CN109400767A - A kind of synthetic method being crosslinked bagasse xylan -4- acetylamino cinnamate-g-AM - Google Patents
A kind of synthetic method being crosslinked bagasse xylan -4- acetylamino cinnamate-g-AM Download PDFInfo
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- CN109400767A CN109400767A CN201811225983.3A CN201811225983A CN109400767A CN 109400767 A CN109400767 A CN 109400767A CN 201811225983 A CN201811225983 A CN 201811225983A CN 109400767 A CN109400767 A CN 109400767A
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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
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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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 the synthetic methods of bagasse xylan -4- acetyl group cinnamate-g-AM a kind of.First using bagasse xylan as raw material, ammonium persulfate and sodium hydrogensulfite are initiation system, and acrylamide is grafted monomers,N,N’Methylene-bisacrylamide is crosslinking agent, synthesizing cross-linked bagasse xylan-g-AM；Again using 4- acetyl group cinnamic acid as esterifying agent, N, N'- diisopropylcarbodiimide (DIC) and ammonium persulfate are composite catalyst, have synthesized crosslinking bagasse xylan -4- acetyl group cinnamate-g-AM through catalytic esterification in dichloromethane solvent.The present invention carries out xylan by grafting esterification composite modified, crosslinking bagasse xylan -4- acetylamino cinnamate-the g-AM of synthesis introduces new active group, making the bioactivity of bagasse xylan is enhanced, and bagasse xylan thermal stability is improved, product is with a wide range of applications in medicine and other fields.
Description
Technical field
The present invention relates to technical field of fine, especially a kind of crosslinking bagasse xylan -4- acetylamino cinnamic acid
The synthetic method of ester-g-AM.
Background technique
Bagasse xylan is a kind of biomass energy of natural reproducible, itself have the function of unique physiological activity and,
Such as promote mitosis and immunological regulation function.Discovery bagasse xylan has bioactivity, but itself in the course of the research
Activity be not obvious, need to be chemically modified by modes such as esterification, etherificate, graft copolymerizations, increase new active group, mention
The bioactivity of high bagasse xylan.
The type of substituent group and substitution quantity have significant shadow to the physiological activity of xylan in xylan and its derivative
It rings.The solubility of substance itself can be improved after chemical modification, while can also be improved its physiological activity.The dissolution of xylan
Property and xylan physiological activity have certain relationship, the xylan of high-dissolvability can preferably play its activity.Propylene
Amide (AM) has good biocompatibility, and solubility is higher in all kinds of solvents, by bagasse xylan and acrylamide
After being grafted, the crystallinity of bagasse xylan can be made to decline, solubility improves.Meanwhile 4- acetylamino cinnamic acid is one
Kind chemical industry and medicine intermediate, the growth that Carcinoma cell differentiation can be induced, inhibit cancer cell.If by bagasse xylan or its grafting
Copolymer and 4- acetylamino cinnamic acid carry out esterification again, can enhance the anti-tumor activity or target of bagasse xylan itself
To tumors destroyed cell.
For the present invention first using bagasse xylan as raw material, ammonium persulfate and sodium hydrogensulfite are initiation system, acrylamide
For grafted monomers, N, N '-methylene-bisacrylamide is crosslinking agent, synthesizing cross-linked bagasse xylan-g-AM；Again with 4- acetyl group
Cinnamic acid is esterifying agent, and N, N'- diisopropylcarbodiimide (DIC) and ammonium persulfate are composite catalyst, molten in methylene chloride
Crosslinking bagasse xylan -4- acetyl group cinnamate-g-AM has been synthesized through catalytic esterification in agent.
Summary of the invention
The purpose of the present invention is the bioactivity to improve bagasse xylan, expand it in the application of anti-cancer field, provide
A kind of synthetic method being crosslinked bagasse xylan -4- acetylamino cinnamate-g-AM.
Specific steps of the invention are as follows:
(1) 5~10g bagasse xylan is obtained into butt sugarcane to constant weight in drying 24 hours in 60 DEG C of vacuum constant temperature drying boxes
Slag xylan.
(2) 0.2~0.6g ammonium persulfate is successively weighed in 50mL beaker, and 15~20mL deionized water is added, in room
Initiator solution is stirred evenly to obtain under temperature, it is spare.
(3) acrylamide (AM) of 2~5g is weighed in 50mL beaker, and 10~20mL deionized water is added, and stirring is equal
It is even to obtain monomer solution, it pours into 100mL constant pressure funnel, it is spare.
