CN106964316A - A kind of zeolite imidazole ester skeleton functionalized ion liquid composite and its preparation and application - Google Patents
A kind of zeolite imidazole ester skeleton functionalized ion liquid composite and its preparation and application Download PDFInfo
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/223—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material containing metals, e.g. organo-metallic compounds, coordination complexes
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
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Abstract
The present invention discloses a kind of zeolite imidazole ester skeleton functionalized ion liquid composite and its preparation and application, belongs to CO2Trapping and storing technology field.The present invention carries out functionalized ion liquid in ZIFs basket structures by " ship construction method in bottle " fabricated in situ of ionic liquid, so that ionic liquid is directly immobilized in ZIFs cages.The present invention is dry process, in the absence of liquid flux, the shortcoming of traditional handicraft can be overcome, while reducing the energy consumption of hot recycling.The zeolite imidazole ester skeleton functionalized ion liquid composite crystallinity of the present invention is high, specific surface area is big, heat endurance and chemical stability preferably, due to functionalized ion liquid and zeolitic imidazolate framework material for CO2The synergy of absorption, it is to CO2Energy of adsorption realize preferably effect, in actual CO2Absorption in, show the good characteristics such as mild condition, running cost are low, extrusion rate is good, and the material regeneration is convenient, circulation absorption effect is good.
Description
Technical field
The invention belongs to CO2Trapping and storage (CO2Capture and storage, CCS) technical field, and in particular to one
Plant zeolite imidazole ester skeleton-functionalized ion liquid composite and preparation method and application.
Background technology
In recent years, ionic liquid is with its unique low-vapor pressure, good heat endurance and higher gas solubility
The features such as in CO2Separation and fixed network cause extensive concern.In addition, the aobvious alkalescence of the ionic liquid of amino functional,
Energy and CO2Sour gas chemically reacts, thus has bigger CO compared to general ionic liquid2Uptake, but its is high
Price and higher viscosity limit it and further apply.Supported ionic liquids are the frontiers of ionic liquid research, will
Ion is immobilized on the porous material, can not only overcome the problem of viscosity of il is high, and can be easier to realize following for material
Ring is utilized and operated continuously, and possibility is provided for the further application of ionic liquid.
Zeolitic imidazolate framework material (Zeolitic Imdazolate Framework, abbreviation ZIFs), is that a class is porous
The metal-organic framework materials with tridimensional network.There is high porosity, big specific surface area because of it, duct is adjustable
Property, good chemistry and heat endurance, in CO2There is extensive purposes in terms of adsorbing separation and storage.Zeolite imidazole ester bone
Frame material is further modified by loading the ionic liquid of amino-functionalization, pore structure, improves it to CO2The selection of absorption
Property, while the introducing of alkali ionic liquid, adds resulting materials and CO2Between interaction, its CO2Adsorbance is also obtained
Improve well.
Using the method simply impregnated more than the load of ionic liquid in the porous material, although simple to operate, but big portion
Segregant liquid adsorbs only on the surface of porous material, is easily come off during absorption with desorption gas so that material
Reusable performance declines.Moreover, porous material is not because ionic liquid can be effectively entered among duct yet, Kong Jie
Structure is not also modified preferably, causes the adsorptive selectivity of its gas not high.
At present, the Ionic liquids technologies using zeolitic imidazolate framework material load amino functional are still not mature enough, and
The performance of these composites and application need further discovery, and this is also the problem of present invention attempts to solve.
The content of the invention
In order to overcome the shortcoming and deficiency of prior art, primary and foremost purpose of the invention is to provide a kind of zeolite imidazole ester bone
The preparation method of frame-functionalized ion liquid composite.Specifically, the present invention passes through functionalized ion liquid " in bottle
Ship construction method " carries out the fabricated in situ of ionic liquid in ZIFs basket structures, so that ionic liquid is directly immobilized in ZIFs cages.
Another object of the present invention is to provide the zeolite imidazole ester skeleton-function of being prepared by above-mentioned preparation method
Change ionic liquid composite material.The material crystalline degree is high, specific surface area is big, heat endurance and chemical stability are preferable.
It is still another object of the present invention to provide answering for above-mentioned zeolite imidazole ester skeleton-functionalized ion liquid composite
With mainly using it for CO2Absorption and trapping.
