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WO1992011400A1 - Composition semblable a des azeotropes de dichloropentafluoropropane, un alcanol ayant de 1 a 3 atomes de carbone et 2-methyl-2-propanol - Google Patents

Composition semblable a des azeotropes de dichloropentafluoropropane, un alcanol ayant de 1 a 3 atomes de carbone et 2-methyl-2-propanol Download PDF

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Publication number
WO1992011400A1
WO1992011400A1 PCT/US1991/009572 US9109572W WO9211400A1 WO 1992011400 A1 WO1992011400 A1 WO 1992011400A1 US 9109572 W US9109572 W US 9109572W WO 9211400 A1 WO9211400 A1 WO 9211400A1
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WIPO (PCT)
Prior art keywords
weight percent
hcfc
compositions
azeotrope
propanol
Prior art date
Application number
PCT/US1991/009572
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English (en)
Inventor
Hillel Magid
David Paul Wilson
Richard M. Hollister
Dennis M. Lavery
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Allied-Signal Inc.
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Publication date
Application filed by Allied-Signal Inc. filed Critical Allied-Signal Inc.
Publication of WO1992011400A1 publication Critical patent/WO1992011400A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
    • C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
    • C23G5/028—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons
    • C23G5/02809—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons containing chlorine and fluorine
    • C23G5/02825—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons containing chlorine and fluorine containing hydrogen
    • C23G5/02841—Propanes
    • C23G5/02851—C2HCl2F5
    • 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
    • C11D7/5068—Mixtures of halogenated and non-halogenated solvents
    • C11D7/5077—Mixtures of only oxygen-containing solvents
    • C11D7/5081—Mixtures of only oxygen-containing solvents the oxygen-containing solvents being alcohols only
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/22—Secondary treatment of printed circuits
    • H05K3/26—Cleaning or polishing of the conductive pattern

Definitions

  • This invention relates to azeotrope-like mixtures of dichloropentafluoropropane, an alkanol having 1-3 carbon atoms and 2-methyl-2-propanol. These mixtures are useful in a variety of vapor degreasing, cold cleaning, and solvent cleaning applications including defluxing and dry cleaning.
  • Fluorocarbon based solvents have been used extensively for the degreasing and otherwise cleaning of solid surfaces, especially intricate parts and difficult to remove soils.
  • vapor degreasing or solvent cleaning consists of exposing a room temperature object to be cleaned to the vapors of a boiling solvent. Vapors condensing on the object provide clean distilled solvent to wash away grease or other contamination. Final evaporation of solvent from the object leaves the object free of residue. This is contrasted with liquid solvents which leave deposits on the object after rinsing.
  • a vapor degreaser is used for difficult to remove soils where elevated temperature is necessary to improve the cleaning action of the solvent, or for large volume assembly line operations where the cleaning of metal parts and assemblies must be done efficiently.
  • the conventional operation of a vapor degreaser consists of immersing the part to be cleaned in a sump of boiling solvent which removes the bulk of the soil, thereafter immersing the part in a sump containing freshly distilled solvent near room temperature, and finally exposing the part to solvent vapors over the boiling sump which condense on the cleaned part.
  • the part can also be sprayed with distilled solvent before final rinsing.
  • Vapor degreasers suitable in the above- described operations are well known in the art.
  • Sherliker et al. in U.S. Patent 3,085,918 disclose such suitable vapor degreasers comprising a boiling sump, a clean sump, a water separator, and other ancillary equipment.
  • Cold cleaning is another application where a number of solvents are used. In most cold cleaning applications, the soiled part is either immersed in the fluid or wiped with cloths soaked in solvents and allowed to air dry.
  • Trichlorotrifluoro ⁇ ethane has been found to have satisfactory solvent power for greases, oils, waxes and the like. It has therefore found widespread use for cleaning electric motors, compressors, heavy metal parts, delicate precision metal parts, printed circuit boards, gyroscopes, guidance systems, aerospace and missile hardware, aluminum parts, etc.
