Structured edible fat composition of and method for preparing the structured edible fat compositions

Abstract

The invention relates to a structured edible fat composition and a method for preparing structured edible fat compositions. More specifically, the invention relates to the field of edible fats derived from vegetable and animal oils free of trans fats and contaminants including 3-monochloropropane-1,2-diol (3-MCPD), 1,3-dichloropropanol (1,3-DCP), 2-monochloropropane-1,3-diol (2-MCPD), and free fatty acids (FFA) for a good sensory profile, having properties, such as fatty acid profile, melting point, and crystallization properties, that can be customized to individual customer needs. In particular, the invention relates to the method for preparing edible fats containing monounsaturated and / or polyunsaturated fatty acid compositions, which can be used to produce edible food and nutraceutical products completely free of trans isomers and other harmful contaminants.

Description

[0001] STRUCTURED EDIBLE FAT COMPOSITION AND METHOD FOR PREPARING THE STRUCTURED EDIBLE

[0002] FAT COMPOSITIONS

[0003] The invention relates to a structured edible fat composition and a method for preparing structured edible fat compositions. More specifically, the invention relates to the field of edible fats derived from vegetable and animal oils, free of trans fats and contaminants including 3-monochloropropane-l,2-diol (3-MCPD), 1,3-dichloropropanol (1,3-DCP), 2- monochloropropane-l,3-diol (2-MCPD), and free fatty acids (FFA) for a good sensory profile, having properties, such as fatty acid profile, melting point, and crystallization properties, that can be customized to individual customer needs. In particular, the invention relates to a method for preparing edible fats containing monounsaturated and / or polyunsaturated fatty acid compositions, which can be used to produce edible food and nutraceutical products completely free of trans isomers and other contaminants.

[0004] Trans fatty acids are known to impair health. Recent human studies have shown that trans fats pass into the fetus, negatively affecting neural development (Elias and Innis 1). This highlights the importance of the revision of trans fat regulations and ensuring their complete elimination from our food. Current industrial processing technologies used to produce and purify edible fats generate trans fats.

[0005] In addition to trans fats, removing saturated fatty acids (except C4-C10; due to a healthy absorption mechanism) and linoleic acid (C18:2) may also be beneficial for health.

[0006] Monounsaturated fatty acids (MUFAs) and polyunsaturated fatty acids (PUFAs) are essential for our health. However, carbon double bonds of the cis configuration naturally occurring in MUFAs and PUFAs convert to toxic trans fats during industrial processing at higher temperatures. Currently, there is no industrial process available to produce edible fats from blended vegetable oils while maintaining healthy fatty acids and without generating unhealthy trans fats.

[0007] Farajzadeh Alan et al. demonstrated a process for producing trans-free fats from palm stearin and sunflower oil. However, the fat is not purified and therefore unsuitable for consumption. The general method for producing trans-free fats is to use vegetable oil or other raw materials rich in saturated fatty acids (not containing sensitive fatty acids with cis double bonds), e.g., Noori et al., Nor aini et al., Mayamol et al., and Noor Lida et al.

[0008] The final step of crude oil purification is the deodorization, a steam distillation process to remove free fatty acids and other volatile compounds at a temperature of 240°C to 270°C depending on the type of raw material [Bockisch, M. Handbuch der Lebensmitteltechnologie - Fette und Ole. 1993, p. 484-486; 531-537], Various studies provide evidence that the deodorization step is the most important for the formation of 3- monochloropropane-l,2-diol (3-MCPD), 3-monochloropropane-l,2-diol esters (3-MCPD- FE) and glycidyl fatty acid esters (G-FE) as a result of heat exposure [Pudel, F et al. On the necessity of edible oil refining and possible sources of 3-MCPD and glycidyl esters. Euro. J. Lipid Sci. Technol . 2011, 113, 368-373; Weisshaar, R. 3-MCPD-esters in edible fats and oils - a new and worldwide problem. Euro. J. Lipid Sci. Technol. 2008, 110, 671-672], Therefore, research projects have been initiated to develop strategies to minimize the content of 3-MCPD-FE and G-FE in refined vegetable oils. In a project initiated and financed by the "Forschungskreis der Ernfahrungsindustrie" (FEI), a promising strategy was found to reduce the heat-induced contaminant formation by relatively mild thermal conditions [Pudel, F. et al. On the necessity of edible oil refining and possible sources of 3-MCPD and glycidyl esters. Eur. J. Lipid Sci. Technol. 2011, 113, 368-373], namely the replacement of the deodorization by a short path distillation process. Short path distillation has been used in many different applications when heat-sensitive compounds have to be distilled [Martins, P. F. et al., Free fatty acids separation from vegetables oil deodorizer distillate using molecular distillation process. Sep. Purif. Technol. 2006, 48, 78-84; Yang, T. et al. Diacylglycerols from butterfat: Production by glycerolysis and short path distillation and analysis of physical properties. J. Amer. Oil Chem. Soc. 2004, 81, 979-987], The gentle deacidification of vegetable oils to avoid losses of valuable substances like tocopherols is also described in the literature [U.R. Unnithan: Refining of edible oil rich in nature carotenes and vitamin E. 1999; CNY US Patent PATN 5932261; Ooi, C.K. et al. Refining of red palm oil. Elaeis 1996, 8, 20-28; Incontech. http: / / www.incontech.com / equip_syst.htm (11 / 04 / 2013)].

