CN102887812A - Synthesis method of 1,1,3,3,3-pentafluoropropene - Google Patents
Synthesis method of 1,1,3,3,3-pentafluoropropene Download PDFInfo
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- CN102887812A CN102887812A CN2011102035302A CN201110203530A CN102887812A CN 102887812 A CN102887812 A CN 102887812A CN 2011102035302 A CN2011102035302 A CN 2011102035302A CN 201110203530 A CN201110203530 A CN 201110203530A CN 102887812 A CN102887812 A CN 102887812A
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- fluorine
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- fluorine propylene
- propylene
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Abstract
The invention discloses a synthesis method of 1,1,3,3,3-pentafluoropropene. The method comprises the following step of: removing halogen hydride from pentafluorohalogenopropane (CF3CH2CF2X, wherein X refers to F, Cl or Br) serving as a raw material in the presence of a catalyst to prepare 1,1,3,3,3-pentafluoropropene. The synthesis method has the advantages of mild reaction process, easiness in operating, high product yield and the like. The synthesized 1,1,3,3,3-pentafluoropropene can be applied in the fields of fluorine-containing resins, fluorine-containing rubber, refrigerants, foaming agents and the like.
Description
Technical field
The present invention relates to a kind of 1,1,3,3, the synthetic method of 3-five fluorine propylene.
Background technology
The halogenated alkanes such as fluorine-containing, chlorine, bromine are widely used in the industries such as refrigeration, cleaning, foaming, constantly be diffused in the atmospheric layer in such production of chemicals, the use procedure simultaneously, make under the irradiation of sunlight, rupture ozone in the cycle consumption earth atmosphere of its C-Cl that contains, C-Br key, cause the destruction of global environment, harm humans existence, the scientific worker begins to seek safer material and substitutes the chloroparaffins such as chloride bromine.
As HF hydrocarbon, the ODP value is that 0, GWP value is lower to 1,1,3,3,3-, five fluorine propylene (being called for short R1225zc), and the integrated environment friendly is better, can be used for the multiple fields such as fluorine resin, fluorine-containing rubber, refrigeration agent, whipping agent.The preparation method of 1,1,3,3,3-, five fluorine propylene mainly contains following several:
(1) US Patent No. 6031141, US6093859, US6369284 etc. have described take R236fa as raw material, the gas phase catalysis dehydrofluorination prepares R1225zc, catalyst system therefor is metal oxide, fluorochemical, oxygen fluoride and their mixtures such as Al, La, Cr, Mg, temperature of reaction is: 300 ℃-450 ℃, about reaction raw materials transformation efficiency 30%-50%, about product selectivity 80%-90%, this technology exists that the catalyzer cost is high, catalyst efficiency is low, the shortcoming of poor stability;
(2) Chinese patent CN101133008 has described in the situation that catalyst-free thermolysis R236fa prepares R1225zc, temperature of reaction is at 700 ℃-1000 ℃, the transformation efficiency of raw material R236fa has 25%-75%, the selectivity of R1225zc has 90%, this technology temperature of reaction is higher, reactor will use resistant to elevated temperatures nickelic or pure nickel material preparation, and cost is higher;
(3) US Patent No. 6376727, US6548720, US6476281 etc. have described again with R216aa(2,2-two chloro-1,1,1,3,3, the 3-HFC-236fa) is raw material, the gas-phase catalytic hydrogenation dechlorination prepares R1225zc, makees catalyzer at activated carbon, 350 ℃-500 ℃ of temperature of reaction with metal loads such as Cr, Cu, Ni, raw material R216aa transformation efficiency is substantially more than 90%, and the selectivity of R1225zc has about 90%, and this technology does not have special instruction to the work-ing life of catalyzer, and raw material is difficult to obtain simultaneously.
Summary of the invention
The object of the present invention is to provide a kind of 1,1,3,3, the preparation method of 3-five fluorine propylene, this technological line has that raw material sources extensively are easy to get, preparation technology is gentle, simple to operate, synthetic five fluorine propylene impurity are few, the advantage such as convenient of purifying.
For reaching goal of the invention the technical solution used in the present invention be:
A kind of 1,1,3,3, the preparation method of 3-five fluorine propylene, take five fluorine halogenopropanes as raw material, synthetic 1,1,3,3,3-, the five fluorine propylene of dehydrohalogenation under catalyst action,
The general formula of described five fluorine halogenopropanes is: CF
3CH
2CF
2X, wherein X is selected from F, Cl, Br,
Described catalyzer is comprised of Primary Catalysts and promotor, and Primary Catalysts is mineral alkali, and promotor is phase-transfer catalyst.
