CN109762106A - A kind of preparation method of the hydrogen sulfide molecule imprinted polymer of " sandwich " structure - Google Patents
A kind of preparation method of the hydrogen sulfide molecule imprinted polymer of " sandwich " structure Download PDFInfo
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- CN109762106A CN109762106A CN201910016586.3A CN201910016586A CN109762106A CN 109762106 A CN109762106 A CN 109762106A CN 201910016586 A CN201910016586 A CN 201910016586A CN 109762106 A CN109762106 A CN 109762106A
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Abstract
The invention discloses a kind of preparation methods of the hydrogen sulfide molecule imprinted polymer of " sandwich " structure, with the modified metal organic framework (POMs@MOFs) of heteropoly acid for carrier, using water as template molecule, monomer, crosslinking agent, pore-foaming agent is added, cross-linking polymerization is carried out in carrier surface, prepare the hydrogen sulfide molecule imprinted polymer with " sandwich " structure, contain double bond and functional group in the monomer, the functional group is carboxyl, amide group, ester group or pyridine groups.Polymer prepared by the present invention realizes that hydrogen sulfide is separated with the selection of carbon dioxide as adsorbent, efficiently removes hydrogen sulfide.
Description
Technical field
The present invention relates to a kind of preparation methods of the hydrogen sulfide molecule imprinted polymer of " sandwich " structure, as well as
Application of the adsorbent in terms of removing hydrogen sulfide, belongs to the technology scope of Air Pollution Control.
Background technique
Here statement only provides background information related to the present invention, without necessarily constituting the prior art.
Hydrogen sulfide (H2It S) is a kind of nothing being widely present in the gases such as natural gas, biogas, coke-stove gas and oil refining exhaust gas
One of the main component that the toxic foul gas of color and air pollution preventing need to remove.Hydrogen sulfide has stronger acidity
And corrosivity, it can one of heavy corrosion industrial equipment and pipeline, and the major pollutants for causing acid rain.In addition, hydrogen sulfide
In the presence of seriously endangering human health, the hydrogen sulfide of low concentration to eye, respiratory system and central nervous system all have an impact as fever,
It itches, have a headache, is dizzy, expiratory dyspnea, sucking a small amount of high-concentration hydrogen sulfide can be even dead in causing asphyxia, stupor in the short time
It dies.Following provisions have been done to the concentration of hydrogen sulfide by occupational safety and health administration, the world (OSHA): concentration is lower than 10ppm's
Hydrogen sulfide is defined as hypotoxicity, and concentration is moderate toxicity between the hydrogen sulfide of 10~30ppm, and concentration is higher than the hydrogen sulfide of 30ppm
It is defined as high toxicity.
There are mainly two types of the minimizing technologies of hydrogen sulfide known for inventor: (1) dry method: the adsorbents such as carbon material, molecular sieve
Absorption method, membrane separation process, metal oxide method, irradiate decomposition method, Claus method；(2) wet process: chemical oxidization method has
Machine alcohol amine absorption process, Alkali absorption method, ionic liquid and biological desulfurization.Compared with wet desulphurization, dry desulfurization is to equipment
No corrosion, operating cost is low, and easy to operate flexible, condition of compatibility is wide, has obtained extensive research.But in industrial gasses
In addition to hydrogen sulfide, also often there is carbon dioxide (CO2).Hydrogen sulfide and carbon dioxide belong to sour gas, and property is similar, are ok
It is removed by alkali adsorbent or absorbent.In addition, the molecular dynamics diameter of hydrogen sulfide isThe molecule power of carbon dioxide
Learning diameter isThey have similar molecular dynamics diameter, so that effect is adsorbed in the selection reduced to hydrogen sulfide physical absorption
Rate.
Molecular engram is a kind of mechanism of action based on Ag-Ab, is printed for preparing the molecule with " memory effect "
The technology of mark polymer (molecularly imprinted polymers, MIPs).Briefly, the system of molecularly imprinted polymer
Standby process be exactly using target molecule as template, function monomer and template in covalent, non-covalent or half covalent mode in conjunction with shape
At presoma, then the polymer stable by the chemical polymerization forming properties of crosslinking agent, finally again removes template, generate with
Template binding site complementary in size and shape.This unique binding site makes molecularly imprinted polymer to target molecule
There is height selective power.But according to the inventors knowledge, since hydrogen sulfide gas is toxic and unstable, not directly it is used as mould
Plate molecule prepares hydrogen sulfide molecule imprinted polymer, thus prepares hydrogen sulfide molecule imprinted polymer and have larger difficulty.
