CN107056579A - A kind of preparation method of 2,3,3,3 tetrafluoropropenes - Google Patents
A kind of preparation method of 2,3,3,3 tetrafluoropropenes Download PDFInfo
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- CN107056579A CN107056579A CN201710389196.1A CN201710389196A CN107056579A CN 107056579 A CN107056579 A CN 107056579A CN 201710389196 A CN201710389196 A CN 201710389196A CN 107056579 A CN107056579 A CN 107056579A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/354—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by hydrogenation
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Abstract
The invention discloses one kind 2,3,3, the preparation method of 3 tetrafluoropropenes, by two reactors and three rectifying columns, test of many times filters out optimum process condition, synthetic route in existing preparation method is overcome long, the problem of conversion ratio and low selectivity so that the conversion ratio that entirely reacts and selectivity are greatly improved, the conversion ratio of hexafluoropropene is more than 99%, 1,1, the conversion ratio of 1,2,3 pentafluoropropene is 100%, 1,1,1,2,3,3 HFC-236fas and 1,1,1, the selectivity of 2,3 pentafluoropropanes is 100%, first reactor H2Conversion completely, the pentafluoropropene of second reactor 1,1,1,2,3 is converted completely, solves unreacted H2With 1, the separation problem of 1,1,2,3 pentafluoropropene, and de- HF reactions make full use of the heat that hydrogenation reaction is produced, heat is comprehensively utilized, and reduces energy consumption, and two step gas-phase process reaction, technological process is simple, and the three wastes are few.
Description
Technical field
The invention belongs to fluorine-containing propene preparation method technical field, it is related to a kind of preparation side of 2,3,3,3- tetrafluoropropenes
Method.
Background technology
2,3,3,3- tetrafluoropropenes are as single work refrigerant, with excellent ambient parameter, and GWP is that 4, ODP is 0, the longevity
Life phase climate performance (LCCP) is less than 2,3,3,3- tetrafluoropropanes, and air analyte and 2,3,3,3- tetrafluoropropanes are identical, and
Its systematic function is better than 2,3,3,3- tetrafluoropropane refrigerants, if replacing 2,3,3,3- tetrafluoros third from 2,3,3,3- tetrafluoropropenes
Alkane refrigerant, then car manufactures can just continue to continue to use former mounted air conditioner system, so, 2,3,3,3- tetrafluoropropenes are considered as
It is the young mobile refrigerant replacement for relatively having potentiality, is received by car manufactures in West Europe at present, opened in 2011
Beginning progressively promotes.
The preparation method of 2,3,3,3- tetrafluoropropenes mainly has 3 kinds：Trifluoro propene method, tetrafluoropropene method and hexafluoropropene
Method, other method is all branch's technique of these three techniques；The step of trifluoro propene method technique 4 reaction 2,3,3,3- tetrafluoros third of synthesis
Alkene, synthetic route is long, and total recovery is low；Tetrachloropropylene method technique can synthesize 2,3,3,3- tetrafluoropropenes, second by two-step reaction
Walk reaction temperature high, the conversion ratio of catalyst is low；General hexafluoropropene technique is two steps hydrogenation, two step defluorinates by the reaction of 4 steps
Change hydrogen reaction, it is more to there is processing step, the low shortcoming of yield, therefore, need to work out conversion ratio and selectivity it is high 2,3,3,3-
The preparation method of tetrafluoropropene.
The content of the invention
It is an object of the invention to provide a kind of preparation method of 2,3,3,3- tetrafluoropropenes, overcome in existing preparation method
Synthetic route is long, conversion ratio and selectivity it is low the problem of.
