CN113842897B - Preparation method of cyclodextrin polymer for adsorbing organic dye - Google Patents

Preparation method of cyclodextrin polymer for adsorbing organic dye Download PDF

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CN113842897B
CN113842897B CN202111236615.0A CN202111236615A CN113842897B CN 113842897 B CN113842897 B CN 113842897B CN 202111236615 A CN202111236615 A CN 202111236615A CN 113842897 B CN113842897 B CN 113842897B
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cyclodextrin
adsorption
water
lignosulfonate
polymer
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CN113842897A (en
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吕东灿
姜广策
王志敏
李鑫
申文波
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Henan Agricultural University
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • 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
    • B01J20/24—Naturally occurring macromolecular compounds, e.g. humic acids or their derivatives
    • 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
    • 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
    • C02F2101/30—Organic compounds
    • C02F2101/308—Dyes; Colorants; Fluorescent agents
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W10/00—Technologies for wastewater treatment
    • Y02W10/30—Wastewater or sewage treatment systems using renewable energies
    • Y02W10/37—Wastewater or sewage treatment systems using renewable energies using solar energy

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Hydrology & Water Resources (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental & Geological Engineering (AREA)
  • Water Supply & Treatment (AREA)
  • Analytical Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

The invention discloses a preparation method of cyclodextrin polymer for adsorbing organic dye, which specifically uses cyclodextrin and lignosulfonate with low price as main raw materials, and prepares lignin/cyclodextrin polymer adsorption material with good adsorption performance by crosslinking the cyclodextrin and lignosulfonate with citric acid.

Description

Preparation method of cyclodextrin polymer for adsorbing organic dye
Technical Field
The invention belongs to the technical field of organic pollutant adsorption materials, and particularly relates to a preparation method of cyclodextrin polymer for adsorbing organic dye.
Background
The adsorption method is a method for removing organic pollutants in water body with higher application value. Cyclodextrin is used as a cyclic oligosaccharide with wide sources, low price and no toxic or side effect, has a three-dimensional chiral cavity in a molecular structure, is hydrophilic outside the cavity and hydrophobic inside the cavity, and can be compounded with a plurality of organic pollutants to achieve the effect of adsorbing the organic matters, so that the cyclodextrin has wide application prospect in the field of organic pollutant sewage treatment, however, the cyclodextrin adsorption material prepared in the prior art has limited effect of treating the organic pollutant sewage due to better water solubility, is difficult to recover after treatment, and reduces the utilization rate of the cyclodextrin adsorption material to cause resource waste; therefore, the cyclodextrin adsorption polymer material needs to be modified to obtain a novel cyclodextrin polymer adsorption material with improved water solubility and improved adsorption performance, so that the cyclodextrin adsorption polymer material has wide application prospect in the field of sewage treatment.
Chinese patent (202110021098.9) discloses a preparation method of cyclodextrin-citric acid graft supported magnetic spheres, which comprises the steps of reacting citric acid, cyclodextrin and a catalyst at low temperature, adding ceramic spheres for high-temperature reaction, and changing the temperature for continuous reaction to obtain a yellow product. The adsorption material with stable performance is prepared by the method, but the preparation process is complex, and the adsorption quantity of the fluorine triol is not high, and only reaches 15.98 mg/g.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a preparation method of cyclodextrin polymer for adsorbing organic dye, which takes cyclodextrin and lignosulfonate with low price as main raw materials and takes citric acid as a cross-linking agent to cross-link the cyclodextrin and lignosulfonate, so as to prepare cyclodextrin polymer with good adsorption performance, wherein the adsorption material has higher adsorption capacity to organic dye methylene blue.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
the preparation method of the cyclodextrin polymer for adsorbing the organic dye specifically comprises the following steps:
(1) Placing lignosulfonate, citric acid, dibasic phosphate, cyclodextrin and deionized water in a dry beaker, and stirring at normal temperature for 10 min to form a uniform and transparent mixed solution;
(2) Placing the mixed solution in the step (1) in a baking oven to react for 6-8 h at 100 ℃, and then heating to 170-180 ℃ to react for 30-60 min;
(3) Grinding the solid matters obtained after the reaction in the step (2), soaking in water, washing with water, filtering, repeating the above operation until the filtrate is clear and transparent after washing with water, and filtering to obtain a solid product; and drying and grinding the solid product to obtain the cyclodextrin polymer adsorption material.