For the present technique route clearly is described, represent this synthetic technology with following reaction equation:
Five required fluorine halogenopropane raw materials of synthetic R1225zc reaction can be 1,1,1,3,3,3-HFC-236fa (R236fa), and R236fa is by 1,1,1,3,3,3-chlordene propane (R230) and HF are synthetic under fluorination catalyst, and this has been that the technology of suitability for industrialized production R236fa has been arranged, and liquid-phase fluorination catalyst is SnCl in this technology
4, TiCl
4, TaCl
5, NbCl
5, SbF
5, SbCl
5Or SbF
nCl
5-n(n:1～4) a kind of; Catalysts for gas phase fluorination is the metal pentafluoride salt such as Cr, Al, Mg, Co, Zn, Ni; Temperature of reaction is at 50 ℃～350 ℃.
Synthetic five required fluorine halogenopropane raw materials of R1225zc can be 1-chloro-1,1,3,3,3-pentafluoropropane (R235fa), and R235fa is by the intermediate product in R230 and the HF reaction preparation R236fa building-up process, synthetic catalyst is SnCl equally
4, TiCl
4, SbF
5, SbCl
5, SbF
nCl
5-n(n:1-4), the series such as Cr, Al, Mg, Co, Zn, Ni; The material proportion of R230 and HF is 1:3～1:10.R235fa also can be 1,1,3,3,3-pentafluoropropane (R245fa) and Cl simultaneously
2The reaction gained, this reaction is known as chlorination reaction, and the R245fa chlorination can be photocatalysis chlorination, thermal chlorination or catalytic chlorination, same R245fa can be with 1,1, and 1,3,3 ,-pentachloropropane (R240) and HF are synthetic under fluorination catalyst, and R245fa has had a large amount of suitability for industrialized production.
The synthetic required five fluorine halogenopropane raw materials of R1225zc can be 1-bromo-1,1,3,3 equally, and 3-pentafluoropropane, 1-bromo-1,1,3,3,3-pentafluoropropane can be 1,1,3,3,3-pentafluoropropane (R245fa) and Br
2The reaction gained, the R245fa bromination can be hot bromination or catalytic bromination, and bromination reaction need to carry out in special material, and general metal all is not suitable for such reaction, temperature of reaction has simultaneously many bromines pentafluoropropane by product and generates at 500 ℃～800 ℃.
As preferred embodiment, reacting described five fluorine halogenopropanes is CF
3CH
2CF
2Cl or CF
3CH
2CF
2Br.
In reaction of the present invention, described Primary Catalysts is that one or more compound alkali, this kind mineral alkali of mineral alkali is to be the metal oxide of alkalescence or one or more compound alkali of metal carbonate, and mineral alkali also can be one or more compound alkali of alkali metal hydroxide or alkaline earth metal hydroxides.The effect of alkaline catalysts is carried out in two steps in this reaction, and the first step is the halogen negative ion in the metal ion attack raw molecule in the Primary Catalysts, reaches the purpose of sloughing halogen atom, and second step is O in the Primary Catalysts
2-, OH
-Or CO
3 2-Attack the H on the close carbon atom of halogen atom in the raw material in negative ion
+Ion makes the whole dehydrohalogenation of this raw molecule form carbon-carbon double bond.
See that from macroscopic perspective the effect of whole catalysis dehalogenation reaction inorganic base catalyst is the hydrogen halide by product that neutralization reaction produces, catalyzer constantly consumes, therefore, the amount of catalyzer can quite or greater than this be reacted the amount of the hydrogen halide that produces with the amount of reacting the hydrogen halide that produces, when the amount of catalyzer is reacted the amount of the hydrogen halide that produces greater than this, will be conducive to the carrying out that reacts.The mole proportioning of preferred five fluorine halogenopropanes and Primary Catalysts is 10: 1～1: 10.Simultaneously the concentration of catalyzer also can affect the carrying out of the dehalogenation reaction, and higher concentration is conducive to reaction, the alkaline ph value of generally selecting mineral alkali greater than 12 or mass concentration greater than 20%.
The present invention promotes reaction to carry out in order to reduce the resistance between organic raw material and the inorganic base catalyst phase interface, and this reaction technology need to add a certain amount of phase-transfer catalyst as promotor.The amount that promotor adds can be allocated according to the speed that reaction is carried out, and the mole proportioning of preferred Primary Catalysts and promotor is 200: 1～100: 1.
