the triglycerides of the artificial vegetable oil composition).

[0122] In one or more embodiments, the artificial vegetable oil composition comprises less than 10% by weight, preferably less than 8% by weight, advantageously less than 6% by weight, and, for example, less than 4.5% by weight, of C8, C10, C12, and C14 fatty acids present in the triglycerides (relative to the total weight of fatty acids in the triglycerides of the artificial vegetable oil composition). This is possible if laurel oil is not used or only a small amount of laurel oil is used in the method.

[0123] In one or more embodiments, the artificial vegetable oil composition is not derived from pikeberry oil, sea buckthorn oil, cherry seed oil, purple mineral seed oil, or oils derived therefrom.

[0124] In one or more embodiments, the artificial vegetable oil composition is not derived from hydrogenated oil.

[0125] In one or more embodiments, the synthetic vegetable oil composition does not contain transesterified oil. Typically, transesterified oil is produced by chemical transesterification, enzymatic transesterification, or a combination thereof. Any suitable transesterification process can be used to produce transesterified oil. Suitable process conditions for transesterification can be, for example, the transesterification process conditions discussed in EP2196094.

[0126] In one or more embodiments, the artificial vegetable oil composition does not contain phospholipids.

[0127] In one or more embodiments, the starting vegetable oil composition is selected from: sunflower oil, rapeseed oil, canola oil, coconut oil, rice bran oil, safflower oil, corn oil, high-oleic sunflower oil, high-oleic rapeseed oil, shea butter, soybean oil, oils derived therefrom, and any combination and / or blend thereof.

[0128] In one or more embodiments, the artificial vegetable oil composition is obtained by the method according to the invention.

[0129] The present invention further relates to the use of the artificial vegetable oil composition prepared according to the present invention in the manufacture of infant formula.

[0130] The present invention further relates to the use of the artificial vegetable oil composition prepared according to the present invention in the manufacture of plant-based foods.

[0131] The present invention further relates to an infant formula food comprising 5% to 100% by weight of an artificial vegetable oil composition prepared according to the present invention.

[0132] Example

[0133] The following examples are for illustrative purposes only and are not intended to limit the scope of the invention in any way.

[0134] Example 1 - Distillation of FFA to obtain a C16-rich fraction, followed by esterification to obtain a C16-rich oil derived from HOSO.

[0135] The starting vegetable oil composition is decomposed into FFA (free fatty acids), water, and glycerol via countercurrent hydrolysis at high temperature and in excess water, as described, for example, in Bailey's Industrial Oil and Fats Products, Volume 2, 4th Edition. Following hydrolysis, the FFA is transferred to a distillation unit, where it is separated (fractionated) into C16-rich and C18-rich fractions, respectively.

[0136] Using FFA from HOSO starting material containing approximately 4% by weight of C16, C16 FFA can be aggregated into one fraction and C18 FFA into another fraction using SPD (short path distillation). If the distillate obtained from the SPD treatment (which is enriched in C16 compared to the starting FFA composition) is processed multiple times, palmitic acid can be aggregated until the desired level is achieved.

[0137] The experiments were conducted at temperatures of 100–115 °C and pressures of approximately 0.001 mbar, and are shown in Table 1.

[0138] Table 1: Composition of distillate after repeated SPD treatment

[0139]

[0140] *Analysis using IUPAC 2.304

[0141] In this case, approximately 26% residual C18 fatty acids were found in the C16-rich fraction. Table 2 shows the initial FFA composition based on HOSO, and the composition of the C16-rich and C18-rich FFA fractions obtained after SPD treatment.

[0142] Table 2: FFA fractions obtained from the hydrolysis of HOSO and multiple SPD treatments. Only C16:0 and C18 FFAs are shown. They together constitute approximately 99% of the HOSO starting composition.

[0143]

[0144] *Analysis using IUPAC 2.304

[0145] The palmitic acid-rich fraction can be blended with the C18-rich fraction at a ratio suitable for obtaining the desired concentration of palmitic acid in the final synthetic vegetable oil composition. For this embodiment, a final concentration of 40% palmitic acid by weight is preferred. The composition of the blend of free fatty acids used in this embodiment is shown in Table 3.

[0146] Table 3: Composition of FFA blends obtained from the HOSO starting vegetable oil composition. Only C16:0 and C18FA are shown. They together constitute approximately 99% of the starting HOSO composition.

[0147]

[0148] *Analysis using IUPAC 2.304

[0149] Subsequently, glycerol was mixed with a free fatty acid blend at a molar ratio of 1:4 (33% excess free fatty acid) in a reaction vessel, wherein the fatty acid blend in this example contained 40% by weight palmitic acid and 59% by weight C18 fatty acid (the composition of the blend is shown in Table 3). 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 over approximately 20 minutes under reduced pressure (200 mbar). Over a period of 30 to 60 minutes, the temperature was gradually increased to 210°C while the pressure was gradually decreased to 33 mbar. After reaching the final reaction temperature, the reaction mixture was maintained under these conditions for 5 hours. The resulting crude oil was then distilled at 240°C under reduced pressure to remove excess free fatty acids, yielding a final synthetic vegetable oil composition rich in C16:0 fatty acids, containing 94% TAG, 3% DAG, and 1% FFA, as shown in Table 4.

[0150] Table 4: Results of the esterification reaction

[0151]

[0152] * AOCS official method Cd 22-91

[0153] **The percentages of diglycerides and monoglycerides are given as % of acylglycerols and analyzed using AOCS Cd 11d-96.

[0154] ***IUPAC 2.205 (7th Edition + Supplement)

[0155] The FA composition of the oil is shown in Table 5.

