CN105149002B - 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 PDFInfo
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- CN105149002B CN105149002B CN201510659602.2A CN201510659602A CN105149002B CN 105149002 B CN105149002 B CN 105149002B CN 201510659602 A CN201510659602 A CN 201510659602A CN 105149002 B CN105149002 B CN 105149002B
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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
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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
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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
Technical field
The present invention relates to a kind of CO2Absorption-catalyst, more particularly to a kind of based on ionic liquid active component, collection
Selective absorption and catalysiss efficient CO2Absorption-catalyst, and the preparation method of the absorption-catalyst.
Background technology
Global warming has become the environmental problem for receiving much concern, with CO2Based on greenhouse gases discharge in a large number, be to lead
Cause the main cause of greenhouse effect aggravation.Say from resource angle, CO2It is again C1Carbon resource the most cheap and abundant in family,
No matter from from the point of view of the utilization of resources or environmental conservation, relevant CO2The research and development of fixed and chemical conversion all have
Significance.Therefore, CO2Trapping becomes the hot spot technology for currently urgently developing with (CCU) technology of utilization.
CO2Inertia is very big, is difficult to be activated, and realizes that its chemistry is fixed and it is extremely difficult to convert, thus adsorbent and catalysis
The performance issue of agent constrains the application and development of CCU technologies.If design is a kind of to integrate capture and the suction of catalysiss
Attached-catalyst, by CO2Efficiently converted in-situ is the higher product of added value after trapping, then can simplify technology path, reduce into
This, promotes the development of CCU technologies.
Ionic liquid is to be made up of anions and canons completely, less than the organic salt being in a liquid state in 100 DEG C of temperature ranges.From
The peculiar properties such as there is sub- liquid steam to force down, nonflammable, heat stability is high, solvability is strong, structure and property scalable.
These characteristics cause ionic liquid to become the fixed CO of the traditional organic amine solvent trapping of replacement2New type ideal solvent.Additionally, unique
Catalytic performance also cause ionic liquid in a mild condition i.e. to various CO2Conversion reaction show excellent catalysis activity and
Selectivity.Therefore, the ionic liquid of ad hoc structure is designed as active component, will be expected to realize CO2Trapping and conversion integration.
However, the shortcomings of ionic liquid has big viscosity, high cost, seriously constrains its application again.
Metal-organic framework materials (MOFs) are that the class generated by self assembly by metal ion and organic ligand is new
Type porous material, with specific surface area it is big, pore passage structure is regular, duct and surface chemical property can the feature such as modulation, absorption,
The aspect such as separation and catalysis shows wide application prospect.
Zeolitic imidazolate framework material (ZIFs) is the one kind in MOFs materials, it be by transition metal atoms Zn or Co with
Imidazoles or imdazole derivatives connection and generate a class is new, the nano-porous materials with zeolite topological.ZIFs is not
Only there is MOFs materials, and compared with MOFs materials, with more excellent heat and hydrothermal stability.ZIF-8 is
Most representational one kind in ZIFs materials, its cage mouth diameter 0.34nm, with CO2Kinetic diameter (0.33nm) phase of molecule
Closely, therefore to CO2With good selectivity.ZIF-8 shows excellent in multiple fields such as absorption, separation, gas storage and catalysis
Different performance.
The content of the invention
It is an object of the invention to provide a kind of ZIF-8 encapsulation amino ions for integrating selective absorption and catalysiss
Liquid type CO2Absorption-catalyst, and the preparation method of the absorption-catalyst, to realize CO2Synchronous absorption and convert, drop
Low CUU technical costss.
ZIF-8 of the present invention encapsulates amino ion liquid type CO2Absorption-catalyst is with metal-organic framework materials
ZIF-8 is carrier, and amino functional ionic liquid 1- (3- aminopropyls) -3- methylimidazolium chlorides are active component, are being prepared
Amino functional ionic liquid original position is immobilized on while ZIF-8 obtaining in the supercage of the ZIF-8 carriers, wherein, per 1g
It is immobilized in the absorption-catalyst to have 1.5～5mmol amino functional ionic liquids.
