CN103570491A - Method of synthesizing 1-chloro-2,3,3,4,4,5,5-heptafluorocyclopentene by gas-phase catalysis - Google Patents
Method of synthesizing 1-chloro-2,3,3,4,4,5,5-heptafluorocyclopentene by gas-phase catalysis Download PDFInfo
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Abstract
The invention relates to a method of synthesizing 1-chloro-2,3,3,4,4,5,5-heptafluorocyclopentene by gas-phase catalysis, and belongs to the chemical synthesis field. According to the method, at least one selected from chromium, magnesium, zinc and aluminium is adopted as an active metal of a catalyst, 1,2-dichloro-3,3,4,4,5,5-hexafluorocyclopentene is adopted as a raw material, AHF is adopted as a fluorinating agent, and a high-temperature gas-state condition is selected to perform a reaction. The selectivity of the method is very high, and the unreacted raw material can be recycled and reutilized. The raw material is prepared by using C5Cl6 and Cl2 as raw materials and the AHF as a fluorinating agent preferably by using the method, namely by using reaction conditions the same as the method. The method adopts a two-step gas-catalytic fluorination technology, and is performed in the same fixed bed reactor. Through separation treatment of intermediate products, the selectivity of the final product is good and byproducts are little. Through recycle and reutilization of the C5Cl2F6, the technology is more optimized, the production cost is reduced, and the method conforms to policies about low energy consumption and environmental-friendly and clean production of our country.
Description
Technical field
The present invention is that the synthetic 1-of a kind of two step gas phase catalysises is chloro-2,3,3,4,4,5, and the method for 5-seven fluorine cyclopentenes relates to a kind ofly by chlorine, anhydrous hydrogen fluoride gas and hexachlorocyclopentadiene, under high temperature gas phase, interacts with catalyzer, generates C
5clF
7method.
Background technology
1-is chloro-2,3,3,4,4,5, and 5-seven fluorine cyclopentenes are synthetic intermediates of a kind of fluorochemicals, and important Chemicals, have very high industrial application value.Non-patent literature (Journal of the American Chemical Society, 86 (23), 5361-2; 1964) introduced a kind of chloro-ly 2,3,3,4,4,5 with 1-, 5-seven fluorine cyclopentenes are raw material, and synthetic 1-is chloro-2,2,3,3,4, the method for 4-hexafluoro cyclopentenes and 2,2,3,3,4,4-hexafluoro cyclopentenes.Patent (JP2010043034) adopts 1-chloro-2,3,3,4,4,5, and synthetic 1,2,2,3,3,4,4-, the seven fluorine cyclopentenes of 5-seven fluorine cyclopentenes and 1-are chloro-2,2,3,3,4,4-hexafluoro cyclopentenes.In addition, patent (JP2001240567) has proposed 1-chloro-2,3,3,4,4,5,5-, seven fluorine cyclopentenes are through hydrogenation synthetic 1,1,2,2,3, the method of 3,4-, seven fluorine pentamethylene, patent (CN200780045548) and patent (US7067468) point out, 1,1,2,2,3,3,4-, seven fluorine pentamethylene are used for removing residual flux, lubricant or oil contaminants as sanitising agent, have been widely used in electronics manufacturing and field of semiconductor manufacture.Therefore, 1-is chloro-2,3,3,4,4,5, and 5-seven fluorine cyclopentenes are being brought into play remarkable effect in organic synthesis technique.