[0156] Table 5: FA composition of esterified oil

[0157]

[0158] *Analysis using IUPAC 2.304

[0159] **Analysis using IUPAC 2.210

[0160] Example 2 – Method for increasing the palmitic acid content of vegetable oil compositions

[0161] The composition of the starting rapeseed oil is shown in Table 6.

[0162] Table 6: Composition of Starting Rapeseed Oil

[0163]

[0164] *Analysis using IUPAC 2.205 (7th edition + supplement)

[0165] **Analysis using IUPAC 2.304

[0166] The starting vegetable oil composition was fractionated into free fatty acids (FFA), glycerol, and water via standard countercurrent hydrolysis under high pressure and excess water. The FFA fraction was transferred to a distillation unit, where it was separated (fractionated) into a palmitic acid-rich fraction and a C18-rich fraction. The resulting fractions have the compositions shown in Table 7.

[0167] The characteristics of the stripping column, the applied temperature, and the reflux determine the fractionation of different fatty acids. In this case, approximately 4% residual C18 fatty acids are found in the C16-rich fraction. In principle, the amount of C18 fatty acids found in the C16-rich fraction can be reduced at the expense of the distillation column's production capacity.

[0168] Table 7: FFA fractions obtained after hydrolysis and fractionation of rapeseed oil. Only C16:0 and C18 FA are shown.

[0169]

[0170] *Analysis using IUPAC 2.304

[0171] The C16:0 fraction was mixed with the C18-rich fraction to obtain the composition of the free fatty acid blend shown in Table 8.

[0172] Table 8: FFA composition of the blends. Only C16:0 and C18 FA are shown.

[0173]

[0174] *Analysis using IUPAC 2.304

[0175] Subsequently, glycerol and a free fatty acid blend were mixed in a reaction vessel at a molar ratio of 1:4 (33% excess free fatty acid), wherein the fatty acid blend in this example contained 40% by weight palmitic acid and 58% by weight C18 fatty acid (the composition of the blend is shown in Table 3). The reaction vessel was equipped with a vacuum inlet, a cold trap, and a condenser for heating to 70°C. The reaction mixture was heated to 150°C over approximately 20 minutes under reduced pressure (200 mbar). Over a period of 30 to 60 minutes, the temperature was gradually increased to 210°C while the pressure was gradually decreased to 33 mbar. After reaching the final reaction temperature, the reaction mixture was maintained under these conditions for 5 hours. Subsequently, the obtained crude oil was distilled at 240°C under reduced pressure to remove excess free fatty acids, thereby obtaining a vegetable oil composition rich in C16:0 fatty acids, containing 96% TAG, 2% DAG, and 1% FFA, as shown in Table 9.

[0176] Table 9: Results of Esterification Reaction

[0177]

[0178] * AOCS official method Cd 22-91

[0179] **The percentages of diglycerides and monoglycerides are given as % of acylglycerols and analyzed using AOCS Cd 11d-96.

[0180] ***IUPAC 2.205 (7th Edition + Supplement)

[0181] The FA composition of the oil is shown in Table 10.

[0182] Table 10: FA composition of vegetable oil compositions

[0183]

[0184] *Analysis using IUPAC 2.304

[0185] **Analysis using IUPAC 2.210

[0186] Example 3 – Method for increasing the amount of palmitic acid in a vegetable oil composition

[0187] In this embodiment, sunflower seed oil as described in Table 11 is used as the starting vegetable oil composition.

[0188] Table 11: FFA composition of starting sunflower seed oil

[0189]

[0190] *Analysis using IUPAC 2.205 (7th edition + supplement)

[0191] **Analysis using IUPAC 2.304

[0192] The starting vegetable oil composition was fractionated into free fatty acids (FFA), glycerol, and water via standard countercurrent hydrolysis under high pressure and excess water. The FFA fraction was transferred to a distillation unit, where it was fractionated into a palmitic acid-rich fraction and a C18-rich fraction, respectively. The resulting fractions had the compositions shown in Table 12. In this case, approximately 4% residual C18 fatty acids were found in the C16-rich fraction.

[0193] Table 12: FFA fractions obtained from the hydrolysis and fractionation of sunflower seed oil. Only C16:0 and C18 FA are shown.

[0194]

[0195] *Analysis using IUPAC 2.304

[0196] The C16:0 fraction was mixed with the C18-rich fraction to obtain the composition of the free fatty acid blend shown in Table 13.

[0197] Table 13: FFA composition of the blends. Only C16:0 and C18 FA are shown.

[0198]

[0199] *Analysis using IUPAC 2.304

[0200] Subsequently, glycerol was mixed with a free fatty acid blend at a molar ratio of 1:6 (100% excess free fatty acids) in a reaction vessel, wherein the fatty acid blend in this example contained 44% by weight palmitic acid and 55% by weight C18 fatty acids (the composition of the blend is shown in Table 8). 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, and the temperature was gradually increased to 210°C over a period of 30 to 60 minutes while the pressure was gradually decreased to 33 mbar. After reaching the final reaction temperature, the reaction mixture was maintained under these conditions for 3 hours. The resulting crude oil was then distilled at 240°C under reduced pressure to remove excess free fatty acids, yielding a C16:0 fatty acid-rich vegetable oil composition containing 95% TAG, 3% DAG, and 0.5% FFA, as shown in Table 14.

[0201] Table 14: Results of the esterification process

[0202]

[0203] * AOCS official method Cd 22-91

[0204] **The percentages of diglycerides and monoglycerides are given as % of acylglycerols and analyzed using AOCS Cd 11d-96.

