CN112094377A - Method for synthesizing bagasse xylan protocatechuate-g-HEMA in ionic liquid - Google Patents
Method for synthesizing bagasse xylan protocatechuate-g-HEMA in ionic liquid Download PDFInfo
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Abstract
The invention discloses a method for synthesizing bagasse xylan protocatechuate-g-HEMA in ionic liquid. Synthesizing bagasse xylan protocatechuate through catalytic esterification reaction in ionic liquid chloridized-1-butyl-3-methylimidazole by taking bagasse xylan as a main raw material, protocatechuic acid as an esterifying agent and p-toluenesulfonic acid as a catalyst; and then the intermediate product is taken as a raw material, hydroxyethyl methacrylate is taken as a grafting monomer, ammonium persulfate is taken as an initiator, and the final product, namely the bagasse xylan protocatechuate-g-HEMA, is synthesized in an aqueous solution. Through the introduction of molecular active groups such as protocatechuic acid, hydroxyethyl methacrylate and the like, the product has certain prospect in the fields of porous transportation carriers, drug carriers, medicines, 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 protocatechuate-g-HEMA in ionic liquid.
Background
The natural polysaccharide has the characteristics of immunity regulation and low toxicity, can play a certain role in prevention and anti-tumor, and becomes a research hotspot at present. Bagasse xylan is known to be an important component of hemicellulose, widely exists in plant cell walls, is a natural polysaccharide high molecular material, is friendly to human bodies, and has high use value. The bagasse xylan has strong intramolecular hydrogen bonds, so that the application range of the bagasse xylan is greatly limited. By applying chemical modification methods such as esterification and grafting and introducing related active groups, the defects of biological activity and physicochemical properties of the original bagasse xylan can be overcome, and the application of the bagasse xylan in the fields of additives, medicaments, carriers and the like is widened.
Protocatechuic acid belongs to one of phenolic acids, is present in various edible plants, is mainly used for treating chronic tracheitis clinically, and has certain biological activity. Protocatechuic acid is introduced to a bagasse xylan unit ring through esterification, hydroxyethyl methacrylate (HEMA) is selected as a grafting monomer to be esterified with bagasse xylan for graft copolymerization, and the synthesized product has a plurality of hydroxyl active sites, so that the biological activity is better than that of similar bagasse xylan derivatives, and the spatial structure of the derivatives is greatly changed compared with that of the original bagasse xylan. From the process, the ionic liquid chloro-1-butyl-3-methylimidazole is used as a reaction solvent, so that a high-efficiency and stable reaction system is provided for the modification process of xylan, and the reaction efficiency and the conversion rate are improved.
The method comprises the steps of taking bagasse xylan as a main raw material, protocatechuic acid as an esterifying agent, p-toluenesulfonic acid as a catalyst, and synthesizing bagasse xylan protocatechuate through catalytic esterification reaction in ionic liquid chloro-1-butyl-3-methylimidazole; and then the intermediate product is taken as a raw material, hydroxyethyl methacrylate is taken as a grafting monomer, ammonium persulfate is taken as an initiator, and the final product, namely the bagasse xylan protocatechuate-g-HEMA, is synthesized in an aqueous solution.
Disclosure of Invention
The invention aims to improve the bioactivity of xylan and provides a method for synthesizing bagasse xylan protocatechuate-g-HEMA in ionic liquid.
The method comprises the following specific steps:
(1) sequentially weighing 30-40 mL of analytically pure N-methylimidazole and 40-50 mL of analytically pure N-butyl chloride into a 250mL four-neck flask provided with a thermometer and a reflux condenser, magnetically stirring at 70-100 ℃, and keeping refluxing for 40-50 hours to obtain light yellow viscous liquid.