[0009] Publication by Alex C.M. Oliveira et al. describes the purification of Alaskan pollock and New Zealand hoki liver oil using short-path distillation at temperatures ranging from 190 to 210°C. It was shown that trans fats were not formed, but other undesirable contaminants may be formed under such conditions. [Purification of Alaskan Walleye Pollock (Gadus chalcogrammus) and New Zealand Hoki (Macruronus novaezelandiae) Liver Oil Using Short Path Distillation. Nutrients 2014, 6, 2059-2076, doi: 10.3390 / nu6052059],

[0010] Publication by Xuebing Xu et al. describes the purification and deodorization of structured lipids by short path distillation at 164 to 206°C. FFA removal was unsuccessful. The most favorable amount of remaining FFA was 0.68%, and the composition was characterized by poor sensory quality [Purification and deodorization of structured lipids by short path distillation. Eur. J. Lipid Sci. Technol. 104 (2002) 745-755],

[0011] Publication by Pudel F. et al. describes 3-MCPD- and glycidyl esters that can be mitigated in vegetable oils by short-path distillation at 150 to 222.4°C. Sensory evaluation of short-path distilled oil reveals poorer quality regarding taste, smell, and color compared to the oil after standard deodorization. The oil after standard deodorization is neutral in taste and smell, while the short-path distilled oil has an unpleasant foreign taste and smell and gives the oil an orange-red color. This requires an additional refining step. [3-MCPD- and glycidyl esters can be mitigated in vegetable oils by use of short path distillation; Euro. J. Lipid Sci. Technol. 2016, 118, 396-405],

[0012] Patent application W02015 / 047170 (publ. 2015-04-02) relates to an edible fat composition comprising a blend of vegetable oils and animal fats with a total fatty acid composition of about 3-15% of C14:0 and about 2-6% of C16:l and a total content of short chain triglycerides (SCT) C4:0 and C6:0 of < 7%. The application relates to a butter fat equivalent, in particular it describes a fat composition made of vegetable oils and animal fat, an alternative to milk fat containing trans fats in the range of 4.86 to 5.46 wt.%. Furthermore, the invention relates to a process for preparing the composition, as well as uses thereof in dairy and confectionery products. Sodium methoxide is used to produce fat in the invention, using a mixture of raw materials, followed by bleaching and distillation at temperatures above 200°C.

[0013] Patent CN102822326A (publ. 2012-12-12) and EP2554648 (published 2013-06-12) describe methods for purifying contaminants using short path distillation to remove heavy taste and bad flavour from edible fats or oils. It provides an oil or fat composition with a low MCPD- FS content X (ppm) and a hydroxyl value Y (mg KOH / g) satisfying a relationship expressed by the formula Y >1.25X+4 and has a content of trans isomers of linoleic acid more than two percentage.

[0014] The method includes a generally used refinement step, top cut distillation step, an acid treatment step, a decolouration step, a water washing step, a deodorisation step, and a thin-film evaporation treatment step. The MCPD-FE is formed during thermal treatment under acidic conditions. The thin-film distillation process is carried out under vacuum (0.02 to 2 kPa) and at high temperature (120-270 °C) to remove MCPD-FS. The amount of trans linoleic acid formed during the thin-film distillation is more than two percentage.

[0015] Patent EP2793612A1 (publ. 2014-10-29) describes a bleaching process for removing 3- MCPD. The description discloses a method for removing glycidyl esters from a vegetable oil, which comprises contacting the oil with at least 0.5% by weight of the oil of an acid- activated bleaching earth and deodorizing the oil at a temperature of less than 200°C for at least 30 minutes.

[0016] Patent EP2584908B1 (publ. 2011-12-29) discloses a non-hardening fat composition, comprising 10-65% by weight of one or more vegetable oils having a slip melting point of no more than 25°C and 35-90% by weight of one or more vegetable fats having a slip melting point of more than 25°C; wherein in said one or more vegetable fats at least 90% by weight of the constituent fatty acid chains are longer than C12, the C16:0 / C18:0-C24:0 ratio is not more than 4 and the SSU / SUS ratio is at least 1, and wherein in said composition the content of S3-type triglycerides is at least 0.5% by weight, wherein the S groups are identical or different saturated fatty acids and the U groups are identical or different unsaturated fatty acids. The fat compositions provide texture at a similar or higher level than state-of-the-art fats with the same or lower saturated fatty acid content in confectionery applications. A method for producing the fat compositions and some applications are also described.

