CN114085142A - Method for synthesizing acyl fluoride compound by gas-phase oxidative cracking reaction of fluorine-containing ether compound - Google Patents
Method for synthesizing acyl fluoride compound by gas-phase oxidative cracking reaction of fluorine-containing ether compound Download PDFInfo
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Abstract
The invention discloses a method for synthesizing acyl fluoride compounds by gas-phase oxidative cracking reaction of fluorine-containing ether compounds, which comprises the steps of inputting the fluorine-containing ether compounds into a vaporizing chamber, heating and vaporizing at the temperature of 180-220 ℃, introducing the vaporized fluorine-containing ether compounds and oxygen into a reaction tube together for high-temperature reaction, wherein the main product generated by cracking is acyl fluoride products; the fluorine-containing ether compound is a hydrofluoroether compound, the structural formula of the hydrofluoroether compound is Rf1-O-Rf2, Rf1 is a C1-C10 perfluoroalkyl group, Rf2 is a C1-C10 hydrofluoroalkyl group, or Rf1 and Rf2 are both C1-C10 hydrofluoroalkyl groups, and the C1-C10 hydrofluoroalkyl group contains 1-6H atoms, preferably 1-4H atoms; the acyl fluoride product contains one or more than two gases of carbonyl fluoride, perfluoroacetyl fluoride, perfluoropropionyl fluoride and perfluorobutyryl fluoride. The hydrofluoroether raw material adopted by the invention is low in price, high-value acyl fluoride gas can be obtained by adopting thermal cracking, and the hydrofluoroether can be well applied to the fields of cleaning agents, etching agents, pesticide intermediates, fluorine-containing material monomers and the like in the electronic industry.
Description
Technical Field
The invention relates to the field of fluorine chemical industry, in particular to a method for synthesizing acyl fluoride compounds by a gas-phase oxidative cracking reaction of fluorine-containing ether compounds.
Background
Carbonyl fluoride is used as a cleaning gas and an etching gas for semiconductor production equipment, a fluorination gas and a raw material for an organic compound, an intermediate for organic synthesis, and a fluorinating agent, and is used as a cleaning gas for semiconductor production equipment. Trifluoroacetyl fluoride and perfluoropropionyl fluoride are important raw materials in the fluorine chemical industry, trifluoroacetyl fluoride can be used for preparing important chemical products such as trifluoroacetic acid, trifluoroiodomethane and the like, perfluoropropionyl fluoride is used for reacting with hexafluoropropylene by a 3M company to synthesize perfluorohexanone as a novel fire extinguishing agent, and the perfluorohexanol can also be used as an initiator, namely perfluoroacyl peroxide, necessary for preparing fluorine-containing polymer; both trifluoroacetyl fluoride and perfluoropropionyl fluoride can be used for cleaning agents, etching agents, pesticide intermediates, fluorine-containing material monomers and the like in the electronic industry.
The current methods for synthesizing carbonyl fluoride mainly include methods of thermal cracking of olefin alkane, electrofluorination, fluorine fluorination, metal fluoride fluorination and the like, and chinese patent CN109734070 discloses a method for cracking waste PTFE into carbonyl fluoride, and also discloses a method for thermal cracking after cleaning waste polytetrafluoroethylene, cutting into small particles of 100 microns. Pyrolysis is not much advantageous compared to mechanical comminution, and the resulting by-products require further purification and are difficult to separate.
Patent CN109607507A discloses a method for preparing carbonyl fluoride by cracking perfluorinated compounds and carbonyl fluoride. The pyrolysis effect of perfluoroolefins C ═ C, perfluoroacyl fluorides-COF and perfluorocarbonyl fluorides-C (o) -is described in the patent.
