Abstract: The present invention relates, in part, to the discovery that, during the fluorination of certain fluoroolefin starting reagents, oligomerization/polymerization of such reagents reduces the conversion process and leads to increased catalyst deactivation. The present invention also illustrates that vaporizing such starting reagents in the presence of one or more organic co-feed reduces such oligomerization/polymerization and improves catalytic stability.

Abstract: The present invention relates, in part, to the discovery that, during the fluorination of certain fluoroolefin starting reagents, oligomerization/polymerization of such reagents reduces the conversion process and leads to increased catalyst deactivation. The present invention also illustrates that vaporizing such starting reagents in the presence of one or more organic co-feed reduces such oligomerization/polymerization and improves catalytic stability.

Abstract: A process for the manufacture of halogenated olefins in semi-batch mode by dehydrohalogenation of halogenated alkanes in the presence of an aqueous base such as KOH which simultaneously neutralizes the resulting hydrogen halide. During the process, aqueous base is continuously added to the haloalkane which results in better yields, lower by-product formation and safer/more controllable operation.

Abstract: Disclosed is a process to separate halogenated organic contaminants such as 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 2,3,3,3-tetrafluoropropene (HFO-1234yf), trifluoropropyne (TFPY) from hydrochloric acid (HCl) with an adsorbent selected from an activated carbon, an MFI molecular sieve, a carbon molecular sieve, silica, and combinations thereof.

Abstract: The invention provides a reactor comprising a reaction chamber having a catalytic surface in contact with reactants in said chamber, and a source for passing electrical current through said catalytic surface. The reactor can be used for dehydrohalogentation reactions, such as dehydrochlorination of HCFC-244bb to HFO-1234yf and for reactions where zero valent metals are employed for catalysis. The invention further provides a process to prepare HFO-1234yf from HCFC-244bb using an electrically heated reaction chamber.

Abstract: The present disclosure provides separation processes for removing heavy organics that are formed in various production processes of HCFO-1233zd(E). Such separation processes allow for the recovery and/or separation of the heavy organics from reactants that are used to form HCFO-1233zd(E), including HF. Such separation or recovery processes may utilize various separation techniques (e.g., decanting, liquid-liquid separation, distillation, and flash distillation) and may also utilize the unique properties of azeotropic or azeotrope-like compositions. Recovery of the heavy organic that is substantially free from HF may allow for their use in subsequent manufacture processes or disposal.

Abstract: A method for producing 1,1,1,2-tetrafluoropropene and/or 1,1,1,2,3-pentafluoropropene using a single set of four unit operations, the unit operations being (1) hydrogenation of a starting material comprising hexafluoropropene and optionally recycled 1,1,1,2,3-pentafluoropropene; (2) separation of the desired intermediate hydrofluoroalkane, such as 1,1,1,2,3,3-hexafluoropropane and/or 1,1,1,2,3-pentafluoropropane; (3) dehydrofluorination of the intermediate hydrofluoroalkane to produce the desired 1,1,1,2-tetrafluoropropene and/or 1,1,1,2,3-pentafluoropropene, followed by another separation to isolate the desired product and, optionally, recycle of the 1,1,1,2,3-pentafluoropropene.

Abstract: The present disclosure provides separation processes that use azeotropic or azeotropic-like compositions of 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) that allow for improved recovery rates of 1-chloro-3,3,3-trifluoropropene during or after manufacturing processes. Such recovery or separation processes can utilize the unique properties of azeotropic or azeotropic-like composition with various combinations of separation techniques (e.g., distillation and decanting) that yield highly pure compositions of 1-chloro-3,3,3-trifluoropropene and simultaneously offer high yields of 1-chloro-3,3,3-trifluoropropene. Such highly pure compositions of 1-chloro-3,3,3-trifluoropropene may find useful applications in polymer technology as monomers or comonomers.

Abstract: Disclosed is a process for the manufacture of 1234yf from 1,1,2,3-tetrachloropropene, abbreviated herein as “TCP,” in three integrated steps: (a) the R-1 hydrofluorination of TCP to form 1233xf in the vapor phase; (b) the R-2 hydrofluorination of 1233xf to form 244bb in either the liquid phase or in the liquid phase followed by the vapor phase; and (c) the R-3 dehydrochlorination of the 244bb in either the liquid or the vapor phase to produce 1234yf; wherein the vapor phase hydrofluorination of TCP in step (a) is carried out at a higher pressure than the liquid phase hydrofluorination of 1233xf; and wherein the HC1 generated during these steps is scrubbed with water to form an acid solution and the organic components are scrubbed with a caustic solution and then dried before further processing.

Abstract: A process for the manufacture of halogenated olefins in semi-batch mode by dehydrohalogenation of halogenated alkanes in the presence of an aqueous base such as KOH which simultaneously neutralizes the resulting hydrogen halide. During the process, aqueous base is continuously added to the haloalkane which results in better yields, lower by-product formation and safer/more controllable operation.

