KR20080066853A - Method for producing fluorinated organic compounds - Google Patents

Abstract

Disclosed is a method for producing fluorinated organic compounds, including hydrofluoropropenes, which preferably comprises converting at least one compound of formula (I): CF3CFnCHmXa-m to at least one compound of formula (II) CF3CZCHZ where each X is independently Cl, I or Br; each Z is independently H or F; n is 1 or 2; m is 1, 2 or 3, provided that when n is 1, m is 1 or 2; a is 2 or 3, and a-m >= 0. Certain embodiments include the step of reacting fluorinated C2 olefin, such as tetrafluoroethylene, with a C1 addition agent under conditions effective to produce a compound of formula (I).

Description

Method for producing fluorinated organic compound {METHOD FOR PRODUCING FLUORINATED ORGANIC COMPOUNDS}

The present invention relates to a new method for preparing fluorinated organic compounds, and more particularly, to a method for preparing fluorinated olefins.

Hydrofluorocarbons (HFC's), in particular tetrafluoropropene (2,3,3,3-tetrafluoro-1-propene (HFO-1234yf) and 1,3,3,3-tetrafluoro-1 Hydrofluoroalkenes such as propene (including HFO-1234ze) are effective coolants, chlorinating agents, thermally conductive media, propellants, blowing agents, swelling agents, gaseous dielectrics, sterilant carriers, Disclosed as polymerization media, particulate removal fluids, carrier fluids, buffering abrasive agents, displacement drying agents and power cycle working fluids. come. Unlike chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs), which potentially damage the earth's ozone layer, HFCs do not contain chlorine and therefore pose no threat to the ozone layer.

Several methods of preparing hydrofluoroalkanes are known. For example, US Pat. No. 4,900,874 (Ihara et al.) Describes a process for making fluorine-containing olefins by contacting hydrogen gas with fluorinated alcohols. Although this seems to be a relatively high yield method, handling hydrogen gas at high temperatures to produce on a commercial scale poses a safety challenge. In addition, the cost of producing such hydrogen gas, such as building an on-site hydrogen plant, can be enormously expensive in many cases.

US Pat. No. 2,931,840 to Marquis describes a process for making fluorine containing olefins by pyrolysis of methyl chloride and tetrafluoroethylene or chlorodifluoromethane. This process is a relatively low yield process in which a large percentage of organic starting materials are converted to unwanted and / or trivial by-products, including a significant amount of carbon black. The carbon black is not only undesirable but also easy to inactivate the catalyst used in the process.

The preparation of R-1234yf has been described in trifluoroacetylacetone and sulfertetrafluoride. Journal of Fluorine Chemistry, Vol. 82, Iss. 2, p. See 171-174 (1997). U. S. Patent No. 5,162, 594 (Krespan) also discloses a process for reacting tetrafluoroethylene with another fluorinated ethylene in the liquid phase to produce a polyfluoroolefin product.

Applicants have discovered a method for preparing fluorinated organic compounds including hydrofluoropropenes. In a broad aspect of the invention, the process comprises halogenated alkanes, and preferably fluorinated alkanes to fluorinated alkenes having unsaturated terminal carbons having halogen substituents, preferably fluorine substituents. To convert. In certain preferred embodiments, the process comprises at least one compound of formula (I):

CF ₃ [C (R ¹ _a R ² _b )] _n C (R ³ _c R ⁴ _d ) (Ⅰ)

At least one compound of formula (II):

CF ₃ [C (R ¹ _a R ² b)] _n-1 CZ = CHZ (II)

Wherein R ¹ , R ² , R ³ and R ⁴ are each independently a hydrogen atom or a halogen atom selected from the group consisting of fluorine, chlorine, bromine and iodine, provided that R ¹ , R At least one of ² , R ³ and R ⁴ is halogen; a and b are independently equal to 0, 1 or 2, provided that (a + b) = 2; b and c are independently 0, 1, 2 or 3, and (c + d) = 3, n is 1, 2, 3 or 4, and each Z is independently H or halogen and is halogen Preferably, it is F, provided that Z to the terminal carbon is halogen, and preferably Z to the terminal carbon is F.

