CN113480717B - Synthesis method of super-crosslinked ionic liquid polymer and application of super-crosslinked ionic liquid polymer in oil-water separation - Google Patents
Synthesis method of super-crosslinked ionic liquid polymer and application of super-crosslinked ionic liquid polymer in oil-water separation Download PDFInfo
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Abstract
The invention belongs to the technical field of synthesis of macromolecular polymers, and discloses a synthesis method and application of a super-crosslinked ionic liquid polymer. The method comprises the following steps: (1) mixing trimethylsilyl imidazole and benzyl chloride, dissolving in tetrahydrofuran, heating for reaction, filtering and collecting solids, washing and drying to obtain a precursor; (2) mixing and dissolving any one of aniline, benzyl alcohol and toluene with 1, 2-dichloroethane, adding dimethoxymethane, ferric trichloride and a precursor, and then reacting in a nitrogen atmosphere to obtain a macromolecular polymer; (3) and alternately centrifuging by using absolute ethyl alcohol and deionized water, removing supernatant after centrifugation, collecting precipitate, drying to obtain solid particles, performing Soxhlet extraction, and grinding to obtain solid powder particles. The method synthesizes the hypercrosslinked polymer through Friedel-crafts alkylation reaction copolymerization to prepare the macromolecular polymer which has high specific surface area, high pore canal and high aperture and can generate different separation effects on oil-water mixture.
Description
Technical Field
The invention relates to the technical field of synthesis of macromolecular polymers, in particular to a synthesis method of a super-crosslinked ionic liquid polymer and application of the super-crosslinked ionic liquid polymer in oil-water separation.
Background
Porous materials are of particular interest because of their unique properties such as large surface area, low skeletal density and high chemical stability, and related research has been attracting material chemists. Over the past few decades, the hot tide of developing porous materials has prompted scientists to develop many new porous materials, such as Metal Organic Frameworks (MOFs), elliptical organic frameworks (COFs), porous organic cages, microporous organic polymers (MOFs), and traditional porous materials, such as zeolites and activated carbon, among others.
The super-hydrophobic material has a micro-nano hierarchical structure with low surface energy, a rough surface and super-smoothness. At present, the most applied methods for preparing superhydrophobic materials are surface coating methods, chemical vapor deposition methods, and sol-gel methods. However, these methods require the use of complex instruments, which are difficult and time-consuming to operate, and the quantities of product obtained are generally low. Furthermore, the mechanical durability of superhydrophobic materials is also an issue because they can be damaged by mechanical abrasion and corrosive substances.
The macromolecular polymer has stable chemical property, can be recycled, and more importantly, individually shows very good hydrophilicity and individually shows very good hydrophobicity. The characteristics of high specific surface area, high pore canal, high aperture and the like of the porous material are combined with the hydrophobic property of the macromolecular polymer, so that the super-hydrophobic porous material for oil-water separation can be theoretically developed, and the problems of complex preparation method and poor mechanical durability of the existing super-hydrophobic material are solved. In addition, the connection between the super-crosslinked macromolecular polymer and the oil removal application is also a research field which is not developed at present, and the technical development is carried out, so that the application field of the super-crosslinked macromolecular polymer can be expanded.
Disclosure of Invention
The invention aims to overcome the defects of the background technology and provide a synthesis method of a hypercrosslinked ionic liquid polymer and application thereof in oil-water separation. The method synthesizes the hypercrosslinked polymer through Friedel-crafts alkylation reaction copolymerization, prepares the macromolecular polymer which has high specific surface area, high pore canal and high aperture and can generate different separation effects on oil-water mixture, and is applied to oil-water separation.
