CN113831452A - Synthesis method of active BX/Nar-g-HPMA/DEAM/DMDAAC acetylsalicylate - Google Patents

Synthesis method of active BX/Nar-g-HPMA/DEAM/DMDAAC acetylsalicylate Download PDF

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CN113831452A
CN113831452A CN202111016387.6A CN202111016387A CN113831452A CN 113831452 A CN113831452 A CN 113831452A CN 202111016387 A CN202111016387 A CN 202111016387A CN 113831452 A CN113831452 A CN 113831452A
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naringin
deam
hpma
dmdaac
bagasse xylan
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李和平
田可欣
赵斌
苏越
邹志明
吕奕菊
谢超煜
刘红丽
郑光禄
杨莹莹
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Guilin University of Technology
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Abstract

The invention discloses a method for synthesizing active BX/Nar-g-HPMA/DEAM/DMDAAC acetylsalicylate. Bagasse xylan and naringin are used as raw materials, hydroxypropyl methacrylate, diethylaminoethyl methacrylate and dimethyl diallyl ammonium chloride are used as mixed grafting monomers, ammonium persulfate is used as an initiator, the bagasse xylan/naringin-g-HPMA/DEAM/DMDAAC graft copolymer is synthesized in a water solvent through a free radical reaction, and on the basis of the intermediate, 1-butyl-2, 3-dimethyl imidazolium ionic liquid is used as a solvent, acetylsalicylic acid is used as an esterifying agent, and a product BX/Nar-g-HPMA/DEAM/DMDAAC acetylsalicylic acid ester with anticancer activity is synthesized through a catalytic esterification reaction. The invention realizes the effective combination of the product and various amino acid residues of the receptor protein, and has wide anticancer and biological medicinal research prospects.

Description

Synthesis method of active BX/Nar-g-HPMA/DEAM/DMDAAC acetylsalicylate
Technical Field
The invention relates to the field of fine chemical engineering and biomass materials, in particular to a method for synthesizing active BX/Nar-g-HPMA/DEAM/DMDAAC acetylsalicylate.
Background
The biomass naringin is a high-quality biomass material and has multiple functions of antibiosis, cancer resistance, spasmolysis, cholagogue and the like. The effect of the naringin on resisting gastric cancer and colon cancer is the most outstanding, and the naringin regulates the expression of cell cycle genes by down regulating Cdk4, Cdk6, Cdk7, Bcl-2, x-IAP and c-IAP-2 and up regulating p18, p19, p21, caspase-3, 7,8,9 and Bak, AIF and Bax in cells, so that the cell cycle stays at S phase or G2/M phase, and the large intestine cancer cells (SW1116, SW837) are induced to die. But the clinical application of the medicine is limited due to the defects of poor absorption in vivo, low oral bioavailability and the like. Meanwhile, researches prove that the medicament containing the carboxymethyl xylan can generate a stimulating nerve reaction with immune cells in vivo, namely, the growth, the metastasis and the activity of cancer cells are inhibited through the action of the carboxymethyl xylan and the immune cells. However, many studies only modify one substance of the compound in one way at present, and the expected effect cannot be achieved. If the purpose of optimizing the physicochemical properties of the raw materials, namely the naringin and the bagasse xylan, is achieved by chemically modifying the raw materials, namely the naringin and the bagasse xylan with an active group through grafting, crosslinking, esterification and the like, a new field for researching the biological activity of the bagasse xylan/naringin composite biomass is developed. The application of the product can not only improve the economic value of the bagasse xylan and promote the reasonable utilization of agricultural and forestry waste resources, but also widen the functional application of the bagasse xylan in the fields of medicines, foods, functional materials and the like.
Acetylsalicylic acid, namely aspirin, has been widely used in the world for a long time as an antipyretic and analgesic, and with the increasingly extensive application and research, acetylsalicylic acid also has the effects of preventing and treating certain cancers, particularly colorectal cancer, and the research result shows that the survival time of colorectal cancer patients insisting on using acetylsalicylic acid is prolonged. However, long-term oral administration of aspirin can irritate the gastric mucosa, resulting in damage to the gastric mucosa, gastric ulcer and gastric bleeding. If bagasse xylan and naringin are used as reactants and acetylsalicylic acid is used as an esterifying agent, the acidity of the bagasse xylan and naringin can be greatly reduced, toxic and side effects on a human body are reduced, and in order to further enhance the anticancer activity and solubility of the bagasse xylan, hydroxypropyl methacrylate, diethylaminoethyl methacrylate and dimethyl diallyl ammonium chloride are used as active grafting monomers, so that the inhibition effect on colorectal cancer cells can be greatly improved through synergistic interaction, meanwhile, part of hydrogen bond effects in a xylan structure are reduced, and the water solubility and the biological activity of the xylan are improved. The protein with the best docking effect is 6O36 protein according to molecular docking, the optimal binding free energy is-8.81 kJ/mol, and the BXG is proved3The A has good affinity to the protein and has stronger effect of inhibiting the activity of the protein.
