[go: up one dir, main page]

CN102001911A - Method for preparing 2,3,3,3-tetrafluoropropene - Google Patents

Method for preparing 2,3,3,3-tetrafluoropropene Download PDF

Info

Publication number
CN102001911A
CN102001911A CN2010102869653A CN201010286965A CN102001911A CN 102001911 A CN102001911 A CN 102001911A CN 2010102869653 A CN2010102869653 A CN 2010102869653A CN 201010286965 A CN201010286965 A CN 201010286965A CN 102001911 A CN102001911 A CN 102001911A
Authority
CN
China
Prior art keywords
reactor
chloro
reaction
hydrogen fluoride
tetrafluoropropane
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN2010102869653A
Other languages
Chinese (zh)
Other versions
CN102001911B (en
Inventor
吕剑
王博
李凤仙
寇联岗
王伟
刘波
杨志强
亢建平
李亚妮
封利民
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shandong Huaan Modern Environmental Protection Technology Co., Ltd.
Original Assignee
Xian Modern Chemistry Research Institute
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Xian Modern Chemistry Research Institute filed Critical Xian Modern Chemistry Research Institute
Priority to CN 201010286965 priority Critical patent/CN102001911B/en
Publication of CN102001911A publication Critical patent/CN102001911A/en
Application granted granted Critical
Publication of CN102001911B publication Critical patent/CN102001911B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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