[0017] Patent applications US2007065565A1 (publ. 2007-03-22) and US2007082112A1 (publ. 2007-04-12) describe edible oil blends having a desired fatty acid profile, such as a desired oleic acid content, a desired polyunsaturated fatty acid content, a desired linoleic or linolenic acid content. Edible oil blends that are virtually trans-free are also provided. Methods for producing edible oil blends are provided, including methods for normalizing the fatty acid profile of the edible oils. Methods for using the edible oil blends for preparing foods are also provided. The edible oil blends typically comprise a first edible oil and a second edible oil, where the first edible oil is a high oleic canola oil and the second, third, or additional edible oil is selected from canola oil, corn oil, cottonseed oil, safflower oil, soybean oil, extra virgin olive oil, sunflower oil, palm oil, MCT oil, and trioleic oil.

[0018] Patent description CN104041603A (publ. 2014-09-17) describes a method for producing a special vegetable fat powder with zero trans fatty acid for milk tea. The method for producing the special vegetable fat powder with zero trans fatty acid for milk tea comprises the following steps: preparing a water phase, preparing an oil phase, and heating the syrup; then mixing and homogenizing the water phase, the oil phase, and the syrup and carrying out heat exchange, and then carrying out spray drying to obtain the vegetable fat powder. Using hydrogenated coconut oil as the fat raw material of the vegetable fat powder can meet the requirements for the preparation of zero trans fatty acid products; taking concentrated milk whey protein as the embedding agent and the emulsifying agent, the full and thick taste and the absence of foreign taste in the vegetable fat powder can be guaranteed due to accurate control of the emulsification temperature; a scraper-type heat exchanger is added and used to exchange the heat of the material liquid, thereby guaranteeing that the microbiological index in the product meets the standard requirements.

[0019] Despite the existing solutions, reducing or completely preventing the formation of harmful fats and contaminants during the production of edible structured fats from MUFAs, and PUFAs rich vegetable oils remains a challenge. There is still a need to obtain edible fats derived from vegetable and animal oils completely free of trans isomers and contaminants including 3-monochloropropane-l,2-diol (3-MCPD), 1,3-dichloropropanol (1,3-DCP), 2- monochloropropane-l,3-diol (2-MCPD), and free fatty acids (FFA), which are formed during high-temperature oil / fat refining processes commonly used in industry. The processes used so far to obtain edible fats utilize two processes at the refining stage, i.e. bleaching and deodorization, but due to the high temperature in the range of 180-270°C used for purification, trans fats and other undesirable contaminants indicated above are formed in the obtained edible fat composition.

[0020] The aim of the invention is to develop a technology for obtaining edible fats customized to the individual consumer needs. The invention provides a method for removing and preventing the formation of all or any of the contaminants, including trans isomers, 3- monochloropropane-l,2-diol (3-MCPD), 1,3-dichloropropanol (1,3-DCP), 2- monochloropropane-l,3-diol (2-MCPD), and free fatty acids (FFA), and ultimately obtaining edible fats. In particular, the technology according to the invention does not generate trans fats during the process. In the purification stage the molecular distillation (short path distillation) at temperatures below 120°C and under reduced pressure is used, ensuring that the resulting composition is edible and the formation of trans fats and the other contaminants is avoided. The inventors avoid the use of any bleaching agents, making the production process more environmentally friendly and sustainable. Thanks to the use of lower temperatures in the distillation process and the lack of bleaching agents, the solution is also economically beneficial.

[0021] Unexpectedly, it turned out that the inventors had created a method of using short path distillation to refine oils and fats, which performs two functions in one step:

[0022] 1) removes FFA (refining and deodorization stage);

[0023] 2) the refining process does not generate contaminants such as trans fats, 3-MCPD, 1,3-DCP, and 2-MCPD. It has been shown that all of these compounds are formed during refining at high temperatures, typically around 200°C. According to the invention, a lower temperature and a higher vacuum are used (from 30°C to 120°C and from 1 mbar to 0.001 mbar), so that these contaminants are not formed at all.

[0024] The total trans fatty acid content in the final fat composition is calculated using the standard methods (PN-EN ISO 12966-1:2015-01; PN-EN ISO 12966-2:2017-05; PN-EN ISO 12966-4:2015-07). The total trans fatty acid content is the sum of all trans isomers of individual fatty acids present in the final fat composition and it is of 0 - 0.2 % or 0.2 - 0.5% or 0.5- 1% or 1-2% (w / w).

[0025] The applied technology resulted in preparing edible fats containing compositions of monounsaturated and polyunsaturated fatty acids free of trans isomers and the harmful fats and contaminants, which can be used to produce edible food and nutraceutical products.

[0026] The subject of the invention is a structured edible fat composition characterized in that the triglycerides comprise at least one unsaturated fatty acid in the form of a monounsaturated or polyunsaturated fatty acid or a combination of both acids and have a content of trans fatty acid isomers of less than 2% by weight.

[0027] Preferably, the structured edible fat composition described above is characterized in that the oil is selected from: coconut oil, macadamia oil, olive oil, olive pomace oil , rapeseed oil, sunflower oil, safflower oil, grape seed oil, palm oil, palm kernel oil, rice bran oil, animal tallow, fish oil, milk fats, butter, soybean oil, corn oil, cottonseed oil, cocoa butter, illipe fat, shea butter, castor oil, coriander oil, hazelnut oil, hemp seed oil, linseed oil, mango seed oil, peanut oil, fully hydrogenated fats and chemically, enzymatically esterified oils and / or mixtures thereof.

