CN104610486A - Ionic liquid functionalized ultra-crosslinking polymer as well preparation method and application thereof - Google Patents

Ionic liquid functionalized ultra-crosslinking polymer as well preparation method and application thereof Download PDF

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CN104610486A
CN104610486A CN201510058041.0A CN201510058041A CN104610486A CN 104610486 A CN104610486 A CN 104610486A CN 201510058041 A CN201510058041 A CN 201510058041A CN 104610486 A CN104610486 A CN 104610486A
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ion liquid
vinyl benzyl
surpasses
linked polymer
cross
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CN104610486B (en
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倪华钢
徐莉群
江腾飞
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Hangzhou Reward Technology Co Ltd
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Hangzhou Reward Technology Co Ltd
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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
    • 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
    • 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
    • Y02P20/50—Improvements relating to the production of bulk chemicals

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Abstract

The invention relates to a novel functionalized organic porous polymer and particularly relates to an ionic liquid functionalized ultra-crosslinking polymer and a preparation method thereof. The ionic liquid functionalized ultra-crosslinking polymer is prepared by reacting the following components in a molar ratio: 0.5-10% of a crosslinking agent, 10-70% of an imidazole ionic liquid and 10-80% of a monomer, wherein the used solvent is 1,2-dichloroethane; the monomer used in the ionic liquid functionalized ultra-crosslinking polymer is one or a combination of two or more of benzene, biphenyl, pyrrole, thiophene, furan, 1,3,5-triphenyl benzene or p-chloromethyl styrene, preferably, p-chloromethyl styrene. The porous polymer can be applicable to gas adsorption, especially capture and separation of CO2 gas.

