CN112898246A - Method for preparing 5-ethoxy methyl furfural - Google Patents
Method for preparing 5-ethoxy methyl furfural Download PDFInfo
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Abstract
A method for preparing 5-ethoxy methyl furfural is characterized in that 5-hydroxymethyl furfural is used as a reaction substrate, a sulfonic acid type high molecular nitrogen-containing polymer is used as a catalyst, and etherification reaction is carried out to obtain the 5-ethoxy methyl furfural. The method has the advantages of mild reaction conditions, short reaction time, simple process, high catalytic etherification efficiency, few byproducts, high product selectivity and low production cost; the sulfonic acid type high-molecular nitrogen-containing polymer catalyst used in the invention has high activity; according to the preferable scheme, the preparation process of the catalyst is simple, and the preparation cost is low.
Description
Technical Field
The invention relates to the field of biomass energy chemical industry, in particular to a method for preparing 5-ethoxy methyl furfural.
Background
With the depletion of non-renewable energy sources such as fossil fuels and the increase of human energy demand, the development and utilization of green renewable new energy sources become urgent.
Biomass is the only renewable organic carbon resource in the nature, and can be converted into high value-added chemicals and biofuels through a chemical approach. The research and development of biomass fuels promote the development of green and sustainable technologies, and have very important strategic significance for realizing fossil resource substitution.
5-Hydroxymethylfurfural (HMF) is an important platform molecule for linking carbohydrates with biomass fuels and can be converted into various fine chemicals through reactions such as oxidation, reduction, etherification and the like. The 5-Ethoxy Methyl Furfural (EMF) is a product of etherification of 5-hydroxymethyl furfural and ethanol, has the properties of high energy density, low toxicity, high stability, good fluidity and the like, and is a potential fuel or fuel additive. The high boiling point (508K) of the 5-ethoxymethylfurfural can be compared with diesel fuel, the energy density is as high as 8.7kWh/L, is obviously higher than that of ethanol (6.1kWh/L), and is equivalent to that of common gasoline (8.8kWh/L) and diesel oil (9.7 kWh/L). EMF also has a higher cetane number, which is a very important factor affecting combustion performance and emissions, and when EMF is added to diesel fuel, the harmful particles and sulfides produced during combustion are significantly reduced. EMF is considered a promising biofuel or fuel additive due to its good fuel properties, oxidation stability, low temperature fluidity, and low smoke and sulfide emissions.
At present, most of methods for preparing EMF by biomass-based HMF etherification have the defects of long reaction time, complex catalyst preparation, poor reaction selectivity, difficult product separation and the like, and a plurality of used catalysts are solid acid catalysts. Acid carbonaceous catalysts based on lignosulfonates (LS-SO), such as Yu3H) EMF was synthesized by catalytic HMF, with 85.5% yield at 80 ℃ for 11h, but the process was longer in reaction time (see One-step catalysis of carbonaceous solid acid derivative from lignin for the synthesis of biological fuel derivatives, RSC Advances,2018,8, 15762-. Preparation of fructose-derived carbon-based magnetic sulfonic acid catalyst (PCM-SO) by Yao et al through carbonization sulfonation3H) In the ethanol system, the substrate is 5-HMF, the 5-EMF yield is 85.6%, but the process is equally long and catalytically inefficient (see magnetic-reactive carbon sources material: an effective catalyst for the synthesis of 5-hydroxymethyifurfural)and 5-ethoxymethylated furfuel from carbohydrates, Russian Journal of General Chemistry,2016,86, 1698-1704.). YIN et al synthesized 5-EMF by free radical oligomerization of bisvinylimidazolium salts on mercaptopropyl-modified silica surface at 5-HMF reaction for 12h at 100 ℃ with a 5-EMF yield of 89.6%, but this process used a catalyst that was complex to prepare, difficult to control conditions and long in reaction time (see Magnetic material transformed cross-linked imide bed polymeric catalysts: an affinity catalyst for the synthesis of a formulating liquid fuel 5-ethoxy-amino acid from carbohydrates, Journal of Materials Chemistry A,2015,3, 4992-4999).
Disclosure of Invention
The invention aims to solve the technical problem of overcoming the defects in the prior art and provide the method for preparing the 5-ethoxymethylfurfural, which has the advantages of mild reaction conditions, short reaction time, simple process, high product selectivity and low production cost.
