CN103333288B - Living things catalysis preparation is containing the method for wood sugar cationic polymer - Google Patents
Living things catalysis preparation is containing the method for wood sugar cationic polymer Download PDFInfo
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- CN103333288B CN103333288B CN201310239715.8A CN201310239715A CN103333288B CN 103333288 B CN103333288 B CN 103333288B CN 201310239715 A CN201310239715 A CN 201310239715A CN 103333288 B CN103333288 B CN 103333288B
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Abstract
The invention discloses the method for living things catalysis preparation containing wood sugar cationic polymer. The method, first taking pyridine/n-hexane solvent pairs as reaction medium, adds wood sugar, immobilized lipase and metering system vinyl acetate, is that under 30～60 DEG C, normal pressure, wood sugar ester monomer has been synthesized in reaction in temperature. With sodium hydrogensulfite, potassium peroxydisulfate composition redox initiation system, adopt wood sugar ester monomer, acrylamide, acrylyl oxy-ethyl-trimethyl salmiac and the deionized water preparation of preparation containing wood sugar cationic polymer again. The synthetic wood sugar ester monomer of enzyme process for the present invention, has overcome that chemical synthesis complex steps in prior art, reaction efficiency are low, contaminated environment, the selective shortcoming such as low; Have advantages of that reaction condition gentleness, environmental friendliness, course of reaction are simply controlled, product easily separates from reaction mixture.
Description
Technical field
The present invention relates to living things catalysis and synthetic field, be specifically related to one synthetic wood sugar ester monomer in pyridine/n-hexane solvent pairs system, and aggregate into the method containing wood sugar cationic polymer.
Background technology
At present; using glycosyl as skeleton or the polymer of side chain be called as " (containing) glycopolymers "; its research is very active; particularly become study hotspot for the glycopolymers with different structure (such as line style, starlike, super cladodification and dendroid) of controlledly synthesis and accurately preparation, but its research range mainly concentrates on biomedicine and technical field of biological material at present. However, due to synthetic difficulty and the complexity of performance, cause the still deficiency of synthetic and performance study to novel Biodegradable polymer/sugar polymer hybrid material, the particularly rare report of research in the application aspect of water treatment and papermaking performance chemicals based on hemicellulose sugar high molecular polymer. At present, in the process of the synthetic sugary high molecular polymer of chemical method, the synthesis path of monomer is often more complicated, and reagent is many, and accessory substance is many. Moreover, chemical method is synthetic also has such as deficiencies such as severe reaction conditions, environment are unfriendly. This has limited the development of sugary high molecular polymer to a certain extent.
In nonaqueous phase dicyandiamide solution, lipase-catalyzed reaction is except having regioselectivity and the stereoselectivity of height, do not need outside the advantage of traditional hydrolases such as radical protection, all right catalytic transesterification, esterification, the synthetic reactions such as ammonia solution, can carry out the catalyzed conversion of water-insoluble materials, greatly expand the effect substrate scope of enzyme, moreover, it also helps recovery and the recycling of enzyme, reduce the energy consumption of separation process, side reaction and microbial contamination that the heat endurance of enzyme and minimizing and anti-sealing cause are improved, can be by controlling different reaction conditions, can on the specific hydroxyl of sugar, react, the sugary unsaturated monomer that preparation structure is determined. for now, less to the synthetic research of sugar ester monomer under nonaqueous phase condition in the world, research field also only limits to biological medicine, there is researcher under nonaqueous phase condition, to utilize the ester exchange reaction of enzymatic methylgalactoside, α-D-glucopyranoside and sucrose abroad, prepared the definite sugar ester of structure, and utilize gained monomer to prepare the polymer such as biocompatible hydrogels. domestic only have Wei Yuanan and Liu Rongli etc. to report that employing lipase has synthesized the research of And Application of Sucrose-based Polymers for fruit antistaling agent under nonaqueous phase condition. because the dissolubility of saccharide compound in organic solvent is very poor, this has hindered the synthetic development of enzyme-catalyzed change sugar ester monomer in nonaqueous phase to a certain extent.
Wood sugar is the one of pentose, is extensively present in occurring in nature with the form of D-wood sugar, special in the discarded part of agricultural product (crust of the cob of for example corn, stalk, cotton boll) content a lot. Xylan is the one of hemicellulose, and numerous research shows that the content of hemicellulose in paper slurry and the swollen performance of paper fibre have close relationship. The increase of hemicellulose contributes to improve the beatability of paper pulp, reduces beating energy consumption simultaneously. Therefore, the synthetic wood sugar ester monomer of application enzymatic method, aggregates into wood sugar polymer, provides new approaches, and can improve the added value of this type of discarded object for the performance that improves paper, makes a silk purse out of a sow's ear, and improves the utilization rate of resource.
