Novel preparation method of bromopropylate

A technology of bromodifen and bromobenzene, which is applied in the new preparation field of bromite, can solve the problems of serious self-polymerization of glyoxylic acid, many wastes, low yield, etc., so as to reduce the generation of wastes and increase the reaction yield. efficiency, improving the reaction selectivity

Inactive Publication Date: 2021-10-29
JIANGSU HEBEN BIOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a new preparation method of bromofen, to solve the problem of serious self-polymerization of glyoxylic acid in the preparation of bromofen in the above background technology, low yield, high cost and many wastes. Happening

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  • Novel preparation method of bromopropylate

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Step 1, the preparation of intermediate 1:

[0028] Put 180.00g of 40% glyoxylic acid into the reaction kettle, dehydrate under the condition of 40-80℃ / -0.095MPa for 1-2 hours, add 296.00g of toluene to reflux with water until it is basically anhydrous (control the moisture below 0.5%), Cool down to 20-50°C and put in 5.55g of acidic catalyst, raise the temperature, add 63.64g of 99% isopropanol dropwise in the reflux state, bring water back to the reflux, control glyoxylic acid below 0.5%, cool to 20-50°C, Add 185.00 g of washing water, separate the phases, and desolventize the organic phase to obtain 115.01 g of 98% isopropyl glyoxylate, namely intermediate 1.

[0029] Step 2, the preparation of intermediate 2:

[0030] Add 5.55g of Lewis acid and 407.00g of 99% bromobenzene to intermediate 1, raise the temperature to 20-50°C, add 185.00g of 98% water-absorbing agent dropwise, stir for 2-5 hours, the reaction is complete, and cool down for 20 Below ℃, add 296.00g of...

Embodiment 2

[0036] Step 1, the preparation of intermediate 1:

[0037] Put 185.00g of 40% glyoxylic acid into the reaction kettle, dehydrate under the condition of 40-80℃ / -0.095MPa for 1-2 hours, add 370.00g of toluene to reflux with water until it is basically anhydrous (control moisture below 0.5%), Cool down to 20-50°C and put in 9.25g of acidic catalyst, raise the temperature, add 66.67g of 99% isopropanol dropwise under reflux, bring water back to the reflux, control glyoxylic acid below 0.5%, cool to 20-50°C, Add 203.50 g of washing water, separate the phases, and desolventize the organic phase to obtain 115.00 g of 98% isopropyl glyoxylate, namely intermediate 1.

[0038] Step 2, the preparation of intermediate 2:

[0039] Add 9.25g Lewis acid, 555.55g, 99% bromobenzene to intermediate 1, raise the temperature to 20-50°C, add dropwise 203.50g, 98% water-absorbing agent, stir and react for 2-5 hours, the reaction is complete, and lower the temperature by 20°C Next, add 370.00 g of...

Embodiment 3

[0045] Step 1, the preparation of intermediate 1:

[0046] Put 185.00g of 40% glyoxylic acid into the reaction kettle, dehydrate under the condition of 40-80℃ / -0.095MPa for 1-2 hours, add 310.00g of toluene to reflux with water until it is basically anhydrous (control moisture below 0.5%), and cool down Add 6.20g of acidic catalyst to 20-50°C, raise the temperature, add 65.00g of 99% isopropanol dropwise under reflux, return with water, control glyoxylic acid below 0.5%, cool to 20-50°C, add 200.00 g of washing water, phase separation, and desolventization of the organic phase to obtain 115.00 g of 98% isopropyl glyoxylate, namely intermediate 1.

[0047] Step 2, the preparation of intermediate 2:

[0048] Add 6.25g Lewis acid, 400.00g, 99% bromobenzene to intermediate 1, raise the temperature to 20-50°C, add dropwise 200.00g, 98% water-absorbing agent, stir and react for 2-5 hours, the reaction is complete, and lower the temperature by 20°C Next, add 350.00 g of washing wat...

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Abstract

The invention discloses a novel preparation method of bromopropylate, which mainly comprises the following four steps: 1) esterification; 2) condensation; 3) oxidation; and 4) refining. Compared with an existing technical route, the method has the advantages that a large amount of water does not exist in the condensation step in the process route, the selection range of a catalyst is wide, the production cost is reduced, the Lewis acid catalyst is adopted for condensation catalysis, the reaction selectivity is improved, the reaction yield is increased, waste is reduced, and the use amount of the existing market can be met.

Description

technical field [0001] The invention belongs to the technical field of synthesis methods of the acaricide bromofen, in particular to a new preparation method of bromofen. Background technique [0002] The chemical name of bromofen is 4,4'-dibromomandelic acid isopropyl ester, molecular formula: C 17 h 16 Br 2 o 3 , is a low-toxic, high-efficiency, broad-spectrum acaricide with strong contact activity and long-lasting effect. It has good contact effect on adults, nymphs and eggs, and the temperature change has little effect on the efficacy. It is widely used in fruit trees, vegetables, tea, cotton and farmland crops to prevent and control various harmful mites such as spider mites, gall mites, barb mites, and nematodes. Due to the unique mechanism of action of bromofen, its usage is gradually expanding. [0003] At present, bromofen is prepared mainly by glyoxylic acid under the condition of catalyst to generate intermediate 1, intermediate 1 is esterified with isopropan...

Claims

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Application Information

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IPC IPC(8): C07C69/732C07C67/31C07C67/52
CPCC07C67/31C07C67/343C07C67/08C07C67/52C07C69/732C07C69/65C07C69/716
Inventor 冯魏陈华贾利华邓桂元邢燕
Owner JIANGSU HEBEN BIOCHEM
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