CN110327984B - Pt @ PCN-224 photocatalyst for preparing artemisinin from dihydroarteannuic acid and preparation method thereof - Google Patents

Pt @ PCN-224 photocatalyst for preparing artemisinin from dihydroarteannuic acid and preparation method thereof Download PDF

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CN110327984B
CN110327984B CN201910626852.4A CN201910626852A CN110327984B CN 110327984 B CN110327984 B CN 110327984B CN 201910626852 A CN201910626852 A CN 201910626852A CN 110327984 B CN110327984 B CN 110327984B
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张亮亮
刘振国
陈妍慧
李佳佩
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Northwestern Polytechnical University
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Abstract

Pt @ PCN-224 and derivatives thereof are used as a photocatalyst for preparing artemisinin from dihydroartemisinic acid, and a preparation method thereof is provided at the same time, belonging to the field of preparation and application of metal organic framework materials; the MOFs has the advantages of large specific surface area and high porosity, is used as a carrier, and porphyrin and Pt nanoparticles are cooperatively used as a photocatalyst, so that the interaction ensures the high activity and high selectivity of the catalyst, and is favorable for improving the catalytic action of the catalyst; photochemical semisynthesis with a biosynthetic precursor (artemisinic acid) to reduce artemisinin extraction or total synthesis costs; the Pt @ PCN-224 photocatalyst for preparing artemisinin from dihydroarteannuic acid has the advantages of simple preparation method and strong operability.

