US2999816A - Azeotropic composition - Google Patents

Azeotropic composition Download PDF

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Publication number
US2999816A
US2999816A US49427A US4942760A US2999816A US 2999816 A US2999816 A US 2999816A US 49427 A US49427 A US 49427A US 4942760 A US4942760 A US 4942760A US 2999816 A US2999816 A US 2999816A
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Prior art keywords
trichloro
methyl alcohol
solvent
azeotropic composition
trifluoroethane
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US49427A
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Edward J Bennett
Howard M Parmelee
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EIDP Inc
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EI Du Pont de Nemours and Co
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Priority to US49427A priority Critical patent/US2999816A/en
Priority to US49436A priority patent/US2999817A/en
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Publication of US2999816A publication Critical patent/US2999816A/en
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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41N—PRINTING PLATES OR FOILS; MATERIALS FOR SURFACES USED IN PRINTING MACHINES FOR PRINTING, INKING, DAMPING, OR THE LIKE; PREPARING SUCH SURFACES FOR USE AND CONSERVING THEM
    • B41N3/00—Preparing for use and conserving printing surfaces
    • B41N3/006—Cleaning, washing, rinsing or reclaiming of printing formes other than intaglio formes
    • 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
    • C11D7/5059—Mixtures containing (hydro)chlorocarbons
    • 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
    • C23G5/02812—Perhalogenated hydrocarbons
    • C23G5/02816—Ethanes
    • C23G5/02819—C2Cl3F3

Definitions

  • This invention relates to an azeotropic composition and particularly to the azeotropic mixture of 1,1,2-trichloro- 1,2,2-trifluoroethane and methyl alcohol.
  • chloroiluoromethanes and chlorofluoroethanes have attained widespread use as speciality solvents in recent years, particularly trichlorofiuorornethane and trichlorotrifluoroethane.
  • Both of these compounds are relatively low boiling liquids (CClgF, 23.8 C.; CCl FCClF 47.6 C.), which are nontoxic and nonfiammable, and which have satisfactory solvent power for greases, oils, waxes and the like. They have therefore found widespread use for cleaning electric motors, compressors, oxygen storage tanks, photographic film, lithographic plates, typewriters, instruments, gauges, sound tape, and as noncor-rosive brines.
  • the chlorofiuoromethanes and chlorofluoroethanes have insufficient solvent power alone. This is particularly true in the electronic industry during the manufacture of printed circuits.
  • Printed circuits are well known in the electronics art; and consist of a circuit formed from a soft metal on a solid, nonconducting surface such as a reinforced phenolic resin. During manufacture, the solid surface is coated with the metal, the desired portion of metal is coated with an impervious coating, and the excess metal is removed by etching with a suitable acid. After the excess metal has been removed, it is necessary to remove the impervious coating because solder joints must be made to the printed circuit and these will not form if the coating is present.
  • the circuits are coated with a rosin flux to permit the joints to be soldered, which rosin flux must then be removed.
  • the chlorofluoromethane and chlorofluoroethane solvents do not have sufficient solvent power to clean printed circuits; that is, to remove the rosin flux.
  • azeotropic composition consisting of about 93.6% by weight of 1,1,2-trichloro-1,2,2-trifluoroethane and about 6.4% by weight of methyl alcohol and boiling at 39 C. at 760 mm. pressure.
  • 1,1,2-trichloro-1,2,2-trifiuoroethane and methyl alcohol when admixed in the above proportions, form an azeotrope which distils at constant composition, the liquid phase and the vapor phase in equilibrium therewith having the same composition.
  • Such mixture is nonflammable and nontoxic in both the liquid phase and the vapor phase. It is useful as a heat exchange medium and as a hydraulic iluid. It is particularly useful as a solvent for greases, oils, waxes, and the like, in cleaning electric motors, compressors, photographic film, oxygen storage tanks, lithographic plates,
  • the azeotrope of this invention has several advantages over the solvents heretofore employed for cleaning printed circuits.
