CN109400735A - A kind of double esterification bagasse xylan-trihydroxybenzoic acid/isophthalic acid ester synthetic method - Google Patents
A kind of double esterification bagasse xylan-trihydroxybenzoic acid/isophthalic acid ester synthetic method Download PDFInfo
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- CN109400735A CN109400735A CN201811225993.7A CN201811225993A CN109400735A CN 109400735 A CN109400735 A CN 109400735A CN 201811225993 A CN201811225993 A CN 201811225993A CN 109400735 A CN109400735 A CN 109400735A
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- 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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Abstract
The invention discloses a kind of double esterification bagasse xylan-trihydroxybenzoic acid/isophthalic acid ester synthetic methods.Using bagasse xylan as primary raw material, withN,NDimethylformamide is solvent,N,NDicyclohexylcarbodiimide is dehydrating agent, and ammonium persulfate is catalyst, and 3,4,5- triacetyl chlorobenzoyl chlorides carry out esterification, synthesize 3,4,5- triacetyl benzoxy bagasse xylan ester of intermediate product.Again using pyridine as catalyst, 3,4,5- triacetyl benzoxy bagasse xylan ester of intermediate product is reacted with M-phthalic acid sodium salt, synthesizes final product bagasse xylan-trihydroxybenzoic acid/isophthalic acid ester.The present invention further enhances bioactivity, thermal stability and the functional characteristic of bagasse xylan and its carboxylate, and product is in the medicine such as antiviral, AntiHIV1 RT activity, food and biological field potential using value with higher.
Description
Technical field
The present invention relates to technical field of fine, and in particular to and a kind of double esterification bagasse xylan-trihydroxybenzoic acid/
The synthetic method of isophthalic acid ester.
Background technique
Xylan is the main component of hemicellulose, has good biocompatibility, biodegradable, is led in medicine
Domain also has immunostimulation behavior, and esterification derivative plays the role of significantly inhibiting HIV, is a kind of novel natural bioactive
Substance.The active lateral group of xylan is modified using double esterification reaction, the structure of xylan can not only be modified, it can also
To introduce the HIV-resistant activity performance of other function active group enhancing xylan.
Studies have shown that bagasse xylan-trihydroxybenzoic acid ester is with anti-inflammatory, antiviral, anti-oxidant and immunoregulatory
Activity.Meanwhile bagasse xylan isophthalic acid ester has the characteristic for inhibiting HIV sick cell to shift in vivo, by 3,4,5-
After trihydroxybenzoic acid and M-phthalic acid and xylan carry out two step esterifications, larger change has occurred in structure, it is living
Property much than mono-esterification modification xylan derivative bioactivity it is good.The space of xylan can also be improved by esterification
Structure and physical and chemical performance expand the application field of xylan.
The present invention is using bagasse xylan as primary raw material, with n,N-Dimethylformamide (DMF) for solvent, bis- hexamethylene of N, N-
Base carbodiimide is dehydrating agent, and ammonium persulfate is catalyst, and 3,4,5- triacetyl chlorobenzoyl chlorides carry out esterification, synthesis
Intermediate product 3,4,5- triacetyl benzoxy bagasse xylan ester.Again using pyridine as catalyst, by intermediate product 3,4,5- tri-
Acetamido benzoate base bagasse xylan ester is reacted with M-phthalic acid sodium salt, synthesizes final product bagasse xylan-trihydroxy benzene
Formic acid/isophthalic acid ester.Bagasse xylan-trihydroxybenzoic acid/isophthalic acid ester double esterification functional derivatives are into one
Step enhances the thermal stability and functional characteristic of bagasse xylan and its carboxylate, expands it in medicine, food and biological field
Application range.
Summary of the invention
The purpose of the present invention is enhancing the HIV-resistant activity of bagasse xylan, a kind of bagasse xylan-trihydroxy benzene first is provided
Acid/isophthalic acid ester synthetic method.
Specific steps of the invention are as follows:
(1) 5~7g bagasse xylan is 24 hours dry in 50 DEG C of vacuum drying ovens, it is poly- to obtain butt bagasse wood
Sugar.