The bagasse xylan/naringin-g-HPMA/DEAM/DMDAAC graft copolymer is synthesized by taking bagasse xylan and naringin (BX/Nar) as main raw materials, hydroxypropyl methacrylate (HPMA), diethylaminoethyl methacrylate (DEAM) and dimethyldiallylammonium chloride (DMDAAC) as mixed graft monomers and ammonium persulfate as an initiator through a free radical reaction in a water solvent; then, on the basis of the intermediate, 1-butyl-2, 3-dimethyl imidazolium ionic liquid is used as a solvent, acetylsalicylic acid is used as an esterifying agent, and a final product BX/Nar-g-HPMA/DEAM/DMDAAC acetylsalicylic acid ester with anticancer activity is synthesized through catalytic esterification reaction.
Disclosure of Invention
The invention aims to improve the biological activity of bagasse xylan/naringin and broaden the application of the bagasse xylan/naringin in the fields of fine chemical engineering, medicines and the like by using bagasse xylan and naringin as raw materials and modifying by esterification, grafting and the like, and provides a synthesis method of bagasse xylan/naringin-g-HPMA/DEAM/DMDAAC acetylsalicylate with anticancer activity.
The method comprises the following specific steps:
(1) and (3) drying 4.0-5.0 g of bagasse xylan in a vacuum constant-temperature drying oven at 60 ℃ for 24 hours to obtain the dry-based bagasse xylan.
(2) And (3) placing 0.3-0.5 g of naringin sugar in a vacuum constant-temperature drying oven at 60 ℃ for drying for 24 hours to obtain dry naringin.
(3) Weighing 0.3-0.7 g of ammonium persulfate in a 50mL beaker, adding 10-20 mL of distilled water to prepare an initiator solution, stirring at room temperature for 5-10 minutes, and pouring into a 100mL constant-pressure dropping funnel for later use.
(4) 3.0-5.0 mL of analytically pure hydroxypropyl methacrylate, 4.0-5.0 mL of analytically pure diethylaminoethyl methacrylate and 4.0-5.0 mL of analytically pure dimethyldiallylammonium chloride are weighed and placed in a 50mL beaker, and after uniform stirring and mixing, a monomer mixed solution is obtained and poured into another 100mL constant-pressure dropping funnel for later use.
(5) 3.0-4.0 g of dry bagasse xylan obtained in the step (1) and 0.2-0.3 g of dry naringin obtained in the step (2) are weighed and placed in a 250mL four-neck flask, then 0.1-0.2 g N, N-dimethylene bisacrylamide and 50-70 mL of distilled water are added, the temperature is increased to 45-65 ℃, and the mixture is stirred for 20-30 minutes to obtain the mixed activation solution of bagasse xylan and naringin.
(6) Firstly, dropwise adding one third of the initiator solution obtained in the step (3) to the bagasse xylan activation solution obtained in the step (5), controlling the temperature at 50-70 ℃ and the dropwise adding time at 1-2 hours, continuously stirring for 20-30 minutes after the addition is finished, synchronously dropwise adding the monomer solution obtained in the step (3) and the initiator solution obtained in the remaining two thirds of the step (2), controlling the dropwise adding time of the monomer and the initiator at 2-5 hours, continuously reacting for 2-3 hours after the dropwise addition is finished, and cooling the obtained material to room temperature.
(7) And (4) precipitating the material obtained in the step (6) by using 20-40 mL of analytically pure absolute ethyl alcohol for 20-30 minutes, and performing suction filtration. 10-15 mL of analytically pure absolute ethanol and 10-20 mL of analytically pure cyclohexane are respectively measured each time, and the precipitate is washed and filtered for 2-3 times. And (3) drying the obtained filter cake in a constant-temperature drying oven at 60 ℃ for 24 hours to constant weight to obtain the crude bagasse xylan/naringin-g-HPMA/DEAM/DMDAAC graft copolymer.