[0028] Preferably, the fat composition is substantially free of trans fats, and when the raw materials contain trace amounts of trans fatty acids the final product contains from 0 to 0.2%, from 0.2 to 0.5 and from 0.5 to 2%.

[0029] Preferably, the composition is free of contaminants including 3-monochloropropane-l,2- diol (3-MCPD), 1,3-dichloropropanol (1,3-DCP), 2-monochloropropane-l,3-diol (2-MCPD) and glycidyl fatty acid esters.

[0030] Preferably, the fat composition is an edible fat and is applicable to edible food and nutraceutical products.

[0031] Preferably, in food products the composition contains fatty acids within the range

[0032] Preferably, in nutraceutical products the composition contains fatty acids within the range

[0033] Another subject of the invention is a method for obtaining a structured edible fat composition comprising a hydrolysis, isolation, esterification, fractionation step, characterized in that it further comprises an interesterification step followed by a single- stage refining method using molecular distillation.

[0034] Preferably, the molecular distillation step is carried out at 30°C to 120°C and at a pressure of 1 mbar to 0.001 mbar.

[0035] Preferably, triglycerides of fatty acids (TGF) are prepared in the esterification step and edible fats are prepared in the interesterification step, wherein the molecular distillation does not generate trans fats or contaminants including 3-monochloropropane-l,2-diol (3-MCPD), 1,3-dichloropropanol (1,3-DCP), 2-monochloropropane-l,3-diol (2-MCPD) and glycidyl fatty acid esters.

[0036] Preferably, free fatty acids (FFA) are removed in the refining step.

[0037] Preferably, during the single-stage refining method using molecular distillation, free fatty acids (FFA) are removed from the resulting edible composition and the FFA content is below 0.4%, wherein the refining process does not generate contaminants including trans fats, 3- MCPD, 1 ,3-DCP and 2-MCPD.

[0038] Preferably, the resulting composition is mixed with additives selected from: decolorized rosemary extract, vitamin E and vitamin D and other fats and oils.

[0039] Preferably, the oil is selected from: coconut oil, macadamia oil, olive oil, olive pomace oil, rapeseed oil, sunflower oil, safflower oil, grape seed oil, palm oil, palm kernel oil, rice bran oil, animal tallow, fish oil, milk fats, butter, soybean oil, corn oil, cottonseed oil, cocoa butter, illipe fat , shea butter, castor oil, coriander oil, hazelnut oil, hemp seed oil, linseed oil, mango seed oil, peanut oil, fully hydrogenated fats and chemically, enzymatically esterified oils and / or mixtures thereof.

[0040] Preferably, in food products the resulting composition contains fatty acids in the range

[0041] Preferably, in nutraceutical products the resulting composition contains fatty acids in the range The attached figures allow for a better understanding of the essence of the invention: Figure 1 shows the prior art based on the flow chart of an example production process from the application W02015 / 047170. Esterification takes place between butyric fatty acid and caproic fatty acid with glycerin to produce SCT-fat (short chain triglycerides). The SCT-fat is then blended with vegetable oils and edible fat. Optionally (*) the blend is deodorized. The blend is then esterified, followed by bleaching and deodorization. The final step, packaging, is dependent on the further application process.

[0042] After esterification, two processes are used: bleaching and deodorization. Deodorization is carried out at higher temperatures (220°C-235°C), with the higher temperature generating trans fats. Approximately 5% trans fats are formed.

[0043] Generally, this process is carried out under vacuum (0.5 to 8 mbar) and at temperatures ranging from 180°C to 270°C, steam or nitrogen.

[0044] Figure 2 shows the solution according to the invention. The technology according to the invention includes 9 steps: 1) hydrolysis, 2) isolation, 3) esterification, 4) fractionation, 5) mixing of fat compositions, 6) interesterification, 7) refining (molecular distillation - short path) also referred to as purification, 8) processing, and 9) packaging.

[0045] Definitions used in the description

[0046] The term "molecular distillation", short path distillation, and wipped film distillation are used interchangeably. It is a distillation technique used in various industries to separate heat-sensitive volatile compounds and extracts.

[0047] As used herein the term "fat" refers to triglycerides of fatty acids (glycerin + three different or the same fatty acids, existing as one compound).

[0048] As used herein the abbreviation "SAF" means saturated fatty acids, the abbreviation "MUFA" means monounsaturated fatty acids, the abbreviation "PUFA" means polyunsaturated fatty acids.

[0049] As used herein the term "fatty acids" denotes aliphatic hydrocarbons with a carboxylic acid group, usually occurring without an alkyl bridge, but in rare cases also with an alkyl bridge. The term "saturated fatty acids" means fatty acids with all carbon single bonds, and "unsaturated fatty acids" means fatty acids with one or more carbon double bonds. The abbreviation "TGF" means triglycerides of fatty acids, the abbreviation "LBF" means low-boiling fractions, the abbreviation "MBF" means medium-boiling fractions, the abbreviation "HBF" means high-boiling fractions.

