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Bromination of hydroxyaromatic compounds and further conversion to dihydroxyaromatic compounds

A hydroxyaromatic and brominated hydroxyaromatic technology is applied in the conversion of monocyclic dihydroxyaromatic compounds and dihydroxybiphenyls, compounds to brominated derivatives, the preparation of brominated hydroxyaromatic compounds, and the field of polyetherimide. Solve problems such as bromophenol not being promoted, and achieve easy-to-achieve effects

Inactive Publication Date: 2006-04-05
SABIC INNOVATIVE PLASTICS IP BV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a result, in general, the industrial production of bromophenols by reaction of phenol with hydrogen bromide or other simple ionic bromides has not been widespread

Method used

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  • Bromination of hydroxyaromatic compounds and further conversion to dihydroxyaromatic compounds
  • Bromination of hydroxyaromatic compounds and further conversion to dihydroxyaromatic compounds
  • Bromination of hydroxyaromatic compounds and further conversion to dihydroxyaromatic compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] A 3-dram vial was charged with 1.37ml (15.56mmol) phenol, 0.112g (0.5mmol) copper bromide, 1.39ml (12.50mmol) 48% hydrobromic acid and 2.20ml acetonitrile. The vial was sealed with a cap with a hole for air flow during the reaction and placed in an aluminum block. The aluminum block was placed in a 450 ml autoclave reactor, pressurized with air to 34.0 atmospheres and heated at 65°C for 1 hour. It was then cooled to room temperature and the pressure reduced. Analysis of the obtained mixture by gas chromatography showed it to contain 7.39% phenol, 28.63% 4-bromophenol, 5.59% 2-bromophenol and 0.68% 2,4-dibromophenol, corresponding to 72% conversion of phenol, There is 82% selectivity to 4-bromophenol and 98% selectivity to total monobromophenol.

Embodiment 2

[0041] A 3-dram vial was charged with 1.59 ml (15.39 mmol) o-cresol, 0.112 g (0.5 mmol) copper bromide, 1.48 ml (12.47 mmol) 48% hydrobromic acid and 1.92 ml acetonitrile. As in Example 1, the vial was sealed and placed, pressurized with air to 34.0 atmospheres and heated at 65°C for 1 hour. It was then cooled to room temperature and the pressure reduced. Analysis of the obtained mixture by gas chromatography showed that it contained 13.23% o-cresol, 27.74% 4-bromo-2-cresol and 0.93% 6-bromo-2-cresol, corresponding to 56% o-cresol - Cresol conversion with 96% selectivity to 4-bromo-2-cresol and 99% selectivity to total monobromophenols.

Embodiment 3

[0043] A 3-dram vial was charged with 1.37 ml (15.56 mmol) of phenol, 0.112 g (0.5 mmol) of copper bromide, 1.30 ml (6.85 mmol) of 30% hydrogen bromide in acetic acid and 2.31 ml of acetonitrile. As in Example 1, the vial was sealed and placed, pressurized with air to 34.0 atmospheres and heated at 65°C for 1 hour. It was then cooled to room temperature and the pressure reduced. Analysis of the obtained mixture by gas chromatography showed that it contained 14.12% phenol, 19.15% 4-bromophenol and 1.15% 2-bromophenol, corresponding to 44% conversion of phenol, 96% selectivity to 4-bromophenol and 100% total monobromophenol selectivity.

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Abstract

Brominated hydroxyaromatic compounds such as p-bromophenol are prepared by contacting a hydroxyaromatic compound with oxygen and a bromine source such as hydrogen bromide or an alkali metal or alkaline earth metal bromide in an acidic medium, in the presence of elemental copper or a copper compound as catalyst. The brominated product of this reaction may be converted alternately to a dihydroxyaromatic compound such as hydroquinone by hydrolyses, or a dihydroxybiphenyl compound such as 4,4'-dihydroxybiphenyl by reductive coupling.

Description

Background technique [0001] This invention relates to the reaction of hydroxyaromatic compounds, and more particularly to the conversion of such compounds to brominated derivatives, monocyclic dihydroxyaromatic compounds and dihydroxybiphenyls. [0002] Monocyclic dihydroxyaromatic compounds such as hydroquinone and dihydroxybiphenyls such as 4,4'-dihydroxybiphenyl (often abbreviated hereinafter as "biphenol") have many uses in the chemical industry. For example, both compounds can be used in the preparation of polymers, especially in the preparation of polycarbonates, polysulfones and polyimides, especially polyetherimides. [0003] Various methods exist for the preparation of hydroquinone and biphenol. As examples of these methods, each compound can be prepared from p-bromophenol, hydroquinone by hydrolysis and from biphenol by reductive coupling in the presence of a noble metal catalyst, base and reducing agent. [0004] Brominated hydroxyaromatic compounds, exemplified b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/62C07C37/02C07C37/18C07C39/27C07C39/08C07C39/15
CPCC07C37/02C07C37/62C07C37/18C07C39/27C07C39/08C07C39/15
Inventor 埃里克·J·普雷斯曼约翰·Y·奥弗里格里戈里·L·索洛维奇克瑞安·C·米尔斯乔纳森·L·马尔
Owner SABIC INNOVATIVE PLASTICS IP BV
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