Description

A kind of ion liquid functionalization surpasses cross-linked polymer and preparation method thereof and application
Technical field
The present invention relates to a kind of novel functionalization organic porous polymer, be specifically related to a kind of ion liquid functionalization and surpass cross-linked polymer and preparation method thereof, this porous polymer is applicable to especially CO2 gas entrapment and the separation of gas adsorption aspect.
Background technology
A large amount of consumption burnings of mineral fuel cause CO 2gas emissions increases severely, and environment and ecologic change are on the rise.CO 2separation, catch and store and more and more come into one's own.Traditional gac is short for work-ing life, not easily modifies and regenerates; The skeleton of metal organic framework compound easily subsides, structural instability, simultaneously also to material sensitive such as alkali, acid and steam, and poor chemical stability; The preparation condition of covalent organic framework polymkeric substance is harsh, not easily suitability for industrialized production.And high gas adsorption amount and selectivity are the research emphasis of porous material always.
The advantages such as the specific surface area that super cross-linked polymer has used catalyst and monomer is easy to get, easy reaction, skeletal density are low and larger, gas adsorption be separated in especially at CO 2gas adsorption be separated aspect and achieve very large progress.Ionic liquid has the features such as specific conductivity is high, Heat stability is good, adjustable dissolving power and acid-basicity at CO 2gas adsorption is rather ripe with the application being separated aspect.The technology of the present invention based on both at CO 2gas adsorption and detaching direction present huge advantage, prepare a kind of ion liquid functionalization and surpass cross-linked polymer, and the chemical physical stability overcoming traditional material is poor, preparation condition is harsh and the not easily defect such as modification, and to CO 2gas has catches and separating power greatly, and this has important practical significance to the solution promoting the energy and environmental problem.
Summary of the invention
The object of the invention is to the deficiency overcoming prior art existence, a kind of novel functionalization organic porous polymer is provided, is applicable to gas adsorption aspect especially CO 2gas entrapment and separation.
The present invention is achieved by following technical proposals:
A kind of ion liquid functionalization surpasses cross-linked polymer preparation method and application, it is characterized in that ion liquid functionalization surpasses cross-linked polymer and formed by mol ratio reaction by following composition:
Linking agent: 0.5 ~ 10%;
Imidazole type ion liquid: 10 ~ 70%;
Monomer: 10 ~ 80%;
Solvent is 1,2-ethylene dichloride.
Above-mentioned ion liquid functionalization surpasses monomer described in cross-linked polymer: the one or more combination in benzene, biphenyl, pyrroles, thiophene, furans, 1，3，5-triphenylbenzene or p-chloromethyl styrene.As better selection, above-mentioned monomer is: p-chloromethyl styrene.
As preferably, above-mentioned ion liquid functionalization surpasses linking agent described in cross-linked polymer and is: the one or more combination in Vinylstyrene, formaldehyde dimethylacetal, methylene iodide, triiodomethane or triiodide boron.As better selection, above-mentioned linking agent is: Vinylstyrene.
As preferably, above-mentioned ion liquid functionalization surpasses imidazole type ion liquid described in cross-linked polymer: 1-(4-vinyl benzyl)-3-Methylimidazole hexafluorophosphate, 1-(4-vinyl benzyl)-3-ethyl imidazol(e) hexafluorophosphate, 1-(4-vinyl benzyl)-3-butyl imidazole hexafluorophosphate, 1-(4-vinyl benzyl)-3-methyl imidazolium tetrafluoroborate, 1-(4-vinyl benzyl)-3-ethyl imidazol(e) a tetrafluoro borate, 1-(4-vinyl benzyl)-3-butyl imidazole a tetrafluoro borate, 1-(4-vinyl benzyl)-3-perfluoro capryl limidazolium hexafluorophosphate, 1-(4-vinyl benzyl)-3-perfluoro capryl tetrafluoroborate, one or more combination in 1-(4-vinyl benzyl)-3-polyoxyethylene glycol limidazolium hexafluorophosphate or 1-(4-vinyl benzyl)-3-polyoxyethylene glycol tetrafluoroborate.As better selection, above-mentioned imidazole type ion liquid is: the one or more combination in 1-(4-vinyl benzyl)-3-Methylimidazole hexafluorophosphate, 1-(4-vinyl benzyl)-3-ethyl imidazol(e) hexafluorophosphate, 1-(4-vinyl benzyl)-3-butyl imidazole hexafluorophosphate, 1-(4-vinyl benzyl)-3-methyl imidazolium tetrafluoroborate, 1-(4-vinyl benzyl)-3-ethyl imidazol(e) a tetrafluoro borate or 1-(4-vinyl benzyl)-3-butyl imidazole a tetrafluoro borate.
Ion liquid functionalization surpasses a preparation method for cross-linked polymer, comprises the following steps:
One, radical copolymerization prepares precursor, under nitrogen protection, in there-necked flask, add imidazole type ion liquid, add dehydrated alcohol, be warming up to 50 DEG C, magnetic agitation, after it dissolves completely, add monomer, linking agent and Diisopropyl azodicarboxylate (initiator) successively, be warming up to 78 DEG C, reaction 24h, obtains faint yellow solid;
