Preparation, Formulation and Application of Structured Oils

Abstract

Abstract: This patent establishes a chemical synthesis method for preparing structured oils by transesterification of low-carbon fatty acid alcohol esters and triglycerides, including the synthesis of various structured oils such as medium-chain triglycerides, short-chain triglycerides, and medium-to-long-chain triglycerides. The prepared medium-chain triglycerides, short-chain triglycerides, and medium-to-long-chain triglycerides are then scientifically formulated to form structured oils with specific functions, applicable to medical, health, and functional food applications.

Description

Technical Field

[0001] This invention belongs to the field of functional oils and fats, specifically including the chemical synthesis and preparation technology of medium-chain fatty acid triglycerides, short-chain fatty acid triglycerides, and medium-chain fatty acid triglycerides. Different types of medium-chain fatty acid triglycerides, short-chain fatty acid triglycerides, and medium-chain fatty acid triglycerides are scientifically combined to form structured oils with specific functions, which can be applied in the fields of medicine, health care, and functional foods. Background Technology

[0002] Medium-chain triglycerides (MCTs), short-chain triglycerides, and long-chain triglycerides attracted scientific attention as early as the 1950s and 1960s. Because they contain medium-chain fatty acids, their metabolic pathways differ from those of long-chain fatty acids, allowing them to provide energy to the body quickly, similar to glucose. Different types of long-chain fatty acids in MCTs can be metabolized into various prostaglandins (E1, E2, E3, etc.) that participate in regulating platelet aggregation, vasodilation, and immune function (Sanders et al., Clin. Sci. 1981.61:317-324), while others participate in cell membrane metabolism. Studies have shown that monounsaturated fatty acids are positively correlated with lowering cholesterol levels; omega-3 fatty acids are positively correlated with alleviating atherosclerosis, reducing blood viscosity, combating chronic inflammation, and reducing allergies; excessive intake of omega-6 fatty acids is positively correlated with obesity, hypertension, diabetes, and Alzheimer's disease (Zeng Xiaofei et al., Omega-3 Fatty Acids: The Guardians of Life [B] 2009). In particular, highly unsaturated omega-3 fatty acids can lower the levels of low-density lipoprotein cholesterol and triglycerides in the serum of diabetic patients and maintain brain and nervous system function. From a clinical perspective, common clinical diseases such as malignant tumors, heart disease, cardiovascular disease, pneumonia, and aging are all related to severe imbalances and breakdowns in the balance of various fatty acids.

[0003] (a) Therapeutic structured medium- and long-chain fatty acid glycerides Structured glycerides of medium- and long-chain fatty acids combine the advantages of ordinary oils while overcoming their shortcomings, providing the body with energy rapidly. To date, a series of structured oil products have been developed and applied in medicine. US 3 450 819 (1969) prepared a mixture of edible animal and vegetable oils rich in essential fatty acids and medium-chain fatty acid glycerides. This can prevent diseases caused by fat malabsorption and fatty acid imbalance, such as hyperlipidemia, obesity, pancreatitis, glycogenotoxicosis, chlamydial urine, and elephantiasis. US 4607052 (1982) regioselectively synthesized structured oils (such as EPA and DHA) linked to highly unsaturated fatty acids at the SN2 position of the glycerol molecule. These can be used to treat fat malabsorption, metabolic diseases, malnutrition caused by liver problems, and for immune regulation. US 4 528 197 (1985) developed a combined parenteral nutrition formula containing oils, amino acids, and carbohydrates. The emulsified oil, after hydrolysis, contains one medium-chain fatty acid and two long-chain fatty acids (the long-chain fatty acid must contain essential fatty acids). This serves as therapeutic nutritional support to correct excessive metabolism in patients and prevent nitrogen imbalance, progressive weight loss, and organ failure. EP 0271909 (1987) developed a structured oil containing medium- and long-chain fatty acid triglycerides. The molecule contains one C8-C10 medium-chain fatty acid, one C14-C18 long-chain fatty acid, and one C20-C22 ultra-long-chain fatty acid. The long-chain fatty acid is preferably an unsaturated fatty acid. This oil was formulated for intravenous injection and used clinically to provide nutritional support to patients with severe trauma, major surgery, and extensive burns, inhibiting excessive protein breakdown, correcting nitrogen imbalance, and preventing organ failure. It was also used to prevent and treat hyperlipidemia and arteriosclerosis. US 4776984 (1988) developed an ω-6 fatty acid structured oil by directly esterifying purified ω-6 fatty acids with glycerol at high temperature. This oil can be used to treat skin diseases. US 4753963 (1988) developed a nutritional agent suitable for both enteral and parenteral administration. This agent is a regioselective medium- to long-chain triglyceride, in which glycerol has caprylic / capric acid at the SN1 and SN3 positions, and a saturated or unsaturated fatty acid at the SN2 position. The saturated fatty acid is a C8-C18 fatty acid, and the unsaturated fatty acids are oleic acid, linoleic acid, and linolenic acid. US 4847296 (1989) developed a novel structural oil containing at least one C12 medium-chain fatty acid, at least one ω-3 or ω-6 long-chain fatty acid, and the remainder being C14- to C24 long-chain fatty acids. This structural oil is suitable as an energy source for patients with severe metabolic stress (such as sepsis, extensive burns, severe trauma, etc.). US 4 871 768 (1989) developed a structured oil containing both ω-3 fatty acids and C8-C10 medium-chain fatty acids, which can minimize infection in patients or secondary infections and protein malnutrition in high-risk patients, and is suitable for diabetic patients and cancer patients. Subsequently, US 5 081 105 (1992) further pointed out that 60% of the fatty acids in the structured oil are medium-chain fatty acids and 40% are ω-3 fatty acids. This structured oil is suitable for nutritional support therapy for cancer patients.EP 0422 490 (1990) developed a medium- to long-chain fatty acid structured oil containing C20-C24 long-chain fatty acids, which is effective in reducing hypercholesterolemia. US 5260336 (1993) developed a structured oil rich in ω-9 fatty acids, with at least one oleic acid chain and one medium-chain fatty acid in the molecule, and the remainder can be C14- to C20 long-chain fatty acids, for use in patients with excessive metabolic diseases and to minimize infection in postoperative patients. US 5 312 836 (1994) developed a structured oil containing short-chain, medium-chain, and long-chain fatty acids in the molecule for use in severely ill patients who have difficulty absorbing nutrients from the intestines and cannot obtain fiber from their daily diet (such as patients who have undergone partial small bowel resection, colon cancer patients, etc.). US 5 962 712 (1999) developed a structured oil containing medium-chain fatty acids, ω-3 fatty acids, and ω-6 fatty acids, which can regulate the body's prostaglandin synthesis pathway, reduce E2 prostaglandins, and increase E1 and E3 prostaglandins. This oil is used for nutritional support and synergistic treatment of various diseases mediated by eicosanoic acid and patients under stress. US 2003 / 003 267 2A1 prepared a regioselective (enzymatic synthesis at the SN2 position of glycerol molecule >5%) medium- and long-chain fatty acid structured oil linked to conjugated linoleic acid, used to inhibit cancer and reduce body fat accumulation. CN102 843 913 (2012) developed a medium- and long-chain fatty acid structured oil containing octadecanoic acid and formulated it with phytosterol esters for the prevention of inflammatory and autoimmune diseases. CN 103891920 (2014) describes the preparation of medium- and long-chain oils mainly containing one medium-chain fatty acid by transesterification of edible oils with medium-chain fatty acid triglycerides. These oils exhibit good cooking properties and can reduce the accumulation of body fat. CN 117694408 (2024) describes the preparation of functional blended oils by compounding natural blackcurrant seed oil, medium- and long-chain oils derived from rapeseed oil (70% content), and diglycerides. These oils are beneficial for controlling obesity and metabolic diseases.

[0004] (ii) Health-promoting structured short- and medium-chain fatty acid glycerides In the health food industry, short-, medium-, and long-chain fatty acid structured oils, with their low-calorie properties, have led to the development of a series of products. Furthermore, short-, medium-, and long-chain fatty acid structured oils with melting points similar to cocoa butter and butter have been prepared to replace expensive cocoa butter and natural butter in margarine, shortening, ice cream, pastries, candies, and biscuits.

[0005] US 2615159 (1952) developed 1-stearoyl-2,3-acetyltriglyceride, which can form polycrystalline forms and has a melting point of 30-37°C, making it suitable for use in margarine. GB 799263 (1954) improved the melting point of fats by transesterification between fats with different melting points, making it a suitable substitute for cocoa butter. US 808634 (1955) developed functional structured fats, which contain at least one C2 acid and one long-chain fatty acid in their molecules. They can be used as food coating agents to prevent water loss and as plasticizers in products such as margarine and shortening.

[0006] EP 0311167 (1988) developed triglycerides containing medium-chain, saturated long-chain, and unsaturated long-chain molecules, suitable for use in shortening and cooking oils to reduce energy intake. US 4952606 (1990) prepared functional oils suitable for daily health maintenance by transesterification of common edible oils (50%), long-chain highly unsaturated fatty acid oils (15% deep-sea fish oil), and medium-chain fatty acid triglycerides. US 5258197 (1993) prepared structured oil molecules containing more than one C2-C4 short-chain acid and more than one C16-C22 long-chain fatty acid, classifying them as low-calorie oils.

[0007] US 2009 / 0123634 describes the enzymatic synthesis of regioselective structured oils, where the glycerol molecule has a short- to medium-chain fatty acid (C2-C4 or C6-C10) at the SN2 position and a fatty acid (C2-C24) at the SN1 and 3- positions. These are low-calorie functional oils beneficial for weight control and health. US 6124486 (2000) describes the preparation of structured oils containing short- to medium-chain fatty acids (C2-C10, C16-C24) using transesterification. These are also low-calorie functional oils beneficial for obesity control and can replace or partially replace common daily oils.

[0008] US 5288512 (1994) prepared medium- and long-chain triglycerides with reduced calorie intake, including MML, MLM, LLM, and LML triglycerides. The medium-chain (M) components were C6-C10 fatty acids, and the long-chain (L) components were C17-C26 saturated fatty acids. US 5589216 (1996) developed medium- and long-chain functional oils that can reduce calories by 70%, with C22 fatty acids accounting for 40-60%. The main molecular structures of the oils were MLM and MML, with a content ≥85%, and MLM-type oils accounting for ≥40%. US 7604966 (2009) prepared regioselective conjugated linoleic acid (LSL) structured oils using enzyme catalysis, with an ω-6 / ω-3 molar ratio of 5:1 to 1:1 and containing 20% ​​oleic acid. These oils can provide rapid energy to the body, are suitable for weight control, and can also be used in low-calorie foods such as margarine, candy, and desserts.

[0009] CN 103891920 (2014) describes the preparation of medium- and long-chain oils containing one medium-chain fatty acid by transesterification of edible oils with medium-chain fatty acid triglycerides. These oils have good cooking properties and can reduce the accumulation of fat in the body.

[0010] (III) Synthesis and Preparation of Structural Fatty Acid Triglycerides The synthesis processes of structured lipids can be broadly classified into two categories: enzymatic synthesis and chemical synthesis. Enzymatic synthesis can be carried out at relatively low temperatures, with esterification or transesterification occurring at the 1,3-position using lipases or with regioselectivity. This results in regioselective esterification products with few byproducts and avoids isomerization of unsaturated fatty acids. However, it has the disadvantages of relatively high preparation costs and long reaction times. This patent focuses solely on innovations in chemical synthesis.