(2) butt bagasse xylan obtained by 2~5g step (1) is weighed to be added in 250mL four-hole boiling flask, sequentially add 10~
20mL analyzes pure n,N-Dimethylformamide, 1~4.5g N, N- dicyclohexylcarbodiimide and 0.2~0.6g ammonium persulfate, control
System temperature processed is 20~25 DEG C, stirs 25 minutes, obtains bagasse xylan activating solution.
(3) it weighs 4~8g, 3,4,5- triacetyl chlorobenzoyl chloride to be placed in 50mL beaker, 20~35mL is added and analyzes pure N,
Dinethylformamide pours into constant pressure funnel after dissolution is mixed.By bagasse xylan activating solution liter obtained by step (2)
Temperature to 60~65 DEG C starts that mixed liquor is added dropwise, and control time for adding is 1~2 hour, after being added dropwise by reaction system in 60~
65 DEG C continuation back flow reaction 4 hours.
(4) after reaction, reaction solution obtained by step (3) is filtered, filter cake is placed in 100mL beaker, with 5~10mL's
Analysis pure acetone, 5~15mL dehydrated alcohol are washed and are filtered, after being repeated 3 times.Gained filter cake is placed in 50 DEG C of constant-temperature vacuums
It is 12 hours dry in drying box, obtain bagasse xylan-triacetyl benzoic ether.
(5) the dehydrated alcohol saturated solution of 30~50mL sodium bicarbonate is placed in 100mL beaker, weighs 3~8g step
(4) gained bagasse xylan-triacetyl benzoic ether is added in beaker, is stirred 10~30 minutes at room temperature, until solution
PH is 8.
(6) reaction solution obtained by step (5) is filtered, filter cake is placed in 100mL beaker, is washed with 10~15mL deionized water
It precipitates and filters, be repeated 3 times, filter cake is placed in 50 DEG C of vacuum drying ovens dry 12 hours to get bagasse xylan 3,
4,5- trihydroxybenzoic acid ester.
(7) 4~8g M-phthalic acid, the sodium hydroxide solution that 20~40mL mass fraction is 3%~5% are sequentially added
Into 250mL four-hole boiling flask, it is stirred to react at room temperature 0.5~1 hour, obtains M-phthalic acid sodium salt solution.
(8) it weighs bagasse xylan-trihydroxybenzoic acid ester obtained by 1~5g step (6) and is added to isophthalic obtained by step (7)
In sodium diformate salting liquid, stir 2~4 hours at room temperature.The hydrochloric acid that 10~15mL mass fraction is 1%~5% is added to adjust
Reaction solution pH to 6~7 adds 1~3mL analysis pure pyridine, is warming up to 30~45 DEG C, stirs lower reaction 3~7 hours.Reaction
After with the hydrochloric acid solution that 20~35mL mass fraction is 5% system pH is adjusted to 4~5, be cooled to 20~30 DEG C, continue anti-
It answers 1 hour.
(9) reaction solution obtained by step (8) is poured into 100mL beaker, 20~30mL dehydrated alcohol is then added thereto,
Precipitating is precipitated to filter, gained filter cake 5~10mL deionized water will be filtered and 5~10mL dehydrated alcohol is successively washed and filtered,
It is repeated 3 times.Gained filter cake is placed in 50 DEG C of vacuum drying ovens dry 24 hours to get bagasse xylan-trihydroxy benzene
Formic acid/isophthalic acid ester.
(10) determination of acid-basetitration bagasse xylan-trihydroxybenzoic acid/isophthalic acid ester double esterification derivative is used
Carboxylic esterification degree of substitution, operating method is as follows: the Product samples of precise about 0.5g are put into 250mL conical flask, are added
Then 5mL deionized water instills a few drop phenolphthalein indicators.The sodium hydroxide solution of 2.5mL0.5mol/L is added, shakes up.20
Concussion saponification 1 hour at DEG C.The inner wall of plug and conical flask is rinsed with 10mL deionized water, then molten with 0.5mol/L normal hydrochloric acid
Liquid is titrated to colourless, as terminal.The volume V of record consumption hydrochloric acid standard solution1.Under the same conditions, with the sugarcane before esterification
Slag xylan carries out blank titration, records the hydrochloric acid standard solution volume V of consumption0.The calculating of carboxylic esterification degree of substitution (DS) is public
Formula is as follows:
In formula: WC--- contain the mass fraction of ester carbonyl group, % in double esterification bagasse xylan;
V0--- titration bagasse xylan uses HCl standard solution volume, Unit/mL;
V1--- HCl standard solution volume used in titration target product, Unit/mL;
CHCl--- the concentration of HCl, unit mol/L;
The quality of m --- sample, unit g;
M --- acyl group is dehydrated the relative molecular mass of xylose units, unit g/mol;
132 --- the relative molecular mass of bagasse xylan dewatering unit, unit g/mol;
DS --- ester carbonyl group degree of substitution.