The purpose of the present invention is achieved through the following technical solutions:
A kind of preparation method of zeolite imidazole ester skeleton-functionalized ion liquid composite, using " ship construction method in bottle "
Fabricated in situ, comprises the following steps:
(1) zeolitic imidazolate framework material is dried in vacuo, to remove the water that is adsorbed in its duct and its other are miscellaneous
Matter;
(2) the dried zeolite imidazole skeleton material of step (1) is put into precursor A or precursor A solution, stirring
It is allowed to fully infiltrate and be uniformly dispersed, precursor A is first passed through the basket structure that adsorption and diffusion enters zeolite imidazole branch framework material
In;
(3) then add precursor B, precursor B by adsorption and diffusion enter zeolite imidazole branch framework material basket structure
In with precursor A response generation function ionic liquids;
(4) suction filtration, the precursor for having neither part nor lot in reaction is removed to filter residue by surname extraction, and vacuum is then carried out to it and is done
It is dry, so as to obtain zeolite imidazole ester skeleton-functionalized ion liquid composite.
Described precursor A is preferably as follows:Imidazoles (a), tertiary phosphine class (b), pyridines (c), pyroles (d) and tertiary amines
(e) one or more of compound, its formula is:
R in formula1、R2Or R3For hydrogen atom or alkyl substituent.
The long alkyl chains of described precursor A alkyl substituents are preferably C1~C3。
Described precursor A is more preferably at least one of N- methylimidazoles and N- methylpyrroles;
Described precursor B formula is R-X;R is alkyl substituent or the alkyl substitution with functionalization group in formula
Base, X is Cl-、Br-Or I-。
Described functionalization group is preferably amido.
The long alkyl chains of described precursor B alkyl substituents or the alkyl substituent with amido are C3~C8。
Described precursor B is preferably at least one of 1- NBBs, 3- bromine propylamine hydrobromic acids and 1- bromooctanes;
Described zeolitic imidazolate framework material is connected by many yuan of rings.Precursor can diffuse into ZIFs by ring window
In cage, then precursor A and B can not escape from window in the functionalized ion liquid that cage situ reacts generation and be limited to cage
In.
Described zeolitic imidazolate framework material is preferably ZIF-2, ZIF-7, ZIF-8, ZIF-11, ZIF-60 and ZIF-68
At least one of, but it is not limited to this several zeolitic imidazolate framework material.
Described precursor A and B mol ratio is preferably 1:1~1:2;More preferably 1:1.1.
A kind of zeolite imidazole ester skeleton-functionalized ion liquid composite, is prepared by above-mentioned preparation method.
It is main in terms of described zeolite imidazole ester skeleton-functionalized ion liquid composite can be used for sour gas trapping
Use it for CO2Absorption and trapping.
The present invention has the following advantages and effect relative to prior art:
(1) present invention is dry process, in the absence of liquid flux, the shortcoming of traditional handicraft can be overcome, while reducing heat
The energy consumption of regeneration.
(2) functionalized ion liquid loaded is limited by ZIFs cage window sizes and can not escaped from ZIFs cages,
Therefore losing issue is avoided.The characteristics of ionic liquid heat endurance is high is remained simultaneously, is improved and is recycled performance.
(3) ZIFs materials are loaded after ionic liquid, and its pore structure and hole size are modified, and trap CO2Selectivity
Increase substantially.
(4) zeolite imidazole ester skeleton-functionalized ion liquid composite for preparing of the present invention, due to functionalization from
Sub- liquid and zeolitic imidazolate framework material are for CO2The synergy of absorption, it is to CO2Energy of adsorption realize preferably effect,
In actual CO2Adsorption operations in, show the good characteristics such as mild condition, running cost are low, extrusion rate is good, and the material
Regeneration is convenient, and circulation absorption effect is good.
Embodiment
With reference to embodiment, the present invention is described in further detail, but the implementation of the present invention is not limited to this.
Embodiment 1
A kind of preparation method of zeolite imidazole ester skeleton-functionalized ion liquid composite, step is as follows:
(1) 16.40g (0.20mol) N- methylimidazoles are added toward 50mL flasks, adds 2g through vacuum drying at 150 DEG C
ZIF-8, stirs 18h at room temperature;
(2) 29.92g (0.22mol) 1- NBBs are added, 24h is stirred at room temperature, suction filtration washs 3 times with ethanol, every time
20mL;
(3) surname extraction 24h is carried out to filter residue with ethanol, then the dry 24h of 80 DEG C of vacuum, product code numbering is [BMIM]
Br@ZIF-8。
(4) take material 0.1g, after the pre-treatments such as drying, degassing, CO is carried out on multiple function apparatus2Breakthrough curve
Experiment, determines its CO2Adsorption capacity.
