CN114247435A - Preparation method of organic color-changing material capable of efficiently adsorbing VOCs (volatile organic compounds) - Google Patents
Preparation method of organic color-changing material capable of efficiently adsorbing VOCs (volatile organic compounds) Download PDFInfo
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- 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
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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
- B01D53/02—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 adsorption, e.g. preparative gas chromatography
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
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Abstract
The invention discloses a preparation method of an organic color-changing material for efficiently adsorbing VOCs (volatile organic compounds), which is characterized in that phenolphthalein is used as a structural framework, a porous color-changing adsorbent material is constructed through imine condensation and reduction reactions, and the adsorbent material can realize rapid and reversible color-changing response to various VOCs molecules, and has rapid adsorption capacity and large adsorption capacity, wherein the adsorption capacity to dichloromethane is up to 2964 mg/g. In addition, the adsorbent material can realize reversible desorption and recovery under the heating condition, and has excellent cycle stability. The organic polymer is expected to be applied to the fields of sensing, adsorption separation and the like of VOC pollutants and the fields of related pollutant treatment, environmental treatment and the like.
Description
Technical Field
The invention belongs to the technical field of organic polymer synthesis and air pollution, and particularly relates to a preparation method of an organic color-changing material for efficiently adsorbing VOCs.
Background
The continuous development of human science and technology greatly changes and improves the life style and quality of people on one hand, and inevitably causes pollution to the earth environment on the other hand. Atmospheric pollution and water pollution in environmental pollution become the primary threats to human health. Among them, pollution of Volatile Organic Compounds (VOCs) released from various artificial leathers, plastics, building materials, etc. is a major source of indoor air pollution. Sick building syndrome caused by long-term exposure to indoor polluted environments is continuously eroding human health. Volatile organic compounds are a general name for organic compounds, and are not defined uniformly in the international range at present. Generally defined as the general name of organic compounds having a melting point lower than room temperature and a boiling point lower than 200 to 260 ℃. As defined above, hundreds of substances can be classified in the VOC array, for example, formaldehyde, benzene, toluene, methylene chloride, carbon tetrachloride, and the like are common VOC pollutants. Due to the diversity of the physicochemical properties of the VOC pollutants, the range and the influence of the VOC pollutants are quite wide, and meanwhile, the method also brings great challenges to the treatment of the VOCs pollution.
At present, the strategies for treating VOCs pollution mainly comprise an adsorption method and a degradation method. The adsorption method mainly adopts some substances such as activated carbon, silica gel, molecular sieve, alumina and the like as harmful gas adsorbents to remove volatile organic compounds in air, has the advantages of high adsorption speed, high and low pollutant concentration, can be used in occasions, can perform reversible desorption under general conditions, and has the defects that a plurality of VOCs pollutants are difficult to be adsorbed simultaneously, and the desorption conditions are generally harsh. The degradation principle is that some active chemical substances are added into the carrier of the adsorbent to remove organic compounds in the air through chemical reaction, and the method has the advantages of simultaneously playing the roles of catalytic oxidation and adsorption on various air pollutants, but has the defects of limited service life and need of replacing materials regularly. Therefore, the porous material which can adsorb various VOCs pollutants simultaneously is developed and has very attractive prospect.
Disclosure of Invention
Aiming at the problems that the existing VOCs adsorbates are difficult to adsorb short plates of various pollutants simultaneously and reversible desorption conditions are harsh, the invention provides a preparation method of a color-changing material for efficiently adsorbing VOCs pollutants, and proposes that a porous color-changing adsorbent material is constructed by using phenolphthalein as a framework, and the adsorbates can detect and adsorb various VOC molecules simultaneously and have large adsorption capacity and adsorption rate.
In order to solve the technical problems, the invention adopts a technical scheme that: a preparation method of an organic color-changing material for efficiently adsorbing VOCs comprises the following steps:
the first step is as follows: phenolphthalein is used as a raw material to prepare phenolphthalein tetra-aldehyde through a doffer reaction;
the second step is that: performing Schiff base condensation reaction on phenolphthalein tetra-aldehyde and a polyamine compound in an organic solvent to obtain an imine polymer;
the third step: and reducing the imine polymer by a reducing agent to obtain the organic color-changing material.
