A kind of preparation method of (e)-2,3-dibromo-2-butene-1,4-diol

A technology of diol and bromate, which is applied in the field of preparation of -2,3-dibromo-2-butene-1,4-diol, to achieve the effects of protecting the environment, operating safely and reducing production costs

Active Publication Date: 2020-04-28
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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Patent Type & Authority Patents(China)
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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