CN114235983B - Method for removing and detecting nipagin ester based on covalent organic framework adsorbent - Google Patents
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Abstract
The invention discloses a method for removing and detecting nipagin ester based on a covalent organic framework adsorbent, which comprises the following steps of 3 O 4 The nano particles react with aldehyde and amino organic monomers in a solvent-thermal way to generate a core-shell type magnetic covalent organic framework compound which can be used as a magnetic solid phase extractant to collect the nipagin Jin Zhifu and sensitively detect and analyze the nipagin Jin Zhifu. The prepared magnetic covalent organic framework compound has large adsorption capacity to the nipagin ester, short adsorption time, and can rapidly remove the nipagin ester in the aqueous solution, and meanwhile, the magnetic covalent organic framework compound can be recycled, so that the removal cost is saved. The magnetic solid phase extraction-liquid phase chromatography-ultraviolet method is simple and quick, has short pretreatment time, shortens the detection time, and can reduce the detection cost.
Description
Technical Field
The invention belongs to the field of nanocomposite and food/environment detection and analysis, and particularly relates to a method for removing and detecting nipagin ester based on a covalent organic framework adsorbent.
Background
The common parabens mainly comprise methyl parahydroxybenzoate, ethyl parahydroxybenzoate, propyl parahydroxybenzoate, butyl parahydroxybenzoate and the like. The paraben is colorless and odorless, has relatively stable chemical properties, has broad-spectrum antibacterial property, is easy to synthesize, has low cost and the like, is often used as a preservative, and is widely applied to industries such as foods, medicines, cosmetics and the like at present. However, the research shows that the nipagin ester is a potential endocrine disrupter, can cause endocrine disturbance, has a certain relation with the formation and development of tumors, and has important significance for the removal and detection of the nipagin ester in foods and environments. However, the food and environmental systems are complex, and accurate detection of the parabens is difficult.
The magnetic solid phase extraction technology has the advantages of easy preparation, easy separation, simple operation, good biocompatibility, recycling and the like, has been used as a sample pretreatment technology with the most prospect aiming at a complex sample system, and is commonly used for enriching and measuring trace pollutants. The magnetic solid phase extractant comprises magnetic nano particles and a surface adsorption material, wherein the adsorption material is a core part and determines the characteristics and the application direction of the magnetic solid phase extraction technology.
The covalent organic framework COFs material is a novel porous nano material, has a high specific surface area, an adjustable porous structure and good chemical and thermal stability, can be self-assembled in a solution to form an ordered crystalline structure, and is widely applied to gas adsorption separation, catalysis, energy storage, sensing and the like.
Disclosure of Invention
Aiming at the defects of the prior art in a complex sample system, the invention aims to provide a method for removing and detecting nipagin ester based on a covalent organic framework adsorbent.
In order to achieve the above purpose, the following specific technical scheme is adopted:
a method for removing and detecting nipagin ester based on a covalent organic framework adsorbent, comprising the steps of:
(a) Pretreating a sample;
(b) Preparing a magnetic covalent organic framework adsorbent;
(c) And removing and detecting the nipagin ester by combining a magnetic solid phase extraction-liquid chromatography-ultraviolet detection analysis technology.
Further, the step (a) includes the steps of: making food or environmental sample into aqueous solution, centrifuging at 5000-10000rpm, removing precipitate, filtering with 0.22 μm filter membrane, retaining supernatant, and preserving at 4deg.C.
Further, the step (b) includes the steps of: fe is added to 3 O 4 Dispersing the nano particles in aldehyde group and amino organic monomer solution dissolved in an organic solvent by ultrasonic for 1-5 minutes, adding glacial acetic acid, transferring into a reaction kettle, performing solvothermal reaction for 1-36 hours, sequentially refluxing and washing with tetrahydrofuran and ethanol, and drying in vacuum for 4-12 hours to obtain the magnetic covalent organic framework adsorbent.