The prior preparation method of trifluoroacetyl fluoride mainly comprises a perfluoroacetyl chloride substitution method, a perfluoroacetic acid conversion method, an acetic anhydride electrolysis method and the like. Chinese patent CN109534972 discloses a method for preparing perfluoro-penta-ketone by cracking hexafluoropropylene dimer, and particularly relates to a method for preparing perfluoro-penta-ketone by cracking hexafluoropropylene dimer. The preparation method comprises the following steps: putting hexafluoropropylene dimer into an oxidation furnace to perform cracking reaction with oxygen under the condition of a first catalyst; and (4) separating the cracking product to obtain trifluoroacetyl fluoride. The patent realizes the condition that perfluoroolefin compounds are cracked to generate perfluoroacyl fluoride under the condition of high temperature of oxygen. CN 109503365 reports a method for simultaneous synthesis of trifluoroacetyl fluoride and perfluorobutanoyl fluoride by cracking olefin. CN1121064A reports a process for the preparation of trifluoroacetyl fluoride by the gas phase reaction of trichloroacetyl chloride with anhydrous hydrogen fluoride.
Chinese CN102260160A reports a preparation method for simultaneously preparing carbonyl fluoride and trifluoroacetyl fluoride, in which oxygen and hexafluoropropylene gas are contacted in a reactor under the condition of a catalyst to obtain a target product.
Disclosure of Invention
The invention aims to provide a method for synthesizing acyl fluoride compounds by gas-phase oxidative cracking reaction of fluorine-containing ether compounds. The novel oxidative cracking reaction method can be used for preparing various acyl fluorides, and by selecting different raw materials, main cracking products are formyl fluoride, perfluoroacetyl fluoride or perfluoropropionyl fluoride and the like correspondingly.
The method for synthesizing the acyl fluoride compound by the gas-phase oxidative cracking reaction of the fluorine-containing ether compound is characterized in that the fluorine-containing ether compound is input into a vaporizing chamber and heated and vaporized at the temperature of 180-220 ℃, the vaporized fluorine-containing ether compound and oxygen are introduced into a reaction tube together for high-temperature reaction, and the main product generated by cracking is an acyl fluoride product; the fluorine-containing ether compound is a hydrofluoroether compound, the structural formula of the hydrofluoroether compound is Rf1-O-Rf2, Rf1 is a C1-C10 perfluoroalkyl group, Rf2 is a C1-C10 hydrofluoroalkyl group, or Rf1 and Rf2 are both C1-C10 hydrofluoroalkyl groups, and the C1-C10 hydrofluoroalkyl group contains 1-6H atoms, preferably 1-4H atoms; the acyl fluoride product contains one or more than two gases of carbonyl fluoride, perfluoroacetyl fluoride, perfluoropropionyl fluoride and perfluorobutyryl fluoride.
The method for synthesizing the acyl fluoride compound by the gas-phase oxidative cracking reaction of the fluorine-containing ether compound is characterized in that the ratio of the volume flow rate of oxygen to the mass flow rate of the hydrofluoroether compound is 2.5-30: 1, preferably 7.5-15: 1, the unit of the volume flow rate is ml/min, and the unit of the mass flow rate is g/min.
The method for synthesizing the acyl fluoride compound by the gas-phase oxidative cracking reaction of the fluorine-containing ether compound is characterized in that the material of the reaction tube is stainless steel 304 or stainless steel 316L, preferably stainless steel 316L.
The method for synthesizing the acyl fluoride compound by the gas-phase oxidative cracking reaction of the fluorine-containing ether compound is characterized in that the reaction temperature is 400-1000 ℃, and preferably 600 ℃.
The method for synthesizing the acyl fluoride compound by the gas-phase oxidative cracking reaction of the fluorine-containing ether compound is characterized in that the reaction residence time is 10-100 s, preferably 30 s.
The method for synthesizing the acyl fluoride compound by the gas-phase oxidative cracking reaction of the fluorine-containing ether compound is characterized in that the main product generated by the high-temperature reaction cracking of the fluorine-containing ether compound and oxygen is one or more than two gases of carbonyl fluoride, perfluoroacetyl fluoride, perfluoropropionyl fluoride and perfluorobutyryl fluoride, and the total volume fraction of the gases in the cracking gas is more than 70%.
