CN103570491B - 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 the method for chloro-2,3,3,4,4,5, the 5-seven fluorine cyclopentenes of a kind of two step gas phase catalytic synthesis 1-, relates to one by chlorine, anhydrous hydrogen fluoride gas and hexachlorocyclopentadiene, interacts under high temperature gas phase with catalyzer, generate C
5clF
7method.
Background technology
Chloro-2,3,3,4,4,5, the 5-seven fluorine cyclopentenes of 1-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) one is described with chloro-2,3,3,4,4,5, the 5-seven fluorine cyclopentenes of 1-for raw material, the method for synthesis chloro-2,2,3,3,4, the 4-hexafluoro cyclopentenes of 1-and 2,2,3,3,4,4-hexafluoro cyclopentenes.Patent (JP2010043034) adopts chloro-2,3,3,4,4,5,5-seven fluorine cyclopentenes synthesis 1,2,2,3,3,4,4-seven fluorine cyclopentenes and chloro-2,2,3,3,4, the 4-hexafluoro cyclopentenes of 1-of 1-.In addition, patent (JP2001240567) proposes 1-chloro-2, and 3,3,4,4,5,5-seven fluorine cyclopentenes is through hydrogenation synthesis 1,1,2,2,3, the method of 3,4-seven fluorine pentamethylene, patent (CN200780045548) and patent (US7067468) are pointed out, 1,1,2,2,3,3,4-seven fluorine pentamethylene is used for removing residual flux, lubricant or oil contaminants as sanitising agent, has been widely used in electronics manufacturing and field of semiconductor manufacture.Therefore, chloro-2,3,3,4,4,5, the 5-seven fluorine cyclopentenes of 1-play remarkable effect in organic synthesis technique.
Patent (Eur.Pat.Appl., 203807) disclosed a kind of interaction by 1,2,3,3,4,4,5,5-octafluoro cyclopentenes and chloro-3,3, the 3-trifluoro propenes of 1,1,2-tri-and synthesizes the method for chloro-2,3,3,4,4,5, the 5-seven fluorine cyclopentenes of 1-as far back as 1986.Patent (JP2001261594A) discloses a kind of by 1,1-bis-chloro-2, and 2,3,3,4,4,5, the hydrogenation of 5-Octafluorocyclopentane obtains 1-chloro-2, and 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 obtains.Non-patent literature (IzvestiyaAkademii Nauk SSSR, Seriya Khimicheskaya, (6), 1430-1; 1990) one is reported by the fluoro-3-chloroprene of 1,1,3,5,5-five and CF
2free radical interacts and obtains the novel method of chloro-2,3,3,4,4,5, the 5-seven fluorine cyclopentenes of 1-.Non-patent literature (Zhurnal Obshchei Khimii, 56 (2), 357-64; 1986) a kind of method being produced chloro-2,3,3,4,4,5, the 5-seven fluorine cyclopentenes of 1-by chloro-2,3, the 3-trifluoro-ethylenes of 1-is also reported.In addition, patent (2001240568) discloses the method for chloro-2,3,3,4,4,5, the 5-seven fluorine cyclopentenes of a kind of liquid phase method synthesis 1-, and the method is with chloro-3,3,4,4,5, the 5-hexafluoro cyclopentenes of 1,2-bis-for raw material, and N, N-METHYLFORMAMIDE is solvent.
In addition, about chloro-3,3,4,4,5, the 5-hexafluoro cyclopentenes (C of 1,2-bis-
5cl
2f
6) synthetic method also have relevant report.It is catalyzer with antimony trifluoride that non-patent literature (J.Am.Chem.Soc., 67,1235 (1945)) proposes a kind of, and octachlorocyclopentene is the method for chloro-3,3,4,4,5, the 5-hexafluoro cyclopentenes of Material synthesis 1,2-bis-.Patent (GE3935493) disclose a kind of take antimony pentachloride as catalyzer, with octachlorocyclopentene and chlorine, hydrogen fluoride for raw material, the method for chloro-3,3,4,4,5, the 5-hexafluoro cyclopentenes of vapor-phase synthesis 1,2-bis-.It is raw material with hexachlorocyclopentadiene that patent (RU2318792) discloses a kind of, the method for chloro-3,3,4,4,5, the 5-hexafluoro cyclopentenes of vapor-phase synthesis 1,2-bis-, and the method adopts antimony pentachloride to be catalyzer.Patent (JPA8333285) report a kind of be catalyzer with butter of antimony, with hexachlorocyclopentadiene, chlorine, hydrogen fluoride is the method for chloro-3,3,4,4,5, the 5-hexafluoro cyclopentenes of Material synthesis 1,2-bis-.
