CN110128593A - The method of bagasse xylan vanilla acid esters-g-HEMA/MAA is synthesized in ionic liquid - Google Patents
The method of bagasse xylan vanilla acid esters-g-HEMA/MAA is synthesized in ionic liquid Download PDFInfo
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- CN110128593A CN110128593A CN201910448760.1A CN201910448760A CN110128593A CN 110128593 A CN110128593 A CN 110128593A CN 201910448760 A CN201910448760 A CN 201910448760A CN 110128593 A CN110128593 A CN 110128593A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0057—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Xylans, i.e. xylosaccharide, e.g. arabinoxylan, arabinofuronan, pentosans; (beta-1,3)(beta-1,4)-D-Xylans, e.g. rhodymenans; Hemicellulose; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F251/00—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
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Abstract
The invention discloses a kind of methods that bagasse xylan vanilla acid esters-g-HEMA/MAA is synthesized in ionic liquid.Using bagasse tapioca as raw material, vanillic acid is esterifying agent, and p-methyl benzenesulfonic acid and 4-dimethylaminopyridine are composite catalyst, catalyzes and synthesizes bagasse xylan vanilla acid esters in ionic liquid 1-butyl-3-methyl imidazolium salt ([Bmim] Cl)；Using ammonium persulfate as initiator, hydroxyethyl methacrylate (HEMA) and methacrylic acid (MAA) are that mixed grafting monomer synthesizes target product bagasse xylan vanilla acid esters-g-HEMA/MAA.Product of the present invention is on the basis of xylan is with having the pharmacological actions vanillic acids such as anti-oxidant, antibacterial, anti-inflammatory, platelet aggregation-against to carry out esterification, and further progress is grafted HEMA and MAA and obtains.The bioactivity such as antitumor that can further improve bagasse xylan have certain application value in fields such as medicine, food, fine chemistry industries.
Description
Technical field
The present invention relates to technical field of polymer materials, bagasse xylan vanillic acid is synthesized in especially a kind of ionic liquid
The method of ester-g-HEMA/MAA.
Background technique
In recent years, xylan is gradually understood and is recognized by people, drug, functional material, in terms of grind
Study carefully, develop and utilize the research of xylan and its derivative is made to have opened up new field.Wherein, the bagasse extracted from bagasse
Xylan has multiple biological activities.In order to further increase the anticancer activity of bagasse xylan, to bagasse xylan
Learning modification is a kind of important approach.
Vanillic acid and its esterification derivative have the effects that stronger anti-oxidant, antibacterial, anti-inflammatory, and some researches show that activity
The occurrence and development of oxygen radical and tumour have close ties, and the damage aoxidized with free radical is considered as that cell DNA is caused to damage
Hurt and then cause one of important mechanisms of cell mutation.Therefore, it if vanillic acid and bagasse xylan are esterified, can combine
The advantages of the two, further increases the anti-tumor activity of bagasse xylan esterification derivative.At present both at home and abroad about polysaccharide
Esterification-Study on graft modification of object is closed mainly based on starch, cellulose, chitosan, esterification-Study on graft modification of xylan
And its exploitation of function product is still in its infancy, in order to improve the water solubility of bagasse xylan derivative, bioactivity with
Compatibility considers to introduce hydroxyethyl methacrylate (HEMA), metering system on the basis of bagasse xylan vanilla is Esterification
Sour (MAA) grafted monomers, further increase the bioactivity of bagasse xylan derivative.
For the present invention using bagasse xylan as primary raw material, vanillic acid is esterifying agent, first in ionic liquid 1- butyl -3- first
Bagasse xylan vanilla acid esters is catalyzed and synthesized in base imidazole salts ([Bmim] Cl)；Then using ammonium persulfate as initiator, HEMA with
MAA is mixed grafting monomer, and synthesis has the bagasse xylan vanilla acid esters-g-HEMA/MAA of anticancer activity in water phase.
Summary of the invention
The purpose of the invention is to improve the anti-tumor activity of xylan, synthesis bagasse wood in a kind of ionic liquid is provided
The method of glycan vanilla acid esters-g-HEMA/MAA.