[0205] ***IUPAC 2.205 (7th Edition + Supplement)

[0206] The FA composition of vegetable oils is shown in Table 15.

[0207] Table 15: FA composition of vegetable oil compositions

[0208]

[0209] *Analysis using IUPAC 2.304

[0210] **Analysis using IUPAC 2.210

[0211] Example 4 – Method for increasing the palmitic acid content of vegetable oil compositions

[0212] The composition of the starting rapeseed oil is shown in Table 16.

[0213] Table 16: Composition of Starting Rapeseed Oil

[0214]

[0215] *Analysis using IUPAC 2.205 (7th edition + supplement)

[0216] **Analysis using IUPAC 2.304

[0217] The starting vegetable oil composition was fractionated into free fatty acids, glycerol, and water via standard countercurrent hydrolysis under high pressure and excess water. The FFA fraction was transferred to a distillation unit, where it was fractionated into a palmitic acid-rich fraction and a C18-rich fraction, respectively. The resulting fractions had the compositions shown in Table 17. In this case, approximately 48% residual C18 fatty acids were found in the C16-rich fraction.

[0218] Table 17: FFA fractions obtained from the hydrolysis and fractionation of rapeseed oil. Only C16:0 and C18 FFAs are shown.

[0219]

[0220] *Analysis using IUPAC 2.304

[0221] The C16:0 fraction was mixed with the C18-rich fraction to obtain the composition of the free fatty acid blend shown in Table 18.

[0222] Table 18: FFA composition of the blends. Only C16:0 and C18 FA are shown.

[0223]

[0224] *Analysis using IUPAC 2.304

[0225] Subsequently, glycerol was mixed with a free fatty acid blend at a molar ratio of 1:4 (33% excess free fatty acids) in a reaction vessel, wherein the fatty acid blend in this example contained 40% by weight palmitic acid and 57% by weight C18 fatty acids (the starting oil was rapeseed oil, and the composition of the blend is shown in Table 3). The reaction vessel was equipped with a vacuum inlet, a cold trap, and a condenser for heating to 70°C. The reaction mixture was heated to 150°C over approximately 20 minutes under reduced pressure (200 mbar). Over a period of 30 to 60 minutes, the temperature was gradually increased to 210°C while the pressure was gradually decreased to 33 mbar. After reaching the final reaction temperature, the reaction mixture was maintained under these conditions for 4.5 hours. The resulting crude oil was then distilled at 240°C under reduced pressure to remove excess free fatty acids, yielding a C16:0 fatty acid-rich synthetic vegetable oil composition containing 95% TAG, 3% DAG, and 1% FFA, as shown in Table 19.

[0226] Table 19: Results of Esterification Reaction

[0227]

[0228] * AOCS official method Cd 22-91

[0229] **The percentages of diglycerides and monoglycerides are given as % of acylglycerols and analyzed using AOCS Cd 11d-96.

[0230] ***IUPAC 2.205 (7th Edition + Supplement)

[0231] The FA composition of the oil is shown in Table 20.

[0232] Table 20: FA composition of vegetable oil compositions

[0233]

[0234] *Analysis using IUPAC 2.304

[0235] **Analysis using IUPAC 2.210

[0236] Example 5 - Method for increasing the palmitic acid content of vegetable oil compositions

[0237] The composition of the initial HOSO oil is shown in Table 21.

[0238] Table 21: HOSO Starting Oil Composition

[0239]

[0240] *Analysis using IUPAC 2.205 (7th edition + supplement)

[0241] **Analysis using IUPAC 2.304

[0242] The starting vegetable oil composition was fractionated into free fatty acids, glycerol, and water via standard countercurrent hydrolysis under high pressure and excess water. The FFA fraction was transferred to a distillation unit, where it was fractionated into a palmitic acid-rich fraction and a C18-rich fraction, respectively. The resulting fractions had the compositions shown in Table 22. In this case, approximately 60% residual C18 fatty acids were found in the C16-rich fraction.

[0243] Table 22: FFA fractions obtained from the hydrolysis and fractionation of HOSO. Only C16:0 and C18 FFAs are shown.

[0244]

[0245] *Analysis using IUPAC 2.304

[0246] In this embodiment, the C16 fraction was used directly for subsequent esterification without the addition of any other fatty acid composition. The composition of the free fatty acids used in this embodiment is shown in Table 23.

[0247] Table 23 – FFA composition of blends obtained from HOSO starting vegetable oil compositions. Only C16:0 and C18FA are shown.

[0248]

[0249] *Analysis using IUPAC 2.304

[0250] Subsequently, glycerol was mixed with a free fatty acid blend at a molar ratio of 1:4 (33% excess free fatty acid) in a reaction vessel, wherein the fatty acid blend in this example contained 40% by weight palmitic acid and 58% by weight C18 fatty acid. 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 over approximately 20 minutes under reduced pressure (200 mbar). Over a period of 30 to 60 minutes, the temperature was gradually increased to 210°C while the pressure was gradually decreased to 33 mbar. After reaching the final reaction temperature, the reaction mixture was maintained under these conditions for 5 hours. The resulting crude oil was then distilled at 240°C under reduced pressure to remove excess free fatty acids, yielding a C16:0 fatty acid-rich vegetable oil composition containing 96% TAG, 3% DAG, and 0.5% FFA, as shown in Table 24.

[0251] Table 24: Results of the esterification process

[0252]

[0253] * AOCS official method Cd 22-91

[0254] **The percentages of diglycerides and monoglycerides are given as % of acylglycerols and analyzed using AOCS Cd 11d-96.