Further, the method comprises the following steps:
the first step is as follows: reacting phenolphthalein, hexamethylenetetramine and trifluoroacetic acid at 100 ℃ for 10-48 h under the protection of nitrogen to obtain phenolphthalein tetraaldehyde;
the second step is that: performing Schiff base condensation reaction on phenolphthalein tetra-aldehyde and a polyamine compound in an organic solution to obtain an imine polymer, wherein the reflux time is 4-24 hours, and the reflux temperature is 60-150 ℃;
the third step: the imine polymer and a reducing agent react in ethanol at a reaction temperature of room temperature to 120 ℃ for 24-48 hours to obtain the organic color-changing material.
The polyamine compound is a primary amine compound having two or more amine groups, such as cyclohexanediamine, ethylenediamine, tris (2-aminoethyl) amine, or p-phenylenediamine.
Further, the reducing agent is sodium borohydride or lithium aluminum hydride.
Further, the molar ratio of the phenolphthalein to the hexamethylenetetramine to the trifluoroacetic acid is 1:10: 70.
Further, the organic solvent is N, N-dimethylformamide, dichloromethane, chloroform or acetonitrile.
Further, the molar ratio of the imine polymer to the reducing agent is 1: 30-100.
The invention has the following beneficial effects:
1. the invention takes phenolphthalein tetra-aldehyde as a raw material, and the phenolphthalein tetra-aldehyde and a primary amine compound (the number of amino groups is not less than 2) are subjected to imine condensation reaction and reduction reaction sequentially to prepare the organic polymer, the raw material phenolphthalein and the corresponding primary amine compound are relatively cheap, the synthesis condition of a target product is mild, and the industrial level is easy to realize; the prepared organic polymer is applied to the fields of sensing, adsorption separation and the like of VOCs and the fields of related pollutant treatment, environmental treatment and the like;
2. tests prove that the organic color-changing material can rapidly absorb and desorb a large amount of VOC molecules and can realize reversible desorption and recovery under heating conditions; meanwhile, the organic color-changing material can also indicate an adsorption process through color change, and has extremely sensitive color-changing sensing characteristics on various VOCs molecules.
Drawings
FIG. 1 is a schematic diagram of the synthesis of phenolphthalein tetraaldehyde in accordance with the present invention;
FIG. 2 is a schematic diagram of the synthesis of the polymer P1 of the present invention and a structural diagram of a polyamine compound L1;
FIG. 3 is a nuclear magnetic spectrum (400MHz, CDCl) of phenolphthalein tetraaldehyde of the present invention3)；
FIG. 4 is a chart of an infrared spectrum of P11 in example 1 of the present invention;
FIG. 5 is a graph of the color change response of P11 to different VOCs in example 1 of the present invention;
FIG. 6 is a graph of the adsorption capacity of P11 for different vapors of VOCs in example 1 of the present invention;
FIG. 7 is a graph comparing the capacity of P11 for five consecutive adsorbtions of methylene chloride in example 1 of the present invention;
FIG. 8 is a chart of an infrared spectrum of P12 in example 2 of the present invention;
FIG. 9 is a graph of the color change response of P12 to different VOCs in example 2 of the present invention;
FIG. 10 is a graph of the adsorption capacity of P12 for different vapors of VOCs in example 2 of the present invention;
FIG. 11 is a graph comparing the capacity of P12 for five consecutive adsorbtions of methylene chloride in example 2 of the present invention.
Detailed Description
The following detailed description of the preferred embodiments of the present invention, taken in conjunction with the accompanying drawings, will make the advantages and features of the invention easier to understand by those skilled in the art, and thus will clearly and clearly define the scope of the invention.
The discoloration experimental conditions for testing VOC adsorption of the polymers of this example are as follows: respectively soaking 10mg of organic color-changing material P1 gray powder in a glass bottle containing 10mL of secondary deionized water, and ultrasonically dispersing the organic color-changing material P1 uniformly, wherein the color of the P1 is changed from gray to purple; 100 microliters of the organic solution was dropped into the above P1 solution by a pipette, and after mixing and shaking, the purple powder in the bottle immediately faded to gray powder, indicating that P1 can adsorb the organic solvent molecules to cause discoloration of the material. The organic solvent comprises formaldehyde, methanol, ethanol, dichloromethane, chloroform, diethyl ether, cyclohexane, toluene, m-xylene, benzene, dimethyl sulfoxide, tetrahydrofuran, acetone, 1, 4-dioxane, acetonitrile, ethyl acetate and the like.