Specific steps of the invention are as follows:
(1) it successively measures 8~10mL and analyzes pure N- methylimidazole and the pure chloro-normal butane of 12~15mL analysis in equipped with temperature
Degree is counted, in the four-hole boiling flask of reflux condensing tube, and 70~100 DEG C are warming up under stirring, is flowed back 48 hours under insulated and stirred, reaction knot
Lurid thick liquid is obtained after beam.
(2) step (1) resulting material is cooled to room temperature, is washed 2~3 times using 10~30mL analysis pure ethyl acetate,
It is placed at 80 DEG C evaporation in rotary evaporator and removes remaining ethyl acetate, obtaining color is lurid 1- butyl -3- methyl
Imidazole salts ([Bmim] Cl) ionic liquid, it is spare.
(3) 4~6g bagasse xylan is placed in in 60 DEG C of vacuum constant temperature baking oven dry 24 hours to constant weight, obtains butt sugarcane
Slag xylan.
(4) butt bagasse xylan obtained by 1~2g step (3) is weighed in equipped with blender, thermometer and reflux unit
In four-hole boiling flask, and 1.0~2.0g vanillic acid and 15~20mL step (1) resulting ionic liquid [Bmim] are added thereto
Cl stirs 20~30 minutes to being uniformly dissolved at 30~40 DEG C.
(5) 0.1~0.2g p-methyl benzenesulfonic acid, 0.05~0.1g 4- dimethylamino pyrrole are added into step (4) resulting material
Pyridine, temperature control are stirred to react 5~9 hours at 30~50 DEG C, are cooled to room temperature after reaction.
(6) step (5) resulting material is analyzed pure soaked in absolute ethyl alcohol 24 hours with 30~50mL, successively respectively with 20~
30mL analyzes pure dehydrated alcohol, 20~30mL distillation water washing, filters each 3 times.
(7) step (6) material is filtered, gained filter cake is put into surface plate, is placed in 60 DEG C of vacuum constant temperature baking oven and is done
To constant weight, bagasse xylan vanilla acid esters is obtained within dry 24 hours.
(8) bagasse xylan vanilla acid esters obtained by 1.0~2.0g step (7) is taken to be added equipped with blender, thermometer and return
In another four-hole boiling flask of flow condenser, and 15~25mL distilled water is added, 40~50 DEG C is warming up under stirring, stirring and dissolving 5
~10 minutes.
(9) 0.10~0.25g ammonium persulfate, 5~10mL distilled water is taken to be added in the small beaker of 100mL respectively, at room temperature
It is uniformly mixing to obtain initiator solution.
(10) 1.0~2.0mL is measured respectively analyzes pure hydroxyethyl methacrylate, the pure metering system of 1.0~2.0mL analysis
The distilled water of acid, 10~15mL, stirs evenly to obtain monomer mixed solution.
(11) 40~70 DEG C will be warming up under the stirring of step (8) resulting material, it is molten drops evenly initiator obtained by step (9)
Liquid, and synchronize and drop evenly monomer mixed solution obtained by step (10), control was added dropwise at 3~5 hours, continues after charging
Reaction 0.5~1.0 hour.
(12) 25~35mL is added to step (11) resulting material to analyze pure acetone precipitating 15~25 minutes, filters and each
Pure dehydrated alcohol is analyzed with 10~15mL and washs precipitating 3 times, filter cake is put into surface plate after suction filtration, and it is permanent to be placed in 60 DEG C of vacuum
24 hours are dried in warm baking oven to constant weight to get final product bagasse xylan vanilla acid esters-g-HEMA/MAA.
(13) grafting rate and grafting efficiency of xylan derivative are measured, the method is as follows: gather the bagasse wood of certain mass
Sugared vanilla acid esters-g-HEMA/MAA is put into Soxhlet extractor after filter paper wraps up, and 50~100mL acetone is added in flask and does
Extractant is placed it in 80~DEG C water bath with thermostatic control and is heated, and sample is in Soxhlet extractor after continuous extraction 24 hours, through mentioning
Sample taking-up after taking, which is put into 60 DEG C of drying boxes, to be dried to constant weight.The calculation formula of grafting rate and grafting efficiency is as follows:
In formula:
G-grafting rate, %；
GE-grafting efficiency, %；
W0- original bagasse xylan quality, unit g；
W1The quality of pure bagasse xylan vanilla acid esters-g-HEMA/MAA, unit g after-extraction；
W2The quality of-crude product bagasse xylan vanilla acid esters-g-HEMA/MAA, unit g.
