A combined production process and application of monoglyceride and diglyceride

Abstract

The present invention provides a combined production process and application of monoglyceride and diglyceride, belonging to the technical field of organic synthesis. The combined production process comprises the following steps: (1) dissolving reaction substrates in a certain volume of solvent, mixing uniformly to obtain a mixed substrate; (2) transferring the mixed substrate in step (1) into a packed bed enzyme reactor equipped with immobilized lipase, and reacting under vacuum conditions to obtain a reaction product; (3) subjecting the reaction product in step (2) to molecular distillation to separate and obtain monoglyceride and diglyceride; The present invention uses a mixed solution of tert-butanol and propylene glycol methyl ether as the solvent, and a mixture of microbial lipase - Candida rugosa and commercial immobilized lipase Lipozyme RM IM as the lipase system. By controlling their ratio and reaction temperature, the mixed enzyme can exhibit better catalytic efficiency and enzyme stability, thereby obtaining monoglyceride and diglyceride with high yield and high purity.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic synthesis, and particularly relates to a combined production process and application of monoglyceride and diglyceride. Background Art

[0002] Oils and fats are mixtures of fatty acid triglycerides and are one of the essential components in foods. They can not only provide calories but also essential fatty acids and various fat-soluble vitamins that the human body cannot synthesize and must obtain from vegetable oils. However, studies have found that excessive intake of triglycerides can cause diseases such as cardiovascular diseases, hypertension, and obesity in humans. In the late 1980s, a diglyceride with physicochemical properties similar to those of triglyceride oils was developed. Compared with triglyceride oils, it has two major nutritional functions: one is to inhibit the increase in postprandial serum triglycerides, mainly due to the 1,3-diglycerol in diglyceride oil playing a role in reducing postprandial serum triglycerides; the other is to inhibit the accumulation of body fat. Studies have found that compared with triglyceride oils, after ingesting diglyceride, individuals have a lower hunger score, lower appetite, a lower amount of food that can be ingested, and a lower desire to eat. Therefore, replacing ordinary edible oils with diglyceride will increase the rate of body fat oxidation and inhibit the appetite of individuals. Although diglyceride is a natural component of oils and fats, its content is relatively low, and diglyceride is also an intermediate product of the metabolism of oils and fats in the human body. Therefore, the functional characteristics, biochemical functions, and mechanisms of diglyceride have attracted much attention and become a hot topic in the research of the oil and fat industry. Monoglyceride is an important polyol non-ionic surfactant. As an important food emulsifier and additive, it has functions such as emulsification, dispersion, and wetting, and has wide applications in grain and oil foods, medicine, cosmetics, detergent industry, and polymer synthesis. Therefore, the preparation and purification of monoglyceride are also one of the research hotspots.

[0003] Esterification reaction of fatty acid and glycerol under the action of a catalyst can obtain diglyceride, and at the same time, by-products monoglyceride and triglyceride are obtained. The preparation methods are divided into chemical methods and enzymatic methods. Chemical methods have disadvantages such as high energy consumption, easy degradation of reaction products, and difficulty in separation and purification, and are not suitable for the production of glycerides. In recent years, people have begun to explore enzymatic preparation.

[0004] As disclosed in Chinese Patent CN103361387A, a method for the enzymatic production of diglyceride with co-production of unsaturated monoglyceride includes the following steps: (1) adding absolute ethanol to natural oil and performing an alcoholysis reaction under the catalysis of immobilized lipase to obtain an alcoholysis product with the production rate of ethyl fatty acid being 5 - 40% w / w, and removing the remaining ethanol; (2) adding 5 - 15% w / w of glycerol to the alcoholysis product obtained in step (1), and then reacting the above mixed substrate in a packed-bed enzyme reactor filled with immobilized lipase under vacuum conditions; (3) subjecting the reaction product obtained in step (2) to molecular distillation, separating to obtain a high-temperature fraction containing diglyceride as the product, and simultaneously obtaining a low-temperature fraction mainly composed of monoglyceride. The reaction system of this invention does not need to add water, thus solving the problem of acid value of the product, and enabling co-production of monoglyceride; moreover, glycerol does not need to be pre-adsorbed, simplifying the production operation.