(8) Placing the bagasse xylan/naringin-g-HPMA/DEAM/DMDAAC obtained in the step (7) into a Soxhlet extractor, and adding 50-60 mL of analytically pure cyclohexane to extract for 12-24 hours; and (3) taking out the materials after extraction, putting the materials into a watch glass, and drying the materials in a vacuum constant-temperature drying oven at the temperature of 60 ℃ for 12 to 24 hours until the weight is constant to obtain the pure bagasse xylan/naringin-g-HPMA/DEAM/DMDAAC graft copolymer.
(9) 30.0-50.0 g of ionic liquid 1-butyl-2, 3-dimethyl imidazolium chloride is weighed into a 250mL four-neck flask, placed into a water bath kettle, and heated to 50-70 ℃.
(10) And (3) weighing 1.0-2.5 g of bagasse xylan/naringin-g-HPMA/DEAM/DMDAAC graft copolymer, adding the bagasse xylan/naringin-g-HPMA/DEAM/DMDAAC graft copolymer into the four-neck flask in the step (9) filled with the ionic liquid, and stirring for 0.5-1 hour. After the reactants are completely dissolved, adding 2.5-5 g of acetylsalicylic acid, stirring and dissolving uniformly, then adding 0.2-0.5 g N, N' -Diisopropylcarbodiimide (DIC) and 0.3-0.8 g of montmorillonite composite catalyst, controlling the temperature at 60-80 ℃, reacting for 4-8 hours under stirring, and cooling the system to room temperature.
(11) And (4) adding 50-70 mL of analytically pure absolute ethyl alcohol into the system obtained in the step (10), precipitating for 20-30 minutes, and performing suction filtration to obtain a precipitate. And sequentially and respectively measuring 10-15 mL of analytically pure absolute ethyl alcohol and 15-20 mL of distilled water to perform suction filtration and washing on the precipitate, and repeating the operation for 2-3 times. And (3) drying the obtained filter cake in a constant-temperature drying oven at 60 ℃ for 24 hours to constant weight to obtain the bagasse xylan/naringin-g-HPMA/DEAM/DMDAAC acetylsalicylate.
(12) The method adopts an acid-base titration method to carry out esterification substitution degree determination on the product BX/Nar-g-HPMA/DEAM/DMDAAC acetylsalicylate, and comprises the following specific steps: accurately weighing about 0.5g of product sample, putting the product sample into a 50mL conical flask, adding 20mL of deionized water into the conical flask, fully shaking the mixture, adding 2-3 drops of phenolphthalein indicator, titrating the sample solution to light red by using a 0.5mol/L NaOH standard solution, and maintaining the red color within 30 seconds without removing the sample solution. Adding 2.5mL of 0.5mol/L sodium hydroxide solution, shaking up, sealing, placing in an electric oscillator at room temperature, shaking for saponification for 4 hours, titrating with 0.5mol/L hydrochloric acid standard solution until the solution system is colorless, and recording the volume of the hydrochloric acid standard solution consumed by titration as V1(ii) a Under the same conditions, a blank titration with BX/Nar-g-HPMA/DEAM/DMDAAC graft copolymer was carried out and the volume V of the standard solution of hydrochloric acid consumed was recorded0. Mass fraction (w) of carboxylic acid acyl groups in the target productc) The calculation formula of BX/Nar-g-HPMA/DEAM/DMDAAC acetylsalicylate Degree of Substitution (DS) is as follows:
Figure BDA0003240325780000041
Figure BDA0003240325780000042
in the formula:
wc-the target product contains the mass fraction of carboxylic acid acyl groups,%;
V0-performing a blank titration consuming a volume of hydrochloric acid standard solution in mL;
V1titrating the volume of the hydrochloric acid standard solution consumed by the target product in mL;
CHCl-hydrochloric acid standard solution concentration, in moL/L;
m is the mass of the target product sample in g;
DS-degree of esterification substitution of LTBX-g-HEMA;
m-molar mass of carboxylic acid acyl groups, g/mol;
132-relative molecular mass of xylan dehydration units.