Patent (Eur.Pat.Appl., 203807) discloses a kind of chloro-3,3 by 1,2,3,3,4,4,5,5-octafluoro cyclopentenes and 1,1,2-tri-as far back as 1986, the 3-trifluoro propene synthetic 1-that interacts is chloro-2,3,3,4,4,5, the method for 5-seven fluorine cyclopentenes.Patent (JP2001261594A) discloses a kind of 1,1-bis-chloro-2,2,3 that passes through, 3,4,4,5, the hydrogenation of 5-Octafluorocyclopentane obtains 1-chloro-2,3,3,4,4,5,5-, seven fluorine cyclopentenes and by product 1-chloro-2,2,3,3,4,4, the method of 5,5-Octafluorocyclopentane, this catalyzer loads to gac by Pd/Cu and makes.Non-patent literature (IzvestiyaAkademii Nauk SSSR, Seriya Khimicheskaya, (6), 1430-1; 1990) reported a kind of by the fluoro-3-chloroprene of 1,1,3,5,5-five and CF
2free radical interacts, and to obtain 1-chloro-2,3,3,4,4,5, the novel method of 5-seven fluorine cyclopentenes.Non-patent literature (Zhurnal Obshchei Khimii, 56 (2), 357-64; 1986) also reported a kind of chloro-ly 2,3 by 1-, it is chloro-2,3,3,4,4,5 that 3-trifluoro-ethylene produces 1-, the method for 5-seven fluorine cyclopentenes.In addition, it is chloro-2,3,3,4,4,5 that patent (2001240568) discloses the synthetic 1-of a kind of liquid phase method, the method for 5-seven fluorine cyclopentenes, and the method is chloro-3,3,4,4,5 with 1,2-bis-, and 5-hexafluoro cyclopentenes is raw material, N, N-METHYLFORMAMIDE is solvent.
In addition, chloro-3,3,4,4,5 about 1,2-bis-, 5-hexafluoro cyclopentenes (C
5cl
2f
6) synthetic method also have relevant report.Non-patent literature (J.Am.Chem.Soc., 67,1235 (1945)) has proposed a kind ofly to take antimony trifluoride as catalyzer, and octachlorocyclopentene is that synthetic 1, the 2-bis-of raw material is chloro-3,3,4,4,5, the method for 5-hexafluoro cyclopentenes.Patent (GE3935493) disclose a kind of take antimony pentachloride as catalyzer, to take octachlorocyclopentene and chlorine, hydrogen fluoride be raw material, synthetic 1, the 2-bis-of gas phase is chloro-3,3,4,4,5, the method for 5-hexafluoro cyclopentenes.Patent (RU2318792) discloses a kind ofly take hexachlorocyclopentadiene as raw material, and synthetic 1, the 2-bis-of gas phase is chloro-3,3,4,4,5, the method for 5-hexafluoro cyclopentenes, and it is catalyzer that the method adopts antimony pentachloride.Patent (JPA8333285) has been reported and a kind ofly take butter of antimony as catalyzer, with hexachlorocyclopentadiene, chlorine, and hydrogen fluoride is that synthetic 1, the 2-bis-of raw material is chloro-3,3,4,4,5, the method for 5-hexafluoro cyclopentenes.
In sum, preparation C
5clF
7method all there is certain problem, it is separated that the Repone K that liquid phase method produces and Potassium monofluoride are difficult to, serious to equipment corrosion, high temperature energy consumption is too large, and three industrial wastes are more, and in liquid phase method raw materials used 1,2-bis-chloro-3,3,4,4,5, the preparation method of 5-hexafluoro cyclopentenes, for example catalyzer antimony pentachloride at high temperature, easily runs off for active main minute.
Summary of the invention
The object of the invention is in order to overcome the defect of above prior art, design a kind of raw material sources convenient; By two step gas phase catalytic fluorinations reactions, generate 1-chloro-2,3,3,4,4,5,5-seven fluorine cyclopentenes; Its selectivity of product is relatively good, and intermediate product can recycle, makes this process energy consumption low; Building-up process can realize serialization, it is chloro-2,3,3,4,4,5 to be applicable to synthetic 1-that industrialization generates, the method for 5-seven fluorine cyclopentenes.
Synthetic 1-chloro-2,3,3,4,4,5, the method of 5-seven fluorine cyclopentenes, by catalyzer, it is carried on porous support, with 1,2-bis-chloro-3,3,4,4,5,5-hexafluoro cyclopentenes is raw material, as fluorizating agent, there is fluoridation and make in anhydrous hydrogen fluoride gas, described catalyst activity metal is at least one in chromium, magnesium, zinc, aluminium under 250 ℃ of-600 ℃ of high temperature gas phases in Gas-phase reactor.
In described reaction, HF and 1,2-bis-are chloro-3,3,4,4,5, and the molar ratio of 5-hexafluoro cyclopentenes is 1 ~ 25:1.
In described reaction, HF and 1,2-bis-are chloro-3,3,4,4,5, and the molar ratio of 5-hexafluoro cyclopentenes is 2 ~ 10:1.
