A method for controlling trichloropropanol esters in fats and oils

Abstract

This invention provides a method for controlling 3-MCPDE in oils and fats, belonging to the field of oil and fat technology. The reaction steps are as follows: glycine and xylose are added to soybean enzymatic hydrolysate, stirred, and then zinc gluconate is added for ultrasonic treatment. The mixture is dried to a moisture content of 18-22% and the pH is adjusted to 6.8-7.0 to obtain the reaction system. The reaction system is then transferred to a sealed container and reacted at 168-172°C for 27-30 minutes to obtain the Maillard reaction product. The control method of this invention is simple and effective, and can effectively control the 3-MCPDE content.

Description

Technical Field

[0001] This invention belongs to the field of oil and fat technology, and specifically relates to a method for controlling trichloropropanol esters in oils and fats. Background Technology

[0002] 3-Monochloropropane-1,2-diol esters (3-MCPDEs) are common contaminants in processed vegetable oils. They are formed by the esterification reaction of chloropropanols with fatty acids. The content of 3-MCPDEs increases after vegetable oils are refined, and they are also present in refined vegetable oil-related products.

[0003] In rats exposed to 3-MCPDEs, the activities of blood urea nitrogen (BUN), creatinine (CRE), reactive oxygen species (ROS), malondialdehyde (MDA), caspase 3, and caspase 9 were significantly increased, while glutathione (GSH) and total antioxidant capacity (T-AOC) were decreased. Rat model studies have shown that 3-MCPDs and 3-MCPDEs are nephrotoxic, including renal tubular proliferation and renal tubular cell apoptosis. The possible toxic mechanisms include apoptosis and activation of pro-inflammatory factors, which induce lesions by inhibiting renal tubular epithelial activity and disrupting mitochondrial functional levels through oxidative stress.

[0004] In vitro / in vivo toxicology studies have shown that 3-MCPDEs are hydrolyzed in large quantities in the gastrointestinal tract to 3-chloropropane-1,2-diol (3-MCPD); in the classification of the International Agency for Research on Cancer (IARC), 3-MCPD is classified as a Group 2B carcinogen (possibly carcinogenic to humans).

[0005] The European Commission stipulates that the sum of 3-MCPD and 3-MCPDE in coconut oil, corn oil, rapeseed oil, sunflower oil, soybean oil, palm kernel oil, and olive oil, as well as oils made solely from these categories, must not exceed 1.25 mg / kg.

[0006] 3-MCPDEs are mainly produced during the deodorization stage of vegetable oil refining, which is the main reason for the high detection content of 3-MCPDEs in refined vegetable oils. Existing methods for controlling 3-MCPDEs in oils usually require changes to the processing technology and methods, mainly including refining process optimization, application of antioxidants, and adsorption by adsorbents. Refining process optimization is generally achieved by adjusting refining parameters. For example, dual-temperature deodorization (treating at 200℃ for 120 min followed by 270℃ for 5 min) can reduce 3-MCPDE by 78%, while short-path distillation achieves a removal rate as high as 93-96%. Appropriately lowering the deodorization temperature can reduce the formation of 3-MCPDE. When the deodorization conditions are 260℃ for 130 min, the formation of 3-MCPDE is 684.49 μg / kg. Adjusting the temperature to 230℃ for 70 min reduces the formation of 3-MCPDE by 68.42%. Currently, related studies report the use of exogenous antioxidants to inhibit the formation of 3-MCPDE; adding natural antioxidants such as olive extract (OE) to a frying model at a dose of 10 mg / kg inhibits the formation of 3-MCPDE, which is superior to the synthetic antioxidant TBHQ (28-65%), but OE has poor thermal stability; In adsorbent technology, mesoporous silica nanoparticles (MSNs) can achieve an adsorption rate of 98% for 3-MCPDE at 35℃ for 15 min, with a maximum adsorption capacity of 412.5 μg / g. They can also be regenerated after elution with petroleum ether. However, their large-scale application is costly and not conducive to large-scale industrial production. In addition, although the generation of 3-MCPDE can be controlled by auxiliary methods such as enzyme treatment, it is highly specific but also costly. Overall, these technologies each have their advantages and disadvantages, either by inhibiting the formation pathway or by directly removing pollutants / precursors. Furthermore, in existing control methods, the 3-MCPDE content increases significantly with increasing temperature and time. Therefore, a simple and effective method for controlling trichloropropanol esters in oils and fats needs to be developed. Summary of the Invention

[0007] To address the technical problems existing in the prior art, this invention provides a method for controlling trichloropropanol esters in oils and fats. The method is simple, effective, and low in cost, while effectively reducing the content of trichloropropanol esters. Furthermore, as the heating temperature of the oil and fat increases and the heating time is extended, the formation of 3-MCPDE is effectively controlled.

