CN110975836A - Shaddock peel adsorbent modified by 3-amino-5-mercapto-1, 2, 4-triazole and preparation method and application thereof - Google Patents
Shaddock peel adsorbent modified by 3-amino-5-mercapto-1, 2, 4-triazole and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a 3-amino-5-mercapto-1, 2, 4-triazole modified shaddock peel adsorbent and a preparation method and application thereof, and belongs to the field of adsorbent preparation. Firstly, drying shaddock peel, performing ball milling to obtain powder, and activating by concentrated sulfuric acid to obtain PP-SC. Then reacting with chloroacetyl chloride under anhydrous condition to obtain PP-CC. And finally, carrying out reflux reaction on PP-CC and 3-amino-5-mercapto-1, 2, 4-triazole to obtain the PP-ATT adsorbent. The preparation method of the adsorbent is simple and feasible, the operation is simple and convenient, and the raw materials are cheap and easy to obtain. The obtained novel shaddock peel modified material has high-efficiency and high-selectivity effects on removal of lead ions in an aqueous solution, and can be recycled. The invention provides a green and efficient adsorbent for treating the lead-containing wastewater, provides a method for recycling agricultural wastes, and brings a new idea for designing and synthesizing a novel adsorbent.
Description
Technical Field
The invention relates to a 3-amino-5-mercapto-1, 2, 4-triazole modified shaddock peel adsorbent, and a preparation method and application thereof, and belongs to the technical field of adsorbent preparation.
Background
Lead (Pb) has long been listed as one of the most harmful pollutants by the world health organization due to its high toxicity, carcinogenicity, bioaccumulation, and non-degradability. With the development of industries such as battery manufacturing, petroleum refining, mineral deposit smelting, coating production and the like, a large amount of lead ions enter a water circulation system, and great threat is caused to organisms. After entering the human body by sucking, lead can cause irreversible damage to nerves, reproduction, brain, kidney, liver and blood systems; even at lower levels, the effect is more severe. Therefore, effective measures are necessary to control lead contamination. Meanwhile, lead is widely used in industry due to its low melting point, corrosion resistance, and heavy plasticity. Therefore, the recovery of lead is also an important issue in the field of engineering for environmental and materials. At present, the main lead removal methods include precipitation, biological, electrochemical, ion exchange and adsorption. The chemical precipitation method can generate secondary pollution and has poor selectivity; biological methods are limited by the fact that specialized microorganisms are few in species and short in life; ion exchange methods and electrochemical methods are relatively costly and have poor reproducibility. The adsorption method is considered to be one of the most effective methods due to the advantages of simple operation, repeatability, selectivity, no secondary pollution and the like. The common adsorbents include activated carbon, resin, natural minerals, agricultural and sideline products, silicon dioxide and the like. The shaddock peel is agricultural waste, and is usually treated by landfill and incineration, so that resource waste and environmental pollution are caused. However, the shaddock peel is rich in amino and hydroxyl and is a post-modified high-quality low-cost material.
Disclosure of Invention
Aiming at the problems and the defects in the prior art, the invention aims to provide a preparation method and application of a 3-amino-5-mercapto-1, 2, 4-triazole modified shaddock peel adsorbent. The modified shaddock peel adsorbent can be used for selectively removing lead ions in an acidic aqueous solution, is low in material cost, simple in synthesis process, easy to separate from the aqueous solution, high in adsorption capacity and reusable.
The invention is realized by the following technical scheme:
a3-amino-5-mercapto-1, 2, 4-triazole modified shaddock peel adsorbent has a structural formula shown in formula (I):
wherein
Is a shaddock peel schematic structure with exposed hydroxyl/amino after being activated by concentrated sulfuric acid;
r is:
the invention also aims to provide a preparation method of the shaddock peel adsorbent modified by 3-amino-5-mercapto-1, 2, 4-triazole, which comprises the following steps:
(1) cutting the pomelo peel into small pieces, drying, and grinding into powder by using a small ball mill; the preparation method comprises the steps of putting shaddock peel powder into a beaker, adding 98 wt% concentrated sulfuric acid for pretreatment, transferring the shaddock peel powder into a round-bottom three-neck flask, performing reflux stirring and activation treatment at 100 ℃ to expose surface functional groups, performing liquid-solid separation after reflux, washing the obtained solid to be neutral by deionized water, and drying to obtain a product PP-SC, wherein the reaction flow is shown in figure 1.
