CN102964206A - Method for simultaneous preparation of 3, 3-dichloro-1, 1, 1-trifluoropropene and 3, 3, 3-trichloro-1, 1, 1-trifluoropropene - Google Patents
Method for simultaneous preparation of 3, 3-dichloro-1, 1, 1-trifluoropropene and 3, 3, 3-trichloro-1, 1, 1-trifluoropropene Download PDFInfo
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- CN102964206A CN102964206A CN2012104226243A CN201210422624A CN102964206A CN 102964206 A CN102964206 A CN 102964206A CN 2012104226243 A CN2012104226243 A CN 2012104226243A CN 201210422624 A CN201210422624 A CN 201210422624A CN 102964206 A CN102964206 A CN 102964206A
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Abstract
The invention discloses a method for simultaneous preparation of 3, 3-dichloro-1, 1, 1-trifluoropropene and 3, 3, 3-trichloro-1, 1, 1-trifluoropropene. The method comprises the steps of: under photocatalytic effect, mixing 3-chloro-1, 1, 1-trifluoropropene and chlorine in a molar ratio of 0.2:1-5:1, and introducing the mixture into a light chlorination reactor; reacting at a reaction temperature of 0-200 DEG C, reaction pressure of 0-1.0MPa and reaction velocity of 50-1500 h<-1> to obtain a reaction products containing 3, 3-dichloro-1, 1, 1-trifluoropropene and 3, 3, 3-trichloro-1, 1,1-trifluoropropene; and washing the reaction products with water and alkali, and distilling to obtain the products of 3, 3-dichloro-1, 1, 1-trifluoropropene and 3, 3, 3-trichloro-1, 1, 1-trifluoropropene. The invention has advantages of simple process, mild reaction conditions, high conversion rate, high selectivity, good controllability, continuous operation and easy amplification.
Description
Technical field
The present invention relates to a kind of method for preparing halogenopropane, particularly a kind of light chlorination process prepares 3,3-dichloro-1,1,1-trifluoro propane and 3,3,3-, three chloro-1,1, the method for 1-trifluoro propane simultaneously.
Background technology
3,3-two chloro-1,1,1-trifluoro propane and 3,3,3-, three chloro-1,1, many chlorine trifluoro propane such as 1-trifluoro propane all are important fine chemicals, can be used as highly effective refrigeration agent, bubbling agent, sanitising agent, solvent, heat-conduction medium, sterilant, aerosol propellant, isolator, fire-fighting medium and energy cycle working fluid etc.; In addition, also can be used for preparing the synthetic multiple downstream of HF hydrocarbon compound, therefore have very large application potential.
China Patent Publication No. CN101168494A, open day on April 30th, 2008, denomination of invention: the preparation method of chlorotrifluoropropylene.This application case discloses that telomerization in the presence of catalyzer prepares pentachloropropane by methyl chloride and chloro-alkenes, pentachloropropane is fluoridized into the trifluoro propylene dichloride with hydrogen fluoride under composite catalyst catalysis, the trifluoro propylene dichloride removes hydrogenchloride and obtains the finished product chlorotrifluoropropylene under the pure liquid catalysis of alkali.Its synthetic 3,3-, two chloro-1,1, the operational path of 1-trifluoro propane is with 1,1,1,3,3-pentachloropropane and anhydrous hydrogen fluoride are raw material, under the effect of the catalyzer such as chromium fluoride, magnesium fluoride and titanium fluoride, 90～130 ° of C of temperature of reaction, the reaction times is 4～10h, 1,1,1,3,3-pentachloropropane and anhydrous hydrogen fluoride mol ratio are synthetic under the condition of 1:4～1:10, and product selectivity is about 85%.This route exists the reaction times longer, and is high to equipment requirements, and operational condition is comparatively harsh, and selectivity is not high, and is the shortcomings such as interval type reacts, reaction efficiency is low.
