CN114534691B - Magnetic modified zeolite-like imidazole ester framework material and preparation and application thereof - Google Patents

Magnetic modified zeolite-like imidazole ester framework material and preparation and application thereof Download PDF

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CN114534691B
CN114534691B CN202011329457.9A CN202011329457A CN114534691B CN 114534691 B CN114534691 B CN 114534691B CN 202011329457 A CN202011329457 A CN 202011329457A CN 114534691 B CN114534691 B CN 114534691B
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zif
modified zeolite
imidazole ester
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CN114534691A (en
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许国旺
周智慧
赵春霞
路鑫
梁雯莹
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Dalian Institute of Chemical Physics of CAS
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • 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
    • B01J20/226—Coordination polymers, e.g. metal-organic frameworks [MOF], zeolitic imidazolate frameworks [ZIF]
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
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    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
    • B01J20/06—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising oxides or hydroxides of metals not provided for in group B01J20/04
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    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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    • B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
    • B01J20/28002—Solid 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 physical properties
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    • B01J2220/00—Aspects relating to sorbent materials
    • B01J2220/40—Aspects relating to the composition of sorbent or filter aid materials
    • B01J2220/46—Materials comprising a mixture of inorganic and organic materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2220/00—Aspects relating to sorbent materials
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Abstract

The invention belongs to the technical field of metal organic porous Materials (MOFs) and analysis, and in particular relates to a magnetic modified zeolite-like imidazole ester framework material-90 (Fe 3 O 4 @PEI-ZIF-90) and application thereof in selective enrichment of sulfonamides in milk. The magnetic Fe 3 O 4 The @ PEI-ZIF-90 material is synthesized by adopting a two-step hot solvent method, and Fe is synthesized first 3 O 4 The @ PEI nano particles are subjected to Schiff base reaction with aldehyde groups in ZIF-90 through amino groups in PEI to form the magnetic zeolite imidazole ester framework material. The material has the excellent characteristics of good selective adsorption, large adsorption capacity and the like. When the sulfonamide in the milk is selectively enriched, the method has the advantages of rapidness, simplicity in operation, high sensitivity and the like.

