Classifications

• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
  • C11D7/50—Solvents
  • C11D7/5036—Azeotropic mixtures containing halogenated solvents
  • C11D7/504—Azeotropic mixtures containing halogenated solvents all solvents being halogenated hydrocarbons
  • C11D7/5045—Mixtures of (hydro)chlorofluorocarbons
• • 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
  • C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
  • C07C17/386—Separation; Purification; Stabilisation; Use of additives by distillation with auxiliary compounds
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
  • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
  • C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
  • C11D7/02—Inorganic compounds
  • C11D7/04—Water-soluble compounds
  • C11D7/08—Acids

Definitions

• the present invention pertains to azeotropic and azeotrope-like compositions of l,2-dichloro-3,3,3-trifluoropropene (HCFC-1223xd) and hydrogen fluoride.
• HFC hydrofluorocarbon
• HFC-245fa 1,1,1,3,3-Pentafluoropropane
• an intermediate in the production of substantially pure 1,1,1 ,3 ,3 -pentafluoropropane is an azeotropic or azeotrope-like mixture of 1 ,2- dichloro-3,3,3-trifluoropropene (HCFC-1223xd) and hydrogen fluoride.
• This intermediate once formed, may thereafter be separated into its component parts by extraction techniques.
• the azeotropic and azeotrope-like compositions find use as anhydrous (non-aqueous) etchants for etching semiconductors in the electronics industry as well as compositions for removing surface oxidation from metals.
• HCFC-1223xd may be used as a pharmaceutical intermediate.
• the invention provides an azeotropic composition consisting essentially of l,2-dichloro-3, 3, 3 -trifluoropropene and hydrogen fluoride.
• the invention further provides an azeotropic or azeotrope-like composition consisting essentially of from about 1 to about 90 weight percent hydrogen fluoride and from about 10 to about 99 weight percent l,2-dichloro-3, 3, 3 -trifluoropropene, which composition has a boiling point of from about 26°C to about 68°C at a pressure of from about 24 psia to about 84 psia.
• the invention provides a method of forming an azeotropic or azeotrope-like composition, which method comprises blending from about 1 to about 90 weight percent hydrogen fluoride and from about 10 to about 99 weight percent of l,2-dichloro-3, 3, 3 -trifluoropropene, which composition has a boiling point of from about 26°C to about 68°C at a pressure of from about 24 psia to about 84 psia.
• the invention provides a process for removing l,2-dichloro-3,3,3-trifluoropropene from a mixture of l,2-dichloro-3,3,3- trifluoropropene and at least one impurity, which process comprises adding hydrogen fluoride to the mixture in an amount sufficient to form an azeotropic or azeotrope-like composition of 1 ,2-dichloro-3,3,3-trifluoropropene and hydrogen fluoride, and thereafter separating the azeotropic composition from the impurity.
• FIG. 1 shows a Vapor-Liquid-Liquid Equilibrium (VLLE) plot for HCFC-1223xd and HF.
• VLLE Vapor-Liquid-Liquid Equilibrium
• This binary azeotrope or azeotrope-like composition is then available for separation into its component parts.
• thermodynamic state of a fluid is defined by its pressure, temperature, liquid composition and vapor composition.
• the liquid composition and vapor phase are essentially equal at a given temperature and pressure range. In practical terms this means that the components cannot be separated during a phase change.
• an azeotrope-like composition means that the composition behaves like a true azeotrope in terms of its constant boiling characteristics and tendency not to fractionate upon boiling or evaporation. During boiling or evaporation, the liquid composition changes only slightly, if at all. This is in contrast with non-azeotrope-like compositions in which the liquid and vapor compositions change substantially during evaporation or condensation.
• One way to determine whether a candidate mixture is azeotrope-like within the meaning of this invention is to distill a sample of it under conditions which would be expected to separate the mixture into its separate components. If the mixture is a non-azeotrope or non-azeotrope-like, the mixture will fractionate, i.e. separate into its various components with the lowest boiling component distilling off first, and so on. If the mixture is azeotrope-like, some finite amount of the first distillation cut will be obtained which contains all of the mixture components and which is constant boiling or behaves like a single substance. Another characteristic of azeotrope-like compositions is that there is a range of compositions containing the same components in varying proportions that are azeotrope-like.
• compositions are included by the term azeotrope-like as used herein.
• azeotrope-like As an example, it is well known that at different pressures the composition of a given azeotrope will vary at least slightly as does the boiling point of the composition. Thus an azeotrope of two components represents a unique type of relationship but with a variable composition depending on the temperature and/or pressure. As is well known in the art, the boiling point of an azeotrope will vary with pressure.
