CN111569846B - Microporous conjugated polyaniline adsorption material, preparation method thereof and application thereof in hexavalent chromium adsorption - Google Patents
Microporous conjugated polyaniline adsorption material, preparation method thereof and application thereof in hexavalent chromium adsorption Download PDFInfo
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/262—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. obtained by polycondensation
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/28—Treatment of water, waste water, or sewage by sorption
- C02F1/285—Treatment of water, waste water, or sewage by sorption using synthetic organic sorbents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/026—Wholly aromatic polyamines
- C08G73/0266—Polyanilines or derivatives thereof
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- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/40—Aspects relating to the composition of sorbent or filter aid materials
- B01J2220/48—Sorbents characterised by the starting material used for their preparation
- B01J2220/4812—Sorbents characterised by the starting material used for their preparation the starting material being of organic character
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/10—Inorganic compounds
- C02F2101/20—Heavy metals or heavy metal compounds
- C02F2101/22—Chromium or chromium compounds, e.g. chromates
Abstract
The invention discloses a microporous conjugated polyaniline adsorption material and a preparation method and application thereof, belonging to the field of functional material synthesis. The polyaniline adsorption material with polyaniline characteristics and microporous conjugated polymer characteristics is prepared by adopting aniline oligomers with two or more amino end capping groups as a connector and chemical substances with two or more bromophenyl groups as a center. The synthetic method is simple and rapid, mild in condition, economical and easy to implement, green and environment-friendly, the prepared adsorbing material not only has the characteristics of multiple oxidation reduction and self-reduction of polyaniline, can realize continuous reduction and detoxification of hexavalent chromium without using any reduction activator, but also has the characteristics of rich micropores and large specific surface area of the microporous conjugated polymer, and can realize excellent adsorption and storage of chromium ions, so that the adsorbing material can be applied to adsorption and purification of a wastewater solution containing hexavalent chromium ions.
Description
Technical Field
The invention belongs to the field of synthesis of functional materials, and particularly relates to a microporous conjugated polyaniline heavy metal ion adsorbent with polyaniline characteristics and different apertures, a synthesis method thereof and application thereof in adsorption of hexavalent chromium in wastewater.
Background
Water is one of the indispensable important resources that earth's life lives depend on for survival and development. However, with the rapid development of the human industrial technology, the world is facing increasingly serious environmental pollution and destruction of water bodies. At present, common water pollutants mainly comprise emerging pollutants such as heavy metal ions, dyes, small molecular organic matters, antibiotics and the like. Among them, heavy metal ions, especially hexavalent chromium ions (Cr (VI)), are a class of water pollutants that are urgently needed to be treated due to their strong oxidizability, biotoxicity and biodegradability. Therefore, how to effectively treat heavy metal ions in water bodies becomes one of the topics of extensive research by researchers.
The method for effectively treating the heavy metal ion wastewater comprises an adsorption method, a chemical precipitation method, a reverse osmosis method, a reduction method, an ion exchange method and the like, however, most treatment methods have high cost, complex treatment process and low treatment efficiency, and are difficult to separate heavy metal ions in the mixed heavy metal ion water body. In contrast, the adsorption method has low cost, simple and easy treatment process, high treatment efficiency and high adsorption speed, and can enhance the selective adsorption of the adsorption material on heavy metal ions in a hole design mode, so that the aims of efficiently separating and recovering the heavy metal ions are fulfilled. Therefore, the adsorption method is considered as one of the most promising technologies for wastewater treatment and heavy metal ion recycling; the development of research works such as the design of an adsorption method and an adsorbent and the like has important scientific research value and practical value.
The adsorption material is the core of the adsorption process. Currently, common heavy metal ion adsorbing materials include activated carbon, silica gel, oxides, molecular sieves, and high molecular polymers such as polyaniline, polypyrrole, and polythiophene. However, for the conventional high molecular polymer, due to the defects of homogeneous linear polymerization and the like, the obtained specific surface area is very small, and the capability of adsorbing heavy metal ions is greatly limited. For other adsorbing materials, the problems of low heavy metal selective adsorption, small adsorption capacity, difficulty in cyclic regeneration and the like still exist, and the application of an adsorption method to heavy metal ion wastewater is limited.
Disclosure of Invention
In view of the defects of the adsorption material, the invention mainly aims to provide a method for preparing a polyaniline adsorption material with microporous conjugated polymer characteristics and polyaniline characteristics. The prepared adsorbing material not only has the characteristics of multiple oxidation reduction and self-reduction of polyaniline, can realize continuous reduction and detoxification of hexavalent chromium without using any reduction activator, but also has the characteristics of abundant micropores and large specific surface area of the microporous conjugated polymer, and can realize excellent adsorption and storage of chromium ions.