  • Trichloroethylene, tetrachloroethylene, and methyl chloroform are unstable and require stabilizers, whereas the azeotropic composition of this invention does not.
  • the azeotropic composition of this invention is more'eifective as a solvent for suchpurposes than trichloroethylene and tetrachloroethylene.
  • Inhibited methyl chloroform (containing dioxane as a stabilizer) is too strong a solvent and attacks the backing of the printed circuits. Isopropyl alcohol-toluene blends are flammable and irritating.
  • the azeotropic mixture-of 1,1,2-trichloro- 1,2,2-trifluoroethane and methyl alcohol does not suffer from any of these defects.
  • the small concentration of methyl alcohol in the azeotropic mixture is insufficient to render the mixture materially more toxic than the trichlorotrifluoroethane.
  • the azeotropic composition of this invention was obtained during the distillation of a mixture of 1780 grams of 1,1,Z-trichloro-1,2,2-trifluoroethane, 140 grams of ethyl alcohol and grams of methyl alcohol through a 1 inch x 38 inch column packed with Ms inch glass helices at a reflux ratio of 10/1 and a take off of 1 ml./min.
  • the first fraction obtained was 994 grams of the azeo trope, containing 93.6% by weight of 1,1,2-trichloro- 1,2,2-trifluoroethane and 6.4% by weight of methyl alcohol and having a boiling point of 39 C. at 760 mm. pressure.
  • the existence of the azeotrope was further confirmed when a mixture, containing 1700 grams of 1,1,2-trichloro-1,2,2-trifluoroethane and 300 grams of methyl alcohol, was distilled through the same column and under the same conditions as above described.
  • the first fraction distilled was 1792.4 grams of the azeotrope, containing 93.7% by weight of 1,1,2-trichloro-1,2,2-trifluoroethane and 6.3% by weight of methyl alcohol,
  • Printed circuit boards are usually prepared by impregnating glass cloth, nylon, or paper laminates with a phenol-formaldehyde resin or an epoxy resin.
  • Printed circuits are prepared by a variety of methods. In a typical procedure, the board consists originally of a phenolic resin impregnated base to which is bonded a sheet of copper, 2 to 4 mils thick, covering one surface of the board. The desired circuit is drawn on the copper with an asphalt based ink, using the silk screen method. The excess copper is then removed by etching with a ferric chloride-hydrochloric acid bath, sometimes containing ammonium chloride, leaving on the board the copper that is covered by the ink.
  • the asphalt ink is removed by cleaning with the azeotropic composition of this invention in an ultrasonic bath (some mechanical scrubbing is often used).
  • the entire surface of the board is coated with a rosin flux and dried.
  • the electronic components (resistors, capacitors, etc.) are then added at the proper places for soldering to the circuit.
  • the board is then passed over a molten solder bath, contacting the desired joints with the molten metal, whereby the soldering is effected. After cooling, the excess rosin flux remaining on the board must be removed since, if present in the final assembly, it will lead to corrosion, poor electrical resistance and other deleterious properties.
  • the board is cleaned by placing it in an ultrasonic bath operating at about 32 kilocycles per second and at about 25 C., where it remains for one minute. If 1,1,2-trichloro-1,2,2-trifluoroethane is used alone as the solvent in the bath, it has no efiect on the rosin flux. If methyl alcohol is used alone as the solvent in the bath, about 40% of the flux is removed. If trichloroethylene is used as the solvent in the bath, about 5% to about 50% of the flux remains after the treatment.
  • azeotropic composition of this invention in cleaning printed circuits is given for illustrative purposes solely, that this invention is not restricted to such specific embodiment and that other techniques may be employed. Also, the azeotropic composition can be used for other purposes as indicated in the general description.
  • this invention provides a novel azeotropic composition which has unusual properties and which is useful for a wide variety of purposes. Accordingly, it will be apparent that this invention constitutes a valuable contribution to and advance in the art.