Bagasse xylan/naringin-g-HPMA/DEAM/DMDAAC acetylsalicylate is synthesized by chemical modification methods such as grafting and esterification. Compared with the original bagasse xylan, the solubility of the xylan in water at room temperature is improved by about 10%, and the thermal stability is also improved. Molecular docking analysis shows that hydrogen bonds exist between the xylan main chain and the grafting monomer on the side chain of the product molecule and 4 receptor proteins, and the sites for generating the hydrogen bonds are wide when the receptor proteins are docked. Realizes the effective combination of the product and various amino acid residues of the receptor protein, and has wide anticancer and biological medicinal research prospects.
Drawings
FIG. 1 is an IR chart of raw bagasse xylan.
FIG. 2 is an IR chart of BX/Nar-g-HPMA/DEAM/DMDAAC acetylsalicylate prepared by example of the present invention.
Figure 3 is an XRD pattern of raw bagasse xylan.
FIG. 4 is an XRD pattern of BX/Nar-g-HPMA/DEAM/DMDAAC acetylsalicylate prepared in accordance with examples of the present invention.
FIG. 5 is an SEM photograph of raw bagasse xylan.
FIG. 6 is an SEM photograph of BX/Nar-g-HPMA/DEAM/DMDAAC acetylsalicylate prepared in the example of the present invention.
FIG. 7 is a diagram of the docking of BX/Nar-g-HPMA/DEAM/DMDAAC acetylsalicylate with 6P8Y receptor protein.
FIG. 8 is the cavity docking diagram of BX/Nar-g-HPMA/DEAM/DMDAAC acetylsalicylate and 6P8Y receptor protein.
Detailed Description
Example (b):
(1) and (3) drying 4.0g of bagasse xylan in a vacuum constant-temperature drying oven at 60 ℃ for 24 hours to obtain the dry-based bagasse xylan.
(2) Placing 0.3g naringin sugar in a vacuum constant temperature drying oven at 60 deg.C, and drying for 24 hr to obtain dry naringin.
(3) 0.6g of ammonium persulfate is weighed into a 50mL beaker, 15mL of distilled water is added to prepare an initiator solution, the initiator solution is stirred for 10 minutes at room temperature, and the initiator solution is poured into a 100mL constant-pressure dropping funnel for later use.
(4) 4.0mL of analytically pure hydroxypropyl methacrylate, 4.5mL of analytically pure diethylaminoethyl methacrylate and 4.3mL of analytically pure dimethyldiallylammonium chloride are weighed out and placed in a 50mL beaker, and after uniform stirring and mixing, a monomer mixed solution is obtained and poured into another 100mL constant-pressure dropping funnel for later use.
(5) Weighing 3.75g of the dry bagasse xylan obtained in the step (1) and 0.25g of the dry naringin obtained in the step (2), placing the dry bagasse xylan and the dry naringin into a 250mL four-neck flask, adding 0.125g N, N-dimethylene bisacrylamide and 60mL of distilled water, heating to 60 ℃, and stirring for 30 minutes to obtain the mixed activation solution of the bagasse xylan and the naringin.
(6) Firstly, dropwise adding one third of the initiator solution obtained in the step (3) to the bagasse xylan activation solution obtained in the step (5), controlling the temperature at 50 ℃ and the dropwise adding time at 1 hour, continuously stirring for 30 minutes after the addition is finished, synchronously dropwise adding the monomer solution obtained in the step (3) and the initiator solution obtained in the remaining two thirds of the step (2), controlling the dropwise adding time of the monomer and the initiator at 3 hours, continuously reacting for 2 hours after the dropwise addition is finished, and cooling the obtained material to room temperature.
(7) And (4) precipitating the material obtained in the step (6) by using 25mL of analytically pure absolute ethyl alcohol for 20-30 minutes, and performing suction filtration. 10mL of analytically pure absolute ethanol and 15mL of analytically pure cyclohexane are respectively measured each time, and the precipitate is washed and filtered for 3 times. And (3) drying the obtained filter cake in a constant-temperature drying oven at 60 ℃ for 24 hours to constant weight to obtain the crude bagasse xylan/naringin-g-HPMA/DEAM/DMDAAC graft copolymer.
(8) Placing the bagasse xylan/naringin-g-HPMA/DEAM/DMDAAC obtained in the step (7) into a Soxhlet extractor, and adding 60mL of analytically pure cyclohexane for extraction for 12 hours; and (3) taking out the materials after extraction, putting the materials into a watch glass, and placing the watch glass in a vacuum constant-temperature drying oven at 60 ℃ for drying for 24 hours until the weight is constant to obtain the pure bagasse xylan/naringin-g-HPMA/DEAM/DMDAAC graft copolymer.