In order to realize the purpose, the invention adopts the following technical scheme:
the invention aims to protect a microporous conjugated polyaniline adsorption material, which is prepared by adopting aniline oligomer with two or more amino end-capped ends as a connector, regulating and controlling the aperture and constructing an aniline-quinone amine structure of polyaniline, and adopting a chemical substance with two or more bromophenyl groups as a center to construct a microporous pore passage.
The second purpose of the invention is to protect the preparation method of the microporous conjugated polyaniline adsorption material, and the specific synthesis steps are that a core and a linker are added into a solvent, under the action of ligands XPhos and NaOtBu and a catalyst, the reaction is carried out for a certain time at a certain temperature, the reaction is centrifuged, and the obtained product is washed by the solvent and dried, thus obtaining the microporous conjugated polyaniline adsorption material. The mechanism is that under the action of ligand XPhos, palladium and bromine-containing groups on a central nucleus are subjected to oxidation addition reaction to form a palladium-aryl compound intermediate, and meanwhile, an amino group on a linker and NaOtBu are subjected to action to remove a hydrogen ion; and finally, the palladium catalyst is reduced and eliminated to leave, so that the amino group is coupled with the aryl group, and finally the polymer with the polyaniline structure is formed.
Wherein the molar ratio of the used centre to the linker is 0.1-3. The central nucleus can be a chemical substance with two or more bromophenyl groups such as tris (4-bromophenyl) amine; the linker may specifically be an aniline oligomer having two or more amino groups blocked, such as tris (4-aminophenyl) amine, p-phenylenediamine, 4' -diaminodiphenylamine, or the like.
The mole ratio of XPhos, naOtBu and catalyst is (0.5-3): 10-500): 1, wherein the amount of catalyst is 1-100% of the total mole amount of the core and linker, and the catalyst is palladium-containing catalyst, such as Pd (dba) 2 、Pd(acac) 2 、Pd(PPh 3 ) 4 、Pd(dppf)Cl 2 、Pd(OAc) 2 、Pd 2 (dba) 3 、Pd(PPh 3 ) 4 、Pd(dppf)Cl 2 Pd (OAc), etc.
The solvent comprises at least one of tetrahydrofuran, chloroform, toluene, dioxane, dimethyl sulfoxide, dimethylformamide, acetone, methanol, ethanol, water and N-methylpyrrolidone.
The reaction temperature is 37-202 ℃, and the reaction time is 0.1-72 h.
The third purpose of the invention is to protect the application of the microporous conjugated polyaniline adsorbing material in the aspect of adsorbing and removing hexavalent chromium in wastewater.
The invention has the following remarkable advantages:
the method for synthesizing the microporous conjugated polyaniline adsorbing material is simple, quick, mild in condition, green, environment-friendly, economical and easy to implement, the obtained adsorbing material has the characteristics of multiple oxidation reduction and self-reduction of polyaniline, can realize continuous reduction and detoxification of hexavalent chromium without using any reduction activator, has the characteristics of abundant micropores and large specific surface area of the microporous conjugated polymer, and can realize excellent adsorption and storage of chromium ions, so that the microporous conjugated polyaniline adsorbing material has excellent adsorption effect and reduction and detoxification effects on hexavalent chromium ions in a water body, and has the advantages of high adsorption speed, high adsorption capacity, self-reduction and good reusability.
Drawings
FIG. 1 is the IR spectrum of the microporous conjugated polyaniline PAPA (a), PTPA (b), PAAPA (c) and their precursors prepared in examples 1-3.
FIG. 2 is a diagram of the microporous conjugated polyanilines PAPA, PTPA and PAAPA prepared in examples 1 to 3 13 C solid nuclear magnetic spectrum.
FIG. 3 is an X-ray diffraction pattern of the microporous conjugated polyanilines PAPA, PTPA and PAAPA prepared in examples 1 to 3.
FIG. 4 is a nitrogen adsorption/desorption graph of the microporous conjugated polyanilines PAPA, PTPA and PAAPA prepared in examples 1 to 3.
FIG. 5 is a diagram showing the pore size distribution of microporous conjugated polyanilines PAPA, PTPA and PAAPA prepared in examples 1 to 3.
Detailed Description
In order to make the content of the present invention more comprehensible, the technical solutions of the present invention are further described below with reference to specific embodiments, but the present invention is not limited thereto.
