CN115282757A - Functionalized ionic liquid for absorbing VOC (volatile organic compounds) and preparation method thereof - Google Patents
Functionalized ionic liquid for absorbing VOC (volatile organic compounds) and preparation method thereof Download PDFInfo
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- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/34—Chemical or biological purification of waste gases
- B01D53/74—General processes for purification of waste gases; Apparatus or devices specially adapted therefor
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- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/18—Absorbing units; Liquid distributors therefor
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- B01D53/34—Chemical or biological purification of waste gases
- B01D53/46—Removing components of defined structure
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- B01D53/34—Chemical or biological purification of waste gases
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- B01D53/48—Sulfur compounds
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- B01D53/34—Chemical or biological purification of waste gases
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- B01D53/54—Nitrogen compounds
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Abstract
The invention belongs to the field of chemical engineering environmental protection, and particularly relates to a functionalized ionic liquid capable of absorbing VOC (volatile organic compounds), and a preparation method of the ionic liquid. The ionic liquid is prepared from the raw materials of butyl sulfonate-methylimidazolium-p-toluenesulfonic acid, 1-butyl-3-methylimidazolium tetrafluoroborate, lead acetate and potassium permanganate. The functional ionic liquid prepared by the invention is used as a solvent, an absorbent and a reaction reagent in a system, so that the VOC is physically dissolved and absorbed and chemically captured in the gas-liquid exchange of the functional ionic liquid, and the high-efficiency treatment of the VOC is realized.
Description
Technical Field
The invention belongs to the field of chemical engineering environmental protection, and particularly relates to a functionalized ionic liquid capable of absorbing VOC (volatile organic compounds), and a preparation method of the ionic liquid.
Background
Volatile Organic Compounds (VOCs) are essentially all organic compounds having a corresponding volatility at ambient temperature. Volatile Organic Compounds (VOCs) generally refer to those organic compounds that have relatively low molecular mass and are volatile under ambient conditions at high saturated vapor pressures. Generally, volatile organic compounds are classified into various complex compounds such as aldehydes, ketones, aromatic hydrocarbons, halogenated hydrocarbons, aliphatic hydrocarbons, and other oxygen-containing compounds and nitrogen-containing compounds according to their components and chemical structures. The VOC gas is an important precursor causing regional compound air pollution characterized by ozone, PM2.5 and acid rain in China, seriously threatens the health of people, and can cause chronic poisoning, damage to the liver and nervous system, general weakness, sleepiness, skin itch and the like after being in an environment polluted by Volatile Organic Compounds (VOC) for a long time. The discharge reduction and the treatment of VOC are urgent and are far from the greatest extent.
The VOC treatment method is divided into two main categories, one category is a recycling method, and the other category is a destructive treatment method. The recycling method comprises a condensation method, an adsorption method, an absorption method and a membrane separation method, which remarkably reflects the recycling of the organic volatile matters, but has low VOC removal rate, can not achieve ideal effect when used alone, and is generally used in combination with other methods as the pretreatment of high-concentration organic volatile matters. Destructive methods include thermal storage thermal combustion (RTO), thermal storage catalytic combustion (RCO), biodegradation, photocatalytic oxidation, and low temperature plasma. The method has high VOC removal rate, but has large investment and outstanding operation safety problem, and is suitable for the treatment of low-concentration VOCs.