(9) 40.0g of ionic liquid 1-butyl-2, 3-dimethylimidazolium chloride is weighed into a 250mL four-neck flask, placed in a water bath and heated to 60 ℃.
(10) And (3) weighing 1.5g of bagasse xylan/naringin-g-HPMA/DEAM/DMDAAC graft copolymer, adding the bagasse xylan/naringin-g-HPMA/DEAM/DMDAAC graft copolymer into the four-neck flask in the step (9) filled with the ionic liquid, and stirring for 0.5-1 hour. After the reactants are completely dissolved, adding 4.0g of acetylsalicylic acid, stirring and dissolving uniformly, then adding 0.3g N, N' -Diisopropylcarbodiimide (DIC) and 0.6g of montmorillonite composite catalyst, controlling the temperature at 60-80 ℃, reacting for 4-8 hours under stirring, and cooling the system to room temperature.
(11) And (4) adding 60mL of analytically pure absolute ethyl alcohol into the system obtained in the step (10), precipitating for 30 minutes, and filtering to obtain a precipitate. 10mL of analytically pure absolute ethyl alcohol and 15mL of distilled water are sequentially measured to carry out suction filtration and washing on the precipitate, and the operation is repeated for 3 times. And (3) drying the obtained filter cake in a constant-temperature drying oven at 60 ℃ for 24 hours to constant weight to obtain the bagasse xylan/naringin-g-HPMA/DEAM/DMDAAC acetylsalicylate.
(12) And (3) measuring the esterification substitution degree of the bagasse xylan/naringin-g-HPMA/DEAM/DMDAAC acetylsalicylate product obtained in the step (9) by using an acid-base titration method, and measuring that the DS is 0.73.
SEM analysis shows that the xylan particles are spherical, the surface is smooth and round, the particle distribution is uniform, and the overall appearance is consistent; the surface of the product particles becomes rough and irregular in shape, the amplified surface is known to be in the form of flakes and particle clusters, the surface arrangement and the particle size are not regular, and the product particles can be found to be larger than xylan particles under the same time of microscope. The IR analysis showed that 1596.17cm of product appeared-1C ═ O of ester carbonyl of HPMA and DEAM and stretching vibration peak of benzene ring skeleton of naringin of (1735.17 cm)-1C ═ O stretching vibration peaks at HPMA and DEAM, DMDAAC and the ester carbonyl of acetylsalicylic acid and naringin; 1488.92cm-1The absorption peak of bending vibration of N-H and stretching vibration of C-N appears, 1602.30cm-1The skeleton vibration absorption peak of the benzene ring in the acetylsalicylic acid and the skeleton vibration peak of the benzene ring in the naringin molecule appear; 1384.54cm-1The C-N bending vibration absorption peak of DEAM is shown, 1249.04cm-1The C-O-C stretching vibration absorption peak of C-N and monomer appears, 1146.33cm-1The C-N stretching vibration absorption peak appears. XRD analysis shows that BX is 12.62. 14.96, 19.16, 23.86 and 31.67 have stronger diffraction peaks with sharp and prominent peak types, which shows that BX has a certain crystal structure; the product is compared with a crude xylan XRD (X-ray diffraction) pattern, the intensity of the diffraction angle is obviously reduced, and the crystallization degree of the bagasse xylan is obviously changed after the bagasse xylan is modified. As can be seen from a molecular docking diagram, due to the hydrophobic effect of xylan and a side chain modification group and a benzene ring in naringin, receptor protein has an obvious active cavity, which indicates that a product can effectively enter the interior of the receptor protein, so that the structure of the receptor protein is changed to a certain extent, the product is proved to have good docking activity on the receptor protein, the effective combination of the product and various amino acid residues of the receptor protein is realized, and the molecular docking diagram has wide anticancer and biomedical research prospects.