In described reaction, temperature of reaction is 290 ~ 550 ℃.
The aftertreatment and the purification step that in described reaction, also comprise this step reaction, described aftertreatment and purification step are: the mixture of fluoridation is removed away after HCl and HF through washing, alkali cleaning, through rectifier unit, separate 1-chloro-2 again, 3,3,4,4,5,5-, seven fluorine cyclopentenes, continue reaction after all the other organism reclaim.
Described 1,2-bis-chloro-3,3,4,4,5,5-hexafluoro cyclopentenes is made by following method: by catalyzer, it is carried on porous support, passes into the mixed gas of chlorine or chlorine and rare gas element, take hexachlorocyclopentadiene as raw material, as fluorizating agent, there is fluoridation and make in anhydrous hydrogen fluoride gas, described catalyst activity metal is at least one in chromium, magnesium, zinc, aluminium under 250 ℃ of-700 ℃ of high temperature gas phases in Gas-phase reactor.
Described 1,2-bis-is chloro-3,3,4,4,5, and 5-hexafluoro cyclopentenes makes HF and C in reaction
5cl
6, Cl
2molar ratio be 5 ~ 25:1:1 ~ 8.
Described 1,2-bis-is chloro-3,3,4,4,5, HF and C in 5-hexafluoro cyclopentenes preparation feedback
5cl
6, Cl
2molar ratio be 7 ~ 20:1:2 ~ 6.
Described 1,2-bis-is chloro-3,3,4,4,5, and it is 290 ~ 500 ℃ that 5-hexafluoro cyclopentenes makes temperature of reaction in reaction.
Described 1,2-bis-chloro-3,3,4,4,5,5-hexafluoro cyclopentenes makes aftertreatment and the purification step that also comprises this step reaction in reaction, and described aftertreatment and purification step are: the mixture of fluoridation is removed away after HCl and HF, then separates 1 through water distilling apparatus through washing, alkali cleaning, 2-bis-chloro-3,3,4,4,5,5-hexafluoro cyclopentenes, continues reaction after all the other organism reclaim.
Before described reaction, need catalyzer to activate, described activation is at N
2or in other inert gas, be heated to 200 ℃ ~ 400 ℃, then activating pretreatment in the HF of HF or inert gas dilution air-flow.
Described activation is for being that 30-80ml/min nitrogen passes in catalyzer by flow velocity, and catalyzer is warmed up to 200 ℃ with 10-30 ℃/min speed and keeps 2 hours, and then is warmed up to 400 ℃ of maintenances 2 hours with 10-30 ℃/min speed; Cool to 330 ℃, then to pass into flow velocity be 30-60ml/min HF, and keep 2 hours at 330 ℃.
Described catalyst activity metal is the mixture of at least one formation in chromium and magnesium, zinc, aluminum metal.
Described support of the catalyst is at least one in gac, aluminum fluoride, aluminum oxide, fluorine alumina, fluorine calcium oxide, Calcium Fluoride (Fluorspan).
Described catalyzer and the weight ratio of carrier are 0.1%-10%.
Described catalyzer and the weight ratio of carrier are 0.5%-5%.
Described Gas-phase reactor is fixed bed, shell and tube or adiabatic reactor.
The material of described reactor is nickelalloy, Hastelloy, Monel metal, because of Kang Hejin or stainless steel.
The present invention has selected at least one active metal as catalyzer in chromium, magnesium, zinc, aluminium, with 1,2-bis-chloro-3,3,4,4,5,5-hexafluoro cyclopentenes, take anhydrous hydrogen fluoride as fluorizating agent, and be chosen under high temperature gas phase condition and react, selectivity of the present invention is very high, and the unreacting material under gas phase condition can reuse after reclaiming.
Its preparation at raw material can adopt existing other method, but preferred method of the present invention adopts same catalyst, and under hot conditions, take equally hexachlorocyclopentadiene, dry chlorine is raw material, and the anhydrous hydrogen fluoride of take makes as fluorizating agent.
