Partially fluorinated alkanes having a tertiary structure

Abstract

Novel partially fluorinated alkanes having the Formula: ##STR1## wherein each R is the same or different and is selected from the group consisting of CF.sub.3, CHF.sub.2, CH.sub.2 F, and CH.sub.3 CF.sub.2, and R' is an alkyl or fluoroalkyl group having 1 to 6 carbon atoms with the proviso that when each R is CF.sub.3, R' is not CF.sub.3 (CF.sub.2).sub.2 -, CH.sub.3 CF.sub.2 -, or CF.sub.3 have utility as solvents in a variety of industrial cleaning applications including cold cleaning, dry cleaning, and defluxing of printed circuit boards.

Description

FIELD OF THE INVENTION

This invention relates to novel partially fluorinated alkanes having a tertiary structure and 4 to 9 carbon atoms. These compounds are useful in a variety of vapor degreasing, cold cleaning, and solvent cleaning applications including defluxing and dry cleaning.

BACKGROUND OF THE INVENTION

Cold cleaning is an application where numerous solvents are used. In most cold cleaning applications, the soiled part is either immersed in the fluid or wiped with rags or similar objects soaked in solvents and allowed to air dry.

In cold cleaning applications, the use of the aerosol packaging concept has long been found to be a convenient and cost effective means of dispensing solvents. Aerosol products utilize a propellant gas or mixture of propellant gases, preferably in a liquified gas rather than a compressed gas state, to generate sufficient pressure to expel the active ingredients, i.e. product concentrates such as solvents, from the container upon opening of the aerosol valve. The propellants may be in direct contact with the solvent, as in most conventional aerosol systems, or may be isolated from the solvent, as in barrier-type aerosol systems.

Vapor degreasing and solvent cleaning with fluorocarbon based solvents have found widespread use in industry for the degreasing and otherwise cleaning of solid surfaces, especially intricate parts and difficult to remove soils.

In its simplest form, 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 behind no residue as would be the case where the object is simply washed in liquid solvent.

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 and quickly, 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. In addition, 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. For example, Sherliker et al. in U.S. Pat. No.3,085,918 disclose such suitable vapor degreasers comprising a boiling sump, a clean sump, a water separator, and other ancillary equipment.

Chlorofluorocarbon solvents, such as trichlorotrifluoroethane, have attained widespread use in recent years as effective, nontoxic, and nonflammable agents useful in degreasing applications and other solvent cleaning applications. One isomer of trichlorotrifluoroethane is 1,1,2-trichloro-1,2,2-trifluoroethane (known in the art as CFC-113). CFC-113 has a boiling point of about 47.degree. C. and 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 and the like.

Another commonly used solvent is chloroform (known in the art as HCC-20) which has a boiling point of about 63.degree. C. Perchloroethylene is a commonly used dry cleaning and vapor degreasing solvent which has a boiling point of about 121.degree. C. These compounds are disadvantageous for use as solvents because they are toxic; also, chloroform causes liver damage when inhaled in excess.

Although chlorine is known to contribute to the solvency capability of a compound, fully halogenated chlorofluorocarbons and hydrochlorocarbons are suspected of causing environmental problems in connection with the earth's protective ozone layer. Thus, the art is seeking new compounds which do not contribute to environmental problems but yet provide the solvency properties of CFC-113. From an environmental standpoint, hydrofluorocarbon and hydrocarbon compounds are of interest because they are considered to be stratospherically safe substitutes for the currently used fully halogenated chlorofluorocarbons. Mathematical models have substantiated that hydrofluorocarbons and hydrocarbons will not adversely affect atmospheric chemistry as not contributing to ozone depletion and to green-house global warming in comparison to the fully halogenated species.

The problems with hydrofluorocarbons as solvents are that known straight chain hydrofluorocarbons such as CH.sub.3 (CF.sub.2).sub.4 H and CH.sub.3 CH.sub.2 (CF.sub.2).sub.3 H do not have the solvency power of CFC-113. A branched hydrofluorocarbon such as CF.sub.3 CH(CF.sub.3).sub.2 is nonflammable but has a boiling point of about 15.degree. C. and thus, is not liquid at room temperature at atmospheric pressure and is not useful in cold cleaning applications. The problems with hydrocarbons as solvents are that branched hydrocarbons such as isobutane are flammable and have such low boiling points that they are not liquid at room temperature and are not useful in cold cleaning applications. The problem with alkanols as solvents is that branched alkanols such as isobutanol are flammable.

It is an object of this invention to provide novel hydrofluorocarbon compounds which are liquid at room temperature and which are useful as solvents for use in vapor degreasing, cold cleaning, and other solvent cleaning applications including defluxing applications and dry cleaning.

Another object of the invention is to provide novel environmentally acceptable solvents for use in the aforementioned applications.