Preferably, the weight ratio of the lignosulfonate, the cyclodextrin and the citric acid in the step (1) is 0.2-6:15:10-15;
more preferably, the weight ratio of the lignosulfonate, the cyclodextrin and the citric acid in the step (1) is 3-6:15:12-15;
preferably, the weight ratio of the dibasic phosphate to the cyclodextrin in the step (1) is 2-4:5;
preferably, the ratio of lignosulfonate to deionized water in the mixed solution in step (1) is 0.001-0.04 g/mL.
The proportion of lignosulfonate, citric acid and cyclodextrin in the preparation method has obvious influence on the adsorption quantity of the prepared cyclodextrin polymer, when the quantity of the citric acid and the cyclodextrin is controlled to be unchanged, the addition proportion of sodium lignosulfonate is positively correlated with the adsorption quantity of an adsorption material on methylene blue, the maximum proportion of sodium lignosulfonate to the cyclodextrin is 2:5, and when the proportion of sodium lignosulfonate to the cyclodextrin is greater than 2:5, the reaction system is suspension with higher viscosity, solid-liquid separation is difficult to realize, and an ideal adsorption material cannot be obtained.
The preparation principle of the cyclodextrin polymer for adsorbing the organic dye is shown in the figure 1, and lignin and cyclodextrin are subjected to esterification reaction with citric acid to generate crosslinking, so that a lignin-cyclodextrin crosslinking product insoluble in water is formed.
The beneficial effects are that:
(1) The invention takes the cyclodextrin and the lignosulfonate with low price as main raw materials, and the lignin/cyclodextrin polymer with good adsorption performance is prepared by crosslinking the cyclodextrin and the lignosulfonate with citric acid.
(2) The cyclodextrin polymer adsorption material prepared by the method has the advantages of improved water solubility, improved adsorption capacity and better adsorption effect than expensive materials such as graphene oxide.
(3) According to the invention, lignosulfonate is added in the cyclodextrin polymer adsorption material, is an industrial production waste, has low utilization value, is often discarded, causes environmental pollution, and can be utilized to increase the economic value and improve the environmental pollution problem caused by the use of the lignosulfonate; the addition of lignosulfonate can provide abundant benzene ring structures for cyclodextrin polymers, and the benzene ring structures can improve the adsorption capacity of organic pollutants, particularly organic pollutants containing benzene rings, through pi-pi conjugation; the polymer can effectively improve the adsorption capacity to organic pollutants, especially pollutants containing benzene ring structures, by combining with unique hydrophobic cavities of cyclodextrin.
Drawings
FIG. 1 is a schematic diagram of the preparation principle of a cyclodextrin polymer adsorbing material for adsorbing organic dye according to the present invention;
FIG. 2 is a Scanning Electron Microscope (SEM) image of the cyclodextrin polymer adsorbing material adsorbing an organic dye prepared in example 1;
FIG. 3 is an infrared spectrum (FTIR) of cyclodextrin and the cyclodextrin polymer adsorbing material adsorbing organic dye prepared in example 1.
Detailed Description
The technical scheme of the invention is described in detail below with reference to the accompanying drawings and specific embodiments. The following examples will assist those skilled in the art in further understanding the present invention, but are not intended to limit the invention in any way. It should be noted that variations and modifications could be made by those skilled in the art without departing from the inventive concept. These are all within the scope of the present invention.