Description

Pt @ PCN-224 photocatalyst for preparing artemisinin from dihydroarteannuic acid and preparation method thereof
Technical Field
The invention belongs to the field of preparation and application of metal organic framework materials, and particularly relates to a Pt @ PCN-224 photocatalyst for preparing artemisinin from dihydroartemisinic acid and a preparation method thereof.
Background
Metal Organic Frameworks (MOFs), which is a porous material with a periodic network structure formed by bonding Metal ions or Metal clusters and Organic ligands through coordination bonds, is a Metal Organic framework material. The MOFs are gradually valued by researchers based on the advantages of high porosity, large specific surface area, designable and adjustable framework structure and the like. In recent decades, MOFs show great application prospects in fluorescence, catalysis, gas adsorption and separation, proton conductors, drug transport, and the like.
Malaria is a worldwide epidemic with severe harm, and about three hundred million people worldwide each year become infected with malaria. Considering that artemisinin combination therapy is the most effective means to treat malaria at present and is also the best drug to combat malaria resistance, the world health organization suggests artemisinin-based combination therapies (ACTs) as a first-line drug. Commercial artemisinin is mainly from plant extracts, and the method for extracting artemisinin from sweet wormwood is based on the extraction principle and mainly comprises an ether extraction method and a solvent gasoline extraction method. Although the extraction method of artemisinin is more, the disadvantages are not few. And the content of artemisinin in natural plants is greatly influenced by factors such as geographical environment, collection time, collection part, air temperature, fertilization and the like, so that the extraction difficulty is further increased. In contrast, the synthesis of artemisinin by chemical route is also very difficult. How to efficiently synthesize the artemisinin also becomes a difficult problem to be solved at present.
An effective method to reduce the cost of artemisinin extraction or total synthesis is photochemical semisynthesis using a biosynthetic precursor (artemisinic acid). The reaction starts with dihydroartemisinic acid and1O2to produce an allyl hydroperoxide intermediate. Then the intermediate product is subjected to a series of intermediate reactions and a final ring closing step to obtain the final product artemisinin. Generated by visible light activation1O2Is a key step of a plurality of organic transformations and is an important link for semi-synchronously synthesizing artemisinin from dihydroartemisinic acid. While many photosensitizers (e.g., metal nanoparticles, porphyrins, and derivatives thereof) have been reported to be effective in generating1O2. However, the use of single metal nanoparticles, porphyrins and their derivatives as photocatalysts still has the problems of high cost or low yield and conversion rate.
Disclosure of Invention
Aiming at the technical problems, the invention discloses a Pt @ PCN-224 photocatalyst for preparing artemisinin from dihydroartemisinic acid and a preparation method thereof, wherein the preparation method is simple and can effectively catalyze the conversion of the dihydroartemisinic acid to the artemisinin.
The technical scheme of the invention is as follows:
pt @ PCN-224 and derivatives thereof are used as a photocatalyst for preparing artemisinin from dihydroarteannuic acid. The derivatives thereof mean metal derivatives thereof, preferably Pt @ PCN-224-Co, Pt @ PCN-224-Ni, Pt @ PCN-224-Zn.
A preparation method of Pt @ PCN-224 and derivatives thereof comprises the following steps:
(1) mixing N, N-dimethylacetamide and acetic acid to obtain a mixed solution A1, and dissolving a Zr6 metal cluster in the mixed solution A1 to obtain a mixed solution A;
(2) dissolving tetracarboxylic phenyl porphyrin or a metal derivative thereof in N, N-dimethylacetamide with the volume being half of that of the mixed solution A1 to obtain a mixed solution B;
(3) dissolving Pt nano particles in N, N-dimethylacetamide with the volume being half of that of the mixed solution A1 to obtain a mixed solution C;
(4) b, C is added into the mixed solution A under the condition of stirring, and the three are completely mixed;
(5) collecting a primary product by centrifugal separation, washing with N, N-dimethylacetamide, washing with acetone, and drying to obtain a final product Pt @ PCN-224 or a derivative thereof;
wherein:
the volume ratio of the N, N-dimethylacetamide to the acetic acid in the mixed solution A1 is 0: 5-4: 1, preferably 2: 3; acetic acid (99.5 percent or more) is directly used without further purification treatment, and N, N-dimethylacetamide solution (> 99.9 percent) is directly used without further purification treatment.
Zr6The mass ratio of the metal cluster to the tetracarboxylic acid phenyl porphyrin or the derivative thereof is 2: 1.
Pt nanoparticles and Zr6The mass ratio of the metal clusters is 1-5: 120.
Further, the derivatives of the tetracarboxyl porphyrin refer to Co-Tcpp, Ni-Tcpp and Zn-Tcpp containing metals Co, Ni and Zn, and products Pt @ PCN-224-Co, Pt @ PCN-224-Ni and Pt @ PCN-224-Zn are obtained respectively.
Further, the stirring speed in the step (4) is 900 rpm.
Further, the environment temperature during stirring in the step (4) is 25 ℃, the stirring time is 0.5-24 hours, preferably 9 hours, and the obtained final product has the most uniform shape and proper size.
Further, said Zr6The metal clusters can be synthesized according to literature methods, i.e.: to 300ml of 1-propanol was added 15ml of 80% by mass of Zr (OBu)4And 100g of benzoic acid. The solution was sonicated for 10-20 minutes. The mixture was heated to reflux overnight with stirring to give a clear solution. Excess 1-propanol was removed by heating under vacuum to give the product as a white solid which crystallized. The solid was washed thoroughly with 1-propanol and dried under vacuum at room temperature to give Zr6 A metal cluster.
