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Method for synthesizing 5-aminomethyl-2-furfuryl alcohol

A technology of furan methanol and a synthesis method, applied in directions such as organic chemistry, can solve the problems of large amount of ammonia, high cost, low product yield and the like, and achieve the effects of less ammonia amount, mild conditions and high product yield

Inactive Publication Date: 2016-10-12
XIAMEN UNIV
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AI Technical Summary

Problems solved by technology

Ammonia consumption is large, cost is high, and product yield is not high

Method used

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  • Method for synthesizing 5-aminomethyl-2-furfuryl alcohol

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Add 10.0g of 5-hydroxymethylfurfural, 40mL of ammonia water with a concentration of 25% to 28%, 150mL of deionized water, 0.5g of Raney nickel in a 400mL autoclave, and feed in 1.2MPa of hydrogen to react at 80°C The reaction was stirred for 5h. After the reaction, the catalyst is recovered by filtration, the filtrate is transferred to a distillation flask, water and ammonia are removed by atmospheric distillation, and the residue is distilled under reduced pressure at 102-105°C and 0.1 Torr to obtain 5-aminomethyl-2-furanmethanol product (see figure 1 ), the product distillation yield exceeds 72%.

Embodiment 2

[0019] In a 400mL autoclave, add 10.0g of 5-hydroxymethylfurfural, 50mL of ammonia water with a concentration of 25% to 28%, 20mL of deionized water, 150mL of methanol, 0.5g of Raney nickel, and feed 1.0MPa of hydrogen into the The reaction was stirred at 100°C for 4h. After the reaction is finished, filter and recover the catalyst, transfer the filtrate to a distillation flask, and distill under normal pressure to recover the solvent and remove ammonia, and distill the residue under reduced pressure at 102-105°C and 0.1 Torr to obtain 5-aminomethyl-2-furan Methanol product, the product distillation yield exceeds 79%.

Embodiment 3

[0021] In a 400mL autoclave, add 10.0g of 5-hydroxymethylfurfural, 20mL of ammonia water with a concentration of 25% to 28%, 10mL of deionized water, 180mL of methanol, 0.5g of Raney nickel, and feed 1.2MPa of hydrogen into the The reaction was stirred at 100°C for 4h. After the reaction is finished, filter and recover the catalyst, transfer the filtrate to a distillation flask, and distill under normal pressure to recover the solvent and remove ammonia, and distill the residue under reduced pressure at 102-105°C and 0.1 Torr to obtain 5-aminomethyl-2-furan For methanol products, the product detection rate exceeds 89%.

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Abstract

The invention discloses a method for synthesizing 5-aminomethyl-2-furfuryl alcohol, and relates to methods for synthesizing organic compounds. The method includes steps of 1), adding mixed liquor of 5-hydroxymethylfurfural and ammonia water into a high-pressure reaction kettle, adding a raney nickel catalyst into the high-pressure reaction kettle, filling the high-pressure reaction kettle with hydrogen and carrying out heating reaction; 2), carrying out reduced-pressure distillation at the temperatures of 102-105 DEG C under 0.1Torr conditions after the reaction is completely carried out and recycling solvents and ammonia to obtain 5-aminomethyl-2-furfuryl alcohol products. The 5-hydroxymethylfurfural is used as a raw material, the inexpensive ammonia water is used as an amine source, the hydrogen is used as a hydrogen source, raney nickel is used as the catalyst, and the 5-aminomethyl-2-furfuryl alcohol can be synthesized by the aid of the one-pot method in water systems or water-alcohol systems under the condition of low-proportion ammonia usage. The solvents are recycled by means of distillation after the reaction is completely carried out, and residues are subjected to reduced-pressure distillation at the temperatures of 102-105 DEG C under the 0.1-Torr conditions, so that the products can be obtained. The method has the advantages that the ammonia water is used as the amine source, the reaction is carried out in the water systems, and the method is low in ammonia usage, mild in condition and high in product yield.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing 5-aminomethyl-2-furanmethanol. Background technique [0002] 5-Aminomethyl-2-furanmethanol is an excellent chemical raw material, and has important potential application value in fine chemical industry, pharmaceutical synthesis and preparation of furan-based polymers due to its unique structural characteristics. For example, it is reported in the literature that the direct oxidation of 5-aminomethyl-2-furylmethanol can prepare the drug intermediate 3-hydroxyl-5-hydroxymethylpyridine (Tetrahedron 1998,54,10703-10712.). 5-Hydroxymethylfurfural can be produced by dehydration of renewable biomass raw materials such as fructose, glucose, sucrose, cellulose, etc. It has broad application prospects in the preparation of pharmaceutical intermediates and polymer monomers as a substitute for petroleum-based chemicals. [0003] At present, in the meth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/52
CPCC07D307/52
Inventor 林鹿陈伟孙勇曾宪海
Owner XIAMEN UNIV
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