In order to achieve the purpose of the invention, the synthesis method of the hypercrosslinked ionic liquid polymer comprises the following steps:
(1) preparing a precursor: fully mixing trimethylsilyl imidazole and benzyl chloride, dissolving in tetrahydrofuran, heating for reaction, filtering and collecting solids, washing, finally performing vacuum drying, and collecting products to obtain a precursor;
(2) taking any one of aniline, benzyl alcohol and toluene, mixing with 1, 2-dichloroethane for dissolving, adding dimethoxymethane, finally adding ferric trichloride and the precursor obtained in the step (1), and then fully reacting in a nitrogen atmosphere to obtain a macromolecular polymer;
(3) carrying out post-treatment on the macromolecular polymer obtained in the step (2): firstly, alternately centrifuging for several times by using absolute ethyl alcohol and deionized water, removing supernatant after centrifugation, collecting precipitate, drying the precipitate, further purifying the obtained solid particles by Soxhlet extraction, and finally grinding the solid particles to obtain solid powder particles, namely the super-crosslinked ionic liquid polymer.
Further, in some embodiments of the present invention, the molar ratio of trimethylsilyl imidazole to benzyl chloride used in step (1) is 0.05-0.12: 0.09-0.26.
Preferably, in some embodiments of the present invention, the molar volume ratio of trimethylsilylimidazole to tetrahydrofuran is 0.05 to 0.12 mol: 40-60 ml.
Further, in some embodiments of the present invention, the heating reaction in step (1) is heating at 40-70 ℃ for 12-30 h.
Further, in some embodiments of the present invention, the washing in step (1) is 1 to 3 times with diethyl ether.
Further, in some embodiments of the present invention, the amount ratio of 1, 2-dichloroethane to precursor in step (2) is 30-50 ml: 1-5 g.
Further, in some embodiments of the present invention, the molar ratio of any one of aniline, benzyl alcohol and toluene to the precursor in the step (2) is 0.015 to 0.03: 0.03-0.06.
Further, in some embodiments of the present invention, the molar ratio of any one of aniline, benzyl alcohol and toluene to dimethoxymethane in the step (2) is 0.015 to 0.03: 0.045-0.06.
Further, in some embodiments of the present invention, the molar ratio of ferric trichloride to precursor in step (2) is 0.18-0.36: 0.03-0.06.
Further, in some embodiments of the present invention, the step (2) is performed under nitrogen atmosphere by first reacting at 40-60 ℃ for 3-5h, and then heating to 75-85 ℃ for 20-30 h.
Further, in some embodiments of the present invention, the step (3) of alternately centrifuging the anhydrous ethanol and the deionized water is performed at 6000-10000 r/min.
Further, in some embodiments of the present invention, the drying in steps (1) and (3) is drying at 60-90 ℃ for 10-25 h.
On the other hand, the invention also provides an application of the super-crosslinked ionic liquid polymer obtained by the synthesis method, namely the super-crosslinked ionic liquid polymer is used for oil-water separation.
Compared with the prior art, the invention has the following advantages:
(1) any one of three substances of aniline, benzyl alcohol and toluene can be selected in the step (2), three types of super-crosslinked macromolecular polymers can be finally obtained, the three types of super-crosslinked macromolecular polymers have larger specific surface areas and can be fully contacted with oil, the individual polymers have different functions on water and oil, some of the polymers have super-hydrophilic and super-oleophobic properties, and some of the polymers have super-oleophilic and super-hydrophobic properties; thereby the polymer shows excellent performance when applied to oil-water separation;
(2) the invention adopts the super-crosslinked polymer for oil removal application, has simple process, cheap equipment and rich pore canal pore diameter structure of the produced super-crosslinked polymer, has higher specific surface area and extremely high separation efficiency.
(3) The invention prepares the macromolecular polymer with high specific surface area, high pore and high pore diameter which can generate different effects on oil-water mixture by Friedel-crafts alkylation, and firstly proposes that the pore and pore diameter structure can generate different contact effects on water or oil by the macromolecular polymer, and the synthesis process is simple and easy to obtain and has low price.
Drawings
FIG. 1 is a left side view showing a water contact angle of a macromolecular polymer represented by aniline, obtained in example 1 of the present invention, one second before contacting the macromolecular polymer with water; the right graph of FIG. 1 shows that the stable water contact angle of the macromolecular polymer represented by aniline of the present invention after contacting water is 138 degrees, and good hydrophobicity is shown, so that the separation efficiency of the mixture of n-hexane, toluene and the like and water is at least 95 percent.