Summary of the invention
In order to solve the deficiencies in the prior art, the object of the present invention is to provide a kind of hydrogen sulfide molecules of " sandwich " structure
The polymer of preparation is realized the selection point of hydrogen sulfide and carbon dioxide by the preparation method of imprinted polymer as adsorbent
From efficiently removing hydrogen sulfide.
To achieve the goals above, the technical solution of the present invention is as follows:
On the one hand a kind of preparation method of hydrogen sulfide molecule imprinted polymer is provided, using water as the mould for replacing hydrogen sulfide
Plate molecule carries out bulk polymerization, suspension polymerisation, emulsion polymerization, precipitation polymerization or surface imprinted polymerization and molecular engram is prepared
Polymer.
The present invention has found that hydrone is similar to the configuration of hydrogen sulfide after study, and performance is stablized, using water as template system
Standby molecularly imprinted polymer can carry out specific adsorption to hydrogen sulfide.
On the other hand a kind of preparation method of the hydrogen sulfide molecule imprinted polymer of " sandwich " structure is provided, with miscellaneous more
The modified metal organic framework (POMs@MOFs) of acid is carrier, and using water as template molecule, monomer, crosslinking agent, pore-foaming agent is added,
Cross-linking polymerization is carried out in carrier surface, prepares the hydrogen sulfide molecule imprinted polymer with " sandwich " structure, it is described
Contain double bond and functional group in monomer, the functional group is carboxyl, amide group, ester group or pyridine groups.
The present invention has found that surface imprinted polymerization is that imprinted polymer is loaded to certain solid-phase matrix after further research
On, the problem of adsorption site is accumulated is alleviated, effective adsorption site is increased, to increase molecularly imprinted polymer to vulcanization
The adsorption effect of hydrogen；Meanwhile being also able to solve the difficult problem of molecularly imprinted polymer regeneration.
The third aspect provides a kind of hydrogen sulfide molecule imprinted polymer that above-mentioned preparation method obtains.
Fourth aspect provides a kind of removal methods of hydrogen sulfide, using above-mentioned hydrogen sulfide molecule imprinted polymer as desulfurization
Agent makes the gas containing hydrogen sulfide by realizing the removing to hydrogen sulfide in gas after desulfurizing agent.
5th aspect provides a kind of regeneration method of above-mentioned hydrogen sulfide molecule imprinted polymer, after removing hydrogen sulfide
After hydrogen sulfide molecule imprinted polymer is using air purging, regenerative vulcanized hydrogen molecule imprinted polymer is obtained.
Desulfurization principle of the invention are as follows: at room temperature, utilize the suction with specific shape and size of material surface
Attached site selects adsorption of hydrogen sulfide, and the hydrogen sulfide then adsorbed is diffused by the duct of MOFs and is transmitted in MOFs frame,
And then it is removed by internal heteropoly acid catalysis.
The present invention has the following characteristics that compared with prior art
1. the desulfurization technology that the present invention combines molecular imprinting technology with absorption method, can be improved the selection of adsorbent
Property, the interference of other gases in industrial gasses is excluded, to improve the desulfuration efficiency of adsorbent.
2. the present invention can not only provide big specific surface area, alleviate imprinted polymer using POMs@MOFs as carrier
Packing phenomenon, and can use the unique oxidation-reduction quality of heteropoly acid and catalysis characteristics, hydrogen sulfide is subjected to catalyzed conversion.
3. the low (< 10m of individual heteropoly acid specific surface area2/ g), and it is not easily recycled regeneration, the present invention is by heteropoly acid
Fixed in MOFs, it is possible to reduce the accumulation of heteropoly acid disperses it relatively evenly, improves the utilization rate and recycling of heteropoly acid
Rate.
4. the material in the present invention by hydrogen sulfide stripping and can convert at room temperature.
In conclusion the present invention be it is a kind of selectivity it is high, simple and easy, corrosion-free, low energy consumption, it is pollution-free, have centainly
Industrial application value.
Specific embodiment
It is noted that described further below be all exemplary, it is intended to provide further instruction to the disclosure.Unless another
It indicates, all technical and scientific terms used herein has usual with disclosure person of an ordinary skill in the technical field
The identical meanings of understanding.
It should be noted that term used herein above is merely to describe specific embodiment, and be not intended to restricted root
According to the illustrative embodiments of the disclosure.As used herein, unless the context clearly indicates otherwise, otherwise singular
Also it is intended to include plural form, additionally, it should be understood that, when in the present specification using term "comprising" and/or " packet
Include " when, indicate existing characteristics, step, operation, device, component and/or their combination.
