Green synthesis process for preparing high-purity horse oil ethyl ester based on enzyme catalysis method
By combining enzyme catalysis with the use of protease and lipase, the problem of unstable enzyme catalyst activity in the synthesis of ethyl horse oil was solved, realizing the green synthesis of high-purity ethyl horse oil and improving product quality and production efficiency.
Patent Information
- Application Number
- CN202511654236.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-11-12
- Publication Date
- 2026-01-09
AI Technical Summary
The enzyme catalyst is easily deactivated by the substrate horse oil during the preparation of high-purity horse oil ethyl ester. Its activity decreases significantly after repeated use, and the enzyme activity is unstable, making repeated use difficult.
Enzymatic catalysis was employed to remove impurities from horse oil through purification. Esterification and alcoholysis reactions were carried out under mild conditions using different types of proteases and lipases. The enzyme catalysis process was optimized by using immobilized enzyme technology and process optimization to improve enzyme stability and selectivity.
It improves the purity and stability of ethyl horse oil, reduces byproduct formation, lowers energy consumption and environmental impact, achieves highly selective and green synthesis, and simplifies subsequent purification steps.
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Abstract
Description
Technical Field
[0001] This invention relates to the field of horse oil ethyl ester processing technology, and more specifically, to a green synthesis process for preparing high-purity horse oil ethyl ester based on enzyme catalysis. Background Technology
[0002] Traditional chemical synthesis methods are often accompanied by high energy consumption, high pollution, and numerous byproducts, causing serious environmental impacts. Against this backdrop, the concept of green chemistry has emerged, emphasizing the reduction or elimination of harmful substances during chemical synthesis, improving atom economy, and achieving sustainable development. Enzymes, as biocatalysts, have become a research hotspot in the field of chemical synthesis due to their high efficiency, specificity, mild reaction conditions, and potential applications in green synthesis. Enzyme catalysis can not only increase reaction rates and selectivity but also proceed under milder conditions, thereby reducing energy consumption and environmental pollution.
[0003] The study of enzyme catalysis mechanisms not only helps to reveal the nature of chemical reactions in living organisms, but also has important application value in green synthesis. A deeper understanding of enzyme catalysis mechanisms allows for the design of more efficient and environmentally friendly synthetic processes, driving the chemical industry towards a green and sustainable future. This research is not only theoretically innovative but also has significant practical application value, and will have a profound impact on promoting green chemistry and sustainable development.
[0004] High-purity horse oil ethyl ester is a compound extracted from horse oil and subjected to ethyl esterification. It is primarily used as a raw material in high-end cosmetics and possesses moisturizing and anti-aging properties. High-purity horse oil ethyl ester is a product of horse oil through refining and ethyl esterification processes, resulting in high purity and suitability for the cosmetic industry. As a high-end raw material, it can enhance the skincare effects of products, such as improving skin elasticity and hydration.
[0005] In existing technologies, enzyme catalysts are easily deactivated by the substrate horse oil during the reaction process, and their activity decreases significantly after repeated use. Enzyme catalysis suffers from the core problems of "unstable enzyme activity and difficulty in repeated use." Horse oil contains free fatty acids, which may interfere with the enzyme catalysis process. Free fatty acids undergo saponification under alkaline catalysis, while enzyme catalysts require high purity raw materials. Summary of the Invention
[0006] This invention provides a green synthesis process for preparing high-purity horse oil ethyl ester based on enzyme catalysis, which solves the technical problems that enzyme catalysts are easily deactivated by the substrate horse oil during the reaction process, and their activity decreases significantly after repeated use, as well as the unstable enzyme activity and difficulty in repeated use.
[0007] In a first aspect, the present invention provides a green synthesis process for preparing high-purity horse oil ethyl ester based on enzyme catalysis, comprising the following steps: (4) Horse oil needs to be purified to remove impurities to obtain crude horse oil; (5) Add solvent and enzyme preparation to crude horse oil, control the temperature at 40–60℃, and react for 24–36 h to obtain refined horse oil ethyl ester. (6) Add lipase to refined horse oil ethyl ester and obtain high-purity horse oil ethyl ester through alcoholysis reaction.
