CN112961123B - Method for preparing 3- (2-furyl) -2-methyl-2-acrolein by catalyzing oxidation condensation of furfural and n-propanol - Google Patents
Method for preparing 3- (2-furyl) -2-methyl-2-acrolein by catalyzing oxidation condensation of furfural and n-propanol Download PDFInfo
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Abstract
A method for preparing 3- (2-furyl) -2-methyl-2-acrolein by catalyzing furfural and n-propanol to carry out oxidative condensation is to use furfural as a substrate and copper salt as a catalyst to prepare 3- (2-furyl) -2-methyl-2-acrolein, mix the furfural and the n-propanol, add metal copper salt and alkaline auxiliary agent, react for 1 to 72 hours at the temperature of 25 to 160 ℃, the oxygen pressure of 0.01 to 9.0MPa and the stirring speed of 100 to 5000r/min to obtain the product. The advantages are that: 1. the reaction process of the 'one-pot method' is adopted, the reaction process is shortened, and the yield of the main product is improved; 2. the homogeneous catalytic system has mild reaction conditions, and can efficiently catalyze furfural and n-propanol to carry out selective oxidation and condensation to synthesize 3- (2-furyl) -2-methyl-2-acrolein; 3. is suitable for various aldehydes including aromatic aldehyde, aliphatic aldehyde and the like, and has the characteristics of few byproducts and high product yield.
Description
Technical Field
The invention relates to a method for preparing 3- (2-furyl) -2-methyl-2-acrolein by oxidizing and condensing furfural, in particular to a method for oxidizing and condensing furfural and n-propanol by using a homogeneous catalyst copper salt as a catalyst.
Background
In recent years, the development of renewable resources to replace fossil fuels has attracted considerable attention in the chemical field. As a sustainable and readily available natural resource, biomass feedstocks can be directly converted into valuable chemicals and liquid fuels. Furan derivatives furfural and 5-hydroxymethylfurfural are considered important biomass-based platform compounds because they are readily prepared from cellulose and hemicellulose by dehydration. In general, furfural can be obtained from agricultural raw materials, corn, wheat bran and sawdust. Because of the furan ring and aldehyde group contained in the structure, the groups are considered as an intermediate for producing high value-added chemicals in the industry. Therefore, it is very interesting to explore the production of high value-added chemicals or biofuels from furfural rather than fossil fuels. Among them, furfural is capable of preparing various chemical substances through simple reaction processes such as hydrogenation, oxidation, reductive amination, nitration, decarburization and condensation. For example, the highly efficient aldol condensation reaction between furfural and acetone has become a key intermediate step in the synthesis of second generation biofuels. Research shows that selective conversion of biomass platform compounds through continuous catalytic reaction is not only beneficial to improving industrial production efficiency, but also capable of reducing energy consumption. In addition, the oxidative esterification of furfural can also produce alkyl furoates which can be used as flavor and fragrance ingredients in the fine chemical industry.
The oxidative condensation reaction of furfural and linear alcohols in the presence of oxygen is an important reaction pathway. However, the catalysts used are all noble metal catalysts, e.g. Au/A l2 O 3 ，Au/Fe x O y HAP, etc., and the preparation method of the catalyst is relatively complicated. . Therefore, the development of a homogeneous catalysis system with high catalysis efficiency, low reaction cost, good selectivity and environmental friendliness is of great significance.
The invention content is as follows:
the invention aims to provide a method for preparing 3- (2-furyl) -2-methyl-2-acrolein by efficiently catalyzing furfural with a copper salt homogeneous catalysis system aiming at the technical analysis and the existing problems, and the method has the advantages that: the method adopts a one-pot reaction process, and simultaneously carries out three reactions of hydrogen transfer, condensation and oxidation between furfural and normal propyl alcohol by virtue of the synergistic effect of a catalyst system. The method has the advantages of simple process, economy, environmental protection, good catalytic effect, high yield of main products, easy separation, mild reaction conditions, low production cost, no potential safety hazard and environmental friendliness.