The present invention further prepares the ZIF-8 encapsulation amino ion liquid type CO there is provided one kind2The side of absorption-catalyst
Method, in being anhydrous acetonitrile dicyandiamide solution first under nitrogen protection, byN- Methylimidazole. is heated to reflux with 3- chloro propyl amine hydrochloric acid salts
Reaction prepares amino functional ionic liquid 1- (3- aminopropyls) -3- methylimidazolium chlorides, then by 1- (3- aminopropyls) -3- first
Base imidazolium chloride is scattered in absolute methanol with zinc nitrate hexahydrate, Deca 2-methylimidazole absolute methanol solution, and heating is anti-
The ZIF-8 encapsulation amino ion liquid type CO should be prepared2Absorption-catalyst.
It is described in the above-mentioned preparation method of the present inventionN- Methylimidazole. is preferably with the mole dosage ratio of 3- chloro propyl amine hydrochloric acid salts
1.2～2: 1.
Further, the present invention be will be describedN- Methylimidazole. and anhydrous second of the 3- chloro propyl amine hydrochloric acid salts at 70～80 DEG C
React 24～72 hours in nitrile dicyandiamide solution, product removed and washed with anhydrous ethyl acetate after acetonitrile, is dried, then with a small amount of
After water dissolution, pH value is adjusted to 8, wash and be dried the precipitation for separating out and obtain amino functional ionic liquid with KOH solution.
In the above-mentioned preparation method of the present invention, for prepare the zinc nitrate hexahydrate of ZIF-8 and 2-methylimidazole mole with
Amount than being 0.1～0.15: 1, and by the 2-methylimidazole and absolute methanol solvent of the zinc nitrate hexahydrate at 20～30 DEG C
React 24～72 hours in system.
Further, the amino functional ionic liquid for being added during ZIF-8 is prepared rubs with zinc nitrate hexahydrate
Your amount ratio is 0.2～0.5: 1.
ZIF-8 encapsulation amino ion liquid type CO prepared by the present invention2Absorption-catalyst can be applicable to be selected in flue gas
Selecting property absorption capture CO2And realize CO2Efficient catalytic conversion.
Further, it is suitable for CO in the flue gas of absorption of the present invention-Catalyst Adsorption conversion2Volumn concentration be
10～20%.
Amino ion liquid type CO is encapsulated using ZIF-8 of the present invention2Absorption-catalyst traps and conversion CO2It is concrete
Method is：Under 25～100 DEG C of adsorption temp, amino ion liquid type CO is encapsulated with the ZIF-82Absorption-catalyst is selected
Selecting property absorption capture CO2, cycloaddition reaction is carried out with epoxide at reaction pressure 2Mpa, 50～120 DEG C of temperature, close
Circlewise carbonic ester.
Usually, the response time of the cycloaddition reaction is 3～40 hours.
Preferably, epoxide of the present invention is epoxychloropropane, the cyclic carbonate of synthesis be 4- chloromethyls-
[1,3] the amyl- 2- ketone of dioxy ring.
The present invention is immobilized on amino functional ionic liquid active component with larger ratio using the method for fabricated in situ
In the supercage of the 3-dimensional metal organic framework material ZIF-8 of surface area and pore volume, a kind of collection absorption capture is prepared and has urged
Change transformation function, the efficient CO that capacity is big, activity is high and cyclic utilization rate is good2Heterogeneous absorption-catalyst, realizes
CO2High selectivity, Large Copacity, the Efficient Conversion of low energy consumption trapping and cyclic carbonate, be CO2Fixed conversion be particularly
CO in flue gas2Industrial utilization provide effective method.
By ionic liquid supported on the porous carrier of bigger serface, ionic liquid consumption can be substantially reduced, be reduced
CO2Resistance to mass tranfer, and be easily isolated and reuse, it is thus possible to significantly improve absorption-catalyst adsoption catalysis efficiency and
Recycling rate.Compared with general mesopore molecular sieve SBA-16, MCM-41, SBA-15 etc., ZIF-8 has unique micropore knot
Structure and bigger specific surface area, and its bore dia and CO2Kinetic diameter it is close, absorption, separate, catalysis etc. field possess
Higher application potential, can be used as the excellent carrier of solid-loaded ionic-liquid.
