CN108276243B - Industrial production method of octafluorocyclopentene - Google Patents
Industrial production method of octafluorocyclopentene Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/204—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being a halogen
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- C07C17/02—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated hydrocarbons
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- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
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- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/46—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom
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Abstract
The invention discloses an industrial production method of octafluorocyclopentene, and belongs to the field of synthesis of fine chemical intermediates. Cyclopentene, chlorine and anhydrous potassium fluoride are used as raw materials, sulfolane is used as a solvent, and the raw materials and the sulfolane are subjected to temperature programming, are gradually chlorinated, and are subjected to high-temperature substitution reaction with the potassium fluoride to generate octafluorocyclopentene. The kettle residue after the product separation can be reused by distilling the solvent sulfolane under reduced pressure; the production process has the advantages of simple steps, environmental protection, high yield, low production cost and high purity of the obtained product, and is beneficial to later-stage application.
Description
Technical Field
The invention relates to an industrial production method of octafluorocyclopentene, and belongs to the field of synthesis of fine chemical intermediates.
Background
The 1,2,3,3,4,4,5, 5-octafluorocyclopentene is abbreviated as octafluorocyclopentene or perfluorocyclopentene, is mainly used for etching and cleaning semiconductors, and can participate in the preparation of organic photochromic materials. Octafluorocyclopentene is considered to be a competitive advantage as one of the next generation etching gases and the most attractive raw material for electronic devices. Octafluorocyclopentene may also be used in the synthesis of high-end dyes. It has less influence on environment and is one new kind of fluoric chemical.
The preparation method of the literature mostly uses the fluorine chloride of cyclopentene as a raw material and is prepared by multi-step fluorination reaction.
Ancient Zhuyufu et al, Ribenson ceramic nitroxide corporation, reported a process for preparing octafluorocyclopentene from octachlorocyclopentene as a starting material by a two-step fluorination reaction. Under the action of gas phase fluorination catalyst, octachlorocyclopentene and anhydrous HF are first halogen exchange reacted to produce 1, 2-dichloro-3, 3,4,4,5, 5-hexafluorocyclopentene, chloroheptafluorocyclopentene, etc. and then reacted with alkali metal fluoride in amide and sulfoxide solvent to produce octafluorocyclopentene. The reaction formula is as follows:
octachlorocyclopentene as a raw material needs to be prepared by self, and dicyclopentadiene as an initial raw material needs to be depolymerized at high temperature to obtain cyclopentadiene monomers, and then the subsequent steps can be carried out.
The synthesis process comprises the following steps:
the research group also tried to prepare octachlorocyclopentadiene as an intermediate by adopting the method, and the following problems existed:
firstly, the dicyclopentadiene which is commercially available needs to be depolymerized at the high temperature of 300-350 ℃ to prepare cyclopentadiene monomers, and the research group finds that the high temperature is not easy to be reached in a small test and is dangerous to operate. If the production is enlarged, the actual operation is more difficult. A small amount of cyclopentadiene monomer is obtained by adopting an electric heating jacket for small trial and subsequent steps are explored.
Secondly, when chlorine is introduced by using a newly prepared cyclopentadiene monomer according to the process of the literature, the cyclopentadiene monomer is easily polymerized into stable dicyclopentadiene after the temperature is increased, the reaction temperature is increased, the tar content of the system is increased, a sample is taken for GC-MS and GC analysis, only about 5 percent of target product is obtained, the reaction system is viscous, and chlorine is introduced to the reaction system and cannot be absorbed, so that the product content is not changed.
Japanese patent discloses that under the condition of using nonafluorocyclopentane chloride as raw material and using isopropanol as solvent and zinc powder, the nonafluorocyclopentane chloride can be used for preparing octafluorocyclopentene by means of dehalogenation reaction, and the isopropanol in the product can be removed by adopting 13X type molecular sieve. In the route, the raw material of the chlorononafluorocyclopentane is not suitable to be obtained. The reaction formula is as follows:
in conclusion, the existing synthesis method of octafluorocyclopentene has the problems of more reaction steps, unavailable raw materials, large amount of hydrogen fluoride, more reaction steps and low product separation yield.
