CN111744460A - Triazine type lignin-based magnetic adsorption material and preparation method thereof - Google Patents
Triazine type lignin-based magnetic adsorption material and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a triazine lignin-based magnetic adsorption material and a preparation method thereof. Mixing lignin and magnetic Fe3O4Dispersing in a solvent medium, reacting with cyanuric chloride at 0-120 ℃ for 2-48 hours under the action of alkali catalysis, and separating and purifying to obtain the triazine lignin-based magnetic adsorption material. The preparation process is simple and convenient, the yield is high, the cost is low, and the prepared magnetic adsorption material contains abundant heteroatoms such as nitrogen and oxygen in the molecular structureThe attachment sites can quickly adsorb heavy metal ions and organic pollutants in a water body in high capacity, have excellent magnetic response performance, have the advantages of easy magnetic separation, recycling and the like, and can be applied to the fields of treatment of wastewater containing heavy metal ions and organic dyes in the industries of mining, electrolysis, printing and dyeing, water body purification and the like.
Description
Technical Field
The invention relates to a triazine type lignin-based magnetic adsorption material and a preparation method thereof, in particular to a magnetic adsorption material prepared from lignin and magnetic Fe3O4A method for preparing triazine lignin-based magnetic adsorption material by reacting with cyanuric chloride belongs to the field of material science.
Background
At present, organic matter pollution and heavy metal ion pollution from water bodies cause serious harm to living environment and human health of living bodies. The method for treating water pollution mainly comprises an adsorption method, a membrane separation method, a chemical precipitation method, a biological method and the like. Among them, the adsorption method is widely used because of advantages such as high treatment efficiency, wide adsorbent sources, and easy operation.
Magnetic Fe3O4Has the advantages of superparamagnetism, high specific surface area, easy surface functionalization modification and the like, and is widely applied to the fields of separation engineering, medicine and the like. Due to magnetic Fe3O4The composite material is easy to prepare, can be subjected to solid-liquid separation under the action of an external magnetic field, is often used as a composite base material of an adsorbent, and is increasingly concerned and valued in the field of environment. However, magnetic Fe3O4Is easy to oxidize and aggregate in the single use process, and usually needs composite modification to improve the physical and chemical properties and dispersion stability. Liu et al (applied surface Science,2018,427,976-3O4The surface modified amino silane layer has Pb (II) ion adsorbing capacity up to 133.3mg/g, and may be separated from water phase fast in outer magnetic field. Tseng et al (ACSSustainable Chemistry)&Magnetic C prepared by Engineering,2019,7(7),6662-3N4@Fe3O4The composite nanosphere not only can adsorb Cr (VI) ions (with the adsorption capacity of 555mg/g), but also can reduce nitroaniline compounds in a water phase. The Chinese patent of invention (application number CN201910049131.1) discloses a preparation method of a polyethylene amine functional magnetic carbon-based nano adsorbent, which has good effect on organic matters such as phenol in wastewaterThe adsorption effect of (1). At present, most of magnetic composite adsorption materials are derived from fossil resources, the cost of base materials is high, the magnetic composite adsorption materials are difficult to degrade in the environment, and secondary pollution is caused to the environment in the processes of production, use and recovery.
The lignin is a natural polymer with abundant reserves in the nature, and has the advantages of being renewable, cheap, environment-friendly and the like. The lignin has a molecular structure containing a large amount of functional groups such as hydroxyl, carboxyl, ether bond, benzene ring and the like, and is easy to modify and use. The invention combines lignin and magnetic Fe3O4The structural characteristics and the reaction activity of the base material are that cyanuric chloride is used as a cross-linking agent to prepare the cheap, green and environment-friendly magnetic adsorption material through a cross-linking reaction. The preparation method disclosed by the invention is simple in preparation process, high in yield and low in cost, the prepared magnetic adsorption material has larger specific surface area and excellent magnetic response performance, the molecular structure contains abundant nitrogen, oxygen and other heteroatom adsorption sites, heavy metal ions and organic pollutants in a water body can be quickly and highly adsorbed, the magnetic adsorption material has the advantages of easiness in magnetic separation, recycling and the like, and the magnetic adsorption material can be applied to the fields of heavy metal ion-containing and organic dye-containing wastewater treatment, water body purification and the like in the industries of mining, electrolysis, printing and dyeing and the like.
Disclosure of Invention
The invention aims to provide a triazine type lignin-based magnetic adsorption material which is green, cheap and excellent in adsorption performance and a preparation method thereof3O4And reacting with cyanuric chloride to prepare the triazine lignin-based magnetic adsorption material.