Absorption-catalyst prepared by the present invention has concentrated the good trapping performance and excellent catalyzed conversion of ionic liquid
Can, while the synergism based on ionic liquid and porous carrier to acid gas adsorption, it is to CO2Selective absorption performance
It is fully reflected, to the CO in typical flue gas temperature range2With preferable absorption property, to epoxide and CO2
Between cycloaddition reaction also have the advantages that high conversion rate, selectivity be good, reusable edible.
Absorption-catalyst prepared by the present invention can efficient absorption CO under normal pressure, effluent gas temperature2, and in a constant temperature
By CO under degree, pressure2Cyclic carbonate is converted into, is shown that active high, selectivity is good, reaction condition is gentle, be easily isolated, can
The advantages of recycling, can realize CO2Synchronous absorption and convert, reduce CUU technical costss.
Specific embodiment
Embodiment 1
Weigh 16.42g (200mmol)N- Methylimidazole., 13.02g (100mmol) 3- chloro propyl amine hydrochloric acid salts, is added to
In 50mL anhydrous acetonitriles, lead to nitrogen protection, 75 DEG C are heated under stirring, back flow reaction 24 hours.After reaction terminates, revolving is removed
Solvent acetonitrile, with the product that anhydrous ethyl acetate washing is obtained, room temperature in vacuo is dissolved in a small amount of water after being dried, and uses KOH solution
PH value is adjusted to 8, the sedimentation method remove KCl, and vacuum drying obtains flaxen amino functional ionic liquid 14g.
1.5g zinc nitrate hexahydrates are weighed, is disperseed together with the above-mentioned amino functional ionic liquid 0.221g for preparing
Dispersion liquid is obtained in 70mL absolute methanols, 3.3g 2-methylimidazoles are dissolved in 70mL absolute methanols, be slowly dropped to
In stating dispersion liquid, 24 hours are stirred vigorously under room temperature.Centrifugation, by the solid for obtaining with absolute methanol washing, vacuum drying
Afterwards, ZIF-8 encapsulation amino ion liquid type CO are obtained2Absorption-catalyst white powder 0.80g, is labeled as IL-1@ZIF-8.
Embodiment 2
1.5g zinc nitrate hexahydrates are weighed, together with the amino functional ionic liquid 0.295g prepared with embodiment 1
It is scattered in 70mL absolute methanols and obtains dispersion liquid, 3.3g 2-methylimidazoles are dissolved in 70mL absolute methanols, is slowly added dropwise
To in above-mentioned dispersion liquid, 36 hours are stirred vigorously under room temperature.Centrifugation, by the solid for obtaining with absolute methanol washing, vacuum
After drying, ZIF-8 encapsulation amino ion liquid type CO are obtained2Absorption-catalyst white powder 0.70g, is labeled as IL-3@ZIF-
8。
Embodiment 3
1.5g zinc nitrate hexahydrates are weighed, together with the amino functional ionic liquid 0.442g prepared with embodiment 1
It is scattered in 70mL absolute methanols and obtains dispersion liquid, 3.3g 2-methylimidazoles are dissolved in 70mL absolute methanols, is slowly added dropwise
To in above-mentioned dispersion liquid, 30 hours are stirred vigorously under room temperature.Centrifugation, by the solid for obtaining with absolute methanol washing, vacuum
After drying, ZIF-8 encapsulation amino ion liquid type CO are obtained2Absorption-catalyst white powder 0.65g, is labeled as IL-5@ZIF-
8。
Embodiment 4
Weigh 1.5g zinc nitrate hexahydrates to be scattered in 70mL absolute methanols, be slowly added dropwise 70mL and be dissolved with 3.3g 2- first
48 hours are stirred vigorously under the absolute methanol of base imidazoles, room temperature.Centrifugation, by the solid for obtaining with absolute methanol washing, true
After sky is dried, pure metallic organic framework ZIF-8 white powder 1.3g are obtained.
Following application examples uses CO2Infrared spectrum analyser, the ZIF-8 using the preparation of embodiment 4 is determined and compared under normal pressure as control
Compared with ZIF-8 encapsulation amino ion liquid type CO prepared by above-described embodiment2Absorption-catalyst is to sour gas CO2Selection absorption
Performance.