Disclosure of Invention
In order to overcome the defects in the prior art, the invention aims to provide an industrial production method of octafluorocyclopentene, which comprises the steps of heating cyclopentene and chlorine by a program, reacting to obtain octachlorocyclopentene, and then reacting with potassium fluoride at a high temperature to obtain the octafluorocyclopentene.
In order to achieve the purpose, the invention provides an industrial production method of octafluorocyclopentene, which is technically characterized by comprising the following steps: the method takes cyclopentene as a raw material, and obtains an octafluorocyclopentene product after temperature programming chlorination and high temperature fluorination in turn. The method comprises the following steps:
first step, chlorination reaction:
introducing chlorine into the cyclopentene, performing addition to obtain 1, 2-dichlorocyclopentane, continuously introducing the chlorine, heating the reaction to 70 ℃ for reaction to obtain 1,2,3, 4-tetrachlorocyclopentane, continuously heating the reaction to 180 ℃ and 210 ℃ for reaction to obtain a crude octachlorocyclopentene product;
in the step, the reaction is carried out in the absence of a solvent, and the molar ratio of the cyclopentene serving as the raw material to the chlorine is 1: 18-20. Stopping the reaction when the content of the intermediate is less than 2%, and purifying the product by reduced pressure distillation;
and step two, substitution fluorination:
after anhydrous potassium fluoride and sulfolane are mixed, the temperature is controlled at 140-.
In the step, qualified octafluorocyclopentene is obtained by adopting a mode of reaction and normal pressure rectification, and is received by a low-temperature cooling device at the cooling temperature of-10-0 ℃. The reaction time is usually 2-5 h; the mol ratio of octachlorocyclopentene to anhydrous potassium fluoride in the raw materials is 1: 10-12.
Through the process, the separation yield of the octafluorocyclopentene product reaches 45-55%, the content of octafluorocyclopentene in the product is more than 99%, the water content is less than 0.2%, and the detection of chloride ions is less than 0.1%.
Further, after the second step reaction, neutralizing the obtained kettle residue with alkali, centrifuging to remove inorganic salts so as to reduce the content of fluorine ions and chloride ions in the process wastewater, and finally distilling under reduced pressure to remove sulfolane and ethanol for recycling. The operation process is as follows:
cooling the material after the fluorination reaction distillation product to 50-70 ℃, adding potassium hydroxide solid to remove redundant anhydrous potassium fluoride and hydrochloride in the system, then centrifugally filtering to obtain centrifugal mother liquor and filter cake (the filter cake contains a large amount of potassium chloride and a small amount of potassium fluoride), leaching the filter cake with ethanol, and retaining the leacheate to finally obtain centrifugal mother liquor containing pyridine sulfolane and the leacheate containing ethanol sulfolane, wherein the filter cake is light yellow solid. And recovering the solvents pyridine, sulfolane and a small amount of ethanol from the filtrate by adopting a reduced pressure distillation method, wherein the recovered solvents are used for next experiment, and the solvents can be recovered for multiple times and can be used for multiple times.
The invention has the beneficial effects that:
1. the method takes cyclopentene, chlorine and anhydrous potassium fluoride as raw materials, and obtains the octafluorocyclopentene with high yield and high content after chlorination reaction and fluorination reaction in sequence, wherein the separation yield of the product can reach 45-55%, the product content is more than 99%, the water content is less than 0.1%, and the chloride ion detection is less than 0.1%.
2. Compared with the traditional process method, the method has the advantages of short process flow, convenient operation and contribution to industrial amplification.
3. In the process, the residue after the octafluorocyclopentene product is separated is neutralized by alkali and then subjected to reduced pressure distillation to respectively recover the sulfolane solvent and ethanol for leaching for reuse.
4. The production process of the invention is pollution-free, green, high in yield, beneficial to reducing production cost, high in product purity and beneficial to later application.
Detailed Description
The present invention will be described in further detail with reference to specific examples, but the present invention is not limited to the specific examples.