It is toxic and unstable in view of hydrogen sulfide gas, that hydrogen sulfide molecule trace is not directly prepared as template molecule is poly-
The deficiency of object is closed, in order to solve technical problem as above, the present disclosure proposes a kind of hydrogen sulfide molecule prints of " sandwich " structure
The preparation method of mark polymer.
A kind of exemplary embodiment of the disclosure provides a kind of preparation method of hydrogen sulfide molecule imprinted polymer, with
Water carries out bulk polymerization, suspension polymerisation, emulsion polymerization, precipitation polymerization or surface imprinted as the template molecule for replacing hydrogen sulfide
Molecularly imprinted polymer is prepared in polymerization.
The disclosure finds that hydrone is similar to the configuration of hydrogen sulfide after study, and performance is stablized, using water as template system
Standby molecularly imprinted polymer can carry out specific adsorption to hydrogen sulfide.
The another embodiment of the disclosure provides a kind of hydrogen sulfide molecule imprinted polymer of " sandwich " structure
Preparation method, with the modified metal organic framework (POMs@MOFs) of heteropoly acid for carrier, using water as template molecule, addition monomer,
Crosslinking agent, pore-foaming agent carry out cross-linking polymerization in carrier surface, prepare the hydrogen sulfide molecule with " sandwich " structure and print
Mark polymer, double bond and functional group are contained in the monomer, and the functional group is carboxyl, amide group, ester group or pyridine
Group.
The disclosure finds that surface imprinted polymerization is that imprinted polymer is loaded to certain solid-phase matrix after further research
On, the problem of adsorption site is accumulated is alleviated, effective adsorption site is increased, to increase molecularly imprinted polymer to vulcanization
The adsorption effect of hydrogen；Meanwhile being also able to solve the difficult problem of molecularly imprinted polymer regeneration.
In one or more embodiments of the embodiment, the metal organic framework is terephthalic acid (TPA) and zirconium chloride
It is prepared.The accumulation of heteropoly acid can be preferably retrieved using the metal organic framework.
In one or more embodiments of the embodiment, the modified metal organic framework of heteropoly acid the preparation method comprises the following steps:
Phthalic acid, zirconium chloride and heteropoly acid are added into hydrochloric acid and dimethylformamide, solvent thermal reaction is carried out.Solvent heat is anti-
It should refer in enclosed system such as autoclave, using organic matter or non-aqueous solvent as solvent, in the spontaneous pressure of certain temperature and solution
Under power, the reaction of original stock progress.
In the series embodiment, the mass ratio of zirconium chloride and phthalic acid is 0.05~10:0.05~10.
In the series embodiment, the mass ratio of zirconium chloride and heteropoly acid is 0.05~10:0.05~10.
In the series embodiment, zirconium chloride, hydrochloric acid and dimethylformamide addition are than being 0.05~10:0.1~10:1
~100, g:mL:mL.
In the series embodiment, the condition of solvent thermal reaction is 100~300 DEG C, and the reaction time is 12~48h.
In one or more embodiments of the embodiment, step are as follows: water and monomer are added in pore-foaming agent after dissolving, then
Carrier is added, is uniformly mixing to obtain suspension, crosslinking agent and initiator will be added into suspension, is sealed after being passed through nitrogen, into
Row reaction, the precipitating after reaction is washed, is dried.
In the series embodiment, the pore-foaming agent is methanol, dimethyl sulfoxide, dimethylformamide, acetonitrile, ethyl acetate
Or acetone.
In the series embodiment, monomer is methacrylic acid, acrylamide, methyl methacrylate or 4-vinylpyridine.
In the series embodiment, crosslinking agent is tetraethoxysilane, phenyl triethoxysilane, ethylene glycol dimethyl propylene
Acid esters or Triallyl isocyanurate.
In the series embodiment, 2,2 '-azo of initiator bis- (2,4- methyl pentane nitriles), azodiisobutyronitrile, peroxide
Change benzoyl or potassium peroxydisulfate.
In the series embodiment, being passed through nitrogen flow is 10~200mL/min, and the time is 5~60min.
In the series embodiment, reaction temperature is 0~75 DEG C.
In the series embodiment, the reaction time is 12~48h.
In the series embodiment, water, monomer, pore-foaming agent, carrier, crosslinking agent input ratio be 0.01~10:0.05~10:
0.1~100:0.1~5:0.01~10, mL:g:mL:g:mL.