Application examples 1
Weigh about 1.0g IL-5@ZIF-8 to be filled in adsorptive reactor, in 80cm3Under the nitrogen stream of/min, from room temperature
Start to be warming up to 140 DEG C of holding constant temperature with the heating rate of 1 DEG C/min, purge 60min；Then absorption is cooled in nitrogen atmosphere
25 DEG C of temperature, is passed through containing 85%N with the gas flow rate of 100ml/min2And 15%CO2Gaseous mixture, adsorption reaction 10min, and in fact
When record data.The CO of sample2Adsorbance is selected according to CO2Infrared spectrum analyser measurement data is calculated, and selection adsorbance is
2.26mmol/g。
Application examples 2
With 50 DEG C of CO2Adsorption reaction temperature measuring IL-5@ZIF-8, other conditions are with application examples 1, CO2Select adsorbance
For 2.29 mmol/g.
Application examples 3
With 75 DEG C of CO2Adsorption reaction temperature measuring IL-5@ZIF-8, other conditions are with application examples 1, CO2Select adsorbance
For 3.05mmol/g.
Application examples 4
IL-1@ZIF-8, CO are determined according to the condition of application examples 12Selection adsorbance is 1.54mmol/g.
Comparative example 1
Weigh about 1.0g ZIF-8 to be filled in adsorptive reactor, in 80cm3Under the nitrogen stream of/min, from room temperature start with
The heating rate of 1 DEG C/min is warming up to 140 DEG C of holding constant temperature, purges 60min；Then adsorption temp 25 is cooled in nitrogen atmosphere
DEG C, it is passed through containing 85%N with the gas flow rate of 100ml/min2And 15%CO2Gaseous mixture, adsorption reaction 10min, and real time record
Data.The CO of sample2Adsorbance is selected according to CO2Infrared spectrum analyser measurement data is calculated, and selection adsorbance is
1.02mmol/g。
Comparative example 2
CO2Adsorption reaction temperature is 50 DEG C, and other conditions are with comparative example 1, CO2Selection adsorbance is 1.13mmol/g.
Comparative example 3
CO2Adsorption reaction temperature is 75 DEG C, and other conditions are with comparative example 1, CO2Selection adsorbance is 1.34mmol/g.
Can be seen that under similarity condition by above-mentioned application examples and comparative example determination data, absorption-catalysis prepared by the present invention
Agent is to CO2Adsorption selectivity be significantly better than ZIF-8.
Application examples 5
0.5g absorption-catalyst IL-5@ZIF-8,9.25g (100mmol) epoxy chlorine are added in 100mL autoclaves
Propane, it is closed, with the CO of 1.0Mpa2Air in kettle is displaced completely, 120 DEG C are to slowly warm up to, and controlling reaction pressure is
2.0Mpa reacts 6 hours.After the cooling of question response kettle, remaining CO is slowly released2, the supernatant is taken after products obtained therefrom is centrifuged
GC analyses are carried out, the yield of 4- chloromethyls-amyl- 2- ketone of [1,3] dioxy ring is 95.5%, selectivity 98.2%.
Application examples 6
Addition 0.5g absorption-catalyst IL-5@ZIF-8,100 DEG C of reaction temperature, other conditions are identical with application examples 5, survey
The yield for obtaining 4- chloromethyls-amyl- 2- ketone of [1,3] dioxy ring is 92.6%, selectivity 100%.
Application examples 7
Addition 0.5g absorption-catalyst IL-3@ZIF-8,100 DEG C of reaction temperature, other conditions are identical with application examples 5, survey
The yield for obtaining 4- chloromethyls-amyl- 2- ketone of [1,3] dioxy ring is 91.8%, selectivity 96.4%.
Application examples 8
Addition 0.5g absorption-catalyst IL-5@ZIF-8,90 DEG C of reaction temperature, other conditions are identical with application examples 5, measure
The yield of 4- chloromethyls-amyl- 2- ketone of [1,3] dioxy ring is 92.91%, selectivity 95.39%.