  • the art has looked towards azeotropic compositions having fluorocarbon components because the fluorocarbon components contribute additionally desired characteristics, like polar functionality, increased solvency power, and stabilizers. Azeotropic compositions are desired because they do not fractionate upon boiling.
  • fluoro ⁇ carbon based azeotropic mixtures or azeotrope-like mixtures which offer alternatives for new and special applications for vapor degreasing and other cleaning applications.
  • fluorocarbon-based azeotrope-like mixtures are of particular interest because they are considered to be stratospherically safe substitutes for presently used fully halogenated chlorofluorocarbons. The latter have been implicated in causing environmental problems associated with the depletion of the earth's protective ozone layer.
  • Mathematical models have substantiated that hydrochlorofluorocarbons, like dichloropentafluoro- propane, have a much lower ozone depletion potential and global warming potential than the fully halo ⁇ genated species.
  • the invention relates to novel azeotrope-like compositions of dichloropentafluoropropane, an alkanol having 1-3 carbon atoms and 2-methyl- 2-propanol which are useful in a variety of industrial cleaning applications including cold cleaning and defluxing of printed circuit boards.
  • novel azeotrope-like compositions comprising from about 81.2 to about 99.99 weight percent dichloropentafluoropropane, from about 0.01 to about 17.8 weight percent of an alkanol having 1-3 carbon atoms and from about 0.01 to about 1 weight percent 2-methyl-2-pro ⁇ anol which boil at about 50.3°C ⁇ about 5.9°C at 760 mm Hg.
  • Dichloropentafluoropropane exists in nine isomeric forms: (1) 2,2-dichloro-l,l,1,3,3-penta- fluoro-propane (HCFC-225a); (2) l,2-dichloro-l,2,3,- 5 3,3- ⁇ entafluoropropane (HCFC-225ba) ; (3) 1,2- dichloro-1,1,2,3,3-pentafluoropropane (HCFC-225bb) ; (4) 1,l-dichloro-2,2,3,3,3-pentafluoropropane (HCFC-225ca); (5) 1,3-dichloro-l,1,2,2,3-pentafluoro ⁇ propane (HCFC-225cb); (6) 1,l-dichloro-1,2,2,3,3-penta-fluoro ⁇
  • HCFC-225cc 1Q pentafluoro-propane
  • HCFC-225d 1,2-dichloro- 1,1,3,3,3-pentafluoropropane
  • HCFC-225ea 1,3- dichloro-1,1,2,3,3-pentafluoropropane
  • HCFC-225eb 1,1-dichloro-l,2,3,3,3-pentafluoropropane
  • m dichloropentafluoropropane will refer to any of the iso ers or an admixture of the isomers in any proportion.
  • the dichloropentafluoropropane component of the invention has good solvent properties.
  • the alkanol components also have good solvent capabilities dissolving polar organic materials and amine hydrochlorides.
  • the azeotrope- like compositions of the invention consist essentially of from about 81.2 to about 97 weight 35 percent dichloropentafluoropropane, from about 3 to about 17.8 weight percent methanol and from -6- about 0.01 to about 1 weight percent 2-methyl-2- propanol and boil at about 47.2°C ⁇ about 1.9°C at 760 mm Hg.
  • the azeotrope- like compositions of the invention consist essentially of from about 85.1 to about 99 weight percent dichloropentafluoropropane, from about 1 to ⁇ Q about 13.9 weight percent ethanol and from about 0.01 to about 1 weight percent 2-methyl-2- ⁇ ro ⁇ anol and boil at about 52.1°C ⁇ about 2.2°C at 760 mm Hg.