Wherein the aldehyde and amino organic monomers described in step (b),
(1) The aldehyde ligand is
Wherein X is C or N;
(2) The amino ligand is
Wherein R is H or OH or CH 3 Or OCH (optical wavelength) 3 Or NO 2 。
Further, the organic solvent in the step (b) is one or more of N, N dimethylacetamide, o-dichlorobenzene, N-butanol, trichlorobenzene, mesitylene and dioxane.
Still further, step (c) comprises the steps of:
(1) Adjusting the pH of the sample solution obtained in step (a) to 4-8;
(2) Adding the magnetic covalent organic framework adsorbent obtained in the step (b) into the solution obtained in the step (1), and uniformly mixing by a uniformly mixing instrument;
(3) Separating the adsorbent from the solution with a magnet, and discarding the supernatant;
(4) Adding eluent into the residues in the step (3), and uniformly mixing by a uniformly mixing instrument, wherein the eluent is dispersed by ultrasonic to obtain a magnetic covalent organic framework adsorbent;
(5) Separating the adsorbent from the solution with a magnet, retaining the supernatant and removing the solvent with a nitrogen blower;
(6) Redissolving the substance in (5) by using a methanol solvent;
(7) The sample solution in (6) was analyzed by high performance liquid chromatography-ultraviolet detection.
Wherein, the amount of the sample solution of the step (1) taken in the step (2) is 1-10mL, and the amount of the magnetic covalent organic framework adsorbent added in the step (2) is 1-100mg; the extraction time is 1-30 minutes.
In the step (4), the eluent is any one of acetone, methanol and ethanol, the using amount of the eluent is 1-5mL, and the mixing time is 1-30 minutes.
Further, the dosage of the redissolved methanol solvent in the step (6) is 1-2mL.
Still further, the high performance liquid chromatography-ultraviolet detection analysis technique described in step (7) uses a chromatographic column C18: 250mm x 4.6mm,5 μm; column oven temperature: 30 ℃; flow rate: 1mL/min; the sample injection volume is 20 mu L; the mobile phase is: the ratio of water to acetonitrile is 55:45; the wavelength of the ultraviolet detector was 254nm.
The beneficial effects of the invention are as follows:
the invention firstly utilizes the magnetic covalent organic framework compound as an adsorbent to remove and detect the nipagin ester in food or environment, and establishes a detection method for rapidly analyzing the nipagin ester in the aqueous solution. The prepared magnetic covalent organic framework compound has large adsorption capacity to the nipagin ester, short adsorption time, and can rapidly remove the nipagin ester in the aqueous solution, and meanwhile, the magnetic covalent organic framework compound can be recycled, so that the removal cost is saved. The magnetic solid phase extraction-liquid phase chromatography-ultraviolet method is simple and quick, has short pretreatment time, shortens the detection time, and can reduce the detection cost.
Drawings
FIG. 1 is a schematic diagram of the removal and detection of parabens in food or environment using a magnetic covalent organic framework adsorbent as the adsorbent;
FIG. 2 is a representation of a magnetic covalent organic framework adsorbent, wherein A is an X-ray powder diffraction pattern, B is an infrared spectrogram, C is a hysteresis regression graph, and D is a projection electron microscope;
FIG. 3 is a graph of optimized conditions for removing and detecting parabens from food or environment using a magnetic covalent organic framework complex as an adsorbent, wherein A extraction time, B adsorbent dosage, C particle intensity, D solution pH, E eluent type, F elution time.
Detailed Description
The principles and features of the present invention are described below in connection with examples, which are set forth only to illustrate the present invention and not to limit the scope of the invention.
Example 1
Preparation of magnetic covalent organic framework adsorbent
Aldehyde-based organic monomers (2, 5-dihydroxyterephthalaldehyde, for example, 0.072 mmol) and amino-based organic monomers (1, 3, 5-tris (4-aminophenyl) benzene, for example, 0.048 mmol) were dissolved in o-dichlorobenzene and n-butanol (1:1, 3 mL), fe 3 O 4 Nanoparticle (50 mg) is ultrasonically dispersed in the solution, the solution is ultrasonically treated for 1 minute, glacial acetic acid (6M, 0.06 mL) is added, the mixture is transferred into a reaction kettle, the solvothermal reaction is carried out for 36 hours, tetrahydrofuran and ethanol are sequentially subjected to reflux washing, and vacuum drying is carried out for 12 hours, so that the magnetic covalent organic framework adsorbent is obtained.
