CN105418843A - Preparation method of porous polymerized ionic liquid used for capture/absorption of CO2 - Google Patents
Preparation method of porous polymerized ionic liquid used for capture/absorption of CO2 Download PDFInfo
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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
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1456—Removing acid components
- B01D53/1475—Removing carbon dioxide
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1493—Selection of liquid materials for use as absorbents
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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
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/34—Monomers containing two or more unsaturated aliphatic radicals
- C08F212/36—Divinylbenzene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/30—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by mixing gases into liquid compositions or plastisols, e.g. frothing with air
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/30—Ionic liquids and zwitter-ions
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2325/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Derivatives of such polymers
- C08J2325/02—Homopolymers or copolymers of hydrocarbons
- C08J2325/16—Homopolymers or copolymers of alkyl-substituted styrenes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2339/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Derivatives of such polymers
- C08J2339/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02C—CAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]
- Y02C20/00—Capture or disposal of greenhouse gases
- Y02C20/40—Capture or disposal of greenhouse gases of CO2
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/151—Reduction of greenhouse gas [GHG] emissions, e.g. CO2
Abstract
A p reparation method of a porous polymerized ionic liquid used for capture/absorption of CO2 belongs to the technical field of polymerized ionic liquids. In the invention, an ionic liquid monomer, of which the cations have amino groups, is polymerized to form the polymerized ionic liquid, wherein CO2 is fed into a polymerizing reactor during the polymerization process so that the CO2 is combined with the amino groups. The polymerized ionic liquid then is used for removing the CO2 at a high temperature and under a low pressure, wherein a large quantity of pores are formed during the CO2 removal process, thereby preparing the polymerized ionic liquid which has large specific surface area and large pore volume. Meanwhile, the amino groups are exposed out of the surface of the polymerized ionic liquid again, so that the porous polymerized ionic liquid can be used for adsorbing the CO2.
Description
Technical field
The present invention relates to a kind of preparation method of the porous polymeric ionic liquid for carbon dioxide adsorption, more specifically, the present invention is by introducing carbonic acid gas in the course of the polymerization process, and the method preparation removed again after polymerization has the porous polymeric ionic liquid of absorbing carbon dioxide ability.
Background technology
Ionic liquid (IonicLiquids) is the eco-friendly functional materials of one developed in recent years.They are the salt be made up of specific positively charged ion and negatively charged ion.It is a large hot issue of this area research by supported ionic liquids, by by ionic liquid supported on different carriers, it is made to have the characteristic of ionic liquid and porous carrier materials concurrently, be conducive to expanding interfacial area, shortening the evolving path, overcome ionic liquid mass transfer problem in actual applications, make it more stable, the separation after using, recycling also easily realize, and will have more advantage in industrial continuous application.Bibliographical information be that the method for particle type materials can be summed up as two classes by supported ionic liquids: (1) by the method for coupling agent or coating, by ionic liquid loaded in inorganic porous material; (2) by quoting polymerisable group on the il, ionic liquid is made linear or crosslinked solid polymer particle through polyreaction.Yoshizawa has synthesized on a series of imidazole side chain with double bond, polymerisable ionic liquid monomer (YoshioM, MukaiT, OhnoH.One-dimensionaliontransportinself-organizedcolumna rionicliquids.J.Am.Chem.Soc., 2004,126 (4): 994-995).This kind of ionic liquid, by radical polymerization, can obtain solid ion liquid polymers.Tang etc. have prepared class powdery ion liquid polymer (TangJB, SunWL, TangHD, RadoszM, a ShenYQ.EnhancedCO
2absorptionofPoly (ionicliquid) sMacromolecules, 2005,38:2037-2039).These ion liquid polymers are amorphous states, are non-porous structure, and this obviously have impact on it as usefulness when catalyzer or sorbent material.If these polymeric ionic liquids are formed vesicular structure, utilize again the designability of its zwitterion liquid structure simultaneously, ionic liquid is not only made to have unique functionalization character, have again the characteristic of solid porous material concurrently simultaneously, and the lower stability coupling agent when using silica gel load ionic liquid can avoided to come off and cause, to be functionalization and supported fabulous combination, in a lot of, there is great application prospect undoubtedly.