Summary of the invention
The object of the invention is the deficiency existing in order to solve above-mentioned prior art, a kind of environmental friendliness is provided, production cost is low, course of reaction is simply controlled, living things catalysis is prepared wood sugar ester in the segregative pyridine/n-hexane of product solvent pairs system, and aggregates into the new method generating containing wood sugar cationic polymer.
Object of the present invention is achieved through the following technical solutions:
Living things catalysis preparation is containing the method for wood sugar cationic polymer, and it comprises the steps:
(1) ratio that is 1:1～10:1 in the volume ratio of pyridine and n-hexane in reactor is made into pyridine/n-hexane solvent pairs reaction medium, be that 1.5～30mg/mL (0.01～0.2mmol/mL) adds wood sugar by wood sugar and the ratio of the consumption of reaction medium, the ratio that is 0.1～100:1 in the weight ratio of biocatalyst and wood sugar adds biocatalyst immobilized lipase, be that 1:1～100:1 adds metering system vinyl acetate by the mol ratio of acry radical donor and wood sugar, it is 30～60 DEG C in temperature, hunting speed is 100～300rpm, under normal pressure, react after 2～72 hours, synthetic wood sugar ester monomer,
(2) to account for the mass percent of the whole reaction system of this step, in the redox initiation system being formed by sodium hydrogensulfite 1～5%, potassium peroxydisulfate 1-10%, the wood sugar monomer 0.01 ~ 10%, acrylamide 10-20%, acrylyl oxy-ethyl-trimethyl salmiac 3-5% and the deionized water 80～70% that add step (1) to make, make containing wood sugar cationic polymer.
In above-mentioned preparation method, described immobilized lipase derives from microorganism, comprises bacillus lipase、Root miehei lipase, lipase from candida sp, Pseudomonas cepacia lipase or thermophilic silk born of the same parents bacterium lipase.
In above-mentioned preparation method, the obtained wood sugar ester of step (1) monomer is to add the n-hexane of 50～200mL to remove unreacted metering system vinyl acetate after reactant mixture is removed to immobilized lipase after filtration, surplus solution carries out rotary evaporation in vacuo at 50～70 DEG C, until last liquid no longer reduces, the wood sugar ester monomer finally obtaining. The present invention steams remaining liquid polymerization with revolving of different amounts and obtains containing wood sugar cationic polymer.
Principle of the present invention: adopt pyridine/n-hexane solvent pairs system, using immobilized lipase as catalyst, catalysis wood sugar and metering system vinyl acetate carry out esterification, obtain wood sugar ester monomer (comprising monoesters 5 ' with 1 ' 5 ' diester), under the effect of initator, wood sugar dibasic acid esters polyisocyanate polyaddition generates containing wood sugar cationic polymer.
Compared with prior art, the present invention has advantages of as follows:
(1) adopt biocatalyst immobilized lipase efficient, high stability to carry out the synthetic wood sugar ester of catalysis wood sugar, overcome the easy inactivation of enzyme in prior art, the shortcoming that reaction efficiency is low; Course of reaction is simply controlled, product is easily separated;
(2) reaction terminating adopts and filters the method for dezymotizing, simple, convenient and rapid, has overcome in prior art that high temperature goes out that enzyme energy consumption is large, the easily shortcoming such as residual of zymoprotein; And immobilised enzymes can Reusability, reduces production costs;
(3) utilized the enzymatic new technology of nonaqueous phase, adopted pyridine/n-hexane solvent pairs as reaction medium, unreacted metering system vinyl acetate can be used organic solvent extraction, and rotary evaporation is removed, and has simplified product separation step, and the product impurity obtaining is few; The organic solvent of removing through evaporation can recycle and reuse, and has reduced production cost;
(4) reaction condition gentleness, without alkali waste discharge, environmental friendliness.
Detailed description of the invention
For better understanding the present invention, below in conjunction with embodiment, the present invention is done further and described in detail, but the scope of protection of present invention is not limited to the scope that embodiment represents.
