CN102559943A - Process method for separating glucose from ionic liquid - Google Patents
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- CN102559943A CN102559943A CN2010106186472A CN201010618647A CN102559943A CN 102559943 A CN102559943 A CN 102559943A CN 2010106186472 A CN2010106186472 A CN 2010106186472A CN 201010618647 A CN201010618647 A CN 201010618647A CN 102559943 A CN102559943 A CN 102559943A
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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 glucose and ion liquid process method.Particularly, the present invention relates to anti-solvent method separating glucose and ion liquid process method.
Background technology
In recent years, the cellulose series biomass research that is converted into water-soluble sugar had caused extensively being absorbed in of domestic and international investigator.But, make cellulosic character very stable owing to have a large amount of hydrogen bonds between cellulose macromolecule.It is water insoluble, and hydrolysis does not take place no reductibility at normal temperatures, and hydrolysis at high temperature is also very slow.Traditional cellulose conversion is in enzyme or inorganic acid aqueous solution, to carry out, and has many adverse factors, and is strong like acid-hydrolysis method corrodibility, and contaminate environment, and the easy secondary hydrolysis of product under acidic conditions are reacted wayward.Enzyme catalysis exist the cellulase catalytic activity low, the recycling rate variance, thereby cause the too high problem of production cost.
Therefore, seek a kind of process greenization and can efficiently transform cellulosic environmentally friendly technology and become the current main path that rationally utilizes biomass energy.Compare with traditional organic solvent; Ionic liquid has many incomparable advantages: as steam force down, characteristics such as non-volatile, not flammable, Heat stability is good, liquid temperature wide ranges, dissolving power are strong, and can regulate himself character through the change of structure.These characteristics make ionic liquid show unique physicochemical property and function, become one type of novel green solvent of present cellulose conversion.At present, there have been a lot of research proof Mierocrystalline celluloses in ionic liquid, can high efficiencyly be converted into water-soluble sugars such as glucose.But,, seriously restrict its process of industrialization because glucose and ion liquid separation difficulty make the conversion of Mierocrystalline cellulose in ionic liquid be stuck in laboratory stage always.
Glucose and ionic liquid all are difficult volatile matter, so common distillating method can't separate it.In addition, ion liquid dissolving power is stronger, find also difficulty very of a kind of extraction agent that can from ionic liquid, extract glucose.So, reach separating glucose and ion liquid purpose, must adopt some novel separate modes.The anti-solvent method utilization be the difference of reactive force between solute and solvent and the anti-solvent.Selected anti-solvent and solvent dissolve each other fully, 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 the solute crystallization is separated out.Up to the present, anti-solvent method does not also appear in the newspapers in the application of glucose aspect ionic liquid separates.We are applied in anti-solvent technology and from ionic liquid, reclaim sugar, have realized sugar and ion liquid effective isolating method.
Summary of the invention
The object of the invention is exactly for after solving cellulose degradation conversion generation glucose; Glucose and ion liquid separation problem; From the angle of Sustainable development, solve the Mierocrystalline cellulose industrialized bottleneck problem of in ionic liquid, degrade, promote the process of industrialization that cellulose series biomass is degraded.
The objective of the invention is to adopt following technical scheme to realize.
The present invention provides a kind of glucose and ionic liquid separation processes method; This method comprises the insoluble solids thing that removes by filter in ionic liquid and the glucose solution; Add anti-solvent then glucose crystallization separated out, and filter, washing obtains glucose solids, distillation filtrating; Reclaim anti-solvent, and the step that ionic liquid is recycled.
Preferably, glucose and ion liquid separating process comprise and make glucose and ionic liquid solution stir the step of solids removed by filtration foreign material among the present invention.
Preferably, glucose and ion liquid separating process also comprise anti-solvent are joined in ionic liquid and the glucose mixed solution among the present invention, stir, add crystal seed, ageing, the step that glucose crystallization is separated out.
Preferably, among the present invention glucose and ion liquid separating process also comprise with the solid-liquid that obtains mutually through filter, wash pure glucose, with remaining liquid phase through fractionation by distillation, reclaim ethanol, make ionic liquid reach the step of recycling.
Glucose and ion liquid separating process comprise the steps: among the present invention
(1) with ionic liquid and glucose solution at a certain temperature, removes by filter insolubles.If there is not insolubles, can omit this step;
(2) with the solution that obtains in the step (1), in stirring, add anti-solvent, and add small amount of seeds, glucose is separated out in crystallization and ageing.
(3) solid-liquid that obtains in the step (2) is filtered mutually, and to the solid phase filter cake with anti-solvent wash, dry pure glucose solids, rest solution is isolated anti-solvent through evaporation, ionic liquid.
