CN112646127A - Porous aromatic skeleton material constructed by taking biphenyl as base block and mechanical ball milling preparation method thereof - Google Patents
Porous aromatic skeleton material constructed by taking biphenyl as base block and mechanical ball milling preparation method thereof Download PDFInfo
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- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/312—Non-condensed aromatic systems, e.g. benzene
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Abstract
A porous aromatic skeleton material constructed by taking biphenyl as a base block and a mechanical ball milling preparation method thereof belong to the technical field of organic porous material preparation. The polymerization reaction was confirmed by analyzing the infrared spectra of the monomers and the product. The scanning electron micrograph shows that PAF-107s are irregular spheres with a size of about 100 nm. By modulating biphenyl, anhydrous FeCl3And dimethanol formal, the porosity of PAF-107s was varied. Ball milled biphenyl and anhydrous FeCl3The BET specific surface area of the synthesized PAF-107a was 83m2g‑1. After the dimethyl formal is introduced into a synthesis system, the BET specific surface area of the PAF-107 is improved. In biphenyl, anhydrous FeCl3And dimethanol formal in a molar ratio of 1: 6: the BET specific surface area of PAF-107c at 6 is as high as 470m2g‑1. Furthermore, at 273K and 298K, ethane, ethylene and acetylene absorptions of PAF-107b were studiedAnd (4) adhesion performance.
Description
Technical Field
The invention belongs to the technical field of organic porous material preparation, and particularly relates to a porous aromatic framework material (marked as PAF-107s) constructed by taking biphenyl as a base block and a mechanical ball milling preparation method thereof.
Background
The organic porous material is a novel porous material which is formed by organic building blocks through polymerization reaction and is connected by covalent bonds. The organic porous material has the advantages of high stability, designable structure, easy functionalization, high porosity and the like due to the structure and the composition. The organic porous material has good application prospect in the fields of gas adsorption and separation, photoelectricity, catalysis and the like. At present, most of organic porous materials are synthesized in an organic solvent system. The organic porous material is applied, on one hand, the cost of raw materials needs to be controlled, and on the other hand, a simple and convenient synthesis process is needed. Mechanical grinding is a fast, efficient and relatively environmentally friendly synthetic route. The invention relates to biphenyl and anhydrous FeCl with different proportions3And dimethanol formal under mechanical grinding to prepare porous aromatic skeleton material (PAF-107 s).
Disclosure of Invention
The invention aims to provide a porous aromatic skeleton material (PAF-107s, including PAF-107a, PAF-107b, PAF-107c and PAF-107d) constructed by taking a plurality of biphenyls as base blocks and a mechanical ball milling preparation method thereof. The raw materials of the reaction comprise cheap biphenyl (Annagi reagent, 85 yuan/500 g) and anhydrous FeCl3(Annagi reagent, 85 yuan/500 g) and dimethanol formal (Annagi reagent, 95 yuan/500 ml). The porous performance of the PAF-107s is changed by adjusting the proportion of the three raw materials.
a. Mechanical milling of biphenyl and anhydrous FeCl3The reaction equation for synthesizing PAF-107a according to the invention is as follows:
infrared spectroscopic polymerization occurs at the para and ortho positions of the attached carbons.
b. Mechanical grinding of biphenyl and anhydrous FeCl in 3 proportions3And dimethanol formal, the reaction equations for the synthesis of PAF-107b, PAF-107c, and PAF-107d according to the present invention are as follows:
infrared spectroscopic polymerization occurs at the ortho and para positions relative to the linking carbon atom. The X-ray photoelectron spectrum and oxygen element analysis show that the product contains oxygen element. The proportion of the product containing ether side bonds is in the range of about 0.9 to 1.5.
The polymerization reaction of this patent uses biphenyl as the main building block and anhydrous FeCl3Used as a catalyst.