(2) In an anhydrous environment, sequentially adding the PP-SC product obtained in the step (1) and chloroacetyl chloride into an N, N-dimethylformamide solution for reflux reaction, performing liquid-solid separation, washing the obtained solid with the N, N-dimethylformamide solution, centrifuging, and performing vacuum drying to obtain a product PP-CC; the reaction route is as follows:
(3) under the protection of nitrogen, sequentially adding the PP-CC product obtained in the step (2) and 3-amino-5-mercapto-1, 2, 4-triazole into N, N-dimethylformamide for reflux reaction, carrying out liquid-solid separation, washing the obtained solid with N, N-dimethylformamide, and carrying out vacuum drying to obtain a PP-ATT product; the synthesis route is as follows:
preferably, in the above production method: in the step (1), the liquid-solid ratio of the concentrated sulfuric acid to the shaddock peel powder is 3: 1-7: 1 mL/g.
Preferably, in the above production method: in the step (2), the liquid-solid ratio of the N, N-dimethylformamide to the PP-SC is 30: 1-50: 1mL/g, and the liquid-solid ratio of the chloroacetyl chloride to the PP-SC is 5: 3-10: 3.
Preferably, in the above production method: in the step (3), the liquid-solid ratio of the N, N-dimethylformamide to the PP-CC is 40: 1-56: 1mL/g, and the mass ratio of the 3-amino-5-mercapto-124 triazole to the PP-CC is 2: 5-1: 1.
Preferably, in the above production method: in the step (1), the reflux is carried out for 5-15 h at 50-100 ℃; in the step (2), the reflux is carried out for 12-24 h at the temperature of 80-100 ℃; in the step (3), the reflux is carried out for 12-24 hours at the temperature of 45-85 ℃.
The 3-amino-5-mercapto-1, 2, 4-triazole modified shaddock peel adsorbent is applied to selective adsorption removal of lead ions in an acidic aqueous solution.
The organic and inorganic reagents were commercially available analytical grade.
Compared with the prior art, the invention has the following beneficial effects:
(1) the 3-amino-5-mercapto-1, 2, 4-triazole modified shaddock peel adsorbent has good selectivity, high adsorption quantity and excellent removal rate on lead ion adsorption.
(2) The adsorbent of the invention has simple preparation process, easy synthesis and low cost of raw materials.
(3) The 3-amino-5-mercapto-1, 2,4 triazole modified shaddock peel adsorbent is non-toxic, stable in performance, easy to separate, reusable and free of secondary pollution to the environment.
(4) The modified shaddock peel adsorbent has good economic and practical values. Has great popularization potential in the aspects of selective removal and recovery of lead ions in aqueous solution.
Drawings
FIG. 1 is a schematic view of the reaction scheme of step (1).
Detailed Description
The present invention will be further described with reference to the following embodiments.
Example 1:
the 3-amino-5-mercapto-1, 2, 4-triazole modified shaddock peel adsorbent has a structural formula as follows:
wherein
Is a shaddock peel schematic structure with exposed hydroxyl/amino after being activated by concentrated sulfuric acid;
r is:
the preparation method of the 3-amino-5-mercapto-1, 2, 4-triazole modified shaddock peel adsorbent comprises the following specific steps:
(1) cutting pericarpium Citri Grandis into pieces of about 1cm, oven drying, and grinding into powder with small ball mill. Taking 10g of shaddock peel powder into a 1L beaker, adding 98 wt% concentrated sulfuric acid according to the liquid-solid ratio of 3:7 of concentrated sulfuric acid to the shaddock peel powder, pretreating for 3h, transferring the mixture into a round-bottom three-neck flask, refluxing for 5h at 50 ℃ to activate surface functional groups, carrying out liquid-solid separation after the reaction is finished, washing the obtained solid to be neutral by deionized water, and carrying out centrifugal drying to obtain a product PP-SC; the reaction scheme is shown in FIG. 1.