Example 1: preparation of microporous conjugated polyaniline PAPA
0.5 mmol of tris (4-bromophenyl) amine, 0.5 mmol of tris (4-aminophenyl) amine and, as catalyst, 0.05mmol of Pd (dba) 2 And adding 0.09mmol of XPhos and 3.5 mmol of NaOtBu into 30 mL of tetrahydrofuran, reacting for 48 hours at 66 ℃, filtering the obtained product, soaking and washing the product by using solutions such as chloroform, boiling water and the like respectively, and drying the product in vacuum to obtain the microporous conjugated polyaniline heavy metal ion adsorbing material PAPA.
Example 2: preparation of microporous conjugated polyaniline PTPA
0.5 mmol of p-phenylenediamine, 0.5 mmol of tris (4-bromophenyl) amine and, as catalyst, 0.05mmol of Pd (dba) 2 Adding 0.09mmol XPhos and 3.5 mmol NaOtBu into 30 mL tetrahydrofuran, reacting at 66 ℃ for 48 h, filtering the obtained product, and respectively soaking the product in chloroform, boiling water and other solutionsSoaking, washing and vacuum drying to obtain the microporous conjugated polyaniline heavy metal ion adsorbing material PTPA.
Example 3: preparation of microporous conjugated polyaniline PAAPA
0.33 mmol of 4,4' -diaminodiphenylamine, 0.5 mmol of tris (4-bromophenyl) amine and, as catalyst, 0.05mmol of Pd (dba) 2 And adding 0.09mmol of XPhos and 3.5 mmol of NaOtBu into 30 mL of tetrahydrofuran, reacting for 48 hours at 66 ℃, filtering the obtained product, soaking and washing the product by using solutions such as chloroform, boiling water and the like respectively, and drying the product in vacuum to obtain the microporous conjugated polyaniline heavy metal ion adsorbing material PAAPA.
FIG. 1 is an infrared spectrum of the microporous conjugated polyaniline PAPA (a), PTPA (b), PAAPA (c) prepared in examples 1-3 and the precursors used therein. It can be seen from the figure that the positions are except for the positions of 710, 1004 and 1070 cm -1 Where denotes C-Br and 3400 and 3300 cm -1 Where denotes NH 2 The infrared spectrogram of the prepared material has all the characteristic vibration peaks of the precursor, and the successful coupling of amino and bromophenyl and the successful synthesis of the polymer are verified.
FIG. 2 is a schematic diagram of the microporous conjugated polyanilines PAPA, PTPA and PAAPA prepared in examples 1 to 3 13 C solid nuclear magnetic spectrum. The results show that the prepared material has two responses at 127 ppm and 141 ppm, and respectively indicate response vibration peaks of carbons on unsubstituted phenyl and substituted phenyl, and the results are consistent with simulation of Chemdraw software, and further confirm successful coupling of amino and bromophenyl and successful synthesis of the polymer.
FIG. 3 is an X-ray diffraction pattern of the microporous conjugated polyanilines PAPA, PTPA and PAAPA prepared in examples 1 to 3. The results show that the materials prepared are amorphous materials.
FIG. 4 is a nitrogen adsorption/desorption graph of the microporous conjugated polyanilines PAPA, PTPA and PAAPA prepared in examples 1 to 3. The results show that the prepared materials all show a nitrogen adsorption and desorption isothermal curve of type I, which indicates the existence of a large number of micropores. The specific surface area of the PAPA is calculated to be 833 m by a BET formula 2 The specific surface area of PTPA reaches 750 m 2 The specific surface area of/g and PAAPA reaches 688 m 2 And/g, the prepared material is proved to have the characteristics of large specific surface area and abundant micropores of the microporous conjugated polymer.
FIG. 5 is a graph showing the distribution of pore diameters of microporous conjugated polyanilines PAPA, PTPA and PAAPA prepared in examples 1 to 3. The result shows that the prepared material has very uniform pore size distribution and is concentrated in a micropore (2 nm) area, the characteristic that the prepared material has abundant micropores of a micropore conjugated polymer is proved, and the potential of the prepared material on the adsorption of heavy metal ions is also proved.
Example 4:
with hexavalent chromium ions (Cr) 2 O 7 2- ) As the heavy metal ions to be adsorbed. 0.03 g of the microporous conjugated polyaniline samples prepared in examples 1 to 3 were added to 20 mL of Cr (VI) aqueous solution with pH =2 and 400 mg/L, and adsorbed for 3 hours at 45 ℃ and with shaking speed of 200 rpm, which indicates that the removal rate of Cr (VI) by PAPA, PTAPA and PAAPA can reach 99.9%.
