CN108246272A - A kind of preparation method of aquogel type heavy metal wastewater thereby adsorbent - Google Patents
A kind of preparation method of aquogel type heavy metal wastewater thereby adsorbent Download PDFInfo
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- CN108246272A CN108246272A CN201810224546.3A CN201810224546A CN108246272A CN 108246272 A CN108246272 A CN 108246272A CN 201810224546 A CN201810224546 A CN 201810224546A CN 108246272 A CN108246272 A CN 108246272A
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- 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
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- 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
- B01J20/28014—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 form
- B01J20/28047—Gels
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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
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Abstract
The invention discloses a kind of preparation methods of aquogel type heavy metal wastewater thereby adsorbent, using cyclodextrin as raw material, pass through 1,3 dicyclohexyl carbodiimide condensation methods have obtained propenoic acid beta cyclodextrin ester, by propenoic acid beta cyclodextrin ester by redox system, with acrylic acid by redox free radical polymerization, while the substances such as quinazolinedione derivatives are added in, aquogel type heavy metal wastewater thereby adsorbent is made, it can effectively heavy metal ion in Adsorption water.This method prepares that hydrogel adsorber operation is simple, and process is easy to control, and can be prepared, had good value for applications on a large scale.
Description
Technical field
The present invention relates to Treatment of Industrial Water fields, and in particular to a kind of hydrogel absorption for administering heavy metal-containing waste water
Agent.
Background technology
Heavy metal wastewater thereby is mainly derived from the industries such as mining, non-ferrous metal and smelting iron and steel, metal material processing, such as mine
Tailing draining, non-ferrous metals smelting works' draining, steel plant's dedusting draining, Metal Processing Factory's pickling draining, electroplate factory's washing draining
And the industry such as rubber, plastics, battery, pigment, chemical fertilizer, pesticide, leather, papermaking.After in heavy metals emission to environment, Zhi Nenggai
Become its form or be transferred, dilute, accumulate in vivo, and cannot be by biology or environment degradable.Heavy metal can pass through richness
Collection effect is into fish, plant, in animal body, the continuous enrichment through food chain, into human body in when oneself through reaching quite high
Concentration.After heavy metal enters human body, it is caused to lose bioactivity with strong interactions of generations such as protein and enzymes, also may be used
It can accumulate in certain organs in human body, cause slow poisoning, ultimately cause serious harm.Due to heavy metal for the mankind and
The health of biology has great harmfulness, so the heavy metal concentration in drinking water and waste water is by stringent limitation.
The processing method of heavy metal wastewater thereby mainly has according to removal principle at present is divided into three kinds.The first is heavy metal ion
Method by the way that chemical reaction removal occurs, second is that heavy metal ion is inhaled under conditions of chemical form is not changed
Attached, concentration, the method for separation, the third is to remove heavy metal in waste water by the effects that flocculation of biological plant, absorption, enrichment
Method.
In Heavy-Metal-Contaminated Environments governance process, the exploitation of new material has become a kind of good try.Hydrogel
It as a kind of high molecular material with three-dimensional net structure, can not only significantly be swollen in water, while keep its original knot
Structure and characteristic, and environmental stimuli can be perceived（Such as temperature, pH etc.）Minor change.Realize that its is right with shrinking by swelling
The influence of stimulation.Hydrogel becomes the novel absorption material of low-cost and pollution-less, they can absorb own wt 20%~100%
Moisture, the also known as super strength water absorbent when moisture of absorption is more than its own weight 100%.Hydrogel material is only with it
Special water suction, water conservation and good biocompatibility is widely used in agricultural, industry, medicine, environmental protection and biological engineering material neck
Domain.Aquogel type heavy metal wastewater thereby adsorbent, preparation process operation is made using cyclodextrin as primary raw material in the present invention
Simply, process is easy to control, excellent adsorption.
Invention content
It, can effectively Adsorption water the present invention provides a kind of preparation method of aquogel type heavy metal wastewater thereby adsorbent
Middle heavy metal ion.