(2) Under an anhydrous environment, uniformly mixing an N, N-dimethylformamide solution and PP-SC according to a liquid-solid ratio of 30:1mL/g, adding chloroacetyl chloride according to a liquid-solid ratio of 5:3 of chloroacetyl chloride to PP-SC, carrying out reflux reaction for 12h at the temperature of 80 ℃, carrying out liquid-solid separation, washing and centrifuging the obtained solid by using N, N-dimethylformamide, and carrying out vacuum drying to obtain a product PP-CC; the synthetic route is as follows:
(3) under the nitrogen protection environment, uniformly mixing PP-CC obtained in the step (2) with N, N-dimethylformamide according to the solid-to-liquid ratio of 1:40g/mL, adding 3-amino-5-mercapto-1, 2, 4-triazole according to the mass ratio of 3-amino-5-mercapto-1, 2, 4-triazole to PP-CC of 2:5, carrying out reflux reaction for 12 hours at 45 ℃, carrying out liquid-solid separation, washing the obtained solid with N, N-dimethylformamide, centrifuging and drying to obtain a product PP-ATT; the synthetic route is as follows:
and (3) measuring the lead ion adsorption performance:
10mg of PP-ATT in the example is put into a lead ion solution with the initial concentration of 200mg/L for oscillation adsorption for 2h, centrifugal separation is carried out, the concentration of the residual lead ions in the supernatant is measured by ICP-OES to be 19.7mg/L, and the adsorption rate is 90.15%. Desorbing the bottom layer solid with thiourea solution (10 wt%) for 12h, washing for 3 times, drying at 65 deg.C for 24h, adding into 200mg/L lead ion solution again, shaking for adsorption for 2h, centrifuging, and measuring the residual lead ion concentration in the supernatant to be 23.12mg/L and the adsorption rate to be 88.44%. The 3-amino-5-mercapto-1, 2, 4-triazole modified shaddock peel adsorbent PP-ATT can be repeatedly used for removing lead ions in an aqueous solution.
Example 2:
the 3-amino-5-mercapto-1, 2, 4-triazole modified shaddock peel adsorbent has a structural formula as follows:
wherein
Is a shaddock peel schematic structure with exposed hydroxyl/amino after being activated by concentrated sulfuric acid;
r is：
The preparation method of the 3-amino-5-mercapto-1, 2, 4-triazole modified shaddock peel adsorbent comprises the following specific steps:
(1) cutting pericarpium Citri Grandis into pieces of about 1cm, oven drying, and grinding into powder with small ball mill. Putting 10g of shaddock peel powder into a 1L beaker, adding 98 wt% concentrated sulfuric acid according to the liquid-solid ratio of 5:7 of concentrated sulfuric acid to the shaddock peel powder, pretreating for 3h, transferring the mixture into a round-bottom three-neck flask, refluxing for 10h at 75 ℃ to activate surface functional groups, carrying out liquid-solid separation after the reaction is finished, washing the obtained solid to be neutral by deionized water, and drying to obtain a product PP-SC; the reaction scheme is shown in figure 1
(2) Under an anhydrous environment, uniformly mixing an N, N-dimethylformamide solution and PP-SC according to a liquid-solid ratio of 40:1mL/g, adding chloroacetyl chloride according to a liquid-solid ratio of 5:2 of chloroacetyl chloride to PP-SC, carrying out reflux reaction for 18h at 90 ℃, carrying out liquid-solid separation, washing the obtained solid with N, N-dimethylformamide, centrifuging, and carrying out vacuum drying to obtain a product PP-CC; the synthetic route is as follows:
(3) under the nitrogen protection environment, uniformly mixing PP-CC obtained in the step (2) with N, N-dimethylformamide according to the solid-liquid ratio of 1:48g/mL, adding 3-amino-5-mercapto-1, 2, 4-triazole according to the mass ratio of 7:10 of 3-amino-5-mercapto-1, 2, 4-triazole to PP-CC, carrying out reflux reaction at 85 ℃ for 18h, carrying out liquid-solid separation, washing the obtained solid with N, N-dimethylformamide, centrifuging and drying to obtain a product PP-ATT; the synthetic route is as follows:
and (3) measuring the lead ion adsorption performance:
10mg of PP-ATT adsorbent in the example is put into a lead ion solution with the initial concentration of 200mg/L for oscillation adsorption for 2h, centrifugal separation is carried out, the concentration of the residual lead ions in the supernatant is measured by ICP-OES to be 13.34mg/L, and the adsorption rate is 93.33%. Desorbing the bottom layer solid with thiourea solution (10 wt%) for 12h, washing, drying at 65 deg.C for 24h, adding into 200mg/L lead ion solution again, shaking for 2h, centrifuging, and measuring the residual lead ion concentration in the supernatant as 16.38mg/L and the adsorption rate as 91.81%. The 3-amino-5-mercapto-1, 2, 4-triazole modified shaddock peel adsorbent PP-ATT can be repeatedly used for removing lead ions in an aqueous solution.
Example 3:
the 3-amino-5-mercapto-1, 2, 4-triazole modified shaddock peel adsorbent has a structural formula as follows:
wherein
Is a shaddock peel schematic structure with exposed hydroxyl/amino after being activated by concentrated sulfuric acid;
r is:
the preparation method of the 3-amino-5-mercapto-1, 2, 4-triazole modified shaddock peel adsorbent comprises the following specific steps:
(1) cutting pericarpium Citri Grandis into pieces of about 1cm, oven drying, and grinding into powder with small ball mill. 10g of shaddock peel powder is taken to be put into a 1L beaker, and 98 wt% concentrated sulfuric acid is added according to the liquid-solid ratio of concentrated sulfuric acid to shaddock peel powder of 7:1 for pretreatment for 3 hours. Transferring the mixture into a round bottom three-neck flask, refluxing for 15h at 100 ℃ to activate surface functional groups, carrying out liquid-solid separation after the reaction is finished, washing the obtained solid to be neutral by using deionized water, and drying to obtain a product PP-SC; the reaction scheme is shown in FIG. 1.
(2) Under an anhydrous environment, uniformly mixing an N, N-dimethylformamide solution and PP-SC according to a liquid-solid ratio of 50:1mL/g, adding chloroacetyl chloride according to a liquid-solid ratio of 10:3 of chloroacetyl chloride to PP-SC, carrying out reflux reaction for 24 hours at 100 ℃, carrying out liquid-solid separation, washing the obtained solid with N, N-dimethylformamide, centrifuging, and carrying out vacuum drying to obtain a product PP-CC; the specific synthetic route is as follows:
(3) under the nitrogen protection environment, uniformly mixing PP-CC obtained in the step (2) with N, N-dimethylformamide according to the solid-to-liquid ratio of 1:56g/mL, adding 3-amino-5-mercapto-1, 2, 4-triazole according to the mass ratio of 1:1 of 3-amino-5-mercapto-1, 2, 4-triazole to PP-CC, carrying out reflux reaction at 65 ℃ for 24 hours, carrying out liquid-solid separation, washing the obtained solid with N, N-dimethylformamide, centrifuging and drying to obtain a product PP-ATT; the specific synthetic route is as follows:
and (3) measuring the lead ion adsorption performance:
10mg of PP-ATT adsorbent in the embodiment is put into a lead ion solution with the initial concentration of 200mg/L for oscillation adsorption for 2h, centrifugal separation is carried out, the concentration of the residual lead ions in the supernatant is measured by ICP-OES to be 2.04mg/L, and the adsorption rate is 98.98%. Desorbing the bottom layer solid with thiourea solution (10 wt%) for 12h, centrifuging, washing, drying at 65 deg.C for 24h, adding into 200mg/L lead ion solution, shaking for 2h, centrifuging, and measuring the residual lead ion concentration in the supernatant to be 3.57mg/L and the adsorption rate to be 98.22%. The 3-amino-5-mercapto-1, 2, 4-triazole modified shaddock peel adsorbent PP-ATT can be repeatedly used for removing lead ions in an aqueous solution.