[0011] Chemically synthesized structured fats and oils have long been a promising industrialization path, characterized by relatively short reaction times, low costs, and competitively priced products. Chemically synthesized structured fats and oils can be broadly categorized into two types: non-regioselective synthesis and regioselective synthesis.

[0012] 1. Transesterification of short-chain triglycerides with long-chain lipids.

[0013] US 791165 (1953) describes a transesterification reaction of hydrogenated lard and triacetylglycerol as raw materials at 250-260°C for 1 hour under the catalysis of lithium aluminum ethoxide or lithium aluminum stearate, yielding a 38% yield of monostearoyl diacetyl triglyceride. Other short-chain acid triglycerides (propionic acid, butyric acid, etc.) can also be used as the reactant. US 808634 (1955) establishes a chemically catalytic transesterification reaction method for short-chain acid triglycerides and long-chain saturated fatty acid triglycerides. Catalysts include sodium metal, sodium hydride, sodium hydroxide, and sodium stearate. The reaction is carried out at 200-260°C for 15 minutes to 6 hours, forming short- to long-chain fatty acid triglycerides containing one or two long chains. US 5434278 (1995) addresses the issue of immiscibility between oils and triacetin, hindering alkaline-catalyzed transesterification. It proposes adding triglycerides of propionate or medium-chain triglycerides to the reactants to create a homogeneous phase. Under sodium alkoxide catalysis, rapid transesterification can then occur at 120–135 °C, producing acetyl-containing short, medium, and long-chain fatty acid triglycerides. US 6124486 (2000) establishes a method using potassium stearate and aluminum acetate as catalysts, employing short-chain triglycerides and long-chain triglycerides as raw materials, to perform transesterification at 230–250 °C, preparing acetylglucosides containing one or two long-chain fatty acids. US 8911813 (2014) prepared a short-to-long chain fatty acid triglyceride mainly containing two long-chain fatty acids by transesterification of short-chain triglycerides (such as triglycerides butyrate, etc.) with long-chain fatty acid triglycerides (such as hydrogenated soybean oil, soybean oil, etc.) under the catalysis of sodium alkoxide.

[0014] 2. Transesterification between long-chain lipids or between medium-chain triglycerides and long-chain lipids.

[0015] US 799263 (1954) developed optimized transesterification conditions and a continuous production method for fatty acid transesterification within the same type of oil, producing reconstructed oils rich in two saturated fatty acids and one unsaturated fatty acid. US 990034 (1961) found that the melting point of oils changes after transesterification, allowing these modified oils to replace or partially replace expensive cocoa butter. US 3450819 (1969) developed a method for esterifying medium-chain fatty acids with glycerol at 140-250°C to form medium-chain triglycerides. These triglycerides were then transesterified with edible oils (such as safflower oil, flaxseed oil, and cod oil) under the catalysis of sodium ethoxide to prepare reconstructed medium- and long-chain triglycerides. US4952606 (1990) used three types of oils as raw materials to prepare medium- and long-chain triglycerides rich in various nutrient-rich fatty acids under the catalysis of sodium ethoxide, which can be used as an intestinal or parenteral nutritional supplement. US 8221818 (2012) describes the inter-oil transesterification of medium-chain triglycerides with local edible oils (rapeseed oil, corn oil, soybean oil, etc.) under the catalysis of sodium ethoxide to form medium- and long-chain triglycerides. When combined with phytosterol esters, these triglycerides can lower LDL cholesterol and total cholesterol levels, reducing body fat accumulation. US 6238926 (2001) established the conditions for intermolecular transesterification of fats by analyzing the transesterification process of triglycerides with sodium ethoxide as a catalyst at 50-150°C. US 2005 / 0196512 describes the preparation of different types of medium- and long-chain triglycerides using various edible oils as raw materials and medium-chain triglycerides under the catalysis of sodium ethoxide. These triglycerides are then combined with phytosterol esters to form modified oils with health-promoting functions. CN1735681 (2006) describes the separation of medium- and long-chain fatty acid triglycerides prepared by sodium ethoxide catalysis using molecular distillation (210~270℃), which can prepare medium- and long-chain fatty acid triglycerides containing one long-chain fatty acid and those containing two long-chain fatty acids. CN102843913 (2012) describes the preparation of functional structured oils by transesterification of oils rich in octadecanoic acid with an appropriate amount of high-oleic rapeseed oil and medium-chain fatty acid triglycerides under sodium ethoxide catalysis. CN111304006 (2020) describes the transesterification of linseed oil with medium-chain fatty acid triglycerides under sodium ethoxide catalysis at 50~90℃, and the content of medium- and long-chain fatty acid triglycerides after the reaction is 32.47~73.51%.

[0016] 3. Regioselective chemical synthesis of structured triglycerides.

[0017] US 1529762 (1978) and US 4753963 (1988) use methyl octanoate as a raw material and glycerol for transesterification under the action of sodium alkoxide to form 1,3-octanoic acid diglyceride, which then reacts with long-chain fatty acid acyl chlorides to form regioselective 1,3-dioctanoyl long-chain fatty acid triglycerides. Alternatively, glycerol, triacetylglycerol, and oils are used as raw materials to form 1,3-fatty acid diglycerides under sodium alkoxide catalysis, which then react with fatty acid anhydrides to form regioselective structured oils. US 4234498 (1980) uses fatty acid anhydrides and dehydrated glycerols for esterification to form 1-fatty acid dehydrated glycerides, which are then acid-cleaved in a fatty acid-containing material system to obtain 1,3-difatty acid glycerides, which can then be used as raw materials to prepare structured oils. US 4607052 (1986) uses 1,3-hydroxyacetone as a starting material, first reacting it with medium-chain fatty acyl chlorides to form 1,3-medium-chain fatty acylacetone, which is then reduced with NaBH4 and reacted with highly unsaturated fatty acyl chlorides (such as EPA, DHA, etc.) to form regioselective 1,3-medium-chain and 2-long-chain fatty acid triglycerides. EP0271909 (1987) established a process for the stepwise esterification of glycerol with fatty acyl chlorides to prepare structured triglycerides with EPA, linolenic acid, and medium-chain fatty acids linked in the same molecule. EP 0311167 (1988) used fatty acyl chlorides to stepwise esterify glycerol to prepare 1-stearoyl glycerol, 2-stearoyl,3-octanoyl glycerol, and 1-stearoyl,2-unsaturated fatty acyl,3-octanoyl triglycerides, achieving the linkage of three different fatty acids in the same molecule. EP 0322027 (1988) and US5288512 (1992) used a mixture of C22 triglycerides (containing 25% monoglyceride, 50% diester, and 25% triglyceride) as raw materials and octanoic acid for esterification at high temperature until the diester content was <4%. Transesterification rearrangement was then carried out under sodium alkoxide catalysis, resulting in a product with an MML / MLM ratio of 43.5%, an LLM / LML ratio of 13.5%, an MMM ratio of 38.5%, and an LLL ratio of 1%. In contrast, direct transesterification of C22 triglycerides with medium-chain fatty acid triglycerides resulted in a product with an MML / MLM ratio of 43.9%. US 5142072 (1992) and US 5142071 (1992) use C22 fatty acid monoglycerides as raw materials to react with medium-chain fatty acid anhydrides to prepare MML / MLM medium- and long-chain fatty acid glycerides. Compared with the preparation of C22 fatty acid monoglycerides with C8~C10 medium-chain fatty acids at 140~250℃, no difatty ketones byproducts are produced. US 5504231 (1996) and US 54922714 (1996) use C22 fatty acid monoglycerides as raw materials to react with C8~C10 medium-chain fatty acids at 235~245℃ without acid or base catalysis. The resulting medium- and long-chain fatty acid glycerides have an MML / MLM content of 91.3%.This process produces difatty ketones as a byproduct. These can be reduced to 100 ppm by adding glycerol (0.1-1.0%) to the crude product and reacting it at 170-215°C for 1-15 minutes. Alternatively, it can be prepared by reacting medium-chain fatty acid diglycerides with fatty acid anhydrides at 80°C.

[0018] 4. Synthesis and preparation of medium-chain fatty acid triglycerides.

[0019] Medium-chain triglycerides (MCTs) are both structural fats and raw materials for the preparation of medium- and long-chain triglycerides. They were originally separated from coconut oil or palm oil by distillation, primarily consisting of C6-C10 fatty acid fats, but production capacity was limited. There are three main synthetic routes: high-temperature transesterification of the corresponding fatty acid lower alcohol esters with glycerol; high-temperature esterification of the corresponding fatty acids with glycerol; or first synthesizing the corresponding fatty acid diglycerides and then esterifying them with fatty acid anhydrides. JPH0193558A (1989) used medium-chain fatty acid methyl esters as raw materials for distributed transesterification with glycerol. The reaction was first catalyzed by sodium alkoxide or other bases at 160-180°C for 2 hours, followed by the addition of ZnO as a catalyst and a reaction at 200-220°C for 3 hours to form medium-chain triglycerides. Polyglycerol esters and dehydrated glycerol esters were formed as byproducts during the reaction. US 3450819 (1969) developed a method for esterifying medium-chain fatty acids with glycerol at 140-250°C to form medium-chain fatty acid triglycerides. US 5504231 (1996) pointed out that prolonged heating of fatty acids at high temperatures can form difatty ketones as a byproduct. CN 118510906 (2024) utilizes fermented short-chain fatty acids and glycerol reacting at 120°C for 5 hours in the presence of sodium hydroxide, followed by a reaction at 180-200°C for 10 hours to prepare triglycerides. CN 117412947 (2024) uses fermented C8 fatty acids reacting with glycerol under the action of lipase to form 1,3-octanoic acid diglyceride, followed by a reaction with octanoic anhydride at 80-150°C to form octanoic acid triglyceride. The resulting product, after treatment with NaHSO3, showed that the content of monochloropropanediol esters and glycidyl fatty acids was ≤0.1 ppm.

[0020] In summary, structured oils have broad application prospects in clinical treatment, nutritional health care, weight control, and functional foods. While chemically catalyzed transesterification between oils is simple, easy to implement, and low-cost, the product is a mixture of various fatty acids, making it difficult to prepare products with a single component and high purity. Although regioselective chemical synthesis methods can prepare triglycerides of specific fatty acids, they often require the use of relatively expensive and somewhat toxic raw materials such as fatty acyl chlorides and fatty acid anhydrides, involving multiple steps to form triglycerides, demanding harsh reaction conditions, and requiring stringent environmental protection standards.

[0021] This patent, building upon existing chemical synthesis of structured oils, seeks new, more convenient, efficient, and economical technical routes. It develops new synthetic methods suitable for large-scale preparation, offering cost advantages over enzymatic synthesis while maintaining the mild conditions of enzymatic synthesis, avoiding unnecessary byproducts and cis-trans structure changes in unsaturated fatty acid double bonds. Furthermore, it can prepare triglycerides of specific fatty acids. We discovered that low-carbon alcohol esters of fatty acids can undergo transesterification reactions with different fatty acid triglycerides at relatively low temperatures under chemical catalysis, efficiently preparing target structured oils. This yields oils with regioselectivity, high specific fatty acid content, and low byproducts, meeting the needs of various applications. Products include medium-chain triglycerides, short-chain and long-chain triglycerides, short-chain, medium-chain, and long-chain triglycerides, as well as medium- and long-chain triglycerides. Summary of the Invention

[0022] (a) Synthesis and preparation of medium-chain fatty acid triglycerides.