[0050] To better understand the invention, the solution is presented in the form of exemplary embodiments. These examples are not intended to limit the invention, but merely to provide a more detailed understanding of its possible implementations.

[0051] Examples

[0052] The technology according to the invention includes 9 steps: 1) hydrolysis, 2) isolation, 3) esterification, 4) fractionation, 5) mixing of fat compositions, 6) interesterification, 7) refining (molecular distillation - short path) also referred to as purification, 8) processing and 9) packaging.

[0053] Step 7) molecular distillation -short path distillation - is crucial for the invention. The method of using molecular distillation (shortened) for refining oils and fats performs two functions in one step:

[0054] 1) FFA is removed after the interesterification step, the product is washed with water to neutral pH, and the oil is separated. The resulting oil may contain 1 to 15 wt.% water. In some cases, additional water may be added, but not exceeding 20 wt.% of the total volume. The resulting oil mixture is distilled by short path distillation. The process is repeated until the FFA content reaches <0.4%.

[0055] 2) The refining process does not generate contaminants such as trans fats, 3-MCPD, 1,3-DCP, and 2-MCPD. It has been proven that all of these compounds are formed during refining at high temperatures, typically around 200°C. In the embodiments of the invention a lower temperature and a higher vacuum (from 30°C to 120°C and from 1 mbar to 0.001 mbar) are used.

[0056] Unlike the prior art, the solution according to the invention does not utilize bleaching and deodorization steps after interesterification of the blend. The refining process at higher temperature(>180°C) contributes to the formation of trans fats and other undesirable contaminants.

[0057] The solution according to the invention provides a method of interesterification of edible fats (without generating trans fats) without the use of bleaching agents and without deodorization stage. It should be noted that the molecular distillation method used in this invention is not intended to purify oils and fats that already contain the above-mentioned contaminants, with the exception of FFA. This method is intended to prevent the formation of the above- mentioned contaminants during the refining of oils and fats after the interesterification process to obtain edible fats.

[0058] In cases where the starting raw materials contain trace amounts of trans fatty acids, the final product may contain the same amount of trans fats, because the technology according to the invention does not assume the elimination of trans fats and other contaminants by removing them, but the use of a method in which these compounds are not formed at all, therefore these compounds are not processed according to the process of the invention and are not removed from the composition, hence in the case of the presence of trans fats (previously contained in the product) their content is usually from 0 to 0.2%, but in some cases from 0.2 to 0.5 and from 0.5 to 2%.

[0059] The raw materials used are selected from: coconut oil, macadamia oil, olive oil, olive pomace oil, rapeseed oil, sunflower oil, safflower oil, grapeseed oil, fish oil, palm oil, palm kernel oil, rice bran oil, animal tallow, milk fats, butter, soybean oil, cottonseed oil, corn oil, cocoa butter, shea butter, castor oil, coriander oil, macadamia oil, hazelnut oil, hemp oil, linseed oil, mango seed oil, peanut oil, rapeseed oil, structured triglycerides, fully hydrogenated fats and chemically, enzymatically esterified oils and mixtures thereof.

[0060] Catalysts used:

[0061] Oxides, hydroxides, methoxides and ethoxides of alkali and alkaline earth metals, such as NaOH, KOH, NaOMe (sodium methoxide), NaOEt.

[0062] GENERAL PROCEDURE

[0063] The raw materials (oils and fats) are selected from: coconut oil, macadamia oil, olive oil, olive pomace oil, rapeseed oil, sunflower oil, safflower oil, grape seed oil, fish oil, palm oil, palm kernel oil, rice bran oil, animal tallow, milk fats, butter, soybean oil, cottonseed oil, corn oil, cocoa butter, shea butter, castor oil, coriander oil, macadamia oil, hazelnut oil, hemp oil, linseed oil, mango seed oil, peanut oil, rapeseed oil, structured triglycerides, fully hydrogenated fats and chemically, enzymatically esterified oils and mixtures thereof. Raw materials (oils and fats) may be subjected to one or more of the following standard industrial processes before use: hydrogenation, fractionation, degumming, neutralization, winterization, bleaching, deodorization.

[0064] Edible fat production procedure

[0065] 1. Hydrolysis

[0066] In a double-walled vacuum reactor equipped with heating, stirring, and a condenser, oil and fats, or a combination thereof are mixed in appropriate proportions. The oil is heated to 80°C and degassed until bubbling ceases. Methanol (2 to 10% w / w) and catalyst (0.1 to 0.5% w / w) are added, followed by stirring for 3 hours at 80°C. The methanol is distilled off at ambient pressure. The mixture is cooled to room temperature and filtered.

