CN102559943B - Process method for separating glucose from ionic liquid - Google Patents
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- CN102559943B CN102559943B CN201010618647.2A CN201010618647A CN102559943B CN 102559943 B CN102559943 B CN 102559943B CN 201010618647 A CN201010618647 A CN 201010618647A CN 102559943 B CN102559943 B CN 102559943B
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Abstract
The invention provides a process method for crystallizing and separating glucose from ionic liquid by an anti-solvent method to obtain a pure product. The process method for separating the glucose from the ionic liquid by the anti-solvent method comprises the following process that firstly, dissolving the glucose into the ionic liquid at a certain temperature; and then adding an anti-solvent into the homogeneous mixed solution to crystallize and separate the glucose. The solid glucose obtained by crystallization is separated out from the solvent by filtering and then the anti-solvent in the residual solution is removed in a spin steaming mode to obtain the mixed solution of the ionic liquid and a trace amount of glucose, so that the aim of repeatedly using is fulfilled.
Description
Technical field
The present invention relates to the processing method of glucose and ionic liquid.Particularly, the present invention relates to the processing method of anti-solvent method separating glucose and ionic liquid.
Background technology
In recent years, the research that cellulose series biomass was converted into water-soluble sugar has caused being extensively absorbed in of domestic and international investigator.But owing to there is a large amount of hydrogen bonds between cellulose macromolecule, make cellulosic character very stable.It is water insoluble, without reductibility, is not hydrolyzed at normal temperatures, and at high temperature hydrolysis is also very slow.Traditional cellulose conversion is to carry out in biological enzyme or inorganic acid aqueous solution, has many disadvantageous factors, as strong in acid-hydrolysis method corrodibility, and contaminate environment, and the easy secondary hydrolysis of product under acidic conditions, react wayward.Enzyme catalysis exist cellulase catalytic activity low, recycling rate variance, thereby cause the too high problem of production cost.
Therefore, find a kind of process greenization and can become the current main path that rationally utilizes biomass energy by the cellulosic environmentally friendly technology of Efficient Conversion.Compare with traditional organic solvent, ionic liquid has advantages of many incomparable: as steam forces down, the feature such as non-volatile, non-combustible, Heat stability is good, liquid temperature wide ranges, dissolving power be strong, and can regulate himself character by the change of structure.These features make ionic liquid show unique physicochemical property and function, become a class novel green solvent of current cellulose conversion.At present, had and much studies have shown that Mierocrystalline cellulose can the high efficiency water-soluble sugars such as glucose that are converted in ionic liquid.But, because the separation difficulty of glucose and ionic liquid makes the conversion of Mierocrystalline cellulose in ionic liquid be stuck in laboratory stage always, seriously restrict its process of industrialization.
Glucose and ionic liquid are all difficult volatile matter, so common distillating method cannot be isolated.In addition, the dissolving power of ionic liquid is stronger, find a kind of extraction agent that can extract glucose from ionic liquid also very difficult.So, reach the object of separating glucose and ionic liquid, must adopt some novel separate modes.Anti-solvent method utilization be the difference of reactive force between solute and solvent and anti-solvent.Selected anti-solvent and solvent dissolve each other completely, and do not dissolve each other or slightly soluble with solute.When anti-solvent joins in the mixed system of solute and solvent, because anti-solvent is stronger than the reactive force of solute and solvent with the reactive force of solvent, the solubleness of solute in solvent is reduced rapidly, form the supersaturated solution of solute, thereby make solute crystallization.Up to the present, at glucose, the application aspect separated with ionic liquid have not been reported anti-solvent method.We are applied in anti-solvent technology from ionic liquid, to reclaim sugar, have realized the effective separated method of sugar with ionic liquid.
Summary of the invention
Object of the present invention is exactly to transform after generation glucose in order to solve cellulose degradation, the separation problem of glucose and ionic liquid, from the angle of Sustainable development, solve the Mierocrystalline cellulose industrialized bottleneck problem of degrading in ionic liquid, promote the process of industrialization of cellulose series biomass degraded.
The object of the invention is to adopt following technical scheme to realize.
The invention provides a kind of glucose processing method separated with ionic liquid, the method comprises the insoluble solids thing removing by filter in ionic liquid and glucose solution, then add anti-solvent that glucose crystallization is separated out, and filter, washing obtains glucose solids, distillation filtrate, reclaim anti-solvent, and the step that ionic liquid is recycled.
Preferably, in the present invention, the separating process of glucose and ionic liquid comprises glucose and ionic liquid solution is stirred, the step of solids removed by filtration foreign material.
