CN112175141A - Synthesis method of active cross-linked BX/SGPS nitro-p-methyl benzoate-g-AM - Google Patents
Synthesis method of active cross-linked BX/SGPS nitro-p-methyl benzoate-g-AM Download PDFInfo
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Abstract
The invention discloses a method for synthesizing active crosslinked BX/SGPS nitro-p-methyl benzoate-g-AM. Bagasse xylan/momordica grosvenori polysaccharide is used as a raw material, acrylamide is used as a grafting monomer, persulfate is used as an initiator,N,Nmethylene bisacrylamide is used as a cross-linking agent, and cross-linked BX/SGPS-g-AM is synthesized through free radical polymerization in a water solvent; then, the acyl chloride product of 3-nitro-p-methyl benzoic acid, 3-nitro-p-methyl benzoyl chloride, is used as esterifying agent, cetyl trimethyl ammonium bromide and pyridine are used as composite catalyst, and the esterification reaction is catalyzed in organic solventThe final product, namely the active crosslinked BX/SGPS nitro-p-methyl benzoate-g-AM, is synthesized. The tumor cell chemotactic movement inhibitor 4-methyl-3-nitrobenzoic acid is adopted for esterification and crosslinking of BX/SGPS-g-AM, the substitution degree is improved to be more than 0.8, and the biological activity and the physical and chemical properties of the bagasse xylan derivative are expanded.
Description
Technical Field
The invention relates to the field of fine chemical engineering, in particular to a method for synthesizing active crosslinked BX/SGPS nitro-p-methyl benzoate-g-AM.
Background
The natural plant polysaccharide generally has biological functions of resisting cancer, resisting aging, resisting oxidation, regulating immunity and the like, and is a safe and low-toxicity renewable resource. In recent years, Bagasse Xylan (BX) has reported some modification studies on xylan in order to improve its biological activity due to its specific structure. The momordica grosvenori polysaccharide (SGPS) is also a characteristic plant resource in Guangxi, has rich biological functions, and if the momordica grosvenori polysaccharide and the bagasse xylan are compounded and chemically modified, a new field of research on the biological activity of the bagasse xylan/momordica grosvenori polysaccharide compound (BX/SGPS) is developed.
Research shows that the momordica grosvenori polysaccharide has the effects of diminishing inflammation, resisting oxidation, resisting tumors, reducing blood sugar and the like in cells, and the momordica grosvenori polysaccharide composition and the momordica grosvenori polysaccharide structure contain primary hydroxyl at C6 and secondary hydroxyl at C2 and C3, so that the momordica grosvenori polysaccharide can be compounded with bagasse xylan and modified at the same time. If the bagasse xylan and the momordica grosvenori polysaccharide are compounded, active groups of monomers such as Acrylamide (AM) and the like are introduced in a grafting manner, a cross-linking agent is added to enable the formed binary graft copolymer to be cross-linked, and the cross-linked graft copolymer is esterified by organic acid to form a product with a network structure, so that the thermal stability of the bagasse xylan and momordica grosvenori polysaccharide compound can be improved, and the compound can be used as a drug carrier to slow down adverse reactions of a human body to chemotherapeutic drugs. On the other hand, the organic acid 4-methyl-3-nitrobenzoic acid can effectively inhibit the growth and the metastasis of tumors, is a potential therapeutic target, and can be subjected to esterification reaction with active hydroxyl on a binary graft copolymer of the bagasse xylan/momordica grosvenori polysaccharide complex to generate ester groups which can further enhance the anti-tumor activity of the compound, thereby providing a basis for the application of multi-targeting drug carriers.
The bagasse xylan/momordica grosvenori polysaccharide copolymer, namely, the crosslinked BX/SGPS-g-AM, is synthesized by taking bagasse xylan/momordica grosvenori polysaccharide as a main raw material, acrylamide as a grafting monomer, persulfate as an initiator and N, N-methylene bisacrylamide as a crosslinking agent through free radical polymerization in a water solvent; then, the intermediate product crosslinked BX/SGPS-g-AM is used as a raw material, the acyl chloride product of 3-nitro-p-methylbenzoic acid, namely 3-nitro-p-methylbenzoyl chloride, is used as an esterifying agent, cetyl trimethylammonium bromide and pyridine are used as composite catalysts, and the final product, namely the active crosslinked BX/SGPS nitro-p-methylbenzoate-g-AM, is synthesized through a catalytic esterification reaction in an organic solvent.