CN106237920A discloses a treatment process and system of VOC-containing industrial waste gas, this process adopts the method of absorbing and burning to handle VOC-containing industrial waste gas, and the absorbent adopts machine oil, wash oil or organic solvent, and the absorbing device adopts the jet nozzle to mix and absorb, absorbs most VOC through gas-liquid mixture, and the VOC-containing industrial waste gas that is not absorbed by the absorbent enters the incinerator to burn and then evacuate, and the treatment efficiency reaches more than 99%. However, the absorbent adopted by the technology still has certain vapor pressure, and can volatilize into a gas phase under certain conditions, SO that VOC in industrial waste gas is absorbed, new VOC can be generated and enter a subsequent incinerator, and new SO can be generated by the incineration process for treating organic volatile matters containing sulfur, nitrogen and the like 2 Or NO 2 There are certain limitations. CN106994293 discloses a device and a process for treating VOC waste gas of an oil refinery, the technology adopts an absorption tower, a desulfurizing tower and a catalytic oxidation unit to treat the waste gas, an absorbent of the absorption tower uses low-temperature diesel oil with the temperature of 5-10 ℃ for absorption, and the absorbed diesel oil is subjected to regeneration treatment. CN108905577A discloses a VOC waste gas purification treatment method, which adopts two-stage alkali spray absorption, and the gas after alkali absorption is passed through three-stage adsorption process to attain the goal of waste gas purification. But alkali absorption is only suitableThe absorption effect of acid VOC gas absorption and spraying absorption is poor, and the treatment of the adsorption waste residue generated in the adsorption process is still a difficult problem. Therefore, the research for developing a new VOC treatment path is still a direction with practical application value, and is an important technical guarantee for effective prevention and control of atmospheric pollution and winning of blue sky guard war in China.
Disclosure of Invention
In view of the above, the present invention aims to provide a functionalized ionic liquid for absorbing VOC and a preparation method thereof.
The technical scheme adopted by the invention is as follows:
a functionalized ionic liquid for absorbing VOC is prepared from butyl sulfonate-methylimidazolium-p-toluenesulfonic acid, 1-butyl-3-methylimidazolium tetrafluoroborate, lead acetate and potassium permanganate, wherein the mass ratio of the substances is 1-8.
Further preferably, the mass ratio of the sulfobutyl-methylimidazolium-p-toluenesulfonic acid to the 1-butyl-3-methylimidazolium tetrafluoroborate to the lead acetate to the potassium permanganate is 1-4.
A method of preparing a functionalized ionic liquid comprising the steps of: dissolving potassium permanganate into deionized water to form a solution with the concentration of 1-5%, adding lead acetate powder, stirring for dissolving, continuously adding 1-butyl-3-methylimidazolium tetrafluoroborate and butyl sulfonate-methylimidazolium-p-toluenesulfonic acid under stirring, and uniformly stirring to obtain the potassium permanganate-sodium sulfovinate-p-toluenesulfonate.
When the functionalized ionic liquid is used, the functionalized ionic liquid is filled into a circulating tank, the liquid is pumped into a liquid inlet of a supergravity absorber by a circulating pump, gas containing VOC (volatile organic compounds) such as ammonia, hydrogen sulfide, thioether, mercaptan and the like is introduced into a gas inlet of the supergravity absorber by a fan, and molecular-level micro-mixing is carried out under the action of a supergravity field under gas-liquid two phases, so that the VOC is removed and is discharged after reaching the standard.
In the invention, the sulfonic acid butyl-methylimidazolium-p-toluenesulfonic acid has strong ammonia capturing reaction capacity, the 3-site N has strong hydrogen sulfide capturing reaction capacity, and captured amino and hydrogen sulfide can be separated under specific conditions, so that the ionic liquid can be recycled.
The 1-butyl-3-methylimidazole tetrafluoroborate has strong dissolving capacity and high absorption capacity on organic volatile matters, and can fully absorb organic volatile matters such as organic aldehyde, acid, dichloroethane, ethyl acetate, toluene, styrene and the like. The absorption saturation can realize the recovery of organic volatile matters through evaporation, and the ionic liquid can be recycled.
Lead acetate can capture and react thiol substances in odor to form nontoxic, tasteless and insoluble yellow precipitate.
The potassium permanganate oxidizes mercaptan and thioether into odorless and tasteless sulfonic acid and high-boiling-point sulfone under the strong acidic condition of acidic ionic liquid sulfonic acid butyl-methylimidazolium-p-toluenesulfonic acid.
