CN107759796A - The preparation method of a kind of porous super cross-linked polymer - Google Patents
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- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
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Abstract
The present invention relates to a kind of porous super crosslinked polymeric materials and its preparation, mainly using aromatic silane compound as reaction monomers, under the catalysis of Lewis acid, using dimethoxymethane or paradimethoxybenzene as outside cross-linking agent, a kind of novel porous super crosslinked polymeric materials for being obtained using Fu Lide Kerafyrms thatch (Fu Ke) alkylated reaction；Experimental method mild condition used in the present invention, cost is relatively low and yield is high etc.；Super crosslinked polymeric materials prepared by the present invention have larger specific surface area and pore volume, good physical and chemical stability and heat endurance and excellent adsorption capacity etc.；The material of preparation has potential application prospect in carbon dioxide adsorption, hydrogen storage and sewage disposal.
Description
Technical field
The present invention relates to the preparation method of a kind of porous super cross-linked polymer, and in particular to more based on phenyl silane
The preparation method of pore structure polymer, belong to high-molecular porous polymeric material field.
Background technology
Organic porous polymer (MOPs) is a kind of built-up as basic construction unit using organic compound, has height
Specific surface area, the polymer porous material containing abundant pore structure.Porous polymer material due to big specific surface area and
Good pore structure, low density, good Chemical Physics and heat endurance, in recent years, catalysis is widely used in, sensed
Device, carbon dioxide capture, gas storage, molecule separate, the field such as insoluble drug release and photoelectricity, receive the pole of numerous researchers
Big concern.Generally by textural classification by MOPs point for covalent organic framework polymer (COFs), from tool microporous polymer (PIMs),
It is conjugated microporous polymer (CMPs) and super cross-linked polymer (HCPs).Wherein, the usual specific surface area of super cross-linked polymer is higher, and
Preparation method is simple and easy, is to realize one of organic porous polymer material of industrialized production earliest.Prepare HCPs's at present
Method mainly functional property monomer directly from condensation methods, polystyrene based precursor post-crosslinking method and with outside cross-linking agent weave rigidity
Simplex method.
Wherein, outside cross-linking agent braiding rigid unitary method reaction condition is gentle, and reaction reagent used is cheap, reaction cost
Low, pore structure is adjustable, and obtained porous polymer has larger specific surface area and enough micropores, and reaction yield is high, institute
To be widely used for synthesizing porous polymeric material, and the HCPs materials of gained have excellent adsorption capacity so that HCPs materials
Material has potential development and application prospect in solid absorbent field.
At present, the species that monomer used in porous polymer material is prepared by outside cross-linking agent braiding rigid unitary method mainly collects
In in rigid aromatic compound, the species of monomer is less, and adjustable structure is little.For this case, in the present invention
In, aromatic silane compound is incorporated into poromeric preparation synthesis by we, is greatly enriched synthesizing porous
The monomeric species of polymer, and utilize the adjustability of structure of silane monomer and the adjustability of functional group, it is possible to achieve to porous
The regulation and control and modification of the performance of polymeric material.
The content of the invention
The invention provides the preparation method of a kind of porous super cross-linked polymer, its object is to by by aromatic silicon
Hydride compounds are incorporated into poromeric preparation, optimize Macroscopic single crystal monomer and crosslinking agent and production technology, and are produced
Go out, function admirable and synthetic yield high porous super crosslinked polymeric materials low with production cost.
To realize the purpose of the present invention, there is provided following technical scheme：
The preparation method of a kind of super crosslinked polymeric materials, it is characterised in that comprise the following steps：
(1) preparing raw material mixed liquor：Using aromatic silane compound as monomer, monomer is dispersed in outside cross-linking agent and solvent
Middle acquisition raw material mixed liquor；
(2) preparation of porous super cross-linked polymer：Lewis acid catalysts are added in the raw material mixed liquor obtained into step (1)
Fu Lide-Kerafyrm thatch (friedel-craft) alkylated reaction occurs afterwards, further surpasses crosslinking and obtains crude product；
(3) purifying of porous super cross-linked polymer：Washing of Filter Cake and extracting after the filtration of crude product that will be obtained in step (2),
Catalyst is removed, described porous super cross-linked polymer can be obtained after drying.
