CN110813248B - O-dihydroxybenzaldehyde modified shaddock peel adsorbent and preparation method and application thereof - Google Patents

O-dihydroxybenzaldehyde modified shaddock peel adsorbent and preparation method and application thereof Download PDF

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CN110813248B
CN110813248B CN201911123729.7A CN201911123729A CN110813248B CN 110813248 B CN110813248 B CN 110813248B CN 201911123729 A CN201911123729 A CN 201911123729A CN 110813248 B CN110813248 B CN 110813248B
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shaddock peel
solid
dimethylformamide
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dihydroxybenzaldehyde
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薛灿
纪红兵
熊超
王仕兴
周贤太
杨祖金
王永庆
胡鹏
黄丽云
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Sun Yat Sen 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
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    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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    • 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
    • C02F1/286—Treatment of water, waste water, or sewage by sorption using natural organic sorbents or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
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Abstract

The invention discloses an o-dihydroxybenzaldehyde modified shaddock peel adsorbent, and a preparation method and application thereof. The pomelo peel is dried, ground and carbonized to obtain a product PP-SC, then the product PP-SC is reacted with chloroacetyl chloride to obtain PP-CC, the PP-CC is further reacted with triethylene tetramine in a refluxing way to prepare PP-TT, and finally the PP-TT and o-dihydroxy benzaldehyde are refluxed in ethanol to obtain a final product PP-DBD. The method is simple to operate, the raw material of the shaddock peel and various reagents are cheap and easy to obtain, the obtained novel shaddock peel modified material has high-flux and high-selectivity adsorption effect on lead ions, a green and efficient adsorption material is provided for treating lead-containing sewage, and meanwhile, the use of agricultural waste shaddock peel also brings a new idea for the design and synthesis of the novel adsorption material.

Description

O-dihydroxybenzaldehyde modified shaddock peel adsorbent and preparation method and application thereof
Technical Field
The invention relates to an o-dihydroxybenzaldehyde modified shaddock peel adsorbent as well as a preparation method and application thereof, belonging to the technical field of adsorbent preparation.
Background
With the development of industries such as battery manufacturing, petroleum refining, mineral production and the like, a large amount of toxic heavy metal ions enter a water circulation system (surface water and underground water) and possibly further enter organisms. Lead is listed in the list of toxic and harmful water pollutants because of its properties of being extremely toxic, bioaccumulation, and difficult to degrade (7 months in 2019, first batch). Even at lower levels, lead causes irreversible damage to the human nervous, intellectual, reproductive, and blood systems. Meanwhile, lead has the advantages of low melting point, high corrosion resistance, high plasticity and the like, so that the lead is widely applied to a plurality of industrial fields. Therefore, selective removal and recycling of lead ions from aqueous solutions is an important issue for research in engineering fields such as environment and materials. At present, the main lead removal methods include precipitation, biological, electrochemical, ion exchange and adsorption. Wherein, the precipitate generated by the chemical precipitation method is difficult to treat, has poor selectivity and can cause secondary pollution; the biological method has fewer special microorganism species for adsorbing the lead ions, and the species competition of the microorganism has no advantages and short service life; the ion exchange method and the electrochemical method have relatively high cost and poor reusability. The adsorption enrichment method is considered as the most effective method for removing the lead ions due to the advantages of simple operation, regenerable adsorbent, good 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 an agricultural waste, and the common treatment is landfill and incineration disposal, which causes resource waste and environmental pollution. The surface of the shaddock peel has a large number of active sites such as amino, hydroxyl and the like, and is a post-modified material with high quality, environmental protection, greenness and low cost.
Disclosure of Invention
Aiming at the problems and the defects in the prior art, the invention provides an o-dihydroxybenzaldehyde modified shaddock peel adsorbent and a preparation method and an application thereof. The o-dihydroxybenzaldehyde modified shaddock peel adsorbent can be used for selective adsorption removal of lead ions in an acidic aqueous solution, and is low in material cost, simple in synthesis process, easy to separate from the aqueous solution, high in adsorbability and reusable.
The invention is realized by the following technical scheme.
