CN102001911B - Method for preparing 2,3,3,3-tetrafluoropropene - Google Patents
Method for preparing 2,3,3,3-tetrafluoropropene Download PDFInfo
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- CN102001911B CN102001911B CN 201010286965 CN201010286965A CN102001911B CN 102001911 B CN102001911 B CN 102001911B CN 201010286965 CN201010286965 CN 201010286965 CN 201010286965 A CN201010286965 A CN 201010286965A CN 102001911 B CN102001911 B CN 102001911B
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Abstract
The invention discloses a method for preparing 2,3,3,3-tetrafluoropropene, comprising the following steps: a. in the presence of a fluorinated catalyst, hydrogen fluoride and 1,1,1,2,2-pentachloropropane or 2,3,3,3-tetrafluoropropene enter into a first reactor to react; b. in the presence of the fluorinated catalyst, 2-chloro-3,3,3 trifluoropropene, 2-chloro-1,1,1,2-tetrafluoropropane, 1,1,1,2,2-pentafluoropropane and hydrogen fluoride enter into a second reactor to react; c. the product flow in the step a enters into a first distillation tower to be separated, the tower top components break away from the reaction system and the tower reactor components enter into a phase separator; d. the lower-layer components in the phase separator are recycled to the first reactor and the upper-layer light components in the phase separator and the product flow in the step b enter into a second distillation tower to be separated; e. the tower reactor components in the second distillation tower are recycled to the second reactor and the tower top components enter into a third distillation tower to be separated; and f. the tower reactor components on the third distillation tower are recycled to the second reactor and the tower top components break away from the reaction system.
Description
Technical field
The present invention relates to a kind of 2,3,3, the preparation method of 3-tetrafluoeopropene (HFO-1234yf), relate in particular to a kind of in the presence of fluorination catalyst, with hydrogen fluoride and 1,1,2,3-tetrachloro propylene (HCC-1230xf) is raw material, obtains 2,3 through two step gas phase fluorination, the preparation method of 3,3-tetrafluoeopropene.
Background technology
At present, 1,1,1,2-Tetrafluoroethane (HFC-134a) is widely used in the mobile air conditioner system as refrigeration agent, and value (GWP) is 1430 because its Greenhouse effect are dived, and can cause global warming, needs the new needs of substitute to conform of exploitation.
2,3,3,3-tetrafluoeopropene, the ozone depletion value (ODP) of diving is zero, and GWP is 4, and atmospheric lifetime is 11 days only, has good physical and chemical performance, is considered to directly substitute the economical scheme of HFC-134a.US Patent No. 2009024009 discloses the synthetic method of a kind of HFO-1234yf.This method is raw material with 1,1,2,3-tetrachloro propylene, at first at Cr
2O
3Under the existence of catalyzer, carry out HF gas phase fluorination 1,1,2 in first reactor, 3-tetrachloro propylene obtains 2-chloro-3,3, and 3-trifluoro propene (HCFC-1233xf) is then in second reactor, at SbCl
5Exist down, HF liquid-phase fluorination HCFC-1233xf obtains 2-chloro-1,1,1, and 2-tetrafluoropropane (HCFC-244bb) is at last in the 3rd reactor, at CsCl/MgF
2There is HCFC-244bb down, at 350～550 ℃ of dehydrochlorinations, obtains HFO-1234yf.But this method needs three-step reaction; And second the step be liquid-phase catalysis reaction, need isolation of intermediate products HCFC-244bb is as the raw material of three-step reaction.
Summary of the invention
Technical problem to be solved by this invention is the deficiency that overcomes in the background technology, provides a kind of reactions steps less, need not the separation of intermediate product, and operational path is simple 2,3,3,3-tetrafluoeopropene preparation method.