  • An azeotropic composition consisting of about 93.6% by weight of 1,1,Z-trichloro-1,2,2-tuifluoroethane and about 6.4% by Weight of methyl alcohol and boiling at 39 C. and 760 mm. pressure.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Detergent Compositions (AREA)
  • Manufacturing Of Printed Wiring (AREA)

Description

J 2,999,816 Patented Sept. 1 2 1961 2,999,816 AZEOTROPIC COMPOSITION Edward J. Bennett, Newark, Del., and Howard M. Parmelee, Woodstown, N.J., assignors to E. I. du Pont de Nemours and Company, Wilmington, DeL, a corporation of Delaware No Drawing. Filed Aug. 15, 1960, Ser. No. 49,427 1 Claim. (Cl. 252-171) This invention relates to an azeotropic composition and particularly to the azeotropic mixture of 1,1,2-trichloro- 1,2,2-trifluoroethane and methyl alcohol.
Several of the chloroiluoromethanes and chlorofluoroethanes have attained widespread use as speciality solvents in recent years, particularly trichlorofiuorornethane and trichlorotrifluoroethane. Both of these compounds are relatively low boiling liquids (CClgF, 23.8 C.; CCl FCClF 47.6 C.), which are nontoxic and nonfiammable, and which have satisfactory solvent power for greases, oils, waxes and the like. They have therefore found widespread use for cleaning electric motors, compressors, oxygen storage tanks, photographic film, lithographic plates, typewriters, instruments, gauges, sound tape, and as noncor-rosive brines.
For certain solvent purposes however, the chlorofiuoromethanes and chlorofluoroethanes have insufficient solvent power alone. This is particularly true in the electronic industry during the manufacture of printed circuits. Printed circuits are well known in the electronics art; and consist of a circuit formed from a soft metal on a solid, nonconducting surface such as a reinforced phenolic resin. During manufacture, the solid surface is coated with the metal, the desired portion of metal is coated with an impervious coating, and the excess metal is removed by etching with a suitable acid. After the excess metal has been removed, it is necessary to remove the impervious coating because solder joints must be made to the printed circuit and these will not form if the coating is present. After the impervious coating is removed, the circuits are coated with a rosin flux to permit the joints to be soldered, which rosin flux must then be removed. The chlorofluoromethane and chlorofluoroethane solvents do not have sufficient solvent power to clean printed circuits; that is, to remove the rosin flux.
It is an object of this invention to provide a novel azeotropic composition which has new and unusual properties. Another object is to provide an axeotropic composition which is valuable as a solvent, and particularly for cleaning printed circuits. A further object is to provide such a composition which is nonfiammable and substantially nontoxic, both in the liquid phase and in the vapor phase. Other objects are to provide new compositions of matter and to advance the art. Still other objects will appear hereinafter.
The above and other objects may be accomplished in accord with this invention which comprises an azeotropic composition consisting of about 93.6% by weight of 1,1,2-trichloro-1,2,2-trifluoroethane and about 6.4% by weight of methyl alcohol and boiling at 39 C. at 760 mm. pressure.
It has been found that 1,1,2-trichloro-1,2,2-trifiuoroethane and methyl alcohol, when admixed in the above proportions, form an azeotrope which distils at constant composition, the liquid phase and the vapor phase in equilibrium therewith having the same composition. Such mixture is nonflammable and nontoxic in both the liquid phase and the vapor phase. It is useful as a heat exchange medium and as a hydraulic iluid. It is particularly useful as a solvent for greases, oils, waxes, and the like, in cleaning electric motors, compressors, photographic film, oxygen storage tanks, lithographic plates,
is a poor solvent therefor, it has been foundthat the small proportion of methyl alcohol present in the azeotrope with the 1,1,2-trichloroe1,2,2-trifluoroethane sufiicientlymodifies the solvent properties of both compo.- nents so as to make the azeotrope an excellent solvent mixture for such'purposes.
