CN105149002A - ZIF-8 encapsulated amino ionic liquid type carbon dioxide adsorbing-catalyzing agent - Google Patents

ZIF-8 encapsulated amino ionic liquid type carbon dioxide adsorbing-catalyzing agent Download PDF

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CN105149002A
CN105149002A CN201510659602.2A CN201510659602A CN105149002A CN 105149002 A CN105149002 A CN 105149002A CN 201510659602 A CN201510659602 A CN 201510659602A CN 105149002 A CN105149002 A CN 105149002A
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zif
ionic liquid
absorption
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catalyst
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CN105149002B (en
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史利娟
卢建军
李庆朝
成晶晶
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Taiyuan University of Technology
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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 discloses a ZIF-8 encapsulated amino ionic liquid type carbon dioxide adsorbing-catalyzing agent. The ZIF-8 encapsulated amino ionic liquid type carbon dioxide adsorbing-catalyzing agent is prepared according to the following steps: taking the metal organic framework material ZIF-8 as a carrier; taking the amino-group functionalized ionic liquid 1-(3-aminopropyl)-3-methylimidazole chloride as an active component; immobilizing the amino-group functionalized ionic liquid in the super-cages of the ZIF-8 carrier in an in-situ manner during preparation of ZIF-8, wherein 1.5 to 5 mmol of the amino-group functionalized ionic liquid is immobilized in each gram of the adsorbing-catalyzing agent. The adsorbing-catalyzing agent integrates the functions of selective adsorbing and catalyzing into a whole, and can be used for synchronously adsorbing and converting carbon dioxide, so as to reduce the cost of the CUU technology.

Description

ZIF-8 encapsulates amino ion liquid type CO 2absorption-catalyst and preparation method
Technical field
The present invention relates to a kind of CO 2absorption-catalyst, particularly relates to a kind of based on ionic liquid active component, integrates the efficient CO of selective absorption and catalysis 2absorption-catalyst, and the preparation method of this absorption-catalyst.
Background technology
Global warming has become the environmental problem received much concern, with CO 2being that main greenhouse gases discharge in a large number, is the main cause causing greenhouse effects to aggravate.From resource angle, CO 2again C 1no matter carbon resource the most cheap and abundant in family, consider from the utilization of resources or the angle of environmental protection, relevant CO 2research and development that are fixing and chemical conversion are all significant.Therefore, CO 2trapping becomes the current hot spot technology urgently developed with (CCU) technology of utilization.
CO 2inertia is very large, is not easily activated, and realize its chemistry and fix and transform very difficult, thus the performance issue of adsorbent and catalyst constrains the application and development of CCU technology.If design a kind of collecting to obtain and the absorption-catalyst of catalysis in one, by CO 2after efficient trapping, converted in-situ is the product that added value is higher, then can simplify technology path, reduce costs, and promotes the development of CCU technology.
Ionic liquid is made up of anions and canons completely, lower than the organic salt be in a liquid state in 100 DEG C of temperature ranges.Ionic liquid has the peculiar properties such as steam forces down, nonflammable, heat endurance is high, solvability is strong, structures and characteristics is adjustable.These characteristics make ionic liquid become alternative traditional organic amine solvent trapping fixation of C O 2new type ideal solvent.In addition, unique catalytic performance also makes ionic liquid in a mild condition namely to multiple CO 2conversion reaction shows excellent catalytic activity and selective.Therefore, the ionic liquid of design ad hoc structure, as active component, will be expected to realize CO 2trapping and conversion integration.But ionic liquid also exists again that viscosity is large, high in cost of production shortcoming, seriously constrains its application.
Metal-organic framework materials (MOFs) is the class novel porous materials generated by self assembly by metal ion and organic ligand, have that specific area is large, pore passage structure is regular, duct and surface chemical property can the features such as modulation, in absorption, be separated and all show wide application prospect in catalysis etc.