  • the azeotrope- j c like compositions of the invention consist essentially of from about 95 to about 99.99 weight percent dichloropentafluoropropane, from about 0.01 to about 4 weight percent 1- ⁇ ro ⁇ anol and from about
  • the azeotrope- like compositions of the invention consist essentially of from about 93.1 to about 99.99 weight
  • the azeotrope-like compositions of the invention consist 5 essentially of from about 81.6 to about 97 weight percent HCFC-225ca, from about 3 to about 17.9 weight percent methanol and from about 0.01 to about 0.5 weight percent 2-methyl-2-propanol and boil at about 45.7°C ⁇ about 0.5°C at 760 mm Hg.
  • the azeotrope-like compositions of the invention consist essentially of from about 85.6 to about 96 weight percent HCFC-225ca
  • the azeotrope-like compositions of the invention consist essentially of from about 88.6 to about 95 weight percent HCFC-225ca, from about 5 to about 10.9 weight percent methanol and from about 0.01 to about 0.5 weight percent 2-methyl-2-propanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 91.5 to about 99 weight percent HCFC-225ca, from about 1 to about 8 weight percent ethanol and from about 0.01 to about 0.5 weight percent 2-methyl-2-propanol and boil at about 50.3°C ⁇ about 0.5°C at 760 mm Hg.
  • the azeotrope-like compositions of the invention consist essentially of from about 93.5 to about 99 weight percent HCFC-225ca, from about 1 to
  • the azeotrope-like compositions of the invention consist essentially of from about 95 to about 98.5 weight percent HCFC-225ca, from about 1.5 to about 4.5 weight percent ethanol and from about 0.01 to about 0.5 weight percent 2-rnethyl-2-propanol,
  • the azeotrope-like compositions of the invention consist essentially of from about 95.5 to about 99.99 weight percent HCFC-225ca, from about 0.01 to about 4 weight percent 2-propanol and from about 0.01 to about 0.5 weight percent 2-methyl-2-propanol and boil at about 51.3°C ⁇ about 0.3°C at 760 mm Hg.
  • the azeotrope-like compositions of the invention consist essentially of from about 97.5 to about 99.99 weight percent HCFC-225ca, from about 0.01 to about 2 weight percent 2-propanol and from about 0.01 to about 0.5 weight percent 2-methyl-2- propanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 83.2 to about 97 weight percent HCFC-225cb, from about 3 to about 15.8 weight percent methanol and from about 0.01 to about 1 weight percent 2-methyl-2-propanol and boil at about 48.6°C ⁇ about 0.6°C at 760 mm Hg.
  • the azeotrope-like compositions of the invention consist essentially of from about 83.7 to about 97 weight percent HCFC-225cb from about 3 to about 15.8 weight percent methanol and from about 0.01 to about 0.5 weight percent 2-methyl-2-propanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 87.1 to about 95 weight percent HCFC-225cb, from about 5 to about 11.9 weight percent 10 methanol and from about 0.01 to about 1 weight percent 2-methyl-2-propanol.
  • the azeotrope-like , - ⁇ compositions of the invention consist essentially of from about 87.6 to about 95 weight percent HCFC-225cb, from about 5 to about 11.9 weight percent methanol and from about 0.01 to about 0.5 weight percent 2-methyl-2-propanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 85.1 to about 97 weight
  • HCFC-225cb 25 percent HCFC-225cb, from about 3 to about 13.9 weight percent ethanol and from about 0.01 to about 1 weight percent 2-methyl-2-propanol and boil at about 53.9°C ⁇ about 0,5°C at 760 mm Hg.
  • the azeotrope-like compositions of the invention consist essentially of from about 85.6 to about 97 weight percent HCFC-225cb, from about 3 to about 13.9 weight percent ethanol and from about 0.01 35 to about 0.5 weight percent 2-methyl-2- ⁇ ro ⁇ anol.
  • the azeotrope-like compositions of the invention consist essentially of from about 88.1 to about 97 weight percent HCFC-225cb, from about 3 to about lo.9 weight percent ethanol and from about 0.01 to about 1 weight percent 2-methyl-2-propanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 88.6 to about 97 weight percent HCFC-225cb, from about 3 to about 10.9 weight percent ethanol and from about 0.01 to about 0.5 weight percent 2-methyl-2-propanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 95 to about 99.99 weight percent HCFC-225cb, from about 0.01 to about 4 weight percent 1-propanol and from about 0.01 to about 1 weight percent 2-methyl-2-propanol and boil at about 56.0°C ⁇ about 0.2°C at 760 mm Hg.