[0005] Again, as disclosed in Chinese Patent CN103074388A, a method for the enzymatic synthesis of monoglyceride and diglyceride under ultra-high pressure includes the following steps: (1) dissolving the reaction substrate in a certain volume of solvent, and then adding a certain amount of lipase and mixing evenly; (2) placing it in an ultra-high pressure device for enzymatic reaction to obtain a mixture of fatty acid and glyceride; (3) separating and purifying the mixture obtained in step (2) through molecular distillation technology to obtain monoglyceride and diglyceride. The method for the enzymatic synthesis of monoglyceride and diglyceride under ultra-high pressure of this invention has mild reaction conditions, high conversion rate, and less loss of enzyme activity, which is beneficial to shortening the reaction time, reducing production costs, and is suitable for large-scale popularization and application.

[0006] However, although the co-production of monoglyceride and diglyceride is achieved in the existing preparation methods, the yields and purities of the finally obtained monoglyceride and diglyceride cannot better meet the requirements. Therefore, a co-production process with relatively high yields and purities of monoglyceride and diglyceride needs to be developed. Summary of the Invention

[0007] Based on the deficiencies existing in the prior art, the present invention aims to provide a co-production process and application of monoglyceride and diglyceride. By selecting lipase and solvent, the present invention enables the substrate to have a high solubility in the solvent, thereby increasing the speed of the enzymatic reaction.

[0008] To achieve the above object, the present invention is implemented by adopting the following technical solutions:

[0009] The present invention provides a co-production process of monoglyceride and diglyceride, including the following steps:

[0010] (1) Dissolving the reaction substrate in a solvent and mixing evenly to obtain a mixed substrate;

[0011] (2) Transfer the mixed substrate from step (1) into a packed bed enzyme reactor containing immobilized lipase, and react under vacuum conditions to obtain a reaction product;

[0012] (3) The reaction product of step (2) is subjected to molecular distillation to separate and obtain monoglyceride and diglyceride.

[0013] The reaction substrate described in the above step (1) is a mixture of oil and glycerol;

[0014] Among them, the oil is selected from vegetable oil or animal oil;

[0015] The animal oil is selected from one or more of fish oil, lard, beef tallow and chicken oil;

[0016] The vegetable oil is selected from one or more of soybean oil, rapeseed oil, corn oil, palm oil, peanut oil, sunflower oil, camellia oil, olive oil and rice bran oil; preferably olive oil and / or rice bran oil.

[0017] The molar ratio of the oil to glycerol is 1:2 - 6; preferably 1:3 - 5; more preferably 1:3 - 4.

[0018] The solvent described in the above step (1) is a mixture of tert-butanol and propylene glycol methyl ether;

[0019] Preferably, the volume ratio of tert-butanol to propylene glycol methyl ether is 60 - 80:20 - 40;

[0020] More preferably, the volume ratio of tert-butanol to propylene glycol methyl ether is 70:30.

[0021] The purpose of adding an organic solvent as a reaction medium is to increase the solubility of the substrate and solve the problem that glycerol and oil are difficult to dissolve in each other. tert-Butanol has been proven to be a suitable solvent medium, but the freezing point of tert-butanol is too high and its application is limited. In the implementation process of the present invention, propylene glycol methyl ether is added to tert-butanol, and the volume ratio of tert-butanol to propylene glycol methyl ether is controlled to be 60 - 80:20 - 40, so that the freezing point of the mixed solvent is reduced and there is no obvious impact on the reaction.

[0022] The mass-volume ratio of the reaction substrate to the solvent is 0.2 - 0.5:1 (g / ml);

[0023] Preferably, the mass-volume ratio of the reaction substrate to the solvent is 0.3 - 0.4:1 (g / ml);

[0024] More preferably, the mass-volume ratio of the reaction substrate to the solvent is 0.35:1 (g / ml).

[0025] The immobilized lipase described in the above step (2) is selected from one or more of Candida cylindracea, Candida rugosa, and Chromobacterium viscosum lipase;

[0026] The immobilized lipase also includes Lipozyme TL IM or / and Lipozyme RM IM;

[0027] Preferably, the lipase is a mixture of Candida rugosa and Lipozyme RM IM;

[0028] More preferably, the mass ratio of Candida rugosa to Lipozyme RM IM is 3-5:1; preferably 4:1.

[0029] In the implementation process of the present invention, a mixture of microbial lipase - Candida rugosa and commercial immobilized lipase Lipozyme RM IM is used. By controlling their ratio, under the condition of relatively low addition amount, it can be more suitable for the solvent system and can exhibit better catalytic efficiency and enzyme stability.