Preferably, in the present invention, the separating process of glucose and ionic liquid also comprises anti-solvent is joined in ionic liquid and glucose mixed solution, stirs, adds crystal seed, ageing, the step that glucose crystallization is separated out.
Preferably, in the present invention the separating process of glucose and ionic liquid also comprise by the solid liquid phase obtaining after filtration, wash to obtain pure glucose, by remaining liquid phase by fractionation by distillation, reclaim ethanol, make ionic liquid reach the step of recycling.
In the present invention, the separating process of glucose and ionic liquid comprises the steps:
(1) by ionic liquid and glucose solution at a certain temperature, remove by filter insolubles.If there is no insolubles, can omit this step;
(2) by the solution obtaining in step (1), add anti-solvent in stirring, and add a small amount of crystal seed, glucose is separated out in crystallization ageing.
(3) solid liquid phase that obtains in step (2) is filtered, and to anti-solvent wash solid phase filter cake for, dryly to obtain pure glucose solids, remaining solution is isolated anti-solvent through evaporating, and obtains ionic liquid.
In the separating process of above glucose and ionic liquid, the temperature of the separating impurity of ionic liquid and glucose solution is preferably 20 ~ 130 ℃, more preferably 40 ~ 80 ℃.
In the separating process of above glucose and ionic liquid, the temperature that anti-solvent is separated out glucose is preferably-10 ~ 70 ℃, more preferably 0 ~ 30 ℃.
In the separating process of above glucose and ionic liquid, anti-solvent is preferably methyl alcohol, ethanol, Virahol, 1-propyl alcohol, acetonitrile, methylene dichloride.Described anti-solvent is ethanol more preferably.
In the separating process of above glucose and ionic liquid, ionic liquid is as the ionic liquid of active solvent in cellulose degradation process, mainly to comprise glyoxaline ion liquid: 1-butyl-3-Methylimidazole villaumite ([BMIM] Cl), 1-ethyl-3-methylimidazole bromine salt ([EMIM] Br), 1-butyl-3-Methylimidazole acetate ([BMIM] [OAC]), 1-ethyl-3-methylimidazole acetate ([EMIM] [OAC]), 1-butyl-3-Methylimidazole hydrosulfate ([BMIM] [HSO
4]), 1-ethyl-3-methylimidazole hydrosulfate ([EMIM] [HSO
4]), 1-hydrogen base-3-Methylimidazole hydrosulfate ([HMIM] [HSO
4]).
In the separating process of above glucose and ionic liquid, the mass ratio of ionic liquid and anti-solvent is preferably 1:5 ~ 1:35, more preferably 1:10 ~ 1:25.
The present invention has following beneficial effect:
The present invention provides a kind of separation method for Mierocrystalline cellulose is converted into glucose in ionic liquid, promotes cellulosic process of industrialization.Compare with the separation method such as conventional distillation, extraction, anti-solvent method operates at a lower temperature, reduces energy expenditure; Solute glucose, because of the crystallization from ion liquid system that adds of anti-solvent, obtains pure glucose solids, and separating effect is thorough, reduces secondary pollution and the too much use of organic solvent.
In addition, the anti-etoh solvent toxicity of selecting in the present invention is little, low price, and boiling point is low.When adding system, anti-etoh solvent separates out after glucose, obtain after filtration the mixing solutions of ionic liquid and glucose, evaporation can be removed ethanol from ionic liquid at a lower temperature, obtain ionic liquid and micro-sugared compounding substances, thereby make ionic liquid recycling.
Below will be for a more detailed description to separating process of the present invention:
The principle of glucose provided by the invention and ionic liquid separating process is: the difference of utilizing reactive force between glucose and ionic liquid and anti-solvent.Selected anti-solvent must dissolve each other completely with solvent glucose, and does not dissolve each other or slightly soluble with solute ions liquid.When anti-solvent joins in the mixed system of glucose and ionic liquid, because anti-solvent is stronger than the reactive force of glucose and ionic liquid with the reactive force of ionic liquid, the solubleness of glucose in ionic liquid is reduced rapidly, form the supersaturated solution of glucose, thereby glucose crystallization is separated out, obtain the crystalline solid that glucose is pure.The present invention preferably anti-etoh solvent and ionic liquid is dissolved each other completely, and with glucose slightly soluble.