Thermogravimetric analysis (TGA) result shows that [BMIM] Br@ZIF-8 start decomposition after 350 DEG C, hence it is evident that higher than pure ionic liquid
The heat decomposition temperature (250 DEG C) of body 1- butyl -3- methylimidazoles (350 DEG C).Elementary analysis result shows [BMIM] Br@ZIF-8
The useful load of intermediate ion liquid is 20.6%.In 15vol%CO2In, in the range of 35~75 DEG C, to CO2Adsorption capacity be
72.2mg/g to 56.8mg/g.
Embodiment 2
A kind of preparation method of zeolite imidazole ester skeleton-functionalized ion liquid composite, step is as follows:
(1) ZIF-8 dries 24h in 150 DEG C of vacuum;
(2) under nitrogen protection, toward addition 10mL ethanol and 2.46g (0.03mol) N- methyl miaows in 50mL three-necked flasks
Azoles, adds the ZIF-8 of 2g dryings, 15h is stirred at room temperature;
(3) 10mL absolute ethyl alcohols are added, 7.01g (0.032mol) 3- bromine propylamine hydrobromic acids is added, is stirred under nitrogen protection
Mix and be heated to reflux 24h, suction filtration is washed 3 times, each 10mL with ethanol;
(4) surname extraction 24h is carried out to filter residue with ethanol, then the dry 24h of 80 DEG C of vacuum, you can obtain target material,
Marked as [APMIM] Br@ZIF-8.
(5) take material 0.1g, after the pre-treatments such as drying, degassing, CO is carried out on multiple function apparatus2Breakthrough curve
Experiment, determines its CO2Adsorption capacity.
Thermogravimetric analysis (TGA) result shows that [APMIM] Br@ZIF-8 start decomposition after 320 DEG C, hence it is evident that higher than pure ion
The heat decomposition temperature (250 DEG C) of liquid 1- amine propyl group -3- methylimidazoles bromines ([APMIM] Br).Elementary analysis result is shown
The useful load of [APMIM] Br@ZIF-8 intermediate ion liquid is 24.0%.In 15vol%CO2In, in the range of 35~75 DEG C, to CO2
Adsorption capacity be 81.4mg/g to 68.3mg/g.
Embodiment 3
A kind of preparation method of zeolite imidazole ester skeleton-functionalized ion liquid composite, step is as follows:
(1) under nitrogen protection, 10mL ethanol and 1.642g (0.02mol) N- methylimidazoles are added toward 50mL flasks, plus
Enter 2g through vacuum drying ZIF-7 at 150 DEG C, 18h is stirred at room temperature;
(2) 20mL ethanol and 4.816g (0.022mol) 3- bromine propylamine hydrobromic acids are added, under nitrogen protection, is stirred at room temperature
24h, suction filtration is washed 3 times, each 20mL with ethanol;
(3) surname extraction 24h is carried out to filter residue with ethanol, then the dry 24h of 80 DEG C of vacuum, product code numbering is [APMIM]
Br@ZIF-7。
(4) take material 0.1g, after the pre-treatments such as drying, degassing, CO is carried out on multiple function apparatus2Breakthrough curve
Experiment, determines its CO2Adsorption capacity.
Thermogravimetric analysis (TGA) result shows that [APMIM] Br@ZIF-7 start decomposition after 310 DEG C, hence it is evident that higher than pure ion
The heat decomposition temperature (250 DEG C) of liquid 1- amine propyl group -3- methylimidazoles bromines ([APMIM] Br).Elementary analysis result is shown
The useful load of [BMIM] Br@ZIF-7 intermediate ion liquid is 18.4%.In 15vol%CO2In, in the range of 35~75 DEG C, to CO2's
Adsorption capacity is 80.2mg/g to 61.8mg/g.
