A process for separating and extracting nervonic acid from Xanthoceras sorbifolia

Abstract

The present invention relates to the technical field of natural product extraction, and in particular to a process for separating and extracting nervonic acid from Xanthoceras sorbifolia. The preparation method thereof comprises the following steps: extracting Xanthoceras sorbifolia kernels to prepare Xanthoceras sorbifolia oil; filtering and refining the Xanthoceras sorbifolia oil through a composite polyethersulfone membrane and preparing mixed fatty acids; and preparing nervonic acid through the mixed fatty acids. The present invention disperses molybdenum disulfide and lithium fluoride treated with hydrochloric acid in a solution, and after the polyethersulfone membrane is treated with a composite nanomaterial prepared by treating molybdenum disulfide and lithium fluoride, the obtained composite polyethersulfone membrane will not cause pollution, and has an adsorption effect on impurities in the Xanthoceras sorbifolia oil, and other impurities are adsorbed when the polyethersulfone membrane filters the Xanthoceras sorbifolia oil, and the Xanthoceras sorbifolia oil is refined, the content of the extraction solvent and other impurities in the Xanthoceras sorbifolia oil is reduced, and the extraction rate and purity of nervonic acid extracted from the Xanthoceras sorbifolia oil are improved.

Description

Technical Field

[0001] The invention relates to the technical field of natural product extraction, and in particular to a process for separating and extracting nervonic acid from Xanthoceras sorbifolia. Background Art

[0002] Nerve acid is a long-chain saturated fatty acid that is widely present in nature, especially in certain plants and animal tissues. Nerve acid has important physiological functions in the body, especially in the nervous system, where it is one of the main components of myelin lipids and plays a key role in maintaining the structure and function of nerve cells. Therefore, nerve acid has broad application prospects in the fields of medicine, health food, etc.

[0003] Nervonic acid is mainly derived from some specific vegetable oils, such as palm oil, perilla oil, maple oil and other oils extracted from plants. Among them, Xanthoceras sorbifolia oil is a vegetable oil containing a higher proportion of nervonic acid. Xanthoceras sorbifolia oil is mainly extracted from the seeds of Xanthoceras sorbifolia. The seeds of Xanthoceras sorbifolia are rich in oil. Xanthoceras sorbifolia oil is usually prepared by pressing or solvent extraction. The Xanthoceras sorbifolia oil prepared by extraction also needs to go through steps such as degumming and purification to reduce impurities in the Xanthoceras sorbifolia oil. General vegetable oil degumming includes hydration degumming and acid degumming, both of which are chemical degumming methods, which require precise control of reaction time and conditions, and have complex operation steps. It is difficult to use membrane degumming. Physical filtration is also a method to reduce impurities in oil, while conventional nanofiltration membranes such as polyethersulfone membranes have insufficient hydrophilicity during filtration, low filtration efficiency, and little filtration effect on impurities in Xanthoceras sorbifolia oil. In addition, the biocompatibility of polyethersulfone membranes is not high. Therefore, conventional polyethersulfone membranes are generally not used for refining Xanthoceras sorbifolia oil. Therefore, the present invention provides a process for separating and extracting nervonic acid from Xanthoceras sorbifolia. After extracting Xanthoceras sorbifolia oil from Xanthoceras sorbifolia, the Xanthoceras sorbifolia oil is subjected to membrane filtration through a prepared composite polyethersulfone membrane to complete the steps of degumming, purification and refining. The composite polyethersulfone membrane has high biocompatibility and can improve the extraction rate and purity of nervonic acid extracted from Xanthoceras sorbifolia oil. Summary of the invention

[0004] In view of the shortcomings of the prior art, the object of the present invention is to provide a process for separating and extracting nervonic acid from Xanthoceras sorbifolia.

[0005] A process for separating and extracting nervonic acid from Xanthoceras sorbifolia comprises the following steps:

[0006] S1: Extraction of Xanthoceras sorbifolia kernels to prepare Xanthoceras sorbifolia oil

[0007] The dried Xanthoceras sorbifolia seeds are crushed and sieved, and then put into an extraction kettle. After extraction, the product oil is released from the separation tank of the extraction kettle, and then the product oil is centrifuged, filtered, and dried to obtain Xanthoceras sorbifolia oil;

[0008] S2: Refining of Xanthoceras sorbifolia L. oil by filtration through composite polyethersulfone membrane and preparation of mixed fatty acids

[0009] The organic membrane in the organic membrane separation device is set to a composite polyethersulfone membrane, the composite polyethersulfone membrane is a polyethersulfone membrane loaded with a composite nanomaterial, the composite nanomaterial is prepared using two-dimensional molybdenum disulfide powder as a raw material, Xanthoceras sorbifolia oil is added to a separation tank of the organic membrane separation device, filtered through the composite polyethersulfone membrane to obtain refined Xanthoceras sorbifolia oil, the refined Xanthoceras sorbifolia oil is weighed, a NaOH-ethanol mixed solution is added, and heated to obtain saponified oil, an equal volume of deionized water is added to the saponified oil to dilute it, and extracted with n-hexane to obtain mixed fatty acids;

[0010] S3: Preparation of nervonic acid by mixing fatty acids

[0011] The mixed fatty acids are mixed with a concentrated ethanol solution, frozen to crystallize, and then filtered with a vacuum circulating water pump. The filter cake is dried to obtain neuraminic acid.