Embodiment there is provided the hydrogen sulfide molecule trace polymerizations that a kind of above-mentioned preparation method obtains for the third of the disclosure
Object.
Embodiment there is provided a kind of removal methods of hydrogen sulfide for the 4th kind of the disclosure, and above-mentioned hydrogen sulfide molecule is printed
Mark polymer makes the gas containing hydrogen sulfide by realizing the removing to hydrogen sulfide in gas after desulfurizing agent as desulfurizing agent.
The 5th kind of the disclosure embodiment there is provided a kind of regeneration method of above-mentioned hydrogen sulfide molecule imprinted polymer,
After hydrogen sulfide molecule imprinted polymer after removing hydrogen sulfide is purged using air, regenerative vulcanized hydrogen molecule trace polymerization is obtained
Object.
In order to enable those skilled in the art can clearly understand the technical solution of the disclosure, below with reference to tool
The technical solution of the disclosure is described in detail in the embodiment of body.
Embodiment 1
(1) preparation of POMs@MOFs
0.41g terephthalic acid (TPA), 0.4167g zirconium chloride and 0.25g phosphomolybdic acid are weighed, 3.3mL concentrated hydrochloric acid (quality is added
Score 37%) and 50mL dimethylformamide, it is transferred in stainless steel cauldron, in 120 DEG C of reaction 12h, obtains POMs@
MOFs。
(2) the hydrogen sulfide molecule imprinted polymer H of " sandwich " structure2The preparation of S-MIPs
1. taking 0.036mL water and 0.5687g acrylamide to be added to 60mL pore-foaming agent, (acetonitrile and ethyl acetate, volume ratio are
It makes it dissolve, adds 0.5g carrier (POMs@MOFs), magnetic agitation 60min in 1:3), obtain aaerosol solution.
2. 3.8mL ethylene glycol dimethacrylate and 0.1g benzoyl peroxide first are added into 1. resulting aaerosol solution
Acyl is passed through 20min nitrogen (flow 100mL/min), is sealed at 4 DEG C and reacts 48h.
Study hydrogen sulfide imprinted polymer H2The absorption property of S-MIPs
0.3g H is weighed respectively2S-MIPs and POMs@MOFs, fills it into quartz ampoule, and packed height is about
2.3cm.At room temperature, it is passed through the gaseous mixture (hydrogen sulfide and nitrogen, nitrogen are carrier gas) that flow is 100mL/min, wherein
The concentration of hydrogen sulfide is 1100mg/m3, using H2S gas analyzer is to tail gas H2S gas concentration carries out dynamic detection, and tail gas makes
Absorption processing is carried out with NaOH solution.The experimental results showed that H2S-MIPs ratio POMs@MOFs has better desulfurization effect, H2S-
Hydrogen sulfide adsorption amount of the MIPs in 150min can reach 24.1mg/g, and POMs@MOFs only has the adsorbance of hydrogen sulfide
19.7mg/g illustrates that molecular imprinting technology may be implemented to increase adsorption site, improves the purpose of desulfurization degree.
Hydrogen sulfide imprinted polymer H2The selection performance of S-MIPs
Weigh 0.3g H2S-MIPs is filled it into quartz ampoule, and packed height is about 2.3cm.At room temperature,
It is passed through the gaseous mixture (hydrogen sulfide, carbon dioxide and nitrogen, nitrogen are carrier gas) that flow is 100mL/min, wherein hydrogen sulfide and two
The concentration of carbonoxide is 1100mg/m3, using H2S gas analyzer is to tail gas H2S gas concentration carries out dynamic detection, uses
CO2Gas analyzer is to tail gas CO2Gas concentration carries out dynamic detection, and tail gas carries out absorption processing using NaOH solution.Experiment knot
Fruit shows in CO2Interference under, H2S-MIPs is able to maintain the characterization of adsorption to hydrogen sulfide, and to the adsorbance of hydrogen sulfide and does not have
There is CO2When as.
Hydrogen sulfide imprinted polymer H2The regenerability of S-MIPs
Weigh 0.3g H2S-MIPs is filled it into quartz ampoule, and packed height is about 2.3cm.At room temperature,
It is passed through the gaseous mixture (hydrogen sulfide and nitrogen, nitrogen are carrier gas) that flow is 100mL/min, wherein the concentration of hydrogen sulfide is
1100mg/m3, using H2S gas analyzer is to tail gas H2S gas concentration carries out dynamic detection, and tail gas is carried out using NaOH solution
Absorption processing.Regeneration method: by used H2S-MIPs is purged with air at room temperature, the H after regeneration2S-
MIPs carries out hydrogen sulfide adsorption experiment again.The experimental results showed that being tested by four adsorption-regeneration cycles, H2S-MIPs regeneration pair
The adsorption efficiency of hydrogen sulfide remains to be maintained at 90% or more.
