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A kind of preparation method of 3-aminomethyltetrahydrofuran

A technology of aminomethyltetrahydrofuran and methyltetrahydrofuran, which is applied in the field of preparation of 3-aminomethyltetrahydrofuran, can solve the problems of expensive catalyst, poor atom economy, difficult recycling and reuse, and achieve low cost, avoid hydrogenation reduction, The effect of high product yield and purity

Active Publication Date: 2021-08-17
XINFA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] Although the overall yield of synthetic route 3 is high, the 3-aminomethyltetrahydrofuran obtained by the method of US Patent Document US5990323 contains 3-hydroxymethyltetrahydrofuran and di(tetrahydrofuran-3-methyl)amine, and the product has low purity and is difficult to further purify
Chinese patent document CN106866588A uses hydroxylamine as a nitrogen donor, which is expensive and poor in atom economy; and the butylene glycol hydroformylation route requires two steps to use noble metal catalysts, which have the disadvantages of expensive catalysts and difficult recycling and reuse

Method used

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  • A kind of preparation method of 3-aminomethyltetrahydrofuran
  • A kind of preparation method of 3-aminomethyltetrahydrofuran
  • A kind of preparation method of 3-aminomethyltetrahydrofuran

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Embodiment 1: Preparation of 3-nitromethylenetetrahydrofuran (Ⅲ)

[0057] In the 500 milliliter four-necked flask that is connected with stirring, thermometer, reflux condenser and dropping funnel, add 180 gram methanol, 2.0 gram 27wt% sodium methylate methanol solution, 25.6 gram (0.42 moles) nitromethane, 20 to 25 ℃ In between, a mixture of 34.4 g (0.4 mol) of tetrahydrofuran-3-one (II) and 50 g of methanol was added dropwise, and it took about 2 hours to complete the dropwise addition. Thereafter, the reaction was stirred at 25-30° C. for 4 hours. Cool to 0 to 5°C, add 100 grams of water, 100 grams of dichloromethane, adjust the pH of the system to 6.5-7.5 with 30 wt% hydrochloric acid, separate layers, and extract the aqueous layer 3 times with dichloromethane, each with 30 grams of dichloromethane methane, combined the organic phases, distilled and recovered dichloromethane to obtain 49.9 g of 3-nitromethylenetetrahydrofuran (III), with a yield of 96.7% and a gas p...

Embodiment 2

[0058] Embodiment 2: Preparation of 3-nitromethylenetetrahydrofuran (Ⅲ)

[0059] In the 500 milliliter four-necked flask that is connected with stirring, thermometer, reflux condenser and dropping funnel, add 180 gram methanol, 1.0 gram sodium hydroxide, 26.2 gram (0.43 mole) nitromethane, between 25 to 30 ℃, A mixture of 34.4 g (0.4 moles) of tetrahydrofuran-3-one (II) and 50 g of methanol was added dropwise for about 2 hours. After that, the reaction was stirred at 30 to 35° C. for 4 hours. Cool to 0 to 5°C, add 100 grams of water, 100 grams of dichloromethane, adjust the pH of the system to 6.5-7.5 with 30 wt% hydrochloric acid, separate layers, and extract the aqueous layer 3 times with dichloromethane, each with 30 grams of dichloromethane methane, combined the organic phases, distilled and recovered dichloromethane to obtain 48.3 g of 3-nitromethylenetetrahydrofuran (III), with a yield of 93.6% and a gas phase purity of 99.4%.

Embodiment 3

[0060] Embodiment 3: Preparation of 3-aminomethyltetrahydrofuran (I)

[0061] Add 200 grams of methanol, 25.8 grams (0.2 moles) of 3-nitromethylenetetrahydrofuran (Ⅲ) prepared in Example 1 in a 500 milliliter stainless steel autoclave, 0.5 grams of 5wt% palladium carbon catalyst, nitrogen replacement three times, pass into Hydrogen, keep the system pressure at 0.3-0.4MPa, react at 30-35°C for 4 hours. Nitrogen was replaced three times, the palladium carbon was removed by filtration, the filter cake was washed twice with methanol, 30 grams of methanol each time, and the filtrates were combined. The filtrate was distilled to recover the solvent, and then distilled under reduced pressure (85-95°C / 2mmHg) to obtain 19.6 g of colorless transparent liquid 3-aminomethyltetrahydrofuran (I), with a yield of 97.2% and a gas phase purity of 99.7%.

[0062] The NMR data of the resulting product are as follows:

[0063] 1 HNMR (400MHz, CDCl 3 ):δppm

[0064] 3.82-3.86(m,2H),3.71-3.75(t...

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Abstract

The invention provides a preparation method of 3-aminomethyltetrahydrofuran, which uses tetrahydrofuran-3-ketone and nitromethane as raw materials to obtain 3-nitromethylene tetrahydrofuran through condensation reaction, and then obtains 3-nitromethylene tetrahydrofuran through catalytic hydrogenation reduction Aminomethyltetrahydrofuran. The method of the invention has cheap and easy-to-obtain raw materials, good stability, and low cost; simple preparation steps, safe and convenient operation, and easy realization of the reaction; less waste water generation, environmental protection; less side reactions, high reaction selectivity, and good atom economy. High purity and yield, suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of 3-aminomethyltetrahydrofuran, which belongs to the technical field of pesticide chemistry. Background technique [0002] Dinotefuran, the English name is dinotefuran, and the chemical name is 1-methyl-2-nitro-3-(tetrahydrofuran-3-methyl)guanidine. It is a new type of neonicotinoid insecticide developed by Mitsui Corporation of Japan. It was released in 2002 It was registered and put on the market in Japan in 2010. At present, pesticide registration certificates have been obtained in many countries. Compared with traditional neonicotinoid insecticides, dinotefuran has better performance. It has the advantages of small amount, long duration, and no phytotoxicity to crops. Dinotefuran blocks the normal central nervous system transmission of insects by controlling the nicotinic acetylcholinesterase receptors in the insect nervous system, eventually leading to paralysis and death. Dinotefuran has good syste...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/14
CPCC07D307/14
Inventor 崔庆荣吕强三万鹏周立山鞠立柱
Owner XINFA PHARMA
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