In recent years, greenhouse gases CO
2a large amount of discharges, result in the Greenhouse effect increasingly sharpened, the global warming caused.Bibliographical information aims at trapping CO
2and the positively charged ion of design is containing amino functionalized ion liquid, it is to CO
2receptivity close to 0.5mol/mol, apparently higher than general ionic liquid (BatesED, MaytonRD, NtaiI.CO
2capturebyatask-specificionicliquid.J.Am.ChemSoc., 2002,124 (6): 926-927), this sorption more comes from amino in ionic liquid and CO
2reaction generate carbaminate, during regeneration carbamate decomposition release CO
2.But such viscosity of il is comparatively large, and during mixing, interfacial area is little, is unfavorable for the dissolving of gas in ionic liquid and diffusion, hinders it at CO
2industrial application in trapping.
Summary of the invention
The object of the present invention is to provide a kind of method with the polymeric ionic liquid of vesicular structure for the preparation of carbon dioxide adsorption.
Of the present invention adopted preparation method utilizes on positively charged ion with amino (NH
2) polymerisable ionic liquid monomer, introduce carbonic acid gas in the course of the polymerization process, carbonic acid gas is made to form carbaminate with amino combination, complete polyreaction simultaneously, the polymeric ionic liquid obtained is carbon dioxide removal under certain temperature and vacuum condition again, amino is restored, thus prepares the polymeric ionic liquid with absorbing carbon dioxide ability.
Concrete preparation method of the present invention is as follows:
With 1-vinyl-3-aminooimidazole hydrobromate and Vinylstyrene for polymer raw, add a certain amount of polymerization starter, be dissolved in that ethanol and water forms mixing solutions, be heated to certain temperature and carry out polyreaction, make reaction maintain certain hour.In reactor, carbon dioxide is passed through in polymerization process.After reaction terminates, remove solvent, at a certain temperature vacuum removal carbonic acid gas is carried out to gained polymeric ionic liquid white powder, obtain the polymeric ionic liquid with vesicular structure.
Above-mentioned 1-vinyl-3-aminooimidazole hydrobromate and Vinylstyrene can be arbitrary proportion, and preferably both mol ratios are 1:1.
Polymerization starter selected in aforesaid method comprises Diisopropyl azodicarboxylate.Its mole dosage is the 0.1-1% of polymerization single polymerization monomer integral molar quantity.
In the mixed solvent of the second alcohol and water composition used in aforesaid method, the volume ratio of second alcohol and water is 1:1-3:1.
In aforesaid method, polyreaction is carried out at 60-100 DEG C, reaction times 6-24 hour.
In aforesaid method, gained polymeric ionic liquid carries out vacuum-treat at 150-240 DEG C, and working pressure is 5-10kPa (absolute pressure); Operating time is 10-24 hour.
Characteristics and advantages of the present invention is: by polymerization process, carbonic acid gas is passed in polymerization reactor, the amino on carbonic acid gas and monomer is made to form carbaminate, the polymeric ionic liquid obtained again by the method carbon dioxide removal of the decompression that heats up, thus forms specific surface area at 100-200m
2the porous polymeric ionic liquid of/g, the channel surfaces of meanwhile obtained polymeric ionic liquid, with a large amount of amino, has the ability of very strong absorbing carbon dioxide.Adopt method of the present invention to prepare polymeric ionic liquid, overcome amino a large amount of in traditional polymeric ionic liquid and be wrapped in inside, the shortcoming of the effect of absorbing carbon dioxide can not be played.The carbon dioxide adsorption ability of the amino polymeric ionic liquid of porous that the inventive method is prepared is 5-10 times of the amino polymeric ionic liquid of atresia.
Embodiment
Below will the present invention is described in further detail by embodiment, but the present invention is not limited to following examples.