The gas phase catalytic fluorination legal system is equipped with HFO-1234yf, and the principal reaction of generation is as follows:
CCl
2＝CClCH
2Cl+3HF——→CF
3CCl＝CH
2+3HCl (1)
CF
3CCl＝CH
2+HF——→CF
3CFClCH
3 (2)
CF
3CFClCH
3——→CF
3CF＝CH
2+HCl (3)
The main side reaction that takes place:
CF
3CFClCH
3+HF——→CF
3CF
2CH
3+HCl (4)
The present invention adopts two reactors, and first reactor mainly carries out the reaction that HF fluoridizes 1,1,2,3-tetrachloro propylene, and under proper reaction conditions, 1,1,2,3-tetrachloro propylene conversion can reach 100%, and primary product is HCFC-1233xf; Second reactor mainly carries out reaction that HF fluoridizes HCFC-1233xf and the reaction of HCFC-244bb dehydrochlorination, (2) and (3) react, HCFC-244bb can take place simultaneously fluoridize generation 1,1,1, the side reaction (4) of 2,2-pentafluoropropane (HFC-245cb) and HFO-1234yf and HF addition generate the side reaction (5) of HFC-245cb.The present invention is circulated to second reactor with the HCl that reaction in second reactor generates with HFO-1234yf all the other products after separating, need not to carry out HCFC-244bb separates, and the HFC-245cb that returns is moved to the left reaction (3) balance, suppress HFO-1234yf and further fluoridized generation HFC-245cb, thereby improved the selectivity of HFO-1234yf.
In order to solve the problems of the technologies described above, of the present invention 2,3,3, the preparation method of 3-tetrafluoeopropene is raw material with 1,1,2,3-tetrachloro propylene, may further comprise the steps:
A. in the presence of fluorination catalyst, hydrogen fluoride and 1,1,2,3-tetrachloro propylene enters first reactor and reacts, and reaction conditions is: reaction pressure 0.1MPa～1.0MPa, HF and 1,1, the mol ratio 5～20 of 2,3-tetrachloro propylene, 2 seconds～30 seconds duration of contact, 220 ℃～350 ℃ of temperature of reaction comprise the 2-chloro-3 that reaction generates in the product that the obtains stream, 3,3-trifluoro propene, hydrogenchloride and unreacted hydrogen fluoride;
B. in the presence of fluorination catalyst, 2-chloro-3,3,3-trifluoro propene, 2-chloro-1,1,1,2-tetrafluoropropane, 1,1,1,2,2-pentafluoropropane and HF enter second reactor and react, and reaction conditions is: reaction pressure 0.1MPa～1.0MPa, 5 seconds～30 seconds duration of contact, 280 ℃～380 ℃ of temperature of reaction, HF and 2-chloro-3,3,3 trifluoro propenes, 2-chloro-1,1,1,2-tetrafluoropropane and 1,1, the mol ratio 2～15 of 1,2,2-pentafluoropropane total amount, comprise 2 in the product stream that obtains, 3,3,3-tetrafluoeopropene, 1,1,1,2, the 2-pentafluoropropane, 2-chloro-1,1,1, the 2-tetrafluoropropane, 2-chloro-3,3, the 3-trifluoro propene, hydrogenchloride and unreacted hydrogen fluoride;
C. the product that obtains of step a, b flows to into first distillation tower and separates, and the tower reactor component is 2-chloro-3,3,3-trifluoro propene, 2-chloro-1,1,1,2-tetrafluoropropane, 1,1,1,2,2-pentafluoropropane and hydrogen fluoride, cat head component are hydrogenchloride and 2,3,3,3-tetrafluoeopropene, go out reactive system, through deacidification, dehydration, rectifying, obtain target product 2,3,3,3-tetrafluoeopropene;
D. the tower reactor component of step c distillation tower enters the second column separation, and the tower reactor component is 2-chloro-3,3,3-trifluoro propene and 2-chloro-1,1,1, and the 2-tetrafluoropropane is circulated to second reactor; The cat head component is HF and a small amount of 1,1,1,2, and the 2-pentafluoropropane is circulated to first reactor or/and second reactor.