[0012] Furthermore, step S1 extracting Xanthoceras sorbifolia kernels to prepare Xanthoceras sorbifolia oil comprises the following steps:

[0013] S1.1: Crush the dried Xanthoceras sorbifolia seeds and pass them through an 80-mesh sieve, put them into an extraction kettle, seal them, evacuate them to a gauge pressure of -0.6 MPa, and then introduce the extraction solvent tetrafluoroethane from the solvent tank into the extraction kettle, and observe through a sight glass until the extraction solvent liquid level submerges the Xanthoceras sorbifolia seeds raw material;

[0014] S1.2: Heat to 40-50°C under stirring, and keep the pressure of the extraction kettle at a gauge pressure of 1.0 MPa to fully dissolve the oil in the Xanthoceras sorbifolia seeds. The extraction time is 50-60 minutes. After extraction, use a pressure pump to introduce the extract into a separation tank, heat and evaporate the extraction solvent, and use a system compressor to recover the evaporated extraction solvent vapor through a condenser to the solvent tank for continued use. The separation tank contains the product oil, and the product oil is released from the separation tank.

[0015] S1.3: The product oil is then centrifuged at a speed of 8000-8200 r / min for 5-10 min, filtered, and dried at 105-110° C. for 3-3.5 h to obtain Xanthoceras sorbifolia oil.

[0016] Furthermore, step S2 is to filtrate and purify the Xanthoceras sorbifolia oil through a composite polyethersulfone membrane to prepare mixed fatty acids, comprising the following steps:

[0017] S2.1: Replace the organic membrane in the organic membrane separation device with a composite polyethersulfone membrane, the composite polyethersulfone membrane is a polyethersulfone membrane loaded with composite nanomaterials, the composite nanomaterials are prepared using two-dimensional molybdenum disulfide powder as a raw material, add Xanthoceras sorbifolia oil into a separation tank of the organic membrane separation device, start the pump to a speed of 40 Hz, adjust the pressure regulating valve of the feed liquid reflux pipe, set the pressure to 1.9 MPa, filter the Xanthoceras sorbifolia oil through the composite polyethersulfone membrane, and obtain refined Xanthoceras sorbifolia oil;

[0018] S2.2: Weigh 10-12 parts by weight of refined Xanthoceras sorbifolia oil, add 50-60 parts by weight of NaOH-ethanol mixed solution, maintain the temperature at 65-70°C in an oil bath, set the heating time to 1.5-2h, and after the heating is completed, cool to room temperature 24-26°C to obtain saponified oil;

[0019] S2.3: Add an equal volume of deionized water to the saponified oil for dilution, and then add 3 mol / L hydrochloric acid to adjust the pH value of the system to 6-6.5, extract with n-hexane, repeat the operation twice, collect the n-hexane solutions of the two extractions, place them in a rotary evaporator for concentration, and spin-dry the n-hexane to obtain mixed fatty acids.

[0020] Furthermore, the preparation method of the two-dimensional molybdenum disulfide powder comprises the following steps:

[0021] S2.1.1: Add lithium fluoride to 3 mol / L hydrochloric acid at a solid-liquid ratio of 1 g: (400-500) mL, stir magnetically for 25 min, then add molybdenum disulfide with an equal mass to lithium fluoride, heat to 45-50°C, stir magnetically for 5-6 h, centrifuge, and collect the precipitate to obtain a solid precipitate;

[0022] S2.1.2: Wash the solid precipitate with LiCl solution for 5-6 times, then add deionized water at a solid-liquid ratio of 1 g: (250-300) mL, ultrasonically treat for 30-50 min, centrifuge to obtain the supernatant, and freeze-dry the supernatant at -20--15°C for 48-52 h to obtain a two-dimensional molybdenum disulfide powder.

[0023] Furthermore, the preparation method of the composite nanomaterial comprises the following steps:

[0024] S2.1.3 Take the two-dimensional molybdenum disulfide powder prepared in step S2.1.2 and add it into deionized water at a solid-liquid ratio of 3 g: (100-200) mL, ultrasonicate for 20-30 min, and magnetically stir for 40-45 min to obtain a molybdenum disulfide dispersion;

[0025] S2.1.4: Then add phytic acid solution accounting for 15-20% of the total volume of the system, ultrasonically treat for 30-35 minutes to obtain a dispersion, heat the dispersion to 180-185°C, react for 12-13 hours, then cool to room temperature 24-26°C, centrifuge the cooled product, remove the supernatant, and freeze-dry at 0°C for 24-25 hours to obtain a composite nanomaterial.

[0026] Furthermore, the preparation method of the composite polyethersulfone membrane comprises the following steps:

[0027] S2.1.5: Take 5-10 parts by mass of piperazine and add it to 100-150 parts by mass of deionized water, then add 10-20 parts by mass of the composite nanomaterial prepared in step S2.1.4, and stir for 20-30 minutes to obtain a suspension;

[0028] S2.1.6: Drop the suspension onto the surface of the polyethersulfone base membrane to fully wet the surface. After 3-5 minutes, dry it at 60-65°C to obtain a preliminarily treated polyethersulfone base membrane.

[0029] S2.1.7: Add TMC organic phase solution to the surface of the preliminarily treated polyethersulfone base membrane to fully wet the surface, let it stand for 30-50 seconds, and heat cross-link in a 90-100°C oven for 30-40 seconds to obtain a composite polyethersulfone membrane.

[0030] Furthermore, step S3, mixing fatty acids to prepare nervonic acid comprises the following steps:

[0031] S3.1: Mix the mixed fatty acid with 90% ethanol solution at a solid-liquid ratio of 1 g: (3-4) mL, and freeze and crystallize at -20°C for 3-4 hours;

[0032] S3.2: Then use a vacuum circulating water pump to filter, and stop filtering when the filter cake does not contain ethanol solution. Dry the filter cake at 20-25°C for 24-30 hours to obtain nervonic acid.

[0033] Furthermore, the concentration of the phytic acid solution in step S2.1.4 is 0.2-0.8wt%.

[0034] Furthermore, the TMC organic phase solution in step S2.1.7 is prepared by dissolving benzoyl chloride in n-hexane to prepare a solution with a mass fraction of 2-3%.

[0035] Furthermore, the volume ratio of NaOH to ethanol in the NaOH-ethanol mixed solution in step S2.2 is 2:(3-4).

