Method for preparing N-(5-methylfurfuryl)aniline and derivatives from biomass carbohydrate
A carbohydrate and biomass technology, applied in the direction of organic chemistry, etc., can solve the problems of 5-methylfurfural, such as cumbersome steps, high preparation cost, and cumbersome process, so as to achieve maximum utilization of resources, low industrialization cost, and simplified operation process Effect
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Embodiment 1
[0033] (1) In a 250ml round bottom flask with a magnetic stirrer, add 3.6g fructose, 10g phosphorous acid, 20ml distilled water, 8ml hydroiodic acid with a mass fraction of 57%, 40ml toluene, react at 90°C for 3h, separate Two-phase solvent, the toluene layer was extracted and washed successively with 15% sodium sulfite, 5% sodium hydroxide, and saturated saline, and the organic phase was collected and dehydrated by anhydrous magnesium sulfate.
[0034] (2) the gained toluene solution containing 5-methylfurfural is analyzed by gas chromatography, quantified with n-decane internal standard, and the productive rate of calculating 5-methylfurfural is 53.8%, and the content of 5-methylfurfural in the toluene solution is 0.26mol / l.
[0035] (3) In a high-pressure reactor with a magnetic stirrer, add 20ml of the above-mentioned toluene solution containing 5-methylfurfural, 7.5mg of Pd / C with a Pd loading of 5wt%, and 6mol of aniline successively, close the kettle, and blow it with h...
Embodiment 2
[0038] (1) Step (1) in Example 1 was used to obtain a toluene solution containing 5-methylfurfural, and the toluene solvent was removed by distillation under reduced pressure to obtain a pure biomass-based 5-methylfurfural product.
[0039] (2) In a high-pressure reactor with a magnetic stirrer, add 20ml of ethanol, 5mg of Pd / C with a Pd loading of 5wt%, 5mol of biomass-based 5-methylfurfural (495ul), and 5.5mol of aniline, and close the kettle , and replace the air in the reactor with hydrogen, and ensure that the initial hydrogen pressure of the reaction is 0.4MPa, place the high-pressure reactor in an electric heating mantle, raise the temperature to 50°C, and stir for 45 minutes. Gas chromatographic analysis was carried out after the reaction. Calculation by the internal standard method showed that the conversion rate of biomass-based 5-methylfurfural was 99.7%, and the yield of N-(5-methylfurfuryl)aniline was 99.2%. That is, the yield of N-(5-methylfurfuryl)aniline prepar...
Embodiment 3
[0041] In an autoclave with a magnetic stirrer, successively add 20ml of ethanol, 10mg of Pd / C with a Pd load of 5wt%, and 5mol of the biomass-based 5-methylfurfural (495ul) obtained from the operation in step (1) of Example 2 , 7.5mol o-toluidine, close the kettle, replace the air in the reactor with hydrogen, and ensure that the initial hydrogen pressure of the reaction is 1.2MPa, place the high-pressure reactor in an electric heating mantle, raise the temperature to 50°C, and stir for 1h. Carry out gas chromatographic analysis after the reaction, calculate by internal standard method, the conversion rate of biomass-based 5-methylfurfural is 95.9%, and the productive rate of o-methyl-N-(5-methylfurfuryl)aniline is 94.6% . That is, the yield of o-methyl-N-(5-methylfurfuryl)aniline prepared from fructose was 50.9%.
[0042] o-Methyl-N-(5-methylfurfuryl)aniline: 1 H NMR (400 MHz, Chloroform- d ) δ 7.12 (td, J = 7.7, 1.6 Hz, 1H, 3-H Ph ), 7.09-7.02 (m, 1H, 5-H Ph ), 6.68 ...
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