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Preparation method of (E)-2, 3-dibromo-2-butene-1, 4-diol

A diol, bromate technology, applied in organic chemistry methods, introduction of halogen preparation, organic chemistry and other directions, to achieve the effects of operational safety, environmental protection, and production cost reduction

Active Publication Date: 2018-12-18
ZHEJIANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, the hydroxyl groups at the two allyl positions in the target product (E)-2,3-dibromo-2-butene-1,4-diol are also easily substituted by hydrobromic acid to form the corresponding side product

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Dissolve 1.2mol (103g) of 2-butyne-1,4-diol, 2.05mol (211g) of sodium bromide, and 0.4mol (60g) of sodium bromate into 420g of water, adjust the temperature of the system to 10-20°C, drop Add 1.2 mol of 50% sulfuric acid 240g, add dropwise in 1.5 hours, keep warm for 60 minutes after dropping, filter, and recrystallize the solid with water to obtain (E)-2,3-dibromo-2-butene-1,4 - 187 grams of diol white crystals, yield 63%, melting point 115.4-116.3°C.

Embodiment 2

[0028] 1.2mol (103g) 2-butyne-1,4-diol, sodium bromide 2.05mol (211g), sodium bromate 0.4mol (60g) are dissolved in the mother liquor after the recrystallization of 850g crude product (embodiment 1 obtained), the temperature of the system was adjusted to 20-30°C, 240 g of 1.2mol 50% sulfuric acid was added dropwise, and the addition was completed in 3.5 hours. -Dibromo-2-butene-1,4-diol white crystals 249g, yield 84%, melting point 114.9-115.6°C.

Embodiment 3

[0030] Dissolve 1.2mol (103g) of 2-butyne-1,4-diol, 2.08mol (214g) of sodium bromide, and 0.42mol (63g) of sodium bromate into 420g of water, adjust the temperature of the system to 20-30°C, drop Add 252g of 1.26mol 50% sulfuric acid, drop it in 2 hours, keep it warm for 40 minutes, filter it, and recrystallize the solid with water to get (E)-2,3-dibromo-2-butene-1,4 - 212 grams of diol white crystals, yield 72%, melting point 115.3-116.0°C.

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Abstract

The invention discloses a preparation method of (E)-2, 3-dibromo-2-butene-1, 4-diol. The method consists of the steps of: (1) preparing an aqueous solution of the mixture of 2-butyne-1, 4-diol, a bromide and a bromate; (2) adding dilute sulfuric acid into the aqueous solution of the mixture dropwise at certain temperature, then further carrying out reaction for 10-120min, and then ending the reaction; and (3) conducting pumping filtration, recrystallization, drying and other steps on the reaction product, thus obtaining a white (E)-2, 3-dibromo-2-butene-1, 4-diol crystal. The method provided by the invention has the advantages of low cost, simple operation, safety, environmental protection, high selectivity, few by-product, high yield, etc.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of (E)-2,3-dibromo-2-butene-1,4-diol. . Background technique [0002] (E)-2,3-dibromo-2-butene-1,4-diol has multiple functional groups such as bromine, double bonds, and hydroxyl, and is an important organic synthesis intermediate; it has remarkable Weeding, bactericidal, insecticidal and other properties, often used in the preparation of biocides; it can also be used as a surfactant in flux and solder paste, known as "the best surface active additive in all fluxes", commonly used For welding of high-precision electronic components. At present, there are many manufacturers of (E)-2,3-dibromo-2-butene-1,4-diol at home and abroad, but their preparation methods are basically similar, all through 2-butyne-1,4- [CN102249861A; CN1676503A], the molar ratio of 2-butyne-1,4-diol to bromine is generally controlled at 1:1~1.2, and the reaction t...

Claims

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Application Information

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IPC IPC(8): C07C29/62C07C33/42
CPCC07B2200/09C07B2200/13C07C29/62C07C33/423
Inventor 肖孝辉林霞罗虹
Owner ZHEJIANG NORMAL UNIVERSITY
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