CN112250796A - Preparation method of BX/SGPS nitro-p-methyl benzoate-g-AM/MA - Google Patents
Preparation method of BX/SGPS nitro-p-methyl benzoate-g-AM/MA Download PDFInfo
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Abstract
The invention discloses a method for synthesizing BX/SGPS nitro-p-methyl benzoate-g-AM/MA. Firstly, synthesizing bagasse xylan/momordica grosvenori polysaccharide-g-AM/MA (BX/SGPS-g-AM/MA) in a water solvent by using mixed bagasse xylan and momordica grosvenori polysaccharide as main raw materials and acrylamide and methyl acrylate as mixed grafting monomers; then carrying out catalytic esterification on the 3-nitro-p-methylbenzoyl chloride and BX/SGPS-g-AM/MA, and synthesizing a final product BX/SGPS nitro-p-methylbenzoate-g-AM/MA in an organic solvent. Compared with the original bagasse xylan, the thermal stability of the target product obtained by the invention is greatly improved, and the target product is expected to be widely applied to the fields of medicines, foods, functional materials and the like.
Description
Technical Field
The invention relates to the technical field of fine chemical engineering, in particular to a method for synthesizing active BX/SGPS nitro-p-methyl benzoate-g-AM/MA.
Background
The hemicellulose is natural high molecular polysaccharide with second content to cellulose in the nature, is green and degradable, has good biocompatibility and has potential utilization value. Xylan is widely present in bagasse as a main component of hemicellulose. The existing research shows that xylan can play a certain anti-cancer role by regulating the immunocompetence of an organism, is a natural high-molecular plant polysaccharide, is green and safe, and can be widely applied to the fields of food, materials, medicines and the like.
Because Bagasse Xylan (BX) has intramolecular hydrogen bonds and is insoluble in water, the deep development and utilization process of the Bagasse Xylan (BX) is greatly limited. Active functional groups are introduced through chemical modification, so that the physical, chemical and biological properties of the xylan can be obviously improved, wherein the xylan is modified through esterification and grafting commonly. The momordica grosvenori is known to have a certain enhancement and regulation effect on the immune function of the organism and contains a large amount of modifiable plant polysaccharide. However, because the respective biological activities of natural xylan and Siraitia Grosvenorii Polysaccharide (SGPS) are weaker, bagasse xylan and siraitia grosvenorii polysaccharide are uniformly mixed according to a certain proportion and then stirred for activation, and then common monomers with high reaction activity, such as Acrylamide (AM), Methyl Acrylate (MA) and the like, are selected for grafting modification, so that the biological activities of the two raw materials are expected to be greatly improved. The research finds that the 4-methyl-3-nitrobenzoic acid can inhibit chemotactic movement of various tumor cells, has potential anticancer activity, and the 4-methyl-3-nitrobenzoic acid is friendly to human body. The grafted product and 4-methyl-3-nitrobenzoic acid have an esterification reaction, and the obtained product has nitro which belongs to a strong electron-withdrawing group, so that benzene rings in the grafted product are passivated and electrophilic substitution reaction is not easy to occur, which means that the product has better stability compared with similar substances.
The method takes mixed bagasse xylan and momordica grosvenori polysaccharide as main raw materials, acrylamide and methyl acrylate as mixed grafting monomers, and firstly synthesizes bagasse xylan/momordica grosvenori polysaccharide-g-AM/MA (BX/SGPS-g-AM/MA) in a water solvent; under the catalysis of N, N-dimethylformamide, 3-nitro-p-methylbenzoic acid reacts with thionyl chloride to generate 3-nitro-p-methylbenzoyl chloride, and then catalytic esterification is carried out on the 3-nitro-p-methylbenzoyl chloride and BX/SGPS-g-AM/MA, so that a final product BX/SGPS nitro-p-methylbenzoate-g-AM/MA is synthesized in an organic solvent.
Disclosure of Invention
The invention aims to improve the biological activity of bagasse xylan and momordica grosvenori polysaccharide and expand the application of the bagasse xylan and momordica grosvenori polysaccharide in the direction of medicaments by chemically modifying the xylan/momordica grosvenori polysaccharide complex through grafting and esterification, and provides a preparation method of BX/SGPS nitro-p-methyl benzoate-g-AM/MA.