[0008] Preferably, in step (1), horse oil is purified by removing impurities through filtration, deacidification or molecular distillation.
[0009] Preferably, in step (2), crude horse oil and enzyme preparation are added to the esterification reactor and stirred in a weight ratio of 1~2: 4~9.
[0010] Preferably, in step (2), the solvent is isooctane or 2-methyltetrahydrofuran.
[0011] Preferably, in step (2), the enzyme preparation is selected from at least one of acetylesterase or carbamate esterase.
[0012] Preferably, the amount of acetylesterase added is 2,000,000 to 2,500,000 U / g, and the amount of ethyl carbamate added is 800,000 to 1,000,000 U / g.
[0013] Preferably, in step (3), the mass ratio of the lipase to refined horse oil ethyl ester is 1:1000 to 1:1800.
[0014] Preferably, in step (3), the reaction system consists of 2.5-5% anhydrous ethanol and 0.5-1.2% Tween 80, and the reaction temperature is 30-60℃.
[0015] In summary, the present invention has the following beneficial effects: 7. In this invention, alkaline protease and papain exhibit the best hydrolysis effect on protein impurities, while neutral protease and trypsin, in specific combinations, can efficiently degrade complex protein structures. This combination can more thoroughly hydrolyze protein impurities in horse oil, reduce byproducts, and improve the purity of the target product, horse oil ethyl ester. All proteases function under mild conditions (low temperature / room temperature, near-neutral or weakly alkaline pH), which is highly compatible with the low energy consumption and low solvent requirements of enzyme catalysis processes. Differences in peptide structure produced by different proteases may affect the functionality of the final product. Walnut peptides prepared by neutral protease have the highest antioxidant activity. In the synthesis of horse oil ethyl ester, protease combinations can enhance product stability or physiological activity by optimizing the precursor peptide structure.
[0016] 2. In this invention, the lipase-catalyzed reaction is typically carried out at low temperature (e.g., 50°C) and normal pressure, which avoids the damage to unsaturated fatty acids in horse oil caused by high temperature and high pressure (e.g., oxidation or isomerization of carbon-carbon double bonds), ensuring the structural integrity and nutritional value of the product. In the transesterification reaction, lipase can selectively enrich polyunsaturated fatty acids, avoiding side reactions caused by traditional acid / base catalysts. High selectivity simplifies subsequent purification steps, making it easier to obtain high-purity horse oil ethyl ester.
[0017] 3. The core advantages of this invention in preparing high-purity horse oil ethyl ester via enzyme catalysis lie in its high selectivity, low environmental impact, energy efficiency, and simplified process. Its green synthesis process utilizes immobilized enzyme technology and process optimization. Enzyme catalysis exhibits high specificity, precisely catalyzing the target reaction and significantly reducing byproduct formation, thereby improving product purity.
[0018] It should be understood that the above general description and the following detailed description are exemplary and explanatory only, and do not limit the scope of protection of the present invention. Detailed Implementation
[0019] The present invention will be further described in detail below with reference to the embodiments. It should be noted that: unless otherwise specified, the conditions in the following embodiments are carried out according to conventional conditions or the conditions recommended by the manufacturer. Unless otherwise specified, the raw materials used in the following embodiments can be obtained from commercially available sources.
[0020] Example Example 1 A green synthesis process for preparing high-purity horse oil ethyl ester based on enzyme catalysis includes the following steps: (8) Horse oil needs to be purified to remove impurities to obtain crude horse oil; (9) Add solvent and enzyme preparation to crude horse oil, control the temperature at 40℃, and react for 24 hours to obtain refined horse oil ethyl ester. (10) Lipase was added to refined horse oil ethyl ester and high-purity horse oil ethyl ester was obtained by alcoholysis reaction.
[0021] In step (1), horse oil is purified by removing impurities through filtration.
[0022] In step (2), crude horse oil and enzyme preparation are added to the esterification reactor at a weight ratio of 1:4 and stirred to carry out the esterification reaction. In step (2), the solvent is isooctane.
[0023] In step (2), the enzyme preparation is selected from acetylesterase or ethyl carbamate, with the amount of acetylesterase added being 2 million U / g and the amount of ethyl carbamate added being 800,000 U / g.