An o-dihydroxybenzaldehyde modified shaddock peel adsorbent has a structural formula as follows:
Figure BDA0002276181410000021
wherein
Figure BDA0002276181410000022
Is concentrated sulfuric acidAfter treatment, the shaddock peel structure with surface hydroxyl and amino groups is exposed;
m is:
Figure BDA0002276181410000023
the preparation method of the o-dihydroxybenzaldehyde modified shaddock peel adsorbent comprises the following steps of:
(1) Drying the shaddock peel, grinding the shaddock peel into powder by using a small ball mill, adding the powder into concentrated sulfuric acid for carbonization treatment to expose surface functional groups, performing liquid-solid separation after reflux reaction, washing the obtained solid to be neutral by using deionized water, and drying to obtain a product PP-SC;
(2) Under an anhydrous environment, sequentially adding the product PP-SC obtained in the step (1) and chloroacetyl chloride into N, N-dimethylformamide for refluxing, performing liquid-solid separation, washing the solid with the N, N-dimethylformamide, centrifuging, and performing vacuum drying to obtain a product PP-CC; the synthetic route is as follows:
Figure BDA0002276181410000024
(3) Sequentially adding the products PP-CC and triethylene tetramine obtained in the step (2) into N, N-dimethylformamide for reflux reaction, then carrying out liquid-solid separation, washing the solid with the N, N-dimethylformamide, centrifuging and drying to obtain a product PP-TT; the synthesis route is as follows:
Figure BDA0002276181410000031
(4) Adding the product PP-TT and o-dihydroxy benzaldehyde obtained in the step (3) into absolute ethyl alcohol for reflux reaction, performing liquid-solid separation, washing the solid with absolute ethyl alcohol, centrifuging, and drying to obtain the o-dihydroxy benzaldehyde modified shaddock ped adsorbent PP-DBD, wherein the synthetic route is as follows:
Figure BDA0002276181410000032
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 5-1 mL/g.
Preferably, in the above preparation method: in the step (2), the liquid-solid ratio of the N, N-dimethylformamide to the PP-SC is 20-40, and the volume ratio of the chloroacetyl chloride to the N, N-dimethylformamide is 1-15.
Preferably, in the above production method: in the step (3), the liquid-solid ratio of the N, N-dimethylformamide to the PP-CC is 30-40.
Preferably, in the above production method: the liquid-solid ratio of the absolute ethyl alcohol to the PP-TT in the step (4) is 40-56, and the mass ratio of the PP-TT to the o-dihydroxybenzaldehyde is 0.8.
Preferably, in the above preparation method: in the step (1), the reflux is carried out for 12 to 24 hours at the temperature of between 60 and 100 ℃; in the step (2), the reflux is carried out for 12 to 36 hours at the temperature of between 80 and 100 ℃; in the step (3), the reflux is performed for 12 to 36 hours at a temperature of between 70 and 90 ℃; in the step (4), the reflux is carried out for 12 to 36 hours at the temperature of between 55 and 75 ℃.
The o-dihydroxybenzaldehyde modified shaddock peel adsorbent is applied to selective adsorption and removal of lead ions in an acidic aqueous solution.
The organic and inorganic reagents were commercially available analytical reagents.
Compared with the prior art, the invention has the following beneficial effects:
(1) The o-dihydroxybenzaldehyde modified shaddock peel adsorbent has high adsorption capacity and adsorption rate on lead ions.
(2) The adsorbent of the invention has simple preparation process, easy synthesis and low cost of raw materials.
(3) The o-dihydroxybenzaldehyde modified shaddock peel adsorbent disclosed by the invention 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 use values. Has great popularization potential in the selective removal and recovery of lead ions.
Detailed Description
The present invention will be further described with reference to the following embodiments.
Example 1:
the o-dihydroxybenzaldehyde modified shaddock peel adsorbent has the structural formula as follows:
Figure BDA0002276181410000041
wherein
Figure BDA0002276181410000042
The shaddock peel schematic structure is a shaddock peel schematic structure with exposed surface hydroxyl and amino after concentrated sulfuric acid treatment;
m is:
Figure BDA0002276181410000043
the preparation method of the o-dihydroxybenzaldehyde modified shaddock peel adsorbent comprises the following specific steps:
(1) Firstly, drying the shaddock peel, grinding the dried shaddock peel into powder by using a small ball mill, then adding the shaddock peel powder into concentrated sulfuric acid (98 wt%) according to the liquid-solid ratio of the concentrated sulfuric acid to the shaddock peel powder of 5mL/g, carbonizing the mixture at 60 ℃ for 12h to expose surface functional groups, carrying out liquid-solid separation after reflux reaction, washing the obtained solid to be neutral by using deionized water, and drying to obtain a product PP-SC.