[0030] As is well known in the art, in an aqueous solution, the hydrogen bonds formed between water molecules and the functional groups of enzyme molecules will break the hydrogen bonds within the enzyme molecules. This makes the enzyme molecules become loose and in an "open" state, causing the enzyme molecules to be in a dynamic equilibrium of "compact" and "open", showing a certain flexibility, and thus playing a catalytic role. On the contrary, in an organic solvent, due to the extremely small amount of water molecules, the hydrogen bonds formed between the enzyme molecules and them are extremely few. Therefore, the hydrogen bonds of the enzyme molecules play a dominant role, making the structure of the enzyme molecules become "rigid". This rigidity limits the transformation of the enzyme molecule structure in a hydrophobic environment and can maintain the same structure and conformation as in water, showing catalytic activity. Its catalytic activity is closely related to the water content in the organic solvent reaction system. Only when the best balance point is reached between the rigidity and thermodynamic stability of the enzyme molecule structure at the optimal water content, the enzyme shows the maximum activity. When the water content is lower than the optimal water content, the enzyme conformation is too "rigid", resulting in a decrease or even loss of activity; when the water content is too high, the flexibility of the enzyme structure is too large, causing changes in the enzyme structure and even inactivation.

[0031] In the implementation process of the present invention, it is found that the enzyme activity is the best when the water content in the reaction system is 0.5-4.0% of the mass of glycerol; preferably, the water content of the reaction system is 1.5-2.5% of the mass of glycerol; more preferably, the water content of the reaction system is 2.0% of the mass of glycerol.

[0032] The addition amount of the immobilized lipase described in the above step (2) is 1-5% of the mass of the oil; preferably 2-4%; more preferably 2.5%.

[0033] The temperature of the reaction described in step (2) above is 50 - 60°C; preferably 55°C; the time is 2 - 4 hours; preferably 3 hours.

[0034] The molecular distillation described in step (3) is carried out in five stages. The first-stage molecular distillation is used for degassing; the second-stage molecular distillation is used for removing glycerol; the third-stage molecular distillation is used for removing free fatty acids; the fourth-stage molecular distillation yields monoglyceride; the fifth-stage molecular distillation removes triglycerides to obtain diglyceride.

[0035] As some preferred embodiments, the temperature of the first-stage molecular distillation is 50 - 90°C and the vacuum degree is 1000 - 2000 Pa; the temperature of the second-stage molecular distillation is 100 - 150°C and the vacuum degree is 50 - 100 Pa; the temperature of the third-stage molecular distillation is 160 - 180°C and the vacuum degree is 1 - 50 Pa; the temperature of the fourth-stage molecular distillation is 180 - 220°C and the vacuum degree is 1 - 50 Pa; the temperature of the fifth-stage molecular distillation is 200 - 220°C and the vacuum degree is 0.5 - 20 Pa.

[0036] As a preferred embodiment, the temperature of the first-stage molecular distillation is 65°C and the vacuum degree is 1500 Pa; the temperature of the second-stage molecular distillation is 110°C and the vacuum degree is 65 Pa; the temperature of the third-stage molecular distillation is 165°C and the vacuum degree is 2.5 Pa; the temperature of the fourth-stage molecular distillation is 180°C and the vacuum degree is 2.5 Pa; the temperature of the fifth-stage molecular distillation is 210°C and the vacuum degree is 1.5 Pa.

[0037] When the molecular distillation in the present invention separates the same components, it can be cyclically distilled 2 - 3 times under the same conditions.

[0038] The reaction product of step (3) mainly contains triglyceride, diglyceride, monoglyceride, ethyl fatty acid, and glycerol. In the present invention, monoglyceride and diglyceride are used as target products, and the purpose of separation is to obtain relatively pure monoglyceride and diglyceride. The commonly used separation method is molecular distillation, and the characteristic of this kind of method is that it is carried out under vacuum conditions, which can greatly reduce the temperature required for separation.

[0039] The present invention also provides a monoglyceride or diglyceride prepared by the above combined production process.

[0040] The present invention also provides an application of the monoglyceride or diglyceride prepared by the above combined production process in the preparation of medicines.

[0041] Compared with the prior art, the beneficial effects of the present invention are as follows:

[0042] (1) The present invention uses a mixed solution of tert-butanol and propylene glycol methyl ether as a solvent, and controls the volume ratio of the two to 60 - 80:20 - 40. This mixed solvent can not only achieve the miscibility of glycerol and oil, but also reduce the melting point of tert-butanol, and at the same time will not have an obvious impact on the reaction.

