Synthetic method of 3-aminomethyl tetrahydrofuran

A technology of aminomethyltetrahydrofuran and a synthesis method, applied in the field of nicotinic insecticide dinotefuran, can solve the problems of unsuitability for industrial large-scale production, cumbersome reaction, long route and the like, and achieves strong safety and operability , The effect of simple process and high overall yield

Active Publication Date: 2017-06-20
XIAN CATALYST NEW MATERIALS CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method has problems such as long route, cumbersome reaction, and lo

Method used

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  • Synthetic method of 3-aminomethyl tetrahydrofuran
  • Synthetic method of 3-aminomethyl tetrahydrofuran
  • Synthetic method of 3-aminomethyl tetrahydrofuran

Examples

Experimental program
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Effect test

Embodiment 1

[0032] like figure 2 As shown, this embodiment includes the following steps:

[0033] Step 1. In a three-neck flask with a volume of 2L, add 1320g (15mol) of 1,4-butenediol, then add 1.32g of phosphotungstic heteropoly acid solid, and react at 250°C for 8h to obtain 2,5-dihydrofuran 1000g (14.3mol), the yield of the 2,5-dihydrofuran is 95.2%;

[0034] Step 2. Mix 1000g (14.3mol) of 2,5-dihydrofuran prepared in step 1 with 2L of methanol in an autoclave with a volume of 5L, and then add 20g of homogeneous catalyst HRhCO[P(Ph) 3 ] 3 , feed reaction gas into the autoclave to raise the pressure in the autoclave to 2 MPa, stir for 10 h at a temperature of 90° C., then lower the temperature, exhaust the gas, release the reaction product liquid, and distill off the methanol. Distillation obtains 3-formaldehyde tetrahydrofuran 1315g, and the yield of described 3-formaldehyde tetrahydrofuran is 92%; Described reaction gas is made of CO and H 2 Mixed according to the volume ratio o...

Embodiment 2

[0044] like figure 2 As shown, this embodiment includes the following steps:

[0045] Step 1. In a three-neck flask with a volume of 2L, add 1320g (15mol) of 1,4-butenediol, add 2g of ZSM-5 molecular sieve, and react at 230°C for 7h to obtain 1018g (14.5mol) of 2,5-dihydrofuran ), the yield of the 2,5-dihydrofuran is 97%;

[0046] Step 2. Mix 1018g (14.5mol) of 2,5-dihydrofuran prepared in Step 1 with 2L of ethanol in an autoclave with a volume of 5L, and then add 0.509g of homogeneous catalyst HRhCO[P(PhF) 3 ] 3 , feed reaction gas into the autoclave to raise the pressure in the autoclave to 4MPa, stir at 90°C for 18 hours, then lower the temperature, exhaust, release the reaction product liquid, and distill off ethanol, Distillation obtains 3-formaldehyde tetrahydrofuran 1396g, and the yield of described 3-formaldehyde tetrahydrofuran is 96%; Described reaction gas is made of CO and H 2 Mixed according to the volume ratio of 1:1;

[0047] Step three, mix 1396g (13.9mol...

Embodiment 3

[0051] like figure 2 As shown, this embodiment includes the following steps:

[0052] Step 1. In a three-neck flask with a volume of 2L, add 1320g (15mol) of 1,4-butenediol, add 4.4g of phosphomolybdoheteropolyacid solid, and react at 230°C for 5h to obtain 966g of 2,5-dihydrofuran (13.8mol), the yield of the 2,5-dihydrofuran is 92%;

[0053] Step 2. Mix 966g (13.8mol) of 2,5-dihydrofuran prepared in step 1 with 2.5L methanol in an autoclave with a volume of 5L, and then add 19.3g of homogeneous catalyst HRhCO[P(PhSO 3 Na) 3 ] 3 , feed reaction gas into the autoclave to raise the pressure inside the autoclave to 7MPa, stir for 15 hours at a temperature of 60°C, then lower the temperature, exhaust the gas, release the reaction product liquid, and distill off the methanol. Distillation obtains 3-formaldehyde tetrahydrofuran 1311g, and the yield of described 3-formaldehyde tetrahydrofuran is 95%; Described reaction gas is made of CO and H 2 Mixed according to the volume rat...

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Abstract

The invention discloses a synthetic method of 3-aminomethyl tetrahydrofuran. The synthetic method comprises the following steps: (1) carrying out cyclization reaction on 1,4-butylene glycol under the action of a fixed acid catalyst, so as to generate 2,5-dihydrofuran; (2) carrying out hydroformylation reaction on 2,5-dihydrofuran under the action of a homogeneous catalyst HRhCO[P(PhX)3]3, so as to obtain 3-formaldehyde tetrahydrofuran; (3) reacting by virtue of 3-formaldehyde tetrahydrofuran and hydroxylamine compounds, so as to obtain 3-formoxime tetrahydrofuran; and (4) carrying out hydrogenation on 3-formoxime tetrahydrofuran, so as to obtain 3-aminomethyl tetrahydrofuran. The synthetic method disclosed by the invention is environmentally friendly and has the beneficial effects that the process is simple, the steps are short, the total yield is very high, the cost is low, the yield of products in each step is higher than 90%, and the total yield of the finally prepared 3-aminomethyl tetrahydrofuran is higher than 80%.

Description

technical field [0001] The invention belongs to the technical field of the nicotinic insecticide dinotefuran, and in particular relates to a synthesis method of a dinotefuran intermediate-3-aminomethyltetrahydrofuran. Background technique [0002] 3-Aminomethyltetrahydrofuran is an important intermediate for the production of dinotefuran. Dinotefuran is a new type of neonicotinoid insecticide developed by Mitsui Corporation in Japan through the synthesis method of 3-aminomethyltetrahydrofuran. It was first introduced in Japan in 2002. It has been registered and put on the market, and has obtained pesticide registration certificates in many countries. [0003] The production technology of existing 3-aminomethyltetrahydrofuran is as follows: [0004] Method 1: The synthesis process of method 1 is as follows figure 1 As shown, diethyl malonate and ethyl bromoacetate undergo nucleophilic substitution reaction under the action of alkaline catalyst sodium ethoxide to generate 1,...

Claims

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Application Information

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IPC IPC(8): C07D307/14
CPCC07D307/14
Inventor 高武谢权王鹏宝曾永康张之翔
Owner XIAN CATALYST NEW MATERIALS CO LTD
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