The experimental conditions used in this example to test the adsorption of VOC vapors by polymers were as follows: after 20mg of the organic color-changing material P1 dry powder is placed in a VOC saturated steam environment for a period of time (0-24h), the weight change of the organic color-changing material P1 before and after adsorption is monitored by a ten-thousandth precision balance until the weight of the P1 powder is not increased any more, the powder is taken out and weighed to calculate the adsorption quantity, three test values are parallelly acquired in each group of experiments, and the average value is taken as a final numerical value. Meanwhile, in order to verify the regeneration capacity and the cycle stability of the organic color-changing material P1 after adsorbing VOCs, a sample adsorbing VOCs is dried in vacuum, then the adsorption amount of the organic color-changing material P1 after desorption to VOCs is tested according to the steps, the steps are continuously repeated for 5 times, and five times of adsorption amount values are recorded to evaluate the cycle stability of the organic color-changing material P1.
Example 1
A preparation method of an organic color-changing material for efficiently adsorbing VOCs comprises the following steps of (1) synthesizing phenolphthalein tetra-aldehyde: phenolphthalein (4g,12.6mmol) and hexamethylenetetramine (18g,128mmol) are weighed into a 250ml two-neck flask, nitrogen is used for protection, then 60ml of trifluoroacetic acid TFA is added, reflux reaction is carried out at 100 ℃ for 24h, cooling is carried out to room temperature, 3mol/L HCl 150ml is added, hydrolysis is carried out at 100 ℃ for 1.5h, a large amount of yellow powder is separated out, crude phenolphthalein tetraaldehyde (2.0g) is filtered and washed, and the crude phenolphthalein tetraaldehyde (56%) is obtained after silica gel column chromatography, and a nuclear magnetic spectrum chart is shown in figure 3.
Synthesis of the polymer P11 (fig. 2): weighing phenolphthalein tetraaldehyde (120mg,0.28mmol) and cyclohexanediamine L11(64mg,0.56mmol) into a 100ml single-mouth reaction bottle, adding 20ml acetonitrile solution for ultrasonic dissolution, placing the mixture into a reaction bottle with 90 ℃ for reflux stirring until the mixture is completely dissolved, carrying out reflux reaction on the reaction solution at 90 ℃ for 24 hours, cooling the reaction solution to room temperature, precipitating a large amount of yellow powder, filtering, collecting and drying; weighing the powder (500mg) into a 250ml single-mouth reaction bottle, adding 100ml ethanol, ultrasonically dissolving, and refluxing and stirring until the powder is completely dissolved; sodium borohydride (516mg,13.6mmol) was then weighed out and dissolved in 50ml of ethanol and added dropwise to the above solution. The reaction solution is stirred at room temperature for 24h, then the solvent is removed by rotary evaporation, 200mL of deionized water is added, the mixture is stirred at room temperature overnight, and the mixture is filtered, washed with water and dried to obtain purple powder P11(350 mg). Nuclear magnetic data were not available due to poor solubility of P11, and the infrared data are shown in fig. 4.
The results of testing the discoloration and adsorption capacity of P11 for different VOCs and the regeneration adsorption cycle performance for dichloromethane according to the experimental conditions given above are shown in fig. 5, 6 and 7, and show that P11 can respond to ethanol, dichloromethane, chloroform, anhydrous ether, benzene, dimethyl sulfoxide, tetrahydrofuran, acetone, 1, 4-dioxane, acetonitrile, methanol and ethyl acetate by discoloration (purple color changes to gray color), and P11 has a larger adsorption capacity for various VOCs vapors, wherein the adsorption capacity for dichloromethane is 2964mg/g (fig. 6), which is higher than that reported in the prior art, and the adsorption capacity for acetone and ethyl acetate is greater than 900 mg/g. Meanwhile, dichloromethane is taken as a research object to examine the regeneration cyclicity of P11, and the test result shows that P11 has excellent cycle stability (FIG. 7).
Example 2
A preparation method of an organic color-changing material for efficiently adsorbing VOCs comprises the following steps of (1) synthesizing phenolphthalein tetra-aldehyde: phenolphthalein (4g,12.6mmol) and hexamethylenetetramine (18g,128mmol) are weighed into a 250ml two-neck flask, nitrogen is used for protection, then 60ml of trifluoroacetic acid TFA is added, reflux reaction is carried out at 100 ℃ for 24h, cooling is carried out to room temperature, 3mol/L HCl 150ml is added, hydrolysis is carried out at 100 ℃ for 1.5h, a large amount of yellow powder is separated out, crude phenolphthalein tetraaldehyde (2.0g) is filtered and washed, and the crude phenolphthalein tetraaldehyde (56%) is obtained after silica gel column chromatography, and a nuclear magnetic spectrum chart is shown in figure 3.