The method comprises the following specific steps:
(1) uniformly mixing bagasse xylan and momordica grosvenori polysaccharide in a mass ratio of 1:1, and drying 8-10 g of the mixture in a vacuum constant-temperature drying oven at 50-60 ℃ for 24 hours to constant weight to obtain a dry-based bagasse xylan/momordica grosvenori polysaccharide compound.
(2) 0.60-0.80 g of ammonium persulfate and 0.30-0.40 g of sodium bisulfite are sequentially weighed in a 50mL beaker, 20-30 mL of distilled water is added, the mixture is uniformly stirred to obtain an initiator solution, and the initiator solution is poured into a 100mL constant-pressure dropping funnel for later use.
(3) Adding 1.0-3.0 g of acrylamide, 1.0-2.5 mL of analytically pure methyl acrylate and 10-25 mL of distilled water into a 50mL beaker, stirring and dissolving to obtain a monomer mixed solution, and pouring the monomer mixed solution into another 100mL constant-pressure dropping funnel for later use.
(4) And (2) putting 6.0-8.0 g of the dry bagasse xylan/momordica grosvenori polysaccharide complex obtained in the step (1) into a 250mL four-neck flask, adding 50-80 mL of distilled water, heating to 50-60 ℃, and stirring and activating for 20-30 minutes.
(5) Firstly, adding one fourth of the mixed initiator solution obtained in the step (2) to the bagasse xylan/momordica grosvenori polysaccharide activation solution obtained in the step (4), stirring for 20-30 minutes, then synchronously dropwise adding the monomer mixed solution obtained in the step (3) and the rest initiator solution obtained in the step (2), controlling the system temperature at 50-70 ℃, dropwise adding time at 2-3 hours, and continuing to react for 2-5 hours after dropwise adding is finished; and after the monomer mixed solution and the initiator solution are dripped, adding 0.10-0.20 g of cross-linking agent N, N-methylene bisacrylamide into the system, and continuing to react for 3-5 hours. After the reaction was complete, the resulting mass was cooled to room temperature.
(6) And (3) adding 40-60 mL of analytically pure acetone into the material obtained in the step (5), precipitating for 20-30 minutes, and after suction filtration, washing and suction filtering the precipitate for 2-3 times by using 20-30 mL of analytically pure anhydrous ethanol and 20-30 mL of analytically pure acetone 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/MA crude product.
(7) And (3) placing the bagasse xylan-g-AM/MA crude product obtained in the step (6) into a Soxhlet extractor, adding 150-200 mL of analytically pure acetone to extract the crude product for 24 hours, placing the material into a watch glass, and drying in a vacuum constant-temperature drying oven at 60 ℃ for 24 hours to constant weight to obtain the pure bagasse xylan/momordica grosvenori polysaccharide-g-AM/MA graft copolymer.
(8) Weighing 2.0-5.0 g of 3-nitro-p-methylbenzoic acid in a 250mL four-neck flask, adding 5-8 mL of analytically pure thionyl chloride and 0.05-0.1 g of analytically pure dimethylformamide, heating the system to 60-70 ℃, and reacting for 2-3 hours under stirring to obtain a 3-nitro-p-methylbenzoyl chloride mixed solution; evaporating the obtained mixed solution at the temperature of 60-75 ℃ for 1-1.5 hours to obtain a light yellow transparent liquid, namely 3-nitro-p-methylbenzoyl chloride.
(9) Weighing 2.0-4.0 g of pure bagasse xylan/momordica grosvenori polysaccharide-g-AM/MA obtained in the step (7), placing the pure bagasse xylan/momordica grosvenori polysaccharide-g-AM/MA into a 250mL four-neck flask, adding 60-90 mL of analytically pure toluene solvent, then adding 0.10-0.40 g of tetrabutyl titanate and 2.0-4.0 mL of analytically pure pyridine catalyst and acid binding agent, slowly adding the 3-nitro-p-methylbenzoyl chloride obtained in the step (8) under stirring, heating to 60-70 ℃, continuing stirring for reaction for 5-8 hours, and cooling the material to room temperature after the reaction is finished.