In above glucose and ion liquid separating process, the temperature of the separating impurity of ionic liquid and glucose solution is preferably 20 ~ 130 ℃, more preferably 40 ~ 80 ℃.
In above glucose and ion liquid separating process, the temperature that anti-solvent is separated out glucose is preferably-10 ~ 70 ℃, more preferably 0 ~ 30 ℃.
In above glucose and ion liquid separating process, anti-solvent is preferably methyl alcohol, ethanol, Virahol, 1-propyl alcohol, acetonitrile, methylene dichloride.Said anti-solvent is ethanol more preferably.
In above glucose and ion liquid separating process; Ionic liquid is mainly to comprise glyoxaline ion liquid as the ionic liquid of active solvent in the cellulose degradation process: 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 above glucose and ion liquid separating process, ionic liquid is preferably 1:5 ~ 1:35, more preferably 1:10 ~ 1:25 with the ratio of the quality of anti-solvent.
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.Separate method with the distillation of using always, extraction etc. and compare, anti-solvent method is operated at a lower temperature, reduces energy expenditure; Solute glucose obtains pure glucose solids because adding crystallization from ion liquid system of anti-solvent is separated out, and separating effect is thorough, reduces the use of secondary pollution and too much organic solvent.
In addition, the anti-etoh solvent toxicity of selecting for use among the present invention is little, low price, and boiling point is low.After anti-etoh solvent adding system is separated out glucose; Through filtering the mixing solutions of ionic liquid and glucose, evaporation can be removed ethanol from ionic liquid at a lower temperature; Obtain ionic liquid and the sugared compounding substances of trace, thereby make the ionic liquid recycling.
Below will make 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 the anti-solvent.Selected anti-solvent must dissolve each other with solvent glucose fully, and does not dissolve each other or slightly soluble with solute ions liquid.When anti-solvent joins in glucose and the ion liquid mixed system; Because anti-solvent is stronger than glucose and ion liquid reactive force with ion liquid reactive force; The solubleness of glucose in ionic liquid is reduced rapidly; Form the supersaturated solution of glucose, thereby glucose crystallization is separated out, obtain the pure crystalline solid of glucose.Preferably anti-etoh solvent of the present invention and ionic liquid dissolve each other fully, and with the glucose slightly soluble.
Employed anti-solvent specifically comprises methyl alcohol, ethanol, Virahol, 1-propyl alcohol, acetonitrile, methylene dichloride in the process method of anti-solvent method separating ionic liquid provided by the invention and glucose.List the application example of ethanol and 2 kinds of anti-solvents of acetonitrile in the embodiments of the invention, other anti-solvents are identical with the application principle of these 2 kinds of anti-solvents; The ionic liquid that 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]); Ionic liquid is preferably 1:5 ~ 1:35 with the ratio of the quality of anti-solvent; 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, the technical process and the working method of anti-solvent method separating ionic liquid provided by the invention and glucose are following:
With glucose dry 24h in 100 ℃ of air dry ovens, ionic liquid is logical nitrogen drying 12h under 40 ~ 150 ℃ earlier.Getting the 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 specified 80 ~ 120 ℃ oil bath pan, and magnetic agitation to mixture formation clear solution, stops heating.Treat the solution cool to room temperature, insert in-10 ~ 70 ℃ the salt solution bath that add anti-solvent, the ratio optimization of ionic liquid and anti-solvent is 1:5 ~ 1:35, magnetic agitation adds a small amount of glucose crystal seed.According to anti-solvent principle, glucose begins to separate out with solid form.Every at a distance from 15 min ~ 30 min sampling, with the filtration of 0.45um syringe filters, the concentration of liquid phase analysis surplus solution, the concentration difference of liquid solution of treating twice mensuration was less than 0.1% o'clock, and decision-making system reaches balance, stops to test.
In the technology of above-mentioned anti-solvent method separating ionic liquid and glucose, the time of separating out of glucose is depended on glucose and ion liquid ratio, stirring intensity, separates out temperature.Ratio, the stirring intensity of the precipitation efficiency of glucose and glucose and anti-solvent, separate out temperature, the time of separating out is relevant.
Separation method provided by the invention is not also seen application at glucose aspect ion liquid the separation.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, process method provided by the invention has the following advantages at least: anti-solvent method is operated at a lower temperature, reduces energy expenditure; Solute glucose obtains pure glucose solids because adding crystallization from ion liquid system of anti-solvent is separated out, and separating effect is thorough, reduces the use of secondary pollution and too much organic solvent.
