Method for synthesizing alpha-bromoketone and coproducing bromohydrocarbon

A technology of brominated hydrocarbons and brominated ketones, which is applied in the field of synthesizing α-bromoketones and co-producing brominated hydrocarbons, can solve the problems of unsafe use, serious environmental pollution, and high production costs, and achieve pollution and hazard avoidance. High economical efficiency and improved utilization

Inactive Publication Date: 2013-08-14
HEBEI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] (1). A large number of organic solvents are used. Some of these solvents are highly toxic and pollute the environment seriously; some have a very low boiling point and are extremely volatile, or even cause combustion and explosion. There are great safety problems in industrial production.
(2). In terms of the selection of brominating agent, although the use of copper bromide can avoid the strong irritation of bromine, and the operation is more convenient, it will produce a large amount of by-product brominated ketone, and the utilization rate of bromine is only 50% %; solid brominated dioxane, pyridine, hydrobromic acid and bromine 1: 1: 1 compound etc. are more convenient in bromination, but still need to use bromine and other compounds to prepare in advance; as for quaternary ammonium The perbromide is not only expensive to prepare, but also unsafe to use
[0013] Chinese patent CN101462935A discloses a method for preparing α-bromoketones by using bromate as a brominating agent in the presence of sodium bisulfite. Although this method uses water as a solvent, it will use a large amount of bromate and bisulfite
Chinese patent CN1807382A discloses a method for preparing α-bromoketones by using bromine as the bromination agent and using water as the solvent for bromination. Although water is used as the solvent, the utilization rate of bromine is only 50%, while the other 50 % generates hydrogen bromide, but nothing is done in this patent

Method used

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  • Method for synthesizing alpha-bromoketone and coproducing bromohydrocarbon
  • Method for synthesizing alpha-bromoketone and coproducing bromohydrocarbon
  • Method for synthesizing alpha-bromoketone and coproducing bromohydrocarbon

Examples

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Effect test

Embodiment 1

[0040] A method for synthesizing α-bromoacetophenone and co-producing bromoethane, its reaction equation is

[0041]

[0042] Its preparation steps are:

[0043] Add 60g (0.5mol) of acetophenone and 60ml of water into a four-necked flask equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser. First add 20ml of water to the dropping funnel, and then add 80g (0.5mol) Bromine, make water cover the surface of bromine, add a few drops of bromine dropwise under stirring, slowly heat, and then continue to add the remaining bromine dropwise after the bromine dropped in at the beginning completely fades, control the reaction temperature to keep the bromine dropped in quickly fades, until After all the bromine has been added, all the bromine is washed into the flask with the water covering the bromine in the dropping funnel. After the bromine faded completely, add 23g (0.5mol) ethanol in the flask by dropping funnel again, and change the reflux device into ...

Embodiment 2

[0047] A method for synthesizing p-chloro-alpha-bromoacetophenone and co-producing 1-bromobutane, its reaction equation is

[0048]

[0049] Its preparation steps are:

[0050] Add 75g (0.5mol) of p-chloroacetophenone, 37g (0.5mol) of 1-butanol, 60ml of water and 1ml of concentrated sulfuric acid into a four-necked flask equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser, drop First add 20ml of water to the liquid funnel, and then add 80g (0.5mol) of bromine, so that the water covers the surface of the bromine, start to add a few drops of bromine under stirring, slowly heat to reflux, and wait until the bromine dropped in at the beginning is completely faded. Continue to add the remaining bromine dropwise, control the reaction temperature to keep the dripped bromine fading rapidly until all the bromine is added, and finally wash all the bromine into the flask with the water covering the bromine in the funnel, when the bromine fades completely, ...

Embodiment 3

[0054] A method for synthesizing p-methoxy-alpha-bromoacetophenone and co-producing 2-bromobutane, its reaction equation is

[0055]

[0056] Its preparation steps are:

[0057] Add 75g (0.5mol) of p-methoxyacetophenone, 37g (0.5mol) of 2-butanol and 60ml of water into a four-necked flask equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser. First add 20ml of water, then add 80g (0.5mol) of bromine, start to add a few drops of bromine under stirring, slowly heat to 50-60°C, wait until the color of the bromine that was dropped at the beginning is completely faded, and then continue to add the remaining bromine dropwise. Keep the bromine dripped at the reaction temperature and fade rapidly until all the bromine is added. Finally, wash all the bromine into the flask with the water covered on the bromine in the funnel. completely. Then steam distillation is carried out until no oil flows out, and the distillation is stopped.

[0058] After cooling...

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Abstract

The invention discloses a method for synthesizing alpha-bromoketone and coproducing bromohydrocarbon. The technical scheme comprises the following steps of: adding arylalkyl ketone compounds, alcohol or epoxy compounds and water into a flask first; dripping bromine into the flask slowly under the conditions of stirring and heating; performing a bromo-reaction on the bromine and the ketone compounds to obtain alpha-bromoketone and bromine hydride; dissolving the bromine hydride in the water to form hydrobromic acid; performing a reaction on the hydrobromic acid and the alcohol or epoxy compounds to obtain bromohydrocarbon ketone compounds; after the reaction is completed, performing steam distillation to obtain a raffinate serving as an alpha-bromoketone crude product after distillation; cooling for separating crystals out; washing and drying the crystals to obtain an alpha-bromoarylalkyl ketone product; separating an aqueous layer from a distillate serving as a bromohydrocarbon crude product; washing an organic layer until the organic layer is neutral; drying by using anhydrous calcium chloride; and distilling to obtain a bromohydrocarbon product. In the method, the water is takenas a solvent, and the bromohydrocarbon is coproduced while the alpha-bromoketone compounds are synthesized; and the gross products of the reaction are the alpha-bromoketone, the bromohydrocarbon and the water, so the method has the characteristics that: the high atom utilization rate of the reaction is high, the generation or the discharging of noxious substances such as bromine hydride gas, strong acid waste water and the like is avoided, and the effects of environmental protection, energy conservation and reduction emission are achieved.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a method for synthesizing α-bromoketone and coproducing brominated hydrocarbons. Background technique [0002] α-Bromoketones are very important chemical intermediates for the synthesis of various medicines, pesticides, and dyes. With the continuous expansion of their application fields, people pay more and more attention to the research on their synthesis methods. Summarizing the research status at home and abroad, it is usually synthesized by α-bromination reaction with different brominating agents in different organic solvents. The focus of these studies was the use of brominating agents, and due attention was not given to the solvents used. So far, the commonly used brominating agents mainly include bromine, copper bromide, solid brominated dioxane, pyridine, hydrobromic acid and bromine 1:1:1 complex, anhydrous aluminum tribromide and bromine A mixture of zinc chl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/63C07C49/80C07C49/813C07C49/84C07C17/16C07C17/093C07C19/075C07C23/08C07C21/14C07C201/12C07C205/45C07C29/64C07C31/36C07C231/12C07C233/33
Inventor 张书文李志云
Owner HEBEI UNIVERSITY
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