CN110586047B - Preparation method of modified dialdehyde starch for adsorbing lead ions - Google Patents
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Abstract
The invention relates to a preparation method of modified dialdehyde starch for adsorbing lead ions, which belongs to the field of preparation of heavy metal ion adsorbents and is characterized in that starch is firstly oxidized into dialdehyde starch, namely DAS, methyl 5-amino isophthalate is introduced to the surface of DAS to obtain methyl 5-amino isophthalate modified dialdehyde starch, namely DASD5-A, and hydrazine acylation is carried out on the surface of DAS to obtain hydrazine acylated modified dialdehyde starch, namely NH2DAS, and finally obtaining 2-acetylthiophene modified dialdehyde starch through Schiff base reaction, namely DAS 2-AT. The method not only widens the method for functionalizing the surface of the dialdehyde starch, but also endows the dialdehyde starch with good adsorption performance to lead ions. The method has the advantages of simple and flexible process, mild reaction conditions, low cost and easy industrial production.
Description
Technical Field
The invention belongs to the field of preparation of adsorbents, and particularly relates to a preparation method of modified dialdehyde starch for adsorbing lead ions.
Background
In recent years, in the case where people are engaged in the development of agriculture and industry, the pollution of heavy metal ions is becoming more serious. Reports of diseases caused by heavy metal ion pollution are frequent, and heavy metal ion pollution becomes a problem which needs to be faced and needs to be solved by human beings urgently.
The adsorption method is an important method for industrially separating and recovering heavy metal ions in water. Common adsorbents include activated carbon, molecular sieves, graphene, and biopolymers. Starch is a natural biopolysaccharide material that has received attention from researchers because it is inexpensive and readily available. The dialdehyde starch (DAS) can be obtained by periodate oxidation of starch, and the C-C bond of 2, 3-position of glucosyl in the starch is broken to generate two aldehyde groups. On the basis, other organic compounds can react with aldehyde groups on the dialdehyde starch through Schiff base reaction, and other functional groups are introduced, so that the modified dialdehyde starch with heavy metal adsorption capacity can be obtained. The modified dialdehyde starch solves the problems of biocompatibility, recoverability and biodegradability of a pure organic ligand. Ding et al synthesized a dialdehyde 8-aminoquinoline starch, which had a certain effect on removing zinc ions in water (Carbohydrate Polymers,2011,83(2): 802-. However, so far, the modified dialdehyde starch has no ideal effect on removing lead ions in water. Therefore, the development of the modified dialdehyde starch with good adsorption effect on lead ions has good application prospect.
Disclosure of Invention
In order to solve the technical problems, the invention provides a preparation method of modified dialdehyde starch for adsorbing lead ions. The modified dialdehyde starch synthesized by the method not only has good poor biocompatibility and water solubility, but also has strong adsorption capacity to lead ions in water.
The technical solution of the invention is as follows:
a preparation method of modified dialdehyde starch for adsorbing lead ions comprises the following steps:
(1) dialdehyde starch, namely preparation of DAS
Weighing 4g to 8g of starch, adding 5mL to 20mL of deionized water, continuously stirring to form a suspension, placing the suspension in a dark box, slowly dropwise adding 80mL to 120mL of sodium periodate with the concentration of 0.5mol/L to 1.2mol/L, and then adjusting the pH value to 3 to 5 by using 0.05mol/L to 0.15mol/L of dilute sulfuric acid. Reacting for 1-6 h in the dark at 30-70 ℃, filtering, adding deionized water for washing to be neutral, and drying in a drying oven at 50-70 ℃ to obtain dialdehyde starch, namely DAS.
(2) 5-amino methyl isophthalate modified dialdehyde starch, namely preparation of DASD5-A
Dissolving 3-7 g of 5-amino methyl isophthalate in a three-necked flask filled with 50-100 mL of organic solution, adding 4-8 g of DAS obtained in the step (1) into the three-necked flask, dropwise adding 0.2-0.5 mL of glacial acetic acid, reacting for 4-12 hours at 30-70 ℃ under the protection of inert atmosphere, washing with an organic solvent, and drying at 50-70 ℃ overnight to obtain 5-amino methyl isophthalate modified dialdehyde starch, namely DASD 5-A.
