CN117486838A - Photocatalytic synthesis method of 2 (5H) -furanone compound - Google Patents

Photocatalytic synthesis method of 2 (5H) -furanone compound Download PDF

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CN117486838A
CN117486838A CN202311429475.8A CN202311429475A CN117486838A CN 117486838 A CN117486838 A CN 117486838A CN 202311429475 A CN202311429475 A CN 202311429475A CN 117486838 A CN117486838 A CN 117486838A
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furfural
photocatalyst
synthesis method
formula
furanone
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刘海超
林莹
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Peking University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C07D307/48—Furfural
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

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  • Organic Chemistry (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention discloses a photocatalytic synthesis method of a 2 (5H) -furanone compound. The photocatalytic synthesis method comprises the following steps: under the catalysis of a photocatalyst, furfural and derivatives thereof are obtained through selective oxidation reaction; the structural formula of the furfural and the derivative thereof is shown as a formula I, and the structural formula of the 2 (5H) -furanone compound is shown as a formula II; the photocatalyst is an inorganic semiconductor photocatalyst and is a composite material of one or two of the following oxyhydroxide: alOOH, scOOH, YOOH, VOOH, crOOH, gaOOH, mnOOH, feOOH, coOOH and InOOH. According to the invention, furfural or furfural derivatives are used as raw materials, and are subjected to selective oxidation in the presence of an inorganic semiconductor photocatalyst to obtain the 2 (5H) -furanone compound, so that the catalytic biomass-based furfural and derivatives thereof on the inorganic semiconductor photocatalyst is realized for the first timePreparing 2 (5H) -furanone compounds by selective oxidation; after the reaction of the method is finished, the catalyst is easy to separate, can be recycled and has good application prospect.

Description

Photocatalytic synthesis method of 2 (5H) -furanone compound
Technical Field
The invention relates to a photocatalytic synthesis method of a 2 (5H) -furanone compound, belonging to the technical field of organic synthesis.
Background
2 (5H) -furanones have been studied as a key synthon for the total synthesis of natural products and drugs. Because of the biological activities of antibiosis, anti-inflammation, antivirus, anti-tumor and the like, the 2 (5H) -furanone compound can be applied to the preparation of pesticides, plant growth regulators, quick-drying paint, prostaglandin, alkaloid and the like. In addition, the alpha, beta-unsaturated aldehyde structure of the 2 (5H) -furanone compound can be used for replacing acrylic ester, and can be used for synthesizing a polymeric material as a lactone monomer. Only reagent amounts of 2 (5H) -furanones are currently available on the market and are expensive. At present, the 2 (5H) -furanone compound is mainly produced by photooxidation of furfural and derivatives thereof by a photosensitizer, the method can face the problem that the photosensitizer is difficult to recycle, and subsequent treatments such as active carbon decolorization and the like are required (environ. Sci. Polut. Res. Int.2021,28, 28911-28925). It is therefore desirable to provide a novel method for synthesizing 2 (5H) -furanones.
Disclosure of Invention
The invention aims to provide a synthesis method of a 2 (5H) -furanone compound, which adopts a one-step photocatalytic oxidation mode to directly oxidize furfural and derivatives thereof to obtain the 2 (5H) -furanone compound, and has the advantages of mild condition, high selectivity and easy recycling of a catalyst.
The synthesis method adopts an inorganic semiconductor photocatalyst and takes a biomass-based platform compound furfural and derivatives thereof as raw materials.
