CN106316777A - Preparation method for 2,3,3,3-tetrafluoropropene - Google Patents
Preparation method for 2,3,3,3-tetrafluoropropene Download PDFInfo
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- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
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Abstract
The invention discloses a preparation method for 2,3,3,3-tetrafluoropropene. The preparation method comprises the following steps: (a) reacting chloropenta fluoroethane and methylmagnesium chloride in an organic solvent, and after the reaction is ended, performing cooling, filteration and rectification to obtain 1,1,1,2,2-perfluoropropane, wherein the methylmagnesium chloride and the chloropenta fluoroethane are in the molar ratio of 1:(1-5), the reacting temperature is 20 to 60 DEG C, and the reacting time is 1 to 5 hours; (b) introducing the 1,1,1,2,2-perfluoropropane which is obtained in the step (a) into an alkaline liquor at 50 to 90 DEG C, collecting a gas product, and drying and condensing the gas product to obtain the product, namely, the 2,3,3,3-tetrafluoropropene; or performing gas phase catalysis on the 1,1,1,2,2-perfluoropropane which is obtained in the step (a) under the action of a catalyst to remove HF and obtain the 2,3,3,3-tetrafluoropropene. The preparation method for the 2,3,3,3-tetrafluoropropene has the advantages that the process is simple, raw materials are easily obtained, and the cost is low.
Description
Technical field
The present invention relates to the preparation method of Fluorine containing olefine, particularly to the preparation method of a kind of 2,3,3,3-tetrafluoropropenes.
Background technology
2,3,3,3-tetrafluoropropenes, molecular formula is CF3CF=CH2, boiling point-28.3 DEG C, No. CAS: 754-12-1, its ODP are
0, GWP is 4, has good lifetime climate performance, atmospheric lifetime only 11 days;There is excellent physical and chemical performance, its molecular weight
Close with HFC-134a, there is saturated vapor pressure higher when relatively low boiling point and room temperature, and have close close with HFC-134a
Degree and critical point, be therefore considered as " the direct substitute " of HFC-134a, becomes the most potential forth generation low-carbon (LC) refrigeration
One of agent.
According to document and patent, current 2,3,3,3-tetrafluoropropene synthetic routes are divided by initiation material mainly to be had: tetrafluoro second
Alkene method, trifluoropropyne method, trifluoro propene method, C3-Fluoroalcohol. method, hexafluoropropene method (HFP), tetrachloropropylene method, HCFC-242 method,
Difluorochloromethane method, CF3COCH2COCF3Method, HFO-1234ze isomerization process etc..Wherein hexafluoropropene method is the road of most study
One of line.As open in US20070179324A, CN102267869A, CN102026947A etc. is initiation material by hexafluoropropene,
Through hydrogenation, dehydrofluorination, the four-step reaction such as repeated hydrogenation, dehydrofluorination obtains CF3CF=CH2.While it is true, these patents carry
The method technique of confession yet suffers from that step is many and complicated, equipment investment big, the shortcomings such as separation costs is higher.
CN105111038A disclose with methyl-magnesium-chloride and tetrafluoroethene for initiation material first after through nucleophilic addition-cancellation
Generate 1,1,2-trifluoro propene, 1,1,2-trifluoro propene again with fluorine gas addition generate 1,1,1,2,2-pentafluoropropane, last 1,1,
1,2,2-pentafluoropropane dehydrofluorination three-step reaction prepares 2, the method for 3,3,3-tetrafluoropropenes, but its weak point is technique road
Line is the longest.
Summary of the invention
For the deficiencies in the prior art, it is an object of the invention to provide that a kind of technique is simple, raw material is easy to get, low cost
The preparation method of 2,3,3,3-tetrafluoropropene.