The azeotrope of this invention has several advantages over the solvents heretofore employed for cleaning printed circuits. Trichloroethylene, tetrachloroethylene, and methyl chloroform, are unstable and require stabilizers, whereas the azeotropic composition of this invention does not. The azeotropic composition of this invention is more'eifective as a solvent for suchpurposes than trichloroethylene and tetrachloroethylene. Inhibited methyl chloroform (containing dioxane as a stabilizer) is too strong a solvent and attacks the backing of the printed circuits. Isopropyl alcohol-toluene blends are flammable and irritating. The azeotropic mixture-of 1,1,2-trichloro- 1,2,2-trifluoroethane and methyl alcohol does not suffer from any of these defects. The small concentration of methyl alcohol in the azeotropic mixture is insufficient to render the mixture materially more toxic than the trichlorotrifluoroethane.
The azeotropic composition of this invention was obtained during the distillation of a mixture of 1780 grams of 1,1,Z-trichloro-1,2,2-trifluoroethane, 140 grams of ethyl alcohol and grams of methyl alcohol through a 1 inch x 38 inch column packed with Ms inch glass helices at a reflux ratio of 10/1 and a take off of 1 ml./min. The first fraction obtained was 994 grams of the azeo trope, containing 93.6% by weight of 1,1,2-trichloro- 1,2,2-trifluoroethane and 6.4% by weight of methyl alcohol and having a boiling point of 39 C. at 760 mm. pressure. Thereafter, there were obtained a fraction consisting of pure 1,1,2-trichloro-1,2,2-trifluoroethane at 42 C. and fractions which are nonazeotropic mixtures of 1,1,2-trich1oro-1,2,2-trifluoroethane with ethyl alcohol and small amounts of methyl alcohol.
The existence of the azeotrope was further confirmed when a mixture, containing 1700 grams of 1,1,2-trichloro-1,2,2-trifluoroethane and 300 grams of methyl alcohol, was distilled through the same column and under the same conditions as above described. The first fraction distilled Was 1792.4 grams of the azeotrope, containing 93.7% by weight of 1,1,2-trichloro-1,2,2-trifluoroethane and 6.3% by weight of methyl alcohol,
having a boiling point of 39 C. at 760* mm. pressure- At this point, insufficient 1,1,2-trichloro-1,2,2trifluor0- ethane remained to maintain the azeotrope, and non azeotropic mixtures of 1,1,Z-trichloro-l,2,2-trifluoroethane, containing higher concentrations of methyl alcohol, distilled.
Printed circuit boards are usually prepared by impregnating glass cloth, nylon, or paper laminates with a phenol-formaldehyde resin or an epoxy resin. Printed circuits are prepared by a variety of methods. In a typical procedure, the board consists originally of a phenolic resin impregnated base to which is bonded a sheet of copper, 2 to 4 mils thick, covering one surface of the board. The desired circuit is drawn on the copper with an asphalt based ink, using the silk screen method. The excess copper is then removed by etching with a ferric chloride-hydrochloric acid bath, sometimes containing ammonium chloride, leaving on the board the copper that is covered by the ink. After washing off the etch solution, the asphalt ink is removed by cleaning with the azeotropic composition of this invention in an ultrasonic bath (some mechanical scrubbing is often used). The entire surface of the board is coated with a rosin flux and dried. The electronic components (resistors, capacitors, etc.) are then added at the proper places for soldering to the circuit. The board is then passed over a molten solder bath, contacting the desired joints with the molten metal, whereby the soldering is effected. After cooling, the excess rosin flux remaining on the board must be removed since, if present in the final assembly, it will lead to corrosion, poor electrical resistance and other deleterious properties.