[0036] Compared with the prior art, the present invention has at least the following beneficial effects:

[0037] 1. The present invention disperses molybdenum disulfide and lithium fluoride treated with hydrochloric acid in a solution. Lithium fluoride can perform surface treatment on molybdenum disulfide. The introduction of lithium fluoride can help molybdenum disulfide to separate into a single-layer or few-layer two-dimensional structure by a physical stripping method, thereby obtaining a high specific surface area and excellent physical and chemical properties. In addition, through the treatment with lithium fluoride, the ions of lithium fluoride react with the surface of molybdenum disulfide to form a stable chemical bond, thereby improving the stability of molybdenum disulfide and allowing the two-dimensional molybdenum disulfide to be better dispersed in a solvent to form a stable colloidal dispersion. Molybdenum disulfide and lithium fluoride are environmentally friendly. After a polyethersulfone membrane is treated with a composite nanomaterial prepared by treating molybdenum disulfide and lithium fluoride, the obtained composite polyethersulfone membrane will not cause pollution and has an adsorption effect on impurities in Xanthoceras sorbifolia oil. When the polyethersulfone membrane filters the Xanthoceras sorbifolia oil, it adsorbs other impurities, refines the Xanthoceras sorbifolia oil, reduces the content of the extraction solvent and other impurities in the Xanthoceras sorbifolia oil, and improves the extraction rate and purity of nervonic acid extracted from the Xanthoceras sorbifolia oil.

[0038] 2. The present invention modifies the surface of two-dimensional molybdenum disulfide powder by phytic acid. The phosphate groups in the phytic acid can form stable chemical bonds on the two-dimensional molybdenum disulfide surface, improve its chemical stability, thereby reducing the oxidation of molybdenum disulfide in the air, and extending the stability and service life of the polyethersulfone membrane whose adsorption performance is improved by introducing molybdenum disulfide. In addition, the nanomaterial prepared from the molybdenum disulfide treated with phytic acid has a large specific surface area, improved surface activity, better selective adsorption and catalytic activity, and high catalytic activity can improve the subsequent adhesion on the polyethersulfone membrane, and high adsorption can make the composite polyethersulfone membrane have better filtering ability and impurity adsorption ability, thereby improving the purity of neuraminic acid extracted from Xanthoceras sorbifolia oil.

[0039] 3. The present invention refines Xanthoceras sorbifolia oil by means of a composite polyethersulfone membrane. After the Xanthoceras sorbifolia oil is extracted from the Xanthoceras sorbifolia kernels, the Xanthoceras sorbifolia oil needs to be degummed and purified. The composite polyethersulfone membrane can directly degumm and purify the Xanthoceras sorbifolia oil by physical filtration. Moreover, during the degumming process, the composite nanomaterial made of molybdenum disulfide and loaded on the composite polyethersulfone membrane can also adsorb impurities in the Xanthoceras sorbifolia oil, thereby improving the purity of the Xanthoceras sorbifolia oil, and further improving the extraction rate and purity of nervonic acid extracted from the Xanthoceras sorbifolia oil. BRIEF DESCRIPTION OF THE DRAWINGS

[0040] The accompanying drawings, which are incorporated herein and constitute a part of the specification, illustrate embodiments of the present disclosure and, together with the description, further serve to explain the principles of the present disclosure and to enable those skilled in the relevant art to make and use the present disclosure.

[0041] Figure 1 This is a process flow chart for separating and extracting nervonic acid from Xanthoceras sorbifolia adopted in an embodiment of the present invention. DETAILED DESCRIPTION

[0042] The following is a detailed description of a process for separating and extracting nervonic acid from Xanthoceras sorbifolia provided by the present invention in conjunction with the accompanying drawings and specific embodiments. At the same time, it is explained here that in order to make the embodiments more detailed, the following embodiments are the best and preferred embodiments, and those skilled in the art may also adopt other alternatives to implement some known technologies; and the accompanying drawings are only for a more specific description of the embodiments, and are not intended to specifically limit the present invention. Embodiment 1:

[0043] A process for separating and extracting nervonic acid from Xanthoceras sorbifolia, such as Figure 1 As shown, the following steps are included:

[0044] S1: Extraction of Xanthoceras sorbifolia kernels to prepare Xanthoceras sorbifolia oil

[0045] S1.1: Crush the dried Xanthoceras sorbifolia seeds and pass them through an 80-mesh sieve, put them into an extraction kettle, seal them, evacuate them to a gauge pressure of -0.6 MPa, and then introduce the extraction solvent tetrafluoroethane from the solvent tank into the extraction kettle, and observe through a sight glass until the extraction solvent liquid level submerges the Xanthoceras sorbifolia seeds raw material;

[0046] S1.2: Heat to 40°C under stirring, and keep the pressure of the extraction kettle at 1.0 MPa to fully dissolve the oil in the Xanthoceras sorbifolia seeds. The extraction time is 50 minutes. After extraction, use a pressure pump to introduce the extract into a separation tank, heat and evaporate the extraction solvent, and use a system compressor to recover the evaporated extraction solvent vapor through a condenser to the solvent tank for continued use. The separation tank contains the product oil, and the product oil is released from the separation tank.

[0047] S1.3: The product oil is then centrifuged at a speed of 8000 r / min for 5 min, filtered, and dried at 105° C. for 3 h to obtain Xanthoceras sorbifolia oil.