• an azeotrope is a liquid mixture that exhibits a maximum or minimum boiling point relative to the boiling points of surrounding mixture compositions.
• 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 components and which will provide a vapor composition essentially identical to the liquid composition undergoing boiling.
• azeotropic compositions are defined to include azeotrope-like compositions which means a composition that 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 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.
• 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., essentially no fractionation of the components of the liquid composition takes place.
• 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 relationship that exists between its 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.
• the present invention provides a composition comprising effective amounts of hydrogen fluoride and HCFC-1223xd to form an azeotropic or azeotrope-like composition.
• effective amount is meant an amount of each component which, when combined with the other component, results in the formation of an azeotrope or azeotrope-like mixture.
• inventive compositions preferably are binary azeotropes that consist essentially of combinations of only hydrogen fluoride with HCFC-1223xd.
• the inventive composition contains from about 1 to about 90 weight percent HF, preferably from about 10 weight percent to about 80 weight percent and most preferably from about 40 weight percent to about 60 weight percent. In the preferred embodiment, the inventive composition contains from about 10 to about 99 weight percent HCFC-1223xd, preferably from about 20 weight percent to about 90 weight percent and most preferably from about 40 weight percent to about 60 weight percent.
• the composition of the present invention has a boiling point of from about 26°C to about 68°C at a pressure of from about 24 psia to about 84 psia.
• An azeotropic or azeotrope-like composition having about 55 ⁇ 5 weight percent HF and about 45 ⁇ 5 weight percent HCFC-1223xd has been found to boil at about 26°C and 23 psia.
• An azeotropic or azeotrope-like composition of about 50 ⁇ 5 weight percent HF and about 50 ⁇ 5 weight percent HCFC-1223xd has been found to boil at about 45°C and 42 psia.
• HCFC-1223xd may be removed from a mixture containing of HCFC-1223xd and an impurity which may, for example, result from manufacturing steps in the preparation of HCFC-1223xd. This is done by adding hydrogen fluoride to a mixture of HCFC-1223xd and the impurity. Hydrogen fluoride is added to the mixture in an amount sufficient to form an azeotropic composition of HCFC-1223xd and hydrogen fluoride, and thereafter the azeotropic composition is separated from the impurity, for example by distillation, scrubbing, or other art recognized separating means.
• the impurity itself does not form a close-boiling azeotropic mixture with HCFC-1223xd, hydrogen fluoride or a mixture of HCFC-1223xd and hydrogen fluoride.
• close-boiling azeotropic mixture means an azeotropic mixture having a boiling point within 10°C of the azeotropic mixture of the invention. The following non-limiting examples serve to illustrate the invention.
• EXAMPLE 1 50 g of l,2-dichloro-3,3,3-trifluoropropene (HCFC-1223xd) is dissolved in 50 g of HF to form a heterogeneous mixture.
• the vapor pressure of the mixture at 26°C is 23 psia.
• EXAMPLE 2 55 g of l,2-dichloro-3, 3, 3 -trifluoropropene is dissolved in 45 g of HF to form a heterogeneous mixture.
• the vapor pressure of the mixture at 45°C is 42 psia.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Wood Science & Technology (AREA)
• Life Sciences & Earth Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Physics & Mathematics (AREA)
• Inorganic Chemistry (AREA)
• Combustion & Propulsion (AREA)
• Thermal Sciences (AREA)
• Materials Engineering (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Detergent Compositions (AREA)
• Weting (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Nitrogen Condensed Heterocyclic Rings (AREA)
• Plural Heterocyclic Compounds (AREA)

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• 2001
  • 2001-01-24 US US09/768,415 patent/US6475971B2/en not_active Expired - Lifetime
• 2002
  • 2002-01-17 CN CNB028039998A patent/CN100406534C/zh not_active Expired - Lifetime
  • 2002-01-17 JP JP2002559520A patent/JP4219168B2/ja not_active Expired - Lifetime
  • 2002-01-17 AU AU2002241953A patent/AU2002241953A1/en not_active Abandoned
  • 2002-01-17 EP EP02707553A patent/EP1354019B1/en not_active Expired - Lifetime
  • 2002-01-17 MX MXPA03006562A patent/MXPA03006562A/es active IP Right Grant
  • 2002-01-17 AT AT02707553T patent/ATE486915T1/de not_active IP Right Cessation
  • 2002-01-17 DE DE60238175T patent/DE60238175D1/de not_active Expired - Lifetime
  • 2002-01-17 WO PCT/US2002/001970 patent/WO2002059231A2/en not_active Ceased
  • 2002-01-17 ES ES02707553T patent/ES2353736T3/es not_active Expired - Lifetime

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