Synthesis method of 2,2,2',4',5'-pentachloroacetophenone

A technology of pentachloroacetophenone and synthetic methods, applied in two fields, can solve problems such as high usage of Lewis acid catalysts, excessive reaction residues, low product purity, etc., to avoid reaction rate, reaction degree, reaction The effect of thoroughness and purity improvement

Pending Publication Date: 2021-07-16

JIANGXI YONGTONG TECH

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Problems solved by technology

[0003] In the prior art, the synthesis of 2,2,2',4',5'-pentachloroacetophenone is mostly based on the catalysis of dichloroacetyl chloride and 1,2,4-trichlorobenzene in Lewis acid aluminum chloride The acetylation reaction is carried out under the following conditions, and the yield is generally about 80% when the yield is good. The disadvantages of this method are inevitable, such as the yield needs t...

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Abstract

The invention provides a synthesis method of 2,2,2',4',5'-pentachloroacetophenone. Raw materials comprise, by weight, 52-75 parts of 1,2,4-trichlorobenzene, 40-62 parts of dichloroacetyl chloride, 32-58 parts of a catalyst and 28-50 parts of water. A conventional temperature curve is broken, temperature change is utilized, and the catalyst is added at different time periods according to the proportion, so that the utilization rate of the catalyst is effectively improved, and the reaction degree is promoted to be more thorough; meanwhile, the catalyst adopts a carrier medium-Lewis acid compound, the carrier medium is prepared by utilizing the activity of microorganisms, and the catalyst is supported on a porous carrier, so that the activity of the catalyst is increased, the yield and the purity are improved, and the reaction rate and the reaction degree are prevented from being slowed down due to catalyst deposition in the reaction process; in addition, after the reaction is finished, an organic layer is washed and filtered by a high-efficiency filter membrane to further remove impurities, so that the purity of the product is effectively improved.

Application Domain

Organic compound preparationCarbonyl compound preparation by condensation +1

Technology Topic

Ptru catalystReaction rate +11

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Examples

Experimental program(15)
Effect test(1)

Example Embodiment

[0022] Example 1

[0023] A method for synthesizing 2,2,2',4',5'-pentachloroacetophenone. The raw materials include 63 parts of 1,2,4 trichlorobenzene, 51 parts of dichloroacetyl chloride, and 45 parts of catalyst in parts by weight. parts, 39 parts of water; the specific method is:

[0024] (1) Put the above-mentioned 1,2,4-trichlorobenzene and 30% of the above-mentioned catalyst by weight in a reaction tank and stir and mix at a stirring rate of 140rpm, keep the temperature at 50°C for 45min, and then add 60% of the catalyst dropwise in 55min For the above weight part of dichloroacetyl chloride, keep the stirring speed constant, add 40% of the above weight part of the catalyst, dropwise add the remaining weight part of dichloroacetyl chloride within 35min, raise the temperature to 70°C, keep the temperature for 1.5h, and then add the remaining weight part catalyst, heat up to 90°C, adjust the stirring speed to 380rpm, and raise the pressure of the reaction tank to 6.5×10 5 Pa, keep the reaction for 6.5h;

[0025] (2) After the reaction is over, release the pressure to normal pressure, slowly add carbon disulfide solvent into the reaction tank while it is hot until it is stirred and dissolved, pour it into water and stir evenly, let it cool to room temperature, separate the oil layer, extract the water layer with solvent, and into the organic layer, washed and filtered with a high-efficiency filter, dried, and distilled under reduced pressure to collect fractions at 150°C/0.025 MPa to obtain white crystals of 2,2,2',4',5'-pentachloroacetophenone.

[0026] The catalyst is a carrier medium-Lewis acid complex, and its preparation method is as follows: Weigh 5 parts of a mixture of aluminum chloride and zinc chloride with a mass ratio of 1.5:1 by weight, and dissolve it in 9 parts by volume under a 350w ultrasonic environment. Add 4 parts of carrier medium to a 1:1 mixed solution of anhydrous methanol and anhydrous ethanol, stir at room temperature for 2.5 minutes at a stirring speed of 160m, distill off the solvent under reduced pressure, activate at 115°C for 6h, and obtain it, store it Store in a desiccator for later use.