(2) And (2) cooling the material obtained in the step (1) to room temperature, firstly washing with 40-80 mL of analytically pure ethyl acetate for 2-3 times, and then putting the washed material in a rotary evaporator at 70-80 ℃ to evaporate and remove residual ethyl acetate to obtain light yellow chlorinated-1-butyl-3-methylimidazole ionic liquid for later use.
(3) Weighing 7-9 g of bagasse xylan, putting into a glass dish, and placing in a vacuum constant-temperature drying oven at 50-60 ℃ for drying for 24 hours to constant weight to obtain dry-based bagasse xylan.
(4) Weighing 6.0-8.0 g of the dry bagasse xylan obtained in the step (3), adding the dry bagasse xylan into a 250mL four-neck flask provided with a stirrer, a thermometer and a reflux device, adding 3.0-4.0 g of protocatechuic acid and 60-70 mL of the ionic liquid chloro-1-butyl-3-methylimidazole obtained in the step (2), and stirring at the temperature of 30-40 ℃ for 30-40 minutes until the system is uniformly dissolved.
(5) And (3) adding 0.90-1.20 g of catalyst p-toluenesulfonic acid into the material obtained in the step (4), stirring and reacting at the temperature of 30-60 ℃ for 5-9 hours, and cooling to room temperature.
(6) And (3) adding 60-100 mL of analytically pure absolute ethyl alcohol into the material system obtained in the step (5), uniformly stirring, soaking for 20-24 hours, washing with 40-60 mL of analytically pure absolute ethyl alcohol and 40-60 mL of distilled water, and performing suction filtration for 2-3 times.
(7) And (4) putting the filter cake obtained in the step (6) into a watch glass, and then putting the watch glass into a vacuum constant-temperature drying oven at 50-60 ℃ for drying for 24 hours to constant weight to obtain the bagasse xylan protocatechuate.
(8) And sequentially adding 0.60-0.80 g of ammonium persulfate and 20-40 mL of distilled water into a 50mL small beaker, uniformly stirring at room temperature to obtain an initiator solution, and pouring the initiator solution into a 100mL constant-pressure dropping funnel for later use.
(9) 3.0-4.0 g of analytically pure hydroxyethyl methacrylate, 10-15 mL of analytically pure acetone and 20-25 mL of distilled water are respectively added into another 50mL of small beaker, and are uniformly stirred to obtain a monomer mixed solution, and the monomer mixed solution is poured into another 100mL of constant-pressure dropping funnel for later use.
(10) Weighing 6.0-8.0 g of the bagasse xylan protocatechuate obtained in the step (7), adding the bagasse xylan protocatechuate into another 250mL four-neck flask, adding 60-70 mL of distilled water while stirring, heating the system to 50-70 ℃, and stirring for 10-20 minutes.
(11) Firstly, adding about one third of the initiator solution obtained in the step (8) to the material obtained in the step (10), stirring for 20-30 minutes, controlling the temperature at 50-70 ℃, starting to synchronously dropwise add the monomer mixed solution obtained in the step (9) and the rest about two thirds of the initiator solution obtained in the step (8), controlling the dropwise adding time at 3-5 hours, continuously reacting for 2-4 hours after dropwise adding is finished, and cooling the obtained material to room temperature.
(12) And (3) adding 50-70 mL of analytically pure acetone into the material obtained in the step (11) for precipitation for 10-20 minutes, and after suction filtration, washing the precipitate with 20-30 mL of analytically pure acetone and 20-30 mL of analytically pure absolute ethyl alcohol in sequence, and carrying out suction filtration 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 protocatechuate-g-HEMA crude product.
(13) Placing the bagasse xylan protocatechuate-g-HEMA crude product obtained in the step (12) into a Soxhlet extractor, and adding 100-150 mL of analytically pure acetone for extraction for 20-24 hours; and taking out the extract, putting the extract into a surface dish, and drying the extract in a vacuum constant-temperature drying oven at the temperature of 50-60 ℃ for 16-24 hours until the weight is constant, thus obtaining the final product, namely the bagasse xylan protocatechuate-g-HEMA.
