CN1258505C - Production of aliphatic fluorocarbons - Google Patents
Production of aliphatic fluorocarbons Download PDFInfo
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- CN1258505C CN1258505C CNB008106355A CN00810635A CN1258505C CN 1258505 C CN1258505 C CN 1258505C CN B008106355 A CNB008106355 A CN B008106355A CN 00810635 A CN00810635 A CN 00810635A CN 1258505 C CN1258505 C CN 1258505C
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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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/269—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of only halogenated hydrocarbons
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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Abstract
Processes for preparing a variety of fluorocarbons are disclosed. Processes are described wherein the yields of desired products are increased by endlessly converting the undesired products to reactive intermediates. Trifluoroethylene is prepared in greater than 50% yield by pyrolizing 1-chloro-2,2,2-trifluoroethane at a temperature about 725 DEG C. 1,1,1,3,3-Pentafluoropropylene is prepared by pyrolyzing 1-chloro-2,2,2-trifluoroethane in the presence of chlorodifluoromethane. Trifluoroethylene is prepared by pyrolyzing 1,2,2,2-tetrafluoroethane. 1-Chloro-2,2-difluoroethylene is prepared by pyrolyzing 1-chloro-2,2,2-trifluoroethane. 1,1-Dichloro-2,2-difluoroethylene is prepared by pyrolyzing 1-chloro-2,2,2-trifluoroethane in the presence of chlorodifluoromethane and hydrogen chloride. 1,1,1,2,3,4,4,4-Octafluoro-2-butene is prepared by pyrolyzing 1-chloro-1,2,2,2-tetrafluoroethane. 1,1,1,2,3,4,4,4-Octafluoro-2-butene is prepared by pyrolyzing, 1,1,2,2,2-pentafluoroethane. 1,2,2,2-Tetrafluoroethane is prepared by pyrolyzing 1,1,2,2,2-pentafluoroethane. 1,1-Dichloro-1,2,2,2-tetrafluoroethane is prepared by pyrolyzing 1-chloro-1,2,2,2-tetrafluoroethane.
Description
Background of invention
1. invention field
The present invention relates to produce the method for aliphatic fluorocarbons.
2. description of Related Art
Compounds of group in aliphatic fluorocarbons belongs to from inertia, high stable material to active unsaturated fluorocarbons scope.As this whole open and employed in the claims, term " aliphatic fluorocarbons " is defined as a kind of fatty compounds with carbon-fluorine bond, and it also can hydrogeneous and chlorine.Aliphatic fluorocarbons can comprise only having single bonded compound has multikey to those compound.This singly-bound compound usually is an inertia and nonflammable.These compounds can be used as inert solvent, lubricant and whipping agent as an example.Fluorocarbon with two keys, fluoroolefins is the very high material of reactive behavior, can be used for producing all cpds and particular polymer.Having the triple-linked fluorocarbon also is that reactive behavior is very high.Production is that extremely chemical industry is paid close attention to the method for the compound of these groups always effectively.
Summary of the invention
The present invention relates to prepare a kind of new production process of purpose aliphatic fluorocarbons product, may further comprise the steps:
A) aliphatic carbon fluorine initial compounds is handled, made at least one chemical bond disconnection in this aliphatic carbon fluorine initial compounds, form a kind of active aliphatic carbon fluorine midbody compound;
B) make the reaction of this activity aliphatic carbon fluorine midbody compound and another active compound, produce purpose aliphatic fluorocarbons product and non-purpose aliphatic fluorocarbons product;
C) from any non-purpose aliphatic fluorocarbons product, separate described purpose aliphatic fluorocarbons product; With
D) any non-purpose aliphatic fluorocarbons product is recycled in the step a).
The front has given definition to term " aliphatic fluorocarbons ".Term " active aliphatic carbon fluorine midbody compound " is meant any aliphatic fluorocarbons, and it can react with aliphatic fluorocarbons and other active aliphatic fluorocarbons.This term comprises the species such as radical, ion or carbene.