The anti-solvent using in the processing method of anti-solvent method separating ionic liquid provided by the invention and glucose specifically comprises methyl alcohol, ethanol, Virahol, 1-propyl alcohol, acetonitrile, methylene dichloride.The application example of listing ethanol and 2 kinds of anti-solvents of acetonitrile in embodiments of the invention, other anti-solvents are identical with the application principle of these 2 kinds of anti-solvents; The ionic liquid the present invention relates to specifically comprises 1-butyl-3-Methylimidazole villaumite ([BMIM] Cl), 1-ethyl-3-methylimidazole bromine salt ([EMIM] Br), 1-butyl-3-Methylimidazole acetate ([BMIM] [OAC]), 1-ethyl-3-methylimidazole acetate ([EMIM] [OAC]), 1-butyl-3-Methylimidazole hydrosulfate ([BMIM] [HSO
4]), 1-ethyl-3-methylimidazole hydrosulfate ([EMIM] [HSO
4]), 1-hydrogen base-3-Methylimidazole hydrosulfate ([HMIM] [HSO
4]); The mass ratio of ionic liquid and anti-solvent is preferably 1:5 ~ 1:35; The temperature of the separate solid impurity of ionic liquid and glucose solution is preferably 40 ~ 80 ℃; The temperature that anti-solvent is separated out glucose is preferably 0 ~ 30 ℃.
According to an embodiment of the invention, technical process and the working method of anti-solvent method separating ionic liquid provided by the invention and glucose are as follows:
First, by glucose dry 24h in 100 ℃ of air dry ovens, ionic liquid is logical nitrogen drying 12h at 40 ~ 150 ℃.Getting glucose quality mark is the ionic liquid of 5 % ~ 40% and the mixing solutions of glucose, joins in the ground triangular flask of 100ml, inserts the oil bath pan of 80 ~ 120 ℃ of appointment, and magnetic agitation, to mixture formation clear solution, stops heating.Treat solution cool to room temperature, insert in the salt solution bath of-10 ~ 70 ℃, add anti-solvent, the ratio optimization of ionic liquid and anti-solvent is 1:5 ~ 1:35, and magnetic agitation adds a small amount of glucose crystal seed.According to anti-solvent principle, glucose starts to separate out with solid form.Every 15 min ~ 30 min samplings, by 0.45um syringe filters, filter, the concentration of liquid phase analysis surplus solution, when the concentration difference of the liquid solution of twice mensuration is less than 0.1%, decision-making system reaches balance, stops experiment.
In the technique of above-mentioned anti-solvent method separating ionic liquid and glucose, the time of separating out of glucose is depended on ratio, stirring intensity, the Precipitation Temperature of glucose and ionic liquid.The precipitation efficiency of glucose is relevant with ratio, stirring intensity, Precipitation Temperature, the time of separating out of glucose and anti-solvent.
Separation method provided by the invention yet there are no application aspect glucose and ionic liquid separated.The present invention provides a kind of separation method for Mierocrystalline cellulose is converted into glucose in ionic liquid, promotes cellulosic process of industrialization.With traditional separation method distillation, extraction phase ratio, processing method provided by the invention at least has the following advantages: anti-solvent method operates at a lower temperature, reduces energy expenditure; Solute glucose, because of the crystallization from ion liquid system that adds of anti-solvent, obtains pure glucose solids, and separating effect is thorough, reduces secondary pollution and the too much use of organic solvent.
In addition, the anti-etoh solvent toxicity of selecting in the present invention is little, low price, and boiling point is low.When adding system, anti-etoh solvent separates out after glucose, obtain after filtration the mixing solutions of ionic liquid and glucose, distillation can be removed ethanol from ionic liquid at a lower temperature, obtain ionic liquid and micro-sugared compounding substances, thereby make ionic liquid recycling.
Embodiment
Below in conjunction with embodiment, the processing method of anti-solvent method separating ionic liquid provided by the invention and glucose is described in further detail, but not thereby limiting the invention.
Embodiment 1
It is anti-solvent that the present embodiment explanation adopts acetonitrile, and in ionic liquid, the massfraction of glucose is 30%, the mass ratio 1:10 of ionic liquid and acetonitrile, and Precipitation Temperature is the technique of separating glucose and ionic liquid [BMIM] Cl under the condition of 30 ℃.