(10) And (4) precipitating the material obtained in the step (9) for 20-30 minutes by using 40-60 mL of analytically pure acetone, and washing and filtering the precipitate for 2-3 times by using 40-50 mL of analytically pure acetone after suction filtration. And (3) drying the filter cake in a constant-temperature drying oven at 50-60 ℃ for 18-24 hours to constant weight to obtain a target product BX/SGPS nitro-p-methyl benzoate-g-AM/MA.
(11) And (3) measuring the esterification substitution degree of the product BX/SGPS nitro-p-methyl benzoate-g-AM/MA obtained in the step (10) by an acid-base titration method, which 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 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 BX/SGPS nitro-p-methyl benzoate-g-AM/MAC) The calculation formula is as follows:
in the formula:
wcthe target product BX/SGPS nitro-p-methyl benzoate-g-AM/MA contains carboxylic acyl by mass percent;
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-degree of esterification substitution of BX/SGPS nitro-p-methylbenzoate-g-AM/MA;
m and 145.5-acyl group of carboxylic esterifying agent and average relative molecular mass of bagasse xylan/mogroside dehydration unit.
The invention carries out esterification reaction on the basis of xylan graft copolymerization to synthesize the final product BX/SGPS MNBA ester-g-AM/MA. Compared with the original bagasse xylan, the thermal stability of the obtained target product is greatly improved, and the target product is expected to be widely applied to the fields of medicines, foods, functional materials and the like.
Drawings
FIG. 1 is an SEM photograph of bagasse xylan.
FIG. 2 is an SEM photograph of BX/SGPS nitro-p-methylbenzoate-g-AM/MA prepared by the example of the present invention.
FIG. 3 is an IR chart of raw bagasse xylan (a) and BX/SGPS nitro-p-methylbenzoate-g-AM/MA (b) prepared in the examples of the present invention.
Figure 4 is an XRD pattern of raw bagasse xylan.
FIG. 5 is an XRD pattern of BX/SGPS nitro-p-methylbenzoate-g-AM/MA prepared in 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 BX/SGPS nitro-p-methyl benzoate-g-AM/MA prepared in the example of the present invention.
Detailed Description
Example (b):
(1) uniformly mixing bagasse xylan and momordica grosvenori polysaccharide in a mass ratio of 1:1, and drying 10g of the mixture in a vacuum constant-temperature drying oven at 50-60 ℃ for 24 hours to constant weight to obtain a dry-based bagasse xylan/momordica grosvenori polysaccharide compound.
(2) 0.60g of ammonium persulfate and 0.30g of sodium bisulfite are sequentially weighed in a 50mL beaker, 30mL of distilled water is added, the mixture is uniformly stirred to obtain an initiator solution, and the initiator solution is poured into a 100mL constant-pressure dropping funnel for later use.
(3) In a 50mL beaker, 1.5g acrylamide, 1.5mL analytically pure methyl acrylate and 15mL distilled water were added, stirred and dissolved to obtain a monomer mixture, which was poured into another 100mL constant pressure dropping funnel for further use.
(4) And (2) putting 6.0g of the dried bagasse xylan/momordica grosvenori polysaccharide complex obtained in the step (1) into a 250mL four-neck flask, adding 60mL of distilled water, heating to 50 ℃, and stirring and activating for 25 minutes.
(5) Firstly, adding one fourth of the mixed initiator solution obtained in the step (2) to the bagasse xylan/momordica grosvenori polysaccharide activation solution obtained in the step (4), stirring for 20 minutes, then synchronously dropwise adding the monomer mixed solution obtained in the step (3) and the rest three fourths of the initiator solution obtained in the step (2), controlling the temperature of the system at 60 ℃ and the dropwise adding time at 3 hours, and continuing to react for 2 hours after the dropwise adding is finished; after the monomer mixed solution and the initiator solution are added dropwise, 0.10g of cross-linking agent N, N-methylene bisacrylamide is added into the system, and the reaction is continued for 5 hours. After the reaction was complete, the resulting mass was cooled to room temperature.
(6) And (3) adding 60mL of analytically pure acetone into the material obtained in the step (5), precipitating for 30 minutes, and after suction filtration, washing and suction filtration the precipitate by using 30mL of analytically pure anhydrous ethanol and 30mL of analytically pure acetone for 3 times. 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/MA crude product.