[0023] As outlined in the technical background, medium-chain triglycerides can be obtained by distillation during the processing of crude coconut oil and palm oil. However, due to their relatively low content in these natural oils, they are merely processing byproducts. During the production of lauric acid from coconut oil, a certain amount of C6-C10 medium-chain fatty acids is also generated, which can be used as raw materials for the synthesis of medium-chain triglycerides. Directly esterifying C6-C10 medium-chain fatty acids or low-carbon alcohol esters with glycerol at high temperatures for extended periods can lead to the formation of unhealthy components such as glycidyl fatty acid esters and chloroglycerol fatty acid esters. Furthermore, using C6-C10 medium-chain fatty acid acyl chlorides or anhydrides as raw materials for esterification with glycerol presents challenges such as high cost, unfriendly production environment, and environmental pollution.

[0024] This patent establishes a synthetic preparation method using transesterification of medium-chain fatty acid low-carbon alcohol esters (C6-C10 medium-chain fatty acid pure products or C1-C4 alcohol esters of mixtures thereof) with triglycerides. Triglycerides include short-chain acid (C1-C6 straight-chain or branched-chain acid) triglycerides, natural oils (coconut oil, palm oil, soybean oil, cottonseed oil, corn oil, etc.) and hydrogenated oils (hydrogenated coconut oil, hydrogenated palm oil, hydrogenated soybean oil, etc.). After sufficient transesterification, the reactants generate a certain amount of medium-chain fatty acid triglycerides, which can then be obtained by vacuum distillation or molecular distillation to achieve high purity. Its technical features are as follows: the reactants need to be pretreated to ensure their acid value is <1.0, preferably <0.5; they need to be vacuum dried at 60℃~150℃ before the reaction until the water content is <0.01%; sodium (potassium) alkoxide or magnesium alkoxide (including but not limited to sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide, etc.) or alkali metal hydroxides (including but not limited to sodium hydroxide, potassium hydroxide) are used as catalysts, and anhydrous soap (alkali metal salts of fatty acids or alkaline earth metal salts or mixtures thereof) may or may not be added as a co-catalyst, with anhydrous soap being preferred. (Alkali metal salts or alkaline earth metal salts of fatty acids or mixtures thereof), the amount of catalyst is 0.1% to 1.5% of the reactants, preferably 0.3% to 0.6%; the molar ratio of medium-chain fatty acid low-carbon alcohol esters to triglycerides is 3:1 to 15:1, preferably 9:1 to 12:1; the reaction temperature is 80℃ to 220℃, preferably 100℃ to 170℃; the reaction time is 1.0 to 5.0 hours, preferably 1.5 to 2.0 hours; a dry N2 atmosphere is maintained throughout the reaction to prevent moisture and oxygen from entering. After the transesterification reaction reaches equilibrium, the material is cooled to below 100°C. Acids (such as phosphoric acid, hydrochloric acid, sulfuric acid, acetic acid, etc.) that neutralize the catalyst base are added in measured amounts. The mixture is stirred thoroughly for 5-15 minutes, and 0.05% filter aid is added for filtration to remove residue. Then, 0.5%-1.0% of activated ultrafine silica powder and filter aid are added, and the mixture is stirred and mixed at 90-95°C for 10-15 minutes. After filtration, residual soap in the material is removed to obtain the crude product. The crude product is then separated by vacuum distillation (falling film vacuum distillation, molecular distillation). Unreacted medium-chain fatty acid low-carbon alcohol esters are recovered by distillation at 50-130°C and 50-100 Pa. Long-chain fatty acid low-carbon alcohol esters formed by the reaction are recovered by distillation at 135-175°C and 30-50 Pa. Medium-chain fatty acid triglyceride products and incompletely converted long-chain fats are separated by distillation at 185-230°C and 0.1-1.0 Pa as distillation residue. This distillation residue can be recycled as reactant. The medium-chain fatty acid triglycerides prepared have high purity (≥90%). Because glycerol is not used, the hydroxyl groups are not easily dehydrated or replaced by chlorine during the conversion process. Therefore, the content of monochloropropanediol ester and glycidyl fatty acid meets the relevant technical standards.

[0025] (II) Establishment and application of an efficient method for the synthesis and preparation of fatty acid triglycerides containing short-chain acids.

[0026] 1. Establishment of an efficient method for the synthesis and preparation of fatty acid triglycerides containing short-chain acids.

[0027] As the technical background review states, as early as the 1950s and 1960s, a method for synthesizing triglycerides of fatty acids containing short-chain acids was established, as seen in US 791165 (1953), US 5434278 (1995), and US 6124486 (2000). This method involves the transesterification of short-chain triglycerides with fatty acid triglycerides at high temperatures (200℃~260℃) under the catalysis of lithium aluminum stearate, potassium stearate, metallic sodium, sodium hydroxide, and potassium stearate and aluminum acetate. At this high temperature, unsaturated fats are very easily oxidized and deteriorate to form trans fats. Subsequently, US patent 5434278 (1995) proposed adding propionic triglycerides or medium-chain fatty acid triglycerides to the reactants to change the immiscibility between oils and triacetic acid triglycerides. Under sodium alkoxide catalysis, transesterification can be achieved at 120°C to 135°C, and the product is a mixture of fatty acid triglycerides containing different short-chain or medium-chain acids. However, there are toxic tripropionic acid triglyceride residues. US patent 8911813 (2014) proposed that triglycerides of butyrate can form a homogeneous phase with long-chain fatty acid triglycerides (such as hydrogenated soybean oil, soybean oil, etc.) and transesterify under sodium alkoxide catalysis to form fatty acid triglycerides containing butyrate. However, as a new type of structured oil, fatty acid triglycerides containing butyrate have not yet been widely promoted and applied.

[0028] We have discovered that low-carbon fatty acid esters (C1-C4 esters of pure C12-C24 fatty acids or mixtures thereof) can undergo transesterification with short-chain (C1-C4) triglycerides, preferably triacetic acid esters, under relatively mild conditions catalyzed by alkali metal or alkaline earth metal alkoxides and fatty acid soaps. This allows for the selective preparation of short-to-long-chain triglyceride products containing one long-chain fatty acid and short-to-long-chain triglyceride products containing two long-chain fatty acids. Similar to the preparation of medium-chain fatty acid triglycerides described above, the reactants require pretreatment, including alkaline washing or treatment with alkaline activated clay to achieve an acid value <1.0, preferably <0.5. Before the reaction, the reactants must be vacuum-dried at 100-150°C until the water content is <0.01%. Metal alkoxides (including but not limited to sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide, etc.) or alkali metal hydroxides (including but not limited to sodium hydroxide, potassium hydroxide, etc.) are used as catalysts, with or without the addition of anhydrous soap (fatty acid alkali). The catalyst is a metal salt or alkaline earth metal salt or a mixture thereof, preferably an anhydrous soap (alkali metal salt or alkaline earth metal salt or a mixture thereof). The amount of catalyst is 0.1% to 1.5% of the reactants, preferably 0.3% to 0.6%. When preparing short-chain triglycerides containing one long-chain fatty acid, the ratio is preferably 1.1:1.0 to 1.2:1.0. When preparing short-chain triglycerides containing two long-chain fatty acids, the ratio is preferably 2.1:1.0 to 4.0:1.0. The reaction temperature can be 90℃ to 200℃, preferably 100℃ to 150℃, and optimally 120℃ to 145℃. The reaction time is 1.0 to 5.0 hours, preferably 1.5 to 2.0 hours. A dry N2 atmosphere is maintained throughout the reaction to prevent moisture and oxygen from entering. After the transesterification reaction reaches equilibrium, the material is cooled to <100℃, and a metered amount of acid (such as phosphoric acid, acetic acid, etc.) to neutralize the catalyst base is added. After stirring thoroughly for 5-15 minutes, the solid impurities are removed by vacuum filtration. Then, 0.5%-1.0% of activated ultrafine silica powder and filter aid are added. The mixture is stirred and mixed at 90-95℃ for 10-15 minutes. The residual soap in the material is removed by vacuum filtration to obtain the crude product. The crude product is separated by vacuum distillation (falling film vacuum distillation, molecular distillation). Unreacted long-chain fatty acid low-carbon alcohol esters and a small amount of unreacted short-chain triglycerides are recovered by distillation at 135℃~170℃ and 50~100Pa. The short-to-long-chain triglyceride product containing one long-chain fatty acid is recovered by distillation at 180℃~215℃ and 1.0~20Pa. The short-to-long-chain triglyceride product containing two long-chain fatty acids is separated by distillation at 230℃~260℃ and 0.1~0.5Pa, with a yield greater than 86% (based on short-chain triglycerides). The unreacted long-chain fatty acid low-carbon alcohol esters and a small amount of unreacted short-chain triglycerides can be recycled as reactants.

[0029] 2. Prepare artificial oils using the established method for synthesizing triglycerides of fatty acids containing short-chain acids.

[0030] As outlined in the technical background, existing patents employ the following technical routes: preparing triglycerides of mono-long-chain di-short-chain acids, such as US 2615159 (1952), US 808634 (1955), and US 5258197 (1993); or obtaining them by transesterification of short-chain acid triglycerides with fats and oils, producing a mixture of triglycerides of mono-long-chain di-short-chain acids and triglycerides of di-long-chain mono-short-chain acids, such as GB799263 (1954), US 6124486 (2000), and US 2009 / 0123634. Although products with suitable melting points for margarine can be prepared, these methods are limited to the use of fats and oils, which contain various types of fatty acids that are difficult to control, or are limited to the use of fatty acyl chlorides or acid anhydrides, which are environmentally unfriendly. This patent employs a novel synthetic preparation route that can selectively prepare triglycerides of mono-long-chain and di-short-chain acids, or a mixture thereof, and can selectively prepare triglycerides of di-long-chain and di-short-chain acids from specific fatty acids or mixtures thereof.

[0031] Using a certain amount of saturated fatty acid low-carbon alcohol esters and a certain amount of unsaturated fatty acid low-carbon alcohol ester mixture as raw materials, wherein the low-carbon alcohol esters refer to esters of fatty acids C1-C4, preferably esters of fatty acids C2; the molar ratio of saturated fatty acid low-carbon alcohol esters to unsaturated fatty acid low-carbon alcohol esters is 80-95:5-20, preferably 85±5:10±5; saturated fatty acids refer to saturated fatty acids of C8-C24, preferably a mixture of saturated fatty acids of C18-C22, more preferably stearic acid + behenic acid ≥80%; unsaturated fatty acids refer to unsaturated fatty acids of C6-C24, preferably unsaturated fatty acids of C18-C22 or mixtures thereof, more preferably oleic acid + linoleic acid ≥80%. When preparing short-chain triglyceride oils containing one long-chain fatty acid, it is more preferable that the proportion of saturated fatty acid low-carbon alcohol esters is <5%; when preparing short-chain triglycerides containing two long-chain fatty acids, it is more preferable that the proportion of saturated fatty acid low-carbon alcohol esters is <10%. When synthesizing short-chain triglyceride oils containing one long-chain fatty acid using the established method described above, the molar ratio of low-carbon alcohol ester to short-chain triglyceride is 1.1~1.3:1; when synthesizing short-chain triglyceride oils containing two long-chain fatty acids, the molar ratio is 2.2~3.0:1. Triacetic acid glyceride is preferred as the reactant for short-chain triglycerides. After distillation and purification, the reaction product has a melting point of 30℃~37℃, and its acid value, saponification value, peroxide value, and other indicators meet the standards for food oils, with trans fatty acids <0.1%. It can form an amorphous polycrystalline product with a melting point similar to butter and cocoa butter, making it more suitable for the processing and production of margarine, ice cream, candy, and desserts.