Specifically, the invention provides a photocatalytic synthesis method of a 2 (5H) -furanone compound, which comprises the following steps:
under the catalysis of a photocatalyst, furfural and derivatives thereof are subjected to selective oxidation reaction to obtain 2 (5H) -furanone compounds;
the structural formula of the furfural and the derivative thereof is shown as formula I:
the structural formula of the 2 (5H) -furanone compound is shown as a formula II:
in the formula I and the formula II, R 1 is-H, -COOH, alkyl with 1-5 carbon atoms or alkyl alcohol with 1-5 carbon atoms, R 2 is-H, alkyl with 1-5 carbon atoms or alkyl alcohol with 1-5 carbon atoms, R 3 is-H, alkyl with 1-5 carbon atoms or alkyl alcohol with 1-5 carbon atoms;
preferably, the alkyl group or the alkyl alcohol has 1 to 3 carbon atoms;
in the formula I, R 4 is-H or-OH;
the photocatalyst is an inorganic semiconductor photocatalyst, is one or two of the following composite materials of oxyhydroxide, and when the photocatalyst is two composite materials, the molar ratio of the two components is 5-1: 1 to 5:
AlOOH, scOOH, YOOH, VOOH, crOOH, gaOOH, mnOOH, feOOH, coOOH and InOOH.
The inorganic semiconductor photocatalytic material adopted by the invention has the advantages of high chemical stability, convenient repeated use, simple synthesis process, low price, environmental friendliness and the like, and can replace photosensitizer to prepare 2 (5H) -furanone chemicals by high-efficiency selective oxidation.
The furfural and the derivatives thereof adopted by the invention are preferably compounds shown in the following structural formula:
in the photocatalytic synthesis method, the dosage of the photocatalyst is as follows: 1mmol of furfural and derivatives thereof are added with 10 to 100mg of photocatalyst.
In the photocatalytic synthesis method, the solvent adopted in the selective oxidation reaction is tetrahydrofuran, 1, 4-dioxane, toluene, cyclohexane, n-hexane, methanol, ethanol or water, and the dosage of the solvent is 10-20 mL/1mmol of furfural and derivatives thereof.
In the photocatalysis synthesis method, the selective oxidation reaction is carried out under the normal pressure condition, the temperature is 10-80 ℃, and the time is 1-24 hours.
In the photocatalysis synthesis method, the selective oxidation reaction adopts a xenon lamp light source, and the power of the xenon lamp light source is 100-400W.
According to the method for preparing the 2 (5H) -furanone compound by photocatalysis, furfural or a furfural derivative is used as a raw material, and selective oxidation is carried out in the presence of an inorganic semiconductor photocatalyst to obtain the 2 (5H) -furanone compound. The invention realizes the preparation of 2 (5H) -furanone compounds by catalyzing the selective oxidation of biomass-based furfural and derivatives thereof on an inorganic semiconductor photocatalyst for the first time; the catalyst has high activity and high selectivity. The biomass-based compound is used as a raw material to prepare the 2 (5H) -furanone compound, which meets the requirements of sustainable development and green chemistry. The 2 (5H) -furanone compound has high selectivity, and is convenient for separating and purifying products. After the synthesis method is finished, the catalyst is easy to separate, can be recycled and has good application prospect.
Detailed Description
The experimental methods used in the following examples are conventional methods unless otherwise specified.
Materials, reagents and the like used in the examples described below are commercially available unless otherwise specified.
In the examples below, the conversion is referred to as (amount of converted reactants/total amount of reactants) x 100%.
In the examples below, the molar selectivity refers to (moles of target product)/(moles of converted reactants) ×100%.
In the following examples, the conditions for liquid chromatography analysis are as follows:
the liquid phase product is analyzed and detected on Shimadzu liquid phase chromatography LC20A, wherein the used analytical column is Shodex Sugar1011 Sugar column, the mobile phase is 1wt% dilute sulfuric acid solution, and the flow rate is 1.0 mL.min -1 Column Wen She was set at 50 ℃.
Example 1:
weighing Al (NO) with corresponding mass 3 ) 3 With Sc (NO) 3 ) 3 Dissolving in 50mL of deionized water, stirring, dissolving, adding NaOH solution, mixing uniformly, placing into a baking oven, keeping at 220 ℃ for 12 hours, filtering the obtained product, washing with deionized water and ethanol for 3 times respectively, and drying in the baking oven at 110 ℃ for 8 hours to obtain the AlOOH-ScOOH composite material (the ratio is 5:1).
