CN106179233A - There is preparation and the application thereof of the metal-organic framework materials of biconjugate effect - Google Patents
There is preparation and the application thereof of the metal-organic framework materials of biconjugate effect Download PDFInfo
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- CN106179233A CN106179233A CN201610596726.5A CN201610596726A CN106179233A CN 106179233 A CN106179233 A CN 106179233A CN 201610596726 A CN201610596726 A CN 201610596726A CN 106179233 A CN106179233 A CN 106179233A
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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
- B01J20/223—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material containing metals, e.g. organo-metallic compounds, coordination complexes
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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
- B01J20/28014—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
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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
- C02F2101/30—Organic compounds
- C02F2101/34—Organic compounds containing oxygen
- C02F2101/345—Phenols
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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
- C02F2101/38—Organic compounds containing nitrogen
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- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
There is preparation and the application thereof of the metal-organic framework materials of biconjugate effect, belong to the technical field that water processes.The architectural feature of this kind of material be its pore passage structure be to be constructed by two distances about 0.5 1.0nm, the planar structure unit that is parallel to each other, can be with upper and lower two plane generation conjugations owing to entering the upper and lower both sides of planar conjugate molecule in duct, thus some organic aromatic molecules with conjugated structure are had stronger adsorption, the most this kind of material can have the high-efficiency adsorbent of organic fragrance pollutant of conjugated structure as removing.As a example by 2 naphthols and 1 naphthylamines, result of study shows that this material not only has record-breaking adsorbance to 2 naphthols and 1 naphthylamines, and has good reproducibility.
Description
Technical field
The present invention relates to a class and there is the preparation of metal-organic framework materials high-efficiency adsorbent and the application of biconjugate effect,
The especially adsorbing and removing to conjugated type contaminant molecule, belongs to the technical field that water processes.
Background technology
At present, the waste water of the discharge such as chemical plant, coke-oven plant pollutes containing substantial amounts of organic fragrance with conjugated structure
Thing, such as beta naphthal and naphthalidine etc., they are important industrial chemicals, can manufacture multiple dyestuff and rubber antioxidant, at environment
In be difficult to degrade, this kind of waste water abnormal smells from the patient weight, toxicity is big, and colourity is deep, particularly has obvious carcinogenesis, to environment, human body and
Organism impact greatly, has been listed in priority pollutants in many countries.And for fragrance pollutant organic in waste water
Processing method includes absorption method, bioanalysis, chemical oxidation, photocatalytic degradation, Electrocatalysis Degradation, Pervaporation etc., wherein inhales
Attached method is simple due to device, easily operates, low energy consumption, and safety is high and is considered as a kind of conventional method of wastewater treatment, therefore
Develop the adsorbent that adsorption capacity is high, the rate of adsorption is fast, simple to operate, with low cost significant.
Metal-organic framework materials (Metal-Organic Frameworks, MOFs), refers to metal ion or metal
Oxygen clusters and organic ligand, be coupled to each other by covalent bond or ionic-covalent bonds, and be self-assembly of has periodic network structure
Crystalline material.MOF material due to huge specific surface area, the high adsorption capacity to numerous materials, flexible and changeable skeleton construction,
Many characteristics such as special topological structure and good structure Scalability and favored by researcher.MOF material is at liquid
Phase adsorbing separation field shows good application prospect.
Summary of the invention
It is an object of the invention to provide a class have biconjugate effect metal-organic framework materials preparation method and should
With, the architectural feature of this kind of material be its pore passage structure be plywood hole, by two be parallel to each other, spacing is 0.5-1.0nm
Planar structure unit is constructed, and can occur altogether with upper and lower two planes owing to entering the upper and lower both sides of planar conjugate molecule in duct
Yoke effect, thus some organic molecules with planar conjugate structure are had stronger adsorption, the most this kind of material
As the similar beta naphthal of removing and the high-efficiency adsorbent of naphthalidine, and field of waste water treatment can be widely used in.
The preparation method of the metal-organic framework materials of the present invention, it is characterised in that comprise the following steps:
(1) will join in organic solvent based on the organic ligand of the planar conjugate structures such as porphyrin, the titanium mountain valley with clumps of trees and bamboo, aromatic rings, super
Sound disperses, and forms ligand solution；
(2) slaine is joined in above-mentioned solution, after reacting 1-120h under the conditions of 20～200 DEG C, is cooled to room temperature,
Filter, obtain product；
(3) by the repeated multiple times washing of product solvent obtained by step (2), to remove the raw material of residual in duct and miscellaneous
Matter, heat drying (such as temperature 30～200 DEG C), obtains the metallic organic framework with plywood hole structure the most under vacuum
Material.