Detailed Description Of The Invention
Described new production method from the initial fluorocarbon of part produce active intermediate and.This method is attended by the fracture of chemical bond, and the fracture method of chemical bond is well-known technology, maybe can produce the similar approach of radical, ion or carbene such as pyrolysis, granular radiation, microwave, plasma body, UV-light, infrared light.Then, make these active intermediates and other active intermediate or react with the common molecule that can produce new key, the result directly or by subsequent step obtains new product.
It is special producing fluorocarbon active intermediates by these paths, wherein forming element fluorine not.This may be because the energy that disconnection carbon-fluorine bond needs is big, and the energy that the formation of fluoro-fluorine bond is obtained is little.As part of the present invention basis, this characteristic that produces the fluorocarbon active intermediate is different with the characteristic that produces the hydrocarbon active intermediate, has some hydrogen and carbon to form among the latter.These two kinds of materials are not further reaction, causes the loss of purpose product yield.
Usually also have many products that make by the very high intermediate of activity.This generally is considered to successfully synthesizing the obstacle of simplification compound.In prepared product, some is desirable, and other are undesirable.The present invention need adopt distillation or other physical method, separates the purpose product from non-purpose product.Then, non-purpose product can be recycled in this technological process, forming the similar activity intermediate again, and the not formation of reason fluorine descends yield.Because little reciprocity principle, also successful recirculation can appear, and this requires the non-purpose product of part to return it to be in the parent material under the working condition.Then, these with the parent material that is added, will form a kind of product mixtures that comprises more purpose products from the active intermediate of non-purpose product.Therefore, can make the recirculation constantly of non-purpose product, thereby improve the yield of purpose product.By the present invention, can make even low initial yield changes the feasible method of industry into.Sometimes, when product was product unusual and highly hope, even extremely low initial yield also may cause industrialized method.
Little reversible example as shown in Table.R125 (seeing the abbreviation table) is made by parent material R133a, and R133a is made with low yield by R125.Therefore,, then it can be recycled in the parent material, as the part that improves the purpose product yield if R125 is non-purpose product.
Except that little reversibility, can help the indirect reaction of non-purpose product recirculation in addition.R125 is shown and can be made into R134a.Routine tests shows that TFE can be made by R134a.Therefore, the available at least two kinds of methods of R125 (the non-purpose by product of TFE) are made it to be converted into TFE; By turning back to parent material R133a and passing through another intermediate R134a, it also plays the parent material of TFE.
In hydrogenous fluorocarbon parent material, also may produce some hydrogen fluoride.This does not represent that those fluorine atoms have lost because be added to hydrogen fluoride on the alkene and form again form parent material and the two desirable carbon-fluorine bond energy needed of product extremely low.Formation by R134 has in the present embodiment illustrated this point, and its supposition is formed by TFE and hydrogen fluoride.In this process,, all can be reclaimed separately and separately or by recirculation, be used to form carbon-fluorine bond any hydrogen fluoride that forms carbon-fluorine bond again that has neither part nor lot in.
In the fluorocarbon parent material of hydrogeneous and chlorine, may produce hydrogenchloride.This does not represent the terminal point of those atoms, can cause forming chloride purpose product because in the present invention reactant is added hydrogenchloride.
Some olefin products can telomerize or polymerization under reaction conditions, and these products still may contain useful carbon-fluorine bond.Volatile telomer can stand with the same the separating and recirculation step of other volatile by product with polymkeric substance.Not too volatile telomer and polymkeric substance may require to carry out machinery and gather and special disposal, but the product of all carbon containing-fluorine bonds all can be by whole recirculation, to improve yield in theory.
The demand of industry is at that time depended in the selection of purpose product and non-purpose product fully.Any those skilled in the art all may understand, and can change the selection of " purpose " in the fluorocarbon and " non-purpose " product, and method of the present invention still can carry out, so that the new purpose product of determining reaches good yield.