[0008] To address the aforementioned technical problems, the present invention adopts the following technical solution: A method for controlling trichloropropanol esters in oils includes Maillard reaction, preparation of antioxidants, post-treatment, and mixing steps, as detailed below: 1. Maillard reaction (1) Enzymatic hydrolysis Soak soybeans in deionized water (I) at room temperature for 6-8 hours. After soaking, drain the water, add deionized water (II), and grind at 7800-8000 rpm for 2-3 minutes. Adjust the pH to 5.8-6.0, then raise the temperature to 45-50℃, add neutral protease and cellulase, and incubate for 1.8-2.0 hours of enzymatic hydrolysis. During the enzymatic hydrolysis, control the stirring speed at 100-110 rpm. After the enzymatic hydrolysis is completed, filter after enzyme inactivation to obtain soybean enzymatic hydrolysate. The cellulase activity is 120,000-150,000 U / g; The activity of the neutral protease is 210,000-230,000 U / g; The mass ratio of soybean, deionized water I, deionized water II, neutral protease, and cellulase is 100:300-320:380-400:0.8-0.9:0.20-0.25. (2) Reaction Add glycine and xylose to soybean enzymatic hydrolysate, stir at 400-430 rpm for 10-15 min, then add zinc gluconate and sonicate for 15-20 min at a power of 180-200 W, a frequency of 36-40 kHz, and a temperature of 30-40 °C. After sonication, dry to a moisture content of 18-22%, and adjust the pH to 6.8-7.0 with 5-6 wt% sodium hydroxide solution to obtain the reaction system. Transfer the reaction system to a sealed container, increase the temperature to 168-172 °C at a rate of 4.5-5.0 °C / min, and maintain the temperature for 27-30 min. After the reaction, allow it to cool naturally to room temperature to obtain the Maillard reaction product. The mass ratio of soybean enzymatic hydrolysate, glycine, xylose, and zinc gluconate is 350:2.8-3.0:4.0-4.2:0.2-0.3.

[0009] 2. Preparation of antioxidants Add 1.0-2.0 wt% citric acid solution to the Maillard reaction product, adjust the pH to 6.0-6.3, add 4-5 times the mass of anhydrous ethanol, stir well, raise the temperature to 48-52℃, stir for 1.4-1.6 h at a stirring speed of 180-200 rpm, after extraction, lower to room temperature, filter, and centrifuge at 3800-4000 rpm for 10-12 min to obtain the ethanol extract; The ethanol extract was placed in a separatory apparatus, and 1.5-1.6 times its volume of ethyl acetate was added. After sealing, the mixture was shaken evenly and allowed to stand for 26-30 minutes. After the two phases had completely separated, the upper ethyl acetate phase was collected, and water was removed to obtain the purified solution. The purified solution was then subjected to vacuum distillation, with the vacuum gauge pressure controlled at -0.092 to -0.095 MPa and the distillation temperature at 124-126℃, to obtain 4-vinyleugenol antioxidant.

[0010] 3. Post-processing Deionized water is heated to 44-47℃, maltodextrin and pectin are added and stirred evenly. Sucrose fatty acid esters are added and stirring is continued for 15-20 minutes. Antioxidants are added, and 1-2 wt% citric acid solution is added to adjust the pH to 3.8-4.0. Then, high-pressure homogenization is performed at a temperature of 44-46℃ for 18-22 minutes and a pressure of 15-20 MPa. After homogenization, spray drying is performed at an inlet air temperature of 162-165℃ and an outlet air temperature of 78-80℃ to obtain functional antioxidants. The mass ratio of deionized water, maltodextrin, pectin, sucrose fatty acid ester, and antioxidant is 200:35-38:10-12:0.4-0.5:48-50.

[0011] 4. Mixing Functional antioxidants were added to palm oil, and the amount of functional antioxidants added was controlled at 1.8-2.3 mg / kg to obtain functional palm oil. The palm oil mentioned is Tianyijia natural pressed edible palm oil.