The reaction of photocatalytic oxidation of furfural was carried out in a photocatalytic reactor with a circulating water bath at a reaction speed of 600rpm. 1mmol of substrate, 10mg of catalyst, 10mL of deionized water were charged into a 50mL reactor and reacted at 20℃through a circulating water bath. The reactor was irradiated with a 300W xenon lamp and the reaction was completed after 12h of rapid stirring. The conversion rate of furfural was 99.5%, the molar selectivity of 5-hydroxy-2 (5H) -furanone was 96.6% and the remaining by-product was formic acid, as analyzed by liquid chromatography.
Example 2:
weighing Y (NO) of corresponding mass 3 ) 3 With Sc (NO) 3 ) 3 Dissolving in 50mL of deionized water, stirring, dissolving, adding NaOH solution, mixing uniformly, placing into a baking oven, keeping at 220 ℃ for 12 hours, filtering the obtained product, washing with deionized water and ethanol for 3 times respectively, and drying in the baking oven at 110 ℃ for 8 hours to obtain the ScOOH-YOOH composite material (the ratio is 1:1).
The reaction of photocatalytic furoic acid oxide was carried out in a photocatalytic reactor with a circulating water bath at a reaction speed of 600rpm. 1mmol of substrate, 25mg of catalyst, 20mL of methanol were added to a 50mL reactor and reacted at 25℃by means of a circulating water bath. The reactor was irradiated with a 200W xenon lamp and the reaction was completed after 8h of rapid stirring. The conversion of furoic acid was 100% and the molar selectivity of 5-hydroxy-2 (5H) -furanone was 93.0% by liquid chromatography, the remainder being formic acid.
Example 3:
weighing V (NO) of corresponding mass 3 ) 3 Dissolving in 50mL deionized water, stirring to dissolve, adding NaOH solution, mixing, oven maintaining at 220deg.C for 12 hr, and processing the obtained productFiltering and washing with deionized water and ethanol for 3 times respectively, and drying in an oven at 110 ℃ for 8 hours to obtain the VOOH material.
The reaction of photocatalytic oxidation of 5-hydroxymethylfurfural was carried out in a photocatalytic reactor with a circulating water bath at a reaction speed of 600rpm. 1mmol of substrate, 20mg of catalyst, 10mL of ethanol were charged into a 50mL reactor and reacted at 40℃by means of a circulating water bath. The reactor was irradiated with 400W xenon lamp and the reaction was completed after 1h with rapid stirring. The conversion of 5-hydroxymethylfurfural was 98.7% and the molar selectivity of 5-hydroxymethyl-5-hydroxy-2 (5H) -furanone was 89.2% as analyzed by liquid chromatography, with the remaining by-product being formic acid.
Example 4:
weighing Y (NO) of corresponding mass 3 ) 3 And V (NO) 3 ) 3 Dissolving in 50mL of deionized water, stirring, dissolving, adding NaOH solution, mixing uniformly, placing into a baking oven, keeping at 220 ℃ for 12 hours, filtering the obtained product, washing with deionized water and ethanol for 3 times respectively, and drying in the baking oven at 110 ℃ for 8 hours to obtain the YOOH-VOOH composite material (the ratio is 1:5).
The reaction of photocatalytic oxidation of 5-hydroxymethylfuroic acid was carried out in a photocatalytic reactor with a circulating water bath at a reaction speed of 600rpm. 1mmol of substrate, 50mg of catalyst, 15mL of deionized water were added to a 50mL reactor and reacted at 80℃through a circulating water bath. The reactor was irradiated with a 300W xenon lamp and the reaction was rapidly stirred for 2h and ended. The conversion of 5-hydroxymethyl furoic acid was 94.3% and the molar selectivity of 5-hydroxymethyl-5-hydroxy-2 (5H) -furanone was 92.7% by liquid chromatography, with the remainder being formic acid.