Other objects and advantages of the invention will become apparent from the following description.

DETAILED DESCRIPTION OF THE INVENTION

We have found a novel class of hydrofluorocarbons which we believe have good solvency characteristics. The present novel compounds are of the Formula: ##STR2## wherein each R is the same or different and is selected from the group consisting of CF.sub.3, CHF.sub.2, CH.sub.2 F, and CH.sub.3 CF.sub.2 -, and R' is an alkyl or fluoroalkyl group having 1 to 6 carbon atoms with the proviso that when each R is CF.sub.3, R' is not CF.sub.3 (CF.sub.2).sub.2 -, CF.sub.3 CF.sub.2 -, or CF.sub.3.

Because C in the Formula above has three alkyl groups thereon, these novel compounds have a tertiary structure. We believe that this tertiary structure provides good solvency power. The R component of the Formula above helps to make the hydrogen of the Formula above more acidic and therefore, more polar; thus, when the present compounds are used as solvents, the compounds have good solvency power for polar contaminants such as polyols and amines. The R' component of the Formula above helps to make the compounds nonpolar; thus, when the present compounds are used as solvents, the compounds also have good solvency power for nonpolar contaminants including hydrocarbons such as mineral oil. We also believe that these novel compounds have boiling points in the range of about 35.degree. to about 80.degree. C. which are comparable to those of CFC-113 and chloroform.

Preferably, R' in the Formula above is selected from the group consisting of CF.sub.3 CHF.sub.2, CH.sub.2 F, CH.sub.3, CF.sub.3 (CF.sub.2).sub.n -, CF.sub.3 CF.sub.2 CHF-, CF.sub.3 CF.sub.2 CH.sub.2 -, CF.sub.3 (CHF).sub.n -, CF.sub.3 CHFCF.sub.2 -, CF.sub.3 CHFCH.sub.2 -, CF.sub.3 (CH.sub.2).sub.n -, CF.sub.3 CH.sub.2 CF.sub.2 -, CF.sub.3 CH.sub.2 CHF-, CHF.sub.2 (CF.sub.2).sub.n -, CHF.sub.2 CF.sub.2 CHF-, CHF.sub.2 CF.sub.2 CH.sub.2 -, CHF.sub.2 (CHF).sub.n -, CHF.sub.2 CHFCF.sub.2 -, CHF.sub.2 CHFCH.sub.2 -, CHF.sub.2 CHFCH.sub.2 -, CHF.sub.2 (CH.sub.2).sub.n -, CHF.sub.2 CH.sub.2 CF.sub.2 -, CHF.sub.2 CH.sub.2 CHF-, CH.sub.2 F(CF.sub.2).sub.n -, CH.sub.2 FCF.sub.2 CHF-, CH.sub.2 FCF.sub.2 CH.sub.2 -, CH.sub.2 F(CHF).sub.n -, CH.sub.2 FCHFCF.sub.2 -, CH.sub.2 FCHFCH.sub.2 -, CH.sub.2 F(CH.sub.2).sub.n -, CH.sub.2 FCH.sub.2 CF.sub.2 -, CH.sub.2 FCH.sub.2 CHF.sub.2 -, CH.sub.3 (CF.sub.2).sub.n -, CH.sub.3 CF.sub.2 CHF-, CH.sub.3 CF.sub.2 CH.sub.2 -, CH.sub.3 (CHF).sub.n -, CH.sub.3 CHFCF.sub.2 -, CH.sub.3 CHFCH.sub.2 -, and CH.sub.3 (CH.sub.2).sub.m (CF.sub.2).sub.n, and m is 1 to 3, and n is 1 or 2 with the proviso that when each R is CF3, R' is not CF.sub.3, CF.sub.3 CF.sub.2 -, or CF.sub.3 (CF.sub.2).sub.2 -.

In the Formula above, when one R is CF.sub.3, the other R is CHF.sub.2, and R' is CH.sub.3, the compound is 2-methyl-1,1,1,3,3-pentafluoropropane. When one R is CF.sub.3, the other R is CH.sub.2 F, and R' is CH.sub.3, the compound is 2-methyl-1,1,1,3-tetrafluoropropane. When one R is CF.sub.3, the other R is CH.sub.2 F, and R' is CHF.sub.2 CHF-, the compound is 2-fluoromethyl-1,1,1,3,4,4-hexafluorobutane. When one R is CF.sub.3, the other R is CH.sub.3 CF.sub.2 -, and R' is CH.sub.3, the compound is 2-methyl-1,1,1,3,3-pentafluorobutane. When one R is CHF.sub.2, the other R is CH.sub.2 F, and R' is CH.sub.3, the compound is 2-methyl-1,1,3-trifluoropropane. When one R is CHF.sub.2, the other R is CH.sub.2 F, and R' is CHF.sub.2 CH.sub.2 -, the compound is 2-fluoromethyl-1,1,4,4-tetrafluorobutane.