The technical scheme is that：
The preparation method of 2,3,3,3- tetrafluoropropenes of one kind of the invention, it is characterised in that specifically include following steps：
Step 1：Hexafluoropropene and hydrogen are pressed 1：0.9~0.99 mol ratio adds first reactor, by pre- place
Reacted in the presence of catalyst after reason, the epimere reaction temperature of the first reactor is 50~140 DEG C, hypomere reaction
Temperature is 160~320 DEG C, and air speed is 0.03~0.20m/s, and reaction pressure is 0.1~0.5Mpa, and reaction obtains containing 1,1,1,2,
3- pentafluoropropenes, 1, the mixture a of 1,1,2,3,3- HFC-236fa, hydrogen fluoride and a small amount of hexafluoropropene；
Step 2：The mixture a that step 1 is obtained is passed through first rectifying column after alkali cleaning, drying and carries out rectifying, described
The tower reactor of first rectifying column obtains 1,1,1,2,3,3- HFC-236fa, and tower top obtains 1,1,1,2,3- pentafluoropropene and a small amount of six
Fluoropropene, is recycled to the first reactor by described 1,1,1,2,3,3- HFC-236fa and is reacted, 1,1,1,2,3- five fluorine
Propylene and a small amount of hexafluoropropene are passed through Second distillation column, and the tower top of the Second distillation column obtains hexafluoropropene, and tower reactor is obtained
1,1,1,2,3- pentafluoropropene, is recycled to first reactor by hexafluoropropene and is reacted；
Step 3：1 that step 2 is obtained, 1,1,2,3- pentafluoropropene is passed through second reactor, while hydrogen is passed through, in warp
Cross in the presence of pretreatment rear catalyst and reacted, the epimere reaction temperature of the second reactor is 100~200 DEG C, on
Section reaction temperature is 180~380 DEG C, and air speed is 0.03~0.31m/s, and reaction pressure is 0.1~0.5Mpa, and reaction obtains containing 1,
1,1,2,3- pentafluoropropane, 2,3,3,3- tetrafluoropropenes, HF and a small amount of H2Mixture b；
Step 4：The mixture b that step 3 is obtained is passed through third distillation column after alkali cleaning, drying, and tower reactor obtains 1,1,1,
2,3- pentafluoropropanes, are recycled in second reactor and are reacted, and tower top obtains the tetrafluoropropene of product 2,3,3,3-.
Catalyst after pretreatment is divided into epimere catalyst and hypomere in the first reactor and second reactor
Catalyst, the epimere catalyst and lower section catalyst are respectively Pd/C, Cr2O3、Cr2O3+ZnO2、Pd/Al2O3In it is any one
Kind.
The epimere catalyst is through 350 DEG C, H2And N2Mol ratio be 1：19, air speed is 0.33mLg-1M/s bars
15h is pre-processed under part, normal temperature is then cooled to, catalyst is taken out and loads first reactor and second reactor epimere.
The lower section catalyst is after HF fluorinations 30h is passed through under the conditions of 350 DEG C, to load first reactor and the second reaction
The hypomere of device.
Hexafluoropropene presses 1 with hydrogen in the step 1：0.95 mol ratio adds first reactor.
The epimere reaction temperature of the first reactor is 100 DEG C, and hypomere reaction temperature is 220 DEG C.
The epimere reaction temperature of the second reactor is 160 DEG C, and hypomere reaction temperature is 260 DEG C.
The air speed of the first reactor is 0.10m/s, and the air speed of second reactor is 0.17m/s.
The beneficial effects of the invention are as follows：
The preparation method of 2,3,3,3- tetrafluoropropenes of one kind of the invention, by two reactors and three rectifying columns, passes through
Test of many times filters out optimum process condition so that the conversion ratio and selectivity entirely reacted is greatly improved, turn of hexafluoropropene
Rate is more than 99%, and the conversion ratio of 1,1,1,2,3- pentafluoropropene is 100%, 1,1,1,2,3,3- HFC-236fa and 1, and 1,1,2,
The selectivity of 3- pentafluoropropanes is 100%, first reactor H2Conversion completely, the pentafluoropropene of second reactor 1,1,1,2,3- is complete
Full conversion, solves unreacted H2With 1, the separation problem of 1,1,2,3- pentafluoropropene, and de- HF reactions make full use of hydrogenation
The heat produced is reacted, heat is comprehensively utilized, reduce energy consumption, two step gas-phase process reaction, technological process is simple, three
It is useless few.