Embodiment 1: 1-vinyl-3-aminooimidazole hydrobromate (about 0.01mol), the 2.36g Vinylstyrene (55% of getting 3g, about 0.01mol) and the initiator Diisopropyl azodicarboxylate of 0.00536g in the there-necked flask of 100ml, the mixing solutions adding 50ml ethanol and water is solvent (volume ratio of ethanol and water is 1:1).CO is passed through to there-necked flask in reaction process
2gas, is heated to 60 DEG C and carries out polyreaction, reaction maintenance 6 hours.Reaction terminates, and by product vacuum suction filtration, removes solvent, and by dehydrated alcohol and washed with de-ionized water 3 times, be placed on vacuum treatment chamber, at 150 DEG C, carry out vacuum-treat, working pressure is 5kPa, treatment time is 10 hours, obtains white solid powder, is porous polymeric ionic liquid.
Embodiment 2: 1-vinyl-3-aminooimidazole hydrobromate (about 0.01mol), the 2.36g Vinylstyrene (55% of getting 3g, about 0.01mol) and the initiator Diisopropyl azodicarboxylate of 0.0536g in the there-necked flask of 100ml, the mixing solutions adding 50ml ethanol and water is solvent (volume ratio of ethanol and water is 3:1).CO is passed through to there-necked flask in reaction process
2gas, is heated to 100 DEG C and carries out polyreaction, reaction maintenance 6 hours.Reaction terminates, and by product vacuum suction filtration, removes solvent, and by dehydrated alcohol and washed with de-ionized water 3 times, be placed on vacuum treatment chamber, at 240 DEG C, carry out vacuum-treat, working pressure is 10kPa, treatment time is 24 hours, obtains white solid powder, is porous polymeric ionic liquid.
Comparative example 1: 1-vinyl-3-aminooimidazole hydrobromate (about 0.01mol), the 2.36g Vinylstyrene (55% of getting 3g, about 0.01mol) and the initiator Diisopropyl azodicarboxylate of 0.00536g in the there-necked flask of 100ml, the mixing solutions adding 50ml ethanol and water is solvent (volume ratio of ethanol and water is 1:1).Obstructed gas in reaction process, is heated to 60 DEG C and carries out polyreaction, reaction maintenance 6 hours.Reaction terminates, and by product vacuum suction filtration, removes solvent, and by dehydrated alcohol and washed with de-ionized water 3 times, be placed on vacuum treatment chamber, at 150 DEG C, carry out vacuum-treat, working pressure is 5kPa, treatment time is 10 hours, obtains white solid powder, is porous polymeric ionic liquid.
Comparative example 2: 1-vinyl-3-aminooimidazole hydrobromate (about 0.01mol), the 2.36g Vinylstyrene (55% of getting 3g, about 0.01mol) and the initiator Diisopropyl azodicarboxylate of 0.0536g in the there-necked flask of 100ml, the mixing solutions adding 50ml ethanol and water is solvent (volume ratio of ethanol and water is 3:1).Obstructed gas in reaction process, is heated to 100 DEG C and carries out polyreaction, reaction maintenance 6 hours.Reaction terminates, and by product vacuum suction filtration, removes solvent, and by dehydrated alcohol and washed with de-ionized water 3 times, be placed on vacuum treatment chamber, at 240 DEG C, carry out vacuum-treat, working pressure is 10kPa, treatment time is 24 hours, obtains white solid powder, is porous polymeric ionic liquid.
Adopt nitrogen low-temperature physics absorption method, obtain adsorption/desorption balance isothermal curve, calculated specific surface area and the BJH method calculated pore of gained polymeric ionic liquid by BET formula.The results are shown in Table 1.
Combine with temperature programmed desorption(TPD) (TPD) method and volumetry and measure the porous functionalization polymeric ionic liquid CO absorption of gained
2performance.First under He, rise to the impurity that 200 DEG C remove polymeric ionic liquid polymer surfaces with the speed of 10 DEG C/min in experiment, rear control temperature is CO absorption at 35 DEG C
2, adsorb 60 minutes.After absorption terminates, then under He purges, with the speed of 10 DEG C/min, temperature rises to 250 DEG C of desorptions, and the desorption gas out NaOH aqueous solution absorbs, and calculates polymeric ionic liquid to CO
2absorbed dose.The results are shown in Table 1.