[0012] Compared with the prior art, the present invention has achieved the following beneficial effects: 1. Using the control method of the present invention, the amount of functional oxidant added is 1.8-2.3 mg / kg; 2. Using the control method of the present invention, when the frying temperature is 170℃, the 3-MCPDE content after frying for 4 minutes is 4.12-4.38 mg / kg, the 3-MCPDE content after frying for 5 minutes is 4.87-5.02 mg / kg, the 3-MCPDE content after frying for 6 minutes is 5.36-5.60 mg / kg, and the 3-MCPDE content after frying for 7 minutes is 6.01-6.28 mg / kg; 3. Using the control method of the present invention, when the frying temperature is 180℃, the 3-MCPDE content after frying for 4 minutes is 7.90-8.09 mg / kg, the 3-MCPDE content after frying for 5 minutes is 7.08-7.31 mg / kg, the 3-MCPDE content after frying for 6 minutes is 12.22-12.56 mg / kg, and the 3-MCPDE content after frying for 7 minutes is 6.88-6.94 mg / kg; 4. Using the control method of the present invention, when the frying temperature is 190℃, the 3-MCPDE content after frying for 4 minutes is 8.02-8.21 mg / kg, the 3-MCPDE content after frying for 5 minutes is 7.14-7.36 mg / kg, the 3-MCPDE content after frying for 6 minutes is 4.40-4.65 mg / kg, and the 3-MCPDE content after frying for 7 minutes is 4.85-5.03 mg / kg. Detailed Implementation

[0013] To provide a clearer understanding of the technical features, objectives, and effects of the present invention, specific embodiments of the present invention are now described.

[0014] Example 1 1. Maillard reaction (1) Enzymatic hydrolysis Soak 100g of soybeans in 300g of deionized water at room temperature for 6 hours. After soaking, drain the water, add 380g of deionized water, and grind at 7800rpm for 3 minutes. Adjust the pH to 5.8, then raise the temperature to 45℃, add 0.8g of neutral protease and 0.20g of cellulase, and incubate for 2.0 hours for enzymatic hydrolysis. During the enzymatic hydrolysis, control the stirring speed at 100rpm. After the enzymatic hydrolysis is completed, filter after enzyme inactivation to obtain soybean enzymatic hydrolysate. The cellulase activity is 120,000 U / g; The activity of the neutral protease is 210,000 U / g; (2) Reaction Add 2.8g glycine and 4.0g xylose to 350g soybean enzymatic hydrolysate, stir at 400rpm for 10min, then add 0.2g zinc gluconate and sonicate for 15min at 180W power, 36kHz frequency, and 30℃. After sonication, dry to a moisture content of 18%, and adjust the pH to 7.0 with 5.0wt% sodium hydroxide solution to obtain the reaction system. Transfer the reaction system to a sealed container, increase the temperature to 168℃ at a rate of 4.5℃ / min, and maintain the temperature for 27min. After the reaction, allow it to cool naturally to room temperature to obtain the Maillard reaction product.

[0015] 2. Preparation of antioxidants Add 1.0 wt% citric acid solution to the Maillard reaction product, adjust the pH to 6.0, add 4 times the mass of anhydrous ethanol, stir well, raise the temperature to 48℃, stir for 1.4 h at a stirring speed of 180 rpm, after extraction, lower to room temperature, filter, and centrifuge at 3800 rpm for 10 min to obtain ethanol extract. The ethanol extract was placed in a separatory apparatus, and 1.6 times the volume of ethyl acetate was added. After sealing, the mixture was shaken evenly and allowed to stand for 26 minutes. After the two phases completely separated, the upper ethyl acetate phase was collected, and water was removed to obtain the purified solution. The purified solution was then subjected to vacuum distillation, with the vacuum gauge pressure controlled at -0.095 MPa and the distillation temperature at 124℃, to obtain 4-vinyleugenol antioxidant.

[0016] 3. Post-processing 200g of deionized water was heated to 44℃, 35g of maltodextrin and 10g of pectin were added, and the mixture was stirred evenly. 0.4g of sucrose fatty acid ester was added, and stirring was continued for 15 minutes. 48g of antioxidant was added, and 1 wt% citric acid solution was added to adjust the pH to 3.8. Then, high-pressure homogenization was performed at a temperature of 44℃ for 18 minutes and a pressure of 15MPa. After homogenization, spray drying was performed at an inlet air temperature of 162℃ and an outlet air temperature of 78℃ to obtain the functional antioxidant.

[0017] 4. Mixing Functional antioxidants were added to palm oil, and the amount of functional antioxidants added was controlled at 1.8 mg / kg to obtain functional palm oil. The palm oil mentioned is Tianyijia natural pressed edible palm oil.