Gained target product of the invention improves the biocompatibility of bagasse xylan, and the vanillic acid of introducing has antioxygen
The pharmacological actions such as change, antibacterial, anti-inflammatory, platelet aggregation-against have in fields such as medicine, food, fine chemistry industries and centainly apply valence
Value.
Detailed description of the invention
Fig. 1 is the infrared spectrogram of former bagasse xylan.
Fig. 2 is the infrared spectrogram for the bagasse xylan vanilla acid esters-g-HEMA/MAA that the present invention synthesizes.
Fig. 3 is the SEM figure of former bagasse xylan.
The SEM figure that Fig. 4 is the bagasse xylan vanilla acid esters-g-HEMA/MAA that the present invention synthesizes.
Fig. 5 is TG the and DTG curve graph of former bagasse xylan.
Fig. 6 is TG the and DTG curve graph for the bagasse xylan vanilla acid esters-g-HEMA/MAA that the present invention synthesizes.
Specific embodiment:
Embodiment:
(1) successively measure 8.0mL analyze pure N- methylimidazole and 12.5mL analyze pure chloro-normal butane in equipped with thermometer,
In the four-hole boiling flask of reflux condensing tube, 75 DEG C are warming up under stirring, is flowed back 48 hours under insulated and stirred, after reaction it is pale yellow
The thick liquid of color.
(2) step (1) resulting material is cooled to room temperature, is washed 3 times using 30mL analysis pure ethyl acetate, is placed in 80 DEG C
Evaporation removes remaining ethyl acetate in lower rotary evaporator, and obtaining color is lurid 1- butyl -3- methylimidazole salt
([Bmim] Cl) ionic liquid, it is spare.
(3) 4~6g bagasse xylan is placed in in 60 DEG C of vacuum constant temperature baking oven dry 24 hours to constant weight, obtains butt sugarcane
Slag xylan.
(4) butt bagasse xylan obtained by 1.5g step (3) is weighed in four equipped with blender, thermometer and reflux unit
In mouth flask, and 1.5g vanillic acid and 20mL step (1) resulting ionic liquid [Bmim] Cl are added thereto, are stirred at 40 DEG C
30 minutes are mixed to being uniformly dissolved.
(5) 0.15g p-methyl benzenesulfonic acid, 0.08g 4-dimethylaminopyridine are added into step (4) resulting material, temperature control exists
It is stirred to react at 50 DEG C 8 hours, is cooled to room temperature after reaction.
(6) step (5) resulting material 40mL is analyzed pure soaked in absolute ethyl alcohol 24 hours, is successively analyzed respectively with 25mL
Pure dehydrated alcohol, filters each 3 times 25mL distillation water washing.
(7) step (6) material is filtered, gained filter cake is put into surface plate, is placed in 60 DEG C of vacuum constant temperature baking oven and is done
To constant weight, bagasse xylan vanilla acid esters is obtained within dry 24 hours.
(8) bagasse xylan vanilla acid esters obtained by 1.5g step (7) is taken to be added equipped with blender, thermometer and reflux condensation mode
In another four-hole boiling flask of device, and 20mL distilled water is added, 50 DEG C, stirring and dissolving 10 minutes are warming up under stirring.
(9) it takes 0.2g ammonium persulfate, 8.0mL distilled water to be added in the small beaker of 100mL respectively, stirs evenly at room temperature
To initiator solution.
(10) measure that 1.5mL analyzes pure hydroxyethyl methacrylate, 1.0mL analyzes pure methacrylic acid, 12mL respectively
Distilled water stirs evenly to obtain monomer mixed solution.
(11) 60 DEG C will be warming up under the stirring of step (8) resulting material, drop evenly initiator solution obtained by step (9),
And synchronize and drop evenly monomer mixed solution obtained by step (10), control was added dropwise at 4 hours, and the reaction was continued after charging
1.0 hour.
