CN109824907A - Super cross-linked polymer of waste plastics base of nitrogenous triazine ring and its preparation method and application - Google Patents
Super cross-linked polymer of waste plastics base of nitrogenous triazine ring and its preparation method and application Download PDFInfo
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- CN109824907A CN109824907A CN201910087855.5A CN201910087855A CN109824907A CN 109824907 A CN109824907 A CN 109824907A CN 201910087855 A CN201910087855 A CN 201910087855A CN 109824907 A CN109824907 A CN 109824907A
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Abstract
The present invention provides a kind of preparation method of the super cross-linked polymer of waste plastics base of nitrogenous triazine ring, steps are as follows: styrofoam being added in methylene chloride and is dissolved, then under conditions of ice-water bath, it is separately added into Cyanuric Chloride and anhydrous aluminum chloride is reacted, continue to react under heating conditions again, obtains head product；Head product is washed, is extracted, is dried to get the super cross-linked polymer of waste plastics base of nitrogenous triazine ring is arrived.The super cross-linked polymer obtained using preparation method of the invention in the market molecular sieve, compared with zeolite and various commercial activated carbons, have that removal effect is significant, low-cost advantage；Meanwhile the super cross-linked polymer of the nitrogenous triazine ring can quickly detect Nitroaromatic explosive in water based on the performance of its fluorescence response.The present invention turns waste into wealth waste and old polystyrol foamed plastic, solves the problems, such as that waste plastic pollutes environment, has good market application prospect.
Description
Technical field
The present invention relates to super CROSSLINKING POLYMER TECHNIQUE field more particularly to a kind of super crosslinkings of waste plastics base of nitrogenous triazine ring
Polymer and its preparation method and application.
Background technique
Triazine ring Quito pore polymer is a kind of organic porous material of the scarce π aroma system of high nitrogen content, can be with gold
Belong to ion formed coordinate bond, with arene molecule occur π-π interaction or formed hydrogen bond, make its absorption, drug release,
Photoelectric functional and catalysis etc. have a wide range of applications.However, currently preparing the poromeric side of triazine ring base
The disadvantages of cost of material that method has preparation is high, and the process conditions of synthesis are harsher.In addition, triazine ring base is poromeric
Application study is mainly the absorption to carbon dioxide in gas molecule and the Selective Separation to carbon dioxide and nitrogen, organic
The catalysis and photocatalysis of reaction are studied, fresh less for the absorption of Organic Pollutants In Water and fluorescence response research.Therefore, traditional
Triazine ring Quito pore polymer of method preparation does not have the advantage of mild preparation process and low cost, rare application yet
In the water pollution problems that solution is got worse.In addition, deposed polystyrene to be transformed into the material of high added value, and to a certain degree
On solve problem of environmental pollution caused by solid waste.
Summary of the invention
In view of this, the present invention provides a kind of preparation method of the super cross-linked polymer of waste plastics base of nitrogenous triazine ring,
It can be synthesized using preparation method provided by the invention with the useless of the adjustable cheap nitrogenous triazine ring in high-specific surface area, aperture
The super cross-linked polymer of waste plastics base of the super cross-linked polymer of plastics base, the nitrogenous triazine ring can be used in different size in water body
The organic pollutant molecule of size is efficiently removed and is quickly detected based on fluorescence response Nitroaromatic explosive in water.
The present invention provides a kind of preparation method of the super cross-linked polymer of waste plastics base of nitrogenous triazine ring, including following step
It is rapid:
Styrofoam is added in methylene chloride and dissolves, then under the conditions of ice-water bath, is separately added into trimerization by S1
Chlorine cyanogen and anhydrous aluminum chloride are reacted, then continue to react under heating conditions, obtain head product；
S2 washs the head product, Soxhlet extraction, dries and hand over to get to the waste plastics base of nitrogenous triazine ring is super
Linked polymer.
Further, in step S1, the styrofoam is selected from discarded styrofoam.
Further, in step S1, the mass ratio of the styrofoam and Cyanuric Chloride is 1:2.8-1:
8.4, the molar ratio of Cyanuric Chloride and anhydrous aluminum chloride is 1:1.