The technical scheme adopted by the invention is as follows:
a method for preparing 3- (2-furyl) -2-methyl-2-acrolein by catalyzing oxidation condensation of furfural and n-propanol takes furfural as a substrate and copper salt as a catalyst to prepare the 3- (2-furyl) -2-methyl-2-acrolein, and the specific method comprises the following steps: mixing furfural and n-propanol, adding a metal copper salt and an alkaline assistant, and reacting for 1-72h at the temperature of 25-160 ℃, the oxygen pressure of 0.01-9.0MPa and the stirring speed of 100-5000r/min to obtain the product.
Furthermore, the dosage of the furfural and the dosage of the n-propanol are respectively 0.1-0.9g and 5-30mL.
Further, the cupric salt is one of cuprous chloride, cuprous iodide, cuprous bromide, cuprous fluoride, cupric chloride, cupric iodide, cupric bromide or cupric fluoride, and the dosage of the cupric salt is 0.05-40mol% of the furfural.
Further, the furfural includes but is not limited to furfural, 5-hydroxymethyl furfural, 5-chloro-2-furfural, 5-bromo-2-furfural and 5-methylfurfural.
Further, the reaction temperature in the oxidation reaction process is 25-160 ℃.
Further, the pressure of the reaction oxygen of the oxidation reaction is 0.1-0.5MPa.
Further, the alkaline assistant includes lithium hydroxide, potassium carbonate, sodium hydroxide, cesium hydroxide, sodium carbonate, potassium phosphate, and the like.
Furthermore, the reaction time of the oxidation reaction process is between 2 and 12 hours.
Furthermore, the weight of the added alkaline auxiliary agent is 1-30% of the mass of the added aldehydes.
The advantages are that: 1. the one-pot reaction process is adopted, the reaction process is shortened, and the yield of the main product is improved; 2. the homogeneous catalytic system has mild reaction conditions, and can efficiently catalyze furfural and n-propanol to carry out selective oxidation and condensation to synthesize 3- (2-furyl) -2-methyl-2-acrolein; 3. the invention can be applied to various aldehydes including aromatic aldehyde, aliphatic aldehyde and the like, and has the characteristics of less by-products and high product yield.
Detailed Description
The invention is further illustrated by the following examples.
Example 1:
a method for preparing 3- (2-furyl) -2-methyl-2-acrolein by efficiently catalyzing and oxidizing furfural comprises the following steps:
the method is characterized by taking furfural as a substrate and copper salt as a catalyst to study the catalytic oxidation-condensation reaction of furfural and n-propanol, and comprises the specific steps of dissolving 0.1g (1.04 mmol) of furfural in 10mL of n-propanol, adding 0.0051g of cuprous chloride catalyst, 0.01g of potassium hydroxide auxiliary agent and 0.3MPa of oxygen, reacting for 4 hours at the temperature of 80 ℃ and the stirring speed of 100r/min, and selectively catalytically oxidizing furfural by using an alkaline auxiliary agent to prepare 3- (2-furyl) -2-methyl-2-acrolein and furfuryl alcohol. The reaction results were analyzed by gas chromatography with a mass spectrometer: the conversion of furfural was 64.7%, and the selectivities to 3- (2-furyl) -2-methyl-2-propenal and furfuryl alcohol were 62.3% and 37.7%, respectively.
Example 2:
a method for preparing 3- (2-furyl) -2-methyl-2-acrolein by efficiently catalyzing and oxidizing furfural comprises the following steps:
the method is characterized by taking furfural as a substrate and copper salt as a catalyst to study the catalytic oxidation-condensation reaction of furfural and n-propanol, and comprises the specific steps of dissolving 0.1g (1.04 mmol) of furfural in 10mL of n-propanol, adding 0.0051g of cuprous chloride catalyst, 0.01g of sodium hydroxide auxiliary agent and 0.3MPa of oxygen, reacting for 4 hours at the temperature of 80 ℃ and the stirring speed of 100r/min, and selectively catalytically oxidizing furfural by using an alkaline auxiliary agent to prepare 3- (2-furyl) -2-methyl-2-acrolein and furfuryl alcohol. The reaction results were analyzed by gas chromatograph/mass spectrometer and gas chromatography: the conversion of furfural was 95.0%, and the selectivity of 3- (2-furyl) -2-methyl-2-propenal and furfuryl alcohol was 89.9% and 10.1%, respectively.
