WO1997007052A1 - Azeotropes de cholorofluoroethanes avec fluorure d'hydrogene - Google Patents

Azeotropes de cholorofluoroethanes avec fluorure d'hydrogene Download PDF

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Publication number
WO1997007052A1
WO1997007052A1 PCT/US1995/010175 US9510175W WO9707052A1 WO 1997007052 A1 WO1997007052 A1 WO 1997007052A1 US 9510175 W US9510175 W US 9510175W WO 9707052 A1 WO9707052 A1 WO 9707052A1
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WO
WIPO (PCT)
Prior art keywords
mole percent
composition
azeotrope
kpa
cci3cf3
Prior art date
Application number
PCT/US1995/010175
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English (en)
Inventor
Barry A. Mahler
Ralph N. Miller
Velliyur Nott Mallikarjuna Rao
Original Assignee
E.I. Du Pont De Nemours And Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by E.I. Du Pont De Nemours And Company filed Critical E.I. Du Pont De Nemours And Company
Priority to PCT/US1995/010175 priority Critical patent/WO1997007052A1/fr
Publication of WO1997007052A1 publication Critical patent/WO1997007052A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B7/00—Halogens; Halogen acids
    • C01B7/19—Fluorine; Hydrogen fluoride
    • C01B7/191—Hydrogen fluoride
    • C01B7/195—Separation; Purification
    • C01B7/196—Separation; Purification by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C19/00—Acyclic saturated compounds containing halogen atoms
    • C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
    • C07C19/10—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine
    • C07C19/12—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine having two carbon atoms