Further, the Pt nanoparticles can be synthesized according to literature methods, i.e.: h2PtCl6·6H2O (50.75 mg, 0.098 mmol) and 222mg poly (vinyl pyrrolidone) (PVP, MW =55,000) were dissolved in 20mL ethylene glycol, the solution was reacted at 180 ℃ for 10 minutes, and the synthetic PVP-protected Pt nanoparticles were precipitated and collected by centrifugation. The sample was then washed with a mixed solution of acetone and ethanol to remove excess free PVP. The average size of the synthesized Pt NPs was measured to be 3 nm.
The beneficial technical effects are as follows:
(1) the invention successfully provides a photocatalyst Pt @ PCN-224 used for preparing artemisinin from dihydroarteannuic acid and a derivative thereof, which takes the advantages of large specific surface area and high porosity of MOFs as a carrier, and takes porphyrin and Pt nanoparticles as the photocatalyst in a synergistic manner, so that the interaction ensures the high activity and high selectivity of the catalyst, and the catalytic action of the catalyst is favorably improved.
(2) The invention successfully provides a Pt @ PCN-224 photocatalyst for preparing artemisinin from dihydroarteannuic acid, and photochemical semisynthesis is carried out by using a biosynthesis precursor (arteannuic acid), so that the extraction or total synthesis cost of artemisinin is reduced.
(3) The invention successfully provides a preparation method of the Pt @ PCN-224 photocatalyst for preparing artemisinin from dihydroarteannuic acid, which has the advantages of simple preparation method, strong operability, loose synthesis conditions, high yield, contribution to enlarged production, minimized energy input and production cost reduction.
(4) The invention successfully provides a preparation method of a Pt @ PCN-224 photocatalyst for preparing artemisinin from dihydroarteannuic acid, which has relatively mild reaction conditions, thereby being beneficial to realizing the encapsulation of the Pt nano particles of the thermosensitive material in the synthesis process of the metal organic framework material and having good application prospects in the aspects of catalysis and the like.
Drawings
FIG. one is an SEM image of Pt @ PCN-224 prepared.
FIG. two is a TEM image of Pt @ PCN-224-1 obtained.
FIG. three is a TEM image of Pt @ PCN-224-3 obtained.
FIG. four is a TEM image of Pt @ PCN-224-5 prepared.
Detailed Description
Example 1
Adding 120mg of Zr6The metal cluster is dissolved in 5ml of mixed solution A of N, N-dimethylacetamide and acetic acid, and the volume ratio of the N, N-dimethylacetamide to the acetic acid in the solution A is 0: 5-4: 1. 60mg of a tetracarboxylic acid phenylporphyrin was dissolved in 2.5ml of N, N-dimethylacetamide to obtain a mixed solution B. Pt nanoparticles (1 mg, 3mg, 5 mg) were dissolved in N, N-dimethylacetamide having a volume of 2.5ml to obtain a mixed solution C. The three are completely mixed under the stirring condition that the rotating speed of magnetons is 900 revolutions per minute, the stirring is carried out under the condition of 25 ℃, and the stirring time is controlled between 0.5 and 24 hours. And (3) centrifugally separating and collecting a primary product, washing with N, N-dimethylacetamide for three times, washing with acetone for one time, and drying to obtain pure phases of Pt @ PCN-224-1, Pt @ PCN-224-3 and Pt @ PCN-224-5 which are final products respectively.
Example 2
Adding 120mg of Zr6The metal clusters were dissolved in 5ml of a mixed solution A of N, N-dimethylacetamide and acetic acid in a volume ratio of 2: 3. 60mg of TCPP-Zn (or TCPP-Co, TCPP-Ni) was dissolved in 2.5ml of N, N-dimethylacetamide to obtain a mixed solution B. 1mg of Pt nanoparticles was dissolved in N, N-dimethylacetamide having a volume of 2.5ml to obtain a mixed solution C. The three are completely mixed under the stirring condition that the rotating speed of magnetons is 900 revolutions per minute and the temperature is 25 DEG CStirred for 9 hours. And (3) centrifugally separating and collecting a primary product, washing with N, N-dimethylacetamide for three times, washing with acetone for one time, and drying to obtain pure phases of Pt @ PCN-224-Zn, Pt @ PCN-224-Co and Pt @ PCN-224-Ni as final products.
Example 3
Dihydroartemisinic acid (25 mg, 0.106 mmol), Pt @ PCN-224 obtained in example 1, example 2 or a derivative thereof (0.002 mmol based on porphyrin), trifluoroacetic acid (8. mu.L) were dispersed in 5ml of dichloromethane to obtain a mixed solution. The mixed solution was slowly bubbled with oxygen for 3 hours under the illumination of LED light. Removing methylene chloride contained in the reaction product by1H NMR further demonstrated the conversion of dihydroartemisinic acid. The Pt @ PCN-224-1 conversion was 98% and the yield was 45% was finally obtained. The conversion of Pt @ PCN-224-3 was 99% with a 50% yield. The Pt @ PCN-224-5 normalization rate was 99%, and the yield was 51%. The conversion of Pt @ PCN-224-Zn was 99%, the yield was 54%, the conversion of Pt @ PCN-224-Co was 99%, the yield was 53%, and the conversion of Pt @ PCN-224-Ni was 99%, the yield was 52%.
The present invention has been described in detail above. The principle and embodiments of the present invention have been explained by using specific examples, and the above description of the examples is only for the purpose of helping understanding the core idea of the present invention, and several improvements and modifications can be made to the present invention without departing from the principle of the present invention, and these improvements and modifications also fall into the protection scope of the present invention.