Example 1
Adding 0.02-g g of sodium lignin sulfonate, 1.5-g g of cyclodextrin, 1.2-g g of citric acid and 0.9 g of monopotassium phosphate into a 500-mL beaker, magnetically stirring at 500 rpm for 10 min, placing the mixture in an oven at 100 ℃ for reaction 8-h, and heating to 190 ℃ for reaction 1-h; grinding the solid substance after the reaction, adding 200 mL water to soak 1 h, filtering, adding the obtained filter residue into 200 mL water to soak 1 h, and suction filtering; washing with water until the filtrate is clear and transparent to obtain a 1.8 g cyclodextrin adsorption material, drying and grinding the solid to obtain the cyclodextrin polymer adsorption material, wherein the adsorption capacity of the cyclodextrin polymer adsorption material to methylene blue is 653 mg/g.
The methylene blue adsorption experiment is a conventional adsorption operation, specifically, 50 mg cyclodextrin adsorption material is added into 50 mL of 1200 mg/L methylene blue solution, and 16 h is adsorbed under the conditions of 25 ℃ and 180 rpm; the suspension was filtered through a 0.45 μm filter, diluted 200-fold, and absorbance was measured at 665 nm. The amount of methylene blue adsorbed (mg/g) by the adsorbent material was calculated from the methylene blue standard solution.
The SEM image of the adsorption material obtained in example 1 at 45000 times is shown in fig. 2, the surface of the lignin-cyclodextrin polymer adsorption material is rough, and the surface of the lignin-cyclodextrin adsorption material is covered with a mesoporous and macroporous structure with an average pore diameter of 54 nm, which is beneficial to adsorption.
The cyclodextrin and the cyclodextrin polymer adsorption material prepared in example 1 were analyzed for the structure of the surface functional group, and the result shows that the cyclodextrin molecule contains more hydroxyl groups and 3400. 3400 cm -1 The absorption is stronger nearby, but the hydroxyl of the polymer is obviously reduced, which indicates that a part of hydroxyl in the polymer and citric acid are subjected to esterification reaction; and in 1740. 1740 cm in polymer -1 The c=o stretching vibration peak in the ester material is generated, which proves that the esterification reaction occurs.
Example 2
Adding 0.6-g-sodium lignin sulfonate, 1.5-g-cyclodextrin, 1.5-g-citric acid and 0.9 g-potassium dihydrogen phosphate into a 500-mL beaker, magnetically stirring at 500 rpm for 10 min, placing the mixture in an oven at 100deg.C for reaction 8-h, and heating to 200deg.C for reaction 1-h; grinding the solid substance after the reaction, adding 200 mL water to soak 1 h, filtering, adding the obtained filter residue into 200 mL water to soak 1 h, and suction filtering; washing with water until the filtrate is clear and transparent to obtain 1.8 g cyclodextrin adsorbing material, drying and grinding the solid to obtain cyclodextrin polymer adsorbing material, wherein the adsorption capacity of the cyclodextrin polymer adsorbing material to methylene blue is 758-mg/g.
The methylene blue adsorption experiment was the same as in example 1.
Example 3
Adding sodium lignin sulfonate 0.05 g, cyclodextrin 1.5 g, citric acid 1.2 g, sodium dihydrogen phosphate 0.6 g and 18 mL of water into a 500 mL beaker, magnetically stirring at 500 rpm for 10 min, placing the mixture in an oven at 100deg.C for reaction 8 h, and heating to 180deg.C for reaction 1 h; grinding the solid substance after the reaction, adding 200 mL water to soak 1 h, filtering, adding the obtained filter residue into 200 mL water to soak 1 h, and suction filtering; washing with water until the filtrate is clear and transparent to obtain a 1.8 g cyclodextrin adsorption material, drying and grinding the solid to obtain the cyclodextrin polymer adsorption material, wherein the adsorption quantity of the cyclodextrin polymer adsorption material to methylene blue is 599 mg/g.