(4) butt bagasse xylan obtained by 3~6g step (1) is weighed in 250mL four-hole boiling flask, and 10 are added thereto
It is stirred 20~30 minutes at~20mL deionized water, with 40~60 DEG C.Start monomer solution obtained by a dropping step (3), controls 2
It is added dropwise within~3 hours；When adding to the 1/2 of monomer solution volume, 0.1~0.2g of crosslinking agent N, N '-di-2-ethylhexylphosphine oxide third is added
Acrylamide.Meanwhile initiator solution obtained by step (2) is added portionwise, every 10~15 minutes 0.4~1.1mL of dropwise addition.To monomer
The reaction was continued 3~5 hours after solution, initiator solution are added dropwise, and material is cooled to room temperature.
(5) 30~40mL is added into step (4) resulting material and analyzes pure acetone, precipitating 20~30 minutes, filtering was used in combination
The washing of 15~20mL dehydrated alcohol filters 3 times, and filter cake is put into surface plate, is placed in 50 DEG C of vacuum constant temperature drying boxes dry 24
Hour to constant weight, obtains crosslinking bagasse xylan-g-AM.
(6) it weighs bagasse xylan-g-AM obtained by 1~2g step (5) to be added in 250mL four-hole boiling flask, then successively
0.8~1.6g 4- acetylamino cinnamic acid, 0.5~2g N, N'- diisopropylcarbodiimide (DIC), 0.1~0.3g mistake is added
Ammonium sulfate and 20~30mL analyze absolute dichloromethane, stir evenly, and control reaction temperature at 60~70 DEG C, stir lower reaction 6~9
Hour.To which after reaction, material is cooled to room temperature.
(7) step (6) resulting material is successively washed with 15~20mL dehydrated alcohol and 10~15mL analysis pure acetone respectively
It washs, filter 3 times.Filter cake is put into surface plate, is placed in 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight to get friendship
Join bagasse xylan -4- acetylamino cinnamate-g-AM.
(8) the carboxylic esterification degree of substitution of the bagasse xylan esterification derivative obtained by determination of acid-basetitration step (7), behaviour
It is as follows to make method: the standard sample of accurate weighing 0.50g is put into 250mL conical flask, and 5mL deionized water is added, then instills
Three drop phenolphthalein indicators.The standard solution of the sodium hydroxide of 2.5mL0.5mol/L is added, shakes up.Concussion saponification 1 is small at 25 DEG C
When.The inner wall of plug and conical flask is rinsed with the deionized water of 10mL, then be titrated to 0.5mol/L hydrochloric acid standard solution it is colourless,
As terminal.It records HCl and consumes volume V1.Under the same conditions, blank titration is carried out with the bagasse xylan before esterification, recorded
The HCl standard solution volume V of consumption0.Carboxylic esterification degree of substitution (DSc) calculation formula is as follows:
In formula:
Wc--- contain the mass fraction of ester carbonyl group, % in product；
V0--- titration bagasse xylan graft copolymerization derivative consumes hydrochloric acid standard solution volume, Unit/mL；
V1--- the hydrochloric acid standard solution volume of titration product consumption, Unit/mL；
CHCl--- hydrochloric acid standard solution concentration, unit moL/L；
The quality of m --- product, unit g；
The relative molecular mass of M and the acyl group and bagasse xylan of 132-carboxylate agents dehydration xylose units.
The present invention carries out composite modified, the crosslinking bagasse xylan -4- acetyl ammonia of synthesis to xylan by grafting esterification
Base cinnamate-g-AM introduces new active group, enhances the anticancer activity of bagasse xylan, and improve bagasse
Xylan thermal stability.
Detailed description of the invention
Fig. 1 is the SEM photograph of former bagasse xylan.
Fig. 2 is the SEM photograph for being crosslinked bagasse xylan -4- acetylamino cinnamic acid-g-AM.
Fig. 3 is the IR figure of former bagasse xylan.
Fig. 4 is the IR figure for being crosslinked bagasse xylan -4- acetylamino cinnamic acid-g-AM.
Fig. 5 is the XRD diagram of former bagasse xylan.
Fig. 6 is the XRD diagram for being crosslinked bagasse xylan -4- acetylamino cinnamic acid-g-AM.
Fig. 7 is TG the and DTG curve of former bagasse xylan.
Fig. 8 is TG the and DTG curve for being crosslinked bagasse xylan -4- acetylamino cinnamic acid-g-AM.
Specific embodiment
Embodiment:
(1) 8g bagasse xylan is obtained into butt bagasse wood to constant weight in drying 24 hours in 60 DEG C of vacuum constant temperature drying boxes
Glycan.
(2) 0.5g ammonium persulfate is successively weighed in 50mL beaker, and 18mL deionized water is added, and stirring is equal at room temperature
Even initiator solution, it is spare.
(3) acrylamide (AM) of 3g is weighed in 50mL beaker, and 15mL deionized water is added, and stirs evenly to obtain monomer
Solution pours into 100mL constant pressure funnel, spare.
