CN113083240B - Preparation method of polymethacrylhydrazone modified guar gum adsorbing material - Google Patents
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
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- C02F1/00—Treatment of water, waste water, or sewage
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
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- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
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Abstract
The invention belongs to the field of natural polymer modification, relates to a preparation method of a polymethacryloylhydrazone modified guar gum adsorbing material, and mainly relates to a preparation method of a polyacryloylhydrazone modified carbohydrate compound. The method comprises the following steps: weighing the following components in a mass ratio of 1: 1, adding acrylic acid and methyl methacrylate into deionized water, adjusting the pH, adding potassium persulfate serving as an initiator and N' N-methylene bisacrylamide serving as a cross-linking agent, and reacting at 70 ℃ for 6 hours to obtain a product A; according to the mol ratio of 1: 1-1: 3, weighing corresponding mass of A and hydrazine hydrate in deionized water, and reacting for 3 hours at the temperature of 60-80 ℃ to obtain a product B; according to a molar ratio of 1: 1-1: and 3, weighing the B with the corresponding mass into ethanol, adding the dialdehyde guar gum and the glacial acetic acid with the corresponding mass, and reacting for 3 hours at 85 ℃ to obtain a product C. The method has the advantages of convenient operation, easily obtained raw materials and low cost. The prepared material has more excellent performance and is suitable for industrial production.
Description
Technical Field
The invention belongs to the field of natural polymer modification, relates to preparation of a high-performance adsorbing material, and particularly relates to a preparation method of a polymethacrylhydrazone modified guar gum adsorbing material.
Background
Various environmental pollution problems are often involved in industrial production, and water pollution is one of the most troublesome problems. The water body pollutants are various, and are generally polluted by heavy metal ions and dye wastewater. The water treatment agent researched at the present stage still has certain limitations, such as low treatment efficiency, poor recycling property, easy secondary pollution and the like. Therefore, aiming at the problems exposed at present, the research and development of a novel water body pollutant treatment material with high efficiency and energy saving has important significance.
Guar gum, a natural high-molecular polysaccharide with wide source and low price, is favored by researchers because of its unique galacto-mannose linear structure, excellent viscosity increasing property, water solubility, the fact that only one group of alcoholic hydroxyl group and most of primary hydroxyl group and secondary hydroxyl group are positioned on the outer side of the molecular chain, and the advantage of having the largest hydrogen bond bonding area, and is often applied to industrial production. However, raw guar gum tends to have the following disadvantages: the rapid swelling and hydration can not be realized, and the dissolution speed is slow; the content of water insoluble substances is high; the viscosity is not easy to control; is easily decomposed by microorganisms and cannot be stored for a long time. These drawbacks have greatly limited the use of guar and therefore it is necessary to modify guar, to modify its physicochemical characteristics, in particular to optimize it with respect to the defects exposed, and to confer it more excellent properties in order to obtain a wider range of applications. The following methods are common at present: physical modification, chemical modification, biological modification and the like.
The acylhydrazone compound is widely applied to the fields of analysis, catalysis, slow release, medicine and biology due to the unique chemical structure, and is a research hotspot of researchers. So far, the acylhydrazone compounds to be researched are often small molecule compounds or compounds formed by combining small molecules with saccharides, and the prepared materials containing acylhydrazone structures can only adsorb or remove heavy metal ions and cannot adsorb or remove dye wastewater, so that the application of the acylhydrazone compounds is greatly limited. Polyacrylic acids or polyacrylamide compounds are widely applied to the development of materials for removing ions or dye wastewater because of good space network structures and large specific surface areas, but the polyacrylic acids or polyacrylamide compounds have strong salt sensitivity and poor ion adsorption effects. Based on the performance deficiency of the existing adsorbing material, the invention adopts the polyacrylate compound to modify the carbohydrate compound to prepare the guar gum compound modified by the polyacrylic acid acylhydrazone.
In summary, the invention firstly uses acrylic acid and methyl methacrylate as raw materials to obtain a product A through aqueous solution free radical polymerization, and performs chemical modification hydrazinolysis on the product A to obtain a hydrazinolysis product B. And finally, preparing the polyacrylic hydrazone modified guar gum compound by taking the B and the dialdehyde guar gum as raw materials through a simple aldehyde-amine condensation reaction. The high polymer material prepared by the invention contains various functional groups, not only has the advantage of natural guar gum polyhydroxy, but also has the advantages of polyacrylic acid polycarboxyl and larger specific surface area, and more importantly has the advantage of good salt resistance of acylhydrazone compounds, so that the high polymer material has more excellent application performance in the aspects of heavy metal ion wastewater and dye wastewater treatment.
