CN108912338A - A kind of preparation of supermolecule organic frame and in Adsorption water body pollutant application - Google Patents
A kind of preparation of supermolecule organic frame and in Adsorption water body pollutant application Download PDFInfo
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- CN108912338A CN108912338A CN201810637744.2A CN201810637744A CN108912338A CN 108912338 A CN108912338 A CN 108912338A CN 201810637744 A CN201810637744 A CN 201810637744A CN 108912338 A CN108912338 A CN 108912338A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/008—Supramolecular polymers
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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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- 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
- C02F2101/00—Nature of the contaminant
- C02F2101/30—Organic compounds
- C02F2101/34—Organic compounds containing oxygen
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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
- C02F2101/34—Organic compounds containing oxygen
- C02F2101/345—Phenols
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Abstract
Present invention design has synthesized a kind of column [5] arene-based supermolecule organic framework materials SOFs-P5G based on naphthalimide functionalization, it is in cyclohexanol, double 4,4 bipyridine salts of column [5] aromatic hydrocarbons and object of main body naphthalimide functionalization are formed with equimolar than self assembly.Supermolecule organic frame SOFs-P5G is shown into extraordinary Adsorption effect to the various organic pollutants in water body.By being monitored with ultra-violet absorption spectrum, SOFs-P5G is calculated, 50% is all larger than to the removal rate of various pollutants, wherein the removal rate to potassium permanganate is up to 99%.The supermolecule organic framework materials SOFs-P5G powder for being adsorbed with pollutant is added in dehydrated alcohol, at 35 ~ 40 DEG C after stirred in water bath 15 minutes, the pollutant being adsorbed is released, it is filtered again, it is dry, so that supermolecule organic framework materials SOFs-P5G is achieved the purpose that Recovery and recycle uses.
Description
Technical field
Column [5] aromatic hydrocarbons that the present invention relates to a kind of with naphthalimide functionalization（P5N）Based on, double 4,4 bipyridine salts（G）
For supermolecule organic frame SOFs-P5G made of object self assembly, it is mainly used for belonging to the separation removal of pollutant in water body
In water-treatment technology field.
Background technique
In in the past few decades, by weaving, leather, a large amount of waste water from dyestuff discharge that papermaking and printing industry generate is
Lead to serious environmental problem, because most of commercial dyes are all highly toxic, or even carcinogenic by concentrated biological body.
Many traditional physico-chemical process have been used for handling dye discoloration.Currently, in the various treatment process of waste water containing dye,
Adsorption process has become one of the most useful technology.Various adsorbents such as silica, clay, active carbon and mesoporous silicon oxide
Have been used for such processing.Adsorbent material（Such as active carbon）It the use of the organic pollutant in absorption waste water is a kind of environmentally protective
Method, but since it is handled, the time is long, and cost recovery is high, therefore this low efficiency for the practical application in industry, spends
Cost is too high, and is unfavorable for conveniently practical application.Therefore, removal pollutant rapidly and efficiently becomes one and great chooses
The project of war.
Summary of the invention
The object of the present invention is to provide a kind of preparation methods of supermolecule organic frame；
It is a further object of the present invention to provide above-mentioned supermolecule organic frames as adsorbent in Adsorption organic pollutant
Application.
One, the preparation of supermolecule organic framework materials
The preparation of supermolecule organic framework materials of the present invention is column [5] aromatic hydrocarbons of main body naphthalimide functionalization in cyclohexanol
（P5N）With double 4,4 bipyridine salts of object（G）Assembled with equimolar ratio, is labeled as SOFs-P5G.
Wherein, column [5] aromatic hydrocarbons of main body naphthalimide functionalization（P5N）Structural formula be：
n=1,2,3,4；
Double 4,4 bipyridine salts of object（G）Structure be as follows：
The assembly model of Subjective and Objective is as follows：
The Analysis on Mechanism that supermolecule polymer gel TDPG is formed below by nuclear-magnetism figure, nuclear-magnetism titration hydrogen spectrogram.Fig. 1 is
The moiety concentrations nuclear-magnetism figure of P5N.In Fig. 1, from（b）~（g）The concentration of P5N is gradually increased, it can be found that H1-7 is moved to High-Field
It is dynamic, illustrate that there are π-π effects between the column aromatic hydrocarbons group of P5N and naphthalimide group and another molecule P5N.Fig. 2 is P5N and G
Nuclear-magnetism titrate hydrogen spectrogram.Wherein（a）P5N；（b）~（h）G containing different equivalents.From fig. 2 it can be seen that on object G
Hydrogen Proton Ha, Hb, Hc, Hd and He are to low field displacement, while the Hydrogen Proton H6 and H7 in main body P5N column aromatic hydrocarbons group is to High-Field
Displacement, illustrates that object G pyridinium moieties enter the cavity of column aromatic hydrocarbons.Main body P5N and object G can be illustrated by the above phenomenon
It is assembled by host and guest's recognition reaction and π-π effect, to obtain supermolecule organic framework materials SOFs-P5G.