[0048] S2: Refining of Xanthoceras sorbifolia L. oil by filtration through composite polyethersulfone membrane and preparation of mixed fatty acids

[0049] S2.1: Replace the organic membrane in the organic membrane separation device with a composite polyethersulfone membrane, the composite polyethersulfone membrane is a polyethersulfone membrane loaded with composite nanomaterials, the composite nanomaterials are prepared using two-dimensional molybdenum disulfide powder as a raw material, add Xanthoceras sorbifolia oil into a separation tank of the organic membrane separation device, start the pump to a speed of 40 Hz, adjust the pressure regulating valve of the feed liquid reflux pipe, set the pressure to 1.9 MPa, filter the Xanthoceras sorbifolia oil through the composite polyethersulfone membrane, and obtain refined Xanthoceras sorbifolia oil;

[0050] The preparation method of two-dimensional molybdenum disulfide powder is specifically as follows:

[0051] S2.1.1: Add lithium fluoride to 3 mol / L hydrochloric acid at a solid-liquid ratio of 1 g:400 mL, stir magnetically for 25 min, then add molybdenum disulfide with an equal mass to lithium fluoride, heat to 45 °C, stir magnetically for 5 h, centrifuge, and collect the precipitate to obtain a solid precipitate;

[0052] S2.1.2: Wash the solid precipitate with LiCl solution for 5 times, then add deionized water at a solid-liquid ratio of 1 g:250 mL, ultrasonically treat for 30 min, centrifuge to obtain the supernatant, and freeze-dry the supernatant at -20°C for 48 h to obtain a two-dimensional molybdenum disulfide powder.

[0053] The preparation method of the composite nanomaterial is specifically as follows:

[0054] S2.1.3: Take the two-dimensional molybdenum disulfide powder prepared in step S2.1.2 and add it into deionized water at a solid-liquid ratio of 3g:100mL, ultrasonicate for 20min, and magnetically stir for 40min to obtain a molybdenum disulfide dispersion;

[0055] S2.1.4: Then add phytic acid solution with a concentration of 0.2wt% of the total volume of the system, and perform ultrasonic treatment for 30 minutes to obtain a dispersion. Heat the dispersion to 180°C, react for 12 hours, and then cool it to room temperature 24°C. Centrifuge the cooled product, remove the supernatant, and freeze-dry it at 0°C for 24 hours to obtain a composite nanomaterial.

[0056] The preparation method of the composite polyethersulfone membrane is specifically as follows:

[0057] S2.1.5: Take 5 parts by mass of piperazine and add it to 100 parts by mass of deionized water, then add 10 parts by mass of the composite nanomaterial prepared in step S2.1.4, and stir for 20 minutes to obtain a suspension;

[0058] S2.1.6: Drop the suspension onto the surface of the polyethersulfone base membrane to fully wet the surface. After 3 minutes, dry it at 60°C to obtain a preliminarily treated polyethersulfone base membrane.

[0059] S2.1.7: Add TMC organic phase solution to the surface of the preliminarily treated polyethersulfone-based membrane. Specifically, the TMC organic phase solution is prepared by dissolving benzoyl chloride in n-hexane to form a 2% mass fraction solution, so that the surface is fully infiltrated, and then allowed to stand for 30 seconds, and thermally cross-linked in a 90°C oven for 30 seconds to obtain a composite polyethersulfone membrane.

[0060] S2.2: Weigh 10 parts by weight of refined Xanthoceras sorbifolia oil, add 50 parts by weight of a NaOH-ethanol mixed solution, wherein the volume ratio of NaOH to ethanol in the NaOH-ethanol mixed solution is 2:3, maintain the temperature at 65°C in an oil bath, set the heating time to 1.5 h, and after the heating is completed, cool to room temperature 24°C to obtain saponified oil;

[0061] S2.3: Add an equal volume of deionized water to the saponified oil for dilution, and then add 3 mol / L hydrochloric acid to adjust the pH value of the system to 6, extract with n-hexane, repeat the operation twice, collect the n-hexane solutions of the two extractions, place them in a rotary evaporator for concentration, and spin-dry the n-hexane to obtain mixed fatty acids.

[0062] S3: Preparation of nervonic acid by mixing fatty acids

[0063] S3.1: Mix the mixed fatty acid with 90% ethanol solution at a solid-liquid ratio of 1 g:3 mL, and freeze and crystallize at -20°C for 3 h;

[0064] S3.2: Then use a vacuum circulating water pump to filter, and stop filtering when the filter cake does not contain ethanol solution. Dry the filter cake at 20°C for 24 hours to obtain nervonic acid.

[0065] Embodiment 2:

[0066] A process for separating and extracting nervonic acid from Xanthoceras sorbifolia, such as Figure 1 As shown, the following steps are included:

[0067] S1: Extraction of Xanthoceras sorbifolia kernels to prepare Xanthoceras sorbifolia oil

[0068] S1.1: Crush the dried Xanthoceras sorbifolia seeds and pass them through an 80-mesh sieve, put them into an extraction kettle, seal them, evacuate them to a gauge pressure of -0.6 MPa, and then introduce the extraction solvent tetrafluoroethane from the solvent tank into the extraction kettle, and observe through a sight glass until the extraction solvent liquid level submerges the Xanthoceras sorbifolia seeds raw material;

[0069] S1.2: Heat to 50°C under stirring, and keep the pressure of the extraction kettle at 1.0MPa to fully dissolve the oil in the Xanthoceras sorbifolia seeds. The extraction time is 60min. After extraction, use a pressure pump to introduce the extract into a separation tank, heat and evaporate the extraction solvent, and use a system compressor to recover the evaporated extraction solvent vapor to the solvent tank through a condenser for continued use. The separation tank contains the product oil, and the product oil is released from the separation tank.

[0070] S1.3: The product oil was then centrifuged at a speed of 8200 r / min for 10 min, filtered, and dried at 110° C. for 3.5 h to obtain Xanthoceras sorbifolia oil.

