CN109174036A - A kind of high molecular polymer adsorbent and the preparation method and application thereof - Google Patents
A kind of high molecular polymer adsorbent and the preparation method and application thereof Download PDFInfo
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- CN109174036A CN109174036A CN201811119769.XA CN201811119769A CN109174036A CN 109174036 A CN109174036 A CN 109174036A CN 201811119769 A CN201811119769 A CN 201811119769A CN 109174036 A CN109174036 A CN 109174036A
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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
- B01J20/261—Synthetic macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/02—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography
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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
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/3085—Chemical treatments not covered by groups B01J20/3007 - B01J20/3078
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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Abstract
The invention discloses a kind of high molecular polymer adsorbents and preparation method thereof, the high molecular polymer adsorbent is specifically prepared as follows: divinylbenzene, olefin amide substance and initiator being added in perforating agent, it is uniformly mixed, it is stirred to react 1~10h at 10~50 DEG C, obtains mixed liquor；Gained mixed liquor is transferred in the stainless steel crystallizing kettle of polytetrafluoroethyllining lining, 4~48h of crystallization makes reactant that polymerization reaction occur in 90~200 DEG C of crystallization casees, takes out stainless steel crystallizing kettle, cooled to room temperature after complete reaction；Solid product taking-up after crystallization is transferred in vacuum oven and is dried in vacuo, target product high molecular polymer PDVB-CONH is obtained2.The present invention effectively increases the adsorption site of material, substantially increases the NOx adsorption capacity of the unit mass of high molecular material by reasonably grafting functional group to macromolecular scaffold.
Description
(1) technical field
The invention belongs to Environmental Chemistries, the technical field of materials chemistry, are related to the processing of air pollutants, in particular to one
Kind high-molecular organic material and preparation method thereof and the application in terms of the adsorption cleaning processing of room temperature NOx.
(2) background technique
With the quickening of process of industrialization, car ownership is significantly greatly increased per capita for the world today, is being driven a vehicle and was being stopped
NOx (the NO+NO that tail gas generates in journey2) one kind is used as to be harmful to the human body substance constantly along with us.Such as in long tunnel and
The semiclosed place such as parking lot meets with blocking and stops, and can continue to generate a large amount of NOx being difficult to be discharged into atmosphere rapidly in vehicle exhaust, and
It is directly absorbed by the body and causes the symptom such as eyes and mucosal irritation, headache, respiratory disease and pulmonary dysfunction, to human health
Generate immense pressure.
The air cleaning in place semiclosed for long tunnel and parking lot etc. at present is mainly carried out by the way of ventilation
Processing, but the effect is unsatisfactory in practical applications.Carrying out enrichment absorption to low concentration of NO x using adsorbent material is that a kind of pole has
The method of effect.Such as the modified active carbon fiber method that Chinese patent (CN106824077A) is proposed, activated carbon fibre has abundant
Microcellular structure NOx can be made to assemble in duct, thus there is good adsorption effect for NOx, but in application process
Middle activated carbon fibre is absorbed to NO2Absorption is preferably, but very weak to NO absorbability, in addition, carbon material by foreign gas influenced compared with
Greatly, especially steam influences, and will lead to adsorbance and declines to a great extent；Zhang et al. (Langmuir., 1993,9:2331-2334)
It is proposed using molecular sieve as a kind of NOx adsorbent material, equally there is also can not be adsorbed completely to NO, therefore be badly in need of
Research and develop under a kind of room temperature it is highly efficient, using the succinct NOx adsorbent material of convenient, preparation flow.
(3) summary of the invention
The object of the invention is just to provide a kind of high molecular polymer and preparation method thereof and room temperature NOx adsorption application.
For achieving the above object, the present invention uses solvent-thermal method, constructs skeleton simultaneously by principal monomer of divinylbenzene
Three-dimensional manometer network duct is provided, by introducing the amide object with double bond alkene structures in polymerization process inside network duct
Matter is prepared for a kind of efficient NOx adsorbent material, and provides its application in room temperature NOx adsorption.