Claims (1)

1. A method for synthesizing active BX/Nar-g-HPMA/DEAM/DMDAAC acetylsalicylate is characterized by comprising the following steps:
(1) drying 4.0-5.0 g of bagasse xylan in a vacuum constant-temperature drying oven at 60 ℃ for 24 hours to obtain dry-based bagasse xylan;
(2) putting 0.3-0.5 g of naringin sugar in a vacuum constant-temperature drying oven at 60 ℃ for drying for 24 hours to obtain dry naringin;
(3) weighing 0.3-0.7 g of ammonium persulfate in a 50mL beaker, adding 10-20 mL of distilled water to prepare an initiator solution, stirring at room temperature for 5-10 minutes, and pouring into a 100mL constant-pressure dropping funnel for later use;
(4) weighing 3.0-5.0 mL of analytically pure hydroxypropyl methacrylate, 4.0-5.0 mL of analytically pure diethylaminoethyl methacrylate and 4.0-5.0 mL of analytically pure dimethyldiallylammonium chloride, placing the materials into a 50mL beaker, stirring and mixing the materials uniformly to obtain a monomer mixed solution, and pouring the monomer mixed solution into another 100mL constant-pressure dropping funnel for later use;
(5) weighing 3.0-4.0 g of dry bagasse xylan obtained in the step (1) and 0.2-0.3 g of dry naringin obtained in the step (2), placing the dry bagasse xylan and the dry naringin into a 250mL four-neck flask, adding 0.1-0.2 g N, N-dimethylene bisacrylamide and 50-70 mL of distilled water, heating to 45-65 ℃, and stirring for 20-30 minutes to obtain a mixed activation solution of bagasse xylan and naringin;
(6) firstly, dropwise adding one third of the initiator solution obtained in the step (3) to the bagasse xylan activation solution obtained in the step (5), controlling the temperature to be 50-70 ℃, the dropwise adding time to be 1-2 hours, continuously stirring for 20-30 minutes after the addition is finished, synchronously dropwise adding the monomer solution obtained in the step (3) and the initiator solution obtained in the remaining two thirds of the step (2), controlling the dropwise adding time of the monomer and the initiator to be 2-5 hours, continuously reacting for 2-3 hours after the dropwise addition is finished, and cooling the obtained material to room temperature;
(7) precipitating the material obtained in the step (6) by using 20-40 mL of analytically pure absolute ethyl alcohol for 20-30 minutes, and performing suction filtration; 10-15 mL of analytically pure absolute ethyl alcohol and 10-20 mL of analytically pure cyclohexane are respectively measured each time, and the precipitate is washed and filtered for 2-3 times; drying the obtained filter cake in a constant-temperature drying oven at 60 ℃ for 24 hours to constant weight to obtain a crude bagasse xylan/naringin-g-HPMA/DEAM/DMDAAC graft copolymer;
(8) placing the bagasse xylan/naringin-g-HPMA/DEAM/DMDAAC obtained in the step (7) into a Soxhlet extractor, and adding 50-60 mL of analytically pure cyclohexane to extract for 12-24 hours; after extraction, taking out the materials, putting the materials into a watch glass, and drying the materials in a vacuum constant-temperature drying oven at 60 ℃ for 12 to 24 hours until the weight is constant to obtain a pure bagasse xylan/naringin-g-HPMA/DEAM/DMDAAC graft copolymer;
(9) weighing 30.0-50.0 g of ionic liquid 1-butyl-2, 3-dimethyl imidazolium chloride into a 250mL four-neck flask, placing the flask in a water bath, and heating to 50-70 ℃;
(10) weighing 1.0-2.5 g of bagasse xylan/naringin-g-HPMA/DEAM/DMDAAC graft copolymer, adding the bagasse xylan/naringin-g-HPMA/DEAM/DMDAAC graft copolymer into the four-neck flask in the step (9) filled with ionic liquid, and stirring for 0.5-1 hour; after the reactants are completely dissolved, adding 2.5-5 g of acetylsalicylic acid, stirring and dissolving uniformly, then adding 0.2-0.5 g N, N' -diisopropylcarbodiimide and 0.3-0.8 g of montmorillonite composite catalyst, controlling the temperature at 60-80 ℃, reacting for 4-8 hours under stirring, and cooling the system to room temperature;
(11) adding 50-70 mL of analytically pure absolute ethanol into the system obtained in the step (10), precipitating for 20-30 minutes, and performing suction filtration to obtain a precipitate; sequentially and respectively measuring 10-15 mL of analytically pure absolute ethyl alcohol and 15-20 mL of distilled water to carry out suction filtration and washing on the precipitate, and repeating the operation for 2-3 times; and (3) drying the obtained filter cake in a constant-temperature drying oven at 60 ℃ for 24 hours to constant weight to obtain the bagasse xylan/naringin-g-HPMA/DEAM/DMDAAC acetylsalicylate.
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