[0032] 3. Using the established method for synthesizing triglycerides of fatty acids containing short-chain acids, prepare low-calorie functional oils for weight control.

[0033] As summarized in the technical background, existing patented preparation methods mainly include: transesterification of short-chain triglycerides with long-chain fats to form triglycerides containing short-chain acids (see US6124486), or esterification of short-chain triglycerides with fatty acid diglycerides and acetic anhydride (see US5258197), or enzymatic catalysis to esterify short-chain acids at the SN2 position of glycerol to form short-to-long-chain fatty acid triglycerides (US2009 / 0123634), etc. The products of triglyceride transesterification have complex compositions, the proportions of various fatty acids cannot be controlled, enzymatic methods are costly, and esterification with diglycerides and anhydrides or acyl chlorides is costly and environmentally unfriendly. This patent adopts a new synthetic preparation route with a simple process. It can selectively prepare products mainly composed of single-long-chain and two-short-chain triglycerides, or triglycerides of two-long-chain and one-short-chain acids, or mixtures thereof. It can also selectively prepare triglycerides of specific fatty acids or mixtures thereof, consisting of two long-chain and one-short-chain acids. The various fatty acids constructed in the product meet the body's needs, and the product is low in calories and nutritionally balanced.

[0034] The main component of functional oils is triglyceride oils containing two long-chain fatty acids and one short-chain acid. Long-chain fatty acids refer to saturated or unsaturated fatty acids of C8-C24, while short-chain acids refer to straight-chain or branched-chain acids of C1-C6, with acetic acid being the preferred short-chain acid. For saturated fatty acids, selections include, but are not limited to, behenic acid, stearic acid, palmitic acid, myristic acid, lauric acid, and a mixture of caprylic and capric acids. For unsaturated fatty acids, selections include, but are not limited to, oleic acid, linoleic acid, linolenic acid, and EPA+DHA. The proportion of saturated fatty acids should be <25%, and the proportion of unsaturated fatty acids should be >75%, with an ω3 to ω6 fatty acid ratio of 1:2-4. The preferred proportions of saturated fatty acids are: behenic acid ≤2.5%, stearic acid ≤5.5%, palmitic acid ≤0.5%, lauric acid ≤6.0%, caprylic / capric acid ≤16.0%, and the preferred proportions of unsaturated fatty acids are: oleic acid ≥40%, linoleic acid ≤25%, α-linolenic acid ≥10%, EPA+DHA ≥1.5%, and other unsaturated fatty acids. As reaction raw materials, saturated fatty acid low carbon alcohol esters can be obtained by compounding the corresponding fatty acids and then esterifying them with the corresponding alcohols. Unsaturated fatty acid low carbon alcohol esters can be obtained by exchanging oils rich in the corresponding unsaturated fatty acids with low carbon alcohol esters and then purifying them. For details, please refer to relevant expired patents and journal articles. For example, the method for preparing low carbon alcohol esters of oleic acid is JPH 06721B2 (1994), Cheng Yapeng et al., China Oils and Fats 2018 43 (9) 1~7; the method for preparing low carbon alcohol esters of linoleic acid is Li Xiaolu et al., Journal of Hebei Agricultural University 1989 12 (1): 127~133, Bi Yanlan et al., Food Science 2020 41 (8): 262~269; the method for preparing low carbon alcohol esters of ω6 fatty acids such as linolenic acid is US 4776984 (1988); the method for preparing low carbon alcohol esters of ω3 fatty acids such as EPA and DHA is Zhang Xiangnian et al., China Food Additives 2000, 3: 1~3; the method for preparing low carbon alcohol esters of nervonic acid is Shi Fumin et al., Food Industry 2013, 2: 61~65.

[0035] Triglycerides containing a specific fatty acid composition with one short-chain acid were prepared according to the established synthetic method. During the reaction, a low-carbon alcohol ester of fatty acid with a carbon chain >12C was first reacted with the short-chain triglyceride until one hour before the end of the reaction, at which point a low-carbon alcohol ester of fatty acid with a carbon chain ≤12C was added. This prevents the product molecule from containing both a fatty acid chain with two carbon chains ≤12C and a short-chain acid simultaneously. Alternatively, triglycerides containing a specific fatty acid composition with a short-chain acid can be prepared first, depending on the type of fatty acid (e.g., ω3, ω6, or ω9), and then mixed in a specific ratio. Antioxidants such as vitamin E and vitamin C palmitate, as well as other nutrients such as vitamins A and D, and phytosterol esters, were added to the resulting product, and it was stored under nitrogen. The product is suitable for low-calorie cooking oils, seasoning oils, and salad dressings for weight control.

[0036] (III) Establishment and application of synthesis and preparation methods for medium and long chain triglycerides.

[0037] 1. Establishment of a method for synthesizing and preparing medium- and long-chain triglycerides.

[0038] As outlined in the technical background review, the chemical synthesis of medium- and long-chain triglycerides typically involves transesterification of medium-chain fatty acid triglycerides and long-chain fatty acid triglycerides (oils) under alkaline catalysis. This preparation method is relatively simple, and the products include two main categories: triglycerides containing two medium-chain fatty acids and one long-chain fatty acid, and triglycerides containing one medium-chain fatty acid and two long-chain fatty acids. Furthermore, since the fatty acid composition of oils is not a single component but rather consists of multiple fatty acids, the resulting products are complex mixtures (US 3450819, CN1735681). When using monoglycerides as raw materials, esterification with medium-chain fatty acids at high temperatures yields medium- to long-chain triglycerides of a single fatty acid, but also forms a difatty ketone byproduct (US5504231). Esterification with medium-chain fatty acid anhydrides, while avoiding the formation of difatty ketone byproducts, is costly and environmentally unfriendly (US5142072). Stepwise esterification with fatty acid acyl chlorides and glycerol also presents similar problems (US4753963, US4607052). Enzymatic catalysis for the preparation of medium- to long-chain triglycerides involves transesterification of specific fatty acids or their lower alcohol esters with medium-chain triglycerides to form medium- to long-chain triglycerides of specific fatty acids (CN1816614, US10590443), but enzymatic transesterification reactions suffer from drawbacks such as high cost.

[0039] We have discovered that low-carbon alcohol esters of fatty acids (C1-C4 alcohol esters of pure C8-C24 fatty acids or mixtures thereof) can undergo transesterification with fatty acid (C8-C24) triglycerides under relatively mild conditions under alkaline catalysis, with or without the addition of fatty acid soap (preferably with soap). This selectively produces triglyceride products containing either one long-chain fatty acid and two medium-chain fatty acids, or two long-chain fatty acids and one medium-chain fatty acid. Because low-carbon alcohol esters of specific fatty acids are readily available and easy to prepare, this method can solve the problem of preparing medium- and long-chain fatty acid glycerides of specific fatty acids, and is simple and environmentally friendly.

[0040] The reactants require pretreatment, such as washing with alkaline water or stirring with alkali-containing activated clay to achieve an acid value <1.0, preferably <0.5. Before the reaction, they must be vacuum dried at 100℃~150℃ until the water content is <0.01%. Metal alkoxides (including but not limited to sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide, etc.) or alkali metal hydroxides (including but not limited to sodium hydroxide, potassium hydroxide, etc.) are used as catalysts. Anhydrous soap (alkali metal salts of fatty acids or alkaline earth metal salts or mixtures thereof) may or may not be added as a co-catalyst, with the addition of anhydrous soap (alkali metal salts of fatty acids or alkaline earth metal salts or mixtures thereof) being preferred. The dosage of both types of catalysts is 0.1%~1.5% of the reactants, preferably... The concentration is selected to be 0.3%~0.6%; the molar ratio of low-carbon alcohol esters of fatty acids to triglycerides is 1.1~3.5:1.0; when using edible oils as raw materials, the preferred molar ratio of low-carbon alcohol esters of medium-chain fatty acids (C8~C12) to triglycerides is 2.2~3.0:1.0; when preparing triglycerides containing 1 long-chain fatty acid and 2 medium-chain fatty acids, the preferred molar ratio is 1.1~1.3:1.0; when using medium-chain triglycerides as raw materials, the preferred molar ratio of low-carbon alcohol esters of long-chain fatty acids (C12~C24) to medium-chain triglycerides is 1.2~2.0:1.0. The reaction temperature is 95℃~220℃, preferably 135℃~150℃; the reaction time is 1.0~5.0 hours, preferably 1.5~2.0 hours; a dry N2 atmosphere is maintained throughout the reaction to prevent moisture and oxygen from entering. After the transesterification reaction reaches equilibrium, the material is cooled to <100℃, and a metered amount of acid (such as phosphoric acid, sulfuric acid, hydrochloric acid, acetic acid, etc.) to neutralize the catalyst base is added. After stirring thoroughly for 5~15 minutes, the mixture is filtered to remove solid impurities. Then, 0.5%~1.0% of activated ultrafine silica powder and filter aid are added, and the mixture is stirred and mixed at 90~95℃ for 10~15 minutes. The residue soap in the material is removed by filtration to obtain the crude product. The crude product is separated by vacuum distillation (falling film vacuum distillation, molecular distillation). Unreacted medium-chain fatty acid lower alcohol esters are recovered by distillation at 60℃~130℃ and 50~100Pa. Unreacted fatty acid lower alcohol esters are also recovered by distillation at 135℃~170℃ and 50~100Pa. A small amount of unreacted medium-chain triglycerides are recovered by distillation at 180℃~210℃ and 5~25Pa. The medium-to-long-chain triglyceride product containing one long-chain fatty acid formed by the reaction is distilled off at 210℃~240℃ and 0.1~0.5Pa. The medium-to-long-chain triglyceride product containing two long-chain fatty acids is separated by distillation at 250℃~260℃ and ≤0.1Pa. The unreacted fatty acid lower alcohol esters and a small amount of unreacted medium-chain triglycerides can be recycled as reactants.

[0041] 2. Prepare medium- and long-chain triglycerides in functional edible oils by establishing a synthetic method for medium- and long-chain triglycerides.