The invention adopts the following technical scheme:
A kind of high molecular polymer adsorbent, is specifically prepared as follows:
(1) divinylbenzene (DVB), olefin amide substance and initiator are added in perforating agent, is uniformly mixed, 10
It is stirred to react 1~10h at~50 DEG C, obtains mixed liquor；Divinylbenzene, perforating agent and the olefin amide class object
The mass ratio of matter is 1~10:1~40:1；The initiator and DVB mass ratio is 0.1~50:1000；The initiator
For the good solvent of divinylbenzene；
(2) mixed liquor obtained by step (1) is transferred in the stainless steel crystallizing kettle of polytetrafluoroethyllining lining, in 90~
4~48h of crystallization takes out reactant generation polymerization reaction not from the crystallization case after complete reaction in 200 DEG C of crystallization casees
Become rusty steel crystallizing kettle, cooled to room temperature；
(3) it will be taken out by the solid product after step (2) crystallization from the stainless steel crystallizing kettle, and be transferred to vacuum drying
It is dried in vacuo in case, obtains target product high molecular polymer PDVB-CONH2。
Further, in step (1), the perforating agent is methanol, ethyl alcohol, glycol, polyethylene glycol, 1,4-butanediol, sweet
Oil, phenol, salicylaldhyde, chloroform, acetylsalicylic acid, oxalic acid, acetic acid, toluene, heptane, n-hexane, hexamethylene,
Benzene, dimethylbenzene, polyvinylpyrrolidone, cetyl trimethylammonium bromide, DMF, benzoic acid, benzamide, tetrahydrofuran, third
One of ketone, cyclopentanone, pyridine, urea, alanine, diethanol amine or ethyl acetate or any several mixture.
Further, in step (1), the perforating agent is preferably benzene, DMF, tetrahydrofuran, acetone, ethyl acetate.
Further, in step (1), described to be stirred to react, mixing speed is 200~600rpm.
Further, in step (1), the olefin amide substance is Methacrylamide, acrylamide, tertiary alkene acyl
Amine, N hydroxymethyl acrylamide, N- hydroxyethyl acrylamide, N- butoxy methyl acrylamide, N- (isobutoxy) methyl-prop
Acrylamide, 2,6- diacrylamine pyridine, N, N- methylene-bisacrylamide, N, N-1,4- phenyl bisacrylamide, 3,5- third
One of acrylamide yl benzoic acid or dimethylamino-propyl Methacrylamide or any several mixture.
Further, in step (1), the initiator is to cease fragrant butyl ether, 2- hydroxy-2-methyl -1- phenyl ketone, hexichol
Ketone, benzoyl peroxide, lauroyl peroxide, isopropyl benzene hydroperoxide, tert-butyl hydroperoxide, potassium peroxydisulfate, persulfuric acid
One of sodium, ammonium persulfate, 2,2- azodiisobutyronitrile, azobisisoheptonitrile or di-isopropyl peroxydicarbonate are any
Several mixtures.
Further, in step (1), the initiator is preferably 2,2- azodiisobutyronitrile.
Further, in step (3), the drying condition is at vacuum degree -1 × 100~-0.2 × 100kpa 30~80
2~48h is dried in vacuo between DEG C, until perforating agent volatilization is complete.
The present invention also provides application of the high molecular polymer adsorbent in NOx adsorption.
Further, illustrate the gaseous mixture that NOx is NO and NO2 that volume ratio is 1:1, but NO and NO in the present invention2Ratio is not
It is only limitted to 1:1.
Compared with prior art, the beneficial effects of the present invention are:
(1) high molecular polymer adsorbent preparation flow prepared by the present invention is simple, operates easy；
(2) high molecular polymer adsorbent prepared by the present invention adsorbs securely NOx under room temperature, is swift in response, by impurity
Gases affect is small；
(3) present invention effectively increases the adsorption site of material by reasonably grafting functional group to macromolecular scaffold,
Substantially increase the NOx adsorption capacity of the unit mass of high molecular material.
Therefore, high-molecular organic material produced by the present invention shows good NOx adsorption capacity, and shows fabulous
Selectivity, at normal temperature to NOx molecule have fabulous enrichment adsorption effect, may be applied not only in vehicle-mounted purifier device
In, it can also be used to the main material in semiclosed place and breathing mask that the NOx such as underground parking easily assemble is applied in industry
Middle NOx reveals place.
(4) Detailed description of the invention
Fig. 1 is the NOx adsorption curve figure of high molecular polymer adsorbent prepared by embodiment 2.
Fig. 2 is the infrared characterization chart of high molecular polymer adsorbent prepared by embodiment 2.