The invention relates to a method for preparing a porous aromatic skeleton material by mechanical ball milling, which comprises the following steps:
(1) synthesis of PAF-107a
(a) Mixing a mixture of 1: 3 Biphenyl and Anhydrous FeCl3Adding the mixture into a stainless steel ball milling tank, and then screwing the ball milling tank;
(b) putting the ball milling tank into a ball mill for ball milling for 0.5 h-2 h;
(c) opening the ball milling tank, washing the obtained product with 1M HCl, water and anhydrous methanol for multiple times in sequence, and then performing Soxhlet extraction with anhydrous methanol for 6-12 h;
(d) drying the soxhlet product in the step (c) for 4-40 hours at 100-150 ℃ under vacuum to obtain PAF-107 a; the test shows that the BET specific surface area of the PAF-107a is 83m2 g-1。
(2) Synthesis of PAF-107b, PAF-107c and PAF-107d
When synthesizing PAF-107b, PAF-107c and PAF-107d, the amount of biphenyl is the same, and anhydrous FeCl is adopted3And dimethyl formal in different amounts. PAF-107b, biphenyl: anhydrous FeCl3: dimethanol formal 1: 3: 3; PAF-107c, biphenyl: anhydrous FeCl3: dimethanol formal 1: 6: 6; PAF-107d, biphenyl: anhydrous FeCl3: dimethanol formal 1: 12: 12.
the method comprises the following specific steps:
(a) will rubThe molar ratio is 1: 3: 3. 1: 6: 6 or 1: 12: 12 biphenyl, anhydrous FeCl3And dimethanol formal are added into a stainless steel ball milling tank, and then the ball milling tank is screwed down;
(b) putting the ball milling tank into a ball mill for ball milling for 0.5 h-2 h;
(c) opening the ball milling tank, washing the obtained product with 1M HCl, water and anhydrous methanol for multiple times in sequence, and then performing Soxhlet extraction with anhydrous methanol for 6-12 h;
(d) drying the soxhlet product in the step (c) for 4-40 hours at 100-150 ℃ under vacuum to obtain PAF-107b, PAF-107c or PAF-107 d; tests show that the PAF-107b, the PAF-107c and the PAF-107d have good stability and porous property, and the BET specific surface areas of the PAF-107b, the PAF-107c and the PAF-107d are 223m2 g-1、470m2 g-1And 314m2 g-1。
Drawings
FIG. 1: the infrared spectra of the synthesized PAF-107a (curve 1 in the figure) and biphenyl (curve 2 in the figure);
FIG. 2: the PAF-107a nitrogen adsorption-desorption isotherm synthesized by the invention;
FIG. 3: the infrared spectra of the synthesized PAF-107b (curve 1 in the figure) and biphenyl (curve 2 in the figure);
FIG. 4: the PAF-107b nitrogen adsorption-desorption isotherm synthesized by the invention;
FIG. 5: scanning electron micrographs of the synthesized PAF-107b of the present invention;
FIG. 6: the X-ray photoelectron energy spectrum of the synthesized PAF-107 b;
FIG. 7: the infrared spectra of PAF-107c (curve 1 in the figure) and biphenyl (curve 2 in the figure) synthesized by the invention;
FIG. 8: the PAF-107c nitrogen adsorption-desorption isotherm synthesized by the invention;
FIG. 9: scanning electron micrographs of the synthesized PAF-107c of the present invention;
FIG. 10: thermogravimetric mapping of the synthesized PAF-107c of the present invention;
FIG. 11: x-ray photoelectron spectroscopy of the synthesized PAF-107 c;
FIG. 12: the infrared spectra of PAF-107d (curve 1 in the figure) and biphenyl (curve 2 in the figure) synthesized by the invention;
FIG. 13: the PAF-107d nitrogen adsorption-desorption isotherm synthesized by the invention;
FIG. 14: scanning electron microscope images of the synthesized PAF-107d of the invention;
FIG. 15: x-ray photoelectron spectroscopy of the synthesized PAF-107 d;
FIG. 16: the adsorption isotherm of ethane, ethylene and acetylene of the PAF-107b synthesized by the invention at 273K;
FIG. 17: the adsorption isotherms of ethane, ethylene and acetylene at 298K for the PAF-107b synthesized in the present invention.