The technical scheme of the invention is as follows: a triazine-type lignin-base magnetic adsorbing material is prepared from lignin and magnetic Fe3O4The triazine type magnetic adsorbing material prepared by the reaction with cyanuric chloride has a chemical structure schematically shown as follows:
The method for preparing the triazine lignin-based magnetic adsorption material comprises the following reaction:
wherein
Is magnetic Fe3O4Particles, X is any one element of N, O, S.
The method is realized by the following steps:
mixing lignin and magnetic Fe3O4Uniformly dispersing in a solvent, adding cyanuric chloride and an alkali catalyst, stirring to react fully, filtering after the reaction is finished, washing a solid filtrate to remove unreacted substances, and drying to obtain the triazine type lignin-based magnetic adsorption material.
The lignin is one or more of alkali lignin, organic solvent soluble lignin, acetic acid lignin, lignin sulfate, lignosulfonate, high-boiling alcohol lignin and enzymolysis lignin.
The magnetic Fe3O4Is hydroxy magnetic Fe3O4Amido magnetic Fe3O4Carboxy magnetic Fe3O4Or mercapto magnetic Fe3O4Any one or more of them.
The solvent is one or more of N, N-dimethylacetamide, tetrahydrofuran, 1, 4-dioxane, dimethyl sulfoxide, toluene, mesitylene and water.
The alkali catalyst is any one or more of sodium hydroxide, sodium carbonate, sodium bicarbonate, potassium hydroxide, potassium carbonate, potassium bicarbonate, sodium acetate, pyridine, triethylamine and ammonia water.
The solvent used for washing is any one or more of hydrochloric acid, acetic acid, N-dimethylformamide, N-dimethylacetamide, ethyl acetate, dichloromethane, tetrahydrofuran, 1, 4-dioxane, dimethyl sulfoxide, toluene, acetonitrile, methanol, ethanol, propanol, N-butanol and water.
The stirring reaction temperature is 0-120 ℃, and the stirring reaction is carried out for 2-48 hours.
The drying mode is vacuum drying at 20-150 ℃ or freeze drying at-20-0 ℃.
Has the advantages that:
1. the preparation method realizes the rapid preparation of the lignin-based magnetic adsorbing material under mild conditions, has simple and convenient preparation process and less required equipment, and is beneficial to realizing industrial production.
2. The lignin raw material used in the invention is renewable natural polymer with abundant reserves, and has good biocompatibility and environmental degradability.
3. The triazine lignin-based magnetic adsorption material introduces lignin macromolecules to protect magnetic Fe3O4The particles are protected from chemical attack and prevent the nanoparticles from agglomerating, increasing the specific surface area of the adsorbent material.
4. The triazine lignin-based magnetic adsorption material contains abundant nitrogen, oxygen and other heteroatom adsorption sites in the molecular structure, and can quickly adsorb heavy metal ions and organic pollutants in a water body at high capacity. Can be separated quickly and efficiently under an external magnetic field, and solves the problem that the adsorption material is difficult to separate. The separated triazine lignin-based magnetic adsorption material can be recycled through simple enrichment and desorption, and is expected to be used in the fields of treatment of wastewater containing heavy metal ions and organic dyes, water purification and the like in the industries of mining, electrolysis, printing and dyeing and the like.
Drawings
Fig. 1 is an infrared spectrum of the triazine-based lignin-based magnetic adsorbent in example 1.
FIG. 2 is a Transmission Electron Microscope (TEM) image of the lignin-based magnetic adsorbent of example 1.
Fig. 3 is a Scanning Electron Microscope (SEM) image of the lignin-based magnetic adsorbent in example 2.
FIG. 4 is a schematic view of the adsorption cycle of Pb (II) ions by the lignin-based magnetic adsorbent in example 2.
Detailed Description
The invention is prepared from lignin and magnetic Fe3O4The triazine lignin-based magnetic adsorption material is prepared by reacting with cyanuric chloride, and the reaction process comprises the following steps:
the preparation method of the triazine lignin-based magnetic adsorption material is characterized by comprising the following steps: the method specifically comprises the following steps:
mixing lignin and magnetic Fe3O4Uniformly dispersing in a solvent, adding cyanuric chloride and an alkali catalyst, and stirring and reacting for 2-48 hours at 0-120 ℃. And after the reaction is finished, filtering, washing the solid filtrate to remove unreacted substances, and drying to obtain the triazine type lignin-based magnetic adsorption material.
The lignin is one or more of alkali lignin, organic soluble lignin, acetic acid lignin, lignin sulfate, lignosulfonate, high-boiling alcohol lignin and enzymolysis lignin.
The magnetic Fe3O4Is hydroxy magnetic Fe3O4Amido magnetic Fe3O4Carboxy magnetic Fe3O4Or mercapto magnetic Fe3O4Any one or more of them.
The solvent is one or more of N, N-dimethylacetamide, tetrahydrofuran, 1, 4-dioxane, dimethyl sulfoxide, toluene, mesitylene and water.