The present invention has synthesized the bagasse xylan with double esterification substituent group-trihydroxy benzene first by secondary esterification
Acid/isophthalic acid ester introduces two kinds of new active groups on the pendant hydroxyl group of xylan, enhances its bioactivity,
In the fields such as medicine, material potential using value with higher.
Detailed description of the invention
Fig. 1 is the SEM photograph of former bagasse xylan.
Fig. 2 is double esterification bagasse xylan-trihydroxybenzoic acid/isophthalic acid ester SEM photograph.
Fig. 3 is the IR figure of former bagasse xylan.
Fig. 4 is double esterification bagasse xylan-trihydroxybenzoic acid/isophthalic acid ester IR figure.
Fig. 5 is the XRD diagram of former bagasse xylan.
Fig. 6 is double esterification bagasse xylan-trihydroxybenzoic acid/isophthalic acid ester XRD diagram.
Fig. 7 is TG the and DTG curve of former bagasse xylan.
Fig. 8 is double esterification bagasse xylan-trihydroxybenzoic acid/isophthalic acid ester TG and DTG curve.
Specific embodiment
Embodiment:
(1) 7g bagasse xylan is 24 hours dry in 50 DEG C of vacuum drying ovens, obtain butt bagasse xylan.
(2) it weighs butt bagasse xylan obtained by 4g step (1) to be added in 250mL four-hole boiling flask, sequentially adds 15mL points
Pure n,N-Dimethylformamide, 2g N, N- dicyclohexylcarbodiimide and 0.3g ammonium persulfate are analysed, control system temperature is 20
DEG C, it stirs 25 minutes, obtains bagasse xylan activating solution.
(3) it weighs 3,4,5- triacetyl chlorobenzoyl chloride of 6g to be placed in 50mL beaker, 25mL is added and analyzes pure N, N- dimethyl
Formamide pours into constant pressure funnel after dissolution is mixed.Bagasse xylan activating solution obtained by step (2) is warming up to 60
DEG C, start that mixed liquor is added dropwise, control time for adding is 1.5 hours, and reaction system is continued reflux instead in 60 DEG C after being added dropwise
It answers 4 hours.
(4) after reaction, reaction solution obtained by step (3) is filtered, filter cake is placed in 100mL beaker, with point of 10mL
Analysis pure acetone, 15mL dehydrated alcohol are washed and are filtered, and after being repeated 3 times, it is dry that gained filter cake is placed in 50 DEG C of constant-temperature vacuums
It is 12 hours dry in case, obtain bagasse xylan-triacetyl benzoic ether.
(5) the dehydrated alcohol saturated solution of 35mL sodium bicarbonate is placed in 100mL beaker, is weighed obtained by 5g step (4)
Bagasse xylan-triacetyl benzoic ether is added in beaker, is stirred 20 minutes at room temperature, until the pH of solution is 8.
(6) reaction solution obtained by step (5) is filtered, filter cake is placed in 100mL beaker, washs precipitating with 15mL deionized water
And filter, it is repeated 3 times, filter cake is placed in 50 DEG C of vacuum drying ovens dry 12 hours to get bagasse xylan 3,4,5-
Trihydroxybenzoic acid ester.
(7) 6g M-phthalic acid, the sodium hydroxide solution that 20mL mass fraction is 5% are added sequentially to tetra- mouthfuls of 250mL
In flask, it is stirred to react at room temperature 30 minutes, obtains M-phthalic acid sodium salt solution.