In certain preferred embodiments, each Z is different, in a particularly preferred embodiment, each Z is different and Z on the terminal carbon is F, ie, the compound is (HFO- 1234ze).

In certain embodiments, the compound of formula (I) preferably comprises a compound wherein each of R ₁ and R ₂ is H and at least one of R ₃ or R ₄ is H. In certain such embodiments wherein the compound of Formula I is a tri-carbon compound, the compound of Formula (IA) is preferred.

CF ₃ CH ₂ CH _m X _{3 -m} (ⅠA)

Wherein each X is independently F, Cl, I or Br; Each Z in formula (II) is independently H or halogen, preferably F when halogen; m is 1 or 2. Preferred among the above compounds for use according to formula (IA) are pentachloropropane (HCC-240); Tetrachlorofluoropropane (HCFC-241); Trichlorodifluoropropane (HCFC-242); Dichlorotrifluoropropane (HCFC-243); Chlorotrifluoropropane (HCFC-244); And pentafluoropropane (HFC-245), including all of its respective isomers, but preferably including HCFC-244fa and HFC-245fa.

Said preferred conversion step of the present invention comprises catalytic conversion of a compound of formula (I), more preferably a compound of formula (IA) to one or more compounds of formula (II) in gas phase or liquid phase. The catalytic conversion step, in a preferred embodiment, is preferably at least about 50%, more preferably at least 70%, and even more preferably, at least for converting the compound of formula (I). Introducing said compound of formula (I) into the reaction system under conditions effective for 90% conversion. The conversion step is generally at least about 60% selectivity, more preferably at least about 80% selectivity to the compound of formula (II), preferably tetrafluoropropene, and even more preferably HFO-1234ze. And even more preferably, a reaction product having at least about 95% selectivity.

An advantageous aspect of the present invention is that relatively high conversions and high selectivity reactions can be used to produce preferred fluoroolefins, preferably C3 fluoroolefins. Moreover, in this particular preferred embodiment said method enables the preparation of the desired fluoroolefins from relatively attractive starting materials. For example, pentafluoropropene, in particular 1,1,3,3,3-pentafluoropropane (HFC-245fa), or chlorotetrafluoropropane, in particular 1-chloro, 1,3,3, 3-tetrafluoropropane (HCFC-244fa) is each compound of formula (I), which may be an advantageous starting material in certain embodiments. For example, such a product can be expected to be relatively easy to handle and generally can be readily prepared in commercial quantities or from other materials that are readily available.

Preferably, the compound of formula (I) is exposed to reaction conditions effective to prepare a reaction product comprising one or more predetermined fluoroolefins, preferably one or more compounds of formula (II). In a preferred aspect of the invention, the conversion step does not necessarily limit, but sometimes includes for convenience what is meant herein as a dehydrohalogenation reaction or, in particular, a dehydrofluorination reaction in certain embodiments. Certain preferred embodiments of the present invention are described below, and without limitation, abbreviations are used for convenience.

I. Formation of Compounds of Formula (II)

In certain preferred embodiments, the conversion step is performed under conditions effective to provide at least about 40%, more preferably at least 55%, and even more preferably at least about 70% of formula (I) conversion. . In certain preferred embodiments the conversion is at least about 90% and, more preferably, about 100%. Moreover, in certain preferred embodiments, the conversion of the compound of formula (I) to produce the compound of formula (II) is at least about 85%, more preferably at least about 90% and, more preferably at least 95%, and more More preferably under conditions effective to provide formula (II) selectivity of about 100%.

The preferred reaction step involved a gas phase reaction (or possibly a combination of gaseous and liquid phase reactions), and it is contemplated that the reaction can be carried out batchwise, continuously or in combination thereof.

A. Gas phase dehydrohalogenation

One very preferred reaction step according to the invention can be described by reactions in which the compound of formula (IB) comprises a compound in which m is 1, wherein the compound of formula (IB)

CF ₃ CH ₂ CHX ₂ (ⅠB)

to be.

