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Preparation method of 3-aminomethyl tetrahydrofuran

A technology of aminomethyltetrahydrofuran and formyltetrahydrofuran, which is applied in the field of preparation of chemical raw material medicine intermediates, can solve the problems of difficult operation, high cost, flammability and safety of palladium carbon, etc., and achieve large production capacity, high selectivity, easy The effect of industrialization amplification

Active Publication Date: 2019-11-05
SHIJIAZHUANG CHIRALS CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] Low efficiency, high cost, difficult operation and Raney nickel, palladium carbon are flammable and unsafe

Method used

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  • Preparation method of 3-aminomethyl tetrahydrofuran
  • Preparation method of 3-aminomethyl tetrahydrofuran
  • Preparation method of 3-aminomethyl tetrahydrofuran

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Add 100 g of modified montmorillonite to the fixed-bed reactor, keep the temperature in the reactor at 120° C., feed maleic glycol at a flow rate of 0.30 L / h, and stop feeding when the feed rate reaches 3000 g. Then the temperature was raised to 150°C at 1°C per minute, and 2,5-dihydrofuran was collected by distillation. Under the catalysis of modified montmorillonite, maleic diol was continuously ring-closed and dehydrated to generate 2,5-dihydrofuran , by continuously collecting the product, the reaction proceeded in the positive direction. The reaction took 6 hours, and a total of 2,5-dihydrofuran was collected. 2050g, the yield was 86.1%, and the chemical purity was 99.5%.

Embodiment 2

[0059] Add 100 g of hydroxyapatite to the fixed-bed reactor, keep the temperature in the reactor at 120° C., feed maleic glycol at a flow rate of 0.30 L / h, and stop feeding when the amount reaches 5000 g. Then, after raising the temperature at 1°C per minute to 150°C, start to collect 2,5-dihydrofuran by distillation. Under the catalysis of hydroxyapatite, maleic diol is continuously ring-closed and dehydrated to generate 2,5-dihydrofuran. By continuously collecting the product, the reaction proceeded in the positive direction. The reaction took 12 hours, and a total of 3833 g of 2,5-dihydrofuran was collected, with a yield of 96.7% and a chemical purity of 99.3%.

Embodiment 3

[0061] Add 100 g of alumina to the fixed bed reactor, keep the temperature in the reactor at 120°C, feed maleic diol at a flow rate of 0.30 L / h, and stop feeding when the amount reaches 4000 g. Then the temperature was raised to 150°C at 1°C per minute, and 2,5-dihydrofuran was collected by distillation. Under the catalysis of alumina, maleic diol was continuously dehydrated to form 2,5-dihydrofuran through ring closure. The product was collected, and the reaction proceeded in the positive direction. The reaction took 10 hours, and a total of 2,5-dihydrofuran was collected, 2933g, with a yield of 92.4% and a chemical purity of 99.1%.

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Abstract

The invention relates to a preparation method of 3-aminomethyl tetrahydrofuran, and the preparation method comprises the following steps: cyclizing compound 1 cis-butenediol to obtain a compound 2, namely 2,5-dihydrofuran, then formylating the 2,5-dihydrofuran to obtain a compound 3, namely 3-formyl tetrahydrofuran, and finally performing reductive amination to obtain a compound 4, namely the 3-aminomethyl tetrahydrofuran. The preparation method has the advantages of simple production process, high utilization rate of materials, large production capacity, high selectivity, durability and highefficiency of catalysts in each step. The preparation method is simple in route and easy to scale up in industrialization.

Description

technical field [0001] The invention relates to a preparation method of 3-aminomethyltetrahydrofuran, which belongs to the technical field of preparation of intermediates of chemical raw materials. Background technique [0002] 3-Aminomethyltetrahydrofuran is a key intermediate of the insecticide dinotefuran, and its structural formula is shown in formula 4. Dinotefuran is a third-generation new neonicotinoid insecticide developed by Mitsui Chemicals in Japan. The structural formula is shown in formula 5. [0003] [0004] Dinotefuran, whose chemical name is 1-methyl-2-nitro-3-(tetrahydro-3-furylmethyl)guanidine, was developed by Japan’s Mitsui Chemicals in 1998 and was first registered in Japan in 2002. In 2003, dinotefuran was listed in South Korea; in 2004, it was the first registered third-generation neonicotinoid insecticide in the United States, and its mechanism of action can selectively control the nicotinic acetylcholine in the insect nervous system Esterase ...

Claims

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Application Information

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IPC IPC(8): C07D307/14B01J27/18
CPCB01J27/1806C07D307/14
Inventor 刘庆彬李耀锋李立斌靳晓坤
Owner SHIJIAZHUANG CHIRALS CHEM CO LTD
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