The above-mentioned purpose of the present invention is achieved through the following technical solutions: the preparation side of a kind of 2,3,3,3-tetrafluoropropene
Method, comprises the following steps:
The preparation of (a) 1,1,1,2,2-pentafluoropropane
Five fluorine monochlorethanes are reacted in organic solvent with methyl-magnesium-chloride, described methyl-magnesium-chloride and five fluorine one
Mol ratio 1:1-5 of ethyl chloride, reaction temperature is 20-60 DEG C, and the response time is 1-5h, and reaction cools down after terminating, and filters, rectification
Obtain 1,1,1,2,2-pentafluoropropane;
The preparation of (b) 2 2,3,3,3-tetrafluoropropene
1 step (a) obtained, 1,1,2,2-pentafluoropropane is passed through in 50-90 DEG C of alkali liquor and reacts, and collects gas phase and produces
Thing drying, condensation obtain product 2,3,3,3-tetrafluoropropene;Or 1,1,1,2,2-pentafluoropropane step (a) obtained exists
Under catalyst action, gas phase catalysis takes off HF and obtains 2,3,3,3-tetrafluoropropene.
Preferably, the organic solvent described in step (a) is the one in oxolane, ether, glycol dimethyl ether or two
The mixture planted.
Preferably, the gross mass of methyl-magnesium-chloride described in step (a) and five fluorine monochlorethanes and organic solvent mass ratio
For 1:2.5-5.5.
Preferably, the alkali liquor described in step (b) is KOH solution, NaOH solution, LiOH solution, Mg (OH)2Solution, Ca
(OH)2One in solution.
Preferably, the alkali liquor mass percentage concentration described in step (b) is 10~60%.
Preferably, the catalyst described in step (b) is metal-oxide, or metallic compound is carried on metal-oxide
Or the metallic compound supported catalyst on activated carbon.Described metal-oxide is preferably with fluohydric acid gas, hydrogen chloride or chlorine fluoro
Hydrocarbon has carried out the oxide of moditied processing, described metallic compound be preferably selected from aluminum, titanium, chromium, manganese, nickel, copper, cobalt, zirconium, niobium,
The metal halide of at least one in molybdenum, stannum, antimony and tantalum or metal oxyhalides.Described catalyst is more preferably Cr2O3-
ZrO2(F)、Cr2O3-NiO/C(F)、Cr2O3-MgO/γ-Al2O3(F)、Cr2O3One in-NiO/MgO (F).
Preferably, when the gas phase catalysis described in step (b) takes off HF, reaction temperature is 200~600 DEG C, and material connects with catalyst
The tactile time is 3~30s, and reaction pressure is normal pressure.
The 2 of the present invention, 3,3,3-tetrafluoropropene syntheti c routes, use the Grignard reagent methyl-magnesium-chloride of strong nucleophilie nucleus ability
(CH3MgCl) and five fluorine monochlorethane (CF3CF2Cl) it is that initiation material prepares 2 through nucleophilic displacement of fluorine dehydrofluorination two-step reaction again,
3,3,3-tetrafluoropropene (CF3CF=CH2).This route raw material five fluorine monochlorethane can use tetrachloroethylene catalytic fluorination to produce five
The by-product of fluoroethane, therefore not only exist technological process short for this route, and the advantage that also cheaper starting materials is easy to get.
Use CH3MgCl and CF3CF2Cl reaction preparation 1,1,1,2,2-pentafluoropropane (CF3CF2CH3), then CH3CF2CF3
Take off HF with alkali liquor or gas phase catalysis takes off HF and prepares CF3CF=CH2.Reaction scheme is schematically as follows:
CF3CF2Cl+CH3MgCl→CF3CF2CH3+MgCl2 (1)
Compared with prior art, the invention have the advantages that
1, technique is simple, and the present invention uses the Grignard reagent methyl-magnesium-chloride of strong nucleophilie nucleus ability and the five fluorine monochlorethanes to be
Beginning raw material prepares 2 through nucleophilic displacement of fluorine dehydrofluorination two-step reaction again, and 3,3,3-tetrafluoropropenes, reaction condition gentleness is controlled, significantly
Simplify technique;
2, raw material is easy to get, low cost, and raw material five fluorine monochlorethane can use tetrachloroethylene catalytic fluorination to produce pentafluoroethane
By-product, reduce further production cost.
Detailed description of the invention
By the following examples the present invention is explained in further detail, but following example only further illustrate
The present invention, is not to limit the scope of protection of the invention.
The most commercially available acquirement of raw material in embodiment, wherein part material is described as follows:
The tetrahydrofuran solution of methyl-magnesium-chloride: purchased from Shangyu, Zhejiang Hua Lun Chemical Co., Ltd.;
Five fluorine monochlorethanes: purchased from Zhejiang Quhuafu Chemical Co., Ltd.