For example, one preferred compound of formula (IB) is chlorotetrafluoropropane, especially 1-chloro, 1,3,3,3-tetrafluoropropane 244fa. In certain preferred embodiments, said stream comprising said compounds of formula (I), preferably (IA) and / or (IB) is preheated to a temperature of about 150 ° C to about 300 ° C, preferably 250 ° C. And introduced into the reaction vessel and maintained at a predetermined temperature, preferably from about 400 ° C to about 700 ° C, more preferably from about 450 ° C to about 600 ° C.

Preferably the container comprises a material resistant to corrosion such as Hastelloy, Inconel, Monel and / or fluoropolymer linings. Preferably, the vessel has suitable means for heating the reaction mixture to a desired reaction temperature, for example a fixed or fluid catalyst bed catalyst filled with a suitable dehydrohalogenation catalyst. It includes.

Accordingly, the dehydrohalogenation reaction step is expected to be carried out using a wide range of process variables and process conditions in view of the overall teachings contained herein. However, in certain embodiments this reaction step preferably comprises a gas phase reaction, preferably in the presence of a catalyst.

Although it is anticipated that a wide range of catalysts and catalyst types can be used in accordance with the present invention, Applicants have found that exceptional results can be obtained when the catalyst comprises a charge neutral metal catalyst. As used herein, the term "neutral charge metal catalyst" means a catalyst comprising a metal atom having a substantially neutral charge. For convenience purposes, such neutral charge metal catalysts are used herein as "M ⁰ " or "M ⁰ catalysts." For catalysts containing certain metals, analogous names, for example, "Ni ⁰ catalyst (Ni ⁰ catalyst is used to refer to a catalyst comprising substantially neutral nickel atoms. In certain preferred embodiments, the present conversion process comprises providing a carbon- and / or metal-based catalyst, more preferably a M ⁰ catalyst (supported or unsupported). Preferably, the M ⁰ catalyst, when used, comprises a Ni ⁰ catalyst, or a Pd ⁰ catalyst, a Fe ⁰ catalyst and combinations thereof. In certain preferred embodiments, the catalyst is essentially an M ⁰ catalyst, preferably a Ni ⁰ catalyst, or a M ⁰ catalyst selected from the group consisting of Pd ⁰ catalysts, Fe ⁰ catalysts, and combinations of two or more thereof. It is composed. When such a catalyst is supported, the support is preferably in certain embodiments Catelus, which is carbon and / or activated carbon. Of course, it is envisaged that other catalysts and catalyst supports may be used, including palladium on carbon, palladium based catalysts (including palladium on aluminum oxide), and many other catalysts may be used in particular embodiments in view of the teachings contained herein. It is expected to be used according to the requirements. Of course, two or more of these catalysts, or other catalysts not described herein, can also be used in combination.

Many embodiments in which supported Ni-based catalysts and even more preferably Ni0-based catalysts (formula (I) compounds comprise one or more or substantially consist of one or more compounds of formula (IA) and / or formula (IB)) Ni (II) acetylacetonate precursor and tetrabutylammonium bromide are first collected to initially form the catalyst and then, for example, to exposure to hydrogen It is generally desirable to convert Ni (II) to Ni (0) by exposure to the same reducing conditions. It is also generally preferred that the catalyst is dried and subjected to fluorination before use. One of the preferred methods of forming a preferred catalyst of this type is disclosed in the examples herein.

For a preferred activated carbon catalyst which is also preferred in many embodiments, including many embodiments in which the compound of formula (I) comprises one or more of, or consists essentially of, a compound of formula (IA) and / or (IB), It is generally desirable to expose activated carbon to drying and fluorination treatments before use. One preferred method of making this type of preferred catalyst is described in the Examples herein.

In general, the catalyst, in particular the activated carbon catalyst, is preferably fluorinated for about several hours (ie 6 hours). In a preferred embodiment, the fluorination of the catalyst comprises exposing the catalyst to an HF stream at about reaction temperature and at a mild pressure, for example about 35 psia.