The technical scheme adopted for solving the technical problems is that 5-hydroxymethyl furfural is used as a reaction substrate, and a sulfonic acid type high-molecular nitrogen-containing polymer is used as a catalyst to carry out etherification reaction to obtain the 5-ethoxy methyl furfural.
Further, the method comprises the following specific operation steps: dissolving 5-hydroxymethylfurfural in ethanol to prepare a reaction substrate solution, adding a sulfonic acid type high-molecular nitrogen-containing polymer catalyst into the reaction substrate solution, mixing, placing in a closed reaction kettle, and continuously stirring for etherification reaction.
Further, the reaction temperature is 80-130 ℃, and preferably 90-120 ℃.
Further, the reaction time is 0.4-5.0 h, preferably 0.5-3.0 h.
Further, the stirring speed is 300-600 r/min, preferably 400-500 r/min.
Further, the mass ratio of the sulfonic acid type high-molecular nitrogen-containing polymer catalyst to the 5-hydroxymethylfurfural is 0.20-0.77: 1, preferably 0.23-0.42: 1. Too low a mass ratio results in insufficient active sites and low conversion of HMF, while too high a mass ratio results in reduced selectivity of the reaction product.
Further, the mass percentage concentration of the 5-hydroxymethylfurfural in the reaction substrate solution is 1-10%, preferably 3.25-5.50%. Too dilute a mass percent concentration can affect the HMF conversion, and too concentrated can result in a poor utilization of the feedstock.
Further, the sulfonic acid type high molecular nitrogen-containing polymer catalyst is prepared by the following method:
(1) preparation of catalyst support PDVTA: dissolving divinylbenzene and triallylamine in acetone, uniformly mixing, adding azobisisobutyronitrile under the atmosphere of nitrogen, and continuously stirring for reaction to obtain a reaction solution; then transferring the reaction solution into an aging kettle, and carrying out heating reaction to obtain a precipitate; filtering the precipitate, washing with acetone, and drying to obtain catalyst carrier PDVTA (poly (divinylbenzene) -triallylamine copolymer);
(2) sulfonated PDVTA: reacting the catalyst carrier PDVTA obtained in the step (1) with a sulfonating agent to obtain light purple precipitate; then washing and drying the light purple precipitate to obtain the catalyst PDVTA-SO3H。
Further, in the step (1) of the preparation method of the sulfonic acid type high molecular nitrogen-containing polymer catalyst, the temperature of the heating reaction is 100-180 ℃, preferably 120-160 ℃; the heating reaction time is 12-50 h, preferably 24-48 h.
Further, in the step (2) of the preparation method of the sulfonic acid type high molecular nitrogen-containing polymer catalyst, the sulfonating agent is one or more of concentrated sulfuric acid, fuming sulfuric acid and chlorosulfonic acid.
Further, in the step (2) of the preparation method of the sulfonic acid type high molecular nitrogen-containing polymer catalyst, the mass ratio of the catalyst carrier PDVTA to the sulfonating agent is 0.04-0.20: 1, preferably 0.05-0.15: 1. If the mass ratio is too small, the degree of sulfonation is insufficient, resulting in a decrease in the active center of the catalyst to be produced.
Further, in the step (2) of the preparation method of the sulfonic acid type high molecular nitrogen-containing polymer catalyst, the reaction temperature is 0-100 ℃, preferably 10-50 ℃; the reaction time is 1-10 h, preferably 4-10 h.
Compared with the prior art, the invention has the beneficial effects that: the reaction condition is mild, the reaction time is short, the process is simple, the catalytic etherification efficiency is high, the byproducts are few, the product selectivity is high, and the production cost is low; the sulfonic acid type high-molecular nitrogen-containing polymer catalyst used in the invention has high activity; according to the preferable scheme, the preparation process of the catalyst is simple, and the preparation cost is low.
Detailed Description
The present invention will be further described with reference to the following specific examples. It should be noted that the described embodiments illustrate only some of the embodiments of the invention, and should not be construed as limiting the scope of the claims. All other changes and modifications which can be made by one skilled in the art based on the embodiments of the present invention without inventive faculty are within the scope of the claims of the present application.
The chemicals used in the examples, unless otherwise specified, were obtained from conventional commercial sources.
