CN115216023B - Iron-based MOFs material with photo-thermal conversion performance and preparation method and application thereof - Google Patents

Iron-based MOFs material with photo-thermal conversion performance and preparation method and application thereof Download PDF

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CN115216023B
CN115216023B CN202210546172.3A CN202210546172A CN115216023B CN 115216023 B CN115216023 B CN 115216023B CN 202210546172 A CN202210546172 A CN 202210546172A CN 115216023 B CN115216023 B CN 115216023B
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mofs material
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CN115216023A (en
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刘媛媛
张洪刚
黄柏标
王泽岩
王朋
郑昭科
程合锋
张倩倩
张晓阳
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Shandong University
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • C08G83/008—Supramolecular polymers
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/1691—Coordination polymers, e.g. metal-organic frameworks [MOF]
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
    • B01J35/39—Photocatalytic properties
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D317/34—Oxygen atoms
    • C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
    • B01J2531/0241—Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
    • B01J2531/025—Ligands with a porphyrin ring system or analogues thereof, e.g. phthalocyanines, corroles
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84—Metals of the iron group
    • B01J2531/842—Iron

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  • Engineering & Computer Science (AREA)
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Abstract

The invention discloses an iron-based MOFs material with photo-thermal conversion performance, a preparation method and application thereof, wherein the preparation method comprises the following steps: mixing an iron source and a pyridine porphyrin organic ligand according to the mass ratio of 1:0.5-2, and performing solvothermal reaction at 150-200 ℃ for 2-5 days to obtain the compound; the pyridine porphyrin organic ligand is 5,10,15, 20-tetra (4-pyridyl) porphyrin; the iron source is selected from ferric chloride hexahydrate, ferric nitrate nonahydrate, ferrocene or ferrous acetate. The iron-based MOFs material can generate synergistic effect with photocatalytic carbon dioxide cycloaddition reaction under the initiation of illumination, shows the catalytic effect of 1+1>2, and can obtain excellent yield under mild conditions.

Description

Iron-based MOFs material with photo-thermal conversion performance and preparation method and application thereof
Technical Field
The invention relates to the technical field of photo-thermal conversion and photo-thermal catalysis, in particular to an iron-based MOFs material with photo-thermal conversion performance, a preparation method and application thereof.
Background
The statements herein merely provide background information related to the present disclosure and may not necessarily constitute prior art.
The large consumption of fossil energy causes the accumulation of carbon dioxide in the atmosphere, which causes a series of environmental problems such as global warming, sea level elevation, and extreme weather. The conversion of waste carbon dioxide into high-value chemicals by cycloaddition reaction with epoxy compounds is a way to effectively utilize carbon dioxide, which is in line with atomic economy, no by-product is generated, and the product cyclic carbonate is an important chemical raw material with higher economic value. The conditions for the industrial reaction are usually high temperature and high pressure, a great deal of energy is consumed and the reaction process has potential safety hazards.
Disclosure of Invention
Aiming at the defects existing in the prior art, the invention aims to provide an iron-based MOFs material with photo-thermal conversion performance, and a preparation method and application thereof.
In order to achieve the above object, the present invention is realized by the following technical scheme:
in a first aspect, the present invention provides a method for preparing an iron-based MOFs material having photo-thermal conversion properties, including the steps of:
mixing an iron source and a pyridine porphyrin organic ligand according to the mass ratio of 1:0.5-2, and performing solvothermal reaction at 150-200 ℃ for 2-5 days to obtain the compound;
the pyridine porphyrin the organic ligand is 5,10,15, 20-tetrakis (4-pyridyl) porphyrin;
the iron source is selected from ferrous oxalate dihydrate, ferrous sulfate heptahydrate, ferrocene or ferrous acetate.
In a second aspect, the invention provides an iron-based MOFs material with photo-thermal conversion performance, which is prepared by the preparation method.