The reaction conditions of the present invention's first reactor is preferably: the mol ratio 10～15 of reaction pressure 0.3MPa～0.6MPa, hydrogen fluoride and 1,1,2,3-tetrachloro propylene; 5 seconds～10 seconds duration of contact; 260 ℃～300 ℃ of temperature of reaction; The reaction conditions of second reactor is preferably: reaction pressure 0.3MPa～0.6MPa; Hydrogen fluoride and 2-chloro-3,3,3-trifluoro propene, 2-chloro-1,1,1, the mol ratio 4～8 of 2-tetrafluoropropane and 1,1,1,2,2-pentafluoropropane total amount; 10 seconds～15 seconds duration of contact; 320 ℃～350 ℃ of temperature of reaction.
Among the present invention, the reacting product stream of first reactor and second reactor enters first distillation tower to be separated, and the cat head component is HCl and HFO-1234yf, and the tower reactor component is HF, HCFC-1233xf, HCFC-244bb and HFC-245cb.The present invention can suitably select according to the level of equipment, general facilities, the working pressure of reactive system and the composition that desire is separated etc. to the operational condition of distillation tower without limits.Working pressure is 0.1MPa～1.0MPa, preferred 0.3MPa～0.6MPa.Generally speaking, for easy and simple to handle, the working pressure of distillation tower is consistent with reactive system.Tower top temperature and tower reactor temperature are determined by working pressure and material component thereof.
Among the present invention, fresh HF raw material can or enter reactive system by first reactor, second reactor simultaneously by any one reactor in first reactor, second reactor.
The present invention to the catalyzer in the fluoridation without limits, any known fluorination catalyst all is applicable to the present invention, for example: chromic oxide, chromium fluoride, the chromic oxide of fluoridizing, aluminum fluoride, the aluminum oxide of fluoridizing, be carried on chromic oxide on gac, aluminum fluoride, the magnesium fluoride, contain chromic oxide and the activated carbon supported SbCl of multiple metal (as Zn, Co, Ni, Ge, In etc.)
5Or TiCl
4Deng.The fluorination catalyst difference that adopts, reaction conditions difference then comprises the mol ratio of temperature of reaction, reaction pressure, duration of contact and material.The present invention preferably contains the chromium-based fluorination catalyst of Al, Zn, Mg, Ni metal powder, and the catalytic activity of this catalyzer is good, the selectivity height, and regenerability is good, and entire life is long.Chinese patent CN1651137A is seen in the preparation that contains the chromium-based catalysts of Al, Zn, Mg, Ni metal powder.
The type of reactor that the present invention is used for fluoridation is not crucial, any suitable gas phase fluorination device all is applicable to the present invention, and the present invention preferentially selects the material calandria type fixed bed reactor made of nickel and alloy (comprising Hastelloy, Inconel, Incoloy and Monel) thereof for example with anti-hydrogen fluoride corrosion effect for use.
Advantage of the present invention:
Of the present invention 2,3,3,3-tetrafluoeopropene preparation method is the gas phase catalytic fluorination successive reaction, has avoided the second step liquid-phase fluorination process of prior art and the sepn process of intermediate product HCFC-244bb, operational path is simple, reactions steps is less, and reactions steps of the present invention was two steps, and the reactions steps of the method for documents was three steps.
Description of drawings
Fig. 1 represents preparation technology's schema of 2,3,3,3-tetrafluoeopropene.
Label meaning in Fig. 1 is as follows.Pipeline: 1,2,4,6,7,9,10,11,12,13,14 and 16; First reactor: 3; First distillation tower: 5; Second column: 8; Second reactor: 15.
Embodiment
The present invention is described in more detail in conjunction with Fig. 1, but do not limit the present invention.
Fresh 1,1,2,3-tetrachloro propylene or 1, the mixture of 1,2,3-tetrachloro propylene and HF is through pipeline 1, enter in first reactor 3 that is filled with fluorination catalyst by pipeline 2 with the HF logistics that recycles through pipeline 11 and to react, the reactor outlet product pipeline 4 of flowing through is mixed into first distillation tower 5 with the second reactor outlet product stream that returns through pipeline 16 and separates.