[0042] As summarized in the technical background, existing patented methods for preparing medium- and long-chain fatty acid triglycerides for health oils include: transesterification of edible oils with medium-chain triglycerides to form triglycerides containing one or two medium chains, such as CN103891920; esterification of long-chain monoglycerides or diglycerides with medium-chain fatty acids or anhydrides to form triglycerides containing one or two medium chains, such as US5288512 and US5589216; and stepwise esterification of medium- and long-chain fatty acyl chlorides with glycerol to form triglycerides containing one medium chain, etc., which makes it difficult to optimize the proportion of long-chain fatty acids. In contrast, this patent adopts a new synthetic preparation route, which can selectively prepare products mainly composed of triglycerides of two long-chain mono- and medium-chain acids, or select specific fatty acids and their mixtures to prepare products mainly composed of triglycerides of one long-chain and two medium-chain acids. The product contains triglycerides of long-chain mono- and medium-chain acids in a molar ratio of 1.0:0.0~0.9, forming a scientific formula that can quickly provide the body with energy while ensuring a balanced intake of various fatty acids, thus achieving health benefits.

[0043] The structure of commonly used edible oils was modified, and medium- and long-chain triglycerides were prepared according to the above-mentioned synthesis method for medium- and long-chain triglycerides. The process included two reactions. The first reaction involved transesterification of medium-chain fatty acid low-carbon alcohol esters with oils to form medium- and long-chain triglycerides containing two long-chain fatty acids, while also producing low-carbon alcohol esters of fatty acids from the oils. The second reaction involved transesterification of the low-carbon alcohol esters of fatty acids from the oils formed in the first reaction with medium-chain fatty acid triglycerides to form medium- and long-chain triglycerides containing one long-chain fatty acid, while also producing low-carbon alcohol esters of medium-chain fatty acids (which can be recycled as raw materials for the first reaction). The crude products of medium- and long-chain triglycerides containing one long-chain fatty acid obtained from the first and second reactions were purified and separated according to the established separation and purification method to obtain medium- and long-chain triglycerides containing one long-chain fatty acid and medium- and long-chain triglyceride products containing two long-chain fatty acids, corresponding to the oils. By externally adding short-chain or medium-chain triglycerides rich in omega-3 fatty acids, the omega-3 fatty acid:omega-6 fatty acid ratio is adjusted to 1.0:2.0~5.0. This avoids deliberately pursuing the optimal fatty acid ratio through structured oils (LSL type) (US 7604966), resulting in a new type of low-cost, health-promoting edible oil. It retains the nutritional functions of various fatty acids while highlighting the rapid energy provision, rapid metabolism, and non-fat accumulation benefits of medium-chain fatty acids. It can be used for synergistic nutritional therapy in individuals with lipid absorption and metabolism abnormalities, cardiovascular and cerebrovascular diseases, and those who are weak, chronically ill, or in emergency situations. It can also be used as a healthy oil in the production of pastries, desserts, and candies.

[0044] Commonly used edible oils include, but are not limited to, peanut oil, rapeseed oil, sunflower seed oil, olive oil, tea seed oil, flaxseed oil, safflower seed oil, grapeseed oil, corn oil, soybean oil, palm oil, coconut oil, and cottonseed oil. These are processed to form medium- and long-chain triglycerides. In addition to adding medium- and long-chain triglycerides or short- and long-chain triglycerides of ω3 fatty acids to make the ω3 fatty acid:ω6 fatty acid ratio 1.0:2.0~5.0, other nutrients can also be added, such as antioxidants vitamin E, vitamin C palmitate and vitamins A and D, lecithin, phytosterol esters, astaxanthin, coenzyme Q10, ergosyl saline, phosphatidylserine, etc., to form the final product, functional edible oils.

[0045] 3. To prepare medium- and long-chain triglycerides suitable for clinical treatment by establishing a synthetic method for medium- and long-chain triglycerides.

[0046] As described in the technical background, long-chain triglycerides of active fatty acids possess the characteristics of rapidly providing energy, enhancing protein synthesis, preventing excessive metabolism under stress, correcting nitrogen imbalances in metabolism, and preventing organ failure. Therapeutic long-chain lipid molecules typically contain essential fatty acids, such as ω3 and ω6 fatty acids, with optimized ratios of ω3, ω6, and ω9, preferably bonded to the SN1 and SN3 positions of glycerol molecules. Since these molecules usually contain only one medium-chain fatty acid, they require bio-enzymatic synthesis or regioselective chemical synthesis to construct long-chain triglycerides containing two active fatty acids within the same molecule, resulting in high preparation costs. In contrast, this patent employs a novel synthetic preparation route, selectively preparing products primarily composed of triglycerides with two long-chain mono- and medium-chain acids or triglycerides primarily composed of mono- and long-chain di- and medium-chain acids. It also allows for the selection of specific fatty acids and mixtures to prepare triglycerides primarily composed of two long-chain and one short-chain acid, ensuring that the amount and ratio of saturated or unsaturated fatty acids meet scientific formulation requirements. This guarantees sufficient medium-chain fatty acids to rapidly provide energy to the body, sufficient essential fatty acids to support bodily functions, and simultaneously ensures the completeness of nutritional components by considering important fatty acids. The product is prepared using the established method through these two pathways.

[0047] Pathway 1: Using oils rich in essential fatty acids, blending them to achieve suitable proportions of various fatty acids to meet synergistic therapeutic and nutritional support functions, and using these as raw materials to prepare products with specific fatty acids, primarily triglycerides of long-chain mono- and medium-chain acids, according to established methods. Specifically, using flaxseed oil, perilla seed oil, borage seed oil, etc., as sources of ω3 fatty acids (content greater than 55%), safflower seed oil, sunflower seed oil, grape seed oil, etc., as sources of ω6 fatty acids (content greater than 65%), and improved varieties of high-oleic sunflower seed oil / high-oleic safflower seed oil, etc., as sources of oleic acid (content greater than 80%), the oils are blended in a specific ratio to achieve an ω3 fatty acid to ω6 fatty acid ratio of 1:2~5, with oleic acid accounting for ≥30%. A blend of oils containing ≥20% flaxseed oil, ≤45% safflower seed oil, and ≥35% high-oleic sunflower seed oil is processed according to the established method to form a crude triglyceride product mainly containing one medium-chain and two long-chain fatty acids. This product is then frozen at 0℃±5℃ overnight to crystallize the partially saturated acid triglycerides, followed by pressure filtration to obtain the final product. Other nutrients are added, such as antioxidants like vitamin E, vitamin C palmitate, and vitamins A and D; EPA, DHA medium- and long-chain or short- and long-chain triglycerides; nervonic acid medium- and long-chain or short- and long-chain triglycerides; lecithin, phytosterol esters; astaxanthin, coenzyme Q10, ergosylphosphatidylserine, etc., to form the final product. This product can be used as a cooking oil or packaged into soft capsules for the prevention and synergistic treatment of diseases with fatty acid metabolism imbalances (such as rheumatoid arthritis, arteriosclerosis and thrombosis, allergic asthma, enteritis, etc.), as well as for energy support in cases of malnutrition and chronic weakness (such as wasting diseases like tumors); it can also be used as a raw material for clinical fat emulsions.

[0048] Pathway Two: Low-carbon alcohol esters of essential fatty acids (such as linoleic acid and linolenic acid), important bioactive fatty acids (such as oleic acid, octadecenetetraic acid, EPA, DHA, and nervonic acid), and a certain amount of other essential fatty acids (such as stearic acid, behenic acid, palmitic acid, myristic acid, and lauric acid) are transesterified with medium-chain or short-chain triglycerides. The corresponding medium-chain triglycerides and short-chain triglycerides are prepared using a synthetic method for medium- and long-chain triglycerides, i.e., triglycerides mainly containing one long-chain fatty acid and two medium-chain fatty acids, and triglycerides mainly containing two long-chain fatty acids and one short-chain fatty acid. These are then compounded, with a molar ratio of triglycerides containing one long-chain and two medium-chain acids to triglycerides containing two long-chain and one short-chain acid of 1.0:0.0~2.0, to prepare fat emulsions suitable for intravenous administration in hospitals and gastrointestinal preparations suitable for oral administration. By avoiding the complex and expensive preparation routes of constructing medium- and long-chain triglycerides containing two active fatty acids in the same molecule using bio-enzymatic synthesis or regioselective chemical synthesis, the product can be made more cost-effective and cover a wider range of beneficiaries.

[0049] The selected saturated fatty acids include, but are not limited to, behenic acid, stearic acid, palmitic acid, and myristic acid. The selected unsaturated fatty acids include, but are not limited to, oleic acid, linoleic acid, linolenic acid, octadecanoic acid, EPA+DHA, and nervonic acid. The proportion of long-chain saturated fatty acids is <15%, the proportion of unsaturated fatty acids is >70%, and the ratio of ω3 fatty acids to ω6 fatty acids is 1:2~4. The preferred proportions of saturated fatty acids are: stearic acid ≤5.5%, palmitic acid ≤2.5%, lauric acid ≤6.0%, and the preferred proportions of unsaturated fatty acids are: oleic acid ≥40%, linoleic acid ≤15%, α-linolenic acid ≥6%, EPA+DHA ≥1.5%, and nervonic acid ≥0.5%. As reactants, saturated fatty acid low-carbon alcohol esters can be obtained by esterifying the corresponding fatty acids with the corresponding alcohols, and unsaturated fatty acid low-carbon alcohol esters can be obtained by ester exchange of oils rich in the corresponding unsaturated fatty acids with low-carbon alcohols followed by purification (see the methods mentioned above).

[0050] Following a method for synthesizing medium- and long-chain fatty acid glycerides, a specific ratio of low-carbon alcohol esters of fatty acids is transesterified with medium-chain triglycerides to form a triglyceride product mainly containing one long-chain fatty acid and two medium-chain fatty acids. Similarly, an ω3 fatty acid low-carbon alcohol ester is transesterified with a short-chain triglyceride to form a triglyceride product mainly containing two long-chain fatty acids and one short-chain fatty acid. These two products are then compounded in a certain ratio and combined with lecithin, oil-soluble vitamins, glycerol, and water to prepare a fat emulsion. Alternatively, the product can be compounded with antioxidants (vitamin E, vitamin C palmitate), other fat-soluble vitamins (vitamin A, D), and other nutritional and health-promoting ingredients such as lecithin, phytosterol esters, coenzyme Q10, astaxanthin, ergosalicyline, and phosphatidylserine to form an oral formulation.

[0051] All the above synthetic preparation processes are based on the chemical process established in this patent, which involves the transesterification of fatty acids or low-carbon alcohol esters with triglycerides under alkaline catalysis or alkali-soap synergistic catalysis. This process synthesizes short-chain triglycerides, medium-chain triglycerides, and medium-to-long-chain triglycerides. Based on the products' low calorie content, melting point characteristics, health and nutritional benefits, and clinical therapeutic properties, formulations suitable for various scenarios have been developed. Any modifications to the synthetic preparation process and product formulation based on this patent fall within the scope of protection of this patent. Detailed Implementation

[0052] (a) Synthesis and preparation of medium-chain fatty acid triglycerides.

[0053] 1. Prepared by the exchange reaction of medium-chain fatty acid low-carbon alcohol esters with short-chain acid triglycerides.