As preferred embodiment, mineral alkali of the present invention be selected from alkalimetal oxide, alkaline earth metal oxide, alkali metal hydroxide, alkaline earth metal hydroxides, alkaline carbonate, alkaline earth metal carbonate, basic metal acid carbonate or the alkaline earth metal carbonate acid one or more, described phase-transfer catalyst is selected from one or more in polyethers, crown ether-like, quaternary ammonium salt, quaternary ammonium bases or the quaternary phosphonium salt.
As further preferred embodiment, described polyethers is that molecular-weight average is 400～2000 polyoxyethylene glycol or polyoxyethylene glycol dialkyl ether, and the molecular formula of polyoxyethylene glycol is H (OCH
2CH
2)
nOH, the molecular formula of polyoxyethylene glycol dialkyl ether is: R (OCH
2CH
2)
nOR, R represents alkyl; Described crown ether-like is 18-hat-6 ethers or 15-crown-5; Described quaternary ammonium salt is selected from benzyltriethylammoinium chloride (TEBA), Tetrabutyl amonium bromide, tetrabutylammonium chloride, 4-butyl ammonium hydrogen sulfate (TBAB), tri-n-octyl methyl ammonium chloride, Dodecyl trimethyl ammonium chloride or tetradecyl trimethyl ammonium chloride; Described quaternary ammonium bases is tetramethylammonium hydroxide or tetraethyl ammonium hydroxide, and the tetramethylammonium hydroxide molecular formula is (CH
3)
4NOH, the tetraethyl ammonium hydroxide molecular formula is (CH
3CH
2)
4NOH.
The temperature of building-up reactions is larger to synthetic rate, and we wish that reaction carries out faster, and again within can span of control, the suitable reactions temperature be 0 ℃～120 ℃ simultaneously, and more excellent temperature of reaction is 50 ℃～90 ℃.
Synthesising reacting time generally is to grow and more be conducive to react completely, but the oversize reaction times can affect output, controlling the rational reaction times is between 1hr～10hr, the more excellent reaction times refers to 2hr～5hr.
The present invention does not have concrete technical requirements to reaction pressure, so long as the general acid-base material of ability can be simple glass reactor or stainless steel pressure reactor, and preferred stainless steel pressure reactor; Reaction pressure can be normal pressure or carry out under certain pressure, as long as reaction pressure meets the service requirements of reactor, general control is between 0.1Mpa～3Mpa.
Embodiment
Come the present invention is further specified below in conjunction with specific embodiment, but do not limit the invention to these embodiments.One skilled in the art would recognize that the present invention contained all alternativess, improvement project and the equivalents that may comprise in claims scope.
Embodiment 1
Be in the band pressure reactor of belt stirrer of 0.25L at volume, add 150gCBrF
2CH
2CF
3Synthesis material, 80g concentration are 40% NaOH solution, and 1g18-is preced with-6 ethers, then the reactor that closes reacts, and opens stirring, and stirring velocity is at 200 rev/mins, open heating rising temperature of reaction, temperature is controlled at 60 ℃-70 ℃, isothermal reaction 2 hours, and reaction pressure changes with temperature of reaction, be controlled between the 0.5Mpa-1.0Mpa, reaction is emitted material after finishing, and obtains crude product material 65g, wherein CF
2=CHCF
3Content is 92%, product yield 64%; Other is unreacted raw material five fluorine N-PROPYLE BROMIDEs and HFC-236fa etc.
Embodiment 2
Be in the band pressure reactor of belt stirrer of 0.25L at volume, add 159gCBrF
2CH
2CF
3Raw material, 100g concentration are 40% KOH solution, the 1g tetrabutylammonium chloride, then the reactor that closes reacts, open stirring, stirring velocity is opened heating rising temperature of reaction at 200 rev/mins, temperature is controlled at 60 ℃-70 ℃, isothermal reaction 2 hours, reaction pressure is controlled between the 0.5Mpa-1.0Mpa, and reaction is emitted material after finishing, condensation is collected and is obtained crude product material 76g, wherein CF
2=CHCF
3Content is 93%, product yield 71%; Other material is unreacted raw material five fluorine N-PROPYLE BROMIDEs and HFC-236fa etc.