(2) Under an anhydrous environment, uniformly mixing N, N-dimethylformamide and PP-SC according to a liquid-solid ratio of 20 mL/g, adding chloroacetyl chloride according to a volume ratio of chloroacetyl chloride to N, N-dimethylformamide of 1; the specific synthetic route is as follows:
Figure BDA0002276181410000051
(3) Uniformly mixing PP-CC and N, N-dimethylformamide obtained in the step (2) according to a solid-liquid ratio of 1; the specific synthetic route is as follows:
Figure BDA0002276181410000052
(4) Uniformly mixing the PP-TT obtained in the step (3) with absolute ethyl alcohol according to a solid-liquid ratio of 1; the specific synthetic route is as follows:
Figure BDA0002276181410000053
and (3) measuring the lead ion adsorption performance:
10mg of PP-DBD is put into a lead ion solution with the initial concentration of 200mg/L for oscillation and adsorption for 2h, then centrifugation is carried out, the concentration of the residual lead ions in the supernatant is measured by ICP-OES to be 16.6mg/L, and the adsorption rate is 91.7%. Stirring and desorbing the adsorbent after adsorbing the lead ions in a thiourea solution (10 wt%) for 12h, washing with deionized water for 5 times, and finally drying the adsorbent at 65 ℃ for 24h. And putting the dried adsorbent into the lead ion solution with the initial concentration of 200mg/L again, oscillating and adsorbing for 2h, centrifuging, and measuring the concentration of the residual lead ions in the supernatant to be 20.9mg/L by utilizing ICP-OES, wherein the adsorption rate is 89.6%. The o-dihydroxybenzaldehyde modified shaddock peel adsorbent PP-DBD can be used for removing lead ions and can be recycled.
Example 2:
the o-dihydroxybenzaldehyde modified shaddock peel adsorbent has the structural formula as follows:
Figure BDA0002276181410000061
wherein
Figure BDA0002276181410000062
The shaddock peel schematic structure is a shaddock peel schematic structure with exposed surface hydroxyl and amino after concentrated sulfuric acid treatment;
m is:
Figure BDA0002276181410000063
the preparation method of the o-dihydroxybenzaldehyde modified shaddock peel adsorbent comprises the following specific steps:
(1) Firstly, drying the shaddock peel, grinding the dried shaddock peel into powder by using a small ball mill, then adding the shaddock peel powder into concentrated sulfuric acid (98 wt%) according to the liquid-solid ratio of the concentrated sulfuric acid to the shaddock peel powder of 6 mL/g, carbonizing the mixture at 80 ℃ for 18h to expose surface functional groups, carrying out liquid-solid separation after reflux reaction, washing the obtained solid sample to be neutral by using deionized water, and drying the solid sample to obtain a product PP-SC.
(2) Under an anhydrous environment, uniformly mixing N, N-dimethylformamide and PP-SC according to a liquid-solid ratio of 30:1mL/g, adding chloroacetyl chloride according to a volume ratio of 1; the specific synthetic route is as follows:
Figure BDA0002276181410000064
(3) Uniformly mixing PP-CC and N, N-dimethylformamide obtained in the step (2) according to a solid-liquid ratio of 1; the specific synthetic route is as follows:
Figure BDA0002276181410000071
(4) Uniformly mixing PP-TT obtained in the step (3) and absolute ethyl alcohol according to a solid-liquid ratio of 1; the specific synthetic route is as follows:
Figure BDA0002276181410000072
and (3) measuring the lead ion adsorption performance:
10mg of PP-DBD is put into a lead ion solution with the initial concentration of 200mg/L for oscillation and adsorption for 2h, then centrifugation is carried out, the concentration of the residual lead ions in the supernatant is measured to be 13.1mg/L by ICP-OES, and the adsorption rate is 93.5%. Stirring and desorbing the adsorbent after adsorbing the lead ions in a thiourea solution (10 wt%) for 12h, washing with deionized water for 5 times, and finally drying the adsorbent at 65 ℃ for 24h. The dried adsorbent was again put into a lead ion solution having an initial concentration of 200mg/L, shaken and adsorbed for 2 hours, and then centrifuged, and the remaining lead ion concentration in the supernatant was measured by ICP-OES as 15.8mg/L, with an adsorption rate of 92.1%. The o-dihydroxybenzaldehyde modified shaddock peel adsorbent PP-DBD can be used for removing lead ions and can be recycled.
Example 3:
the o-dihydroxybenzaldehyde modified shaddock peel adsorbent has the structural formula as follows:
Figure BDA0002276181410000073
wherein
Figure BDA0002276181410000081
Pomelo with exposed surface hydroxyl and amino groups for concentrated sulfuric acid treatmentThe structure of the leather is shown schematically, and the leather is shown schematically,
m is:
Figure BDA0002276181410000082
the preparation method of the o-dihydroxybenzaldehyde modified shaddock peel adsorbent comprises the following specific steps:
(1) Firstly, drying the shaddock peel, grinding the dried shaddock peel into powder by using a small ball mill, then adding the shaddock peel powder into concentrated sulfuric acid (98 wt%) according to a liquid-solid ratio of the concentrated sulfuric acid to the shaddock peel powder of 7 mL/g, carrying out carbonization treatment for 24h at 100 ℃ to expose surface functional groups, carrying out liquid-solid separation after reflux reaction, washing an obtained solid sample to be neutral by using deionized water, and drying to obtain a product PP-SC.