The board is cleaned by placing it in an ultrasonic bath operating at about 32 kilocycles per second and at about 25 C., where it remains for one minute. If 1,1,2-trichloro-1,2,2-trifluoroethane is used alone as the solvent in the bath, it has no efiect on the rosin flux. If methyl alcohol is used alone as the solvent in the bath, about 40% of the flux is removed. If trichloroethylene is used as the solvent in the bath, about 5% to about 50% of the flux remains after the treatment. If the same cleaning operation is repeated on another circuit board using the azeotropic mixture of 1,1,2-trichloro-l,2,2-tnifluoroethane and methyl alcohol as the solvent, the rosin flux is completely removed. Neither the 1,l,2-trichloro-1,2,2-triflnoroethane, the methyl alcohol, nor the azeotropic mixture thereof has any effect on the board which constitutes the backing of the printed circuit.
It will be understood that the preceding detailed description of the use of the azeotropic composition of this invention in cleaning printed circuits is given for illustrative purposes solely, that this invention is not restricted to such specific embodiment and that other techniques may be employed. Also, the azeotropic composition can be used for other purposes as indicated in the general description.
From the preceding description, it will be apparent that this invention provides a novel azeotropic composition which has unusual properties and which is useful for a wide variety of purposes. Accordingly, it will be apparent that this invention constitutes a valuable contribution to and advance in the art.
The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:
An azeotropic composition consisting of about 93.6% by weight of 1,1,Z-trichloro-1,2,2-tuifluoroethane and about 6.4% by Weight of methyl alcohol and boiling at 39 C. and 760 mm. pressure.
References Cited in the file of this patent Industrial Solvents, Mellan, 2nd ed. (1950), pp. 48- 79, 372-373, 448-453.
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Cited By (47)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3275563A (en) * 1962-08-03 1966-09-27 Dick Co Ab Offset erasing fluid
US3340199A (en) * 1964-04-02 1967-09-05 Ici Ltd Azeotropic halogenated hydrocarbonalcohol solvent composition
US3400077A (en) * 1965-12-22 1968-09-03 Allied Chem Fluorinated hydrocarbon containing compositions
US3431211A (en) * 1965-03-05 1969-03-04 Du Pont Azeotropic compositions
US3477952A (en) * 1966-07-01 1969-11-11 Du Pont Azeotropic composition
US3530073A (en) * 1968-09-30 1970-09-22 Union Carbide Corp Azeotropic composition
US3539462A (en) * 1968-10-17 1970-11-10 Union Carbide Corp Azeotropic composition
US3625763A (en) * 1968-12-04 1971-12-07 Bunker Ramo Conformal coating stripping method and composition
US3663255A (en) * 1969-12-01 1972-05-16 Dow Chemical Co Composition containing chlorinated hydrocarbons ketones and glycol ethers, for reflowing organic surfaces
US3691092A (en) * 1970-10-29 1972-09-12 Du Pont 1,1,1,3,3,3-hexafluoro-2-propanol/c1 to c4 alkanol complexes
US3846327A (en) * 1972-05-30 1974-11-05 Union Carbide Corp Azeotropic composition
US3846332A (en) * 1971-08-02 1974-11-05 Airco Inc Azeotropes of 1-chloro-2,2,2-trifluoroethyl difluoromethyl ether with acetone, methyl ethylketone and tetrahydrofuran
US3881949A (en) * 1973-02-27 1975-05-06 Du Pont Vapor degreaser process employing trichlorotrifluoroethane and ethanol
US3915875A (en) * 1973-03-23 1975-10-28 Mc Donnell Douglas Corp Low temperature fluid