2,3,3, the preparation method of 3-tetrafluoeopropene
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 a raw material, obtains 2,3 through two step gas phase fluorination, 3, the preparation method of 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, 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.U.S. Pat 2009024009 discloses the synthetic method of a kind of HFO-1234yf.This method is with 1,1,2, and 3-tetrachloro propylene is a raw material, 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,, obtains HFO-1234yf at 350～550 ℃ of dehydrochlorinations.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)
Figure BSA00000276873100011
The present invention adopts two reactors, and first reactor mainly carries out HF and fluoridizes 1,1,2, the reaction of 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 the 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 1,1,1,2, the side reaction (4) of 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, with 1,1,2,3-tetrachloro propylene is a raw material, 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 1,1,2, the mol ratio 5～20 of 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, the 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 1,1,1,2, the mol ratio 2～15 of 2-pentafluoropropane total amount, comprise 2 in the product stream that obtains, 3,3, the 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 tower still component is a 2-chloro-3,3,3-trifluoro propene, 2-chloro-1,1,1,2-tetrafluoropropane, 1,1,1,2,2-pentafluoropropane and hydrogen fluoride, the cat head component is hydrogenchloride and 2,3,3, the 3-tetrafluoeopropene, go out reactive system,, obtain target product 2 through deacidification, dehydration, rectifying, 3,3, the 3-tetrafluoeopropene;
D. the tower still component of step c distillation tower enters the second column separation, and tower still component is a 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: reaction pressure 0.3MPa～0.6MPa, hydrogen fluoride and 1,1,2, the mol ratio 10～15 of 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-1,1,1,2-tetrafluoropropane and 1,1,1,2, the mol ratio 4～8 of 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 tower still component is HF, HCFC-1233xf, HCFC-244bb and HFC-245cb.The present invention can suitably select according to the working pressure of the level of equipment, general facilities, reactive system and the isolating composition of desire 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 still temperature are by working pressure and material component decision 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, fluorizated chromic oxide, aluminum fluoride, fluorizated aluminum oxide, 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 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 2,3,3, preparation technology's schema of 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 1,1,2, the mixture of 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 still 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 still 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
At internal diameter is to add 50 milliliters of chromium-based fluorination catalysts that contain Al, Zn, Mg, Ni in the carbon steel pipe of 38mm, and 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 1,1,2, the mol ratio of 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.
Embodiment 2
Operation substantially the same manner as Example 1, different is 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, different is 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, different is to change the first reactor reaction temperature into 350 ℃, the results are shown in Table 1.
Embodiment 5
Operation substantially the same manner as Example 1, different is changes material into 2 seconds the results are shown in Table 1 duration of contact.
Embodiment 6
Operation substantially the same manner as Example 1, different is will change 10 seconds duration of contact into to the results are shown in Table 1.
Embodiment 7
Operation substantially the same manner as Example 1, different is will change 30 seconds duration of contact into to the results are shown in Table 1.
Embodiment 8
Operation substantially the same manner as Example 1, different is with HF and 1,1,2, the mol ratio of 3-tetrachloro propylene changes 5 into, the results are shown in Table 1.
Embodiment 9
Operation substantially the same manner as Example 1, different is with HF and 1,1,2, the mol ratio of 3-tetrachloro propylene changes 15 into, the results are shown in Table 1.
Embodiment 10
Operation substantially the same manner as Example 1, different is with HF and 1,1,2, the mol ratio of 3-tetrachloro propylene changes 20 into, the results are shown in Table 1.
Embodiment 11
Operation substantially the same manner as Example 1, different is to change reaction pressure into 0.3MPa, the results are shown in Table 1.
Embodiment 12
Operation substantially the same manner as Example 1, different is to change reaction pressure into 0.6MPa, the results are shown in Table 1.
Embodiment 13
Operation substantially the same manner as Example 1, different is to change reaction pressure into 1.0MPa, the results are shown in Table 1.
Table 1
Figure BSA00000276873100061
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 14
At internal diameter is to add 50 milliliters of chromium-based fluorination catalysts that contain Al, Zn, Mg, Ni in the carbon steel pipe of 38mm, 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, different is changes the temperature of reaction of second reactor into 280 ℃, the results are shown in Table 2.
Embodiment 16
Operation substantially the same manner as Example 14, different is changes the temperature of reaction of second reactor into 320 ℃, the results are shown in Table 2.
Embodiment 17
Operation substantially the same manner as Example 14, different is changes the temperature of reaction of second reactor into 380 ℃, the results are shown in Table 2.
Embodiment 18
Operation substantially the same manner as Example 14, different is to change 5 seconds duration of contact into, the results are shown in Table 2.
Embodiment 19
Operation substantially the same manner as Example 14, different is to change 15 seconds duration of contact into, the results are shown in Table 2.
Embodiment 20
Operation substantially the same manner as Example 14, different is to change 30 seconds duration of contact into, the results are shown in Table 2.
Embodiment 21
Operation substantially the same manner as Example 14, different mol ratios with HF and HCFC-1233xf change 2 into and the results are shown in Table 2.
Embodiment 22
Operation substantially the same manner as Example 14, different mol ratios with HF and HCFC-1233xf change 8 into, the results are shown in Table 2.
Embodiment 23
Operation substantially the same manner as Example 14, different mol ratios with HF and HCFC-1233xf change 15 into, the results are shown in Table 2.
Embodiment 24
Operation substantially the same manner as Example 14, different change reaction pressure into 0.3MPa, the results are shown in Table 2.
Embodiment 25
Operation substantially the same manner as Example 14, different change reaction pressure into 0.6MPa, the results are shown in Table 2.
Embodiment 26
Operation substantially the same manner as Example 14, different change 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
At internal diameter is to add 50 milliliters in the carbon steel pipe of 38mm to contain Al, 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,, the results are shown in Table 3 with organic composition in the gas chromatographic analysis reaction product.
Embodiment 28
Operation substantially the same manner as Example 27, different molar ratios with HFC-245cb, HCFC-244bb and HCFC-1233xf change 0.2: 0.5: 1 into, the results are shown in Table 3.
Embodiment 29
Operation substantially the same manner as Example 27, different molar ratios with HFC-245cb, HCFC-244bb and HCFC-1233xf change 0.5: 0.1: 1 into, the results are shown in Table 3.
Embodiment 30
Operation substantially the same manner as Example 27, different molar ratios with HFC-245cb, HCFC-244bb and HCFC-1233xf change 0.5: 0.5: 1 into, the results are shown in Table 3.
Table 3
Figure BSA00000276873100091
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 are with 1,1,2, and 3-tetrachloro propylene is a raw material, 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, hydrogen fluoride and 1,1,2, the mol ratio 5～20 of 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 1,1,1,2, the mol ratio 2～15 of 2-pentafluoropropane total amount, comprise 2,3 in the product stream that obtains, 3, the 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 tower still component is a 2-chloro-3,3,3-trifluoro propene, 2-chloro-1,1,1,2-tetrafluoropropane, 1,1,1,2,2-pentafluoropropane and hydrogen fluoride, the cat head component is hydrogenchloride and 2,3,3, the 3-tetrafluoeopropene, go out reactive system,, obtain target product 2 through deacidification, dehydration, rectifying, 3,3, the 3-tetrafluoeopropene;
D. the tower still component of step c distillation tower enters the second column separation, and tower still component is a 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 a 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: reaction pressure 0.3MPa～0.6MPa, hydrogen fluoride and 1,1,2, the mol ratio 10～15 of 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-1,1,1,2-tetrafluoropropane and 1,1,1,2, the mol ratio 4～8 of 2-pentafluoropropane total amount; 10 seconds～15 seconds duration of contact; 320 ℃～350 ℃ of temperature of reaction.
CN 201010286965 2010-09-20 2010-09-20 Method for preparing 2,3,3,3-tetrafluoropropene Active CN102001911B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN 201010286965 CN102001911B (en) 2010-09-20 2010-09-20 Method for preparing 2,3,3,3-tetrafluoropropene