[0255] ***IUPAC 2.205 (7th Edition + Supplement)

[0256] The FA composition of the oil is shown in Table 25.

[0257] Table 25: FA composition of vegetable oil compositions

[0258]

[0259] *Analysis using IUPAC 2.304

[0260] **Analysis using IUPAC 2.210

[0261] Example 6 - Method for increasing the palmitic acid content of vegetable oil compositions

[0262] The composition of the initial HOSO oil is shown in Table 26.

[0263] Table 26: Composition of HOSO Starting Oil

[0264]

[0265] *Analysis using IUPAC 2.205 (7th edition + supplement)

[0266] **Analysis using IUPAC 2.304

[0267] The starting vegetable oil composition was fractionated into free fatty acids, glycerol, and water via standard countercurrent hydrolysis under high pressure and excess water. The FFA fraction was transferred to a distillation unit, where it was separated (fractionated) into a palmitic acid-rich fraction and a C18-rich fraction. The resulting fractions had the compositions shown in Table 27. In this case, approximately 10% residual C18 fatty acids were found in the C16-rich fraction.

[0268] Table 27: FFA fractions obtained from the hydrolysis and fractionation of HOSO. Only C16:0 and C18 FFAs are shown.

[0269]

[0270] *Analysis using IUPAC 2.304

[0271] The C16:0 fraction was mixed with the C18-rich fraction to obtain the composition of the free fatty acid blend shown in Table 28.

[0272] Table 28: Composition of FFA blends obtained from HOSO starting vegetable oil compositions. Only C16:0 and C18FA are shown.

[0273]

[0274] *Analysis using IUPAC 2.304

[0275] Subsequently, glycerol was mixed with a free fatty acid blend at a molar ratio of 1:4 (33% excess free fatty acid) in a reaction vessel, wherein the fatty acid blend in this example contained 45% by weight palmitic acid and 54% by weight C18 fatty acid (the composition of the blend is shown in Table 18). The reaction vessel was equipped with a vacuum inlet, a cold trap, and a condenser for heating to 70°C. The reaction mixture was heated to 150°C over approximately 20 minutes under reduced pressure (200 mbar). Over a period of 30 to 60 minutes, the temperature was gradually increased to 210°C while the pressure was gradually decreased to 33 mbar. After reaching the final reaction temperature, the reaction mixture was maintained under these conditions for 5 hours. The resulting crude oil was then distilled at 240°C under reduced pressure to remove excess free fatty acids, yielding a C16:0 fatty acid-rich vegetable oil composition containing 98% TAG, 1% DAG, and 0.5% FFA, as shown in Table 29.

[0276] Table 29: Results of the esterification process

[0277]

[0278] * AOCS official method Cd 22-91

[0279] **The percentages of diglycerides and monoglycerides are given as % of acylglycerols and analyzed using AOCS Cd 11d-96.

[0280] ***IUPAC 2.205 (7th Edition + Supplement)

[0281] The FA composition of the oil is shown in Table 30.

[0282] Table 30: FA composition of vegetable oil compositions

[0283]

[0284] *Analysis using IUPAC 2.304

[0285] **Analysis using IUPAC 2.210

[0286] Example 7 - Method for increasing the palmitic acid content of vegetable oil compositions

[0287] The composition of the initial HOSO oil is shown in Table 31.

[0288] Table 31: Starting HOSO Oil Composition

[0289]

[0290] *Analysis using IUPAC 2.205 (7th edition + supplement)

[0291] **Analysis using IUPAC 2.304

[0292] The starting vegetable oil composition was fractionated into free fatty acids (FFA), glycerol, and water via standard countercurrent hydrolysis under high pressure and excess water. The FFA fraction was transferred to a distillation unit, where it was fractionated into a palmitic acid-rich fraction and a C18-rich fraction, respectively. The resulting fractions had the compositions shown in Table 32. In this case, approximately 9% residual C18 fatty acids were found in the C16-rich fraction.

[0293] Table 32: FFA fractions obtained from the hydrolysis and fractionation of HOSO. Only C16:0 and C18 FFAs are shown.

[0294]

[0295] *Analysis using IUPAC 2.304

[0296] The C16:0 fraction was mixed with the C18-rich fraction to obtain the composition of the free fatty acid blend shown in Table 33.

[0297] Table 33 – Composition of FFA blends obtained from HOSO starting vegetable oil compositions. Only C16:0 and C18FA are shown.

[0298]

[0299] *Analysis using IUPAC 2.304

[0300] Subsequently, glycerol was mixed with a free fatty acid blend at a molar ratio of 1:6 (100% excess free fatty acids) in a reaction vessel, wherein the fatty acid blend in this example contained 37% by weight palmitic acid and 61% by weight C18 fatty acids (the composition of the blend is shown in Table 23). The reaction vessel was equipped with a vacuum inlet, a cold trap, and a condenser for heating to 70°C. The reaction mixture was heated to 150°C over approximately 20 minutes under reduced pressure (200 mbar). Over a period of 30 to 60 minutes, the temperature was gradually increased to 210°C while the pressure was gradually decreased to 33 mbar. After reaching the final reaction temperature, the reaction mixture was maintained under these conditions for 3 hours. The resulting crude oil was then distilled at 240°C under reduced pressure to remove excess free fatty acids, yielding a C16:0 fatty acid-rich vegetable oil composition containing 94% TAG, 3% DAG, and 1% FFA, as shown in Table 34.

