CN101597208B - Method for preparing fluorinated alkene by high temperature wet-cracking - Google Patents
Method for preparing fluorinated alkene by high temperature wet-cracking Download PDFInfo
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Abstract
The invention relates to a method for preparing fluorinated alkene by high temperature wet-cracking, belonging to the field of organic synthesis. The method is characterized in that under the condition of normal pressure and the temperature of 600-1000DEG C, hydrogen fluoride alkane with the molecular formula of HnFmC3 (n +m=8, n is more than or equal to 1 and less than or equal to 8, and m is more than or equal to 2 and less than 8) is taken as raw gas to have cracking reaction in the environment of water vapor or ammonia water vapor; no catalyst is used in the method, so that the generation cost is reduced, by-products are few, the selectivity of the product is high, subsequent purification and separation are convenient, the whole technique is easy to control, and the method is very suitable for producing the fluorinated alkene in industrialization-scale.
Description
Technical field
The present invention relates to the synthetic field of organism, particularly relate to a kind of method of preparing fluorinated alkene by high temperature wet-cracking.
Background technology
HCFC (CFCs) like methyl chlorofluoride and CClF3 etc., is widely used as the thinner of refrigeration agent, whipping agent and gaseous disinfectant with its good performance.In recent years, it is found that fluorochlorohydrocarbon class thing has destruction to earth atmosphere, also produce Greenhouse effect, this problem receives extensive concern.Therefore, the whole world is just striving to find and is having life-span weak point, the halogenated hydrocarbon substitute of low Greenhouse effect.According to present case; Hydrogen fluorohydrocarbon compounds (HFCs) or the only preparation of the compound of carbon containing, hydrogen and fluorine element; Become a very popular topic, study and provide eco-friendly solvent, whipping agent, refrigeration agent, clean-out system, aerosol propellants, heat-transfer medium, dielectric, fire-fighting medium and power cycle working liquid.
The HFCs compounds mainly is to be used for CFC alternative s and HCFCs, be widely used as refrigeration agent (like HFC-134a, CF3CH2F), whipping agent (HFC-245fa, CF3CH2CHF2) and fire-fighting medium (HFC-236, CF3CH2CF3 and HFC-227, CF3CHFCF3) etc.Yet the GWP of HFCs compounds (Global warming index) is higher relatively, and present research mainly concentrates on the short Fluorine containing olefine of synthetic atmospheric lifetime, eliminates the HFCs compound, as is applied to the HFC-134a of automative air conditioning.
Fluorine containing olefine is a kind of very useful monomer in the polyreaction of synthetic Viton.Some Fluorine containing olefine can also be used as refrigeration agent of new generation, the low GWP exponential CFCs of a new generation such as whipping agent surrogate.
U.S. Pat 6703533, US6369284, Japanese Patent JP09095459 and JP09067281, and disclose among the patent WO2004018093 under 500 ℃; 1,1,1,3; 3, the 3-HFC-236fa generates 1,1 through catalyst action; 3,3, the method for 3-five fluorine propylene; Perfluoro alkane, especially hydrochlorofluorocar,ons generally do not take place to decompose under 300 ℃ with other perfluor verivates and all show extraordinary thermostability, but require long RT-RT to be meant under given temperature of reaction and pressure under this temperature; The gas that is meant certain volume is in the mean time that reaction zone stops, and this scission reaction of Financial cost implement to(for) technical scale is very unreasonable, and can produce a large amount of by products; These materials can resolve into all possible fragment molecule under 500 ℃～800 ℃, generate very complicated and difficult isolating mixture, at high temperature are prone to resolve into the fragment molecule in order to prevent fluorocarbon; Catalyzer in the disclosed technical scheme of above-mentioned patent documentation is selected from oxide compound, fluorochemical, Sellaite, zinc fluoride; And the mixed fluoride thing of magnesium and zinc, lanthanum fluoride, the low temperature catalysts such as mixture of fluorizated lanthanum trioxide and three-dimensional carbonaceous material and these materials.In chemical reaction; Catalyzer not only too costliness make reaction cost very high; And the catalytic preparation Fluorine containing olefine comprises activation, the catalyst deactivation of Preparation of catalysts, raw catalyst, complex procedures, and reaction is difficult to control; To the processing of catalyzer, activation or reaction for a long time and to the space-time yield of reactor drum strict requirement is arranged all, under the situation that has the polymer by product to produce, be filled with the reactor drum easy blocking of catalyzer.Be called in the disclosed scheme of specification sheets of " catalytic pyrolysis monochlorodifluoromethane system tetrafluoroethylene " such as being 89101961.8 at application number; The selectivity of its product tetrafluoroethylene can reach 98%; The transformation efficiency of monochlorodifluoromethane is 40%; Temperature of reaction still needs complicated catalystsystem between 400-700 ℃.