Embodiment
With reference to embodiment, the present invention is described in detail.
The preparation method of 2,3,3,3- tetrafluoropropenes of one kind of the invention, specifically includes following steps：
Step 1：Hexafluoropropene and hydrogen are pressed 1：0.9~0.99 mol ratio adds first reactor, by pre- place
Reacted in the presence of catalyst after reason, the epimere reaction temperature of the first reactor is 50~140 DEG C, hypomere reaction
Temperature is 160~320 DEG C, and air speed is 0.03~0.20m/s, and reaction pressure is 0.1~0.5Mpa, and reaction obtains containing 1,1,1,2,
3- pentafluoropropenes, 1, the mixture a of 1,1,2,3,3- HFC-236fa, hydrogen fluoride and a small amount of hexafluoropropene；
Step 2：The mixture a that step 1 is obtained is passed through first rectifying column after alkali cleaning, drying and carries out rectifying, described
The tower reactor of first rectifying column obtains 1,1,1,2,3,3- HFC-236fa, and tower top obtains 1,1,1,2,3- pentafluoropropene and a small amount of six
Fluoropropene, is recycled to the first reactor by described 1,1,1,2,3,3- HFC-236fa and is reacted, 1,1,1,2,3- five fluorine
Propylene and a small amount of hexafluoropropene are passed through Second distillation column, and the tower top of the Second distillation column obtains hexafluoropropene, and tower reactor is obtained
1,1,1,2,3- pentafluoropropene, is recycled to first reactor by hexafluoropropene and is reacted；
Step 3：1 that step 2 is obtained, 1,1,2,3- pentafluoropropene is passed through second reactor, while hydrogen is passed through, in warp
Cross in the presence of pretreatment rear catalyst and reacted, the epimere reaction temperature of the second reactor is 100~200 DEG C, on
Section reaction temperature is 180~380 DEG C, and air speed is 0.03~0.31m/s, and reaction pressure is 0.1~0.5Mpa, and reaction obtains containing 1,
1,1,2,3- pentafluoropropane, 2,3,3,3- tetrafluoropropenes, HF and a small amount of H2Mixture b；
Step 4：The mixture b that step 3 is obtained is passed through third distillation column after alkali cleaning, drying, and tower reactor obtains 1,1,1,
2,3- pentafluoropropanes, are recycled in second reactor and are reacted, and tower top obtains the tetrafluoropropene of product 2,3,3,3-.
Catalyst after pretreatment is divided into epimere catalyst and hypomere in the first reactor and second reactor
Catalyst, the epimere catalyst and lower section catalyst are respectively Pd/C, Cr2O3、Cr2O3+ZnO2、Pd/Al2O3In it is any one
Kind.
The epimere catalyst is through 350 DEG C, H2And N2Mol ratio be 1：19, air speed is 0.33mLg-1M/s bars
15h is pre-processed under part, normal temperature is then cooled to, catalyst is taken out and loads first reactor and second reactor epimere.
The lower section catalyst is after HF fluorinations 30h is passed through under the conditions of 350 DEG C, to load first reactor and the second reaction
The hypomere of device.
Hexafluoropropene presses 1 with hydrogen in the step 1：0.95 mol ratio adds first reactor.
The epimere reaction temperature of the first reactor is 100 DEG C, and hypomere reaction temperature is 220 DEG C.
The epimere reaction temperature of the second reactor is 160 DEG C, and hypomere reaction temperature is 260 DEG C.
The air speed of the first reactor is 0.10m/s, and the air speed of second reactor is 0.17m/s.
