CN107096510B - A kind of preparation method and applications of supermolecule adsorbent - Google Patents
A kind of preparation method and applications of supermolecule adsorbent Download PDFInfo
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- CN107096510B CN107096510B CN201710243354.2A CN201710243354A CN107096510B CN 107096510 B CN107096510 B CN 107096510B CN 201710243354 A CN201710243354 A CN 201710243354A CN 107096510 B CN107096510 B CN 107096510B
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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
- B01J20/26—Synthetic macromolecular compounds
- B01J20/262—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. obtained by polycondensation
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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
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28054—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their surface properties or porosity
- B01J20/28057—Surface area, e.g. B.E.T specific surface area
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- 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
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- 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
- C02F2101/10—Inorganic compounds
- C02F2101/20—Heavy metals or heavy metal compounds
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- 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
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
- C02F2103/30—Nature of the water, waste water, sewage or sludge to be treated from the textile industry
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Abstract
The invention discloses a kind of preparation method and applications of supermolecule adsorbent, belong to light-duty chemical field.The present invention is crosslinked pyridone macrocyclic compound by using crosslinking agents such as epoxychloropropane, Cyanuric Chlorides to obtain a kind of porous adsorbent material.Adsorbent cost obtained is low, and adsorption capacity is big, and adsorptivity is stablized, and such adsorbent material can be repeatedly used, and has great energy-saving and emission-reduction and environmental-friendly advantage.
Description
Technical field
The present invention relates to a kind of preparation method and applications of supermolecule adsorbent, belong to light-duty chemical field.
Background technique
With industrial development, industrial wastewater and sanitary wastewater pollution problem are got worse, and reinforce sewage treatment, especially work
The processing of industry waste water is particularly important.The waste water containing dyestuff of printworks discharge, pesticide is largely used in agricultural production
Being good for for mankind itself has also directly been threatened with ecological environment security is not only compromised by heavy metal pollutions such as mining, exhaust gas discharges
Health.
Water quality is good without secondary dirt after there is absorption method adsorbance height, adsorbent and absorbate can utilize and handle again
The advantages that dye, therefore absorption method becomes one of the main method of current industrial wastewater treatment.The type of current adsorbent is abundant, takes off
Color effect is different, and studying, there is low cost, high adsorption capacity and the adsorbent having wide range of applications to become current research
Hot spot.
Macrocyclic compound has the inner cavity aperture of specific dimensions, is capable of combination of the realization of selectivity to object, Ke Yishi
Existing Selective recognition.Macrocyclic compound is to carry out liquid by being dissolved into organic solvent not soluble in water to the separation of object
Mutually come what is realized, on the one hand this method has used a large amount of organic solvent (often toxic or inflammable) for extraction, on the other hand super
Molecular compound can be dissolved into the loss that super molecular compound is caused in water.To improve disadvantages described above, researcher is by β-ring
The adsorbent of dextrin, calixarenes or column aromatic hydrocarbons is immobilized to arrive silicon dioxide microsphere, in the matrix such as cellulose, chitosan；Or
It is crosslinked by reagents such as epoxychloropropane.However existing supermolecule adsorbent material there are specific surface areas small, adsorption capacity
Insufficient disadvantage.
Pyridone macrocyclic compound has not givey rigid planar structure, rich electrical inner cavity to metal ion, puts down
Having the organic matter of hydrophobic effect in face molecule and structure has selectivity.In research process before, inventors have found that pyridine
Ketone macrocyclic compound adsorption effect itself is poor；Inventor is prepared for the absorption of the cellulose base based on pyridone macrocyclic compound
Agent, but there are also to be reinforced for its adsorption capacity.
Summary of the invention
To solve the above-mentioned problems, the present invention provides in metal ion, planar molecule and the structure in a kind of pair of waste water
There is the organic matter of hydrophobic effect that there is the preparation method and application of supermolecule adsorbent of removal capacity, and absorbate and suction
Attached dose can be utilized with secondary recovery, save cost, and be achieved the purpose that environmental-friendly.The tool of macrocyclic compound used in the present invention
There are rigidity, not givey skeleton, can effectively increase the specific surface area of adsorbent material, enhances adsorption effect.
The first purpose of this invention is a kind of preparation method of supermolecule adsorbent, and the method is by the big ring of pyridone
Compound is reacted under weak base effect with cross-linking reagent, and to get pyridone macrocyclic compound modified adsorbent, (supermolecule is inhaled
Attached dose).
In one embodiment of the invention, the pyridone macrocyclic compound is five yuan of macrocyclic compound of pyridone
Or the hexa-atomic macrocyclic compound of pyridone.