In sum, C is prepared
5clF
7method all there is certain problem, liquid phase method produce Repone K be difficult to be separated with Potassium monofluoride, 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, such as catalyzer antimony pentachloride at high temperature, and active main point easily runs off.
Summary of the invention
The object of the invention is the defect in order to overcome above prior art, designing a kind of raw material sources convenient; Chloro-2,3,3,4,4,5, the 5-seven fluorine cyclopentenes of 1-are generated by two step gas phase catalytic fluorination reactions; Its selectivity of product is relatively good, and intermediate product can recycle, makes this process energy consumption low; Building-up process can realize serialization, be applicable to the method for chloro-2,3,3,4,4,5, the 5-seven fluorine cyclopentenes of synthesis 1-that industrialization generates.
Synthesis 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 obtain in anhydrous hydrogen fluoride gas, described catalyst activity metal is at least one in chromium, magnesium, zinc, aluminium under 250 DEG C of-600 DEG C of high temperature gas phases in Gas-phase reactor.
In described reaction, the molar ratio of chloro-3,3,4,4,5, the 5-hexafluoro cyclopentenes of HF and 1,2-bis-is 1 ~ 25:1.
In described reaction, the molar ratio of chloro-3,3,4,4,5, the 5-hexafluoro cyclopentenes of HF and 1,2-bis-is 2 ~ 10:1.
In described reaction, temperature of reaction is 290 ~ 550 DEG C.
Aftertreatment and the purification step of the reaction of this step is also comprised in described reaction, described aftertreatment and purification step are: by the mixture of fluoridation through washing, alkali cleaning except going out after HCl and HF, 1-chloro-2 is separated again through rectifier unit, 3,3,4,4,5,5-seven fluorine cyclopentenes, all the other organism continue reaction after reclaiming.
Described 1,2-bis-chloro-3,3,4,4,5,5-hexafluoro cyclopentenes is obtained 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, anhydrous hydrogen fluoride gas is as fluorizating agent, and under 250 DEG C of-700 DEG C of high temperature gas phases, in Gas-phase reactor, fluoridation occurs and obtain, described catalyst activity metal is at least one in chromium, magnesium, zinc, aluminium.
HF and C in the obtained reaction of described 1,2-bis-chloro-3,3,4,4,5,5-hexafluoro cyclopentenes
5cl
6, Cl
2molar ratio be 5 ~ 25:1:1 ~ 8.
HF and C in described 1,2-bis-chloro-3,3,4,4,5,5-hexafluoro cyclopentenes preparation feedbacks
5cl
6, Cl
2molar ratio be 7 ~ 20:1:2 ~ 6.
In the obtained reaction of described 1,2-bis-chloro-3,3,4,4,5,5-hexafluoro cyclopentenes, temperature of reaction is 290 ~ 500 DEG C.
Described 1,2-bis-chloro-3,3,4,4,5,5-hexafluoro cyclopentenes obtains in reaction the aftertreatment and purification step that also comprise the reaction of this step, and described aftertreatment and purification step are: the mixture of fluoridation except going out after HCl and HF, then is separated 1 through water distilling apparatus through washing, alkali cleaning, 2-bis-chloro-3,3,4,4,5,5-hexafluoro cyclopentenes, all the other organism continue reaction after reclaiming.
Need before described reaction to activate catalyzer, described activation is at N
2or be heated to 200 DEG C ~ 400 DEG C in other inert gas, then activating pretreatment in the HF air-flow of HF or inert gas dilution.
Described activation is for being that 30-80ml/min nitrogen passes in catalyzer by flow velocity, and catalyzer is warmed up to 200 DEG C with 10-30 DEG C/min speed and keeps 2 hours, and then is warmed up to 400 DEG C of maintenances 2 hours with 10-30 DEG C/min speed; Cool to 330 DEG C, then to pass into flow velocity be 30-60ml/min HF, and keep 2 hours at 330 DEG C.
The mixture that described catalyst activity metal is chromium and magnesium, at least one in zinc, aluminum metal is formed.
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 be nickelalloy, Hastelloy, Monel metal, because of Kang Hejin or stainless steel.