[0018] Example 2 1. Maillard reaction (1) Enzymatic hydrolysis Soak 100g of soybeans in 310g of deionized water at room temperature for 7 hours. After soaking, drain the water, add 390g of deionized water, grind at 7900rpm for 3 minutes, adjust the pH to 6.0, then raise the temperature to 47℃, add 0.8g of neutral protease and 0.23g of cellulase, and incubate for 2.0 hours of enzymatic hydrolysis. During the enzymatic hydrolysis, control the stirring speed at 110rpm. After the enzymatic hydrolysis is completed, filter after enzyme inactivation to obtain soybean enzymatic hydrolysate. The cellulase activity is 140,000 U / g; The activity of the neutral protease is 220,000 U / g; (2) Reaction Add 2.8g glycine and 4.2g xylose to 350g soybean enzymatic hydrolysate, stir at 420rpm for 13min, then add 0.3g zinc gluconate and sonicate for 18min at 190W, 38kHz, and 35℃. After sonication, dry to a moisture content of 20%, and adjust the pH to 6.8 with 5.5wt% sodium hydroxide solution to obtain the reaction system. Transfer the reaction system to a sealed container, increase the temperature to 170℃ at a rate of 4.8℃ / min, and maintain the temperature for 28min. After the reaction, allow it to cool naturally to room temperature to obtain the Maillard reaction product.

[0019] 2. Preparation of antioxidants Add 1.5 wt% citric acid solution to the Maillard reaction product, adjust the pH to 6.2, add 5 times the mass of anhydrous ethanol, stir well, raise the temperature to 50℃, stir for 1.5 h at a stirring speed of 190 rpm, after extraction, lower to room temperature, filter, and centrifuge at 3900 rpm for 12 min to obtain ethanol extract. The ethanol extract was placed in a separatory apparatus, and 1.5 times the volume of ethyl acetate was added. After sealing, the mixture was shaken evenly and allowed to stand for 28 minutes. After the two phases completely separated, the upper ethyl acetate phase was collected, and water was removed to obtain the purified solution. The purified solution was then subjected to vacuum distillation, with the vacuum gauge pressure controlled at -0.094 MPa and the distillation temperature at 125 °C, to obtain 4-vinyleugenol antioxidant.

[0020] 3. Post-processing Heat 200g of deionized water to 45℃, add 37g of maltodextrin and 12g of pectin, stir well, add 0.5g of sucrose fatty acid ester, continue stirring for 18min, add 50g of antioxidant, add 1.5wt% citric acid solution to adjust the pH to 4.0, and then perform high-pressure homogenization at 45℃ for 20min and 18MPa. After homogenization, perform spray drying at an inlet air temperature of 164℃ and an outlet air temperature of 80℃ to obtain the functional antioxidant.

[0021] 4. Mixing Functional antioxidants were added to palm oil, and the amount of functional antioxidants added was controlled at 2.0 mg / kg to obtain functional palm oil. The palm oil mentioned is Tianyijia natural pressed edible palm oil.

[0022] Example 3 1. Maillard reaction (1) Enzymatic hydrolysis Soak 100g of soybeans in 320g of deionized water at room temperature for 8 hours. After soaking, drain the water, add 400g of deionized water, grind at 8000rpm for 2 minutes, adjust the pH to 6.0, then raise the temperature to 50℃, add 0.9g of neutral protease and 0.25g of cellulase, and incubate for 1.8 hours for enzymatic hydrolysis. During the enzymatic hydrolysis, control the stirring speed at 110rpm. After the enzymatic hydrolysis is completed, filter after enzyme inactivation to obtain soybean enzymatic hydrolysate. The cellulase activity is 150,000 U / g; The activity of the neutral protease is 230,000 U / g; (2) Reaction Add 3.0g glycine and 4.0g xylose to 350g soybean enzymatic hydrolysate, stir at 430rpm for 15min, then add 0.3g zinc gluconate and sonicate for 20min at 200W power, 40kHz frequency, and 40℃. After sonication, dry to a moisture content of 22%, and adjust the pH to 6.8 with 6.0wt% sodium hydroxide solution to obtain the reaction system. Transfer the reaction system to a sealed container, increase the temperature to 172℃ at a rate of 5.0℃ / min, and maintain the temperature for 30min. After the reaction, allow it to cool naturally to room temperature to obtain the Maillard reaction product.