[0054] Pretreatment of the reactants ensured their acid value and water content met requirements. 25.82 g of vacuum-dried, deacidified, and dehydrated acetyl triglyceride, 99.18 g of ethyl caprylate, and 1.25 g of anhydrous soap (containing 1.07 g potassium oleate and 0.18 g sodium oleate) were added to a 250 ml three-necked flask and sheared-stirred for 5-10 minutes to form a slurry. A stirring and distillation collection device was installed in the reaction flask, and dry nitrogen gas was introduced to maintain a nitrogen atmosphere. 1.00 g of freshly prepared sodium ethoxide was added, and the mixture was rapidly stirred to disperse it in the materials. The temperature was increased under a nitrogen atmosphere. When the temperature exceeded 100°C, ethyl acetate formed by transesterification began to distill off. The temperature was maintained at 120°C-130°C for 1 hour, during which time the ethyl acetate formed by the reaction was rapidly distilled off. The temperature was then increased to 140°C-150°C and maintained for 2.5 hours, with reduced pressure under a N2 atmosphere to ensure the timely distillation of the ethyl acetate produced. When cooled to <65℃, add a measured amount of phosphoric acid to neutralize sodium ethoxide, stir for 5-10 minutes, then add 0.13 g of diatomaceous earth as a filter aid, stir thoroughly, and then filter to remove soap and formed inorganic salts. Add 0.30 g of activated SiO2 ultrafine powder and an appropriate amount of diatomaceous earth as a filter aid to the filtrate, stir at 90-95℃ for 15-20 minutes, and then filter again. The filtrate is the crude product.

[0055] The crude product was added to a falling film vacuum distillation apparatus, and unreacted ethyl caprylate was recovered at temperatures greater than 50℃~130℃ and 50~100Pa (which can be reused). Short-chain triglycerides containing one medium-chain fatty acid and short-chain triglycerides containing two medium-chain fatty acids were distilled off at 150℃~200℃ and 35~50Pa. Finally, caprylate triglyceride was produced at 215℃~235℃ and 20~35Pa, yielding 39.06 grams.

[0056] According to the national standards for edible oils, its acid value, peroxide value, saponification value, etc., all meet the requirements.

[0057] 2. Prepared by transesterification reaction of medium-chain fatty acid low-carbon alcohol esters with coconut oil, palm oil, etc.

[0058] Pretreatment of the reactants ensures their acid value and moisture content meet requirements. Take 52.98 g of vacuum-dried, deacidified, and dehydrated coconut oil, 107.02 g of ethyl caprylate, and 1.60 g of anhydrous soap (containing 1.44 g of potassium oleate and 0.16 g of sodium oleate), and add them to a 250 ml three-necked flask. Stir and shear for 5-10 minutes to form a slurry. Attach a stirring and distillation collection device to the reaction flask and maintain a nitrogen atmosphere by purging with dry nitrogen. Add 0.72 g of freshly prepared sodium ethoxide, stir rapidly to disperse it in the material, and heat under a nitrogen atmosphere to 170-180°C for 1.5-2.5 hours. Cool to <65°C, add a measured amount of phosphoric acid to neutralize the sodium ethoxide, stir for 5-10 minutes, then add 0.10 g of diatomaceous earth as a filter aid. After thorough stirring, filter to remove the soap and any formed inorganic salts. Add 0.30 g of activated SiO2 ultrafine powder and 0.05 g of diatomaceous earth as a filter aid to the filtrate, stir at 90-95°C for 15-20 minutes, and then filter by suction. The filtrate is the crude product.

[0059] The crude product was added to a falling film vacuum distillation apparatus, and unreacted ethyl caprylate (which can be reused) was recovered at temperatures greater than 50℃~130℃ and 50~100Pa. Other fatty acid ethyl esters were formed by transesterification at 160℃~200℃ and 35~50Pa. Finally, 15.30 grams of ethyl caprylate triglyceride formed in the reaction was distilled off by molecular distillation at 220℃~235℃ and 0.1~0.5Pa.

[0060] According to the national standards for edible oils, its acid value, peroxide value, saponification value, etc., all meet the requirements.

[0061] The same experiment was conducted using palm oil and soybean oil as raw materials, and the resulting caprylic / capric triglycerides were 9.20 g and 8.05 g, respectively.

[0062] (ii) Synthesis and preparation of triglycerides containing short-chain acids and fatty acid substitutes.

[0063] 1. Synthesis and preparation of fatty triglycerides that replace natural butter and cocoa butter short-chain acids.

[0064] Take 32.44 g of deacidified and dehydrated triacetin, and 207.56 g of deacidified and dehydrated low-carbon alcohol esters of fatty acids (the fatty acids consist of saturated and unsaturated fatty acids in a weight ratio of 92:8; the saturated fatty acid composition is behenic acid:stearic acid:palmitic acid 1:4:1; the unsaturated fatty acid composition is oleic acid:linoleic acid 4:1). Add 2.40 g of anhydrous soap (including 2.16 g of potassium oleate and 0.24 g of sodium oleate) to a 250 ml three-necked flask. Stir and shear for 5-10 minutes to form a slurry. Attach a stirring and distillation collection device to the reaction flask and maintain a nitrogen atmosphere by purging with dry nitrogen gas. Add 0.7 g of freshly prepared sodium ethoxide. Add 2 grams of the solution and stir rapidly to disperse it in the material. Heat the mixture under a nitrogen atmosphere. React at 120℃~130℃ for 1.5 hours, during which a large amount of ethyl acetate will distill off. Then react at 145℃~155℃ for 1 hour until equilibrium is reached. Cool to <65℃, add a measured amount of phosphoric acid to neutralize the sodium ethoxide, stir for 5~10 minutes, then add 0.12 grams of diatomaceous earth as a filter aid. After thorough stirring, filter to remove soap and formed inorganic salts. Add 0.30 grams of activated SiO2 ultrafine powder and 0.05 grams of diatomaceous earth as a filter aid to the filtrate, stir at 90~95℃ for 15~20 minutes, and then filter again. The filtrate is the crude product.

[0065] The crude product is added to a falling film vacuum distillation apparatus, and unreacted fatty acid ethyl esters are recovered at temperatures above 150℃~175℃ and 50~100Pa (which can be recycled). Distillation can be repeated until the fatty acid ethyl ester content is ≤0.5%. Finally, 115.30 grams of the product formed by the reaction is distilled off at 190℃~250℃ and 0.1~0.5Pa. The main component is a triglyceride with one acetyl group and two fatty acid acyl groups. It is light yellow, with a melting point of 31℃~35℃. Its acid value, peroxide value, and saponification value meet the requirements for food additives, and the trans fatty acid content is ≤0.1%.

[0066] This product is suitable as a substitute for natural butter and cocoa butter in the manufacture of margarine, ice cream, puff pastry, and other similar products.

[0067] 2. Preparation of ω3 fatty acid triglycerides (EPA, DHA, α-linolenic acid) and nervonic acid triglycerides containing short-chain acids. The preparation method is the same as in 1. above, except that the reaction temperature is controlled at 110~135℃ until the reaction reaches equilibrium. Using EPA+DHA ethyl ester with a purity ≥70%, α-linolenic acid ethyl ester with a purity ≥85%, and nervonic acid ethyl ester with a purity ≥40%, transesterification was carried out at a molar ratio of triacetylglycerol to ethyl ester of 1:2.2. The yields of the products, based on triacetylglycerol, were ≥90.5%, 96.3%, and 88.9%, respectively. The products were mainly two long-chain and one short-chain triglycerides.

[0068] 3. Synthesis and preparation of low-calorie triglycerides containing short-chain fatty acids.

[0069] Constructing low-carbon alcohol esters of fatty acids. Saturated fatty acids are composed of components containing 8% stearic acid, 2% behenic acid, and 20% caprylic / capric acid, while unsaturated fatty acids are composed of components containing ≥40% oleic acid, 20% linoleic acid, and 10% α-linolenic acid. These components are then combined to form fatty acids. Low-carbon alcohol esters of stearic acid are prepared by alkaline-catalyzed transesterification of hydrogenated soybean oil with anhydrous ethanol. Low-carbon alcohol esters of behenic acid, caprylic / capric acid, etc., are prepared by dehydration of the corresponding fatty acids with ethanol under acid catalysis. Low-carbon alcohol esters rich in oleic acid are prepared by alkaline-catalyzed transesterification of improved high-oleic sunflower seed oil with anhydrous ethanol followed by purification. Low-carbon alcohol esters rich in linoleic acid are prepared by alkaline-catalyzed transesterification of safflower seed oil with anhydrous ethanol followed by purification. Low-carbon alcohol esters of α-linolenic acid are prepared by alkaline-catalyzed transesterification of perilla seed oil or flaxseed oil with anhydrous ethanol followed by purification.

[0070] First, mix low carbon alcohol esters such as stearic acid, behenic acid, and palmitic acid with low carbon alcohol esters of unsaturated fatty acids such as oleic acid, linoleic acid, and α-linolenic acid. Then, add low carbon alcohol esters of caprylic / capric acid separately in the later stages of the reaction.

[0071] Take 35.12 g of triacetin, 224.39 g of fatty acid ethyl esters (of which 44.00 g of caprylic / capric acid ethyl ester is separated and not mixed), and combine saturated and unsaturated fatty acids according to the stoichiometric ratio to form a low-carbon alcohol ester. First, add the low-carbon alcohol ester without caprylic / capric acid, the deacidified and dehydrated fatty acid low-carbon alcohol ester, and triacetin to a 500 ml three-necked flask, add 2.40 g of anhydrous soap (including 2.16 g of potassium oleate and 0.24 g of sodium oleate), and shear and stir for 5-10 minutes to form a slurry. Attach a stirring and distillation collection device to the reaction flask, and purge with dry nitrogen to maintain a nitrogen atmosphere. Add 0.93 g of freshly prepared sodium ethoxide, stir rapidly to disperse it in the material, and heat under a nitrogen atmosphere. React at 120℃-130℃ for 1.5 hours. Then add 44.00 g of caprylic / capric acid low-carbon alcohol ester, and react at 145℃-155℃ for 1 hour until equilibrium is reached. When cooled to <65℃, add a measured amount of phosphoric acid to neutralize sodium ethoxide, stir for 5-10 minutes, then add 0.13 g of diatomaceous earth as a filter aid, stir thoroughly, and then filter to remove soap and formed inorganic salts. Add 0.35 g of activated SiO2 ultrafine powder and an appropriate amount of diatomaceous earth as a filter aid to the filtrate, stir at 90-95℃ for 15-20 minutes, and then filter again. The filtrate is the crude product.

[0072] The crude product was added to a falling film vacuum distillation apparatus. Unreacted ethyl caprylate was recovered at temperatures above 60℃~130℃ and 50~100Pa, and unreacted fatty acid ethyl esters were recovered at temperatures above 150℃~175℃ and 50~100Pa (this can be recycled). Distillation could be repeated until the residual fatty acid ethyl ester was ≤0.5%. Finally, 124.69 grams of the product formed by the reaction was distilled off at 190℃~250℃ and 0.1~0.5Pa. The main component was a triglyceride with one acetyl group and two fatty acid acyl groups. It was a light yellow oily liquid with no odor. The acid value, peroxide value, and saponification value met the requirements for food additives, and the trans fatty acid content was ≤0.1%.

[0073] Low-calorie weight-control formula: 1000g of a product containing 1 acetyl and 2 fatty acid acyl triglycerides of the above-mentioned specific fatty acid composition, 0.3g of vitamin E + vitamin C palmitate (50%), 8g of phytosterol esters, and 15g of soybean lecithin. Store under nitrogen. Suitable for daily cooking as a low-calorie weight-control oil, and also for use as a low-calorie edible oil in processed food products such as pastries, desserts, and candies.