Definitions

  • This invention relates to azeotropic compositions of hydrogen fluoride with halogenated hydrocarbons and their use in manufacturing processes, and more particularly to azeotropes of perhalogenated ethanes with HF and use thereof.
  • 1-Dichlorotet'rafluoroethane i.e., CF3CCI2F or CFC-114a
  • CF3CCI2F or CFC-114a 1-Dichlorotet'rafluoroethane
  • 1, 1,2-tetrafluoroethane i.e., CF3CH2F or HFC-134a
  • a supported metal hydrogenation catalyst see e.g., C. Gervasutti et al. , J. Fluorine Chem., 1981/82, 19, pgs. 1-20.
  • HFC-134a is an environmentally acceptable potential replacement for chlorofluorocarbon (i.e., CFC) refrigerants, blowing agents, aerosol propellants and sterilants that are being viewed with concern in connection with the destruction of stratospheric ozone.
  • CFC chlorofluorocarbon
  • 1, 1-dichlorotetrafluoroethane employed in the hydrogenolysis route to HFC-134a has as low a content of 1, 2-dichlorotetrafluoroethane (i.e., CF2CICF2CI or CFC-114) as practicable since the presence of CFC-114 during hydrogenolysis can lead to formation of 1, 1,2, 2-tetrafluoroethane (i.e., CHF 2 CHF2 or HFC-134; see e.g., J. L. Bitner et al., U.S. Dep. Comm. Off.
  • HFC-134 mixed in HFC-134a may be objectionable for some applications depending on concentration and, since the two isomers boil only 7°C apart, separation of the isomers in high purity is difficult.
  • CF3CCI 2 F can be obtained by reacting CCI3CF3 (i.e., 1, 1, 1-trichlorotri ' fluoroethane or CFC-113a) with HF using various catalysts. Normally, excess HF is used to achieve relatively favorable reactor rates. In vapor- phase processes, typical reactor products contain HCl, unreacted CF3CCI3 and HF as well as CF3CCI2F.
  • the reactor products contain predominately HCl, CF3CCI2F and HF as well as traces of CF3CCI3.
  • HF may be removed from the halogenated hydrocarbon components of the product mixture using conventional aqueous solution scrubbing techniques .
  • aqueous solution scrubbing techniques can create aqueous waste disposal concerns .
  • processes utilizing HF in such product mixtures as well as halogenated hydrocarbons therein such as CFC-113a and CFC-114a.
  • Both CF3CCI2F and CCI3CF3 can be fluorinated by catalytic reaction with HF to form CF3CF3 (i.e., perfluoroethane or PFC-116) a useful etchant compound (see e.g., PCT Patent Publication No. WO 93/17988) .
  • the present invention provides a process for recovering HF from a product mixture comprising HF and at least one compound having the formula CF3CCl2 + F ⁇ _ x (where x is 0 or 1) .
  • the process comprises (1) distilling the product mixture to remove all products which have a lower boiling point than the lowest boiling azeotrope containing HF and said at least one compound; and (2) distilling said azeotrope to recover HF as an azeotropic composition containing HF and said at least one compound.
  • compositions which consist essentially of hydrogen fluoride in combination with an effective amount of a compound selected from the group consisting of CCI 3 CF 3 and CCI 2 FCF3 to form an azeotrope or azeotrope-like composition with hydrogen fluoride, said composition containing from about 10 to 27 mole percent CCI3CF3 or from about 35 to 56 mole percent CCI 2 FCF3.
  • the process of this invention involves azeotropic distillation of HF with at least one compound selected from the group consisting of CF3CCI3 and CF3CCI 2 F.
  • the product mixtures distilled in accordance with this invention can be obtained from a variety of sources. These sources include product mixtures produced by hydrofluorination of CCI3CF3. Product mixtures may also be provided by adding CFC-113a and/or CFC-114a to HF-containing compositions.
  • the product mixture is distilled to remove all products which have a lower boiling point than the lowest boiling azeotrope containing HF and CF3CCI2F and/or CF3CCI3.
  • low- boiling materials can include, for example, HCl, and low boiling halogenated hydrocarbons such as CCIF2CF3 and CF 3 CF3.
  • distillate and azeotropes with higher boiling points can be advantageously removed from appropriate sections of the distillation column.
  • the lowest boiling azeotrope containing HF and CF3CCI 2 F and/or CF 3 CCI3 is then distilled such that HF is recovered as an azeotropic composition containing HF together with
  • the mixture (after distilling components boiling at lower temperatures than the lowest boiling azeotrope of HF with CF3CCI2F and/or CF3CCI3) consists essentially of HF and CF 3 CCI 2 F
  • HF may be recovered as an azeotrope consisting essentially of CF 3 CCI 2 F and H . If excess amounts of CF 3 CCI 2 F or HF remain after azeotropes are recovered from these mixtures, such excess may be recovered as a relatively pure compound.
  • HF may be recovered as an azeotrope consisting essentially of CF 3 CCI 3 and HF. If excess amounts of CF 3 CCI 3 or HF remain after azeotropes are recovered from these mixtures, such excess may be recovered as a relatively pure compound.
  • the distillation of azeotropes containing HF and CF3CCI 2 F and/or CF3CCI 3 typically may be done at a wide variety of temperatures and pressures.
  • the temperature is between about -25°C and 150°C (e.g., from 20°C to 125°C) and the pressure is between 50 kPa and 4750 kPa (e.g., from 140 kPa to 4020 kPa) .
  • Examples of temperatures and pressures suitable for azeotropic formation are provided below.
  • the process of this invention includes embodiments where azeotropic compositions containing from about 10 to 27 mole percent CCI 3 CF 3 or from about 35 to 56 mole percent CCI 2 FCF 3 are recovered.
  • HF may be recovered for example, from a product mixture including CCI 2 FCF 3 formed by the reaction of CCI 3 CF 3 with HF.
  • an azeotropic composition consisting essentially of HF and unreacted CCI 3 CF 3 (e.g., 73 to 90 mole percent HF and 27 to 10 mole percent CCI 3 CF 3 ) may be recovered and recycled to a reactor for said reaction of CCI 3 CF 3 and HF.
  • processes for producing CF 3 CF 3 by fluorination of perhalogenated ethanes containing chlorine and fluorine including CCI 3 CF 3 and CCI 2 FCF 3 can readily employ azeotropes of HF with CCI 2 FCF 3 and/or CCI 3 CF 3 .
  • the distillation equipment and its associated feed lines, effluent lines and associated units should be constructed of materials resistant to hydrogen fluoride, hydrogen chloride and chlorine.
  • Typical materials of construction include stainless steels, in particular of the austenitic type, and the well-known high nickel alloys, such as Monel® nickel-copper alloys, Hastelloy® nickel- based alloys and, Inconel® nickel-chromium alloys.
  • stainless steels in particular of the austenitic type
  • high nickel alloys such as Monel® nickel-copper alloys, Hastelloy® nickel- based alloys and, Inconel® nickel-chromium alloys.
  • polymeric plastics as polytrifluorochloroethylene and polytetra ⁇ fluoroethylene, generally used as linings.
  • compositions which consist essentially of hydrogen fluoride and an effective amount of a compound selected from CCI3CF3 and CCI2FCF3 to form an azeotropic combination with hydrogen fluoride.