The method for synthesizing the acyl fluoride compound by the gas-phase oxidative cracking reaction of the fluorine-containing ether compound is characterized in that the hydrofluoroether compound is at least one of non-isolated hydrofluoroethers HFE356, HFE 448, HFE374, HFE 347, HFE458 and HFE365 and isolated hydrofluoroethers HFE7100, HFE7200, HFE7300 and HFE7500 produced by 3M company.
The method for synthesizing the acyl fluoride compound by the gas-phase oxidative cracking reaction of the fluorine-containing ether compound is characterized in that the hydrofluoroether compound is at least one of isolated hydrofluoroethers HFE7100, HFE7200, HFE7300 and HFE7500 produced by 3M company.
The isolated hydrofluoroether HFE7100 produced by 3M company is cracked, the main products are perfluorobutyryl fluoride and carbonyl fluoride, and the byproducts are other acyl fluoride, other alkanes and the like.
The isolated hydrofluoroether HFE7200 produced by 3M company is cracked, the main products are perfluorobutyryl fluoride and perfluoroacetyl fluoride, and the byproducts are other acyl fluoride, other alkanes and the like.
The isolated hydrofluoroether HFE7300 produced by 3M company is cracked, the main products are perfluoropropionyl fluoride and carbonyl fluoride, and the byproducts are other acyl fluoride, other alkanes and the like.
The domestic hydrofluoroether series has more H than HFE7100, HFE7200, HFE7300, HFE7500, etc. produced by 3M company, more by-products in the cracking process, and more reaction complexity and side reactions as the content of H is higher. Hydrofluoroether HFE356 contains 4 hydrogens, and the main products of the cleavage include various by-products such as methane, acetyl fluoride and the like, in addition to tetrafluoropropionyl fluoride and carbonyl fluoride, which are incompletely fluorinated.
The hydrofluoroether HFE458 cleaves the major product as perfluoroacetyl fluoride with the concomitant formation of various types of by-products.
All of the above reaction cracking and the like are equally applicable to HFE374, HFE365, HFE449 and the like.
Further, the cracked gas is detected and analyzed in the reaction process, and the specific process is as follows: although the cracked gas is introduced into the absorbent to be absorbed, the absorbent may be an alcohol such as methanol, ethanol, or propanol, but methanol is preferred because methanol has a higher reactivity and reacts with acyl fluoride at a higher rate. The amines in the absorption liquid are used to neutralize the HF generated by the reaction of the acyl fluoride with the alcohols, with the aim of removing the acid. Therefore, the absorption liquid is a methanol solution containing amine compounds, components such as perfluoropropionyl fluoride, perfluoroacetyl fluoride, carbonyl fluoride and perfluorobutyryl fluoride in the pyrolysis gas can react with methanol to generate corresponding ester compounds and HF byproducts, the amine compounds in the methanol solution are used for neutralizing and reacting the HF byproducts to finally form sample detection liquid, and then the sample detection liquid is detected and analyzed through gas chromatography.
Since acyl fluoride is corrosive and highly reactive, it reacts readily with moisture in the air and cannot be directly quantified by gas chromatography. Therefore, after the methanol is absorbed and reacts with the methanol to generate products such as dimethyl carbonate, perfluoromethyl acetate, perfluoromethyl propionate, perfluoromethyl butyrate and the like, the products are detected by gas chromatography, so that various products have no corrosiveness and are calibrated by standard samples. The content of products such as dimethyl carbonate, perfluoromethyl acetate, perfluoromethyl propionate, perfluoromethyl butyrate and the like can be obtained through detection and analysis, the content of corresponding acyl fluoride raw materials can be deduced, and the pyrolysis gas generated by the reaction is indirectly analyzed through the method.
Wherein, the content of the amine compound in the methanol solution is required to achieve the following absorption effect: after the amine compound in the methanol solution neutralizes and reacts the HF byproduct generated by absorption, the pH of the mixed solution is neutral or alkalescent, namely the pH is 7-9.