Further, in step S1, the reaction time of the ice-water bath condition is 10h.
Further, in step S1, the reaction temperature under the heating condition is 70 DEG C, reaction time 12h.
Further, in step S2, the process of washing are as follows: washed respectively 3 times using methylene chloride, acetone and water.
Further, in step S2, the process of Soxhlet extraction be with methanol Soxhlet extraction for 24 hours.
The present invention also provides a kind of super cross-linked polymerics of waste plastics base of nitrogenous triazine ring using the preparation of above-mentioned preparation method
The super cross-linked polymer of waste plastics base of object, nitrogenous triazine ring of the invention is made by styrofoam.
Further, adsorption capacity of the super cross-linked polymer of waste plastics base of the nitrogenous triazine ring to 2,4- chlorophenesic acid
112.96-680.27mg·g-1。
The super cross-linked polymer of waste plastics base of nitrogenous triazine ring of the invention is used not only for different size in water body
The organic pollutant molecule of size is efficiently removed, and can quickly be detected nitrobenzene in water based on fluorescence response and be exploded
Object.
Technical solution provided by the invention has the benefit that be contained using what preparation method provided by the invention obtained
The super cross-linked polymer of waste plastics base of nitrogen triazine ring has high specific surface area；It is obtained using preparation method of the invention nitrogenous
The super cross-linked polymer of waste plastics base of triazine ring in the market molecular sieve, compared with zeolite and various commercial activated carbons, have
Removal effect is significant, low-cost advantage；Preparation method process warm provided by the invention and, by waste and old polystyrol foam mould
Material is turned waste into wealth, and solves the problems, such as that waste plastic pollutes environment, has good market application prospect；Present invention preparation
The waste plastics base super cross-linked polymer of nitrogenous triazine ring Nitroaromatic explosive in water can quickly be detected based on fluorescence response.
Detailed description of the invention
Fig. 1 is the process of the preparation method of the super cross-linked polymer of waste plastics base of the nitrogenous triazine ring of the embodiment of the present invention 1
Schematic diagram.
Fig. 2 be the embodiment of the present invention 1 prepare nitrogenous triazine ring the super cross-linked polymer EPS-CC-3 of waste plastics base with respectively
The absorption property comparing result of kind commercial activated carbons.
Fig. 3 is the SEM image of raw material polystyrene foamed plastic of the present invention.
Fig. 4 is the useless modeling of waste plastics the base super cross-linked polymer EPS-CC-3, nitrogenous triazine ring of the nitrogenous triazine ring of the present invention
Expect the super cross-linked polymer EPS-CC-2 of base, nitrogenous triazine ring the super cross-linked polymer EPS-CC-1 of waste plastics base SEM image.
Specific embodiment
To make the object, technical solutions and advantages of the present invention clearer, below in conjunction with attached drawing to embodiment party of the present invention
Formula is further described.
Referring to FIG. 1, the embodiment provides a kind of super cross-linked polymers of waste plastics base of nitrogenous triazine ring
Preparation method, comprising the following steps:
Styrofoam is dissolved in methylene chloride, then in ice-water bath by step S1 at room temperature
Under the conditions of, be separately added into crosslinking agent Cyanuric Chloride and catalyst anhydrous aluminum chloride reaction 10h, after reaction again at 70 DEG C next time
Stream heating reaction 12h, obtains head product；Styrofoam is selected from discarded styrofoam；Polystyrene
The mass ratio of foamed plastic and Cyanuric Chloride is 1:2.8-1:8.4, and the molar ratio of Cyanuric Chloride and anhydrous aluminum chloride is 1:1.
Step S2 is washed head product 3 times respectively using methylene chloride, acetone and water, then uses methanol Soxhlet extraction for 24 hours,
It is dried in vacuum overnight, obtains the super cross-linked polymer of waste plastics base of nitrogenous triazine ring.
Adjustable contain by adjusting a series of available apertures of mass ratio of Cyanuric Chloride and styrofoam
The super cross-linked polymer of waste plastics base of nitrogen triazine ring.
The super cross-linked polymer of nitrogenous triazine ring prepared by the present invention is using Friedel-Crafts reaction as principle, in lewis acid
Catalyst it is existing under the conditions of, using in reaction equation crosslinking agent and polystyrene Fu Ke alkylation reaction occurs and is prepared.