[0043] (2) It was unexpectedly found during the implementation process that a small amount of water in the reaction system can better promote enzyme activity, and the enzyme activity is the best when the water content in the system is 0.5 - 4.0% of the mass of glycerol.

[0044] (3) During the implementation of the present invention, a mixture of microbial lipase - Candida rugosa and commercial immobilized lipase Lipozyme RM IM is used. By controlling their ratio, under the condition of a relatively small addition amount, it can be more suitable for the solvent system and can exhibit better catalytic efficiency and enzyme stability.

[0045] (4) The preparation method of the present invention is simple, and it can obtain monoglyceride and diglyceride with high yield and high purity at the same time. Detailed implementation manners

[0046] Next, in combination with the implementation manners of the present invention, the technical solutions in the implementation manners of the present invention will be clearly and completely described. Obviously, the described implementation manners are only a part of the implementation manners of the present invention, rather than all of the implementation manners. Based on the implementation manners in the present invention, all other implementation manners obtained by those of ordinary skill in the art without making creative efforts belong to the scope protected by the present invention.

[0047] The experimental methods used in the following examples are all conventional methods unless otherwise specified; the water used is all deionized water; the materials, reagents, etc. used, unless otherwise specified, can all be obtained from commercial channels.

[0048] Example 1 A combined production process of monoglyceride and diglyceride

[0049] It includes the following steps:

[0050] (1) Dissolve olive oil and glycerol with a molar ratio of 1:1 in a mixed solution of tert-butanol and propylene glycol methyl ether with a volume ratio of 60:40, and mix evenly to obtain a mixed substrate; the mass ratio of olive oil and glycerol to the volume of tert-butanol and propylene glycol methyl ether is 0.2:1 (g / ml).

[0051] (2) Transfer the mixed substrate from step (1) into a packed-bed enzyme reactor containing immobilized lipase. The water content is 0.5% of the mass of glycerol, and the reaction is carried out under vacuum conditions at a temperature of 50 °C for 4 hours to obtain a reaction product. The immobilized lipase is a mixture of Candida rugosa and Lipozyme RM IM with a mass ratio of 3:1. The addition amount of the immobilized lipase is 1% of the mass of the oil.

[0052] (3) The reaction product of step (2) is subjected to molecular distillation in five stages. The temperature of the first-stage molecular distillation is 50 °C and the vacuum degree is 1000 Pa for degassing. The temperature of the second-stage molecular distillation is 100 °C and the vacuum degree is 50 Pa for removing glycerol. The temperature of the third-stage molecular distillation is 160 °C and the vacuum degree is 10 Pa for removing free fatty acids. The temperature of the fourth-stage molecular distillation is 180 °C and the vacuum degree is 10 Pa to obtain monoglyceride. The temperature of the fifth-stage molecular distillation is 200 °C and the vacuum degree is 2 Pa to remove triglyceride and obtain diglyceride.

[0053] Example 2 A combined production process of monoglyceride and diglyceride

[0054] It includes the following steps:

[0055] (1) Dissolve olive oil and glycerol with a molar ratio of 1:3 in a mixed solution of tert-butanol and propylene glycol methyl ether with a volume ratio of 80:20, and mix evenly to obtain a mixed substrate. The mass ratio of olive oil and glycerol to the volume of tert-butanol and propylene glycol methyl ether is 0.5:1 (g / ml).

[0056] (2) Transfer the mixed substrate from step (1) into a packed-bed enzyme reactor containing immobilized lipase. The water content is 4.0% of the mass of glycerol, and the reaction is carried out under vacuum conditions at a temperature of 60 °C for 2 hours to obtain a reaction product. The immobilized lipase is a mixture of Candida rugosa and Lipozyme RM IM with a mass ratio of 5:1. The addition amount of the immobilized lipase is 5% of the mass of the oil.

[0057] (3) The reaction product of step (2) is subjected to molecular distillation in five stages. The temperature of the first-stage molecular distillation is 90 °C and the vacuum degree is 2000 Pa for degassing. The temperature of the second-stage molecular distillation is 150 °C and the vacuum degree is 100 Pa for removing glycerol. The temperature of the third-stage molecular distillation is 180 °C and the vacuum degree is 50 Pa for removing free fatty acids. The temperature of the fourth-stage molecular distillation is 220 °C and the vacuum degree is 50 Pa to obtain monoglyceride. The temperature of the fifth-stage molecular distillation is 220 °C and the vacuum degree is 20 Pa to remove triglyceride and obtain diglyceride.