Example 1
This example prepared 5-ethoxymethylfurfural by formulating 0.130g of 5-hydroxymethylfurfural and 5mL of ethanol as a reaction substrate solution and then adding 42.5mg of PDVTA-SO3Adding an H catalyst into the reaction substrate solution, mixing, placing in a closed reaction kettle, continuously stirring, carrying out etherification reaction at 110 ℃, reacting for 0.5H, and stirring at the speed of 500r/min to obtain the 5-ethoxymethylfurfural.
The sulfonic acid type high molecular nitrogen-containing polymer catalyst used in this example was prepared by the following method:
(1) preparation of catalyst support PDVTA: dissolving 3.124g of divinylbenzene and 0.824g of triallylamine in 25mL of acetone, stirring for 30min, mixing uniformly, adding 0.1g of azobisisobutyronitrile as an initiator under the nitrogen atmosphere, and continuously stirring and reacting for 12h at 40 ℃ to obtain a reaction solution; then transferring the reaction solution into a high-pressure kettle, and reacting for 24 hours at 120 ℃ to obtain a precipitate; filtering the precipitate, washing with acetone, and drying at 100 deg.C for 10 hr to obtain catalyst carrier PDVTA;
(2) sulfonated PDVTA: taking 1g of the catalyst carrier PDVTA obtained in the step (1) to a 100mL round-bottom flask, adding 40mL of dichloromethane, and introducing N2Slowly dripping 5mL of mixed solution of chlorosulfonic acid and dichloromethane by using a constant-pressure dropping funnel under the condition of ice-water bath, stirring for reacting for 4 hours, and then slowly dripping ethanol to the system to obtain a light purple precipitate; then washing and drying the light purple precipitate to obtain the catalyst PDVTA-SO3H。
Sulfonic acid type high molecular nitrogen-containing Polymer catalyst PDVTA-SO used in the following examples3Preparation method of H and PDVTA-SO of this example3The preparation method of the H catalyst is the same.
The test method comprises the following steps: and cooling the reaction liquid after the etherification reaction to room temperature, carrying out gas phase analysis, and detecting the conversion rate of the 5-hydroxymethylfurfural and the selectivity of the 5-ethoxymethylfurfural.
The following examples each test method for the conversion of 5-hydroxymethylfurfural and the selectivity of 5-ethoxymethylfurfural was the same as the test method of this example.
According to the detection, the conversion rate of the 5-hydroxymethylfurfural in the embodiment is 99.8%, and the selectivity of the 5-ethoxymethylfurfural is 87.7%.
Example 2
This example prepared 5-ethoxymethylfurfural by formulating 0.132g of 5-hydroxymethylfurfural and 5mL of ethanol as a reaction substrate solution and then formulating 50mg of PDVTA-SO3Adding an H catalyst into the reaction substrate solution, mixing, placing in a closed reaction kettle, continuously stirring, carrying out etherification reaction at 90 ℃, reacting for 1.5H, and stirring at the speed of 400r/min to obtain the 5-ethoxymethylfurfural.
According to the detection, the conversion rate of the 5-hydroxymethylfurfural in the embodiment is 75.0%, and the selectivity of the 5-ethoxymethylfurfural is 92.3%.
Example 3
This example prepared 5-ethoxymethylfurfural by formulating 0.129g of 5-hydroxymethylfurfural and 5mL of ethanol as a reaction substrate solution and then adding 50mg of PDVTA-SO3Adding H catalyst into the reaction substrate solution, mixing and placing in a closed stateContinuously stirring the mixture in the reaction kettle, carrying out etherification reaction at the temperature of 90 ℃, reacting for 3 hours at the stirring speed of 500r/min, and obtaining the 5-ethoxy methyl furfural.
According to the detection, the conversion rate of the 5-hydroxymethylfurfural in the embodiment is 85.5%, and the selectivity of the 5-ethoxymethylfurfural is 91.3%.
Example 4
This example prepared 5-ethoxymethylfurfural by formulating 0.131g of 5-hydroxymethylfurfural and 5mL of ethanol as a reaction substrate solution and then formulating 40mg of PDVTA-SO3Adding an H catalyst into the reaction substrate solution, mixing, placing in a closed reaction kettle, continuously stirring, carrying out etherification reaction at 100 ℃, reacting for 1H, and stirring at the speed of 500r/min to obtain the 5-ethoxymethylfurfural.
According to the detection, the conversion rate of the 5-hydroxymethylfurfural in the embodiment is 93.7%, and the selectivity of the 5-ethoxymethylfurfural is 89.8%.