In a third aspect, the invention provides an application of the iron-based MOFs material with photo-thermal conversion performance in the production of cyclic carbonate by photo-thermal synergistic catalysis of cycloaddition reaction of carbon dioxide and an epoxy compound.
The beneficial effects achieved by one or more embodiments of the present invention are as follows:
the prepared iron-based MOFs material has good optical absorption capacity in ultraviolet, visible and near infrared regions, has excellent photo-thermal conversion characteristics, can absorb light energy to convert the light energy into heat energy, and improves the system temperature. And has the characteristic of p-type semiconductor, the band gap position is correct, and the photocatalysis reaction can occur. So that the iron-based MOFs material can be heated under the initiation of illuminationThe catalysis and the photocatalysis carbon dioxide cycloaddition reaction produce synergistic effect and show 1+1>2, excellent yields can be obtained under mild conditions (under light, the yield of the product propylene carbonate can reach 106.13mmol g by taking FeTPyP as a catalyst -1 h -1 ). It is particularly interesting to introduce solar energy into the reaction instead of thermal energy as in conventional reactions, driving the reaction under mild conditions.
In addition, the iron-based MOFs material prepared by the method has good structural stability and performance stability, has no obvious loss of performance in five cycle tests and no obvious change of structure, and can be used as a catalyst for potential industrial application.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the description serve to explain the invention.
FIG. 1 is an X-ray powder diffraction (XRD) pattern and a fitting XRD pattern of FeTPyP prepared in example 1 of the present invention;
FIG. 2 is a Scanning Electron Microscope (SEM) picture and element distribution diagram of FeTPyP prepared in example 1 of the present invention;
FIG. 3 is a diagram of embodiment 1 of the present invention FeTPyP and ligand H prepared 2 Fourier infrared (FT-IR) spectrograms of TPyP;
FIG. 4 is X-ray photoelectron Spectrometry (XPS), wherein (a) is FeTPyP and ligand H prepared in example 1 of the present invention 2 N of TPyP 1s (b) Fe which is FeTPyP prepared in example 1 of the present invention 2p Is a high resolution spectrogram of (2);
FIG. 5 shows FeTPyP and ligand H prepared in example 1 of the present invention 2 An ultraviolet visible Diffuse Reflectance Spectrum (DRS) map of TPyP;
FIG. 6 is a graph showing the photocurrent density response of FeTPyP prepared in example 1 of the present invention;
FIG. 7 is an XPS valence band spectrum of FeTPyP prepared in example 1 of the present invention;
FIG. 8 shows FeTPyP and ligand H prepared in example 1 of the present invention 2 TPyP and blank controlA photo-thermal conversion performance test result diagram of (2);
FIG. 9 is a graph showing the results of stability test of FeTPyP prepared in example 1 of the present invention;
FIG. 10 is an XRD spectrum of FeTPyP prepared in example 1 of the present invention before and after the cyclic stability test;
FIG. 11 is a FT-IR chart of FeTPyP prepared in example 1 of the invention before and after a cyclic stability test;
FIG. 12 shows XPS patterns of FeTPyP prepared in example 1 of the present invention before and after the cyclic stability test, wherein (a) and (b) are N respectively 1s And Fe (Fe) 2p Is a high resolution spectrum of XPS of (C).
FIG. 13 is a visual illustration of the catalytic performance differences under different conditions on FeTPyP prepared in example 1 of the present invention.
Detailed Description
It should be noted that the following detailed description is illustrative and is intended to provide further explanation of the invention. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
In a first aspect, the present invention provides a method for preparing an iron-based MOFs material having photo-thermal conversion properties, including the steps of:
mixing an iron source and a pyridine porphyrin organic ligand according to the mass ratio of 1:0.5-2, and performing solvothermal reaction at 150-200 ℃ for 2-5 days to obtain the compound;
the pyridine porphyrin organic ligand is 5,10,15, 20-tetra (4-pyridyl) porphyrin;
the iron source is selected from ferrous oxalate dihydrate, ferrous sulfate heptahydrate, ferrocene or ferrous acetate.