(7) And (3) placing the bagasse xylan-g-AM/MA crude product obtained in the step (6) into a Soxhlet extractor, adding 200mL of analytically pure acetone to extract the crude product for 24 hours, placing the material into a watch glass, and drying in a vacuum constant-temperature drying oven at 60 ℃ for 24 hours to constant weight to obtain the pure bagasse xylan/momordica grosvenori polysaccharide-g-AM/MA graft copolymer.
(8) Weighing 2.6g of 3-nitro-p-methylbenzoic acid in a 250mL four-neck flask, adding 6mL of analytically pure thionyl chloride and 0.1g of analytically pure dimethylformamide, heating the system to 65 ℃, and reacting for 3 hours under stirring to obtain a 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.
(9) Weighing 3.0g of the pure bagasse xylan/momordica grosvenori polysaccharide-g-AM/MA obtained in the step (7), placing the pure bagasse xylan/momordica grosvenori polysaccharide-g-AM/MA into a 250mL four-neck flask, adding 60mL of analytically pure toluene solvent, then adding 0.15g of tetrabutyl titanate and 3.4mL of analytically pure pyridine catalyst and acid binding agent, slowly adding the 3-nitro-p-methylbenzoyl chloride obtained in the step (8) under stirring, heating to 70 ℃, continuing stirring for reacting for 8 hours, and cooling the material to room temperature after the reaction is finished.
(10) And (4) precipitating the material obtained in the step (9) by using 40mL of analytically pure acetone for 30 minutes, and after suction filtration, washing and suction filtration are respectively carried out on the obtained precipitate by using 50mL of analytically pure acetone for 3 times. And (3) drying the filter cake in a constant-temperature drying oven at 60 ℃ for 18-24 hours to constant weight to obtain a target product BX/SGPS nitro-p-methyl benzoate-g-AM/MA.
(11) The substitution degree of the product BX/SGPS nitro-p-methyl benzoate-g-AM/MA is measured by an acid-base titration method to be 0.80.
The IR analysis is carried out on the product BX/SGPS nitro-p-methyl benzoate-g-AM/MA, and the spectrum is 3421.98cm-1The peak is the stretching vibration absorption peak of-OH in the molecular chain of the compound, 1532.88cm-1And 1354.32cm-1The absorption peak of N-O stretching vibration of the aromatic nitro compound is 744.68cm-1Is a bending vibration absorption peak of a benzene ring C-H; from these characteristic peaks, successful introduction of AM, MA and MNBA molecules into the product can be demonstrated. XRD analysis shows that the product has diffraction peaks at 15.7 °, 19.2 °, 20.6 °, 28.3 °, 29.5 °, 31.6 ° and 40.4 ° and the like, the peak shape is sharp and narrow, and the integral diffraction peak is not obvious; the diffraction peak pattern was not changed as a whole and the fine peak pattern was changed as compared with the original xylan, indicating that the crystallinity of the modified xylan derivative was changed. BySEM analysis shows that after esterification grafting modification, the product has irregular appearance, large surface roughness, more pores and complex internal structure, and the appearance of xylan is greatly changed through multi-step modification. TG-DTG analysis shows that the loss amount of the sample is 5% in the temperature range of 0-100 ℃, and the mass reduction of the sample can be caused by evaporation of partial residual water in the sample; the mass loss of the sample is about 10% in the temperature range of 100-200 ℃, probably due to the loss of crystal water in the sample; the mass loss of the sample is about 45% in the temperature range of 200-350 ℃, and the mass loss of the whole sample is the most at the stage, mainly caused by the breakage of sugar molecular chains in xylan and momordica grosvenori polysaccharide and unreacted residues; about 20% of the mass of the sample is lost in the range of 350-550 ℃, which is probably caused by branched chains introduced by grafting esterification modification and the breakage of ester bonds; the mass of the sample at 550-800 ℃ is reduced by 10%. Compared with TG and DTG graphs of BX, the heat stability of BX/SGPS nitro-p-methyl benzoate-g-AM/MA product modified by grafting and esterification is improved to a greater extent.