First distillation tower, 5 cat head component HFO-1234yf and HCl enter the product after-treatment system by pipeline 6, obtain the HFO-1234yf product by deacidification, dehydration, rectifying; First distillation tower, 5 tower reactor components are HF, HCFC-1233xf, HCFC-244bb and HFC-245cb, enter second column 8 by pipeline 7 and separate.
Second column 8 cat head components are HF and small amount of H FC-245cb, and its part enters first reactor by pipeline 9,11 circulations, and its another part enters second reactor 15 by pipeline 9,12 circulations; Second column 8 tower reactor components are HCFC-1233xf, HCFC-244bb and HFC-245cb, mix mutually through pipeline 12 with second column 8 cat head component HF and small amount of H FC-245cb through pipeline 10, enter second reactor 15 by pipeline 14, under the effect of catalyzer, react; Reacting product stream mixes with first reactor reaction outlet product stream by pipeline 16, enters distillation tower 5 and separates.The fresh HF that adds enters first reactor and second reactor respectively through pipeline 1,13.
Embodiment 1
Be to add 50 milliliters of chromium-based fluorination catalysts that contain Al, Zn, Mg, Ni in the carbon steel pipe of 38mm at internal diameter, method for preparing catalyst is seen Chinese patent CN1651137A.First reactor is warming up to 260 ℃, feeds HF and 1,1,2,3-tetrachloro propylene reacts, control HF and 1, the mol ratio of 1,2,3-tetrachloro propylene is 10, be 5 seconds duration of contact, reaction pressure 0.1MPa, behind the reaction 20h, reaction product is after washing, alkali cleaning, alkali drying are removed HCl and HF, composition with the gas chromatographic analysis reaction product the results are shown in Table 1.
Operation substantially the same manner as Example 1, difference are to change the first reactor reaction temperature into 220 ℃, the results are shown in Table 1.
Embodiment 3
Operation substantially the same manner as Example 1, difference are to change the first reactor reaction temperature into 300 ℃, the results are shown in Table 1.
Embodiment 4
Operation substantially the same manner as Example 1, difference are to change the first reactor reaction temperature into 350 ℃, the results are shown in Table 1.
Operation substantially the same manner as Example 1, difference are to change material into 2 seconds duration of contact to the results are shown in Table 1.
Operation substantially the same manner as Example 1, difference are to the results are shown in Table 1 with changing 10 seconds duration of contact into.
Operation substantially the same manner as Example 1, difference are to the results are shown in Table 1 with changing 30 seconds duration of contact into.
Embodiment 8
Operation substantially the same manner as Example 1, difference are that the mol ratio with HF and 1,1,2,3-tetrachloro propylene changes 5 into, the results are shown in Table 1.
Embodiment 9
Operation substantially the same manner as Example 1, difference are that the mol ratio with HF and 1,1,2,3-tetrachloro propylene changes 15 into, the results are shown in Table 1.
Operation substantially the same manner as Example 1, difference are that the mol ratio with HF and 1,1,2,3-tetrachloro propylene changes 20 into, the results are shown in Table 1.
Operation substantially the same manner as Example 1, difference are to change reaction pressure into 0.3MPa, the results are shown in Table 1.
Operation substantially the same manner as Example 1, difference are to change reaction pressure into 0.6MPa, the results are shown in Table 1.
Operation substantially the same manner as Example 1, difference are to change reaction pressure into 1.0MPa, the results are shown in Table 1.
Table 1
Other product comprises CF
3CFClCH
3(HCFC-244bb), CF
3CF
2CH
3(HFC-245cb) and the trace CF
3CHClCHF
2(HCFC-244db), CF
3CHFCH
2F (HFC-245eb) etc.