[0024] In step (3), the mass ratio of lipase to refined horse oil ethyl ester is 1:1000.
[0025] In step (3), the reaction system consists of 2.5% anhydrous ethanol and 0.5% Tween 80, and the reaction temperature is 30℃.
[0026] Example 2 A green synthesis process for preparing high-purity horse oil ethyl ester based on enzyme catalysis includes the following steps: (11) Horse oil needs to be purified to remove impurities to obtain crude horse oil; (12) Add solvent and enzyme preparation to crude horse oil, control the temperature at 45℃, and react for 28 hours to obtain refined horse oil ethyl ester. (13) Lipase was added to refined horse oil ethyl ester and high-purity horse oil ethyl ester was obtained by alcoholysis reaction.
[0027] In step (1), the horse oil is purified by removing impurities through filtration.
[0028] In step (2), crude horse oil and enzyme preparation are added to the esterification reactor at a weight ratio of 1:5 and stirred to carry out the esterification reaction. In step (2), the solvent is isooctane.
[0029] In step (2), the enzyme preparation is selected from acetylesterase or ethyl carbamate, with the amount of acetylesterase added being 2.2 million U / g and the amount of ethyl carbamate added being 850,000 U / g.
[0030] In step (3), the mass ratio of lipase to refined horse oil ethyl ester is 1:1200.
[0031] In step (3), the reaction system consists of 3% anhydrous ethanol and 0.8% Tween 80, and the reaction temperature is 38℃.
[0032] Example 3 A green synthesis process for preparing high-purity horse oil ethyl ester based on enzyme catalysis includes the following steps: (14) Horse oil needs to be purified to remove impurities to obtain crude horse oil; (15) Add solvent and enzyme preparation to crude horse oil, control the temperature at 50℃, and react for 30 hours to obtain refined horse oil ethyl ester. (16) Lipase was added to refined horse oil ethyl ester and high-purity horse oil ethyl ester was obtained by alcoholysis reaction.
[0033] In step (1), the horse oil is purified by removing impurities through filtration.
[0034] In step (2), crude horse oil and enzyme preparation are added to the esterification reactor at a weight ratio of 1:7, stirred, and the esterification reaction is carried out. In step (2), the solvent is isooctane.
[0035] In step (2), the enzyme preparation is selected from acetylesterase or ethyl carbamate, with the amount of acetylesterase added being 2.3 million U / g and the amount of ethyl carbamate added being 900,000 U / g.
[0036] In step (3), the mass ratio of lipase to refined horse oil ethyl ester is 1:1500.
[0037] In step (3), the reaction system consists of 3.5% anhydrous ethanol and 0.9% Tween 80, and the reaction temperature is 45℃.
[0038] Example 4 A green synthesis process for preparing high-purity horse oil ethyl ester based on enzyme catalysis includes the following steps: (17) Horse oil needs to be purified to remove impurities to obtain crude horse oil; (18) Add solvent and enzyme preparation to crude horse oil, control the temperature at 55℃, and react for 32 hours to obtain refined horse oil ethyl ester. (19) Lipase was added to refined horse oil ethyl ester and high-purity horse oil ethyl ester was obtained by alcoholysis reaction.
[0039] In step (1), the horse oil is purified by removing impurities through filtration.
[0040] In step (2), crude horse oil and enzyme preparation are added to the esterification reactor in a weight ratio of 2:5, stirred, and the esterification reaction is carried out. In step (2), the solvent is isooctane.
[0041] In step (2), the enzyme preparation is selected from acetylesterase or ethyl carbamate, with the amount of acetylesterase added being 2.4 million U / g and the amount of ethyl carbamate added being 950,000 U / g.
[0042] In step (3), the mass ratio of lipase to refined horse oil ethyl ester is 1:1600.
[0043] In step (3), the reaction system consists of 4% anhydrous ethanol and 1% Tween 80, and the reaction temperature is 55℃.
[0044] Example 5 A green synthesis process for preparing high-purity horse oil ethyl ester based on enzyme catalysis includes the following steps: (20) Horse oil needs to be purified to remove impurities to obtain crude horse oil; (21) Add solvent and enzyme preparation to crude horse oil, control the temperature at 60℃, and react for 36 hours to obtain refined horse oil ethyl ester. (22) Lipase was added to refined horse oil ethyl ester and high-purity horse oil ethyl ester was obtained by alcoholysis reaction.
