CN105837509B - A kind of preparation method of the 2-methylimidazole Zn complex with hierarchical porous structure - Google Patents

A kind of preparation method of the 2-methylimidazole Zn complex with hierarchical porous structure Download PDF

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CN105837509B
CN105837509B CN201610204762.2A CN201610204762A CN105837509B CN 105837509 B CN105837509 B CN 105837509B CN 201610204762 A CN201610204762 A CN 201610204762A CN 105837509 B CN105837509 B CN 105837509B
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methylimidazole
solvable
methanol
polystyrene microsphere
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CN105837509A (en
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师唯
荆鹏
程鹏
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Nankai University
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/58Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/22Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/223Solid 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
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/22Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/223Solid 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
    • B01J20/226Coordination polymers, e.g. metal-organic frameworks [MOF], zeolitic imidazolate frameworks [ZIF]
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/28Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
    • B01J20/28054Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J20/28057Surface area, e.g. B.E.T specific surface area
    • B01J20/28066Surface area, e.g. B.E.T specific surface area being more than 1000 m2/g
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/28Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
    • B01J20/28054Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J20/28078Pore diameter
    • B01J20/2808Pore diameter being less than 2 nm, i.e. micropores or nanopores
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/28Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
    • B01J20/28054Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J20/28078Pore diameter
    • B01J20/28083Pore diameter being in the range 2-50 nm, i.e. mesopores
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/28Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
    • B01J20/28054Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J20/28078Pore diameter
    • B01J20/28085Pore diameter being more than 50 nm, i.e. macropores
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2220/00Aspects relating to sorbent materials
    • B01J2220/40Aspects relating to the composition of sorbent or filter aid materials
    • B01J2220/48Sorbents characterised by the starting material used for their preparation
    • B01J2220/4806Sorbents characterised by the starting material used for their preparation the starting material being of inorganic character
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2220/00Aspects relating to sorbent materials
    • B01J2220/40Aspects relating to the composition of sorbent or filter aid materials
    • B01J2220/48Sorbents characterised by the starting material used for their preparation
    • B01J2220/4812Sorbents characterised by the starting material used for their preparation the starting material being of organic character

Abstract

A kind of preparation method of the 2 methylimidazole Zn complexes with hierarchical porous structure, steps are as follows:1) it using the solvable polystyrene microsphere of arrangement as template, is uniformly mixed with methanol and 2 methylimidazoles, obtains solution a;2) zinc nitrate hydrate is dissolved in methanol and obtains solution b, solution b is added dropwise in solution a after five minutes, it stirs 24 hours at room temperature, centrifugation is washed to obtain white solid with ethyl alcohol, then N is used, N dimethylformamides or toluene remove the solvable polystyrene microsphere template of arrangement at 80 DEG C, obtain the 2 methylimidazole Zn complexes with hierarchical porous structure.It is an advantage of the invention that:Preparation method is simple, and raw material sources are extensive, at low cost, is easy to industrial amplification production;Material prepared by this method has high specific surface area, while having macropore, mesoporous and micropore;To organic solvent large amount of adsorption, and there is certain hydrophobicity.