The foregoing is merely preferred embodiment of the present disclosure, are not limited to the disclosure, for the skill of this field
For art personnel, the disclosure can have various modifications and variations.It is all within the spirit and principle of the disclosure, it is made any to repair
Change, equivalent replacement, improvement etc., should be included within the protection scope of the disclosure.
Claims (10)
1. a kind of preparation method of hydrogen sulfide molecule imprinted polymer, characterized in that using water as the template point for replacing hydrogen sulfide
Son carries out bulk polymerization, suspension polymerisation, emulsion polymerization, precipitation polymerization or surface imprinted polymerization and molecular engram polymerization is prepared
Object.
2. a kind of preparation method of the hydrogen sulfide molecule imprinted polymer of " sandwich " structure, characterized in that modified with heteropoly acid
Metal organic framework be carrier, using water as template molecule, be added monomer, crosslinking agent, pore-foaming agent, be crosslinked in carrier surface
Polymerization reaction prepares the hydrogen sulfide molecule imprinted polymer with " sandwich " structure, contains double bond and function in the monomer
Energy group, the functional group are carboxyl, amide group, ester group or pyridine groups.
3. preparation method as claimed in claim 2, characterized in that the metal organic framework is terephthalic acid (TPA) and four chlorinations
Zirconium is prepared.
4. preparation method as claimed in claim 2, characterized in that the preparation method of the modified metal organic framework of heteropoly acid
Are as follows: phthalic acid, zirconium chloride and heteropoly acid are added into hydrochloric acid and dimethylformamide, solvent thermal reaction is carried out；
Preferably, the mass ratio of zirconium chloride and phthalic acid is 0.05~10:0.05~10；
Preferably, the mass ratio of zirconium chloride and heteropoly acid is 0.05~10:0.05~10；
Preferably, zirconium chloride, hydrochloric acid and dimethylformamide addition are than being 0.05~10:0.1~10:1~100, g:mL:
mL。
5. preparation method as claimed in claim 4, characterized in that the condition of solvent thermal reaction is 100~300 DEG C, when reaction
Between be 12~48h.
6. preparation method as claimed in claim 2, characterized in that step are as follows: water and monomer are added in pore-foaming agent after dissolving,
Carrier is added, suspension is uniformly mixing to obtain, crosslinking agent and initiator will be added into suspension, is sealed after being passed through nitrogen,
It is reacted, the precipitating after reaction is washed, is dried.
7. preparation method as claimed in claim 6, characterized in that being passed through nitrogen flow is 10~200mL/min, time 5
~60min；
Or, the reaction time is 12~48h；Reaction temperature is 0~75 DEG C；
Or, the input ratio of water, monomer, pore-foaming agent, carrier, crosslinking agent is 0.01~10:0.05~10:0.1~100:0.1~5:
0.01~10, mL:g:mL:g:mL；
Or, pore-foaming agent is methanol, dimethyl sulfoxide, dimethylformamide, acetonitrile, ethyl acetate or acetone；
Or, monomer is methacrylic acid, acrylamide, methyl methacrylate or 4-vinylpyridine；
Or, crosslinking agent is that tetraethoxysilane, phenyl triethoxysilane, ethylene glycol dimethacrylate or triallyl are different
Cyanurate；
Or, initiator is 2,2 '-azos bis- (2,4- methyl pentane nitriles), azodiisobutyronitrile, benzoyl peroxide or persulfuric acid
Potassium.
8. the hydrogen sulfide molecule imprinted polymer that a kind of any preparation method of claim 1~7 obtains.
9. a kind of removal methods of hydrogen sulfide, characterized in that using hydrogen sulfide molecule imprinted polymer according to any one of claims 8 as
Desulfurizing agent makes the gas containing hydrogen sulfide by realizing the removing to hydrogen sulfide in gas after desulfurizing agent.
10. a kind of regeneration method of hydrogen sulfide molecule imprinted polymer according to any one of claims 8, characterized in that vulcanize removing
After hydrogen sulfide molecule imprinted polymer after hydrogen is purged using air, regenerative vulcanized hydrogen molecule imprinted polymer is obtained.
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