Comprehensive two step gas-phase reactions, its process is as follows:
The present invention adopts two step gas phase catalytic fluorination techniques, and two steps are carried out in same fixed-bed reactor, and reactor can be tubular fixed-bed reactor.Reaction product is quality optionally, is the processing of intermediate product, if improper yield, product purity and the process economy that will directly affect second step reaction of intermediate product processing.The first step reaction of the present invention is addition-substitution reaction, and reaction generates 1,2-dichloro hexafluoro cyclopentenes, 1,2,3-trichlorine five fluorine cyclopentenes, a small amount of object product 1-chloro-2,3,3,4,4,5,5-, seven fluorine cyclopentenes, by product HCl and unreacted raw material, only have HCl is removed, just can make reaction carry out to positive dirction; The same unreacted C of the first step
5cl
6(hexachlorocyclopentadiene) also will affect purity and the product yield of second step reaction product, and the present invention, by after distilling, returns to raw material in the first step reaction, has both reduced the waste of reaction raw materials, has alleviated again the aftertreatment burden of rear single step reaction.(1) AHF(anhydrous hydrogen fluoride) and C reaction and sepn process are as follows:
5cl
6, Cl
2with mass flowmeter and volume pump, send in reaction cycle logistics respectively, three's molar ratio is 5 ~ 25:1:1 ~ 8, preferably 7 ~ 20:1:2 ~ 6.After hybrid chamber vaporization, preheating, enter in fixed-bed reactor, temperature of reaction is 200 ~ 700 ℃, preferably 290 ~ 500 ℃.Reaction pressure does not have strict restriction.AHF, Cl
2with C
5cl
6under catalyst action, carry out replacing and generating 1,2-dichloro hexafluoro cyclopentenes, 1,2 after first addition, 3-trichlorine five fluorine cyclopentenes, a small amount of object product 1-are chloro-2,3,3,4,4,5,5-seven fluorine cyclopentenes, by product HCl.Reaction product is sent into the tripping device of HCl together with unreacted raw material; (2) conventional separatory method for the separation of HCl, through washing, alkali cleaning, then washes, and finally carries out separatory, the incoming stock tripping device of separatory organic materials out; (3) separation of raw material is to adopt the distillation method of knowing separated, separates unreacted raw material C
5cl
6enter the first step reaction, lower boiling organism 1,2-dichloro hexafluoro cyclopentenes, comprises on a small quantity 1,2,3-trichlorine five fluorine cyclopentenes are by volume pump, after hybrid chamber vaporization, preheating and AHF enter second step reaction.Second step reaction and separated; (4) in second step reactor, the ratio of AHF and organic materials is 1 ~ 25:1,2 ~ 10:1 preferably, 250 ~ 600 ℃ of temperature of reaction, preferably 290 ~ 500 ℃, from the logistics out of second step reactor, comprise target product 1-chloro-2,3,3,4,4,5,5-seven fluorine cyclopentenes, unreacted AHF and 1,2-dichloro hexafluoro cyclopentenes, 1,2,3-trichlorine five fluorine cyclopentenes, by product HCl etc.; (5) conventional separatory method for the separation of HCl, through washing, alkali cleaning, then washes away unreacted AHF and by product HCl, finally carries out separatory, separatory organic materials out enters rectifier unit through super-dry is laggard, and tower top flows out finished product 1-chloro-2,3,3,4,4,5,5-, seven fluorine cyclopentenes.(6) tower bottom of rectifying tower material collection recycle.
Catalyzer is dried before using, pre-treatment.Pre-treatment is at N by catalyzer
2or in other inert gas, be heated to 200 ℃ ~ 400 ℃; Then activating pretreatment in the HF of HF or inert gas dilution air-flow, just obtains highly active catalyzer.
The present invention by the separating treatment to intermediate product, makes the selectivity of final product good, and by product is few, and the separating treatment to second step reaction product simultaneously allows C
5cl
2f
6recycle, this technique is more optimized, production cost reduces, and meets the policy of China's less energy-consumption, environment protection clean production.
Embodiment
Following examples are described further above-mentioned technological process.
Embodiment 1 ~ 4: the first step reaction
The fixed-bed reactor that are Cr catalyzer to filling active ingredient pass into the nitrogen that flow velocity is 30 ~ 80ml/min, and are warmed up to 200 ℃, keep 2h.Subsequently with same N
2flow velocity rises to 400 ℃ by the temperature of reactor, keeps 2h, cools to afterwards 330 ℃, passes into anhydrous HF, after activation treatment 2h with the flow velocity of 50ml/min.Reaction bed temperature is adjusted to temperature of reaction, passes into gasification, preheated raw material C
5cl
6, HF and Cl
2mixture.Reaction product through washing, after alkali cleaning, dry after.The composition of analyzing organic product with gas chromatograph, the results are shown in table 1.