All this method of recirculation also has another advantage.It provides a kind of and has more made full use of parent material and reduce the method that refuse produces.Usually must handle with special methods refuse, so that their unlikely environment that enters.In the present invention, the requirement of this processing and expense can be exempted or be reduced many.
The present invention relates to find to prepare the novel method of fluorocarbon and some wonderful products that obtain by these methods.The present invention also relates to find to be different from fully the activated carbon fluorine cpd intermediate of reactive hydrocarbon compound intermediate, and how to handle these differences, could increase the yield of purpose product.
In first preferred embodiment, the present invention relates to the production of aliphatic fluorocarbons, comprise a kind of active aliphatic fluorocarbons intermediate that is used to produce, form new product, separate purpose product and the non-purpose product of whole recirculation to improve the method for purpose product yield.
In second preferred embodiment, this active intermediate produces by the pyrolysis of aliphatic fluorocarbons.
In the 3rd preferred embodiment, the present invention relates to a kind of preparation TFE method, be included in pyrolysis R133a under about temperature below 725 ℃, its TFE yield is greater than 50%.
In the 4th preferred embodiment, the present invention relates to prepare the method for PFP, be included in R22 and have pyrolysis R133a down.
In the 5th preferred embodiment, the present invention relates to the method for a kind of OFB of preparation, comprise pyrolysis R124.
In the 6th preferred embodiment, the present invention relates to the method for a kind of CDFE of preparation, comprise pyrolysis R133a.
In the 7th preferred embodiment, the present invention relates to the method for a kind of DCDFE of preparation, be included in R22 and hydrogenchloride and have pyrolysis R133a down.
In the 8th preferred embodiment, the present invention relates to the method for a kind of OFB of preparation, comprise pyrolysis R125.
In the 9th preferred embodiment, the present invention relates to the method for a kind of R134a of preparation, comprise pyrolysis R125.
In the tenth preferred embodiment, the present invention relates to the method for a kind of R114a of preparation, comprise pyrolysis R124.
In the 11 preferred embodiment, the present invention relates to the method for a kind of PFB of preparation, comprise pyrolysis R125.
In the 12 preferred embodiment, the present invention relates to the method for a kind of R125 of preparation, comprise pyrolysis R133a.
In might form these active intermediates such as carbene, radical and ionic method, what present embodiment selected is pyrolysis.But, can adopt any described method, and the method that relates to also is that those skilled in the art are well-known.
The pyrolysis of compound generally high temperature, the different residence time and have or the different condition of diluent free under finish.Pyrolysis can intermittently or under the condition of continuity be finished.Adopt the condition of continuity, reaction tubes can be made with the various materials that comprise quartz, aluminum oxide, Inconel(nickel alloys) or Monel metal.The external diameter of the present used pipe of embodiment is 1 ", exception be that the alumina tube external diameter is 3/8 ".Various pipes are put into 12 " electrical heater, it is depicted as comfort zone.Measure temperature with the thermopair in the tube hub thermowell.For 3/8 " alumina tube, temperature measuring is in central point pipe outside.
Each reagent is all by 1/16 behind each self calibration " or 1/8 " in the glass rotameter injection tube.Sometimes another end of reactor is limited, so that reach required reactor pressure.Pressure boost can make transformation efficiency increase, but yield reduces.
The residence time can be used for determining transformation efficiency, and it influences yield subsequently.Usually, the extremely low residence time and extremely low transformation efficiency can obtain best yield, but may industrial be unpractical.The used residence time can change between part second to about 30 seconds.Preferred residence time scope is determined with the experience to each reaction-ure mixture.Can determine higher pressure by the operation factor.Can relax pressure-dependent problem by reducing the residence time.
Certainly, the input speed of reactant is the function of reaction zone size.For equipment described here, the used input speed of each reactant per hour about 0.018 mole to per hour changing between about 4 moles.In described reactor.Also per hour can adopt about 10 moles speed, but transformation efficiency can be very low.