FIG. 1 shows the IR spectrum of biphenyl and PAF-107a, corresponding to example 1. In the infrared absorption of biphenyl, 728cm-1And 695cm-1There are 2 distinct infrared absorption peaks, which are characteristic of the five adjacent hydrogens in biphenyl. For PAF-107a, at 808cm-1、755cm-1And 693cm-1There are 3 relatively distinct infrared absorption peaks, indicating that there are mainly 4 and 2 adjacent hydrogen hydrocarbon oscillation peaks in PAF-107 a. This suggests that the reaction is biased to occur in the ortho and para positions of the linking carbon atoms in the biphenyl.
FIG. 2 shows the nitrogen adsorption-desorption scheme for PAF-107a, corresponding to example 1. The BET specific surface area of PAF-107a was 83m2g-1；
FIG. 3 shows the IR spectrum of biphenyl and PAF-107b, corresponding to example 2. In the infrared absorption of biphenyl, 728cm-1And 695cm-1There are 2 distinct infrared absorption peaks, which are characteristic of the five adjacent hydrogens in biphenyl. For PAF-107b, at 811cm-1、760cm-1And 700cm-1There are 3 relatively distinct infrared absorption peaks, indicating that there are mainly 4 and 2 adjacent hydrogen hydrocarbon oscillation peaks in PAF-107 b. In PAF-107b, 2920cm-1And 2840cm-1There are several relatively broad absorption peaks between, indicating the presence of-CH in PAF-107b2or-CH3；1100cm-1There is a relatively distinct absorption peak indicating the possible presence of a C-O-C bond in PAF-107 b.
FIG. 4 shows the nitrogen adsorption-desorption scheme for PAF-107b, corresponding to example 2. The BET specific surface area of PAF-107b was 223m2 g-1；
FIG. 5 is a scanning electron micrograph of PAF-107b, corresponding to example 2. PAF-107b is an irregular sphere about 100nm in size.
FIG. 6 shows the X-ray photoelectron spectrum of PAF-107b, corresponding to example 2. The PAF-107b contains not only C but also O, and the C/O ratio is about 15.9.
FIG. 7 shows the IR spectrum of biphenyl and PAF-107c, corresponding to example 3. In the infrared absorption of biphenyl, 728cm-1And 695cm-1There are 2 distinct infrared absorption peaks, which are characteristic of the five adjacent hydrogens in biphenyl. For PAF-107c, at 811cm-1、760cm-1And 700cm-1There are 3 relatively distinct infrared absorption peaks, indicating that there are mainly 4 and 2 adjacent hydrogen hydrocarbon oscillation peaks in PAF-107 c. In PAF-107c, 2920cm-1And 2810cm-1There are several relatively broad absorption peaks between, indicating the presence of-CH in PAF-107c2or-CH3；1099cm-1There is a relatively distinct absorption peak indicating the possible presence of a C-O-C bond in PAF-107C.
FIG. 8 shows the nitrogen adsorption-desorption scheme for PAF-107c, corresponding to example 3. PAF-107c BET of 470m2g-1；
FIG. 9 is a scanning electron micrograph of PAF-107c, corresponding to example 3. PAF-107c is an irregular sphere about 100nm in size.
FIG. 10 shows a thermogram of PAF-107c, corresponding to example 3. Thermogravimetric analysis shows that the thermal decomposition temperature of PAF-107c exceeds 400 ℃, indicating that it has high stability.
FIG. 11 shows the X-ray photoelectron spectrum of PAF-107c, corresponding to example 3. The PAF-107C contains not only C but also O, and the C/O ratio is about 8.5.