U.S. Pat 2002/0032356 discloses a kind of method that in the golden cracking reactor of lining, prepares perfluorinated monomers tetrafluoroethylene and R 1216; Its technical scheme is in the reactor drum that has served as a contrast one deck gold or other precious metal, to carry out scission reaction; The gold of small pieces of cloth used for patches plays a part catalyzer on the inwall, and the reagent of reaction and equipment cost are all too high.
So far, under the catalyst-free condition, be that the method for raw material produced in high yields Fluorine containing olefine is not also appeared in the newspapers with the hydro fluoroalkanes of three carbon atoms.
Summary of the invention
The present invention is directed to the blank of above-mentioned technical field and the defective of prior art; Provide a kind of high temperature wet cracking hydro fluoroalkanes to prepare the method for the Fluorine containing olefine of corresponding carbon number, it is reflected in water vapor or the ammonia vapor and carries out, and does not use any catalyzer; Selectivity of product is high, and technology is easy to control.
A kind of method of preparing fluorinated alkene by high temperature wet-cracking is characterized in that being H with the molecular formula under the normal pressure 600-1000 ℃ temperature
nF
mC
3Hydro fluoroalkanes be that unstripped gas is carried out scission reaction in water vapor or ammonia vapor environment, n+m=8 wherein, 1≤n≤6,2≤m≤7.
The charge flow rate of said unstripped gas is 10-100ml/min, and said water vapor or ammonia vapor charge flow rate are 0.3～0.9g/min.
The charge flow rate of said unstripped gas is 30ml/min.
The RT of said unstripped gas is 0.01-10s.
The RT of said unstripped gas is 0.03-1s.
The temperature of said scission reaction is 700～900 ℃.
The temperature of said scission reaction is 750～850 ℃.
Said hydro fluoroalkanes is CF
3CH
2CF
3, CF
3CH
2CHF
2, CF3CH2CHF2, CF2HCH2CHF2 or CF3CHFCF3.
Method of the present invention is under water vapour or ammoniacal liquor steam condition, and normal pressure is heated to 600～1000 ℃ makes the hydro fluoroalkanes generation scission reaction that contains three carbon atoms produce the Fluorine containing olefine that contains three carbon atoms, and scission reaction is following:
Do not use catalyzer, this process has been avoided desired critical conditions and operational drawback under the situation of using catalyzer, has saved the expensive catalysts expense, is suitable for commercial scale prodn; And the selectivity of product that is obtained is very high, and the experimental result of embodiment 1 can find out that the dry method cracking that the selectivity of the reaction product Fluorine containing olefine of wet method cleavage method of the present invention is higher than under the same terms prepares Fluorine containing olefine, shown in table 1 and table 2.Can find out that from the data of other embodiment wet method cracking of the present invention prepares Fluorine containing olefine and has following characteristics: the first, thermo-cracking does not make the HFCs of three carbon atoms be cracked into the fragmentation compound of 1 C or 2 C in a large number; Like CO, CO2, ethane and ethene etc.; Like table 1,3,4,5,6, shown in 7; " other " product proportion in the table explains that its by product ratio of cleavage method of the present invention is very low between 0～16.6%, the selectivity that obtains Fluorine containing olefine is very high; Skilled in the art will recognize that; Obtain the reaction product of highly selective; Can simplify complicated later separation program in a large number, save the PT significantly, operation, Material Cost, second; The product Fluorine containing olefine that obtains is stable under reaction conditions, and the compound that contains Wasserstoffatoms still less or fluorine atom takes place to reset or generate.