Example 1: the synthesis route of octachlorocyclopentene in this example is shown in the following reaction formula:
the experimental steps are as follows:
adding 68g (1mol, 97%) of liquid cyclopentene into a 250ml four-port reaction kettle equipped with a mechanical stirring and reflux condensing device, and connecting with an alkaline tail gas absorption device;
when the temperature in the system is 25 ℃, chlorine gas is introduced into the kettle, the temperature of the system rises at this time, the temperature during backflow is 45 ℃ (the atmospheric boiling point of cyclopentene is 44.2 ℃), the chlorine gas is introduced to carry out addition reaction, no gas is produced during the beginning, the chlorine gas is completely absorbed, the backflow stops along with the progress of the reaction, and the ventilation speed of the chlorine gas is optimal to be 1 g/min. At this point, a sample was taken for gas phase analysis and the feed cyclopentene was < 2%. And then slowly raising the temperature in the system to 70 ℃, continuously introducing chlorine gas for deep chlorination, converting the system into a mixture of polychlorinated cyclopentane, continuously raising the temperature of the later-stage system to 180 ℃, continuously introducing chlorine gas, controlling the temperature rise speed to be 10 ℃/h, controlling the maximum reaction temperature to be 210 ℃, sampling and analyzing, and stopping the reaction when the over-chlorination state is less than 2%. The reaction product is octachlorocyclopentene and a small amount of polymer; a total of about 1420g of chlorine were passed. The utilization rate of the chlorine can be improved by adopting a continuous device during industrial amplification.
The temperature is reduced to 100 ℃, residual chlorine and hydrogen chloride gas in the system are removed by using a water pump under reduced pressure, and then the system is connected with a mechanical pump.
The reduced pressure distillation is carried out by a mechanical pump, and the product is collected (116 ℃ C./4 mmHg). 223.1g of octachlorocyclopentene is obtained, m/z is 343.6 by GC-MS detection, and other fragment peaks are consistent with those of a standard sample. The product purity is 98 percent, and the product yield is 63.6 percent.
Example 2: the synthetic route for octachlorocyclopentene in this example is an enlargement of example 1
The experimental steps are as follows:
680g (10mol, 97%) of liquid cyclopentene is added into a 2L four-port reaction kettle provided with a mechanical stirring and reflux condensing device, and then connected with an alkaline tail gas absorption device;
at room temperature, chlorine gas is introduced into the kettle, the temperature of the system rises at this time, the temperature during reflux is 45 ℃ (the atmospheric boiling point of cyclopentene is 44.2 ℃), and chlorine gas is introduced to perform addition reaction, so that no gas is produced at the beginning, the chlorine gas is completely absorbed, the reflux stops along with the reaction, and the aeration speed of the chlorine gas is optimal to be 1 g/min. At this point, a sample can be taken for gas phase analysis, and the cyclopentene raw material is less than 2%. Then slowly heating the system to 110 ℃, continuously introducing chlorine gas for deep chlorination, converting the system into a mixture of polychlorinated cyclopentane, continuously heating the system to 180 ℃ in the later period, continuously introducing chlorine gas, controlling the heating speed to 10 ℃/h and the highest reaction temperature to 210 ℃, sampling and analyzing, stopping the reaction when the excessive chlorination state is less than 2%, and obtaining reaction products of octachlorocyclopentene and a small amount of polymers; a total of 12780g of chlorine was passed in.
The temperature is reduced to 100 ℃, residual chlorine and hydrogen chloride gas in the system are removed by using a water pump under reduced pressure, and then the system is connected with a mechanical pump.
The reduced pressure distillation is carried out by a mechanical pump, and the product is collected (116 ℃ C./4 mmHg). 2140.4g of octachlorocyclopentene is obtained, the product purity is 98 percent, and the product yield is 61.7 percent.
Example 3: the synthetic route of octafluorocyclopentene in this example is shown in the following reaction formula:
the experimental steps are as follows:
290g (5mol, 99%, 10eq) of anhydrous potassium fluoride and 1012g of sulfolane are added into a 2L four-port reaction kettle provided with a mechanical stirring and rectifying condensing device, and the temperature is raised to 140 ℃ by stirring.