C
5cl
6transformation efficiency=(C that reaction consumes
5cl
6measure/add C
5cl
6amount) * 100%
The selectivity of F6=(summation of F6 growing amount/growing amount) * 100%
The selectivity of F5=(summation of F5 growing amount/growing amount) * 100%
F6 structure is as follows:
F5 structure is as follows:
Table 1. the first step reaction experiment result
Embodiment 5 ~ 8: second step reaction
The catalyzer that is Zn by active metal component packs same fixed-bed reactor into, by the described mode of the first step reaction, carries out pre-treatment.Reaction bed temperature is adjusted to temperature of reaction, uses respectively volume pump and gas meter by C
5cl
2f
6send into HF that hybrid chamber gasifies, preheating.Reaction product, after washing, alkali cleaning, is collected organic product.The composition of analyzing organic product with gas chromatograph, the results are shown in table 2.
Table 2. second step reaction experiment result
Claims (18)
1. synthesize 1-chloro-2,3,3,4,4,5, the method of 5-seven fluorine cyclopentenes, by catalyzer, it is carried on porous support, with 1,2-bis-chloro-3,3,4,4,5,5-hexafluoro cyclopentenes is raw material, as fluorizating agent, there is fluoridation and make in anhydrous hydrogen fluoride gas, described catalyst activity metal is at least one in chromium, magnesium, zinc, aluminium under 250 ℃ of-600 ℃ of high temperature gas phases in Gas-phase reactor.
2. method according to claim 1, in described reaction, HF and 1,2-bis-are chloro-3,3,4,4,5, and the molar ratio of 5-hexafluoro cyclopentenes is 1 ~ 25:1.
3. method according to claim 2, in described reaction, HF and 1,2-bis-are chloro-3,3,4,4,5, and the molar ratio of 5-hexafluoro cyclopentenes is 2 ~ 10:1.
4. method according to claim 1, in described reaction, temperature of reaction is 290 ~ 550 ℃.
5. method according to claim 1, the aftertreatment and the purification step that in described reaction, also comprise this step reaction, described aftertreatment and purification step are: the mixture of fluoridation is removed away after HCl and HF, then separates 1-chloro-2,3 through rectifier unit through washing, alkali cleaning, 3,4,4,5,5-seven fluorine cyclopentenes, continue reaction after all the other organism reclaim.
6. according to the arbitrary described method of claim 1-5, described 1,2-bis-chloro-3,3,4,4,5,5-hexafluoro cyclopentenes is made by following method: by catalyzer, it is carried on porous support, pass into the mixed gas of chlorine or chlorine and rare gas element, take hexachlorocyclopentadiene as raw material, anhydrous hydrogen fluoride gas is as fluorizating agent, under 250 ℃ of-700 ℃ of high temperature gas phases, in Gas-phase reactor, fluoridation occur and make, described catalyst activity metal is at least one in chromium, magnesium, zinc, aluminium.
7. method according to claim 6, described 1,2-bis-is chloro-3,3,4,4,5, and 5-hexafluoro cyclopentenes makes HF and hexachlorocyclopentadiene in reaction, Cl
2molar ratio be 5 ~ 25:1:1 ~ 8.
8. method according to claim 7, described 1,2-bis-is chloro-3,3,4,4,5, HF and hexachlorocyclopentadiene, Cl in 5-hexafluoro cyclopentenes preparation feedback
2molar ratio be 7 ~ 20:1:2 ~ 6.
9. method according to claim 6, described 1,2-bis-is chloro-3,3,4,4,5, and it is 290 ~ 500 ℃ that 5-hexafluoro cyclopentenes makes temperature of reaction in reaction.
10. method according to claim 6, described 1,2-bis-chloro-3,3,4,4,5,5-hexafluoro cyclopentenes makes aftertreatment and the purification step that also comprises this step reaction in reaction, and described aftertreatment and purification step are: the mixture of fluoridation is removed away after HCl and HF through washing, alkali cleaning, through water distilling apparatus, separate 1,2-bis-chloro-3,3 again, 4,4,5,5-hexafluoro cyclopentenes, continues reaction after all the other organism reclaim.