The sulfonic acid butyl-methylimidazolium-p-toluenesulfonic acid, the 1-butyl-3-methylimidazolium tetrafluoroborate, the lead acetate and the potassium permanganate adopted by the invention respectively have absorption characteristics, but more importantly, the mutual connection effect among the raw materials is a determining factor for determining the high absorption efficiency of the ionic liquid. The specific relation is as follows: the sulfonic group of the sulfonic acid butyl-methylimidazolium-p-toluenesulfonic acid can free hydrogen ions, so that the system shows acidity, and the oxidizing property of potassium permanganate is stronger under the condition of the system with the sulfonic acid butyl-methylimidazolium-p-toluenesulfonic acid. Butyl-methylimidazolium sulfonate-p-toluenesulfonic acid, ammonium nitrogen in 1-butyl-3-methylimidazolium tetrafluoroborate and acetate anion in lead acetate, BF 4 The anion pair and water can form stable hydrogen bonds to promote the sulfonic acid butyl-methylimidazolium-p-toluenesulfonic acid, 1-butyl-3-methylimidazolium tetraThe fluoroborate forms a stable macromolecular complex group with the acetate, thereby being beneficial to VOC and SO 2 、N x And O is combined, and the four compounds selected by the invention form a synergistic effect, so that the prepared ionic liquid has the combined action of physical absorption and chemical reaction, and further the VOC is efficiently absorbed.
The functional ionic liquid prepared by the invention is used as a solvent, an absorbent and a reaction reagent in a system, so that the VOC is physically dissolved and absorbed and chemically captured in the gas-liquid exchange of the functional ionic liquid, thereby achieving the high-efficiency treatment of the VOC. The saturated ionic liquid can be conveniently desorbed by heating, so that the ionic liquid can be recycled.
Drawings
FIG. 1 is a diagram showing the equipment connection of the VOC gas absorption experiment.
Detailed Description
The following examples are given to illustrate specific embodiments of the present invention, but are not intended to limit the scope of the present invention in any way.
Example 1: a functionalized ionic liquid for absorbing VOC is prepared from the following raw materials, namely butyl sulfonate-methylimidazolium-p-toluenesulfonic acid, 1-butyl-3-methylimidazolium tetrafluoroborate, lead acetate and potassium permanganate, wherein the mass ratio of the raw materials is 1.
Example 2: a functionalized ionic liquid for absorbing VOC is prepared from butyl sulfonate-methylimidazolium-p-toluenesulfonic acid, 1-butyl-3-methylimidazolium tetrafluoroborate, lead acetate and potassium permanganate, wherein the mass ratio of the substances is 1.
Example 3: a functionalized ionic liquid for absorbing VOC is prepared from butyl sulfonate-methylimidazolium-p-toluenesulfonic acid, 1-butyl-3-methylimidazolium tetrafluoroborate, lead acetate and potassium permanganate, wherein the mass ratio of the substances is 1.
Example 4: a functionalized ionic liquid for absorbing VOC is prepared from the following raw materials, namely butyl sulfonate-methylimidazolium-p-toluenesulfonic acid, 1-butyl-3-methylimidazolium tetrafluoroborate, lead acetate and potassium permanganate, wherein the mass ratio of the raw materials is 1.
Example 5: a functionalized ionic liquid for absorbing VOC is prepared from butyl sulfonate-methylimidazolium-p-toluenesulfonic acid, 1-butyl-3-methylimidazolium tetrafluoroborate, lead acetate and potassium permanganate, wherein the mass ratio of the substances is 1.
Example 6: a functionalized ionic liquid for absorbing VOC is prepared from the following raw materials, namely butyl sulfonate-methylimidazolium-p-toluenesulfonic acid, 1-butyl-3-methylimidazolium tetrafluoroborate, lead acetate and potassium permanganate, wherein the mass ratio of the raw materials is 1.
The ionic liquids of examples 1-6 were prepared using the following procedure: dissolving potassium permanganate into deionized water to form a solution with the concentration of 1-5%, adding lead acetate powder, stirring for dissolving, continuously adding 1-butyl-3-methylimidazolium tetrafluoroborate and butyl sulfonate-methylimidazolium-p-toluenesulfonic acid under stirring, and uniformly stirring to obtain the potassium permanganate solution.
Example 7:
a functionalized ionic liquid for absorbing VOC is prepared from the following raw materials of butyl sulfonate-methylimidazolium-p-toluenesulfonic acid, 1-butyl-3-methylimidazolium tetrafluoroborate and lead acetate, wherein the mass ratio of the raw materials is 1.