By glucose dry 24h in 100 ℃ of air dry ovens, ionic liquid is logical nitrogen drying 12h at 50 ℃.Get glucose quality mark and be 30% ionic liquid [BMIM] Cl and the mixing solutions of glucose, join in the ground triangular flask of 100ml, insert the oil bath pan of 90 ℃, magnetic agitation, forms clear solution to mixture, stops heating.Treat solution cool to room temperature, insert in the water-bath of 30 ℃, add anti-solvent acetonitrile, the mass ratio of [BMIM] Cl and acetonitrile is 1:10, and magnetic agitation adds a small amount of crystal seed.According to anti-solvent principle, glucose starts to separate out with solid form.Every 30min sampling, by 0.45um syringe filters, filter the concentration of high performance liquid chromatography liquid phase analysis solution.When the concentration difference of the liquid solution of twice mensuration is less than 0.1%, decision-making system reaches balance, stops experiment.Remove by filter the glucose solids in mixing solutions, revolve and steam filtrate, obtain ionic liquid and acetonitrile.The time of separating out of glucose is 5h, and maximum eduction rate is 32.8%.
Embodiment 2
It is anti-solvent that the present embodiment explanation adopts ethanol, and in ionic liquid, the massfraction of glucose is 30%, the mass ratio 1:5 of ionic liquid and ethanol, and Precipitation Temperature is the technique of separating glucose and ionic liquid [BMIM] Cl under the condition of 30 ℃.
By glucose dry 24h in 100 ℃ of air dry ovens, ionic liquid is logical nitrogen drying 12h at 90 ℃.Get glucose quality mark and be 30% ionic liquid [BMIM] Cl and the mixing solutions of glucose, join in the ground triangular flask of 100ml, insert the oil bath pan of 90 ℃, magnetic agitation, forms clear solution to mixture, stops heating.Treat solution cool to room temperature, insert in the water-bath of 30 ℃, add anti-etoh solvent, the mass ratio of [BMIM] Cl and ethanol is 1:5, and magnetic agitation adds a small amount of crystal seed.According to anti-solvent principle, glucose starts to separate out with solid form.Every 30min sampling, by 0.45um syringe filters, filter the concentration of high performance liquid chromatography liquid phase analysis solution.When the concentration difference of the liquid solution of twice mensuration is less than 0.1%, decision-making system reaches balance, stops experiment.Remove by filter the glucose solids in mixing solutions, revolve and steam filtrate, obtain ionic liquid and ethanol.The time of separating out of glucose is 6h, and maximum eduction rate is 67.5%.
Embodiment 3
It is anti-solvent that the present embodiment explanation adopts ethanol, and in ionic liquid, the massfraction of glucose is 30%, the mass ratio 1:15 of ionic liquid and ethanol, and Precipitation Temperature is the technique of separating glucose and ionic liquid [BMIM] Cl under the condition of 0 ℃.
By glucose dry 24h in 100 ℃ of air dry ovens, ionic liquid is logical nitrogen drying 12h at 90 ℃.Get glucose quality mark and be 30% ionic liquid [BMIM] Cl and the mixing solutions of glucose, join in the ground triangular flask of 100ml, insert the oil bath pan of 90 ℃, magnetic agitation, forms clear solution to mixture, stops heating.Treat solution cool to room temperature, insert in the salt solution bath of 0 ℃, add anti-etoh solvent, the mass ratio of [BMIM] Cl and ethanol is 1:15, and magnetic agitation adds a small amount of crystal seed.According to anti-solvent principle, glucose starts to separate out with solid form.Every 30min sampling, by 0.45um syringe filters, filter the concentration of high performance liquid chromatography liquid phase analysis solution.When the concentration difference of the liquid solution of twice mensuration is less than 0.1%, decision-making system reaches balance, stops experiment.Remove by filter the glucose solids in mixing solutions, revolve and steam filtrate, obtain ionic liquid and ethanol.The time of separating out of glucose is 4h, and maximum eduction rate is 77.4%.
Embodiment 4
It is anti-solvent that the present embodiment explanation adopts ethanol, and in ionic liquid, the massfraction of glucose is 40%, the mass ratio 1:25 of ionic liquid and ethanol, and Precipitation Temperature is the technique of separating glucose and ionic liquid [BMIM] Cl under the condition of 30 ℃.
By glucose dry 24h in 100 ℃ of air dry ovens, ionic liquid is logical nitrogen drying 12h at 90 ℃.Get glucose quality mark and be 40% ionic liquid [BMIM] Cl and the mixing solutions of glucose, join in the ground triangular flask of 100ml, insert the oil bath pan of 90 ℃, magnetic agitation, forms clear solution to mixture, stops heating.Treat solution cool to room temperature, insert in the water-bath of 30 ℃, add anti-etoh solvent, the mass ratio of [BMIM] Cl and ethanol is 1:25, and magnetic agitation adds a small amount of crystal seed.According to anti-solvent principle, glucose starts to separate out with solid form.Every 15min sampling, by 0.45um syringe filters, filter the concentration of high performance liquid chromatography liquid phase analysis solution.When the concentration difference of the liquid solution of twice mensuration is less than 0.1%, decision-making system reaches balance, stops experiment.Remove by filter the glucose solids in mixing solutions, revolve and steam filtrate, obtain ionic liquid and ethanol.The time of separating out of glucose is 0.5h, and maximum eduction rate is 83.5%.