Abstract: The invention relates to a process to prepare tetrahalopropenes, such as 2-chloro-3,3,3-trifluoropropene (1233xf). The process comprises atomizing a feed material, such as 1,2,3-tetrachloropropene (1230xa) and the like, and mixing it with superheated HF to form a vaporized composition of feed material and HF with substantially instantaneous contact with a vapor phase fluorination catalyst. The invention extends catalyst life and forestalls catalyst deactivation.

Abstract: The invention relates to a process to prepare tetrahalopropenes, such as 2-chloro-3,3,3-trifluoropropene (1233xf). The process comprises atomizing a feed material, such as 1,1,2,3-tetrachloropropene (1230xa) and the like, and mixing it with superheated HF to form a vaporized composition of feed material and HF with substantially instantaneous contact with a vapor phase fluorination catalyst. The invention extends catalyst life and forestalls catalyst deactivation.

Abstract: The present invention is directed to a combination reactor system for exothermic reactions comprising a trickle-bed reactor and a shell-and-tube reactor. This combination allows the system to efficiently remove heat while also providing the ability to control both the temperature and/or reaction progression. The trickle-bed reactor removes heat efficiently from the system by utilizing latent heat and does not require the use of a cooling or heating medium. The shell-and-tube reactor is used to further progress the reaction and provides a heat exchanger in order to introduce fluid at the desired temperature in the shell-and-tube reactor. Also, additional reactant or reactants and/or other fluids may be introduced to the shell-and-tube section of the reactor under controlled temperature conditions.

Abstract: The present disclosure provides separation processes that use azeotropic or azeotropic-like compositions of 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) that allow for improved recovery rates of 1-chloro-3,3,3-trifluoropropene during or after manufacturing processes. Such recovery or separation processes can utilize the unique properties of azeotropic or azeotropic-like composition with various combinations of separation techniques (e.g., distillation and decanting) that yield highly pure compositions of 1-chloro-3,3,3-trifluoropropene and simultaneously offer high yields of 1-chloro-3,3,3-trifluoropropene. Such highly pure compositions of 1-chloro-3,3,3-trifluoropropene may find useful applications in polymer technology as monomers or comonomers.

Abstract: Disclosed is a process to dry 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) or its mixtures by washing with water and or alkaline solution. The resulting liquid mixture, containing HCFO-1233zd, other organic, and water, is allowed to settle, and thereafter, the lighter water layer is decanted off from the top of the mixture. The heavier HCFO-1233zd layer is then withdrawn from the bottom of the decanter to a desiccant dryer (e.g., molecular sieve, activated alumina, silica gel, and the like) to further remove the residual soluble moisture from the HCFO-1233zd to about 80 ppm or less.

Abstract: In certain aspects, the present invention relates to methods for increasing the cost efficiency and safety of the hydrogenation of a fluorinated olefin by controlling the reaction conditions and parameters. In further aspects, the hydrogenation reaction is provided in a two stage reaction wherein the reactant amounts, temperature and other parameters are controlled such that the conversion percentage, selectivity, and reaction parameters are all within commercially acceptable levels.

Abstract: A process is described wherein otherwise unusable by-products from a process for the manufacture of trans HCFO-1233zd(E) are converted to a valuable product by introducing them into a process for the production of HFC-245fa. The process includes the catalytic hydrofluorination of a reaction mixture comprising the HCFO-1233zd production by-products.

Abstract: The invention relates to a composition comprising 2-choro-1,1,1,2-tetrafluoropropane (244bb) and less than about 2% by weight 1,1,1,2,2-pentafluoropropane (245cb).

Abstract: A method for producing 1,1,1,2-tetrafluoropropene and/or 1,1,1,2,3-pentafluoropropene using a single set of four unit operations, the unit operations being (1) hydrogenation of a starting material comprising hexafluoropropene and optionally recycled 1,1,1,2,3-pentafluoropropene; (2) separation of the desired intermediate hydrofluoroalkane, such as 1,1,1,2,3,3-hexafluoropropane and/or 1,1,1,2,3-pentafluoropropane; (3) dehydrofluorination of the intermediate hydrofluoroalkane to produce the desired 1,1,1,2-tetrafluoropropene and/or 1,1,1,2,3-pentafluoropropene, followed by another separation to isolate the desired product and, optionally, recycle of the 1,1,1,2,3-pentafluoropropene.

Abstract: Disclosed is a process to dry 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) or its mixtures by washing with water and or alkaline solution. The resulting liquid mixture, containing HCFO-1233zd, other organic, and water, is allowed to settle, and thereafter, the lighter water layer is decanted off from the top of the mixture. The heavier HCFO-1233zd layer is then withdrawn from the bottom of the decanter to a desiccant dryer (e.g., molecular sieve, activated alumina, silica gel, and the like) to further remove the residual soluble moisture from the HCFO-1233zd to about 80 ppm or less.