A kind of preparation method of aquogel type heavy metal wastewater thereby adsorbent, it is characterised in that this method includes the following steps：
1）1, the 3- dicyclohexyls carbonization two for weighing beta-cyclodextrin and 3.18~13.18 parts by weight of 12 parts by weight through pre-treatment is sub-
Amine solid is dissolved in 100 parts by weight n,N-Dimethylformamide, is slowly added dropwise at room temperature sub- with 1,3- dicyclohexyls carbonization two
The acrylic acid of amine identical weight part, after 30min at 60 DEG C the reaction was continued 12h.After reaction, it is precipitated using vacuum filtration
Solid, and using 100 parts by weight mass fraction be 3% acetic acid solution and 50 parts by weight mass fractions be 5% potassium carbonate it is molten
Liquid carries out carrying out washing treatment, washs 3 times repeatedly, is dried in vacuo to obtain solid product acrylic acid beta-cyclodextrin ester；
2）0.60 parts by weight of acrylic acid and 0.40 parts by weight of acrylic acid-beta-cyclodextrin ester are dissolved in 5 parts by weight distilled water, simultaneously
11.6 parts by weight sodium hydrogensulfites and 2.35~3.25 parts by weight are added in the reaction system（3- substituted-phenyl -1- methyl quinolines
Oxazoline -2,4（1H, 3H）Diketone）- 6- carboxylate methyl esters are sealed in reaction bulb, after leading to nitrogen 20min, add in 13.92 parts by weight mistakes
Ammonium sulfate and 7.62~8.52 parts by weight 1H-2- acetyl group benzimidazoles are uniformly mixed, and add in NaH2PO4Buffer solution holding pH=
6.0~7.5, it polymerize 24 h at room temperature, taking-up soak is 0.8%, V in mass fraction(acetone):V(water)=1:In 1 solution,
It places 3 days at room temperature, slightly leaching for a moment, is cleaned 5 ~ 6 times with distilled water, hydrogel is dried in the air at room temperature in acetone soln after taking-up
Constant weight is dried under vacuum at 50 DEG C after dry, is placed in after drying at room temperature, is put into vacuum drying chamber, be dried to obtain water-setting again
Glue-type heavy metal wastewater thereby adsorbent.
Advantageous effect：Generally all contain various chelant functional groups, such as carboxylic for the hydrogel of Adsorption heavy metal ion
Base, amino, hydroxyl, sulfonic group etc..Hydrogel can be swollen and absorb large quantity of moisture in water, while can absorb the dirt in water
Contaminate substance.Hydrogel removes removing heavy metals, is based primarily upon in gel containing chelant functional group, being capable of Absorptive complex wave heavy metal.（3- takes
For phenyl -1- methylquinazolins -2,4（1H, 3H）Diketone）- 6- carboxylate methyl esters are the chemical combination of a typical phenyl ring and ring structure
Object has multiple adsorption sites on molecular structure, collaborative combination is mixed with 1H-2- acetylbenzene benzimidazole compounds, can with again
Metal forms complex, can tightly combine the heavy metal ion for being adsorbed onto hydrogel surface, it is therefore prevented that the ion hair of absorption
Raw desorption.
Specific embodiment
Embodiment 1
1）1, the 3- dicyclohexyl carbodiimide solids of beta-cyclodextrin and 3.18 parts by weight of 12 parts by weight through pre-treatment are weighed,
It is dissolved in 100 parts by weight n,N-Dimethylformamide, is slowly added dropwise at room temperature identical with 1,3- dicyclohexyl carbodiimides
The acrylic acid of parts by weight, after 30min at 60 DEG C the reaction was continued 12h.After reaction, the solid being precipitated using vacuum filtration,
And using 100 parts by weight mass fraction be 3% acetic acid solution and 50 parts by weight mass fractions be 5% solution of potassium carbonate carry out
Carrying out washing treatment washs 3 times, is dried in vacuo to obtain solid product acrylic acid beta-cyclodextrin ester repeatedly；
2）0.60 parts by weight of acrylic acid and 0.40 parts by weight of acrylic acid-beta-cyclodextrin ester are dissolved in 5 parts by weight distilled water, simultaneously
11.6 parts by weight sodium hydrogensulfites and 2.35 parts by weight are added in the reaction system（3- substituted-phenyl -1- methylquinazolin -2,
4（1H, 3H）Diketone）- 6- carboxylate methyl esters are sealed in reaction bulb, after leading to nitrogen 20min, add in 13.92 parts by weight ammonium persulfates and
7.62 parts by weight 1H-2- acetyl group benzimidazoles are uniformly mixed, and add in NaH2PO4Buffer solution keeps pH=6.0~7.5, in room temperature
24 h of lower polymerization, taking-up soak are 0.8%, V in mass fraction(acetone):V(water)=1:In 1 solution, place 3 days at room temperature,
Slightly leaching for a moment, is cleaned 5 ~ 6 times with distilled water in acetone soln after taking-up, true at 50 DEG C after hydrogel is dried at room temperature
Sky is dry to constant weight, is placed in after drying at room temperature, is put into vacuum drying chamber, is dried to obtain aquogel type heavy metal wastewater thereby again
Adsorbent.