172g (98 percent, 0.5mol) of self-made octachlorocyclopentene and 180g of sulfolane are mixed and then are dripped into the system, the dripping time is 2 hours, the temperature of the system is slowly increased in the dripping process, the temperature increasing speed is about 5 ℃/h, the reflux of the system is obvious after the dripping is finished, and the product is extracted from the top end of a rectifying tower. The atmospheric boiling point of the product octafluorocyclopentene is 27 ℃.
When the product fraction is reduced, the temperature of the system is continuously increased to 170 ℃ at most; the product is cooled to-10-0 ℃ by a low-temperature cooling device in the product collection process, so that the evaporation loss of the product is prevented.
This example collected 79.6g of octafluorocyclopentene product, 99.7% GC, less than 0.2% moisture, less than 0.1% chloride detection, and 75% product yield. 212.0 m/z by GC-MS, F NMR spectral data: -117.048ppm (4F), -129.197ppm (2F), -148.448ppm (2F); both GC-MS and FNMR were consistent with the peak formation of the standard sample.
Example 4:
the experimental steps are as follows:
290g (5mol, 99%, 10eq) of anhydrous potassium fluoride and 1012g of sulfolane are added into a 2L four-port reaction kettle provided with a mechanical stirring and rectifying condensing device, and the temperature is raised to 150 ℃ by stirring.
172g (98 percent, 0.5mol) of self-made octachlorocyclopentene and 180g of sulfolane are mixed and then are dripped into the system, the dripping time is 1.5h, the temperature of the system is slowly increased in the dripping process, the temperature increasing speed is about 10 ℃/h, the reflux of the system is obvious after the dripping is finished, and the product is extracted from the top end of a rectifying tower.
When the product fraction is reduced, the temperature of the system is continuously increased to 170 ℃ at most; the product is cooled to-10-0 ℃ by a low-temperature cooling device in the product collection process.
The octafluorocyclopentene product 82.7g, GC 99.2% and product yield 78% are collected in the example.
Example 5:
the experimental steps are as follows:
to a 5L four port reactor equipped with mechanical stirring and rectification condensing units, 580g (10mol, 99%, 10eq) of anhydrous potassium fluoride and 2025g of sulfolane were added, and the temperature was raised to 140 ℃ with stirring.
343.7g (98 percent and 1mol) of self-made octachlorocyclopentene and 360g of sulfolane are mixed and then are dripped into the system, the dripping time is 3h, the temperature of the system is slowly increased in the dripping process, the temperature increasing speed is about 10 ℃/h, the reflux of the system is obvious after the dripping is finished, and the product is extracted from the top end of a rectifying tower.
When the product fraction is reduced, the temperature of the system is continuously increased to 170 ℃ at most, the reaction is carried out in a heat preservation way until no fraction is extracted, and the reaction is stopped; the product is cooled to-10-0 ℃ by a low-temperature cooling device in the product collection process.
In the example, 180.2g of octafluorocyclopentene product, 99.2 percent of GC and 85 percent of product yield are collected.
Example 6:
the experimental steps are as follows:
290g (5mol, 99%, 10eq) of anhydrous potassium fluoride and 1012g of sulfolane are added into a 2L four-port reaction kettle provided with a mechanical stirring and rectifying condensing device, and the temperature is raised to 150 ℃ by stirring.
172g (98 percent, 0.5mol) of self-made octachlorocyclopentene and 180g of sulfolane are mixed and then are dripped into the system, the dripping time is 2 hours, the temperature of the system is slowly increased in the dripping process, the temperature increasing speed is about 10 ℃/h, the reflux of the system is obvious after the dripping is finished, and the product is extracted from the top end of a rectifying tower.
Keeping the temperature at 170 ℃ after the dripping is finished until no fraction is discharged from the product; the product is cooled to-10-0 ℃ by a low-temperature cooling device in the product collection process.