[0074] (III) Synthesis, preparation and application of medium and long chain fatty acid triglycerides.

[0075] 1. Synthetic preparation of edible oils into medium- and long-chain fatty acid triglycerides.

[0076] Medium- and long-chain fatty acid triglycerides were prepared by a three-step transesterification reaction.

[0077] Step 1: Pre-treatment of reactants to ensure their acid value and moisture content meet requirements. Take 106.13 g of vacuum-dried and dehydrated peanut oil, 28.87 g of vacuum-dried and dehydrated ethyl caprylate, and 1.35 g of anhydrous soap (including 1.22 g of potassium oleate and 0.13 g of sodium oleate), and add them to a 250 ml three-necked flask. Stir for 5-10 minutes to form a slurry. Attach a stirring and distillation collection device to the reaction flask and purge with dry nitrogen to maintain a nitrogen atmosphere. Add 1.30 g of freshly prepared sodium ethoxide, stir rapidly to disperse it in the material, and heat under a nitrogen atmosphere at 160℃-175℃ for 1.5-2.5 hours until equilibrium is reached. Cool to <65℃, add a measured amount of phosphoric acid to neutralize the sodium ethoxide, stir for 5-10 minutes, then add 0.10 g of diatomaceous earth as a filter aid. After thorough stirring, filter to remove the soap and any formed inorganic salts. Add 0.40 g of activated SiO2 ultrafine powder and 0.05 g of diatomaceous earth as a filter aid to the filtrate, stir at 90-95°C for 15-20 minutes, and then filter by suction. The filtrate is the crude product.

[0078] The crude product was added to a falling film vacuum distillation apparatus. Unreacted ethyl caprylate (which can be recycled) was recovered at 60℃~130℃ and 50~100Pa. The transesterified fatty acid ethyl esters (used in step 2) were separated by distillation at 150℃~175℃ and 35~50Pa. Multiple distillations were performed until the fatty acid ethyl ester content was ≤0.5%. Finally, 86.55 grams of the product formed in the reaction were distilled off by molecular distillation at 190℃~250℃ and 0.1~0.5Pa. The main component was a triglyceride consisting of two long-chain and one medium-chain triglyceride.

[0079] The second step involves a transesterification reaction between the peanut oil fatty acid ethyl ester produced in the first step and caprylic / capric triglyceride. 75.42 g of caprylic / capric triglyceride and 59.58 g of peanut oil fatty acid ethyl ester were used, and the transesterification was carried out under the same conditions as in the first step, yielding a crude product which was then vacuum distilled. The resulting caprylic / capric triglyceride (which can be recycled for use in the first step synthesis) was distilled off at 60℃~125℃ and 50~100 Pa. Unreacted fatty acid ethyl esters (used in the second step) were separated by distillation at 150℃~175℃ and 35~50 Pa. This process can be repeated until the fatty acid ethyl ester content is ≤0.5%. Finally, 84.30 g of the product was distilled off by molecular distillation at 190℃~250℃ and 0.1~0.5 Pa. The main component is a long-chain di- and medium-chain triglyceride.

[0080] The third step involves preparing medium- and long-chain glycerides of ω3 fatty acids using the method described in the second step. A transesterification reaction is performed between ethyl α-linolenic acid (≥85%) and ethyl EPA+DHA (≥70%) and caprylic / capric triglycerides. Short- and long-chain glycerides of ω3 fatty acids are then prepared, with yields of 96.26% and 85.39%, respectively (based on caprylic / capric triglycerides).

[0081] Health-promoting oil formula one: 100g of two long-chain and one medium-chain triglycerides based on peanut oil, 40g of one long-chain and two medium-chain triglycerides based on peanut oil, 13g of medium- and long-chain alpha-linolenic acid glycerides (or EPA+DHA medium- and long-chain glycerides), 0.05g of vitamin E+vitamin C palmitate (50% each), 1.2g of phytosterol esters, and 2.2g of soybean lecithin. Store under nitrogen.

[0082] Formula 2 for health-promoting oils: 200g of two long-chain and one medium-chain triglycerides based on peanut oil, 18g of a short-chain and two long-chain triglycerides of α-linolenic acid (or a short-chain and two long-chain triglycerides of EPA+DHA), 0.06g of vitamin E+vitamin C palmitate (50% each), 1.7g of phytosterol esters, and 3.3g of soybean lecithin. Store under nitrogen.

[0083] The two types of health-promoting oils mentioned above are suitable for use as cooking oils and for supplementary nutritional therapy in individuals with abnormal lipid absorption and metabolism, cardiovascular and cerebrovascular diseases, as well as those who are weak, chronically ill, or in emergency situations. They can also be used as healthy fats in the production of pastries, desserts, and candies.

[0084] Other edible oils such as rapeseed oil, sunflower oil, olive oil, tea seed oil, flaxseed oil, safflower oil, grapeseed oil, corn oil, soybean oil, palm oil, coconut oil, and cottonseed oil can also be formulated into similar health-promoting oils using the above process.

[0085] 2. Medium- and long-chain fatty acid triglycerides suitable for clinical treatment and health care.

[0086] (1) Using natural oils as raw materials, construct various fatty acid triglycerides of medium and long chain fatty acids to meet the synergistic therapeutic needs.

[0087] Using flaxseed oil, perilla seed oil, and borage seed oil as sources of ω3 fatty acids (content greater than 55%), safflower seed oil, sunflower seed oil, and grape seed oil as sources of ω6 fatty acids (content greater than 65%), and improved high-oleic sunflower seed oil / high-oleic safflower seed oil as sources of oleic acid (content greater than 80%), the oils were mixed in a specific ratio to achieve an ω3 fatty acid to ω6 fatty acid ratio of 1:2~5 and an oleic acid content ≥30%. A mixed oil of 20% flaxseed oil, 45% safflower seed oil, and 35% high-oleic sunflower seed oil was used. 105.0 g of this mixed oil and 28.5 g of ethyl caprylate were used as reactants. Following the established process, 85.63 g of crude triglyceride product, mainly containing one medium-chain and two long-chain fatty acids, was prepared. The product was placed overnight in an ice-salt bath at -10℃ to allow some saturated fatty acid glycerides to crystallize. After removal by low-temperature pressure filtration, 78.12 g of purified product was obtained.

[0088] Product formula: 200g of triglycerides of one medium-chain and two long-chain fatty acids of the above-mentioned specific fatty acids, 0.1g of vitamin E and vitamin C palmitate (50% each), 3g of short-chain and long-chain (or medium-chain and long-chain) triglycerides containing EPA and DHA, 1.6g of short-chain and long-chain (or medium-chain and long-chain) triglycerides of nervonic acid, 3g of soybean lecithin, and 1.6g of phytosterol esters. Store under nitrogen.

[0089] The product can be used as a cooking oil, with a daily intake of 25-40 grams, for the prevention and synergistic treatment of diseases with imbalanced fatty acid metabolism (such as rheumatoid arthritis, arteriosclerosis and thrombosis, allergic asthma, enteritis, etc.), as well as for energy support in cases of malnutrition and chronic weakness (such as wasting diseases like tumors); it can also be used as a raw material for clinical fat emulsions.

[0090] (2) Triglycerides with a single long chain and two medium chains were prepared by transesterification reaction of oleic acid (content ≥90%), linoleic acid (content ≥85%), α-linolenic acid ethyl ester (content ≥85%) and saturated fatty acid ethyl ester (stearic acid: palmitic acid molar ratio 4:1) with caprylic / capric triglycerides. The formulation is based on the following proportions: 8.50% α-linolenic acid medium- and long-chain fatty acid triglycerides, 24.50% linoleic acid medium- and long-chain fatty acid triglycerides, 5.00% stearic acid + palmitic acid (molar ratio 4:1) mono- and di- and medium-chain triglycerides, 60% oleic acid medium- and long-chain fatty acid triglycerides, 1.50% triglycerides containing (EPA + DHA) short- and long-chain (or medium- and long-chain) fatty acids, and 0.50% triglycerides containing nervonic acid short- and long-chain (or medium- and long-chain) fatty acids. 0.03% of antioxidants (such as vitamin E, vitamin C palmitate, etc.) are added, and the mixture is stored under nitrogen.

[0091] Take 200g of the above-mentioned specific fatty acid health oil, 11g of lecithin, and 22.5g of osmotic regulator glycerin, and add double-distilled water to a final volume of 1 liter. Through repeated homogenization and stirring, a fat emulsion with a particle size of <1 micrometer is formed. After filtration, a final emulsion of 0.24~0.75 micrometers is formed. This emulsion is then placed in a pyrogen-free container and sterilized at 105℃ for 25 minutes. After one week, the emulsion is re-examined, and the microparticles are ≤1 micrometer and the endotoxin is ≤1 nanogram. This forms an intravenous injection solution for nutritional support in critically ill patients.

[0092] The aforementioned specific fatty acid health oils can be packaged into soft capsules for use by specific patients to supplement nutrition and energy, prevent excessive metabolism under stress (severe trauma, large-area burns, major surgery, etc.), and correct nitrogen imbalance in the body. They can also be used for the prevention and synergistic treatment of fatty acid metabolism disorders (such as rheumatoid arthritis, arteriosclerosis and thrombosis, allergic asthma, enteritis, etc.), as well as for malnutrition and chronic weakness (wasting diseases such as tumors).

Claims

1. A chemical process for preparing reconstructed triglycerides by transesterification of C1-C6 low-carbon alcohol esters of straight-chain or branched C2-C24 fatty acids with triglycerides under alkaline catalysis or alkaline soap synergistic catalysis, and the application of the synthesized products in nutritional health care, clinical treatment and weight control, and as a substitute for oils in health food processing.

2. According to the chemical process method of claim 1, the low-carbon alcohol esters and triglycerides require pretreatment before transesterification. This involves washing with alkaline water (0.05-0.5% hydroxide or carbonate solution or a mixture thereof) or using alkaline activated clay for adsorption to remove acidic substances, resulting in an acid value <1.0, preferably <0.

5. Vacuum drying is then performed below the boiling point of the materials. For triglycerides, the drying temperature is preferably 120℃-150℃; for low-carbon alcohol esters, the drying temperature is preferably 110℃-140℃, until the water content is <0.01%. The low-carbon alcohol esters of fatty acids are derived from vegetable oils and animal fats. Vegetable oils include, but are not limited to, peanut oil, perilla seed oil, sunflower seed oil, flaxseed oil, safflower seed oil, grape seed oil, cauliflower seed oil, olive oil, corn oil, soybean oil, palm oil, coconut oil, cottonseed oil, and hydrogenated oils. Animal fats refer to deep-sea fish oils, including but not limited to tuna oil, cod oil, saury oil, and filefish oil.

3. According to the chemical process method of claim 1, the alkaline catalyst refers to an alkali metal or alkaline earth metal alkali metal alcohol, hydroxide, or alkaline earth metal hydroxide, and the co-catalyst soap refers to a straight-chain or branched C2-C24 acid or fatty acid of alkali metal or alkaline earth metal or a mixture thereof. Depending on the specific target product being prepared, the molar ratio of triglycerides to lower alcohol esters of fatty acids is 1.00:1.00~6.

