CN113244896A - Persimmon peel imprinting composite material and preparation method thereof - Google Patents
Persimmon peel imprinting composite material and preparation method thereof Download PDFInfo
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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
- B01J20/26—Synthetic macromolecular compounds
- B01J20/268—Polymers created by use of a template, e.g. molecularly imprinted polymers
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- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
The invention discloses a persimmon peel imprinted composite material and a preparation method thereof, and the method is characterized in that the characteristic that persimmon peel contains rich plant tannin is utilized, a surface imprinting technology is adopted, the persimmon tannin is used as a functional monomer, metal ions are used as a template, imprinted polymers are formed on the surface of the persimmon peel under the action of a cross-linking agent, and the metal ions are eluted by an acid solution to prepare the persimmon peel imprinted composite material. The material has the excellent performances of stable structure, large adsorption capacity to metal ions of the template, repeated use for many times and the like. The method has the advantages of simple process flow and low preparation cost, can realize the value-added utilization of the waste biomass, and has good economic benefit and social benefit.
Description
Technical Field
The invention relates to the fields of ion imprinting technology and biomass value-added utilization, in particular to a persimmon peel imprinting composite material and a preparation method thereof.
Background
The ion imprinting technology generates a recognition cavity site with space size and structure specificity to target ions through the interaction and coordination of a functional monomer and template ions. The recognition site can realize selective adsorption of target ions and has important significance for enriching and recovering low-concentration trace ions. In recent years, ion imprinting has been used in the fields of solid phase extraction, chromatography, electrochemical sensors, and pharmaceutical analysis, and has become a hot spot of current research.
The functional monomer provides functional groups for the whole imprinting process, and the selection of the monomer has great influence on the performance of the imprinted composite material. The tannic acid structurally contains a large number of phenolic hydroxyl groups, and the synergistic effect of the phenolic hydroxyl groups enables the complex reaction to be more easily carried out on catechol and biphenyltriol of the tannin. The phenolic hydroxyl groups can form stable five-membered chelate rings after complexing metal ions, which is also the main reason why tannin can adsorb the metal ions. Research proves that the ion imprinting composite material designed by using the tannic acid as the functional monomer realizes the high-efficiency adsorption of target ions. However, due to the water solubility of tannic acid, when tannic acid is used as a functional monomer, modification or group grafting needs to be carried out on a substrate material, so that tannic acid and the substrate are fixed in a covalent bond form, and the preparation steps are complicated, thereby influencing industrial application. The plant tannin is also called plant polyphenol, has a plurality of phenolic hydroxyl groups on the molecular structure, has large relative molecular mass and wide distribution, is widely present in persimmons, and is a natural high molecular compound with rich resources, low price and easy obtainment. Based on the high adsorption performance of the tannin as the surface of the functional monomer, if the high-efficiency directional adsorbent can be designed by utilizing natural plant wastes rich in plant tannin through an ion imprinting technology, the method has great environmental benefit and economic benefit.
Disclosure of Invention
The invention aims to provide a preparation method of a persimmon peel imprinted composite material, which is low in cost and simple in steps.
The invention also aims to provide the persimmon peel imprinting composite material prepared by the method, which has good adsorption performance.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows: a preparation method of a persimmon peel imprinted composite material comprises the following steps:
1) coating persimmon tannin cross-linked polymer on the surface of the persimmon peel under the action of a cross-linking agent by using persimmon tannin on the surface of the persimmon peel as a functional monomer and metal ions as a template by adopting a surface imprinting technology;
2) and (2) carrying out metal ion elution on the product obtained in the step 1) to prepare the persimmon peel imprinted composite material.
Preferably, the specific operation of step 1) is as follows: mixing dried persimmon peel with solution containing gallium ions, and stirring at room temperature for 2-4 hr to obtain Ga solution3+Completely chelating persimmon tannin on the surface of the persimmon peel; adding the cross-linking agent into the mixed solution, and stirring for 12-36h at 50-70 ℃ in a water bath.
Preferably, the persimmon peel is powder particles with the particle size of less than 74 microns.
Preferably, the solution containing gallium ions is a gallium chloride solution, and the concentration of the gallium ions is 0.01-0.05 mol/L.
Preferably, the cross-linking agent is glutaraldehyde, and the addition amount of the cross-linking agent is 1.25-12.5mL/gDried persimmon peel。
Preferably, the specific operation of step 2) is: washing the product obtained in the step 1) by deionized water, then putting the product into an acid solution for soaking for 2-4h, washing and filtering until the filtrate does not contain Ga3+And drying to obtain the finished product.
Preferably, the acid solution is hydrochloric acid or nitric acid with the concentration of 1 mol/L.
The invention also provides the persimmon peel imprinting composite material prepared by the method.
The persimmon peel imprinting composite material provided by the invention has good strong acid and strong alkali resistance, stable structure, repeated utilization and excellent specificity identification performance; the persimmon peel imprinted composite material has the advantages of fast adsorption on template ions and large adsorption capacity, and within the research range of the invention, the equilibrium adsorption amount of the persimmon peel imprinted composite material on the template metal ions is 51.78mg/g, and the adsorption equilibrium time is 60 min.