The preparation method of described a kind of porous super cross-linked polymer, its aromatic silane compound monomer are dimethyl two
In phenyl silane, methyl triphenyl silane, tri-phenyl-silane, methyl ethylene diphenyl silane or vinyl tri-phenyl-silane
It is one or more of.
The preparation method of described a kind of porous super cross-linked polymer, its outside cross-linking agent is for dimethoxymethane or to diformazan
Epoxide benzene.
The preparation method of described a kind of porous super cross-linked polymer, its solvent be dichloromethane, chloroform, carbon tetrachloride,
One kind in 1,2- dichloroethanes or tetrahydrofuran, preferably 1,2- dichloroethanes.
The preparation method of described a kind of porous super cross-linked polymer, its friedel-craft catalysts are anhydrous ferric chloride
(FeCl3), anhydrous Aluminum chloride (AlCl3) or anhydrous stannic chloride (SnCl4) in one kind, preferably anhydrous ferric chloride.
The preparation method of described a kind of porous super cross-linked polymer, monomer and outside cross-linking agent rubs in its raw material mixed liquor
You are than being 1:2 ~ 12, the mol ratio of catalyst and monomer is 1 ~ 9:Between 1.
The preparation method of described a kind of porous super cross-linked polymer, lasting stirring is kept in its friedel-craft course of reaction, is added
Temperature control is after entering catalyst：25-85 DEG C of isothermal reaction 1-60 h.
The preparation method of described a kind of porous super cross-linked polymer, its tool for washing and being washed in extractive process after filtering
Body operating procedure is：Crude product is washed with solvent several times, until the filtrate color of last time washing uses rope close to after colourless
Family name's extractor extracts 24 h.Washing and extracting solvent for use are one in methanol, ethanol, acetone, tetrahydrofuran or dichloromethane
Kind is several.
The method have the characteristics that：Reaction condition is gentle, and reaction cost is low, and it is adjustable to react the pore structure of products therefrom, institute
Product has larger specific surface area and adjustable, reaction yield is high, and the porous super crosslinked polymeric materials of gained have excellent
Carbon dioxide capture, hydrogen storage and Dye Adsorption ability, applied to multiple fields, before there is good application and development
Scape.
Brief description of the drawings
Fig. 1 is the infared spectrum (IR) of the porous super cross-linked polymer in embodiment 1；
Fig. 2 is the nitrogen adsorption-desorption thermoisopleth (77 K) of the porous super cross-linked polymer in embodiment 1.
Embodiment
With specific experimental procedure, the present invention is further illustrated below.Following examples be intended to illustrate invention and
It is not the further limitation to the present invention.
Embodiment 1
The preparation method of a kind of porous super cross-linked polymer, comprises the following steps：
(1) preparing raw material mixed liquor：Using 2.13 g (10 mmol) dimethyl diphenyl silane as monomer, 4.56 g (60
Mmol) dimethoxymethane is outside cross-linking agent, and 15 mL 1,2- dichloroethanes is solvent, in three mouthfuls of burnings equipped with reflux condensing tube
Above raw material is added in bottle, the h of magnetic agitation 0.5, obtains raw material mixed liquor；
(2) preparation of porous super cross-linked polymer：Using anhydrous ferric chloride as catalyst, the raw material obtained into step (1) mixes
4.87 g (30 mmol) catalyst is added in liquid, Friedel-Crafts alkylation occurs, super crosslinking obtains crude product；
Lasting stirring is kept during Friedel-Crafts alkylation, temperature controlled detailed process is after adding catalyst：First,
25 DEG C are warming up to, the h of isothermal reaction 5；Then, 80 DEG C are warming up to, the h of isothermal reaction 19；
(3) purifying of porous super cross-linked polymer：The filtration of crude product that will be obtained in step (2), is washed simultaneously to its filter cake
Extracting, catalyst is removed, then the porous of described brown is made after drying 24 h to 72 h at 60 DEG C in vacuum drying chamber
Super cross-linked polymer.
The concrete operation step washed in simultaneously extractive process is washed after filtering is：Crude product is washed with methanol several times, directly
To last time washing filtrate color close to colourless；Then, 24 h are extracted with apparatus,Soxhlet's methanol.