  • the azeotrope-like compositions of the invention consist essentially of from about 95.9 to about 99.99 weight percent HCFC-225cb, from about 0.01 to about 4 weight percent 1-propanol and from about 0.01 to about 0.5 weight percent 2-methyl-2- propanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 97 to about 99.99 weight percent HCFC-225cb, from about 0.01 to about 2 weight percent 1-propanol and from about 0.01 to about 1 weight percent 2-methyl-2-propanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 97.5 to about 99.99 weight percent
  • 1-propanol and from about 0.01 to about 0.5 weight percent 2-methyl-2- ⁇ ropanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 93.1 to about 99 weight percent HCFC-225cb, from about 1 to about 6 weight percent 2- ⁇ ropanol and from about 0.01 to about 1
  • the azeotrope-like compositions of the invention consist essentially of from about 93.6
  • HCFC-225cb 25 to about 99 weight percent HCFC-225cb, from about 1 to about 6 weight percent 2-propanol and from about 0.01 to about 0.5 weight percent 2-methyl-2-propanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 94.5 to about 98.5 weight percent HCFC-225cb, from about 1.5 to about 4.5 weight 35 percent 2-propanol and from about 0.01 to about 1 weight percent 2-methyl-2-propanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 95 to about 98.5 weight percent
  • HCFC-225cb from about 1.5 to about 4.5 weight percent 2-pro ⁇ anol and from about 0.01 to about 0.5 weight percent 2-methyl-2-pro ⁇ anol.
  • the azeotrope-like compositions of the invention consist essentially of from about 81.7 to about 97 weight percent of a 5 mixture of HCFC-225ca and HCFC-225cb, wherein the amount of HCFC-225ca and HCFC-225cb in said mixture may vary from about 0.01 to about 99.99 weight percent HCFC-225ca and from about 0.01 to about 99.99 weight percent HCFC-225cb, from about 3 to about 17.8 weight percent methanol and from about 0.01 to about 0.5 0 weight percent 2-methyl-2- ⁇ ropanol and boil at about 47.2°C ⁇ about 1.8°C at 760 mm Hg.
  • the 5 azeotrope-like compositions of the invention consist essentially of from about 87.6 to about 95 weight percent of a mixture of HCFC-225ca and HCFC-225cb, wherein the amount of HCFC-225ca and HCFC-225cb in 0 said mixture may vary from about 0.01 to about 99.99 weight percent HCFC-225ca and from about 0.01 to about 99.99 weight percent HCFC-225cb, from about 5 to about 11.9 weight percent methanol and from about 0.01 to about 0.5 weight percent 2-methyl-2- ⁇ ropanol. 5
  • the azeotrope-like compositions of the invention consist essentially of from about 85.6 to about 99 weight percent of a mixture of 5 HCFC-225ca and HCFC-225cb, wherein the amount of
  • HCFC-225ca and HCFC-225cb in said mixture may vary from about 0.01 to about 99.99 weight percent HCFC-225ca and from about 0.01 to about 99.99 weight percent HCFC-225cb, from about 1 to about 13.9 weight ⁇ 0 percent ethanol and from about 0.01 to about 0.5 weight percent 2-methyl-2- ⁇ ropanol and boil at about 52.1°C ⁇ about 2.2°C at 760 mm Hg.
  • the azeotrope-like compositions of the invention consist essentially of from about 89.5 to about 98.5 weight percent of a mixture of HCFC-225ca and HCFC-225cb, wherein the amount of HCFC-225ca and HCFC-225cb in said mixture may vary from about 0.01 to about 99.99 weight percent HCFC-225ca and from about 0.01 to about 99.99 weight percent HCFC-225cb, from about 1.5 to about 10 weight percent ethanol and from about 0.01 to about 0.5 weight percent 2-methyl-2-propanol.