Example 5:
weighing Cr (NO) with corresponding mass 3 ) 3 With Ga (NO) 3 ) 3 Dissolving in 50mL of deionized water, stirring, dissolving, adding NaOH solution, mixing uniformly, placing into a baking oven, keeping at 220 ℃ for 12 hours, filtering the obtained product, washing with deionized water and ethanol for 3 times respectively, and drying in the baking oven at 110 ℃ for 8 hours to obtain the CrOOH-GaOOH composite material (the ratio is 3:1).
The reaction of photocatalytic oxidation of 5-methylfurfural was carried out in a photocatalytic reactor with a circulating water bath at a reaction speed of 600rpm. 1mmol of substrate, 100mg of catalyst, 20mL of tetrahydrofuran were charged into a 50mL reactor and reacted at 10℃by means of a circulating water bath. The reactor was irradiated with a 100W xenon lamp and the reaction was completed after 24h with rapid stirring. The conversion of 5-methylfurfural was 99.4%, the molar selectivity of 5-methyl-5-hydroxy-2 (5H) -furanone was 86.8% and the remaining by-product was formic acid, as analyzed by liquid chromatography.
Example 6:
respectively weighing Mn (NO) 3 ) 3 With Fe (NO) 3 ) 3 Dissolving in 50mL of deionized water, stirring, dissolving, adding NaOH solution, mixing uniformly, placing into a baking oven, keeping at 220 ℃ for 12 hours, filtering the obtained product, washing with deionized water and ethanol for 3 times respectively, and drying in the baking oven at 110 ℃ for 8 hours to obtain the MnOOH-FeOOH composite material (the ratio is 2:1).
The reaction of photocatalytic oxidation of furandicarboxylic acid was carried out in a photocatalytic reactor with a circulating water bath at a reaction speed of 600rpm. 1mmol of substrate, 50mg of catalyst, 10mL of 1, 4-dioxane were charged into a 50mL reactor and reacted at 30℃through a circulating water bath. The reactor was irradiated with a 200W xenon lamp and the reaction was completed after 12h of rapid stirring. The conversion of furandicarboxylic acid was 94.8%, the molar selectivity of 2-hydroxy-5-oxo-2, 5-dihydrofuran-2-carboxylic acid was 85.3% and the remaining by-product was formic acid, as analyzed by liquid chromatography.
Example 7:
co (NO) of corresponding mass is respectively weighed 3 ) 3 With Fe (NO) 3 ) 3 Dissolving in 50mL of deionized water, stirring, dissolving, adding NaOH solution, mixing uniformly, placing into a baking oven, keeping at 220 ℃ for 12 hours, filtering the obtained product, washing with deionized water and ethanol for 3 times respectively, and drying in the baking oven at 110 ℃ for 8 hours to obtain the FeOOH-CoOOH composite material (the ratio is 1:4).
The reaction of photocatalytic oxidation of 4-hydroxymethylfurfural was carried out in a photocatalytic reactor with a circulating water bath at a reaction speed of 600rpm. 1mmol of substrate, 25mg of catalyst, 15mL of toluene were charged into a 50mL reactor and reacted at 60℃through a circulating water bath. The reactor was irradiated with a 300W xenon lamp and the reaction was rapidly stirred for 16h and ended. The conversion of 4-hydroxymethylfurfural was 96.1% by liquid chromatography, the molar selectivity of 4-hydroxymethyl-5-hydroxy-2 (5H) -furanone was 94.8% and the remaining by-product was formic acid.
Example 8:
co (NO) of corresponding mass is respectively weighed 3 ) 3 With Ga (NO) 3 ) 3 Dissolving in 50mL of deionized water, stirring, dissolving, adding NaOH solution, mixing uniformly, placing into a baking oven, keeping at 220 ℃ for 12 hours, filtering the obtained product, washing with deionized water and ethanol for 3 times respectively, and drying in the baking oven at 110 ℃ for 8 hours to obtain the CoOOH-GaOOH composite material (the ratio is 1:2).
