CN102675073A - Method for preparing 2, 4-dichloroacetophenone - Google Patents
Method for preparing 2, 4-dichloroacetophenone Download PDFInfo
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- CN102675073A CN102675073A CN2012101636528A CN201210163652A CN102675073A CN 102675073 A CN102675073 A CN 102675073A CN 2012101636528 A CN2012101636528 A CN 2012101636528A CN 201210163652 A CN201210163652 A CN 201210163652A CN 102675073 A CN102675073 A CN 102675073A
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- dichloroacetophenone
- acylating agent
- dichlorobenzene
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Abstract
The invention discloses a method for producing 2, 4-dichloroacetophenone. The method mainly includes acylation, hydrolysis, washing, distillation and crystallization, and m-dichlorobenzene and acetic anhydride are in acylation reaction under the effects of anhydrous aluminum trichloride. The method has the advantages that the m-dichlorobenzene is used as a raw material, the acetic anhydride is used as an acylating agent, A1C13 is used as a catalyst to prepare the 2, 4-dichloroacetophenone by means of reaction, and yield of obtained products is higher than that of products prepared by using acetyl chloride as an acylating agent; as the acetic anhydride is used as the acylating agent, the A1C13 is used as the catalyst and the m-dichlorobenzene which is extracted from chlorinated aromatics waste is comprehensively used as the raw material to prepare the 2, 4-dichloroacetophenone, by-products in a benzene chlorination process are disposed, reusing rate of chlorinated aromatics is increased, and the method has high economical and economical benefits.
Description
Technical field
Main task of the present invention is to provide a kind of working method of 2,4 dichloro benzene ethyl ketone, specifically is that a kind of chlorinated aromatics waste that utilizes is made the method that acylating agent is produced the 2,4 dichloro benzene ethyl ketone for the raw acetic acid acid anhydride.
Background technology
The 2,4 dichloro benzene ethyl ketone is preparation ω-bromo-2,4 dichloro benzene ethyl ketone or ω-2, the raw material of 4-Trichloroacetophenon, and both are midbodys that preparation presses down sterilant such as mould azoles, Wocosin 50TK, etaconazole for the backs, also are the midbodys of sterilant Zaprawa enolofos, weedicide difenzoquat.Meta Dichlorobenzene is a Synthetic 2, the main raw material of 4-dichloroacetophenone.My company is the enterprise of professional treatment chlorinated aromatics waste; The chlorinated aromatics waste is a common solid-liquid waste during petrochemical complex is produced, and contains wherein that a small amount of chlorobenzene, Meta Dichlorobenzene, santochlor, orthodichlorobenzene, trichlorobenzene and some are lowly boiled, high boiling material and other produces or residual various solid, liquid impurity in process of production in a large number.Contain Meta Dichlorobenzene about 15% in this waste, adopt rectifying separation and crystallization phases bonded mode that above-mentioned waste is handled, finally obtain the higher Meta Dichlorobenzene product of purity.In order to satisfy market to product demand, developed a kind of Meta Dichlorobenzene that utilizes and made the working method that acylating agent is produced the 2,4 dichloro benzene ethyl ketone for the raw acetic acid acid anhydride, also there is not to find relevant report at present.
Since between dichloro cost an arm and a leg, account for very big proportion aborning.Therefore improve technology and reduce consumption, improve yield, reduce cost, become the problem that each manufacturer presses for solution.Along with improving constantly of rapid development of national economy and living standards of the people, the consumption of domestic 2,4 dichloro benzene ethyl ketone will be increasing.
General Synthetic 2, the method for 4 one dichloroacetophenones are that a dichlorobenzene is a raw material between adopting, and use Acetyl Chloride 98Min. to obtain the thick product of 2,4 one dichloroacetophenones as acylating agent through Fridel-Crafts acylations, obtain more purified product through purifying again.Acyl chlorides has certain drawback as acylating agent, and the boiling point of Acetyl Chloride 98Min. is 51～52 ~ C, inflammable substance, and its steam and air can form mixture chance naked light, high heat energy causes combustion explosion; Decomposes discharges the phosgene and the HCl gas of severe toxicity; Meet water, water vapor or ethanol vigorous reaction even blast; Meet naked light meeting presence of fire, therefore, Acetyl Chloride 98Min. is made acylating agent has the harsh requirement of comparison in actually operating.According to bibliographical information, than high as acylating agent with Acetyl Chloride 98Min., yield can reach 85% to the employing diacetyl oxide as the acylating agent products therefrom.So we select to adopt Meta Dichlorobenzene and diacetyl oxide is raw material, adopting A1C13 is that catalyst reaction obtains title product.