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN 201010286965 CN102001911B (en) 2010-09-20 2010-09-20 Method for preparing 2,3,3,3-tetrafluoropropene

Publications (2)

Publication Number Publication Date
CN102001911A true CN102001911A (en) 2011-04-06
CN102001911B CN102001911B (en) 2013-09-25

Family

ID=43809655

Family Applications (1)

Application Number Title Priority Date Filing Date
CN 201010286965 Active CN102001911B (en) 2010-09-20 2010-09-20 Method for preparing 2,3,3,3-tetrafluoropropene

Country Status (1)

Country Link
CN (1) CN102001911B (en)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102351637A (en) * 2011-08-31 2012-02-15 浙江师范大学 Method for preparing 2,3,3,3-tetrafluoropropene
CN102584520A (en) * 2011-12-30 2012-07-18 浙江师范大学 Preparation method of 1,1,1,3-tetrafluoropropene
WO2013022676A1 (en) * 2011-08-07 2013-02-14 Dow Global Technologies, Llc Process for the production of chlorinated propenes
CN102992946A (en) * 2011-09-14 2013-03-27 中化蓝天集团有限公司 2-chloro-3,3,3-trifluoropropylene preparation method
KR20140071458A (en) * 2011-09-30 2014-06-11 허니웰 인터내셔날 인코포레이티드 Process for producing 2,3,3,3-tetrafluoropropene
KR20140097149A (en) * 2011-11-04 2014-08-06 하이유 왕 Process for producing 2,3,3,3-tetrafluoropropene
CN104010999A (en) * 2011-12-22 2014-08-27 阿克马法国公司 Method for preparing fluorinated olefin compounds
CN104496747A (en) * 2014-12-30 2015-04-08 山东东岳化工有限公司 Preparation method of 2, 3, 3, 3-tetrafluoropropene
US9795941B2 (en) 2012-09-30 2017-10-24 Blue Cube Ip Llc Weir quench and processes incorporating the same
CN108430960A (en) * 2016-01-06 2018-08-21 大金工业株式会社 Method for producing 2,3,3,3-tetrafluoropropene
US10065157B2 (en) 2012-10-26 2018-09-04 Blue Cube Ip Llc Mixer and processes incorporating the same
CN109438171A (en) * 2018-11-27 2019-03-08 浙江三美化工股份有限公司 A kind of method that gas phase continuously synthesizes 2,3,3,3- tetrafluoropropene
CN109796300A (en) * 2018-12-29 2019-05-24 浙江巨化技术中心有限公司 A kind of continuous preparation method of 2,3,3,3- tetrafluoropropene
CN112313199A (en) * 2018-06-06 2021-02-02 霍尼韦尔国际公司 Process for the dehydrochlorination of HCFC-244bb to produce HFO-1234yf
CN116120147A (en) * 2023-01-05 2023-05-16 淄博飞源化工有限公司 Method for preparing 2, 3-tetrafluoropropene and hydrogen chloride by recycling and co-producing
CN116120147B (en) * 2023-01-05 2025-08-01 淄博飞源化工有限公司 Method for preparing 2, 3-tetrafluoropropene and hydrogen chloride by recycling and co-producing