FIG. 2 is a left graph showing the water contact angle of a macromolecular polymer represented by benzyl alcohol according to example 2 of the present invention, which is one second before the macromolecular polymer is contacted with water; the right graph of FIG. 2 shows that the stable water contact angle of the macromolecular polymer represented by benzyl alcohol of the present invention after contacting water is 0 deg., and shows good hydrophilicity, so that the separation efficiency of the mixture of chloroform, carbon tetrachloride and the like and water is as high as at least 95%.
FIG. 3 is a left side view showing a water contact angle of a macromolecular polymer represented by toluene obtained in example 3 of the present invention, in a second before contacting with water; the right graph of FIG. 3 shows that the stable water contact angle of the macromolecular polymer represented by toluene of the present invention is 0 ℃ after contacting water, but the macromolecular polymer shows good hydrophilicity and cannot separate oil-water mixtures.
FIG. 4 is a schematic diagram showing the separation of a mixture of p-toluene and water, which is a macromolecular polymer represented by aniline, obtained in example 1 of the present invention.
FIG. 5 is a schematic diagram showing the separation of a mixture of chloroform and water from a macromolecular polymer represented by benzyl alcohol obtained in example 2 of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is described in further detail below with reference to the accompanying drawings and embodiments. Additional aspects and advantages of the invention will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the invention. It is to be understood that the following description is only illustrative of the present invention and is not to be construed as limiting the present invention.
The terms "comprises," "comprising," "includes," "including," "has," "having," "contains," "containing," or any other variation thereof, as used herein, are intended to cover a non-exclusive inclusion. For example, a composition, process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, process, method, article, or apparatus.
When an amount, concentration, or other value or parameter is expressed as a range, preferred range, or as a range of upper preferable values and lower preferable values, this is to be understood as specifically disclosing all ranges formed from any pair of any upper range limit or preferred value and any lower range limit or preferred value, regardless of whether ranges are separately disclosed. For example, when a range of "1 to 5" is disclosed, the described range should be interpreted to include the ranges "1 to 4", "1 to 3", "1 to 2 and 4 to 5", "1 to 3 and 5", and the like. When a range of values is described herein, unless otherwise stated, the range is intended to include the endpoints thereof and all integers and fractions within the range.
The indefinite articles "a" and "an" preceding an element or component of the invention are not intended to limit the number requirement (i.e., the number of occurrences) of the element or component. Thus, "a" or "an" should be read to include one or at least one, and the singular form of an element or component also includes the plural unless the number clearly indicates the singular.
Furthermore, the description below of the terms "one embodiment," "some embodiments," "an example," "a specific example," or "some examples," etc., means that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the invention. In this specification, the schematic representations of the terms used above are not necessarily for the same embodiment or example. Further, the technical features of the embodiments of the present invention may be combined with each other as long as they do not conflict with each other.
Example 1
Synthesis of a macromolecular Polymer represented by Aniline (i.e., Aniline was added in step (2)):
(1) preparation of a precursor: fully mixing 7.2g of trimethylsilylimidazole and 11.34g of benzyl chloride, dissolving in 50ml of tetrahydrofuran, heating at 60 ℃ for 24 hours, filtering to collect solid, washing the solid collected by filtering with diethyl ether for 3 times, drying at 80 ℃ in a vacuum drying oven for 18 hours, and finally collecting a product to obtain a precursor;
(2) dissolving 40ml of 1, 2-dichloroethane and 1.39g of aniline in a small beaker, adding 3.42g of dimethoxymethane, finally adding 7.31g of ferric trichloride and 2.13g of precursor obtained in the step (1), fully reacting in the atmosphere of nitrogen, firstly reacting at 50 ℃ for 4h, and then heating to 80 ℃ for 20 h;
(3) carrying out post-treatment on the macromolecular polymer obtained in the step (2): firstly, using absolute ethyl alcohol and deionized water to centrifuge for 5min at 6000r/min alternately for 5 times, centrifuging, then removing supernatant, collecting precipitate, drying the precipitate at 80 ℃ for 12h, carrying out Soxhlet extraction on obtained solid particles for further purification, and finally grinding to obtain solid powder particles, namely the super-crosslinked ionic liquid polymer represented by aniline.
