E.i. Dupont De Nemours and Company

E. I. Du Pont De Nemours + Company

The Chemours Company Fc, LLC

Ralph Newton Miller

Barry Asher Mahler

Allen Capron Sievert

Velliyur Nott Mallikarjuna Rao

Mario Joseph Nappa

Viacheslav Alexandrovich Petrov

V N Rao

Vinci Martinez Felix

Ralph Thomas Baker

Mark Richard Deschere

Olagappan Muthu

Steven Henry Swearingen

V N Mallikarjuna Rao

Sara W Boehmer

Barbara Haviland Minor

Charles Joseph Noelke

Velliyur Nott Rao

Donald J Toton

Chien-Ping Chai Kao

Velliyur N Mallikarjuna Rao

Maria U D Beug-Deeb

Maria U Beug-Deeb

A liquid phase process is disclosed for producing halogenated alkane adducts of the formula CARRCBRR(where A, B, R, R, R, and Rare as defined in the specification) which involves contacting a corresponding halogenated alkane, AB, with a corresponding olefin, CRR&#x2550;CRRin a dinitrile or cyclic carbonate ester solvent which divides the reaction mixture into two liquid phases and in the presence of a catalyst system containing (i) at least one catalyst selected from monovalent and divalent copper; and optionally (ii) a promoter selected from aromatic or aliphatic heterocyclic compounds which contain at least one carbon-nitrogen double bond in the heterocyclic ring. When hydrochlorofluorocarbons are formed, the chlorine content may be reduced by reacting the hydrochlorofluorocarbons with HF. Azeotropes of CClFCHCFwith HF and azeotropes of CFCHCHFwith HF are also disclosed; as are process for producing such azeotropes.

Process for the manufacture of halocarbons and selected compounds and azeotropes with HF

Disclosed herein are processes for the production of hydrofluoroolefins by dehydrofluorination. Also disclosed herein are processes for separation of hydrofluoroolefins from hydrofluorocarbons and from hydrogen fluoride.

Processes for production and purification of hydrofluoroolefins

A process is disclosed for the manufacture of CFCF&#x2550;CHand CFCH&#x2550;CHF. The process involves dehydrofluorinating CFCHFCHF in the presence of a dehydrofluorination catalyst to produce a product mixture comprising CFCF&#x2550;CHand CFCH&#x2550;CHF, and recovering said CFCF&#x2550;CHand CFCH&#x2550;CHF from the product mixture. The present invention also provides a composition comprising (a) the Z-isomer of CFCH&#x2550;CHF and (b) HF; wherein the HF is present in an effective amount to form an azeotropic combination with the Z&#x2014;CFCH&#x2550;CHF.

Tetrafluoropropene production processes

Disclosed herein are azeotrope compositions comprising 1,2,3,3,3-pentafluoropropene and hydrogen fluoride. The azeotrope compositions are useful in processes to produce and in processes to purify 1,2,3,3,3-pentafluoropropene. Additionally, disclosed herein are azeotrope and near-azeotrope compositions comprising 1,1,1,2,3,4,4,5,5,5-decafluoropentane and hydrogen fluoride.

Azeotrope compositions comprising nonafluoropentene and hydrogen fluoride and uses thereof

Disclosed herein are azeotrope or near-azeotrope compositions comprising 2,3,3,3-tetrafluoropropene (HFC-1234yf) and hydrogen fluoride (HF). These compositions are useful in processes to produce and purify HFC-1234yf. Additionally, disclosed herein are processes for the manufacture of HFC-1234yf.

Azeotrope compositions comprising 2,3,3,3-tetrafluoropropene and hydrogen fluoride and uses thereof

Disclosed herein are azeotrope and near-azeotrope compositions comprising E-1,3,3,3-tetrafluoropropene and hydrogen fluoride. These azeotrope and near-azeotrope compositions are useful in processes to produce E-1,3,3,3-tetrafluoropropene and in processes to purify E-1,3,3,3-tetrafluoropropene from mixtures of E-1,3,3,3-tetrafluoropropene with 1,1,1,3,3-pentafluoropropane and/or with hydrogen fluoride.

Azeotrope compositions comprising E-1,3,3,3-tetrafluoropropene and hydrogen fluoride and uses thereof

Disclosed herein are azeotrope compositions comprising 1,2,3,3,3-pentafluoropropene and hydrogen fluoride. The azeotrope compositions are useful in processes to produce and in processes to purify 1,2,3,3,3-pentafluoropropene.