The reaction equation of above-mentioned preparation method are as follows:
Below with reference to embodiment to the preparation side of the super cross-linked polymer of waste plastics base of nitrogenous triazine ring provided by the invention
Method is described in detail.
Embodiment 1:
Weigh 1.0023g styrofoam (Expandable Polystyrene；EPS it) is dissolved at room temperature
In 100mL methylene chloride, then under conditions of ice-water bath, it is separately added into crosslinking agent Cyanuric Chloride and the anhydrous chlorination of catalyst
Aluminium, wherein the mass ratio of styrofoam and Cyanuric Chloride is 1:8.4, and the molar ratio of Cyanuric Chloride and aluminium chloride is
1:1, the reaction system first react 10h under conditions of ice-water bath, and then above-mentioned system is transferred to stirring condensing reflux
In device, 12h is reacted under conditions of 70 DEG C；Head product after reaction is respectively washed 3 times with methylene chloride, acetone and water respectively,
Last methanol Soxhlet extraction obtains the super cross-linked polymer EPS- of waste plastics base of nitrogenous triazine ring after being dried in vacuum overnight afterwards for 24 hours
CC-3。
The super cross-linked polymer EPS-CC-3 of waste plastics base of nitrogenous triazine ring prepared by the embodiment of the present invention 1 and various business
The absorption property comparing result of active carbon is shown in Fig. 2, and as shown in Figure 2, the super crosslinking of the waste plastics base of nitrogenous triazine ring of the invention is poly-
It is excellent to the absorption property of 2,4- chlorophenesic acid to close object EPS-CC-3, is higher than various commercial activated carbons.
The super cross-linked polymer EPS-CC-3 of waste plastics base of nitrogenous triazine ring prepared by the embodiment of the present invention 1 and various business
The preparation cost comparison of active carbon is shown in Table 1.
Table 1: the super cross-linked polymer EPS-CC-3 of the waste plastics base of nitrogenous triazine ring is prepared into various commercial activated carbons
This comparison
As shown in Table 1, the system of the super cross-linked polymer EPS-CC-3 of the waste plastics base of the nitrogenous triazine ring of the embodiment of the present invention 1
Standby cost price is not high, and its absorption property is much better than commercially available active carbon.
Embodiment 2:
Weigh 1.0023g styrofoam (Expandable Polystyrene；EPS it) is dissolved at room temperature
In 100mL methylene chloride, then under conditions of ice-water bath, it is separately added into crosslinking agent Cyanuric Chloride and catalyst anhydrous aluminum chloride
10h is reacted, wherein the mass ratio of styrofoam and Cyanuric Chloride is 1:2.8, mole of Cyanuric Chloride and aluminium chloride
It is transferred in the device being condensed back with stirring than being 1:1, then by above-mentioned system, reacts 12h under conditions of 70 DEG C；After reaction
Head product respectively wash 3 times with methylene chloride, acetone and water respectively, later for 24 hours with methanol Soxhlet extraction, be dried in vacuum overnight,
Obtain the super cross-linked polymer EPS-CC-1 of waste plastics base of nitrogenous triazine ring.
Embodiment 3:
Weigh 1.0023g styrofoam (Expandable Polystyrene；EPS it) is dissolved at room temperature
In 100mL methylene chloride, then under conditions of ice-water bath, it is separately added into crosslinking agent Cyanuric Chloride and the anhydrous chlorination of catalyst
Aluminium, wherein the mass ratio of styrofoam and Cyanuric Chloride is 1:5.6, and the molar ratio of Cyanuric Chloride and aluminium chloride is
1:1, the reaction system react 10h under conditions of ice-water bath, then above-mentioned system is transferred to the dress being condensed back with stirring
In setting, 12h is reacted under conditions of 70 DEG C；Head product after reaction is respectively washed 3 times with methylene chloride, acetone and water respectively, it
Afterwards for 24 hours with methanol Soxhlet extraction, it is dried in vacuum overnight, obtains the super cross-linked polymer EPS-CC- of waste plastics base of nitrogenous triazine ring
2。
The super cross-linked polymer EPS-CC-3 of waste plastics base of nitrogenous triazine ring prepared by the embodiment of the present invention 1, embodiment 2 are made
The waste plastics of nitrogenous triazine ring prepared by the super cross-linked polymer EPS-CC-1 of the waste plastics base of standby nitrogenous triazine ring, embodiment 3
The specific surface area and pore-size distribution parameter of the super cross-linked polymer EPS-CC-2 of base is shown in Table 2.