Embodiment 4
A kind of preparation method of zeolite imidazole ester skeleton-functionalized ion liquid composite, step is as follows:
(1) under nitrogen protection, 10mL ethanol and 1.642g (0.02mol) N- methylimidazoles are added toward 50mL flasks, plus
Enter 2g through vacuum drying ZIF-60 at 150 DEG C, 18h is stirred at room temperature;
(2) 20mL ethanol and 4.816g (0.022mol) 3- bromine propylamine hydrobromic acids are added, under nitrogen protection, is stirred at room temperature
24h, suction filtration is washed 3 times, each 20mL with ethanol;
(3) surname extraction 24h is carried out to filter residue with ethanol, then the dry 24h of 80 DEG C of vacuum, product code numbering is [APMIM]
Br@ZIF-60。
(4) take material 0.1g, after the pre-treatments such as drying, degassing, CO is carried out on multiple function apparatus2Breakthrough curve
Experiment, determines its CO2Adsorption capacity.
Thermogravimetric analysis (TGA) result shows that [APMIM] Br@ZIF-60 start decomposition after 340 DEG C, hence it is evident that higher than pure ion
The heat decomposition temperature (250 DEG C) of liquid 1- amine propyl group -3- methylimidazoles bromines ([APMIM] Br).Elementary analysis result is shown
The useful load of [BMIM] Br@ZIF-60 intermediate ion liquid is 15.6%.In 15vol%CO2In, in the range of 35~75 DEG C, to CO2
Adsorption capacity be 78.5mg/g to 59.8mg/g.
Embodiment 5
A kind of preparation method of zeolite imidazole ester skeleton-functionalized ion liquid composite, step is as follows:
(1) under nitrogen protection, 10mL ethanol and 1.642g (0.02mol) N- methylimidazoles are added toward 50mL flasks, plus
Enter 2g through vacuum drying ZIF-2 at 150 DEG C, 18h is stirred at room temperature;
(2) 20mL ethanol and 4.816g (0.022mol) 3- bromine propylamine hydrobromic acids are added, under nitrogen protection, is stirred at room temperature
24h, suction filtration is washed 3 times, each 20mL with ethanol;
(3) surname extraction 24h is carried out to filter residue with ethanol, then the dry 24h of 80 DEG C of vacuum, product code numbering is [APMIM]
Br@ZIF-2。
(4) take material 0.1g, after the pre-treatments such as drying, degassing, CO is carried out on multiple function apparatus2Breakthrough curve
Experiment, determines its CO2Adsorption capacity.
Thermogravimetric analysis (TGA) result shows that [APMIM] Br@ZIF-2 start decomposition after 310 DEG C, hence it is evident that higher than pure ion
The heat decomposition temperature (250 DEG C) of liquid 1- amine propyl group -3- methylimidazoles bromines ([APMIM] Br).Elementary analysis result is shown
The useful load of [BMIM] Br@ZIF-2 intermediate ion liquid is 15.6%.In 15vol%CO2In, in the range of 35~75 DEG C, to CO2's
Adsorption capacity is 68.9mg/g to 52.5mg/g.
Embodiment 6
A kind of preparation method of zeolite imidazole ester skeleton-functionalized ion liquid composite, step is as follows:
(1) under nitrogen protection, 10mL ethanol and 1.642g (0.02mol) N- methylimidazoles are added toward 50mL flasks, plus
Enter 2g through vacuum drying ZIF-11 at 150 DEG C, 18h is stirred at room temperature;
(2) 20mL ethanol and 4.816g (0.022mol) 3- bromine propylamine hydrobromic acids are added, under nitrogen protection, is stirred at room temperature
24h, suction filtration is washed 3 times, each 20mL with ethanol;
(3) surname extraction 24h is carried out to filter residue with ethanol, then the dry 24h of 80 DEG C of vacuum, product code numbering is [APMIM]
Br@ZIF-11。
(4) take material 0.1g, after the pre-treatments such as drying, degassing, CO is carried out on multiple function apparatus2Breakthrough curve
Experiment, determines its CO2Adsorption capacity.
Thermogravimetric analysis (TGA) result shows that [APMIM] Br@ZIF-11 start decomposition after 295 DEG C, hence it is evident that higher than pure ion
The heat decomposition temperature (250 DEG C) of liquid 1- amine propyl group -3- methylimidazoles bromines ([APMIM] Br).Elementary analysis result is shown
The useful load of [BMIM] Br@ZIF-11 intermediate ion liquid is 19.2%.In 15vol%CO2In, in the range of 35~75 DEG C, to CO2
Adsorption capacity be 72.6mg/g to 63.1mg/g.