[0071] S2: Refining of Xanthoceras sorbifolia L. oil by filtration through composite polyethersulfone membrane and preparation of mixed fatty acids

[0072] S2.1: Replace the organic membrane in the organic membrane separation device with a composite polyethersulfone membrane, the composite polyethersulfone membrane is a polyethersulfone membrane loaded with composite nanomaterials, the composite nanomaterials are prepared using two-dimensional molybdenum disulfide powder as a raw material, add Xanthoceras sorbifolia oil into a separation tank of the organic membrane separation device, start the pump to a speed of 40 Hz, adjust the pressure regulating valve of the feed liquid reflux pipe, set the pressure to 1.9 MPa, filter the Xanthoceras sorbifolia oil through the composite polyethersulfone membrane, and obtain refined Xanthoceras sorbifolia oil;

[0073] The preparation method of two-dimensional molybdenum disulfide powder is specifically as follows:

[0074] S2.1.1: Add lithium fluoride to 3 mol / L hydrochloric acid at a solid-liquid ratio of 1 g:400 mL, stir magnetically for 25 min, then add molybdenum disulfide with an equal mass to lithium fluoride, heat to 50 °C, stir magnetically for 6 h, centrifuge, and collect the precipitate to obtain a solid precipitate;

[0075] S2.1.2: The solid precipitate was washed with LiCl solution for 6 times, and then deionized water was added at a solid-liquid ratio of 1 g:250 mL. The mixture was ultrasonically treated for 50 min, and the supernatant was taken by centrifugation. The supernatant was freeze-dried at -15°C for 52 h to obtain a two-dimensional molybdenum disulfide powder.

[0076] The preparation method of the composite nanomaterial is specifically as follows:

[0077] S2.1.3: Take two-dimensional molybdenum disulfide powder and add it into deionized water at a solid-liquid ratio of 3g:100mL, ultrasonicate for 30min, and magnetically stir for 45min to obtain a molybdenum disulfide dispersion;

[0078] S2.1.4: Then add phytic acid solution with a concentration of 0.8wt% of the total volume of the system, and perform ultrasonic treatment for 20 minutes to obtain a dispersion. Heat the dispersion to 185°C and react for 13 hours. Then let it stand and cool to room temperature 26°C. Centrifuge the cooled product, remove the supernatant, and freeze-dry it at 0°C for 25 hours to obtain a composite nanomaterial.

[0079] The preparation method of the composite polyethersulfone membrane is specifically as follows:

[0080] S2.1.5: Take 5 parts by mass of piperazine and add it to 100 parts by mass of deionized water, then add 10 parts by mass of the composite nanomaterial, and stir for 30 minutes to obtain a suspension;

[0081] S2.1.6: Drop the suspension onto the surface of the polyethersulfone base membrane to fully wet the surface. After 5 minutes, dry it at 65°C to obtain a preliminarily treated polyethersulfone base membrane.

[0082] S2.1.7: Add TMC organic phase solution to the surface of the preliminarily treated polyethersulfone-based membrane. The TMC organic phase solution is prepared by dissolving benzoyl chloride in n-hexane to form a 2% mass fraction solution, so that the surface is fully infiltrated, and then let it stand for 50 seconds, and heat cross-linked in an oven at 100°C for 40 seconds to obtain a composite polyethersulfone membrane.

[0083] S2.2: Weigh 10 parts by weight of refined Xanthoceras sorbifolia oil, add 50 parts by weight of a NaOH-ethanol mixed solution, wherein the volume ratio of NaOH to ethanol in the NaOH-ethanol mixed solution is 2:3, maintain the temperature at 70°C in an oil bath, set the heating time to 2h, and after the heating is completed, cool to room temperature 26°C to obtain saponified oil;

[0084] S2.3: Add an equal volume of deionized water to the saponified oil for dilution, and then add 3 mol / L hydrochloric acid to adjust the pH value of the system to 6.5, extract with n-hexane, repeat the operation twice, collect the n-hexane solutions of the two extractions, place them in a rotary evaporator for concentration, and spin-dry the n-hexane to obtain mixed fatty acids.

[0085] S3: Preparation of nervonic acid by mixing fatty acids

[0086] S3.1: Mix the mixed fatty acid with 90% ethanol solution at a solid-liquid ratio of 1 g:3 mL, and freeze and crystallize at -20°C for 4 hours;

[0087] S3.2: Then use a vacuum circulating water pump to filter, and stop filtering when the filter cake does not contain ethanol solution. Dry the filter cake at 25°C for 30 hours to obtain nervonic acid.

[0088] Embodiment 3:

[0089] A process for separating and extracting nervonic acid from Xanthoceras sorbifolia, such as Figure 1 As shown, the following steps are included:

[0090] S1: Extraction of Xanthoceras sorbifolia kernels to prepare Xanthoceras sorbifolia oil

[0091] S1.1: Crush the dried Xanthoceras sorbifolia seeds and pass them through an 80-mesh sieve, put them into an extraction kettle, seal them, evacuate them to a gauge pressure of -0.6 MPa, and then introduce the extraction solvent tetrafluoroethane from the solvent tank into the extraction kettle, and observe through a sight glass until the extraction solvent liquid level submerges the Xanthoceras sorbifolia seeds raw material;

[0092] S1.2: Heat to 40°C under stirring, and keep the pressure of the extraction kettle at 1.0 MPa to fully dissolve the oil in the Xanthoceras sorbifolia seeds. The extraction time is 50 minutes. After extraction, use a pressure pump to introduce the extract into a separation tank, heat and evaporate the extraction solvent, and use a system compressor to recover the evaporated extraction solvent vapor through a condenser to the solvent tank for continued use. The separation tank contains the product oil, and the product oil is released from the separation tank.

[0093] S1.3: The product oil is then centrifuged at a speed of 8000 r / min for 5 min, filtered, and dried at 105° C. for 3 h to obtain Xanthoceras sorbifolia oil.

