CN102992948B - Method for preparing bromobenzene by recovering by-product multiple-substituted bromobenzene in bromobenzene synthesis - Google Patents
Method for preparing bromobenzene by recovering by-product multiple-substituted bromobenzene in bromobenzene synthesis Download PDFInfo
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- CN102992948B CN102992948B CN201210492879.7A CN201210492879A CN102992948B CN 102992948 B CN102992948 B CN 102992948B CN 201210492879 A CN201210492879 A CN 201210492879A CN 102992948 B CN102992948 B CN 102992948B
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Abstract
The invention relates to a method for preparing bromobenzene by recovering by-product multiple-substituted bromobenzene in bromobenzene synthesis, thereby realizing comprehensive utilization of the by-product multiple-substituted bromobenzene in the bromobenzene synthesis process. The method comprises the step of putting multiple-substituted bromobenzene, benzene and a certain proportion of a catalyst together for halogenation transfer reaction; the conversion rate of the multiple-substituted bromobenzene is greater than 90%.
Description
Technical field
The present invention relates to the many methods of preparing bromobenzene that reclaim for bromobenzene of the synthetic middle by-product of a kind of bromobenzene.
Background technology
Bromobenzene is the synthetic important intermediate of sterilant bifenthrin, conventionally in bromobenzene preparation process, can produce a certain amount of manyly for bromobenzene, is accumulated in bromobenzene rectification residue more.This part contains many for bromobenzene isomer, is generally difficult to separate be used, and causes the wasting of resources and waste sludge discharge.
In prior art, have no the many open reports of preparing bromobenzene that reclaim through catalyst treatment for bromobenzene of by-product.
Summary of the invention
The object of the invention is to propose a kind of many methods of preparing bromobenzene for bromobenzene processing recovery of by-product in bromobenzene preparation process, effectively utilize for bromobenzene many by-product, increase the utilization ratio of bromine resource.
Above-mentioned purpose of the present invention is achieved through the following technical solutions:
A kind of many methods of preparing bromobenzene for bromobenzene are provided, and are to obtain bromobenzene by how carrying out halo shift reaction with benzene for bromobenzene under catalyst action.This process reaction equation is as follows:
In method of the present invention, described many can be general formula for bromobenzene
the mixture of one or more in the multiple bromobenzene representing, the integer that wherein n is 2 ~ 5; In preferred bromobenzene preparation process, by-product is many for bromobenzene mixture.
Described catalyzer can be to meet formula M X
blewis acid in any one or multiple mixture, wherein M is iron, aluminium, boron, titanium, tin, gallium, antimony, pick, tellurium or niobium element, X is halogens, b is the cationic valence state number of M; Preferred catalyzer is iron trichloride, alchlor, tin tetrachloride, titanium tetrachloride or aluminum chloride.
In method of the present invention, described benzene with how be preferably 1 ~ 10:1 for the mol ratio of bromobenzene, more preferably 2 ~ 5:1.
In method of the present invention, preferred catalyzer usage quantity is many for 0.1 ~ 20% of bromobenzene weight.
In method of the present invention, described halo shift reaction is preferably carried out under the pressure of 0 ~ 1MPa.
In method of the present invention, described halo shift reaction temperature is preferably controlled between 50-150 DEG C, more preferably 80 ~ 120 DEG C.
In method of the present invention, described preferred 3-8hr of halo shift reaction time.
How the present invention will carry out halo shift reaction with benzene for bromobenzene under Louis acid catalysis obtains bromobenzene, be applied to can make the many of by-product in bromobenzene preparation effectively utilize for bromobenzene in bromobenzene preparation, increase the utilization ratio of bromine resource, avoid bromobenzene produce in many discarded for bromobenzene of by-product, reach the object of cleaner production.
Embodiment
Embodiment 1:
In 1000ml reaction vessel, how for bromobenzene, (normalizing is containing bromobenzene 6% to drop into 100g, paradibromobenzene 69.5%, o-dibromobenzene 23.7%), benzene 500g, drop into again catalyzer iron trichloride 10g, be warming up to 80 DEG C of synthesis under normal pressure 8hr, product gas spectrum normalizing composition bromobenzene 94.5%, paradibromobenzene 2.8%, o-dibromobenzene 2.1%, its transformation efficiency 95%.
Embodiment 2:
In 1000ml reaction vessel, drop into 200g many for bromobenzene (normalizing is containing bromobenzene 1.5%, dibromobenzene 85%, tribromo-benzene 10.5%), benzene 400g, drop into catalyzer alchlor 30g again, be warming up to 120 DEG C, pressure 0.04MPa reacts 3hr, product gas spectrum normalizing composition bromobenzene 94.1%, dibromobenzene 0.1%, tribromo-benzene 2.8%, its transformation efficiency 97%.