Disclosure of Invention
The invention aims to improve the biological activity of bagasse xylan/momordica grosvenori polysaccharide complex by compounding bagasse xylan with momordica grosvenori polysaccharide and modifying the complex by esterification, grafting and other methods, broadens the application of the bagasse xylan/momordica grosvenori polysaccharide complex in the fields of fine chemical engineering, medicines and the like, and provides a synthetic method of active crosslinked BX/SGPS nitro-p-methyl benzoate-g-AM.
The method comprises the following specific steps:
(1) respectively placing 5-8 g of bagasse xylan and 5-8 g of momordica grosvenori polysaccharide in a vacuum constant-temperature drying oven at 60 ℃ for drying for 24 hours to obtain dry-base bagasse xylan and dry-base momordica grosvenori polysaccharide.
(2) Weighing 0.60-1.20 g of ammonium persulfate and 0.30-0.60 g of sodium bisulfite in a 50mL beaker, adding 20-30 mL of distilled water to prepare a redox system initiator solution, and pouring the redox system initiator solution into a 100mL constant-pressure dropping funnel for later use.
(3) Weighing 3.0-6.0 g of acrylamide, placing the acrylamide in a 50mL beaker, adding 15-30 mL of distilled water, stirring and dissolving uniformly to obtain a monomer solution, and pouring the monomer solution into another 100mL constant-pressure dropping funnel for later use.
(4) Respectively weighing 3.0-6.0 g of the dry-based bagasse xylan obtained in the step (1) and 3.0-6.0 g of the dry-based momordica grosvenori polysaccharide obtained in the step (1), adding the dry-based bagasse xylan and the dry-based momordica grosvenori polysaccharide into a 250mL four-neck flask, adding 50-100 mL of distilled water, heating to 50-55 ℃ under stirring, and continuing stirring for 20-30 minutes to obtain the bagasse xylan/momordica grosvenori polysaccharide compound activating solution.
(5) Adding about one third of the redox system initiator solution obtained in the step (2) into the bagasse xylan/momordica grosvenori polysaccharide complex activating solution obtained in the step (4), stirring for 10-20 minutes, then synchronously dropwise adding the rest initiator solution obtained in the step (2) and the monomer solution obtained in the step (3), controlling the system temperature at 50-65 ℃ and the dropwise adding time at 3-5 hours, adding 0.20-0.40 g of cross-linking agent N, N-methylene bisacrylamide after dropwise adding is completed, continuously reacting for 3-5 hours, and cooling the materials to room temperature.
(6) And (3) precipitating the material obtained in the step (5) for 20-30 minutes by using 40-60 mL of analytically pure acetone, carrying out suction filtration, and washing and carrying out suction filtration for 2-3 times by using 60-80 mL of analytically pure acetone and 30-60 mL of analytically pure anhydrous ethanol in sequence. And (3) drying the filter cake in a constant-temperature drying oven at 60 ℃ for 18-24 hours to constant weight to obtain a bagasse xylan/momordica grosvenori polysaccharide-g-AM crude product.
(7) Placing the bagasse xylan/momordica grosvenori polysaccharide-g-AM crude product obtained in the step (6) into a Soxhlet extractor, and adding 150-200 mL of analytically pure acetone for extraction for 16-24 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 16-24 hours until the weight is constant to obtain a pure intermediate product of bagasse xylan/momordica grosvenori polysaccharide-g-AM.
(8) Weighing 3.0-6.0 g of 3-nitro-p-methylbenzoic acid into a 250mL four-neck flask, adding 3.0-6.0 mL of analytically pure thionyl chloride, adding 0.05-0.10 g of analytically pure N, N-dimethylformamide solution, heating to 55-70 ℃, and stirring for reacting for 2-3 hours to obtain 3-nitro-p-methylbenzoyl chloride mixed solution; evaporating the obtained mixed solution at 60-75 ℃ for 1-1.5 hours to obtain a light yellow transparent liquid, namely 3-nitro-p-methyl benzoyl chloride, and pouring the light yellow transparent liquid into a 100mL constant-pressure dropping funnel for later use.