Be to add 50 milliliters of chromium-based fluorination catalysts that contain Al, Zn, Mg, Ni in the carbon steel pipe of 38mm at internal diameter, method for preparing catalyst is seen Chinese patent CN1651137A, second reactor is warming up to 350 ℃, feeding HF and HCFC-1233xf reacts, the mol ratio of control HF and HCFC-1233xf is 4, be 10 seconds duration of contact, reaction pressure 0.1MPa, behind the reaction 20h, reaction product is after HCl and HF are removed in washing, alkali cleaning, with organic composition in the gas chromatographic analysis reaction product, the results are shown in Table 2.
Embodiment 15
Operation substantially the same manner as Example 14, difference are that the temperature of reaction with second reactor changes 280 ℃ into, the results are shown in Table 2.
Operation substantially the same manner as Example 14, difference are that the temperature of reaction with second reactor changes 320 ℃ into, the results are shown in Table 2.
Embodiment 17
Operation substantially the same manner as Example 14, difference are that the temperature of reaction with second reactor changes 380 ℃ into, the results are shown in Table 2.
Embodiment 18
Operation substantially the same manner as Example 14, difference are to change 5 seconds duration of contact into, to the results are shown in Table 2.
Embodiment 19
Operation substantially the same manner as Example 14, difference are to change 15 seconds duration of contact into, to the results are shown in Table 2.
Embodiment 20
Operation substantially the same manner as Example 14, difference are to change 30 seconds duration of contact into, to the results are shown in Table 2.
Embodiment 21
Operation substantially the same manner as Example 14, difference changes the mol ratio of HF and HCFC-1233xf into 2 and the results are shown in Table 2.
Embodiment 22
Operation substantially the same manner as Example 14, difference changes the mol ratio of HF and HCFC-1233xf into 8, the results are shown in Table 2.
Embodiment 23
Operation substantially the same manner as Example 14, difference changes the mol ratio of HF and HCFC-1233xf into 15, the results are shown in Table 2.
Embodiment 24
Operation substantially the same manner as Example 14, difference changes reaction pressure into 0.3MPa, the results are shown in Table 2.
Embodiment 25
Operation substantially the same manner as Example 14, difference changes reaction pressure into 0.6MPa, the results are shown in Table 2.
Embodiment 26
Operation substantially the same manner as Example 14, difference changes reaction pressure into 1.0MPa, the results are shown in Table 2.
Table 2
Other product comprises CF
3CFClCH
3(HCFC-244bb), CF
3CF
2CH
3(HFC-245cb) and the trace CF
3CHClCHF
2(HCFC-244db), CF
3CHFCH
2F (HFC-245eb) etc.
Embodiment 27
Be to add 50 milliliters in the carbon steel pipe of 38mm to contain Al at internal diameter, Zn, Mg, the chromium-based fluorination catalyst of Ni, method for preparing catalyst is seen Chinese patent CN1651137A, be warming up to 350 ℃, feed HCFC-1233xf, HCFC-244bb, HFC-245cb and HF react, control HFC-245cb, the molar ratio of HCFC-244bb and HCFC-1233xf 0.1: 0.2: 1, HF and mol ratio (HCFC-1233xf+HCFC-244bb+HFC-245cb) are 4, be 10 seconds duration of contact, reaction pressure 0.1MPa, behind the reaction 20h, reaction product is through washing, after HCl and HF are removed in alkali cleaning, with organic composition in the gas chromatographic analysis reaction product, the results are shown in Table 3.
Embodiment 28
Operation substantially the same manner as Example 27, difference changes the molar ratio of HFC-245cb, HCFC-244bb and HCFC-1233xf into 0.2: 0.5: 1, the results are shown in Table 3.
Embodiment 29
Operation substantially the same manner as Example 27, difference changes the molar ratio of HFC-245cb, HCFC-244bb and HCFC-1233xf into 0.5: 0.1: 1, the results are shown in Table 3.
Embodiment 30
Operation substantially the same manner as Example 27, difference changes the molar ratio of HFC-245cb, HCFC-244bb and HCFC-1233xf into 0.5: 0.5: 1, the results are shown in Table 3.