Embodiment 3:
In 1000ml reaction vessel, how for bromobenzene, (normalizing is containing bromobenzene 0.8%, dibromobenzene 15.3% to drop into 100g, tribromo-benzene 35.4%, tetrabromo-benzene 43.5%), benzene 250g, then drop into catalyzer tin tetrachloride 20g, be warming up to 150 DEG C, pressure 0.07MPa reacts 2hr, product gas spectrum normalizing composition bromobenzene 94%, tribromo-benzene 0.4%, tetrabromo-benzene 0.5%, its transformation efficiency 99%.
Embodiment 4:
In 1000ml reaction vessel, how for bromobenzene, (normalizing is containing bromobenzene 6%, dibromobenzene 85.3% to drop into 100g, tribromo-benzene 7.7%), benzene 300g, then drop into catalyzer titanium tetrachloride 5g, be warming up to 90 DEG C, pressure 0.01MPa, reaction 5hr, product gas spectrum normalizing composition bromobenzene 95.3%, dibromobenzene 1.5%, o-dibromobenzene 2.2%, its transformation efficiency 96%.
Embodiment 5:
In 1000ml reaction vessel, how for bromobenzene, (normalizing is containing bromobenzene 22.4%, dibromobenzene 75.1% to drop into 100g, tribromo-benzene 1.5%), benzene 400g, then drop into catalyzer aluminum chloride 15g, be warming up to 100 DEG C, pressure 0.02MPa, reaction 4hr, product gas spectrum normalizing composition bromobenzene 96.7%, dibromobenzene 0.7%, tribromo-benzene 1.5%, its transformation efficiency 97%.
Embodiment 6:
In 1000ml reaction vessel, how for bromobenzene, (normalizing is containing bromobenzene 22.4%, dibromobenzene 75.1% to drop into 100g, tribromo-benzene 1.5%), benzene 400g, then drop into catalyzer aluminum chloride 18g, be warming up to 70 DEG C, pressure 0.5MPa, reaction 4hr, product gas spectrum normalizing composition bromobenzene 96.1%, dibromobenzene 1.3%, tribromo-benzene 1.6%, its transformation efficiency 96%.
Claims (6)
1. a method of preparing bromobenzene more than for bromobenzene, is characterized in that, will how under catalyst action, to carry out halo shift reaction with benzene for bromobenzene and obtain bromobenzene; This process reaction equation is as follows; Described catalyzer is tin tetrachloride or titanium tetrachloride; Described benzene be how 1～10:1 for the mol ratio of bromobenzene; Described catalyzer usage quantity is many for 0.1～20% of bromobenzene weight; Described many be general formula for bromobenzene
the mixture of one or more in the multiple bromobenzene representing, the integer that wherein n is 2～5
2. method claimed in claim 1, is characterized in that: described many be the many for bromobenzene mixture of by-product in bromobenzene preparation process for bromobenzene.
3. method claimed in claim 1, is characterized in that: described halo shift reaction is carried out under the pressure of 0～1MPa.
4. method claimed in claim 1, is characterized in that: described halo shift reaction temperature is controlled between 50-150 DEG C.
5. method claimed in claim 1, is characterized in that: described halo shift reaction temperature is controlled between 80-120 DEG C.
6. method claimed in claim 1, is characterized in that: the described halo shift reaction time is 3-8hr.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201210492879.7A CN102992948B (en) | 2012-11-27 | 2012-11-27 | Method for preparing bromobenzene by recovering by-product multiple-substituted bromobenzene in bromobenzene synthesis |
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| CN201210492879.7A CN102992948B (en) | 2012-11-27 | 2012-11-27 | Method for preparing bromobenzene by recovering by-product multiple-substituted bromobenzene in bromobenzene synthesis |
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| CN102992948B true CN102992948B (en) | 2014-06-18 |
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| CN112194562A (en) * | 2020-09-03 | 2021-01-08 | 潍坊摩根化工有限公司 | Preparation method of bromobenzene |
| CN117886664A (en) * | 2024-03-12 | 2024-04-16 | 寿光市诚信盐业有限公司 | Method for preparing bromobenzene from poly-substituted bromobenzene mixture |
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Non-Patent Citations (1)
| Title |
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| 周福强等，.溴代苯合成工艺的改进.《海湖盐与化工》.1999,第28卷(第2期),第28-29页. * |
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