CN109762106B - Preparation method of hydrogen sulfide molecularly imprinted polymer with sandwich structure - Google Patents
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Abstract
The invention discloses a preparation method of a hydrogen sulfide molecularly imprinted polymer with a sandwich structure, which comprises the steps of taking a heteropoly acid modified metal organic frameworks (POMs @ MOFs) as a carrier, taking water as a template molecule, adding a monomer, a cross-linking agent and a pore-forming agent, and carrying out cross-linking polymerization reaction on the surface of the carrier to prepare the hydrogen sulfide molecularly imprinted polymer with the sandwich structure, wherein the monomer contains double bonds and functional groups, and the functional groups are carboxyl groups, amide groups, ester groups or pyridine groups. The polymer prepared by the invention is used as an adsorbent to realize the selective separation of hydrogen sulfide and carbon dioxide and efficiently remove the hydrogen sulfide.
Description
Technical Field
The invention relates to a preparation method of a hydrogen sulfide molecularly imprinted polymer with a sandwich structure and application of the hydrogen sulfide molecularly imprinted polymer as an adsorbent in removing hydrogen sulfide, belonging to the technical field of air pollution control.
Background
The statements herein merely provide background information related to the present disclosure and may not necessarily constitute prior art.
Hydrogen sulfide (H)2S) is colorless and toxic malodorous gas widely existing in natural gas, methane, coke oven gas, oil refining waste gas and other gases, and is one of main components for preventing air pollution and needing to be removed. Hydrogen sulfide has the advantages ofThe strong acidity and corrosiveness can severely corrode industrial equipment and pipelines, and are also one of the main pollutants causing acid rain. In addition, the existence of hydrogen sulfide seriously harms human health, the low concentration of hydrogen sulfide has effects on eyes, respiratory system and central nervous system such as fever, itching, headache, dizziness and dyspnea, and the inhalation of a small amount of high concentration of hydrogen sulfide can cause asphyxia, coma and even death in a short time. The world Occupational Safety and Health Administration (OSHA) makes the following provisions on the concentration of hydrogen sulfide: hydrogen sulfide at concentrations below 10ppm is defined as low toxicity, hydrogen sulfide at concentrations between 10 and 30ppm is moderately toxic, and hydrogen sulfide at concentrations above 30ppm is defined as high toxicity.
The removal methods of hydrogen sulfide known to the inventors are mainly of two types: (1) and (3) dry method: adsorption methods for adsorbents such as carbon materials and molecular sieves, membrane separation methods, metal oxide oxidation methods, radiation decomposition methods, claus methods; (2) and (2) wet method: chemical oxidation, organic alcohol amine absorption, alkali absorption, ionic liquid processes, and biological desulfurization. Compared with wet desulphurization, dry desulphurization basically has no corrosion to equipment, low operation cost, simple and flexible operation, wide adaptation conditions and extensive research. However, in addition to hydrogen sulfide, carbon dioxide (CO) is often present in industrial gases2). Both hydrogen sulfide and carbon dioxide are acid gases, similar in nature, that can be removed by alkaline adsorbents or absorbents. Furthermore, the hydrogen sulfide has a molecular kinetic diameter of
The carbon dioxide has a molecular kinetic diameter of
They have similar molecular kinetic diameters, thereby reducing the selective adsorption efficiency for the physical adsorption of hydrogen sulfide.
Molecular imprinting is a technique for preparing Molecularly Imprinted Polymers (MIPs) having a "memory effect" based on an antigen-antibody mechanism of action. Briefly, the preparation process of the molecularly imprinted polymer is to use a target molecule as a template, combine a functional monomer with the template in a covalent, non-covalent or semi-covalent manner to form a precursor, then form a polymer with stable performance through chemical polymerization of a cross-linking agent, and finally remove the template to generate a binding site complementary to the template in size and shape. The unique binding site enables the molecular imprinting polymer to have high selection capability for target molecules. However, as far as the inventor knows, the preparation of the hydrogen sulfide molecular imprinted polymer is difficult because hydrogen sulfide gas is toxic and unstable and cannot be directly used as a template molecule to prepare the hydrogen sulfide molecular imprinted polymer.
Disclosure of Invention
In order to solve the defects of the prior art, the invention aims to provide a preparation method of a hydrogen sulfide molecularly imprinted polymer with a sandwich structure, which takes the prepared polymer as an adsorbent to realize selective separation of hydrogen sulfide and carbon dioxide and efficiently remove the hydrogen sulfide.