In some embodiments, the organic solvent used for the solvothermal reaction is N, N' -dimethylformamide, in which the pyridinium porphyrin has better solubility, while being more polar and having excellent stability.
In some embodiments, the iron source is ferrocene, and the iron source has the highest yield, stable property, low price and available raw materials.
In some embodiments, the mass ratio of the iron source to the pyridinium porphyrin organic ligand is 1:0.8-1.2.
In some embodiments, the method further comprises the steps of suction filtration, washing and drying of the prepared iron-based MOFs material.
Preferably, the solvent used for the washing is ethanol, N' -dimethylformamide, chloroform or acetone.
Further preferably, the unreacted raw materials are removed by washing with chloroform, and then the chloroform is removed by washing with ethanol.
Preferably, the drying is vacuum drying. Drying conditions are drying at 50 to 100 ℃ for 6 to 24 hours; preferably at 60 c for 12 hours.
In a second aspect, the invention provides an iron-based MOFs material with photo-thermal conversion performance, which is prepared by the preparation method.
In a third aspect, the invention provides an application of the iron-based MOFs material with photo-thermal conversion performance in the production of cyclic carbonate by photo-thermal synergistic catalysis of cycloaddition reaction of carbon dioxide and an epoxy compound.
In order to make the technical solution of the present invention more clearly understood by those skilled in the art, the following detailed description will be made with reference to specific embodiments.
Example 1
A preparation method of an iron-based MOFs material (FeTPyP) with photo-thermal conversion performance comprises the following steps:
(1) To N, N' -dimethylformamide (40 mL) was added 150mg of ferrocene and 150mg of 5,10,15, 20-tetra (4-pyridyl) porphyrin, and the mixture was sonicated at room temperature for 20 minutes, followed by thorough mixing.
(2) Transferring the solution obtained in the step (1) into a 100mL high-temperature reaction kettle, putting into a 180 ℃ oven, preserving heat for 3 days, taking out, and naturally cooling to room temperature.
(3) And (3) collecting the product obtained in the step (2), filtering, washing with chloroform and ethanol respectively, and drying in a vacuum drying oven at 60 ℃ for 12 hours to obtain FeTPyP.
Phase analysis of the FeTPyP prepared:
x-ray powder derivatives of FeTPyP preparedThe emission spectrum (XRD) is shown in figure 1, and the result is similar to the spectrum obtained by structural simulation, so that the synthesized material is proved to be a single phase. Scanning Electron Microscope (SEM) testing (fig. 2) showed that FeTPyP was either in the form of sheets or in the form of bulk structures formed by stacking sheets, the Mapping test shows that the Fe and N elements are uniformly distributed. Further characterization of material success by Fourier IR (FT-IR) and X-ray photoelectron spectroscopy (XPS), FT-IR spectra of FIG. 3 and N of FIG. 4 (a) 1S The XPS spectrum of FIG. 4 (b) demonstrates the coordination of Fe with N, fe 2p The XPS spectrum of (C) shows that the valence state of Fe is both divalent and trivalent.
Photophysical property analysis of the prepared FeTPyP:
the ultraviolet visible Diffuse Reflectance Spectrum (DRS) of fig. 5 shows that the absorption region of FeTPyP is red shifted compared to that of pyridinoporphyrin, and the absorption range is wider, and the band gap width of FeTPyP can be calculated to be 1.1eV. The photocurrent test of fig. 6 shows that FeTPyP has a negative photocurrent response under light irradiation, and the response degree increases with the increase of the applied voltage, and the FeTPyP is a characteristic of a p-type semiconductor. The XPS valence band spectrum of FIG. 7 shows that the valence band position of FeTPyP is at 1.85eV, while the conduction band position can be calculated to be at 0.75eV.