Example 5
This example prepared 5-ethoxymethylfurfural by formulating 0.130g of 5-hydroxymethylfurfural and 5mL of ethanol as a reaction substrate solution and then adding 30mg of PDVTA-SO3Adding an H catalyst into the reaction substrate solution, mixing, placing in a closed reaction kettle, continuously stirring, carrying out etherification reaction at 100 ℃, reacting for 1.5H, and stirring at the speed of 400r/min to obtain the 5-ethoxymethylfurfural.
According to the detection, the conversion rate of the 5-hydroxymethylfurfural in the embodiment is 91.2%, and the selectivity of the 5-ethoxymethylfurfural is 91.1%.
Example 6
This example prepared 5-ethoxymethylfurfural by formulating 0.128g of 5-hydroxymethylfurfural and 5mL of ethanol as a reaction substrate solution and then formulating 40mg of PDVTA-SO3Adding an H catalyst into the reaction substrate solution, mixing, placing in a closed reaction kettle, continuously stirring, carrying out etherification reaction at 120 ℃, reacting for 2H, wherein the stirring speed is 500r/min, and obtaining the 5-ethoxymethylfurfural.
According to the detection, the conversion rate of the 5-hydroxymethylfurfural in the embodiment is 99.8%, and the selectivity of the 5-ethoxymethylfurfural is 80.3%.
Example 7
This example prepared 5-ethoxymethylfurfural by formulating 0.129g of 5-hydroxymethylfurfural and 5mL of ethanol as a reaction substrate solution and then formulating 40mg of PDVTA-SO3Adding an H catalyst into the reaction substrate solution, mixing, placing in a closed reaction kettle, continuously stirring, carrying out etherification reaction at 110 ℃, reacting for 1H, and stirring at the speed of 400r/min to obtain the 5-ethoxymethylfurfural.
According to the detection, the conversion rate of the 5-hydroxymethylfurfural in the embodiment is 99.5%, and the selectivity of the 5-ethoxymethylfurfural is 84.3%.
Example 8
This example prepared 5-ethoxymethylfurfural by formulating 0.128g of 5-hydroxymethylfurfural and 5mL of ethanol as a reaction substrate solution and then formulating 40mg of PDVTA-SO3Adding an H catalyst into the reaction substrate solution, mixing, placing in a closed reaction kettle, continuously stirring, carrying out etherification reaction at 100 ℃, reacting for 1.5H, and stirring at the speed of 500r/min to obtain the 5-ethoxymethylfurfural.
According to the detection, the conversion rate of the 5-hydroxymethylfurfural in the embodiment is 92.5%, and the selectivity of the 5-ethoxymethylfurfural is 91.3%.
Example 9
This example prepared 5-ethoxymethylfurfural by formulating 0.133g of 5-hydroxymethylfurfural and 5mL of ethanol as a reaction substrate solution and then adding 50mg of PDVTA-SO3Adding an H catalyst into the reaction substrate solution, mixing, placing in a closed reaction kettle, continuously stirring, carrying out etherification reaction at 110 ℃, reacting for 3H, wherein the stirring speed is 400r/min, and obtaining the 5-ethoxymethylfurfural.
According to the detection, the conversion rate of the 5-hydroxymethylfurfural in the embodiment is 99.7%, and the selectivity of the 5-ethoxymethylfurfural is 80.2%.
Example 10
This example prepared 5-ethoxymethylfurfural by formulating 0.131g of 5-hydroxymethylfurfural and 5mL of ethanol as a reaction substrate solution and then adding 30mg of PDVTA-SO3H catalyst is added into the reaction bottomAnd mixing the solution, placing the mixture in a closed reaction kettle, continuously stirring, carrying out etherification reaction at 120 ℃ for 3 hours at the stirring speed of 400r/min, and obtaining the 5-ethoxy methyl furfural.
According to the detection, the conversion rate of the 5-hydroxymethylfurfural in the embodiment is 99.0%, and the selectivity of the 5-ethoxymethylfurfural is 79.2%.
Claims (10)
1. A method for preparing 5-ethoxy methyl furfural is characterized in that 5-hydroxymethyl furfural is used as a reaction substrate, a sulfonic acid type high molecular nitrogen-containing polymer is used as a catalyst, and etherification reaction is carried out to obtain the 5-ethoxy methyl furfural.
