CN111116525B - 2, 5-dimethylfuran and method for preparing 2, 5-dimethylfuran by hydrogenation of 5-hydroxymethylfurfural - Google Patents
2, 5-dimethylfuran and method for preparing 2, 5-dimethylfuran by hydrogenation of 5-hydroxymethylfurfural Download PDFInfo
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Abstract
The invention provides 2, 5-dimethylfuran and a method for preparing 2, 5-dimethylfuran by hydrogenation of 5-hydroxymethylfurfural, wherein the method comprises the following steps: under the nitrogen atmosphere, 5-hydroxymethylfurfural and a catalyst react in an alcohol solvent at the temperature of 200-250 ℃ for 1-7h, solid-liquid separation is carried out after the reaction, and a liquid-phase product is collected and purified; the active component of the supported copper-based catalyst is CuO, and the carrier is MgO-ZrO 2 The alcohol in the alcohol solvent is selected from more than one of methanol, isopropanol and 2-butanol; according to the invention, the biomass derivative 5-hydroxymethylfurfural is used as a raw material, the supported copper-based material is used as a catalyst, the alcohol solvent is used as a hydrogen donor, a noble metal catalyst and high-pressure hydrogen which is difficult to store and transport are not needed, so that the reaction condition is mild, the reaction raw material is a renewable biomass derivative, and a new way is further provided for the utilization of renewable biomass energy.
Description
Technical Field
The invention belongs to the technical field of energy chemical industry, and particularly relates to 2, 5-dimethylfuran and a method for preparing the 2, 5-dimethylfuran by hydrogenation of 5-hydroxymethylfurfural.
Background
For coal, oil and natural gasThe excessive dependence and consumption of fossil energy has caused human beings to face serious energy and environmental crisis. There is much interest in developing and utilizing renewable clean energy sources such as solar energy, wind energy, tidal energy, and biomass energy. The biomass energy has the advantages of low pollution, wide distribution, rich sources, large reserves and the like. The effective utilization of biomass resources can alleviate the human need for fossil energy to some extent. 2, 5-dimethylfuran is widely recognized as a promising liquid fuel. Compared with ethanol, 2, 5-dimethylfuran has a low boiling point (92 ℃), is storage-stable, and has a higher volumetric energy density (31.5 kJ cm) -3 40% higher than ethanol, making it consume one third of the energy it produces for fermentation of ethanol in its production evaporation stage, higher boiling point (92-94, ethanol 78 ℃), higher octane number (RON = 119) and lower oxygen content (O/C = 0.17) compared to gasoline. Meanwhile, 2, 5-dimethylfuran is insoluble in water and is more easily mixed with gasoline than ethanol. The 2, 5-dimethylfuran mixed gasoline shows more efficient application in a single-cylinder gasoline direct injection gasoline engine. There are many methods for synthesizing 2, 5-dimethylfuran, and the most common method is that 2, 5-dimethylfuran is synthesized by a selective hydrogenation method from 5-hydroxymethylfurfural. The Cu-Ru/C bimetallic catalyst can obtain the highest yield (79%) of 2, 5-dimethylfuran under the condition of double-solvent extraction. In ZnCl 2 Under the condition of the-Pd/C catalyst, the yield of the 2, 5-dimethylfuran can reach 85 percent. Others like Pd/C, pd/Fe 2 O 3 A relatively high yield of 2, 5-dimethylfuran can be obtained. However, these methods require the direct use of gaseous hydrogen for the hydrogenation of 5-hydroxymethylfurfural, and use of noble metal catalysts increases the operating cost, and thus the development of a cheap green liquid hydrogen donor and a cheap commercially available metal catalyst is of great significance for the production of 2, 5-dimethylfuran.
Disclosure of Invention
Aiming at the defects in the prior art, the invention mainly aims to provide a method for preparing 2, 5-dimethylfuran by hydrogenating 5-hydroxymethylfurfural.
It is a second object of the present invention to provide the above 2, 5-dimethylfuran.
In order to achieve the above purpose, the solution of the invention is as follows:
a method for preparing 2, 5-dimethylfuran by hydrogenation of 5-hydroxymethylfurfural comprises the following steps:
under the nitrogen atmosphere, 5-hydroxymethylfurfural reacts with a catalyst in an alcohol solvent at the temperature of 200-250 ℃ for 1-7h, solid-liquid separation is carried out after the reaction, a liquid-phase product is collected, and 2, 5-dimethylfuran is obtained after purification.