As shown in fig. 2, the X-powder diffraction patterns of the magnetic covalent organic framework adsorbent demonstrate the formation of crystalline covalent organic frameworks in the adsorbent at 2.9 °, 4.9 °, 5.8 ° and 7.5 °; 1614cm in infrared chart of magnetic covalent organic framework adsorbent -1 、1589cm -1 (C=N) and 631cm -1 、585cm -1 (Fe-O) demonstrated successful Synthesis of Fe 3 O 4 The @ COFs complex; from Fe 3 O 4 Fe can be seen in the hysteresis regression curve of the @ COFs composite 3 O 4 @ COFs and Fe 3 O 4 The saturation magnetization of (C) was 36.2emu g respectively -1 And 58.8emu g -1 The magnetization intensity is reduced because the covalent organic framework material is wrapped outside the magnetic ball, but the requirement of quick separation can be met; fe (Fe) 3 O 4 The transmission electron microscope image of @ COFs shows that the composite material is of a core-shell structure and the COF layer thickness is about 30nm.
Example 2
And (3) removing the preservative propyl p-hydroxybenzoate.
Making food or environmental sample into aqueous solution, centrifuging at 8000rpm, removing precipitate, filtering with 0.22 μm filter membrane, retaining supernatant, and preserving at 4deg.C. The adsorption capacity of the propyl p-hydroxybenzoate is optimized by utilizing the magnetic covalent organic framework composite material, and the calculation formula is as follows:
Q＝(C 0 －C)V/m
wherein C is 0 For the initial concentration of propyl parahydroxybenzoate before adsorption, C is the concentration of propyl parahydroxybenzoate in the supernatant after adsorption, V is the volume of the solution, and m is the mass of the magnetic covalent organic framework composite material applied in the adsorption process. As shown in fig. 3, the optimal adsorption condition is that the dosage of the magnetic covalent organic framework material is 2mg, the adsorption time is 5 minutes, and the pH of the optimal adsorption solution is 4.0, and the ionic strength does not affect the adsorption effect, so that the specific method for removing the propyl p-hydroxybenzoate comprises the following steps:
and (3) adjusting the pH of the sample pretreatment liquid to 4.0, taking 3mL of sample solution, adding 2mg of the magnetic covalent organic framework composite material, carrying out ultrasonic treatment for 10 seconds, uniformly mixing by a uniformly mixer for 5 minutes, wherein the magnetic covalent organic framework composite material reaches adsorption balance on propyl p-hydroxybenzoate in the solution, and the maximum adsorption capacity of the magnetic covalent organic framework material is 500mg/g.
Example 3
And (3) removing the preservative methyl parahydroxybenzoate.
The procedure and method were essentially the same as in example 2, except that methyl parahydroxybenzoate was contained in the sample solution.
Example 4
And (5) removing the preservative ethyl p-hydroxybenzoate.
The procedure and method were essentially the same as in example 2, except that ethyl parahydroxybenzoate was contained in the sample solution.
Example 5
And (3) removing the preservative butyl p-hydroxybenzoate.
The procedure and method were essentially the same as in example 2, except that butyl p-hydroxybenzoate was contained in the sample solution.
Example 6
Co-removal of the preservative, nipagin ester.
The procedure and method were substantially the same as in example 2, except that methyl parahydroxybenzoate, ethyl parahydroxybenzoate, propyl parahydroxybenzoate and butyl parahydroxybenzoate were contained in the sample solution.
Example 7
And (5) detecting and analyzing the preservative nipagin ester.