US3936387A (en) * 1972-02-04 1976-02-03 Phillips Petroleum Company Azeotrope of 1,2-dichloro-1-fluoroethane and methanol
DE2533357A1 (en) * 1974-07-25 1976-02-05 Du Pont AZEOTROPIC COMPOSITION
US3940342A (en) * 1973-09-13 1976-02-24 Phillips Petroleum Company Azeotrope of 1,2-dichloro-1,1,2-trifluoroethane and trichlorofluoromethane
US3957531A (en) * 1971-09-27 1976-05-18 Imperial Chemical Industries Limited Two tank cleaning process using a contaminated cleaning mixture capable of forming an azeotrope
US4002573A (en) * 1973-09-13 1977-01-11 Phillips Petroleum Company Azeotropes of 1,2-dichloro-1,1,2-trifluoroethane
US4024086A (en) * 1975-08-06 1977-05-17 Phillips Petroleum Company Constant boiling admixtures
US4035258A (en) * 1973-08-27 1977-07-12 Phillips Petroleum Company Azeotropic compositions
US4062794A (en) * 1975-12-08 1977-12-13 Allied Chemical Corporation Azeotrope-like compositions of trichlorotrifluoroethane, methanol, ethanol, isopropanol and nitromethane
US4303558A (en) * 1978-09-15 1981-12-01 Imperial Chemical Industries Limited Cleaning composition comprising 1,1,2-trichloro-1,2,2-trifluoroethane and an alcohol
US4440963A (en) * 1982-08-09 1984-04-03 Phillips Petroleum Company Production of MTBE and ETBE
US4654160A (en) * 1985-10-11 1987-03-31 Allied Corporation Azeotrope-like compositions of trichlorotrifluoroethane, methanol, acetone, nitromethane and hexane
US4655956A (en) * 1985-10-02 1987-04-07 Allied Corporation Azeotrope-like compositions of trichlorotrifluoroethane, methanol, nitromethane and hexane
US4662948A (en) * 1984-11-28 1987-05-05 Electric Power Research Institute On-site removal of PCB and dioxins from soils
US4683075A (en) * 1986-07-23 1987-07-28 Allied Corporation Azeotrope-like compositions of trichlorotrifluoroethane, methanol, nitromethane, acetone, and methyl acetate
EP0230455A1 (en) * 1985-07-10 1987-08-05 SMITH, Richard Daniel Treatment of cellulosic materials
US4715900A (en) * 1987-01-08 1987-12-29 E. I. Du Pont De Nemours And Company Azeotropic compositions of trichlorotrifluoroethane, dichlorodifluoroethane and methanol/ethanol
US4767561A (en) * 1987-09-23 1988-08-30 E. I. Du Pont De Nemours And Company Azeotrope or azeotrope-like composition of trichlorotrifluoroethane, methanol and 1,2-dichloroethylene
EP0327282A1 (en) * 1988-02-02 1989-08-09 E.I. Du Pont De Nemours And Company Stabilized azeotrope or azeotrope-like composition of 1,1,2-trichloro-1,2,2-trifluoroethane, methanol and 1,2-dichloroethylene
US4873015A (en) * 1988-10-31 1989-10-10 Allied-Signal Inc. Azeotrope-like compositions of 1,1,2-trichloro-1,2,2-trifluoroethane, methanol, nitromethane and dimethoxymethane
US4900470A (en) * 1988-12-01 1990-02-13 Allied-Signal Inc. Azeotrope-like compositions of 1,1,2-trichloro-1,2,2-trifluoroethane, methanol, nitromethane and 1-chloropropane
US4904407A (en) * 1988-12-01 1990-02-27 Allied-Signal Inc. Azeotrope-like compositions of 1,1,2-trichloro-1,2,2-trifluoroethane, methanol, nitromethane, 1,2-dichloroethylene and 1-chloropropane
US4936923A (en) * 1989-03-01 1990-06-26 E. I. Du Pont De Nemours And Company Azeotropic compositions of 1,1,2-trichlorotrifluoroethane with cis-1,2-dichloroethylene and n-propanol or isopropanol with or without nitromethane
US4954289A (en) * 1989-06-12 1990-09-04 E. I. Du Pont De Nemours And Company Azeotropes of hydrogen-containing halocarbons with butanes
US4971085A (en) * 1988-12-27 1990-11-20 Allied-Signal Inc. Azeotrope-like compositions of 1,1,2-trichloro-1,2,3-trifluoroethane, methanol, nitromethane, 1,2-dichloroethylene, acetone and hexane