Wherein the catalyst is a supported metal catalyst, the supported metal catalyst is a supported copper-based catalyst, and the supported copper-based catalyst is CuO/MgO-ZrO 2 I.e. the active component is CuO and the carrier is MgO-ZrO 2 。
Further, the alcohol in the alcohol solvent is selected from more than one of methanol, isopropanol and 2-butanol.
2, 5-dimethyl furan is obtained by the method.
Due to the adoption of the scheme, the invention has the beneficial effects that:
firstly, the biomass derivative 5-hydroxymethylfurfural is used as a raw material to synthesize the 2, 5-dimethylfuran, the 5-hydroxymethylfurfural can be prepared from biomass resource lignocellulose (from plants widely existing in the nature), fossil energy is not consumed, the energy problem facing the world can be partially relieved, and cheap alcohol solvent is used as a hydrogen donor, so that the direct use of hydrogen which needs to be stored and transported in a high-pressure steel cylinder is avoided, the reaction condition is mild, the yield of the 2, 5-dimethylfuran is high and can reach 63.6%, and a new way is further provided for the utilization of renewable biomass energy.
Second, traditionally, supported catalysts require the use of H when used 2 The reduction is carried out at high temperatures, so that the active species are reduced from the oxide to the metal, whereas the catalyst of the invention is a bimetallic oxide (MgO-ZrO) 2 ) The carrier and Cu in the catalyst are CuO, and the CuO does not need to be reduced at high temperature by hydrogen before use, because the CuO is reduced to metallic Cu in situ by dehydrogenation reaction of alcohol in the reaction, thereby avoiding the need of transferringAnd 5, carrying out hydrogen reduction. In addition, the invention uses cheap load type copper-based catalyst as the raw material of the catalyst, thereby avoiding the use of noble metal catalyst and saving the cost.
Drawings
FIG. 1 is a gas chromatogram of 2, 5-dimethylfuran of example 1 according to the invention.
Detailed Description
The invention provides 2, 5-dimethylfuran and a method for preparing the 2, 5-dimethylfuran by hydrogenation of 5-hydroxymethylfurfural.
The method for preparing 2, 5-dimethylfuran by hydrogenation of 5-hydroxymethylfurfural comprises the following steps:
under the protection of nitrogen, 5-hydroxymethylfurfural reacts with a catalyst in an alcohol solvent at the temperature of 200-250 ℃ for 1-7h, solid-liquid separation is carried out after the reaction, a liquid-phase product is collected, and 2, 5-dimethylfuran is obtained after purification.
The reaction route is as follows:
in particular, the amount of the solvent to be used,
during the reaction, isopropanol is firstly adsorbed on CuO/MgO/ZrO 2 Alkoxy is generated on the surface of the catalyst, then beta-H elimination is carried out, two active H species are generated, and one acetone is released. 5-hydroxymethyl furfural is used as a high-oxidation organic compound, the molecule contains C = O and C-O, negatively charged H species attack carbonyl carbon, 5-hydroxymethyl furfural is converted into 2, 5-dihydroxymethyl furan, then H species generated by isopropanol continuously attack, 2, 5-dihydroxymethyl furan undergoes substitution reaction and is converted into 5-methyl-2-furyl methanol, and one molecule of H is removed 2 And (O). Then, similar reaction process continues to occur to obtain the target product 2, 5-dimethylfuran, and meanwhileRemoving one molecule of H 2 O。
For the reaction, when the temperature is less than 200 ℃, the reaction is slower to proceed, and the yield of 2, 5-dimethylfuran is too low; when the temperature is higher than 250 ℃, the yield of the 2, 5-dimethylfuran is obviously reduced, so the reaction temperature is 200-250 ℃.
Wherein the catalyst is a supported metal catalyst, the supported metal catalyst is a supported copper-based catalyst, and the supported copper-based catalyst is CuO/MgO-ZrO 2 . The catalyst is prepared by a coprecipitation method.
