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Production technology for 3-hydroxymethyltetrahydrofuran

A technology of hydroxymethyltetrahydrofuran and formyltetrahydrofuran, which is applied in the field of 3-hydroxymethyltetrahydrofuran production technology, can solve the problems of poor atom economy, unfavorable industrial production, cumbersome post-processing, etc., and achieve strong production operability , short steps, no effects of highly toxic reagents

Active Publication Date: 2018-09-14
HUBEI JINGHONG CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] The first step of the route is shorter, but LiAlH is used 4 , the post-processing is cumbersome and the operation risk is high, which is not conducive to industrial production; the second step of the route is longer, and there are steps of adding protective groups and deprotecting groups, the atom economy is not good, and the cost is high; the third route uses regulated The highly toxic 2-chloroethanol, and the NaBH used for reduction 4 , high operational risk

Method used

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  • Production technology for 3-hydroxymethyltetrahydrofuran
  • Production technology for 3-hydroxymethyltetrahydrofuran
  • Production technology for 3-hydroxymethyltetrahydrofuran

Examples

Experimental program
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Effect test

Embodiment 1

[0030] This embodiment includes the following steps:

[0031] The first step, in the reaction kettle, add 8.81kg (100mol) of 1,4-butenediol and 0.615kg (1.2mol) of tris(pentafluorophenyl)borane, react at 135°C for 4.5h, and distill under reduced pressure to obtain 2,5-dihydrofuran 6.71kg (95.7mol), the yield is 95.7%; H NMR (400MHz, CDCl 3 ):5.80(s,2H),4.55(s,4H);

[0032] The second step, in the autoclave, dissolve 6.71kg (95.7mol) of 2,5-dihydrofuran in 9.5L toluene, add RhCl (CO) (DPPB) 8.5g (14.4mmol), NaB (3,5 -(CF 3 ) 2 C 6 h 3 ) 4 12.7g (14.4mmol), after replacing the gas in the kettle with nitrogen for three times, feed H 2 Mix gas with CO (volume ratio 1:1) to a total pressure of 4MPa, heat up to 100°C, react for 2.5h, cool to room temperature, slowly vent, filter, and distill under reduced pressure to obtain 9.03kg (90.15mol ), the yield was 94.2%; H NMR (400MHz, CDCl 3 ):9.60(d,1H),3.92(m,2H),3.87(m,2H),3.05(m,1H),2.16(m,2H);

[0033] The 3rd step, add 3-f...

Embodiment 2

[0035] This embodiment includes the following steps:

[0036] The first step, in the reaction kettle, add 8.81kg (100mol) of 1,4-butenediol and 1.024kg (2mol) of tris(pentafluorophenyl)borane, react at 125°C for 5h, and distill under reduced pressure to obtain 2, 5-dihydrofuran 6.48kg (92.5mol), the yield is 92.5%;

[0037] In the second step, in an autoclave, dissolve 6.48kg (92.5mol) of 2,5-dihydrofuran in 9L of toluene, add 6.5g (11.1mmol) of RhCl(CO)(DPPB), NaB(3,5- (CF 3 ) 2 C 6 h 3 ) 4 9.8g (11.1mmol), after replacing the gas in the kettle with nitrogen for three times, feed H 2 Mix gas with CO (volume ratio 1:1) to a total pressure of 4MPa, heat up to 90°C, react for 4h, cool to room temperature, slowly vent, filter, and distill under reduced pressure to obtain 8.87kg (88.6mol) of 3-formyltetrahydrofuran , the yield is 95.8%;

[0038] The third step, add 3-formyl tetrahydrofuran 8.87kg (88.6mol) in the autoclave, 5%Pd / C 0.44kg, and 100L ethanol, after three time...

Embodiment 3

[0040] This embodiment includes the following steps:

[0041]The first step, in the reaction kettle, add 8.81kg (100mol) of 1,4-butenediol and 0.512kg (1mol) of tris(pentafluorophenyl)borane, react at 125°C for 6h, and distill under reduced pressure to obtain 2, 5-dihydrofuran 6.81kg (97.1mol), the yield is 97.1%;

[0042] In the second step, in an autoclave, dissolve 6.81kg (97.1mol) of 2,5-dihydrofuran in 10L of toluene, add 5.7g (9.71mmol) of RhCl(CO)(DPPB), NaB(3,5- (CF 3 ) 2 C 6 h 3 ) 4 8.5g (9.71mmol), after replacing the gas in the kettle with nitrogen for three times, feed H 2 Mix gas with CO (volume ratio 1:1) to a total pressure of 4MPa, heat up to 95°C, react for 3h, cool to room temperature, slowly vent, filter, and distill under reduced pressure to obtain 9.39kg (93.8mol) of 3-formyl tetrahydrofuran , the yield is 96.6%;

[0043] The third step, add 3-formyl tetrahydrofuran 9.39kg (93.8mol) in the autoclave, 5%Pd / C 0.47kg, and 110L ethanol, after the gas i...

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Abstract

The invention discloses a production technology for 3-hydroxymethyltetrahydrofuran, and belongs to the field of pesticide intermediate synthetic processes. The production technology is capable of using 2-butene-1,4-diol as a starting raw material, and synthesizing the 3-hydroxymethyltetrahydrofuran through a three-step reaction of dehydration cyclization, hydroformylation and reduction. The production technology is moderate in reaction conditions, low in cost, less in three wastes, and suitable for the industrial production.

Description

technical field [0001] The invention relates to the technical field of synthesis of pesticide intermediates, in particular to a production process of 3-hydroxymethyltetrahydrofuran. Background technique [0002] Dinotefuran is a new type of neonicotinoid insecticide developed by Japan Mitsui Chemicals Co., Ltd. Its structure is as follows: [0003] [0004] Dinotefuran does not contain chlorine atoms and aromatic rings, has a characteristic structure of 3-tetrahydrofurylmethyl, and has strong water solubility. It can kill insects through contact and stomach poisoning, and has the characteristics of convenient use, strong systemic absorption, and long-lasting effect; it can be used on various crops such as rice and wheat. In 2002, dinotefuran was listed in Japan; in 2003, it was listed in South Korea; in 2004, it was registered in the United States for the first time; in 2013, it was registered in China. Since the listing of dinotefuran, its sales have continued to grow,...

Claims

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Application Information

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IPC IPC(8): C07D307/12
CPCC07D307/12
Inventor 杨辉崔军霞王勇丽吴志强赵亚运
Owner HUBEI JINGHONG CHEM
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