[0027] The carrier medium is a modified porous mixture with a porosity of 72. The materials used and the preparation method are as follows: Weigh kaolin 22, bentonite 18, and zeolite molecular sieve 14 by weight and mix them into a muffle furnace for activation and sterilization. 400 Activate at ℃ for 45in, cool naturally to room temperature and pass through a 50-mesh sieve to obtain mixed coarse powder; put the mixed coarse powder in the microbial culture solution with a solid-to-liquid ratio of 1:4.5, inoculate microbial cells at 32°C for 18 days, filter , the filter residue was washed 4 times with absolute ethanol, and baked at 58°C until constant weight, wherein the microorganisms were of the genus Bacillus;

[0028] The high-efficiency filter membrane includes a filter membrane main body and an impurity adsorption layer, and the material of the filter membrane main body is ceramic; the impurity adsorption layer evenly covers the surface of the filter membrane main body;

[0029] The preparation method of the impurity adsorption layer is as follows: select air-dried corn stalks, place them in a tubular carbonization furnace, pass in argon as a protective gas, increase the temperature to 500°C at a rate of 13°C/min, keep the temperature constant for 1.5h, and naturally Cool to normal temperature, ball mill, and sieve with a 400-mesh sieve to obtain corn stalk activated carbon, mix corn stalk activated carbon and microbial culture at a mass ratio of 1:2.5, ultrasonically stir for 1.5h, let stand for 18h, filter and Collect the solid, wash the solid with ethanol until neutral, dry it, then mix it with polybutylene succinate, citric acid monohydrate, and polyurethane in a mass ratio of 1:33:0.4:0.3, and heat up to Stir and disperse at 35°C and 600r/min for 2 hours to obtain the impurity adsorption layer dispersion, and then immerse the main body of the filter membrane in the impurity adsorption layer dispersion by immersion for a residence time of 9 seconds, then take it out and dry it in the air;

[0030]The preparation of the microbial culture is as follows: Azotobacter terescens, Bacillus megaterium, and Bacillus colloidus with a mass ratio of 1:2:3.5 are used as microbial clusters, placed in a constant temperature oscillator, and added with a mass ratio of 1 : 3.5 metal salt mixture of potassium salt and sodium salt, in which the mass ratio of microbial clusters to metal salt mixture is 1:3, cultured at a constant temperature for 60 hours at a temperature of 45°C, washed and filtered 4 times, and the filter residue is the microorganism Cultures.

Example Embodiment

[0031] Example 2

[0032] A method for synthesizing 2,2,2',4',5'-pentachloroacetophenone. The raw materials include 52 parts of 1,2,4 trichlorobenzene, 40 parts of dichloroacetyl chloride, and 58 parts of catalyst in parts by weight. part, 50 parts of water; the specific method is:

[0033] (1) Put the above-mentioned 1,2,4-trichlorobenzene and 30% of the above-mentioned catalyst by weight in a reaction tank and stir and mix at a stirring rate of 80 rpm, keep the temperature at 40°C for 55 minutes, and then add 60% of the catalyst dropwise within 60 minutes For the above weight part of dichloroacetyl chloride, keep the stirring rate constant, add 40% of the above weight part of the catalyst, dropwise add the remaining weight part of dichloroacetyl chloride within 30min, raise the temperature to 65°C, keep the temperature for 2h, and then add the remaining weight part catalyst, the temperature was raised to 95°C, the stirring speed was adjusted to 300rpm, and the pressure of the reaction tank was raised to 5.5×10 5 Pa, keep the reaction for 5h;

[0034] (2) After the reaction is over, release the pressure to normal pressure, slowly add carbon disulfide solvent into the reaction tank while it is hot until it is stirred and dissolved, pour it into water and stir evenly, let it cool to room temperature, separate the oil layer, extract the water layer with solvent, and into the organic layer, washed and filtered with a high-efficiency filter, dried, and distilled under reduced pressure to collect fractions at 135°C/0.025 MPa to obtain white crystals of 2,2,2',4',5'-pentachloroacetophenone.