In one embodiment of the invention, the pyridone macrocyclic compound, chemical formula are
Wherein n=1 or 2.
In one embodiment of the invention, the method is to hand over pyridone macrocyclic compound with cross-linking reagent
Connection reaction, connect cross-linking reagent with the secondary amine on pyridone.
In one embodiment of the invention, the cross-linking reagent be epoxychloropropane, glutaraldehyde, trichloro-triazine,
2,3,5,6- tetrafluoro terephthalonitrile or chlorination.
In one embodiment of the invention, the weak base is potassium carbonate, sodium carbonate, triethylamine, sodium acetate or pyrrole
Pyridine.
In one embodiment of the invention, the pyridone macrocyclic compound, cross-linking reagent, weak base molar ratio be
10:(20-100):(40-100)。
In one embodiment of the invention, the method is that the addition of pyridone macrocyclic compound is filled certain volume
In the round-bottomed flask of solvent, cross-linking reagent and weak base are added, it is small that control reaction temperature reacts 1-20 under the conditions of 20-100 DEG C
Shi Hou is rinsed with water after having reacted, filters, and is put into vacuum oven dry, the obtained pyridone macrocyclic compound function
The adsorbent of energyization.
In one embodiment of the invention, the pyridone macrocyclic compound, cross-linking reagent, weak base additive amount be
10mmol、20-100mmol、40-100mmol。
In one embodiment of the invention, the solvent be methanol, methylene chloride, tetrahydrofuran, acetone or N,
Dinethylformamide.
A second object of the present invention is to provide the supermolecule adsorbents being prepared according to the method described above.
Third object of the present invention is to provide the applications of the supermolecule adsorbent.
In one embodiment of the invention, the application is the application in field of waste water treatment, especially weaving print
Contaminate the removal and the application of recycling aspect of dyestuff raffinate in waste liquid.
In one embodiment of the invention, the application is the removal and recycling aspect of pesticide paraquat in waste water
Using.
In one embodiment of the invention, the application is answered in removal dye molecule or heavy metal ions
With especially adsorbing the application of positively charged dye molecule or heavy metal ions.
In one embodiment of the invention, the heavy metal ion, can be Cu2+、Hg2+、Pb2+、Fe3+、Ni2+、
Cr3+Etc. heavy metal ion.
In one embodiment of the invention, the dye molecule can be the dyestuffs such as methylene blue, crystal violet, especially
It is the positively charged dye molecule of absorption, and for neutrality, anionic dye also has adsorption effect, but effect is not so good as to contaminate cation
The adsorption effect of material.
In one embodiment of the invention, the pesticide molecule is positively charged pesticide molecule, as paraquat (1,
1'- dimethyl -4,4'- bipyridyl chloride).
Beneficial effects of the present invention:
(1) present invention, which reacts supermolecule adsorbent obtained with pyridone macrocyclic compound using crosslinking agent, reduces extraction
The dosage of organic solvent and the loss of adsorbent is avoided in the process, simplifies extraction step, adsorption capacity with higher, from
And realize the removal to common contaminants such as heavy metal ions in wastewater, dyestuffs.
(2) the method for the present invention is simple, easy to operate, and the supermolecule adsorbent obtained by the method for the present invention is to metal ion, dye
Material molecule and paraquat etc. have higher adsorption effect, and adsorption capacity is strong, adsorption rate is fast (3-15min), wherein to Cu2+、
Hg2+、Pb2+、Fe3+、Ni2+、Cr3+Adsorbance respectively reach 518.4mg/g, 213.4mg/g, 654.8mg/g, 713.4mg/g,
320.5mg/g, 918.4mg/g, to methylene blue, crystal violet, the adsorbance of methyl orange respectively reach 920mg/g, 298mg/g,
80mg/g reaches 239.2mg/g to the adsorbance of paraquat.
(3) supermolecule adsorbent of the invention is applied widely, in temperature range room temperature~50 DEG C, pH range 3~10,
The application range of adsorbent is expanded to a certain extent；And also there is higher adsorption efficiency to low concentration pollutant.
(4) supermolecule adsorbent of the invention is can to repeat the absorbate recycled by desorption, to quilt
The structure of adsorbate does not have destruction, and the recycling rate of waterused of adsorbent is improved by desorption, has cost
It is cheap, adsorption capacity is big, performance is stable, regenerability is good and advantages of environment protection.
Detailed description of the invention
Fig. 1: the structural schematic diagram of supermolecule adsorbent；
Fig. 2: the infared spectrum of supermolecule adsorbent；
Fig. 3: scanning electron microscope (SEM) photograph before (a) pyridone macrocyclic compound is crosslinked；(b) it is scanned after the crosslinking of pyridone macrocyclic compound
Electron microscope.