(14) Method for determining ester of bagasse xylan protocatechuate-g-HEMA by acid-base titrationDegree of substitution: accurately weighing 0.50g of sample, placing the sample in a conical flask with the volume of 50mL, adding 10mL of distilled water into the conical flask, shaking up, adding 2-3 drops of phenolphthalein indicator with the mass fraction of 5%, and titrating the indicator to be light red by using a 0.1mol/L NaOH standard solution, wherein the color of the indicator does not fade within 30 seconds; 2.5mL of a 0.5mol/L NaOH standard solution was added to the flask, followed by saponification at room temperature for 4 hours with shaking, and further titration with a 0.5mol/L hydrochloric acid standard solution was continued until colorless. The volume of the hydrochloric acid standard solution used for titration was recorded as V1(ii) a Under the same conditions, a blank control was performed with the original bagasse xylan, and the volume V of HCl standard solution consumed was recorded0. Mass fraction (w) of protocatechuic acid acyl group in target productc) The calculation formula of the bagasse xylan protocatechuate-g-HEMA substitution Degree (DS) is as follows:
in the formula:
wc-mass fraction of protocatechuic acid acyl groups in the target product,%;
V0titration of bagasse xylan uses HCI standard solution volume, in mL;
V1titration of the standard solution volume of HCl used for the target product, in mL;
CHCl-HCl standard solution concentration, unit mol/L;
m is the mass of a target product, namely bagasse xylan protocatechuate-g-HEMA sample, and the unit is g;
m-relative molecular mass of protocatechuic acid acyl groups;
132-relative molecular mass of bagasse xylan dewatering units;
DS-degree of substitution of bagasse xylan protocatechuate-g-HEMA.
The invention synthesizes the target product of bagasse xylan protocatechuate-g-HEMA through an esterification and grafting modification method, and introduces molecular active groups such as protocatechuic acid, hydroxyethyl methacrylate and the like, so that the product has certain prospect in the fields of porous transportation carriers, drug carriers, medicines, functional materials and the like.
Drawings
FIG. 1 is an SEM image of raw bagasse xylan.
FIG. 2 is an SEM image of bagasse xylan protocatechuate-g-HEMA prepared in an example of the present invention.
FIG. 3 is an infrared spectrum of the original bagasse xylan.
FIG. 4 is an infrared spectrum of bagasse xylan protocatechuate-g-HEMA prepared in accordance with an embodiment of the present invention.
Figure 5 is an XRD pattern of raw bagasse xylan.
FIG. 6 is an XRD pattern of bagasse xylan protocatechuate-g-HEMA prepared in accordance with an example of the present invention.
FIG. 7 is a graph showing TG and DTG profiles of raw bagasse xylan.
FIG. 8 is a graph showing TG and DTG profiles of bagasse xylan protocatechuate-g-HEMA prepared in accordance with an example of the present invention.
Detailed Description
Example (b):
(1) 32mL of analytically pure N-methylimidazole and 50mL of analytically pure N-butyl chloride were measured out in this order in a 250mL four-necked flask equipped with a thermometer and a reflux condenser, and magnetically stirred at 75 ℃ while maintaining reflux for 48 hours to give a pale yellow viscous liquid.
(2) And (2) cooling the material obtained in the step (1) to room temperature, washing the material for 3 times by adopting 60mL of analytically pure ethyl acetate, and then putting the material in a rotary evaporator at the temperature of 80 ℃ to evaporate and remove residual ethyl acetate to obtain light yellow chlorinated-1-butyl-3-methylimidazole ionic liquid for later use.
(3) Weighing 6.5g of bagasse xylan, putting into a glass dish, and placing in a vacuum constant-temperature drying oven at 60 ℃ for drying for 24 hours to constant weight to obtain dry-based bagasse xylan.