[0301] Table 34: Results of Esterification Reaction

[0302]

[0303] * AOCS official method Cd 22-91

[0304] **The percentages of diglycerides and monoglycerides are given as % of acylglycerols and analyzed using AOCS Cd 11d-96.

[0305] ***IUPAC 2.205 (7th Edition + Supplement)

[0306] The FA composition of the oil is shown in Table 35.

[0307] Table 35: FA composition of vegetable oil compositions

[0308]

[0309] *Analysis using IUPAC 2.304

[0310] **Analysis using IUPAC 2.210

[0311] Example 8 - Method for increasing the palmitic acid content of vegetable oil compositions

[0312] The composition of the starting safflower seed oil is shown in Table 36.

[0313] Table 36: Composition of Safflower Seed Starting Oil

[0314]

[0315] *Analysis using IUPAC 2.205 (7th edition + supplement)

[0316] **Analysis using IUPAC 2.304

[0317] The starting vegetable oil composition was fractionated into free fatty acids, glycerol, and water via standard countercurrent hydrolysis under high pressure and excess water. The FFA fraction was transferred to a distillation unit, where it was fractionated into a palmitic acid-rich fraction and a C18-rich fraction, respectively. The resulting fractions had the compositions shown in Table 37. In this case, approximately 19% residual C18 fatty acids were found in the C16-rich fraction.

[0318] Table 37: FFA fractions obtained from the hydrolysis and fractionation of safflower seed oil. Only C16:0 and C18 FFAs are shown.

[0319]

[0320] *Analysis using IUPAC 2.304

[0321] The C16:0 fraction was mixed with the C18-rich fraction to obtain the composition of the free fatty acid blend shown in Table 38.

[0322] Table 38: Composition of FFA blends obtained from safflower seed starting oil compositions. Only C16:0 and C18 FA are shown.

[0323]

[0324] *Analysis using IUPAC 2.304

[0325] Subsequently, glycerol was mixed with a free fatty acid blend at a molar ratio of 1:6 (100% excess free fatty acids) in a reaction vessel, wherein the fatty acid blend in this example contained 40% by weight palmitic acid and 59% by weight C18 fatty acids (the composition of the blend is shown in Table 28). 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 over approximately 20 minutes under reduced pressure (200 mbar). Over a period of 30 to 60 minutes, the temperature was gradually increased to 210°C while the pressure was gradually decreased to 33 mbar. After reaching the final reaction temperature, the reaction mixture was maintained under these conditions for 3 hours. The resulting crude oil was then distilled at 240°C under reduced pressure to remove excess free fatty acids, yielding a C16:0 fatty acid-rich synthetic vegetable oil composition containing 93% TAG, 4% DAG, and 1% FFA, as shown in Table 39.

[0326] Table 39: Results of Esterification Reaction

[0327]

[0328] * AOCS official method Cd 22-91

[0329] **The percentages of diglycerides and monoglycerides are given as % of acylglycerols and analyzed using AOCS Cd 11d-96.

[0330] ***IUPAC 2.205 (7th Edition + Supplement)

[0331] The FA composition of the oil is shown in Table 40.

[0332] Table 40: FA composition of vegetable oil compositions

[0333]

[0334] *Analysis using IUPAC 2.304

[0335] **Analysis using IUPAC 2.210

[0336] Example 9 - Method for increasing the palmitic acid content of vegetable oil compositions

[0337] The composition of the starting soybean oil is shown in Table 41.

[0338] Table 41: Starting Soybean Oil Compositions

[0339]

[0340] *Analysis using IUPAC 2.205 (7th edition + supplement)

[0341] **Analysis using IUPAC 2.304

[0342] The starting vegetable oil composition was fractionated into free fatty acids, glycerol, and water via standard countercurrent hydrolysis under high pressure and excess water. The FFA fraction was transferred to a distillation unit, where the FFA was separated or fractionated into a palmitic acid-rich fraction and a C18-rich fraction, respectively. The resulting fractions had the compositions shown in Table 42. In this case, approximately 8% residual C18 fatty acids were found in the C16-rich fraction.

[0343] Table 42: FFA fractions obtained from the hydrolysis and fractionation of soybean oil. Only C16:0 and C18 FFAs are shown.

[0344]

[0345] *Analysis using IUPAC 2.304

[0346] The C16:0 fraction was mixed with the C18-rich fraction to obtain the composition of the free fatty acid blend shown in Table 43.

[0347] Table 43: FFA composition of the blends. Only C16:0 and C18 FA are shown.

[0348]

[0349] *Analysis using IUPAC 2.304

[0350] Subsequently, glycerol was mixed with a free fatty acid blend at a molar ratio of 1:6 (100% excess free fatty acids) in a reaction vessel, wherein the fatty acid blend in this example contained 40% by weight palmitic acid and 59% by weight C18 fatty acids (the starting oil was soybean oil, and the composition of the blend is shown in Table 33). The reaction vessel was equipped with a vacuum inlet, a cold trap, and a condenser for heating to 70°C. The reaction mixture was heated to 150°C over approximately 20 minutes under reduced pressure (200 mbar). Over a period of 30 to 60 minutes, the temperature was gradually increased to 210°C while the pressure was gradually decreased to 33 mbar. After reaching the final reaction temperature, the reaction mixture was maintained under these conditions for 3 hours. The resulting crude oil was then distilled at 240°C under reduced pressure to remove excess free fatty acids, yielding a C16:0 fatty acid-rich vegetable oil composition containing 96% TAG, 2% DAG, and 0.5% FFA, as shown in Table 44.

[0351] Table 44: Results of Esterification Reaction

[0352]

[0353] * AOCS official method Cd 22-91

[0354] **The percentages of diglycerides and monoglycerides are given as % of acylglycerols and analyzed using AOCS Cd 11d-96.