Embodiment 2
Identical with embodiment 1, difference is：Weigh 4.18 parts by weight 1,3- dicyclohexyl carbodiimides solid,
2.45 parts by weight（3- substituted-phenyl -1- methylquinazolins -2,4（1H, 3H）Diketone）- 6- carboxylate methyl esters and 7.72 weights
Measure part 1H-2- acetyl group benzimidazoles.
Embodiment 3
Identical with embodiment 1, difference is：Weigh 5.18 parts by weight 1,3- dicyclohexyl carbodiimides solid,
2.55 parts by weight（3- substituted-phenyl -1- methylquinazolins -2,4（1H, 3H）Diketone）- 6- carboxylate methyl esters and 7.82 weights
Measure part 1H-2- acetyl group benzimidazoles.
Embodiment 4
Identical with embodiment 1, difference is：Weigh 6.18 parts by weight 1,3- dicyclohexyl carbodiimides solid,
2.65 parts by weight（3- substituted-phenyl -1- methylquinazolins -2,4（1H, 3H）Diketone）- 6- carboxylate methyl esters and 7.92 weights
Measure part 1H-2- acetyl group benzimidazoles.
Embodiment 5
Identical with embodiment 1, difference is：Weigh 7.18 parts by weight 1,3- dicyclohexyl carbodiimides solid,
2.75 parts by weight（3- substituted-phenyl -1- methylquinazolins -2,4（1H, 3H）Diketone）- 6- carboxylate methyl esters and 8.02 weights
Measure part 1H-2- acetyl group benzimidazoles.
Embodiment 6
Identical with embodiment 1, difference is：Weigh 8.18 parts by weight 1,3- dicyclohexyl carbodiimides solid,
2.85 parts by weight（3- substituted-phenyl -1- methylquinazolins -2,4（1H, 3H）Diketone）- 6- carboxylate methyl esters and 8.12 weights
Measure part 1H-2- acetyl group benzimidazoles.
Embodiment 7
Identical with embodiment 1, difference is：Weigh 9.18 parts by weight 1,3- dicyclohexyl carbodiimides solid,
2.95 parts by weight（3- substituted-phenyl -1- methylquinazolins -2,4（1H, 3H）Diketone）- 6- carboxylate methyl esters and 8.22 weights
Measure part 1H-2- acetyl group benzimidazoles.
Embodiment 8
Identical with embodiment 1, difference is：Weigh 10.18 parts by weight 1,3- dicyclohexyl carbodiimides solid,
3.05 parts by weight（3- substituted-phenyl -1- methylquinazolins -2,4（1H, 3H）Diketone）- 6- carboxylate methyl esters and 8.32 weights
Measure part 1H-2- acetyl group benzimidazoles.
Embodiment 9
Identical with embodiment 1, difference is：Weigh 11.18 parts by weight 1,3- dicyclohexyl carbodiimides solid,
3.15 parts by weight（3- substituted-phenyl -1- methylquinazolins -2,4（1H, 3H）Diketone）- 6- carboxylate methyl esters and 8.42 weights
Measure part 1H-2- acetyl group benzimidazoles.
Comparative example 1
Identical with embodiment 1, difference is：It is added without when preparing the hydrogel adsorbent（3- substituted-phenyl -1- methyl quinolines
Oxazoline -2,4（1H, 3H）Diketone）- 6- carboxylate methyl esters.
Comparative example 2
Identical with embodiment 1, difference is：1H-2- acetyl group benzimidazoles are added without when preparing the hydrogel adsorbent.
Comparative example 3
Identical with embodiment 1, difference is：It prepares（3- substituted-phenyl -1- methylquinazolins -2,4（1H, 3H）Diketone）-
6- carboxylate methyl esters are added without Cs2CO3。
Comparative example 4
Identical with embodiment 1, difference is：CrO is added without when preparing 1H-2- acetyl group benzimidazoles3。
Comparative example 5
Identical with embodiment 1, difference is：It is added without when preparing the hydrogel adsorbent（3- substituted-phenyl -1- methyl quinolines
Oxazoline -2,4（1H, 3H）Diketone）- 6- carboxylate methyl esters and 1H-2- acetyl group benzimidazoles.
Comparative example 6
Identical with embodiment 1, difference is：PH is maintained at 5.0.