The test experiment of the photo-thermal conversion performance comprises the following steps:
15mg of FeTPyP prepared in example 1 was weighed into a square quartz reactor, 3mL of styrene oxide was added, and after thorough mixing, a xenon lamp with a power of 300W was placed above the reactor, the distance was fixed at 15 cm, and the real-time temperature of the system was measured and recorded using an infrared thermometer.
Experimental results:
as shown in fig. 8, feTPyP exhibits excellent light-heat conversion performance, which is manifested as an increase in system temperature. Within 10 minutes, the temperature of FeTPyP can be raised from room temperature (25 ℃) to 62 ℃, and the temperature can be kept stable. In contrast, ligand pyridinylporphyrin can only be raised to 53 ℃, the temperature of blank solution rise is lower, and the final temperature is less than 40 ℃.
Light and/or heat catalyzed carbon dioxide cycloaddition reaction test experiments were performed as follows:
15mg of FeTPyP prepared in example 1 and 0.5mmol of cocatalyst (tetrabutylammonium bromide, TBAB) were weighed into a square quartz reactor, 3mL of styrene oxide was added, and after thorough mixing, carbon dioxide was used to exhaust for 20 minutes, the reactor was subjected to catalytic experiments under different test conditions (see table 1), carbon dioxide was continuously introduced during the reaction to maintain the internal pressure of the reactor at the same level as the environment, the reaction was performed for 5 hours, and samples were taken and the product styrene carbonate was detected by gas chromatography.
Experimental results:
as shown in Table 1, with FeTPyP prepared in example I as a catalyst and TBAB as a cocatalyst, carbon dioxide was reacted with styrene oxide at an ideal rate of styrene carbonate production without external heat supply in a total light condition, with a yield of 530.67mmol g in five hours -1 (item 1). Then controlling the temperature and illumination, and performing pure thermal catalysis and pure photocatalysis experiments as comparison experiments, wherein the reaction rate can be improved by comparing the items 2 and 4; the addition of light can also increase the reaction rate, comparing items 3 and 4. Experiments were then carried out with removal of catalyst FeTPyP (entry 5) and removal of cocatalyst TBAB (entry 6), both of which were found to have an important effect on increasing the reaction rate.
Table 1. Cycloaddition yields of carbon dioxide and styrene carbonate under different reaction conditions. [a]
Note that each label in table 1 has the following meaning:
[a] reaction conditions are as follows: feTPyP (15 mg), TBAB (0.5 mmol), styrene oxide (3 mL), carbon dioxide (1 bar), reaction time (5 h).
[b] Yield was determined by GC-MS, units: mmol/g.
[c] No cocatalyst TBAB.
[d] Catalyst-free FeTPyP.
[e] The temperature is controlled by the circulating water, "-" means the temperature is the natural temperature of the system which is not controlled.
Importantly, as shown in fig. 9, there was no significant loss in catalytic efficiency over five cycles of experiments, demonstrating good catalytic stability of the FeTPyP prepared. In addition, XRD (FIG. 10), FT-IR (FIG. 11), XPS (FIG. 12) and other data of FeTPyP before and after the reaction were not significantly changed, further demonstrating the stability of their structures.
Example 2
A preparation method of an iron-based MOFs material (FeTPyP) with photo-thermal conversion performance comprises the following steps:
(1) To N, N' -dimethylformamide (40 mL) was added 150mg of ferrous acetate and 200mg of 5,10,15, 20-tetrakis (4-pyridyl) porphyrin, followed by sonication at room temperature for 20 minutes, followed by thorough mixing.
(2) Transferring the solution obtained in the step (1) into a 100mL high-temperature reaction kettle, putting into a 200 ℃ oven, preserving heat for 4 days, taking out, and naturally cooling to room temperature.
(3) And (3) collecting the product obtained in the step (2), filtering, washing with chloroform and ethanol respectively, and drying in a vacuum drying oven at 80 ℃ for 10 hours to obtain FeTPyP.