In addition, the anti-etoh solvent toxicity of selecting for use among the present invention is little, low price, and boiling point is low.After anti-etoh solvent adding system is separated out glucose; Through filtering the mixing solutions of ionic liquid and glucose, distillation can be removed ethanol from ionic liquid at a lower temperature; Obtain ionic liquid and the sugared compounding substances of trace, thereby make the ionic liquid recycling.
Embodiment
To combine embodiment that the process method of anti-solvent method separating ionic liquid provided by the invention and glucose is done further detailed explanation below, but therefore not limit the present invention.
Embodiment 1
It is anti-solvent that acetonitrile is adopted in present embodiment explanation, and the massfraction of glucose is 30% in the ionic liquid, and the mass ratio 1:10 of ionic liquid and acetonitrile separates out temperature and be the technology of separating glucose and ionic liquid [BMIM] Cl under 30 ℃ the condition.
With glucose dry 24h in 100 ℃ of air dry ovens, ionic liquid is logical nitrogen drying 12h under 50 ℃.Get the 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 90 ℃ oil bath pan, magnetic agitation forms clear solution to mixture, stops heating.Treat the solution cool to room temperature, insert in 30 ℃ the water-bath that add anti-solvent acetonitrile, the mass ratio of [BMIM] Cl and acetonitrile is 1:10, magnetic agitation adds small amount of seeds.According to anti-solvent principle, glucose begins to separate out with solid form.Every at a distance from the 30min sampling, filter the concentration of performance liquid chromatography liquid phase analysis solution with the 0.45um syringe filters.The concentration difference of liquid solution of treating twice mensuration was less than 0.1% o'clock, and decision-making system reaches balance, stopped experiment.Remove by filter the glucose solids in the mixing solutions, revolve and steam filtrating, get 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 ethanol is adopted in present embodiment explanation, and the massfraction of glucose is 30% in the ionic liquid, and ionic liquid and alcoholic acid mass ratio 1:5 separate out temperature and be the technology of separating glucose and ionic liquid [BMIM] Cl under 30 ℃ the condition.
With glucose dry 24h in 100 ℃ of air dry ovens, ionic liquid is logical nitrogen drying 12h under 90 ℃.Get the 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 90 ℃ oil bath pan, magnetic agitation forms clear solution to mixture, stops heating.Treat the solution cool to room temperature, insert in 30 ℃ the water-bath that add anti-etoh solvent, [BMIM] Cl and alcoholic acid mass ratio are 1:5, magnetic agitation adds small amount of seeds.According to anti-solvent principle, glucose begins to separate out with solid form.Every at a distance from the 30min sampling, filter the concentration of performance liquid chromatography liquid phase analysis solution with the 0.45um syringe filters.The concentration difference of liquid solution of treating twice mensuration was less than 0.1% o'clock, and decision-making system reaches balance, stopped experiment.Remove by filter the glucose solids in the mixing solutions, revolve and steam filtrating, get 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 ethanol is adopted in present embodiment explanation, and the massfraction of glucose is 30% in the ionic liquid, and ionic liquid and alcoholic acid mass ratio 1:15 separate out temperature and be the technology of separating glucose and ionic liquid [BMIM] Cl under 0 ℃ the condition.
With glucose dry 24h in 100 ℃ of air dry ovens, ionic liquid is logical nitrogen drying 12h under 90 ℃.Get the 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 90 ℃ oil bath pan, magnetic agitation forms clear solution to mixture, stops heating.Treat the solution cool to room temperature, insert in 0 ℃ the salt solution bath that add anti-etoh solvent, [BMIM] Cl and alcoholic acid mass ratio are 1:15, magnetic agitation adds small amount of seeds.According to anti-solvent principle, glucose begins to separate out with solid form.Every at a distance from the 30min sampling, filter the concentration of performance liquid chromatography liquid phase analysis solution with the 0.45um syringe filters.The concentration difference of liquid solution of treating twice mensuration was less than 0.1% o'clock, and decision-making system reaches balance, stopped experiment.Remove by filter the glucose solids in the mixing solutions, revolve and steam filtrating, get 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 ethanol is adopted in present embodiment explanation, and the massfraction of glucose is 40% in the ionic liquid, and ionic liquid and alcoholic acid mass ratio 1:25 separate out temperature and be the technology of separating glucose and ionic liquid [BMIM] Cl under 30 ℃ the condition.
