CN112175142A - Synthesis method of bagasse xylan bromopyruvate-g-AM/MA - Google Patents
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Abstract
The invention discloses a method for synthesizing active bagasse xylan bromopyruvate-g-AM/MA. Bagasse xylan is used as a main raw material, ammonium persulfate/sodium bisulfite is used as an initiator of a redox system, acrylamide and methyl acrylate are used as grafting monomers, and a bagasse xylan ternary graft copolymer, namely bagasse xylan-g-AM/MA, is synthesized in a water solvent through a free radical reaction; further taking 3-bromopyruvic acid as an esterifying agent and trifluoromethanesulfonic acid as a catalyst, and synthesizing the product bagasse xylan bromopyruvate-g-AM/MA through catalytic esterification. Compared with the original bagasse xylan, the water solubility of the target product obtained by the invention is improved to a certain extent, the activity of the product is 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 biomass materials, in particular to a method for synthesizing bagasse xylan bromopyruvate-g-AM/MA with bioactivity.
Background
Cancer is always one of major diseases endangering human health and life on the global scale, and the research and development of high-efficiency and low-toxicity anticancer drugs is a long-standing pursuit of many scholars. Xylan is a plant polysaccharide, has certain biological activities such as anticancer and the like, but has the defects of complex molecular chain structure, poor water solubility, low reaction activity and the like, so that the further application of xylan is limited. Related active groups are introduced by a chemical modification method, so that the activity of xylan is enhanced, and the application of xylan in related fields such as medicines, foods and materials can be expanded.
Esterification and graft modification are common means for chemically modifying xylan, and the selection of an esterifying agent and a grafting monomer is an important factor influencing the modification result. Because the reaction activity of xylan in aqueous solution is reduced due to the action of network hydrogen bonds in the molecule, monomers such as Acrylamide (AM) and Methyl Acrylate (MA) are grafted on xylan chains to improve the dissolution and activity performance of xylan. 3-bromopyruvate is a glycolytic inhibitor and a tumor energy blocker, and can reduce the generation of ATP by inhibiting the biological activity of glycolytic enzyme, thereby inhibiting the propagation and growth of tumor cells and achieving the purpose of killing the tumor cells. The xylan grafted product is esterified with 3-bromopyruvic acid, and the obtained final product has the capacity of reacting with some biological macromolecules due to the introduction of bromine-containing active groups. The 3-bromopyruvic acid is an alkylating agent with higher reaction activity and more active chemical property, so that the process is more green and environment-friendly. In addition, the water solubility of the final product was found to be improved to some extent at room temperature by measuring the water solubility of the final product.
The bagasse xylan is used as a main raw material, ammonium persulfate/sodium bisulfite is used as an oxidation-reduction system initiator, acrylamide and methyl acrylate are used as grafting monomers, and a bagasse xylan ternary graft copolymer, namely bagasse xylan-g-AM/MA, is synthesized in a water solvent through a free radical reaction; and further taking the intermediate product as an initial raw material, 3-bromopyruvic acid as an esterifying agent and trifluoromethanesulfonic acid as a catalyst, and synthesizing a final product of bagasse xylan bromopyruvate-g-AM/MA through catalytic esterification.
Disclosure of Invention
The invention aims to improve the bioactivity of bagasse xylan and expand the application range by grafting and esterifying the xylan, and provides a preparation method of bagasse xylan bromopyruvate-g-AM/MA.
The method comprises the following specific steps:
(1) firstly, 10.0-12.0 g of bagasse xylan is placed in a vacuum constant-temperature drying oven at 50-60 ℃ to be dried for 24 hours until the weight is constant, and the dry-based bagasse xylan is obtained.
(2) Weighing 0.40-1.0 g of ammonium persulfate and 0.20-0.50 g of sodium bisulfite in a 50mL beaker, adding 20-30 mL of distilled water, stirring uniformly to obtain an initiator solution, and pouring into a 100mL constant-pressure dropping funnel for later use.
(3) Adding 1.0-3.0 g of acrylamide, 1.0-2.0 mL of analytically pure methyl acrylate and 10-20 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) Weighing 6.0-8.0 g of the dry bagasse xylan obtained in the step (1), adding the dry bagasse xylan 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 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 three fourths of the initiator solution obtained in the step (2), controlling the system temperature at 50-70 ℃ and the dropwise adding time at 2-3 hours, continuing to react for 3-5 hours after the dropwise adding is finished, and cooling the obtained materials 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 filtration the precipitate with 20-30 mL of analytically pure acetone and 20-30 mL of analytically pure absolute ethyl alcohol for 2-3 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-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 on 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-g-AM/MA graft copolymer.
(8) Weighing 2.0-4.0 g of the intermediate product bagasse xylan-g-AM/MA obtained in the step (7) into another 250mL four-neck flask, respectively adding 0.8-2.0 g of esterifying agent 3-bromopyruvic acid, 0.10-0.24 g of catalyst trifluoromethanesulfonic acid and 40-60 mL of analytically pure dichloroethane, heating to 50-60 ℃ under stirring, continuing stirring for reaction for 5-8 hours, and cooling to room temperature.