(4) Weighing 6.0g of the dry bagasse xylan obtained in the step (3) and adding the dry bagasse xylan into a 250mL four-neck flask equipped with a stirrer, a thermometer and a reflux device, adding 3.0g of protocatechuic acid and 60mL of the ionic liquid chloro-1-butyl-3-methylimidazole obtained in the step (2), and stirring at 30 ℃ for 40 minutes until the system is uniformly dissolved.
(5) And (4) adding 0.90g of catalyst p-toluenesulfonic acid into the material obtained in the step (4), stirring and reacting at the temperature of 30-60 ℃ for 9 hours, and cooling to room temperature.
(6) And (3) adding 80mL of analytically pure absolute ethyl alcohol into the material system obtained in the step (5), uniformly stirring, soaking for 24 hours, then washing with 50mL of analytically pure absolute ethyl alcohol and 50mL of distilled water, and carrying out suction filtration for 3 times.
(7) And (4) putting the filter cake obtained in the step (6) into a watch glass, and then putting the watch glass into a vacuum constant-temperature drying oven at 50 ℃ for drying for 24 hours to constant weight to obtain the bagasse xylan protocatechuate.
(8) 0.60g of ammonium persulfate and 40mL of distilled water are sequentially added into a 50mL small beaker, stirred uniformly at room temperature to obtain an initiator solution, and the initiator solution is poured into a 100mL constant-pressure dropping funnel for later use.
(9) 3.0g of analytically pure hydroxyethyl methacrylate, 10mL of analytically pure acetone and 20mL of distilled water are respectively added into another 50mL small beaker, and are uniformly stirred to obtain a monomer mixed solution, and the monomer mixed solution is poured into another 100mL constant-pressure dropping funnel for later use.
(10) Weighing 6.0g of the bagasse xylan protocatechuate obtained in the step (7) and adding the weighed bagasse xylan protocatechuate into another 250mL four-neck flask, adding 60mL of distilled water while stirring, raising the temperature of the system to 50 ℃, and stirring for 20 minutes.
(11) And (3) adding about one third of the initiator solution obtained in the step (8) to the material obtained in the step (10), stirring for 30 minutes, controlling the temperature at 60 ℃, starting to synchronously dropwise add the monomer mixed solution obtained in the step (9) and the rest about two thirds of the initiator solution obtained in the step (8), controlling the dropwise adding time at 4 hours, continuing to react for 4 hours after the dropwise adding is finished, and cooling the obtained material to room temperature.
(12) And (3) adding 50mL of analytically pure acetone into the material obtained in the step (11) for precipitation for 10 minutes, and after suction filtration, washing the precipitate with 30mL of analytically pure acetone and 30mL of analytically pure absolute ethyl alcohol in sequence, and carrying out suction filtration 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 protocatechuate-g-HEMA crude product.
(13) Placing the bagasse xylan protocatechuate-g-HEMA crude product obtained in the step (12) into a Soxhlet extractor, and adding 150mL of analytically pure acetone for extraction for 24 hours; taking out the extract, putting the extract into a surface dish, and placing the surface dish in a vacuum constant-temperature drying oven at 50 ℃ for drying for 24 hours until the weight is constant, thus obtaining the final product, namely the bagasse xylan protocatechuate-g-HEMA.
(14) The esterification degree of substitution DS of the obtained product bagasse xylan protocatechuate-g-HEMA is measured to be 0.18.