[0035] The catalyst is a carrier medium-Lewis acid complex, and its preparation method is as follows: Weigh 3 parts of a mixture of aluminum chloride and zinc chloride with a mass ratio of 1:1 by weight, and dissolve it in 8 parts by volume under a 200w ultrasonic environment Add 2 parts of carrier medium to a 1:2 mixed solution of anhydrous methanol and anhydrous ethanol, stir at room temperature for 2 hours at a stirring rate of 120 rpm, distill off the solvent under reduced pressure, and activate at 100°C for 4 hours to obtain, Store in a desiccator for later use.

[0036] The carrier medium is a modified porous mixture with a porosity of 85%. The materials used and the preparation method are as follows: 30 parts by weight of kaolin, 25 parts of bentonite, and 18 parts of zeolite molecular sieve are mixed and put into a muffle furnace for activation and deactivation. Bacteria treatment, activated at 500°C for 60 minutes, naturally cooled to room temperature and passed through a 50-mesh sieve to obtain mixed coarse powder; the mixed coarse powder was added to the microbial culture solution at a solid-liquid ratio of 1:6, and inoculated with microbial cells at 35°C Cultivate under high temperature for 20 days, filter, wash the filter residue 5 times with absolute ethanol, and bake at 65°C until constant weight, wherein the microbial cells are Bacillus genus;

[0037] The high-efficiency filter membrane includes a filter membrane main body and an impurity adsorption layer, and the filter membrane main body material is textile fiber; the impurity adsorption layer evenly covers the surface of the filter membrane main body;

[0038] The preparation method of the impurity adsorption layer is as follows: select air-dried corn stalks, place them in a tubular carbonization furnace, pass in argon as a protective gas, heat up to 450°C at a rate of 10°C/min, keep the temperature for 2 hours, and cool naturally To normal temperature, ball mill, and sieve with a 400-mesh sieve to obtain corn stalk activated carbon, mix corn stalk activated carbon and microbial culture at a mass ratio of 1:4, ultrasonically stir for 1 hour, let stand for 12 hours, filter and collect the solid , wash the solid with ethanol to neutrality, dry it, then mix it with polybutylene succinate, citric acid monohydrate, and polyurethane in a mass ratio of 1:36:0.6:0.4, and heat up to 30°C , stirring and dispersing at 500r/min for 1h to obtain the impurity adsorption layer dispersion, and then immerse the main body of the filter membrane in the impurity adsorption layer dispersion by dipping, the residence time is 6s, take it out and dry it;

[0039] The preparation of the microbial culture is as follows: Azotobacter rufica, Bacillus megaterium, and Bacillus colloidus with a mass ratio of 1:1:2 are used as microbial clusters, placed in a constant temperature oscillator, and added with a mass ratio of 1 : 1 metal salt mixture of potassium salt and sodium salt, in which the mass ratio of microbial clusters to metal salt mixture is 1:4, cultured at a constant temperature for 72 hours at a temperature of 50°C, washed and filtered 5 times, and the filter residue is the microorganism Cultures.

Example Embodiment

[0040] Example 3

[0041] A method for synthesizing 2,2,2',4',5'-pentachloroacetophenone. The raw materials include 5 parts of 1,2,4 trichlorobenzene, 62 parts of dichloroacetyl chloride and 32 parts of catalyst in parts by weight. parts, 28 parts of water; the specific method is:

[0042] (1) Put the above-mentioned 1,2,4-trichlorobenzene and 30% of the above-mentioned catalyst by weight in a reaction tank and stir and mix them at a stirring rate of 200rpm, keep the temperature at 60°C for 35min, then add 60% of the catalyst dropwise within 50min For the above weight parts of dichloroacetyl chloride, keep the stirring rate constant, add 40% of the above weight parts of the catalyst, dropwise add the remaining weight parts of dichloroacetyl chloride within 40 minutes, raise the temperature to 75 ° C, keep it warm for 1 hour, and then add the remaining weight parts The catalyst is heated up to 85°C, the stirring speed is adjusted to 450rpm, and the pressure of the reaction tank is raised to 7×10 5 Pa, keep the reaction for 8h;