Description

Magnetic modified zeolite-like imidazole ester framework material and preparation and application thereof
Technical Field
The invention belongs to the technical field of metal organic porous materials and analysis, and in particular relates to a magnetic modified zeolite-like imidazole ester framework material (Fe 3 O 4 @ PEI-ZIF-90) and its application.
The magnetically modified imidazole ester framework material provided by the invention has a simple synthesis process, and can realize high selectivity and separation of sulfonamide substances in complex samples. The magnetic material has good application prospect in the field of food safety.
Technical Field
In 1995, yaghi OM first proposed Metal-organic frameworks (MOFs) with a range of advantages such as large specific surface area and pore channels, which can be used for gas storage, catalysis, and separation and adsorption of compounds. MOFs material has rich pi-pi bond, can absorb small molecular compounds in complex matrix, has special groups on the surface, and can be modified, so that certain performances of the MOFs material are improved. ZIFs belong to MOFs, have the advantages of metal frameworks, have the characteristics of natural zeolite, and have high chemical stability and thermal stability, so that the ZIFs can be used for separation, adsorption, storage and the like of substances.
Sulfonamide (SAs) substances are used as antibacterial agents in the course of livestock and poultry farming due to their low cost and good bactericidal capacity. Incorrect use and handling of sulfonamide antibiotics can result in some sulfonamide residues in the animal, which can lead to an imbalance in the microbial system in the animal. When sulfonamides are used for a long period of time, they cause excessive accumulation, which can cause a series of toxic effects on organisms, such as emesis and hematopoietic disorders. The maximum residual amount standard is adopted by many countries for sulfanilamide substances in animal-derived foods. Therefore, it is very important to develop a method for enriching trace sulfonamide substances.
Disclosure of Invention
The invention aims to provide a magnetically modified zeolite-like imidazole ester framework material (Fe) with simple preparation and high selectivity and enrichment for sulfonamides 3 O 4 @PEI-ZIF-90)。
A magnetically modified zeolite-like imidazole ester skeleton material adopts Fe 3 O 4 @ PEI-ZIF-90. Fe (Fe) 3 O 4 PEI represents a polyethyleneimine modified magnetic nanomaterial, fe 3 O 4 PEI-ZIF-90 is composed of Fe 3 O 4 The @ PEI nanoparticle is prepared by chemical reaction with ZIF-90.
The magnetic modified zeolite-like imidazole ester framework material (Fe 3 O 4 The specific synthesis method of @ PEI-ZIF-90) is as follows: adopts a two-step solvothermal reduction method. First, fe is synthesized 3 O 4 PEI nanoparticles, then reacted with ZIF-90. Because of Fe 3 O 4 @PEI contains abundant amino functional groups, ZIF-90 contains aldehyde functional groups, so Fe 3 O 4 The @ PEI nano particles can react with ZIF-90 to generate Fe 3 O 4 PEI-ZIF-90 material. The specific synthesis steps are as follows:
first, the synthesized Fe 3 O 4 Dispersing the PEI nano particles in DMF and carrying out ultrasonic treatment for 20-30min. Dispersing imidazole-2-formaldehyde in DMF, heating for 1-2h, cooling to room temperature, then adding DMF solution dissolved with zinc nitrate hexahydrate, and stirring for 30-40min. Finally adding Fe dispersed therein 3 O 4 After ultrasonic treatment of DMF solution of PEI nano particles for a period of time, transferring the mixture into a reaction kettle for reaction for 15-20h at 50-150 ℃. After cooling to room temperature, washing with DMF for 2-3 times, 10-15mL each time, then with dichloromethane for 3-5 times, 10-15mL each time, until the washing liquid becomes clear, finally dispersing in 25-30mL of dichloromethane, and standing for 15-18h; the methylene dichloride is removed, and the product is put into a vacuum drying oven and dried for 15-18h at 110-150 ℃.
The magnetic modified zeolite-like imidazole ester framework material is synthesized by adopting a two-step hot solvent method, and Fe is synthesized first 3 O 4 PEI nanoparticle, then Fe is synthesized 3 O 4 PEI-ZIF-90. The synthesis process is simple; fe (Fe) 3 O 4 The PEI nanoparticle contains rich amino functional groups, and can fully react with the ZIF-90 material, so that the obtained material has rich magnetism. ZIF-90 material itself contains abundant pi-pi bond, can carry out selective adsorption to target substance. When the magnetic nano particles modify the ZIF-90, the crystal form of the ZIF-90 material is not changed, so that the characteristics of the ZIF-90 are maintained.
The material can be directly used for adsorbing sulfonamide substances in complex matrixes, and has quick and simple operation. Has great application prospect in food safety.
The sulfa-like substances are sulfachloropyridazine, sulfadiazine, sulfamonomethoxine, sulfamethazine, sulfamethylthiadiazole, sulfamethoxazole and sulfathiazole.
The magnetic modified zeolite-like imidazole ester framework material has stronger chemical stability and magnetism, and can shorten the sample pretreatment time.
The material has the excellent characteristics of good selective adsorption, large adsorption capacity and the like. When the sulfonamide in the milk is selectively enriched, the method has the advantages of rapidness, simplicity in operation, high sensitivity and the like.
Drawings
FIG. 1 shows (a) Fe of the first embodiment of the present invention 3 O 4 (b) ZIF-90 and (c) Fe 3 O 4 IR chart of PEI-ZIF-90.