The methylene blue adsorption experiment was the same as in example 1.
Example 4
Adding 0.2 g g g of calcium lignin sulfonate, 1.5 g g g of cyclodextrin, 1.0 g g of citric acid and 0.9 g of sodium dihydrogen phosphate into a 500 mL beaker, magnetically stirring at 500 rpm for 10 min, placing the mixture in an oven to react at 100 ℃ for 8 h, and heating to 170 ℃ to react for 30 min; grinding the solid substance after the reaction, adding 200 mL water to soak 1 h, filtering, adding the obtained filter residue into 200 mL water to soak 1 h, and suction filtering; washing with water until the filtrate is clear and transparent to obtain 1.7. 1.7 g cyclodextrin adsorption material, drying and grinding the solid to obtain cyclodextrin polymer adsorption material, wherein the adsorption capacity of the material to methylene blue is 650 mg/g.
The methylene blue adsorption experiment was the same as in example 1.
Example 5
Adding 0.3-g-sodium lignin sulfonate, 1.5-g-cyclodextrin, 1.5-g-citric acid and 0.9 g-sodium dihydrogen phosphate into a 500-mL beaker, magnetically stirring at 500 rpm for 10 min, placing the mixture in an oven at 100deg.C for reaction 6-h, and heating to 180deg.C for reaction 45 min; grinding the solid substance after the reaction, adding 200 mL water to soak 1 h, filtering, adding the obtained filter residue into 200 mL water to soak 1 h, and suction filtering; washing with water until the filtrate is clear and transparent to obtain 2.1 g cyclodextrin adsorbing material, drying and grinding the solid to obtain cyclodextrin polymer adsorbing material, wherein the adsorption capacity of the cyclodextrin polymer adsorbing material to methylene blue is 692 mg/g.
The methylene blue adsorption experiment was the same as in example 1.
Example 6
Adding 0.4 g g g sodium lignin sulfonate, 1.5 g g g cyclodextrin, 1.2 g g g citric acid and 0.6 g sodium dihydrogen phosphate into a 500 mL beaker, magnetically stirring at 500 rpm for 10 min, placing the mixture in an oven to react at 100deg.C for 8 h, and heating to 170deg.C for 30 min; grinding the solid substance after the reaction, adding 200 mL water to soak 1 h, filtering, adding the obtained filter residue into 200 mL water to soak 1 h, and suction filtering; washing with water until the filtrate is clear and transparent to obtain 1.7. 1.7 g cyclodextrin adsorbing material, drying and grinding the solid to obtain cyclodextrin polymer adsorbing material, wherein the adsorption capacity of the cyclodextrin polymer adsorbing material to methylene blue is 679 mg/g.
The methylene blue adsorption experiment was the same as in example 1.
Example 7
Adding 0.4 g g g of calcium lignin sulfonate, 1.5 g g g of cyclodextrin, 1.5 g g g of citric acid and 0.9 g of sodium dihydrogen phosphate into a 500 mL beaker, magnetically stirring at 500 rpm for 10 min, placing the mixture in an oven to react at 100 ℃ for 8 h, and heating to 170 ℃ to react for 30 min; grinding the solid substance after the reaction, adding 200 mL water to soak 1 h, filtering, adding the obtained filter residue into 200 mL water to soak 1 h, and suction filtering; washing with water until the filtrate is clear and transparent to obtain 2.0 g cyclodextrin adsorption material, drying and grinding the solid to obtain cyclodextrin polymer adsorption material, wherein the adsorption capacity of the material to methylene blue is 601 mg/g.
The methylene blue adsorption experiment was the same as in example 1.