[0043] (2) After the reaction is over, release the pressure to normal pressure, slowly add carbon disulfide solvent into the reaction tank while it is hot until it is stirred and dissolved, pour it into water and stir evenly, let it cool to room temperature, separate the oil layer, extract the water layer with solvent, and into the organic layer, washed and filtered with a high-efficiency filter, dried, and distilled under reduced pressure to collect fractions at 135°C/0.025 MPa to obtain white crystals of 2,2,2',4',5'-pentachloroacetophenone.

[0044] The catalyst is a carrier medium-Lewis acid complex, and its preparation method is as follows: Weigh 8 parts of a mixture of aluminum chloride and zinc chloride with a mass ratio of 2:1 by weight, and dissolve it in 10 parts by volume under a 500w ultrasonic environment Add 6 parts of carrier medium to a 3:2 mixed solution of anhydrous methanol and anhydrous ethanol, stir at room temperature for 3 hours at a stirring rate of 200 rpm, distill off the solvent under reduced pressure, and activate at 130°C for 8 hours to obtain, Store in a desiccator for later use.

[0045] The carrier medium is a modified porous mixture with a porosity of 60%. The materials used and the preparation method are as follows: 15 parts of kaolin, 12 parts of bentonite, and 10 parts of zeolite molecular sieve are weighed in parts by weight and put into a muffle furnace for activation and deactivation. Bacteria treatment, activated at 300°C for 30 minutes, naturally cooled to room temperature and passed through a 50-mesh sieve to obtain mixed coarse powder; the mixed coarse powder was added to the microbial culture solution at a solid-to-liquid ratio of 1:3, and inoculated with microbial cells at 30°C Cultivate under high temperature for 15 days, filter, wash the filter residue 3 times with absolute ethanol, and bake at 50°C to constant weight, wherein the microorganisms are of the genus Bacillus;

[0046] The high-efficiency filter membrane includes a filter membrane main body and an impurity adsorption layer, and the material of the filter membrane main body is stainless steel; the impurity adsorption layer evenly covers the surface of the filter membrane main body;

[0047] The preparation method of the impurity adsorption layer is as follows: select air-dried corn stalks, place them in a tubular carbonization furnace, feed argon as a protective gas, heat up to 550°C at a rate of 15°C/min, keep the temperature constant for 1 hour, and cool naturally To normal temperature, ball mill, and sieve with a 400-mesh sieve to obtain corn stalk activated carbon, mix corn stalk activated carbon and microbial culture at a mass ratio of 1:1, ultrasonically stir for 2 hours, let stand for 24 hours, filter and collect the solid , wash the solid with ethanol to neutrality, dry it, then mix it with polybutylene succinate, citric acid monohydrate, and polyurethane in a mass ratio of 1:30:0.2:0.2, and heat up to 40°C , stirring and dispersing at 700r/min for 3h to obtain the impurity adsorption layer dispersion, and then dipping the main body of the filter membrane into the impurity adsorption layer dispersion by immersion, the residence time is 12s, take it out and dry it;

[0048] The preparation of the microbial culture is as follows: Azotobacter rotundum, Bacillus megaterium, and Bacillus colioids with a mass ratio of 1:3:5 are used as microbial clusters, placed in a constant temperature oscillator, and added with a mass ratio of 1 : 5 metal salt mixture of potassium salt and sodium salt, in which the mass ratio of microbial clusters to metal salt mixture is 1:2, cultured at a constant temperature for 48 hours at a temperature of 40°C, washed and filtered for 3 times, and the filter residue is the microorganism Cultures.

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Synthesis method of 2,2,2',4',5'-pentachloroacetophenone

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