Two, Friedel-Crafts alkylation surpasses crosslinking reaction, under nitrogen protection, adds the precursor and 1 of step one gained in there-necked flask successively, 2-ethylene dichloride, under room temperature after swelling 2h, adds FERRIC CHLORIDE ANHYDROUS under ice-water bath condition, be warming up to 47 DEG C, reaction 18h, obtains tan product;
Three, anionresin, under nitrogen protection, adds the product of gained in step 2, ethanol and Tetrafluoroboric acid sodium water solution (or phosphofluoric acid aqueous solutions of potassium) successively, is warming up to 30 DEG C in there-necked flask, reaction 24h; After reaction terminates, filtration under diminished pressure, uses deionized water successively, methyl alcohol and washing with acetone, and product, after methyl alcohol extracting 24h, puts into vacuum drying oven, dry 24h at 60 DEG C.
Ion liquid functionalization surpasses an application for cross-linked polymer, and under 273K and 1bar, imidazole type ion liquid content is 40%, and the aperture that ion liquid functionalization surpasses cross-linked polymer is 1.7nm, CO 2adsorptive capacity is 12.11wt%, CO 2isosteric heat of adsorption is 35.7KJ/mol, gas adsorption selectivity (CO 2/ N 2) be 89, show CO 2gas catches/separating power greatly.
Embodiment
Below in conjunction with embodiment, the present invention is described in further detail, and following examples are explanation of the invention and the present invention is not limited to following examples.
Embodiment 1:
A kind of ion liquid functionalization surpasses cross-linked polymer specific configuration composition, and ratio is as follows:
Concrete preparation method: first; under nitrogen protection, add imidazole type ion liquid 0.859g 1-(4-vinyl benzyl chloride)-3-butyl imidazole hexafluorophosphate in 100ml there-necked flask, then add dehydrated alcohol 15ml; be warming up to 50 DEG C; magnetic agitation, after it dissolves completely, adds 3.058g p-chloromethyl styrene successively; 0.16g divinylbenzene and 0.2g Diisopropyl azodicarboxylate; be warming up to 78 DEG C, through free radical copolymerization 24h, obtain faint yellow solid and be precursor.Secondly; under nitrogen protection; 1.25g precursor and 40ml 1 is added successively in 100ml there-necked flask; 2-ethylene dichloride; under room temperature after swelling 2h, under ice-water bath condition, add 1.305g FERRIC CHLORIDE ANHYDROUS, be warming up to 47 DEG C; surpass crosslinking reaction 18h through Friedel-Crafts alkylation, obtain tan product.Finally, anionresin.Take 3.2g Potassium Hexafluorophosphate, use 100ml deionized water dissolving; Under nitrogen protection, in 250ml there-necked flask, add above-mentioned tan product, add 10ml dehydrated alcohol, then add the 100ml phosphofluoric acid aqueous solutions of potassium prepared, be warming up to 30 DEG C, reaction 24h; After reaction terminates, filtration under diminished pressure, use deionized water successively, methyl alcohol and washing with acetone, product is after methyl alcohol extracting 24h, put into vacuum drying oven, at 60 DEG C, namely dry 24h obtains 1-(4-vinyl benzyl chloride)-3-butyl imidazole phosphofluoric acid salt ion liquid functionalization and surpasses cross-linked polymer.
1-(4-vinyl benzyl chloride)-3-butyl imidazole phosphofluoric acid salt ion liquid functionalization surpasses the embody rule of cross-linked polymer: the aperture of material is 1.2nm, under 273K and 1bar condition, and CO 2adsorptive capacity be 7.89wt%, CO 2isosteric heat of adsorption be 32.1KJ/mol, gas adsorption selectivity (CO 2/ N 2) be 67.
Embodiment 2:
A kind of ion liquid functionalization surpasses cross-linked polymer specific configuration composition, and ratio is as follows:
Concrete preparation method is with embodiment 1.
1-(4-vinyl benzyl chloride)-3-butyl imidazole Tetrafluoroboric acid salt ion liquid functionalization surpasses the embody rule of cross-linked polymer: the aperture of material is 1.5nm, under 273K and 1bar condition, and CO 2adsorptive capacity be 8.49wt%, CO 2isosteric heat of adsorption be 32.8KJ/mol, gas adsorption selectivity (CO 2/ N 2) be 73.
Embodiment 3:
A kind of ion liquid functionalization surpasses cross-linked polymer specific configuration medicine, and ratio is as follows:
Concrete preparation method is with embodiment 1.
1-(4-vinyl benzyl chloride)-3-butyl imidazole phosphofluoric acid salt ion liquid functionalization surpasses the embody rule of cross-linked polymer: the aperture of material is 1.7nm, under 273K and 1bar condition, and CO 2adsorptive capacity is 12.11wt%, CO 2isosteric heat of adsorption is 35.7KJ/mol, gas adsorption selectivity (CO 2/ N 2) be 89.
In addition, it should be noted that, the specific embodiment described in this specification sheets can be different.All equivalences of doing according to the preparation process described in inventional idea of the present invention and principle or simple change, be included in the protection domain of patent of the present invention.Those skilled in the art can make various amendment or supplement or adopt similar mode to substitute to described specific embodiment; only otherwise depart from composition of the present invention or surmount this scope as defined in the claims, protection scope of the present invention all should be belonged to.