Example 3:
a method for preparing 3- (2-furyl) -2-methyl-2-acrolein by efficiently catalyzing and oxidizing furfural comprises the following steps:
the method is characterized by taking furfural as a substrate and copper salt as a catalyst to study the catalytic oxidation-condensation reaction of furfural and n-propanol, and comprises the specific steps of dissolving 0.1g (1.04 mmol) of furfural in 10mL of n-propanol, adding 0.0051g of cuprous chloride catalyst and 0.01g of lithium hydroxide auxiliary agent, reacting for 4 hours under the conditions of oxygen atmosphere of 0.3MPa at the temperature of 100 ℃ and the stirring speed of 100r/min, and selectively catalytically oxidizing furfural by using an alkaline auxiliary agent to prepare 3- (2-furyl) -2-methyl-2-acrolein and furfuryl alcohol. The reaction results were analyzed by gas chromatograph/mass spectrometer and gas chromatography: the conversion of furfural was 92.3%, and the selectivity of 3- (2-furyl) -2-methyl-2-propenal and furfuryl alcohol was 99.2% and 0.8%, respectively.
Example 4:
a method for preparing 3- (2-furyl) -2-methyl-2-acrolein by efficiently catalyzing and oxidizing furfural comprises the following steps:
the method is characterized by taking furfural as a substrate and copper salt as a catalyst to study the catalytic oxidation-condensation reaction of furfural and n-propanol, and comprises the specific steps of dissolving 0.1g (1.04 mmol) of furfural in 10mL of n-propanol, adding 0.0051g of cuprous chloride catalyst, 0.01g of lithium hydroxide as an auxiliary agent and 0.3MPa of oxygen, reacting for 4 hours at the temperature of 80 ℃ and the stirring speed of 100r/min, and selectively catalytically oxidizing furfural by using an alkaline auxiliary agent to prepare 3- (2-furyl) -2-methyl-2-acrolein and furfuryl alcohol. The reaction results were analyzed by gas chromatography with a mass spectrometer: the conversion rate of furfural was 94.8%, and the selectivity of 3- (2-furyl) -2-methyl-2-propenal and furfuryl alcohol was 97.5% and 2.5%, respectively.
Example 5:
a method for preparing 3- (2-furyl) -2-methyl-2-acrolein by efficiently catalyzing and oxidizing furfural comprises the following steps:
the method is characterized by taking furfural as a substrate and copper salt as a catalyst to study the catalytic oxidation-condensation reaction of furfural and n-propanol, and comprises the specific steps of dissolving 0.1g (1.04 mmol) of furfural in 10mL of n-propanol, adding 0.0051g of cuprous chloride catalyst and 0.01g of lithium hydroxide as an auxiliary agent, reacting for 4 hours under the conditions of oxygen atmosphere of 0.3MPa at the temperature of 60 ℃ and stirring speed of 100r/min, and selectively catalytically oxidizing furfural by using an alkaline auxiliary agent to prepare 3- (2-furyl) -2-methyl-2-acrolein and furfuryl alcohol. The reaction results were analyzed by gas chromatography with a mass spectrometer: the conversion of furfural was 95.3%, and the selectivity of 3- (2-furyl) -2-methyl-2-propenal and furfuryl alcohol was 92.2% and 7.8%, respectively.
Example 6:
a method for preparing 3- (2-furyl) -2-methyl-2-acrolein by efficiently catalyzing and oxidizing furfural comprises the following steps:
the method comprises the steps of dissolving 0.1g (1.04 mmol) of furfural in 10mL of n-propanol, adding 0.0051g of cuprous chloride serving as a catalyst and 0.01g of lithium hydroxide serving as an auxiliary agent into the n-propanol, reacting for 4 hours under the conditions of temperature of 40 ℃ and stirring speed of 100r/min under the oxygen atmosphere of 0.3MPa, and selectively catalyzing and oxidizing the furfural by using an alkaline auxiliary agent to prepare the 3- (2-furyl) -2-methyl-2-acrolein and furfuryl alcohol. The reaction results were analyzed by gas chromatography with a mass spectrometer: the conversion of furfural was 58.1%, and the selectivities to 3- (2-furyl) -2-methyl-2-propenal and furfuryl alcohol were 92.3% and 7.7%, respectively.