Zeolitic imidazolate framework material (ZIFs) is the one in MOFs material, and it is the nano-porous materials that the class being connected by transition metal atoms Zn or Co and imidazoles or imdazole derivatives and being generated is novel, have zeolite topological.ZIFs not only has the advantage of MOFs material, and compares with MOFs material, has more excellent heat and hydrothermal stability.ZIF-8 is the representational one of most in ZIFs material, and its cage mouth diameter 0.34nm, with CO 2the kinetic diameter (0.33nm) of molecule is close, therefore to CO 2have well selective.ZIF-8 shows excellent performance in multiple fields such as absorption, separation, gas storage and catalysis.
Summary of the invention
The object of this invention is to provide a kind of ZIF-8 integrating selective absorption and catalysis and encapsulate amino ion liquid type CO 2absorption-catalyst, and the preparation method of this absorption-catalyst, to realize CO 2synchronous absorption and conversion, reduce CUU technical costs.
ZIF-8 of the present invention encapsulates amino ion liquid type CO 2absorption-catalyst is for carrier with metal-organic framework materials ZIF-8, amino functional ionic liquid 1-(3-aminopropyl)-3-methylimidazolium chloride is active component, obtain immobilized for amino functional ionic liquid original position in the supercage of described ZIF-8 carrier while preparation ZIF-8, wherein, immobilized in absorption-catalyst described in every 1g have 1.5 ~ 5mmol amino functional ionic liquid.
The present invention and then provide one and prepare described ZIF-8 and encapsulate amino ion liquid type CO 2the method of absorption-catalyst is in first anhydrous acetonitrile dicyandiamide solution under nitrogen protection, by n-methylimidazole and 3-chloro propyl amine hydrochloric acid salt heating reflux reaction prepare amino functional ionic liquid 1-(3-aminopropyl)-3-methylimidazolium chloride, again 1-(3-aminopropyl)-3-methylimidazolium chloride and zinc nitrate hexahydrate are scattered in absolute methanol, drip glyoxal ethyline absolute methanol solution, add thermal response and prepare described ZIF-8 and encapsulate amino ion liquid type CO 2absorption-catalyst.
In the above-mentioned preparation method of the present invention, described in n-methylimidazole is preferably 1.2 ~ 2: 1 with the mole dosage ratio of 3-chloro propyl amine hydrochloric acid salt.
Further, the present invention is by described n24 ~ 72 hours are reacted in-methylimidazole and the 3-chloro propyl amine hydrochloric acid salt anhydrous acetonitrile dicyandiamide solution at 70 ~ 80 DEG C, with anhydrous ethyl acetate washing, drying after product removing acetonitrile, again with after a small amount of water-soluble solution, by KOH solution adjust ph to 8, the washing also dry precipitation separated out obtains amino functional ionic liquid.
In the above-mentioned preparation method of the present invention, be 0.1 ~ 0.15: 1 for the preparation of the zinc nitrate hexahydrate of ZIF-8 and the mole dosage ratio of glyoxal ethyline, and described glyoxal ethyline and zinc nitrate hexahydrate are reacted 24 ~ 72 hours in the absolute methanol dicyandiamide solution at 20 ~ 30 DEG C.
And then the amino functional ionic liquid added in the process of preparation ZIF-8 is 0.2 ~ 0.5: 1 with the mole dosage ratio of zinc nitrate hexahydrate.
ZIF-8 prepared by the present invention encapsulates amino ion liquid type CO 2absorption-catalyst can be applicable to selective absorption in flue gas and catches CO 2and realize CO 2efficient catalytic transform.
And then, be suitable for CO in the flue gas of absorption of the present invention-Catalyst Adsorption conversion 2volumn concentration be 10 ~ 20%.
ZIF-8 of the present invention is utilized to encapsulate amino ion liquid type CO 2absorption-catalyst traps and conversion CO 2concrete grammar be: under the adsorption temp of 25 ~ 100 DEG C, encapsulate amino ion liquid type CO with described ZIF-8 2cO is caught in the absorption of absorption-catalyst choice 2, then cycloaddition reaction is carried out, synthesizing annular carbonate with epoxide at reaction pressure 2Mpa, temperature 50 ~ 120 DEG C.
Usually, the reaction time of described cycloaddition reaction is 3 ~ 40 hours.
Preferably, epoxide of the present invention is epoxychloropropane, and the cyclic carbonate of synthesis is 4-chloromethyl-[1,3] dioxy ring penta-2-ketone.
