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Synthesis of 2-n-methylaminomethyl-5-n-methyliminomethylfuran

A technology of methyliminomethylfuran and methylaminomethyl, applied in the field of organic compound synthesis, can solve problems such as few reports on furan synthesis, and achieve the effects of low equipment requirements, low cost and high yield

Inactive Publication Date: 2020-05-29
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few reports on the synthesis of 2-N-methylaminomethyl-5-N-methyliminomethylfuran

Method used

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  • Synthesis of 2-n-methylaminomethyl-5-n-methyliminomethylfuran
  • Synthesis of 2-n-methylaminomethyl-5-n-methyliminomethylfuran
  • Synthesis of 2-n-methylaminomethyl-5-n-methyliminomethylfuran

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 1.89g of HMF and 4.65g of methylamine into the 50mL reactor, shake and mix properly. Then add 25mL formic acid solution (7mol / L). Heat the reaction, the temperature is 170°C, the reaction time is 3h, and the mixture is mixed evenly by rotation at a speed of 300r / min. After the reaction is complete, put it in water to cool. The reaction solution was taken out, and the solvent was removed by rotary evaporation at 80°C until the solution mass no longer decreased. After the rotary evaporation, concentrated NaOH solution was added to the solution to adjust the pH to pH=12, and the residue was extracted several times with an equal volume of ethyl acetate, the extracts were combined, and the extractant was recovered by distillation under reduced pressure. Distill at 200°C under a pressure of 2000 Pa to obtain 2-N-methylaminomethyl-5-N-methyliminomethylfuran. As determined by GC, its purity is above 99%, and the product molar yield is 31.2%.

Embodiment 2

[0027] Add 1.89g of HMF and 9.03g of N-methylformamide solution (98%) into a 50mL reactor, shake and mix well. Then add 25mL formic acid solution (7mol / L). Heat the reaction, the temperature is 170°C, the reaction time is 3h, and the mixture is mixed evenly by rotation at a speed of 300r / min. After the reaction is complete, put it in water to cool. The reaction solution was taken out, and the solvent was removed by rotary evaporation at 80°C until the solution mass no longer decreased. After the rotary evaporation, concentrated NaOH solution was added to the solution to adjust the pH to pH=12, and the residue was extracted several times with an equal volume of ethyl acetate, the extracts were combined, and the extractant was recovered by distillation under reduced pressure. Distill at 200°C under a pressure of 2000 Pa to obtain 2-N-methylaminomethyl-5-N-methyliminomethylfuran. As determined by GC, its purity is above 99%, and the product molar yield is 35.0%.

Embodiment 3

[0029] Add 1.89g of HMF and 10.95g of N-methylacetamide solution (>99%) into a 50mL reactor, shake and mix properly. Then add 25mL formic acid solution (7mol / L). Heat the reaction, the temperature is 170°C, the reaction time is 3h, and the mixture is mixed evenly by rotation at a speed of 300r / min. After the reaction is complete, put it in water to cool. The reaction solution was taken out, and the solvent was removed by rotary evaporation at 80°C until the solution mass no longer decreased. After the rotary evaporation, concentrated NaOH solution was added to the solution to adjust the pH to pH=12, and the residue was extracted several times with an equal volume of ethyl acetate, the extracts were combined, and the extractant was recovered by distillation under reduced pressure. Distill at 200°C under a pressure of 2000 Pa to obtain 2-N-methylaminomethyl-5-N-methyliminomethylfuran. As determined by GC, its purity is above 99%, and the product molar yield is 32.3%.

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Abstract

The invention discloses synthesis of 2-N-methylaminomethyl-5-N-methylaminomethyl furan, and relates to the field of synthesis method of organic compounds. According to the synthesis method, 5-hydroxymethyl furfural, organic amine, and a formic acid water solution are mixed in a reactor; the mixture is heated to carry out reactions, after reactions, rotation evaporation is performed to remove the solvent to obtain a solution A; adding a NaOH solution into the solution A, adjusting the pH of the solution until pH is not less than 10 to obtain a solution B; extracting the solution B by ethyl acetate, merging extracting agents, carrying out reduced pressure distillation to recover the extracting agent namely ethyl acetate to obtain a solution C; and subjecting the solution C to reduced pressure distillation to obtain 2-N-methylaminomethyl-5-N-methylaminomethyl furan. The purity of obtained 2-N-methylaminomethyl-5-N-methylaminomethyl furan is more than 99%. HMF and organic amine are taken as the raw materials, a formic acid water solution is taken as the reaction solution, and 2-N-methylaminomethyl-5-N-methylaminomethyl furan is prepared by a one-pot method. The operation is simple, thereaction system is green and environmentally friendly, the reaction solvent can be repeatedly used, the feed concentration is large, and the yield is high.

Description

technical field [0001] The invention relates to a synthesis method of organic compounds, in particular to a synthesis method of 2-N-methylaminomethyl-5-N-methyliminomethylfuran. Background technique [0002] 5-Hydroxymethylfurfural (HMF) is an extremely important platform compound in the catalytic conversion of biomass. Many of its downstream products are widely used and can be converted into various furan substances with high added value, such as 2,5- Dimethylfuran (DMF), 2,5-furandimethanol (FDM), 2,5-furandicarbaldehyde (DFF), 2,5-furandicarboxylic acid (FDCA), etc. HMF undergoes ammonia substitution reaction to synthesize a large class of HMF amino derivatives. For example, Chinese patent CN106349195A reports a synthesis method of N,N-dimethyltetrahydrofurfurylamine. This method mainly uses furfural as a raw material, reacts with N,N-dimethylformamide or N,N-dimethylacetamide and formic acid to form N,N-dimethylfurfurylamine, and then catalytically hydrogenates it to ob...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/52
CPCC07D307/52
Inventor 孙勇司志浩唐兴曾宪海林鹿
Owner XIAMEN UNIV
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