Honeywell International Inc.

Alliedsignal Inc.

Riegel, Clifford

Stephen A Cottrell

Hsueh Sung Tung

Yuon Chiu

Daniel C Merkel

Haluk Kopkalli

Haiyou Wang

Konstantin A Pokrovski

Gustavo Cerri

Hang Thanh Pham

Robert C Johnson

Kevin D Uhrich

Peter Scheidle

Rajiv R Singh

John Joseph Senetar

Raymond Hilton Thomas

George R Cook

Richard Durick Horwath

Orlando George Rodrigues

Gus Cerri

Merwyn E Howells

Ian R Shankland

Haridasan K Nair

Matthew H Luly

Joshua Close

HsuehSung Tung

Roy P Robinson

Jeffrey Warren McKown

Charles Francis Swain

Robert A Smith

Clifford Scott Riegel

Philip DePrato

Curtis A Brescher

Daniel J Brenner

Stephen Delo

Clifford Riegel

Jarrad Garrison

Hseuhsung Tung

Robert E Wilson

Chad L Marks

William R Jones

Kevin D Ulrich

Youn Chiu

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.

Process for dehydrohalogenation of halogenated alkanes

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.

Process for the manufacture of fluorinated olefins

The invention provides an improved process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) by reacting 2-chloro-3,3,3,-trifluoropropene (HCFO-1233xf) with hydrogen fluoride, in a liquid phase reaction in the presence of hydrogen chloride and a liquid phase fluorination catalyst. The hydrogen chloride is added into the reaction from an external source at a pressure of about 100 psig or more. The HCFC-244bb is an intermediate in the production of 2,3,3,3-tetrafluoropropene-1 (HFO-1234yf).

Process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb)

Disclosed is a method for capturing and recycling iron catalyst used in the production of haloalkane compounds and more particularly, to an improved process for the manufacture of the compound 1,1,1,3,3-pentachloropropane (HCC-240fa), in which an electromagnetic separation unit (EMSU) is used to facilitate the reaction. When energized, the EMSU functions to remove all iron particles from the reactor effluent; when de-energized, the iron particles captured by the EMSU can be flushed back into the reactor for re-use in the continued production of HCC-240fa. The present invention is also useful in the manufacturing processes for other haloalkane compounds such as HCC-250 and HCC-360.

Method for capturing and recycling iron catalyst used in the production of haloalkane compounds

The invention provides an improved process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) by reacting 2-chloro-3,3,3,-trifluoropropene (HCFO-1233x1) with hydrogen fluoride, in a liquid phase reaction in the presence of hydrogen chloride and a liquid phase fluorination catalyst. The hydrogen chloride is added into the reaction from an external source at a pressure of about 100 psig or more. The HCFC-244bb is an intermediate in the production of 2,3,3,3-tetrafluoropropene-1 (HFO-1234yf).

Provided are azeotropic or azeotrope-like mixtures of 1,1,3,3-tetrachloroprop-1-ene (HCO-1230za) and hydrogen fluoride. Such compositions are useful as feed stock in the production of HFC-245fa and HCFO-1233zd.

Azeotropic compositions of 1,1,3,3-tetrachloroprop-1-ene and hydrogen fluoride

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.

Disclosed are a reactor and agitator useful in a high pressure process for making 1-chloro-3,3,3-trifluoropropene (1233zd) from the reaction of 1,1,1,3,3-pentachloropropane (240fa) and HF, wherein the agitator includes one or more of the following design improvements:

Reactor and agitator useful in a process for making 1-chloro-3,3,3-trifluoropropene

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.

Process for drying HCFO-1233zd

Disclosed is a process for the manufacture of 1234yf from 1,1,2,3-tetrachloropropene, abbreviated herein as 'TCP,' in three integrated steps: 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.

Methods of making 2,3,3,3-tetrafluoro-2-propene

Disclosed is a process for the production of 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) which includes reacting a propane feedstock comprising tetrachlorofluoropropanes, trichlorodifluoropropanes, dichlorotrifluoropropanes, or a mixture thereof, in the presence of a solid catalyst. The process generally comprises the following four steps: (i) providing a propane feedstock comprising trichlorodifluoropropanes and dichlorotrifluoropropanes, (ii) reacting the feedstock in a vapor phase reactor in the presence of HF and in the presence of a solid catalyst under conditions effective to form a product stream comprising HCFO-1233zd and unconverted starting materials, (iii) recovering or removing HCl and HF, and (iv) isolating HCFO-1233zd(E), HCFO-1233zd(Z), or both.

Process for making HCFO-1233zd

The present invention is directed to processes for the production of 1233zd from 240fa and HF, with or without a catalyst, at a commercial scale. The 240fa and HF are fed to a reactor operating at high pressure. The resulting product stream comprising 1233zd, HCl, HF, and other byproducts is treated to one or more purification techniques including phase separation and one or more distillations to provide purified 1233zd, which meets commercial product specifications, i.e., having a GC purity of 99.5% or greater.

Integrated process for the production of 1-chloro-3,3,3-trifluoropropene

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.

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Baton Rouge, LA, United States of America

Stephen A Cottrell