  • the azeotrope-like compositions of the invention consist essentially of
  • HCFC-225cb 35 weight percent HCFC-225cb, from about 0.01 to about 6 weight percent 2-propanol and from about 0.01 to aobut 0.5 weight percent 2-methyl-2- ⁇ ropanol and boil at about 53.6°C ⁇ about 2.6°C at 760 mm Hg.
  • the azeotrope-like compositions of the invention consist essentially of from about 95 to about 98.5 weight percent of a mixture of HCFC-225ca and HCFC-225cb, wherein the amount of HCFC-225ca and HCFC-225cb in said mixture may vary from about 0.01 to about 99.99 weight percent HCFC-225ca and from about 0.01 to about 99.99 weight percent HCFC-225cb, from about 1.5 to about 4.5 weight percent 2- ⁇ ro ⁇ anol and from about 0.01 to about 0.5 weight percent 2-methyl-2-propanol.
  • the azeotrope-like compositions of the invention consist essentially of from about 87.5 to about 99 weight percent 225d, from about 1 to about 12 weight percent methanol and from about 0.01 to about 0.5 weight percent 2-methyl-2- ⁇ ropanol and boil at about 45.2°C ⁇ about 0.7°C and preferably boil at about 45.2°C ⁇ about 0.4°C at 760 mm Hg.
  • the azeotrope-like compositions of the invention consist essentially of from about 91.5 to about 98 weight percent 225d, from about 2 to about 8 weight percent methanol and from about 0.01 to about 0.5 weight percent 2-methyl-2-propanol and boil at about 45.2°C ⁇ about 0.7°C and preferably boil at about 45.2°C ⁇ about 0.4°C at 760 mm Hg.
  • the azeotrope-like compositions of the invention consist essentially of from about 91.5 to about 99 weight percent 225d, from about 1 to about 8 weight percent ethanol and from about 0.01 to about 0.5 weight percent 2-methyl-2-propanol and boil at about 49.8°C ⁇ about 0.7°C and preferably boil at about 49.8°C ⁇ about 0.4°C at 760 mm Hg.
  • the azeotrope-like compositions of the invention consist essentially of from about 94.5 to about 99 weight percent 225d, from about 1 to about 5 weight percent ethanol and from about 0.01 to about 0.5 weight percent 2-methyl-2-propanol and boil at about 49.8°C ⁇ . about 0.7°C and preferably boil at about 49.8°C ⁇ about 0.4°C at 760 mm Hg.
  • the azeotrope-like compositions of the invention consist essentially of from about 95.5 to about 99.99 weight percent 225d, from about 0.01 to about 4 weight percent 2-propanol and from about 0.01 to about 0.5 weight percent 2-methyl-2-pro ⁇ anol and boil at about 50.5°C ⁇ about 0.5°C and preferably boil at about 50.5°C ⁇ about 0.3°C at 760 mm Hg.
  • the azeotrope-like compositions of the invention consist essentially of from about 97.5 to about 99.99 weight percent 225d, from about 0.01 to about 2 weight percent ethanol and from about 0.01 to about 0.5 weight percent 2-methyl-2-propanol and boil at about 50.5°C ⁇ about 0.5°C and preferably boil at about 50.5°C ⁇ about 0.3°C at 760 mm Hg.
  • compositions within the indicated ranges, as well as certain compositions outside the indicated ranges, are azeotrope-like, as defined more particularly below.
  • thermodynamic state of a fluid is defined by four variables: pressure, temperature, liquid composition and vapor composition, or P-T-X-Y, respectively.
  • An azeotrope is a unique characteristic of a system of two or more components where X and Y are equal at a stated P and
  • azeotrope- like composition is intended to mean that the composition behaves like a true azeotrope in terms of its constant-boiling characteristics or tendency not to fractionate upon boiling or evaporation. Such compositions may or may not be a true azeotrope.