Compared with the prior art, the invention has the following beneficial effects:
1. the invention adopts the biomass persimmon peel as the raw material, plant tannin in the persimmon peel as the functional monomer, and reduces the input cost of exogenous functional monomer by polydentate chelation of the poly-o-phenol structure of the plant tannin and metal ions.
2. The method has the advantages of low cost and simple operation, is easy for large-scale industrial application, realizes value-added utilization of biomass, and has good economic and environmental benefits.
Drawings
FIG. 1 is an SEM image of a persimmon peel imprinted composite material before pickling in example 1 of the present invention.
FIG. 2 is an EDX spectrum of a persimmon peel imprinted composite material before acid washing in example 1 of the present invention.
Fig. 3 is a TOC control trend graph of supernatant after soaking the persimmon peel imprinted composite material prepared in example 1 in acid-base solutions with different concentrations.
FIG. 4 shows Ga adsorbed by persimmon peel imprinted composite material prepared in example 3 of the present invention with time3+The adsorption capacity of (2) is changed.
FIG. 5 shows Ga in the imprinted composite material of persimmon peel under different cycle times3+Comparative adsorption performance of (c).
Detailed Description
The invention is described in further detail below with reference to the figures and specific examples.
Example 1: preparation of persimmon peel imprinted composite material
(1) Adopts surface imprinting technology, uses persimmon tannin on the surface of persimmon peel as a functional monomer, Ga3+Coating persimmon tannin cross-linked polymer on the surface of persimmon peel under the action of a cross-linking agent glutaraldehyde as a template: collecting 0.4g dried persimmon peel with particle size less than 74 μm, and adding 30mL GaCl with concentration of 0.05mol/L3The solution was stirred for 2h, then 2mL of the crosslinker glutaraldehyde was added and stirred for 24h in a water bath at 55 ℃.
(2) Washing the product obtained in the step (1) by deionized water, and soaking the product in 1mol/L HCl solution for 2 hours until Ga can not be detected in the soaking solution3+And washing with deionized water, and drying to obtain the persimmon peel imprinted composite material.
FIG. 1 is an SEM image of a persimmon peel imprinted composite material before pickling; FIG. 2 is an EDX chart of the imprinted composite material of persimmon peel before acid washing. Ga can be seen from FIGS. 1 and 23+The imprinting layer is successfully loaded on the surface of the persimmon peel.
Example 2: preparation of persimmon peel imprinted composite material
(1) Adopts surface imprinting technology, uses persimmon tannin on the surface of persimmon peel as a functional monomer, Ga3+Coating persimmon tannin cross-linked polymer on the surface of persimmon peel under the action of a cross-linking agent glutaraldehyde as a template: taking 0.6g dried persimmon peel with particle size less than 74 μm, adding 30mL GaCl with concentration of 0.05mol/L3The solution was stirred for 2h, then 5mL of the crosslinker glutaraldehyde were added and stirred for 24h in a water bath at 55 ℃.
(2) Washing the product obtained in the step (1) by deionized water, and adding HNO with the concentration of 1mol/L3Soaking in the solution for 2h until no Ga is detected in the soaking solution3+And washing with deionized water, and drying to obtain the persimmon peel imprinted composite material.
SEM-EDX of the persimmon peel imprinted composite synthesized in this example is similar to that of example 1.
Example 3: preparation of persimmon peel imprinted composite material
(1) Adopts surface imprinting technology, uses persimmon tannin on the surface of persimmon peel as a functional monomer, Ga3+Coating persimmon tannin on the surface of persimmon peel under the action of cross-linking agent glutaraldehyde as templateBipolymer: taking 0.2g dried persimmon peel with particle size less than 74 μm, adding 30mL GaCl with concentration of 0.02mol/L3The solution was stirred for 2h, then 1.5mL of the crosslinker glutaraldehyde was added and stirred for 24h in a water bath at 55 ℃.
(2) Washing the product obtained in the step (1) by deionized water, and soaking the product in 1mol/L HCl solution for 2 hours until Ga can not be detected in the soaking solution3+And washing with deionized water, and drying to obtain the persimmon peel imprinted composite material.
SEM-EDX of the persimmon peel imprinted composite synthesized in this example is similar to that of example 1.
Example 4: preparation of persimmon peel imprinted composite material
The procedure for preparing the persimmon peel imprinted composite material in this example was substantially the same as in example 1, except that the amount of the crosslinking agent added was 0.5 mL.
SEM-EDX of the persimmon peel imprinted composite synthesized in this example is similar to that of example 1.
Example 5: preparation of persimmon peel imprinted composite material
The procedure for preparing the persimmon peel imprinted composite material in this example was substantially the same as in example 1, except that the amount of the crosslinking agent added was 1 mL.
SEM-EDX of the persimmon peel imprinted composite synthesized in this example is similar to that of example 1.
Example 6: preparation of persimmon peel imprinted composite material
The procedure for preparing the persimmon peel imprinted composite material in this example was substantially the same as in example 1, except that the amount of the crosslinking agent was 4 mL.
