CN111792987A - Synthetic method for preparing 3, 5-dichloro-2-pentanone from methyl acetoacetate - Google Patents
Synthetic method for preparing 3, 5-dichloro-2-pentanone from methyl acetoacetate Download PDFInfo
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- CN111792987A CN111792987A CN202010695070.9A CN202010695070A CN111792987A CN 111792987 A CN111792987 A CN 111792987A CN 202010695070 A CN202010695070 A CN 202010695070A CN 111792987 A CN111792987 A CN 111792987A
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- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
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- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
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Abstract
The invention discloses a synthetic method for preparing 3, 5-dichloro-2-pentanone from methyl acetoacetate, which comprises the following steps: s1: preparation of a reactor: preparing two reactors, namely a first reactor and a second reactor; s2: cleaning a reactor: placing the first reactor and the second reactor in clean water for cleaning, washing the first reactor and the second reactor after cleaning, and drying the first reactor and the second reactor after washing; s3: hydrolysis to form salt: adding methyl acetoacetate into the first reactor, dropwise adding 30% liquid caustic soda under cooling of circulating water, and continuously reacting for 6h after dropwise adding is finished to obtain a hydrolyzed material. The synthetic method for preparing 3, 5-dichloro-2-pentanone from methyl acetoacetate has strict working steps, avoids using flammable and explosive materials, improves safety, reduces reaction operation, improves reaction efficiency and effectively reduces cost.
Description
Technical Field
The invention relates to the technical field of synthesis, and particularly relates to a synthesis method for preparing 3, 5-dichloro-2-pentanone from methyl acetoacetate.
Background
3, 5-dichloro-2-pentanone is an important intermediate for synthesizing various pesticides and medicines (prothioconazole, clomeprazole and the like).
In the existing 3, 5-dichloro-2-pentanone synthesis route, ethylene oxide is used as a starting raw material, and the route is flammable and explosive and is not easy to transport for a long distance, so that the route has strong regional limitation; the gamma-butyrolactone and ethyl acetate are used for replacing the route, although ethylene oxide is avoided, the route needs to use catalyst metal sodium, and sodium has strong reducibility and can react with water violently to cause hydrogen to burn and even explode, so that the industrial large-scale use has great potential safety hazard; in addition, in the above route, a plurality of solvents are used in some steps, the solvent recovery is complex, the cost is high, the yield of some steps is low, the post-reaction treatment is complex, and the method is obviously not suitable for industrial production.
Disclosure of Invention
Based on the technical problems of strict working steps, use of flammable and explosive materials, poor safety, reduction of reaction efficiency and increase of cost in the background technology, the invention provides a synthetic method for preparing 3, 5-dichloro-2-pentanone from methyl acetoacetate.
The invention provides a synthetic method for preparing 3, 5-dichloro-2-pentanone from methyl acetoacetate, which comprises the following steps:
s1: preparation of a reactor: preparing two reactors, namely a first reactor and a second reactor;
s2: cleaning a reactor: placing the first reactor and the second reactor in clean water for cleaning, washing the first reactor and the second reactor after cleaning, and drying the first reactor and the second reactor after washing;
s3: hydrolysis to form salt: adding methyl acetoacetate into the first reactor, dropwise adding 30% liquid caustic soda under cooling of circulating water, and continuously reacting for 6h after dropwise adding is finished to obtain a hydrolyzed material;
s4: 1, 2-dichloroethane alkylation reaction: adding 1, 2-dichloroethane, dimethyl sulfoxide and tetrabutylammonium bromide into the hydrolysate in the first reactor, heating to reflux reaction, monitoring the reaction degree by adopting a high performance liquid chromatography, decompressing and concentrating to remove a dimethyl sulfoxide solvent and excessive dichloroethane after the reaction is completed, washing the liquid, and directly putting a lower-layer organic phase into a second reactor;
s5: chlorine chlorination and decarboxylation: cooling the second reactor, introducing chlorine gas, controlling the reaction temperature at 20-30 deg.C, monitoring the reaction degree by high performance liquid chromatography, adding water for azeotropic distillation after the reaction is finished, distilling off the light yellow organic phase and the water phase fraction, standing for layering, and separating out the lower light yellow organic phase to obtain 3, 5-dichloro-2-pentanone.
Preferably, in S1, the specifications of the first reactor and the second reactor are the same.
Preferably, in S2, the first reactor and the second reactor are flushed with distilled water after the completion of the flushing.