Two, absorption of the supermolecule organic frame SOFs-P5G to each pollutant
12 clean 50mL volumetric flasks are taken, weigh the contaminant compound adsorbed respectively（Such as：Methylene blue, gold
Orange, bismark brown Y, Giemsa stain agent, methyl orange, rhodamine B, tonyred 1, tonyred 2, picric acid, alpha naphthol, permanganic acid
Potassium, potassium bichromate）In beaker, adding 10mL distilled water is completely dissolved solid, then respectively liquid relief to ready colorimetric
Guan Zhong, is then diluted to 25mL scale with distilled water, and configuration concentration is 1 × 10-3mol·L−1Aqueous solution, for use.
The above-mentioned configured each pollutant aqueous solution of 50uL is pipetted respectively（1.0×10-3mol/L）In 5mL reagent bottle
In, distilled water dilution is then added and is settled to 5mL scale, shakes up, forming concentration is 1.0 × 10-5Each pollutant of mol/L is dilute
Solution is stood, for use.
12 parts of above-mentioned supermolecule organic frame SOFs-P5G powder prepared are weighed, every part is 2 milligrams, is added separately to
Above-mentioned configured concentration is 1.0 × 10-5In each pollutant weak solution of mol/L, it is stirred at room temperature after forty minutes, it is quiet
It sets.It was found that the color fade of each pollutant weak solution.Fig. 3 is SOFs-P5G to 12 kinds of pollutant Adsorption efficiency bar shapeds
Figure（From left to right：Methylene blue, gold orange, bismark brown Y, Giemsa stain agent, methyl orange, rhodamine B, tonyred 1, tonyred
2, picric acid, alpha naphthol, potassium permanganate, potassium bichromate）.As seen from Figure 3, supermolecule organic frame prepared by the present invention
SOFs-P5G powder is for pollutant methylene blue, gold orange, bismark brown Y, Giemsa stain agent, methyl orange, rhodamine B, the Sudan
Red 1, tonyred 2, picric acid, alpha naphthol, potassium permanganate, potassium bichromate all has good Adsorption effect.By with purple
Outer absorption spectrum monitoring, is calculated its removal rate to various pollutants.As a result, its removal rate for all contaminants
Both greater than 50 %, wherein the removal rate of potassium permanganate is up to 99 %.
Three, supermolecule organic frame SOFs-P5G desorption
The above-mentioned supermolecule organic framework materials SOFs-P5G powder for being adsorbed with pollutant is added in dehydrated alcohol, 35 ~
Behind stirred in water bath 15 minutes of 40 DEG C, the pollutant being adsorbed is released；It is filtered, it is dry, keep supermolecule organic
Frame material SOFs-P5G achievees the purpose that Recovery and recycle uses.Fig. 4 is supermolecule organic framework materials SOFs-P5G to first
Base orange（a）, rhodamine B（b）, picric acid（c）, potassium permanganate（d）Removal efficiency bar chart is recycled for multiple times.As shown in Figure 4,
For the pollutant in adsorbed water body after supermolecule organic framework materials SOFs-P5G desorption, still there is very high removal
Rate.
