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Method for synthesizing 5-amino-1-pentanol by taking furfural as initial raw material

A technology of furfural and amino groups, applied in the field of synthesizing 5-amino-1-pentanol, can solve the problems of high energy consumption, low efficiency, high price and the like, and achieve the effects of simple preparation process, good catalytic performance and mild reaction conditions

Active Publication Date: 2022-07-29
HEBEI UNIV OF TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

At present, only reagent quantities of 5-AP are available on the market, and the price is expensive
[0003] Li Baoqiang et al. (Fine Chemical Intermediates, 2014, 44(6), 40-42) used 1,5-pentanediol (1,5-PD) to react with concentrated hydrochloric acid, and then used ammonia for amination (Scheme 1, Route A) generates 5-AP, which is inefficient and generates a lot of waste
Huang Zhiwei et al. (patent CN201910113732.4, CN201810871231.8) self-catalyzed dihydropyran derived from biomass furfural to form 2-hydroxytetrahydropyran (2-HTPH), and then directly aminated on a metal catalyst to obtain 5-AP (scheme 1, route B); This method starts from biomass furfural, and through multi-step reaction, energy consumption is high

Method used

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  • Method for synthesizing 5-amino-1-pentanol by taking furfural as initial raw material

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Experimental program
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Effect test

Embodiment 1

[0063] Step 1. Add furfural (3.6mmol), N,N,N-trimethyl-N-sulfobutylammonium hydrogen sulfate ionic liquid hydroxylamine salt (5.4mol) and zinc chloride (0.144mmol) into a 100ml three-necked flask 6ml of p-xylene and 6ml of N,N,N-trimethyl-N-sulfobutylammonium hydrogen sulfate ionic liquid were added to the mixture, stirred, refluxed and condensed, and the reaction was stopped after 8 hours of reaction at normal pressure and 100°C. After the reaction solution was cooled, the supernatant was taken and analyzed by gas chromatography. The reaction result showed that the conversion rate of furfural was 100%, and the yield of furfural was 99%. The toluene layer was taken, and the solvent was distilled off under reduced pressure to obtain high-purity furfuronitrile.

[0064] Step 2. Put 2 mmol of furonitrile, 0.1 g of Ru / g-C with a loading of 5% 3 N 4 The catalyst, 20 mL of isopropanol, and 500 μL of ammonia water (25 wt %) were added to a 50 mL autoclave. First, the air in the rea...

Embodiment 2

[0070] The other parts of step 1 are the same as in Example 1, the difference is that the added N,N,N-trimethyl-N-sulfobutylammonium hydrogen sulfate ionic liquid hydroxylamine salt is 4.32mmol, and the reaction result is that the furfural conversion rate is 69.2% , the yield of furfuronitrile was 66.7%. The three-step series reaction is required to be carried out under the optimal conditions for the first two-step reaction. When the first two-step reaction yield does not reach 99%, there are many by-products after removing the solvent, so the subsequent steps 2 and 3 are not carried out.

Embodiment 3

[0072] The other parts of step 1 are the same as in Example 1, the difference is that the N,N,N-trimethyl-N-sulfobutylammonium hydrogen sulfate ionic liquid hydroxylamine salt added is 4.68mmol, and the reaction result is a furfural conversion rate of 78.5% , the yield of furfuronitrile was 75.2%. The three-step series reaction is carried out under the optimal conditions of the first two-step reaction. When the first two-step reaction yield does not reach 99%, there are many by-products after removing the solvent, so the subsequent steps 2 and 3 are not carried out.

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Abstract

The invention relates to a method for synthesizing 5-amino-1-pentanol by taking furfural as an initial raw material. The method comprises a three-step method and a two-step method. According to the three-step method, 5-AP is synthesized through a three-step cascade reaction of a reaction of furfural and ionic liquid type hydroxylamine salt for synthesis of furfuryl nitrile, a reaction of preparation of furfuryl amine through hydrogenation of furfuryl nitrile and a reaction of hydrogenolysis of furfuryl amine into 5-AP, furfuryl amine is obtained through high selectivity of a catalyst, and in the third step, tetrahydrofurfuryl amine and piperidine with high added values are produced while 5-AP is generated. In the two-step method, the reaction for preparing furfuryl amine through hydrogenation of furfuryl nitrile and the reaction for preparing 5-AP through hydrogenolysis of furfuryl amine are coupled into one-step reaction, so that the reaction steps are reduced. The method has the advantages of mild conditions, high selectivity and high atom utilization rate.

Description

technical field [0001] The invention relates to a method for synthesizing 5-amino-1-pentanol with furfural as an initial raw material, and belongs to the technical field of fine chemicals. Background technique [0002] Amino alcohol is an important bifunctional compound, which contains both amino group and hydroxyl group in the molecule, and has the general properties of alcohol and amine. It is widely used in the synthesis of medicine and pesticide. 5-Amino-1-pentanol (5-AP) is an important pharmaceutical intermediate, which can be used in the synthesis of anti-inflammatory and anticancer drugs, especially as a starting material for the synthesis of the alkaloid Mannheim. With the development of the alkaloid Mannheim in pharmaceutical applications, the market demand for 5-AP is also increasing. Currently, there are only reagent quantities of 5-AP available on the market, and they are expensive. [0003] Li Baoqiang et al. (Fine Chemical Intermediates, 2014, 44(6), 40-42) ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C215/08C07C213/00B01J27/24
CPCC07C213/00C07D307/52C07D307/68B01J27/24C07C215/08Y02P20/584
Inventor 王延吉张树兴丁晓墅卢遥张东升赵新强
Owner HEBEI UNIV OF TECH
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