Compared with the prior art, the invention has the beneficial effects that:
1. the hydrofluoroether adopted by the invention is low in price, high-value acyl fluoride gas can be obtained by adopting thermal cracking, and the hydrofluoroether can be applied to the fields of cleaning agents, etching agents, pesticide intermediates, fluorine-containing material monomers and the like in the electronic industry.
2. Provides a new direction for acyl fluoride synthesis, and can synthesize a new synthetic route.
3. The waste hydrofluoroether can provide a new recycling treatment method.
Detailed Description
The present invention is further illustrated by the following examples, which should not be construed as limiting the scope of the invention.
Example 1: pumping 1kg of HFE7100 into a gasification chamber through a peristaltic pump for preheating vaporization, controlling the flow rate by a flow controller to be 4g/min and oxygen to be 30mL/min, controlling the temperature of the gasification chamber to be 200 ℃, introducing the vaporized HFE7100 raw material and oxygen (the oxygen flow is 30mL/min) into a reaction tube together for high-temperature oxidative cracking reaction, controlling the cracking temperature to be 600 ℃, controlling the reaction residence time to be 30s, precooling the cracked gas flow after the reaction to be below 80 ℃, introducing the cracked gas flow into absorption liquid (the absorption liquid is mixed liquid of methanol and triethylamine) for absorption to form sample detection liquid, and collecting excessive gas (including excessive oxygen) insoluble in the absorption liquid by an air bag. After the reaction, the liquid weight of the absorption liquid is increased by 0.891kg, and the weight of the air bag is increased by 0.108 kg. The results of the gas analysis of the absorption liquid and the gas bag are shown in Table 1.
The acyl fluoride products can react with methanol, and other products cannot react with the methanol, so that the acyl fluoride products can be absorbed by the methanol absorption liquid to increase the weight. We therefore calculated the yield by the differential method. In example 1, the weight of the liquid absorbed by methanol was increased by 0.891kg for 1kg of the starting material, and the weight of the other gases was collected by the air bag by 0.108kg, and it is considered that the weight of the acyl fluoride product was increased by the methanol absorption liquid.
In table 1, the yield of the acyl fluoride-based product was 0.891kg of the mass of the methanol-absorbed solution increased in absorption weight per 1kg of the mass of the raw material by 100%. The yield of other products is 0.108kg of the weight of the air bag absorbing weight gain per 1kg of the raw material by 100%. During the high-temperature oxidative cracking reaction, the total introduced mass of oxygen is small and is almost negligible compared with HFE7100 raw material. In the experiment, the calculation result of the total yield in table 1 may be less than 100% due to the operation error and the trace amount of gas leakage in the gas bag, so the pyrolysis effect of the present application is mainly evaluated by the yield of the acyl fluoride product.
TABLE 1
In table 1, the acyl fluoride products refer to perfluorobutyryl fluoride, carbonyl fluoride and other acyl fluorides, and the molar ratios of the perfluorobutyryl fluoride, the carbonyl fluoride and the other acyl fluorides are 34.6%, 55.3% and 10.1%, respectively.
In the following examples, the ratios of the acyl fluoride products are all molar ratios, and the yield of the acyl fluoride products is calculated by the formula shown in example 1.
Example 2: pumping 1kg of HFE7200 into a gasification chamber through a peristaltic pump for preheating vaporization, controlling the flow rate by a flow controller to be 4g/min and oxygen to be 30mL/min, controlling the temperature of the gasification chamber to be 200 ℃, introducing the vaporized HFE7200 raw material and oxygen (the oxygen flow is 30mL/min) into a reaction tube together for high-temperature oxidative cracking reaction, controlling the cracking temperature to be 600 ℃, controlling the reaction residence time to be 30s, precooling the cracked gas flow after the reaction to be below 80 ℃, introducing the cracked gas flow into an absorption liquid (the absorption liquid is a mixed liquid of methanol and triethylamine) for absorption to form a sample detection liquid, and collecting the excessive gas insoluble in the absorption liquid by an air bag. After the reaction, the liquid of the absorption liquid is increased by 0.899kg, and the air bag is increased by 0.099 kg. The results of the gas analysis of the absorption liquid and the gas bag are shown in Table 2.