Preferably, in the S3, the hydrolysis temperature of the methyl acetoacetate is 25-35 ℃, and the temperature of the heat preservation reaction is 25-35 ℃.
Preferably, in S4, the alkylation reaction temperature is reflux temperature, and the reflux temperature is 75-85 ℃.
Preferably, in the S5, the chlorination and decarboxylation reaction temperature of the chlorine is 4-6 ℃, and the reaction temperature is 5-10 ℃.
Preferably, the molar ratio of the methyl acetoacetate to the liquid alkali, the 1, 2-dichloroethane and the chlorine gas is 1: (2-2.5): (5-20):1.
Preferably, the molar ratio of tetrabutylammonium bromide to methyl acetoacetate is 1: 20-25.
The invention has the advantages that methyl acetoacetate, 1, 2-dichloroethane, dimethyl sulfoxide, tetrabutyl ammonium bromide and the like are adopted as raw materials, flammable and explosive materials are avoided, and the safety is improved;
the process steps are strict, the operation is simple and convenient, and 3, 5-dichloro-2-pentanone with the content as high as 99% can be obtained on the lower layer;
tetrabutylammonium bromide is used as a catalyst, so that the reaction yield is improved, wherein 1, 2-dichloroethane chloroalkylation reaction is carried out, and sodium hydroxide is used as alkali, so that the effect is good, and the tetrabutylammonium bromide is low in price and easy to obtain; the chlorination reaction and the decarboxylation reaction are simultaneously carried out, so that the reaction operation is reduced, the reaction efficiency is improved, and the cost is effectively reduced.
The synthetic method for preparing 3, 5-dichloro-2-pentanone from methyl acetoacetate has strict working steps, avoids using flammable and explosive materials, improves safety, reduces reaction operation, improves reaction efficiency and effectively reduces cost.
Detailed Description
The present invention will be further illustrated with reference to the following specific examples.
Example one
The embodiment provides a synthetic method for preparing 3, 5-dichloro-2-pentanone from methyl acetoacetate, which comprises the following steps:
s1: preparation of a reactor: preparing two reactors, namely a first reactor and a second reactor;
s2: cleaning a reactor: placing the first reactor and the second reactor in clean water for cleaning, washing the first reactor and the second reactor after cleaning, and drying the first reactor and the second reactor after washing;
s3: hydrolysis to form salt: adding methyl acetoacetate into the first reactor, dropwise adding 30% liquid caustic soda under cooling of circulating water, and continuously reacting for 6h after dropwise adding is finished to obtain a hydrolyzed material;
s4: 1, 2-dichloroethane alkylation reaction: adding 1, 2-dichloroethane, dimethyl sulfoxide and tetrabutylammonium bromide into the hydrolysate in the first reactor, heating to reflux reaction, monitoring the reaction degree by adopting a high performance liquid chromatography, decompressing and concentrating to remove a dimethyl sulfoxide solvent and excessive dichloroethane after the reaction is completed, washing the liquid, and directly putting a lower-layer organic phase into a second reactor;
s5: chlorine chlorination and decarboxylation: cooling the second reactor, introducing chlorine gas, controlling the reaction temperature at 20 ℃, monitoring the reaction degree by adopting a high performance liquid chromatography, adding water for azeotropic distillation after the reaction is finished, distilling a light yellow organic phase and a water phase fraction, standing for layering, and separating a lower light yellow organic phase to obtain the 3, 5-dichloro-2-pentanone.
In this embodiment, in S1, specifications of the first reactor and the second reactor are the same, in S2, the first reactor and the second reactor are washed with distilled water after cleaning, in S3, the hydrolysis temperature of methyl acetoacetate is 25 ℃, the incubation temperature is 25 ℃, in S4, the alkylation temperature is reflux temperature, the reflux temperature is 75 ℃, in S5, the chlorination and decarboxylation reaction temperature of chlorine is 4 ℃, the reaction temperature is 5 ℃, and the molar ratio of methyl acetoacetate to liquid alkali, 1, 2-dichloroethane, and chlorine is 1: 2: 5:1, the molar ratio of tetrabutylammonium bromide to methyl acetoacetate is 1: 20.