[0355] ***IUPAC 2.205 (7th Edition + Supplement)

[0356] The FA composition of the oil is shown in Table 45.

[0357] Table 45: FA composition of vegetable oil compositions

[0358]

[0359] *Analysis using IUPAC 2.304

[0360] **Analysis using IUPAC 2.210

[0361] Example 10 - Method for increasing the palmitic acid content of vegetable oil compositions

[0362] The composition of the starting coconut oil is shown in Table 46.

[0363] Table 46: Coconut Starting Oil Compositions

[0364]

[0365] *Analysis using IUPAC 2.304

[0366] The starting vegetable oil composition was fractionated into free fatty acids, glycerol, and water via standard countercurrent hydrolysis under high pressure and excess water. The FFA fraction was transferred to a distillation unit, where it was fractionated into a C8:0–C14:0 rich fraction (second fraction) and a C16–C18 rich fraction (third fraction). The C16–C18 fraction could then be further distilled to obtain a C16:0 rich fraction (fourth fraction) and a C18 rich fraction (fifth fraction). The resulting fractions have the compositions shown in Table 47.

[0367] Table 47: FFA fractions obtained from the hydrolysis and fractionation of coconut oil.

[0368]

[0369] *Analysis using IUPAC 2.304

[0370] **IUPAC 2.205 (7th Edition + Supplement)**

[0371] The FFA fractions were mixed at the different ratios shown (see Table 48).

[0372] Table 48 – Composition of the three blends used as examples

[0373]

[0374] The free fatty acid composition of these three blends is shown in Table 49.

[0375] Table 49 – FFA composition of three blends obtained from the starting coconut vegetable oil composition.

[0376]

[0377] *Analysis using IUPAC 2.304

[0378] **IUPAC 2.205 (7th Edition + Supplement)**

[0379] In three separate reactions, the glycerol in question was mixed with a free fatty acid blend at a molar ratio of 1:4 (33% excess free fatty acid) in reaction vessels. The reaction vessels were equipped with a vacuum inlet, a cold trap, and a condenser heated to 70°C. The reaction mixture was heated to 150°C over approximately 20 minutes under reduced pressure (200 mbar). The temperature was gradually increased to 210°C over a period of 30 to 60 minutes, while the pressure was gradually decreased to 33 mbar. After reaching the final reaction temperature of 210°C, the reaction mixture was maintained under these conditions for 4.5 hours. The resulting crude oil was then distilled at 240°C under reduced pressure to remove excess free fatty acids, yielding the resulting C16:0 fatty acid-rich synthetic vegetable oil composition. The results for the three esterified blends are shown in Table 50.

[0380] Table 50: Results of Esterification Reactions

[0381]

[0382] * AOCS official method Cd 22-91

[0383] **The percentages of diglycerides and monoglycerides are given as % of acylglycerols and analyzed using AOCS Cd 11d-96.

[0384] The FA composition of the oil is shown in Table 51.

[0385] Table 51: FA composition of vegetable oil compositions of three blends

[0386]

[0387] *Analysis using IUPAC 2.304

[0388] **Analysis using IUPAC 2.210

[0389] ***IUPAC 2.205 (7th Edition + Supplement)

[0390] As can be seen, when compared to palm oil or any fraction of palm oil, a vegetable oil composition with a high palmitic acid content can be obtained by using coconut oil (as shown in Example 10) according to the method of the invention. Furthermore, the stearic acid (C18:0) content in the vegetable oil composition obtained from coconut oil is higher than that in the vegetable oil composition obtained from palm oil (Example 11). Therefore, the vegetable oil composition obtained from coconut oil provides a C16:0 to C18:0 weight ratio close to that found in human breast milk fat.

[0391] Example 11 - Comparative Example: Fatty acid composition of palm oil and palm oil fractions

[0392] Table 52: Comparative Example: Fatty Acid Composition of Palm Oil and Palm Oil Fractions

[0393]

[0394] *Analysis using IUPAC 2.304

[0395] **Analysis using IUPAC 2.210

[0396] As can be seen, when compared with palm oil or any fraction of palm oil, vegetable oil compositions with similar palmitic acid content can be obtained by utilizing the method according to the invention (as shown in Examples 1 to 10). The method according to the invention provides significant enrichment of palmitic acid in the starting vegetable oil composition in an efficient manner. The method efficiently utilizes palmitic acid in the starting oil composition with low palmitic acid content. Therefore, artificial vegetable oil compositions not derived from oils such as palm oil, palm kernel oil, and their derived oils can be used in infant formula.

Claims

1. A method for increasing the palmitic acid content of a starting vegetable oil composition, the method comprising the following steps: A) The starting vegetable oil composition is provided, wherein the starting vegetable oil composition contains less than 35% by weight of palmitic acid in triglycerides relative to the total weight of fatty acids in triglycerides in the starting vegetable oil composition; the starting vegetable oil composition is not selected from palm oil, palm kernel oil, oils derived therefrom, and any combination thereof; B) subjecting the starting vegetable oil composition to a hydrolysis or alcoholysis process to form glycerol, free fatty acids and / or their non-glycerol esters; C). Distill the free fatty acids and / or their non-glycerides obtained in step B) to obtain at least one fatty acid composition rich in palmitic acid; D) Esterification of glycerol, the fatty acid composition rich in palmitic acid and / or its non-glycerides, and optionally a supplementary fatty acid composition and / or its non-glycerides, to form a crude vegetable oil blend; E). The crude vegetable oil blend is separated to obtain a mixture of residual reactants and an artificial vegetable oil composition.