[0058] Example 3 A combined production process of monoglyceride and diglyceride

[0059] It includes the following steps:

[0060] (1) Dissolve olive oil and glycerol with a molar ratio of 1:2 in a mixed solution of tert-butanol and propylene glycol methyl ether with a volume ratio of 70:30, and mix evenly to obtain a mixed substrate; the mass ratio of olive oil and glycerol to the volume of tert-butanol and propylene glycol methyl ether is 0.35:1 (g / ml);

[0061] (2) Transfer the mixed substrate in step (1) into a packed bed enzyme reactor equipped with immobilized lipase. The water content is 1.0% of the mass of glycerol, and the reaction is carried out under vacuum conditions. The reaction temperature is 55°C and the time is 3 hours to obtain a reaction product; the immobilized fat is a mixture of Candida rugosa and Lipozyme RM IM with a mass ratio of 4:1; the addition amount of the immobilized lipase is 2% of the mass of the oil;

[0062] (3) The reaction product in step (2) is subjected to molecular distillation in five stages. The temperature of the first-stage molecular distillation is 65°C and the vacuum degree is 1500 Pa for degassing; the temperature of the second-stage molecular distillation is 110°C and the vacuum degree is 65 Pa for removing glycerol; the temperature of the third-stage molecular distillation is 165°C and the vacuum degree is 2.5 Pa for removing free fatty acids; the temperature of the fourth-stage molecular distillation is 180°C and the vacuum degree is 2.5 Pa to obtain monoglyceride; the temperature of the fifth-stage molecular distillation is 210°C and the vacuum degree is 1.5 Pa to remove triglyceride and obtain diglyceride.

[0063] Comparative Example 1

[0064] The difference from Example 3 is that: in step (2), only Lipozyme RM IM is used as the immobilized lipase, and the others are the same as in Example 3.

[0065] Comparative Example 2

[0066] The difference from Example 3 is that: in step (2), the mass ratio of Candida rugosa and Lipozyme RM IM is 1:1, and the others are the same as in Example 3.

[0067] Comparative Example 3

[0068] The difference from Example 3 is that: no water is added to the reaction system in step (2), and the others are the same as in Example 3.

[0069] Comparative Example 4

[0070] The difference from Example 3 is that: the water content in the reaction system in step (2) is 5% of the mass of glycerol, and the others are the same as in Example 3.

[0071] Comparative Example 5

[0072] The difference from Example 3 is that: in step (1), propylene glycol methyl ether is replaced by tert-amyl alcohol, and the others are the same as in Example 3.

[0073] Effect data:

[0074] Detect the contents and purities of monoglyceride and diglyceride. The detection method is gas chromatography. For details, refer to the national food safety standard GB1886.65. The detection results are shown in Table 1 below.

[0075] Table 1

[0076]

[0077] According to the detection results in Table 1 above, it can be known that the combined production process provided by the present invention can realize the separation and purification of monoglyceride and diglyceride. The obtained monoglyceride can meet the conditions that the yield is higher than 38% under the condition that the purity is greater than 90%. In particular, the purity of monoglyceride in Example 3 can reach 96% and the yield is 46.3%; the obtained diglyceride can meet the conditions that the yield is higher than 32% under the condition that the purity is greater than 85%. In particular, the purity of diglyceride in Example 3 can reach 92.4% and the yield is 34.4%.

[0078] In Comparative Example 1, only the microbial lipase - Candida rugosa was used to catalyze the reaction system, which would affect the catalytic efficiency to a certain extent, and further affect the formation of monoglyceride and diglyceride. It can be seen from the detection results in Table 1 above that when the purity is comparable to that of the examples, the yields of monoglyceride and diglyceride are significantly reduced.

[0079] In Comparative Example 2, the mass ratio of the two enzymes, namely Candida rugosa and Lipozyme RM IM, was changed, which would also affect the catalytic efficiency of the enzymes to a certain extent, and further affect the formation of monoglyceride and diglyceride. It can be seen from the detection results in Table 1 above that when the purity is comparable to that of the examples, the yields of monoglyceride and diglyceride are increased compared with those in Comparative Example 1, indicating that the mixed use of the two enzymes has a higher catalytic efficiency than a single enzyme, but the yields are significantly lower than those in the examples, indicating that the mass ratio of the two enzymes has a significant impact on the catalytic efficiency.