(9) Weighing 3.0-6.0 g of pure bagasse xylan/momordica grosvenori polysaccharide-g-AM obtained in the step (7), placing the pure bagasse xylan/momordica grosvenori polysaccharide-g-AM into a 250mL four-neck flask, adding 60-80 mL of analytically pure toluene solvent, adding 0.2-0.4 g of catalyst hexadecyltrimethylammonium bromide and 3.0-12 mL of analytically pure pyridine catalyst and acid binding agent under stirring, slowly adding the 3-nitro-p-methylbenzoyl chloride obtained in the step (8) under stirring, heating to 65-90 ℃ under stirring, continuing stirring for reaction for 5-8 hours, and cooling the material to room temperature after the reaction is finished.
(10) And (3) precipitating the material obtained in the step (9) for 20-30 minutes by using 40-60 mL of analytically pure acetone, and after suction filtration, washing and suction filtering the precipitate for 2-3 times by using 60-80 mL of analytically pure acetone and 30-60 mL of analytically pure absolute ethyl alcohol respectively. And (3) drying the filter cake in a constant-temperature drying oven at 60 ℃ for 18-24 hours to constant weight to obtain the product, namely the crosslinked BX/SGPS nitro-p-methyl benzoate-g-AM.
(11) And (3) measuring the esterification substitution degree of the product crosslinked BX/SGPS nitro-p-methyl benzoate-g-AM obtained in the step (10) by using an acid-base titration method, which comprises the following specific steps: accurately weighing about 0.5g of a product sample into a 50mL conical flask, adding 20mL of deionized water into the conical flask, fully shaking, adding 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 indicator. 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 condition, the bagasse xylan/momordica grosvenori polysaccharide graft copolymer is used for blank titration, and the volume V of the consumed hydrochloric acid standard solution is recorded0. Mass fraction (w) of carboxylic acid acyl groups in the target productc) Esterification substitution Degree (DS) of crosslinked BX/SGPS nitro-p-methyl benzoate-g-AMC) The calculation formula is as follows:
in the formula:
wc-the target product contains the mass fraction of carboxylic acid acyl groups,%;
V0blank titration of the bagasse xylan/momordica grosvenori polysaccharide graft product consumes the volume of a hydrochloric acid standard solution in unit 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;
DSc-the degree of esterification substitution of crosslinked BX/SGPS nitro-p-methylbenzoate-g-AM;
m and 145.5-acyl group of carboxylic esterifying agent and average relative molecular mass of bagasse xylan/mogroside dehydration unit.
The invention synthesizes the active crosslinking BX/SGPS nitro-p-methyl benzoate-g-AM derivative by compounding excessive bagasse xylan with momordica grosvenori polysaccharide and modifying the compound by methods of esterification, grafting and the like. The tumor cell chemotactic movement inhibitor 4-methyl-3-nitrobenzoate is adopted to carry out esterification and crosslinking of BX/SGPS-g-AM, and the substitution degree is improved to be more than 0.8. The synthesis process improves the utilization rate of hydroxyl, simultaneously expands the biological activity and the physical and chemical properties of the bagasse xylan derivative, and widens the application of the bagasse xylan derivative in the fields of fine chemical engineering, medicine and the like.
Drawings
FIG. 1 is an SEM photograph of raw bagasse xylan.
FIG. 2 is an SEM photograph of cross-linked BX/SGPS nitro-p-methylbenzoate-g-AM prepared in accordance with an example of the present invention.
FIG. 3 is an IR plot of a bagasse xylan/mogroside complex and cross-linked BX/SGPS nitro-p-methylbenzoate-g-AM prepared in accordance with an embodiment of the present invention; wherein: a is an IR picture of a bagasse xylan/siraitia grosvenorii polysaccharide complex, and b is an IR picture of cross-linked BX/SGPS nitro-p-methyl benzoate-g-AM prepared in an embodiment of the invention.
Figure 4 is an XRD pattern of raw bagasse xylan.
FIG. 5 is an XRD pattern of cross-linked BX/SGPS nitro-p-methylbenzoate-g-AM prepared in accordance with an example of the present invention.
FIG. 6 is a graph showing TG and DTG curves of raw bagasse xylan.