The present invention have selected the active metal of at least one in chromium, magnesium, zinc, aluminium as catalyzer, with 1,2-bis-chloro-3,3,4,4,5,5-hexafluoro cyclopentenes, take anhydrous hydrogen fluoride as fluorizating agent, and select to react under high temperature gas phase condition, 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 other method existing, but preferred method of the present invention, namely adopts same catalyst, equally under the high temperature conditions with hexachlorocyclopentadiene, dry chlorine for raw material, be that fluorizating agent obtains with anhydrous hydrogen fluoride.
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 optionally fine or not, is the process of intermediate product, if the improper of intermediate product process will directly affect yield, product purity and the process economy of second step reaction.The first step reaction of the present invention is addition-substitution reaction, reaction generation 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 and HCl is removed, reaction just can be made to carry out to positive dirction; The unreacted C of the same 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 distillation, returns raw material in the first step reaction, both decreased the waste of reaction raw materials, alleviate again the aftertreatment burden of rear single step reaction.Reaction and sepn process as follows: (1) AHF(anhydrous hydrogen fluoride) and C
5cl
6, Cl
2send in reaction cycle logistics with mass flowmeter and volume pump respectively, the molar ratio of three is 5 ~ 25:1:1 ~ 8, preferably 7 ~ 20:1:2 ~ 6.Enter in fixed-bed reactor after hybrid chamber vaporization, preheating, temperature of reaction is 200 ~ 700 DEG C, preferably 290 ~ 500 DEG C.Reaction pressure does not have strict restriction.AHF, Cl
2with C
5cl
6generation 1,2-dichloro hexafluoro cyclopentenes, 1,2,3-trichlorine five fluorine cyclopentenes, a small amount of chloro-2,3,3,4,4,5, the 5-seven fluorine cyclopentenes of object product 1-, by product HCl is replaced carry out first addition under catalyst action after.Reaction product sends into the tripping device of HCl together with unreacted raw material; (2) the separatory method that the separation of HCl is conventional, through washing, alkali cleaning, then washes, finally carries out separatory, the incoming stock tripping device of separatory organic materials out; (3) separation of raw material adopts the distillation method known to be separated, and separates unreacted raw material C
5cl
6enter the first step reaction, lower boiling organism 1,2-dichloro hexafluoro cyclopentenes, comprise 1,2,3-a small amount of trichlorine five fluorine cyclopentenes by volume pump, after hybrid chamber vaporization, preheating and AHF enter second step reaction.Second step reaction and separation; (4) in second step reactor, the ratio of AHF and organic materials is 1 ~ 25:1, preferably 2 ~ 10:1, temperature of reaction 250 ~ 600 DEG C, preferably 290 ~ 500 DEG C, comprise target product 1-chloro-2,3 from the logistics out of second step reactor, 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) the separatory method that the separation of HCl is conventional, through washing, alkali cleaning, then washes away unreacted AHF and by product HCl, finally carries out separatory, separatory organic materials out through super-dry laggard enter rectifier unit, 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 carries out drying, pre-treatment before using.Pre-treatment is at N by catalyzer
2or in other inert gas, be heated to 200 DEG C ~ 400 DEG C; Then activating pretreatment in the HF air-flow of HF or inert gas dilution, just obtains highly active catalyzer.
The present invention is by separating treatment to intermediate product, and make the selectivity of final product good, by product is few, simultaneously to the separating treatment of second step reaction product, 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 is reacted
The fixed-bed reactor being Cr catalyzer to filling active ingredient pass into the nitrogen that flow velocity is 30 ~ 80ml/min, and are warmed up to 200 DEG C, keep 2h.Subsequently with same N
2the temperature of reactor is risen to 400 DEG C by flow velocity, keeps 2h, cools to 330 DEG C afterwards, pass 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 is after washing, alkali cleaning, after drying.With the composition of chromatographic organic product, the results are shown in table 1.
C
5cl
6transformation efficiency=(C that reaction consumes
5cl
6measure/add C
5cl
6amount) × 100%
Selectivity=(summation of F6 growing amount/growing amount) × 100% of F6
Selectivity=(summation of F5 growing amount/growing amount) × 100% of F5
F6 structure is as follows:
F5 structure is as follows:
Table 1. the first step reaction experiment result
Embodiment 5 ~ 8: second step reacts
Be that the catalyzer of Zn loads same fixed-bed reactor by active metal component, carry out pre-treatment by the mode described in the first step reaction.Reaction bed temperature is adjusted to temperature of reaction, uses volume pump and gas meter by C respectively
5cl
2f
6send into HF that hybrid chamber carries out gasifying, preheating.Organic product, after washing, alkali cleaning, is collected by reaction product.With the composition of chromatographic organic product, the results are shown in table 2.