Table 1 polymeric ionic liquid surface area, pore volume and absorbing carbon dioxide ability
Data as can be seen from table 1, in embodiment 1 and 2, be pore-creating agent by carbonic acid gas, in the course of the polymerization process the amino of carbonic acid gas on ionic liquid monomer is combined and forms carbaminate, carbon dioxide removal after completion of the polymerization reaction again, the polymeric ionic liquid that amino method of restoring is obtained does not use the polymeric ionic liquid of carbonic acid gas pore-creating agent to have larger specific surface area and pore volume than in comparative example 1 and 2, illustrates that this method prepares the effective ways of porous polymeric ionic liquid.Meanwhile, a large amount of amino exposed in duct can effective absorbing carbon dioxide, and the carbon dioxide adsorption ability of polymeric ionic liquid obtained in embodiment 1 and 2 has obvious lifting.
Claims (7)
1. the preparation method for the porous polymeric ionic liquid of collecting carbonic anhydride/absorption, it is characterized in that, comprise the following steps: with 1-vinyl-3-aminooimidazole hydrobromate and Vinylstyrene for polymer raw, add a certain amount of polymerization starter, be dissolved in the mixing solutions that ethanol and water form, be heated to certain temperature and carry out polyreaction, make reaction maintain certain hour; In reactor, carbon dioxide is passed through in polymerization process; After reaction terminates, remove solvent, at a certain temperature vacuum removal carbonic acid gas is carried out to gained polymeric ionic liquid white powder, obtain the polymeric ionic liquid with vesicular structure.
2. in accordance with the method for claim 1, it is characterized in that, the mol ratio of 1-vinyl-3-aminooimidazole hydrobromate and Vinylstyrene is 1:1.
3. in accordance with the method for claim 1, it is characterized in that, the polymerization starter selected comprises Diisopropyl azodicarboxylate, and Diisopropyl azodicarboxylate mole dosage is the 0.1-1% of polymerization single polymerization monomer integral molar quantity.
4. in accordance with the method for claim 1, it is characterized in that, in the mixed solvent of the second alcohol and water composition used, the volume ratio of second alcohol and water is 1:1-3:1.
5. in accordance with the method for claim 1, it is characterized in that, polyreaction is carried out at 60-100 DEG C, reaction times 6-24 hour.
6. in accordance with the method for claim 1, it is characterized in that, gained polymeric ionic liquid carries out vacuum-treat at 150-240 DEG C, and working pressure is 5-10kPa; Operating time is 10-24 hour.
7. according to the porous polymeric ionic liquid that the method described in any one of claim 1-6 prepares.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107141497A (en) * | 2017-04-20 | 2017-09-08 | 国家纳米科学中心 | The preparation and its application of ionic organic porous films with solvent response |
| CN109364993A (en) * | 2018-12-17 | 2019-02-22 | 太原理工大学 | For normal pressure catalyzed conversion CO2Poly ion liquid catalyst and preparation method thereof |
| CN111871152A (en) * | 2020-07-30 | 2020-11-03 | 浙江大学 | Functionalized ionic liquid and preparation method and application thereof |
| CN112191237A (en) * | 2020-09-27 | 2021-01-08 | 华侨大学 | Preparation and application of porous polyion liquid compound and method for adsorbing carbon dioxide by using porous polyion liquid compound |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107141497A (en) * | 2017-04-20 | 2017-09-08 | 国家纳米科学中心 | The preparation and its application of ionic organic porous films with solvent response |
| CN109364993A (en) * | 2018-12-17 | 2019-02-22 | 太原理工大学 | For normal pressure catalyzed conversion CO2Poly ion liquid catalyst and preparation method thereof |
| CN109364993B (en) * | 2018-12-17 | 2021-03-30 | 太原理工大学 | For catalytic conversion of CO at normal pressure2Polyion liquid catalyst and preparation method thereof |
| CN111871152A (en) * | 2020-07-30 | 2020-11-03 | 浙江大学 | Functionalized ionic liquid and preparation method and application thereof |
| CN112191237A (en) * | 2020-09-27 | 2021-01-08 | 华侨大学 | Preparation and application of porous polyion liquid compound and method for adsorbing carbon dioxide by using porous polyion liquid compound |
| CN112191237B (en) * | 2020-09-27 | 2023-05-30 | 华侨大学 | Preparation and application of porous polyionic liquid compound and method for adsorbing carbon dioxide by using porous polyionic liquid compound |
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