Embodiment 1
100mL Pd/C catalyst is fitted into container, in 350 DEG C, H2And N2Mol ratio be 1：19, air speed is
0.33mL·g-115h is pre-processed under the conditions of m/s, normal temperature is then cooled to, catalyst is taken out and loads first reactor epimere, will
200mLCr2O3Catalyst is passed through under the conditions of 350 DEG C after HF fluorinations 30h, loads the hypomere of first reactor, by step 1 six
Fluoropropene presses 1 with hydrogen：0.95 mol ratio adds first reactor, is reacted in the presence of catalyst, control first
100 DEG C of the epimere reaction temperature of reactor, 220 DEG C of hypomere reaction temperature, reaction pressure 0.5Mpa is constant, by improving constantly the
After the air speed of one reactor, stable reaction reaction obtain contain 1,1,1,2,3- pentafluoropropene (HFO-1225ye), 1,1,1,2,3,
The mixture a of 3- HFC-236fas (HFC-236ea), hydrogen fluoride and a small amount of hexafluoropropene (HFP), mixture a is taken after alkali cleaning
Sample is analyzed, and its analysis result is as shown in table 1.
The first reactor of table 1 exports Analysis of Organic Substances data
As it can be seen from table 1 in 0.03~0.07m/s of low-speed, hexafluoropropene almost reacts completely, and conversion ratio is more than
99.9%, the change of its yield is not obvious, with the continuous improvement of air speed, and air speed is in 0.13~0.20m/s, turn of hexafluoropropene
Rate dramatic decrease, the yield of reaction also drastically declines, so the air speed of first reactor is controlled in 0.10m/s.
Embodiment 2
1 that step 2 is obtained, 1,1,2,3- pentafluoropropene is passed through second reactor, while being passed through hydrogen, control second is anti-
160 DEG C of the epimere reaction temperature of device is answered, hypomere reaction temperature is 260 DEG C, and reaction pressure 0.5Mpa is constant, by improving constantly the
1,1,1,2,3- pentafluoropropane, 2,3,3,3- tetrafluoropropenes, HF and a small amount of H are obtained after the air speed of two reactors, stable reaction2's
Mixture b, the sampling analysis after alkali cleaning, its analysis result is as shown in table 2.
The second reactor of table 2 exports Analysis of Organic Substances data
As can be seen from Table 2：In 0.03~0.17m/s of low-speed, 1,1,1,2,3- pentafluoropropene almost all is anti-
Should, conversion ratio is more than 99.9%, and reaction yield is also higher, with the continuous improvement of air speed, reach 0.22m/s and more than, 1,1,
Conversion ratio, the reaction yield of 1,2,3- pentafluoropropene drastically decline, so second reactor air speed is preferably 0.17m/s.
Embodiment 3
100mL Pd/C catalyst is fitted into container, in 350 DEG C, H2And N2Mol ratio be 1：19, air speed is
0.33mL·g-115h is pre-processed under the conditions of m/s, normal temperature is then cooled to, catalyst is taken out and loads first reactor epimere, will
200mLCr2O3Catalyst is passed through under the conditions of 350 DEG C after HF fluorinations 30h, loads the hypomere of first reactor, by step 1 six
Fluoropropene presses 1 with hydrogen：0.95 mol ratio adds first reactor, is reacted in the presence of catalyst, control first
The air speed 0.10m/s of reactor, 220 DEG C of hypomere reaction temperature, reaction pressure 0.5Mpa is constant, by constantly raising the first reaction
Reaction obtains containing 1,1,1,2,3- pentafluoropropene, 1,1,1,2,3,3- HFC-236fa, hydrogen fluoride after device epimere temperature, stable reaction
With the mixture a of a small amount of hexafluoropropene, by mixture a after alkali cleaning sampling analysis, its analysis result is as shown in table 3.
The first reactor of table 3 exports Analysis of Organic Substances data
From table 3 it can be seen that rise of the first reactor epimere reaction with temperature, hexafluoropropene conversion ratio is improved, reaction
Yield is almost unchanged, but temperature, at 50~80 DEG C, the conversion ratio of hexafluoropropene is significantly improved, and reaction yield change is not obvious,
Temperature is at 80~160 DEG C, and the conversion ratio of hexafluoropropene, reaction yield change are little, from control energy consumption and consumption of raw materials angle,
The temperature of first reactor epimere is preferably controlled in 100 DEG C.