Embodiment 3
In the stainless steel autoclave of the belt stirrer of 0.25L, add 112g raw material CF
3CH
2CClF
2, 90g concentration is 40% KOH solution, then the 1g poly(oxyethylene glycol) 400 reacts, temperature of reaction is 60 ℃-70 ℃, and reaction pressure is controlled between the 0.7Mpa-1.2Mpa, 2 hours reaction times, reaction finishes to emit material, and condensation is collected and obtained crude product material 79g, wherein products C F
2=CHCF
3Content is 82%, and product yield 75%, other material are unreacted raw material five fluorine chloropropanes etc.
Embodiment 4
In the stainless steel autoclave of the belt stirrer of 0.25L, add 87g reaction raw materials CF
3CH
2CF
3, 80g concentration is 40% KOH solution, the 1g Dodecyl trimethyl ammonium chloride, reactor closes, open stirring, heat up, then react, temperature of reaction is 60 ℃-70 ℃, in 3 hours reaction times, reaction pressure is controlled between the 0.8Mpa-1.5Mpa, and reaction finishes to emit material, condensation is collected and is obtained crude product 55g, wherein products C F
2=CHCF
3Content 91%, product yield 67%, other material are raw material HFC-236fa and R 1216 etc.
Embodiment 5
In the stainless steel autoclave of the belt stirrer of 0.25L, add 76g reaction raw materials CF
3CH
2CF
3, 120g concentration is 18% LiOH solution, 1g hydroxide trimethylammonium ethyl ammonium, reactor closes, open stirring, heat up, then react, temperature of reaction is 60 ℃-70 ℃, in 3 hours reaction times, reaction pressure is controlled between the 0.8Mpa-1.5Mpa, and reaction finishes to emit material, condensation is collected and is obtained crude product 59g, wherein products C F
2=CHCF
3Content 73%, product yield 65%, other material are raw material HFC-236fa and R 1216 etc.
Embodiment 6
In three mouthfuls of glass flask of 0.5L, band stirs and reflux exchanger, is 35% NaOH solution to wherein adding 300g concentration, and the 1g tetramethylammonium hydroxide starts stirring, and heat temperature raising when temperature of reaction is 80 ℃, drips CBrF in reactor
2CH
2CF
3Raw material, reaction pressure are 0.1Mpa, and freezing collection reaction gas phase sample drips the 350g raw material altogether, receives that thick product is 231g, wherein CF
2=CHCF
3Content 58%, product yield 61%, all the other are reaction raw materials.
Embodiment 7
In three mouthfuls of glass flask of 0.5L, band stirs and reflux exchanger, is 35% NaOH solution to wherein adding 350g concentration, and 1g18-is preced with-6 ethers, starts stirring, and heat temperature raising when temperature of reaction is 70 ℃, drips CClF in reactor
2CH
2CF
3Raw material, reaction pressure are 0.1Mpa, and freezing collection reaction gas phase sample drips the 300g raw material altogether, receives that thick product is 196g, wherein CF
2=CHCF
3Content 51%, product yield 43%, all the other are reaction raw materials.
Claims (10)
1. one kind 1,1,3,3, the preparation method of 3-five fluorine propylene is characterized in that take five fluorine halogenopropanes as raw material, synthetic 1,1,3,3,3-, the five fluorine propylene of dehydrohalogenation under catalyst action,
The general formula of described five fluorine halogenopropanes is: CF
3CH
2CF
2X, wherein X is selected from F, Cl, Br,
Described catalyzer is comprised of Primary Catalysts and promotor, and Primary Catalysts is mineral alkali, and promotor is phase-transfer catalyst.
2. according to claimed in claim 11,1,3,3, the preparation method of 3-five fluorine propylene is characterized in that described five fluorine halogenopropanes are CF
3CH
2CF
2Cl or CF
3CH
2CF
2Br.
3. according to claimed in claim 11,1,3,3, the preparation method of 3-five fluorine propylene, the alkaline ph value that it is characterized in that described mineral alkali more than or equal to 12 or mass concentration more than or equal to 20%.
4. according to claimed in claim 11,1,3,3, the preparation method of 3-five fluorine propylene, it is characterized in that described mineral alkali be selected from alkalimetal oxide, alkaline earth metal oxide, alkali metal hydroxide, alkaline earth metal hydroxides, alkaline carbonate, alkaline earth metal carbonate, basic metal acid carbonate or the alkaline earth metal carbonate acid one or more, described phase-transfer catalyst is selected from one or more in polyethers, crown ether-like, quaternary ammonium salt, quaternary ammonium bases or the quaternary phosphonium salt.