Example 8
Adding 0.5-g-sodium lignin sulfonate, 1.5-g-cyclodextrin, 1.0-g-citric acid, 0.9 g-sodium dihydrogen phosphate and 15 mL of water into a 500-mL beaker, magnetically stirring at 500 rpm for 10 min, placing the mixture into an oven at 100deg.C for reaction at h, and heating to 170deg.C for reaction for 30 min; grinding the solid substance after the reaction, adding 200 mL water to soak 1 h, filtering, adding the obtained filter residue into 200 mL water to soak 1 h, and suction filtering; washing with water until the filtrate is clear and transparent to obtain a 2.1 g cyclodextrin adsorption material, drying and grinding the solid to obtain the cyclodextrin polymer adsorption material, wherein the adsorption capacity of the cyclodextrin polymer adsorption material to methylene blue is 624 mg/g.
The methylene blue adsorption experiment was the same as in example 1.
Comparative example 1
Adding cyclodextrin 1.5 g, citric acid 1.5 g, potassium dihydrogen phosphate 0.9 g and 15 mL of water into a 500 mL beaker, magnetically stirring at 500 rpm for 10 min, placing the mixture into an oven at 100deg.C for reaction 8 h, and heating to 200deg.C for reaction 1 h; grinding the solid substance after the reaction, adding 200 mL water to soak 1 h, filtering, adding the obtained filter residue into 200 mL water to soak 1 h, and suction filtering; washing with water until the filtrate is clear and transparent to obtain a cyclodextrin adsorbing material of 1.9 and g, drying and grinding the solid to obtain a cyclodextrin polymer adsorbing material, wherein the adsorption quantity of the cyclodextrin polymer adsorbing material to methylene blue is 460 mg/g.
The methylene blue adsorption experiment was the same as in example 1.
Comparative example 1 was essentially the same as example 2 in the preparation of cyclodextrin polymer adsorbent material, except that sodium lignin sulfonate was not added; the prepared adsorption material is used for an adsorption experiment on methylene blue solution, and the adsorption amount of the material on methylene blue is 460 mg/g and is obviously lower than the adsorption amount 758/mg/g of methylene blue in example 2.
Finally, it is noted that the above-mentioned embodiments are merely for illustrating the technical solution of the present invention, and that other modifications and equivalents thereof by those skilled in the art should be included in the scope of the claims of the present invention without departing from the spirit and scope of the technical solution of the present invention.

Claims (4)

1. The preparation method of the cyclodextrin polymer for adsorbing the organic dye is characterized by comprising the following steps of:
(1) Placing lignosulfonate, citric acid, dibasic phosphate, cyclodextrin and deionized water into a dry beaker, stirring at normal temperature for 10 min to form a uniform and transparent mixed solution, wherein the weight ratio of the lignosulfonate to the cyclodextrin to the citric acid is 0.2-6:15:10-15, and the maximum ratio of the lignosulfonate to the cyclodextrin is 2:5;
(2) Placing the mixed solution in the step (1) in a baking oven to react for 6-8 h at 100 ℃, and then heating to 170-180 ℃ to react for 30-60 min;
(3) Grinding the solid matters obtained after the reaction in the step (2), soaking in water, washing with water, filtering, repeating the above operation until the filtrate is clear and transparent after washing with water, and filtering to obtain a solid product; and drying and grinding the solid product to obtain the cyclodextrin polymer adsorption material.
2. The method for preparing cyclodextrin polymer of adsorbing organic dye according to claim 1, wherein the weight ratio of lignin sulfonate, cyclodextrin and citric acid in the step (1) is 3-6:15:12-15.
3. The method of claim 1, wherein the weight ratio of the dibasic phosphate to cyclodextrin is 2-4:5.
4. The method for preparing cyclodextrin polymer of adsorbing organic dye according to claim 1, wherein the ratio of lignosulfonate to deionized water in the mixed solution in the step (1) is 0.001-0.04 g/mL.
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JP2015084659A (en) * 2013-10-28 2015-05-07 積水アクアシステム株式会社 Microorganism, methods for water purification, methods for treating waste water and adsorbing materials for anionic substances
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