Table 2. second step reaction experiment result
Claims (9)
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, under 250 DEG C of-600 DEG C of high temperature gas phase, in Gas-phase reactor, there is fluoridation obtain in anhydrous hydrogen fluoride gas;
In described reaction, the molar ratio of chloro-3,3,4,4,5, the 5-hexafluoro cyclopentenes of HF and 1,2-bis-is 1 ~ 25:1;
Aftertreatment and the purification step of the reaction of this step is also comprised in described reaction, described aftertreatment and purification step are: by the mixture of fluoridation through washing, alkali cleaning except going out after HCl and HF, 1-chloro-2 is separated again through rectifier unit, 3,3,4,4,5,5-seven fluorine cyclopentenes, all the other organism continue reaction after reclaiming;
Described 1,2-bis-chloro-3,3,4,4,5,5-hexafluoro cyclopentenes is obtained 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, under 250 DEG C of-700 DEG C of high temperature gas phase, in Gas-phase reactor, there is fluoridation and obtain in anhydrous hydrogen fluoride gas;
In described catalyzer, active metal is at least one in chromium, magnesium, zinc, aluminium;
HF and hexachlorocyclopentadiene, Cl in the obtained reaction of described 1,2-bis-chloro-3,3,4,4,5,5-hexafluoro cyclopentenes
2molar ratio be 5 ~ 25:1:1 ~ 8;
Described 1,2-bis-chloro-3,3,4,4,5,5-hexafluoro cyclopentenes obtains in reaction the aftertreatment and purification step that also comprise the reaction of this step, and described aftertreatment and purification step are: the mixture of fluoridation except going out after HCl and HF, then is separated 1 through water distilling apparatus through washing, alkali cleaning, 2-bis-chloro-3,3,4,4,5,5-hexafluoro cyclopentenes, all the other organism continue reaction after reclaiming;
Need before described reaction to activate catalyzer, described activation is at N
2or be heated to 200 DEG C ~ 400 DEG C in other inert gas, then activating pretreatment in the HF air-flow of HF or inert gas dilution;
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 Gas-phase reactor is fixed bed or shell and tube reactor.
2. method according to claim 1, in described reaction, the molar ratio of chloro-3,3,4,4,5, the 5-hexafluoro cyclopentenes of HF and 1,2-bis-is 2 ~ 10:1.
3. method according to claim 1, the temperature of reaction of chloro-3,3,4,4,5, the 5-hexafluoro cyclopentenes of described HF and 1,2-bis-is 290 ~ 550 DEG C.
4. method according to claim 1, HF and hexachlorocyclopentadiene, Cl in described 1,2-bis-chloro-3,3,4,4,5,5-hexafluoro cyclopentenes preparation feedbacks
2molar ratio be 7 ~ 20:1:2 ~ 6.
5. method according to claim 1, in the obtained reaction of described 1,2-bis-chloro-3,3,4,4,5,5-hexafluoro cyclopentenes, temperature of reaction is 290 ~ 500 DEG C.
6. method according to claim 1, described activation is for being that 30-80ml/min nitrogen passes in catalyzer by flow velocity, catalyzer is warmed up to 200 DEG C with 10-30 DEG C/min speed and keeps 2 hours, and then is warmed up to 400 DEG C of maintenances 2 hours with 10-30 DEG C/min speed; Cool to 330 DEG C, then to pass into flow velocity be 30-60ml/min HF, and keep 2 hours at 330 DEG C.
7. method according to claim 1, in described catalyzer, active metal is at least one in chromium and magnesium, zinc, aluminium.
8. method according to claim 1, described catalyzer and the weight ratio of carrier are 0.5%-5%.
9. according to the arbitrary described method of claim 1-8, the material of described reactor be nickelalloy, Hastelloy, Monel metal, because of Kang Hejin or stainless steel.
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| 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 |
| JP6623476B2 (en) * | 2016-04-12 | 2019-12-25 | 国立研究開発法人産業技術総合研究所 | Method for producing 1-chloroheptafluorocyclopentene |
| CN107188778B (en) * | 2017-05-18 | 2020-08-21 | 北京宇极科技发展有限公司 | Preparation method of octafluorocyclopentene |
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 |
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| 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 |
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