The preparation method of the catalyst includes but is not limited to the following methods:
21.10g of Mg (NO) 3 ) 2 ·6H 2 O、4.71g Zr(NO 3 ) 4 ·5H 2 O and 9.94g Cu (NO) 3 ) 2 ·3H 2 O into a beaker containing 200mL of deionized water to make Mg (NO) 3 ) 2 ·6H 2 O：Zr(NO 3 ) 4 ·5H 2 O：Cu(NO 3 ) 2 ·3H 2 O = 8. Sealing the beaker with a sealing film to avoid splashing of the liquid, stirring at a speed of 500r/min until the solid is completely dissolved, and carrying out the operation at normal temperature.
Configuring 1mol/L of Na 2 CO 3 200mL of solution is ready for use.
Na is mixed with 2 CO 3 The solution is added dropwise to the prepared Mg (NO) 3 ) 2 、Zr(NO 3 ) 4 And Cu (NO) 3 ) 2 And the pH of the solution was always controlled to be 10.
After the pH value is stabilized, stirring is continued for 2h, then stirring is stopped, and standing and aging are carried out for 24h.
And washing the aged catalyst in a suction filtration mode until the pH value of the filtrate is neutral.
And (3) placing the washed catalyst in an oven at 120 ℃ for 12 hours, taking out the catalyst, cooling to normal temperature, and grinding the catalyst into powder.
The powdery catalyst is put into a tube furnace and calcined for 4 hours at 650 ℃ in the air atmosphere, and the temperature rise speed is 5 ℃/min.
The alcohol in the alcohol solvent is selected from more than one of methanol, isopropanol and 2-butanol. Isopropanol is preferred because it is the best selective for 2, 5-dimethylfuran over other solvents.
The 2, 5-dimethylfuran of the invention is obtained by the process described above.
The present invention will be further described with reference to the following examples.
Example 1:
the method for preparing 2, 5-dimethylfuran by hydrogenation of 5-hydroxymethylfurfural of the present example includes the following steps:
0.2mmol of 5-hydroxymethylfurfural, 3mL of isopropanol and 20mg of CuO/MgO-ZrO are sequentially added 2 Loading into 10mL stainless steel reactor, purging with nitrogen for 10s, sealing the reactor, reacting at 250 deg.C for 3 hr, taking out solid-liquid mixture, and separating to obtain 2, 5-dimethylfuran solution.
The product after the reaction was analyzed by gas chromatography (see FIG. 1), and the gas chromatography result showed that the yield of 2, 5-dimethylfuran was 54.8%. The industrial application adopts a proper pressure-resistant reactor according to the requirement, the reaction temperature can be controlled to be 250 ℃, and the reaction lasts for 3 hours. Through the reaction, the 5-hydroxymethyl furfural can be synthesized into the 2, 5-dimethylfuran, the operation is simple and convenient, and the reaction selectivity is good.
Example 2:
the method for preparing 2, 5-dimethylfuran by hydrogenation of 5-hydroxymethylfurfural of the present example includes the following steps:
0.2mmol of 5-hydroxymethylfurfural, 3mL of methanol and 20mg of CuO/MgO-ZrO are sequentially added 2 Loading into 10mL stainless steel reactor, purging with nitrogen gas for 10s, sealing the reactor, reacting at 250 deg.C for 3 hr, taking out solid-liquid mixture, and separating to obtain 2, 5-dimethylfuran solution.
The product after the reaction was analyzed by gas chromatography, and the gas chromatography result showed that the yield of 2, 5-dimethylfuran was 34.8%. The industrial application adopts a proper pressure-resistant reactor according to the requirement, the reaction temperature can be controlled to be 250 ℃, and the reaction lasts for 3 hours. Through the reaction, 5-hydroxymethylfurfural can be synthesized into 2, 5-dimethylfuran, the operation is simple and convenient, and the reaction selectivity is good.
Example 3:
the method for preparing 2, 5-dimethylfuran by hydrogenation of 5-hydroxymethylfurfural of the present example includes the following steps:
0.2mmol of 5-hydroxymethylfurfural, 3mL of isopropanol and 25mg of CuO/MgO-ZrO are sequentially added 2 Loading into 10mL stainless steel reactor, purging with nitrogen for 10s, sealing the reactor, reacting at 250 deg.C for 3 hr, taking out solid-liquid mixture, and separating to obtain 2, 5-dimethylfuran solution.