Chinese patent Granted publication CN101560138B, November 3 2010 day for announcing, denomination of invention: the preparation method of pentafluoropropane.This patent disclosure the preparation method of a kind of pentafluoropropane (245fa), take vinylchlorid and trifluorochloromethane as raw material, straight chain alcohol, phosphate mixture are solvent, under the composite catalyst effects such as tindichloride, platinum chloride, iron trichloride, at 120～140 ° of C of temperature of reaction, reaction pressure 1.2～1.5MPa, the reaction times is 2～3h, can obtain the trifluoro propylene dichloride, yield about 91%.The shortcomings such as to be this route be not described specifically structure and the selectivity of reaction product weak point, and reaction exists equipment requirements highly, and operational condition is relatively harsher, and reaction can only the gap be carried out, reaction efficiency is low.
Summary of the invention
The present invention is directed to the deficiencies in the prior art part, provide that a kind of technique is simple, reaction conditions is gentle, yield is high, product selectivity prepares 3,3-dichloro-1,1,1-trifluoro propane in the time of good and 3,3,3-, three chloro-1,1, the method for 1-trifluoro propane.
In order to solve the problems of the technologies described above, the technical solution used in the present invention is: a kind of 3,3-, two chloro-1 that prepare simultaneously, 1,1-trifluoro propane and 3,3,3-three chloro-1,1, the method for 1-trifluoro propane, under photocatalysis, with 3-chloro-1,1,1-trifluoro propane is to pass into the optical chlorinating reaction device after 0.2:1～5:1 mixes with chlorine in molar ratio, is 0～200 ℃ in temperature of reaction, reaction pressure 0～1.0MPa, reaction velocity is to react under the condition of 50～1500h-1, obtains containing 3,3-, two chloro-1,1,1-trifluoro propane and 3,3,3-three chloro-1,1, the reaction product of 1-trifluoro propane, with reaction product through the washing, namely obtain 3 after alkali cleaning and the rectifying, 3-dichloro-1,1,1-trifluoro propane and 3,3,3-three chloro-1,1,1-trifluoro propane product.
Further:
Described light-catalysed light source is visible light or UV-light.
Described optical source wavelength is 300～700nm.
Described 3-chloro-1,1, the mol ratio of 1-trifluoro propane and chlorine are 0.6:1～4:1.
Described temperature of reaction is 20～150 ℃.
Described reaction pressure is 0.2～0.8MPa.
Described reaction velocity is 200～1000h
-1
This reaction belongs to the free radical type chain reaction, and reaction mechanism is: Cl
2Under illumination, form chlorine radical (Cl), chlorine radical and 3-chloro-1,1,1-trifluoro propane and 3, the 3-dichloro-1,1,1-trifluoro propane bumps, from 3-chloro-1,1,1-trifluoro propane and 3,3-, two chloro-1, win a hydrogen atom in 1, the 1-trifluoro propane, generate HCl, 3-chloro-1,1,1-trifluoro propane and 3, the 3-dichloro-1,1,1-trifluoro propane changes CF into
3CH
2CHCl. with CF
3CH
2CCl
2., CF then
3CH
2CHCl. with CF
3CH
2CCl
2. again with Cl
2Bump, from Cl
2In win a chlorine atom, generate at last 3,3-dichloro-1,1,1-trifluoro propane and 3,3,3-, three chloro-1,1,1-trifluoro propane, so continuous reaction is gone down, until chain reaction finishes; Because of 3,3-two chloro-1,1,1-trifluoro propane (76 ℃ of boiling points) and 3,3,3-, three chloro-1, the boiling point of 1,1-trifluoro propane (105 ℃ of boiling points) differs larger, and reaction product namely obtains 3 after the conventional processing such as washing, alkali cleaning, rectifying, 3-dichloro-1,1,1-trifluoro propane and 3,3,3-three chloro-1,1,1-trifluoro propane product.Reaction equation is suc as formula 1), 2) shown in.