Embodiment 4
100mL Pd/C catalyst is fitted into container, in 350 DEG C, H2And N2Mol ratio be 1：19, air speed is
0.33mL·g-115h is pre-processed under the conditions of m/s, normal temperature is then cooled to, catalyst is taken out and loads first reactor epimere, will
200mLCr2O3Catalyst is passed through under the conditions of 350 DEG C after HF fluorinations 30h, loads the hypomere of first reactor, by step 1 six
Fluoropropene presses 1 with hydrogen：0.95 mol ratio adds first reactor, is reacted in the presence of catalyst, control first
The air speed 0.10m/s of reactor, 100 DEG C of epimere reaction temperature, reaction pressure 0.5Mpa is constant, by constantly raising the first reaction
Reaction obtains containing 1,1,1,2,3- pentafluoropropene, 1,1,1,2,3,3- HFC-236fa, hydrogen fluoride after device hypomere temperature, stable reaction
With the mixture a of a small amount of hexafluoropropene, by mixture a after alkali cleaning sampling analysis, its analysis result is as shown in table 4.
The first reactor of table 4 exports Analysis of Organic Substances data
As can be seen from Table 4：First reactor hypomere temperature is improved with the rise of temperature, the conversion ratio of hexafluoropropene,
But temperature is at 160~220 DEG C, and the conversion ratio of hexafluoropropene is almost unchanged, and the yield of 1,1,1,2,3- pentafluoropropene is increased sharply,
Temperature is at 220~320 DEG C, and conversion ratio, the reaction yield of hexafluoropropene are almost unchanged, and from control and energy consumption angle, first is anti-
The temperature of device hypomere is answered to be preferably controlled in 220 DEG C.
Embodiment 5
1 that step 2 is obtained, 1,1,2,3- pentafluoropropene is passed through second reactor, while being passed through hydrogen, control second is anti-
The air speed 0.17m/s of device is answered, hypomere reaction temperature is 260 DEG C, and reaction pressure 0.5Mpa is constant, by constantly raising the second reaction
1,1,1,2,3- pentafluoropropane, 2,3,3,3- tetrafluoropropenes, HF and a small amount of H are obtained after the epimere temperature of device, stable reaction2It is mixed
Compound b, the sampling analysis after alkali cleaning, its analysis result is as shown in table 5.
The second reactor of table 5 exports Analysis of Organic Substances data
As can be seen from Table 5, temperature is at 100~150 DEG C, and the conversion ratio of 1,1,1,2,3- pentafluoropropene is obviously improved,
Reaction yield change is also obvious, and temperature is at 160~200 DEG C, conversion ratio, the reaction yield of 1,1,1,2,3- pentafluoropropene
Change is not substantially, therefore the temperature of second reactor epimere is preferably controlled in 160 DEG C.
Embodiment 6
1 that step 2 is obtained, 1,1,2,3- pentafluoropropene is passed through second reactor, while being passed through hydrogen, control second is anti-
The air speed 0.17m/s of device is answered, epimere reaction temperature is 160 DEG C, and reaction pressure 0.5Mpa is constant, by constantly raising the second reaction
1,1,1,2,3- pentafluoropropane, 2,3,3,3- tetrafluoropropenes, HF and a small amount of H are obtained after the hypomere temperature of device, stable reaction2It is mixed
Compound b, the sampling analysis after alkali cleaning, its analysis result is as shown in table 6.
The second reactor of table 6 exports Analysis of Organic Substances data
As can be seen from Table 6, temperature is at 180~260 DEG C, and 1,1,1,2,3- pentafluoropropene conversion ratio is not obvious, reaction
Yield change is obvious, and temperature is at 280~380 DEG C, and the conversion ratio of 1,1,1,2,3- pentafluoropropene, reaction yield change are equal
Not substantially, therefore, the hypomere temperature of second reactor preferably controls 260 DEG C.