TABLE 2
Example 3: pumping 1kg of HFE7300 into a gasification chamber through a peristaltic pump for preheating vaporization, controlling the flow rate by a flow controller to be 4g/min and oxygen to be 30mL/min, controlling the temperature of the gasification chamber to be 200 ℃, introducing the vaporized HFE7300 raw material and oxygen (the oxygen flow is 30mL/min) into a reaction tube together for high-temperature oxidative cracking reaction, controlling the cracking temperature to be 600 ℃, controlling the reaction residence time to be 30s, precooling the cracked gas flow after the reaction to be below 80 ℃, introducing the cracked gas flow into an absorption liquid (the absorption liquid is a mixed liquid of methanol and triethylamine) for absorption to form a sample detection liquid, and collecting the excessive gas insoluble in the absorption liquid by an air bag. After the reaction is finished, the liquid weight of the absorption liquid is increased by 0.810kg, and the gas bag is increased by 0.188 kg. The results of the gas analysis of the absorption liquid and the gas bag are shown in Table 3.
TABLE 3
Example 4: pumping 1kg of HFE356 into a gasification chamber through a peristaltic pump for preheating vaporization, controlling the flow rate by a flow controller to be 4g/min and oxygen to be 30mL/min, controlling the temperature of the gasification chamber to be 200 ℃, introducing the vaporized HFE356 raw material and oxygen (the oxygen flow is 30mL/min) into a reaction tube together for high-temperature oxidative cracking reaction, controlling the cracking temperature to be 600 ℃, controlling the reaction retention time to be 30s, precooling the cracked gas flow after the reaction to be below 80 ℃, introducing an absorption liquid (the absorption liquid is a mixed liquid of methanol and triethylamine) to absorb to form a sample detection liquid, and collecting the excessive gas insoluble in the absorption liquid by an air bag. After the reaction is finished, the liquid weight of the absorption liquid is increased by 0.769kg, and the air bag is increased by 0.231 kg. The results of the gas analysis of the absorption liquid and the gas bag are shown in Table 4.
TABLE 4
Example 5: pumping 1kg of HFE458 into a gasification chamber through a peristaltic pump for preheating vaporization, controlling the flow rate by a flow controller to be 4g/min and oxygen to be 30mL/min, controlling the temperature of the gasification chamber to be 200 ℃, introducing the vaporized HFE458 raw material and oxygen (the oxygen flow is 30mL/min) into a reaction tube together for high-temperature oxidative cracking reaction, controlling the cracking temperature to be 600 ℃, controlling the reaction retention time to be 30s, precooling the cracked gas flow after the reaction to be below 80 ℃, introducing an absorption liquid (the absorption liquid is a mixed liquid of methanol and triethylamine) into the reaction tube for absorption to form a sample detection liquid, and collecting the excessive gas insoluble in the absorption liquid by an air bag. After the reaction is finished, the liquid weight of the absorption liquid is increased by 0.629kg, and the weight of the air bag is increased by 0.371 kg. The results of the gas analysis of the absorption liquid and the gas bag are shown in Table 5.
TABLE 5
Example 6: pumping 1kg of HFE449 into a gasification chamber through a peristaltic pump for preheating vaporization, controlling the flow rate by a flow controller to be 4g/min and oxygen to be 30mL/min, controlling the temperature of the gasification chamber to be 200 ℃, introducing the vaporized HFE449 raw material and oxygen (the oxygen flow is 30mL/min) into a reaction tube together for high-temperature oxidative cracking reaction, controlling the cracking temperature to be 600 ℃, controlling the reaction residence time to be 30s, precooling the cracked gas flow after the reaction to be below 80 ℃, introducing an absorption liquid (the absorption liquid is a mixed liquid of methanol and triethylamine) into the reaction tube for absorption to form a sample detection liquid, and collecting the excessive gas insoluble in the absorption liquid by an air bag. After the reaction, the weight of the absorption liquid is increased by 0.721kg, and the weight of the air bag is increased by 0.278 kg. The results of the gas analysis of the absorption liquid and the gas bag are shown in Table 6.