  • the composition of the vapor formed during boiling or evaporation is identical or substantially identical to the original liquid composition.
  • the liquid composition if it changes at all, changes only minimally. This is contrasted with non-azeotrope-like compositions in which the liquid composition changes substantially during boiling or evaporation.
  • one way to determine whether a candidate mixture is "azeotrope-like" within the meaning of this invention is to distill a sample thereof under conditions (i.e. resolution - number of plates) which would be expected to separate the mixture into its separate components. If the mixture is non-azeo- tropic 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 a first distillation cut will be obtained which contains all of the mixture components and which is constant boiling or behaves as a single substance.
  • azeotrope-like compositions there is a range of compositions containing the same components in varying proportions which are azeotrope- like. All such compositions are intended to be covered 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.
  • an azeotrope of A and B represents a unique type of relationship but with a variable composition depending on temperature and/or pressure.
  • azeotrope-like compositions of the invention may be used to clean solid surfaces by treating said surfaces with said compositions in any manner well known in the art such as by dipping or spraying or use of conventional degreasing apparatus.
  • the azeotrope-like compositions dicussed herein are useful as solvents for various cleaning applications including vapor degreasing, defluxing, cold cleaning, dry cleaning, dewatering, decontamination, spot cleaning, aerosol propelled rework, extraction, particle removal, and surfactant cleaning applications.
  • These azeotrope- like compositions are also useful as blowing agents, Rankine cycle and absorption refrigerants, and power fluids.
  • the alkanol components of the invention are known materials. Preferably, they should be used in sufficiently high purity so as to avoid the introduction of adverse influences upon the solvent or constant boiling properties of the system.
  • alkanols may be used in the present invention.
  • Most dichloropentafluoro ⁇ propane isomers like the preferred HCFC-225ca isomer, are not available in commercial quantities, therefore until such time as they become commercially available, they may be prepared by following the organic syntheses disclosed herein.
  • 1,l-dichloro-2,2,3,3,3-pentafluoropropane may be prepared by reacting 2,2,3,3,3-pentafluoro-1-propanol and p-toluenesulfonate chloride together to form 2,2,3,3,3-pentafluoropropyl-p-toluenesulfonate.
  • Synthesis of 2.2-dichloro-l.1.1.3.3-penta- fluoropropane ( 225B ) This compound may be prepared by reacting a dimethylformamide solution of 1,1,1- trichloro-2,2,2-trifluoromethane with chlorotrimethyl- silane in the presence of zinc, forming l-(trimethyl- siloxy)-2,2-dichloro-3,3,3-trifluoro-N,N-dimethylpropyl amine.
  • the l-(trimethylsiloxy)-2,2-dichloro-3,3,3- trifluoro-N,N-dimethyl propylamine is reacted with sulfuric acid to form 2,2-dichloro-3,3,3-trifluoro- propionaldehyde.
  • the 2,2-dichloro-3,3,3-trifluoropro- pionaldehyde is then reacted with sulfur tetra- fluoride to produce 2,2-dichloro-l,1,1,3,3-penta- fluoropropane.
  • Part B Synthesis of 1,1,2,2,3-pentafluoro ⁇ propane.
  • a 500 ml flask was equipped with a mechanical stirrer and a Vigreaux distillation column, which in turn was connected to a dry-ice trap, and maintained under a nitrogen atmosphere.
  • the flask was charged with 400 ml N-methylpyr ⁇ rolidone, 145 gm (0.507 mol) 2,2,3,3-tetrafluoro- ⁇ ropyl-p-toluenesulfonate (produced in Part A above), and 87 gm (1.5 mol) spray-dried KF.
  • the mixture was then heated to 190-200°C for about 3.25 hours during which time 61 gm volatile product distilled into the cold trap (90% crude yield). Upon distillation, the fraction boiling at 25-28°C was collected.