Embodiment 1
Be 1:10 60mg wood sugar, 0.6g(wood sugar than the mass ratio of enzyme) mol ratio that derives from immobilized lipase, 4mmoL(wood sugar and the acry radical donor of bacillus subtilis is 1:10) metering system vinyl acetate and 2ml pyridine/n-hexane (volume ratio is 3:1) solvent pairs medium put into tool plug triangular flask; be placed in vibration in 30 DEG C, the water-bath constant temperature oscillator of 150rpm; after reaction 48h, 95% wood sugar transforms. Remove by filter immobilized lipase, add 100mL n-hexane, at 50 DEG C, carry out rotary evaporation in vacuo to liquid and no longer reduce. With sodium hydrogensulfite 1%(to represent with respect to this reaction system mass percent, as follows), under the redox initiation system that forms of potassium peroxydisulfate 1%, adopt wood sugar ester monomer 10%, acrylamide 10%, acrylyl oxy-ethyl-trimethyl salmiac 3% and the deionized water 75% of preparation to prepare containing wood sugar cationic polymer, product is gel, water insoluble.
Embodiment2
Be 10:1 the mass ratio of 60mg wood sugar, 6mg(wood sugar and enzyme) mol ratio that derives from immobilized lipase, 0.4mmoL(wood sugar and the acry radical donor of antarctic candida is 1:1) metering system vinyl acetate and 2ml pyridine/n-hexane (3:1) solvent pairs medium put into tool plug triangular flask; be placed in vibration in 50 DEG C, the water-bath constant temperature oscillator of 300rpm; after reaction 72h, 55% wood sugar transforms. Remove by filter immobilized lipase, add 150mL n-hexane, at 60 DEG C, carry out rotary evaporation in vacuo to liquid and no longer reduce. With sodium hydrogensulfite 2%(to represent with respect to reaction system mass percent, as follows), under the redox initiation system that forms of potassium peroxydisulfate 5%, adopt wood sugar ester monomer 1%, acrylamide 10%, acrylyl oxy-ethyl-trimethyl salmiac 3% and the deionized water 79% of preparation to prepare containing wood sugar cationic polymer, product is water-soluble, and weight average molecular weight (Mw) is about 1000 ~ 1100kDa.
Embodiment3
Be 1:100 the mass ratio of 3mg wood sugar, 300mg(wood sugar and enzyme) mol ratio that derives from immobilized lipase, 2mmoL(wood sugar and the acry radical donor of thermophilic silk born of the same parents bacterium is 1:100) metering system vinyl acetate and 2ml pyridine/n-hexane (1:1) solvent pairs medium put into tool plug triangular flask; be placed in vibration in 60 DEG C, the water-bath constant temperature oscillator of 100rpm; after reaction 2h, 60% wood sugar transforms. Remove by filter immobilized lipase, add 200mL n-hexane, at 70 DEG C, carry out rotary evaporation in vacuo to liquid and no longer reduce. With sodium hydrogensulfite 5%(to represent with respect to reaction system mass percent, as follows), under the redox initiation system that forms of potassium peroxydisulfate 10%, adopt wood sugar ester monomer 0.01%, acrylamide 10%, acrylyl oxy-ethyl-trimethyl salmiac 3% and the deionized water 72% of preparation to prepare containing wood sugar cationic polymer, product is soluble in water, and weight average molecular weight (Mw) is about 150 ~ 200kDa.
Embodiment4
Be 1:20 the mass ratio of 30mg wood sugar, 600mg(wood sugar and enzyme) mol ratio that derives from immobilized lipase, 1mmoL(wood sugar and the acry radical donor of Pseudomonas cepacia is 1:5) metering system vinyl acetate and 2ml pyridine/n-hexane (2:1) solvent pairs medium put into tool plug triangular flask; be placed in vibration in 40 DEG C, the water-bath constant temperature oscillator of 200rpm; after reaction 48h, 93% wood sugar transforms. Remove by filter immobilized lipase, add 50mL n-hexane, at 50 DEG C, carry out rotary evaporation in vacuo to liquid and no longer reduce. With sodium hydrogensulfite 1%(to represent with respect to reaction system mass percent, as follows), under the redox initiation system that forms of potassium peroxydisulfate 3%, adopt wood sugar ester monomer 5%, acrylamide 10%, acrylyl oxy-ethyl-trimethyl salmiac 5% and the deionized water 76% of preparation to prepare containing wood sugar cationic polymer. This polymer gel, water insoluble.