TABLE 6
And (3) comparison test: cleavage of fluorine-containing dioxa compounds
The dioxa compound can be cracked at high temperature and can generate a target perfluoroacyl fluoride structure, but the structure is variable, so that side reactions are generated in the reaction process, and the target acyl fluoride is difficult to obtain.
Comparative example 1: pumping 1kg of perfluoro (2, 5-dimethyl-3, 6-dioxanonanoic acid) methyl ester into a gasification chamber through a peristaltic pump for preheating vaporization, controlling the flow rate by a flow controller to be 4g/min and the oxygen flow to be 30mL/min, controlling the temperature of the gasification chamber to be 200 ℃, introducing the vaporized perfluoro (2, 5-dimethyl-3, 6-dioxanonanoic acid) methyl ester raw material and the oxygen (the oxygen flow to be 30mL/min) into a reaction tube together for carrying out high-temperature oxidative cracking reaction, controlling the cracking temperature to be 600 ℃, controlling the reaction retention time to be 30s, precooling the cracked gas flow after the reaction to be below 80 ℃, introducing into an absorption liquid (the absorption liquid is a mixed liquid of methanol and triethylamine) for absorption to form a sample detection liquid, and collecting excessive gas insoluble in the absorption liquid by an air bag. After the reaction is finished, the liquid weight of the absorption liquid is increased by 0.446kg, and the weight of the air bag is increased by 0.553 kg. The results of the gas analysis of the absorption liquid and the gas bag are shown in Table 7.
TABLE 7
Comparative example 2: pumping 1kg of perfluorodiethylene glycol dimethyl ether into a gasification chamber through a peristaltic pump for preheating vaporization, controlling the flow rate by a flow controller to be 4g/min and oxygen to be 30mL/min, controlling the temperature of the gasification chamber to be 200 ℃, introducing the vaporized perfluorodiethylene glycol dimethyl ether raw material and oxygen (the oxygen flow is 30mL/min) into a reaction tube together for high-temperature oxidative cracking reaction, controlling the cracking temperature to be 600 ℃, controlling the reaction residence time to be 30s, precooling the cracked gas flow after the reaction to be below 80 ℃, introducing the cracked gas flow into an absorption liquid (the absorption liquid is a mixed liquid of methanol and triethylamine) for absorption to form a sample detection liquid, and collecting the excessive gas insoluble in the absorption liquid by an air bag. After the reaction is finished, the weight of the liquid of the absorption liquid is increased by 0.326kg, and the weight of the air bag is increased by 0.674 kg. The results of the gas analysis of the absorption liquid and the gas bag are shown in Table 8.
TABLE 8
The cracking of the dioxygen compounds is less effective and the by-products and impurities are more abundant than the cracking of hydrofluoroethers.
The statements in this specification merely set forth a list of implementations of the inventive concept and the scope of the present invention should not be construed as limited to the particular forms set forth in the examples.
Claims (8)
1. A method for synthesizing acyl fluoride compounds by gas-phase oxidative cracking reaction of fluorine-containing ether compounds is characterized in that the fluorine-containing ether compounds are input into a vaporizing chamber to be heated and vaporized at the temperature of 180-220 ℃, the vaporized fluorine-containing ether compounds and oxygen are introduced into a reaction tube together to carry out high-temperature reaction, and the main products generated by cracking are acyl fluoride products; the fluorine-containing ether compound is a hydrofluoroether compound, the structural formula of the hydrofluoroether compound is Rf1-O-Rf2, Rf1 is a C1-C10 perfluoroalkyl group, Rf2 is a C1-C10 hydrofluoroalkyl group, or Rf1 and Rf2 are both C1-C10 hydrofluoroalkyl groups, and the C1-C10 hydrofluoroalkyl group contains 1-6H atoms, preferably 1-4H atoms; the acyl fluoride product contains one or more than two gases of carbonyl fluoride, perfluoroacetyl fluoride, perfluoropropionyl fluoride and perfluorobutyryl fluoride.