Example 3
A preparation method of an iron-based MOFs material (FeTPyP) with photo-thermal conversion performance comprises the following steps:
(1) To N, N' -dimethylformamide (40 mL) was added 150mg of ferrous oxalate dihydrate and 100mg of 5,10,15, 20-tetrakis (4-pyridyl) porphyrin, followed by sonication at room temperature for 20 minutes, and thoroughly mixed.
(2) Transferring the solution obtained in the step (1) into a 100mL high-temperature reaction kettle, putting into a baking oven at 150 ℃, preserving heat for 5 days, taking out, and naturally cooling to room temperature.
(3) And (3) collecting the product obtained in the step (2), filtering, washing with chloroform and ethanol respectively, and drying in a vacuum drying oven at 100 ℃ for 12 hours to obtain FeTPyP.
The above description is only of the preferred embodiments of the present invention and is not intended to limit the present invention, but various modifications and variations can be made to the present invention by those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims (8)

1. The application of an iron-based MOFs material with photo-thermal conversion performance in the production of cyclic carbonate by photo-thermal synergistic catalysis of cycloaddition reaction of carbon dioxide and an epoxy compound is characterized in that: the preparation method of the iron-based MOFs material with the photo-thermal conversion performance comprises the following steps:
mixing an iron source and a pyridine porphyrin organic ligand according to the mass ratio of 1:0.5-2, and performing solvothermal reaction at 150-200 ℃ for 2-5 days to obtain the compound;
the pyridine porphyrin organic ligand is 5,10,15, 20-tetra (4-pyridyl) porphyrin;
the iron source is selected from ferrous oxalate dihydrate, ferrous sulfate heptahydrate, ferrocene or ferrous acetate.
2. The application of the iron-based MOFs material with photo-thermal conversion performance in the production of cyclic carbonate by photo-thermally synergically catalyzing cycloaddition reaction of carbon dioxide and an epoxy compound by light driving, according to claim 1, is characterized in that: the organic solvent used in the solvothermal reaction is N, N' -dimethylformamide.
3. The application of the iron-based MOFs material with photo-thermal conversion performance in the production of cyclic carbonate by photo-thermally synergically catalyzing cycloaddition reaction of carbon dioxide and an epoxy compound by light driving, according to claim 1, is characterized in that: the iron source is ferrocene.
4. The application of the iron-based MOFs material with photo-thermal conversion performance in the production of cyclic carbonate by photo-thermally synergically catalyzing cycloaddition reaction of carbon dioxide and an epoxy compound by light driving, according to claim 1, is characterized in that: the mass ratio of the iron source to the pyridine porphyrin organic ligand is 1:0.8-1.2.
5. The application of the iron-based MOFs material with photo-thermal conversion performance in the production of cyclic carbonate by photo-thermally synergically catalyzing cycloaddition reaction of carbon dioxide and an epoxy compound by light driving, according to claim 1, is characterized in that: the method also comprises the steps of suction filtration, washing and drying of the prepared iron-based MOFs material.
6. The application of the iron-based MOFs material with photo-thermal conversion performance in the production of cyclic carbonate by photo-thermally synergically catalyzing cycloaddition reaction of carbon dioxide and an epoxy compound by light driving, according to claim 5, is characterized in that: the solvent adopted in the washing is ethanol, N' -dimethylformamide, chloroform or acetone.
7. The application of the iron-based MOFs material with photo-thermal conversion performance in the production of cyclic carbonate by photo-thermally synergically catalyzing cycloaddition reaction of carbon dioxide and an epoxy compound by light driving, according to claim 5, is characterized in that: washing with chloroform and then ethanol.
8. The application of the iron-based MOFs material with photo-thermal conversion performance in the production of cyclic carbonate by photo-thermally synergically catalyzing cycloaddition reaction of carbon dioxide and an epoxy compound by light driving, according to claim 5, is characterized in that: the drying is vacuum drying.
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