(4) butt bagasse xylan obtained by 5g step (1) is weighed in 250mL four-hole boiling flask, and 15mL is added thereto
It is stirred 25 minutes at deionized water, with 45 DEG C.Start monomer solution obtained by a dropping step (3), control was added dropwise at 3 hours；
When adding to the 1/2 of monomer solution volume, crosslinking agent 0.15g N, N '-methylene-bisacrylamide is added.Meanwhile it being added portionwise
Initiator solution obtained by step (2), every 10 minutes dropwise addition 1mL.Continue after monomer solution, initiator solution are added dropwise anti-
It answers 4 hours, material is cooled to room temperature.
(5) 35mL is added into step (4) resulting material and analyzes pure acetone, precipitating 30 minutes, filters and anhydrous with 20mL
Ethanol washing filters 3 times, and filter cake is put into surface plate, is placed in 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight, obtains
It is crosslinked bagasse xylan-g-AM.
(6) it weighs bagasse xylan-g-AM obtained by 1g step (5) to be added in 250mL four-hole boiling flask, then sequentially add
0.8g 4- acetylamino cinnamic acid, 1.2g N, N'- diisopropylcarbodiimide (DIC), 0.2g ammonium persulfate and 30mL analysis
Absolute dichloromethane stirs evenly, and controls reaction temperature at 68 DEG C, stirs lower reaction 8 hours.It is to after reaction, material is cold
But to room temperature.
(7) step (6) resulting material successively washed with 20mL dehydrated alcohol and 15mL analysis pure acetone respectively, filter 3
It is secondary.Filter cake is put into surface plate, is placed in 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight to get crosslinking bagasse wood
Glycan -4- acetylamino cinnamate-g-AM.
(8) it is carried out using esterification degree of the acid-base titration to crosslinking bagasse xylan 4- acetylamino cinnamate-g-AM
Measurement, measuring DS is 0.1762.
Product samples are analyzed through IR, 1726.05cm-1It is the carbon-oxygen bond absorption peak of AM and the carbon-oxygen bond characteristic absorption of ester bond
Peak, 1689.76cm-1Place is amide stretching vibration absworption peak, 1669.71cm-1Place is carbon-carbon double bond stretching vibration absworption peak；
1593.67cm-1It is the characteristic absorption peak i.e. phenyl ring skeleton stretching vibration absworption peak of phenyl ring.By SEM map analysis, produce after the reaction
Object surface irregularity has sheet packed structures, there is obviously gap and damaged rill, it was demonstrated that by modified former knot
Change is sent out in structure surface.By TG the and DTG curve of TG and DTG curve map analysis graft esterification product, at 200 DEG C to 250 DEG C
Stage, mass loss reach up to 23%, mainly crosslinking bagasse xylan -4- acetylamino cinnamic acid-g-AM's itself
Caused by decomposition, final product is significantly improved in 800 DEG C of Shi Yuyuan bagasse xylans compared to thermal stability.It is analyzed by XRD diagram,
Product after esterification modification is that peak crystallization increases at 18.35 °, 19.21 °, 22.09 °, 26.64 ° ° in 2 θ of powder angle, and peak type is stronger
Illustrate that crystalline content is more, crystal region is complete.
Claims (1)
1. a kind of synthetic method for being crosslinked bagasse xylan 4- acetylamino cinnamate-g-AM, it is characterised in that specific steps
Are as follows:
(1) 5 ~ 10g bagasse xylan it is poly- to be obtained into butt bagasse wood to constant weight in drying 24 hours in 60 DEG C of vacuum constant temperature drying boxes
Sugar；
(2) 0.2 ~ 0.6g ammonium persulfate is successively weighed in 50mL beaker, and 15 ~ 20mL deionized water is added, and is stirred at room temperature
Uniform initiator solution is mixed, it is spare；
(3) weigh the acrylamide of 2 ~ 5g in 50mL beaker, and be added 10 ~ 20mL deionized water, stir evenly monomer is molten
Liquid pours into 100mL constant pressure funnel, spare；
(4) butt bagasse xylan obtained by 3 ~ 6g step (1) is weighed in 250mL four-hole boiling flask, and 10 ~ 20mL is added thereto
It is stirred 20 ~ 30 minutes at deionized water, with 40 ~ 60 DEG C；Start monomer solution obtained by a dropping step (3), control was dripped at 2 ~ 3 hours