Summary of the invention
The present invention solved is will separate the Meta Dichlorobenzene of purifying in the chlorinated aromatics waste through effectively improving raw material availability after handling at this operational path.Both protected environment, satisfied the part demand of market again, had high social and economic worth the 2,4 dichloro benzene ethyl ketone.
In order to solve above technical problem, the working method of a kind of 2,4 dichloro benzene ethyl ketone of the present invention; Mainly constitute by acidylate, hydrolysis, washing, distillation, crystallization five big steps; It is characterized in that: said acylation reaction is: Meta Dichlorobenzene carries out acylation reaction with diacetyl oxide under the effect of aluminum trichloride (anhydrous), during reaction, the diacetyl oxide dropping temperature remains on 45 ℃-55 ℃; Drip and finish to be warming up to 90 ~ 95 ℃ gradually, the about 3h of refluxing and stirring reaction.
The invention has the advantages that:
1, utilize Meta Dichlorobenzene to be raw material, the diacetyl oxide acid anhydride is an acylating agent, and adopting A1C13 is that catalyst reaction is produced the 2,4 dichloro benzene ethyl ketone, and products therefrom is than high as acylating agent with Acetyl Chloride 98Min.;
2, utilize Meta Dichlorobenzene to be raw material, the diacetyl oxide acid anhydride is an acylating agent, and adopting A1C13 is that catalyst reaction is produced the 2,4 dichloro benzene ethyl ketone, solved Acetyl Chloride 98Min. as the acylating agent production process because decomposes discharges the phosgene and the HCl gas of severe toxicity; Meet water, water vapor or ethanol vigorous reaction even blast; Meet the document of naked light meeting presence of fire, improved the essential safety degree; Safe operation process is controlled, and is workable;
3, the diacetyl oxide acid anhydride is an acylating agent, and employing A1C13 is a catalyzer, and adopting the Meta Dichlorobenzene that extracts in the comprehensive utilization chlorinated aromatics waste is raw material production 2; The 4-dichloroacetophenone; Not only solve the handling problems of by product in the benzene chlorination process, and improved the cyclic utilization rate of chlorinated aromatics, reduced productive expense; Realize the comprehensive utilization of useless resource admittedly, avoid environmental pollution; Simultaneously satisfied the part demand of market again, had high social and economic worth the 2,4 dichloro benzene ethyl ketone.
Embodiment
In reaction kettle, add the 1.0mol Meta Dichlorobenzene, add the 1.3mol aluminum trichloride (anhydrous), stir and slowly drip the 1.0mol diacetyl oxide down; The temperature of reaction solution remains on 45 ℃-55 ℃ during dropping, drips the speed that finishes by 1 ℃/minute and is warming up to 90 ~ 95 ℃, the about 3h of refluxing and stirring reaction; After reaction finishes, in reaction solution, add 10% hydrochloric acid 200ml, place the cooling layering in 80 ℃ of following hydrolysis; Tell organic layer, be added drop-wise in the washing still that 200ml water is housed in 50 ℃ of washings, product is 120-140 ℃ of following underpressure distillation behind the standing demix; Collect 135 ℃ of front-end volatiles, it is that the above white crystals of 99 % is the 2,4 dichloro benzene ethyl ketone that crystallisation by cooling obtains purity.
Claims (1)
1. one kind 2; The working method of 4-dichloroacetophenone mainly is made up of acidylate, hydrolysis, washing, distillation, crystallization five big steps, and it is characterized in that: said acylation reaction is: Meta Dichlorobenzene carries out acylation reaction with diacetyl oxide under the effect of aluminum trichloride (anhydrous); During reaction; The diacetyl oxide dropping temperature remains on 45 ℃-55 ℃, drips to finish to be warming up to 90 ~ 95 ℃ gradually the about 3h of refluxing and stirring reaction.