Embodiment 1
(1) preparation of 1,1,1,2,2-pentafluoropropane
Use nitrogen to replace three times 2L rustless steel autoclave, be subsequently adding the tetrahydrofuran solution of methyl-magnesium-chloride
(concentration of methyl-magnesium-chloride is 2mol/Kg) 250g and oxolane 750g, stirs at a temperature of 50 DEG C and is passed through five fluorine
Monochlorethane 160g, is further continued for after having led to reacting 3 hours.Reaction terminates, and stops stirring, is cooled to 0 DEG C, i.e. obtains 1,1 after filtration,
1,2,2-pentafluoropropane synthesis liquid, purity 99.5% after rectification and purification.Calculate on the basis of methyl-magnesium-chloride, 1,1,1,2,2-five
Fluoro-propane yield 81.3%.
(2) preparation of 2,3,3,3-tetrafluoropropene
Step (1) is reacted 1,1,1,2, the 2-pentafluoropropane obtained, and the mass percentage concentration being passed through excess is 40%, temperature
Degree is the potassium hydroxide solution of 70 DEG C, and collection gas-phase product drying, condensation obtain 2,3,3,3-tetrafluoropropene products, purity
99.5%, yield 98.2%.
Above-mentioned two-step reaction total recovery is 79.8%.
Embodiment 2
(1) preparation of 1,1,1,2,2-pentafluoropropane
Use nitrogen to replace three times 2L rustless steel autoclave, be subsequently adding the tetrahydrofuran solution of methyl-magnesium-chloride
(concentration of methyl-magnesium-chloride is 2mol/Kg) 250g and oxolane 750g, glycol dimethyl ether 200g, at a temperature of 60 DEG C
Stirring, while being passed through five fluorine monochlorethane 350g, is further continued for after having led to reacting 1 hour.Reaction terminates, and stops stirring, is cooled to 5
DEG C, i.e. obtain 1,1,1,2,2-pentafluoropropane synthesis liquid, purity 99.5% after rectification and purification after filtration.On the basis of methyl-magnesium-chloride
Calculate, 1,1,1,2,2-pentafluoropropane yield 85.6%.
(2) preparation of 2,3,3,3-tetrafluoropropene
Step (1) is reacted 1,1,1,2, the 2-pentafluoropropane obtained, and the mass percentage concentration being passed through excess is 60%, temperature
Degree is the sodium hydroxide solution of 50 DEG C, and collection gas-phase product drying, condensation obtain 2,3,3,3-tetrafluoropropene products, purity
99.5%, yield 99.1%.
Above-mentioned two-step reaction total recovery is 84.8%.
Embodiment 3
(1) preparation of 1,1,1,2,2-pentafluoropropane
Use nitrogen to replace three times 2L rustless steel autoclave, be subsequently adding the tetrahydrofuran solution of methyl-magnesium-chloride
(concentration of methyl-magnesium-chloride is 2mol/Kg) 250g and oxolane 750g, stirs at a temperature of 20 DEG C and is passed through five fluorine
Monochlorethane 200g, is further continued for after having led to reacting 5 hours.Reaction terminates, and stops stirring, is cooled to 10 DEG C, i.e. obtains 1 after filtration,
1,1,2,2-pentafluoropropane synthesis liquid, purity 99.5% after rectification and purification.Calculate on the basis of methyl-magnesium-chloride, 1,1,1,2,2-
Pentafluoropropane yield 73.5%.
(2) preparation of 2,3,3,3-tetrafluoropropene
Step (1) is reacted 1,1,1,2, the 2-pentafluoropropane obtained, and the mass percentage concentration being passed through excess is 20%, temperature
Degree is the aqua calcis of 90 DEG C, and collection gas-phase product drying, condensation obtain 2,3,3,3-tetrafluoropropene products, purity
99.5%, yield 98.1%.
Above-mentioned two-step reaction total recovery is 72.1%.