SEM-EDX of the persimmon peel imprinted composite synthesized in this example is similar to that of example 1.
Example 7: preparation of persimmon peel imprinted composite material
The procedure for preparing the persimmon peel imprinted composite material in this example was substantially the same as in example 1, except that the amount of the crosslinking agent was 5 mL.
SEM-EDX of the persimmon peel imprinted composite synthesized in this example is similar to that of example 1.
Table 1 shows the properties of the imprinted composite material under different amounts of the cross-linking agent, and the results show that the addition of the cross-linking agent glutaraldehyde causes the surface area of the imprinted composite material of persimmon peel to show a tendency of decreasing first and then increasing, which indicates that the amount of the cross-linking agent has a significant effect on the performance of the imprinted composite material of persimmon peel.
Table 1 shows the results of characterization of the properties of the imprinted composite persimmon peel material at different crosslinking agents
Example 8: stability of persimmon peel imprinted composite material
10mg of the persimmon peel imprinted composite material synthesized in example 1 was weighed, added to 10mL of HCl and NaOH solutions with concentrations of (1-6mol/L), respectively, stirred at room temperature for 24 hours, filtered, and the Total Organic Carbon (TOC) concentration of the supernatant was determined, and the results are shown in FIG. 3.
Fig. 3 is a TOC contrast trend graph of the supernatant of the dried persimmon peel and persimmon peel imprinted composite material after being soaked in acid-base solutions with different concentrations, and the result shows that the persimmon peel imprinted composite material only has about 5mg/L of organic substances leached in a strong acid-base solution, and has good structural stability.
Example 9: preparation of persimmon peel imprinting composite material and Ga-doped persimmon peel imprinting composite material3+Adsorption performance of
100mL of GaCl with the concentration of 60mg/L is prepared3Solution, 1g of the persimmon peel imprinted composite material prepared in example 3 is added into the solution, stirring and adsorption are carried out, as can be seen from figure 4, adsorption balance is achieved after 60min, and detection shows that the product can be used for detecting Ga3+The equilibrium adsorption capacity of the adsorbent can reach 51.78 mg/g.
Example 10: ga-based persimmon peel imprinted composite material under different cycle times3+Adsorption efficiency of
GaCl with the preparation concentration of 60mg/L3Adding 10g/L of the persimmon peel imprinted composite material prepared in the example 3 into the solution, adsorbing for 60min, filtering, and treating the persimmon peel with 1mol/L HCl solutionEluting the imprinted composite material for 5 times, and detecting Ga in the imprinted composite material of persimmon peel under five times of tests3+The adsorption capacity of (2) is shown in FIG. 5.
FIG. 5 shows Ga in persimmon peel imprinted composite material after five times of cyclic reuse3+The results show that the persimmon peel imprinted composite material synthesized by using the persimmon peel as the raw material has the characteristics of high stability and cyclic utilization.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
Claims (8)
1. The preparation method of the persimmon peel imprinted composite material is characterized by comprising the following steps:
1) coating persimmon tannin cross-linked polymer on the surface of the persimmon peel under the action of a cross-linking agent by using persimmon tannin on the surface of the persimmon peel as a functional monomer and metal ions as a template by adopting a surface imprinting technology;
2) and (2) carrying out metal ion elution on the product obtained in the step 1) to prepare the persimmon peel imprinted composite material.
2. The preparation method of the persimmon peel imprinted composite material as claimed in claim 1, wherein the specific operations of step 1) are as follows: mixing dried persimmon peel with solution containing gallium ions, and stirring at room temperature for 2-4 hr to obtain Ga solution3+Completely chelating persimmon tannin on the surface of the persimmon peel; adding the cross-linking agent into the mixed solution, and stirring for 12-36h at 50-70 ℃ in a water bath.
3. The method for preparing the persimmon peel imprinted composite material as claimed in claim 1 or 2, wherein the persimmon peel is powder particles with a particle size of less than 74 μm.
4. The method for preparing the persimmon peel imprinted composite material as claimed in claim 2, wherein the gallium ion-containing solution is a gallium chloride solution, and the concentration of gallium ions is 0.01-0.05 mol/L.
5. The preparation method of the persimmon peel imprinted composite material as claimed in claim 1 or 2, wherein the cross-linking agent is glutaraldehyde, and the addition amount of the cross-linking agent is 1.25-12.5mL/gDried persimmon peel。
6. The preparation method of the persimmon peel imprinted composite material as claimed in claim 1, wherein the step 2) is specifically performed by: washing the product obtained in the step 1) by deionized water, then putting the product into an acid solution for soaking for 2-4h, washing and filtering until the filtrate does not contain Ga3+And drying to obtain the finished product.
7. The method for preparing the persimmon peel imprinted composite material as claimed in claim 6, wherein the acid solution is hydrochloric acid or nitric acid with a concentration of 1 mol/L.
8. The persimmon peel imprinted composite material prepared by the preparation method of any one of claims 1 to 7.
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| CN112452302A (en) * | 2020-11-06 | 2021-03-09 | 辽宁大学 | Three-dimensional gallium imprinted Chinese gall tannin silicon-based composite material and application thereof in gallium recovery |
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