The present invention adopts the method for fabricated in situ, have in the supercage compared with the 3-dimensional metal organic framework material ZIF-8 of Large ratio surface sum pore volume by immobilized for amino functional ionic liquid active component, prepare and a kind ofly integrate that absorption catches with catalyzed conversion function, the efficient CO that capacity is large, activity is high and cyclic utilization rate is good 2heterogeneous absorption-catalyst, achieves CO 2high selectivity, Large Copacity, low energy consumption trapping and cyclic carbonate Efficient Conversion, be CO 2fixing conversion particularly CO in flue gas 2industrial utilization provide effective method.
By ionic liquid supported on the porous carrier of bigger serface, can significantly reduce ionic liquid consumption, reduce CO 2resistance to mass tranfer, and be easy to be separated and reuse, thus can significantly improve the adsoption catalysis efficiency of absorption-catalyst and recycle rate.Compared with general mesopore molecular sieve SBA-16, MCM-41, SBA-15 etc., ZIF-8 has unique microcellular structure and larger specific area, and its bore dia and CO 2kinetic diameter close, have higher application potential in fields such as absorption, separation, catalysis, can as the excellent carrier of solid-loaded ionic-liquid.
Absorption-catalyst prepared by the present invention has concentrated the good trapping performance of ionic liquid and excellent catalyzed conversion performance, simultaneously based on ionic liquid and porous carrier to the synergy of acid gas adsorption, it is to CO 2selective absorption performance be fully reflected, to the CO in typical flue gas temperature range 2there is good absorption property, to epoxide and CO 2between cycloaddition reaction also there is the advantages such as high, selective good, the reusable edible of conversion ratio.
Absorption-catalyst prepared by the present invention can efficient adsorption CO under normal pressure, effluent gas temperature 2, and by CO under uniform temperature, pressure 2be converted into cyclic carbonate, show active high, selective good, reaction condition is gentle, be easy to the advantages such as separation, reusable edible, can realize CO 2synchronous absorption and conversion, reduce CUU technical costs .
Detailed description of the invention
Embodiment 1
Take 16.42g (200mmol) n-methylimidazole, 13.02g (100mmol) 3-chloro propyl amine hydrochloric acid salt, joins in 50mL anhydrous acetonitrile, and logical nitrogen protection, is heated to 75 DEG C, back flow reaction 24 hours under stirring.After reaction terminates, revolve and steam removing solvent acetonitrile, wash the product obtained with anhydrous ethyl acetate, be dissolved in after room temperature in vacuo drying in a small amount of water, by KOH solution adjust ph to 8, precipitation method removing KCl, vacuum drying, obtains flaxen amino functional ionic liquid 14g.
Take 1.5g zinc nitrate hexahydrate, be scattered in 70mL absolute methanol together with the above-mentioned amino functional ionic liquid 0.221g prepared and obtain dispersion liquid, 3.3g2-methylimidazole is dissolved in 70mL absolute methanol, is slowly added drop-wise in above-mentioned dispersion liquid, vigorous stirring 24 hours under room temperature.Centrifugation, by the solid that obtains with after absolute methanol washing, vacuum drying, obtains ZIF-8 and encapsulates amino ion liquid type CO 2absorption-catalyst white powder 0.80g, is labeled as IL-1ZIF-8.
Embodiment 2
Take 1.5g zinc nitrate hexahydrate, be scattered in 70mL absolute methanol together with the amino functional ionic liquid 0.295g that embodiment 1 prepares and obtain dispersion liquid, 3.3g2-methylimidazole is dissolved in 70mL absolute methanol, slowly be added drop-wise in above-mentioned dispersion liquid, vigorous stirring 36 hours under room temperature.Centrifugation, by the solid that obtains with after absolute methanol washing, vacuum drying, obtains ZIF-8 and encapsulates amino ion liquid type CO 2absorption-catalyst white powder 0.70g, is labeled as IL-3ZIF-8.