Embodiment 4
(1) preparation of 1,1,1,2,2-pentafluoropropane
Use nitrogen to replace three times 2L rustless steel autoclave, be subsequently adding the tetrahydrofuran solution of methyl-magnesium-chloride
(concentration of methyl-magnesium-chloride is 2mol/Kg) 250g and ether 750g, stirs at a temperature of 60 DEG C and is passed through five fluorine one chlorine
Ethane 250g, is further continued for after having led to reacting 2 hours.Reaction terminates, and stops stirring, is cooled to 0 DEG C, i.e. obtains 1,1,1,2 after filtration,
2-pentafluoropropane synthesis liquid, purity 99.5% after rectification and purification.Calculate on the basis of methyl-magnesium-chloride, 1,1,1,2,2-five fluorine third
Alkane yield 81.5%.
(2) preparation of 2,3,3,3-tetrafluoropropene
Step (1) is reacted 1,1,1,2, the 2-pentafluoropropane obtained, is passed through and is filled with the Cr after HF is fluorinated activation in advance2O3
(30wt%)-ZrO2(70wt%) reacting in the reactor of (F) catalyst, reaction temperature is 300 DEG C, and reaction pressure is normal
Pressure, 1,1,1,2,2-pentafluoropropane and catalyst contact time 10s, obtain 2,3,3,3-tetrafluoropropenes, yield 62.3%.
Above-mentioned two-step reaction total recovery 50.7%.
Embodiment 5
(1) preparation of 1,1,1,2,2-pentafluoropropane
Use nitrogen to replace three times 2L rustless steel autoclave, be subsequently adding the tetrahydrofuran solution of methyl-magnesium-chloride
(concentration of methyl-magnesium-chloride is 2mol/Kg) 250g, oxolane 500g, ether 250g, stir at a temperature of 30 DEG C
It is passed through five fluorine monochlorethane 160g, is further continued for after having led to reacting 4 hours.Reaction terminates, and stops stirring, is cooled to 8 DEG C, after filtration
Obtain 1,1,1,2,2-pentafluoropropane synthesis liquid, purity 99.5% after rectification and purification.Calculate on the basis of methyl-magnesium-chloride, 1,1,
1,2,2-pentafluoropropane yield 85.3%.
(2) preparation of 2,3,3,3-tetrafluoropropene
Step (1) is reacted 1,1,1,2, the 2-pentafluoropropane obtained, is passed through and is filled with the Cr after HF is fluorinated activation in advance2O3
(10wt%) reacting in the reactor of-NiO (5wt%)/C (F) catalyst, reaction temperature is 500 DEG C, and reaction pressure is normal
Pressure, 1,1,1,2,2-pentafluoropropane and catalyst contact time 5s, obtain 2,3,3,3-tetrafluoropropenes, yield 73.5%.
Above-mentioned two-step reaction total recovery 62.7%.
Embodiment 6
(1) preparation of 1,1,1,2,2-pentafluoropropane
Use nitrogen to replace three times 2L rustless steel autoclave, be subsequently adding the tetrahydrofuran solution of methyl-magnesium-chloride
(concentration of methyl-magnesium-chloride is 2mol/Kg) 250g and oxolane 750g, stirs at a temperature of 50 DEG C and is passed through five fluorine
Monochlorethane 160g, is further continued for after having led to reacting 3 hours.Reaction terminates, and stops stirring, is cooled to 3 DEG C, i.e. obtains 1,1 after filtration,
1,2,2-pentafluoropropane synthesis liquid, purity 99.5% after rectification and purification.Calculate on the basis of methyl-magnesium-chloride, 1,1,1,2,2-five
Fluoro-propane yield 81.3%.
(2) preparation of 2,3,3,3-tetrafluoropropene
Step (1) is reacted 1,1,1,2, the 2-pentafluoropropane obtained, is passed through and is filled with the Cr after HF is fluorinated activation in advance2O3
(10wt%)-MgO (10wt%)/γ-Al2O3(F) reacting in the reactor of catalyst, reaction temperature is 600 DEG C, reaction
Pressure is normal pressure, 1,1,1,2,2-pentafluoropropane and catalyst contact time 20s, obtains 2,3,3,3-tetrafluoropropenes, yield
67.7%.
Above-mentioned two-step reaction total recovery 55.0%.