[0067] 2. Isolation

[0068] Individual fatty acid alkyl esters are separated by molecular distillation and fractionation, or other conventional isolation techniques, or a combination thereof. Three fractions are collected:

[0069] - low-boiling fractions (LBF) [25°C to 80°C, 8 mbar to 1 mbar];

[0070] - medium-boiling fractions (MBF) [80°C to 150°C, 8 mbar to 1 mbar];

[0071] - high-boiling fractions (HBF) [150°C to 220°C, 8 mbar to 1 mbar],

[0072] 3. Esterification

[0073] In a double-walled vacuum reactor equipped with heating and stirring, LBF, MBF, and HBF are mixed separately or in combination in appropriate proportions. The oil is carefully heated to 25°C to 30°C and degassed until bubbling ceases. Glycerol (1:0.33 molar equivalent to fatty acid esters), and in some cases other fatty alcohols, e.g., cetyl alcohol, or polyols such as sorbitol or sucrose, and a catalyst (2 to 10% w / w) are added and then stirred for 4 hours at 80°C. The mixture is cooled to room temperature and filtered. Structural triglycerides are formed.

[0074] 4. Fractionation

[0075] Structural triglycerides are separated by fractional crystallization (-20°C to 35°C). In some cases, structural triglycerides are separated by short-path distillation (70°C to 90°C, 0.1 mbar to 0.001 mbar). 5. Mixing fat compositions

[0076] Raw oils and fats, including structural triglycerides, are mixed individually or in combinations in appropriate proportions. Thorough mixing of the ingredients is essential.

[0077] 6. Interesterification

[0078] In a double-walled vacuum reactor equipped with heating, stirring, and a condenser, oil and fats, or a combination thereof are mixed in appropriate proportions. The oil is heated to 80°C and degassed until bubbling ceases. A catalyst (0.1 to 0.5% w / w) is added, and the mixture is then stirred for 1 to 8 hours at 70°C until the desired melting point is reached. Methanol is distilled off at ambient pressure. The mixture is washed with water until a neutral pH is achieved, and the oil is separated using conventional separation techniques.

[0079] 7. Refining

[0080] Oils and fats are refined using short-path distillation. In some cases, additional water is added to the oil prior to distillation. Distillation is performed at 30°C to 120°C and under pressure of 1 mbar to 0.001 mbar. The process continues until the FFA content reach <0.4%. Structured edible fats are produced.

[0081] 8. Processing

[0082] Edible fats are blended with, among others, rosemary extract (<0.2% w / w) and other essential vitamin oils such as vitamin E and vitamin D. In some cases, edible fats are blended with other edible oils and fats to prepare various fat compositions. Edible fat blends are prepared.

[0083] 9. Packaging

[0084] Fat blends are packaged in appropriate containers.

[0085] Example 1

[0086] Fat blends

[0087] Confectionery fat

[0088] It is produced using a l-to-9 process from a combination of coconut oil, rice bran oil, soybean oil, corn oil, olive oil, and palm oil. Olive oil is sometimes replaced with olive pomace oil or crude olive pomace oil. Palm oil is sometimes replaced with palm kernel oil or other sources of oils and fats. The product has the following fatty acid composition:

[0089] Example la

[0090] Preparation of a milk fat replacer

[0091] Produced according to the process comprising steps 1 to 9 described above.

[0092] Stage 1. Hydrolysis

[0093] In a double-walled vacuum reactor equipped with heating, stirring and a condenser, fully hydrogenated palm oil (1030 g) was heated to 80°C and all air bubbles were removed. Sodium methoxide (13 g) and methanol (380 ml) were added and heated to 80°C for 4 hours. The resulting mixture was cooled to room temperature and filtered.

[0094] Stage 2. Isolation

[0095] The resulting mixture was diluted with methanol (150 ml) and cooled under controlled conditions to allow precrystallization. The resulting crystals were separated and dried in vacuo. They contain palmitic acid methyl ester and stearic acid methyl ester in a weight ratio of 1:2, respectively.

[0096] Step 3. Esterification

[0097] In a double-walled vacuum reactor equipped with heating, stirring and a condenser, the product from the previous batch (500 g) was mixed. The reaction mixture was degassed. Glycerol (53.1 g) and sodium methoxide (3 g) were added. The mixture was then heated to 110°C for 5 hours under vacuum. The resulting mixture was washed with cold water. The resulting solid fat was separated.

[0098] Step 4. Fractionation

[0099] It was then distilled using molecular distillation (100°C, 0.1, 0.001 mbar).

[0100] Step 5 Mixing

[0101] The resulting triglycerides (100 g) are mixed with palm oil (450 g) and coconut oil (450 g), respectively.

[0102] Stage 6. Interesterification

[0103] In a double-walled vacuum reactor equipped with heating, a stirrer, and a condenser, the above mixture is stirred and heated to 70°C for 1 hour under vacuum until bubble formation ceases. Sodium methoxide (0.5% w / w) is added, and stirring is continued for 2 hours at 70°C. The resulting mixture is cooled to room temperature and washed successively with water until the pH of the washes becomes neutral and then the fat is separated.

[0104] Stage 7. Refining, Stage 8. Processing and Stage 9. Packaging.