(3) Hydrazine acylated modified dialdehyde starch, namely NH2Preparation of DAS
Dissolving 4-8 g of DASD5-A obtained in the step (2) in 50-100 mL of organic solvent, dropwise adding 1-5 mL of hydrazine hydrate, reacting for 12-24 hours at 30-70 ℃ under the protection of inert atmosphere, washing with the organic solvent, and drying overnight at 50-70 ℃ to obtain hydrazine acylated modified dialdehyde starch, namely NH2-DAS。
(4) 2-acetylthiophene modified dialdehyde starch, namely DAS2-AT preparation
4g to 8g of NH obtained in the step (3)2Dissolving DAS in 50-100 mL of organic solvent, adding 4-8 g of 2-acetylthiophene, reacting for 4-12 hours AT 30-70 ℃ under the protection of inert atmosphere, washing with the organic solvent, and drying overnight AT 50-70 ℃ to obtain 2-acetylthiophene modified dialdehyde starch, namely DAS 2-AT.
Further, the starch in the step (1) is potato starch, corn starch, tapioca starch or sweet potato starch.
Further, the organic solvent in the steps (2), (3) and (4) is absolute ethyl alcohol, absolute methyl alcohol or absolute DMSO.
Further, the inert atmosphere in the steps (2), (3) and (4) is nitrogen or argon. The invention has the beneficial effects that:
the invention has the beneficial effects that the dialdehyde starch is aminated, and then the Schiff base reaction is utilized to introduce the 2-acetylthiophene functional group which has chelation effect on lead ions on the surface of the dialdehyde starch. The method not only widens the method for functionalizing the surface of the dialdehyde starch, but also endows the dialdehyde starch with good adsorption performance to lead ions. The method has the advantages of simple process, mild reaction conditions, low cost and easy industrial production.
Drawings
FIG. 1 is a surface SEM image of modified dialdehyde starch (DAS2-AT) in the invention.
FIG. 2 is an XRD pattern of a modified dialdehyde starch (DAS2-AT) in the invention.
FIG. 3 is a FT-IR diagram of modified dialdehyde starch (DAS2-AT) in the invention.
Detailed Description
Example 1
(1) Preparation of dialdehyde starch (DAS)
Weighing 4g of potato starch, adding 5mL of deionized water, continuously stirring to form a suspension, placing the suspension in a dark box, slowly dropwise adding 80mL of 0.5mol/L sodium periodate, and then adjusting the pH value to 3 by using 0.05mol/L dilute sulfuric acid. Reacting for 1h in the dark at the temperature of 30 ℃, filtering, adding deionized water for washing to be neutral, and drying in an oven at the temperature of 50 ℃ to obtain dialdehyde starch (DAS).
(2) Preparation of 5-amino methyl isophthalate modified dialdehyde starch (DASD5-A)
Dissolving 3g of methyl 5-aminoisophthalate in a three-necked flask containing 50mL of an organic solution, adding 4g of DAS obtained in step (1) to the three-necked flask, dropwise adding 0.2mL of glacial acetic acid, reacting at 30 ℃ for 4 hours under the protection of nitrogen, washing with absolute ethanol, and drying at 50 ℃ overnight to obtain methyl 5-aminoisophthalate modified dialdehyde starch (DASD 5-A).
(3) Hydrazine acylated modified dialdehyde starch (NH)2DAS) preparation
Dissolving 4g of DASD5-A obtained in the step (2) in 50mL of organic solvent, dropwise adding 1mL of hydrazine hydrate, reacting at 30 ℃ for 12 hours under the protection of nitrogen, washing with the organic solvent, and drying at 50 ℃ overnight to obtain hydrazine acylated modified dialdehyde starch (NH)2-DAS)。
(4) Preparation of 2-acetylthiophene modified dialdehyde starch (DAS2-AT)
4g of NH obtained in step (3)2DAS is dissolved in 50mL of organic solvent, 4g of 2-acetylthiophene is added, reaction is carried out for 4 hours AT 30 ℃ under the protection of nitrogen, washing is carried out by the organic solvent, and drying is carried out overnight AT 50 ℃ to obtain 2-acetylthiophene modified dialdehyde starch (DAS 2-AT).
Example 2
(1) Preparation of dialdehyde starch (DAS)
6g of corn starch is weighed, 10mL of deionized water is added and continuously stirred to form a suspension, the suspension is placed in a dark box, then 100mL of 1.0mol/L sodium periodate is slowly and dropwise added, and then the pH value is adjusted to 4 by 0.1mol/L dilute sulfuric acid. Reacting at 50 ℃ in a dark place for 4h, filtering, adding deionized water for washing to be neutral, and drying in an oven at 60 ℃ to obtain dialdehyde starch (DAS).
(2) Preparation of 5-amino methyl isophthalate modified dialdehyde starch (DASD5-A)
5g of methyl 5-aminoisophthalate was dissolved in 80mL of a three-necked flask containing an organic solution, 6g of DAS obtained in step (1) was added to the three-necked flask, 0.3mL of glacial acetic acid was added dropwise, and after reaction at 60 ℃ for 8 hours under argon atmosphere, the DAS was washed with anhydrous methanol and dried at 60 ℃ overnight to obtain methyl 5-aminoisophthalate-modified dialdehyde starch (DASD 5-A).