00. The amount of alkaline catalyst is 0.01%~5.00% of the total reactants, preferably 0.2%~1.0%, more preferably 0.3%~0.7%; the amount of soap as a co-catalyst is 0.01%~15.00% of the total reactants, preferably 0.2%~5.0%, more preferably 0.3%~1.0%. The transesterification reaction is carried out under an inert protective gas atmosphere, including but not limited to nitrogen (which can isolate oxygen), group 0 element gases such as helium and argon, or low-molecular-weight hydrocarbon gases. After replacing the oxygen in the reaction vessel (reactor) with a protective gas, a small airflow is maintained to prevent air infiltration. The transesterification reaction is carried out at 50°C to 250°C, preferably 110°C to 190°C, and more preferably 125°C to 170°C; the reaction time is typically 0.5 to 4.0 hours, preferably 1.0 to 3.0 hours, and more preferably 1.5 to 2.0 hours. After the reaction reaches equilibrium, the catalyst is neutralized and passivated with an inorganic acid. The inorganic salts and catalyst soaps formed during neutralization are removed by filtration, centrifugation, or pressure filtration. Residual soaps in the material are further removed by activated ultrafine SiO2 and diatomaceous earth as a filter aid to form the primary product. The chemical process method of claim 1, the alkaline catalyst refers to the alkali metal or alkaline earth metal alcohol, hydroxide and alkaline earth metal hydroxide, and the co-catalyst soap refers to the straight-chain or branched C2~C24 acid or fatty acid alkali metal or alkaline earth metal or mixture thereof. Depending on the specific target product being prepared, the molar ratio of triglycerides to lower alcohol esters of fatty acids is 1.00:1.00~6.

00. The amount of alkaline catalyst is 0.01%~5.00% of the total reactants, preferably 0.2%~1.0%, more preferably 0.3%~0.7%; the amount of soap as a co-catalyst is 0.01%~15.00% of the total reactants, preferably 0.2%~5.0%, more preferably 0.3%~1.0%. The transesterification reaction is carried out under an inert protective gas atmosphere, including but not limited to nitrogen (which can isolate oxygen), group 0 element gases such as helium and argon, or low-molecular-weight hydrocarbon gases. After replacing the oxygen in the reaction vessel (reactor) with a protective gas, a small airflow is maintained to prevent air infiltration. The transesterification reaction is carried out at 50°C to 250°C, preferably 110°C to 190°C, and more preferably 125°C to 170°C; the reaction time is typically 0.5 to 4.0 hours, preferably 1.0 to 3.0 hours, and more preferably 1.5 to 2.0 hours. After the reaction reaches equilibrium, the catalyst is neutralized and passivated with an inorganic acid. The inorganic salts and catalyst soaps formed during neutralization are removed by filtration, centrifugation, or pressure filtration. Residual soaps in the material are further removed by activated ultrafine SiO2 and diatomaceous earth as a filter aid to form the primary product.

4. The primary product prepared according to claim 3 is purified by vacuum distillation. This includes conventional vacuum distillation, falling film vacuum distillation, and molecular distillation. Preferably, medium-chain fatty acid low-carbon alcohol esters (such as methyl or ethyl esters of octanoic acid and decanoic acid) in the distillate are distilled off at 50℃~135℃ and 40~200Pa, which can be recycled; long-chain fatty acid low-carbon alcohol esters, medium-chain or short-chain fatty acid triglycerides in the transesterification are distilled off at 140℃~215℃ and 1.0~50Pa (which can be recycled), and multiple (2~3) distillations can be performed until the ester content of the non-product is ≤0.5%; finally, the target product triglyceride is obtained by molecular distillation at 200℃~260℃ and 0.01~0.5Pa, which can be either the distillate or the residue.

5. If the distilled product obtained according to claim 4 has a high acid value, it can be washed with 0.1-0.5% alkaline solution to remove acidic substances; if the color is dark, it can be decolorized with 0.5% bleaching activated clay or activated carbon at 90-105°C; if there is an odor, it can be deodorized by conventional oil deodorization method, i.e., steam deodorization at 200-230°C for 1-2 hours under vacuum.

6. Caprylic / capric triglycerides are prepared according to the process methods of claims 1 to 5. Caprylic / capric triglycerides and other medium-chain fatty acid triglycerides are prepared by transesterification of ethyl caprylic / capric triglycerides with short-chain triglycerides, coconut oil (or hydrogenated coconut oil), palm oil (or hydrogenated palm oil), etc.

7. A substitute oil for butter and cocoa butter is prepared according to the process method of claims 1 to 5. A low-carbon alcohol ester consisting of more than 80% saturated fatty acids (including but not limited to mixtures of two or more behenic acid, stearic acid, lauric acid, etc.) and less than 20% unsaturated fatty acids (including but not limited to low-carbon alcohol esters composed of single fatty acids such as oleic acid, linoleic acid, and linolenic acid, or mixtures thereof) undergoes a transesterification reaction with a short-chain triglyceride to prepare triglycerides mainly containing one short chain and two long chains, and triglycerides mainly containing two short chains and one long chain. The melting point of the product is similar to that of butter and cocoa butter, and it can be used as a substitute oil in food processing, such as in the manufacture of margarine, shortening, pastries, desserts, biscuits, and candies.

8. A low-calorie, weight-controlling functional oil is prepared according to the process method of claims 1-5. The process involves transesterification of low-carbon alcohol esters of saturated fatty acids (composed of stearic acid, behenic acid, caprylic / capric acid, etc.) with low-carbon alcohol esters of unsaturated fatty acids (composed of ω3, ω6 fatty acids, oleic acid, etc., with a molar ratio of ω3:ω6 of 1:3-4), wherein the proportion of saturated fatty acid low-carbon alcohol esters is ≤30%, and the proportion of unsaturated fatty acid low-carbon alcohol esters is ≥70%. This is followed by transesterification with short-chain triglycerides to prepare short-chain and long-chain triglycerides composed of special fatty acids. The product mainly consists of triglycerides with one short-chain acid and two long-chain fatty acids. It features balanced nutrition and low calories, making it suitable for use as a cooking oil for weight control and also as a functional oil in food processing.

9. The process method according to claims 1-5 reconstructs edible oils into functional oils. Edible oils include, but are not limited to, peanut oil, soybean oil, rapeseed oil, olive oil, tea seed oil, corn oil, sunflower seed oil, safflower seed oil, flaxseed oil, perilla seed oil, chia seed oil, tuna oil, cod oil, saury oil, and filefish oil. Specifically, the first step involves transesterifying caprylic / capric acid low-carbon alcohol esters with edible oils to form triglycerides mainly containing one medium-chain and two long-chain fatty acids, while simultaneously generating low-carbon alcohol esters of edible oil fatty acids; the second step involves transesterifying the generated low-carbon alcohol esters of edible oil fatty acids with medium-chain fatty acid triglycerides to form triglycerides mainly containing two medium-chain and one long-chain fatty acids, while simultaneously generating low-carbon alcohol esters of medium-chain fatty acids (which can be recycled back to the first transesterification step). The medium-chain triglycerides prepared in the first and second steps are compounded, with 60%–100% triglycerides containing one medium-chain and two long-chain fatty acids, and 0%–40% triglycerides containing two medium-chain and one long-chain fatty acid. The mixture is frozen to -10°C to 0°C overnight to precipitate some of the hypersaturated fatty acid triglycerides, which are then removed by pressure filtration, yielding the filtrate (product). An ω3 fatty acid triglyceride containing one short-chain and two long-chain triglycerides, or a ω3 fatty acid triglyceride containing two medium-chain and one long-chain triglyceride, is added to achieve an ω3:ω6 fatty acid ratio of 1:3–4. Other nutrients such as vitamins A and D, phospholipids, phytosterol esters, and ergothioneine can also be added. The mixture is stored under nitrogen. This product is suitable for use as a health-promoting seasoning or cooking oil, and for synergistic nutritional therapy in individuals with abnormal lipid absorption and metabolism, cardiovascular and cerebrovascular diseases, and those who are weak, chronically ill, or in emergency situations. It can also be used as a raw material for fat emulsions and as a healthy oil in pastries, desserts, and candies.

10. A health-promoting oil with a more scientific and reasonable fatty acid composition is prepared according to the process methods of claims 1-5. Flaxseed oil, perilla seed oil, borage seed oil, etc., are used as sources of ω3 fatty acids; safflower seed oil, sunflower seed oil, grape seed oil, etc., are used as sources of ω6 fatty acids; and improved varieties of high-oleic sunflower seed oil / high-oleic safflower seed oil, etc., are used as sources of oleic acid. The oils are mixed in a certain proportion, such that the ratio of ω3 fatty acids to ω6 fatty acids is 1:2-5, and the oleic acid content is ≥30%. Using this mixed oil as raw material, triglycerides mainly containing one medium-chain and two long-chain fatty acids are prepared according to the process methods of claims 1-5. Saturated fatty acid oils are crystallized out at 0℃ to -10℃ and filtered off to obtain the product. In addition, other nutrients such as vitamin E and vitamin C palmitate, vitamins A and D, EPA, DHA medium- and long-chain or short- and long-chain triglycerides, nervonic acid medium- and long-chain or short- and long-chain triglycerides, phospholipids, phytosterol esters, astaxanthin, coenzyme Q10, ergosylphosphatidylserine, etc., are added to form the final product. It can be used as a cooking oil or packaged into soft capsules for the prevention and synergistic treatment of diseases with fatty acid imbalance (such as rheumatoid arthritis, arteriosclerosis and thrombosis, allergic asthma, enteritis, etc.), as well as for energy support in cases of malnutrition and chronic weakness (such as wasting diseases like tumors); it can also be used as a raw material for clinical fat emulsions.

11. A method for preparing therapeutically functional medium- and long-chain triglycerides according to the process described in claims 1 to 5. Low-carbon alcohol esters rich in ω3 fatty acids (purity ≥80%, including but not limited to α-linolenic acid, EPA, DHA, octadecanoic acid, etc.), low-carbon alcohol esters of ω6 fatty acids (purity ≥80%, including but not limited to linoleic acid, γ-linolenic acid, arachidonic acid, etc.), low-carbon alcohol esters of ω9 fatty acids (purity ≥90%, including but not limited to oleic acid, nervonic acid, eicosadecanoic acid, etc.), and low-carbon alcohol esters of combined saturated fatty acids, derived from edible vegetable oils, are reacted with medium-chain triglycerides to prepare ω3, ω6, ω9, and combined saturated fatty acid triglycerides according to the process described in claims 1 to 5. These medium- and long-chain triglycerides are mainly glycerides containing a single long chain and two medium chains. This product is formulated for therapeutic purposes, with a ω3:ω6 ratio of medium- and long-chain triglycerides at 1:3-4 (by weight), oleic acid medium- and long-chain triglycerides comprising ≥40%, and saturated fatty acids ≤5.0%. It also includes antioxidants, phospholipids, vitamins, phytosterol esters, coenzyme Q10, ergosylglycerol, phosphatidylserine, and other nutrients to form a health-promoting oil. This health-promoting oil can be prepared into an intravenous medium- and long-chain triglyceride fat emulsion using conventional pharmaceutical-grade fat emulsion preparation methods, or formulated into soft capsules. It is used to supplement nutrition and energy for specific patients, preventing excessive metabolism in patients under stress (severe trauma, extensive burns, major surgery, etc.), correcting nitrogen imbalances, and preventing organ failure.