[0023] 2. Preparation of antioxidants Add 2.0 wt% citric acid solution to the Maillard reaction product, adjust the pH to 6.3, add 5 times the mass of anhydrous ethanol, stir well, raise the temperature to 52℃, stir for 1.6 h at a stirring speed of 200 rpm, after extraction, lower to room temperature, filter, and centrifuge at 4000 rpm for 12 min to obtain ethanol extract. The ethanol extract was placed in a separatory apparatus, and 1.5 times the volume of ethyl acetate was added. After sealing, the mixture was shaken evenly and allowed to stand for 30 minutes. After the two phases completely separated, the upper ethyl acetate phase was collected, and water was removed to obtain the purified solution. The purified solution was then subjected to vacuum distillation, with the vacuum gauge pressure controlled at -0.092 MPa and the distillation temperature at 126℃, to obtain 4-vinyleugenol antioxidant.

[0024] 3. Post-processing 200g of deionized water was heated to 47℃, 38g of maltodextrin and 12g of pectin were added, and the mixture was stirred evenly. 0.5g of sucrose fatty acid ester was added, and stirring was continued for 20 minutes. 50g of antioxidant was added, and 2wt% citric acid solution was added to adjust the pH to 4.0. Then, high-pressure homogenization was performed at a temperature of 46℃ for 22 minutes and a pressure of 20MPa. After homogenization, spray drying was performed at an inlet air temperature of 165℃ and an outlet air temperature of 80℃ to obtain the functional antioxidant.

[0025] 4. Mixing Functional antioxidants were added to palm oil, and the amount of functional antioxidants added was controlled at 2.3 mg / kg to obtain functional palm oil. The palm oil mentioned is Tianyijia natural pressed edible palm oil.

[0026] Comparative Example 1 The changes made in Example 2 are as follows: In the Maillard reaction step, the reaction step is as follows: 350g of soybean enzymatic hydrolysate is dried to a moisture content of 20%, and 5.5wt% sodium hydroxide solution is added to adjust the pH to 6.8 to obtain the reaction system; the reaction system is transferred to a sealed container, and the temperature is increased to 170℃ at a rate of 4.8℃ / min, and the reaction is maintained at this temperature for 28min. After the reaction is completed, the temperature is naturally lowered to room temperature to obtain the Maillard reaction product. The rest of the operations are exactly the same.

[0027] Comparative Example 2 The changes made in Example 2 are as follows: The post-processing step is omitted, and the antioxidant obtained in the antioxidant preparation step is directly used in the mixing step; The rest of the operations are exactly the same.

[0028] Performance testing The functional palm oil obtained by this invention was used as a heating oil, and the 3-MCPDE content (mg / kg) produced by frying at different temperatures and times was tested. The results are as follows:

[0029] In the preparation of antioxidants, this invention first involves enzymatic hydrolysis, where cellulase and protease degrade macromolecules in soybean raw materials, releasing small peptides, free amino acids, reducing sugars, etc., providing more active sites for subsequent Maillard reactions. Simultaneously, this process disrupts the cell structure of the raw materials, improving substrate contact efficiency in subsequent reactions. During the Maillard reaction stage, glycine and xylose are ultrasonically assisted and combine with zinc gluconate to generate the Maillard reaction product 4-vinyleugenol, which possesses strong antioxidant properties, enhancing the high-temperature oxidative stability of palm oil and reducing oil degradation. In the post-processing stage, the combined encapsulation of maltodextrin and pectin, combined with emulsification of sucrose fatty acid esters, and high-pressure homogenization, forms a uniform microcapsule system of antioxidants. Upon addition to palm oil, this system achieves molecular-level dispersion, forming a continuous protective layer within the oil. This allows the antioxidants to maintain stable antioxidant activity even at high temperatures, achieving a long-lasting inhibition of 3-MCPDE.

[0030] Comparative Example 1 omitted the addition of glycine and xylose in the Maillard reaction stage and also omitted zinc gluconate. The soybean enzymatic hydrolysate was directly subjected to a high-temperature Maillard reaction. The Maillard reaction product obtained had low antioxidant activity, and there were no effective components in the system to inhibit the reaction between chlorine sources and glycerides. During high-temperature frying, the chlorination reaction was unimpeded, resulting in a large amount of 3-MCPDE being generated. With the extension of frying time, the 3-MCPDE content increased rapidly. Comparative Example 2 omitted the post-processing steps, including the compounding and high-pressure homogenization of maltodextrin, pectin, and sucrose fatty acid esters. The antioxidant was directly added to the palm oil. The antioxidant had poor dispersibility and was prone to agglomeration in the palm oil, failing to form a uniform antioxidant film in the oil system. During high-temperature frying, there was no antioxidant protection in some areas, resulting in a significant increase in the 3-MCPDE content. Furthermore, the stability and long-term effectiveness of the antioxidant were poor. With the extension of frying time, the 3-MCPDE content increased significantly.