  • This compound may be prepared by reacting 2,2,3,3-tetrafluoro-1-propanol and p-toluenesulfonate chloride to form 2,2,3,3-tetra- fluoropropyl-p-toluesulfonate. Next, the 2,2,3,3-
  • Synthesis of 1.3-dichloro-l.1.2.3.3-penta- fluoropropane (225ea) This compound may be prepared by reacting trifluoroethylene with dichlorotri- fluoromethane to produce l,3-dichloro-l,l,2,3,3,- pentafluoropropane and 1,1-dichloro-l,2,3,3,3-penta- fluoropropane.
  • the l,3-dichloro-l,l,2,3,3-penta- fluoropropane is seperated from its isomers using fractional distillation and/or preparative gas chromatography.
  • 1,l-aichloro-l,2,3,3,3-penta- fluoropropane (225eb..
  • This compound may be prepared by reacting trifluoroethylene with dichlorodifluoro ⁇ methane to produce 1,3-dichloro-l,1,2,3,3-pentafluoro ⁇ propane and 1,1-dichloro-l,2,3,3,3-pentafluoro ⁇ propane.
  • the 1,1-dichloro-l,2,3,3,3-pentafluoro ⁇ propane is separated from its isomer using fractional distillation and/or preparative gas chromatography.
  • 225eb may be prepared by a synthesis disclosed by 0. Paleta et al., Bull. Soc Chim.
  • the 1,1-dichloro-l,2,3,3,3- ⁇ enta- fluoropropane can be separated from its two isomers using fractional distillation and/or preparative gas chromatography. It should be understood that the present compositions may include additional components which form new azeotrope-like compositions. Any such compositions are considered to be within the scope of the present invention as long as the compositions are constant-boiling or essentially constant-boiling and contain all of the essential components described herein.
  • Inhibitors may be added to the present azeotrope-like compositions to inhibit decomposition of the compositions; react with undesirable decomposition products of the compositions; and/or prevent corrosion of metal surfaces.
  • Any or all of the following classes of inhibitors may be employed in the invention: epoxy compounds such as propylene oxide; nitroalkanes such as nitromethane; ethers such as 1-4-dioxane; unsaturated compounds such as 1,4- butyne diol; acetals or ketals such as dipropoxy methane; ketones such as methyl ethyl ketone; alcohols such as tertiary amyl alcohol; esters such as triphenyl phosphite; and amines such as triethyl amine.
  • Other suitable inhibitors will readily occur to those skilled in the art.
  • This example is directed to the preparation of 5 a preferred dichloropentafluoropropane component of the invention, 1,l-dichloro-2,2,3,3,3- ⁇ entafluoro ⁇ propane (225ca) .
  • Part C Synthesis of 1,l-dichloro-2,2,3,3,3- pentafluoropropane. Chlorine(289ml/min) and l-chloro-2,2,3,3,3-pentafluoro- ⁇ ropane(produced in Part B above), (1.72g/min) were fed simultaneously into a 1 inch(2.54cm) X 2 inches(5.08cm) monel reactor at 300°C. The process was repeated until 184g crude product had collected in the cold traps exiting the reactor.
  • compositional range over which 225cb, methanol and 2-methyl-2-propanol exhibit constant- boiling behavior was determined. This was accomplished by charging approximately 92 weight percent 225cb and 8 weight percent methanol into an ebulliometer.
  • the ebulliometer consisted of a heated sump in which the 225cb/methanol binary mixture was brought to a boil. The upper part of the ebulliometer connected to the sump was cooled thereby acting as a condenser for the boiling vapors, allowing the system to operate at total reflux.
  • 225cb-based mixtures were estimated by applying a barometric correction factor of about 26 mmHg/°C, to the observed values.
  • this corrected boiling point is generally accurate up to ⁇ 0.4°C and serves only as a rough comparison of boiling points determined on different days.