  • effective amount is meant an amount which, when combined with HF, results in the formation of an azeotrope or azeotrope-like mixture.
  • an azeotrope or an azeotrope-like composition is an admixture of two or more different components which, when in liquid form under given pressure, will boil at a substantially constant temperature, which temperature may be higher or lower than the boiling temperatures of the individual components, and which will provide a vapor composition essentially identical to the liquid composition undergoing boiling.
  • azeotrope is a liquid mixture that exhibits a maximum or minimum boiling point relative to the boiling points of surrounding mixture compositions.
  • An azeotrope is homogeneous if only one liquid phase is present.
  • An azeotrope is heterogeneous if more than one liquid phase is present.
  • a characteristic of minimum boiling azeotropes is that the bulk liquid composition is then identical to the vapor composition in equilibrium therewith, and distillation is ineffective as a separation technique.
  • azeotrope-like composition means a composition which behaves like an azeotrope (i.e., has constant-boiling characteristics or a tendency not to fractionate upon boiling or evaporation) .
  • the composition of the vapor formed during boiling or evaporation of such compositions is the same as or substantially the same as the original liquid composition.
  • the liquid composition if it changes at all, changes only to a minimal or negligible extent . This is to be contrasted with non-azeotrope-like compositions in which during boiling or evaporation, the liquid composition changes to a substantial degree.
  • the essential features of an azeotrope or an azeotrope-like composition are that at a given pressure, the boiling point of the liquid composition is fixed and that the composition of the vapor above the boiling composition is essentially that of the boiling liquid composition (i.e., no fractionation of the components of the liquid composition takes place) . It is also recognized in the art that both the boiling point and the weight percentages of each component of the azeotropic composition may change when the azeotrope or azeotrope-like liquid composition is subjected to boiling at different pressures.
  • an azeotrope or an azeotrope-like composition may be defined in terms of the unique relationship that exists among components or in terms of the compositional ranges of the components or in terms of exact weight percentages of each component of the composition characterized by a fixed boiling point at a specified pressure. It is also recognized in the art that various azeotropic compositions (including their boiling points at particular pressures) may be calculated (see, e.g., W. Schotte, Ind. Eng. Chem. Process Des. Dev. 1980, 19, pp 432-439) . Experimental identification of azeotropic compositions involving the same components may be used to confirm the accuracy of such calculations and/or to modify the calculations for azeotropic compositions at the same or other temperatures and pressures.
  • compositions may be formed which consist essentially of azeotropic combinations of hydrogen fluoride with a compound selected from CCI3CF3 and CCI2FCF 3 .
  • These include a composition consisting essentially of from about 90 to about 73 mole percent HF and from about 10 to 27 mole percent CCI3CF3 (which forms an azeotrope boiling at a temperature from between about 20°C and about 150°C and a pressure between about 140 kPa and about 4750 kPa) ; and a composition consisting essentially of from about 65 to about 44 mole percent HF and from about 35 to about 56 mole percent CCI 2 FCF3 (which forms an azeotrope boiling at a temperature between about -25°C and 125°C and a pressure between about 50 kPa and about 4020 kPa) .
  • PTx Method To determine the relative volatility of HF with each of CFC-114a and CFC-113a, the so-called PTx Method was used. In this procedure, the total absolute pressure in a cell of known volume is measured at a constant temperature for various known binary compositions . Use of the PTx Method is described in greater detail in "Phase Equilibrium in Process Design", Wiley-Interscience Publisher, 1970, written by Harold R. Null, on pages 124 to 126, the entire disclosure of which is hereby incorporated by reference. Samples of the vapor and liquid, or vapor and each of the two liquid phases under those conditions where two liquid phases exist, were obtained and analyzed to verify their respective compositions.
  • an activity coefficient equation model such as the Non-Random, Two- Liquid (NRTL) equation
  • NRTL equation Use of an activity coefficient equation, such as the NRTL equation, is described in greater detail in "The Properties of Gases and Liquids", 4th Edition, publisher McGraw Hill, written by Reid, Prausnitz and Poling, on pages 241 to 387; and in “Phase Equilibria in Chemical Engineering", published by
  • CFC-114a are formed at a variety of temperatures and pressures. At a pressure of 40 psia (276 kPa) and 20°C, the azeotrope vapor composition was found to be about 65 mole percent HF and about 35 mole percent CFC-114a. This is a heterogeneous azeotrope with the liquid portion being two phases between about 5.7 mole percent HF and about 97.4 mole percent HF. At a pressure of 365 psia (2516 kPa) and 100°C, the azeotrope vapor composition was found to be about 57 mole percent HF and 43 mole percent CFC-114a.
  • the present invention provides an azeotrope or azeotrope-like composition consisting essentially of from about 65 to 44 mole percent HF and from about 35 to 56 mole percent CFC-114a, said composition having a boiling point from about -25°C at 50 kPa to about 125°C at 4020 kPa. It has been found that azeotropes of HF and
  • CFC-113a are formed at a variety of temperatures and pressures.
  • the azeotrope vapor composition was found to be about 90 mole percent HF and about 10 mole percent CFC-113a. This is a heterogeneous azeotrope with the liquid portion being two phases between about 2.5 mole percent HF and about 99 mole percent HF .
  • the azeotrope vapor composition was found to be about 81 mole percent HF and about 19 mole percent CFC-113a.
  • azeotropic composition of about 73 mole percent HF and about 27 mole percent CFC-113a can be formed at 1 ' 50°C and 688 psia (4750 kPa) .
  • the present invention provides an azeotrope or azeotrope-like composition consisting essentially of from about 90 to 73 mole percent HF and from about 10 to 27 mole percent CFC-113a, said composition having a boiling point from 20°C at about 140 kPa to about 150°C at about 4750 kPa.
  • Processes for producing CFC-114a from CFC-113a by catalytic fluorination with HF can result in reactor effluent containing CFC-113a, CFC-1.14a, and HF.
  • CFC-114a/HF CFC-113a/HF azeotropes
  • the CFC-113a/HF azeotrope is useful as feed to produce additional CFC-114a.
  • the CFC-114a/HF azeotrope is useful as feed to produce CFC-115 and/or PFC-116. It will also be apparent to one of ordinary skill in the art that distillation including azeotropes with HF can typically be run under more convenient conditions than distillation without HF (e.g., where HF is removed prior to distillation) .