[0094] S2: Refining of Xanthoceras sorbifolia L. oil by filtration through composite polyethersulfone membrane and preparation of mixed fatty acids

[0095] S2.1: Replace the organic membrane in the organic membrane separation device with a composite polyethersulfone membrane, the composite polyethersulfone membrane is a polyethersulfone membrane loaded with composite nanomaterials, the composite nanomaterials are prepared using two-dimensional molybdenum disulfide powder as a raw material, add Xanthoceras sorbifolia oil into a separation tank of the organic membrane separation device, start the pump to a speed of 40 Hz, adjust the pressure regulating valve of the feed liquid reflux pipe, set the pressure to 1.9 MPa, filter the Xanthoceras sorbifolia oil through the composite polyethersulfone membrane, and obtain refined Xanthoceras sorbifolia oil;

[0096] The preparation method of two-dimensional molybdenum disulfide powder is specifically as follows:

[0097] S2.1.1: Add lithium fluoride to 3 mol / L hydrochloric acid at a solid-liquid ratio of 1 g:500 mL, stir magnetically for 25 min, then add molybdenum disulfide with an equal mass to lithium fluoride, heat to 45 °C, stir magnetically for 5 h, centrifuge, and collect the precipitate to obtain a solid precipitate;

[0098] S2.1.2: Wash the solid precipitate with LiCl solution for 5 times, then add deionized water at a solid-liquid ratio of 1 g:300 mL, ultrasonically treat for 30 min, centrifuge to obtain the supernatant, and freeze-dry the supernatant at -20°C for 48 h to obtain a two-dimensional molybdenum disulfide powder.

[0099] The preparation method of the composite nanomaterial is specifically as follows:

[0100] S2.1.3: Take two-dimensional molybdenum disulfide powder and add it into deionized water at a solid-liquid ratio of 3g:200mL, ultrasonicate for 20min, and magnetically stir for 40min to obtain a molybdenum disulfide dispersion;

[0101] S2.1.4: Then add phytic acid solution with a concentration of 0.2wt% of the total volume of the system, and perform ultrasonic treatment for 30 minutes to obtain a dispersion. Heat the dispersion to 180°C, react for 12 hours, and then cool it to room temperature 24°C. Centrifuge the cooled product, remove the supernatant, and freeze-dry it at 0°C for 24 hours to obtain a composite nanomaterial.

[0102] The preparation method of the composite polyethersulfone membrane is specifically as follows:

[0103] S2.1.5: Take 10 parts by mass of piperazine and add it to 150 parts by mass of deionized water, then add 10 parts by mass of the composite nanomaterial, and stir for 20 minutes to obtain a suspension;

[0104] S2.1.6: Drop the suspension onto the surface of the polyethersulfone base membrane to fully wet the surface. After 3 minutes, dry it at 60°C to obtain a preliminarily treated polyethersulfone base membrane.

[0105] S2.1.7: Add TMC organic phase solution to the surface of the preliminarily treated polyethersulfone-based membrane. The TMC organic phase solution is prepared by dissolving benzoyl chloride in n-hexane to form a 3% mass fraction solution, so that the surface is fully infiltrated, and then let it stand for 30 seconds, and heat cross-link in a 90°C oven for 30 seconds to obtain a composite polyethersulfone membrane.

[0106] S2.2: Weigh 12 parts by weight of refined Xanthoceras sorbifolia oil, add 60 parts by weight of a NaOH-ethanol mixed solution, wherein the volume ratio of NaOH to ethanol in the NaOH-ethanol mixed solution is 2:4, maintain the temperature at 65°C in an oil bath, set the heating time to 1.5 h, and after the heating is completed, cool to room temperature 24°C to obtain saponified oil;

[0107] S2.3: Add an equal volume of deionized water to the saponified oil for dilution, and then add 3 mol / L hydrochloric acid to adjust the pH value of the system to 6, extract with n-hexane, repeat the operation twice, collect the n-hexane solutions of the two extractions, place them in a rotary evaporator for concentration, and spin-dry the n-hexane to obtain mixed fatty acids.

[0108] S3: Preparation of nervonic acid by mixing fatty acids

[0109] S3.1: Mix the mixed fatty acid with 90% ethanol solution at a solid-liquid ratio of 1 g:4 mL, and freeze and crystallize at -20°C for 3 h;

[0110] S3.2: Then use a vacuum circulating water pump to filter, and stop filtering when the filter cake does not contain ethanol solution. Dry the filter cake at 20°C for 24 hours to obtain nervonic acid.

[0111] Comparative Example 1:

[0112] Compared with Example 1, the difference of Comparative Example 1 is that step S2.1 is not performed, and mixed fatty acids are directly prepared using Xanthoceras sorbifolia oil, specifically: "Step 1: weigh 10 parts by mass of Xanthoceras sorbifolia oil, add 50 parts by mass of a NaOH-ethanol mixed solution, wherein the volume ratio of NaOH to ethanol in the NaOH-ethanol mixed solution is 2:3, maintain the temperature at 65°C in an oil bath, set the heating time to 1.5h, and after the heating is completed, cool to room temperature 24°C to obtain saponified oil;

[0113] Step 2: Add an equal volume of deionized water to the saponified oil for dilution, then add 3 mol / L hydrochloric acid to adjust the pH value of the system to 6, extract with n-hexane, repeat the operation twice, collect the n-hexane solutions of the two extractions, place them in a rotary evaporator for concentration, and spin-dry the n-hexane to obtain a mixed fatty acid. The other steps remain unchanged, and the extraction rate and purity of the nervonic acid in Comparative Example 1 are calculated.

[0114] Comparative Example 2:

[0115] Compared with Example 1, the difference of Comparative Example 2 is that step S2.1.1 and step S2.1.2 are not performed, and molybdenum disulfide powder is used instead of two-dimensional molybdenum disulfide powder in step S2.1.3, specifically: "S2.1.3: Take molybdenum disulfide powder and add it into deionized water with a solid-liquid ratio of 3g:100mL, ultrasonicate for 20min, and magnetically stir for 40min to obtain a molybdenum disulfide dispersion". The other steps remain unchanged, and the extraction rate and purity of neuraminic acid of Comparative Example 2 are calculated.