(9) And (3) precipitating and filtering the material obtained in the step (8) by using 40-60 mL of analytically pure acetone, and then sequentially washing and filtering the material for 2-3 times by using 40-50 mL of analytically pure absolute ethyl alcohol and 40-50 mL of analytically pure acetone. 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 bagasse xylan bromopyruvate-g-AM/MA.
(10) And (3) measuring the esterification substitution degree of the bagasse xylan bromopyruvate-g-AM/MA product obtained in the step (9) by using an acid-base titration method, which comprises the following specific steps: accurately weighing about 0.5g of product sample into a 50mL conical flask, adding 20mL of distilled 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 conditions, a blank titration was carried out with the pure bagasse xylan graft product, and the volume V of the hydrochloric acid-depleted standard solution was recorded0. Mass fraction (w) of carboxylic acid acyl groups in the target productc) Bagasse xylan bromopyruvate-g-AM/MA Degree of Substitution (DS)C) The calculation formula of (a) 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 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 substitution by esterification of bagasse xylan bromopyruvate-g-AM/MA;
m and 132-acyl group of Carboxylic acid esterifying agent and relative molecular mass of the bagasse xylan anhydroxylose unit.
(11) And (3) determining the solubility of the dry-base bagasse xylan obtained in the step (1) and the bagasse xylan bromopyruvate-g-AM/MA product obtained in the step (9). The procedure for determining the solubility of the product obtained is as follows: placing a round-bottom flask in an electromagnetic constant-temperature stirring water bath at room temperature, adding 10g of distilled water into the flask, adding the product obtained in the step (9) in batches with the bagasse xylan bromopyruvate-g-AM/MA, recording the mass of each addition, sampling uninterruptedly and observing the crystal shape and the dissolution degree under a polarizing microscope until the crystal is not dissolved any more,the stirring was stopped. Separating the undissolved product by centrifuge according to the mass (m) of added bagasse xylan bromopyruvate-g-AM/MA1) And mass (m) of distilled water0) The solubility (S) of bagasse xylan bromopyruvate-g-AM/MA in water at room temperature was calculated. The calculation formula is as follows:
in the formula:
m1-mass of bagasse xylan bromopyruvate-g-AM/MA in g;
m0-mass of distilled water in g;
s-solubility of bagasse xylan bromopyruvate-g-AM/MA in water.
The method is characterized in that esterification reaction is carried out on the basis of xylan grafting reaction to synthesize the final product bagasse xylan bromopyruvate-g-AM/MA. The water solubility of the obtained target product is improved to a certain extent compared with the original bagasse xylan, the activity of the product is improved, and the 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 raw bagasse xylan.
FIG. 2 is an SEM photograph of bagasse xylan bromopyruvate-g-AM/MA prepared by an example of the present invention.
FIG. 3 is an IR chart of raw bagasse xylan (a) and an IR chart of bagasse xylan bromopyruvate-g-AM/MA prepared by the example of the present invention (b).
Figure 4 is an XRD pattern of raw bagasse xylan.
FIG. 5 is an XRD pattern of bagasse xylan bromopyruvate-g-AM/MA 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 bagasse xylan bromopyruvate-g-AM/MA prepared in accordance with an embodiment of the present invention.
Detailed Description
Example (b):
(1) firstly, 10.0g of bagasse xylan is placed in a vacuum constant-temperature drying oven at 50-60 ℃ to be dried for 24 hours to reach constant weight, and the dry-based bagasse xylan is obtained.
(2) 0.70g of ammonium persulfate and 0.20g of sodium bisulfite are weighed into a 50mL beaker, then 30mL of distilled water is added, and the mixture is stirred uniformly 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) Weighing 6.0g of the dry bagasse xylan obtained in the step (1), adding the dry bagasse xylan into a 250mL four-neck flask, adding 60mL of distilled water, heating to 50-60 ℃, and stirring and activating for 25 minutes.
(5) And (3) firstly adding about one fourth of the mixed initiator solution obtained in the step (2) to the bagasse xylan 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 about three fourths of the initiator solution obtained in the step (2), controlling the system temperature at 60 ℃ and the dropwise adding time at 3 hours, continuing to react for 4 hours after the dropwise adding is finished, and cooling the obtained material 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 acetone and 30mL of analytically pure absolute ethyl alcohol 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-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 180mL of analytically pure acetone to extract the crude product for 24 hours, placing the material on a watch glass, and drying the material in a vacuum constant-temperature drying oven at 60 ℃ for 24 hours until the weight is constant, so as to obtain the pure bagasse xylan-g-AM/MA graft copolymer.
(8) Weighing 2.0g of the intermediate product bagasse xylan-g-AM/MA obtained in the step (7) into another 250mL four-neck flask, respectively adding 1.0g of esterifying agent 3-bromopyruvic acid, 0.20g of catalyst trifluoromethanesulfonic acid and 50mL of analytically pure dichloroethane, heating to 60 ℃ while stirring, continuing to stir for reaction for 8 hours, and then cooling to room temperature.