(2) Under an anhydrous environment, uniformly mixing N, N-dimethylformamide and PP-SC according to a liquid-solid ratio of 40; the specific synthetic route is as follows:
Figure BDA0002276181410000083
(3) Uniformly mixing PP-CC and N, N-dimethylformamide obtained in the step (2) according to a solid-liquid ratio of 1; the specific synthetic route is as follows:
Figure BDA0002276181410000084
(4) Uniformly mixing PP-TT obtained in the step (3) and absolute ethyl alcohol according to a solid-liquid ratio of 1; the specific synthetic route is as follows:
Figure BDA0002276181410000091
and (3) measuring the lead ion adsorption performance:
10mg of PP-DBD is put into a lead ion solution with the initial concentration of 200mg/L for oscillation adsorption for 2h, centrifugation is carried out, the concentration of the residual lead ions in the supernatant is measured by ICP-OES to be 3.1mg/L, and the adsorption rate is 98.5%. Stirring and desorbing the adsorbent after adsorbing the lead ions in a thiourea solution (10 wt%) for 12h, washing with deionized water for 5 times, and finally drying the adsorbent at 65 ℃ for 24h. And (3) putting the dried adsorbent into the lead ion solution with the initial concentration of 200mg/L again, oscillating and adsorbing for 2h, centrifuging, and measuring the concentration of the residual lead ions in the supernatant to be 5.3mg/L by utilizing ICP-OES, wherein the adsorption rate is 97.4%. The o-dihydroxybenzaldehyde modified shaddock peel adsorbent PP-DBD can be used for removing lead ions and can be recycled.
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 preparation method of the o-dihydroxybenzaldehyde modified shaddock peel adsorbent for adsorbing lead ions is characterized in that the structural formula is as follows:
Figure FDA0003886521690000011
wherein
Figure FDA0003886521690000012
The shaddock peel structure is a shaddock peel structure with exposed surface hydroxyl and amino after concentrated sulfuric acid treatment;
m is:
Figure FDA0003886521690000013
the preparation method comprises the following steps:
(1) Drying the shaddock peel, grinding the shaddock peel into powder by using a small ball mill, adding the powder into concentrated sulfuric acid for carbonization treatment to expose surface functional groups, performing liquid-solid separation after reflux reaction, washing the obtained solid to be neutral by using deionized water, and drying to obtain a product PP-SC;
(2) Under an anhydrous environment, sequentially adding the product PP-SC obtained in the step (1) and chloroacetyl chloride into N, N-dimethylformamide for refluxing, performing liquid-solid separation, washing the solid with the N, N-dimethylformamide, centrifuging, and performing vacuum drying to obtain a product PP-CC; the synthetic route is as follows:
Figure FDA0003886521690000014
(3) Sequentially adding the products PP-CC and triethylene tetramine obtained in the step (2) into N, N-dimethylformamide for reflux reaction, then carrying out liquid-solid separation, washing the solid with the N, N-dimethylformamide, centrifuging and drying to obtain a product PP-TT; the synthesis route is as follows:
Figure FDA0003886521690000021
(4) Adding the product PP-TT and o-dihydroxy benzaldehyde obtained in the step (3) into absolute ethyl alcohol for reflux reaction, then carrying out liquid-solid separation, washing the solid with absolute ethyl alcohol, centrifuging, and drying to obtain the o-dihydroxy benzaldehyde modified shaddock ped adsorbent PP-DBD, wherein the synthetic route is as follows:
Figure FDA0003886521690000022
2. the method of claim 1, wherein: in the step (1), the liquid-solid ratio of the concentrated sulfuric acid to the shaddock peel powder is 5-1 mL/g.
3. The method of claim 1, wherein: in the step (2), the liquid-solid ratio of the N, N-dimethylformamide to the PP-SC is 20-40, and the volume ratio of the chloroacetyl chloride to the N, N-dimethylformamide is 1-15.
4. The method of claim 1, wherein: in the step (3), the liquid-solid ratio of the N, N-dimethylformamide to the PP-CC is 30-40, and the volume ratio of the triethylene tetramine to the N, N-dimethylformamide is 2-5.
5. The method of claim 1, wherein: the liquid-solid ratio of the absolute ethyl alcohol to the PP-TT in the step (4) is 40-56, and the mass ratio of the PP-TT to the o-dihydroxybenzaldehyde is 0.8.
6. The production method according to claim 1, characterized in that: in the step (1), the reflux is carried out for 12 to 24 hours at the temperature of between 60 and 100 ℃; in the step (2), the reflux is carried out for 12 to 36 hours at the temperature of between 80 and 100 ℃; in the step (3), the reflux is performed for 12 to 36 hours at a temperature of between 70 and 90 ℃; in the step (4), the reflux is carried out for 12 to 36 hours at the temperature of between 55 and 75 ℃.
7. The use of o-dihydroxybenzaldehyde modified pomelo peel adsorbent prepared by the preparation method of claim 1 in selective adsorption removal of lead ions in acidic aqueous solution.
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