Embodiment 5
It is anti-solvent that the present embodiment explanation adopts ethanol, and in ionic liquid, the massfraction of glucose is 40%, the mass ratio 1:35 of ionic liquid and ethanol, and Precipitation Temperature is the technique of separating glucose and ionic liquid [BMIM] Cl under the condition of-10 ℃.
By glucose dry 24h in 100 ℃ of air dry ovens, ionic liquid is logical nitrogen drying 12h at 90 ℃.Get glucose quality mark and be 40% ionic liquid [BMIM] Cl and the mixing solutions of glucose, join in the ground triangular flask of 100ml, insert the oil bath pan of 90 ℃, magnetic agitation, forms clear solution to mixture, stops heating.Treat solution cool to room temperature, insert in the salt solution bath of-10 ℃, add anti-etoh solvent, the mass ratio of [BMIM] Cl and ethanol is 1:35, and magnetic agitation adds a small amount of crystal seed.According to anti-solvent principle, glucose starts to separate out with solid form.Every 15min sampling, by 0.45um syringe filters, filter the concentration of high performance liquid chromatography liquid phase analysis solution.When the concentration difference of the liquid solution of twice mensuration is less than 0.1%, decision-making system reaches balance, stops experiment.Remove by filter the glucose solids in mixing solutions, revolve and steam filtrate, obtain ionic liquid and ethanol.The time of separating out of glucose is 0.5h, and maximum eduction rate is 88.7%.
Claims (6)
1. a glucose processing method separated with ionic liquid, the method comprises the steps:
(1) by the ionic liquid of certain glucose content and glucose mixture, filter, remove insolubles;
(2) in whipping process, will resist solvent to be added in the solution that step (1) obtains, add glucose crystal seed, and ageing, crystallization glucose;
(3) solid liquid phase obtaining in step (2) is filtered, the anti-solvent wash of filter cake, obtains pure glucose solids, and remaining solution is isolated anti-solvent through evaporation, obtains ionic liquid, is reused for cellulosic degradation process;
Wherein, described anti-solvent is selected from methyl alcohol, ethanol, Virahol, 1-propyl alcohol, acetonitrile, methylene dichloride;
Described ionic liquid is as the ionic liquid of active solvent in cellulose degradation process, to be selected from glyoxaline ion liquid: 1-butyl-3-Methylimidazole villaumite ([BMIM] Cl), 1-ethyl-3-methylimidazole bromine salt ([EMIM] Br), 1-butyl-3-Methylimidazole acetate ([BMIM] [OAC]), 1-ethyl-3-methylimidazole acetate ([EMIM] [OAC]), 1-butyl-3-Methylimidazole hydrosulfate ([BMIM] [HSO
4]), 1-ethyl-3-methylimidazole hydrosulfate ([EMIM] [HSO
4]), 1-hydrogen base-3-Methylimidazole hydrosulfate ([HMIM] [HSO
4]);
In the mixing solutions of described ionic liquid and glucose, glucose quality mark is 5%~40%;
The mass ratio of described ionic liquid and anti-solvent is 1:5~1:35;
The temperature that described anti-solvent is separated out glucose is-10~70 ℃.
2. processing method according to claim 1, is characterized in that, the temperature that the solution filter of ionic liquid and glucose is removed solid impurity is 20~130 ℃.
3. processing method according to claim 1 and 2, is characterized in that, the temperature that the solution filter of ionic liquid and glucose is removed solid impurity is 40~80 ℃.
4. processing method according to claim 1, is characterized in that, the temperature that anti-solvent is separated out glucose is 0~30 ℃.
5. processing method according to claim 1 and 2, is characterized in that, described anti-solvent is ethanol.
6. processing method according to claim 1 and 2, is characterized in that, the mass ratio of described ionic liquid and anti-solvent is 1:10~1:25.
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CN1301334C (en) * | 2005-07-01 | 2007-02-21 | 江南大学 | Method for extracting high purity glucose and functional oligose from crystalline glucose mother liquid |
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