Also available inert diluent changes the residence time of reaction zone internal reaction thing.Inert diluent can be such as nitrogen, noble gas, materials such as perfluoro alkane and water vapor.Employing is easy to the inert diluent of condensation, can make separating of the big thinner of product and volume easier.
Robert P.Salmon and Edward R.Ritter provide the reference relevant with the present invention, see " Experimental Flow Tube Study on Pyrolysis of2-Chloro-1,1,1-Trifluoroethane ",
Chem.Phys.Processes Combust., 1996, the 507-510 pages or leaves.People such as Salmon have reported 2% 2-chloro-1,1 in the circulation quartz tube reactor, the pyrolysis of the mixture of 1-Halothane [R133a] and 98% nitrogen under barometric point and 700-875 ℃ of temperature.Under the temperature below 777 ℃, trifluoro-ethylene [TFE] is the product of maximum, and other product of formation comprises 1,1,1,4,4,4-hexafluoro-2-butylene [HFB] and 2-chloro-vinylidene fluoride [CDFE].But, below 725 ℃, do not form the TFE of any degree about.The yield of TFE sharply descends under high temperature more, but 1,1,1,3,3-five fluorine propylene [PFP] yields but steadily increase.At high temperature other product of Xing Chenging comprises 1,1,1-three fluoro-2-propine.
Combination with temperature range, the residence time, thinner and reactant is tested, and the result has obtained many results that do not describe in the literature now.A viewed wonderful result is can also make other product by good yield by the chemical of introducing other.These results are disclosed in table and the following description.The yield that provides is the numerical value of stable state, but does not reflect because the ultimate value that whole recirculation draws.
Under selected pyrolytical condition (test 1-3), begin with R133a, can produce yield and surpass 50% TFE, exceed the available any expectation of work from Salmon etc.
Be lower than 10% (test 4) down during the same reactant R133a of pyrolysis at about 700 ℃ and transformation efficiency, CDFE becomes the good important products of yield.For Salmon and the Ritter reference of pointing out that wherein CDFE should only just form under comparatively high temps, this is unexpected.
Find that also TFE also can be made with good yield by R134a (test 15).
Salmon and Ritter report, used temperature is less than about 750 ℃ or higher temperature, and the pyrolysis product that PFP can not become R133a occurs, and even so, even surpass 800 ℃ up to temperature, and the PFP of very low yield is also only arranged.Find now, add (test 6-9) among the R22 to R133a, under 725-750 ℃ of temperature, just can make PFP by good yield.
A very situation of difference is arranged, in the presence of hydrogenchloride, (test 10) and carry out same pyrolysis, can prepare DCDFE.Estimation hydrogenchloride can not participated in this class reaction.
Can prepare OFB by good yield by R124 (test 11 and 12) or R125 (test 13 and 14).R125 also can prepare PFB, and R124 also can prepare R114a.
The pyrolysis of R133a almost produces R125 (test 2 and 5) usually.The pyrolysis of R125 (test 14) produces R134a, and conversely, it produces TFE (test 15) again.
Should be appreciated that this specification sheets and claims by explanation and the elaboration of unrestriced method, to its various improvement and change of making, can not depart from the spirit and scope of the present invention.