Method technical process of the present invention is simple, and reaction conditions is gentle, and is low for equipment requirements, and general conventional photoreactor such as embedded light-source type lining tetrafluoro carbon steel fixed-bed reactor, light source external placed type quartz tube reactor etc. all can be realized the present invention.
Among the present invention, light wavelength all can promote the carrying out that react in the scope of Uv and visible light, and in the actually operating, the wavelength of control light source be relatively difficulty of certain specific value, also there is no need, and a wavelength that only needs control light source gets final product in certain interval.The present invention considers that from the secure context to the operator wavelength of used light source is preferably 300～700nm.
3-chloro-1,1,1-trifluoro propane and chlorine replace generation 3,3-dichloro-1,1,1-trifluoro propane and 3,3,3-, three chloro-1,1, belong to thermopositive reaction during 1-trifluoro propane, and it is very important in time to remove reaction heat.Temperature is too low, and the difficult realization of operational condition and energy consumption are also larger; Temperature is too high, and the tendency that side reaction occurs is larger.So temperature of reaction of the present invention is controlled to be 0～200 ℃, preferred 20 ℃～150 ℃.
Reaction velocity is larger, and material is just shorter in the residence time of photo catalysis reactor; So along with the increase of reaction velocity, 3-chloro-1,1, the transformation efficiency of 1-trifluoro propane will descend, but the selectivity of 3,3-dichloro-1,1,1-trifluoro propane will increase.The reactor air speed is less, and the residence time is longer, 3,3,3-, three chloro-1,1, and 1-trifluoro propane selectivity will increase, but the production capacity of unit volume reactor is just less, is unfavorable for suitability for industrialized production.So reactor air speed of the present invention is controlled to be 50h
-1～1500h
-1, preferred 200h
-1～1000h
-1
According to test-results, 3-chloro-1,1, the material ratio of 1-trifluoro propane and chlorine is higher, and the selectivity of 3,3-dichloro-1,1,1-trifluoro propane is higher; 3-chloro-1,1, the material ratio of 1-trifluoro propane and chlorine is lower, 3,3,3-, three chloro-1,1,1-trifluoro propane selectivity will increase.But material ratio is larger, and under same reactor air speed, the reactor production capacity descends.So 3-chloro-1,1 among the present invention, the mol ratio of 1-trifluoro propane and chlorine are 0.2:1～5:1, preferred 0.6:1～4:1.
In addition, except above temperature of reaction, material proportion, reactor air speed affect reaction conversion ratio and the selectivity, reaction pressure also is one of important factor that affects reaction effect.On reaction kinetics, increase pressure energy and increase speed of response, reason is that gas molecula number is added in the unit volume, effective collision is also added, and impels the increase of speed of response.Pressure is too low in addition, and unit volume reactor production capacity is lower, and is uneconomical; But pressure is too high, equipment material is required harsh.So the present invention considers various factors, the selective pressure span of control is 0～1.0MPa, preferred 0.2～0.8MPa.
Advantage of the present invention is:
1, the controllability of reaction preference is better, can according to actual needs, regulate flexibly the production capacity of two kinds of products.
2, feed stock conversion is high, 3-chloro-1,1, and the peak rate of conversion of 1-trifluoro propane can reach 96.1%; Product selectivity is good, and 3,3-dichloro-1,1,1-trifluoro propane selectivity is up to 98.1%, 3,3,3-, three chloro-1,1, and 1-trifluoro propane selectivity is up to 53.7%.
3, technical process is simple, and reaction conditions is gentle, and general conventional photoreactor all can be realized the present invention.
But 4 operate continuouslys realize suitability for industrialized production easily.
Embodiment
By the following examples the present invention is carried out more specific description, but the present invention is not limited to described embodiment.