The sample pretreatment and adsorption method was essentially the same as in example 2, except (1) the eluent type and elution time were optimized, as shown in fig. 3, the optimal elution solvent was methanol in an amount of 1mL and the elution time was 5 minutes; (2) liquid chromatography-ultraviolet detection analysis conditions; chromatographic column C18 column: 250mm x 4.6mm,5 μm; column oven temperature: 30 ℃; flow rate: 1mL/min; the sample injection volume is 20 mu L; the mobile phase is: the ratio of water to acetonitrile is 55:45; the wavelength of the ultraviolet detector was 254nm.
Example 8
Detection and analysis of nipagin ester in lake water and beverage.
In order to verify the practicability of the magnetic covalent organic framework material for magnetic solid phase extraction of the nipagin ester, a liquid chromatography-ultraviolet detection analysis method and a labeling recovery method are adopted to measure the lake water and three beverages of the cola company, each sample is measured for 3 times in parallel, the recovery rate and the relative standard deviation of the labeling sample are obtained, the result is shown in a table 1, the recovery rate of the lake water and the three beverages is higher, and the method has a huge application prospect in the detection analysis of the nipagin ester in the aqueous solution.
TABLE 1 liquid phase-ultraviolet analysis results of magnetic solid phase extraction of nipagin ester by magnetic covalent organic framework material
Claims (1)
1. A method for removing and detecting a nipagin ester based on a covalent organic framework adsorbent, comprising the steps of:
(a) Pretreating a sample;
(b) Preparing a magnetic covalent organic framework adsorbent;
(c) Combining magnetic solid phase extraction-liquid chromatography-ultraviolet detection analysis technology to detect and remove the nipagin ester;
said step (a) comprises the steps of: preparing food or environmental sample into aqueous solution, centrifuging at 5000-10000rpm, removing precipitate, filtering with 0.22 μm filter membrane, retaining supernatant, and preserving at 4deg.C;
said step (b) comprises the steps of: fe is added to 3 O 4 Dispersing the nano particles in aldehyde organic monomer and amino organic monomer solution dissolved in an organic solvent by ultrasonic, adding glacial acetic acid by ultrasonic for 1-5 minutes, transferring into a reaction kettle, performing solvothermal reaction for 1-36 hours, sequentially refluxing and washing with tetrahydrofuran and ethanol, and drying in vacuum for 4-12 hours to obtain the magnetic covalent organic framework adsorbent;
(1) The aldehyde group organic monomer is
Wherein X is C;
(2) The amino organic monomer is
Wherein R is OH;
the organic solvent is o-dichlorobenzene and n-butanol;
step (c) comprises the steps of:
(1) Adjusting the pH of the sample solution obtained in step (a) to 4;
(2) Adding the magnetic covalent organic framework adsorbent obtained in the step (b) into the solution obtained in the step (1), and uniformly mixing by a uniformly mixing instrument;
(3) Separating the adsorbent from the solution with a magnet, and discarding the supernatant;
(4) Adding eluent into the residues in the step (3), and uniformly mixing by a uniformly mixing instrument, wherein the eluent is dispersed by ultrasonic to obtain a magnetic covalent organic framework adsorbent;
(5) Separating the adsorbent from the solution with a magnet, retaining the supernatant and removing the solvent with a nitrogen blower;
(6) Redissolving the substance in (5) by using a methanol solvent;
(7) Analyzing the sample solution in (6) by high performance liquid chromatography-ultraviolet detection;
the amount of the sample solution obtained in the step (1) in the step (2) is 3mL, and the amount of the added magnetic covalent organic framework adsorbent is 2mg; the extraction time is 5 minutes;
the eluent in the step (4) is any one of acetone, methanol and ethanol, the dosage of the eluent is 1-5mL, and the mixing time is 1-30 minutes;
the dosage of the redissolved methanol solvent in the step (6) is 1-2mL;
the high performance liquid chromatography-ultraviolet detection analysis technique of step (7) using a chromatographic column C18 column: 250mm x 4.6mm,5 μm; column oven temperature: 30 ℃; flow rate: 1mL/min; the sample injection volume is 20 mu L; the mobile phase is: the ratio of water to acetonitrile is 55:45; the wavelength of the ultraviolet detector was 254nm.
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