Disclosure of Invention
Technical description: aiming at the defects of the existing heavy metal ion wastewater and dye wastewater treatment materials and the innovation of water treatment materials, the invention aims to prepare a novel polymethacryloylhydrazone modified guar gum adsorption material by using acrylic acid, methyl methacrylate, hydrazine hydrate and dialdehyde guar gum as raw materials through aqueous solution free radical polymerization and aldehyde-amine condensation reaction in sequence, so that the performance of the polymethacryloylhydrazone modified guar gum adsorption material in the aspect of heavy metal ion wastewater and dye wastewater treatment is more excellent.
The technical scheme is as follows: according to the invention, the preparation and application of the novel polymethacryloylhydrazone modified guar gum adsorbing material comprise the following steps:
A. weighing the components in a mass ratio of 1: 1, dissolving acrylic acid and methyl methacrylate in deionized water with a certain volume, adding a proper amount of sodium hydroxide solution, and stirring for 10 min; adding potassium persulfate serving as an initiator, stirring to dissolve the potassium persulfate, adding N' N-methylene bisacrylamide serving as a cross-linking agent, stirring to dissolve the potassium persulfate, reacting at 60-80 ℃ for 5-6 hours to obtain a crude hydrogel product, soaking the crude hydrogel product in absolute ethyl alcohol for 24 hours, drying at 40 ℃ in a vacuum drying oven for 24 hours, and grinding into powder to obtain a product A;
B. according to a molar ratio of 1: 2.5, weighing and placing the A with the corresponding mass in deionized water with a certain volume, mechanically stirring at a high speed for 1-3 h at the temperature of 60-80 ℃, adding hydrazine hydrate with the corresponding mass, mechanically stirring and reacting for 3-6 h at the temperature of 60-80 ℃, and treating a reaction solution with absolute ethyl alcohol to obtain a product B;
C. according to a molar ratio of 1:2, weighing the B with the corresponding mass, placing the B in absolute ethyl alcohol with a certain volume, stirring the mixture for about 1 hour at the temperature of 65-85 ℃, adding the dialdehyde guar gum with the corresponding mass, adding glacial acetic acid, reacting the mixture for 2-4 hours at the temperature of 65-85 ℃, and treating the reaction solution with the absolute ethyl alcohol to obtain a product C.
In an embodiment, in the step [0007] a, the solid content is 20%, and the weight ratio of 1: 1 of acrylic acid and methyl methacrylate was dissolved in 20mL of deionized water.
In the embodiment, the potassium persulfate initiator in the step [0007] A is used as an initiator, and the addition amount of the potassium persulfate initiator is 0.24-0.6 wt% of the total mass of the mixed solution; n 'N-methylene bisacrylamide is used as a cross-linking agent, and the addition amount of the N' N-methylene bisacrylamide is 0.05-0.2 wt% of the total mass of the mixed solution.
In an embodiment, the step [0007] A of soaking the crude hydrogel with absolute ethanol is to remove unreacted acrylic acid and methyl methacrylate small molecules.
In embodiments, the molar ratio of added A to hydrazine hydrate in step [0007] B is 1: 2.
In an embodiment, the step [0007] B comprises treating the reaction solution with absolute ethanol to precipitate the product B and remove unreacted small molecules.
In an embodiment, the dialdehyde guar in the reaction described in step [0007] C is self-made in the laboratory.
In embodiments, the molar ratio of addition B and dialdehyde guar in step [0007] C is 1: 2.
In embodiments, said C in step [0007] C adds glacial acetic acid as catalyst.
In the embodiment, the novel polymethacryloylhydrazone modified guar gum adsorbing material prepared in the step [0007] has more excellent performance in the aspects of heavy metal ion wastewater and dye wastewater treatment.
In an embodiment, step [0007]]The prepared novel polymethacryloylhydrazone modified guar gum adsorbing material is used for copper ions (Cu)2+) And the rapid and efficient treatment of Methylene Blue (MB) dye wastewater and Malachite Green (MG) dye wastewater.
The novel polymethacryloylhydrazone modified guar gum adsorbing material prepared by the invention has the effect of adsorbing copper ions (Cu)2+) The equilibrium adsorption capacity is 196MG/g, the equilibrium adsorption capacity of Methylene Blue (MB) dye wastewater is 1418.05MG/g, and the equilibrium adsorption capacity of Malachite Green (MG) dye wastewater is 1375.58 MG/g.
In the embodiment, all the medicines are analytically pure and are commercially available.