(3) Hydrazine acylated modified dialdehyde starch (NH)2DAS) preparation
Dissolving 6g of DASD5-A obtained in the step (2) in 80mL of organic solvent, dropwise adding 3mL of hydrazine hydrate, reacting at 50 ℃ for 18 hours under the protection of argon, washing with anhydrous methanol, and drying at 60 ℃ overnight to obtain hydrazine acylated modified dialdehyde starch (NH)2-DAS)。
(4) Preparation of 2-acetylthiophene modified dialdehyde starch (DAS2-AT)
Mixing 6g of NH obtained in step (3)2DAS is dissolved in 80mL of organic solvent, 6g of 2-acetylthiophene is added, after reaction for 8 hours AT 50 ℃ under the protection of argon, anhydrous methanol is used for washing, and drying is carried out overnight AT 60 ℃ to obtain 2-acetylthiophene modified dialdehyde starch (DAS 2-AT).
Example 3
(1) Preparation of dialdehyde starch (DAS)
Weighing 8g of cassava starch, adding 20mL of deionized water, continuously stirring to form a suspension, placing the suspension in a dark box, slowly dropwise adding 120mL of 1.2mol/L sodium periodate, and then adjusting the pH value to 4 by using 0.15mol/L dilute sulfuric acid. Reacting for 6h in the dark at 60 ℃, filtering, adding deionized water for washing to be neutral, and drying in an oven at 70 ℃ to obtain dialdehyde starch (DAS).
(2) Preparation of 5-amino methyl isophthalate modified dialdehyde starch (DASD5-A)
7g of methyl 5-aminoisophthalate was dissolved in a three-necked flask containing 100mL of an organic solution, 8g of DAS obtained in step (1) was added to the three-necked flask, 0.5mL of glacial acetic acid was added dropwise, and after reaction at 70 ℃ for 12 hours under the protection of argon gas, the DAS was washed with anhydrous DMSO and dried at 80 ℃ overnight to obtain methyl 5-aminoisophthalate-modified dialdehyde starch (DASD 5-A).
(3) Hydrazine acylated modified dialdehyde starch (NH)2DAS) preparation
Dissolving 8g of DASD5-A obtained in the step (2) in 100mL of organic solvent, dropwise adding 5mL of hydrazine hydrate, reacting at 70 ℃ for 24 hours under the protection of argon, washing with anhydrous DMSO, and drying at 70 ℃ overnight to obtain hydrazine acylated modified dialdehyde starch (NH)2-DAS)。
(4) Preparation of 2-acetylthiophene modified dialdehyde starch (DAS2-AT)
8g of NH obtained in step (3)2DAS is dissolved in 100mL of organic solvent, 8g of 2-acetylthiophene is added, after reaction for 12 hours AT 70 ℃ under the protection of argon, the obtained product is washed by anhydrous DMSO and dried overnight AT 70 ℃, and 2-acetylthiophene modified dialdehyde starch (DAS2-AT) is obtained.
Example 4
(1) Preparation of dialdehyde starch (DAS)
Weighing 4g of sweet potato starch, adding 12mL of deionized water, continuously stirring to form a suspension, placing the suspension in a dark box, slowly dropwise adding 100mL of 0.8mol/L sodium periodate, and then adjusting the pH value to 3 by using 0.1mol/L dilute sulfuric acid. Reacting for 4h at 30 ℃ in the dark, filtering, adding deionized water for washing to be neutral, and drying in an oven at 50 ℃ to obtain dialdehyde starch (DAS).
(2) Preparation of 5-amino methyl isophthalate modified dialdehyde starch (DASD5-A)
5g of methyl 5-aminoisophthalate was dissolved in 50mL of anhydrous methanol solution in a three-necked flask, 4g of DAS obtained in step (1) was added to the three-necked flask, 0.2mL of glacial acetic acid was added dropwise, and after reaction at 50 ℃ for 10 hours under the protection of argon gas, the DAS was washed with anhydrous methanol and dried at 60 ℃ overnight to obtain methyl 5-aminoisophthalate-modified dialdehyde starch (DASD 5-A).
(3) Hydrazine acylated modified dialdehyde starch (NH)2DAS) preparation
Dissolving 4g of DASD5-A obtained in the step (2) in 50mL of anhydrous methanol, dropwise adding 2.5mL of hydrazine hydrate, reacting at 50 ℃ for 18 hours under the protection of argon, washing with anhydrous methanol, and drying at 50 ℃ overnight to obtain hydrazine acylated modified dialdehyde starch (NH)2-DAS)。
(4) Preparation of 2-acetylthiophene modified dialdehyde starch (DAS2-AT)
4g of NH obtained in step (3)2DAS is dissolved in 80mL of organic solvent, 4g of 2-acetylthiophene is added, after reaction for 10 hours AT 60 ℃ under the protection of argon, anhydrous methanol is used for washing, and drying is carried out overnight AT 60 ℃ to obtain 2-acetylthiophene modified dialdehyde starch (DAS 2-AT).