(9) And (3) precipitating and filtering the material obtained in the step (8) by using 40mL of analytically pure acetone, and then washing and filtering the material for 3 times by using 50mL of analytically pure absolute ethyl alcohol and 50mL 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 the product bagasse xylan bromopyruvate-g-AM/MA.
(10) Measuring the product bagasse xylan bromopyruvate-g-AM/MA substitution degree DS by an acid-base titration methodcIs 0.38.
(11) And (3) measuring the solubility of the dry bagasse xylan obtained in the step (1) and the bagasse xylan bromopyruvate-g-AM/MA product obtained in the step (9), wherein the measured solubility S is respectively 0.3% and 28.6%. After the bagasse xylan is subjected to esterification grafting, the solubility of the product is greatly improved.
The product was IR analyzed to obtain a spectrum of 1728.99cm-1The peak is the coincidence peak of the stretching vibration absorption peak of the carbonyl in the ester group and the 3-bromopyruvic acid and is coincided with the carbonyl stretching vibration peak of the MA; 655.10cm-1The position is a carbon bromine bond stretching vibration absorption peak in the 3-bromopyruvic acid, thereby indicating that the esterification grafting reaction occurs. SEM analysis shows that the xylan derivative after esterification grafting modification has irregular particle shapes, is mutually crosslinked, has a complex internal structure and has larger change of the appearance than that before modification. According to an XRD diagram, the bagasse xylan bromopyruvate-g-AM/MA has obvious diffraction peaks at 11.3 degrees, 12.7 degrees, 19.5 degrees, 22.7 degrees, 25.7 degrees, 31.8 degrees and 33.4 degrees, and compared with the original xylan, the modified xylan derivative has small change of the diffraction peaks within an angle of 10-30 degrees; after 30 degrees, a new obvious diffraction peak appears, and after 31.8 degrees and 33.4 degrees, a plurality of fine diffraction peaks appear, which indicates that the modified xylan forms a new crystallization area and the crystallinity is increased. Through TG-DTG analysis, the sample loss is about 6% in the temperature range of 0-150 ℃, the mass loss of the product is small, the stability of the product is high, and the mass of the product in the temperature range of 800 ℃ is basically unchanged; under the low temperature state, the mass loss of the bagasse xylan bromopyruvate-g-AM/MA is slow, and the thermal stability of the product is improved.
Claims (1)
1. A method for synthesizing activated bagasse xylan bromopyruvate-g-AM/MA is characterized by comprising the following specific steps:
(1) firstly, 10.0-12.0 g of bagasse xylan is placed in a vacuum constant-temperature drying oven at 50-60 ℃ to be dried for 24 hours until the weight is constant, so that dry-based bagasse xylan is obtained;
(2) weighing 0.40-1.0 g of ammonium persulfate and 0.20-0.50 g of sodium bisulfite in a 50mL beaker, then adding 20-30 mL of distilled water, stirring uniformly 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, 1.0-2.0 mL of analytically pure methyl acrylate and 10-20 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) weighing 6.0-8.0 g of the dry bagasse xylan obtained in the step (1), adding the dry bagasse xylan into a 250mL four-neck flask, adding 50-80 mL of distilled water, heating to 50-60 ℃, 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 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 three fourths of the initiator solution obtained in the step (2), controlling the system temperature at 50-70 ℃, dropwise adding time at 2-3 hours, continuing to react for 3-5 hours after dropwise adding is finished, and 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 filtration for 2-3 times by using 20-30 mL of analytically pure acetone and 20-30 mL of analytically pure absolute ethyl alcohol in sequence; the filter cake is placed in a constant-temperature drying oven at 60 ℃ and dried for 24 hours to constant weight, and a bagasse xylan-g-AM/MA crude product is obtained;
(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 on 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-g-AM/MA graft copolymer;
(8) weighing 2.0-4.0 g of bagasse xylan-g-AM/MA obtained in the step (7) into another 250mL four-neck flask, respectively adding 0.8-2.0 g of esterifying agent 3-bromopyruvic acid, 0.10-0.24 g of catalyst trifluoromethanesulfonic acid and 40-60 mL of analytically pure dichloroethane, heating to 50-60 ℃ while stirring, continuing to stir for reaction for 5-8 hours, and cooling to room temperature;
(9) precipitating and filtering the material obtained in the step (8) by using 40-60 mL of analytically pure acetone, and then sequentially washing and filtering the material for 2-3 times by using 40-50 mL of analytically pure absolute ethyl alcohol and 40-50 mL of analytically pure acetone; 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 bagasse xylan bromopyruvate-g-AM/MA.
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| 李和平等: "木聚糖的化学修饰及其衍生物的应用研究进展", 《化工进展》 * |
| 李和平等: "蔗渣木聚糖-丙烯酰胺/丙烯酸丁酯三元接枝共聚物的合成与表征", 《化工新型材料》 * |
| 钱敬侠等: "蔗渣木聚糖没食子酸酯-g-MAA/BA 的合成及抗癌活性", 《精细化工》 * |
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