The octafluorocyclopentene product 65.7g, GC 99.3% and product yield 62% are collected in the example. This example demonstrates that reducing the ratio of fluorinating reagent has a greater effect on yield.
Example 7:
the experimental steps are as follows:
to a 2L four port reactor equipped with a mechanical stirring and rectifying condenser, 348g (6mol, 99%, 12eq) of anhydrous potassium fluoride and 1012g of sulfolane were added, and the temperature was raised to 140 ℃ with stirring.
172g (98 percent, 0.5mol) of self-made octachlorocyclopentene and 180g of sulfolane are mixed and then are dripped into the system, the dripping time is 2 hours, the temperature of the system is slowly increased in the dripping process, the temperature increasing speed is about 10 ℃/h, the reflux of the system is obvious after the dripping is finished, and the product is extracted from the top end of a rectifying tower.
After the dripping is finished, keeping the temperature at 170 ℃ until no fraction is discharged from the product, wherein the time is 2 hours; the product is cooled to-10-0 ℃ by a low-temperature cooling device in the product collection process.
The octafluorocyclopentene product 81.6g, GC 99.2% and product yield 77% are collected in the example. This example demonstrates a fluorination reagent ratio of 10: 1 to 12: 1 does not contribute much to the yield.
And (3) solvent recovery:
and (3) cooling the rectified kettle residue to 60 ℃, centrifuging, washing a filter cake with 100mL of ethanol, wherein the filter cake mainly comprises potassium chloride, potassium fluoride and a small amount of solvent, and is light yellow and is discarded as solid waste.
And (3) carrying out reduced pressure distillation on the filtrate and the washing liquid by using an oil pump and a water pump respectively, recovering sulfolane and ethanol, wherein the recovered solvent can be reused for many times, and the recovery rate of the solvent is more than 90%.
Claims (7)
1. An industrial production method of octafluorocyclopentene is characterized by comprising the following steps: first step, chlorination reaction: introducing chlorine into the cyclopentene, performing addition to obtain 1, 2-dichlorocyclopentane, continuously introducing the chlorine, heating the reaction to 70 ℃ for reaction to obtain 1,2,3, 4-tetrachlorocyclopentane, continuously heating the reaction to 180 ℃ and 210 ℃ for reaction to obtain a crude octachlorocyclopentene product; and step two, substitution fluorination: after anhydrous potassium fluoride and sulfolane are mixed, the temperature is controlled at 140-.
2. The industrial production method of octafluorocyclopentene according to claim 1, wherein: in the first-step chlorination reaction, the reaction is carried out in the absence of a solvent, and the equivalent ratio of chlorine to cyclopentene is 18-20: 1.
3. the industrial production method of octafluorocyclopentene according to claim 1, wherein: in the first-step chlorination reaction, the crude octachlorocyclopentene is subjected to a reduced pressure rectification mode to obtain a pure octachlorocyclopentene.
4. The industrial production method of octafluorocyclopentene according to claim 1, wherein: in the second step of substitution fluorination, the molar ratio of anhydrous potassium fluoride to octachlorocyclopentene is 10-12: 1.
5. the industrial production method of octafluorocyclopentene according to claim 1, wherein: in the second step of the substitution fluorination, octafluorocyclopentene is synthesized by adopting a mode of rectifying a product while reacting, and is received by adopting a low-temperature cooling device.
6. The industrial production method of octafluorocyclopentene according to claim 1, wherein: and centrifuging and distilling the material obtained after the product is subjected to reactive distillation in the second step under reduced pressure to obtain a solvent for recycling in the next batch.
7. The industrial production method of octafluorocyclopentene according to claim 6, wherein the solvent application operation specifically comprises: naturally cooling the material after the fluorination reaction rectification product to 50-70 ℃, obtaining centrifugate and filter cake containing a large amount of potassium chloride and a small amount of potassium fluoride through centrifugal filtration, leaching the filter cake with ethanol, retaining leacheate, respectively recovering the sulfolane solution and the ethanol leacheate under reduced pressure, and recycling the obtained solvent for next use.
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