Synthesis of the polymer P12 (fig. 2): weighing phenolphthalein tetraaldehyde L1(120mg,0.28mmol) and ethylenediamine L12(34mg,0.56mmol) into a 100ml single-mouth reaction bottle, adding 20ml acetonitrile solution for ultrasonic dissolution, placing the mixture into a reaction bottle with a single mouth, refluxing and stirring at 90 ℃ until the mixture is completely dissolved, carrying out reflux reaction on the reaction solution at 90 ℃ for 24 hours, cooling to room temperature, precipitating a large amount of yellow powder, filtering, collecting and drying; weighing the powder (400mg) into a 250ml single-mouth reaction bottle, adding 100ml ethanol, ultrasonically dissolving, and refluxing and stirring until the powder is completely dissolved; sodium borohydride (516mg,13.6mmol) was then weighed out and dissolved in 50ml of ethanol and added dropwise to the above solution. The reaction solution was stirred at room temperature for 24h, then the solvent was removed by rotary evaporation, 200mL of deionized water was added and stirred at room temperature overnight, followed by suction filtration, washing with water and drying to give P12(350mg, 95%) as a purple powder. The infrared data are shown in FIG. 8, since P12 is poorly soluble and does not give nuclear magnetic data.
The results of testing the discoloration and adsorption capacity of P12 for different VOCs and the regeneration adsorption cycle performance for dichloromethane according to the experimental conditions given above are shown in fig. 9, fig. 10 and fig. 11, and show that P12 can respond to acetic acid, formaldehyde, ethanol, methanol, dichloromethane, ethyl acetate, acetone, diethyl ether, acetonitrile, etc. with discoloration (brown to yellow), while P12 has a larger adsorption capacity for many VOCs vapors, wherein the adsorption capacity for dichloromethane is 1771mg/g, and the adsorption capacity for acetone and ethyl acetate is greater than 700 mg/g. Meanwhile, dichloromethane is taken as a research object to examine the regeneration cyclicity of P12, and the test result shows that P12 has excellent cycle stability (FIG. 11).
The above description is only an embodiment of the present invention, and not intended to limit the scope of the present invention, and all equivalent structural changes made by using the contents of the present specification and the drawings, or applied directly or indirectly to other related technical fields, are included in the scope of the present invention.
Claims (7)
1. A preparation method of an organic color-changing material for efficiently adsorbing VOCs is characterized by comprising the following steps: the method comprises the following steps:
the first step is as follows: phenolphthalein is used as a raw material to prepare phenolphthalein tetra-aldehyde through a doffer reaction;
the second step is that: performing Schiff base condensation reaction on phenolphthalein tetra-aldehyde and a polyamine compound in an organic solvent to obtain an imine polymer;
the third step: and reducing the imine polymer by a reducing agent to obtain the organic color-changing material.
2. The method for preparing the organic color-changing material for efficiently adsorbing VOCs according to claim 1, wherein the method comprises the following steps: the method comprises the following steps:
the first step is as follows: reacting phenolphthalein, hexamethylenetetramine and trifluoroacetic acid at 100 ℃ for 10-48 h under the protection of nitrogen to obtain phenolphthalein tetraaldehyde;
the second step is that: performing Schiff base condensation reaction on phenolphthalein tetra-aldehyde and a polyamine compound in an organic solution to obtain an imine polymer, wherein the reflux time is 4-24 hours, and the reflux temperature is 60-150 ℃;
the third step: the imine polymer and a reducing agent react in ethanol at a reaction temperature of room temperature to 120 ℃ for 24-48 hours to obtain the organic color-changing material.
3. The method for preparing the organic color-changing material for efficiently adsorbing VOCs according to claim 2, wherein the method comprises the following steps: the polyamine compound is cyclohexanediamine, ethylenediamine, tris (2-aminoethyl) amine or p-phenylenediamine.
4. The method for preparing the organic color-changing material for efficiently adsorbing VOCs according to claim 2, wherein the method comprises the following steps: the reducing agent is sodium borohydride or lithium aluminum hydride.
5. The method for preparing the organic color-changing material for efficiently adsorbing VOCs according to claim 2, wherein the method comprises the following steps: the molar ratio of phenolphthalein to hexamethylenetetramine to trifluoroacetic acid is 1:10: 70.
6. The method for preparing the organic color-changing material for efficiently adsorbing VOCs according to claim 2, wherein the method comprises the following steps: the organic solvent is N, N-dimethylformamide, dichloromethane, trichloromethane or acetonitrile.
7. The method for preparing the organic color-changing material for efficiently adsorbing VOCs according to claim 2, wherein the method comprises the following steps: the molar ratio of the imine polymer to the reducing agent is 1: 30-100.