2. The method of claim 1, wherein the starting vegetable oil composition comprises less than 30% by weight, such as less than 25% by weight, such as less than 20% by weight, or such as less than 12% by weight of palmitic acid in the triglycerides, relative to the total weight of fatty acids in the triglycerides.

3. The method according to any one of the preceding claims, wherein the starting vegetable oil composition comprises at least 1% by weight of palmitic acid in the triglycerides relative to the total weight of fatty acids in the triglycerides.

4. The method according to any one of the preceding claims, wherein the starting vegetable oil composition comprises 2 to 12% by weight of palmitic acid in the triglycerides relative to the total weight of fatty acids in the triglycerides.

5. The method according to any one of the preceding claims, wherein the starting vegetable oil composition is selected from the group consisting of: sunflower oil, rapeseed oil, canola oil, safflower oil, corn oil, coconut oil, rice bran oil, high-oleic sunflower oil, high-oleic rapeseed oil, shea butter, soybean oil, oils derived therefrom, and any combination thereof.

6. The method according to any one of the preceding claims, wherein the starting vegetable oil composition does not contain pikeperi fruit oil, sea buckthorn oil, cherry seed oil, purple mineral seed oil, oils derived therefrom, or any combination thereof.

7. The method according to any one of the preceding claims, wherein the starting vegetable oil composition is free of hydrogenated oil.

8. The method according to any one of the preceding claims, wherein the iodine value of the starting vegetable oil composition is at least 6, preferably at least 8, more preferably at least 15, such as at least 20, such as at least 25, such as at least 30, such as at least 35, such as at least 40, such as at least 45, such as at least 50, such as at least 55 or such as at least 60.

9. The method according to any one of the preceding claims, wherein the iodine value of the starting vegetable oil composition is 160 or less, such as 150 or less, such as 140 or less, such as 130 or less.

10. The method according to any one of the preceding claims, wherein in step B), the free fatty acid comprises C16:0 fatty acid and C18 fatty acid, and / or its non-glycerides.

11. The method according to any one of the preceding claims, wherein in step B), the free fatty acid comprises palmitic acid and lauric acid (C12:0), and / or their non-glycerides.

12. The method according to any one of the preceding claims, wherein step B) further comprises separating the free fatty acid and / or its non-glycerides from the glycerol and any water / alcohol.

13. The method according to any one of the preceding claims, wherein the method further comprises using the glycerol obtained in step B) in esterification step D).

14. The method according to any one of the preceding claims, wherein in step C), a fatty acid composition rich in lauric acid and / or a fatty acid composition rich in C18 fatty acids and / or their non-glycerides are also obtained.

15. The method according to any one of the preceding claims, wherein after step C), the fatty acid composition rich in palmitic acid and / or its non-glycerides comprises at least 30% by weight of palmitic acid, such as at least 35% by weight of palmitic acid, for example at least 40% by weight of palmitic acid, preferably at least 50% by weight of palmitic acid, more preferably at least 75% by weight of palmitic acid, preferably 85% to 97% by weight of palmitic acid, and for example 90% to 99% by weight of palmitic acid.

16. The method according to any one of the preceding claims, wherein the supplementary fatty acid composition in step D) is a fatty acid composition rich in C18 fatty acids and / or their non-glycerides.

17. The method of claim 16, wherein the method comprises using the fatty acid composition rich in C18 fatty acids and / or non-glycerides obtained in step C) in the esterification step D).

18. The method according to any one of the preceding claims, wherein the esterification in step D) comprises the following sub-steps: i) Blending the fatty acid composition rich in palmitic acid and / or its non-glycerides, optionally the fatty acid composition, with glycerol to form a blend of glycerol and free fatty acids; ii) Heating the blend under reduced pressure for a period of time; iii) Further increase the temperature and heat the blend for a period of time, while simultaneously further reducing the pressure relative to step ii); iv). The blend is held at the temperature and pressure of step iii) for a period of time.

19. The method of claim 18, wherein in step ii), the blend is heated to at least 140°C.

20. The method according to claim 16 or 17, wherein in step ii), the blend is heated to a maximum of 240°C.

21. The method according to any one of claims 18 to 20, wherein in step iii), the blend is heated to at least 160°C.

22. The method according to any one of claims 18 to 21, wherein in step iii), the blend is heated to a maximum of 250°C.

23. The method according to any one of claims 18 to 22, wherein the time period in step ii) or step iii) is in the range of 15 minutes to 5 hours, such as in the range of 30 minutes to 4 hours.

24. The method according to any one of the preceding claims, wherein during the esterification step D), the distribution of fatty acids at the sn1, sn2 and sn3 positions of the glycerol backbone is statistically distributed.

25. The method according to any one of the preceding claims, wherein the method includes the additional step of using residual reactants obtained during the method and recycling them back into the method.

26. The method of claim 25, wherein the step of using and recycling the residual reactants obtained during the method back into the method comprises using a mixture of the residual reactants obtained from step E) and providing it to the esterification step D).

27. The method according to any one of the preceding claims, wherein in step E), the residual reactant comprises: any free fatty acid and / or its non-glycerol esters, monoglycerides, glycerol, and water that did not react in esterification step D).

28. The method according to any one of the preceding claims, wherein the separation in step E) is achieved by distillation.

29. The method according to any one of the preceding claims, wherein the method further comprises bleaching and / or neutralizing and / or deodorizing the vegetable oil composition obtained from the separation in step E).