With glucose dry 24h in 100 ℃ of air dry ovens, ionic liquid is logical nitrogen drying 12h under 90 ℃.Get the 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 90 ℃ oil bath pan, magnetic agitation forms clear solution to mixture, stops heating.Treat the solution cool to room temperature, insert in 30 ℃ the water-bath that add anti-etoh solvent, [BMIM] Cl and alcoholic acid mass ratio are 1:25, magnetic agitation adds small amount of seeds.According to anti-solvent principle, glucose begins to separate out with solid form.Every at a distance from the 15min sampling, filter the concentration of performance liquid chromatography liquid phase analysis solution with the 0.45um syringe filters.The concentration difference of liquid solution of treating twice mensuration was less than 0.1% o'clock, and decision-making system reaches balance, stopped experiment.Remove by filter the glucose solids in the mixing solutions, revolve and steam filtrating, get 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 ethanol is adopted in the present embodiment explanation, and the massfraction of glucose is 40% in the ionic liquid, and ionic liquid and alcoholic acid mass ratio 1:35 separate out the technology of temperature for separating glucose and ionic liquid [BMIM] Cl under-10 ℃ the condition.
With glucose dry 24h in 100 ℃ of air dry ovens, ionic liquid is logical nitrogen drying 12h under 90 ℃.Get the 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 90 ℃ oil bath pan, magnetic agitation forms clear solution to mixture, stops heating.Treat the solution cool to room temperature, insert in-10 ℃ the salt solution bath that add anti-etoh solvent, [BMIM] Cl and alcoholic acid mass ratio are 1:35, magnetic agitation adds small amount of seeds.According to anti-solvent principle, glucose begins to separate out with solid form.Every at a distance from the 15min sampling, filter the concentration of performance liquid chromatography liquid phase analysis solution with the 0.45um syringe filters.The concentration difference of liquid solution of treating twice mensuration was less than 0.1% o'clock, and decision-making system reaches balance, stopped experiment.Remove by filter the glucose solids in the mixing solutions, revolve and steam filtrating, get ionic liquid and ethanol.The time of separating out of glucose is 0.5h, and maximum eduction rate is 88.7%.
Claims (10)
1. glucose and ionic liquid separation processes method; This method comprises anti-solvent is added in glucose and the ion liquid mixture solution; Glucose crystallization from ionic liquid is separated out,, obtain pure glucose through filtering, washing; And evaporated filtrate is isolated anti-solvent, the step that anti-solvent and ionic liquid are reused.
2. process method according to claim 1 is characterized in that said method comprises the step of glucose and ionic liquid solution being filtered, removing solid insoluble.
3. process method according to claim 1, its characteristic are that also said method comprises the anti-solvent of adding in glucose and ion liquid mixing solutions, the step that glucose crystallization is separated out.
4. process method according to claim 1, its characteristic are that also said method comprises the step that the separation of crystalline dextrose, anti-solvent and ionic liquid are recycled.
5. process method according to claim 1 is characterized in that said method comprises the steps:
(1) with the ionic liquid and the glucose mixture of certain glucose content, filters, remove insolubles;
(2) in whipping process, will resist solvent to be added in the solution that step (1) obtains, add the glucose crystal seed, and ageing, glucose is separated out in crystallization;
(3) solid-liquid that obtains in the step (2) is filtered mutually, filter cake is used anti-solvent wash, pure glucose solids, rest solution is isolated ethanol through evaporation, ionic liquid, be reused for the degradation process of Mierocrystalline cellulose etc.
6. process method according to claim 5 is characterized in that, the solution of ionic liquid and glucose filters the temperature of removing solid impurity and is preferably 20 ~ 130 ℃, more preferably 40 ~ 80 ℃.
7. process method according to claim 5 is characterized in that, the temperature that anti-solvent is separated out glucose is preferably 10 ~ 70 ℃, more preferably 0 ~ 30 ℃.
8. process method according to claim 5 is characterized in that, said anti-solvent comprises methyl alcohol, ethanol, Virahol, 1-propyl alcohol, acetonitrile, methylene dichloride; Preferred said anti-solvent is an ethanol.
9. process method according to claim 5; It is characterized in that; Said ionic liquid is mainly to comprise glyoxaline ion liquid as the ionic liquid of active solvent in the cellulose degradation process: 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]).
10. process method according to claim 5 is characterized in that, said ionic liquid is preferably 1:5 ~ 1:35, more preferably 1:10 ~ 1:25 with the ratio of the quality of anti-solvent.
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| WO2017161619A1 (en) * | 2016-03-24 | 2017-09-28 | 陈铭 | Method for separating polypeptide from imidazolium ionic liquid |
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| RU2662192C1 (en) * | 2017-03-13 | 2018-07-24 | Федеральное государственное бюджетное научное учреждение "Федеральный научный центр пищевых систем им. В.М. Горбатова" РАН | Method for obtaining crystalline anhydrous dextrose |
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