In the implementation scheme, the step [0007] is convenient to synthesize, the chemical technology used in the whole experimental process is the most common experimental operation, and the prepared novel polymethacryloylhydrazone modified guar gum adsorbing material has more excellent performance in the aspects of heavy metal ion wastewater and dye wastewater treatment, and is suitable for industrial production.
Drawings
Fig. 1 is a scanning electron microscope image of a novel polymethacryloylhydrazone modified guar gum adsorbing material.
Fig. 2 is a scanning electron microscope image of the novel polymethacryloylhydrazone-modified guar gum adsorbing material after adsorbing copper ions.
Fig. 3 is a scanning electron microscope image of Methylene Blue (MB) adsorbed by the novel polymethacryloylhydrazone-modified guar gum adsorbing material.
Fig. 4 is a scanning electron microscope image of Malachite Green (MG) adsorbed by the novel polymethacryloylhydrazone modified guar gum adsorbing material.
Detailed Description
The present invention will be described in detail below with reference to examples to enable those skilled in the art to better understand the present invention, but the present invention is not limited to the following examples.
Example 1
Preparation of product a:
weighing the components in a mass ratio of 1: 1, dissolving acrylic acid and methyl methacrylate in deionized water with a certain volume, adding a proper amount of sodium hydroxide solution, and stirring for 10 min; adding potassium persulfate serving as an initiator, stirring to dissolve the potassium persulfate, adding N' N-methylene bisacrylamide serving as a cross-linking agent, stirring to dissolve the potassium persulfate, reacting at 60-80 ℃ for 5-6 hours to obtain a crude hydrogel product, soaking the crude hydrogel product in absolute ethyl alcohol for 24 hours, drying at 40 ℃ in a vacuum drying oven for 24 hours, and grinding into powder to obtain a product A.
Example 2
Preparation of product B:
according to a molar ratio of 1: 2.5, weighing the corresponding mass of A, placing the A in deionized water with a certain volume, mechanically stirring the A at a high speed for 1-3 hours at the temperature of 60-80 ℃, adding the hydrazine hydrate with a corresponding mass, mechanically stirring the A and the hydrazine hydrate for reaction for 3-6 hours at the temperature of 60-80 ℃, and treating the reaction liquid with absolute ethyl alcohol to obtain a product B.
Example 3
Preparation of product C:
according to a molar ratio of 1:2, weighing the B with the corresponding mass, placing the B in absolute ethyl alcohol with a certain volume, stirring the mixture for about 1 hour at the temperature of 65-85 ℃, adding the dialdehyde guar gum with the corresponding mass, adding glacial acetic acid, reacting the mixture for 2-4 hours at the temperature of 65-85 ℃, and treating the reaction solution with the absolute ethyl alcohol to obtain a product C.
When the prepared polyacrylic acid modified saccharide macromolecular Schiff base compound is used for treating heavy metal ion wastewater and dye wastewater, the addition amount of the adsorbent is 0.01g, and the adsorbent can adsorb copper ions (Cu)2+) The equilibrium adsorption capacity is 196MG/g, the equilibrium adsorption capacity of Methylene Blue (MB) dye wastewater is 1418.05MG/g, and the equilibrium adsorption capacity of Malachite Green (MG) dye wastewater is 1375.58 MG/g.
Example 4
Preparation of product a:
weighing the components in a mass ratio of 1: 1, dissolving acrylic acid and methyl methacrylate in deionized water with a certain volume, adding a proper amount of sodium hydroxide solution, and stirring for 10 min; adding potassium persulfate serving as an initiator, stirring to dissolve the potassium persulfate, adding N' N-methylene bisacrylamide serving as a cross-linking agent, stirring to dissolve the potassium persulfate, reacting at 60-80 ℃ for 5-6 hours to obtain a crude hydrogel product, soaking the crude hydrogel product in absolute ethyl alcohol for 24 hours, drying at 40 ℃ in a vacuum drying oven for 24 hours, and grinding into powder to obtain a product A.
Example 5
Preparation of product B:
according to a molar ratio of 1: and 2, weighing the A and the hydrazine hydrate with corresponding mass, placing the A and the hydrazine hydrate into deionized water with a certain volume, mechanically stirring the mixture at the temperature of between 60 and 80 ℃ for reacting for 3 to 6 hours, and treating the reaction liquid with absolute ethyl alcohol to obtain a product B.
Example 6
Preparation of product C:
according to a molar ratio of 1: and 2, weighing the B and the dialdehyde guar gum with corresponding mass, placing the B and the dialdehyde guar gum into absolute ethyl alcohol with a certain volume, adding glacial acetic acid, reacting for 2-4 h at 65-85 ℃, and treating the reaction liquid with the absolute ethyl alcohol to obtain a product C.