Embodiment 1
With 3-chloro-1,1,1-trifluoro propane and chlorine mix the embedded light-source type lining tetrafluoro carbon steel fixed-bed reactor that pass into the 640ml that possesses the material feeding condition, (carry out substitution reaction under wavelength 500 ~ 600nm) katalysis, control 3-chloro-1,1 at visible light, 1-trifluoro propane and chlorine mol ratio are 1.5:1, temperature of reaction is 0 ℃, and reaction pressure is 0.8Mpa, and reaction velocity is 50h
-1, obtain containing 3,3-, two chloro-1,1,1-trifluoro propane and 3,3,3-, three chloro-1,1, the reaction product of 1-trifluoro propane, with reaction product through washing, rectifying after the alkali cleaning, the cut when collecting 76 ℃ and 105 ℃, namely obtain 3,3-, two chloro-1,1,1-trifluoro propane and 3,3,3-, three chloro-1,1,1-trifluoro propane product, its purity is respectively 99.4% and 99.2%.By the reactor outlet material sampling analysis being drawn 3-chloro-1,1,1-trifluoro conversion of propane: 62.7%; 3,3-dichloro-1,1,1-trifluoro propane selectivity: 75.6%; 3,3,3-, three chloro-1,1,1-trifluoro propane selectivity: 23.4%.
Embodiment 2
With 3-chloro-1,1,1-trifluoro propane and chlorine mix the light source external placed type quartz tube reactor that passes into the 640ml that possesses the material feeding condition, (carry out substitution reaction under wavelength 300 ~ 400nm) katalysis, control 3-chloro-1,1 in UV-light, 1-trifluoro propane and chlorine mol ratio 3:1,200 ℃ of temperature of reaction, reaction pressure 0.4Mpa, reaction velocity 1500h
-1, obtaining containing 3,3-dichloro-1,1,1-trifluoro propane and 3,3,3-, three chloro-1,1, the reaction product of 1-trifluoro propane is with reaction product rectifying after washing, alkali cleaning.Cut when collecting 76 ℃ and 105 ℃ namely obtains 3,3-dichloro-1,1,1-trifluoro propane and 3,3,3-, three chloro-1,1,1-trifluoro propane product, and its purity is respectively 99.6% and 99.5%.By the reactor outlet material sampling analysis being drawn 3-chloro-1,1,1-trifluoro conversion of propane: 32.2%; 3,3-dichloro-1,1,1-trifluoro propane selectivity: 93.9%; 3,3,3-, three chloro-1,1,1-trifluoro propane selectivity: 3.8%.
Embodiment 3
With 3-chloro-1,1,1-trifluoro propane and chlorine mix the embedded light-source type pottery fixed-bed reactor that pass into the 640ml that possesses the material feeding condition, (carry out substitution reaction under wavelength 300 ~ 400nm) katalysis, control 3-chloro-1,1 in UV-light, 1-trifluoro propane and chlorine mol ratio 5:1,150 ℃ of temperature of reaction, reaction pressure 0Mpa, reaction velocity 1000h
-1, obtain containing 3,3-, two chloro-1,1,1-trifluoro propane and 3,3,3-, three chloro-1,1, the reaction product of 1-trifluoro propane, with reaction product through washing, rectifying after the alkali cleaning, the cut when collecting 76 ℃ and 105 ℃, namely obtain 3,3-, two chloro-1,1,1-trifluoro propane and 3,3,3-, three chloro-1,1,1-trifluoro propane product, its purity is respectively 99.5% and 99.4%.By the reactor outlet material sampling analysis being drawn 3-chloro-1,1,1-trifluoro conversion of propane: 18.1%; 3,3-dichloro-1,1,1-trifluoro propane selectivity: 98.1%; 3,3,3-, three chloro-1,1,1-trifluoro propane selectivity: 1.3%.