The gas phase dehydrohalogenation reaction can be carried out, for example, by introducing the compound of formula (I), and preferably (IA), in gaseous form into a suitable reaction vessel or reactor. Preferably the container comprises a material resistant to corrosion such as Hastelloy, Inconel, Monel and / or fluoropolymer linings. Preferably, the vessel preferably has suitable means for heating the reaction mixture to a desired reaction temperature, as described herein, and is a fixed bed or fluid catalyst filled with a catalyst, for example a suitable dehydrohalogenation catalyst. It includes a bed.

Depending on the catalyst used and the relevant factors such as the most preferred reaction products, a wide range of reaction temperatures can be used, but in particular those containing compounds of formula (I) (more preferably, formula (IA) and / or It is generally preferred that the reaction temperature of the dehydrohalogenation step (consisting essentially of the compound of (IB)) is from about 400 ° C to about 800 ° C, preferably from about 400 ° C to about 700 ° C.

It is anticipated that a wide range of reaction pressures may be used, again due to related factors such as the particular catalyst and most preferred reaction products used in general. The reaction pressure can be, for example, superatmospheric, atmospheric or vacuum, and in certain preferred embodiments is about 1 to about 120 psia.

In certain embodiments, an inert diluent gas, such as nitrogen, may be used in combination with other reactor feeds. When such diluents are used, it is generally preferred that the compound of formula (I) comprises from about 50% to over 99% by weight, based on the combined weight of the diluent and the compound of formula (I).

It is anticipated that the amount of catalyst used may vary depending on the particular parameters present in each embodiment. In certain preferred embodiments, the contact time is from about 0.1 seconds to about 1000 seconds, preferably from about 3 seconds to about 50 seconds.

In embodiments in which the compound of formula (I) comprises or consists essentially of the compound of formula (IA) and / or formula (IB), and especially in which the product of the desired formula (II) is HFO-1234ze, Applicants It has been found to be preferred to use a M ⁰ catalyst, preferably a catalyst comprising substantially neutral palladium, nickel iron and / or carbon, such as a palladium catalyst on carbon or nickel on a carbon catalyst.

Preferably, in this dehydrohalogenation embodiment described in this section, the conversion of the compound of formula (I) is at least about 50%, more preferably at least about 65%, and even more preferably at least about 90 % to be. In such embodiments, preferably, the selectivity to HFO-1234ze is at least about 70%, more preferably at least about 80%, more preferably at least about 95%.

B. Liquid Phase Reduction

One possible reaction step is to dehydrohalogen the compound of formula (I), for example 1-chloro, 1,3,3,3 tetrafluoropropane (HCFC-244fa), such as potassium hardoxide (KOH). And a reaction to form a compound of formula (II) in contact with the agent. This reaction can be described by the following scheme, but not necessarily by way of explanation:

CF ₃ CH ₂ CHFCl  + KOH  → CF ₃ CH = CHF  + KCl  + H ₂ O

In a preferred aspect of this embodiment, a phase transfer agent, such as crown 18-ether, is included in the reaction mixture, and the KOH is preferably from about 10% to 50% by weight, more Preferably, an aqueous solution comprising about 20% to about 30% by weight KOH is provided.

In certain preferred embodiments, the KOH solution is introduced into the reaction vessel at a relatively cold temperature, preferably from about −10 ° C. to about 10 ° C., preferably about 0 ° C. A suitable amount of the compound of formula (I), preferably about 0.1 to about 100 moles, preferably 0.9 to 10 moles per mole KOH, is then added to the reaction vessel. The reaction mixture is preferably slowly heated to about 40 ° C. to about 80 ° C., more preferably about 50 ° C. to 60 ° C. while applying mechanical energy (stirring or stirring). Since the preferred reaction is an exothermic reaction, it can be increased to a temperature of about 60 ℃ to about 95 ℃, more preferably, about 65 ℃ to about 75 ℃. The reaction pressure in this embodiment may vary depending on the specific process parameters of each application, but in certain embodiments ranges from about 0 to about 200 psig during the course of the reaction. In certain embodiments, the exothermic heat of the reaction is removed from the reaction mixture (eg by cooling) to maintain a reaction temperature within the aforementioned range. The overall reaction time in this particular preferred embodiment is about 1 to about 40 hours, more preferably about 1 to about 10 hours and even more preferably about 2 to 6 hours.