Description

A kind of preparation method of the 2-methylimidazole Zn complex with hierarchical porous structure
Technical field
The present invention relates to hydrophobic organic solvent sorbing materials, and in particular to a kind of 2- methyl miaows with hierarchical porous structure The preparation method and applications of azoles Zn complex.
Background technology
Metal-organic framework materials (MOFs) due to its composition and hole controllability, be widely used in catalysis, fluorescence and The fields such as gas absorption, however the pore size of majority MOFs is less than 2nm, certain larger-size molecules cannot enter in duct Portion limits its related application.
The MOFs with hierarchical porous structure makes it while having micropore, mesoporous and macropore under synthesis meso-scale, can be promoted The connectivity in the ducts MOFs, the more surface-active sites of exposure, and then improve the performances such as its catalysis and absorption.
Invention content
It is above-mentioned there are problem the purpose of the present invention is being directed to, a kind of 2-methylimidazole zinc with hierarchical porous structure is provided and is matched Close the preparation method and applications of object.
Technical scheme of the present invention:
A kind of preparation method of the 2-methylimidazole Zn complex with hierarchical porous structure, includes the following steps:
1) it using the solvable polystyrene microsphere of arrangement as template, is uniformly mixed, obtains molten with methanol, 2-methylimidazole The amount ratio of liquid a, the solvable polystyrene microsphere template of arrangement, methanol and 2-methylimidazole are 0.2g:58mL:1.311g;
2) zinc nitrate hydrate is dissolved in methanol, the amount ratio of zinc nitrate hydrate and methanol is 0.298g:2mL is obtained Solution b is added dropwise in solution a after five minutes by solution b, stirs 24 hours at room temperature, centrifugation obtains white after being washed with ethyl alcohol Then solid removes the solvable polystyrene microsphere template of arrangement with n,N-Dimethylformamide at 80 DEG C, obtain having more The 2-methylimidazole Zn complex of grade pore structure.
The synthetic method of the solvable polystyrene microsphere template of the arrangement, includes the following steps:
1) styrene, methacrylic acid are uniformly mixed with water at 80 DEG C, obtain solution c, styrene, methacrylic acid Amount ratio with water is 54mL:6mL:450mL;
2) by potassium peroxydisulfate obtained solution d soluble in water, the amount ratio of potassium peroxydisulfate and water is 0.6g:30mL;
3) solution d is added in solution c, is persistently stirred 24 hours, obtained white solid used respectively after centrifugation water and Respectively three times, it is 1 then to use volume ratio to ethyl alcohol for washing:1 water and the mixed liquor dispersing solid of ethyl alcohol form suspension, with 4000r/min is centrifuged off supernatant, and solid is dried, the solvable polystyrene microsphere template arranged.
A kind of application of the prepared 2-methylimidazole Zn complex with hierarchical porous structure, for adsorbing methanol, second Alcohol, n-hexane, pentane, toluene, benzene, dichloromethane, petroleum ether, methyl-silicone oil, n,N-Dimethylformamide or vegetable oil.
It is an advantage of the invention that:
1. the preparation method is simple, raw material sources are extensive, at low cost, are easy to industrial amplification production;
2. material prepared by this method has high specific surface area while having macropore, mesoporous and micropore, be conducive to enhance The diffusion of hydrophobicity and organic solvent;
3. pair organic solvent large amount of adsorption has certain hydrophobicity.
Description of the drawings
Fig. 1 is the X-ray powder diffraction figure of the 2-methylimidazole Zn complex with hierarchical porous structure.
Fig. 2 is the 77K nitrogen adsorption desorption data of the 2-methylimidazole Zn complex with hierarchical porous structure, and illustration is aperture Distribution map.
Fig. 3 is adsorpting data figure of the 2-methylimidazole Zn complex to different organic solvents for having hierarchical porous structure.
Fig. 4 is sorption cycle datagram of the 2-methylimidazole Zn complex to ethyl alcohol for having hierarchical porous structure.
Specific implementation mode
In order to more specifically meticulously introduce this patent, a specific embodiment is now enumerated for explanation, exemplary embodiments It is directed to reference when specific implementation, and is not suitable for limiting the present invention.
Embodiment 1:
A kind of preparation method of the 2-methylimidazole Zn complex with hierarchical porous structure, steps are as follows:
1) preparation of the solvable polystyrene microsphere template arranged
54mL styrene, 6mL methacrylic acids are uniformly mixed with 450mL water at 80 DEG C, solution c is obtained;By 0.6g Potassium peroxydisulfate is dissolved in obtained solution d in 30mL water;Solution d is added in solution c, persistently stirs 24 hours, will be obtained after centrifugation White solid uses water and ethyl alcohol respectively, and respectively three times, it is 1 then to use volume ratio for washing:1 water and the mixed liquor dispersing solid of ethyl alcohol, Suspension is formed, supernatant is centrifuged off with 4000r/min, solid is dried, the solvable polystyrene microsphere mould arranged Plate.
2) it using the solvable polystyrene microsphere of 0.2g arrangements as template, is stirred with the 2-methylimidazole of 58mL methanol cores 1.311g It mixes uniformly mixed, obtains solution a;
3) 0.298g zinc nitrate hydrates are dissolved in 2mL methanol and obtain solution b, solution is added dropwise in solution b after five minutes It in a, stirs 24 hours at room temperature, centrifugation is washed to obtain white solid with ethyl alcohol, then uses n,N-Dimethylformamide or toluene The solvable polystyrene microsphere template that arrangement is removed at 80 DEG C obtains having the 2-methylimidazole zinc of hierarchical porous structure to coordinate Object.
Embodiment 2:
For the prepared 2-methylimidazole Zn complex with hierarchical porous structure for adsorbing ethyl alcohol, method is as follows:
It takes bottle one and weighs the quality (M of empty bottleIt is empty), weigh the 0.1g 2-methylimidazoles obtained with multilevel hierarchy Zn complex (MSample) be added in bottle, 1mL ethyl alcohol is then added and is sufficiently mixed, ethyl alcohol not to be adsorbed is sucked out after five minutes simultaneously Weigh the gross mass (M of bottle and sampleAlways), then utilize formula (MAlways-MIt is empty-MSample)/MSampleCalculate absorption of the sample to ethyl alcohol Amount.
The prepared 2-methylimidazole Zn complex with hierarchical porous structure is used respectively according to above-mentioned identical method In absorption methanol, ethyl alcohol, n-hexane, pentane, toluene, benzene, dichloromethane, petroleum ether, methyl-silicone oil and vegetable oil.
Fig. 1 is the X-ray powder diffraction figure of the 2-methylimidazole Zn complex with hierarchical porous structure, show its have compared with Good crystallinity.Fig. 2 is the 77K nitrogen adsorption desorption data of the 2-methylimidazole Zn complex with hierarchical porous structure, and illustration is Graph of pore diameter distribution.As can be seen from the figure its micropore with about 1nm, the mesoporous and macropore of about 50nm, specific surface Product is 1058g/m2.Fig. 3 is adsorpting data of the 2-methylimidazole Zn complex to different organic solvents for having hierarchical porous structure Figure.As a result show that the material all has the organic solvent tested the adsorbance of 196wt% or more.Fig. 4 is that have hole in one's power The 2-methylimidazole Zn complex of structure is to Ethanol Adsorption loop-around data figure.As a result adsorbance does not have after showing the material circulation 10 times There is apparent reduction.
It will be clear that the present invention is not limited to embodiment here, those skilled in the art are done by present inventive concept The obvious improvement and modification gone out all should be within protection scope of the present invention.