The product was IR analyzed and the spectrum was 1734.85cm-1A stretching vibration peak of ester carbonyl is added, and ester bonds formed after esterification of xylan are superposed with ester bonds of graft monomer hydroxyethyl methacrylate; 1464.86cm-1A skeleton vibration absorption peak of a protocatechuic acid benzene ring structure; 3220.13cm-1Peaks appeared in the range of association of protocatechuic phenolic hydroxyl groups with hydroxyl groups of polysaccharide compounds, the peaks being broader than the log glycan; from these characteristic peaks, it can be judged that characteristic groups of protocatechuic acid and hydroxyethyl methacrylate are introduced into the product. XRD analysis shows that compared with diffraction peaks of BX, the number of diffraction peaks of bagasse xylan protocatechuate-g-HEMA is reduced, and only a stronger diffraction peak is at a position of 20 degrees, which indicates that the crystallization degree of the product is reduced after modification. Performing TG-DTG analysis on the product, wherein the first stage is 0-100 ℃, the bagasse xylan reduces the mass of the whole sample by about 10%, and the mass loss of the part is mainly the loss of water; at the temperature rise stage of 100-200 ℃, the quality of bagasse xylan is hardly lost; the second stage is 200-310 ℃, the mass loss of the bagasse xylan is large and accounts for about 63% of the mass of the whole sample, and the mass loss of the bagasse xylan is probably caused by the breakage of hydroxyl bonds such as beta-1, 4 glycosidic bonds of a xylan main chain; the third stage is 310-800 ℃, the loss of the sample mass accounts for 20% -30%, the rate of mass loss is small compared with the second stage, the temperature range is long, and the mass loss at the stage is mainly concentrated on the breakage of residues, so the mass loss is relatively small. SEM analysis shows that the BX surface is relatively flatThe product is slow, smooth and mellow, and even holes are generated; the bagasse xylan protocatechuate-g-HEMA has a large number of folds and ravines on the surface and a plurality of porous structures. The structural representation shows that after esterification and graft copolymerization modification, a plurality of active groups are introduced on the surface of the bagasse xylan protocatechuate-g-HEMA molecule.
Claims (1)
1. A method for synthesizing bagasse xylan protocatechuate-g-HEMA in ionic liquid is characterized by comprising the following specific steps:
(1) sequentially weighing 30-40 mL of analytically pure N-methylimidazole and 40-50 mL of analytically pure N-butyl chloride into a 250mL four-neck flask provided with a thermometer and a reflux condenser, magnetically stirring at 70-100 ℃, and keeping refluxing for 40-50 hours to obtain light yellow viscous liquid;
(2) cooling the material obtained in the step (1) to room temperature, firstly washing with 40-80 mL of analytically pure ethyl acetate for 2-3 times, and then placing in a rotary evaporator at 70-80 ℃ to evaporate residual ethyl acetate to obtain light yellow chlorinated-1-butyl-3-methylimidazole ionic liquid for later use;
(3) weighing 7-9 g of bagasse xylan, putting into a glass dish, and drying in a vacuum constant-temperature drying oven at 50-60 ℃ for 24 hours to constant weight to obtain dry-based bagasse xylan;
(4) weighing 6.0-8.0 g of the dry bagasse xylan obtained in the step (3), adding the dry bagasse xylan into a 250mL four-neck flask provided with a stirrer, a thermometer and a reflux device, adding 3.0-4.0 g of protocatechuic acid and 60-70 mL of the ionic liquid chloro-1-butyl-3-methylimidazole obtained in the step (2), and stirring for 30-40 minutes at the temperature of 30-40 ℃ until the system is uniformly dissolved;
(5) adding 0.90-1.20 g of catalyst p-toluenesulfonic acid into the material obtained in the step (4), stirring and reacting at the temperature of 30-60 ℃ for 5-9 hours, and cooling to room temperature;
(6) adding 60-100 mL of analytically pure absolute ethyl alcohol into the material system obtained in the step (5), uniformly stirring, soaking for 20-24 hours, then washing with 40-60 mL of analytically pure absolute ethyl alcohol and 40-60 mL of distilled water, and carrying out suction filtration for 2-3 times;