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  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Cette invention se rapporte à un procédé pour récupérer le fluorure d'hydrogène (HF) contenu dans un mélange de produits renfermant HF et au moins un composé ayant la formule CF3CCl2+xF1-x (où x est égal à 0 ou à 1). Ce procédé consiste à distiller ledit mélange de produits pour éliminer tous les produits qui possèdent un point d'ébullition plus bas que l'azéotrope au point d'ébullition le plus bas contenant HF et au moins un composé ayant ladite formule; et à distiller cet azéotrope pour récupérer HF en tant que composition azéotrope contenant HF et au moins un composé ayant ladite formule. Cette invention se rapporte également à des compositions azéotropes et de type azéotrope qui se composent essentiellement de fluorure d'hydrogène combiné à environ 10 à 27 % en mole de CCl3CF3 ou à environ 35 à 56 % en mole de CCl2FCF3.
PCT/US1995/010175 1995-08-11 1995-08-11 Azeotropes de cholorofluoroethanes avec fluorure d'hydrogene WO1997007052A1 (fr)

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PCT/US1995/010175 WO1997007052A1 (fr) 1995-08-11 1995-08-11 Azeotropes de cholorofluoroethanes avec fluorure d'hydrogene

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998056742A1 (fr) * 1997-06-13 1998-12-17 Daikin Industries, Ltd. Melange azeotrope d'iodure de perfluoroalkyle et de fluorure d'hydrogene, et procede pour isoler et purifier des iodures de perfluoroalkyle
US6028026A (en) * 1997-08-25 2000-02-22 E. I. Du Pont De Nemours And Company Cubic chromium trifluoride and its use for halogenated hydrocarbon processing
US6031141A (en) * 1997-08-25 2000-02-29 E. I. Du Pont De Nemours And Company Fluoroolefin manufacturing process
US6107267A (en) * 1997-08-25 2000-08-22 E. I. Du Pont De Nemours And Company Compositions comprising CF3 CF2 CHF2 and their manufacture
US6224781B1 (en) 1997-08-25 2001-05-01 E. I. Du Pont De Nemours And Company Compositions comprising hydrofluorocarbons and their manufacture
US9950974B2 (en) 2016-08-31 2018-04-24 Honeywell International Inc. Azeotropic or azeotrope-like compositions of 1,3,3-trichloro-3-fluoro-1-ene (HCFO-1231zd) and hydrogen fluoride (HF)
US9950973B2 (en) 2016-08-31 2018-04-24 Honeywell International Inc. Azeotropic or azeotrope-like compositions of 1,3-dichloro-3,3-difluoroprop-1-ene (HCFO-1232zd) and hydrogen fluoride (HF)
US10029964B2 (en) 2016-08-30 2018-07-24 Honeywell International Inc. Azeotropic or azeotrope-like compositions of 3,3,3-trifluoropropyne and water