Porous super crosslinked polymeric materials prepared by the preparation method according to the porous super cross-linked polymer of described one kind, it compares
Surface area is 1044 m2 g-1。
Embodiment 2
The preparation method of a kind of porous super cross-linked polymer, comprises the following steps：
(1) preparing raw material mixed liquor：Using 2.74 g (10 mmol) methyl triphenyl silane as monomer, 2.28 g (30 mmol)
Dimethoxymethane is outside cross-linking agent, and 30 mL dichloromethane are solvent, are added in the three-necked flask equipped with reflux condensing tube
Above raw material, the h of magnetic agitation 0.5, obtain raw material mixed liquor；
(2) preparation of porous super cross-linked polymer：Using anhydrous Aluminum chloride as catalyst, the raw material obtained into step (1) mixes
8.00 g (60 mmol) catalyst is added in liquid, Friedel-Crafts alkylation occurs, super crosslinking obtains crude product；
Lasting stirring is kept during Friedel-Crafts alkylation, temperature controlled detailed process is after adding catalyst：First,
45 DEG C are warming up to, the h of isothermal reaction 5；Then, 83 DEG C are warming up to, the h of isothermal reaction 43；
(3) purifying of porous super cross-linked polymer：The filtration of crude product that will be obtained in step (2), is washed simultaneously to its filter cake
Extracting, catalyst of going out, then the porous of described brown is made after drying 24 h to 72 h at 60 DEG C in vacuum drying chamber
Super cross-linked polymer.
The concrete operation step washed in simultaneously extractive process is washed after filtering is：Crude product is washed with ethanol several times, directly
To last time washing filtrate color close to colourless；Then, 24 h are extracted with apparatus,Soxhlet's methanol.
Porous super crosslinked polymeric materials prepared by the preparation method according to the porous super cross-linked polymer of described one kind, it compares
Surface area is 1083 m2 g-1。
Embodiment 3
The preparation method of a kind of porous super cross-linked polymer, comprises the following steps：
(1) preparing raw material mixed liquor：Using 2.60 g (10 mmol) tri-phenyl-silane as monomer, 6.85 g (90 mmol) diformazan
Epoxide methane is outside cross-linking agent, and 30 mL chloroforms are solvent, and above raw material is added in the three-necked flask equipped with reflux condensing tube,
The h of magnetic agitation 0.5, obtain raw material mixed liquor；
(2) preparation of porous super cross-linked polymer：Using anhydrous stannic chloride as catalyst, the raw material obtained into step (1) mixes
23.45 g (90 mmol) catalyst is added in liquid, Friedel-Crafts alkylation occurs, super crosslinking obtains crude product；
Lasting stirring is kept during Friedel-Crafts alkylation, temperature controlled detailed process is after adding catalyst：It is warming up to
80 DEG C, the h of isothermal reaction 48；
(3) purifying of porous super cross-linked polymer：The filtration of crude product that will be obtained in step (2), is washed simultaneously to its filter cake
Extracting, catalyst of going out, then the porous of described brown is made after drying 24 h to 72 h at 60 DEG C in vacuum drying chamber
Super cross-linked polymer.
The concrete operation step washed in simultaneously extractive process is washed after filtering is：Washed with methanol, acetone and tetrahydrofuran
Crude product several times, until the filtrate color of last time washing is close to colourless；Then, with apparatus,Soxhlet's ethanolic extraction 24
h。
Porous super crosslinked polymeric materials prepared by the preparation method according to the porous super cross-linked polymer of described one kind, it compares
Surface area is 1101 m2 g-1。
Embodiment 4
The preparation method of a kind of porous super cross-linked polymer, comprises the following steps：
(1) preparing raw material mixed liquor：With 1.06 g (5 mmol) dimethyl diphenyl silane, 1.12 g (5 mmol) methyl
Vinyl diphenyl silane is monomer, and 2.76 g (20 mmol) paradimethoxybenzene is outside cross-linking agent, 15 mL carbon tetrachloride
For solvent, above raw material is added in the three-necked flask equipped with reflux condensing tube, the h of magnetic agitation 0.5, obtains raw material mixed liquor；
(2) preparation of porous super cross-linked polymer：Using anhydrous ferric trichloride as catalyst, the raw material obtained into step (1) mixes
Close and 1.62 g (10 mmol) catalyst is added in liquid, Friedel-Crafts alkylation occurs, super crosslinking obtains crude product；
Lasting stirring is kept during Friedel-Crafts alkylation, temperature controlled detailed process is after adding catalyst：It is warming up to
60 DEG C, the h of isothermal reaction 48；
(3) purifying of porous super cross-linked polymer：The filtration of crude product that will be obtained in step (2), is washed simultaneously to its filter cake
Extracting, catalyst is removed, then the porous of described brown is made after drying 24 h to 72 h at 60 DEG C in vacuum drying chamber
Super cross-linked polymer.