The charge flow rate 10-100ml/min of preferred feedstock gas of the present invention neither wastes equipment in this scope, then be easy to generate more by product greater than 100ml/min, and this scope can be taken into account the transformation efficiency and the selectivity of scission reaction simultaneously; The charge flow rate of water vapor or ammonia vapor is the charge flow rate of 0.3-0.9g/min. with respect to unstripped gas, and when water vapor or ammonia vapor charge flow rate very little the time, reactant is prone to decompose produce and stops up, and when the water vapor charge flow rate is too many, then can reduce transformation efficiency.The data of embodiment 2,4,5 can find out that under this condition, the stability of scission reaction is better, and the transformation efficiency of unstripped gas and product selectivity all do not have significantly fluctuation.Preferred feedstock gas charge flow rate of the present invention is 30ml/min, and transformation efficiency and selectivity can be taken into account like this, and maximization improves reaction efficiency.
Among the present invention, the RT of unstripped gas is 0.03-10s, the oversize then easy more by product that generates of RT; RT is too short; Then transformation efficiency is too low, and the unstripped gas cycle index increases, and has increased industrial energy consumption (transformation efficiency refers to the ratio of reactant single through the reactor drum post consumption); In order further to take into account transformation efficiency and selectivity, the preferred RT of the present invention is 0.05～3s.
Reaction product of the present invention comprises hydrogen fluoride; Have very strong corrosive nature, for the factory that does not possess corrosion-resistant conversion unit, the corrosive nature of reaction product will cause these factories to have to often update the equipment; To increase equipment cost greatly; Available ammonia vapor replaces water vapor in the scission reaction environment of the present invention, ammonia vapor on the one hand can in and hydrogen fluoride, avoid hydrogen fluoride to corrosion on Equipment; Ammonia vapor and hydrofluoric neutralization reaction can promote scission reaction to carry out to forward, improve reaction efficiency; On the other hand, feed ammonia vapor and also can prevent problems such as conversion unit line clogging, also do not need extra high cracking temperature, the selectivity in the time of 750 ℃ is the highest, sees table 7, can reduce industrial energy consumption equally.Ammonia vapor and the preferred 0.3～0.9g/min of charge flow rate.
The scission reaction temperature that the present invention adopts is being carried out more than 600 ℃, and top temperature is no more than 1000 ℃, and is preferred more than 650 ℃, is no more than 950 ℃; Be preferably 700～900 ℃ again, more preferably 750～850 ℃, cracking temperature is meant the gas temperature of reaction zone central interior.As shown in table 4 by experimental data, can find out at 650～950 ℃, along with temperature raises; The transformation efficiency of unstripped gas raises gradually; And the selectivity of tetrafluoeopropene reduces gradually, no matter is in water vapor or ammonia vapor environment, the relative optimization of transformation efficiency in the time of 750～800 ℃ and selectivity.
The preferred CF of the present invention
3CH
2CF
3, CF
3CH
2CHF
2, CF3CH2CHF2, CF2HCH2CHF2 or CF3CHFCF3, particularly CF
3CH
2CF
3CF3CH2CHF2 prepares the Fluorine containing olefine of three carbon atoms, and above-mentioned two kinds of hydrogen fluorohydrocarbons all are the raw materials that is commonly used at present as refrigeration agent, whipping agent, fire-fighting medium, and these reagent its Global warming index in use are higher relatively; People are eager to study novel substance to replace their application in life at present; The present invention is a raw material with them, and being unlikely to has wasted old material when adopting novel material, neither wastes resource and has solved environmental problem again.