After the designated reaction time, the reaction mixture is preferably cooled down to, for example, about 20 ° C. to about 40 ° C. to facilitate collection of the reaction product. Preferably, the conversion to a preferred yield of about 35% to about 95%, and the selectivity to HFO-1234ze are at least about 70% and about 100%, respectively, more preferably at least 90% to about 100%.

II. Formation of Compounds of Formula (I)

It is anticipated that a wide range of raw materials may be known and available for the supply of compounds of formula (I) according to the invention. For example, in certain embodiments it may be desirable to supply pentachloropropane (HCC-240) and subject the compound to one or more reactions to produce one or more compounds consistent with Formula (I). Various other methods for preparing compounds consistent with Formula (I) are described in US Pat. No. 5,710,352; 5,969,198; And 6,023,004, each of which is incorporated herein by reference. Another method described in US Pat. No. 5,728,904 is economical, suitable for large scale use, and using readily available raw materials. The method of this patent uses three steps: 1) formation of CCl ₃ CH ₂ CCl ₃ by reaction of CCl ₄ with vinylidene chloride; 2) in the presence of a fluorination catalyst selected from TiCl ₄ SnCl ₄ or mixtures thereof Conversion of CCl ₃ CH ₂ CCl ₃ to CF ₃ CH ₂ CF ₂ Cl by reaction with HF; And 3) reduction of CF ₃ CH ₂ CF ₂ Cl to CF ₃ CH ₂ CF ₂ H. Furthermore, commercial amounts of HFC-245fa may be used as starting materials for the process for direct conversion to fluoroolefins (eg, CF ₃ CH = CFH) by dehydrohalogenation according to the process disclosed herein. For, Morristown, NJ. Available from Honeywell International Inc.

Additional features of the invention are provided in the following examples, which should not be construed as limiting the claims in any way.

Example  1-21

These examples illustrate vapor phase dehydrohalogenation from CF ₃ CH ₂ CHF ₂ (HFC-245fa) to CF ₃ CH = CHF (HFC-1234ze). A 22-inch (1 / 2-inch diameter) Monel tube reactor was charged with 50 cc of catalyst as detailed in Table I below. The reactor is installed inside a heater with three zones (top, middle, bottom). The inlet of the reactor is connected to a pre-heater maintained at about 250 ° C. by electrical heating. Organic (HFC-245fa) was supplied from the cylinder holding 65 ° C. The flow of inert nitrogen gas (20 sccm) was maintained from beginning to end. The reactor temperature was brought to the temperature shown in the table above. The HFC-245fa is transferred to a preheater maintained at a temperature of about 250 ° C. through a gas-flow regulator. The gas stream exiting the preheater is passed through the catalyst bed at a predetermined temperature and at a pressure of about 2.5-5.3 psig over a period of time. On-line GC and GCMS were used to analyze samples taken at regular time intervals from the reactor outlet line. Finally, the reactor eluate was introduced into a 20-60% KOH scrubber solution, and the eluate was then condensed from the scrubber solution to collect the product. Then the desired product CF ₃ CH = CFH (HFC-1234ze) was separated from the mixture by distillation. Depending on the reaction conditions, the conversion of HFC-245fa is about 50% to about 100%, and the selectivity for HFC-1234fa is about 60% to about 100%. The trace amounts of the byproducts obtained were CHF ₃ and CH ₂ = CHF.

The results are shown in Table I below.

