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WO1991018967A1 - Compositions analogues a l'azeotrope de dichloropentafluoropropane, ethanol et 1,2-dichloroethylene - Google Patents

Compositions analogues a l'azeotrope de dichloropentafluoropropane, ethanol et 1,2-dichloroethylene Download PDF

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Publication number
WO1991018967A1
WO1991018967A1 PCT/US1991/003218 US9103218W WO9118967A1 WO 1991018967 A1 WO1991018967 A1 WO 1991018967A1 US 9103218 W US9103218 W US 9103218W WO 9118967 A1 WO9118967 A1 WO 9118967A1
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Prior art keywords
compositions
weight percent
azeotrope
dichloro
dichloroethylene
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PCT/US1991/003218
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English (en)
Inventor
Hillel Magid
David Paul Wilson
Dennis M. Lavery
Richard M. Hollister
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Allied-Signal Inc.
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Publication of WO1991018967A1 publication Critical patent/WO1991018967A1/fr

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    • 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
    • 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

Definitions

  • This invention relates to azeotrope-like mixtures of dichloropentafluoropropane, ethanol, and 1,2-dichloro- ethylene. These mixtures are useful in a variety of vapor degreasing, cold cleaning, and solvent cleaning applications including defluxing and dry cleaning.
  • I QQ ⁇ discloses azeotrope-like compositions of dichloropentafluoropropane and an alkanol having 1 to 4 carbon atoms.
  • Fluorocarbon based solvents have been used 5 extensively for the degreasing and otherwise cleaning of solid surfaces, especially intricate parts and difficult to remove soils.
  • vapor degreasing or solvent 0 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 leaves the object of residue. This • j _ 5 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 conventional operation of a vapor degreaser consists of immersing the part to be cleaned in a sump of boiling solvent which
  • the part 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
  • 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
  • Trichlorotri luoroethane 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
  • 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 dichloropentafluoropropane, have a much lower ozone depletion potential and global warming potential than the fully halogenated species.
  • the invention relates to novel azeotrope-like compositions which are useful in a variety of industrial cleaning applications. Specifically, the invention relates to compositions of dichloropentafluoropropane, ethanol and 1,2-dichloroethylene which are essentially constant boiling, environmentally acceptable and which remain liquid at room temperature. DETAILED DESCRIPTION OF THE INVENTION
  • novel 5 azeotrope-like compositions consisting essentially of from about 61 to about 93 weight percent dichloropentafluoropropane, from about 1 to about 12 weight percent ethanol and from about 6 to about 27 weight percent 1,2-dichloroethylene which boil at about 0 52.0°C ⁇ about 3.0°C at 760 mm Hg.
  • Dichloropentafluoropropane exists in nine isomeric forms: (1) 2,2-dichloro-l,1,1,3,3-pentafluoropropane (HCFC-225a) ; (2) 1,2-dichloro-l,2,3,3,3-pentafluoro- 5 propane (HCFC-225ba) ; (3) 1,2-dichloro-l,1,2,3,3- pentafluoropropane (HCFC-225bb) ; (4) 1,1-dichloro- 2,2,3,3,3-pentafluoropropane (HCFC-225ca); (5) 1,3- dichloro-l,1,2,2,3-pentafluoropropane ⁇ HCFC-225cb) ; (6) 1,1-dichloro-1,2,2,3,3-pentafluoropropane Q (HCFC-225cc) ; (7) 1,2-dichloro-l,1,3,3,3-penta- fluoropropane (HCFC-
  • dichloropentafluoropropane will refer to any of the isomers or admixtures of the isomers in any proportion.
  • the 1,l-dichloro-2,2,3,3,3-pentafluoropropane isomer is the preferred isomer.
  • the 1,2-dichloroethylene component of the invention 0 exists in two isomeric forms, cis-l,2-dichloroethylene and trans-l,2-dichloroethylene.
  • dichloroethylene will refer to either isomer or admixtures of the isomers in any proportion.
  • the cis-1,2- dichloroethylene isomer is the preferred isomer. 5
  • the dichloropentafluoropropane component of the invention has good solvent properties. Ethanol and
  • 1,2-dichloroethylene too, are good solvents. Ethanol dissolves polar organic materials and amine hydrochlorides while 1,2-dichloroethylene enhances the solubility of oils. Thus, when these components are combined in effective amounts, an efficient azeotropic solvent results.
  • the azeotrope-like compositions of the invention consist essentially of from about 68 to about 93 weight percent dichloropentafluoro- propane, from about 1 to about 12 weight percent ethanol and from about 6 to about 20 weight percent 1,2-dichloro ⁇ ethylene.
  • the azeotrope-like compositions of the invention consist essentially of from about 71 to about 93 weight percent dichloropentafluoro ⁇ propane, from about 1 to about 9 weight percent ethanol and from about 6 to about 20 weight percent 1,2-dichloro ⁇ ethylene.
  • 1,l-dichloro-2,2,3,3,3-pentafluoropropane 225ca
  • the azeotrope-like compositions of the invention consist essentially of from about 64 to about 93 weight percent 1,l-dichloro-2,2,3,3,3-pentafluoropropane, from about 1 to about 9 weight percent ethanol and from about 6 to about
  • the azeotrope-like compositions consist essentially of from about 71 to about 93 weight percent 1,l-dichloro-2,2,3,3,3-pentafluoropropane, from about 1 to about 9 weight percent ethanol and from about 6 to about 20 weight percent 1,2-dichloroethylene.
  • the azeotrope-like compositions consist essentially of from about 73 to about 89 weight percent 1,l-dichloro-2,2,3,3,3-pentafluoropropane, from about 1 to about 9 weight percent ethanol and from about 10 to about 18 weight percent 1,2-dichloroethylene.
  • the azeotrope-like compositions consist essentially of from about 74.5 to about 88.5 weight percent 1,l-dichloro-2,2,3,3,3-pentafluoropropane, from about 1.5 to about 7.5 weight percent ethanol and from about 10 to about 18 weight percent 1,2-dichloroethylene.
  • 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 T. In practice, this means that the components of a mixture cannot be separated during distillation, and therefore are useful in vapor phase solvent cleaning as described above.
  • 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 composition ay 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 a 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-azeotropic 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 having a variable composition depending on temperature and/or pressure.