[0031] Unless otherwise specified, all proportions mentioned in this invention are mass proportions, and all percentages are mass percentages.

[0032] Finally, it should be noted that the above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Although the present invention has been described in detail with reference to the foregoing embodiments, those skilled in the art can still modify the technical solutions described in the foregoing embodiments or make equivalent substitutions for some of the technical features. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A method for controlling trichloropropanol esters in oils and fats, characterized in that, This includes Maillard reaction, preparation of antioxidants, post-treatment, and mixing steps; The Maillard reaction includes enzymatic hydrolysis and reaction steps; The reaction steps are as follows: add glycine and xylose to soybean enzymatic hydrolysate, stir, add zinc gluconate and sonicate, dry to a moisture content of 18-22%, adjust pH to 6.8-7.0 to obtain the reaction system; transfer the reaction system to a sealed container and react at 168-172℃ for 27-30 min to obtain Maillard reaction product; The post-processing steps are as follows: the temperature of deionized water is raised to 44-47℃, maltodextrin and pectin are added and stirred evenly, sucrose fatty acid ester is added and stirring is continued for 15-20 minutes, antioxidant is added, the pH value is adjusted to 3.8-4.0, and then high-pressure homogenization is performed, followed by spray drying to obtain functional antioxidant.

2. The method for controlling trichloropropanol esters in oils and fats according to claim 1, characterized in that, The enzymatic hydrolysis step is as follows: Soak soybeans in deionized water (I) at room temperature for 6-8 hours. After soaking, drain the water, add deionized water (II), and grind at 7800-8000 rpm for 2-3 minutes. Adjust the pH to 5.8-6.0, then raise the temperature to 45-50℃, add neutral protease and cellulase, and incubate for 1.8-2.0 hours of enzymatic hydrolysis. During the enzymatic hydrolysis, control the stirring speed at 100-110 rpm. After the enzymatic hydrolysis is completed, filter after enzyme inactivation to obtain soybean enzymatic hydrolysate.

3. The method for controlling trichloropropanol esters in oils and fats according to claim 2, characterized in that, The cellulase activity is 120,000-150,000 U / g; The activity of the neutral protease is 210,000-230,000 U / g; The mass ratio of soybean, deionized water I, deionized water II, neutral protease and cellulase is 100:300-320:380-400:0.8-0.9:0.20-0.

25.

4. The method for controlling trichloropropanol esters in oils and fats according to claim 1, characterized in that, In the reaction step, the mass ratio of soybean enzymatic hydrolysate, glycine, xylose, and zinc gluconate is 350:2.8-3.0:4.0-4.2:0.2-0.

3.

5. The method for controlling trichloropropanol esters in oils and fats according to claim 1, characterized in that, The steps for preparing the antioxidant are as follows: add 1.0-2.0 wt% citric acid solution to the Maillard reaction product, adjust the pH to 6.0-6.3, add 4-5 times the mass of anhydrous ethanol, stir evenly, raise the temperature to 48-52℃, stir for 1.4-1.6 h at a stirring speed of 180-200 rpm, after extraction, lower to room temperature, filter, and centrifuge at 3800-4000 rpm for 10-12 min to obtain the ethanol extract; The ethanol extract was placed in a separatory apparatus, and 1.5-1.6 times its volume of ethyl acetate was added. After sealing, the mixture was shaken evenly and allowed to stand for 26-30 minutes. After the two phases had completely separated, the upper ethyl acetate phase was collected, and water was removed to obtain the purified solution. The purified solution was then subjected to vacuum distillation, with the vacuum gauge pressure controlled at -0.092 to -0.095 MPa and the distillation temperature at 124-126℃, to obtain 4-vinyleugenol antioxidant.

6. The method for controlling trichloropropanol esters in oils and fats according to claim 1, characterized in that, In the post-processing step, the mass ratio of deionized water, maltodextrin, pectin, sucrose fatty acid ester, and antioxidant is 200:35-38:10-12:0.4-0.5:48-50.

7. The method for controlling trichloropropanol esters in oils and fats according to claim 1, characterized in that, The mixing step involves adding a functional antioxidant to palm oil, controlling the amount of the added functional antioxidant to be 1.8-2.3 mg / kg, to obtain functional palm oil.

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