2. The method for preparing 5-ethoxymethylfurfural according to claim 1, characterized by comprising the following specific operation steps: dissolving 5-hydroxymethylfurfural in ethanol to prepare a reaction substrate solution, adding a sulfonic acid type high-molecular nitrogen-containing polymer catalyst into the reaction substrate solution, mixing, placing in a closed reaction kettle, and continuously stirring for etherification reaction.
3. The method for preparing 5-ethoxymethylfurfural according to claim 2, characterized in that the reaction temperature is 80 to 130 ℃, preferably 90 to 120 ℃; the reaction time is 0.4-5.0 h, preferably 0.5-3.0 h.
4. The method for preparing 5-ethoxymethylfurfural according to claim 2 or 3, characterized in that the stirring speed is 300 to 600r/min, preferably 400 to 500 r/min.
5. The method for preparing 5-ethoxymethylfurfural according to any one of claims 2 to 4, wherein the mass ratio of the sulfonic acid-type high-molecular nitrogen-containing polymer catalyst to the 5-hydroxymethylfurfural is 0.20 to 0.77:1, preferably 0.23 to 0.42: 1.
6. The method for preparing 5-ethoxymethylfurfural according to any one of claims 2 to 5, wherein the concentration of 5-hydroxymethylfurfural in the reaction substrate solution is 1 to 10% by mass, preferably 3.25 to 5.50% by mass.
7. The method for preparing 5-ethoxymethylfurfural according to any one of claims 2 to 6, wherein the sulfonic acid type high-molecular nitrogen-containing polymer catalyst is prepared by the following method:
(1) preparation of catalyst support PDVTA: dissolving divinylbenzene and triallylamine in acetone, uniformly mixing, adding azobisisobutyronitrile under the atmosphere of nitrogen, and continuously stirring for reaction to obtain a reaction solution; then transferring the reaction solution into an aging kettle, and carrying out heating reaction to obtain a precipitate; filtering the precipitate, washing with acetone, and drying to obtain catalyst carrier PDVTA;
(2) sulfonated PDVTA: reacting the catalyst carrier PDVTA obtained in the step (1) with a sulfonating agent to obtain light purple precipitate; then washing and drying the light purple precipitate to obtain the catalyst PDVTA-SO3H。
8. The method for preparing 5-ethoxymethylfurfural according to claim 7, wherein in the step (1) of the method for preparing the sulfonic acid-type high-molecular nitrogen-containing polymer catalyst, the temperature of the heating reaction is 100 to 180 ℃, preferably 120 to 160 ℃; the heating reaction time is 12-50 h, preferably 24-48 h.
9. The method for preparing 5-ethoxymethylfurfural according to claim 7 or 8, wherein in step (2) of the method for preparing a sulfonic acid-type high-molecular nitrogen-containing polymer catalyst, the sulfonating agent is one or more of concentrated sulfuric acid, fuming sulfuric acid, and chlorosulfonic acid; the mass ratio of the catalyst carrier PDVTA to the sulfonating agent is 0.04-0.20: 1, preferably 0.05-0.15: 1.
10. The method for preparing 5-ethoxymethylfurfural according to any one of claims 7 to 9, wherein in the step (2) of the method for preparing the sulfonic acid-type high-molecular nitrogen-containing polymer catalyst, the reaction temperature is 0 to 100 ℃, preferably 10 to 50 ℃; the reaction time is 1-12 h, preferably 4-10 h.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116217524A (en) * | 2023-02-23 | 2023-06-06 | 中国科学院广州能源研究所 | Method for synthesizing 5-ethoxymethyl furfural by catalyzing biomass or derivative thereof with modified polyurethane sponge carbon |
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| CN102911141A (en) * | 2011-08-05 | 2013-02-06 | 中国科学院大连化学物理研究所 | Method for preparing 5-ethyoxyl methylfurfural |
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2021
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Patent Citations (2)
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| CN102911141A (en) * | 2011-08-05 | 2013-02-06 | 中国科学院大连化学物理研究所 | Method for preparing 5-ethyoxyl methylfurfural |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116217524A (en) * | 2023-02-23 | 2023-06-06 | 中国科学院广州能源研究所 | Method for synthesizing 5-ethoxymethyl furfural by catalyzing biomass or derivative thereof with modified polyurethane sponge carbon |
| CN116217524B (en) * | 2023-02-23 | 2024-03-08 | 中国科学院广州能源研究所 | Method for synthesizing 5-ethoxymethyl furfural by catalyzing biomass or derivative thereof with modified polyurethane sponge carbon |
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