  • azeotrope-like within the meaning of the invention is to state that such mixtures boil within about ⁇ 3.0°C (at 760 mm Hg) of the 52.0°C boiling point disclosed herein.
  • the boiling point of the azeotrope will vary with the pressure.
  • the 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 of the invention are useful as solvents for a variety of 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 dichloropentafluoropropane, ethanol, and 1,2-dichloroethylene 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 solvents or constant boiling properties of the system. Com ercially available ethanol and 1,2-dichloro- ethylene may be used in the present invention. Most dichloropentafluoropropane isomers, like the preferred HCFC-225ca isomer, however, 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- ⁇ ropanol and p-toluenesulfonate chloride together to form 2,2,3,3,3- pentafluoropropyl.-p-toluenesulfonate.
  • N-methyl- pyrrolidone, lithium chloride, and the 2,2,3,3,3- pentafluoropropyl-p-toluenesulfonate are reacted together to form l-chloro-2,2,3,3,3-pentafluoropropane.
  • This compound may be prepared by reacting a dimethylformamide solution of 1,1,l-trichloro-2,2,2- trifluoromethane with chlorotrimethylsilane in the presence of zinc, forming l-(trimethylsiloxy)-
  • 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-methylpyrrolidone, 145 gm (0.507 mol) 2,2,3,3- tetrafluoropropyl-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.
  • Synthesis of 1.1-dichloro-l.2.2.3.3-pentafluoro ⁇ propane (225cc) 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- tetrafluoropropyl-p-toluenesulfonate is reacted with potassium fluoride in N-methylpyrrolidone to form 1,1,2,2,3-pentafluoropropane.
  • 1,1,2,2,3- pentafluoropropane is reacted with chlorine to form 1,1-dichloro-l,2,2,3,3-pentafluoropropane.
  • This isomer is commercially available from P.C.R. Incorporated of Gainsville, Florida. 5
  • this compound may be prepared by adding equimolar amounts of 1,1,1,3,3-pentafluoropropane and chlorine gas to a borosilicate flask that has been purged of air. The flask is then irradiated with a mercury lamp. Upon completion of the irradiation, the contents of 0 the flask are cooled. The resulting product will be 1,2-dichloro-l,1,3,3,3-pentafluoropropane.
  • 1.3-dichloro-l.1.2.3.3-pentafluoro ⁇ propane (225ea).
  • This compound may be prepared by 5 reacting trifluoroethylene with dichlorotri- fluoromethane to produce 1,3-dichloro-l,1,2,3,3,- pentafluoropropane and 1,1-dichloro-l,2,3,3,3-penta- fluoropropane.
  • the 1,3-dichloro-l,1,2,3,3-pentafluoro ⁇ propane is seperated from its isomers using fractional Q distillation and/or preparative gas chromatography.
  • 225eb 1.1-dichloro-l.2.3.3.3-pentafluoro ⁇ propane (225eb) .
  • This compound may be prepared by reacting trifluoroethylene with dichlorodifluoromethane to produce 1,3-dichloro-l,1,2,3,3-pentafluoropropane and 1,1-dichloro-l,2,3,3,3-pentafluoropropane.
  • the 1,l-dichloro-1,2,3,3,3-pentafluoropropane is separated from its isomer using fractional distillation and/or preparative gas chromatography.
  • 225eb may 0 be prepared by a synthesis disclosed by 0. Paleta et al.. Bull. Soc. Chim. Fr., (6) 920-4 (1986).
  • the 1,l-dichloro-1,2,3,3,3-pentafluoropropane can be separated from its two isomers using fractional distillation and/or preparative gas chromat
  • 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 1,l-dichloro-2,2,3,3,3-pentafluoropropane (HCFC-225ca) .
  • Part B Synthesis of l-chloro-2,2,3,3,3- pentafluoropropane.
  • a 1 liter flask fitted with a thermometer, Vigreaux column and distillation receiving head was charged with 248.5g(0.82mol) 2,2,3,3,3- pentafluoropropyl-p-toluenesulfonate(produced in Part A above), 375ml N-methylpyrrolidone, and 46.7 g(l.lmol) lithium chloride.
  • the mixture was then heated with stirring to 140°C at which point, product began to distill over. Stirring and heating were continued until a pot temperature of 198°C had been reached at which point, there was no further distillate being collected.
  • the crude product was re-distilled to give 107.2g(78%) of product.
  • Part C Synthesis of 1,l-dichloro-2,2,3,3,3- pentafluoropropane. Chlorine (289ml/min) and l-chloro-2,2,3,3,3-pentafluoropropane(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 225ca, ethanol and cis-l,2-dichloroethylene exhibit constant-boiling behavior was determined. This was accomplished by charging selected 225ca-based binary compositions into an ebulliometer, bringing them to a boil, adding measured amounts of a third component and finally recording the temperature of the ensuing boiling mixture. In each case, a minimum in the boiling point versus composition curve occurred indicating that a constant boiling composition formed.
  • the ebulliometer consisted of a heated sump in which the 225ca-based 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. After bringing the 225ca-based binary mixture to boil at atmospheric pressure, measured amounts of a third component were titrated into the ebulliometer. The change in boiling point was measured with a platinum resistance thermometer.
  • Example is constant boiling Tempera ure (° ⁇ Z1
  • trans-1,2-dichloroethylene 0.1 to about 25 weight percent trans-1,2-dichloroethylene are studied. This is accomplished by charging selected dichloropentafluoropropane-based binary compositions into an ebulliometer, bringing them to a boil, adding measured amounts of a third component and finally recording the temperature of the ensuing boiling mixture. In each case, a minimum in the boiling point versus composition curve occurs indicating that a constant boiling composition forms between each dichloropentafluoropropane component, ethanol and 75-99.9/0.1-25 weight percent mixture of cis-1,2-dichloroethylene/trans-1,2-dichloroethylene.
  • azeotropic properties of the dichloropenta- fluoropropane components listed in Table III with ethanol and a mixture of from about 90 to about 99.9 weight percent cis-1,2-dichloroethylene and from about 0.1 to about 10 weight percent trans-1,2-dichloroethylene are studied by repeating the experiment outlined in Examples 16-26 above except that a 90-99.9/0.1-10 weight percent mixture of cis-1,2-dichloroethylene/trans-l,2-dichloro ⁇ ethylene is substituted for the 75-99.9/0.1-25 weight percent mixture of cis-1,2-dichloroethylene/trans-l,2- dichloroethylene.
  • azeotropic properties of the dichloropenta- fluoropropane components listed in Table III with ethanol and a mixture of from about 95-99.9 weight percent cis-1,2-dichloroethylene and from about 0.1 to about 5 weight percent tr.ans-1,2-dichloroethylene are studied by repeating the experiment outlined in Examples 16-26 above except that a 95-99.9/0.1-5 weight percent mixture of cis-1,2-dichloroethylene/trans-l,2-dichloroethylene is substituted for the 75-99.9/0.1-25 weight percent mixture of cis-1,2-dichloroethylene/trans-l,2-dichloro- ethylene.