(8) it weighs bagasse xylan-trihydroxybenzoic acid ester obtained by 4g step (6) and is added to isophthalic two obtained by step (7)
In formic acid sodium salt solution, stir 3 hours at room temperature.The hydrochloric acid that 10mL mass fraction is 3% is added and adjusts reaction solution pH to 6, then
2mL is added and analyzes pure pyridine, is warming up to 35 DEG C, stirs lower reaction 4 hours.It is after reaction 5% with 25mL mass fraction
System pH is adjusted to 5 by hydrochloric acid solution, is cooled to 25 DEG C, and the reaction was continued 1 hour.
(9) reaction solution obtained by step (8) is poured into 100mL beaker, 25mL dehydrated alcohol is then added thereto, be precipitated
Precipitating filters, and will filter gained filter cake 10mL deionized water and 10mL dehydrated alcohol is successively washed and filtered, be repeated 3 times.It will
Gained filter cake is placed in 50 DEG C of vacuum drying ovens dry 24 hours to get bagasse xylan-trihydroxybenzoic acid/isophthalic two
Formic acid esters.
(10) using acid-base titration to bagasse xylan 3,4,5-trihydroxy benzoic acid/isophthalic diformazan obtained by step (10)
Acid esters esterification degree is measured, and measures DS=0.79.
Product samples are analyzed through IR it is found that in 1689.38cm-1Place is the characteristic absorption peak of ester carbonyl group, 1280.72cm-1Out
The stretching vibration absworption peak of existing C-O-C, is the characteristic absorption peak of esters, it was demonstrated that Gallic Acid base bagasse wood
Glycan ester-OH reacted really and generates double esterification derivative with M-phthalic acid.In 3200~3600cm-1Between
Xylan and bagasse xylan-trihydroxybenzoic acid/isophthalic acid ester have a stronger eigen vibration peak, belong to O-H and stretch
Contracting vibration peak.Compare bagasse xylan XRD diagram and bagasse xylan-trihydroxybenzoic acid/isophthalic acid ester XRD diagram and
Diffraction data learns that the X-ray powder diffraction peak of log glycan is unobvious, and bagasse xylan-trihydroxybenzoic acid/isophthalic two
Formic acid esters occurs high and narrow at 11.1 °, 22.3 °, 24.9 °, 27.6 °, 33.2 °, 38.6 °, 39.7 °, 49.9 °, 62.1 °
Diffraction maximum;Compared with the XRD diagram of former bagasse xylan, show that crystallinity significantly improves, crystalline content increases, and crystal region is opposite
Completely.It is according to thermogravimetric analysis figure it is found that mainly de- due to residual ethanol, water in bagasse xylan etc. before 200 DEG C
Except caused;200~300 DEG C of losses have reached 45%;The mass loss rate of bagasse xylan is about 15% after 300 DEG C.230
There is a small ladder peak before DEG C, this partial loss is mainly due to bagasse xylan-trihydroxybenzoic acid/isophthalic acid ester
In the removing of residual water caused by, mass loss and bagasse xylan are close.It can be seen that bagasse xylan-trihydroxy benzene first
Acid/isophthalic acid ester thermal stability increases.