Embodiment 7
A kind of preparation method of zeolite imidazole ester skeleton-functionalized ion liquid composite, step is as follows:
(1) under nitrogen protection, 10mL ethanol and 1.622g (0.02mol) N- methylpyrroles are added toward 50mL flasks, plus
Enter 2g through vacuum drying ZIF-60 at 150 DEG C, 18h is stirred at room temperature;
(2) 20mL ethanol and 4.246g (0.022mol) 1- bromooctanes are added, under nitrogen protection, 24h is stirred at room temperature, takes out
Filter, is washed 3 times, each 20mL with ethanol;
(3) surname extraction 24h is carried out to filter residue with ethanol, then the dry 24h of 80 DEG C of vacuum, product code numbering is
[OctMPyr]Br@ZIF-60。
(4) take material 0.1g, after the pre-treatments such as drying, degassing, CO is carried out on multiple function apparatus2Breakthrough curve
Experiment, determines its CO2Adsorption capacity.
Thermogravimetric analysis (TGA) result show [OctMPyr] Br@ZIF-60 start after 325 DEG C decomposition, hence it is evident that higher than it is pure from
The heat decomposition temperature (220 DEG C) of sub- liquid 1- octyl groups -3- methylpyrroles bromine ([OctMPyr] Br).Elementary analysis result is shown
The useful load of [OctMPyr] Br@ZIF-60 intermediate ion liquid is 16.3%.In 15vol%CO2In, it is right in the range of 35~75 DEG C
CO2Adsorption capacity be 70.9mg/g to 62.4mg/g
Above-described embodiment is preferably embodiment, but embodiments of the present invention are not by above-described embodiment of the invention
Limitation, other any Spirit Essences without departing from the present invention and the change made under principle, modification, replacement, combine, simplification,
Equivalent substitute mode is should be, is included within protection scope of the present invention.
Claims (8)
1. a kind of preparation method of zeolite imidazole ester skeleton-functionalized ion liquid composite, it is characterised in that including following
Step:
(1) zeolitic imidazolate framework material is dried in vacuo;
(2) the dried zeolite imidazole skeleton material of step (1) is put into precursor A or precursor A solution, stirring is allowed to
Fully infiltrate and be uniformly dispersed;
(3) then add precursor B, precursor B by adsorption and diffusion enter zeolite imidazole branch framework material basket structure in
Precursor A response generation function ionic liquids;
(4) suction filtration, is removed the precursor for having neither part nor lot in reaction by surname extraction to filter residue, then it is dried in vacuo, from
And obtain zeolite imidazole ester skeleton-functionalized ion liquid composite;
Described zeolitic imidazolate framework material be ZIF-2, ZIF-7, ZIF-8, ZIF-11, ZIF-60 and ZIF-68 at least
It is a kind of;
Described precursor A is as follows:Imidazoles, tertiary phosphine class, pyridines, the one or more of pyroles and tertiary amine compounds,
Its formula is:
R in formula1、R2Or R3For hydrogen atom or alkyl substituent;
The long alkyl chains of described precursor A alkyl substituents are C1~C3;
Described precursor B formula is R-X;R is alkyl substituent or the alkyl substituent with functionalization group, X in formula
For Cl-、Br-Or I-;
The long alkyl chains of described precursor B alkyl substituents or the alkyl substituent with functionalization group are C3~C8。
2. the preparation method of zeolite imidazole ester skeleton-functionalized ion liquid composite according to claim 1, it is special
Levy and be:
Described precursor A and B mol ratio is 1:1~1:2.
3. the preparation method of zeolite imidazole ester skeleton-functionalized ion liquid composite according to claim 1 or 2,
It is characterized in that:
Described functionalization group is amido.
4. the preparation method of zeolite imidazole ester skeleton-functionalized ion liquid composite according to claim 1 or 2,
It is characterized in that:
Described precursor A is at least one of N- methylimidazoles and N- methylpyrroles.
5. the preparation method of zeolite imidazole ester skeleton-functionalized ion liquid composite according to claim 1 or 2,
It is characterized in that:
Described precursor B is at least one of 1- NBBs, 3- bromine propylamine hydrobromic acids and 1- bromooctanes.
6. a kind of zeolite imidazole ester skeleton-functionalized ion liquid composite, it is characterised in that appointed by Claims 1 to 5
Preparation method described in one is prepared.
7. zeolite imidazole ester skeleton-functionalized ion liquid composite described in claim 6 is in terms of sour gas trapping
In application.
8. application according to claim 7, it is characterised in that:
Described zeolite imidazole ester skeleton-functionalized ion liquid composite is in CO2Absorption and trapping in application.
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