It is 1: 1 HF and Fluorine containing olefine miscellany that process of the present invention has generated mol ratio, also comprises unconverted reactant HFCs compound.Each component in the reaction product can be separated through traditional method, like rectifying.The reactor outlet product of process of the present invention can rectifying separation; Lower boiling HF and Fluorine containing olefine miscellany are components before the rectifying tower; Pure HFC is stayed the rectifying tower still, and Fluorine containing olefine can separate in the miscellany through method commonly used and HF, like compression rectification or add in the alkali method with HF etc.
Embodiment
Cracking reactor: indium scandium pipe, long 30cm, 1/8 inch of external diameter (0.31cm), thickness of pipe is 0.11cm.Electrically heated is adopted in reaction, measures reaction zone temperature with thermopair.
Reaction outlet product is analyzed the online detection of GC by GC-MS.
Embodiment 1: be HFC-236fa water vapour wet method cracking dehydrofluorination and the contrast of dry method scission reaction.
Wet method cracked parameter: the pipe temperature is a temperature of reaction in the reactor drum, reactant CF
3CH
2CF
3Charge flow rate is 30ml/min, and the water vapour flow calculates with the steam output of 0.6g/min, and the reaction times is 0.04s.Experimental result is listed in table 1, and main by product is CO, CO2.
CF
3CH
2CF
3——→CF
3CH＝CF
2+HF
Table 1 wet method cracking HFC-236fa experimental result
With the cracking dehydrofluorination that does not add water vapor or ammonia vapor condition is contrast:
The pipe temperature is a temperature of reaction in the reactor drum, and reactant CF3CH2CF3 charge flow rate is 30ml/min, and the reaction times is 0.04s, and experimental result is listed in table 2, and main by product is CO, CO2.
Table 2 dry method cracking HFC-236fa experimental result
The result of table 1, table 2 shows; Under the water vapor condition, the selectivity of the Fluorine containing olefine that identical temperature obtains obviously will be higher than the selectivity that does not have under the water vapor condition, and by product is also much lower; Water vapor and ammonia vapor can prevent the conversion unit line clogging; Impel reaction forward to carry out, the effect of regulating the equilibrium temperature condition is arranged simultaneously, make reaction be easy to control.
2 850 ℃ of following steam vapour amounts of embodiment are to the influence of wet method cracking HFC-236fa dehydrofluorination
Reactor drum is the same, and the pipe temperature is a temperature of reaction in the reactor drum, and reactant CF3CH2CF3 charge flow rate is 30ml/min, and the water vapour flow calculates with the PM steam output, and the reaction times approximately is that its reaction conditions of 0.04s and corresponding experiment result are listed in table 3.Main by product is CO, CO2.
The experimental result of 850 ℃ of following water vapour wet method cracking HFC-236fa of table 3
The result is illustrated in the water vapor amount flow range that the present invention selectes, and 850 ℃ of following transformation efficiencys do not have to change basically, and selectivity is along with the increase of water vapor amount improves a little.
Embodiment 3. temperature of reaction are taken off the influence of HF reaction to water vapour wet method cracking HFC-245fa
Reaction process is following:
The pipe temperature is a temperature of reaction in the reactor drum, and reactant CF3CH2CHF2 charge flow rate is 30ml/min, and the water vapour flow calculates with the steam output of 0.6g/min, and the reaction times is 0.04s.Reaction conditions and result see table 4, and main by product is CO, CO2.
Table 4 temperature of reaction is to the influence of water vapour wet method cracking HFC-245fa experimental result
Experimental result shows that along with temperature raises, the transformation efficiency of wet method cracking HFC-245fa increases gradually under these conditions, and the trans and selectivity cis tetrafluoeopropene reduces gradually.Reach more than 95% at 750～800 ℃ of transformation efficiencys, by product is about 0.2～1.1%, and the gained result is consistent with the rule of table 1.
Embodiment 4 is the influences of 800 ℃ of following water vapor amounts to wet method cracking HFC-245fa
Other conditions are with embodiment 3, and the result sees table 5.Main by product is CO, CO2.