In order to achieve the purpose, the technical scheme of the invention is as follows:
on the one hand, the preparation method of the hydrogen sulfide molecularly imprinted polymer is provided, and the molecularly imprinted polymer is prepared by using water as a template molecule for replacing hydrogen sulfide and performing bulk polymerization, suspension polymerization, emulsion polymerization, precipitation polymerization or surface imprinting polymerization.
According to the invention, researches show that the configuration of water molecules is similar to that of hydrogen sulfide, the performance is stable, and the molecularly imprinted polymer prepared by taking water as a template can specifically adsorb the hydrogen sulfide.
On the other hand, the preparation method of the hydrogen sulfide molecularly imprinted polymer with the sandwich structure is provided, wherein a heteropoly acid modified metal organic frameworks (POMs @ MOFs) is used as a carrier, water is used as a template molecule, a monomer, a cross-linking agent and a pore-forming agent are added, and the cross-linking polymerization reaction is carried out on the surface of the carrier to prepare the hydrogen sulfide molecularly imprinted polymer with the sandwich structure, wherein the monomer contains double bonds and functional groups, and the functional groups are carboxyl groups, amide groups, ester groups or pyridine groups.
Through further research, the invention discovers that the surface imprinting polymerization is to load the imprinted polymer on a certain solid-phase substrate, thus relieving the problem of accumulation of adsorption sites and increasing effective adsorption sites, thereby increasing the adsorption effect of the molecularly imprinted polymer on hydrogen sulfide; meanwhile, the problem of difficult regeneration of the molecularly imprinted polymer can be solved.
In a third aspect, a hydrogen sulfide molecularly imprinted polymer obtained by the preparation method is provided.
The fourth aspect provides a method for removing hydrogen sulfide, wherein the hydrogen sulfide molecularly imprinted polymer is used as a desulfurizer, and the hydrogen sulfide in the gas is removed after the gas containing hydrogen sulfide passes through the desulfurizer.
The fifth aspect provides a regeneration method of the above hydrogen sulfide molecularly imprinted polymer, wherein the hydrogen sulfide molecularly imprinted polymer after hydrogen sulfide removal is purged with air to obtain a regenerated hydrogen sulfide molecularly imprinted polymer.
The desulfurization principle of the invention is as follows: under the condition of room temperature, hydrogen sulfide is selectively adsorbed by utilizing adsorption sites with specific shapes and sizes on the surface of the material, and then the adsorbed hydrogen sulfide is diffused and transferred into an MOFs frame through pores of the MOFs and is further removed by catalysis of internal heteropoly acid.
Compared with the prior art, the invention has the following characteristics:
1. the desulfurization technology combining the molecular imprinting technology and the adsorption method can improve the selectivity of the adsorbent and eliminate the interference of other gases in industrial gas, thereby improving the desulfurization efficiency of the adsorbent.
2. According to the invention, POMs @ MOFs are used as a carrier, so that a large specific surface area can be provided, the accumulation phenomenon of imprinted polymers can be relieved, and hydrogen sulfide can be catalytically converted by utilizing the unique redox property and catalytic property of heteropoly acid.
3. Low specific surface area of heteropolyacid alone (<10m2And/g) and is not easy to recycle, the invention fixes the heteropoly acid in MOFs, can reduce the accumulation of the heteropoly acid, disperse the heteropoly acid more uniformly, and improve the utilization rate and the recovery rate of the heteropoly acid.
4. The material of the present invention can remove and convert hydrogen sulfide at room temperature.
In conclusion, the method has the advantages of high selectivity, simplicity, feasibility, no corrosion, low energy consumption, no pollution and certain industrial application value.
Detailed Description
It should be noted that the following detailed description is exemplary and is intended to provide further explanation of the disclosure. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs.
It is noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of example embodiments according to the present disclosure. As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, and it should be understood that when the terms "comprises" and/or "comprising" are used in this specification, they specify the presence of stated features, steps, operations, devices, components, and/or combinations thereof, unless the context clearly indicates otherwise.
In view of the defects that hydrogen sulfide gas is toxic and unstable and cannot be directly used as a template molecule to prepare the hydrogen sulfide molecularly imprinted polymer, the present disclosure provides a preparation method of the hydrogen sulfide molecularly imprinted polymer with a "sandwich" structure in order to solve the above technical problems.