example two
The embodiment provides a synthetic method for preparing 3, 5-dichloro-2-pentanone from methyl acetoacetate, which comprises the following steps:
s1: preparation of a reactor: preparing two reactors, namely a first reactor and a second reactor;
s2: cleaning a reactor: placing the first reactor and the second reactor in clean water for cleaning, washing the first reactor and the second reactor after cleaning, and drying the first reactor and the second reactor after washing;
s3: hydrolysis to form salt: adding methyl acetoacetate into the first reactor, dropwise adding 30% liquid caustic soda under cooling of circulating water, and continuously reacting for 6h after dropwise adding is finished to obtain a hydrolyzed material;
s4: 1, 2-dichloroethane alkylation reaction: adding 1, 2-dichloroethane, dimethyl sulfoxide and tetrabutylammonium bromide into the hydrolysate in the first reactor, heating to reflux reaction, monitoring the reaction degree by adopting a high performance liquid chromatography, decompressing and concentrating to remove a dimethyl sulfoxide solvent and excessive dichloroethane after the reaction is completed, washing the liquid, and directly putting a lower-layer organic phase into a second reactor;
s5: chlorine chlorination and decarboxylation: cooling the second reactor, introducing chlorine gas, controlling the reaction temperature at 22 ℃, monitoring the reaction degree by adopting a high performance liquid chromatography, adding water for azeotropic distillation after the reaction is finished, distilling a light yellow organic phase and a water phase fraction, standing for layering, and separating a lower light yellow organic phase to obtain the 3, 5-dichloro-2-pentanone.
In this example, in S1, specifications of the first reactor and the second reactor are the same, in S2, the first reactor and the second reactor are washed with distilled water after cleaning, in S3, the hydrolysis temperature of methyl acetoacetate is 27 ℃, the incubation temperature is 27 ℃, in S4, the alkylation temperature is reflux temperature, the reflux temperature is 77 ℃, in S5, the chlorination and decarboxylation reaction temperature of chlorine is 4 ℃, the reaction temperature is 6 ℃, and the molar ratio of methyl acetoacetate to liquid alkali, 1, 2-dichloroethane, and chlorine is 1: 2.1: 7:1, the molar ratio of tetrabutylammonium bromide to methyl acetoacetate is 1: 21.
EXAMPLE III
The embodiment provides a synthetic method for preparing 3, 5-dichloro-2-pentanone from methyl acetoacetate, which comprises the following steps:
s1: preparation of a reactor: preparing two reactors, namely a first reactor and a second reactor;
s2: cleaning a reactor: placing the first reactor and the second reactor in clean water for cleaning, washing the first reactor and the second reactor after cleaning, and drying the first reactor and the second reactor after washing;
s3: hydrolysis to form salt: adding methyl acetoacetate into the first reactor, dropwise adding 30% liquid caustic soda under cooling of circulating water, and continuously reacting for 6h after dropwise adding is finished to obtain a hydrolyzed material;
s4: 1, 2-dichloroethane alkylation reaction: adding 1, 2-dichloroethane, dimethyl sulfoxide and tetrabutylammonium bromide into the hydrolysate in the first reactor, heating to reflux reaction, monitoring the reaction degree by adopting a high performance liquid chromatography, decompressing and concentrating to remove a dimethyl sulfoxide solvent and excessive dichloroethane after the reaction is completed, washing the liquid, and directly putting a lower-layer organic phase into a second reactor;
s5: chlorine chlorination and decarboxylation: cooling the second reactor, introducing chlorine gas, controlling the reaction temperature at 25 ℃, monitoring the reaction degree by adopting a high performance liquid chromatography, adding water for azeotropic distillation after the reaction is finished, distilling a light yellow organic phase and a water phase fraction, standing for layering, and separating a lower light yellow organic phase to obtain the 3, 5-dichloro-2-pentanone.
In this embodiment, in S1, specifications of the first reactor and the second reactor are the same, in S2, the first reactor and the second reactor are washed with distilled water after cleaning, in S3, the hydrolysis temperature of methyl acetoacetate is 30 ℃, the incubation temperature is 30 ℃, in S4, the alkylation temperature is reflux temperature, the reflux temperature is 80 ℃, in S5, the chlorination and decarboxylation reaction temperature of chlorine is 5 ℃, the reaction temperature is 7 ℃, and the molar ratio of methyl acetoacetate to liquid alkali, 1, 2-dichloroethane, and chlorine is 1: 2.3: 12:1, the molar ratio of tetrabutylammonium bromide to methyl acetoacetate is 1: 23.