When the prepared polyacrylic acid modified saccharide macromolecular Schiff base compound is used for treating heavy metal ion wastewater and dye wastewater, the addition amount of the adsorbent is 0.01g, and the adsorbent can adsorb copper ions (Cu)2+) The equilibrium adsorption amounts are respectively 103MG/g, the equilibrium adsorption amount of Methylene Blue (MB) dye wastewater is respectively 810.12MG/g, and the equilibrium adsorption amount of Malachite Green (MG) dye wastewater is respectively 769.81 MG/g.
Example 7
Preparation of product a:
weighing the components in a mass ratio of 1: 1, dissolving acrylic acid and methyl methacrylate in deionized water with a certain volume, adding a proper amount of sodium hydroxide solution, and stirring for 10 min; adding potassium persulfate serving as an initiator, stirring to dissolve the potassium persulfate, adding N' N-methylene bisacrylamide serving as a cross-linking agent, stirring to dissolve the potassium persulfate, reacting at 60-80 ℃ for 5-6 hours to obtain a crude hydrogel product, soaking the crude hydrogel product in absolute ethyl alcohol for 24 hours, drying at 40 ℃ in a vacuum drying oven for 24 hours, and grinding into powder to obtain a product A.
Example 8
Preparation of product B:
according to a molar ratio of 1: weighing corresponding mass of A and hydrazine hydrate, placing the A and the hydrazine hydrate into deionized water with a certain volume, mechanically stirring the mixture at the temperature of 60-80 ℃ for reaction for 3-6 hours, and treating the reaction solution with absolute ethyl alcohol to obtain a product B.
Example 9
Preparation of product C:
according to a molar ratio of 1: and 2, weighing the B and the dialdehyde guar gum with corresponding mass, placing the B and the dialdehyde guar gum into absolute ethyl alcohol with a certain volume, adding glacial acetic acid, reacting for 2-4 h at 65-85 ℃, and treating the reaction liquid with the absolute ethyl alcohol to obtain a product C.
When the prepared polyacrylic acid modified saccharide macromolecular Schiff base compound is used for treating heavy metal ion wastewater and dye wastewater, the addition amount of the adsorbent is 0.01g, and the adsorbent can adsorb copper ions (Cu)2+) The equilibrium adsorption amounts of the Methylene Blue (MB) dye wastewater and the Malachite Green (MG) dye wastewater are respectively 68MG/g, 681.26MG/g and 591.81MG/g respectively.
Example 10
Preparation of product a:
weighing the components in a mass ratio of 1: 1, dissolving acrylic acid and methyl methacrylate in deionized water with a certain volume, adding a proper amount of sodium hydroxide solution, and stirring for 10 min; adding potassium persulfate serving as an initiator, stirring to dissolve the potassium persulfate, adding N' N-methylene bisacrylamide serving as a cross-linking agent, stirring to dissolve the potassium persulfate, reacting at 60-80 ℃ for 5-6 hours to obtain a crude hydrogel product, soaking the crude hydrogel product in absolute ethyl alcohol for 24 hours, drying at 40 ℃ in a vacuum drying oven for 24 hours, and grinding into powder to obtain a product A.
Example 11
Preparation of product B:
according to a molar ratio of 1: weighing corresponding mass of A and hydrazine hydrate, placing the A and the hydrazine hydrate into deionized water with a certain volume, mechanically stirring the mixture at the temperature of 60-80 ℃ for reaction for 3-6 hours, and treating the reaction solution with absolute ethyl alcohol to obtain a product B.
Example 12
Preparation of product C:
according to a molar ratio of 1: and 2, weighing the B and the dialdehyde guar gum with corresponding mass, placing the B and the dialdehyde guar gum into absolute ethyl alcohol with a certain volume, adding glacial acetic acid, reacting for 2-4 h at 65-85 ℃, and treating the reaction liquid with the absolute ethyl alcohol to obtain a product C.
When the prepared polyacrylic acid modified saccharide macromolecular Schiff base compound is used for treating heavy metal ion wastewater and dye wastewater, the addition amount of the adsorbent is 0.01g, and the adsorbent can adsorb copper ions (Cu)2+) The equilibrium adsorption amounts of the Methylene Blue (MB) dye wastewater and the Malachite Green (MG) dye wastewater are respectively 73MG/g, 806.12MG/g and 689.46MG/g, respectively.
In fig. 1, the surface of the novel polymethacryloylhydrazone modified guar gum adsorbing material is in a very porous structure, so that the surface area is very large, more adsorption sites can be provided, and the adsorption process is facilitated.