The experimental result of 800 ℃ of following water vapour wet method cracking HFC-245fa of table 5
Experimental result shows, at 800 ℃, and in the steam rates scope selected of the present invention, transformation efficiency and selectivity are all highly stable.
Embodiment 5. is the influences of 850 ℃ of following water vapor amounts to wet method cracking HFC-245fa.
Other conditions are with embodiment 3, and the result sees table 5.Main by product is CO, CO2.
The experimental result of 850 ℃ of following water vapour wet method cracking HFC-245fa of table 6
Conclusion is with embodiment 2.
Embodiment 6 is the influence of differing temps to ammoniacal liquor steam wet method cracking HFC-245fa.
Reactor drum is the same, and the pipe temperature is a temperature of reaction in the reactor drum, and reactant CF3CH2CHF2 charge flow rate is 30ml/min, and the water vapour flow calculates with the steam output of 0.6g/min, and the reaction times is 0.04s.Reaction conditions and result see table 7.Main by product is CO, CO2.
The experimental result of table 7 ammoniacal liquor steam wet method cracking HFC-245fa
Table 7 shows that transformation efficiency raises along with temperature of reaction raises, and selectivity reduces, and in the time of 750 ℃, selects performance to reach more than 95%.
The foregoing description data declaration; Under crack reacting condition of the present invention; Temperature is the principal element that influences selectivity of product, under relatively low temperature, under 750-800 ℃ of degrees celsius; Can obtain the product of highly selective, industrial energy consumption is not higher than existing those and has adopted the reaction of catalysis system yet.In terms of existing technologies; The present invention does not adopt complicated operation, cost expensive catalysts system; And the selectivity of gained split product can use the scission reaction of catalysis system to compare favourably with those; Simplify response procedures greatly, lowered reaction cost, be fit to the industrialized mass production Fluorine containing olefine.
Claims (8)
1. the method for a preparing fluorinated alkene by high temperature wet-cracking is characterized in that under the normal pressure 600-1000 ℃ temperature, is H with the molecular formula
nF
mC
3Hydro fluoroalkanes be that unstripped gas is carried out scission reaction in water vapor or ammonia vapor environment, n+m=8 wherein, 1≤n≤6,2≤m≤7.
2. method according to claim 1, the charge flow rate of said unstripped gas are 10-100ml/min, and the charge flow rate of said water vapor or ammonia vapor is 0.3～0.9g/min.
3. method according to claim 2, the charge flow rate of said unstripped gas are 30ml/min.
4. according to claim 1,2 or 3 described methods, the RT of said unstripped gas is 0.01-10s.
5. method according to claim 4, the RT of said unstripped gas are 0.03-1s.
6. according to claim 1,2 or 3 described methods, the temperature of said scission reaction is 700～900 ℃.
7. method according to claim 6, the temperature of said scission reaction are 750～850 ℃.
8. according to claim 1,2 or 3 described methods, said unstripped gas is CF
3CH
2CF
3, CF
3CH
2CHF
2, CF
3CH
2CHF
2, CF
2HCH
2CHF
2Or CF
3CHFCF
3
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| CN110639157B (en) * | 2019-09-24 | 2021-01-29 | 九江中船化学科技有限公司 | Efficient composite fire extinguishing agent and preparation method thereof |
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| CN1428320A (en) * | 2001-12-25 | 2003-07-09 | 中昊晨光化工研究院 | Method for producing metafluoroethylene by pyrolysis of difluoro-chloroethane |
| CN1639094A (en) * | 2002-03-01 | 2005-07-13 | 大金工业株式会社 | Process for producing fluoromonomer |
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| CN1428320A (en) * | 2001-12-25 | 2003-07-09 | 中昊晨光化工研究院 | Method for producing metafluoroethylene by pyrolysis of difluoro-chloroethane |
| CN1639094A (en) * | 2002-03-01 | 2005-07-13 | 大金工业株式会社 | Process for producing fluoromonomer |
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