The abbreviation table
CDFE=1-chloro-2, the 2-difluoroethylene
DCDFE=1,1-two chloro-2,2-difluoroethylene
HFB=1,1,1,4,4,4-hexafluoro-2-butylene
OFB=1,1,1,2,3,4,4,4-octafluoro-2-butylene
The PFB=perfluorinated butane
PFP=1,1,1,3,3-five fluorine propylene
R114a=1,1-two chloro-1,2,2,2-Tetrafluoroethane
The R12=Refrigerant 12
R123=1,1-two chloro-2,2,2-Halothane
R124=1-chloro-1,2,2, the 2-Tetrafluoroethane
R125=1,1,2,2, the 2-pentafluoride ethane
The R13=monochlorotrifluoromethane
R133a=1-chloro-2,2, the 2-Halothane
R134=1,1,2, the 2-Tetrafluoroethane
R134a=1,2,2, the 2-Tetrafluoroethane
The R22=monochlorodifluoromethane
The TEFE=tetrafluoroethylene
The TFE=trifluoro-ethylene
Table
| Test number | Reactant [a] A/B | Condition [b] T/RT/ pipe | Mole of feed/hour | Mole/100 gram chargings | Mole consumes or generates/100 gram chargings | Yield % | |||||
| Consume | Generate | ||||||||||
| 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 | R133a R133a R133a R133a R133a R133a/R22 R133a/R22 R133a/R22 R133a/R22 R133a/R22 R124 R124 R125 R125 R134a | 725/26/Q[2% is at N 2In] 725/26/Q[10% is at N 2In] 725/3.6/A[20% is at N 2In] 700/3.6/A[20% is at N 2In] 723-774/50/I 725/26/Q 750/26/Q 730/26/Q 725/26/Q 745/26/I[is in HCl under the atmospheric pressure] 700/3.6/A 715/3.6/A 800/3.6/A 840/0.9/A 870/0.9/M | 0.018 0.088 0.177 0.177 0.372 0.088/0.088 0.088/0.097 0.088/0.097 0.088/0.097 0.044/0.044 0.885 0.885 0.885 3.688 3.688 | A/B 0.844 0.844 0.844 0.844 0.844 0.488/0.488 0.468/0.515 0.468/0.515 0.468/0.515 0.488/0.488 0.733 0.733 0.833 0.833 0.98 | A | B | Product C [c] | Product D [c] | Product C | Product D | Other product |
| 0.494 0.267 0.128 0.071 0.684 0.345 0.438 0.341 0.316 0.378 0.228 0.357 0.286 0.178 0.076 | 0.443 0.485 0.457 0.446 0.326 | TFE/0.398 TFE/0.182 TFE/0.074 CDFE/0.061 TFE/0.037 TFE/0.084 PFP/0.371 PFP/0.318 PFP/0.295 DCDFE/0.128 0FB/0.065 0FB/0.14 0FB/0.099 0FB/0.054 TFE/0.04 | HFB/0.051 R125/0.208 PFP/0.335 R12 and 13/0.107 R114a/0.05 R114a/0.06 PFB/0.021 R134a/0.049 TeFE/0.013 | 80.6 68.1 58.1 85.8 5.3 10.6 40.2 39.8 38.8 18.2 28.5 39.2 34.6 39.7 52.6 | 19.1 30.4 42.5 15.2 21.9 16.8 7.3 23.1 17.1 | R125 HFB，R123 R133a R134 | |||||
[a]: R124=1-chloro-1,2,2,2-Tetrafluoroethane [c]: CDFE=1-chloro-2,2-difluoroethylene
R125=1,1,2,2,2-pentafluoride ethane DCDFE=1,1-two chloro-2,2-difluoroethylene
R133a=1-chloro-2,2,2-Halothane HFB=1,1,1,4,4,4-hexafluoro-2-butylene
R134a=1,2,2,2-Tetrafluoroethane OFB=1,1,1,2,3,4,4,4-octafluoro-2-butylene
R22=monochlorodifluoromethane PFB=perfluorinated butane
PFP=1,1,1,3,3-five fluorine propylene
[b]: T/RT/ pipe: R114a=1,1-two fluoro-1,2,2,2-Tetrafluoroethane
The T=temperature, ℃ R12=Refrigerant 12
The RT=residence time, second R123=1,1-two chloro-2,2,2-Halothane
The formation of pipe=pipe; The R13=monochlorotrifluoromethane
The A=aluminum oxide; The I=Inconel(nickel alloys); The M=Monel metal; The quartzy R134=1 of Q=, 1,2, the 2-Tetrafluoroethane
The TeFE=tetrafluoroethylene
The TFE=trifluoro-ethylene
Other abbreviation sees that notes show [a]
Claims (12)
1. method for preparing purpose aliphatic fluorocarbons product may further comprise the steps:
A) aliphatic carbon fluorine initial compounds is handled, made at least one chemical bond disconnection in the described aliphatic carbon fluorine initial compounds, form a kind of active aliphatic carbon fluorine midbody compound;
B) make this activity aliphatic carbon fluorine midbody compound be converted into i) this purpose aliphatic fluorocarbons product or a kind of intermediate and ii) at least a non-purpose aliphatic fluorocarbons product that causes this purpose aliphatic fluorocarbons product;
C) from any b) separate described purpose aliphatic fluorocarbons product in the non-purpose aliphatic fluorocarbons product that forms; With
D) should constantly be recycled in the step a) as aliphatic carbon fluorine initial compounds by non-purpose aliphatic fluorocarbons product.
