Preparation method of polybrominated biphenyl ether monomer

A technology of polybrominated diphenyl ethers and monomers, applied in ether preparation, organic chemistry, etc., can solve the problems of dangerous experimental operation, difficult preparation and storage, etc., and achieve the effect of simple and safe operation and wide application range

Inactive Publication Date: 2013-01-09
SHANDONG ANALYSIS & TEST CENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

High-concentration fuming sulfuric acid and fuming nitric acid are not easy to

Method used

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  • Preparation method of polybrominated biphenyl ether monomer
  • Preparation method of polybrominated biphenyl ether monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: the preparation of BDE-47

[0027] Compound 1: Suspend iodine (1.0 g, 4 mmol) in 9.0 g of 98% sulfuric acid with a mass concentration of 9.0 g, add sodium iodate (3.2 g, 16 mmol) at 55°C, and complete the addition within 30 minutes. Then react at 55° C. for 2 h to obtain a dark brown reaction liquid, which is directly used in the next reaction without purification.

[0028] Compound 3: Cool the above reaction solution to 20-30°C, dilute with 9.0g mass concentration of 98% sulfuric acid, add 1,3-dibromobenzene (13.1g, 56mmol) within 30min, and react at 20-30°C for 24h. Cool in an ice-water bath to 0-5°C, add 6.0 g of ice water dropwise, collect the solid by suction filtration, wash with 10 mL of water and 10 mL of acetone, and dry naturally in the dark to obtain 4.3 g of a beige solid, 78.2%. .

[0029] BDE-47: Add 80g of dioxane, 40g of water, 2,4-dibromophenol (0.25g, 1mmol), potassium tert-butoxide (0.12g, 1.1mmol) into the reaction flask, stir at room...

Embodiment 2

[0030] Embodiment 2: the preparation of BDE-28

[0031] The preparation of compound 3 was the same as in Example 1.

[0032] BDE-28: Add 100g of dioxane, 40g of water, p-bromophenol (0.17g, 1mmol), potassium tert-butoxide (0.12g, 1.1mmol) into the reaction flask, stir at room temperature for 15min, then slowly add in 30min Compound 3 (0.76g, 1.1mmol), after completion, the temperature was raised to 75°C, and the reaction was stirred for 2h. The solvent was distilled off under reduced pressure, and the resulting white residue was subjected to column chromatography to obtain 0.33 g of a white solid, 81%. 1 H NMR: (600MHz, CDCl 3 )7.78(d,1H,J=1.8Hz),7.44(dd,2H,J=1.8and 7.2Hz),7.39(dd,1H,J=2.4and 9.0Hz),6.84(d,1H,J=8.4 Hz),6.83(d,1H,J=7.2Hz),6.82(d,1H,J=7.2Hz); 13 C NMR (150MHz, CDCl 3 ): 155.91, 153.24, 135.96, 131.82, 130.13, 130.95, 121.93, 119.52, 118.64, 118.18, 117.26, 116.14ppm.

Embodiment 3

[0033] Embodiment 3: the preparation of BDE-100

[0034] The preparation of compound 3 was the same as in Example 1.

[0035] BDE-100: Add 90g of dioxane, 45g of water, 2,4,6-tribromophenol (0.33g, 1mmol), potassium tert-butoxide (0.12g, 1.1mmol) into the reaction flask, and stir at room temperature for 30min , and then slowly added compound 3 (0.76g, 1.1mmol) within 30min, and then raised the temperature to 85°C and stirred for 2h. The solvent was distilled off under reduced pressure, and the resulting white residue was subjected to column chromatography to obtain 0.50 g of a white solid, 89%. 1 H NMR: (600MHz, CDCl 3 )7.77-7.79(m,3H), 7.25-7.27(m,1H),6.27(d,1H,J=9.0Hz); 13 C NMR (150MHz, CDCl 3 ): 151.66, 148.73, 136.32, 135.46, 131.56, 119.45, 119.69, 115.32, 115.33, 112.65ppm.

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Abstract

The invention relates to a preparation method of a polybrominated biphenyl ether monomer. The method comprises the steps that iodine is oxidized by sodium iodate and is subjected to reaction with bromobenzene to obtain a series of diaryl iodonium salt, and the diaryl iodonium salt and the bromobenzene are subjected to reaction under catalysis of alkali, and polybrominated biphenyl ether is obtained. According to the method, any type of polybrominated biphenyl ether monomer can be prepared, and the method can support detection and activity researches of the type of compounds.

Description

technical field [0001] The invention relates to a method for synthesizing polybrominated diphenyl ether compound monomers. Background technique [0002] According to the number of bromine atoms and the position of polybrominated diphenyl ethers, there are 209 homologues in total. Carrying out environmental research on such compounds as soon as possible will help to understand the environmental behavior and fate of polybrominated diphenyl ethers more comprehensively, so as to make an objective and reliable environmental assessment. Risk Assessment. At present, the synthesis of polybrominated diphenyl ethers in the world is mainly carried out by Sweden. The Marsh team is working on it, and its synthesis method is made by coupling reaction of iodonium salt and bromophenol. Wherein the preparation of iodonium salt needs to use 65% fuming sulfuric acid and 100% fuming nitric acid, the concentration of two kinds of acids plays a key role to reaction. High-concentration fuming ...

Claims

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Application Information

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IPC IPC(8): C07C43/225C07C41/01
Inventor 纪文华高乾善赵汝松苑金鹏陈相峰林云良高红梅
Owner SHANDONG ANALYSIS & TEST CENT
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