FIG. 2 shows (A) ZIF-90 of the first embodiment of the present invention, (a) Fe in (B) 3 O 4 And (b) Fe 3 O 4 Diffraction angle spectrum of @ PEI-ZIF-90.
FIG. 3 is a diagram of Fe according to the first embodiment of the present invention 3 O 4 (A) scanning electron microscope image of @ PEI-ZIF-90, (B) atomic energy level image
Fig. 4 is a liquid chromatography-mass spectrum after milk sample processing. (A) With Fe 3 O 4 A total profile of the mixture after @ PEI-ZIF-90 material treatment, (B) an extraction profile of SCP, (C) an extraction profile of SDZ, (D) an extraction profile of SMM, (E) an extraction profile of SMR, (F) an extraction profile of SMT, (G) an extraction profile of SMX, and (H) an extraction profile of STZ.
The invention is specifically illustrated below with reference to the drawings and this example is only to be understood and not to be limiting.
Detailed Description
Example 1
Synthesizing the magnetic modified zeolite-like imidazole ester material. The synthesis process comprises the following two steps:
in the first step, fe is synthesized by adopting a hot solvent method 3 O 4 PEI nanoparticles: into a 250mL flat-bottomed flask, 100mL of ethylene glycol, 2.0g of ferric trichloride hexahydrate, 8.0g of sodium acetate, 2.0g of polyethyleneimine (600 Da) were added, stirring was performed at 60 ℃ for 20min, transferred to a 200mL reaction kettle, reacted at 220 ℃ for 2h, and the solid product Fe 3 O 4 PEI was washed 3 times with ethanol and 20mL each time, then 3 times with DMF and 20mL each time; finally 450mg of Fe 3 O 4 PEI was dispersed in 20mL DMF and sonicated for 25min.
And the second step adopts a hot solvent method to modify ZIF-90 in one step:
1.4414g ICA was added to 50mL DMF solution, heated in 65℃water bath for 1h, cooled to room temperature; 2.9749g of zinc nitrate hexahydrate was added to 25mL of DMF solution and sonicated until complete dissolution. Adding DMF solution containing zinc nitrate hexahydrate into DMF solution containing ICA, stirring for 30min to disperse Fe in DMF 3 O 4 Adding the @ PEI nano material into the mixed solution, carrying out ultrasonic treatment for 15min, putting the mixed solution into a reaction kettle with a polytetrafluoroethylene lining, reacting for 18h at 100 ℃, cooling to room temperature, washing a solid product with DMF for 3 times, 20mL each time, 3 times with dichloromethane, 20mL each time, finally dispersing in 30mL of dichloromethane, standing for 15h, drying with a vacuum drying oven, and drying at 120 ℃ for 15h. Obtaining Fe 3 O 4 Magnetic zeolite imidazole ester material @ PEI-ZIF-90.
FIG. 1 shows (a) Fe 3 O 4 ，(b)ZIF-90，(c)Fe 3 O 4 IR chart of PEI-ZIF-90, from chart (a) 604cm -1 It can be known that Fe 3 O 4 The nanoparticle has-Fe-O-bond, 876cm from the graph (b) -1 As can be seen, ZIF-90 has a peak of-C (O) -H, which is a bending vibration of-C-H in aldehyde group, 876cm is seen from FIG. C -1 The peak at the position disappeared and appeared to be 604cm -1 The peaks of (2) indicate Fe 3 O 4 PEI reacted with ZIF-90 with Schiff base.
FIG. 2 shows (A) ZIF-90, (B) Fe (a) 3 O 4 And (b) Fe 3 O 4 XRD pattern of @ PEI-ZIF-90, it can be seen that the Fe was synthesized 3 O 4 The @ PEI-ZIF-90 material has a good crystal structure and uses Fe 3 O 4 Modification of ZIF-90 material by PEI does not change the crystal form of ZIF-90 because of Fe 3 O 4 The characteristic peak of XRD pattern of the @ PEI-ZIF-90 material contains Fe 3 O 4 And characteristic peaks of ZIF-90.
FIG. 3 shows (A) Fe 3 O 4 PEI-ZIF-90 scanning electron microscope and (B) Fe 3 O 4 Energy dispersive X-ray spectrogram of PEI-ZIF-90. From the graph (A), fe can be seen 3 O 4 The morphology of the @ PEI-ZIF-90 material is regular octahedronThe elements contained in the material can be seen from the diagram (B).
Example two
Selectively enrich sulfonamide in milk
a. Pretreatment of milk samples: taking 2.0mL of milk, adding 5.0mL of ethyl acetate, swirling for 30s, centrifuging at 15000rpm and 4 ℃ for 10min, taking the supernatant (as an extracting solution), repeating the steps of adding ethyl acetate, swirling and centrifuging for 3 times to the supernatant, combining the extracting solutions, and drying with nitrogen for later use.
b. Enrichment and elution of sulfonamides: adding 500 mu L of acetonitrile to the blow-dried sample, and adding 10mg of Fe prepared in the first example 3 O 4 The magnetic material @ PEI-ZIF-90 is vortexed for 5s and oscillated for 20min, the supernatant is removed after magnetic solid-liquid separation by adopting magnetite, the solid product is washed 3 times by acetonitrile, 500 mu L of methanol containing formic acid with the volume concentration of 3% is added, vortexed for 5s and oscillated for 8min for elution. 200 μl of eluate was lyophilized and then added with water: acetonitrile=2:1 (v/v) 200 μl mutual solubility, and finally detection was performed by liquid chromatography-mass spectrometry.
Fig. 4 is a liquid chromatography-mass spectrum after milk sample processing. (A) With Fe 3 O 4 A general profile of the mixture after treatment with PEI-ZIF-90, (B) an extraction of sulfachloropyridazine, (C) an extraction of sulfadiazine, (D) an extraction of sulfamonomethoxine, (E) an extraction of sulfamethyidine, (F) an extraction of sulfamebendazole, (G) an extraction of sulfamexazole, and (H) an extraction of sulfathiazole. From the figure, it can be seen that the milk sample contains sulfamonomethoxine, sulfamonomethoxine and sulfamethoxazole.
The magnetically modified zeolite-like imidazole ester Fe 3 O 4 The PEI-ZIF-90 material has the characteristics of simple preparation and strong selective adsorptivity, and has good adsorption effect on sulfonamides substances.