Specific embodiment
Embodiment 1: the preparation of the pyridone macrocyclic compound supermolecule adsorbent of epoxychloropropane crosslinking
The big ring supermolecule adsorbent of pyridone is prepared as follows:
Pyridone macrocyclic compound, potassium carbonate and epoxychloropropane are added in DMF solution, the molar ratio of three is 1:2:
4, reaction time 5h, reaction temperature are 60 DEG C, as the carry out system viscosity of reaction is gradually increased.Stop mistake after reacting
Filter is dried in vacuo spare using obtained solid using washing, ethanol washing later respectively.
Fig. 2 is the infared spectrum of the pyridone macrocyclic compound adsorbent of epoxychloropropane crosslinking, as shown in Fig. 2,
3300cm-1The more sharp amido peak in left and right becomes the broad peak that more intensity is bigger after epoxychloropropane is crosslinked, and illustrates there is hydroxyl
Base generates.Epoxychloropropane is demonstrated to be crosslinked successfully.The surface topography such as scanning electron microscope of pyridone macrocyclic compound crosslinking front and back
Shown in Fig. 3, the surface of adsorbent becomes more coarse hole generation after crosslinking, and coarse surface can increase surface favorably
In the progress of absorption.
Embodiment 2: application of the big ring adsorbent of pyridone of epoxychloropropane crosslinking in terms of adsorbing metal ions
The supermolecule adsorbent 25mg that embodiment 1 is obtained, is placed in the certain density metal ion solution of 150mL, stirs
It is adsorbed under the conditions of mixing, the adsorbance for measuring after a certain period of time and calculating adsorbent to them.
(1)Cu2+: temperature is 25 DEG C, time 10min, pH 4, and original metal ion concentration is 96mg/L；Supermolecule is inhaled
Attached dose of maximal absorptive capacity reaches 518.4mg/g；Adsorption efficiency is 90%.
(2)Cu2+: temperature is 25 DEG C, time 10min, pH 4, and the amount of adsorbent is 2.5mg, and original metal ion is dense
Degree is 4mg/L；The adsorption efficiency of supermolecule adsorbent is 86%.It can be seen that adsorbent of the invention to low-concentration metallic from
Son also has higher adsorption efficiency.
(3)Hg2+: temperature is 25 DEG C, time 15min, pH 4.5, and original metal ion concentration is 42mg/L；Supermolecule
The maximal absorptive capacity of adsorbent reaches 213.4mg/g；Adsorption efficiency is 85%.
(4)Pb2+: temperature is 22 DEG C, time 7min, pH 4.2, and original metal ion concentration is 136mg/L；Supermolecule
The maximal absorptive capacity of adsorbent reaches 654.8mg/g.
(5)Fe3+: temperature is 25 DEG C, time 10min, pH 4.5, and original metal ion concentration is 140mg/L；Oversubscription
The maximal absorptive capacity of sub- adsorbent reaches 713.4mg/g.
(6)Ni2+: temperature is 25 DEG C, time 10min, pH 4.5, and original metal ion concentration is 60mg/L；Supermolecule
The maximal absorptive capacity of adsorbent reaches 320.5mg/g.
(7)Cr3+: temperature is 23 DEG C, time 15min, pH 4.4, and original metal ion concentration is 190mg/L；Oversubscription
The maximal absorptive capacity of sub- adsorbent reaches 918.4mg/g.
Embodiment 3: application of the big ring adsorbent of pyridone of epoxychloropropane crosslinking in terms of adsorpting dye molecule
By 25mg supermolecule adsorbent, being placed in 150mL concentration is in certain density dye solution, and absorption is after a certain period of time
The adsorbance for measuring and calculating adsorbent to them.
(1) methylene blue: temperature is 50 DEG C, time 10min, pH 7.9, initial dye concentration 155mg/L；Epoxy
The adsorbance of the big ring adsorbent of pyridone of chloropropane crosslinking is 920mg/g, and adsorption rate is respectively 99%.
(2) crystal violet: temperature is 50 DEG C, time 8min, pH 8.2, initial dye concentration 58mg/L；Epoxy chloropropionate
The adsorbance of the big ring adsorbent of pyridone of alkane crosslinking is 280mg/g, and adsorption rate is respectively 85%.