Claims (1)
1. A preparation method of BX/SGPS nitro-p-methyl benzoate-g-AM/MA is characterized by comprising the following specific steps:
(1) uniformly mixing bagasse xylan and momordica grosvenori polysaccharide in a mass ratio of 1:1, and drying 8-10 g of the mixture in a vacuum constant-temperature drying oven at 50-60 ℃ for 24 hours to constant weight to obtain a dry-based bagasse xylan/momordica grosvenori polysaccharide compound; (ii) a
(2) Sequentially weighing 0.60-0.80 g of ammonium persulfate and 0.30-0.40 g of sodium bisulfite in a 50mL beaker, adding 20-30 mL of distilled water, uniformly stirring to obtain an initiator solution, and pouring the initiator solution into a 100mL constant-pressure dropping funnel for later use;
(3) adding 1.0-3.0 g of acrylamide, 1.0-2.5 mL of analytically pure methyl acrylate and 10-25 mL of distilled water into a 50mL beaker, stirring and dissolving to obtain a monomer mixed solution, and pouring the monomer mixed solution into another 100mL constant-pressure dropping funnel for later use;
(4) taking 6.0-8.0 g of the dry bagasse xylan/momordica grosvenori polysaccharide complex obtained in the step (1) into a 250mL four-neck flask, adding 50-80 mL of distilled water, heating to 50-60 ℃, and stirring and activating for 20-30 minutes;
(5) firstly, adding one fourth of the mixed initiator solution obtained in the step (2) to the bagasse xylan/momordica grosvenori polysaccharide activation solution obtained in the step (4), stirring for 20-30 minutes, then synchronously dropwise adding the monomer mixed solution obtained in the step (3) and the rest initiator solution obtained in the three fourth of the step (2), controlling the system temperature at 50-70 ℃, dropwise adding time at 2-3 hours, and continuing to react for 2-5 hours after dropwise adding is finished; after the monomer mixed solution and the initiator solution are dripped, 0.10-0.20 g of cross-linking agent is added into the systemN, NContinuing to react for 3-5 hours by using methylene bisacrylamide; after the reaction is finished, cooling the obtained material to room temperature;
(6) adding 40-60 mL of analytically pure acetone into the material obtained in the step (5), precipitating for 20-30 minutes, and after suction filtration, washing and suction filtering the precipitate for 2-3 times by using 20-30 mL of analytically pure absolute ethanol and 20-30 mL of analytically pure acetone in sequence; 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/MA crude product;
(7) placing the bagasse xylan-g-AM/MA crude product obtained in the step (6) into a Soxhlet extractor, adding 150-200 mL of analytically pure acetone to extract the crude product for 24 hours, placing the material into a watch glass, and drying in a vacuum constant-temperature drying oven at 60 ℃ for 24 hours to constant weight to obtain a pure bagasse xylan/momordica grosvenori polysaccharide-g-AM/MA graft copolymer;
(8) weighing 2.0-5.0 g of 3-nitro-p-methylbenzoic acid in a 250mL four-neck flask, adding 5-8 mL of analytically pure thionyl chloride and 0.05-0.1 g of analytically pure dimethylformamide, heating the system to 60-70 ℃, and reacting for 2-3 hours under stirring to obtain a 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;
(9) weighing 2.0-4.0 g of pure bagasse xylan/momordica grosvenori polysaccharide-g-AM/MA obtained in the step (7), placing the pure bagasse xylan/momordica grosvenori polysaccharide-g-AM/MA into a 250mL four-neck flask, adding 60-90 mL of analytically pure toluene solvent, then adding 0.10-0.40 g of tetrabutyl titanate and 2.0-4.0 mL of analytically pure pyridine catalyst and acid binding agent, slowly adding the 3-nitro-p-methylbenzoyl chloride obtained in the step (8) under stirring, heating to 60-70 ℃, 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 washing and filtering the precipitate for 2-3 times by using 40-50 mL of analytically pure acetone respectively after suction filtration; and (3) drying the filter cake in a constant-temperature drying oven at 50-60 ℃ for 18-24 hours to constant weight to obtain a target product BX/SGPS nitro-p-methyl benzoate-g-AM/MA.
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