FIG. 7 is a TG and DTG curve of cross-linked BX/SGPS nitro-p-methyl benzoate-g-AM prepared in the example of the present invention.
Detailed Description
Example (b):
(1) respectively placing 5.5g of bagasse xylan and 5.5g of momordica grosvenori polysaccharide in a vacuum constant-temperature drying oven at 60 ℃ for drying for 24 hours to obtain dry-base bagasse xylan and dry-base momordica grosvenori polysaccharide.
(2) 0.80g of ammonium persulfate and 0.40g of sodium bisulfite are weighed into a 50mL beaker, 25mL of distilled water is added to prepare a redox system initiator solution, and the redox system initiator solution is poured into a 100mL constant pressure dropping funnel for later use.
(3) 5.0g of acrylamide is weighed and placed in a 50mL beaker, 20mL of distilled water is added, the monomer solution is obtained after uniform stirring and dissolution, and the monomer solution is poured into another 100mL constant pressure dropping funnel for standby.
(4) Respectively weighing 5.0g of the dry bagasse xylan obtained in the step (1) and 5.0g of the dry momordica grosvenori polysaccharide obtained in the step (1), adding the dry bagasse xylan and the dry momordica grosvenori polysaccharide into a 250mL four-neck flask, adding 80mL of distilled water, heating to 55 ℃ under stirring, and continuing stirring for 30 minutes to obtain the bagasse xylan/momordica grosvenori polysaccharide compound activating solution.
(5) Adding one third of the redox system initiator solution obtained in the step (2) into the bagasse xylan/momordica grosvenori polysaccharide complex activating solution obtained in the step (4), stirring for 15 minutes, then synchronously dropwise adding the rest initiator solution obtained in the step (2) and the monomer solution obtained in the step (3), controlling the system temperature at 55 ℃ and the dropwise adding time at 3 hours, adding 0.20g of cross-linking agent N, N-methylene bisacrylamide after the dropwise adding is finished, continuously reacting for 5 hours, and cooling the materials to room temperature.
(6) And (3) precipitating the material obtained in the step (5) for 25 minutes by using 50mL of analytically pure acetone, carrying out suction filtration, and washing and carrying out suction filtration on the obtained precipitate for 3 times by using 70mL of analytically pure acetone and 50mL of analytically pure anhydrous ethanol in sequence. And (3) drying the filter cake in a constant-temperature drying oven at 60 ℃ for 24 hours to constant weight to obtain a bagasse xylan/momordica grosvenori polysaccharide-g-AM crude product.
(7) Placing the bagasse xylan/momordica grosvenori polysaccharide-g-AM crude product obtained in the step (6) into a Soxhlet extractor, and adding 180mL of analytically pure acetone for extraction for 18 hours; and 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, thereby obtaining pure intermediate product bagasse xylan/momordica grosvenori polysaccharide-g-AM.
(8) Weighing 5.0g of 3-nitro-p-methylbenzoic acid into a 250mL four-neck flask, adding 5.0mL of analytically pure thionyl chloride, then adding 0.10g of analytically pure N, N-dimethylformamide solution, heating to 65 ℃, and stirring for reacting for 2.5 hours to obtain 3-nitro-p-methylbenzoyl chloride mixed solution; the resulting mixed solution was evaporated at 70 ℃ for 1 hour to give a pale yellow transparent liquid, i.e., 3-nitro-p-methylbenzoyl chloride, which was poured into a 100mL constant pressure dropping funnel for use.
(9) Weighing 5.0g of the pure bagasse xylan/momordica grosvenori polysaccharide-g-AM obtained in the step (7), placing the pure bagasse xylan/momordica grosvenori polysaccharide-g-AM into a 250mL four-neck flask, adding 60mL of analytically pure toluene solvent, adding 0.3g of catalyst hexadecyltrimethylammonium bromide and 9.0mL of analytically pure pyridine catalyst and acid binding agent under stirring, slowly adding the 3-nitro-p-methylbenzoyl chloride obtained in the step (8) under stirring, heating to 75 ℃ under stirring, continuing stirring for reaction for 7 hours, and cooling the material to room temperature after the reaction is finished.