Fig. 3 is the BET adsorption desorption curve and graph of pore diameter distribution of high molecular polymer adsorbent prepared by embodiment 2.
(5) specific embodiment
The present invention is described further combined with specific embodiments below, but the scope of the present invention is not limited in
This.
Embodiment 1
It takes 50.0g n-hexane in beaker, 12.5g (80%) divinylbenzene, 2.0g acrylamide and 0.1g2 is added,
2- azodiisobutyronitrile, mixed solution, with the revolving speed of 300rpm, stir 4h, are sufficiently mixed solution at 20 DEG C.It will stir later
Mixed solution after mixing is transferred in the stainless steel crystallizing kettle of polytetrafluoroethyllining lining, and crystallization makes instead for 24 hours under 100 DEG C of environment
It answers object to polymerize, stainless steel cauldron is taken out after reaction, after naturally cool to room temperature.Solid product after crystallization is taken out and is turned
It moves in beaker to be put into vacuum oven and be dried in vacuo for 24 hours under 70 DEG C, -1 × 100kpa, obtain sample high molecular polymer
PDVB-CONH2-1。
Embodiment 2
Take 50.0g tetrahydrofuran in beaker, be added 12.5g (80%) divinylbenzene, 2.0g acrylamide and
0.1g2,2- azodiisobutyronitrile, mixed solution, with the revolving speed of 300rpm, stir 4h, are sufficiently mixed solution at 20 DEG C.It
The mixed solution after stirring is transferred in the stainless steel crystallizing kettle of polytetrafluoroethyllining lining afterwards, the crystallization under 100 DEG C of environment
It polymerize reactant for 24 hours, stainless steel cauldron is taken out after reaction, after naturally cool to room temperature.Solid after crystallization is produced
Object taking-up is transferred in beaker to be put into vacuum oven to be dried in vacuo for 24 hours under 70 DEG C, -1 × 100kpa, obtains sample high score
Sub- polymer P DVB-CONH2-2。
Embodiment 3
It takes 50.0g acetone in beaker, 12.5g (80%) divinylbenzene, 2.0g acrylamide and 0.1g2,2- is added
Azodiisobutyronitrile, mixed solution, with the revolving speed of 300rpm, stir 4h, are sufficiently mixed solution at 20 DEG C.It later will stirring
Mixed solution afterwards is transferred in the stainless steel crystallizing kettle of polytetrafluoroethyllining lining, and crystallization makes to react for 24 hours under 100 DEG C of environment
Object polymerize, and stainless steel cauldron is taken out after reaction, after naturally cool to room temperature.Solid product after crystallization is taken out into transfer
It is put into vacuum oven at 70 DEG C, is dried in vacuo under -1 × 100kpa for 24 hours in beaker, obtain sample high molecular polymer
PDVB-CONH2-3。
Embodiment 4
Take 50.0g ethyl acetate in beaker, be added 12.5g (80%) divinylbenzene, 2.0g acrylamide and
0.1g2,2- azodiisobutyronitrile, mixed solution, with the revolving speed of 300rpm, stir 4h, are sufficiently mixed solution at 20 DEG C.It
The mixed solution after stirring is transferred in the stainless steel crystallizing kettle of polytetrafluoroethyllining lining afterwards, the crystallization under 100 DEG C of environment
It polymerize reactant for 24 hours, stainless steel cauldron is taken out after reaction, after naturally cool to room temperature.Solid after crystallization is produced
Object taking-up is transferred in beaker to be put into vacuum oven to be dried in vacuo for 24 hours under 70 DEG C, -1 × 100kpa, obtains sample high score
Sub- polymer P DVB-CONH2-4。
Embodiment 5
It takes 50.0g acetone in beaker, 12.5g (80%) divinylbenzene is added, acrylamide and 0.1g2,2- is not added
Azodiisobutyronitrile, mixed solution, with the revolving speed of 300rpm, stir 4h, are sufficiently mixed solution at 20 DEG C.It later will stirring
Mixed solution afterwards is transferred in the stainless steel crystallizing kettle of polytetrafluoroethyllining lining, and crystallization makes to react for 24 hours under 100 DEG C of environment