Embodiment 7
(1) preparation of 1,1,1,2,2-pentafluoropropane
Use nitrogen to replace three times 2L rustless steel autoclave, be subsequently adding the tetrahydrofuran solution of methyl-magnesium-chloride
(concentration of methyl-magnesium-chloride is 2mol/Kg) 250g and oxolane 750g, stirs at a temperature of 20 DEG C and is passed through five fluorine
Monochlorethane 160g, is further continued for after having led to reacting 5 hours.Reaction terminates, and stops stirring, is cooled to 3 DEG C, i.e. obtains 1,1 after filtration,
1,2,2-pentafluoropropane synthesis liquid, purity 99.5% after rectification and purification.Calculate on the basis of methyl-magnesium-chloride, 1,1,1,2,2-five
Fluoro-propane yield 83.3%.
(2) preparation of 2,3,3,3-tetrafluoropropene
Step (1) is reacted 1,1,1,2, the 2-pentafluoropropane obtained, is passed through and is filled with the Cr after HF is fluorinated activation in advance2O3
(10wt%) reacting in the reactor of-NiO (5wt%)/MgO (F) catalyst, reaction temperature is 400 DEG C, and reaction pressure is
Normal pressure, 1,1,1,2,2-pentafluoropropane and catalyst contact time 10s, obtain 2,3,3,3-tetrafluoropropenes, yield 72.1%.
Above-mentioned two-step reaction total recovery 60.1%.
Claims (9)
1. one kind 2, the preparation method of 3,3,3-tetrafluoropropenes, it is characterised in that comprise the following steps:
The preparation of (a) 1,1,1,2,2-pentafluoropropane
Five fluorine monochlorethanes are reacted in organic solvent with methyl-magnesium-chloride, described methyl-magnesium-chloride and five fluorine one chloroethenes
Mol ratio 1:1-5 of alkane, reaction temperature is 20-60 DEG C, and the response time is 1-5h, and reaction cools down after terminating, and filters, and rectification obtains
1,1,1,2,2-pentafluoropropane;
The preparation of (b) 2,3,3,3-tetrafluoropropene
1 step (a) obtained, 1,1,2,2-pentafluoropropane is passed through in 50-90 DEG C of alkali liquor and reacts, and collects gas-phase product warp
Be dried, condensation obtains product 2,3,3,3-tetrafluoropropene;Or 1,1,1,2,2-pentafluoropropane step (a) obtained is in catalysis
Under agent effect, gas phase catalysis takes off HF and obtains 2,3,3,3-tetrafluoropropene.
The preparation method of 2,3,3,3-tetrafluoropropenes the most according to claim 1, it is characterised in that having described in step (a)
Machine solvent is one or both the mixture in oxolane, ether, glycol dimethyl ether.
The preparation method of 2,3,3,3-tetrafluoropropenes the most according to claim 1, it is characterised in that the first described in step (a)
The gross mass of base magnesium chloride and five fluorine monochlorethanes and organic solvent mass ratio are 1:2.5-5.5.
The preparation method of 2,3,3,3-tetrafluoropropenes the most according to claim 1, it is characterised in that the alkali described in step (b)
Liquid is KOH solution, NaOH solution, LiOH solution, Mg (OH)2Solution, Ca (OH)2One in solution.
The preparation method of 2,3,3,3-tetrafluoropropenes the most according to claim 1, it is characterised in that the alkali described in step (b)
Liquid mass percentage concentration is 10~60%.
The preparation method of 2,3,3,3-tetrafluoropropenes the most according to claim 1, it is characterised in that urging described in step (b)
Agent is metal-oxide, or the metallic compound supported catalyst that metallic compound is carried on metal-oxide or activated carbon
Agent.
The preparation method of 2,3,3,3-tetrafluoropropenes the most according to claim 6, it is characterised in that described metal-oxide
For having carried out the oxide of fluorination treatment with fluohydric acid gas, hydrogen chloride or chlorine fluorohydrocarbon, described metallic compound be selected from aluminum, titanium,
At least one metal halide in chromium, manganese, nickel, copper, cobalt, zirconium, niobium, molybdenum, stannum, antimony and tantalum or metal oxyhalides.
The preparation method of 2,3,3,3-tetrafluoropropenes the most according to claim 7, it is characterised in that described catalyst is
Cr2O3-ZrO2(F)、Cr2O3-NiO/C(F)、Cr2O3-MgO/γ-Al2O3(F)、Cr2O3One in-NiO/MgO (F).