While the present invention has been described in detail with reference to the specific embodiments thereof, the present invention is not limited to the embodiments described above, and various changes can be made without departing from the spirit of the present invention within the knowledge of those skilled in the art.
Claims (7)
1. The 3-amino-5-mercapto-1, 2, 4-triazole modified shaddock peel adsorbent is characterized in that the structural formula is shown as the formula (I):
wherein
Is a shaddock peel schematic structure with exposed hydroxyl/amino after being activated by concentrated sulfuric acid;
r is:
2. the preparation method of the 3-amino-5-mercapto-1, 2, 4-triazole modified shaddock peel adsorbent as claimed in claim 1, is characterized by comprising the following steps:
(1) cutting the pomelo peel into small pieces, drying, and grinding into powder by using a small ball mill; putting the shaddock peel powder into a beaker, adding 98 wt% concentrated sulfuric acid for pretreatment, transferring the shaddock peel powder to a round-bottom three-neck flask, performing reflux stirring and activation treatment at 100 ℃ to expose surface functional groups, performing liquid-solid separation after reflux, washing the obtained solid to be neutral by using deionized water, and drying to obtain a product PP-SC;
(2) in an anhydrous environment, sequentially adding the PP-SC product obtained in the step (1) and chloroacetyl chloride into an N, N-dimethylformamide solution for reflux reaction, performing liquid-solid separation, washing the obtained solid with the N, N-dimethylformamide solution, centrifuging, and performing vacuum drying to obtain a product PP-CC;
(3) and (3) under the protection of nitrogen, sequentially adding the PP-CC product obtained in the step (2) and 3-amino-5-mercapto-1, 2, 4-triazole into N, N-dimethylformamide for reflux reaction, carrying out liquid-solid separation, washing the obtained solid with N, N-dimethylformamide, and carrying out vacuum drying to obtain the PP-ATT product.
3. The method of claim 2, wherein: in the step (1), the liquid-solid ratio of the concentrated sulfuric acid to the shaddock peel powder is 3: 1-7: 1 mL/g.
4. The method of claim 2, wherein: in the step (2), the liquid-solid ratio of the N, N-dimethylformamide to the PP-SC is 30: 1-50: 1mL/g, and the liquid-solid ratio of the chloroacetyl chloride to the PP-SC is 5: 3-10: 3.
5. The method of claim 2, wherein: in the step (3), the liquid-solid ratio of the N, N-dimethylformamide to the PP-CC is 40: 1-56: 1mL/g, and the mass ratio of the 3-amino-5-mercapto-1, 2, 4-triazole to the PP-CC is 2: 5-1: 1.
6. The method of claim 2, wherein: the reflux in the step (1) is carried out for 5-15 h at the temperature of 50-100 ℃; the reflux in the step (2) is carried out for 12-24 h at the temperature of 80-100 ℃; in the step (3), the reflux is carried out for 12-24 h at the temperature of 45-85 ℃.
7. The application of the 3-amino-5-mercapto-1, 2, 4-triazole modified pomelo peel adsorbent in claim 1 in selective adsorption and removal of lead ions in acidic aqueous solution.
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