Object polymerize, and stainless steel cauldron is taken out after reaction, after naturally cool to room temperature.Solid product after crystallization is taken out into transfer
It is put into vacuum oven at 70 DEG C, is dried in vacuo under -1 × 100kpa for 24 hours in beaker, obtain sample high molecular polymer
PDVB-CONH2-5。
Embodiment 6
It takes 50.0g acetone in beaker, 12.5g (80%) divinylbenzene, 1.0g acrylamide and 0.1g2,2- is added
Azodiisobutyronitrile, mixed solution, with the revolving speed of 300rpm, stir 4h, are sufficiently mixed solution at 20 DEG C.It later will stirring
Mixed solution afterwards is transferred in the stainless steel crystallizing kettle of polytetrafluoroethyllining lining, and crystallization makes to react for 24 hours under 100 DEG C of environment
Object polymerize, and stainless steel cauldron is taken out after reaction, after naturally cool to room temperature.Solid product after crystallization is taken out into transfer
It is put into vacuum oven at 70 DEG C, is dried in vacuo under -1 × 100kpa for 24 hours in beaker, obtain sample high molecular polymer
PDVB-CONH2-6。
Embodiment 7
It takes 50.0g acetone in beaker, 12.5g (80%) divinylbenzene, 2.5g acrylamide and 0.1g2,2- is added
Azodiisobutyronitrile, mixed solution, with the revolving speed of 300rpm, stir 4h, are sufficiently mixed solution at 20 DEG C.It later will stirring
Mixed solution afterwards is transferred in the stainless steel crystallizing kettle of polytetrafluoroethyllining lining, and crystallization makes to react for 24 hours under 100 DEG C of environment
Object polymerize, and stainless steel cauldron is taken out after reaction, after naturally cool to room temperature.Solid product after crystallization is taken out into transfer
It is put into vacuum oven at 70 DEG C, is dried in vacuo under -1 × 100kpa for 24 hours in beaker, obtain sample high molecular polymer
PDVB-CONH2-7。
Embodiment 8
It takes 50.0g acetone in beaker, 12.5g (80%) divinylbenzene, 3.3g acrylamide and 0.1g2,2- is added
Azodiisobutyronitrile, mixed solution, with the revolving speed of 300rpm, stir 4h, are sufficiently mixed solution at 20 DEG C.It later will stirring
Mixed solution afterwards is transferred in the stainless steel crystallizing kettle of polytetrafluoroethyllining lining, and crystallization makes to react for 24 hours under 100 DEG C of environment
Object polymerize, and stainless steel cauldron is taken out after reaction, after naturally cool to room temperature.Solid product after crystallization is taken out into transfer
It is put into vacuum oven at 70 DEG C, is dried in vacuo under -1 × 100kpa for 24 hours in beaker, obtain sample high molecular polymer
PDVB-CONH2-8。
Embodiment 9
It takes 50.0g acetone in beaker, 12.5g (80%) divinylbenzene, 5.0g acrylamide and 0.1g2,2- is added
Azodiisobutyronitrile, mixed solution, with the revolving speed of 300rpm, stir 4h, are sufficiently mixed solution at 20 DEG C.It later will stirring
Mixed solution afterwards is transferred in the stainless steel crystallizing kettle of polytetrafluoroethyllining lining, and crystallization makes to react for 24 hours under 100 DEG C of environment
Object polymerize, and stainless steel cauldron is taken out after reaction, after naturally cool to room temperature.Solid product after crystallization is taken out into transfer
It is put into vacuum oven at 70 DEG C, is dried in vacuo under -1 × 100kpa for 24 hours in beaker, obtain sample high molecular polymer
PDVB-CONH2-9.NOx absorption test, test condition NO:250ppm+ are carried out to the high molecular material of embodiment 1-9 preparation
NO2: under the conditions of the dry gas of 250ppm, adsorption curve is shown in attached drawing 1 by taking embodiment 2 as an example；Embodiment 1-9 Surface Texture property representation
BET data sees attached list 1；Adsorption capacity data obtained by embodiment 1-9 see attached list 2；
1. embodiment 1-9 Surface Texture property representation of subordinate list
2. embodiment 1-9 NOx adsorption capacities chart of subordinate list
| Embodiment | NO/mg·g-1 | NO2/mg·g-1 |
| Embodiment 1 | 6.6 | 12.0 |