The preparation method of the hydrogen sulfide molecularly imprinted polymer is characterized in that water is used as a template molecule for replacing hydrogen sulfide, and bulk polymerization, suspension polymerization, emulsion polymerization, precipitation polymerization or surface imprinting polymerization is carried out to prepare the molecularly imprinted polymer.
According to research, the water molecules and hydrogen sulfide are similar in configuration and stable in performance, and the molecularly imprinted polymer prepared by taking water as a template can specifically adsorb the hydrogen sulfide.
The other embodiment of the disclosure provides a preparation method of a hydrogen sulfide molecularly imprinted polymer with a 'sandwich' structure, which comprises the steps of taking a heteropoly acid modified metal organic frameworks (POMs @ MOFs) as a carrier, taking water as a template molecule, adding a monomer, a cross-linking agent and a pore-forming agent, and carrying out cross-linking polymerization reaction on the surface of the carrier to prepare the hydrogen sulfide molecularly imprinted polymer with the 'sandwich' structure, wherein the monomer contains double bonds and functional groups, and the functional groups are carboxyl groups, amide groups, ester groups or pyridine groups.
Further research shows that the surface imprinting polymerization is to load the imprinting polymer on a certain solid-phase substrate, so that the problem of adsorption site accumulation is relieved, and effective adsorption sites are increased, thereby increasing the adsorption effect of the molecular imprinting polymer on hydrogen sulfide; meanwhile, the problem of difficult regeneration of the molecularly imprinted polymer can be solved.
In one or more embodiments of this embodiment, the metal-organic framework is prepared from terephthalic acid and zirconium tetrachloride. The metal organic framework can better search the accumulation of heteropoly acid.
In one or more embodiments of this embodiment, the preparation of the heteropolyacid-modified metal-organic framework comprises: adding phthalic acid, zirconium tetrachloride and heteropoly acid into hydrochloric acid and dimethylformamide to carry out solvothermal reaction. The solvothermal reaction is a reaction of an original mixture in a closed system such as an autoclave by using an organic or non-aqueous solvent as a solvent at a certain temperature and under the autogenous pressure of the solution.
In the series of embodiments, the mass ratio of the zirconium tetrachloride to the phthalic acid is 0.05-10: 0.05-10.
In the series of embodiments, the mass ratio of the zirconium tetrachloride to the heteropoly acid is 0.05-10: 0.05-10.
In the series of examples, the addition ratio of zirconium tetrachloride to hydrochloric acid to dimethylformamide is 0.05-10: 0.1-10: 1-100, and g: mL: mL.
In the series of embodiments, the solvothermal reaction is carried out under the conditions of 100-300 ℃ for 12-48 h.
In one or more embodiments of this embodiment, the steps are: adding water and a monomer into a pore-foaming agent for dissolving, then adding a carrier, uniformly stirring to obtain a suspension, adding a cross-linking agent and an initiator into the suspension, introducing nitrogen, sealing, reacting, washing and drying the precipitate after the reaction.
In this series of embodiments, the porogen is methanol, dimethyl sulfoxide, dimethylformamide, acetonitrile, ethyl acetate, or acetone.
In this series of examples, the monomer is methacrylic acid, acrylamide, methyl methacrylate or 4-vinylpyridine.
In this series of examples, the crosslinking agent is tetraethoxysilane, phenyltriethoxysilane, ethylene glycol dimethacrylate, or triallyl isocyanurate.
In this series of examples, the initiator is 2, 2' -azobis (2, 4-dimethylvaleronitrile), azobisisobutyronitrile, benzoyl peroxide or potassium persulfate.
In the series of embodiments, the flow rate of the introduced nitrogen is 10-200 mL/min, and the time is 5-60 min.
In this series of examples, the reaction temperature is 0 to 75 ℃.
In the series of embodiments, the reaction time is 12-48 h.
In the series of embodiments, the input ratio of water, the monomer, the pore-forming agent, the carrier and the cross-linking agent is 0.01-10: 0.05-10: 0.1-100: 0.1-5: 0.01-10, and the input ratio of mL to g to mL.
In a third embodiment of the present disclosure, a hydrogen sulfide molecularly imprinted polymer obtained by the above preparation method is provided.
In a fourth embodiment of the present disclosure, the above-mentioned hydrogen sulfide molecularly imprinted polymer is used as a desulfurizing agent, and after a gas containing hydrogen sulfide passes through the desulfurizing agent, the hydrogen sulfide in the gas is removed.