The concrete operation step washed in simultaneously extractive process is washed after filtering is：Washed slightly with ethanol, acetone, dichloromethane
Product several times, until the filtrate color of last time washing is close to colourless；Then, 24 h are extracted with apparatus,Soxhlet's methanol.
Porous super crosslinked polymeric materials prepared by the preparation method according to the porous super cross-linked polymer of described one kind, it compares
Surface area is 1082 m2 g-1。
Embodiment 5
The preparation method of a kind of porous super cross-linked polymer, comprises the following steps：
(1) preparing raw material mixed liquor：With 1.37 g (5 mmol) methyl triphenyl silane and 1.30 g (5 mmol) triphenyl
Silane is monomer, and 8.29 g (60 mmol) paradimethoxybenzene is outside cross-linking agent, and 30 mL 1,2- dichloroethanes is solvent,
Above raw material is added in three-necked flask equipped with reflux condensing tube, the h of magnetic agitation 0.5, obtains raw material mixed liquor；
(2) preparation of porous super cross-linked polymer：Using aluminum trichloride (anhydrous) as catalyst, the raw material obtained into step (1) mixes
Close and 8.00 g (60 mmol) catalyst is added in liquid, Friedel-Crafts alkylation occurs, super crosslinking obtains crude product；
Lasting stirring is kept during Friedel-Crafts alkylation, temperature controlled detailed process is after adding catalyst：It is warming up to
80 DEG C, the h of isothermal reaction 1；
(3) purifying of porous super cross-linked polymer：The filtration of crude product that will be obtained in step (2), is washed simultaneously to its filter cake
Extracting, catalyst of going out, then the porous of described brown is made after drying 24 h to 72 h at 60 DEG C in vacuum drying chamber
Super cross-linked polymer.
The concrete operation step washed in simultaneously extractive process is washed after filtering is：It is some that crude product is washed with methanol and ethanol
It is secondary, until the filtrate color of last time washing is close to colourless；What is extracted in washing and extract after the filtering concretely comprises the following steps：
24 h are extracted with apparatus,Soxhlet's tetrahydrofuran.
Porous super crosslinked polymeric materials prepared by the preparation method according to the porous super cross-linked polymer of described one kind, it compares
Surface area is 499 m2 g-1。
Embodiment 6
The preparation method of a kind of porous super cross-linked polymer, comprises the following steps：
(1) preparing raw material mixed liquor：With 0.78 g (3 mmol) tri-phenyl-silane, 0.86 g (3 mmol) vinyl triphen
Base silane and 1.10 g (4 mmol) methyl triphenyl silane are monomer, and 8.29 g (60 mmol) paradimethoxybenzene is outer
Crosslinking agent, 30 mL tetrahydrofurans are solvent, and above raw material, magnetic agitation are added in the three-necked flask equipped with reflux condensing tube
0.5 h, obtain raw material mixed liquor；
(2) preparation of porous super cross-linked polymer：Using anhydrous ferric trichloride as catalyst, the raw material obtained into step (1) mixes
Close and 9.73 g (60 mmol) catalyst is added in liquid, Friedel-Crafts alkylation occurs, super crosslinking obtains crude product；
Lasting stirring is kept during Friedel-Crafts alkylation, temperature controlled detailed process is after adding catalyst：It is warming up to
50 DEG C, the h of isothermal reaction 60；
(3) purifying of porous super cross-linked polymer：The filtration of crude product that will be obtained in step (2), is washed simultaneously to its filter cake
Extracting, catalyst of going out, then the porous of described brown is made after drying 24 h to 72 h at 60 DEG C in vacuum drying chamber
Super cross-linked polymer.