Example 7:
a method for preparing 3- (2-furyl) -2-methyl-2-acrolein by efficiently catalyzing and oxidizing furfural comprises the following steps:
the method comprises the steps of dissolving 0.1g (1.04 mmol) of furfural in 10mL of n-propanol, adding 0.0051g of cuprous chloride serving as a catalyst and 0.01g of lithium hydroxide serving as an auxiliary agent into the n-propanol, reacting for 4 hours under the conditions of 25 ℃ and 100r/min of stirring speed and oxygen atmosphere and selectively catalyzing and oxidizing furfural by using an alkaline auxiliary agent to prepare 3- (2-furyl) -2-methyl-2-acrolein and furfuryl alcohol. The reaction results were analyzed by gas chromatography with a mass spectrometer: the conversion rate of furfural was 35.2%, and the selectivity of 3- (2-furyl) -2-methyl-2-propenal and furfuryl alcohol was 68.8% and 31.2%, respectively.
Example 8:
a method for preparing 3- (2-furyl) -2-methyl-2-acrolein by efficiently catalyzing and oxidizing furfural comprises the following steps:
the method is characterized by taking furfural as a substrate and copper salt as a catalyst to study the catalytic oxidation-condensation reaction of furfural and n-propanol, and comprises the specific steps of dissolving 0.1g (1.04 mmol) of furfural in 10mL of n-propanol, adding 0.01g of cuprous iodide with initial dosage, 0.01g of lithium hydroxide as an auxiliary agent, reacting for 4 hours under the conditions of oxygen atmosphere of 0.3MPa at the temperature of 80 ℃ and stirring speed of 100r/min, and selectively catalytically oxidizing furfural by using an alkaline auxiliary agent to prepare 3- (2-furyl) -2-methyl-2-acrolein and furfuryl alcohol. The reaction results were analyzed by gas chromatography with a mass spectrometer: the conversion of furfural was 94.9%, and the selectivity of 3- (2-furyl) -2-methyl-2-propenal and furfuryl alcohol was 87.4% and 12.6%, respectively.
Example 9:
a method for preparing 3- (2-furyl) -2-methyl-2-acrolein by efficiently catalyzing and oxidizing furfural comprises the following steps:
the method is characterized by taking furfural as a substrate and copper salt as a catalyst to study the catalytic oxidation-condensation reaction of furfural and n-propanol, and comprises the specific steps of dissolving 0.1g (1.04 mmol) of furfural in 10mL of n-propanol, adding 0.0075g of cuprous bromide as a catalyst and 0.01g of lithium hydroxide as an auxiliary agent, reacting for 4 hours under the conditions of oxygen atmosphere and stirring speed of 100r/min at 80 ℃ under the oxygen atmosphere, and selectively catalytically oxidizing furfural by using an alkaline auxiliary agent to prepare 3- (2-furyl) -2-methyl-2-acrolein and furfuryl alcohol. The reaction results were analyzed by gas chromatography with a mass spectrometer: the conversion of furfural was 93.8%, and the selectivity of 3- (2-furyl) -2-methyl-2-propenal and furfuryl alcohol was 95.6% and 4.4%, respectively.
Example 10:
a method for preparing 3- (2-furyl) -2-methyl-2-acrolein by efficiently catalyzing and oxidizing furfural comprises the following steps:
the method is characterized by taking furfural as a substrate and copper salt as a catalyst to study the catalytic oxidation-condensation reaction of furfural and n-propanol, and comprises the specific steps of dissolving 0.1g (1.04 mmol) of furfural in 10mL of n-propanol, adding 0.0088g of copper chloride catalyst and 0.01g of lithium hydroxide auxiliary agent, reacting for 4 hours under the conditions of oxygen atmosphere of 0.3MPa at the temperature of 80 ℃ and stirring speed of 100r/min, and selectively catalytically oxidizing furfural by using an alkaline auxiliary agent to prepare 3- (2-furyl) -2-methyl-2-acrolein and furfuryl alcohol. The reaction results were analyzed by gas chromatography with a mass spectrometer: the conversion of furfural was 61.3%, and the selectivity of 3- (2-furyl) -2-methyl-2-propenal and furfuryl alcohol was 71.8% and 28.2%, respectively.