(3) methyl orange: temperature is 50 DEG C, time 8min, pH 8.2；The adsorbance of the big ring adsorbent of pyridone is
80mg/g。
Embodiment 4: application of the big ring adsorbent of pyridone of epoxychloropropane crosslinking in terms of adsorbing pesticide
By 25mg supermolecule adsorbent, being placed in 150mL concentration is in 40mg/L paraquat solution, and absorption is surveyed after a certain period of time
The adsorbance determined and calculate adsorbent to them.Adsorption conditions are as follows: temperature is 50 DEG C, time 10min, pH 7；Epoxy chloropropionate
The adsorbance of the big ring adsorbent of pyridone of alkane crosslinking is 239.2mg/g, and adsorption rate is respectively 99%.
Embodiment 5: Studies On Preparation And Properties of Cellulose-based Adsorbents reproducibility test
Influence of the reuse of adsorbent to its adsorption capacity, the results showed that adsorbent adsorb heavy metal ion or
After the adsorbates such as dyestuff, the dilute hydrochloric acid solution that 0.1mol/L can be used carries out desorption, first five time is reused its absorption and held
Less, the 6th time adsorption test its adsorption capacity only declines 2% for amount variation.
Although the present invention has been described by way of example and in terms of the preferred embodiments, it is not intended to limit the invention, any to be familiar with this skill
The people of art can do various change and modification, therefore protection model of the invention without departing from the spirit and scope of the present invention
Enclosing subject to the definition of the claims.
Claims (6)
1. a kind of for adsorbing the supermolecule adsorbent of organic pollutant and heavy metal ion, which is characterized in that the supermolecule
The preparation method of adsorbent is to react pyridone macrocyclic compound to get supermolecule under weak base effect with cross-linking reagent
Adsorbent；The cross-linking reagent be epoxychloropropane, glutaraldehyde, trichloro-triazine, 2,3,5,6- tetrafluoro terephthalonitrile or
Chlorination.
2. supermolecule adsorbent according to claim 1, which is characterized in that the pyridone macrocyclic compound is pyridone
5-membered ring compounds or the hexa-atomic cycle compound of pyridone.
3. supermolecule adsorbent according to claim 1, which is characterized in that the weak base is potassium carbonate, sodium carbonate, three second
Amine, sodium acetate or pyridine.
4. supermolecule adsorbent according to claim 1, which is characterized in that the pyridone macrocyclic compound, crosslinking examination
Agent, weak base molar ratio be 10:(20-100): (40-100).
5. supermolecule adsorbent according to claim 4, which is characterized in that the addition of pyridone macrocyclic compound is filled one
Determine in the round-bottomed flask of volume of solvent, add cross-linking reagent and weak base, control reaction temperature is reacted under the conditions of 20-100 DEG C
It after 1-20 hours, is rinsed with water, filters after having reacted, be put into vacuum oven dry, the obtained big cyclisation of pyridone
Close the adsorbent of object functionalization.
6. supermolecule adsorbent according to claim 5, which is characterized in that the solvent is methanol, methylene chloride, tetrahydro
Furans, acetone or N,N-dimethylformamide.
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| CN109046280B (en) * | 2018-08-23 | 2021-04-02 | 四川大学 | Beta-cyclodextrin polymer adsorbent and preparation method and application thereof |
| CN109126740B (en) * | 2018-09-04 | 2020-12-29 | 江南大学 | Preparation of nanofiber membrane and application of nanofiber membrane in wastewater treatment |
| CN109364880B (en) * | 2018-10-30 | 2021-02-12 | 西北师范大学 | Supramolecular organic framework material with cyclic analysis function and application of supramolecular organic framework material in removal of organic dye in water body |
| CN110305333B (en) * | 2019-07-26 | 2022-03-11 | 中山大学 | Column [5] arene polymer microsphere and preparation method and application thereof |
| CN110841600B (en) * | 2019-11-27 | 2021-06-25 | 江南大学 | Preparation method and application of macrocyclic compound functionalized magnetic nanoparticles |
| CN111635357B (en) * | 2020-06-24 | 2021-07-27 | 江南大学 | Deodorant containing macrocyclic compound and preparation method thereof |
| CN112899481B (en) * | 2021-01-15 | 2022-09-27 | 浙江大学 | Method for adsorbing and separating potassium and sodium |
| CN113845606B (en) * | 2021-09-28 | 2022-12-16 | 称意科技研发园(江苏)有限公司 | Modified cyclodextrin dye adsorbent and preparation method thereof |
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Effective date of registration: 20200921 Address after: 510000 unit 2311, main building, 371-1 Wushan Road, Tianhe District, Guangzhou City, Guangdong Province Patentee after: Intercontinental Institute of Environmental Sciences (Guangzhou) Co.,Ltd. Address before: 1800 No. 214122 Jiangsu city of Wuxi Province Li Lake Avenue Patentee before: Jiangnan University |