Claims (1)

1. a kind of preparation method of the 2-methylimidazole Zn complex with hierarchical porous structure, it is characterised in that including following step Suddenly:
1) synthetic method of the solvable polystyrene microsphere template arranged, includes the following steps:
Styrene, methacrylic acid are uniformly mixed with water at 80 DEG C, obtain solution c, styrene, methacrylic acid and water Amount ratio is 54mL:6mL:450mL;
By potassium peroxydisulfate obtained solution d soluble in water, the amount ratio of potassium peroxydisulfate and water is 0.6g:30mL;
Solution d is added in solution c, persistently stirs 24 hours, white solid will be obtained after centrifugation and is respectively washed with water and ethyl alcohol respectively It washs three times, it is 1 then to use volume ratio:1 water and the mixed liquor dispersing solid of ethyl alcohol are formed suspension, are centrifuged with 4000r/min Supernatant is removed, solid is dried, the solvable polystyrene microsphere template arranged;
2) it using the solvable polystyrene microsphere of arrangement as template, is mixed with methanol and 2-methylimidazole, obtains solution a, arranged The amount ratio of the solvable polystyrene microsphere template, methanol and the 2-methylimidazole that arrange is 0.2g:58mL:1.311g;
3) zinc nitrate hydrate is dissolved in methanol, the amount ratio of zinc nitrate hydrate and methanol is 0.298g:2mL obtains solution Solution b is added dropwise in solution a after five minutes by b, stirs 24 hours at room temperature, and centrifugation is washed to obtain white solid with ethyl alcohol, Then the solvable polystyrene microsphere template for removing arrangement at 80 DEG C with n,N-Dimethylformamide or toluene obtains having more The 2-methylimidazole Zn complex of grade pore structure.
CN201610204762.2A 2016-04-01 2016-04-01 A kind of preparation method of the 2-methylimidazole Zn complex with hierarchical porous structure Expired - Fee Related CN105837509B (en)

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CN106861637A (en) * 2017-03-30 2017-06-20 丽水学院 A kind of method that use Zn-ef ficiency doping improves the water stabilities of ZIF 67
CN109433238B (en) * 2018-10-10 2021-02-19 北京化工大学 Iron-nitrogen doped oxygen reduction carbon catalyst with ordered hierarchical pores and preparation method thereof
CN110305331B (en) * 2019-07-02 2021-09-28 南开大学 Method for constructing hierarchical porous MOF (metal organic framework) by ligand selective retention method

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