Example 5
The adsorption experiment of the modified dialdehyde starch prepared by the invention on lead ions comprises the following specific steps: 50mg of the modified dialdehyde starch (DAS2-AT) obtained in each of example 1, example 2, example 3 and example 4 was taken and placed in 50mL of 200mg/L lead ion solution, and the solution was adsorbed AT 30 ℃ for 3 hours, then centrifuged for 10min, and the supernatant was taken and the concentration of the remaining lead ions was measured by an atomic absorption spectrometer to calculate the adsorption rate of the modified dialdehyde starch to the lead ions, and the results are shown in Table 1. As can be seen from the analysis of Table 1, the modified dialdehyde starch obtained by the technical scheme provided by the invention has good adsorption performance on lead ions.
TABLE 1 adsorption Performance of modified dialdehyde starch (DAS2-AT) for lead ions
| Sample (I) | Adsorption Rate (%) |
| Example 1 | 95 |
| Example 2 | 92 |
| Example 3 | 93 |
| Example 4 | 97 |
Claims (6)
1. A preparation method of modified dialdehyde starch for adsorbing lead ions is characterized in that: the method comprises the following specific steps:
(1) dialdehyde starch, namely preparation of DAS
Weighing 4g to 8g of starch, adding 5mL to 20mL of deionized water, continuously stirring to form a suspension, placing the suspension in a dark box, slowly dropwise adding 80mL to 120mL of sodium periodate with the concentration of 0.5mol/L to 1.2mol/L, and then adjusting the pH value to 3 to 5 by using 0.05mol/L to 0.15mol/L of dilute sulfuric acid; reacting for 1-6 h in the dark at 30-60 ℃, filtering, adding deionized water for washing to be neutral, and drying in a drying oven at 50-70 ℃ to obtain dialdehyde starch, namely DAS;
(2) 5-amino methyl isophthalate modified dialdehyde starch, namely preparation of DASD5-A
Dissolving 3g to 7g of 5-amino methyl isophthalate in a three-neck flask filled with 50mL to 100mL of organic solution, adding 4g to 8g of DAS obtained in the step (1) into the three-neck flask, dropwise adding 0.2mL to 0.5mL of glacial acetic acid, reacting for 4 hours to 12 hours under the protection of inert atmosphere, washing with an organic solvent, and drying overnight to obtain 5-amino methyl isophthalate modified dialdehyde starch which is DASD 5-A;
(3) hydrazine acylated modified dialdehyde starch, namely NH2Preparation of DAS
Dissolving 4-8 g of DASD5-A obtained in the step (2) in 50-100 mL of organic solvent, dropwise adding 1-5 mL of hydrazine hydrate, reacting for 12-24 hours under the protection of inert atmosphere, washing with the organic solvent, and drying overnight to obtain hydrazine acylated modified dialdehyde starch, namely NH2-DAS；
(4) 2-acetylthiophene modified dialdehyde starch, namely DAS2-AT preparation
4g to 8g of NH obtained in the step (3)2Dissolving DAS in 50-100 mL of organic solvent, adding 4-8 g of 2-acetylthiophene, reacting for 4-12 hours under the protection of inert atmosphere, washing and drying overnight by using the organic solvent to obtain 2-acetylthiophene modified dialdehyde starch, namely DAS 2-AT.
2. The preparation method of the modified dialdehyde starch for adsorbing the lead ions according to claim 1, which is characterized in that: the starch in the step (1) is potato starch, corn starch, cassava starch or sweet potato starch.
3. The preparation method of the modified dialdehyde starch for adsorbing the lead ions according to claim 1, which is characterized in that: the organic solvent in the steps (2), (3) and (4) is ethanol, methanol or DMSO.
4. The preparation method of the modified dialdehyde starch for adsorbing the lead ions according to claim 1, which is characterized in that: and (3) the inert atmosphere in the steps (2), (3) and (4) is nitrogen or argon.
5. The preparation method of the modified dialdehyde starch for adsorbing the lead ions according to claim 1, which is characterized in that: the reaction temperature in the steps (2), (3) and (4) is 30-70 ℃.
6. The preparation method of the modified dialdehyde starch for adsorbing the lead ions according to claim 1, which is characterized in that: the drying temperature in the steps (2), (3) and (4) is 50-70 ℃.
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