[0105] Distillation (100°C, 0.001 mbar) in a molecular distillator. The milk fat replacer is collected and mixed with rosemary extract (0.05%), and then packaged. Example lb

[0106] Preparation of CBR, HR-CBR and encapsulation fat

[0107] Produced in process 1-9

[0108] Step 1. Hydrolysis

[0109] In a double-walled vacuum reactor equipped with heating, stirring and a condenser, the fully hydrogenated rice bran oil (1000 g) was heated to 80°C and all air bubbles were removed. Sodium methoxide (10 g) and methanol (360 ml) were added and heated to 80°C for 5 hours. The resulting mixture was filtered.

[0110] Stage 2. Isolation

[0111] The resulting mixture was diluted with methanol (150 ml) and cooled under controlled conditions to allow precrystallization. The resulting crystals were separated at different intervals, and three combinations were prepared.

[0112] A) palmitic acid:stearic acid weight ratio of 2:1, respectively;

[0113] B) palmitic acid:stearic acid weight ratio of 1:2, respectively; and

[0114] C) palmitic acid:stearic acid weight ratio of 1:4, respectively.

[0115] All combinations were dried in vacuo.

[0116] Step 3. Esterification

[0117] In a double-walled vacuum reactor equipped with heating, stirring, and a condenser, combinations A, B, and C were individually esterified. Each combination was mixed. The mixture was degassed. Glycerol (0.33% w / w) and sodium methoxide (6% w / w) were added. The mixture was then heated to 110°C for 5 hours under vacuum. The resulting mixture was washed with cold water. The resulting solid fat was separated using conventional separation techniques.

[0118] Step 4. Fractionation

[0119] Each of the triglycerides were separately distilled, using molecular distillation (100°C, 0.1 to 0.001 mbar).

[0120] Step 5. Mixing

[0121] The resulting triglycerides were mixed with olive oil (20% w / w) to obtain mixtures I, II and III, respectively. Mixture I, Combination A (80% w / w) + olive oil (20% w / w)

[0122] Mixture II, Combination B (80% w / w) + olive oil (20% w / w)

[0123] Mixture III, Combination C (80% w / w) + olive oil (20% w / w)

[0124] Stage 6. Interesterification

[0125] In a double-walled vacuum reactor equipped with heating, a stirrer, and a condenser, the above mixtures were stirred separately and heated to 70°C for 1 hour under vacuum until bubble formation ceased. Sodium methoxide (0.5% w / w) was added, and stirring was continued for 2 hours at 70°C. The resulting mixture was cooled to room temperature and washed successively with water until the pH of the washes was neutral and then separated using conventional separation techniques. All individual fats were collected separately.

[0126] Stage 7. Refining, Stage 8. Processing and Stage 9. Packaging.

[0127] All individual fats were separately distilled (100°C, 0.001 mbar) in a molecular distiller. Each edible fat was collected and mixed with rosemary extract (0.05%) and then packed.

[0128] Edible fats obtained from mixture I are suitable for a cocoa butter replacer (CBR).

[0129] Edible fats obtained from mixture II are suitable for heat-resistant CBR.

[0130] Edible fats obtained from mixture III are suitable for encapsulation and coating.

[0131] Example 2

[0132] Fat for infant formulas

[0133] Produced by the 1-9 process from olive oil, rice bran oil, palm oil, and coconut oil. In some cases, olive oil is replaced with olive pomace oil or crude olive pomace oil. In some cases, palm oil is replaced with palm kernel oil. Specifically, the 1-4 process is used to prepare palmitic-rich structural triglycerides from rice bran oil, palm oil, or palm kernel oil, or caprylic- and capric-rich triglycerides from coconut oil. The 5-9 process is further used to produce baby fat using olive oil, coconut oil, macadamia oil, and palmitic-rich structural triglycerides in various combinations. The product has the following fatty acid composition:

[0134] Example 2a

[0135] Preparation of heart-healthy nutri-fat oil

[0136] Step 1. Hydrolysis

[0137] In a double-walled vacuum reactor equipped with heating, stirring, and a condenser, coconut oil was heated to 80°C and all air bubbles were removed. Sodium methoxide (1% w / w) and methanol (6% w / w) were added and heated to 80°C for 4 hours. The resulting mixture was filtered.

[0138] Stage 2. Isolation

[0139] The resulting mixture was distilled using molecular distillation. Three fractions were collected. - Low-boiling fractions (LBF) [80°C, 1 mbar to 0.1 mbar];

[0140] - Medium-boiling fractions (MBF) [150°C, 1 mbar to 0.1 mbar];

[0141] - High-boiling fractions (HBF) [220°C, 0.1 mbar to 0.01 mbar].

[0142] Step 3. Esterification

[0143] In a double-walled vacuum reactor equipped with heating, stirring, and a condenser, MBF and HBF (weight ratio of 8:2, respectively) were mixed. Glycerol (0.33% w / w) and sodium methoxide (6% w / w) were added. The mixture was then heated to 110°C for 5 hours. The resulting mixture was filtered.