(10) And (3) precipitating the material obtained in the step (9) for 20-30 minutes by using 50mL of analytically pure acetone, and after suction filtration, washing and suction filtration 2 times by using 70mL of analytically pure acetone and 50mL of analytically pure absolute ethyl alcohol respectively. And (3) drying the filter cake in a constant-temperature drying oven at 60 ℃ for 24 hours to constant weight to obtain the product, namely the crosslinked BX/SGPS nitro-p-methyl benzoate-g-AM.
(11) Measuring the esterification substitution degree of the product crosslinked BX/SGPS nitro-p-methyl benzoate-g-AM obtained in the step (10) by an acid-base titration method to obtain DScIs 0.83.
SEM analysis on the product crosslinked BX/SGPS nitro-p-methyl benzoate-g-AM shows that after compounding, esterification, grafting and modification, the crosslinked BX/SGPS nitro-p-methyl benzoate-g-AM has rough surface, irregular appearance and a plurality of branches, spherical polysaccharide can be seen to be wrapped in the crosslinked BX/SGPS nitro-p-methyl benzoate-g-AM, the pore structure is complex, and the appearance of xylan is greatly changed due to the introduction of esterified grafting molecules, which is obviously different from the surface structure of original bagasse xylan particles. IR analysis showed 2929.64cm of crosslinked BX/SGPS nitro-p-methyl benzoate-g-AM-1(ii) methylene stretching vibration absorption peak of 1663.64cm-1Characteristic absorption peak of amide group in acrylamide, 1735.51cm-1C ═ O stretching vibration absorption peak of ester group, 1624.44cm-1Has a stretching vibration absorption peak of 1533.09cm in the aromatic ring C ═ C bond-1And 1353.92cm-1N-O stretching vibration absorption peak of aromatic nitro compound, 743.64cm-1The new characteristic peaks show that the grafted monomer acrylamide and the esterifying agent 3-nitro-p-methyl benzoic acid react with hydroxyl on the bagasse xylan/momordica grosvenori polysaccharide complex, and the molecular chain of the bagasse xylan/momordica grosvenori polysaccharide complex is introduced with the characteristic groups of acrylamide and 4-methyl-3-nitrobenzoic acid. XRD analysis shows that the crosslinked BX/SGPS nitrobenzoate-g-AM has diffraction peaks at 14.5 degrees, 20.2 degrees, 21.3 degrees, 24.7 degrees, 31.3 degrees, 32.6 degrees, 37.3 degrees and the like, the peak shape is narrow and sharp, and the integral diffraction peak is not obvious. Compared with the original BX/SGPS, the diffraction peak pattern is not changed as a whole, the fine peak pattern is reduced, and the crystallinity of the modified derivative is reduced. According to the TG-DTG curve of the analyzed product, the crosslinked BX/SGPS nitrobenzoate-g-AM after the compound esterification graft modification can be divided into four stages in the temperature range of 0-800 ℃. The loss of the sample is 12% in the temperature range of 0 ℃ to 200 ℃, and the mass reduction of the sample can be caused by the loss of part of residual water and crystal water in the sample; the mass loss of the sample is about 40% in the temperature range of 200 ℃ to 350 ℃, which may be caused by the cleavage of the glycosidic linkages of xylan and mogroside in the sample; sample mass at a temperature in the range of 350 ℃ to 600 ℃About 38% loss, which may be caused by the cleavage of branches after graft esterification and the cleavage of ester bonds; the sample quality is basically unchanged at 600-800 ℃; it can be seen that the thermal stability of the esterified graft-modified product is improved to some extent.