The fifth embodiment of the disclosure provides a regeneration method of the above hydrogen sulfide molecularly imprinted polymer, and the hydrogen sulfide molecularly imprinted polymer after hydrogen sulfide removal is purged with air to obtain a regenerated hydrogen sulfide molecularly imprinted polymer.
In order to make the technical solutions of the present disclosure more clearly understood by those skilled in the art, the technical solutions of the present disclosure will be described in detail below with reference to specific embodiments.
Example 1
(1) Preparation of POMs @ MOFs
0.41g of terephthalic acid, 0.4167g of zirconium tetrachloride and 0.25g of phosphomolybdic acid were weighed, 3.3mL of concentrated hydrochloric acid (mass fraction: 37%) and 50mL of dimethylformamide were added, and the mixture was transferred to a stainless steel reaction vessel and reacted at 120 ℃ for 12 hours to obtain POMs @ MOFs.
(2) Hydrogen sulfide molecularly imprinted polymer H with sandwich structure2Preparation of S-MIPs
① dissolving 0.036mL of water and 0.5687g of acrylamide in 60mL of a pore-forming agent (acetonitrile and ethyl acetate in a volume ratio of 1:3), adding 0.5g of a carrier (POMs @ MOFs), and magnetically stirring for 60min to obtain a suspension solution.
② to the suspension ①, 3.8mL of ethylene glycol dimethacrylate and 0.1g of benzoyl peroxide were added, and the mixture was sealed under a nitrogen atmosphere (flow rate: 100mL/min) for 20min and reacted at 4 ℃ for 48 hours.
Study of Hydrogen sulfide imprinted Polymer H2Adsorption Performance of S-MIPs
Respectively weighing 0.3g H2S-MIPs and POMs @ MOFs, and the quartz tube is filled with the materials, and the filling height is about 2.3 cm. Introducing mixed gas (hydrogen sulfide and nitrogen, nitrogen as carrier gas) with flow rate of 100mL/min at room temperature, wherein the concentration of hydrogen sulfide is 1100mg/m3By using H2S gas analyzer for tail gas H2And (4) dynamically detecting the concentration of the S gas, and absorbing the tail gas by using a NaOH solution. The experimental result shows that H2S-MIPs has better desulfurization effect than POMs @ MOFs, H2The hydrogen sulfide adsorption capacity of S-MIPs in 150min can reach 24.1mg/g, and the adsorption capacity of POMs @ MOFs to hydrogen sulfide is only 19.7mg/g, which shows that the molecular imprinting technology can realize the purposes of increasing adsorption sites and improving desulfurization rate.
Hydrogen sulfide imprinted polymer H2Selectivity Performance of S-MIPs
Weighing 0.3g H2And S-MIPs, and filling the quartz tube with the filling height of about 2.3 cm. Introducing mixed gas (hydrogen sulfide, carbon dioxide and nitrogen, nitrogen) with the flow rate of 100mL/min at room temperatureGas as carrier gas), wherein the concentration of hydrogen sulfide and carbon dioxide are both 1100mg/m3By using H2S gas analyzer for tail gas H2Dynamic detection of S gas concentration by using CO2Gas analyzer for tail gas CO2And (4) dynamically detecting the gas concentration, and absorbing the tail gas by using NaOH solution. The experimental results show that in CO2Under the interference of (2), H2The S-MIPs can maintain the adsorption characteristic on the hydrogen sulfide, and the adsorption quantity on the hydrogen sulfide is high, and no CO is generated2The same applies.
Hydrogen sulfide imprinted polymer H2Reproducibility of S-MIPs
Weighing 0.3g H2And S-MIPs, and filling the quartz tube with the filling height of about 2.3 cm. Introducing mixed gas (hydrogen sulfide and nitrogen, nitrogen as carrier gas) with flow rate of 100mL/min at room temperature, wherein the concentration of hydrogen sulfide is 1100mg/m3By using H2S gas analyzer for tail gas H2And (4) dynamically detecting the concentration of the S gas, and absorbing the tail gas by using a NaOH solution. The regeneration method comprises the following steps: will use H2Blowing the S-MIPs by air at room temperature, and regenerating H2And performing hydrogen sulfide adsorption experiments on the S-MIPs. The experimental result shows that through four times of adsorption-regeneration cycle experiments, H2The adsorption efficiency of the S-MIPs regeneration on the hydrogen sulfide can still be kept above 90%.
The above description is only a preferred embodiment of the present disclosure and is not intended to limit the present disclosure, and various modifications and changes may be made to the present disclosure by those skilled in the art. Any modification, equivalent replacement, improvement and the like made within the spirit and principle of the present disclosure should be included in the protection scope of the present disclosure.