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5706432B2 (en) 2009-10-09 2015-04-22 ダウ グローバル テクノロジーズ エルエルシー Method for producing chlorinated and / or fluorinated propene
WO2011044514A2 (en) 2009-10-09 2011-04-14 Dow Global Technologies, Inc Isothermal multitube reactors and processes incorporating the same
CN102686544B (en) 2009-10-09 2017-02-15 蓝立方知识产权公司 Processes for the production of chlorinated and/or fluorinated propenes and higher alkenes
CA2836493A1 (en) 2011-05-31 2012-12-06 Max Markus Tirtowidjojo Process for the production of chlorinated propenes
WO2012166394A1 (en) 2011-05-31 2012-12-06 Dow Global Technologies, Llc Process for the production of chlorinated propenes
US8927792B2 (en) 2011-06-08 2015-01-06 Dow Agrosciences, Llc Process for the production of chlorinated and/or fluorinated propenes
EP3366661A1 (en) 2011-08-07 2018-08-29 Blue Cube IP LLC Process for the production of chlorinated propenes
EP2782889B1 (en) 2011-11-21 2016-12-21 Blue Cube IP LLC Process for the production of chlorinated alkanes
JP6059246B2 (en) 2011-12-02 2017-01-11 ブルー キューブ アイピー エルエルシー Method for producing chlorinated alkane
WO2013082410A1 (en) 2011-12-02 2013-06-06 Dow Global Technologies, Llc Process for the production of chlorinated alkanes
CN104024188B (en) 2011-12-13 2018-05-01 蓝立方知识产权有限责任公司 The method for producing chlorination propane and propylene
CN110128239A (en) 2011-12-22 2019-08-16 蓝立方知识产权有限责任公司 The method for producing tetrachloromethane
US9512049B2 (en) 2011-12-23 2016-12-06 Dow Global Technologies Llc Process for the production of alkenes and/or aromatic compounds
WO2014046977A1 (en) 2012-09-20 2014-03-27 Dow Global Technologies, Llc Process for the production of chlorinated propenes
WO2014046970A1 (en) 2012-09-20 2014-03-27 Dow Global Technologies, Llc Process for the production of chlorinated propenes
JP6247311B2 (en) 2012-12-18 2017-12-13 ブルー キューブ アイピー エルエルシー Method for producing chlorinated propene
CA2894168C (en) 2012-12-19 2018-04-24 Dow Global Technologies Llc Process for the production of chlorinated propenes
JP2016507590A (en) 2013-02-27 2016-03-10 ブルー キューブ アイピー エルエルシー Method for producing chlorinated propene
US9403741B2 (en) 2013-03-09 2016-08-02 Blue Cube Ip Llc Process for the production of chlorinated alkanes

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1976885A (en) * 2004-04-29 2007-06-06 霍尼韦尔国际公司 Processes for synthesis of 1,3,3,3-tetrafluoropropene and 2,3,3,3-tetrafluoropropene
CN101589010A (en) * 2006-10-31 2009-11-25 纳幕尔杜邦公司 Processes for producing 2,3,3,3-tetrafluoropropene and/or 1,2,3,3-tetrafluoropropene
CN101597209A (en) * 2008-03-20 2009-12-09 霍尼韦尔国际公司 Be used to prepare 2,3,3, the integrated process of 3-tetrafluoeopropene
CN101665404A (en) * 2008-08-15 2010-03-10 霍尼韦尔国际公司 Method for producing 2,3,3,3-tetrafluoropropene
CN101665405A (en) * 2008-07-31 2010-03-10 霍尼韦尔国际公司 Method for producing 2,3,3,3-tetrafluoropropene

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1976885A (en) * 2004-04-29 2007-06-06 霍尼韦尔国际公司 Processes for synthesis of 1,3,3,3-tetrafluoropropene and 2,3,3,3-tetrafluoropropene
CN101589010A (en) * 2006-10-31 2009-11-25 纳幕尔杜邦公司 Processes for producing 2,3,3,3-tetrafluoropropene and/or 1,2,3,3-tetrafluoropropene
CN101597209A (en) * 2008-03-20 2009-12-09 霍尼韦尔国际公司 Be used to prepare 2,3,3, the integrated process of 3-tetrafluoeopropene
CN101665405A (en) * 2008-07-31 2010-03-10 霍尼韦尔国际公司 Method for producing 2,3,3,3-tetrafluoropropene
CN101665404A (en) * 2008-08-15 2010-03-10 霍尼韦尔国际公司 Method for producing 2,3,3,3-tetrafluoropropene