FIG. 12 shows the IR spectrum of biphenyl and PAF-107d, corresponding to example 4. In the infrared absorption of the biphenyl, the infrared absorption,728cm-1and 695cm-1There are 2 distinct infrared absorption peaks, which are characteristic of the five adjacent hydrogens in biphenyl. For PAF-107d, at 811cm-1、760cm-1And 700cm-1There are 3 relatively distinct infrared absorption peaks, indicating that there are mainly 4 and 2 adjacent hydrogen hydrocarbon oscillation peaks in PAF-107 d. In PAF-107d, 2926cm-1Has a relatively broad absorption peak, indicating the presence of-CH in PAF-107d2or-CH3；1096cm-1There is a relatively distinct absorption peak indicating the possible presence of a C-O-C bond in PAF-107 d.
FIG. 13 shows the nitrogen adsorption-desorption scheme for PAF-107d, corresponding to example 4. The BET specific surface area of PAF-107d was 341m2 g-1；
FIG. 14 is a scanning electron micrograph of PAF-107d, corresponding to example 4. PAF-107d is an irregular sphere about 100nm in size.
FIG. 15 shows the X-ray photoelectron spectrum of PAF-107d, corresponding to example 4. The PAF-107d contains not only C but also O, and the C/O ratio thereof is about 7.5.
FIG. 16 shows that PAF-107b is CH at 273K4、C2H6And C3H8Adsorption isotherms correspond to example 2. At 273K and 1 bar, C2H6、C2H4And C2H2The adsorption amounts of (A) were 21, 22 and 37cm, respectively3 g-1。
FIG. 17 shows that PAF-107b is CH at 298K4、C2H6And C3H8Adsorption isotherms correspond to example 2. At 298K and 1 bar, CH4、C2H6And C3H8The adsorption amounts of (A) were 16, 15 and 28cm, respectively3g-1。
Detailed Description
Example 1:
(a) biphenyl (300mg, 1.944mmol) and anhydrous FeCl were weighed3(946.8mg, 5.832mmol) was added to a stainless steel ball mill pot in a molar ratio of biphenyl to catalyst of 1:3; (b) sealing and screwing a stainless steel ball milling tank, and putting the stainless steel ball milling tank into a ball mill for ball milling for 2 hours; (c) opening the ball milling tank, and washing the brown product with 1M HCl, water and anhydrous methanol for multiple times in sequence; (d) soxhlet extraction of the product with anhydrous methanol for 12 h; (e) the soxhlet product was dried at 120 ℃ under vacuum for 12h to give PAF-107a (160 mg).
Example 2:
(a) weighing biphenyl (300mg, 1.944mmol) and anhydrous FeCl3(946.8mg, 5.832mmol) and dimethanol formal (0.51mL, 5.832mmol) were added to a stainless steel ball mill jar with biphenyl, anhydrous FeCl3And dimethanol formal in a molar ratio of 1: 3: 3; (b) sealing and screwing a stainless steel ball milling tank, and putting the stainless steel ball milling tank into a ball mill for ball milling for 2 hours; (c) opening the ball milling tank, and washing the brown product with 1M HCl, water and anhydrous methanol for multiple times in sequence; (d) soxhlet extraction of the product with anhydrous methanol for 12 h; (e) the soxhlet product was dried at 120 ℃ under vacuum for 12h to give PAF-107b (324 mg).
Example 3:
(a) weighing biphenyl (300mg, 1.944mmol) and anhydrous FeCl3(1.893g, 11.66mmol) and dimethanol formal (0.99mL, 11.66mmol) were added to a stainless steel ball mill jar with biphenyl, anhydrous FeCl3And dimethanol formal in a molar ratio of 1: 6: 6; (b) sealing and screwing a stainless steel ball milling tank, and putting the stainless steel ball milling tank into a ball mill for ball milling for 2 hours; (c) opening the ball milling tank, and washing the brown product with 1M HCl, water and anhydrous methanol for multiple times in sequence; (d) soxhlet extraction of the product with anhydrous methanol for 12 h; (e) the soxhlet product was dried at 120 ℃ under vacuum for 12h to give PAF-107c (378 mg).