2. The method according to claim 1, wherein the hydrofluoroether compound is at least one of non-isolative hydrofluoroethers HFE356, HFE 448, HFE374, HFE 347, HFE458, and HFE 365.
3. The method according to claim 1, wherein the hydrofluoroether compound is at least one of isolated hydrofluoroethers HFE7100, HFE7200, HFE7300, and HFE7500 manufactured by 3M.
4. The method for synthesizing acyl fluoride compounds according to claim 1, wherein the ratio of the volume flow rate of oxygen to the mass flow rate of hydrofluoroether compounds is 2.5-30: 1, preferably 7.5-15: 1, the volume flow rate is ml/min, and the mass flow rate is g/min.
5. The method for synthesizing acyl fluoride compounds according to claim 1, wherein the reaction tube is made of stainless steel 304 or 316L, preferably 316L.
6. The method for synthesizing acyl fluoride compounds according to claim 1, wherein the reaction temperature is 400-1000 ℃, preferably 600 ℃.
7. The method for synthesizing acyl fluoride compounds by gas-phase oxidative cracking of fluorine-containing ether compounds according to claim 1, wherein the reaction residence time is 10 s-100 s, preferably 30 s.
8. The method for synthesizing acyl fluoride compound by gas-phase oxidative cracking of fluorine-containing ether compound according to claim 1, wherein the main product obtained by the high-temperature reaction cracking of fluorine-containing ether compound with oxygen is one or more gases selected from carbonyl fluoride, perfluoroacetyl fluoride, perfluoropropionyl fluoride and perfluorobutyryl fluoride, and the total volume fraction of the gases in the cracked gas is more than 70%.
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Citations (6)
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| GB2058763A (en) * | 1979-08-31 | 1981-04-15 | Du Pont | Preparation of Fluorocarbonyl and Compounds |
| US5710317A (en) * | 1994-07-28 | 1998-01-20 | Asahi Glass Company Ltd. | Preparation of difluoroacetic acid fluoride and difluoroacetic acid esters |
| CN1371353A (en) * | 1999-08-31 | 2002-09-25 | 旭硝子株式会社 | Process for producing vic-dichloro acid fluoride |
| CN102762525A (en) * | 2010-02-17 | 2012-10-31 | 中央硝子株式会社 | Method for producing semiconductor gas |
| CN102822134A (en) * | 2010-03-29 | 2012-12-12 | 中央硝子株式会社 | Method for producing difluoroacetyl chloride |
| CN104781220A (en) * | 2012-11-14 | 2015-07-15 | 大金工业株式会社 | Method for producing dry etching gas |
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2021
- 2021-10-28 CN CN202111261691.7A patent/CN114085142A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2058763A (en) * | 1979-08-31 | 1981-04-15 | Du Pont | Preparation of Fluorocarbonyl and Compounds |
| US5710317A (en) * | 1994-07-28 | 1998-01-20 | Asahi Glass Company Ltd. | Preparation of difluoroacetic acid fluoride and difluoroacetic acid esters |
| CN1371353A (en) * | 1999-08-31 | 2002-09-25 | 旭硝子株式会社 | Process for producing vic-dichloro acid fluoride |
| CN102762525A (en) * | 2010-02-17 | 2012-10-31 | 中央硝子株式会社 | Method for producing semiconductor gas |
| CN102822134A (en) * | 2010-03-29 | 2012-12-12 | 中央硝子株式会社 | Method for producing difluoroacetyl chloride |
| CN104781220A (en) * | 2012-11-14 | 2015-07-15 | 大金工业株式会社 | Method for producing dry etching gas |
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