Synthesis method of tetrahydrofuran-3-formaldehyde

A technology of tetrahydrofuran and synthetic methods, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, organic chemistry, etc., can solve the problems of low product yield and high cost of tetrahydrofuran-3-formaldehyde, and achieve High purity, beneficial to recovery and recycling, and the effect of improving reaction selectivity

Inactive Publication Date: 2021-02-19
DALIAN JOIN KING FINE CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention aims at the above problems, and researches and designs a synthetic method for tetrahydrofuran-3-carbaldehyde to solve the disadvantages of relatively high cost and low product yield in the traditional method of synthesizing tetrahydrofuran-3-carbaldehyde

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] In the 500ml autoclave, drop into 150g of 2,5-dihydrofuran, rhodium content is 5% rhodium carbon catalyst 2.5g, three (p-fluorophenyl) phosphine 1.6g, 2,6-di-tert-butyl p-cresol 15.0g mg, close the autoclave.

[0023] Nitrogen was replaced three times to replace air, water gas was replaced three times to replace nitrogen, and the pressure was reduced to 3.0Mpa. Raise the temperature of the system to 40-50°C, pass water and gas to keep the pressure at 3.0-3.5Mpa and react for about 10 hours. After the pressure no longer drops, take a sample and test it with gas chromatography (GC) to confirm that the reaction of 2,5-dihydrofuran is complete.

[0024] After the reaction, cool the system down to room temperature, release the pressure and exhaust, take out the reaction solution, and distill under reduced pressure at 100°C with a vacuum of 5mmHg. Stop distilling until no distillate comes out, and obtain 214.7g of the target product, of which tetrahydrofuran-3 - The formalde...

Embodiment 2

[0026] Put 150 g of 2,5-dihydrofuran, 5.0 g of the catalyst recovered in Example 1, and 15.0 mg of 2,6-di-tert-butyl-p-cresol into a 500 ml autoclave, and close the autoclave.

[0027] Nitrogen is replaced three times to replace air, water gas is replaced three times to replace nitrogen, and the pressure is reduced to 3.0Mpa. Raise the temperature of the system to 40-50°C, pass water and gas to keep the pressure at 3.0-3.5Mpa and react for about 12 hours. When the pressure no longer drops, take a sample for GC detection and confirm that the 2,5-dihydrofuran reaction is complete.

[0028] After the reaction, the system was cooled to room temperature, the pressure was released and exhausted, and the reaction solution was taken out, and distilled under reduced pressure at 100°C with a vacuum degree of 5mmHg, and the distillation was stopped until no distillate was produced, and 214.9g of the target product was obtained, of which tetrahydrofuran-3 - The formaldehyde content is 99....

Embodiment 3

[0030] In the 500ml autoclave, drop into 150g of 2,5-dihydrofuran, 5.3g of catalyst recovered after five times of mechanical application, 50mg of 5% rhodium carbon catalyst, 25mg of tri(p-fluorophenyl)phosphine, 2,6-di-tert-butyl p-cresol 15.0mg, close the autoclave.

[0031] Nitrogen is replaced three times to replace air, water gas is replaced three times to replace nitrogen, and the pressure is reduced to 3.0Mpa. Raise the temperature of the system to 40-50°C, pass water and gas to keep the pressure at 3.0-3.5Mpa and react for about 10 hours. When the pressure no longer drops, take a sample for GC detection to confirm that the reaction of 2,5-dihydrofuran is complete.

[0032] After the reaction, the system was cooled to room temperature, the pressure was released and exhausted, and the reaction liquid was taken out, and distilled under reduced pressure at 100°C with a vacuum degree of 5mmHg. After distilling until no distillate was produced, the distillation was stopped to...

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PUM

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Abstract

The invention discloses a synthesis method of tetrahydrofuran-3-formaldehyde, which comprises the steps of S1, mixing 2,5-dihydrofuran, a rhodium-carbon catalyst, a phosphine ligand cocatalyst and a polymerization inhibitor, and carrying out hydroformylation reaction under the action of water gas; and S2, after the reaction is completed, taking out the reaction liquid, and carrying out reduced pressure distillation to obtain tetrahydrofuran-3-formaldehyde. By adopting the rhodium-carbon catalyst, the cost can be reduced, the polymerization inhibitor is introduced, the side reaction of dimerization of 2,5-dihydrofuran can be prevented, the reaction selectivity is improved, the solvent-free reaction is adopted in the whole reaction system, the post-treatment process is further simplified while the production capacity is improved, the catalyst is favorably recycled and reused at the same time, the obtained product has high purity and high yield, and the method is very suitable for industrial large-scale production.

Description

technical field [0001] The invention belongs to the technical field of fine chemical synthesis, and in particular relates to a synthesis method of tetrahydrofuran-3-carbaldehyde. Background technique [0002] Dinotefuran was discovered and produced by Mitsui Chemicals, and jointly developed by Mitsui Chemicals, Beixing Chemicals and Valent. It is a third-generation neonicotinoid insecticide and has a good market development prospect. Tetrahydrofuran-3-carbaldehyde is a key intermediate for the preparation of dinotefuran, and in addition, tetrahydrofuran-3-carbaldehyde is more and more widely used. [0003] At present, the mainstream synthesis method of tetrahydrofuran-3-carbaldehyde is to use 2,5-dihydrofuran and water gas synthesis gas to carry out hydroformylation reaction. The catalyst usually uses a rhodium compound precursor and an organic phosphine ligand as a cocatalyst. The solvent is selected from toluene, Organic solvents such as dichloroethane, as reported in doc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/12B01J31/24
CPCC07D307/12B01J31/2404B01J2531/822Y02P20/584
Inventor 王俊春王荣良肖利锋吕超王延波
Owner DALIAN JOIN KING FINE CHEM CO LTD
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