example four
The embodiment provides a synthetic method for preparing 3, 5-dichloro-2-pentanone from methyl acetoacetate, which comprises the following steps:
s1: preparation of a reactor: preparing two reactors, namely a first reactor and a second reactor;
s2: cleaning a reactor: placing the first reactor and the second reactor in clean water for cleaning, washing the first reactor and the second reactor after cleaning, and drying the first reactor and the second reactor after washing;
s3: hydrolysis to form salt: adding methyl acetoacetate into the first reactor, dropwise adding 30% liquid caustic soda under cooling of circulating water, and continuously reacting for 6h after dropwise adding is finished to obtain a hydrolyzed material;
s4: 1, 2-dichloroethane alkylation reaction: adding 1, 2-dichloroethane, dimethyl sulfoxide and tetrabutylammonium bromide into the hydrolysate in the first reactor, heating to reflux reaction, monitoring the reaction degree by adopting a high performance liquid chromatography, decompressing and concentrating to remove a dimethyl sulfoxide solvent and excessive dichloroethane after the reaction is completed, washing the liquid, and directly putting a lower-layer organic phase into a second reactor;
s5: chlorine chlorination and decarboxylation: cooling the second reactor, introducing chlorine gas, controlling the reaction temperature at 28 ℃, monitoring the reaction degree by adopting a high performance liquid chromatography, adding water for azeotropic distillation after the reaction is finished, distilling a light yellow organic phase and a water phase fraction, standing for layering, and separating a lower light yellow organic phase to obtain the 3, 5-dichloro-2-pentanone.
In this embodiment, in S1, specifications of the first reactor and the second reactor are the same, in S2, the first reactor and the second reactor are washed with distilled water after cleaning, in S3, the hydrolysis temperature of methyl acetoacetate is 33 ℃, the incubation temperature is 33 ℃, in S4, the alkylation temperature is reflux temperature, the reflux temperature is 83 ℃, in S5, the chlorination and decarboxylation reaction temperature of chlorine is 5 ℃, the reaction temperature is 9 ℃, and the molar ratio of methyl acetoacetate to liquid alkali, 1, 2-dichloroethane, and chlorine is 1: 2.4: 18:1, the molar ratio of tetrabutylammonium bromide to methyl acetoacetate is 1: 24.
EXAMPLE five
The embodiment provides a synthetic method for preparing 3, 5-dichloro-2-pentanone from methyl acetoacetate, which comprises the following steps:
s1: preparation of a reactor: preparing two reactors, namely a first reactor and a second reactor;
s2: cleaning a reactor: placing the first reactor and the second reactor in clean water for cleaning, washing the first reactor and the second reactor after cleaning, and drying the first reactor and the second reactor after washing;
s3: hydrolysis to form salt: adding methyl acetoacetate into the first reactor, dropwise adding 30% liquid caustic soda under cooling of circulating water, and continuously reacting for 6h after dropwise adding is finished to obtain a hydrolyzed material;
s4: 1, 2-dichloroethane alkylation reaction: adding 1, 2-dichloroethane, dimethyl sulfoxide and tetrabutylammonium bromide into the hydrolysate in the first reactor, heating to reflux reaction, monitoring the reaction degree by adopting a high performance liquid chromatography, decompressing and concentrating to remove a dimethyl sulfoxide solvent and excessive dichloroethane after the reaction is completed, washing the liquid, and directly putting a lower-layer organic phase into a second reactor;
s5: chlorine chlorination and decarboxylation: cooling the second reactor, introducing chlorine gas, controlling the reaction temperature at 30 ℃, monitoring the reaction degree by adopting a high performance liquid chromatography, adding water for azeotropic distillation after the reaction is finished, distilling a light yellow organic phase and a water phase fraction, standing for layering, and separating a lower light yellow organic phase to obtain the 3, 5-dichloro-2-pentanone.
In this embodiment, in S1, specifications of the first reactor and the second reactor are the same, in S2, the first reactor and the second reactor are washed with distilled water after cleaning, in S3, the hydrolysis temperature of methyl acetoacetate is 35 ℃, the incubation temperature is 35 ℃, in S4, the alkylation temperature is reflux temperature, the reflux temperature is 85 ℃, in S5, the chlorination and decarboxylation reaction temperature of chlorine is 6 ℃, the reaction temperature is 10 ℃, and the molar ratio of methyl acetoacetate to liquid alkali, 1, 2-dichloroethane, and chlorine is 1: 2.5: 20:1, the molar ratio of tetrabutylammonium bromide to methyl acetoacetate being 1: 25.
study on the synthesis of 3, 5-dichloro-2-pentanone:
the synthesis was carried out using 3, 5-dichloro-2-pentanone, respectively, using examples one to five, the yields and contents being recorded:
| examples | Yield of | Content (wt.) |
| Example one | 98％ | 91％ |
| Example two | 97％ | 92％ |
| EXAMPLE III | 99％ | 93％ |
| Example four | 98％ | 92％ |
| EXAMPLE five | 98％ | 91％ |
The result shows that the yield and the content of the 3, 5-dichloro-2-pentanone are greatly improved in the third embodiment.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.