Organic solvent described in above-mentioned steps is the organic solvent that can synthesize metal-organic framework materials, can be methanol, second
Alcohol, N, N '-dimethyl Methanamide, N, N ' dimethyl acetylamide, N, in N ' diethylformamide, N-Methyl pyrrolidone etc.
Plant or several；
Described slaine is the salt that can form metal-organic framework materials；Aluminium salt, zinc salt, mantoquita, magnesium can be selected from
Salt, iron salt, nickel salt, cobalt salt etc.；
The proportioning of planar conjugate structure organic ligand and slaine prepare according to common metal organic framework material in joining
Than.
Add after slaine in step (2) further or simultaneously, also can add regulator, described regulator be sour or
Alkali, as pH adjusting agent and mineralizer, consumption is typically not intended to, and preferably reconciles pH value 1-12；Can be formic acid, acetic acid, propanoic acid,
Benzoic acid, ammonia, Fluohydric acid., hydrochloric acid, nitric acid etc..
Described cleaning solvent can be water, methanol, ethanol, N, N ' dimethylformamide, N, N ' dimethyl acetylamide, two
Methyl sulfoxide, acetone, chloroform etc..
The reaction vessel used can be hydrothermal reaction kettle, flask, microwave reactor.
What the present invention prepared that the organic ligand and carrying out of the planar conjugate structure of employing adsorbs has planar conjugate structure
Organic molecule all can be selected from porphyrin, the titanium mountain valley with clumps of trees and bamboo, aromatic rings (naphthalene, naphthols, naphthylamines, nitronaphthalene), indole, pyridine, quinoline, carbazole
Deng.
Solvent used by absorption, can be water or organic solvent such as: methanol, ethanol, octane, heptane etc..Adsorption experiment can
To be intermittent reaction and fixed bed reaction.
The present invention relates to there is the metallic organic framework material of plywood hole structure as high-efficiency adsorbent, utilize biconjugate effect
Adsorbing and removing has organic fragrance pollutant of conjugated structure, such as beta naphthal and the adsorbing and removing of naphthalidine in waste water.
Compared with prior art, advantages of the present invention and having the beneficial effect that:
1. proposing and utilizing the metal-organic framework materials with plywood hole structure is adsorbent, by biconjugate effect,
Conjugation organic pollutant molecule can be adsorbed efficiently.Owing to, in this plywood hole structure, organic pollutant molecule can be same
Time and two conjugate planes effects of metal-organic framework materials, this is significantly better than common adsorbents only one of which conjugate planes with dirty
Dye thing molecular action.
2., due to the existence of this biconjugate effect, there is the metal-organic framework materials of plywood hole to conjugated type pollutant
Molecular force is very strong, and therefore adsorption rate is fast, and removal efficiency is high.
3. the metal-organic framework materials with plywood hole is high to the adsorbance of beta naphthal and naphthalidine, exceedes resin, carbon
The most of adsorbent such as material.
4. have plywood hole metal-organic framework materials absorption beta naphthal and naphthalidine after can well regenerate, permissible
Reusability.
Accompanying drawing explanation
Fig. 1 is the schematic diagram of the metal-organic framework materials absorption conjugated type molecule with biconjugate effect.
Fig. 2 is the metal-organic framework materials Al-PMOF structure chart with biconjugate effect.
Fig. 3 is the N under 77K of the metal-organic framework materials Al-PMOF with biconjugate effect2Adsorption/desorption isothermal
Line.
In Fig. 4, (a) (b) is the scanning electron microscope (SEM) photograph of the metal-organic framework materials Al-PMOF with biconjugate effect.
Fig. 5 is at 30 DEG C, and the adsorbance of the beta naphthal solution of 100ppm is become by Al-PMOF that embodiment 1 obtains in time
The curve (a) changed；The time dependent curve (b) of adsorbance to the naphthalidine solution of 100ppm.
Fig. 6 is at 30,40,50 DEG C, the Al-PMOF that embodiment 1 the obtains adsorption isotherm (a) to beta naphthal solution；Right
The adsorption isotherm (b) of naphthalidine solution.
Fig. 7 is the reproducibility that beta naphthal and naphthalidine are adsorbed by metal-organic framework materials Al-PMOF.
Detailed description of the invention
Below by specific embodiment, the present invention will be further described, but the invention is not limited in this.
Embodiment 1 has the preparation of the metal-organic framework materials Al-PMOF of biconjugate effect
2.5g part porphyrin (3.16mmol) is joined and fills 500mL N, in the flask of N '-dimethyl Methanamide, super
Sound 30min.Being subsequently adding 2.4g ANN aluminium nitrate nonahydrate (6.32mmol), stirring makes it dissolve.Add 250mL propanoic acid, 150
At DEG C, condensing reflux reacts 3 days, obtains dark red solid.This solid is through centrifugal, N, and N '-dimethyl Methanamide and methanol are repeatedly
Washing, is finally dried 12h in 150 DEG C of vacuum drying ovens, obtains Al-PMOF.