Claims (1)
1. a kind of double esterification bagasse xylan-Gallic Acid/isophthalic acid ester synthetic method, feature exist
In specific steps are as follows:
(1) 5 ~ 7g bagasse xylan is 24 hours dry in 50 DEG C of vacuum drying ovens, obtain butt bagasse xylan;
(2) it weighs butt bagasse xylan obtained by 2 ~ 5g step (1) to be added in 250mL four-hole boiling flask, sequentially adds 10 ~ 20mL points
It analyses pureN,NDimethylformamide, 1 ~ 4.5gN,NDicyclohexylcarbodiimide and 0.2 ~ 0.6 g ammonium persulfate, control system
Temperature is 20 ~ 25 DEG C, stirs 25 minutes, obtains bagasse xylan activating solution;
(3) it weighs 4 ~ 8g, 3,4,5- triacetyl chlorobenzoyl chloride to be placed in 50mL beaker, it is pure that 20 ~ 35mL analysis is addedN,NDiformazan
Base formamide pours into constant pressure funnel after dissolution is mixed;Bagasse xylan activating solution obtained by step (2) is warming up to 60
~ 65 DEG C, start that mixed liquor is added dropwise, control time for adding is 1 ~ 2 hour, continues reaction system in 60 ~ 65 DEG C after being added dropwise
Back flow reaction 4 hours;
(4) after reaction, reaction solution obtained by step (3) is filtered, filter cake is placed in 100mL beaker, with the analysis of 5 ~ 10mL
Pure acetone, 5 ~ 15mL dehydrated alcohol are washed and are filtered, after being repeated 3 times;It is dry that gained filter cake is placed in 50 DEG C of constant-temperature vacuums
It is 12 hours dry in case, obtain bagasse xylan-triacetyl benzoic ether;
(5) the dehydrated alcohol saturated solution of 30 ~ 50mL sodium bicarbonate is placed in 100mL beaker, is weighed obtained by 3 ~ 8g step (4)
Bagasse xylan-triacetyl benzoic ether is added in beaker, is stirred 10 ~ 30 minutes at room temperature, until the pH of solution is 8;
(6) reaction solution obtained by step (5) is filtered, filter cake is placed in 100mL beaker, washs precipitating with 10 ~ 15mL deionized water
And filter, it is repeated 3 times, filter cake is placed in 50 DEG C of vacuum drying ovens dry 12 hours to get bagasse xylan 3,4,5-
Trihydroxybenzoic acid ester;
(7) 4 ~ 8g M-phthalic acid, the sodium hydroxide solution that 20 ~ 40mL mass fraction is 3% ~ 5% are added sequentially to 250mL tetra-
In mouth flask, it is stirred to react at room temperature 0.5 ~ 1 hour, obtains M-phthalic acid sodium salt solution;
(8) it weighs bagasse xylan-trihydroxybenzoic acid ester obtained by 1 ~ 5g step (6) and is added to isophthalic diformazan obtained by step (7)
In acid sodium-salt solution, stir 2 ~ 4 hours at room temperature;Be added 10 ~ 15mL mass fraction be 1% ~ 5% hydrochloric acid adjust reaction solution pH to
6 ~ 7,1 ~ 3mL analysis pure pyridine is added, is warming up to 30 ~ 45 DEG C, is stirred lower reaction 3 ~ 7 hours;After reaction with 20 ~ 35mL
Mass fraction is that system pH is adjusted to 4 ~ 5 by the hydrochloric acid solution of 5 %, is cooled to 20 ~ 30 DEG C, the reaction was continued 1 hour;
(9) reaction solution obtained by step (8) is poured into 100mL beaker, 20 ~ 30mL dehydrated alcohol is then added thereto, be precipitated
Precipitating filters, and will filter gained filter cake 5 ~ 10mL deionized water and 5 ~ 10mL dehydrated alcohol is successively washed and filtered, repeat 3
It is secondary;By gained filter cake be placed in 50 DEG C of vacuum drying ovens dry 24 hours to get bagasse xylan-trihydroxybenzoic acid/
Isophthalic acid ester.
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN106565857A (en) * | 2016-10-26 | 2017-04-19 | 桂林理工大学 | Method for synthesizing double-active sulfo bagasse xylan isophthalate |
CN107540789A (en) * | 2017-09-15 | 2018-01-05 | 桂林理工大学 | Biologically active derivatives bagasse xylan cloves acid esters g AM synthetic method |
CN107586352A (en) * | 2017-10-01 | 2018-01-16 | 桂林理工大学 | A kind of preparation method with antitumor activity bagasse xylan gallic acid/ferulic acid ester |
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2018
- 2018-10-21 CN CN201811225993.7A patent/CN109400735A/en active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106565857A (en) * | 2016-10-26 | 2017-04-19 | 桂林理工大学 | Method for synthesizing double-active sulfo bagasse xylan isophthalate |
CN107540789A (en) * | 2017-09-15 | 2018-01-05 | 桂林理工大学 | Biologically active derivatives bagasse xylan cloves acid esters g AM synthetic method |
CN107586352A (en) * | 2017-10-01 | 2018-01-16 | 桂林理工大学 | A kind of preparation method with antitumor activity bagasse xylan gallic acid/ferulic acid ester |
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