[0045] In step (1), the horse oil is purified by removing impurities through filtration.
[0046] In step (2), crude horse oil and enzyme preparation are added to the esterification reactor in a weight ratio of 2:9, stirred, and the esterification reaction is carried out. In step (2), the solvent is isooctane.
[0047] In step (2), the enzyme preparation is selected from acetylesterase or ethyl carbamate, with the amount of acetylesterase added being 2.5 million U / g and the amount of ethyl carbamate added being 1 million U / g.
[0048] In step (3), the mass ratio of lipase to refined horse oil ethyl ester is 1:1800.
[0049] In step (3), the reaction system consists of 5% anhydrous ethanol and 1.2% Tween 80, and the reaction temperature is 60℃.
[0050] Comparative Example 1 Same as Example 1, except that no enzyme preparation was added to the crude horse oil, and no esterification reaction was carried out.
[0051] Comparative Example 2 Same as Example 1, except that no solvent was added to the crude horse oil.
[0052] Comparative Example 3 Same as Example 1, except that the temperature of the crude horse oil esterification reaction is controlled at 70°C.
[0053] Comparative Example 4 Same as Example 1, except that the time for the crude horse oil esterification reaction is controlled at 6 hours.
[0054] Comparative Example 5 Same as Example 1, except that no lipase was added to the refined horse oil ethyl ester.
[0055] Table 1. Oil yield test results of the green-synthesized horse oil ethyl esters in Examples 1-5 and Comparative Examples 1-4 The above description is merely an exemplary embodiment of the present invention, but the scope of protection of the present invention is not limited thereto. Any variations or substitutions that can be easily conceived by those skilled in the art within the technical scope disclosed in the present invention should be included within the scope of protection of the present invention. Therefore, the scope of protection of the present invention should be determined by the scope of the claims.
Claims
1. A green synthesis process for preparing high-purity horse oil ethyl ester based on enzyme catalysis, characterized in that, Includes the following steps: (1) Horse oil needs to be purified to remove impurities to obtain crude horse oil; (2) Add solvent and enzyme preparation to crude horse oil, control the temperature at 40–60℃, and react for 24–36 h to obtain refined horse oil ethyl ester; (3) Lipase was added to the refined horse oil ethyl ester and high-purity horse oil ethyl ester was obtained by alcoholysis reaction.
2. The green synthesis process for preparing high-purity horse oil ethyl ester based on enzyme catalysis according to claim 1, characterized in that, In step (1), horse oil is purified by removing impurities through filtration, deacidification, or molecular distillation.
3. The green synthesis process for preparing high-purity horse oil ethyl ester based on enzyme catalysis according to claim 1, characterized in that, In step (2), crude horse oil and enzyme preparation are added to the esterification reactor in a weight ratio of 1~2: 4~9 and stirred.
4. The green synthesis process for preparing high-purity horse oil ethyl ester based on enzyme catalysis according to claim 1, characterized in that, In step (2), the solvent is isooctane or 2-methyltetrahydrofuran.
5. The green synthesis process for preparing high-purity horse oil ethyl ester based on enzyme catalysis according to claim 1, characterized in that, In step (2), the enzyme preparation is selected from at least one of acetylesterase or carbamate esterase.
6. The green synthesis process for preparing high-purity horse oil ethyl ester based on enzyme catalysis according to claim 5, characterized in that, The amount of acetylesterase added is 2,000,000 to 2,500,000 U / g, and the amount of ethyl carbamate added is 800,000 to 1,000,000 U / g.
7. The green synthesis process for preparing high-purity horse oil ethyl ester based on enzyme catalysis according to claim 1, characterized in that, In step (3), the mass ratio of the lipase to refined horse oil ethyl ester is 1:1000 to 1:1800.
8. The green synthesis process for preparing high-purity horse oil ethyl ester based on enzyme catalysis according to claim 1, characterized in that, In step (3), the reaction system consists of 2.5-5% anhydrous ethanol and 0.5-1.2% Tween 80, and the reaction temperature is 30-60℃.