Application examples 9
Absorption-the catalyst being collected by centrifugation after reacting in application examples 5 washs colourless to supernatant with absolute methanol, vacuum
Reuse after 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 CO2Absorption-catalyst, is the ammonia with metal-organic framework materials ZIF-8 as carrier
Base functionalized ion liquid 1- (3- aminopropyls) -3- methylimidazolium chlorides are active component, anhydrous second under nitrogen protection
In nitrile dicyandiamide solution, byN- Methylimidazole. prepares amino functional ionic liquid 1- with 3- chloro propyl amine hydrochloric acid salt heating reflux reactions
(3- aminopropyls) -3- methylimidazolium chlorides, then 1- (3- aminopropyls) -3- methylimidazolium chlorides and zinc nitrate hexahydrate are divided
Dissipate in absolute methanol, Deca 2-methylimidazole absolute methanol solution, heating is reacted, by ammonia while ZIF-8 is prepared
Base functionalized ion liquid original position is immobilized in the supercage of the ZIF-8 carriers, the ZIF-8 encapsulation amino ionic liquid for preparing
Build CO2Absorption-catalyst, wherein, it is immobilized in absorption-catalyst described in per 1g to have 1.5～5mmol amino functional ionic liquid
Body.
2. ZIF-8 described in claim 1 encapsulates amino ion liquid type CO2The preparation method of absorption-catalyst, is protected in nitrogen
In anhydrous acetonitrile dicyandiamide solution under shield, byN- Methylimidazole. prepares amino functional with 3- chloro propyl amine hydrochloric acid salt heating reflux reactions
Change ionic liquid 1- (3- aminopropyls) -3- methylimidazolium chlorides, then by 1- (3- aminopropyls) -3- methylimidazolium chlorides and six
Nitric hydrate zinc is scattered in absolute methanol, Deca 2-methylimidazole absolute methanol solution, and reacting by heating prepares described
ZIF-8 encapsulates amino ion liquid type CO2Absorption-catalyst.
3. preparation method according to claim 2, it is characterized in that will be describedN- Methylimidazole. and 3- chloro propyl amine hydrochloric acid salts with
1.2～2: 1 mole dosage ratio reacts 24～72 hours in 70～80 DEG C of anhydrous acetonitrile dicyandiamide solution, and product is removed
After acetonitrile with anhydrous ethyl acetate washing, be dried, then with a small amount of water dissolution after, with KOH solution adjust pH value to 8, wash and do
The precipitation of dry precipitation obtains amino functional ionic liquid.
4. preparation method according to claim 2, is characterized in that the amino functional ionic liquid, 2-methylimidazole
React 24～72 hours in 20～30 DEG C of absolute methanol dicyandiamide solution with zinc nitrate hexahydrate, wherein zinc nitrate hexahydrate with
The mole dosage ratio of 2-methylimidazole is 0.1～0.15: 1, amino functional ionic liquid and zinc nitrate hexahydrate mole with
Amount is than being 0.2～0.5: 1.
5. ZIF-8 described in claim 1 encapsulates amino ion liquid type CO2Absorption-catalyst is in selective absorption flue gas
CO2And catalyzed conversion CO2On application.
6. application according to claim 5, is characterized in that the CO in the flue gas2Volumn concentration is 10～20%.
7. the application according to claim 5 or 6, is characterized in that under 25～100 DEG C of adsorption temp, with the ZIF-8
Encapsulation amino ion liquid type CO2Absorption-catalyst choice absorption capture CO2, then at reaction pressure 2Mpa, temperature 50～120
Cycloaddition reaction synthesizing annular carbonate is carried out at DEG C with epoxide.
8. application according to claim 7, is characterized in that described epoxide is epoxychloropropane.
9. application according to claim 7, the time that it is characterized in that the cycloaddition reaction is 3～40 hours.
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| CN102989506B (en) * | 2012-12-18 | 2015-07-01 | 常州大学 | Preparation method of novel immobilized ionic liquid catalyst |
| CN103058189B (en) * | 2013-01-28 | 2014-08-20 | 北京化工大学 | Absorption and adsorption coupling method for capturing carbon dioxide |
| CN103920534B (en) * | 2014-03-04 | 2016-01-27 | 大连理工大学 | Immobilized alkaline ionic liquid catalyst of a kind of metal-organic framework materials and preparation method thereof |
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