Example 2
Synthesis of a macromolecular Polymer represented by benzyl alcohol (i.e., benzyl alcohol was added in step (2)):
(1) preparing a precursor: fully mixing 7.21g of trimethylsilylimidazole and 11.36g of benzyl chloride, dissolving in 50ml of tetrahydrofuran, heating at 60 ℃ for 24 hours, filtering to collect solid, washing the solid collected by filtering with diethyl ether for 3-5 times, drying at 80 ℃ in a vacuum drying oven for 18 hours, and finally collecting a product to obtain a precursor;
(2) dissolving 40ml of 1, 2-dichloroethane and 1.62g of benzyl alcohol in a small beaker, adding 3.44g of dimethoxymethane, finally adding 7.34g of ferric trichloride and 2.26g of precursor obtained in the step (1), fully reacting the mixture in the atmosphere of nitrogen, firstly reacting for 4 hours at 50 ℃, and then heating to 80 ℃ for reacting for 20 hours;
(3) carrying out post-treatment on the macromolecular polymer obtained in the step (2): firstly, using absolute ethyl alcohol and deionized water to centrifuge for 5min at 6000r/min alternately for 5 times, centrifuging, removing supernatant, collecting precipitate, drying the precipitate at 80 ℃ for 12h, carrying out Soxhlet extraction on obtained solid particles for further purification, and finally grinding to obtain solid powder particles, namely the hypercrosslinked ionic liquid polymer represented by benzyl alcohol.
Example 3
Synthesis of a macromolecular Polymer represented by toluene (i.e., toluene was added in step (2)):
(1) preparing a precursor: fully mixing 7.4g of trimethylsilylimidazole, dissolving in 50ml of tetrahydrofuran, heating at 60 ℃ for 24 hours, filtering to collect solid, washing the solid collected by filtering with diethyl ether for 3 times, drying at 80 ℃ in a vacuum drying oven for 18 hours, and finally collecting a product to obtain a precursor;
(2) dissolving 40ml of 1, 2-dichloroethane and 1.38g of toluene in a small beaker, adding 3.56g of dimethoxymethane, finally adding 7.44g of ferric trichloride and 2.23g of the precursor obtained in the step (1), fully reacting the mixture in the atmosphere of nitrogen, firstly reacting at 50 ℃ for 4h, and then heating to 80 ℃ for 24 h;
(3) carrying out post-treatment on the macromolecular polymer obtained in the step (2): firstly, using absolute ethyl alcohol and deionized water to centrifuge for 5min at 6000r/min alternately, 5 times in total, centrifuging, removing supernatant, collecting precipitate, drying the precipitate at 80 ℃ for 18h, carrying out Soxhlet extraction on obtained solid particles for further purification, and finally grinding to obtain solid powder particles, namely the super-crosslinked ionic liquid polymer represented by toluene.
Effects of the embodiment
Contact angle measurement:
the solid powders of examples 1 to 3 were each pressed into a flake shape, and then subjected to measurement of water contact angle; FIGS. 1 to 3 show a macromolecular polymer represented by aniline, a macromolecular polymer represented by benzyl alcohol and a macromolecular polymer represented by toluene, respectively.
Verification of oil-water separation property:
tests show that a proper amount of macromolecular polymer represented by aniline can effectively separate deionized water and toluene or a mixture of deionized water and normal hexane, and the separation efficiency of the two kinds of macromolecular polymer can reach at least 95%.
A proper amount of macromolecular polymer represented by benzyl alcohol can separate deionized water and chloroform or a mixture of the deionized water and carbon tetrachloride, and the separation efficiency of the two kinds of polymers can reach at least 95%.