2. according to the process of claim 1 wherein that the chemical bond of described aliphatic carbon fluorine initial compounds is disconnected by described aliphatic carbon fluorine initial compounds is carried out pyrolysis.
3. according to the method for claim 2, comprise with greater than 50% yield under the temperature below 725 ℃ to 1-chloro-2,2, the 2-Halothane is carried out pyrolysis, forms trifluoro-ethylene.
4. according to the method for claim 2, be included in the monochlorodifluoromethane existence down in 725-750 ℃, to 1-chloro-2,2, the 2-Halothane is carried out pyrolysis, forms 1,1,1,3,3-five fluorine propylene.
5. according to the method for claim 2, comprise that to 1-chloro-1,2,2, the 2-Tetrafluoroethane carries out pyrolysis, form 1,1,1,2,3,4,4,4-octafluoro-2-butylene.
6. according to the method for claim 2, be included in 700 ℃ and transformation efficiency less than 10% time, to 1-chloro-2,2, the 2-Halothane is carried out pyrolysis, forms 1-chloro-2, the 2-difluoroethylene.
7. according to the method for claim 2, be included under the existence of monochlorodifluoromethane and hydrogenchloride, to 1-chloro-2,2, the 2-Halothane is carried out pyrolysis, forms 1,1-two chloro-2,2-difluoroethylene.
8. according to the method for claim 2, comprise that the 2-pentafluoride ethane carries out pyrolysis, form 1,1,1,2,3,4,4,4-octafluoro-2-butylene 1,1,2,2.
9. according to the method for claim 2, comprise that the 2-pentafluoride ethane carries out pyrolysis, form 1,2,2, the 2-Tetrafluoroethane 1,1,2,2.
10. according to the method for claim 2, comprise that to 1-chloro-1,2,2, the 2-Tetrafluoroethane carries out pyrolysis, form 1,1-two chloro-1,2,2,2-Tetrafluoroethane.
11., comprise that the 2-pentafluoride ethane carries out pyrolysis according to the method for claim 2, form perfluorinated butane to 1,1,2,2.