Comparative example 7
Identical with embodiment 1, difference is：When preparing the hydrogel adsorbent at 55 DEG C the reaction was continued 12h.
Comparative example 8
Identical with embodiment 1, difference is：Pre-treatment is not carried out to beta-cyclodextrin when preparing the hydrogel adsorbent.
The sewage 1L at Jing Zhou industrial enterprise untreated sewage mouth is taken, measures wherein Cu2+And Cd2+Content be respectively
Then 9.76 mg/L and 12.4mg/L add in the hydrogel adsorbent that 1g embodiments 1 ~ 9 are prepared with comparative example 1 ~ 8, stirring
30min measures the content of two metal ion species in sewage after standing.
Hydrogel performance of the adsorbent test result
| Test specimens | Cu2+（mg/l） | Cd2+（mg/l） |
| Embodiment 1 | 0.85 | 1.74 |
| Embodiment 2 | 3.57 | 5.53 |
| Embodiment 3 | 3.41 | 5.61 |
| Embodiment 4 | 3.42 | 5.69 |
| Embodiment 5 | 3.59 | 5.75 |
| Embodiment 6 | 3.55 | 5.62 |
| Embodiment 7 | 3.75 | 5.94 |
| Embodiment 8 | 3.93 | 5.33 |
| Embodiment 9 | 3.69 | 5.86 |
| Comparative example 1 | 4.36 | 7.62 |
| Comparative example 2 | 5.67 | 8.77 |
| Comparative example 3 | 6.33 | 9.64 |
| Comparative example 4 | 6.48 | 9.73 |
| Comparative example 5 | 7.24 | 10.25 |
| Comparative example 6 | 8.32 | 11.47 |
| Comparative example 7 | 5.76 | 8.95 |
| Comparative example 8 | 4.18 | 6.81 |
By above-mentioned analysis of experimental results, embodiment 2-9 has certain Adsorption of Cu2+And Cd2+Effect, but effect is not notable, and
Embodiment 1 really has extraordinary adsorption effect, Cu2+And Cd2+Content only have 0.85 and 1.74 mg/l, it is seen that 1,3- bis-
Cyclohexylcarbodiimide solid,（3- substituted-phenyl -1- methylquinazolins -2,4（1H, 3H）Diketone）- 6- carboxylate methyl esters and
The ratio of 1H-2- acetyl group benzimidazole dosages is for Cu2+And Cd2+Influence it is very big, it is possible the reason of, although three has
The site combined with heavy metal ion, be combined with each other between them due to the intermolecular forces of chemical bond, so as to reduce bound site
Point is the same as the chelating chance of heavy metal ion.And embodiment 1 can increase considerably binding site with a huge sum of money under this ratio
Belong to the chelating chance of ion.In addition 1 ~ 5 explanation of comparative example（3- substituted-phenyl -1- methylquinazolins -2,4（1H, 3H）Diketone）-
The missing of 6- carboxylate methyl esters and 1H-2- acetyl group benzimidazoles all has an impact adsorption of metal ions removal, and comparative example 6 can
To find out, hydrogel to the more demanding of pH, it is possible the reason of pH can influence the property of hydrogel in itself.Comparative example 7 can be seen
Go out at 55 DEG C and reacted, metal ion removal rate declines, the possible reason is beta-cyclodextrin and the carbonization of 1,3- dicyclohexyl
Diimine solid does not dissolve adequately in the solution, and part residual is in the solution.Comparative example 8 illustrates to prepare hydrogel absorption
The selection of agent raw material has prominent influence to its absorption property.