Embodiment 3
Take 1.5g zinc nitrate hexahydrate, be scattered in 70mL absolute methanol together with the amino functional ionic liquid 0.442g that embodiment 1 prepares and obtain dispersion liquid, 3.3g2-methylimidazole is dissolved in 70mL absolute methanol, slowly be added drop-wise in above-mentioned dispersion liquid, vigorous stirring 30 hours under room temperature.Centrifugation, by the solid that obtains with after absolute methanol washing, vacuum drying, obtains ZIF-8 and encapsulates amino ion liquid type CO 2absorption-catalyst white powder 0.65g, is labeled as IL-5ZIF-8.
Embodiment 4
Taking 1.5g zinc nitrate hexahydrate is scattered in 70mL absolute methanol, slowly drips the absolute methanol that 70mL is dissolved with 3.3g2-methylimidazole, vigorous stirring 48 hours under room temperature.Centrifugation, by the solid that obtains with after absolute methanol washing, vacuum drying, obtains pure metallic organic framework ZIF-8 white powder 1.3g.
Following application examples uses CO 2infrared spectrum analyser, the ZIF-8 prepared with embodiment 4 in contrast, measures and to compare ZIF-8 prepared by above-described embodiment under normal pressure and encapsulate amino ion liquid type CO 2absorption-catalyst is to sour gas CO 2adsorption selectivity.
Application examples 1
Taking about 1.0gIL-5ZIF-8 is filled in adsorptive reactor, at 80cm 3the nitrogen of/min flows down, and is warming up to 140 DEG C and keeps constant temperature, purge 60min from room temperature with the heating rate of 1 DEG C/min; Then be cooled to adsorption temp 25 DEG C in nitrogen atmosphere, pass into containing 85%N with the gas flow rate of 100ml/min 2and 15%CO 2gaseous mixture, adsorption reaction 10min, and real-time recorded data.The CO of sample 2adsorption selection amount is according to CO 2infrared spectrum analyser measurement data calculates, and adsorption selection amount is 2.26mmol/g.
Application examples 2
With the CO of 50 DEG C 2adsorption reaction temperature measuring IL-5ZIF-8, other conditions are with application examples 1, CO 2adsorption selection amount is 2.29mmol/g.
Application examples 3
With the CO of 75 DEG C 2adsorption reaction temperature measuring IL-5ZIF-8, other conditions are with application examples 1, CO 2adsorption selection amount is 3.05mmol/g.
Application examples 4
IL-1ZIF-8, CO is measured according to application examples 1 condition 2adsorption selection amount is 1.54mmol/g.
Comparative example 1
Taking about 1.0gZIF-8 is filled in adsorptive reactor, at 80cm 3the nitrogen of/min flows down, and is warming up to 140 DEG C and keeps constant temperature, purge 60min from room temperature with the heating rate of 1 DEG C/min; Then be cooled to adsorption temp 25 DEG C in nitrogen atmosphere, pass into containing 85%N with the gas flow rate of 100ml/min 2and 15%CO 2gaseous mixture, adsorption reaction 10min, and real-time recorded data.The CO of sample 2adsorption selection amount is according to CO 2infrared spectrum analyser measurement data calculates, and adsorption selection amount is 1.02mmol/g.
Comparative example 2
CO 2adsorption reaction temperature is 50 DEG C, and other conditions are with comparative example 1, CO 2adsorption selection amount is 1.13mmol/g.
Comparative example 3
CO 2adsorption reaction temperature is 75 DEG C, and other conditions are with comparative example 1, CO 2adsorption selection amount is 1.34mmol/g.
As can be seen from above-mentioned application examples and comparative example determination data, under similarity condition, absorption-catalyst prepared by the present invention is to CO 2adsorption selectivity be significantly better than ZIF-8.
Application examples 5
0.5g absorption-catalyst I L-5ZIF-8 is added, 9.25g (100mmol) epoxychloropropane in 100mL autoclave, airtight, with the CO of 1.0Mpa 2displace air in still completely, be slowly warming up to 120 DEG C, controlling reaction pressure is that 2.0Mpa reacts 6 hours.After the cooling of question response still, slowly release remaining CO 2, get supernatant liquor after products obtained therefrom is centrifugal and carry out GC analysis, the productive rate of 4-chloromethyl-[1,3] dioxy ring penta-2-ketone is 95.5%, selective 98.2%.