[0080] In Comparative Example 3, water was not added to the reaction system during the reaction, making the enzyme conformation too "rigid", which would affect the catalytic activity of the enzyme to a certain extent, reduce the catalytic effect of the enzyme, and further reduce the yields of monoglyceride and diglyceride.

[0081] In Comparative Example 4, too much water was added to the reaction system, making the flexibility of the enzyme structure in the reaction system too large, causing changes and even inactivation of the enzyme structure, thereby reducing the yields of monoglyceride and diglyceride.

[0082] Comparative Example 5: Changing the type of solvent will affect the freezing point of the reaction system to a certain extent, thereby affecting the yields of monoglyceride and diglyceride, resulting in a certain degree of reduction in the yields.

[0083] In summary, it can be seen that by using the co-production process provided by the present invention, monoglyceride and diglyceride with high yields and high purities can be obtained simultaneously.

[0084] Finally, it should be noted that the above content is only used to illustrate the technical solution of the present invention, rather than limiting the protection scope of the present invention. Any simple modification or equivalent replacement of the technical solution of the present invention by those of ordinary skill in the art shall not depart from the essence and scope of the technical solution of the present invention.

Claims

1. A combined production process of monoglyceride and diglyceride, characterized in that: It includes the following steps: (1) Dissolve the reaction substrate in a solvent and mix evenly to obtain a mixed substrate; (2) Transfer the mixed substrate in step (1) into a packed bed enzyme reactor loaded with immobilized lipase and react under vacuum conditions to obtain a reaction product; (3) Subject the reaction product in step (2) to molecular distillation to separate and obtain monoglyceride and diglyceride; The solvent described in step (1) is a mixture of tert-butanol and propylene glycol methyl ether; the volume ratio of the two is 60-80:20-40; The immobilized lipase described in step (2) is a mixture of Candida rugosa and Lipozyme RM IM; the mass ratio is 3-5:1; The reaction substrate described in step (1) is a mixture of oil, glycerol and water, and the content of water is 0.5-4.0% of the mass of glycerol; The molecular distillation described in step (3) is carried out in five stages. The first-stage molecular distillation is for degassing, the distillation temperature is 50-90°C, and the vacuum degree is 1000-2000 Pa; the second-stage molecular distillation is for removing glycerol, the distillation temperature is 100-150°C, and the vacuum degree is 50-100 Pa; the third-stage molecular distillation is for removing free fatty acids, the distillation temperature is 160-180°C, and the vacuum degree is 1-50 Pa; the fourth-stage molecular distillation obtains monoglyceride, the distillation temperature is 180-220°C, and the vacuum degree is 1-50 Pa; the fifth-stage molecular distillation removes triglyceride, the distillation temperature is 200-220°C, and the vacuum degree is 0.5-20 Pa to obtain diglyceride.

2. The combined production process according to claim 1, characterized in that: The mass-volume ratio of the reaction substrate to the solvent is 0.2-0.5 g:1 mL.

3. The combined production process according to claim 1, characterized in that: The oil is selected from vegetable oil or animal oil.

4. The combined production process according to claim 3, characterized in that: The animal oil is selected from one or more of fish oil, lard, beef tallow and chicken oil.

5. The co-production process according to claim 3, characterized in that: The vegetable oil is selected from one or more of soybean oil, rapeseed oil, corn oil, palm oil, peanut oil, sunflower seed oil, camellia oil, olive oil and rice bran oil.

6. The combined production process according to claim 1, characterized in that: The content of water is 2.0% of the mass of glycerol.

7. The combined production process according to claim 1, characterized in that: The addition amount of the immobilized lipase is 1-5% of the mass of the oil.

8. The combined production process according to claim 1, characterized in that: The reaction temperature described in step (2) is 50-60°C; the time is 2-4 hours.

9. The combined production process according to claim 1, characterized in that: The temperature of the first-stage molecular distillation is 65°C, and the vacuum degree is 1500 Pa; the temperature of the second-stage molecular distillation is 110°C, and the vacuum degree is 65 Pa; the temperature of the third-stage molecular distillation is 165°C, and the vacuum degree is 2.5 Pa; the temperature of the fourth-stage molecular distillation is 180°C, and the vacuum degree is 2.5 Pa; the temperature of the fifth-stage molecular distillation is 210°C, and the vacuum degree is 1.5 Pa.

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