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108929192A (en) * 2011-08-07 2018-12-04 蓝立方知识产权有限责任公司 The method for producing the propylene of chlorination
WO2013022676A1 (en) * 2011-08-07 2013-02-14 Dow Global Technologies, Llc Process for the production of chlorinated propenes
CN103717559A (en) * 2011-08-07 2014-04-09 陶氏环球技术有限责任公司 Process for the production of chlorinated propenes
CN102351637A (en) * 2011-08-31 2012-02-15 浙江师范大学 Method for preparing 2,3,3,3-tetrafluoropropene
CN102351637B (en) * 2011-08-31 2013-10-23 浙江师范大学 A kind of preparation method of 2,3,3,3-tetrafluoropropene
CN102992946B (en) * 2011-09-14 2014-11-12 中化蓝天集团有限公司 Preparation method of 2-chloro-3,3,3-trifluoropropylene
CN102992946A (en) * 2011-09-14 2013-03-27 中化蓝天集团有限公司 2-chloro-3,3,3-trifluoropropylene preparation method
KR102003550B1 (en) 2011-09-30 2019-07-25 허니웰 인터내셔날 인코포레이티드 Process for producing 2,3,3,3-tetrafluoropropene
JP2018109053A (en) * 2011-09-30 2018-07-12 ハネウェル・インターナショナル・インコーポレーテッドＨｏｎｅｙｗｅｌｌ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｉｎｃ． Method for producing 2,3,3,3-tetrafluoropropene
EP3808721A1 (en) * 2011-09-30 2021-04-21 Honeywell International Inc. Process for preparing 2-chloro-3,3,3-trifluoropropene
US9540295B2 (en) 2011-09-30 2017-01-10 Honeywell International Inc. Process for producing 2-chloro-3,3,3-trifluoropropene and 2,3,3,3-tetrafluoropropene
JP2014534177A (en) * 2011-09-30 2014-12-18 ハネウェル・インターナショナル・インコーポレーテッド Method for producing 2,3,3,3-tetrafluoropropene
KR20140071458A (en) * 2011-09-30 2014-06-11 허니웰 인터내셔날 인코포레이티드 Process for producing 2,3,3,3-tetrafluoropropene
EP2751057A4 (en) * 2011-09-30 2015-08-12 Honeywell Int Inc Process for producing 2,3,3,3-tetrafluoropropene
KR20140097149A (en) * 2011-11-04 2014-08-06 하이유 왕 Process for producing 2,3,3,3-tetrafluoropropene
KR102052141B1 (en) 2011-11-04 2019-12-04 허니웰 인터내셔날 인코포레이티드 Process for producing 2,3,3,3-tetrafluoropropene
US9187387B2 (en) 2011-12-22 2015-11-17 Arkema France Method for preparing fluorinated olefin compounds
CN104010999A (en) * 2011-12-22 2014-08-27 阿克马法国公司 Method for preparing fluorinated olefin compounds
CN104010999B (en) * 2011-12-22 2016-01-06 阿克马法国公司 Prepare the method for fluorinated olefin compound
CN102584520A (en) * 2011-12-30 2012-07-18 浙江师范大学 Preparation method of 1,1,1,3-tetrafluoropropene
CN102584520B (en) * 2011-12-30 2013-11-27 浙江师范大学 A kind of preparation method of 1,3,3,3-tetrafluoropropene
US9795941B2 (en) 2012-09-30 2017-10-24 Blue Cube Ip Llc Weir quench and processes incorporating the same
US10065157B2 (en) 2012-10-26 2018-09-04 Blue Cube Ip Llc Mixer and processes incorporating the same
CN104496747A (en) * 2014-12-30 2015-04-08 山东东岳化工有限公司 Preparation method of 2, 3, 3, 3-tetrafluoropropene
CN104496747B (en) * 2014-12-30 2018-12-28 山东东岳化工有限公司 A kind of preparation method of 2,3,3,3- tetrafluoropropene
CN108430960A (en) * 2016-01-06 2018-08-21 大金工业株式会社 Method for producing 2,3,3,3-tetrafluoropropene
CN112313199A (en) * 2018-06-06 2021-02-02 霍尼韦尔国际公司 Process for the dehydrochlorination of HCFC-244bb to produce HFO-1234yf
US12304880B2 (en) 2018-06-06 2025-05-20 Honeywell International Inc. Method for dehydrochlorination of HCFC-244BB to manufacture HFO-1234YF
CN109438171A (en) * 2018-11-27 2019-03-08 浙江三美化工股份有限公司 A kind of method that gas phase continuously synthesizes 2,3,3,3- tetrafluoropropene
CN109438171B (en) * 2018-11-27 2022-02-01 浙江三美化工股份有限公司 Method for continuously synthesizing 2,3,3, 3-tetrafluoropropene in gas phase
CN109796300A (en) * 2018-12-29 2019-05-24 浙江巨化技术中心有限公司 A kind of continuous preparation method of 2,3,3,3- tetrafluoropropene
CN116120147A (en) * 2023-01-05 2023-05-16 淄博飞源化工有限公司 Method for preparing 2, 3-tetrafluoropropene and hydrogen chloride by recycling and co-producing
CN116120147B (en) * 2023-01-05 2025-08-01 淄博飞源化工有限公司 Method for preparing 2, 3-tetrafluoropropene and hydrogen chloride by recycling and co-producing