(12) 30mL is added into step (11) resulting material to analyze pure acetone precipitating 25 minutes, filters and uses 12mL every time
Pure dehydrated alcohol washing precipitating 3 times is analyzed, filter cake is put into surface plate after suction filtration, is placed in 60 DEG C of vacuum constant temperature baking oven and does
Dry 24 hours to constant weight to get final product bagasse xylan vanilla acid esters-g-HEMA/MAA.
(13) measuring products obtained therefrom esterification degree of substitution is 0.17, grafting rate 46.78%, grafting efficiency 24.15%.
Product is analyzed through IR, in 1733.31cm-1Place has increased the stretching vibration peak of an ester carbonyl group, the esterification of chain timbers glycan newly
The ester bond of the ester bond and hydroxyethyl methacrylate that are formed afterwards and the carboxyl peak of methacrylic acid coincide together；
1469.37cm-1Place is the skeletal vibration absorption peak of vanillic acid benzene ring structure；3400cm-1The peak of left and right broadens, and is vanillic acid phenol
The hydroxyl peak of hydroxyl and compound of polysaccharide coincides together.Sem analysis shows former bagasse xylan particle surface pattern for circle
Or it is approximate circle, particle is more complete, and surface is more smooth；There are a large amount of folds, gully on xylan derivative surface, in mutually winding
Network, and there are many cavernous structures.It is analyzed through TG-DTG, the thermal decomposition of product can be divided into 4 stages, and the first stage is 0
~200 DEG C, the mainly loss of moisture etc.；Second stage at 200~300 DEG C, for by after esterification or graft modification with
The fracture of the chemical bond of xylan backbone connection；Phase III is bagasse xylan vanilla acid esters-g- at 300~467 DEG C
The main chain break of HEMA/MAA；For fourth stage at 467~800 DEG C, mass loss is very fast；The mass loss in each stage 20%~
32%, the thermal stability of modified bagasse xylan derivative significantly improves.
Claims (1)
1. synthesizing the method for bagasse xylan vanilla acid esters-g-HEMA/MAA in a kind of ionic liquid, it is characterised in that specific step
Suddenly are as follows:
(1) it is pure successively to measure 8 ~ 10mL analysisNMethylimidazole and 12 ~ 15mL analyze pure chloro-normal butane in equipped with thermometer,
In the four-hole boiling flask of reflux condensing tube, it is warming up to 70 ~ 100 DEG C under stirring, flows back 48 hours under insulated and stirred, after reaction
Lurid thick liquid；
(2) step (1) resulting material is cooled to room temperature, is washed 2 ~ 3 times using 10 ~ 30mL analysis pure ethyl acetate, is placed in 80
Evaporation removes remaining ethyl acetate in rotary evaporator at DEG C, and obtaining color is lurid 1- butyl -3- methylimidazole salt
Ionic liquid, it is spare；
(3) 4 ~ 6g bagasse xylan is placed in in 60 DEG C of vacuum constant temperature baking oven dry 24 hours to constant weight, obtains butt bagasse wood
Glycan；
(4) butt bagasse xylan obtained by 1 ~ 2g step (3) is weighed in four mouthfuls of burnings equipped with blender, thermometer and reflux unit
In bottle, and 1.0 ~ 2.0g vanillic acid and 15 ~ 20mL step (1) resulting ionic liquid are added thereto, are stirred at 30 ~ 40 DEG C
20 ~ 30 minutes to being uniformly dissolved；
(5) 0.1 ~ 0.2g p-methyl benzenesulfonic acid, 0.05 ~ 0.1g 4-dimethylaminopyridine, control are added into step (4) resulting material
Temperature is stirred to react 5 ~ 9 hours at 30 ~ 50 DEG C, is cooled to room temperature after reaction；
(6) 30 ~ 50mL of step (5) resulting material is analyzed pure soaked in absolute ethyl alcohol 24 hours, successively respectively with 20 ~ 30mL points