US4973362A (en) * 1988-12-27 1990-11-27 Allied-Signal Inc. Azeotrope-like compositions of 1,1,2-trichloro-1,2,2-trifluoroethane, methanol, nitromethane, 1,2-dichloroethylene and hexane
US4973421A (en) * 1988-01-22 1990-11-27 Daikin Industries, Ltd. Azeotropic solvent composition
EP0411778A1 (en) * 1989-08-03 1991-02-06 E.I. Du Pont De Nemours And Company Ternary azeotropic compositions of 2,3-dichloro-1,1,1,3,3-pentafluoropropane with trans-1,2-dichloroethylene and methanol
US5023010A (en) * 1990-07-23 1991-06-11 E. I. Du Pont De Nemours And Company Binary azeotropic compositions of 1,1,1,2,3,3-hexafluoro-3-methoxypropane with methanol or isopropanol or N-propanol
US5026498A (en) * 1990-10-03 1991-06-25 E. I. Du Pont De Nemours And Company Binary azeotropic compositions of 1,1,1,2,3,3-hexafluoro-3-methoxypropane with one of trans-1,2-dichloroethylene, cis-1,2-dichloroethylene, 1,1-dichloro-1,2-difluoroethane or 1,2-dichloro-1,1,-difluoroethane
US5034149A (en) * 1990-03-21 1991-07-23 E. I. Du Pont De Nemours And Company Binary azeotropic compositions of 3-chloro-1,1,1-trifluoropropane with methanol or ethanol, or trans-1,2-dichloroethylene
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US3960746A (en) * 1974-07-25 1976-06-01 E. I. Du Pont De Nemours And Company Azeotrope-like compositions of methanol, nitromethane and trichlorotrifluoroethane
US4024086A (en) * 1975-08-06 1977-05-17 Phillips Petroleum Company Constant boiling admixtures
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US4303558A (en) * 1978-09-15 1981-12-01 Imperial Chemical Industries Limited Cleaning composition comprising 1,1,2-trichloro-1,2,2-trifluoroethane and an alcohol
US4440963A (en) * 1982-08-09 1984-04-03 Phillips Petroleum Company Production of MTBE and ETBE
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US4655956A (en) * 1985-10-02 1987-04-07 Allied Corporation Azeotrope-like compositions of trichlorotrifluoroethane, methanol, nitromethane and hexane
US4654160A (en) * 1985-10-11 1987-03-31 Allied Corporation Azeotrope-like compositions of trichlorotrifluoroethane, methanol, acetone, nitromethane and hexane
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US4973421A (en) * 1988-01-22 1990-11-27 Daikin Industries, Ltd. Azeotropic solvent composition
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US4873015A (en) * 1988-10-31 1989-10-10 Allied-Signal Inc. Azeotrope-like compositions of 1,1,2-trichloro-1,2,2-trifluoroethane, methanol, nitromethane and dimethoxymethane
US4904407A (en) * 1988-12-01 1990-02-27 Allied-Signal Inc. Azeotrope-like compositions of 1,1,2-trichloro-1,2,2-trifluoroethane, methanol, nitromethane, 1,2-dichloroethylene and 1-chloropropane
US4900470A (en) * 1988-12-01 1990-02-13 Allied-Signal Inc. Azeotrope-like compositions of 1,1,2-trichloro-1,2,2-trifluoroethane, methanol, nitromethane and 1-chloropropane
US4971085A (en) * 1988-12-27 1990-11-20 Allied-Signal Inc. Azeotrope-like compositions of 1,1,2-trichloro-1,2,3-trifluoroethane, methanol, nitromethane, 1,2-dichloroethylene, acetone and hexane
US4973362A (en) * 1988-12-27 1990-11-27 Allied-Signal Inc. Azeotrope-like compositions of 1,1,2-trichloro-1,2,2-trifluoroethane, methanol, nitromethane, 1,2-dichloroethylene and hexane
US4936923A (en) * 1989-03-01 1990-06-26 E. I. Du Pont De Nemours And Company Azeotropic compositions of 1,1,2-trichlorotrifluoroethane with cis-1,2-dichloroethylene and n-propanol or isopropanol with or without nitromethane
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