Table 2: the super friendship of waste plastics base of the super cross-linked polymer EPS-CC-3 of the waste plastics base of nitrogenous triazine ring, nitrogenous triazine ring
Linked polymer EPS-CC-1, nitrogenous triazine ring the super cross-linked polymer EPS-CC-2 of waste plastics base specific surface area and pore-size distribution
Parameter
As shown in Table 2, the super cross-linked polymer EPS-CC-3 of waste plastics base for the nitrogenous triazine ring that prepared by the embodiment of the present invention 1
Specific surface area with higher.
The present invention implements the super cross-linked polymer EPS-CC-3 of waste plastics base of nitrogenous triazine ring of 1 preparation, embodiment 3 contains
The super cross-linked polymer EPS-CC-2 of the waste plastics base of nitrogen triazine ring and various document report materials are to 2,4 dichloro phenol (2,4-
Dichlorophenol absorption property comparison) is shown in Table 3.
Table 3: the super friendship of waste plastics base of the super cross-linked polymer EPS-CC-3 of the waste plastics base of nitrogenous triazine ring, nitrogenous triazine ring
The absorption property of linked polymer EPS-CC-2 and various document report materials compares
As shown in Table 3, the super cross-linked polymer EPS-CC-3 that prepared by the embodiment of the present invention 1 is at 25 DEG C to 2,4- chlorophenesic acid
Adsorptive value be 680.27mgg-1, considerably beyond other materials.
The styrofoam that Example 1 and Example 2 of the present invention, embodiment 3 use is in laboratory
Waste plastics, the SEM (Scanning Electron Microscope, scanning electron microscope) of raw material polystyrene foamed plastic
Image is shown in Fig. 3, the super crosslinking of waste plastics base of the super cross-linked polymer EPS-CC-3 of the waste plastics base of nitrogenous triazine ring, nitrogenous triazine ring
Polymer EPS-CC-2, nitrogenous triazine ring the SEM image of the super cross-linked polymer EPS-CC-1 of waste plastics base see that Fig. 4, Fig. 4 a are
The SEM image of the super cross-linked polymer EPS-CC-1 of the waste plastics base of nitrogenous triazine ring, Fig. 4 b are the waste plastics base of nitrogenous triazine ring
The SEM image of super cross-linked polymer EPS-CC-2, Fig. 4 c are the super cross-linked polymer EPS-CC-3 of waste plastics base of nitrogenous triazine ring
SEM image, from fig. 4, it can be seen that the super cross-linked polymer EPS-CC-3 of the waste plastics base of nitrogenous triazine ring be stratiform micropore knot
Structure, micropore quantity is more, and remains the structure of raw material polystyrene foamed plastic.
Take respectively 5mg embodiment 1, embodiment 2, nitrogenous triazine ring in embodiment 3 the super cross-linked polymer of waste plastics base
Being placed in 40mL concentration is 20mgL-12,4- chlorophenesic acid solution in, the pH value ranges of 2,4- chlorophenesic acid solution is 3-10,
The absorbance that solution after absorption is surveyed with ultraviolet-uisible spectrophotometer, measures a length of 284nm of 2,4- chlorophenesic acid maximum absorption wave.
It is 40,60,80,100,200mgL that concentration, which is respectively configured,-12,4- chlorophenesic acid solution, utilize UV, visible light point
Light luminosity measures absorbance of 2, the 4- chlorophenesic acid at 284nm, establishes the standard curve between absorbance and concentration, i.e. Y=
0.0122X+0.0071 (Y: absorbance；X:2,4- chlorophenesic acid concentration, unit mgL-1)；The calculating of equilibrium adsorption capacity is public
Formula: qe=((C0-Ce)V)/m(qeFor equilibrium adsorption capacity, unit mgg-1；C0、CeRespectively 2,4 dichloro phenol is initial dense
Degree and equilibrium concentration, unit mgL-1；V is liquor capacity, unit L；M is sorbent used quality, unit g).