A proper amount of macromolecular polymer represented by toluene can separate deionized water and chloroform, or a mixture of deionized water and carbon tetrachloride and a mixture of deionized water and toluene, or a mixture of deionized water and n-hexane, however, the two separation effects are not obvious.
It will be understood by those skilled in the art that the foregoing is only a preferred embodiment of the present invention, and is not intended to limit the invention, and that any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the scope of the present invention.
Claims (13)
1. A method for synthesizing a hypercrosslinked ionic liquid polymer is characterized by comprising the following steps:
(1) preparing a precursor: fully mixing trimethylsilyl imidazole and benzyl chloride, dissolving in tetrahydrofuran, heating for reaction, filtering and collecting solids, washing, finally performing vacuum drying, and collecting products to obtain a precursor;
(2) taking any one of aniline and benzyl alcohol, mixing and dissolving the aniline and benzyl alcohol with 1, 2-dichloroethane, adding dimethoxymethane, finally adding ferric trichloride and the precursor obtained in the step (1), and then fully reacting in a nitrogen atmosphere to obtain a macromolecular polymer;
(3) carrying out post-treatment on the macromolecular polymer obtained in the step (2): firstly, alternately centrifuging with absolute ethyl alcohol and deionized water for several times, removing supernatant after centrifugation, collecting precipitate, drying the precipitate, further purifying the obtained solid particles by Soxhlet extraction, and finally grinding to obtain solid powder particles, namely the super-crosslinked ionic liquid polymer.
2. The method for synthesizing a hypercrosslinked ionic liquid polymer as claimed in claim 1, wherein the molar ratio of trimethylsilyl imidazole to benzyl chloride used in step (1) is 0.05-0.12: 0.09-0.26.
3. The method for synthesizing a hypercrosslinked ionic liquid polymer as claimed in claim 1, wherein the molar volume ratio of trimethylsilyl imidazole to tetrahydrofuran is 0.05-0.12 mol: 40-60 ml.
4. The method for synthesizing a hypercrosslinked ionic liquid polymer as claimed in claim 1, wherein the heating reaction in step (1) is heating at 40-70 ℃ for 12-30 h.
5. The method for synthesizing a hypercrosslinked ionic liquid polymer as claimed in claim 1, wherein the washing in step (1) is 1-3 times with diethyl ether.
6. The method for synthesizing a hypercrosslinked ionic liquid polymer as claimed in claim 1, wherein the dosage ratio of 1, 2-dichloroethane to precursor in step (2) is 30-50 ml: 1-5 g.
7. The method for synthesizing a hypercrosslinked ionic liquid polymer as claimed in claim 1, wherein the molar ratio of any one of aniline and benzyl alcohol to the precursor in step (2) is 0.015-0.03: 0.03-0.06.
8. The method for synthesizing a hypercrosslinked ionic liquid polymer as claimed in claim 1, wherein the molar ratio of any one of aniline and benzyl alcohol to dimethoxymethane in step (2) is 0.015-0.03: 0.045-0.06.
9. The method for synthesizing a hypercrosslinked ionic liquid polymer as claimed in claim 1, wherein the molar ratio of ferric trichloride to precursor in step (2) is 0.18-0.36: 0.03-0.06.
10. The method for synthesizing a hypercrosslinked ionic liquid polymer as claimed in claim 1, wherein the step (2) of reacting under nitrogen atmosphere is carried out by reacting at 40-60 ℃ for 3-5h, and then heating to 75-85 ℃ for 20-30 h.
11. The method as claimed in claim 1, wherein the step (3) of alternately centrifuging anhydrous ethanol and deionized water is performed at 6000-10000 r/min.
12. The method for synthesizing a hypercrosslinked ionic liquid polymer as claimed in claim 1, wherein the drying in steps (1) and (3) is at 60-90 ℃ for 10-25 h.
13. Use of the hypercrosslinked ionic liquid polymer obtained by the synthesis method according to any one of claims 1 to 12 for oil-water separation.
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