The product after the reaction was analyzed by gas chromatography, and the gas chromatography result showed that the yield of 2, 5-dimethylfuran was 58.5%. The industrial application adopts a proper pressure-resistant reactor according to the requirement, the reaction temperature can be controlled to be 250 ℃, and the reaction lasts for 3 hours. Through the reaction, 5-hydroxymethylfurfural can be synthesized into 2, 5-dimethylfuran, the operation is simple and convenient, and the reaction selectivity is good.
Example 4:
the method for preparing 2, 5-dimethylfuran by hydrogenation of 5-hydroxymethylfurfural of the present example includes the following steps:
sequentially adding 0.2mmol of 5-hydroxymethylfurfural, 3mL of ethanol and 20mg of CuO/MgO-ZrO 2 Loading into 10mL stainless steel reactor, purging with nitrogen gas for 10s, sealing the reactor, reacting at 250 deg.C for 3 hr, taking out solid-liquid mixture, and separating to obtain 2, 5-dimethylfuran solution.
The product after the reaction was analyzed by gas chromatography, and the gas chromatography result showed that the yield of 2, 5-dimethylfuran was 46.9%. The industrial application adopts a proper pressure-resistant reactor according to the requirement, the reaction temperature can be controlled to be 250 ℃, and the reaction lasts for 3 hours. Through the reaction, the 5-hydroxymethyl furfural can be synthesized into the 2, 5-dimethylfuran, the operation is simple and convenient, and the reaction selectivity is good.
Example 5:
the method for preparing 2, 5-dimethylfuran by hydrogenation of 5-hydroxymethylfurfural of the present example includes the following steps:
sequentially adding 0.2mmol 5-hydroxymethylfurfural, 3mL isopropanol, 25mg CuO/MgO-ZrO 2 Loading into 10mL stainless steel reactor, purging with nitrogen gas for 10s, sealing the reactor, reacting at 200 deg.C for 3 hr, taking out solid-liquid mixture, and separating to obtain 2, 5-dimethylfuran solution.
The product after the reaction was analyzed by gas chromatography, and the gas chromatography result showed that the yield of 2, 5-dimethylfuran was 38.0%. The industrial application adopts a proper pressure-resistant reactor as required, the reaction temperature can be controlled to be 200 ℃, and the reaction lasts for 3 hours. Through the reaction, 5-hydroxymethylfurfural can be synthesized into 2, 5-dimethylfuran, the operation is simple and convenient, and the reaction selectivity is good.
Example 6:
the method for preparing 2, 5-dimethylfuran by hydrogenation of 5-hydroxymethylfurfural of the present example includes the following steps:
0.2mmol of 5-hydroxymethylfurfural, 3mL of isopropanol and 25mg of CuO/MgO-ZrO are sequentially added 2 Loading into 10mL stainless steel reactor, purging with nitrogen gas for 10s, sealing the reactor, reacting at 250 deg.C for 4 hr, taking out solid-liquid mixture, and separating to obtain 2, 5-dimethylfuran solution.
The product after the reaction was analyzed by gas chromatography, and the gas chromatography result showed that the yield of 2, 5-dimethylfuran was 63.6%. The industrial application adopts a proper pressure-resistant reactor as required, and the reaction temperature can be controlled to be 250 ℃ for 4 hours. Through the reaction, the 5-hydroxymethyl furfural can be synthesized into the 2, 5-dimethylfuran, the operation is simple and convenient, and the reaction selectivity is good.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. It will be readily apparent to those skilled in the art that various modifications to these embodiments and the generic principles defined herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present invention is not limited to the above-described embodiments. Those skilled in the art should appreciate that many modifications and variations are possible in light of the above teaching without departing from the scope of the invention.
Claims (2)
1. A method for preparing 2, 5-dimethylfuran by hydrogenation of 5-hydroxymethylfurfural is characterized by comprising the following steps: the method comprises the following steps:
under the nitrogen atmosphere, 5-hydroxymethylfurfural reacts with a catalyst in an alcohol solvent, solid-liquid separation is carried out after the reaction, a liquid-phase product is collected, and 2, 5-dimethylfuran is obtained after purification;
the catalyst is a supported copper-based catalyst, the active component of the supported copper-based catalyst is CuO, and the carrier is MgO-ZrO 2 ；
The reaction temperature is 200-250 ℃, and the reaction time is 1-7h.
2. The method of claim 1, wherein: the alcohol in the alcohol solvent is selected from more than one of methanol, isopropanol and 2-butanol.
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