[0144] Step 4. Fractionation

[0145] Then it was distilled using molecular distillation (210°C, 0.1 mbar to 0.001 mbar).

[0146] Step 5 Mixing

[0147] The resulting triglycerides are mixed with olive oil, weight ratio of 1:3 , respectively.

[0148] Stage 6. Interesterification

[0149] In a double-walled vacuum reactor equipped with heating, a stirrer, and a condenser, the above mixture is stirred and heated to 70°C for 1 hour under vacuum until bubble formation stops. Sodium methoxide (0.5% w / w) is added, and stirring is continued for 2 hours at 70°C. The resulting mixture is cooled to room temperature and washed successively with water until the pH of the washes becomes neutral and then it is separated.

[0150] Stage 7. Refining, Stage 8. Processing and Stage 9. Packaging.

[0151] Distillation (100°C, 0.001 mbar) in a molecular distiller. The pure fat is collected and mixed with rosemary extract (0.05%), and then packaged.

[0152] Heart-healthy Nutri-fat is obtained.

[0153] Nutri-Fat Fatty Acid Profile

Claims

Patent claims1. A structured edible fat composition characterized in that edible fats comprise at least one unsaturated fatty acid in the form of a monounsaturated or polyunsaturated fatty acid or a combination of both and have a trans fatty acid content of less than 2% by weight.

2. The structured edible fats composition according to claim 1, characterized in that the oil is selected from: coconut oil, macadamia oil, olive oil, olive pomace oil, rapeseed oil, sunflower oil, safflower oil, grape seed oil, palm oil, palm kernel oil, rice bran oil, animal tallow, fish oil, milk fats, butter, soybean oil, corn oil, cottonseed oil, cocoa butter, illipe fat, shea butter, castor oil, coriander oil, hazelnut oil, hemp seed oil, linseed oil, mango seed oil, peanut oil, fully hydrogenated fats and chemically, enzymatically esterified oils and / or mixtures thereof.

3. The fat composition according to claim 1, characterized in that it is substantially free of trans fats, and when the raw materials comprise trace amounts of trans fatty acids the final product comprises from 0 to 0.2%, from 0.2 to 0.5 and from 0.5 to 2%.

4. The fat composition according to claim 1, characterized in that it is free of the contaminants including 3-monochloropropane-l,2-diol (3-MCPD), 1,3- dichloropropanol (1,3-DCP), 2-monochloropropane-l,3-diol (2-MCPD) and glycidyl esters.

5. The fat composition according to claim 1, characterized in that it is an edible fat and is used to edible food and nutraceutical products.

6. The fat composition according to claim 1, characterized in that it contains fatty acids in food products in the range7. The fat composition according to claim 1, characterized in that it contains fatty acids in nutraceutical products in the range8. A method for preparing structured edible fat compositions according to claims 1 to7, comprising the steps of hydrolysis, isolation, esterification, fractionation, characterized in that it further comprises an interesterification step, followed by a single-stage refining method using molecular distillation.

9. The method for preparing the composition according to claim 8, characterized in that the molecular distillation is carried out at 30°C to 120°C and at a pressure of 1 mbar to 0.001 mbar.

10. The method for preparing the composition according to claim 8, characterized in that the esterification step comprises the preparation of fatty acid triglycerides (TGF), and the interesterification step comprises the preparation of edible fats, wherein said molecular distillation does not generate trans fats or contaminants including 3-monochloropropane-l,2-diol (3-MCPD), 1,3-dichloropropanol (1,3- DCP), 2-monochloropropane-l,3-diol (2-MCPD) and glycidyl esters.

11. The method for preparing the composition according to claim 8, characterized in that free fatty acids (FFA) are removed in the refining step.

12. The method for preparing the composition according to claim 8, characterized in that during the single-stage refining method using molecular distillation, free fatty acids (FFA) are removed from the obtained edible composition and the FFA content is below 0.4%, wherein the refining process does not generate contaminants including trans fats, 3-MCPD, 1,3-DCP and 2-MCPD.

13. The method for preparing the composition according to claim 8, characterized in that the obtained composition is mixed with additives selected from: deodorised rosemary extract, vitamin E and vitamin D and other fats and oils.

14. The method for preparing the composition according to claim 8, characterized in that the oil is selected from: coconut oil, macadamia oil, olive oil, olive pomace oil, rapeseed oil, sunflower oil, safflower oil, grape seed oil, palm oil, palm kernel oil, rice bran oil, animal tallow, fish oil, milk fats, butter, soybean oil, corn oil, cottonseed oil, cocoa butter, illipe fat, shea butter, castor oil, coriander oil, hazelnut oil, hemp seed oil, linseed oil, mango seed oil, peanut oil, fully hydrogenated fats and chemically, enzymatically esterified oils and / or mixtures thereof.

15. The method for preparing the composition according to claim 8, characterized in that said composition in food products contains fatty acids in the range16. The method for preparing the composition according to claim 8, characterized in that said composition in nutraceutical products contains fatty acids in the range

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