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0317981A2 (fr) * 1987-11-26 1989-05-31 Asahi Glass Company Ltd. Procédé de production de 1,1-dichloro-1,2,2,2,-tétrafluoroéthane
EP0354697A1 (fr) * 1988-08-01 1990-02-14 E.I. Du Pont De Nemours And Company Procédé pour la séparation d'HF par distillation azéotropique
EP0509449A2 (fr) * 1991-04-15 1992-10-21 Daikin Industries, Ltd. Mélange azéotrope de fluorure d'hydrogène et de 1,1,1-trifluoro-2-chloroéthane et procédé pour l'épuration d'1,1,1-Trifluoro-2-chloréthane
WO1995012566A1 (fr) * 1993-11-01 1995-05-11 E.I. Du Pont De Nemours And Company Prodece pour produire du 1,1-dichlorotetrafluoroethane hautement pur

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0317981A2 (fr) * 1987-11-26 1989-05-31 Asahi Glass Company Ltd. Procédé de production de 1,1-dichloro-1,2,2,2,-tétrafluoroéthane
EP0354697A1 (fr) * 1988-08-01 1990-02-14 E.I. Du Pont De Nemours And Company Procédé pour la séparation d'HF par distillation azéotropique
EP0509449A2 (fr) * 1991-04-15 1992-10-21 Daikin Industries, Ltd. Mélange azéotrope de fluorure d'hydrogène et de 1,1,1-trifluoro-2-chloroéthane et procédé pour l'épuration d'1,1,1-Trifluoro-2-chloréthane
WO1995012566A1 (fr) * 1993-11-01 1995-05-11 E.I. Du Pont De Nemours And Company Prodece pour produire du 1,1-dichlorotetrafluoroethane hautement pur

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998056742A1 (fr) * 1997-06-13 1998-12-17 Daikin Industries, Ltd. Melange azeotrope d'iodure de perfluoroalkyle et de fluorure d'hydrogene, et procede pour isoler et purifier des iodures de perfluoroalkyle
US6271189B1 (en) 1997-06-13 2001-08-07 Daikin Industries, Ltd. Azeotropic mixture of perfluoroalkyl iodide and hydrogen fluoride, and method for isolating and purifying perfluoroalkyl iodides
US6380148B2 (en) 1997-06-13 2002-04-30 Daikin Industries Azeotropic mixture of perfluoroalkyl iodide and hydrogen fluoride, and method for isolating and purifying perfluoroalkyl iodides
US6028026A (en) * 1997-08-25 2000-02-22 E. I. Du Pont De Nemours And Company Cubic chromium trifluoride and its use for halogenated hydrocarbon processing
US6031141A (en) * 1997-08-25 2000-02-29 E. I. Du Pont De Nemours And Company Fluoroolefin manufacturing process
US6107267A (en) * 1997-08-25 2000-08-22 E. I. Du Pont De Nemours And Company Compositions comprising CF3 CF2 CHF2 and their manufacture
US6224781B1 (en) 1997-08-25 2001-05-01 E. I. Du Pont De Nemours And Company Compositions comprising hydrofluorocarbons and their manufacture
US6635187B1 (en) 1997-08-25 2003-10-21 E. I. Du Pont De Nemours And Company Compositions comprising hydrofluorocarbons and their manufacture
US10029964B2 (en) 2016-08-30 2018-07-24 Honeywell International Inc. Azeotropic or azeotrope-like compositions of 3,3,3-trifluoropropyne and water
US9950974B2 (en) 2016-08-31 2018-04-24 Honeywell International Inc. Azeotropic or azeotrope-like compositions of 1,3,3-trichloro-3-fluoro-1-ene (HCFO-1231zd) and hydrogen fluoride (HF)
US9950973B2 (en) 2016-08-31 2018-04-24 Honeywell International Inc. Azeotropic or azeotrope-like compositions of 1,3-dichloro-3,3-difluoroprop-1-ene (HCFO-1232zd) and hydrogen fluoride (HF)

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