During preparation: the method comprises the following steps: dissolving lead acetate in deionized water to form 0.1-4% solution, stirring for dissolving, adding 1-butyl-3-methylimidazolium tetrafluoroborate and butyl-methylimidazolium sulfonate-p-toluenesulfonic acid under stirring, and stirring to obtain the final product.
Example 8:
a functionalized ionic liquid for absorbing VOC is prepared from the following raw materials, namely sulfonic acid butyl-methylimidazolium-p-toluenesulfonic acid, 1-butyl-3-methylimidazolium tetrafluoroborate and potassium permanganate, wherein the mass ratio of the materials is 1.
During preparation: dissolving potassium permanganate into deionized water to form a solution with the concentration of 1-5%, adding 1-butyl-3-methylimidazolium tetrafluoroborate and butyl sulfonate-methylimidazolium-p-toluenesulfonic acid under stirring, and uniformly stirring to obtain the potassium permanganate-sodium sulfovinate.
Example 9:
a functionalized ionic liquid for absorbing VOC is prepared from butyl sulfonate-methylimidazolium-p-toluenesulfonic acid, lead acetate and potassium permanganate, wherein the mass ratio of the substances is 1.
During preparation: dissolving potassium permanganate into deionized water to form a solution with the concentration of 1-5%, adding lead acetate powder, stirring for dissolving, continuously adding butyl sulfonate-methylimidazolium-p-toluenesulfonic acid under stirring, and uniformly stirring to obtain the potassium permanganate-sodium hydrogen sulfonate.
Example 10:
a functional ionic liquid for absorbing VOC is prepared from 1-butyl-3-methylimidazolium tetrafluoroborate, lead acetate and potassium permanganate, wherein the mass ratio of the materials is 4.
During preparation: dissolving potassium permanganate into deionized water to form a solution with the concentration of 1-5%, adding lead acetate powder, stirring for dissolving, continuously adding 1-butyl-3-methylimidazole tetrafluoroborate under stirring, and uniformly stirring to obtain the product.
Example 11
A functionalized ionic liquid for absorbing VOC is prepared from butyl sulfonate-methylimidazolium-p-toluenesulfonic acid and 1-butyl-3-methylimidazolium tetrafluoroborate in a mass ratio of 1.
Example 12
A functionalized ionic liquid for absorbing VOC is prepared from butyl sulfonate-methylimidazolium-p-toluenesulfonic acid and lead acetate according to the mass ratio of 8.
Example 13
A functional ionic liquid for absorbing VOC is prepared from butyl sulfonate-methylimidazolium-p-toluenesulfonic acid and potassium permanganate, wherein the mass ratio of the substances is (8).
Example 14
A functional ionic liquid for absorbing VOC is prepared from 1-butyl-3-methylimidazolium tetrafluoroborate and potassium permanganate, wherein the mass ratio of the materials is (8).
VOC gas absorption experiments were performed on the ionic liquids prepared in examples 1-14, and the experimental methods were: a simulated VOC gas was first prepared and charged into 14 gassing bottles with a mixed liquid according to the ratio of ethanol/acetone/toluene/xylene/ethyl acetate/ethyl sulfide/ethanethiol 3. The ionic liquids from examples 1-14 were then charged into another 14 gas washing bottles and recorded as experiments 1-14 in sequence. Introducing air discharged from an air compressor into a gas production cylinder, and detecting the VOC value (not methane total hydrocarbon) of gas at the outlet of the gas production cylinder, wherein the VOC value is generally 2500-3000mg/L and has unpleasant odor of hydrogen sulfide and mercaptan. The gas outlet of the gas generating bottle is connected with the gas inlet of the gas washing bottle, and is introduced into the deep part of the functional ionic liquid, the VOC (volatile organic compounds) value (non-methane total hydrocarbon) of the inlet and the outlet of each gas washing bottle is measured, and the numerical values obtained by 14 groups of experimental records are as follows:
from the above data, it can be seen that when potassium permanganate is not added to the raw materials, the absorption solution cannot oxidize gas, but only ammonium nitrogen in butyl-methylimidazolium sulfonate-p-toluenesulfonic acid, 1-butyl-3-methylimidazolium tetrafluoroborate and acetate anion in lead acetate, BF 4 The anion pair and water can both form stable hydrogen bonds, the synergistic effect is poor, and the VOC removing effect is influenced.