Claims (1)
1. A synthetic method of active crosslinking BX/SGPS nitro-p-methyl benzoate-g-AM is characterized by comprising the following specific steps:
(1) respectively placing 5-8 g of bagasse xylan and 5-8 g of momordica grosvenori polysaccharide in a vacuum constant-temperature drying oven at 60 ℃ for drying for 24 hours to obtain dry-based bagasse xylan and dry-based momordica grosvenori polysaccharide;
(2) weighing 0.60-1.20 g of ammonium persulfate and 0.30-0.60 g of sodium bisulfite in a 50mL beaker, adding 20-30 mL of distilled water to prepare a redox system initiator solution, and pouring the redox system initiator solution into a 100mL constant-pressure dropping funnel for later use;
(3) weighing 3.0-6.0 g of acrylamide, placing the acrylamide in a 50mL beaker, adding 15-30 mL of distilled water, stirring and dissolving uniformly to obtain a monomer solution, and pouring the monomer solution into another 100mL constant-pressure dropping funnel for later use;
(4) respectively weighing 3.0-6.0 g of the dry-based bagasse xylan obtained in the step (1) and 3.0-6.0 g of the dry-based momordica grosvenori polysaccharide obtained in the step (1), adding the dry-based bagasse xylan and the dry-based momordica grosvenori polysaccharide into a 250mL four-neck flask, adding 50-100 mL of distilled water, heating to 50-55 ℃ under stirring, and continuing stirring for 20-30 minutes to obtain a bagasse xylan/momordica grosvenori polysaccharide compound activating solution;
(5) adding one third of the redox system initiator solution obtained in the step (2) into the bagasse xylan/momordica grosvenori polysaccharide complex activating solution obtained in the step (4), stirring for 10-20 minutes, then starting to synchronously dropwise add the initiator solution obtained in the rest step (2) and the monomer solution obtained in the step (3), controlling the system temperature at 50-65 ℃ and the dropwise adding time at 3-5 hours, adding 0.20-0.40 g of cross-linking agent N, N-methylene bisacrylamide after dropwise adding is finished, continuing to react for 3-5 hours, and cooling the materials to room temperature;
(6) precipitating the material obtained in the step (5) for 20-30 minutes by using 40-60 mL of analytically pure acetone, carrying out suction filtration, and washing and carrying out suction filtration for 2-3 times on the precipitate by using 60-80 mL of analytically pure acetone and 30-60 mL of analytically pure anhydrous ethanol in sequence;
drying the filter cake in a constant-temperature drying oven at 60 ℃ for 18-24 hours to constant weight to obtain a bagasse xylan/momordica grosvenori polysaccharide-g-AM crude product;
(7) placing the bagasse xylan/momordica grosvenori polysaccharide-g-AM crude product obtained in the step (6) into a Soxhlet extractor, and adding 150-200 mL of analytically pure acetone for extraction for 16-24 hours; 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 60 ℃ for 16-24 hours until the weight is constant to obtain pure intermediate product bagasse xylan/momordica grosvenori polysaccharide-g-AM;
(8) weighing 3.0-6.0 g of 3-nitro-p-methylbenzoic acid into a 250mL four-neck flask, adding 3.0-6.0 mL of analytically pure thionyl chloride, adding 0.05-0.10 g of analytically pure N, N-dimethylformamide solution, heating to 55-70 ℃, and stirring for reacting for 2-3 hours to obtain 3-nitro-p-methylbenzoyl chloride mixed solution; evaporating the obtained mixed solution at 60-75 ℃ for 1-1.5 hours to obtain a light yellow transparent liquid, namely 3-nitro-p-methyl benzoyl chloride, and pouring the light yellow transparent liquid into a 100mL constant-pressure dropping funnel for later use;
(9) weighing 3.0-6.0 g of pure bagasse xylan/momordica grosvenori polysaccharide-g-AM obtained in the step (7), placing the pure bagasse xylan/momordica grosvenori polysaccharide-g-AM into a 250mL four-neck flask, adding 60-80 mL of analytically pure toluene solvent, adding 0.2-0.4 g of catalyst hexadecyltrimethylammonium bromide and 3.0-12 mL of analytically pure pyridine catalyst and acid binding agent under stirring, slowly adding the 3-nitro-p-methylbenzoyl chloride obtained in the step (8) under stirring, heating to 65-90 ℃ under stirring, continuing stirring for reaction for 5-8 hours, and cooling the material to room temperature after the reaction is finished;
(10) precipitating the material obtained in the step (9) for 20-30 minutes by using 40-60 mL of analytically pure acetone, and after suction filtration, washing and suction filtering the precipitate for 2-3 times by using 60-80 mL of analytically pure acetone and 30-60 mL of analytically pure absolute ethyl alcohol respectively;
and (3) drying the filter cake in a constant-temperature drying oven at 60 ℃ for 18-24 hours to constant weight to obtain the product, namely the crosslinked BX/SGPS nitro-p-methyl benzoate-g-AM.
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