Four, Adsorption basis mechanism of the SOFs-P5G to each pollutant
By the way that by taking Adsorption of Methyl Orange as an example, We conducted the discussion of adsorption mechanism.We conducted methyl oranges to SOFs- first
The nuclear-magnetism titration experiments of P5G（See Fig. 5）.All from Fig. 5 it will be seen that peak Hydrogen Proton Ha, Hb, Hc and Hd on pyridiniujm
It is displaced to High-Field, the Hydrogen Proton H1, H2, H3 and H4 in methyl orange are displaced to low field, are illustrated in methyl orange and SOFs-P5G
Pyridiniujm between exist through the electrostatic interaction of zwitterion（See Fig. 3）.Meanwhile also being proved by two-dimentional nuclear-magnetism, such as
Shown in Fig. 6, A, B, tetra- reference points of C and D are the Hydrogen Proton H1 in Hydrogen Proton H6 on column aromatic hydrocarbons, H7 and H11 and methyl orange respectively,
The reference point of H2, H3 and H4 illustrate there is C-H- π and π-π effect between methyl orange and column aromatic hydrocarbons.It can be pushed away by these phenomenons
It surveys, during removing each pollutant, there are a variety of interaction forces（Such as：C-H- π effect, π-π effect, zwitterion
Electrostatic interaction etc.）, therefore, SOFs-P5G can be used for that pollutant each in aqueous solution is efficiently separated and removed.And it is this
Suction-operated is to be formed and with classes of compounds weak interaction force, but these weak interaction forces are easy to be broken
It is bad, therefore desorption can be carried out and separate each pollutant, reach the recycling of adsorbent material, this absorption point
There is important application value in molecule removal field from performance.
Detailed description of the invention
Fig. 1 is the concentration nucleus magnetic hydrogen spectrum figure of P5N.
The nuclear-magnetism that Fig. 2 is P5N and G titrates hydrogen spectrogram.
Fig. 3 is SOFs-P5G to 12 kinds of pollutant Adsorption efficiency bar charts.
Fig. 4 is SOFs-P5G pairs of supermolecule organic framework materials（a）Methyl orange,（b）Rhodamine B,（c）Picric acid,（d）It is high
Removal efficiency bar chart is recycled for multiple times in potassium manganate.
Fig. 5 is that methyl orange titrates hydrogen spectrogram to the nuclear-magnetism of SOFs-P5G.
Fig. 6 is the two-dimentional nuclear-magnetism hydrogen spectrogram of methyl orange and SOFs-P5G.
Specific embodiment
Below by specific embodiment to the preparation of supermolecule organic framework materials SOFs-P5G of the present invention and absorption waste water
The performance of middle organic pollutant is described further.
The preparation of embodiment 1, supermolecule organic framework materials SOFs-P5G
（1）The synthesis of main body P5N：In 50ml acetonitrile, 0.58g is added（5×10-3mol）Column [5] aromatic hydrocarbons P5 of bromo,
0.43g（1.5×10-3mol）Naphthalamide derivatives, in 80 DEG C of reaction 48h；To be cooled to room temperature after reaction, rotation
Solvent is evaporated off, sample upper prop is mixed, with petroleum ether:Ethyl acetate=10:1~10:5（v/v）Elution, it is solidifying for obtaining yellow solid product
Glue factor P5N；Yield is 75.6%.
（2）The synthesis of object G：1.9801g is added in 100ml acetonitrile（1.89 g, 6.3 mmol）1,10- dibromo-decane
With 4,4'- bipyridyl（5.56g, 35.7 mmol）, it is stirred at reflux at 90 ~ 100 DEG C 18 hours；It is cooled to room temperature, is leaked with Bu Shi
Bucket is filtered, and with acetonitrile and ethanol washing 3 ~ 5 times, obtaining 3.3g pistac powdery product is guest compound G.It produces
Rate is 86%.
（3）The synthesis of supermolecule organic framework materials SOFs-P5G：In 0.2ml cyclohexanol, main body P5N is added
（0.0050g, 4.5 × 10-6mol）, object G（0.0047g, 4.5 × 10-6mol）, heating makes it completely dissolved, is subsequently cooled to
Room temperature, drying, obtains stable supermolecule organic framework materials SOFs-P5G.