It adds complete；When adding to the 1/2 of monomer solution volume, 0.1 ~ 0.2g of crosslinking agent is added N,N’Methylene-bisacrylamide；Together
When, initiator solution obtained by step (2) is added portionwise, every 10 ~ 15 minutes 0.4 ~ 1.1mL of dropwise addition；To monomer solution, initiator
The reaction was continued 3 ~ 5 hours after solution is added dropwise, and material is cooled to room temperature；
(5) 30 ~ 40mL is added into step (4) resulting material and analyzes pure acetone, precipitating 20 ~ 30 minutes, filters and with 15 ~ 20mL
Dehydrated alcohol washing filters 3 times, and filter cake is put into surface plate, is placed in 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to perseverance
Weight, obtains crosslinking bagasse xylan-g-AM；
(6) it weighs bagasse xylan-g-AM obtained by 1 ~ 2g step (5) to be added in 250mL four-hole boiling flask, then sequentially add
0.8 ~ 1.6g 4- acetylamino cinnamic acid, 0.5 ~ 2g N, N'- diisopropylcarbodiimide (DIC), 0.1 ~ 0.3g ammonium persulfate
Absolute dichloromethane is analyzed with 20 ~ 30mL, is stirred evenly, controls reaction temperature at 60 ~ 70 DEG C, is stirred lower reaction 6 ~ 9 hours；To anti-
After answering, material is cooled to room temperature；
(7) step (6) resulting material successively washed with 15 ~ 20mL dehydrated alcohol and 10 ~ 15mL analysis pure acetone respectively, filtered
3 times；Filter cake is put into surface plate, is placed in 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight to get crosslinking bagasse
Xylan -4- acetylamino cinnamate-g-AM.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112175140A (en) * | 2020-09-06 | 2021-01-05 | 桂林理工大学 | Synthesis method of active BX/SGPS quaternary graft copolymerization derivative |
| CN112175142A (en) * | 2020-09-06 | 2021-01-05 | 桂林理工大学 | Synthesis method of bagasse xylan bromopyruvate-g-AM/MA |
| CN112175141A (en) * | 2020-09-06 | 2021-01-05 | 桂林理工大学 | Synthesis method of active cross-linked BX/SGPS nitro-p-methyl benzoate-g-AM |
| CN112239512A (en) * | 2020-09-06 | 2021-01-19 | 桂林理工大学 | Synthesis method of active bromine-containing bagasse xylan ester-g-AM |
| CN112250797A (en) * | 2020-09-06 | 2021-01-22 | 桂林理工大学 | Synthesis method of active bagasse xylan bromopyruvate-g-AM/MA/BzA |
| CN112250796A (en) * | 2020-09-06 | 2021-01-22 | 桂林理工大学 | Preparation method of BX/SGPS nitro-p-methyl benzoate-g-AM/MA |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5296578A (en) * | 1992-09-18 | 1994-03-22 | Donlar Corporation | Production of polysuccinimide and polyaspartic acid from maleic anhydride and ammonia |
| CN107417857A (en) * | 2017-09-15 | 2017-12-01 | 桂林理工大学 | Active anticancer derivative bagasse xylan cloves acid esters g AM/MMA synthetic method |
| 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 |
-
2018
- 2018-10-21 CN CN201811225983.3A patent/CN109400767A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5296578A (en) * | 1992-09-18 | 1994-03-22 | Donlar Corporation | Production of polysuccinimide and polyaspartic acid from maleic anhydride and ammonia |
| CN107417857A (en) * | 2017-09-15 | 2017-12-01 | 桂林理工大学 | Active anticancer derivative bagasse xylan cloves acid esters g AM/MMA synthetic method |
| 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 |
Non-Patent Citations (1)
| Title |
|---|
| 乔丽萍等: "酚酸生物活性研究进展", 《中国食品学报》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112175140A (en) * | 2020-09-06 | 2021-01-05 | 桂林理工大学 | Synthesis method of active BX/SGPS quaternary graft copolymerization derivative |
| CN112175142A (en) * | 2020-09-06 | 2021-01-05 | 桂林理工大学 | Synthesis method of bagasse xylan bromopyruvate-g-AM/MA |
| CN112175141A (en) * | 2020-09-06 | 2021-01-05 | 桂林理工大学 | Synthesis method of active cross-linked BX/SGPS nitro-p-methyl benzoate-g-AM |
| CN112239512A (en) * | 2020-09-06 | 2021-01-19 | 桂林理工大学 | Synthesis method of active bromine-containing bagasse xylan ester-g-AM |
| CN112250797A (en) * | 2020-09-06 | 2021-01-22 | 桂林理工大学 | Synthesis method of active bagasse xylan bromopyruvate-g-AM/MA/BzA |
| CN112250796A (en) * | 2020-09-06 | 2021-01-22 | 桂林理工大学 | Preparation method of BX/SGPS nitro-p-methyl benzoate-g-AM/MA |
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Application publication date: 20190301 |