Claims (5)
1. a kind of preparation method of aquogel type heavy metal wastewater thereby adsorbent, it is characterised in that this method includes the following steps：
1）1, the 3- dicyclohexyls carbonization two for weighing beta-cyclodextrin and 3.18~13.18 parts by weight of 12 parts by weight through pre-treatment is sub-
Amine solid is dissolved in 100 parts by weight n,N-Dimethylformamide, is slowly added dropwise at room temperature sub- with 1,3- dicyclohexyls carbonization two
The acrylic acid of amine identical weight part, after 30min at 60 DEG C the reaction was continued 12h,
After reaction, the solid being precipitated using vacuum filtration, and utilize the acetic acid solution that the mass fraction of 100 parts by weight is 3%
With the solution of potassium carbonate progress carrying out washing treatment that 50 parts by weight mass fractions are 5%, wash 3 times repeatedly, be dried in vacuo to obtain solid product
Acrylic acid beta-cyclodextrin ester；
2）0.60 parts by weight of acrylic acid and 0.40 parts by weight of acrylic acid-beta-cyclodextrin ester are dissolved in 5 parts by weight distilled water, simultaneously
11.6 parts by weight sodium hydrogensulfites and 2.35~3.25 parts by weight are added in the reaction system（3- substituted-phenyl -1- methyl quinolines
Oxazoline -2,4（1H, 3H）Diketone）- 6- carboxylate methyl esters are sealed in reaction bulb, after leading to nitrogen 20min, add in 13.92 parts by weight mistakes
Ammonium sulfate and 7.62~8.52 parts by weight 1H-2- acetyl group benzimidazoles are uniformly mixed, and add in NaH2PO4Buffer solution holding pH=
6.0~7.5, it polymerize 24 h at room temperature, taking-up soak is 0.8%, V in mass fraction(acetone):V(water)=1:In 1 solution,
It places 3 days at room temperature, slightly leaching for a moment, is cleaned 5 ~ 6 times with distilled water, hydrogel is dried in the air at room temperature in acetone soln after taking-up
Constant weight is dried under vacuum at 50 DEG C after dry, is placed in after drying at room temperature, is put into vacuum drying chamber, be dried to obtain water-setting again
Glue-type heavy metal wastewater thereby adsorbent.
2. according to the preparation method of aquogel type heavy metal wastewater thereby adsorbent a kind of in claim 1, it is characterised in that step 1）
The pre-treating method of middle beta-cyclodextrin is：The beta-cyclodextrin of 50 parts by weight is weighed, is dissolved in 100 parts by weight distilled water, is recrystallized
Twice, it is collected after vacuum drying 12h at 110 DEG C.
3. according to the preparation method of aquogel type heavy metal wastewater thereby adsorbent a kind of in claim 1, it is characterised in that step 1）
In 1,3- dicyclohexyl carbodiimides, purity 99%.
4. according to the preparation method of aquogel type heavy metal wastewater thereby adsorbent a kind of in claim 1, it is characterised in that step 2）
In（3- substituted-phenyl -1- methylquinazolins -2,4（1H, 3H）Diketone）The preparation method of -6- carboxylate methyl esters is：By 10 parts by weight
3- substituted-phenyl -1- methylquinazolins -2,4（1H, 3H）Mono- dimethyl methyl phthalein amine of the N of diketone and 70 parts by weight, N is added to
In reaction bulb, it is added with stirring the Cs of 19 parts by weight2CO3, after reacting at room temperature 30min, the iodomethane of 30 parts by weight is slowly added dropwise,
Continue to be stirred to react 12h after being added dropwise, after completion of the reaction pour into reaction solution in 100ml water, be vigorously stirred 30min, gained
Solid filters, after washing, drying to obtain the final product（3- substituted-phenyl -1- methylquinazolins -2,4（1H, 3H）Diketone）- 6- carboxylate methyl esters.
5. according to the preparation method of aquogel type heavy metal wastewater thereby adsorbent a kind of in claim 1, characterization step 2）Middle 1H-
The preparation method of 2- acetyl group benzimidazoles is：3.24 parts by weight 2- are added in round-bottomed flask（1- hydroxyethyls) benzo miaow
Azoles, 15 pbw of glacial acetic acid, stirring are warming up to 90 DEG C, weigh 1.60 parts by weight CrO3It is dissolved in the distilled water of 5 parts by weight, prepares
CrO3Solution, by CrO3Solution is slowly dropped in round-bottomed flask, is heated to reflux 5min, and reaction solution then is poured into 200 parts by weight
In ice water, green flocculent deposit is generated, is filtered, precipitation is removed, the dichloromethane extraction of 90 parts by weight of filtrate is collected organic
Layer, is dried with anhydrous sodium sulfate, and revolving removes solvent after filtering, and it is 1H-2- acetyl group benzimidazoles to obtain yellow-brown solid.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109705368A (en) * | 2018-12-24 | 2019-05-03 | 西北师范大学 | A kind of supermolecule and preparation method thereof based on benzimidazole iodo salt |
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| CN101816923A (en) * | 2010-04-07 | 2010-09-01 | 东北林业大学 | Method for preparing metal ion adsorbent |
| US20170173560A1 (en) * | 2015-04-20 | 2017-06-22 | Cornell University | Porous cyclodextrin polymeric materials and methods of making and using same |
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| CN109705368A (en) * | 2018-12-24 | 2019-05-03 | 西北师范大学 | A kind of supermolecule and preparation method thereof based on benzimidazole iodo salt |
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Application publication date: 20180706 |