Embodiment5
Be 1:50 the mass ratio of 15mg wood sugar, 750mg(wood sugar and enzyme) mol ratio that derives from immobilized lipase, 1mmoL(wood sugar and the acry radical donor of root Mucor is 1:10) metering system vinyl acetate and 2ml pyridine/n-hexane (4:1) solvent pairs medium put into tool plug triangular flask; be placed in vibration in 40 DEG C, the water-bath constant temperature oscillator of 150rpm; after reaction 24h, 75% wood sugar transforms. Remove by filter immobilized lipase, add 100mL n-hexane, at 60 DEG C, carry out rotary evaporation in vacuo to liquid and no longer reduce. With sodium hydrogensulfite 3%(to represent with respect to reaction system mass percent, as follows), under the redox initiation system that forms of potassium peroxydisulfate 5%, adopt wood sugar ester monomer 1%, acrylamide 15%, acrylyl oxy-ethyl-trimethyl salmiac 4% and the deionized water 72% of preparation to prepare containing wood sugar cationic polymer. This polymer is water-soluble, and weight average molecular weight (Mw) is about 550 ~ 600kDa.
Embodiment6
Be 1:1 the mass ratio of 15mg wood sugar, 15mg(wood sugar and enzyme) mol ratio that derives from immobilized lipase, 1mmoL(wood sugar and the acry radical donor of Pseudomonas cepacia is 1:10) metering system vinyl acetate and 2ml pyridine/n-hexane (10:1) solvent pairs medium put into tool plug triangular flask; be placed in vibration in 40 DEG C, the water-bath constant temperature oscillator of 200rpm; after reaction 48h, 53% wood sugar transforms. Remove by filter immobilized lipase, add 100mL n-hexane, at 60 DEG C, carry out rotary evaporation in vacuo to liquid and no longer reduce. With sodium hydrogensulfite 1%(to represent with respect to reaction system mass percent, as follows), under the redox initiation system that forms of potassium peroxydisulfate 2%, adopt wood sugar ester monomer 0.01%, acrylamide 10%, acrylyl oxy-ethyl-trimethyl salmiac 3% and the deionized water 84% of preparation to prepare containing wood sugar cationic polymer. This polymer is soluble in water, and weight average molecular weight (Mw) is about 250 ~ 300kDa.
Embodiment7
Be 1:2 the mass ratio of 60mg wood sugar, 120mg(wood sugar and enzyme) mol ratio that derives from immobilized lipase, 1mmoL(wood sugar and the acry radical donor of root Mucor is 1:2.5) metering system vinyl acetate and 2ml pyridine/n-hexane (3:1) solvent pairs medium put into tool plug triangular flask; be placed in vibration in 40 DEG C, the water-bath constant temperature oscillator of 200rpm; after reaction 48h, 78% wood sugar transforms. Remove by filter immobilized lipase, add 100mL n-hexane, at 60 DEG C, carry out rotary evaporation in vacuo to liquid and no longer reduce. With sodium hydrogensulfite 3%(to represent with respect to reaction system mass percent, as follows), under the redox initiation system that forms of potassium peroxydisulfate 5%, adopt wood sugar ester monomer 5%, acrylamide 15%, acrylyl oxy-ethyl-trimethyl salmiac 4% and the deionized water 68% of preparation to prepare containing wood sugar cationic polymer. This polymer gel, water insoluble.
Embodiment8
Being 2:1 the mass ratio of 30mg wood sugar, 15mg(wood sugar and enzyme) immobilized lipase, 1mmoL (mol ratio of wood sugar and acry radical donor is 1:5) metering system vinyl acetate and 2ml pyridine/n-hexane (8:1) solvent pairs medium that derive from thermophilic silk born of the same parents bacterium put into tool plug triangular flask; be placed in vibration in 60 DEG C, the water-bath constant temperature oscillator of 200rpm; after reaction 60h, 70% wood sugar transforms. Remove by filter immobilized lipase, add 100mL n-hexane, at 60 DEG C, carry out rotary evaporation in vacuo to liquid and no longer reduce. With sodium hydrogensulfite 2%(to represent with respect to reaction system mass percent, as follows), under the redox initiation system that forms of potassium peroxydisulfate 4%, adopt wood sugar ester monomer 1%, acrylamide 10%, acrylyl oxy-ethyl-trimethyl salmiac 3% and the deionized water 80% of preparation to prepare containing wood sugar cationic polymer. This polymer is water-soluble, and weight average molecular weight (Mw) is about 600 ~ 650kDa.