(7) putting the filter cake obtained in the step (6) into a watch glass, and then putting the watch glass into a vacuum constant-temperature drying oven at 50-60 ℃ for drying for 24 hours to constant weight to obtain bagasse xylan protocatechuate;
(8) sequentially adding 0.60-0.80 g of ammonium persulfate and 20-40 mL of distilled water into a 50mL small beaker, uniformly stirring at room temperature to obtain an initiator solution, and pouring the initiator solution into a 100mL constant-pressure dropping funnel for later use;
(9) respectively adding 3.0-4.0 g of analytically pure hydroxyethyl methacrylate, 10-15 mL of analytically pure acetone and 20-25 mL of distilled water into another 50mL of small beaker, uniformly stirring to obtain a monomer mixed solution, and pouring the monomer mixed solution into another 100mL of constant-pressure dropping funnel for later use;
(10) weighing 6.0-8.0 g of the bagasse xylan protocatechuate obtained in the step (7), adding the bagasse xylan protocatechuate into another 250mL four-neck flask, adding 60-70 mL of distilled water while stirring, heating the system to 50-70 ℃, and stirring for 10-20 minutes;
(11) firstly, adding one third of the initiator solution obtained in the step (8) to the material obtained in the step (10), stirring for 20-30 minutes, controlling the temperature to be 50-70 ℃, starting to synchronously dropwise add the monomer mixed solution obtained in the step (9) and the rest two thirds of the initiator solution obtained in the step (8), controlling the dropwise adding time to be 3-5 hours, continuously reacting for 2-4 hours after dropwise adding is finished, and cooling the obtained material to room temperature;
(12) adding 50-70 mL of analytically pure acetone into the material obtained in the step (11), precipitating for 10-20 minutes, and after suction filtration, washing the precipitate with 20-30 mL of analytically pure acetone and 20-30 mL of analytically pure absolute ethyl alcohol in sequence, and carrying out suction filtration for 2-3 times; drying the filter cake in a constant-temperature drying oven at 60 ℃ for 24 hours to constant weight to obtain a bagasse xylan protocatechuate-g-HEMA crude product;
(13) placing the bagasse xylan protocatechuate-g-HEMA crude product obtained in the step (12) into a Soxhlet extractor, and adding 100-150 mL of analytically pure acetone for extraction for 20-24 hours; and taking out the extract, putting the extract into a surface dish, and drying the extract in a vacuum constant-temperature drying oven at the temperature of 50-60 ℃ for 16-24 hours until the weight is constant, thus obtaining the final product, namely the bagasse xylan protocatechuate-g-HEMA.
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| CN110128593A (en) * | 2019-05-28 | 2019-08-16 | 桂林理工大学 | The method of bagasse xylan vanilla acid esters-g-HEMA/MAA is synthesized in ionic liquid |
| CN110194817A (en) * | 2019-05-28 | 2019-09-03 | 桂林理工大学 | A kind of synthetic method of activity bagasse xylan vanilla acid esters-g-HEMA/MAA/EA |
| CN110591004A (en) * | 2019-09-12 | 2019-12-20 | 桂林理工大学 | Synthetic method of bioactive bagasse xylan oxalate-g-HEMA |
| CN110698594A (en) * | 2019-10-22 | 2020-01-17 | 桂林理工大学 | Synthesis method of bagasse xylan citrate-g-BMA with anticancer activity |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110128593A (en) * | 2019-05-28 | 2019-08-16 | 桂林理工大学 | The method of bagasse xylan vanilla acid esters-g-HEMA/MAA is synthesized in ionic liquid |
| CN110194817A (en) * | 2019-05-28 | 2019-09-03 | 桂林理工大学 | A kind of synthetic method of activity bagasse xylan vanilla acid esters-g-HEMA/MAA/EA |
| CN110591004A (en) * | 2019-09-12 | 2019-12-20 | 桂林理工大学 | Synthetic method of bioactive bagasse xylan oxalate-g-HEMA |
| CN110698594A (en) * | 2019-10-22 | 2020-01-17 | 桂林理工大学 | Synthesis method of bagasse xylan citrate-g-BMA with anticancer activity |
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Application publication date: 20201218 |