The adsorption isotherm of embodiment 2Al-PMOF absorption beta naphthal
First, prepare the aqueous solution of the beta naphthal of certain initial concentration, in the taper filling 250mL beta naphthal aqueous solution
In Ping, adding 10mg Al-PMOF, whole system is placed in 30,40,50 DEG C of constant-temperature tables concussion 24h, and centrifugal acquisition is clear subsequently
Liquid, uses ultraviolet-uisible spectrophotometer test solution peak value at 273.5nm, obtains respective concentration after dilution, and with just
The concentration of beginning solution contrasts, and obtains the material adsorption isotherm to beta naphthal at a temperature of three kinds, then carries out acquired results
Langmuir simulation is calculated Al-PMOF at 30 DEG C and the maximal absorptive capacity of beta naphthal is up to 549.5mg/g.
The adsorption isotherm of embodiment 3Al-PMOF absorption naphthalidine
First, prepare the aqueous solution of the naphthalidine of certain initial concentration, in the taper filling 250mL naphthalidine aqueous solution
In Ping, adding 10mg Al-PMOF, whole system is placed in 30,40,50 DEG C of constant-temperature tables concussion 24h, and centrifugal acquisition is clear subsequently
Liquid, uses ultraviolet-uisible spectrophotometer test solution peak value at 304.5nm, obtains respective concentration after dilution, and with just
The concentration of beginning solution contrasts, and obtains the material adsorption isotherm to naphthalidine at a temperature of three kinds, then carries out acquired results
Langmuir simulation is calculated Al-PMOF at 30 DEG C and the maximal absorptive capacity of naphthalidine is up to 571.4mg/g.
The dynamics research of embodiment 4Al-PMOF absorption beta naphthal
First, the aqueous solution of the beta naphthal of preparation 100ppm initial concentration, in the taper filling 250mL2-naphthols aqueous solution
In Ping, adding 10mg Al-PMOF, whole system is placed in 30 DEG C of shaking tables shakes the different time, is obtained clearly by centrifugal subsequently
Liquid, uses ultraviolet-uisible spectrophotometer test solution peak value at 273.5nm, obtains respective concentration after dilution, and with just
The concentration of beginning solution contrasts.Research finds, the absorption of beta naphthal is reached to adsorb saturated by Al-PMOF at 6h.
The dynamics research of embodiment 5Al-PMOF absorption naphthalidine
First, the aqueous solution of the naphthalidine of preparation 100ppm initial concentration, in the taper filling 250mL1-naphthylamines aqueous solution
In Ping, adding 10mg Al-PMOF, whole system is placed in 30 DEG C of shaking tables shakes the different time, is obtained clearly by centrifugal subsequently
Liquid, uses ultraviolet-uisible spectrophotometer test solution peak value at 304.5nm, obtains respective concentration after dilution, and with just
The concentration of beginning solution contrasts.Research finds, the absorption of naphthalidine is reached to adsorb saturated by Al-PMOF at 6h.
The reproducibility research of embodiment 6Al-PMOF absorption beta naphthal
We use solvent elution method to regenerate, and add ethanol and repeatedly wash in the Al-PMOF after absorption beta naphthal,
Then 150 DEG C of freeze-day with constant temperature 10h under vacuum 0.1MPa, are reused for the adsorbing and removing of beta naphthal, and this process repeats five times,
Every time after regeneration, adsorbance does not significantly decreases.
The reproducibility research of embodiment 7Al-PMOF absorption naphthalidine
We use solvent elution method to regenerate, and add ethanol and repeatedly wash in the Al-PMOF after absorption naphthalidine,
Then 150 DEG C of freeze-day with constant temperature 10h under vacuum 0.1MPa, are reused for the adsorbing and removing of naphthalidine, and this process repeats five times,
Every time after regeneration, adsorbance does not significantly decreases.
Embodiment 8 ADSORPTION IN A FIXED BED is tested
Fixed bed is used to carry out breakthrough curve experiment.The height of bed is 0.1m～1.5m, and internal diameter is 10mm～40mm, Al-PMOF
Packed height is 0.1m～1.2m, and by peristaltic pump constant speed, beta naphthal or the naphthalidine solution of the certain concentration of preparation are added bed
In, utilize ultraviolet-uisible spectrophotometer timing detection outflow concentration, and calculate corresponding adsorbance.
Claims (10)
1. a metal-organic framework materials, it is characterised in that pore passage structure is plywood hole, be by two be parallel to each other, spacing
Planar structure unit for 0.5-1.0nm is constructed, and this material has biconjugate effect.