Embodiment 2, supermolecule organic frame SOFs-P5G efficiently separating and removing to pollutant
Configuration concentration is 5mL 1 × 10-5Each pollutant of M（Methylene blue, gold orange, bismark brown Y, Giemsa stain agent, first
Base orange, rhodamine B, tonyred 1, tonyred 2, picric acid, alpha naphthol, potassium permanganate, potassium bichromate）Aqueous solution；Weigh oversubscription
Sub- organic framework materials SOFs-P5G powder weighs 12 parts, and every part is 2 milligrams, is added separately to above-mentioned each pollutant weak solution
In, it shakes after forty minutes, stands, take residual supernatant to do and carry out uv-spectrophotometric test, record its absorbance.Then basis
Langbobier law calculates the concentration of its residual solution, to calculate eliminating rate of absorption.Supermolecule organic frame SOFs-P5G
1 is shown in Table for various pollutants removal rate：
Embodiment 3, supermolecule organic frame SOFs-P5G recycling
The aqueous solution for the organic framework materials SOFs-P5G powder for having adsorbed each pollutant is filtered, drying and processing.So
Dry powder is moved to afterwards in 12 5 milliliters of reagent bottles respectively, 4 milliliters of dehydrated alcohols are added, the water-bath for being 35 degrees Celsius in temperature
Middle concussion 15 minutes, discovery aqueous solution color become the color of each pollutant before adsorbing, illustrate organic framework materials SOFs-
P5G releases each pollutant of absorption.Then it is once being filtered, with ethanol washing 3 ~ 5 times, drying obtains original
The organic framework materials SOFs-P5G powder of beginning.The organic framework materials SOFs-P5G powder of recycling can also carry out repeatedly simultaneously
Recycling.
Claims (8)
1. a kind of preparation method of supermolecule organic frame SOFs-P5G, be in cyclohexanol, main body naphthalimide functionalization
Column [5] aromatic hydrocarbons is formed with equimolar than self assembly with double 4,4 bipyridine salts of object；
The structural formula of column [5] aromatic hydrocarbons of the main body naphthalimide functionalization is：
n=1,2,3,4；
The structural formula of double 4,4 bipyridine salts of the object is as follows：
。
2. the preparation method of supermolecule organic frame SOFs-P5G as described in claim 1, it is characterised in that：Main body naphthalimide
Double contents of 4,4 bipyridine salts in system of column [5] aromatic hydrocarbons and object of functionalization are 1.5 ~ 2.5g/mL.
3. the supermolecule organic frame SOFs-P5G of method preparation as described in claim 1 is for the pollution in Adsorption water body
Object.
4. supermolecule organic frame SOFs-P5G as claimed in claim 3 is for the pollutant in Adsorption water body, feature
It is：Pollutant is to have dyestuff.
5. supermolecule organic frame SOFs-P5G as claimed in claim 4 is for the pollutant in Adsorption water body, feature
It is：The organic dyestuff be methylene blue, gold orange, bismark brown Y, Giemsa stain agent, methyl orange, rhodamine B, tonyred 1,
Tonyred 2.
6. supermolecule organic frame SOFs-P5G as claimed in claim 3 is for the pollutant in Adsorption water body, feature
It is：The pollutant is potassium permanganate, potassium bichromate.
7. supermolecule organic frame SOFs-P5G as claimed in claim 3 is for the pollutant in Adsorption water body, feature
It is：The pollutant is picric acid, alpha naphthol.
8. supermolecule organic frame SOFs-P5G as claimed in claim 3 is for the pollutant in Adsorption water body, feature
It is：The supermolecule organic framework materials SOFs-P5G for having adsorbed pollutant is added to dehydrated alcohol, in 35 ~ 40 DEG C of water-baths
Middle stirring can release pollutant, and supermolecule organic framework materials SOFs-P5G is made to reach Recovery and recycle use.
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| CN112242577A (en) * | 2020-10-16 | 2021-01-19 | 苏州大学 | Recycling method of lithium ion battery anode material |
| CN113097644A (en) * | 2021-04-01 | 2021-07-09 | 长兴常兴化工有限公司 | Preparation method of SOFs-P5G/PVDF lithium ion battery diaphragm |
| CN116376046A (en) * | 2023-05-10 | 2023-07-04 | 五邑大学 | Method for preparing metal-organic polymer based on cage-shaped supermolecular monomer |
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| CN113097644A (en) * | 2021-04-01 | 2021-07-09 | 长兴常兴化工有限公司 | Preparation method of SOFs-P5G/PVDF lithium ion battery diaphragm |
| CN113097644B (en) * | 2021-04-01 | 2023-03-31 | 河南锂动电源有限公司 | Preparation method of SOFs-P5G/PVDF lithium ion battery diaphragm |
| CN116376046A (en) * | 2023-05-10 | 2023-07-04 | 五邑大学 | Method for preparing metal-organic polymer based on cage-shaped supermolecular monomer |
| CN116376046B (en) * | 2023-05-10 | 2024-08-09 | 五邑大学 | Method for preparing metal-organic polymer based on cage-shaped supermolecular monomer |
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