12. according to the method for claim 2, comprise that to 1-chloro-2,2, the 2-Halothane is carried out pyrolysis, form 1,1,2,2, the 2-pentafluoride ethane.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14473999P | 1999-07-21 | 1999-07-21 | |
| US60/144,739 | 1999-07-21 |
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|---|---|
| CN1361758A CN1361758A (en) | 2002-07-31 |
| CN1258505C true CN1258505C (en) | 2006-06-07 |
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| CNB008106355A Expired - Fee Related CN1258505C (en) | 1999-07-21 | 2000-07-21 | Production of aliphatic fluorocarbons |
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| EP (1) | EP1198441A4 (en) |
| JP (1) | JP2003505439A (en) |
| KR (1) | KR20020029086A (en) |
| CN (1) | CN1258505C (en) |
| AU (1) | AU6359400A (en) |
| BR (1) | BR0012650A (en) |
| CA (1) | CA2380285A1 (en) |
| CZ (1) | CZ2002183A3 (en) |
| PL (1) | PL352765A1 (en) |
| WO (1) | WO2001007384A1 (en) |
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| JP4864879B2 (en) | 2004-04-29 | 2012-02-01 | 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 synthesizing 1,3,3,3-tetrafluoropropene |
| JP4864878B2 (en) * | 2004-04-29 | 2012-02-01 | ハネウェル・インターナショナル・インコーポレーテッド | Synthesis method of 1,3,3,3-tetrafluoropropene |
| US9024092B2 (en) | 2006-01-03 | 2015-05-05 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US8084653B2 (en) | 2004-04-29 | 2011-12-27 | Honeywell International, Inc. | Method for producing fluorinated organic compounds |
| US7674939B2 (en) | 2004-04-29 | 2010-03-09 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US7659434B2 (en) | 2004-04-29 | 2010-02-09 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US8383867B2 (en) | 2004-04-29 | 2013-02-26 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US9102579B2 (en) | 2004-04-29 | 2015-08-11 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| US7951982B2 (en) | 2004-04-29 | 2011-05-31 | Honeywell International Inc. | Method for producing fluorinated organic compounds |
| KR101404981B1 (en) * | 2005-11-03 | 2014-06-10 | 허니웰 인터내셔널 인코포레이티드 | Method for producing fluorinated organic compounds |
| CN103044190B (en) * | 2012-12-21 | 2014-12-24 | 巨化集团技术中心 | Preparation method of trifluoroethylene |
| EP3230240B1 (en) * | 2014-12-11 | 2018-06-13 | Arkema France | Process for the preparation of 1-chloro-2,2-difluoroethane |
| JP2018516268A (en) * | 2015-06-04 | 2018-06-21 | アーケマ・インコーポレイテッド | Process for producing fluorinated olefins |
| CN107337578B (en) * | 2017-08-03 | 2020-07-24 | 北京宇极科技发展有限公司 | Method for synthesizing perfluoro-2-butene by gas phase catalysis |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DD43244A (en) * | ||||
| US2413695A (en) * | 1943-06-19 | 1947-01-07 | Kinetic Chemicals Inc | Fluorinated compounds and pyrolytic methods for preparing them |
| US2627529A (en) * | 1947-10-23 | 1953-02-03 | Socony Vacuum Oil Co Inc | Pyrolysis of difluoromonochloroethane |
| FR1337360A (en) * | 1962-07-25 | 1963-09-13 | Pechiney Saint Gobain | Process for obtaining vinylidene fluoride |
| USRE29534E (en) * | 1972-08-18 | 1978-02-07 | E. I. Du Pont De Nemours And Company | Purification of perfluorosulfonyl fluoride perfluorovinyl ethers by thermal decomposition of unstable isomers |
| ATE32334T1 (en) * | 1984-08-20 | 1988-02-15 | Solvay | PROCESS FOR THE PYROLYTIC DEHYDROCHLORATION OF HALOGENOALKANES IN THE PRESENCE OF CHLORINATED COMPOUNDS AS INITIATOR AND SUCH INITIATOR. |