[0116] Comparative Example 3:

[0117] Compared with Example 1, the difference of Comparative Example 3 is that step S2.1.3 and step S2.1.4 are not performed, and two-dimensional molybdenum disulfide powder is used instead of the composite nanomaterial in step S2.1.5, specifically: "S2.1.5: Take 5 parts by mass of piperazine and add it to 100 parts by mass of deionized water, and then add 10 parts by mass of two-dimensional molybdenum disulfide powder, stir for 20 minutes, and obtain a suspension", and the other steps remain unchanged. The extraction rate and purity of neuraminic acid in Comparative Example 3 are calculated.

[0118] Comparative Example 4:

[0119] Compared with Example 1, the difference of Comparative Example 4 is that, in step S2.1, a composite polyethersulfone membrane is not used, but a polyethersulfone membrane is used instead, specifically: "S2.1: Replace the organic membrane in the organic membrane separation equipment with a commercially available polyethersulfone membrane, add the Xanthoceras sorbifolia oil into the separation tank of the organic membrane separation equipment, start the pump to a speed of 40 Hz, adjust the pressure regulating valve of the slurry reflux pipe, set the pressure to 1.9 MPa, and filter the Xanthoceras sorbifolia oil through the composite polyethersulfone membrane to obtain refined Xanthoceras sorbifolia oil", and the other steps remain unchanged, and the extraction rate and purity of neuraminic acid of Comparative Example 4 are calculated.

[0120] Calculation of neuraminic acid extraction rate:

[0121] The extraction rate of neuraminic acid = the mass of Xanthoceras sorbifolia oil / the mass of neuraminic acid*100%.

[0122] The purity of nervonic acid was determined by GC-MS analysis.

[0123] The extraction rate and purity of the nervonic acid of Examples 1-3 were calculated and the data of Comparative Examples 1-4 were compiled into Table 1.

[0124] Table 1

[0125]

[0126] The extraction rates of Examples 1-3 were 3.78%, 3.62% and 3.71% respectively, and the purity of nervonic acid was 99.31%, 99.15% and 99.27%, all higher than the control example. It can be seen that the process for separating and extracting nervonic acid from Xanthoceras sorbifolia of the present invention has a higher extraction rate and purity.

[0127] Comparative Example 1 is a refinement of Xanthoceras sorbifolia oil without using the composite polyethersulfone membrane, and the extraction rate of nervonic acid is 2.66% and the purity is 96.28%. It can be seen that not using the composite polyethersulfone membrane will result in impurities remaining in the Xanthoceras sorbifolia oil, thereby affecting the purity and extraction rate of nervonic acid.

[0128] The extraction rates of Comparative Example 2 and Comparative Example 3 were 2.99% and 2.85% respectively, and the purity of neuraminic acid was 97.13% and 97.69%. It can be seen that the complexation of lithium fluoride and molybdenum disulfide, as well as the surface modification of molybdenum disulfide with phytic acid, both improved the adsorption capacity of the polyethersulfone membrane for impurities after the nanomaterial prepared with molybdenum disulfide as the main raw material was complexed with the polyethersulfone membrane, thereby improving the purity and extraction rate of neuraminic acid.

[0129] The extraction rate of comparative example 4 is 2.83%, and the purity is 96.93%. It can be seen that the polyethersulfone membrane has some effect on the improvement of the purity and extraction rate of neuraminic acid, and the composite polyethersulfone membrane prepared by the present invention has a greater effect on improving the purity and extraction rate of neuraminic acid.

[0130] The above embodiments are merely illustrative of the principles and effects of the present invention, and are not intended to limit the present invention. Anyone familiar with the art may modify or alter the above embodiments without departing from the spirit and scope of the present invention. Therefore, all equivalent modifications or alterations made by a person of ordinary skill in the art without departing from the spirit and technical ideas disclosed by the present invention shall still be covered by the claims of the present invention.

Claims

1. A process for separating and extracting nervonic acid from Xanthoceras sorbifolia, characterized in that: The steps include: S1: Extraction of Xanthoceras sorbifolia kernels to prepare Xanthoceras sorbifolia oil The dried Xanthoceras sorbifolia seeds are crushed and sieved, and then put into an extraction kettle. After extraction, the product oil is released from the separation tank of the extraction kettle, and then the product oil is centrifuged, filtered, and dried to obtain Xanthoceras sorbifolia oil; S2: Refining of Xanthoceras sorbifolia L. oil by filtration through composite polyethersulfone membrane and preparation of mixed fatty acids The organic membrane in the organic membrane separation device is set to a composite polyethersulfone membrane, the composite polyethersulfone membrane is a polyethersulfone membrane loaded with a composite nanomaterial, the composite nanomaterial is prepared using two-dimensional molybdenum disulfide powder as a raw material, Xanthoceras sorbifolia oil is added to a separation tank of the organic membrane separation device, filtered through the composite polyethersulfone membrane to obtain refined Xanthoceras sorbifolia oil, the refined Xanthoceras sorbifolia oil is weighed, a NaOH-ethanol mixed solution is added, and heated to obtain saponified oil, an equal volume of deionized water is added to the saponified oil to dilute it, and extracted with n-hexane to obtain mixed fatty acids; The preparation method of two-dimensional molybdenum disulfide powder comprises the following steps: S2.1.1: adding lithium fluoride to 3 mol / L hydrochloric acid at a material-liquid ratio of 1 g: (400-500) mL, magnetically stirring for 25 min, then adding molybdenum disulfide with an equal mass to lithium fluoride, heating to 45-50° C., magnetically stirring for 5-6 h, centrifuging, taking the precipitate, and obtaining a solid precipitate; S2.1.2: Wash the solid precipitate with LiCl solution for 5-6 times, then add deionized water at a solid-liquid ratio of 1 g: (250-300) mL, ultrasonically treat for 30-50 min, centrifuge to obtain the supernatant, and freeze-dry the supernatant at -20--15°C for 48-52 h to obtain a two-dimensional molybdenum disulfide powder; The preparation method of the composite nanomaterial comprises the following steps: S2.1.3 Take the two-dimensional molybdenum disulfide powder prepared in step S2.1.2 and add it into deionized water at a solid-liquid ratio of 3 g: (100-200) mL, ultrasonicate for 20-30 min, and magnetically stir for 40-45 min to obtain a molybdenum disulfide dispersion; S2.1.4: Then add 15-20% of the total volume of the system phytic acid solution, ultrasonically treat for 30-35 minutes to obtain a dispersion, heat the dispersion to 180-185°C, react for 12-13 hours, then cool to room temperature 24-26°C, centrifuge the cooled product, remove the supernatant, and freeze-dry at 0°C for 24-25 hours to obtain a composite nanomaterial; The preparation method of the composite polyethersulfone membrane comprises the following steps: S2.1.5: Take 5-10 parts by mass of piperazine and add it to 100-150 parts by mass of deionized water, then add 10-20 parts by mass of the composite nanomaterial prepared in step S2.1.4, and stir for 20-30 minutes to obtain a suspension; S2.1.6: Drop the suspension onto the surface of the polyethersulfone base membrane to fully wet the surface. After 3-5 minutes, dry it at 60-65°C to obtain a preliminarily treated polyethersulfone base membrane. S2.1.7: Add TMC organic phase solution to the surface of the preliminarily treated polyethersulfone-based membrane to fully wet the surface, let it stand for 30-50 seconds, and heat cross-link in an oven at 90-100°C for 30-40 seconds to obtain a composite polyethersulfone membrane; S3: Preparation of nervonic acid by mixing fatty acids The mixed fatty acids are mixed with an ethanol solution, frozen and crystallized, and then filtered with a vacuum circulating water pump. The filter cake is dried to obtain neuraminic acid.