In fig. 2, a scanning electron microscope image of the novel polymethacryloylhydrazone modified guar gum adsorbing material after adsorbing copper ions shows that the material of the present invention has a large specific surface area after adsorbing copper ions, and does not curl like other adsorbing materials after adsorbing metal ions, which indicates that the material of the present invention has good salt resistance and is also beneficial for performing a material repeatability experiment.
In fig. 3, a scanning electron microscope image of the novel polymethacryloylhydrazone modified guar gum adsorbing material adsorbing Methylene Blue (MB) shows that the methylene blue after adsorption can be well attached to the surface of the novel polymethacryloylhydrazone modified guar gum adsorbing material, and the porous structure before adsorption is covered to form a block-shaped body with a rough surface, which indicates that the material of the invention can well adsorb methylene blue dye wastewater.
In fig. 4, a scanning electron microscope image of the novel polymethacryloylhydrazone modified guar gum adsorbing material adsorbing Malachite Green (MG) shows that the malachite green after adsorption can be well attached to the surface of the novel polymethacryloylhydrazone modified guar gum adsorbing material, and the porous structure before adsorption is covered to form a relatively smooth block, which shows that the material of the present invention can well adsorb malachite green dye wastewater.
The above-described embodiments of the present invention should not be construed as limiting the scope of the present invention. Any other corresponding changes and modifications made according to the technical idea of the present invention should be included in the protection scope of the claims of the present invention.
Claims (9)
1. A preparation method of a polymethacrylhydrazone modified guar gum adsorbing material is characterized by comprising the following steps:
A. weighing the components in a mass ratio of 3: 1-1: 3, dissolving acrylic acid and methyl methacrylate in deionized water with a certain volume, adding a proper amount of sodium hydroxide solution, and stirring for 10 min; adding potassium persulfate serving as an initiator, stirring to dissolve the potassium persulfate, adding N' N-methylene bisacrylamide serving as a cross-linking agent, stirring to dissolve the potassium persulfate, reacting at 50-90 ℃ for 5-10 hours to obtain a crude hydrogel product, soaking the crude hydrogel product in absolute ethyl alcohol for 24 hours, drying at 40 ℃ in a vacuum drying oven for 24 hours, and grinding into powder to obtain a product A;
B. according to a molar ratio of 3: 1-1: 3, weighing and placing the A with the corresponding mass in deionized water with a certain volume, mechanically stirring the A at a high speed for 1-3 hours at the temperature of 50-90 ℃, adding hydrazine hydrate with the corresponding mass, mechanically stirring the A with the hydrazine hydrate at the temperature of 50-90 ℃ for reaction for 3-6 hours, and treating the reaction liquid with absolute ethyl alcohol to obtain a product B;
C. according to a molar ratio of 3: 1-1: and 3, weighing the B with the corresponding mass, placing the B in absolute ethyl alcohol with a certain volume, stirring for a certain time at 50-90 ℃, adding the dialdehyde guar gum with the corresponding mass, adding glacial acetic acid, reacting for 1-6 h at 50-90 ℃, and treating the reaction solution with the absolute ethyl alcohol to obtain a product C.
2. The method of claim 1, wherein: and step A, weighing the components in a mass ratio of 1: 1 of acrylic acid and methyl methacrylate was dissolved in 20mL of deionized water.
3. The method of claim 1, wherein: and step A, adding a sodium hydroxide solution, and adjusting the pH of the reaction system to 3-7.
4. The method of claim 1, wherein: step A, taking the potassium persulfate initiator as an initiator, wherein the addition amount of the potassium persulfate initiator is 0.1-0.8 wt% of the total mass of the mixed solution; n 'N-methylene bisacrylamide is used as a cross-linking agent, and the addition amount of the N' N-methylene bisacrylamide is 0.02-0.6 wt% of the total mass of the mixed solution.
5. The method of claim 1, wherein: the molar ratio of the added A and the hydrazine hydrate in the step B is 1: 2.
6. The method of claim 1, wherein: and D, preparing dialdehyde guar gum in the reaction in the step C, wherein the dialdehyde guar gum is prepared by a laboratory.
7. The method of claim 1, wherein: and C, adding B and dialdehyde guar gum at a molar ratio of 1: 2.
8. The method of claim 1, wherein: and C, adding glacial acetic acid as a catalyst.
9. The production method according to any one of claims 1 to 8, characterized in that: application of prepared polymethacryloylhydrazone modified guar gum adsorbing material to copper ions (Cu)2+) And treating Methylene Blue (MB) dye wastewater and Malachite Green (MG) dye wastewater.
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