| Embodiment 2 | 32.6 | 51.0 |
| Embodiment 3 | 29.3 | 52.2 |
| Embodiment 4 | 37.9 | 56.7 |
| Embodiment 5 | 31.0 | 46.7 |
| Embodiment 6 | 28.3 | 47.5 |
| Embodiment 7 | 25.0 | 55.7 |
| Embodiment 8 | 23.2 | 58.7 |
| Embodiment 9 | 23.5 | 63.2 |
Claims (10)
1. a kind of high molecular polymer adsorbent, it is characterised in that: the high molecular polymer adsorbent is specifically according to as follows
It is prepared by method:
(1) divinylbenzene, olefin amide substance and initiator are added in perforating agent, is uniformly mixed, at 10~50 DEG C
It is stirred to react 1~10h, obtains mixed liquor；The quality of the divinylbenzene, perforating agent and the olefin amide substance
Than for 1~10:1~40:1；The initiator and the divinylbenzene mass ratio are 0.1~50:1000；Described draws
Send out the good solvent that agent is divinylbenzene；
(2) mixed liquor obtained by step (1) is transferred in the stainless steel crystallizing kettle of polytetrafluoroethyllining lining, in 90~200 DEG C
4~48h of crystallization in crystallization case takes out stainless steel crystallizing kettle from the crystallization case, naturally cools to room after complete reaction
Temperature；
(3) it will take out, be transferred in vacuum oven from the stainless steel crystallizing kettle by the solid product after step (2) crystallization
Vacuum drying, obtains target product high molecular polymer PDVB-CONH2。
2. high molecular polymer adsorbent as described in claim 1, it is characterised in that: in step (1), the perforating agent is
Methanol, ethyl alcohol, glycol, polyethylene glycol, 1,4-butanediol, glycerol, phenol, salicylaldhyde, chloroform, acetyl salicylic
Acid, oxalic acid, acetic acid, toluene, heptane, n-hexane, hexamethylene, benzene, dimethylbenzene, polyvinylpyrrolidone, cetyl trimethyl
Ammonium bromide, DMF, benzoic acid, benzamide, tetrahydrofuran, acetone, cyclopentanone, pyridine, urea, alanine, diethanol amine or second
One of acetoacetic ester or any several mixture.
3. high molecular polymer adsorbent as claimed in claim 2, it is characterised in that: in step (1), the perforating agent is
Benzene, DMF, tetrahydrofuran, acetone or ethyl acetate.
4. high molecular polymer adsorbent as described in claim 1, it is characterised in that: in step (1), described is stirred to react
In, mixing speed is 200~600rpm.
5. high molecular polymer adsorbent as described in claim 1, it is characterised in that: in step (1), the olefin amide
Substance is Methacrylamide, acrylamide, tertiary acrylamide, N hydroxymethyl acrylamide, N- hydroxyethyl acrylamide, N- fourth
Oxygroup Methacrylamide, N- (isobutoxy) Methacrylamide, 2,6- diacrylamine pyridine, N, N- methylene bisacrylamide
Amide, N, N-1, in 4- phenyl bisacrylamide, 3,5- acrylamide yl benzoic acid or dimethylamino-propyl Methacrylamide
One or any of several mixture.
6. high molecular polymer adsorbent as described in claim 1, it is characterised in that: in step (1), the initiator is
Cease fragrant butyl ether, 2- hydroxy-2-methyl -1- phenyl ketone, benzophenone, benzoyl peroxide, lauroyl peroxide, isopropylbenzene mistake
Hydrogen oxide, tert-butyl hydroperoxide, potassium peroxydisulfate, sodium peroxydisulfate, ammonium persulfate, 2,2- azodiisobutyronitrile, azo two different heptan
One of nitrile or di-isopropyl peroxydicarbonate or any several mixture.
7. high molecular polymer adsorbent as claimed in claim 6, it is characterised in that: in step (1), the initiator is
2,2- azodiisobutyronitriles.
8. high molecular polymer adsorbent as described in claim 1, it is characterised in that: in step (3), the drying condition is
At vacuum degree -1 × 100~-0.2 × 100kpa, 2~48h is dried in vacuo between 30~80 DEG C, until perforating agent is evaporated completely
Entirely.
9. application of the high molecular polymer adsorbent as described in claim 1 in NOx adsorption.
10. application as claimed in claim 9, it is characterised in that: the NOx is the NO and NO that volume ratio is 1:12Mixing
Gas.
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