The reaction of photocatalytic oxidation of 4-methylfurfural was carried out in a photocatalytic reactor with a circulating water bath at a reaction speed of 600rpm. 1mmol of substrate, 50mg of catalyst, 10mL of cyclohexane were charged into a 50mL reactor and reacted at 40℃by means of a circulating water bath. The reactor was irradiated with 400W xenon lamp and the reaction was completed after 10h of rapid stirring. The conversion rate of the 4-methylfurfural was 100% and the molar selectivity of 4-methyl-5-hydroxy-2 (5H) -furanone was 93.5% by liquid chromatography analysis, with the remaining by-product being formic acid.
Example 9:
co (NO) of corresponding mass is respectively weighed 3 ) 3 With In (NO) 3 ) 3 Dissolving in 50mL of deionized water, stirring, dissolving, adding NaOH solution, mixing uniformly, placing into a baking oven, keeping at 220 ℃ for 12 hours, filtering the obtained product, washing with deionized water and ethanol for 3 times respectively, and drying in the baking oven at 110 ℃ for 8 hours to obtain the CoOOH-InOOH composite material (the ratio is 1:1).
The reaction of photocatalytic oxidation of 3-methylfurfural was carried out in a photocatalytic reactor with a circulating water bath at a reaction speed of 600rpm. 2mmol of substrate, 30mg of catalyst, 20mL of n-hexane were charged into a 50mL reactor and reacted at 20℃by a circulating water bath. The reactor was irradiated with a 300W xenon lamp and the reaction was completed after 4h of rapid stirring. The conversion rate of 3-methylfurfural was 98.6%, the molar selectivity of 3-methyl-5-hydroxy-2 (5H) -furanone was 87.7% and the remaining by-product was formic acid, as analyzed by liquid chromatography.

Claims (5)

1. A photocatalytic synthesis method of 2 (5H) -furanone compounds comprises the following steps:
under the catalysis of a photocatalyst, furfural and derivatives thereof are subjected to selective oxidation reaction to obtain 2 (5H) -furanone compounds;
the structural formula of the furfural and the derivative thereof is shown as formula I:
the structural formula of the 2 (5H) -furanone compound is shown as a formula II:
in the formula I and the formula II, R 1 is-H, -COOH, alkyl with 1-5 carbon atoms or alkyl alcohol with 1-5 carbon atoms, R 2 is-H, alkyl with 1-5 carbon atoms or alkyl alcohol with 1-5 carbon atoms, R 3 is-H, alkyl with 1-5 carbon atoms or alkyl alcohol with 1-5 carbon atoms;
in the formula I, R 4 is-H or-OH;
the photocatalyst is an inorganic semiconductor photocatalyst and is a composite material of one or two of the following oxyhydroxide:
AlOOH, scOOH, YOOH, VOOH, crOOH, gaOOH, mnOOH, feOOH, coOOH and InOOH.
2. The photocatalytic synthesis method according to claim 1, characterized in that: the dosage of the photocatalyst is as follows: 1mmol of furfural and derivatives thereof are added with 10 to 100mg of photocatalyst.
3. The photocatalytic synthesis method according to claim 1 or 2, characterized in that: the solvent adopted in the selective oxidation reaction is tetrahydrofuran, 1, 4-dioxane, toluene, cyclohexane, n-hexane, methanol, ethanol or water.
4. The photocatalytic synthesis method according to claim 1 or 2, characterized in that: the selective oxidation reaction is carried out under normal pressure, the temperature is 10-80 ℃, and the time is 1-24 h.
5. The photocatalytic synthesis method according to claim 1 or 2, characterized in that: the selective oxidation reaction adopts a xenon lamp light source, and the power of the xenon lamp light source is 100-400W.
CN202311429475.8A 2023-10-31 2023-10-31 Photocatalytic synthesis method of 2 (5H) -furanone compound Pending CN117486838A (en)

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