It analyses pure dehydrated alcohol, 20 ~ 30mL distillation water washing, filter each 3 times；
(7) step (6) material is filtered, gained filter cake is put into surface plate, is placed in 60 DEG C of vacuum constant temperature baking oven dry 24
Hour to constant weight, obtains bagasse xylan vanilla acid esters；
(8) bagasse xylan vanilla acid esters obtained by 1.0 ~ 2.0g step (7) is taken to be added equipped with blender, thermometer and reflux condensation mode
In another four-hole boiling flask of device, and 15 ~ 25mL distilled water is added, 40 ~ 50 DEG C, stirring and dissolving 5 ~ 10 minutes are warming up under stirring；
(9) 0.10 ~ 0.25g ammonium persulfate, 5 ~ 10mL distilled water is taken to be added in the small beaker of 100mL respectively, stirring is equal at room temperature
It is even to obtain initiator solution；
(10) measure respectively 1.0 ~ 2.0mL analyzes pure hydroxyethyl methacrylate, 1.0 ~ 2.0mL analyzes pure methacrylic acid, 10 ~
The distilled water of 15mL stirs evenly to obtain monomer mixed solution；
(11) 40 ~ 70 DEG C will be warming up under the stirring of step (8) resulting material, drop evenly initiator solution obtained by step (9), and
It synchronizes and drops evenly monomer mixed solution obtained by step (10), control was added dropwise at 3 ~ 5 hours, and the reaction was continued after charging
0.5 ~ 1.0 hour；
(12) 25 ~ 35mL is added to step (11) resulting material to analyze pure acetone precipitating 15 ~ 25 minutes, filter and every time with 10 ~
15mL analyzes pure dehydrated alcohol washing precipitating 3 times, and filter cake is put into surface plate after suction filtration, is placed in 60 DEG C of vacuum constant temperature baking oven
Middle drying 24 hours to constant weight to get final product bagasse xylan vanilla acid esters-g-HEMA/MAA.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110724232A (en) * | 2019-10-22 | 2020-01-24 | 桂林理工大学 | Method for synthesizing active bagasse xylan citrate-g-GMA |
| CN111560097A (en) * | 2020-06-25 | 2020-08-21 | 桂林理工大学 | Synthesis method of active cross-linked bagasse xylan/camellia nitidissima shikimate-g-NVP |
| CN112094377A (en) * | 2020-09-06 | 2020-12-18 | 桂林理工大学 | Method for synthesizing bagasse xylan protocatechuate-g-HEMA in ionic liquid |
| CN112094376A (en) * | 2020-09-06 | 2020-12-18 | 桂林理工大学 | Method for synthesizing bagasse xylan protocatechuate-g-HEMA/MAA in ionic liquid |
| CN113842373A (en) * | 2021-08-28 | 2021-12-28 | 桂林理工大学 | Preparation method of curcumin-coated LTBX-g-EGDMA/HEMA/IMA nanoparticles |
| CN114152656A (en) * | 2020-09-08 | 2022-03-08 | 三诺生物传感股份有限公司 | Glucose biosensor |
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| CN109438622A (en) * | 2018-10-21 | 2019-03-08 | 桂林理工大学 | The method of anticancer activity phenylalanine esterification bagasse xylan-g-CHMA is synthesized in ionic liquid |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110724232A (en) * | 2019-10-22 | 2020-01-24 | 桂林理工大学 | Method for synthesizing active bagasse xylan citrate-g-GMA |
| CN111560097A (en) * | 2020-06-25 | 2020-08-21 | 桂林理工大学 | Synthesis method of active cross-linked bagasse xylan/camellia nitidissima shikimate-g-NVP |
| CN112094377A (en) * | 2020-09-06 | 2020-12-18 | 桂林理工大学 | Method for synthesizing bagasse xylan protocatechuate-g-HEMA in ionic liquid |
| CN112094376A (en) * | 2020-09-06 | 2020-12-18 | 桂林理工大学 | Method for synthesizing bagasse xylan protocatechuate-g-HEMA/MAA in ionic liquid |
| CN114152656A (en) * | 2020-09-08 | 2022-03-08 | 三诺生物传感股份有限公司 | Glucose biosensor |
| CN113842373A (en) * | 2021-08-28 | 2021-12-28 | 桂林理工大学 | Preparation method of curcumin-coated LTBX-g-EGDMA/HEMA/IMA nanoparticles |
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