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Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63156565A (en) * | 1986-12-19 | 1988-06-29 | Agency Of Ind Science & Technol | Method for developing regular structure of thin organic film |
| WO1994001102A1 (en) * | 1992-06-30 | 1994-01-20 | Legomer Partners, L.P. | Aminimide-containing molecules and materials as molecular recognition agents |
| CN1081398A (en) * | 1992-07-20 | 1994-02-02 | 中国科学院上海冶金研究所 | Effective carbon-dioxide absorbent and preparation method thereof |
| CN103752282A (en) * | 2013-12-26 | 2014-04-30 | 燕山大学 | Method for removing heavy metals in water by utilizing resin/Schiff base composite material |
| CN104923186A (en) * | 2015-06-02 | 2015-09-23 | 中山大学 | Amine-terminated hyperbranched polymer solid amine adsorption material as well as preparation method and application thereof |
| CN106390931A (en) * | 2015-07-29 | 2017-02-15 | 中国科学院大连化学物理研究所 | Applications of covalent organic compound having azo functional group as gas adsorption material |
| CN108586623A (en) * | 2018-03-23 | 2018-09-28 | 昆明理工大学 | A kind of cellulose base Schiff base catalyst and its preparation method and application |
| CN110590756A (en) * | 2019-09-01 | 2019-12-20 | 南通大学 | Phenolphthalein Schiff base fluorescent probe and preparation method and application thereof |
| CN111054178A (en) * | 2020-03-17 | 2020-04-24 | 北京零微科技有限公司 | Formaldehyde removal purification material and preparation method and application thereof |
| CN111659357A (en) * | 2019-03-06 | 2020-09-15 | 中南大学 | Polymeric Schiff base type adsorption material, preparation and application thereof in heavy metal adsorption |
| CN113477234A (en) * | 2021-07-19 | 2021-10-08 | 华东理工大学 | Preparation method of MOF loaded aerogel for adsorbing VOCs |
| CN113666896A (en) * | 2021-07-28 | 2021-11-19 | 深圳先进技术研究院 | Alpha-naphtholphthalein derivative multifunctional fluorescent probe and preparation method and application thereof |
-
2021
- 2021-12-25 CN CN202111604789.8A patent/CN114247435B/en active Active
Patent Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63156565A (en) * | 1986-12-19 | 1988-06-29 | Agency Of Ind Science & Technol | Method for developing regular structure of thin organic film |
| WO1994001102A1 (en) * | 1992-06-30 | 1994-01-20 | Legomer Partners, L.P. | Aminimide-containing molecules and materials as molecular recognition agents |
| CN1081398A (en) * | 1992-07-20 | 1994-02-02 | 中国科学院上海冶金研究所 | Effective carbon-dioxide absorbent and preparation method thereof |
| CN103752282A (en) * | 2013-12-26 | 2014-04-30 | 燕山大学 | Method for removing heavy metals in water by utilizing resin/Schiff base composite material |
| CN104923186A (en) * | 2015-06-02 | 2015-09-23 | 中山大学 | Amine-terminated hyperbranched polymer solid amine adsorption material as well as preparation method and application thereof |
| CN106390931A (en) * | 2015-07-29 | 2017-02-15 | 中国科学院大连化学物理研究所 | Applications of covalent organic compound having azo functional group as gas adsorption material |
| CN108586623A (en) * | 2018-03-23 | 2018-09-28 | 昆明理工大学 | A kind of cellulose base Schiff base catalyst and its preparation method and application |
| CN111659357A (en) * | 2019-03-06 | 2020-09-15 | 中南大学 | Polymeric Schiff base type adsorption material, preparation and application thereof in heavy metal adsorption |
| CN110590756A (en) * | 2019-09-01 | 2019-12-20 | 南通大学 | Phenolphthalein Schiff base fluorescent probe and preparation method and application thereof |
| CN111054178A (en) * | 2020-03-17 | 2020-04-24 | 北京零微科技有限公司 | Formaldehyde removal purification material and preparation method and application thereof |
| CN113477234A (en) * | 2021-07-19 | 2021-10-08 | 华东理工大学 | Preparation method of MOF loaded aerogel for adsorbing VOCs |
| CN113666896A (en) * | 2021-07-28 | 2021-11-19 | 深圳先进技术研究院 | Alpha-naphtholphthalein derivative multifunctional fluorescent probe and preparation method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| 赵秋丽等: "含萘酰亚胺基元的水杨醛席夫碱的合成及其溶致变色效应", 《分子科学学报》 * |
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