2. A process for separating and extracting nervonic acid from Xanthoceras sorbifolia according to claim 1, characterized in that: Step S1: extracting Xanthoceras sorbifolia kernels to prepare Xanthoceras sorbifolia oil, comprising the following steps: S1.1: Crush the dried Xanthoceras sorbifolia seeds and pass them through an 80-mesh sieve, put them into an extraction kettle, seal them, evacuate them to a gauge pressure of -0.6 MPa, and then introduce the extraction solvent tetrafluoroethane from the solvent tank into the extraction kettle, and observe through a sight glass until the extraction solvent liquid level submerges the Xanthoceras sorbifolia seeds raw material; S1.2: Heat to 40-50°C under stirring, and keep the pressure of the extraction kettle at a gauge pressure of 1.0 MPa to fully dissolve the oil in the Xanthoceras sorbifolia seeds. The extraction time is 50-60 minutes. After extraction, use a pressure pump to introduce the extract into a separation tank, heat and evaporate the extraction solvent, and use a system compressor to recover the evaporated extraction solvent vapor through a condenser to the solvent tank for continued use. The separation tank contains the product oil, and the product oil is released from the separation tank. S1.3: The product oil is then centrifuged at a speed of 8000-8200 r / min for 5-10 min, filtered, and dried at 105-110° C. for 3-3.5 h to obtain Xanthoceras sorbifolia oil.

3. A process for separating and extracting nervonic acid from Xanthoceras sorbifolia according to claim 2, characterized in that: Step S2: filtering and refining Xanthoceras sorbifolia oil through a composite polyethersulfone membrane to prepare mixed fatty acids, comprising the following steps: S2.1: Replace the organic membrane in the organic membrane separation device with a composite polyethersulfone membrane, the composite polyethersulfone membrane is a polyethersulfone membrane loaded with composite nanomaterials, the composite nanomaterials are prepared using two-dimensional molybdenum disulfide powder as a raw material, add Xanthoceras sorbifolia oil into a separation tank of the organic membrane separation device, start the pump to a speed of 40 Hz, adjust the pressure regulating valve of the feed liquid reflux pipe, set the pressure to 1.9 MPa, filter the Xanthoceras sorbifolia oil through the composite polyethersulfone membrane, and obtain refined Xanthoceras sorbifolia oil; S2.2: Weigh 10-12 parts by weight of refined Xanthoceras sorbifolia oil, add 50-60 parts by weight of NaOH-ethanol mixed solution, maintain the temperature at 65-70°C in an oil bath, set the heating time to 1.5-2h, and after the heating is completed, cool to room temperature 24-26°C to obtain saponified oil; S2.3: Add an equal volume of deionized water to the saponified oil for dilution, and then add 3 mol / L hydrochloric acid to adjust the pH value of the system to 6-6.5, extract with n-hexane, repeat the operation twice, collect the n-hexane solutions of the two extractions, place them in a rotary evaporator for concentration, and spin-dry the n-hexane to obtain mixed fatty acids.

4. A process for separating and extracting nervonic acid from Xanthoceras sorbifolia according to claim 3, characterized in that: Step S3: mixing fatty acids to prepare nervonic acid, comprising the following steps: S3.1: Mix the mixed fatty acid with 90% ethanol solution at a solid-liquid ratio of 1 g: (3-4) mL, and freeze and crystallize at -20°C for 3-4 hours; S3.2: Then use a vacuum circulating water pump to filter, and stop filtering when the filter cake does not contain ethanol solution. Dry the filter cake at 20-25°C for 24-30 hours to obtain nervonic acid.

5. The process for separating and extracting nervonic acid from Xanthoceras sorbifolia according to claim 1, characterized in that: The concentration of the phytic acid solution in step S2.1.4 is 0.2-0.8 wt %.

6. The process for separating and extracting nervonic acid from Xanthoceras sorbifolia according to claim 1, characterized in that: The TMC organic phase solution in step S2.1.7 is specifically prepared by dissolving benzoyl chloride in n-hexane to prepare a solution with a mass fraction of 2-3%.

7. The process for separating and extracting nervonic acid from Xanthoceras sorbifolia according to claim 3, characterized in that: The volume ratio of NaOH to ethanol in the NaOH-ethanol mixed solution in step S2.2 is 2:(3-4).

Images