Claims (7)

1. A preparation method of a photocatalyst Pt @ PCN-224 and derivatives thereof for preparing artemisinin by using dihydroarteannuic acid is characterized by comprising the following steps:
(1) mixing N, N-dimethylformamide and acetic acid to obtain a mixed solution A1, and adding Zr6Dissolving the metal clusters in the mixed solution A1 to obtain a mixed solution A;
(2) dissolving tetracarboxylic phenyl porphyrin or a metal derivative thereof in N, N-dimethylformamide with the volume being half of that of the mixed solution A1 to obtain a mixed solution B;
(3) dissolving Pt nano particles in N, N-dimethylformamide with the volume being half of that of the mixed solution A1 to obtain a mixed solution C;
(4) b, C is added into the mixed solution A under the condition of stirring, and the three are completely mixed;
(5) collecting a primary product by centrifugal separation, washing the primary product with N, N-dimethylformamide, washing with acetone, and drying to obtain a final product Pt @ PCN-224 or a derivative thereof;
wherein:
the volume ratio of the N, N-dimethylformamide to the acetic acid in the mixed solution A1 is 0: 5-4: 1;
Zr6the mass ratio of the metal cluster to the tetracarboxylic acid phenyl porphyrin or the derivative thereof is 2: 1;
pt nanoparticles and Zr6The mass ratio of the metal clusters is 1-5: 100;
the synthesis method of the Pt nano-particles comprises the following steps: h2PtCl6·6H2O (50.75 mg, 0.098 mmol) and 222mg polyvinylpyrrolidone (PVP, MW =55,000) were dissolved in 20mL of ethylene glycol, the solution was reacted at 180 ℃ for 10 minutes, the synthetic PVP protected Pt nanoparticles were precipitated, the nanoparticles were collected by centrifugation, and then the sample was washed with a mixed solution of acetone and ethanol to remove excess free PVP, the average size of the synthetic Pt NPs was 3 nm.
2. The preparation method of the photocatalyst Pt @ PCN-224 and the derivatives thereof for preparing artemisinin from dihydroarteannuic acid as claimed in claim 1, wherein the volume ratio of N, N-dimethylformamide to acetic acid in the mixed solution A1 is 2: 3.
3. The method for preparing photocatalyst Pt @ PCN-224 and derivatives thereof for artemisinin preparation by dihydroarteannuic acid as claimed in claim 1, wherein the derivatives of tetracarboxylporphyrin are Co-TCPP, Ni-TCPP and Zn-TCPP containing metals Co, Ni and Zn, and the products Pt @ PCN-224-Co, Pt @ PCN-224-Ni and Pt @ PCN-224-Zn are obtained respectively.
4. The method for preparing the photocatalyst Pt @ PCN-224 and the derivatives thereof for preparing artemisinin from dihydroarteannuic acid as claimed in claim 1, wherein the stirring speed in step (4) is 900 rpm.
5. The method for preparing the photocatalyst Pt @ PCN-224 and the derivatives thereof for preparing artemisinin from dihydroarteannuic acid as claimed in claim 1, wherein the ambient temperature during stirring in step (4) is 25 ℃.
6. The method for preparing the photocatalyst Pt @ PCN-224 and the derivatives thereof for preparing artemisinin from dihydroarteannuic acid as claimed in claim 4, wherein the stirring time in step (4) is 0.5-24 hours.
7. The method for preparing the photocatalyst Pt @ PCN-224 and the derivatives thereof for preparing artemisinin from dihydroarteannuic acid as claimed in claim 6, wherein stirring is carried out at 25 ℃ for 9 hours in the step (4).
CN201910626852.4A 2019-07-12 2019-07-12 Pt @ PCN-224 photocatalyst for preparing artemisinin from dihydroarteannuic acid and preparation method thereof Active CN110327984B (en)

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