Table 1: HFC-245fa → CF ₃ CH = CFH (HFO-1234ze)

Example # / catalyst HFC-245fa, gm / hour T, ℃ % Conversion rate of 245fa % Selectivity for 1234ze Example 1 / A 15 495 30 100 Example 2 / A 15 525 68 100 Example 3 / A 15 565 100 85 Example 4 / B 15 515 82 100 Example 5 / C 15 515 86 100 Example 6 / D 15 515 91 100 Example 7 / E 15 515 100 100 Example 8 / F 15 475 78 45 Example 9 / G 15 475 82 43 Example 10 / H 15 475 85 43 Example 11 / I 15 475 85 44 Example 12 / J 15 515 68 100 Example 13 / K 15 515 76 100 Example 14 / L 15 515 88 98 Example 15 / M 15 515 100 96 Example 16 / A 15 515 68 100 Example 17 / AA 15 515 76 100 Example 18 / A 15 515 88 98 Example 19 / AA 15 515 100 96 Example 20 / C 520 96 80 60 Example 21 / G 500 63 100 73

Catalyst (100 cc): A is activated carbon; AA is acid treated activated carbon; B is 0.2 wt% Ni / C; C is 0.8 wt% Ni / C; D is 1.1 wt% Ni / C; E is 1.8 wt% Ni / C; F is 0.4 wt% Ni / Cr ₂ O ₃ ; G is 0.6 wt% Ni / Cr ₂ O ₃ ; H is 0.7 wt% Ni / Cr ₂ O ₃ ; I is 1 wt% Ni / Cr ₂ O ₃ ; J is 0.4 wt% Ni / Al ₂ O ₃ ; K is 0.6 wt% Ni / Al ₂ O ₃ ; L is 0.7 wt% wt% Ni / Al ₂ O ₃ ; M is 1 wt% wt% Ni / Al ₂ O ₃ ; The product, 1234ze, is obtained as a mixture of cis-1234ze (2-5 mol%) and trans-1234ze (95-98 mol%).

Example  22-24

These examples illustrate the gas phase dehydrohalogenation reaction from CF ₃ CH ₂ CHFCl (HCFC-244fa) to CF ₃ CH = CHF (HFO-1234ze). The procedure of Examples 1 to 21 was repeated except that HCFC-244fa was used instead of HFC-245fa. Small amounts of byproducts (coupling less than 0.5%) identified by GC / MS were CF ₃ Cl and CF ₃ CH ₂ Cl.

The results are shown in Table 2 below.

Table 1: HFC-244fa → CF ₃ CH = CFH (HFO-1234ze)

Example # / catalyst HFC-244fa, gm / hour T, ℃ % Conversion rate of 244fa % Selectivity for 1234ze Example 19 / AA 15 515 100 96 Example 20 / C 520 96 80 60 Example 21 / G 500 63 100 73

Catalyst-as defined in Table 1: A is activated carbon; AA is acid treated activated carbon; B is 0.2 wt% Ni / C; C is 0.8 wt% Ni / C; D is 1.1 wt% Ni / C; E is 1.8 wt% Ni / C; F is 0.4 wt% Ni / Cr ₂ O ₃ ; G is 0.6 wt% Ni / Cr ₂ O ₃ ; H is 0.7 wt% Ni / Cr ₂ O ₃ ; I is 1 wt% Ni / Cr ₂ O ₃ ; J is 0.4 wt% Ni / Al ₂ O ₃ ; K is 0.6 wt% Ni / Al ₂ O ₃ ; L is 0.7 wt% wt% Ni / Al ₂ O ₃ ; M is 1 wt% wt% Ni / Al ₂ O ₃ .

Example  25

This example illustrates the gas phase dehydrohalogenation reaction from CF ₃ CH ₂ CHFCl (HCFC-244fa) to CF ₃ CH = CHF (HFO-1234ze). About 150 grams of 20% KOH solution, 1 gram of 18-Crown ether and 10 grams of CF ₃ CHClCH ₂ F were charged to a 300 ml teflon-lined autoclave. The mixture was stirred at 50 ° C. for 6 hours. The reaction process is monitored by collecting samples and analyzing them by GC and MS every 30 minutes. After the predetermined reaction period, the top gas mixture was transferred to a collection cylinder at -70 ° C. Analysis, and overall material weighing confirms a yield of 55%.