Table 3
Other product comprises CF
3CFClCH
3(HCFC-244bb), CF
3CF
2CH
3(HFC-245cb) and the trace CF
3CHClCHF
2(HCFC-244db), CF
3CHFCH
2F (HFC-245eb) etc.
Claims (2)
1. one kind 2,3,3, the preparation method of 3-tetrafluoeopropene, this method is raw material with 1,1,2,3-tetrachloro propylene, is made up of following steps:
A. in the presence of fluorination catalyst, hydrogen fluoride and 1,1,2,3-tetrachloro propylene enters first reactor and reacts, and reaction conditions is: reaction pressure 0.1MPa～1.0MPa, hydrogen fluoride and 1,1, the mol ratio 5～20 of 2,3-tetrachloro propylene, 2 seconds～30 seconds duration of contact, 220 ℃～350 ℃ of temperature of reaction comprise the 2-chloro-3 that reaction generates in the product that the obtains stream, 3,3-trifluoro propene, hydrogenchloride and unreacted hydrogen fluoride;
B. in the presence of fluorination catalyst, 2-chloro-3,3, the 3-trifluoro propene, 2-chloro-1,1,1, the 2-tetrafluoropropane, 1,1,1,2,2-pentafluoropropane and hydrogen fluoride enter second reactor and react, and reaction conditions is: reaction pressure 0.1MPa～1.0MPa, 5 seconds～30 seconds duration of contact, 280 ℃～380 ℃ of temperature of reaction, hydrogen fluoride and 2-chloro-3,3,3 trifluoro propenes, 2-chloro-1,1,1,2-tetrafluoropropane and 1,1,1, the mol ratio 2～15 of 2,2-pentafluoropropane total amount, comprise 2,3 in the product stream that obtains, 3,3-tetrafluoeopropene, 1,1,1,2,2-pentafluoropropane, 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoro propene, hydrogenchloride and unreacted hydrogen fluoride;
C. the product that obtains of step a, b flows to into first distillation tower and separates, and the tower reactor component is 2-chloro-3,3,3-trifluoro propene, 2-chloro-1,1,1,2-tetrafluoropropane, 1,1,1,2,2-pentafluoropropane and hydrogen fluoride, cat head component are hydrogenchloride and 2,3,3,3-tetrafluoeopropene, go out reactive system, through deacidification, dehydration, rectifying, obtain target product 2,3,3,3-tetrafluoeopropene;
D. the tower reactor component of step c distillation tower enters the second column separation, and the tower reactor component is 2-chloro-3,3,3-trifluoro propene and 2-chloro-1,1,1, and the 2-tetrafluoropropane is circulated to second reactor; The cat head component is hydrogen fluoride and a small amount of 1,1,1,2, and the 2-pentafluoropropane is circulated to first reactor or/and second reactor.
2. according to claim 12,3,3, the preparation method of 3-tetrafluoeopropene is characterized in that the reaction conditions of first reactor described in the step a is: the mol ratio 10～15 of reaction pressure 0.3MPa～0.6MPa, hydrogen fluoride and 1,1,2,3-tetrachloro propylene; 5 seconds～10 seconds duration of contact; 260 ℃～300 ℃ of temperature of reaction; The reaction conditions of second reactor described in the step b is: reaction pressure 0.3MPa～0.6MPa; Hydrogen fluoride and 2-chloro-3,3,3-trifluoro propene, 2-chloro-1,1,1, the mol ratio 4～8 of 2-tetrafluoropropane and 1,1,1,2,2-pentafluoropropane total amount; 10 seconds～15 seconds duration of contact; 320 ℃～350 ℃ of temperature of reaction.
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Effective date of registration: 20160519 Address after: 255300 Zhoucun City, Shandong province constant access road, No. 979, Patentee after: Shandong Huaan Modern Environmental Protection Technology Co., Ltd. Address before: 710065 Shaanxi province Xi'an Yanta District Zhang eight road No. 168 Patentee before: Xi'an Inst. of Modern Chemistry |