  • compositional range over which 225cb, ethanol and 2-methyl-2-propanol exhibit constant boiling behavior was determined by repeating the experiment outlined in Example 2 above except that a 95.5/4.5 weight percent mixture of 225cb and ethanol respectively was initially charged to the ebulliometer and 2-methyl-2-propanol was added. Observed boiling points were normalized by following the procedure outlined in Example 2. The results indicated that compositions of 225cb/ethanol/2-methyl- 2-propanol of about 95.5/4.5/1 weight percent respectively and preferably compositions of about 95.5/4.5/0.5 weight percent respectively exhibited constant boiling behavior at 53.9°C ⁇ about 0.5°C at 760 mm Hg.
  • compositional range over which 225cb, 2-propanol and 2-methyl-2-propanol exhibit constant boiling behavior was determined by repeating the experiment outlined in Example 2 above except that a 97/3 weight percent mixture of 225cb and 2- ⁇ ropanol respectively was initially charged to the ebulliometer and 2-methyl-2-propanol was added. Observed boiling points were normalized by following the procedure outlined in Example 2. The results indicated that compositions of 225cb/2- ⁇ ro ⁇ anol/2- methyl-2-propanol of about 97/3/1 weight percent respectively and preferably compositions of about
  • compositional range over which 225cb, 1- ⁇ ropanol and 2-methyl-2-propanol exhibit constant boiling behavior was determined by repeating the experiment outlined in Example 2 above except that a 99.5/0.5 weight percent mixture of 225cb/l-propanol respectively was initially charged to the ebullimeter and 2-methyl-2-propanol was added. Observed boiling points were normalized by following the procedure outlined in Example 2.
  • **The amount of HCFC-225ca and HCFC-225cb within said mixture is varied from about 0.01 to about 99.99 weight percent HCFC-225ca and from about 0.01 to about 99.99 weight percent HCFC-225cb.

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Abstract

Des compositions stables semblables a des azéotropes de dichloropentafluoropropane, un alcanol ayant de 1 à 3 atomes de carbone et 2-méthyl-2-propanol sont utiles dans une variété d'applications de nettoyage industriel y compris le nettoyage à froid et le défluxage de plaques à circuits imprimés.
PCT/US1991/009572 1990-12-18 1991-12-18 Composition semblable a des azeotropes de dichloropentafluoropropane, un alcanol ayant de 1 a 3 atomes de carbone et 2-methyl-2-propanol WO1992011400A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0347924A1 (fr) * 1988-06-22 1989-12-27 Asahi Glass Company Ltd. Utilisation de solvants d'hydrocarbures halogénés comme agents nettoyants
EP0381216A1 (fr) * 1989-02-01 1990-08-08 Asahi Glass Company Ltd. Mélange azéotropique ou semblable à un mélange azéotropique à base d'hydrocarbures hydrogénés, chlorés et fluorés
US4970013A (en) * 1989-12-11 1990-11-13 E. I. Dupont De Nemours And Company Binary azeotropic composition of 2,3-dichloro-1,1,1,3-3-pentafluoropropane and methanol
WO1991005035A1 (fr) * 1989-10-06 1991-04-18 Allied-Signal Inc. Compositions de dichloropentafluoropropane semblables a l'azeotrope et un alcanol possedant entre 1 et 4 atomes carbone

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0347924A1 (fr) * 1988-06-22 1989-12-27 Asahi Glass Company Ltd. Utilisation de solvants d'hydrocarbures halogénés comme agents nettoyants
EP0381216A1 (fr) * 1989-02-01 1990-08-08 Asahi Glass Company Ltd. Mélange azéotropique ou semblable à un mélange azéotropique à base d'hydrocarbures hydrogénés, chlorés et fluorés
WO1991005035A1 (fr) * 1989-10-06 1991-04-18 Allied-Signal Inc. Compositions de dichloropentafluoropropane semblables a l'azeotrope et un alcanol possedant entre 1 et 4 atomes carbone
US4970013A (en) * 1989-12-11 1990-11-13 E. I. Dupont De Nemours And Company Binary azeotropic composition of 2,3-dichloro-1,1,1,3-3-pentafluoropropane and methanol

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