Embodiment9
Be 1:5 the mass ratio of 30mg wood sugar, 150mg(wood sugar and enzyme) mol ratio that derives from immobilized lipase, 2mmoL(wood sugar and the acry radical donor of antarctic candida is 1:10) metering system vinyl acetate and 2ml pyridine/n-hexane (5:1) solvent pairs medium put into tool plug triangular flask; be placed in vibration in 40 DEG C, the water-bath constant temperature oscillator of 200rpm; after reaction 48h, 98% wood sugar transforms. Remove by filter immobilized lipase, add 100mL n-hexane, at 60 DEG C, carry out rotary evaporation in vacuo to liquid and no longer reduce. With sodium hydrogensulfite 3%(to represent with respect to reaction system mass percent, as follows), under the redox initiation system that forms of potassium peroxydisulfate 5%, adopt wood sugar ester monomer 2%, acrylamide 15%, acrylyl oxy-ethyl-trimethyl salmiac 5% and the deionized water 70% of preparation to prepare containing wood sugar cationic polymer. This polymer is not soluble in water, and weight average molecular weight (Mw) is about 1300-1350kDa.
Embodiment10
Be 1:2 the mass ratio of 60mg wood sugar, 120mg(wood sugar and enzyme) mass ratio that derives from immobilized lipase, 4mmoL(wood sugar and the acry radical donor of bacillus subtilis is 1:10) metering system vinyl acetate and 2ml pyridine/n-hexane (3:1) solvent pairs medium put into tool plug triangular flask; be placed in vibration in 40 DEG C, the water-bath constant temperature oscillator of 200rpm; after reaction 12h, 52% wood sugar transforms. Remove by filter immobilized lipase, add 100mL n-hexane, at 60 DEG C, carry out rotary evaporation in vacuo to liquid and no longer reduce. With sodium hydrogensulfite 3%(to represent with respect to reaction system mass percent, as follows), under the redox initiation system that forms of potassium peroxydisulfate 5%, adopt wood sugar ester monomer 2%, acrylamide 15%, acrylyl oxy-ethyl-trimethyl salmiac 4% and the deionized water 71% of preparation to prepare containing wood sugar cationic polymer. This polymer is not soluble in water, the about 1250-1300kDa of weight average molecular weight (Mw).
Claims (1)
1. living things catalysis preparation, containing the method for wood sugar cationic polymer, is characterized in that comprising the steps:
(1) ratio that is 1:1～10:1 in the volume ratio of pyridine and n-hexane in reactor is made into pyridine/n-hexane solvent pairs reaction medium, be that 1.5～30mg/mL adds wood sugar by wood sugar and the ratio of the consumption of reaction medium, the ratio that is 0.1～100:1 in the weight ratio of biocatalyst and wood sugar adds biocatalyst immobilized lipase, be that 1:1～100:1 adds metering system vinyl acetate by the mol ratio of acry radical donor metering system vinyl acetate and wood sugar, it is 30～60 DEG C in temperature, hunting speed is 100～300rpm, under normal pressure, react after 2～72 hours, synthetic wood sugar ester monomer, described immobilized lipase derives from microorganism, comprises bacillus lipase、Root miehei lipase, Pseudomonas cepacia lipase or thermophilic silk born of the same parents bacterium lipase; Obtained wood sugar ester monomer is to add the n-hexane of 50～200mL to remove unreacted metering system vinyl acetate after reactant mixture is removed to immobilized lipase after filtration, surplus solution carries out rotary evaporation in vacuo at 50～70 DEG C, until last liquid no longer reduces, the wood sugar ester monomer finally obtaining;
(2) to account for the mass percent of the whole reaction system of this step, in the redox initiation system being formed by sodium hydrogensulfite 0.1～5%, potassium peroxydisulfate 0.1-10%, the wood sugar ester monomer 0.01 ~ 10%, acrylamide 10-20%, acrylyl oxy-ethyl-trimethyl salmiac 3-5% and the deionized water 80～70% that add step (1) to make, make containing wood sugar cationic polymer.
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| CN101301590A (en) * | 2008-01-16 | 2008-11-12 | 浙江大学 | Sugar-containing polymer compound film with blocked pore and preparation thereof |
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| "Permethacrylated carbohydrates: synthesis and reactivity in glycosidation reaction";Christelle Zandanel等;《Tetrahedron》;20090904;第65卷;第9395-9402页 * |
| "含糖聚合物的合成";孟建文等;《高分子通报》;20021030(第5期);第66-72页 * |
| "混合溶剂中酶法催化合成木糖酯及其结构鉴定研究";冯广莉等;《现代食品科技》;20130615;第29卷(第6期);第1222-1226页 * |
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