Embodiment 4
With 3-chloro-1,1,1-trifluoro propane and chlorine mix the embedded light-source type lining tetrafluoro carbon steel fixed-bed reactor that pass into the 640ml that possesses the material feeding condition, (carry out substitution reaction under wavelength 600 ~ 700nm) katalysis, control 3-chloro-1,1 at visible light, 1-trifluoro propane and chlorine mol ratio 0.6:1,20 ℃ of temperature of reaction, reaction pressure 1.0Mpa, reaction velocity 200h
-1, obtain containing 3,3-, two chloro-1,1,1-trifluoro propane and 3,3,3-, three chloro-1,1, the reaction product of 1-trifluoro propane, with reaction product through washing, rectifying after the alkali cleaning, the cut when collecting 76 ℃ and 105 ℃, namely obtain 3,3-, two chloro-1,1,1-trifluoro propane and 3,3,3-, three chloro-1,1,1-trifluoro propane product, its purity is respectively 99.3% and 99.4%.By the reactor outlet material sampling analysis being drawn 3-chloro-1,1,1-trifluoro conversion of propane: 94.2%; 3,3-dichloro-1,1,1-trifluoro propane selectivity: 54.3%; 3,3,3-, three chloro-1,1,1-trifluoro propane selectivity: 43.6%.
Embodiment 5
With 3-chloro-1,1,1-trifluoro propane and chlorine divide and mix the embedded light-source type lining tetrafluoro carbon steel fixed-bed reactor that pass into the 640ml that possesses the material feeding condition, (carry out substitution reaction under wavelength 400 ~ 500nm) katalysis, control 3-chloro-1,1 at visible light, 1-trifluoro propane and chlorine mol ratio 4:1,100 ℃ of temperature of reaction, reaction pressure 0.2Mpa, reaction velocity 400h
-1, obtain containing 3,3-, two chloro-1,1,1-trifluoro propane and 3,3,3-, three chloro-1,1, the reaction product of 1-trifluoro propane, with reaction product through washing, rectifying after the alkali cleaning, the cut when collecting 76 ℃ and 105 ℃, namely obtain 3,3-, two chloro-1,1,1-trifluoro propane and 3,3,3-, three chloro-1,1,1-trifluoro propane product, its purity is respectively 99.6% and 99.7%.By the reactor outlet material sampling analysis being drawn 3-chloro-1,1,1-trifluoro conversion of propane: 23.4%; 3,3-dichloro-1,1,1-trifluoro propane selectivity: 97.6%; 3,3,3-, three chloro-1,1,1-trifluoro propane selectivity: 2.1%.
Embodiment 6
With 3-chloro-1,1,1-trifluoro propane and chlorine mix the light source external placed type quartz tube reactor that passes into the 640ml that possesses the material feeding condition, (carry out substitution reaction under wavelength 300 ~ 400nm) katalysis, control 3-chloro-1,1 in UV-light, 1-trifluoro propane and chlorine mol ratio 0.2:1,130 ℃ of temperature of reaction, reaction pressure 0.6Mpa, reaction velocity 900h
-1, obtain containing 3,3-, two chloro-1,1,1-trifluoro propane and 3,3,3-, three chloro-1,1, the reaction product of 1-trifluoro propane, with reaction product through washing, rectifying after the alkali cleaning, the cut when collecting 76 ℃ and 105 ℃, namely obtain 3,3-, two chloro-1,1,1-trifluoro propane and 3,3,3-, three chloro-1,1,1-trifluoro propane product, its purity is respectively 99.8% and 99.6%.By the reactor outlet material sampling analysis being drawn 3-chloro-1,1,1-trifluoro conversion of propane: 96.1%; 3,3-dichloro-1,1,1-trifluoro propane selectivity: 42.2%; 3,3,3-, three chloro-1,1,1-trifluoro propane selectivity: 53.7%.