The alkali catalyst is any one or more of sodium hydroxide, sodium carbonate, sodium bicarbonate, potassium hydroxide, potassium carbonate, potassium bicarbonate, sodium acetate, pyridine, triethylamine and ammonia water.
The solvent used for washing is any one or more of hydrochloric acid, acetic acid, N-dimethylformamide, N-dimethylacetamide, ethyl acetate, dichloromethane, tetrahydrofuran, 1, 4-dioxane, dimethyl sulfoxide, toluene, acetonitrile, methanol, ethanol, propanol, N-butanol and water.
The drying mode is vacuum drying at 20-150 ℃ or freeze drying at-20-0 ℃.
Example 1:
2.0g of alkali lignin and 0.4g of magnetic Fe are added into a three-necked bottle3O40.4g of potassium carbonate and 100mL of tetrahydrofuran are stirred evenly at room temperature, then 0.2g of cyanuric chloride is added, and the temperature is raised to 65 ℃ for reaction for 12 hours. After the reaction was complete, the reaction was cooled to room temperature and a grey solid precipitated. Filtering, washing the filtered solid with tetrahydrofuran, water and ethanol in sequence to remove unreacted substances, and drying in vacuum at 60 ℃ to obtain the brown lignin-based magnetic adsorbing material (yield 76%).
Through infrared spectrum analysis, the molecular structure of the lignin-based magnetic adsorption material contains functional groups such as hydroxyl, triazine ring and the like (figure 1).
The specific surface area of the lignin-based magnetic adsorption material is 137m determined by BET analysis2/g。
Through inductively coupled plasma spectroscopy analysis, the adsorption capacity of the lignin-based magnetic adsorption material on Cu (II) ions in an aqueous solution with the pH value of 6 is 96 mg/g.
Example 2:
0.55g of lignin acetate and 1.1g of amino magnetic Fe were added to a three-necked flask3O40.4g of sodium carbonate and 100mL of 1, 4-dioxane are stirred evenly at room temperature, then 0.16g of cyanuric chloride is added, and the temperature is raised to 90 ℃ for reaction for 10 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and a black solid was precipitated. Filtering, washing the filtered solid with 1, 4-dioxane, water and ethyl acetate in sequence to remove unreacted substances, and drying in vacuum at 70 ℃ to obtain the black lignin-based magnetic adsorption material (yield is 71%).
The specific surface area of the lignin-based magnetic adsorption material is 103m determined by BET analysis2/g。
According to the analysis of the inductively coupled plasma spectrum, the adsorption capacity of the lignin-based magnetic adsorption material to Pb (II) ions in an aqueous solution with the pH value of 6 is 137 mg/g.
After the lignin-based magnetic adsorption material is washed, desorbed and re-adsorbed by dilute hydrochloric acid for 5 times, the adsorption capacity of the lignin-based magnetic adsorption material on Pb (II) ions is 118mg/g, and the cyclic adsorption efficiency E is more than 86% (figure 4).
The calculation formula of the circulating adsorption efficiency E is as follows:
in the formula: qnThe adsorption capacity, Q, of the adsorption material to heavy metal ions after n times of desorption/adsorption0Is the initial adsorption capacity of the adsorption material for heavy metal ions.
Example 3:
adding 1.6g of enzymolysis lignin and 0.8g of carboxyl magnetic Fe into a three-necked flask3O40.4g of sodium hydroxide and 150mL of toluene are stirred evenly at room temperature, then 0.2g of cyanuric chloride is added, and the temperature is raised to 100 ℃ for reaction for 14 h. After the reaction was completed, the reaction mixture was cooled to room temperature, and a dark solid was precipitated. Filtering, washing the solid filtrate with toluene, water and tetrahydrofuran in sequence to remove unreacted substances, and drying in vacuum at 80 ℃ to obtain the brown lignin-based magnetic adsorption material (yield is 78%).
The saturation magnetization of the lignin-based magnetic adsorption material is 15.4emu/g through the specific magnetic saturation method.
Through ultraviolet spectrum analysis, the adsorption capacity of the lignin-based magnetic adsorption material to Congo red in an aqueous solution with the pH value of 6 is 241mg/g, and the adsorption efficiency E of 5-time circulation is more than 80%.
Example 4:
1.0g of sodium lignosulfonate and 1.0g of mercapto magnetic Fe are added into a three-necked bottle3O40.3g of cyanuric chloride and 150mL of 1, 4-dioxane are stirred evenly at room temperature, 0.4g of potassium hydroxide is added, and the temperature is raised to 100 ℃ for reaction for 8 hours. After the reaction is finished, the reaction product is cooled to room temperature, and a solid crude product is separated out. Filtering, washing the solid filtrate with 1, 4-dioxane, water and ethanol in sequence to remove unreacted substances, and vacuum drying at 60 ℃ to obtain the black lignin-based magnetic adsorption material (yield 74%).