5. according to claimed in claim 41,1,3,3, the preparation method of 3-five fluorine propylene, it is characterized in that described polyethers is that molecular-weight average is 400～2000 polyoxyethylene glycol or polyoxyethylene glycol dialkyl ether, described crown ether-like is 18-hat-6 ethers or 15-crown-5, described quaternary ammonium salt is selected from benzyltriethylammoinium chloride, Tetrabutyl amonium bromide, tetrabutylammonium chloride, 4-butyl ammonium hydrogen sulfate, tri-n-octyl methyl ammonium chloride, Dodecyl trimethyl ammonium chloride or tetradecyl trimethyl ammonium chloride, and described quaternary ammonium bases is tetramethylammonium hydroxide or tetraethyl ammonium hydroxide.
6. according to claimed in claim 11,1,3,3, the preparation method of 3-five fluorine propylene is characterized in that temperature of reaction is 0 ℃～120 ℃, and the reaction times is 1hr～10hr.
7. according to claimed in claim 61,1,3,3, the preparation method of 3-five fluorine propylene is characterized in that temperature of reaction is 50 ℃～90 ℃, and the reaction times refers to 2hr～5hr.
8. according to claimed in claim 11,1,3,3, the preparation method of 3-five fluorine propylene is characterized in that the mole proportioning of described five fluorine halogenopropanes and Primary Catalysts is 10: 1～1: 10.
9. according to claimed in claim 11,1,3,3, the preparation method of 3-five fluorine propylene, the mole proportioning that it is characterized in that described Primary Catalysts and promotor is 200: 1～100: 1.
10. according to claimed in claim 11,1,3,3, the preparation method of 3-five fluorine propylene is characterized in that reaction pressure is 0.1Mpa～3Mpa.
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Cited By (7)
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| CN103172489A (en) * | 2013-03-14 | 2013-06-26 | 巨化集团技术中心 | Synthesis method of 1,1,1,4,4,4-hexafluorine-2-butene |
| CN105935593A (en) * | 2016-01-14 | 2016-09-14 | 浙江师范大学 | Catalyst for converting HFC-245fa into trans 1,3,3-tetrafluoropropene and preparation method thereof |
| CN106732772A (en) * | 2016-03-31 | 2017-05-31 | 台湾塑胶工业股份有限公司 | Cracking catalyst for 1, 2-dichloroethane, process for producing the same and use thereof |
| CN107434759A (en) * | 2016-05-25 | 2017-12-05 | 浙江省化工研究院有限公司 | A kind of method for preparing 1,1,3,3,3- pentafluoropropenes |
| CN111454120A (en) * | 2020-05-19 | 2020-07-28 | 常州新东化工发展有限公司 | Preparation method of 1,1,3,3, 3-pentafluoropropene |
| CN114375287A (en) * | 2019-09-12 | 2022-04-19 | 关东电化工业株式会社 | Method for purifying fluoroolefin having structure = CF2 or = CHF, high-purity fluoroolefin, and method for producing same |
| WO2024075666A1 (en) * | 2022-10-03 | 2024-04-11 | 関東電化工業株式会社 | Fluoroolefin production method |
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| CN103172489A (en) * | 2013-03-14 | 2013-06-26 | 巨化集团技术中心 | Synthesis method of 1,1,1,4,4,4-hexafluorine-2-butene |
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| CN105935593B (en) * | 2016-01-14 | 2018-06-22 | 浙江师范大学 | It is a kind of to be converted into catalyst of trans- 1,3,3,3- tetrafluoropropenes and preparation method thereof for HFC-245fa |
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| CN114375287A (en) * | 2019-09-12 | 2022-04-19 | 关东电化工业株式会社 | Method for purifying fluoroolefin having structure = CF2 or = CHF, high-purity fluoroolefin, and method for producing same |
| CN111454120A (en) * | 2020-05-19 | 2020-07-28 | 常州新东化工发展有限公司 | Preparation method of 1,1,3,3, 3-pentafluoropropene |
| CN111454120B (en) * | 2020-05-19 | 2022-04-29 | 常州新东化工发展有限公司 | Preparation method of 1,1,3,3, 3-pentafluoropropene |
| WO2024075666A1 (en) * | 2022-10-03 | 2024-04-11 | 関東電化工業株式会社 | Fluoroolefin production method |
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