Application examples 6
Add 0.5g absorption-catalyst I L-5ZIF-8, reaction temperature 100 DEG C, other conditions are identical with application examples 5, and the productive rate recording 4-chloromethyl-[1,3] dioxy ring penta-2-ketone is 92.6%, and selective 100%.
Application examples 7
Add 0.5g absorption-catalyst I L-3ZIF-8, reaction temperature 100 DEG C, other conditions are identical with application examples 5, and the productive rate recording 4-chloromethyl-[1,3] dioxy ring penta-2-ketone is 91.8%, and selective 96.4%.
Application examples 8
Add 0.5g absorption-catalyst I L-5ZIF-8, reaction temperature 90 DEG C, other conditions are identical with application examples 5, and the productive rate recording 4-chloromethyl-[1,3] dioxy ring penta-2-ketone is 92.91%, and selective 95.39%.
Application examples 9
By colourless to supernatant for the absorption of collected by centrifugation after reaction in application examples 5-catalyst absolute methanol washing, reuse after vacuum 80 DEG C of dryings, method is with application examples 5.Recycle result as shown in table 1.

Claims (9)

1.ZIF-8 encapsulates amino ion liquid type CO 2absorption-catalyst, for carrier with metal-organic framework materials ZIF-8, amino functional ionic liquid 1-(3-aminopropyl)-3-methylimidazolium chloride is active component, obtain immobilized for amino functional ionic liquid original position in the supercage of described ZIF-8 carrier while preparation ZIF-8, wherein, immobilized in absorption-catalyst described in every 1g have 1.5 ~ 5mmol amino functional ionic liquid.
2. ZIF-8 described in claim 1 encapsulates amino ion liquid type CO 2the preparation method of absorption-catalyst is in anhydrous acetonitrile dicyandiamide solution under nitrogen protection, by n-methylimidazole and 3-chloro propyl amine hydrochloric acid salt heating reflux reaction prepare amino functional ionic liquid 1-(3-aminopropyl)-3-methylimidazolium chloride, again 1-(3-aminopropyl)-3-methylimidazolium chloride and zinc nitrate hexahydrate are scattered in absolute methanol, drip glyoxal ethyline absolute methanol solution, add thermal response and prepare described ZIF-8 and encapsulate amino ion liquid type CO 2absorption-catalyst.
3. preparation method according to claim 2, is characterized in that described n-methylimidazole and 3-chloro propyl amine hydrochloric acid salt with 1.2 ~ 2: 1 mole dosage to react than in the anhydrous acetonitrile dicyandiamide solution of 70 ~ 80 DEG C 24 ~ 72 little time, with anhydrous ethyl acetate washing, drying after product removing acetonitrile, again with after a small amount of water-soluble solution, by KOH solution adjust ph to 8, the washing also dry precipitation separated out obtains amino functional ionic liquid.
4. preparation method according to claim 2, described amino functional ionic liquid, glyoxal ethyline and zinc nitrate hexahydrate is it is characterized in that to react 24 ~ 72 hours in the absolute methanol dicyandiamide solution of 20 ~ 30 DEG C, wherein zinc nitrate hexahydrate is 0.1 ~ 0.15: 1 with the mole dosage ratio of glyoxal ethyline, and amino functional ionic liquid is 0.2 ~ 0.5: 1 with the mole dosage ratio of zinc nitrate hexahydrate.
5. ZIF-8 described in claim 1 encapsulates amino ion liquid type CO 2absorption-catalyst is CO in selective absorption flue gas 2and catalyzed conversion CO 2on application.
6. application according to claim 5, is characterized in that the CO in described flue gas 2volumn concentration is 10 ~ 20%.
7. the application according to claim 5 or 6, is characterized in that under the adsorption temp of 25 ~ 100 DEG C, encapsulates amino ion liquid type CO with described ZIF-8 2cO is caught in the absorption of absorption-catalyst choice 2, then cycloaddition reaction synthesizing annular carbonate is carried out with epoxide at reaction pressure 2Mpa, temperature 50 ~ 120 DEG C.
8. application according to claim 7, is characterized in that described epoxide is epoxychloropropane.
9. application according to claim 7, is characterized in that the time of described cycloaddition reaction is 3 ~ 40 hours.
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