Claims (8)
1. the preparation method of the tetrafluoropropene of one kind 2,3,3,3-, it is characterised in that specifically include following steps：
Step 1：Hexafluoropropene and hydrogen are pressed 1：0.9~0.99 mol ratio adds first reactor, after pretreatment
Catalyst in the presence of reacted, the epimere reaction temperature of the first reactor is 50~140 DEG C, hypomere reaction temperature
For 160~320 DEG C, air speed is 0.03~0.20m/s, and reaction pressure is 0.1~0.5Mpa, and reaction obtains containing 1,1,1,2,3- five
Fluoropropene, 1, the mixture a of 1,1,2,3,3- HFC-236fa, hydrogen fluoride and a small amount of hexafluoropropene；
Step 2：The mixture a that step 1 is obtained is passed through first rectifying column after alkali cleaning, drying and carries out rectifying, described first
The tower reactor of rectifying column obtains 1,1,1,2,3,3- HFC-236fa, and tower top obtains 1,1,1,2,3- pentafluoropropene and a small amount of hexafluoro third
Alkene, is recycled to the first reactor by described 1,1,1,2,3,3- HFC-236fa and is reacted, 1,1,1,2,3- pentafluoropropene
Second distillation column is passed through with a small amount of hexafluoropropene, the tower top of the Second distillation column obtains hexafluoropropene, and tower reactor obtains 1,1,
1,2,3- pentafluoropropene, is recycled to first reactor by hexafluoropropene and is reacted；
Step 3：1 that step 2 is obtained, 1,1,2,3- pentafluoropropene is passed through second reactor, while hydrogen is passed through, by pre-
Reacted in the presence of processing rear catalyst, the epimere reaction temperature of the second reactor is 100~200 DEG C, and epimere is anti-
It is 180~380 DEG C to answer temperature, and air speed is 0.03~0.31m/s, and reaction pressure is 0.1~0.5Mpa, and reaction obtains containing 1,1,1,
2,3- pentafluoropropanes, 2,3,3,3- tetrafluoropropenes, HF and a small amount of H2Mixture b；
Step 4：The mixture b that step 3 is obtained is passed through third distillation column after alkali cleaning, drying, and tower reactor obtains 1,1,1,2,3-
Pentafluoropropane, is recycled in second reactor and is reacted, and tower top obtains the tetrafluoropropene of product 2,3,3,3-.
2. the preparation method of 2,3,3,3- tetrafluoropropenes of one kind as claimed in claim 1, it is characterised in that first reaction
Catalyst after pretreatment is divided into epimere catalyst and lower section catalyst, the epimere catalyst in device and second reactor
It is respectively Pd/C, Cr with lower section catalyst2O3、Cr2O3+ZnO2、Pd/Al2O3In any one.
3. the preparation method of 2,3,3,3- tetrafluoropropenes of one kind as claimed in claim 2, it is characterised in that the epimere catalysis
Agent is through 350 DEG C, H2And N2Mol ratio be 1：19, air speed is 0.33mLg-115h is pre-processed under the conditions of m/s, is then dropped
Temperature takes out catalyst and loads first reactor and second reactor epimere to normal temperature.
4. the preparation method of 2,3,3,3- tetrafluoropropenes of one kind as claimed in claim 2, it is characterised in that the hypomere catalysis
Agent is after HF fluorinations 30h is passed through under the conditions of 350 DEG C, to load the hypomere of first reactor and second reactor.
5. the preparation method of 2,3,3,3- tetrafluoropropenes of one kind as claimed in claim 1, it is characterised in that in the step 1
Hexafluoropropene presses 1 with hydrogen：0.95 mol ratio adds first reactor.
6. the preparation method of 2,3,3,3- tetrafluoropropenes of one kind as claimed in claim 1, it is characterised in that first reaction
The epimere reaction temperature of device is 100 DEG C, and hypomere reaction temperature is 220 DEG C.
7. the preparation method of 2,3,3,3- tetrafluoropropenes of one kind as claimed in claim 1, it is characterised in that second reaction
The epimere reaction temperature of device is 160 DEG C, and hypomere reaction temperature is 260 DEG C.
8. the preparation method of 2,3,3,3- tetrafluoropropenes of one kind as claimed in claim 1, it is characterised in that first reaction
The air speed of device is 0.10m/s, and the air speed of second reactor is 0.17m/s.
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