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| Application Number | Priority Date | Filing Date | Title |
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| CN2012101636528A CN102675073A (en) | 2012-05-24 | 2012-05-24 | Method for preparing 2, 4-dichloroacetophenone |
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| CN2012101636528A CN102675073A (en) | 2012-05-24 | 2012-05-24 | Method for preparing 2, 4-dichloroacetophenone |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107141203A (en) * | 2017-06-28 | 2017-09-08 | 江苏隆昌化工有限公司 | A kind of recycling processing method of the rich meta of mixed dichlorobenzene separation by-product |
| CN108911995A (en) * | 2018-07-20 | 2018-11-30 | 上海化工研究院有限公司 | A kind of stable isotope labeling R- Clorprenaline and preparation method thereof |
| CN109180418A (en) * | 2018-10-09 | 2019-01-11 | 江苏扬农化工集团有限公司 | A kind of propylene oxide co-production object resource utilization synthetic pesticide intermediate 2,4 dichloro benzene ethyl ketone method |
| CN109251137A (en) * | 2018-09-14 | 2019-01-22 | 新昌县泰如科技有限公司 | The synthetic method of one kind 2,4- dichloroacetophenone |
| CN109384657A (en) * | 2018-12-18 | 2019-02-26 | 苏州开元民生科技股份有限公司 | A kind of parahydroxyacet-ophenone synthetic method |
| CN109721480A (en) * | 2018-11-14 | 2019-05-07 | 新昌县泰如科技有限公司 | The synthetic method of one kind 2,4- dichloroacetophenone |
| CN110922322A (en) * | 2019-11-01 | 2020-03-27 | 江苏隆昌化工有限公司 | Clean production method for improving reaction yield of 2, 4-dichloroacetophenone |
| CN111253233A (en) * | 2020-03-17 | 2020-06-09 | 浙江禾本科技股份有限公司 | Transposition method of acetophenone isomer |
| CN113429279A (en) * | 2021-06-09 | 2021-09-24 | 江苏瑞恒新材料科技有限公司 | Resource utilization method of 2, 4-dichloroacetophenone wastewater |
| CN113620797A (en) * | 2021-08-09 | 2021-11-09 | 宁夏瑞泰科技股份有限公司 | Method for preparing 2, 4-dichloroacetophenone |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101898947A (en) * | 2010-08-19 | 2010-12-01 | 江苏隆昌化工有限公司 | Method for producing 2,4-dichloroacetophenone by using solid waste chlorobenzene tar as raw material |
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2012
- 2012-05-24 CN CN2012101636528A patent/CN102675073A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101898947A (en) * | 2010-08-19 | 2010-12-01 | 江苏隆昌化工有限公司 | Method for producing 2,4-dichloroacetophenone by using solid waste chlorobenzene tar as raw material |
Non-Patent Citations (1)
| Title |
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| 王雅珍等: "2,4-二氯苯乙酮合成工艺的研究", 《化学工程师》, no. 11, 2008, pages 53 - 55 * |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107141203A (en) * | 2017-06-28 | 2017-09-08 | 江苏隆昌化工有限公司 | A kind of recycling processing method of the rich meta of mixed dichlorobenzene separation by-product |
| CN108911995A (en) * | 2018-07-20 | 2018-11-30 | 上海化工研究院有限公司 | A kind of stable isotope labeling R- Clorprenaline and preparation method thereof |
| CN109251137A (en) * | 2018-09-14 | 2019-01-22 | 新昌县泰如科技有限公司 | The synthetic method of one kind 2,4- dichloroacetophenone |
| CN109180418B (en) * | 2018-10-09 | 2021-03-30 | 江苏扬农化工集团有限公司 | Method for synthesizing pesticide intermediate 2, 4-dichloroacetophenone by recycling propylene oxide co-product materials |
| CN109180418A (en) * | 2018-10-09 | 2019-01-11 | 江苏扬农化工集团有限公司 | A kind of propylene oxide co-production object resource utilization synthetic pesticide intermediate 2,4 dichloro benzene ethyl ketone method |
| CN109721480A (en) * | 2018-11-14 | 2019-05-07 | 新昌县泰如科技有限公司 | The synthetic method of one kind 2,4- dichloroacetophenone |
| CN109384657B (en) * | 2018-12-18 | 2021-08-31 | 苏州开元民生科技股份有限公司 | Synthetic method of p-hydroxyacetophenone |
| CN109384657A (en) * | 2018-12-18 | 2019-02-26 | 苏州开元民生科技股份有限公司 | A kind of parahydroxyacet-ophenone synthetic method |
| CN110922322A (en) * | 2019-11-01 | 2020-03-27 | 江苏隆昌化工有限公司 | Clean production method for improving reaction yield of 2, 4-dichloroacetophenone |
| CN111253233A (en) * | 2020-03-17 | 2020-06-09 | 浙江禾本科技股份有限公司 | Transposition method of acetophenone isomer |
| CN111253233B (en) * | 2020-03-17 | 2023-02-28 | 浙江禾本科技股份有限公司 | Transposition method of acetophenone isomer |
| CN113429279A (en) * | 2021-06-09 | 2021-09-24 | 江苏瑞恒新材料科技有限公司 | Resource utilization method of 2, 4-dichloroacetophenone wastewater |
| CN113429279B (en) * | 2021-06-09 | 2022-04-19 | 江苏瑞恒新材料科技有限公司 | Resource utilization method of 2, 4-dichloroacetophenone wastewater |
| CN113620797A (en) * | 2021-08-09 | 2021-11-09 | 宁夏瑞泰科技股份有限公司 | Method for preparing 2, 4-dichloroacetophenone |
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Application publication date: 20120919 |