Claims (16)
1. A preparation method of a hydrogen sulfide molecularly imprinted polymer is characterized in that a heteropoly acid modified metal organic framework is used as a carrier, water is used as a template molecule for replacing hydrogen sulfide, and surface imprinting polymerization is carried out to prepare the molecularly imprinted polymer.
2. A preparation method of a hydrogen sulfide molecularly imprinted polymer with a sandwich structure is characterized in that a heteropoly acid modified metal organic framework is used as a carrier, water is used as a template molecule, a monomer, a cross-linking agent and a pore-forming agent are added, and a cross-linking polymerization reaction is carried out on the surface of the carrier to prepare the hydrogen sulfide molecularly imprinted polymer with the sandwich structure, wherein the monomer contains double bonds and functional groups, and the functional groups are carboxyl groups, amide groups, ester groups or pyridine groups.
3. The process according to claim 2, wherein the metal-organic framework is prepared from terephthalic acid and zirconium tetrachloride.
4. The process according to claim 2, wherein the heteropolyacid-modified metal-organic framework is prepared by: adding phthalic acid, zirconium tetrachloride and heteropoly acid into hydrochloric acid and dimethylformamide for solvothermal reaction;
the mass ratio of the zirconium tetrachloride to the phthalic acid is 0.05-10: 0.05-10;
the mass ratio of the zirconium tetrachloride to the heteropoly acid is 0.05-10: 0.05-10;
the adding ratio of the zirconium tetrachloride to the hydrochloric acid to the dimethylformamide is 0.05-10: 0.1-10: 1-100, and the g: mL: mL.
5. The process according to claim 4, wherein the solvothermal reaction is carried out at 100 to 300 ℃ for 12 to 48 hours.
6. The method of claim 2, comprising the steps of: adding water and a monomer into a pore-foaming agent for dissolving, then adding a carrier, uniformly stirring to obtain a suspension, adding a cross-linking agent and an initiator into the suspension, introducing nitrogen, sealing, reacting, washing and drying the precipitate after the reaction.
7. The method according to claim 6, wherein the flow rate of nitrogen gas is 10 to 200mL/min for 5 to 60 min.
8. The method according to claim 6, wherein the reaction time is 12 to 48 hours; the reaction temperature is 0-75 ℃.
9. The method according to claim 6, wherein the ratio of the water, the monomer, the pore-forming agent, the carrier and the crosslinking agent is 0.01-10: 0.05-10: 0.1-100: 0.1-5: 0.01-10, and the ratio of mL to g to mL.
10. The method according to claim 6, wherein the porogen is methanol, dimethyl sulfoxide, dimethylformamide, acetonitrile, ethyl acetate or acetone.
11. The process according to claim 6, wherein the monomer is methacrylic acid, acrylamide, methyl methacrylate or 4-vinylpyridine.
12. The process according to claim 6, wherein the crosslinking agent is tetraethoxysilane, phenyltriethoxysilane, ethylene glycol dimethacrylate or triallyl isocyanurate.
13. The process according to claim 6, wherein the initiator is 2, 2' -azobis (2, 4-dimethylvaleronitrile), azobisisobutyronitrile, benzoyl peroxide or potassium persulfate.
14. A hydrogen sulfide molecularly imprinted polymer obtained by the preparation method of any one of claims 1 to 13.
15. A method for removing hydrogen sulfide, characterized in that the hydrogen sulfide molecularly imprinted polymer as described in claim 14 is used as a desulfurizing agent, and hydrogen sulfide in a gas is removed by passing the gas containing hydrogen sulfide through the desulfurizing agent.
16. A method for regenerating a hydrogen sulfide molecularly imprinted polymer as claimed in claim 14, characterized in that the hydrogen sulfide molecularly imprinted polymer after removal of hydrogen sulfide is purged with air to obtain a regenerated hydrogen sulfide molecularly imprinted polymer.
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| CN111892791B (en) * | 2020-07-31 | 2022-07-19 | 北京化工大学 | Preparation method of composite material, composite material and application thereof |
| CN113083371B (en) * | 2021-04-24 | 2022-11-15 | 太原理工大学 | Phosphotungstic acid loaded iron-based MOF material and preparation and application thereof |
| CN114797410A (en) * | 2022-04-18 | 2022-07-29 | 苏州金宏气体股份有限公司 | Desulfurizing agent for purifying carbon dioxide and preparation method thereof |
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