Claims (7)
1. one kind prepares 3,3-, two chloro-1,1 simultaneously, 1-trifluoro propane and 3,3,3-, three chloro-1, the method of 1,1-trifluoro propane is characterized in that, under photocatalysis, with 3-chloro-1,1,1-trifluoro propane is to pass into the optical chlorinating reaction device after 0.2:1～5:1 mixes with chlorine in molar ratio, be 0～200 ℃ in temperature of reaction, reaction pressure is 0～1.0MPa, and reaction velocity is 50～1500h
-1Condition under react, obtain containing 3,3-dichloro-1,1,1-trifluoro propane and 3,3,3-three chloro-1,1, the reaction product of 1-trifluoro propane namely obtains 3,3-, two chloro-1,1 with reaction product after washing, alkali cleaning and rectifying, 1-trifluoro propane and 3,3,3-, three chloro-1,1,1-trifluoro propane product.
2. 3,3-dichloro-1,1,1-trifluoro propane and 3,3,3-, three chloro-1,1 of preparing simultaneously according to claim 1, the method for 1-trifluoro propane is characterized in that described light-catalysed light source is visible light or UV-light.
3. 3,3-dichloro-1,1,1-trifluoro propane and 3,3,3-, three chloro-1,1 of preparing simultaneously according to claim 2, the method for 1-trifluoro propane is characterized in that described optical source wavelength is 300～700nm.
4. 3,3-dichloro-1,1,1-trifluoro propane and 3,3,3-, three chloro-1,1 of preparing simultaneously according to claim 1, the method for 1-trifluoro propane is characterized in that described 3-chloro-1,1, the mol ratio of 1-trifluoro propane and chlorine is 0.6:1～4:1.
5. 3,3-dichloro-1,1,1-trifluoro propane and 3,3,3-, three chloro-1,1 of preparing simultaneously according to claim 1, the method for 1-trifluoro propane is characterized in that described temperature of reaction is 20～150 ℃.
6. 3,3-dichloro-1,1,1-trifluoro propane and 3,3,3-, three chloro-1,1 of preparing simultaneously according to claim 1, the method for 1-trifluoro propane is characterized in that described reaction pressure is 0.2～0.8MPa.
7. 3,3-dichloro-1,1,1-trifluoro propane and 3,3,3-, three chloro-1,1 of preparing simultaneously according to claim 1, the method for 1-trifluoro propane is characterized in that described reaction velocity is 200～1000h
-1
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103449961A (en) * | 2013-08-15 | 2013-12-18 | 巨化集团技术中心 | Synthesis method of 1,1-dichloro-3,3,3-trifluoropropane |
| CN112979409A (en) * | 2019-12-13 | 2021-06-18 | 浙江省化工研究院有限公司 | Method for preparing 3,3, 3-trichloro-1, 1, 1-trifluoropropane by gas-phase catalytic chlorination |
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| CN101168494A (en) * | 2007-11-27 | 2008-04-30 | 常熟三爱富中昊化工新材料有限公司 | Preparation method for chlorotrifluoropropylene |
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| CN101168494A (en) * | 2007-11-27 | 2008-04-30 | 常熟三爱富中昊化工新材料有限公司 | Preparation method for chlorotrifluoropropylene |
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| R. N. HASZELDINE: "Reactions of Fluorocarbon Radicals. Part V.* Alternative Syntheses for Trifluoromethylacetylene (3 : 3 : 3-Trifluoropropyne),and the Influence of Polyfluoro-groups on Adjacent Hydrogen and Halogen Atoms", 《JOURNAL OF THE CHEMICAL SOCIETY 》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103449961A (en) * | 2013-08-15 | 2013-12-18 | 巨化集团技术中心 | Synthesis method of 1,1-dichloro-3,3,3-trifluoropropane |
| CN103449961B (en) * | 2013-08-15 | 2015-09-09 | 巨化集团技术中心 | The synthetic method of chloro-3,3, the 3-trifluoro propane of a kind of 1,1-bis- |
| CN112979409A (en) * | 2019-12-13 | 2021-06-18 | 浙江省化工研究院有限公司 | Method for preparing 3,3, 3-trichloro-1, 1, 1-trifluoropropane by gas-phase catalytic chlorination |
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Application publication date: 20130313 |