2. the synthetic method of the metal-organic framework materials described in claim 1, it is characterised in that comprise the following steps:
(1) organic ligand of planar conjugate structure is joined in organic solvent, ultrasonic disperse, form ligand solution；
(2) slaine is joined in above-mentioned solution, after reacting 1-120h under the conditions of 20～200 DEG C, be cooled to room temperature, mistake
Filter, obtains product；
(3) by the repeated multiple times washing of product solvent obtained by step (2), with the raw material remained in removing duct and impurity,
Heat drying the most under vacuum, obtains the metal-organic framework materials with plywood hole structure.
3. according to the synthetic method of claim 2, it is characterised in that described organic solvent is methanol, ethanol, N, N '-dimethyl
Methanamide, N, N ' dimethyl acetylamide, N, one or more in N ' diethylformamide, N-Methyl pyrrolidone etc..
4. according to the synthetic method of claim 2, it is characterised in that described slaine is for can form metallic organic framework material
The salt of material, selected from aluminium salt, zinc salt, mantoquita, magnesium salt, iron salt, nickel salt, cobalt salt；The organic ligand of planar conjugate structure selected from porphyrin,
The titanium mountain valley with clumps of trees and bamboo, aromatic rings, indole, pyridine, quinoline, carbazole.
5. according to the synthetic method of claim 2 simultaneously, it is characterised in that add after slaine in step (2) or, be additionally added
Regulator, regulator is acid or alkali, and as pH adjusting agent and mineralizer, regulator is selected from formic acid, acetic acid, propanoic acid, benzoic acid, ammonia
Water, Fluohydric acid., hydrochloric acid, nitric acid.
6. according to the synthetic method of claim 5, it is characterised in that pH value 1-12 reconciled by regulator.
7. according to the synthetic method of claim 2, it is characterised in that cleaning solvent is selected from water, methanol, ethanol, N, N ' dimethyl
Methanamide, N, N ' dimethyl acetylamide, dimethyl sulfoxide, acetone, chloroform.
8. the application of the metal-organic framework materials described in claim 1, it is characterised in that for having planar conjugate structure
The absorption of organic molecular compound.
9. according to the application of claim 8, it is characterised in that the solvent used by absorption, for water or organic solvent.
10. according to the application of claim 8, it is characterised in that absorption is intermittent reaction and fixed bed reaction.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108452771A (en) * | 2018-02-14 | 2018-08-28 | 中山大学 | COFs composite material and preparation method and application of the carbon-based photonic crystal-derived from MOF containing porphyrin |
| CN111266088A (en) * | 2020-01-13 | 2020-06-12 | 武汉工程大学 | Efficient porous adsorbent for treating phenolic wastewater and preparation method thereof |
| CN114307967A (en) * | 2020-09-30 | 2022-04-12 | 湖南中烟工业有限责任公司 | Organic-inorganic composite aerogel for reducing phenolic ketone harmful substances in mainstream smoke and preparation and application thereof |
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| US20070116729A1 (en) * | 2005-11-18 | 2007-05-24 | Palepu Nageswara R | Lyophilization process and products obtained thereby |
| CN103483394A (en) * | 2013-09-17 | 2014-01-01 | 天津师范大学 | Organic complex with metal zinc as center body, preparation method thereof and application thereof |
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2016
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US20070116729A1 (en) * | 2005-11-18 | 2007-05-24 | Palepu Nageswara R | Lyophilization process and products obtained thereby |
| CN103483394A (en) * | 2013-09-17 | 2014-01-01 | 天津师范大学 | Organic complex with metal zinc as center body, preparation method thereof and application thereof |
Non-Patent Citations (2)
| Title |
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| ALEXANDRA FATEEVA ET AL.: "A Water-Stable Porphyrin-Based Metal–Organic Framework Active for Visible-Light Photocatalysis", 《ANGEW. CHEM.》 * |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108452771A (en) * | 2018-02-14 | 2018-08-28 | 中山大学 | COFs composite material and preparation method and application of the carbon-based photonic crystal-derived from MOF containing porphyrin |
| CN111266088A (en) * | 2020-01-13 | 2020-06-12 | 武汉工程大学 | Efficient porous adsorbent for treating phenolic wastewater and preparation method thereof |
| CN111266088B (en) * | 2020-01-13 | 2022-03-15 | 武汉工程大学 | Efficient porous adsorbent for treating phenolic wastewater and preparation method thereof |
| CN114307967A (en) * | 2020-09-30 | 2022-04-12 | 湖南中烟工业有限责任公司 | Organic-inorganic composite aerogel for reducing phenolic ketone harmful substances in mainstream smoke and preparation and application thereof |
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