Method for preparing 2,5-dimethyl furan by catalyzing selective hydrodeoxygenation of 5-hydroxymethyl furfural

A technology of hydroxymethylfurfural and dimethylfuran, which is applied in the field of biofuel preparation, can solve the problems of disadvantages, long reaction time, and low yield, and achieve the effects of less waste discharge, simple operation process, and high yield

Inactive Publication Date: 2015-04-29
HUAIYIN TEACHERS COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Since 2007, there have been relatively few research reports on the preparation of 2,5-DMF, and the reaction system used either requires a high reaction temperature (300 °C) (Green Chemistry, 2012, 14: 2457-2461) or requires Very long reaction time (24 h) (ChemSusChem, 2013, 6: 1158-1162) or high hydrogen pressure (62 bar) (Green Chemistry, 2010, 12: 1253-1262), and 2,5-DMF The productive rate is low, therefore, these reaction systems are not conducive to the large-scale production of 2,5-DMF

Method used

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  • Method for preparing 2,5-dimethyl furan by catalyzing selective hydrodeoxygenation of 5-hydroxymethyl furfural
  • Method for preparing 2,5-dimethyl furan by catalyzing selective hydrodeoxygenation of 5-hydroxymethyl furfural
  • Method for preparing 2,5-dimethyl furan by catalyzing selective hydrodeoxygenation of 5-hydroxymethyl furfural

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Example 1: Add 2.5% 5-HMF, 30% Ru / AC and 20 g THF into the autoclave, seal it with H 2 Replace the air in the kettle; then H 2 The pressure was adjusted to 20 bar, the temperature was raised to 180 °C, and the reaction was carried out at a stirring speed of 500 rpm for 120 min; after the reaction was completed, the high-pressure reactor was rapidly lowered to room temperature and opened, and the hydrodeoxygenation reaction liquid was filtered and detected by a gas chromatograph It can be seen that the conversion rate of 5-HMF is 90.7%, and the yield of 2,5-DMF is 80.6%; then the filtrate is subjected to atmospheric distillation at 66 °C to obtain THF and the initial steamed residual liquid, and the initial steamed residual liquid is then Carried out vacuum distillation at 75 °C to obtain 2,5-DMF and H 2 A mixture of O, 2,5-DMF and H 2 After O is automatically stratified, the upper layer is purified 2,5-DMF, which can be seen by nuclear magnetic resonance spectromete...

Embodiment 2

[0024] Example 2: Add 3.75% 5-HMF, 20% Ru / AC and 25 g THF into the autoclave, seal it with H 2 Replace the air in the kettle; then H 2 The pressure was adjusted to 25 bar, the temperature was raised to 220 °C, and the reaction was carried out at a stirring speed of 600 rpm for 100 min; after the reaction was completed, the high-pressure reactor was quickly lowered to room temperature and opened, and the hydrodeoxygenation reaction solution was filtered and detected by a gas chromatograph It can be seen that the conversion rate of 5-HMF is 100%, and the yield of 2,5-DMF is 94.5%; then the filtrate is subjected to atmospheric distillation at 66 °C to obtain THF and the initial steamed residual liquid, and the initial steamed residual liquid is then Carried out vacuum distillation at 75 °C to obtain 2,5-DMF and H 2 A mixture of O, 2,5-DMF and H 2 After automatic stratification of O, the upper layer is purified 2,5-DMF, and the purity of 2,5-DMF is 98% as detected by NMR spect...

Embodiment 3

[0025] Example 3: Add 2.5% 5-HMF, 40% Ru / AC and 20 g THF into the autoclave, seal it with H 2 Replace the air in the kettle; then H 2 Adjust the pressure to 20 bar, heat up to 200 °C, and react at a stirring speed of 400 rpm for 120 min; after the reaction, the high-pressure reactor was quickly lowered to room temperature and opened, and the hydrodeoxygenation reaction liquid was filtered and detected by gas chromatography It can be seen that the conversion rate of 5-HMF was 100%, and the yield of 2,5-DMF was 94.7%; the filtered Ru / AC was washed 10 times with 5 mL THF, and dried in vacuum at 65 °C for 24 h; The dried Ru / AC was added to fresh THF and subjected to the next round of hydrodeoxygenation reaction under the same reaction conditions as above, from image 3 It can be seen that the conversion rate of 5-HMF can still reach more than 98% when Ru / AC is used for the second and third times, and the yield of 2,5-DMF can also reach more than 91%; After the reaction solutio...

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Abstract

The invention discloses a method for preparing 2,5-dimethyl furan by catalyzing selective hydrodeoxygenation of 5-hydroxymethyl furfural. The method comprises the following steps: by taking a supported metal as a catalyst, taking hydrogen as a hydrogen source, taking an organic solvent as a reaction solvent, converting 5-hydroxymethyl furfural into the 2,5-dimethyl furan under the proper reaction temperature, reaction time and stirring speed. According to the method disclosed by the invention, the reaction conditions are mild, and the equipment requirement is low; the operation process is simple and easy to master; the target product yield is high and can be 94.7 percent; the target products can be separated and purified by utilizing a method for combining simple atmospheric distillation with reduced pressure distillation; and moreover, the catalyst and the reaction solvent can be recycled and can be repeatedly used, the waste emission amount is small, and the method is green and environmentally friendly and has extremely high practicality and good industrial prospects.

Description

technical field [0001] The invention belongs to the field of biofuel preparation and relates to a preparation method, in particular to a method for preparing 2,5-dimethylfuran by catalyzing the selective hydrodeoxygenation of 5-hydroxymethylfurfural. Background technique [0002] With the increasingly prominent contradiction between the demand and storage of fossil fuels and the rising global greenhouse gas emissions, the search for a biofuel that can gradually replace fossil fuels and meet the requirements of carbon neutrality has attracted more and more attention. Among them, bio-liquid fuels are particularly important for transportation, which accounts for more than 30% of the total energy consumption. Ethanol is currently the only biological liquid fuel that can be produced on a large scale, but its low energy density (23 MJ / L), high volatility (boiling point of 78.4 °C), and miscibility with water all have disadvantages. limit its practical application. Compared wit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/36
CPCC07D307/36
Inventor 胡磊吴真周守勇徐继明
Owner HUAIYIN TEACHERS COLLEGE
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