When the raw materials are not added with lead acetate, ammonium nitrogen in the butyl sulfonate-methylimidazolium-p-toluenesulfonic acid and 1-butyl-3-methylimidazolium tetrafluoroborate cannot form stable hydrogen bonds with acetate anions in the lead acetate, BF4 anion pairs and water, the molecular complexing ability is influenced, and the VOC removal effect is influenced.
When the 1-butyl-3-methylimidazolium tetrafluoroborate is not added into the raw materials, although the sulfonic group of the butyl sulfonate-methylimidazolium-p-toluenesulfonic acid can free hydrogen ions, the oxidability of potassium permanganate is stronger under the system condition of the presence of the butyl sulfonate-methylimidazolium-p-toluenesulfonic acid, but the process of absorbing VOC in the 1-butyl-3-methylimidazolium tetrafluoroborate is avoided, so that the prepared ionic liquid has the combined action of physical absorption and chemical reaction and is remarkably reduced, and the VOC removal effect is influenced.
When the sulfonic acid butyl-methylimidazolium-p-toluenesulfonic acid is not added into the raw materials, the oxidability of potassium permanganate is influenced, the absorption of 1-butyl-3-methylimidazolium tetrafluoroborate is also influenced to form a stable macromolecular complex group, and the VOC removal effect is influenced.
When only the sulfonic acid butyl-methylimidazolium-p-toluenesulfonic acid and 1-butyl-3 methylimidazolium tetrafluoroborate are used as raw materials, the absorption liquid only has physical absorption and does not have the combined action with chemical reaction.
When only butyl sulfonate-methylimidazolium-p-toluenesulfonic acid and lead acetate are used as raw materials, the absorption of the butyl sulfonate-methylimidazolium-p-toluenesulfonic acid and the reaction of the lead acetate exist, and the effects of physical absorption and chemical reaction are poor.
When only butyl sulfonate-methylimidazolium-p-toluenesulfonic acid and potassium permanganate are used as raw materials, hydrogen ions can be liberated from sulfonic acid groups of the butyl sulfonate-methylimidazolium-p-toluenesulfonic acid, so that the oxidizing property of the potassium permanganate is stronger under the system condition of the butyl sulfonate-methylimidazolium-p-toluenesulfonic acid, and the combined action of physical absorption and chemical reaction is poor.
When only 1-butyl-3-methylimidazole tetrafluoroborate and potassium permanganate are used as raw materials, the absorption capacity of the 1-butyl-3-methylimidazole tetrafluoroborate and the oxidation capacity of the potassium permanganate are weak, and the synergistic effect of physical absorption and chemical reaction is poor.
Finally, the above embodiments are only used for illustrating the technical solutions of the present invention and not for limiting, and other modifications or equivalent substitutions made by the technical solutions of the present invention by those of ordinary skill in the art should be covered within the scope of the claims of the present invention as long as they do not depart from the spirit and scope of the technical solutions of the present invention.
Claims (3)
1. A functionalized ionic liquid for absorbing VOCs characterized by: the raw materials used are sulfonic acid butyl-methylimidazolium-p-toluenesulfonic acid, 1-butyl-3-methylimidazolium tetrafluoroborate, lead acetate and potassium permanganate, and the mass ratio of the materials is 1-8.
2. The functionalized ionic liquid of claim 1, wherein: the mass ratio of the sulfobutyl-methylimidazolium-p-toluenesulfonic acid to the 1-butyl-3-methylimidazolium tetrafluoroborate to the lead acetate to the potassium permanganate is 1.
3. A process for the preparation of the functionalized ionic liquid of claim 1, comprising the steps of: dissolving potassium permanganate into deionized water to form a solution with the concentration of 1-5%, adding lead acetate powder, stirring for dissolving, continuously adding 1-butyl-3-methylimidazolium tetrafluoroborate and butyl sulfonate-methylimidazolium-p-toluenesulfonic acid under stirring, and uniformly stirring to obtain the potassium permanganate solution.
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| CN117717878A (en) * | 2024-01-31 | 2024-03-19 | 成都理工大学 | Ionic liquid and method for efficiently absorbing toluene waste gas at normal pressure |
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