The saturation magnetization of the lignin-based magnetic adsorption material is 10.2emu/g through the specific magnetic saturation method.
Through ultraviolet spectrum analysis, the adsorption capacity of the lignin-based magnetic adsorption material to methyl orange in an aqueous solution with the pH value of 6 is 337mg/g, and the adsorption efficiency E of 5 cycles is more than 85%.
Example 5:
2.0g of organic soluble lignin and 0.6g of amino magnetic Fe are added into a three-necked bottle3O40.2g of triethylamine and 100mL of dimethyl sulfoxide are stirred uniformly at room temperature, then 0.2g of cyanuric chloride is added, and the temperature is raised to 100 ℃ for reaction for 12 hours. After the reaction is finished, the reaction product is cooled to room temperature, and a solid crude product is separated out. Filtering, washing the solid filtrate with tetrahydrofuran, water and ethanol in sequence to remove unreacted substances, and drying in vacuum at 50 ℃ to obtain the black lignin-based magnetic adsorption material (yield is 84%).
The saturation magnetization of the lignin-based magnetic adsorption material is 12.4emu/g through the specific magnetic saturation method.
Through inductively coupled plasma spectrum analysis, the adsorption capacity of the lignin-based magnetic adsorption material to Cd (II) ions in an aqueous solution with the pH value of 6 is 106mg/g, and the adsorption efficiency E of 5 cycles is more than 80%.
Claims (10)
1. A triazine type lignin-based magnetic adsorption material is characterized in that: from lignin and magnetic Fe3O4The triazine type magnetic adsorbing material prepared by the reaction with cyanuric chloride has a chemical structure schematically shown as follows:
2. The method for preparing the triazine type lignin-based magnetic adsorption material of claim 1, wherein: the reaction is as follows:
wherein
Is magnetic Fe3O4Particles, X is any one element of N, O, S.
3. The method for preparing the triazine type lignin-based magnetic adsorption material according to claim 2, wherein: the method is realized by the following steps:
mixing lignin and magnetic Fe3O4Uniformly dispersing in a solvent, adding cyanuric chloride and an alkali catalyst, stirring to react fully, filtering after the reaction is finished, washing a solid filtrate to remove unreacted substances, and drying to obtain the triazine type lignin-based magnetic adsorption material.
4. The method for preparing a triazine type lignin-based magnetic adsorption material according to claim 2 or 3, wherein: the lignin is one or more of alkali lignin, organic solvent soluble lignin, acetic acid lignin, lignin sulfate, lignosulfonate, high-boiling alcohol lignin and enzymolysis lignin.
5. The method for preparing a triazine type lignin-based magnetic adsorption material according to claim 2 or 3, wherein: the magnetic Fe3O4Is hydroxy magnetic Fe3O4Amido magnetic Fe3O4Carboxy magnetic Fe3O4Or mercapto magnetic Fe3O4Any one or more of them.
6. The method for preparing the triazine type lignin-based magnetic adsorption material according to claim 3, wherein the method comprises the following steps: the solvent is one or more of N, N-dimethylacetamide, tetrahydrofuran, 1, 4-dioxane, dimethyl sulfoxide, toluene, mesitylene and water.
7. The method for preparing the triazine type lignin-based magnetic adsorption material according to claim 3, wherein the method comprises the following steps: the alkali catalyst is any one or more of sodium hydroxide, sodium carbonate, sodium bicarbonate, potassium hydroxide, potassium carbonate, potassium bicarbonate, sodium acetate, pyridine, triethylamine and ammonia water.
8. The method for preparing the triazine type lignin-based magnetic adsorption material according to claim 3, wherein the method comprises the following steps: the solvent used for washing is any one or more of hydrochloric acid, acetic acid, N-dimethylformamide, N-dimethylacetamide, ethyl acetate, dichloromethane, tetrahydrofuran, 1, 4-dioxane, dimethyl sulfoxide, toluene, acetonitrile, methanol, ethanol, propanol, N-butanol and water.
9. The method for preparing the triazine type lignin-based magnetic adsorption material according to claim 3, wherein the method comprises the following steps: the stirring reaction temperature is 0-120 ℃, and the stirring reaction is carried out for 2-48 hours.
10. The method for preparing the triazine type lignin-based magnetic adsorption material according to claim 3, wherein the method comprises the following steps: the drying mode is vacuum drying at 20-150 ℃ or freeze drying at-20-0 ℃.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115845812A (en) * | 2023-01-06 | 2023-03-28 | 大连工业大学 | Preparation method and application of magnetic lignin adsorption material |
| CN115845812B (en) * | 2023-01-06 | 2024-05-03 | 大连工业大学 | Preparation method and application of magnetic lignin adsorption material |
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