Claims (5)

1. ion liquid functionalization surpasses a cross-linked polymer, it is characterized in that: by mole% meter, comprises following component:
Linking agent: 0.5 ~ 10%;
Imidazole type ion liquid: 10 ~ 70%;
Monomer: 10 ~ 80%;
Solvent is 1,2-ethylene dichloride, and described monomer is the one or more combination in benzene, biphenyl, pyrroles, thiophene, furans, 1，3，5-triphenylbenzene or p-chloromethyl styrene.
2. ion liquid functionalization according to claim 1 surpasses cross-linked polymer, it is characterized in that described linking agent is the one or more combination in Vinylstyrene, formaldehyde dimethylacetal, methylene iodide, triiodomethane or triiodide boron.
3. ion liquid functionalization according to claim 1 surpasses cross-linked polymer, it is characterized in that described imidazole type ion liquid is: 1-(4-vinyl benzyl)-3-Methylimidazole hexafluorophosphate, 1-(4-vinyl benzyl)-3-ethyl imidazol(e) hexafluorophosphate, 1-(4-vinyl benzyl)-3-butyl imidazole hexafluorophosphate, 1-(4-vinyl benzyl)-3-methyl imidazolium tetrafluoroborate, 1-(4-vinyl benzyl)-3-ethyl imidazol(e) a tetrafluoro borate, 1-(4-vinyl benzyl)-3-butyl imidazole a tetrafluoro borate, 1-(4-vinyl benzyl)-3-perfluoro capryl limidazolium hexafluorophosphate, 1-(4-vinyl benzyl)-3-perfluoro capryl tetrafluoroborate, one or more combination in 1-(4-vinyl benzyl)-3-polyoxyethylene glycol limidazolium hexafluorophosphate or 1-(4-vinyl benzyl)-3-polyoxyethylene glycol tetrafluoroborate.
4. ion liquid functionalization surpasses a preparation method for cross-linked polymer, it is characterized in that comprising the following steps:
One, radical copolymerization prepares precursor, under nitrogen protection, in there-necked flask, add imidazole type ion liquid, add dehydrated alcohol, be warming up to 50 DEG C, magnetic agitation, after it dissolves completely, add monomer, linking agent and Diisopropyl azodicarboxylate (initiator) successively, be warming up to 78 DEG C, reaction 24h, obtains faint yellow solid;
Two, Friedel-Crafts alkylation surpasses crosslinking reaction, under nitrogen protection, adds the precursor and 1 of step one gained in there-necked flask successively, 2-ethylene dichloride, under room temperature after swelling 2h, adds FERRIC CHLORIDE ANHYDROUS under ice-water bath condition, be warming up to 47 DEG C, reaction 18h, obtains tan product;
Three, anionresin, under nitrogen protection, adds the product of gained in step 2, ethanol and Tetrafluoroboric acid sodium water solution (or phosphofluoric acid aqueous solutions of potassium) successively, is warming up to 30 DEG C in there-necked flask, reaction 24h; After reaction terminates, filtration under diminished pressure, uses deionized water successively, methyl alcohol and washing with acetone, and product, after methyl alcohol extracting 24h, puts into vacuum drying oven, dry 24h at 60 DEG C.
5. one kind surpasses the purposes of cross-linked polymer according to the ion liquid functionalization of claim 4 gained, it is characterized in that under 273K and 1bar condition, it is 40% that imidazole type ion liquid functionalization surpasses cross-linked polymer content, and the aperture that ion liquid functionalization surpasses cross-linked polymer is 1.7nm, CO 2adsorptive capacity is 12.11wt%, CO 2isosteric heat of adsorption is 35.7KJ/mol, gas adsorption selectivity (CO 2/ N 2) be 89.
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CN105327687A (en) * 2015-11-19 2016-02-17 华侨大学 CO2 absorbent as well as preparation method and application thereof
CN105854837A (en) * 2016-04-12 2016-08-17 苏州大学 Recyclable material for adsorbing metal ions in wastewater
CN108070049A (en) * 2016-11-15 2018-05-25 中国科学院大连化学物理研究所 A kind of preparation method of quaternary ammonium salt ionic liquid polymer
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CN110093054A (en) * 2018-01-30 2019-08-06 比亚迪股份有限公司 Cross-linking type copolymer and polymer dielectric and preparation method thereof and all-solid lithium-ion battery
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