| DE3729106A1 (en) * | 1987-09-01 | 1989-03-09 | Hoechst Ag | PROCESS FOR OBTAINING PURE TETRAFLUOROETHYLENE |
| WO1990008755A1 (en) * | 1989-02-03 | 1990-08-09 | E.I. Du Pont De Nemours And Company | Manufacture of 1,1,1,2-tetrafluoroethane |
| CA2016686A1 (en) * | 1989-06-13 | 1990-12-13 | Maher Y. Elsheikh | Gas phase catalytic process for production of vinylidene fluoride |
| US5155082A (en) * | 1991-04-12 | 1992-10-13 | Allied-Signal Inc. | Catalyst for the manufacture of chlorofluorocarbons, hydrochlorofluorocarbons and hydrofluorocarbons |
| JP2661441B2 (en) * | 1991-11-27 | 1997-10-08 | ダイキン工業株式会社 | Method for producing 1,1,1-trifluoro-2-chloroethane and / or 1,1,1,2-tetrafluoroethane |
| US5177271A (en) * | 1992-04-30 | 1993-01-05 | Elf Atochem North America, Inc. | Production of vinylidene fluoride |
| FR2690687B1 (en) * | 1992-04-30 | 1995-01-27 | Atochem North America Elf | Process for the production of vinylidene fluoride. |
| DE4214739A1 (en) * | 1992-05-04 | 1993-11-11 | Bayer Ag | Process for the preparation of hexafluorochlorobutenes |
| DK0775100T3 (en) * | 1994-08-08 | 2000-11-27 | Ici Plc | Process for the preparation of trifluoroethylene |
| US5475167A (en) * | 1995-02-17 | 1995-12-12 | E. I. Du Pont De Nemours And Company | Process for the manufacture of pentafluoroethane |
| US5654494A (en) * | 1995-08-18 | 1997-08-05 | Alliedsignal Inc. | Process for the manufacture of 1,1,1,2-tetrafluoroethane |
| JP3818398B2 (en) * | 1995-12-29 | 2006-09-06 | ダイキン工業株式会社 | Process for producing 1,1,1,3,3-pentafluoropropane |
| FR2748473B1 (en) * | 1996-05-13 | 1998-07-24 | Atochem Elf Sa | SYNTHESIS OF 1-CHLORO-3,3,3 TRIFLUOROPROPENE AND ITS FLUORINATION IN 1,1,1,3,3 PENTAFLUOROPROPANE |
| US6369284B1 (en) * | 1997-01-31 | 2002-04-09 | E. I. Du Pont De Nemours And Company | Catalytic manufacture of pentafluoropropenes |
| JP3520900B2 (en) * | 1997-12-12 | 2004-04-19 | ダイキン工業株式会社 | Method for producing pentafluoroethane, catalyst for fluorination and method for producing the same |
| WO1999051553A1 (en) * | 1998-04-03 | 1999-10-14 | E.I. Du Pont De Nemours And Company | Process for the production of fluorocarbons |
-
2000
- 2000-07-21 KR KR1020027000863A patent/KR20020029086A/en not_active Application Discontinuation
- 2000-07-21 CA CA002380285A patent/CA2380285A1/en not_active Abandoned
- 2000-07-21 CZ CZ2002183A patent/CZ2002183A3/en unknown
- 2000-07-21 EP EP00950495A patent/EP1198441A4/en not_active Withdrawn
- 2000-07-21 JP JP2001512473A patent/JP2003505439A/en active Pending
- 2000-07-21 PL PL00352765A patent/PL352765A1/en not_active Application Discontinuation
- 2000-07-21 CN CNB008106355A patent/CN1258505C/en not_active Expired - Fee Related
- 2000-07-21 WO PCT/US2000/019863 patent/WO2001007384A1/en not_active Application Discontinuation
- 2000-07-21 AU AU63594/00A patent/AU6359400A/en not_active Abandoned
- 2000-07-21 BR BR0012650-0A patent/BR0012650A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1361758A (en) | 2002-07-31 |
| AU6359400A (en) | 2001-02-13 |
| WO2001007384A1 (en) | 2001-02-01 |
| JP2003505439A (en) | 2003-02-12 |
| EP1198441A1 (en) | 2002-04-24 |
| BR0012650A (en) | 2002-04-09 |
| KR20020029086A (en) | 2002-04-17 |
| PL352765A1 (en) | 2003-09-08 |
| EP1198441A4 (en) | 2003-01-22 |
| CZ2002183A3 (en) | 2002-11-13 |
| CA2380285A1 (en) | 2001-02-01 |
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