30. The method according to any one of the preceding claims, wherein the content of palmitic acid in the artificial vegetable oil composition is more than twice the content of palmitic acid in the starting vegetable oil composition.

31. The method according to any one of the preceding claims, wherein the content of palmitic acid in the artificial vegetable oil composition is more than two and a half times higher than the content of palmitic acid in the starting vegetable oil composition.

32. The method according to any one of the preceding claims, wherein no chemical catalyst is used in any of the method steps.

33. The method according to any one of the preceding claims, wherein no enzyme is used in any of the method steps.

34. The method according to any one of the preceding claims, wherein the method comprises a single esterification step D).

35. A synthetic vegetable oil composition, wherein, relative to the total weight of fatty acids in triglycerides in the synthetic vegetable oil composition, the synthetic vegetable oil composition has 20% to 60% by weight of palmitic acid in triglycerides, the synthetic vegetable oil composition is not derived from palm oil, palm kernel oil and oils derived therefrom, wherein, of the total palmitic acid in the triglycerides of the vegetable oil composition, the proportion of palmitic acid at the sn2- position is in the range of 25% to 35%.

36. The synthetic vegetable oil composition according to claim 35, wherein the proportion of palmitic acid at the sn2- position in the total palmitic acid of the triglycerides of the vegetable oil composition is in the range of 25 to 35%, preferably, the proportion of palmitic acid (C16:0) at the sn2- position in the total palmitic acid of the triglycerides of the vegetable oil composition is 30 to 35% by weight.

37. The artificial vegetable oil composition according to claim 35 or 36, wherein the proportion of palmitic acid at the sn2- position in the total palmitic acid of the triglycerides in the artificial vegetable oil composition is 33%.

38. The artificial vegetable oil composition according to any one of claims 35 to 37, wherein, relative to the total weight of fatty acids in triglycerides in the artificial vegetable oil composition, the artificial vegetable oil composition comprises 30% to 60% by weight, such as 35% to 60% by weight, preferably 35% to 50% by weight, palmitic acid in triglycerides.

39. The artificial vegetable oil composition according to any one of claims 35 to 38, wherein, relative to the total weight of fatty acids in the triglycerides in the artificial vegetable oil composition, the artificial vegetable oil composition contains less than 4% by weight, preferably less than 2% by weight, palmitoleic acid (C16:1) present in the triglycerides.

40. The artificial vegetable oil composition according to any one of claims 35 to 39, wherein, relative to the total weight of fatty acids in the triglycerides in the artificial vegetable oil composition, the artificial vegetable oil composition contains less than 10% by weight, preferably less than 8% by weight, and advantageously less than 6% of linolenic acid (C18:3) present in the triglycerides.

41. The artificial vegetable oil composition according to any one of claims 35 to 40, wherein, relative to the total weight of fatty acids in the triglycerides in the artificial vegetable oil composition, the artificial vegetable oil composition contains less than 5% by weight, preferably less than 4% by weight, of stearic acid (C18:O) present in the triglycerides.

42. The artificial vegetable oil composition according to any one of claims 35 to 40, wherein, relative to the total weight of fatty acids in the triglycerides in the artificial vegetable oil composition, the artificial vegetable oil composition comprises 5 to 25% by weight, preferably 8 to 20% by weight, and advantageously 10 to 20% by weight of stearic acid (C18:O) present in the triglycerides.

43. The artificial vegetable oil composition according to any one of claims 35 to 42, wherein the total weight ratio of palmitic acid (C16:0) to stearic acid (C18:0) in the artificial vegetable oil composition is 2:1 to 5:1, preferably 2:1 to 4:

1.

44. The artificial vegetable oil composition according to any one of claims 35 to 43, wherein, relative to the total weight of fatty acids in the triglycerides in the artificial vegetable oil composition, the artificial vegetable oil composition contains less than 5% by weight, preferably less than 3% by weight, of C20 to C24 fatty acids present in the triglycerides.

45. The artificial vegetable oil composition according to any one of claims 35 to 44, wherein, relative to the total weight of fatty acids in triglycerides in the artificial vegetable oil composition, the artificial vegetable oil composition comprises less than 10% by weight, preferably less than 8% by weight, advantageously less than 6% by weight, and, for example, less than 4.5% by weight of C8, C10, C12, and C14 fatty acids present in triglycerides.

46. ​​The artificial vegetable oil composition according to any one of claims 35 to 45, wherein the artificial vegetable oil composition is not derived from pikeperi fruit oil, sea buckthorn oil, cherry seed oil, purple mineral seed oil, or oils derived therefrom.

47. The artificial vegetable oil composition according to any one of claims 35 to 46, wherein the artificial vegetable oil composition is not derived from hydrogenated oil.

48. The artificial vegetable oil composition according to any one of claims 35 to 47, wherein the artificial vegetable oil composition does not contain transesterified oil and / or phospholipids.

49. The artificial vegetable oil composition according to any one of claims 35 to 47, wherein the starting vegetable oil composition is selected from: sunflower seed oil, rapeseed oil, canola seed oil, safflower seed oil, corn oil, high-oleic sunflower seed oil, high-oleic rapeseed oil, shea butter, coconut oil, rice bran oil, soybean oil, oils derived therefrom, and any combination thereof.

50. Use of the artificial vegetable oil composition according to any one of claims 35 to 49 in the manufacture of infant formula.

51. Use of the synthetic vegetable oil composition according to any one of claims 35 to 49 in the manufacture of plant-based food products.

52. An infant formula comprising 5% to 100% by weight of an artificial vegetable oil composition according to any one of claims 34 to 49 for manufacturing plant-based food products.

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