Also Published As

Publication number Publication date
CN102001911B (en) 2013-09-25

Similar Documents

Publication Publication Date Title
CN102001911B (en) Method for preparing 2,3,3,3-tetrafluoropropene
CN102001910B (en) Method for preparing 2,3,3,3-tetrafluoropropene
CN100488925C (en) Method for producing 1,1,1,3-tetrafluoroethylene
US10329227B2 (en) Process for the preparation of 2,3,3,3-tetrafluoropropene
CN101351427B (en) Method for producing fluorinated organic compounds
CN102164881B (en) Process for producing 1,3,3,3-tetrafluoropropene
JP5930077B2 (en) Method for producing 2,3,3,3-tetrafluoropropene
CN106349005B (en) A kind of method of coproduction trifluoropropyl alkenes product and tetrafluoropropene class product
CN103189338A (en) Integrated process to coproduce trans-1-chloro-3,3,3-trifluoropropene, trans-1,3,3,3-tetrafluoropropene, and 1,1,1,3,3-pentafluoropropane
CN101544536B (en) Process for the manufacture of fluorinated olefins
JP5971305B2 (en) Method for producing 2,3,3,3-tetrafluoropropene
CN101215220A (en) Preparation method for 1,1,1,3-tetrafluoropropene
CN104185616A (en) Integrated process to coproduce trans-1-chloro-3,3,3-trifluoropropene, trans-1,3,3,3-tetrafluoropropene, and 1,1,1,3,3-pentafluoropropane
CN107522592B (en) Method for coproducing various halogenated olefins and fluorinated alkanes
CN103429558A (en) Integrated process to co-produce trans-1-chloro-3,3,3-trifluoropropene, trans-1,3,3,3-tetrafluoropropene, and 1,1,1,3,3-pentafluoropropane
EP3325435B1 (en) Process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf)
CN104710274B (en) Process for co-producing 1,3,3,3-tetrafluoropropene and/or 2,3,3,3-tetrafluoropropene
CN100488926C (en) Method for producign 1,1,1,3,3-propane pentafluoride
CN101117305A (en) Method for preparing 1,1,1,2-tetrafluoro thane
CN105102402B (en) Produce the reaction system and method for fluorinated organic compound
KR20170015474A (en) Method for producing chloropropene and method for producing 2,3,3,3-tetrafluoropropene
CN102701903A (en) Method for preparing 3, 3, 3-trifluoropropene
CN116120147B (en) Method for preparing 2, 3-tetrafluoropropene and hydrogen chloride by recycling and co-producing

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
C41 Transfer of patent application or patent right or utility model
TR01 Transfer of patent right

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