Claims (3)

1. The application of the magnetically modified zeolite-like imidazole ester framework material is characterized in that:
the magnetically modified zeolite-like imidazole ester skeleton is added into a liquid matrix containing sulfonamides substances, so that sulfonamides substances can be adsorbed and enriched;
the preparation method is to synthesize by a two-step hydrothermal method,
first, fe is synthesized by a hydrothermal method 3 O 4 Dispersing the synthesized nano particles in N, N-Dimethylformamide (DMF) for standby;
secondly, dissolving ICA in DMF, heating for a period of time, adding DMF solution dissolved with zinc nitrate hexahydrate into DMF solution dissolved with imidazole-2-formaldehyde (ICA), and stirring for a period of time; finally adding DMF solution dispersed with magnetic nano particles, carrying out heating reaction after ultrasonic treatment for a period of time to obtain the magnetic modified zeolite-like imidazole ester framework material Fe 3 O 4 @PEI-ZIF-90。
2. The use of the magnetically modified zeolite-like imidazole ester framework material according to claim 1, wherein the preparation method is characterized in that:
in the first step, fe is synthesized by adopting a hot solvent method 3 O 4 PEI nanoparticles: adding 100-150 g mL of ethylene glycol, 1.5-2.5 g g of ferric trichloride hexahydrate, 9.0-10.0 g g of sodium acetate and 2.0-3.0 g 600Da of polyethyleneimine into a container, stirring for 20-30min, transferring into a reaction kettle, reacting for 2-3 h, washing with ethanol, washing with DMF, and finally dispersing in DMF;
the two steps comprise the following specific processes:
400-500 mg Fe 3 O 4 Dispersing @ PEI in 10-20 mL DMF, and performing ultrasonic treatment for 20-30 min;
dispersing 1-2 g ICA in 50-100 mL DMF, heating in water bath at 50-100 ℃ for 1-2 h;
adding 2.5-4.0. 4.0 g zinc nitrate hexahydrate into 20-30 mL DMF, and performing ultrasonic treatment until the zinc nitrate hexahydrate is completely dissolved;
adding DMF solution containing zinc nitrate hexahydrate into DMF solution containing ICA, stirring for 30-40min, and adding Fe 3 O 4 Ultrasound is carried out for 10-15 min on DMF solution of PEI nano particles; transferring to a reaction kettle, reacting at 50-150 ℃ for 15-20h, and cooling to room temperature; the solid product was washed 2-3 times with DMF, 10-20 per mL, then 3-5 times with dichloromethane,10-20 per mL, dispersing in 25-30mL dichloromethane, standing for 15-18h; and removing dichloromethane, and placing the product into a vacuum drying oven to be dried at 110-150 ℃ for 15-18h.
3. The use of a magnetically modified zeolite-like imidazole ester scaffold material according to claim 1, characterized in that: the liquid matrix is milk extract.
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