The adsorption effect that experiment measures the super cross-linked polymer of waste plastics base of nitrogenous triazine ring when pH is 5 is best；And
30-400mg·L-12,4- chlorophenesic acid solution in, add 5mg the embodiment of the present invention 1 prepare nitrogenous triazine ring useless modeling
Expect the super cross-linked polymer EPS-CC-3 of base, EPS-CC-3 obtains its absorption for 2,4- chlorophenesic acid after adsorption equilibrium at room temperature
Amount is 112.96-680.27mgg-1。
In the absence of conflict, the feature in embodiment and embodiment herein-above set forth can be combined with each other.
The foregoing is merely presently preferred embodiments of the present invention, is not intended to limit the invention, it is all in spirit of the invention and
Within principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.
Claims (10)
1. a kind of preparation method of the super cross-linked polymer of waste plastics base of nitrogenous triazine ring, which comprises the following steps:
Styrofoam is added in methylene chloride and dissolves, then under conditions of ice-water bath, is separately added into three polychlorostyrene by S1
Cyanogen and anhydrous aluminum chloride are reacted, then continue to react under heating conditions, obtain head product；
S2 washs the head product, is Soxhlet extraction, dry to get poly- to the super crosslinking of the waste plastics base of nitrogenous triazine ring
Close object.
2. the preparation method of the super cross-linked polymer of waste plastics base of nitrogenous triazine ring according to claim 1, feature exist
In in step S1, the styrofoam is selected from discarded styrofoam.
3. the preparation method of the super cross-linked polymer of waste plastics base of nitrogenous triazine ring according to claim 1, feature exist
In in step S1, the mass ratio of the styrofoam and Cyanuric Chloride is 1:2.8-1:8.4, Cyanuric Chloride and nothing
The molar ratio of water aluminium chloride is 1:1.
4. the preparation method of the super cross-linked polymer of waste plastics base of nitrogenous triazine ring according to claim 1, feature exist
In in step S1, the reaction time of the ice-water bath condition is 10h.
5. the preparation method of the super cross-linked polymer of waste plastics base of nitrogenous triazine ring according to claim 1, feature exist
In in step S1, the reaction temperature under the heating condition is 70 DEG C, reaction time 12h.
6. the preparation method of the super cross-linked polymer of waste plastics base of nitrogenous triazine ring according to claim 1, feature exist
In, in step S2, the process of washing are as follows: washed respectively 3 times using methylene chloride, acetone and water.
7. the preparation method of the super cross-linked polymer of waste plastics base of nitrogenous triazine ring according to claim 1, feature exist
In, in step S2, the process of Soxhlet extraction be with methanol Soxhlet extraction for 24 hours.
8. a kind of super cross-linked polymer of waste plastics base of nitrogenous triazine ring, which is characterized in that by any one of claim 1 to 7 institute
The preparation method stated is made.
9. the super cross-linked polymer of waste plastics base of nitrogenous triazine ring according to claim 8, which is characterized in that described nitrogenous
The super cross-linked polymer of waste plastics base of triazine ring is 112.96-680.27mgg to the adsorption capacity of 2,4 dichloro phenol-1。
10. the application of the super cross-linked polymer of waste plastics base of nitrogenous triazine ring according to any one of claims 8, which is characterized in that described
The super cross-linked polymer of waste plastics base of nitrogenous triazine ring can in adsorbed water body different size size organic pollutant molecule with
And Nitroaromatic explosive in water is quickly detected based on fluorescence response.
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Cited By (1)
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| CN110465276A (en) * | 2019-07-16 | 2019-11-19 | 哈尔滨工程大学 | Super crosslinking efficient uranium absorption material of phenyl phosphate porous polymer of one kind and preparation method thereof |
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| CN108314856A (en) * | 2018-02-12 | 2018-07-24 | 西北工业大学 | A kind of preparation method of the level hole polystyrene material based on triazine skeleton |
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Application publication date: 20190531 |