Example 5:
with hexavalent chromium ions (Cr) 2 O 7 2- ) As the heavy metal ions to be adsorbed. 0.03 g of the microporous conjugated polyaniline samples prepared in examples 1 to 3 were added to 20 mL of hexavalent chromium ion aqueous solution with pH =2 and 100-1000 mg/L, respectively, and adsorbed for 3 hours at 45 ℃ and with an oscillation speed of 200 rpm, as calculated by a Langmuir model, the adsorption capacities of PAPA, PTAPA and PAAPA to hexavalent chromium ions reached 521 mg/g, 420 mg/g and 174 mg/g, respectively.
Example 6:
with hexavalent chromium ions (Cr) 2 O 7 2- ) As the heavy metal ions to be adsorbed. 0.03 g of the microporous conjugated polyaniline samples prepared in examples 1 to 3 were added to 20 mL of hexavalent chromium ion aqueous solution with pH =2 and 400 mg/L, and adsorbed at 25 ℃ and oscillation speed of 200 rpm, and the results show that the PAPA, PTAPA and PAAPA all reach adsorption balance within 20 min, which indicates that the materials have the ability of rapidly adsorbing hexavalent chromium ions and are beneficial to rapidly treating wastewater solution containing heavy metal ions in real time.
Example 7:
with hexavalent chromium ions (Cr) 2 O 7 2- ) As the heavy metal ions to be adsorbed. 0.03 g of the microporous conjugated polyaniline sample prepared in the embodiment 1-3 is added into a hexavalent chromium ion aqueous solution with the concentration of 20 mL, the pH =2 and the concentration of 200 mg/L respectively, the solution is adsorbed for 3 hours under the conditions of 45 ℃ and the oscillation speed of 200 rpm, then the adsorbing material is taken out through centrifugal separation, and is re-added into another hexavalent chromium ion aqueous solution with the concentration of 20 mL, the pH =2 and the concentration of 200 mg/L without any desorption and reduction treatment for the next cycle of adsorption experiment, and the experiment proves that the repeated cycle is carried out for 10 times, the reduction rates of PAPA, PTAPA and PAAPA on hexavalent chromium ions reach 99.9%, and the accumulated adsorption capacities of PAPA, PTAPA and PAAPA on chromium ions respectively reach 1026.13, 998.13 and 931.93 mg/g, so that the material prepared by the invention has ultrahigh chromium ion adsorption capacity and self-reduction characteristic, can be activated without any original activator, and is expected to be used as a new generation adsorbing material for detoxification to realize adsorption storage and continuous detoxification of chromium ions.
The above description is only a preferred embodiment of the present invention, and all the equivalent changes and modifications made according to the claims of the present invention should be covered by the present invention.
Claims (4)
1. An application of a microporous conjugated polyaniline adsorption material in the aspect of adsorbing and removing hexavalent chromium in wastewater is characterized in that: the microporous conjugated polyaniline adsorption material is prepared by adopting tri (4-aminophenyl) amine, p-phenylenediamine or 4,4' -diaminodiphenylamine as a linker and tri (4-bromophenyl) amine as a center, and has polyaniline characteristics and microporous conjugated polymer characteristics; adding a center and a linker into tetrahydrofuran, reacting for a certain time at a certain temperature under the action of ligands XPhos and NaOtBu and a catalyst, centrifuging, washing an obtained product with a solvent, and drying to obtain the product;
the solvent comprises at least one of tetrahydrofuran, dioxane, dimethyl sulfoxide, dimethylformamide, acetone, methanol, ethanol, water and N-methylpyrrolidone;
the reaction temperature is 37-202 ℃, and the reaction time is 0.1-72 h.
2. Use according to claim 1, characterized in that: the molar ratio of the used centre to linker is 0.1-3.
3. Use according to claim 1, characterized in that: the mole ratio of XPhos, naOtBu and catalyst is (0.5-3): 10-500): 1, wherein the amount of catalyst is 1-100% of the total mole of the core and linker.
4. Use according to claim 1 or 3, characterized in that: the catalyst is a palladium-containing catalyst.
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| CN114100575A (en) * | 2021-10-25 | 2022-03-01 | 福州大学 | Preparation method and application of nitrogen-containing defect site porous carbon based on microporous organic polymer |
| CN114196018B (en) * | 2021-12-06 | 2023-04-11 | 福州大学 | Thiazolothiazolyl polymer and preparation method and application thereof |
| CN114335558A (en) * | 2021-12-07 | 2022-04-12 | 西安交通大学 | Preparation method of conjugate microporous polyaniline modified battery current collector and application of conjugate microporous polyaniline modified battery current collector in lithium-sulfur battery |
| CN114307989B (en) * | 2022-01-04 | 2024-02-20 | 杭州博华科技创新有限公司 | Formaldehyde-removing nano emulsion composition and preparation method thereof |
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