Claims (8)
1. A synthetic method for preparing 3, 5-dichloro-2-pentanone from methyl acetoacetate is characterized by comprising the following steps:
s1: preparation of a reactor: preparing two reactors, namely a first reactor and a second reactor;
s2: cleaning a reactor: placing the first reactor and the second reactor in clean water for cleaning, washing the first reactor and the second reactor after cleaning, and drying the first reactor and the second reactor after washing;
s3: hydrolysis to form salt: adding methyl acetoacetate into the first reactor, dropwise adding 30% liquid caustic soda under cooling of circulating water, and continuously reacting for 6h after dropwise adding is finished to obtain a hydrolyzed material;
s4: 1, 2-dichloroethane alkylation reaction: adding 1, 2-dichloroethane, dimethyl sulfoxide and tetrabutylammonium bromide into the hydrolysate in the first reactor, heating to reflux reaction, monitoring the reaction degree by adopting a high performance liquid chromatography, decompressing and concentrating to remove a dimethyl sulfoxide solvent and excessive dichloroethane after the reaction is completed, washing the liquid, and directly putting a lower-layer organic phase into a second reactor;
s5: chlorine chlorination and decarboxylation: cooling the second reactor, introducing chlorine gas, controlling the reaction temperature at 20-30 deg.C, monitoring the reaction degree by high performance liquid chromatography, adding water for azeotropic distillation after the reaction is finished, distilling off the light yellow organic phase and the water phase fraction, standing for layering, and separating out the lower light yellow organic phase to obtain 3, 5-dichloro-2-pentanone.
2. The synthesis method for preparing 3, 5-dichloro-2-pentanone from methyl acetoacetate according to claim 1, wherein in S1, the specifications of the first reactor and the second reactor are the same.
3. The method as claimed in claim 1, wherein the first reactor and the second reactor are flushed with distilled water after the cleaning step in S2.
4. The synthesis method for preparing 3, 5-dichloro-2-pentanone from methyl acetoacetate according to claim 1, wherein in S3, the hydrolysis temperature of methyl acetoacetate is 25-35 ℃, and the temperature for the heat preservation reaction is 25-35 ℃.
5. The synthesis method for preparing 3, 5-dichloro-2-pentanone from methyl acetoacetate according to claim 1, wherein in S4, the alkylation reaction temperature is reflux temperature, and the reflux temperature is 75-85 ℃.
6. The synthesis method for preparing 3, 5-dichloro-2-pentanone from methyl acetoacetate according to claim 1, characterized in that the chlorination and decarboxylation reaction temperature of chlorine in S5 is 4-6 ℃ and the reaction temperature is 5-10 ℃.
7. The synthesis method for preparing 3, 5-dichloro-2-pentanone from methyl acetoacetate according to claim 1, characterized in that the molar ratio of methyl acetoacetate to liquid alkali, 1, 2-dichloroethane and chlorine is 1: (2-2.5): (5-20):1.
8. The synthesis method for preparing 3, 5-dichloro-2-pentanone from methyl acetoacetate according to claim 1, wherein the molar ratio of tetrabutylammonium bromide to methyl acetoacetate is 1: 20-25.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103709023A (en) * | 2013-12-24 | 2014-04-09 | 秦永其 | Synthesis method for 3,5-dichloro-2-pentanone |
| CN105461533A (en) * | 2015-11-24 | 2016-04-06 | 大连世慕化学有限公司 | Synthetic method of 3, 5-dichloro-2-pentanone |
| CN111205176A (en) * | 2020-01-14 | 2020-05-29 | 大连九信精细化工有限公司 | Synthetic method of 3, 5-dihalogen-2-pentanone |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103709023A (en) * | 2013-12-24 | 2014-04-09 | 秦永其 | Synthesis method for 3,5-dichloro-2-pentanone |
| CN105461533A (en) * | 2015-11-24 | 2016-04-06 | 大连世慕化学有限公司 | Synthetic method of 3, 5-dichloro-2-pentanone |
| CN111205176A (en) * | 2020-01-14 | 2020-05-29 | 大连九信精细化工有限公司 | Synthetic method of 3, 5-dihalogen-2-pentanone |
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Application publication date: 20201020 |