Azeotrope compositions comprising 1,2,3,3,3-pentafluoropropene and hydrogen fluoride and uses thereof

Disclosed herein are azeotrope and near-azeotrope compositions comprising 1,1,1,2,2,4,5,5,6,6,7,7,7-tridecafluoro-3-heptene (HFC-162-13mczy, CFCFCH&#x2550;CFCFCFCF) and 1,1,1,2,2,3,5,5,6,6,7,7,7-tridecafluoro-3-heptene (HFC-162-13mcyz, CFCFCF&#x2550;CHCFCFCF) and hydrogen fluoride (HF) and to azeotrope and near-azeotrope compositions comprising 1,1,1,2,2,3,4,5,5,6,6,7,7,7-tetradecafluoroheptane and hydrogen fluoride (HF). These compositions are useful in processes to produce and purify HFC-162-13mcyz, HFC-162-13mczy and HFC-63-14mee.

Azeotrope compositions comprising tridecafluoro-3-heptene and hydrogen fluoride and uses thereof

The present invention provides extractive distillation processes for removing difluoromethane (HFC-32) from a mixture comprising HFC-32 and at least one of chlorodifluoromethane (CFC-12), 1,1,1-trifluoroethane (HFC-143a), chloropentafluoroethane (CFC-115), and pentafluoroethane (HFC-125) using hydrocarbon, chlorocarbon, and oxygen-containing extractive agents.

Purification of difluoromethane by extractive distillation

A process for the production of HFC-227ea from HF and HFP is provided. This process takes advantage of an azeotropic composition of HF and HFC-227ea in order to produce HFC-227ea essentially free of HF and recycle unreacted HF back to the reactor. The recycle of said azeotropic composition, also allows the use of HFC-227ea as a diluent to aid in control of reactor temperature for a highly exothermic reaction.

Vapor phase production of 1,1,1,2,3,3,3-heptafluoropropane from hydrogen fluoride and hexafluoropropylene

A liquid phase process is disclosed for producing halogenated alkane adducts of the formula CARRCBRR(where A, B, R, R, R, and Rare as defined in the specification) which involves contacting a corresponding halogenated alkane, AB, with a corresponding olefin, CRR&#x2550;CRRin a dinitrile or cyclic carbonate ester solvent which divides the reaction mixture into two liquid phases and in the presence of a catalyst system containing (i) at least one catalyst selected from monovalent and divalent copper; and optionally (ii) a promoter selected from aromatic or aliphatic heterocyclic compounds which contain at least one carbon-nitrogen double bond in the heterocyclic ring. When hydrochlorofluorocarbons are formed, the chlorine content may be reduced by reacting the hydrochlorofluorocarbons with HF. New compounds disclosed include CFCFCClCHCCl, CFCClCHCHCl and CFCClCHCHClF. These compounds are useful as intermediates for producing hydrofluorocarbons. Azeotropes of CClFCHCFwith HF and azeotropes of CFCHCHFwith HF are also disclosed; as are process for producing such azeotropes. A process for purification of certain hydrofluorocarbons and/or chloro-precursors thereof from mixtures of such compounds with HF is also disclosed.

The invention relates to azeotropic compositions of halogenated propanes with HF.

Processes for the purification and use of 2-chloro-1,1,1,2,3,3,3-heptafluoropropane and zeotropes thereof with HF

Nitrogen trifluoride (NF ) containing less than 10 parts-per-million molar impurities, e.g., tetrafluoromethane (PFC-14), is disclosed. Azeotropic and extractive distillation processes using entraining agents for separating NF and PFC-14 from each other and from mixtures with other electronics industry materials are disclosed.

Process for purifying perfluorinated products

Disclosed are processes for separating 1,1,1,3,3-pentafluoropropane (HFC-245fa) from hydrogen fluoride (HF) by distillation, wherein hydrocarbons, chloroflurocarbons, hydrochlorofluorocarbons and fluorocarbons are used as entraining agents. The processes comprise: contacting a first mixture comprising HFC-245fa and HF with an entraining agent selected from the group consisting of hydrocarbons, chlorofluorocarbons, hydrochlorofluorocarbons and fluorocarbons to form a second mixture, distilling the second mixture and thereby separating the HFC-245fa from HF and entraining agent, and recovering HFC-245fa substantially-free of HF.

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Newark, DE, United States of America

Ralph Newton Miller