The concrete operation step washed in simultaneously extractive process is washed after filtering is：It is that solvent washs with ethanol and tetrahydrofuran
Crude product several times, until the filtrate color of last time washing is close to colourless；Then, extracted with apparatus,Soxhlet's dichloromethane
24 h。
Porous super crosslinked polymeric materials prepared by the preparation method according to the porous super cross-linked polymer of described one kind, it compares
Surface area is 959 m2 g-1。
Claims (8)
1. the preparation method of a kind of porous super cross-linked polymer, it is characterised in that comprise the following steps：
(1) preparing raw material mixed liquor：Using aromatic silane compound as monomer, monomer is dispersed in outside cross-linking agent and solvent
Middle acquisition raw material mixed liquor；
(2) preparation of porous super cross-linked polymer：Lewis acid catalysts are added in the raw material mixed liquor obtained into step (1)
Fu Lide-Kerafyrm thatch (friedel-craft) alkylated reaction occurs afterwards, further surpasses crosslinking and obtains crude product；
(3) purifying of porous super cross-linked polymer：Washing of Filter Cake and extracting after the filtration of crude product that will be obtained in step (2),
Catalyst and unreacted monomer are removed, described porous super cross-linked polymer can be obtained after drying.
2. the preparation method of a kind of porous super cross-linked polymer according to claims 1, it is characterised in that the fragrance
Race's silane compound monomer is dimethyl diphenyl silane, methyl triphenyl silane, tri-phenyl-silane, methyl ethylene diphenyl
One or more in silane or vinyl tri-phenyl-silane.
3. the preparation method of a kind of porous super cross-linked polymer according to claims 1, it is characterised in that the diplomacy
It is dimethoxymethane or paradimethoxybenzene to join agent.
4. the preparation method of a kind of porous super cross-linked polymer according to claims 1, it is characterised in that the solvent
For one kind in dichloromethane, chloroform, carbon tetrachloride, 1,2- dichloroethanes or tetrahydrofuran.
5. the preparation method of the porous super cross-linked polymer according to claims 1, it is characterised in that the friedel-craft is anti-
It is anhydrous ferric trichloride (FeCl to answer catalyst3), anhydrous Aluminum chloride (AlCl3) or anhydrous stannic chloride (SnCl4) in one kind.
6. the preparation method of a kind of porous super cross-linked polymer according to claims 1, it is characterised in that the raw material
The mol ratio of monomer and outside cross-linking agent is 1 in mixed liquor:2 ~ 12, the mol ratio of catalyst and monomer is 1 ~ 9:Between 1.
7. the preparation method of a kind of porous super cross-linked polymer according to claims 1, it is characterised in that its friedel-craft
Lasting stirring is kept in course of reaction, temperature control is after adding catalyst：25-85 DEG C of isothermal reaction 1-60h.
8. the preparation method of a kind of porous super cross-linked polymer according to claims 1, it washs and extracted after filtering
During the concrete operation step that washs be：Crude product is washed with solvent several times, until the filtrate color of last time washing
Close to after colourless, 24 h are extracted with apparatus,Soxhlet's.Washing and extracting solvent for use be methanol, ethanol, acetone, tetrahydrofuran or
One or more in dichloromethane.
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| CN108948412A (en) * | 2018-05-17 | 2018-12-07 | 齐鲁工业大学 | A kind of siliceous poromeric preparation method for supercapacitor |
| CN109019751A (en) * | 2018-10-17 | 2018-12-18 | 齐鲁工业大学 | A kind of organic liquid waste adsorption treatment method |
| CN109317120A (en) * | 2018-10-19 | 2019-02-12 | 福州大学 | A kind of super crosslinked polymeric materials and preparation method thereof |
| CN109880150A (en) * | 2019-01-25 | 2019-06-14 | 浙江大学 | A kind of preparation method of super-hydrophobic high specific surface micro-pore Polymer adsorption material |
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