Example 4:
(a) weighing biphenyl (300mg, 1.944mmol) and anhydrous FeCl3(6.306g, 23.33mmol) and dimethanol formal (1.98mL, 23.33mmol) were added to a stainless steel ball mill jar with biphenyl, anhydrous FeCl3And dimethanol formal in a molar ratio of 1: 12: 12; (b) sealing and screwing a stainless steel ball milling tank, and putting the stainless steel ball milling tank into a ball mill for ball milling for 2 hours; (c) opening the ball milling tank, and washing the brown product with 1M HCl, water and anhydrous methanol for multiple times in sequence; (d) soxhlet extraction of the product with anhydrous methanol for 12 h; (e) the Soxhlet product was dried at 120 ℃ under vacuum for 12h to give PAF-107d (360mg)。
In conclusion, the invention grinds biphenyl and anhydrous FeCl with different proportions through a machine3And dimethanol formal to synthesize PAF-107 s. Nitrogen adsorption shows that all PAF-107s are porous materials, and the BET specific surface area of the PAF-107s is improved after dimethyl formal is introduced into a synthesis system. In biphenyl, anhydrous FeCl3And dimethanol formal in a molar ratio of 1: 6: the BET specific surface area of PAF-107c at 6 is as high as 470m2 g-1. In addition, at 273K and 298K, the ethane, ethylene and acetylene adsorption performance of PAF-107b was investigated.
From the above, it will be apparent to those skilled in the art that other various changes and modifications may be made based on the technical solution and concept of the present invention, and all such changes and modifications are within the scope of the appended claims.
Claims (10)
1. A mechanical ball milling preparation method of a porous aromatic skeleton material constructed by taking biphenyl as a base block comprises the following steps:
(a) mixing a mixture of 1: 3 Biphenyl and Anhydrous FeCl3Ball milling for 0.5-2 h after mixing;
(b) washing the ball-milled product obtained in the step (a) with 1M HCl, water and anhydrous methanol for multiple times in sequence, and then performing Soxhlet extraction with anhydrous methanol for 6-12 h;
(c) and (c) drying the soxhlet product obtained in the step (b) for 4-40 hours at 100-150 ℃ under vacuum to obtain the porous aromatic skeleton material PAF-107 a.
2. A mechanical ball milling preparation method of a porous aromatic skeleton material constructed by taking biphenyl as a base block comprises the following steps:
(a) mixing a mixture of 1: 3: 3. 1: 6: 6 or 1: 12: 12 biphenyl, anhydrous FeCl3Mixing the mixture with dimethyl acetal, and ball milling for 0.5-2 h;
(b) washing the ball-milled product obtained in the step (a) with 1M HCl, water and anhydrous methanol for multiple times in sequence, and then performing Soxhlet extraction with anhydrous methanol for 6-12 h;
(c) and (c) drying the soxhlet product in the step (b) for 4-40 hours at 100-150 ℃ under vacuum to obtain porous aromatic skeleton materials PAF-107b, PAF-107c or PAF-107 d.
3. A porous aromatic skeleton material PAF-107a constructed by taking biphenyl as a base block is characterized in that: is prepared by the method of claim 1.
4. The porous aromatic skeleton material PAF-107a constructed by taking biphenyl as a base block as claimed in claim 3, wherein: the BET specific surface area is 83m2g-1。
5. A porous aromatic skeleton material PAF-107b constructed by taking biphenyl as a base block is characterized in that: is prepared by the method of claim 2.
6. The porous aromatic skeleton material PAF-107b constructed by taking biphenyl as a base block as claimed in claim 5, wherein: the BET specific surface area is 223m2g-1。
7. A porous aromatic skeleton material PAF-107c constructed by taking biphenyl as a base block is characterized in that: is prepared by the method of claim 2.
8. The porous aromatic skeleton material PAF-107c constructed by taking biphenyl as a base block as claimed in claim 7, wherein: the BET specific surface area is 470m2g-1。
9. A porous aromatic skeleton material PAF-107d constructed by taking biphenyl as a base block is characterized in that: is prepared by the method of claim 2.
10. The porous aromatic skeleton material PAF-107d constructed by taking biphenyl as a base block as claimed in claim 9, wherein: the BET specific surface area is 314m2g-1。
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