The preparation method of 2,3,3,3-tetrafluoropropenes the most according to claim 1, it is characterised in that the gas described in step (b)
During catalysis de-HF, reaction temperature is 200~600 DEG C mutually, and material and catalyst contact time are 3~30s, and reaction pressure is normal pressure.
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018228975A1 (en) * | 2017-06-12 | 2018-12-20 | Novaliq Gmbh | Process for the preparation of semifluorinated alkanes using grignard reagents |
CN113943204A (en) * | 2021-10-30 | 2022-01-18 | 山东东岳化工有限公司 | Method for recycling pentafluoro-chloroethane |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1696095A (en) * | 2005-04-30 | 2005-11-16 | 赵士良 | Method for improving synthesis of coenzyme Q10 |
CN1762942A (en) * | 2005-07-21 | 2006-04-26 | 昆明通发实业有限公司 | A kind of preparation method for isodeca-deca-isoprene-yl alcohol |
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 |
CN101610987A (en) * | 2006-10-31 | 2009-12-23 | 纳幕尔杜邦公司 | Contain 2,3,3,3-tetrafluoeopropene and/or 1,2,3, the composition and method of making the same of 3-tetrafluoeopropene |
WO2010131760A1 (en) * | 2009-05-12 | 2010-11-18 | Daikin Industries, Ltd. | Process for preparing fluorine-containing propane |
US20110270000A1 (en) * | 2010-04-29 | 2011-11-03 | Honeywell International Inc. | Method for producing tetrafluoropropenes |
CN102770400A (en) * | 2010-02-12 | 2012-11-07 | 大金工业株式会社 | Process for producing fluorine-containing alkene compound |
CN104271235A (en) * | 2012-05-02 | 2015-01-07 | 墨西哥化学阿玛科股份有限公司 | Process for preparing a c3-c7 (hydro) fluoroalkene by dehydrohalogenation |
US20150315108A1 (en) * | 2004-04-29 | 2015-11-05 | Sudip Mukhopadhyay | Method for producing fluorinated organic compounds |
CN105111038A (en) * | 2015-08-18 | 2015-12-02 | 巨化集团技术中心 | Method for preparing 2,3,3,3-tetrafluoropropene by using methyl magnesium chloride |
-
2016
- 2016-08-17 CN CN201610686087.1A patent/CN106316777B/en active Active
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20150315108A1 (en) * | 2004-04-29 | 2015-11-05 | Sudip Mukhopadhyay | Method for producing fluorinated organic compounds |
CN1696095A (en) * | 2005-04-30 | 2005-11-16 | 赵士良 | Method for improving synthesis of coenzyme Q10 |
CN1762942A (en) * | 2005-07-21 | 2006-04-26 | 昆明通发实业有限公司 | A kind of preparation method for isodeca-deca-isoprene-yl alcohol |
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 |
CN101610987A (en) * | 2006-10-31 | 2009-12-23 | 纳幕尔杜邦公司 | Contain 2,3,3,3-tetrafluoeopropene and/or 1,2,3, the composition and method of making the same of 3-tetrafluoeopropene |
WO2010131760A1 (en) * | 2009-05-12 | 2010-11-18 | Daikin Industries, Ltd. | Process for preparing fluorine-containing propane |
CN102770400A (en) * | 2010-02-12 | 2012-11-07 | 大金工业株式会社 | Process for producing fluorine-containing alkene compound |
US20110270000A1 (en) * | 2010-04-29 | 2011-11-03 | Honeywell International Inc. | Method for producing tetrafluoropropenes |
CN104271235A (en) * | 2012-05-02 | 2015-01-07 | 墨西哥化学阿玛科股份有限公司 | Process for preparing a c3-c7 (hydro) fluoroalkene by dehydrohalogenation |
CN105111038A (en) * | 2015-08-18 | 2015-12-02 | 巨化集团技术中心 | Method for preparing 2,3,3,3-tetrafluoropropene by using methyl magnesium chloride |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2018228975A1 (en) * | 2017-06-12 | 2018-12-20 | Novaliq Gmbh | Process for the preparation of semifluorinated alkanes using grignard reagents |
CN113943204A (en) * | 2021-10-30 | 2022-01-18 | 山东东岳化工有限公司 | Method for recycling pentafluoro-chloroethane |
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