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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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 ar

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0029] Example 1

[0030] This embodiment includes the following steps:

[0031] The first step, in the reactor, add 8.81kg (100mol) of 1,4-butenediol, 0.615kg (1.2mol) of tris(pentafluorophenyl)borane, react at 135℃ 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] In the second step, in an autoclave, dissolve 6.71kg (95.7mol) of 2,5-dihydrofuran in 9.5L of 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 three times, pass H 2 And CO (volume ratio 1:1) mixed gas to a total pressure of 4MPa, heated to 100 ℃, reacted for 2.5h, cooled to room temperature, slowly vented, filtered, and vacuum distillation to obtain 3-formyltetrahydrofuran 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);

[0...

Example Embodiment

[0034] Example 2

[0035] This embodiment includes the following steps:

[0036] The first step is to add 8.81kg (100mol) of 1,4-butenediol and 1.024kg (2mol) of tris(pentafluorophenyl)borane to the reaction kettle, react at 125℃ 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 toluene, add RhCl(CO)(DPPB) 6.5g (11.1mmol), NaB(3,5- (CF 3 ) 2 C 6 H 3 ) 4 9.8g (11.1mmol), after replacing the gas in the kettle with nitrogen three times, pass H 2 Mix gas with CO (1:1 by volume) to a total pressure of 4MPa, heat to 90℃, react for 4h, cool to room temperature, vent slowly, filter, and distill under reduced pressure to obtain 8.87kg (88.6mol) of 3-formyltetrahydrofuran , The yield was 95.8%;

[0038] The third step is to add 8.87 kg (88.6 mol) of 3-formyl tetrahydrofuran (88.6 mol), 5% Pd / C 0.44 kg, and 100 L ethanol into the autoclave...

Example Embodiment

[0039] Example 3

[0040] This embodiment includes the following steps:

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

[0042] In the second step, in an autoclave, dissolve 6.81kg (97.1mol) of 2,5-dihydrofuran in 10L of toluene, add RhCl(CO)(DPPB)5.7g (9.71mmol), NaB(3,5- (CF 3 ) 2 C 6 H 3 ) 4 8.5g (9.71mmol), after replacing the gas in the kettle with nitrogen three times, pass H 2 Mix gas with CO (volume ratio 1:1) to a total pressure of 4MPa, heat 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-formyltetrahydrofuran , The yield was 96.6%;

[0043] In the third step, add 9.39kg (93.8mol) of 3-formyltetrahydrofuran, 5% Pd / C 0.47kg, and 110L ethanol into the autoclave. After replacing the gas...

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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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