11. methods according to claim 6, before described reaction need catalyzer to activate, and described activation is at N
2or in other inert gas, be heated to 200 ℃ ~ 400 ℃, then activating pretreatment in the HF of HF or inert gas dilution air-flow.
12. methods according to claim 11, described activation is is that 30-80ml/min nitrogen passes in catalyzer by flow velocity, catalyzer is warmed up to 200 ℃ with 10-30 ℃/min speed and keeps 2 hours, and then is warmed up to 400 ℃ of maintenances 2 hours with 10-30 ℃/min speed; Cool to 330 ℃, then to pass into flow velocity be 30-60ml/min HF, and keep 2 hours at 330 ℃.
13. according to the arbitrary described method of claim 1-12, and described catalyst activity metal is the mixture of at least one formation in chromium and magnesium, zinc, aluminum metal.
14. according to the arbitrary described method of claim 1-12, and described support of the catalyst is at least one in gac, aluminum fluoride, aluminum oxide, fluorine alumina, fluorine calcium oxide, Calcium Fluoride (Fluorspan).
15. according to the arbitrary described method of claim 1-14, and described catalyzer and the weight ratio of carrier are 0.1%-10%.
16. methods according to claim 15, described catalyzer and the weight ratio of carrier are 0.5%-5%.
17. according to the arbitrary described method of claim 1-16, and described Gas-phase reactor is fixed bed, shell and tube or adiabatic reactor.
18. according to the arbitrary described method of claim 17, and the material of described reactor is nickelalloy, Hastelloy, Monel metal, because of Kang Hejin or stainless steel.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104907065A (en) * | 2014-03-12 | 2015-09-16 | 北京宇极科技发展有限公司 | Fluorination catalyst, and preparation method and use thereof |
| CN104907063A (en) * | 2014-03-12 | 2015-09-16 | 北京宇极科技发展有限公司 | Chromium base catalyst, and preparation method and use thereof |
| CN107188778A (en) * | 2017-05-18 | 2017-09-22 | 北京宇极科技发展有限公司 | The preparation method of octafluoro cyclopentene |
| JP2017190294A (en) * | 2016-04-12 | 2017-10-19 | 国立研究開発法人産業技術総合研究所 | Manufacturing method of 1-chloroheptafluorocyclopentene |
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|---|---|---|---|---|
| US5180861A (en) * | 1989-10-28 | 1993-01-19 | Bayer Aktiengesellschaft | Process for the preparation of polychloro-fluoro-cyclo-pentenes |
| CN1680233A (en) * | 1997-09-17 | 2005-10-12 | 森陶硝子株式会社 | Method for producing perhalogenated cyclopentene |
-
2012
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5180861A (en) * | 1989-10-28 | 1993-01-19 | Bayer Aktiengesellschaft | Process for the preparation of polychloro-fluoro-cyclo-pentenes |
| CN1680233A (en) * | 1997-09-17 | 2005-10-12 | 森陶硝子株式会社 | Method for producing perhalogenated cyclopentene |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104907065A (en) * | 2014-03-12 | 2015-09-16 | 北京宇极科技发展有限公司 | Fluorination catalyst, and preparation method and use thereof |
| CN104907063A (en) * | 2014-03-12 | 2015-09-16 | 北京宇极科技发展有限公司 | Chromium base catalyst, and preparation method and use thereof |
| CN104907065B (en) * | 2014-03-12 | 2019-08-02 | 北京宇极科技发展有限公司 | Fluorination catalyst, Preparation method and use |
| JP2017190294A (en) * | 2016-04-12 | 2017-10-19 | 国立研究開発法人産業技術総合研究所 | Manufacturing method of 1-chloroheptafluorocyclopentene |
| CN107188778A (en) * | 2017-05-18 | 2017-09-22 | 北京宇极科技发展有限公司 | The preparation method of octafluoro cyclopentene |
| CN107188778B (en) * | 2017-05-18 | 2020-08-21 | 北京宇极科技发展有限公司 | Preparation method of octafluorocyclopentene |
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|---|---|
| CN103570491B (en) | 2015-05-27 |
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