Example 11:
a method for preparing 3- (2-furyl) -2-methyl-2-acrolein by efficiently catalyzing and oxidizing furfural comprises the following steps:
the method is characterized by taking furfural as a substrate and copper salt as a catalyst to study the catalytic oxidation-condensation reaction of furfural and n-propanol, and comprises the specific steps of dissolving 0.1g (1.04 mmol) of furfural in 10mL of n-propanol, adding 0.011g of copper bromide as the catalyst and 0.01g of lithium hydroxide as an auxiliary agent, reacting for 4 hours under the conditions of oxygen atmosphere and stirring speed of 100r/min at 80 ℃ and oxygen atmosphere, and selectively catalytically oxidizing furfural by using an alkaline auxiliary agent to prepare 3- (2-furyl) -2-methyl-2-acrolein and furfuryl alcohol. The reaction results were analyzed by gas chromatography with a mass spectrometer: the conversion of furfural was 84.1%, and the selectivity of 3- (2-furyl) -2-methyl-2-propenal and furfuryl alcohol was 66.8% and 33.2%, respectively.
The above examples show that: by adopting the method provided by the invention, furfural and n-propanol can be efficiently catalyzed to carry out oxidation condensation reaction to generate 3- (2-furyl) -2-methyl-2-acrolein; the catalyst has the advantages of cheap and easily obtained raw materials, mild reaction conditions, simple and easy reaction process, capability of meeting the technical and economic requirements, and wide application prospect.
It should be further noted that the embodiment of the present invention is not limited to the technical solution of the present invention, and other catalysts involved in the technical solution, such as cuprous chloride, cuprous fluoride, cupric iodide, cupric bromide or cupric fluoride, and auxiliaries, such as potassium carbonate, cesium hydroxide, sodium carbonate, potassium phosphate, can achieve the objects of the present invention within the limits of the dosage of the reactants, the reaction temperature, the reaction time, the stirring speed, etc., defined in the technical solution of the present invention, so as to achieve the technical effects of the present invention.
Claims (5)
1. A method for preparing 3- (2-furyl) -2-methyl-2-acrolein by catalyzing oxidation condensation of furfural and n-propanol is characterized in that furfural is used as a substrate, copper salt is used as a catalyst to prepare the 3- (2-furyl) -2-methyl-2-acrolein, and the specific method comprises the following steps: mixing furfural and n-propanol, adding a metal copper salt and an alkaline assistant, and reacting at the temperature of 25-160 ℃, the oxygen pressure of 0.01-9.0MPa and the stirring speed of 100-5000r/min for 1-72h to obtain a product;
the copper salt is one of cuprous chloride, cuprous iodide, cuprous bromide, cuprous fluoride, cupric chloride, cupric iodide, cupric bromide or cupric fluoride, and the using amount is 0.05-40mol% of the furfural;
the alkaline assistant is one of lithium hydroxide, potassium carbonate, sodium hydroxide, cesium hydroxide, sodium carbonate and potassium phosphate.
2. The method for preparing 3- (2-furyl) -2-methyl-2-acrolein by catalyzing the oxidative condensation of furfural and n-propanol according to claim 1, wherein: the dosage of the furfural and the dosage of the n-propanol are respectively 0.1-0.9g and 5-30mL.
3. The method for preparing 3- (2-furyl) -2-methyl-2-acrolein by catalyzing oxidative condensation of furfural and n-propanol according to claim 1, wherein: the pressure of the oxygen in the oxidation reaction is 0.1-0.5MPa.
4. The method for preparing 3- (2-furyl) -2-methyl-2-acrolein by catalyzing oxidative condensation of furfural and n-propanol according to claim 1, wherein: the reaction time of the oxidation reaction process is between 2 and 12 hours.
5. The method for preparing 3- (2-furyl) -2-methyl-2-acrolein by catalyzing oxidative condensation of furfural and n-propanol according to claim 1, wherein: the weight of the added alkaline auxiliary agent is 1 to 30 percent of the weight of the added furfural.
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