As such, it has been described with some specific embodiments of the invention, and various changes, modifications, and improvements are readily apparent to those skilled in the art. Such alterations, modifications, and improvements are evident from this disclosure, although not explicitly described herein, are part of the above description and are included within the spirit and scope of the present invention. Accordingly, the foregoing description is by way of example only, and not limitation. The invention is defined only by the following claims and equivalents thereto.

Claims (19)

First expression of CF ₃ CH ₂ CH _m X _{3 -m} At least one compound of the following second formula: CF ₃ CZ = CHF A method for producing a fluorinated organic compound comprising the step of converting to at least one compound. Wherein each X is independently Cl, I or Br; Z is independently H or F; m is 1, 2 or 3. The method of claim 1, wherein said converting step is performed under conditions effective to provide at least about 40% conversion of at least one compound according to said first formula. The method of claim 1, wherein said converting step is performed under conditions effective to provide at least about 80% conversion of at least one compound according to the first formula. The method of claim 1, wherein said converting step is performed under conditions effective to provide at least about 90% conversion of at least one compound according to said first formula. The method of claim 1, wherein said converting step is performed under conditions effective to provide at least about 95% conversion of at least one compound according to said first formula. The method of claim 1, wherein said converting step is performed under conditions effective to provide selectivity of at least about 90% of at least one compound according to said second formula. Formula (Ⅰ): CF ₃ [C (R ¹ _a R ² b)] _n C (R ³ _c R ⁴ _d ) (Ⅰ) At least one compound of formula (II): CF ₃ [C (R ¹ _a R ² b)] _n-1 CZ = CHZ (II) A method for producing a fluorinated organic compound comprising the step of converting to at least one compound. Wherein R ¹ , R ² , R ³ and R ⁴ are each independently a hydrogen atom or a halogen atom selected from the group consisting of fluorine, chlorine, bromine and iodine, provided that R ¹ , R ² , R ³ and R ⁴ At least one of is halogen; a and b are independently 0, 1 or 2, wherein (a + b) = 2; b and c are independently equal to 0, 1, 2 or 3, (c + d) = 3, n is 1, 2, 3 or 4, and each Z is independently H or halogen provided In addition, Z to the terminal carbon is halogen. 8. The method of claim 7, wherein said converting step is performed under conditions effective to provide at least about 40% conversion of at least one compound according to formula (I). 8. The method of claim 7, wherein said converting step is performed under conditions effective to provide at least about 90% conversion of at least one compound according to formula (I). 8. The method of claim 7, wherein said converting step is performed under conditions effective to provide selectivity of at least about 90% of at least one compound according to formula (II). 8. The method of claim 7, wherein Z on the terminal carbon is fluorine. 14. The method of claim 13, wherein n is one. 15. The method of claim 14, wherein the compound of formula (II) comprises HFO-1234ze. 8. A compound according to claim 7, wherein the compound of formula (I) is pentachloropropane (HCC-240); Tetrachlorofluoropropane (HCFC-241); Trichlorodifluoropropane (HCFC-242); Dichlorotrifluoropropane (HCFC-243); Chlorotrifluoropropane (HCFC-244); Pentafluoropropane (HFC-245) and all of their respective isomers and combinations thereof. 8. The method of claim 7, wherein said compound of formula (I) comprises HCFC-244fa. 8. The method of claim 7, wherein the compound of formula (I) comprises HCFC-245fa. 8. The process of claim 7, wherein said converting step comprises catalytically converting from said compound of formula (I) to one or more compounds of formula (II). 18. The process of claim 17, wherein catalytically converting the compound of formula (I) comprises exposing the compound of formula (I) to a neutral charge metal catalyst. 18. The process of claim 17, wherein catalytically converting the compound of formula (I) comprises exposing the compound of formula (I) to a Ni ⁰ catalyst.