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Abstract

Nouvelles compositions analogues à l'azéotrope comprenant du dichloropentafluoropropane, de l'éthanol et 1,2-dichloroéthylène utiles dans une variété d'applications de nettoyage industriel y compris le nettoyage à froid et de décapage de cartes de circuits imprimés.
PCT/US1991/003218 1990-06-06 1991-05-09 Compositions analogues a l'azeotrope de dichloropentafluoropropane, ethanol et 1,2-dichloroethylene WO1991018967A1 (fr)

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US533,972 1990-06-06

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1989012674A1 (fr) * 1988-06-22 1989-12-28 Asahi Glass Company Ltd. Solvants hydrocarbures halogenes et leur utilisation
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
EP0411778A1 (fr) * 1989-08-03 1991-02-06 E.I. Du Pont De Nemours And Company Compositions ternaires azéotropiques de 2,3-dichloro-1,1,1,3,3-pentafluoropropane, trans-1,2-dichloréthylène et méthanol

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1989012674A1 (fr) * 1988-06-22 1989-12-28 Asahi Glass Company Ltd. Solvants hydrocarbures halogenes et leur utilisation
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
EP0411778A1 (fr) * 1989-08-03 1991-02-06 E.I. Du Pont De Nemours And Company Compositions ternaires azéotropiques de 2,3-dichloro-1,1,1,3,3-pentafluoropropane, trans-1,2-dichloréthylène et méthanol

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