The present novel compounds may be prepared by adapting known methods for preparing hydrofluorocarbons. For example, 2-methyl-1,1,1,3,3-pentafluoropropane may be prepared by reacting commercially available 1,1,1-trifluoro-2-propanone with CF.sub.2 carbene to form 2-trifluoromethyl-1,1-difluoro-1-propene which may then be hydrogenated to form 2-methyl-1,1,1,3,3-pentafluoropropane.

As another example, 2-methyl-1,1,1,3-tetrafluoropropane may be prepared by reacting commercially available methacrylic acid with hydrogen fluoride to form 2-methyl-3-fluoropropanoic acid which may then be fluorinated to form 2-methyl-1,1,1,3-tetrafluoropropane.

As another example, 2-fluoromethyl-1,1,1,3,4,4-hexafluorobutane may be prepared by fluorinating commercially available 3-chloropropionic acid to form 1,1,1,3-tetrafluoropropane which may then be reacted with CHF.sub.2 CF carbene to form 2-fluoromethyl-1,1,1,3,4,4-hexafluorobutane.

As another example, 2-methyl-1,1,1,3,3-pentafluorobutane may be prepared by fluorinating commercially available 2-methyl-1-buten-3-yne to form 3-methyl-1,2,3,4-tetrafluoro-1-butene which may then be reacted with hydrogen fluoride to form 2-methyl-1,2,3,3,4-pentafluorobutane. The 2-methyl-1,2,3,3,4-pentafluorobutane may then be dehalogenated to form 3-methyl-2,3,4-trifluoro-1-butene which may then be reacted with hydrogen fluoride to form 2-methyl-1,2,3,3-tetrafluorobutane. The 2-methyl-1,2,3,3-tetrafluorobutane may then be dehalogenated to form 2-methyl-1,3,3-trifluoro-1-butene which may then be fluorinated to form 2-methyl-1,1,2,3,3-pentafluorobutane. The 2-methyl-1,1,2,3,3-pentafluorobutane may then be dehydrohalogenated to form 2-methyl-1,1,3,3-tetrafluoro-1-butene which may then be reacted with hydrogen fluoride to form 2-methyl-1,1,1,3,3-pentafluorobutane. The boiling point of 2-methyl-1,1,1,3,3-pentafluorobutane is calculated to be about 60.degree. C. Because of its boiling point, 2-methyl-1,1,1,3,3-pentafluorobutane would be particularly useful as a solvent substitute for chloroform.

For example, 2-methyl-1,1,3-trifluoropropane may be prepared by reacting commercially available fluoroacetone with a CF.sub.2 carbene to form 2-fluoromethyl-1,1,3-trifluoro-1-propene which may then be hydrogenated to form 2-methyl-1,1,3-trifluoropropane.

As another example, 2-fluoromethyl-1,1,4,4-tetrafluorobutane may be prepared by oxidizing commercially available 3-fluoro-1,2-propanediol to form a product which may then be reacted with CF.sub.2 carbene to form 2-fluoromethyl-1,1,4,4-tetrafluoro-1,3-butadiene which may then be hydrogenated to form 2-fluoromethyl-1,1,4,4-tetrafluorobutane.

Preferably, each R in the Formula above is the same. When each R is CHF.sub.2 and R' is CF.sub.3, the compound is 2-difluoromethyl-1,1,1,3,3-pentafluoropropane. When each R is CHF.sub.2 R' is CHF.sub.2, the compound is 2-difluoromethyl-1,1,3,3-tetrafluoropropane. When each R is CHF.sub.2 and R' is CH.sub.2 F, the compound is 2-fluoromethyl-1,1,3,3-tetrafluoropropane. When each R is CHF.sub.2 and R' is CH.sub.3, the compound is 2-methyl-1,1,3,3-tetrafluoropropane. When each R is CH.sub.2 F and R' is CHF.sub.2, the compound is 2-fluoromethyl-1,1,3-trifluoropropane. When each R is CH.sub.2 F and R' is CH.sub.2 F, the compound is 2-fluoromethyl-1,3-difluoropropane. When each R is CH.sub.3 CF.sub.2 - and R' is CF.sub.3, the compound is 3-trifluoromethyl-2,2,4,4-tetrafluoropentane.

As another preparation example, 2-difluoromethyl-1,1,1,3,3-pentafluoropropane may be prepared by fluorinating commercially available 1,1,1,3,3-pentachloro-2-propanone to form 1,1,1,3,3-pentafluoro-2-propanone which may then be reacted with CF.sub.2 carbene to form 2-difluoromethyl-1,1,3,3,3-tetrafluoro-1-propene. The 2-difluoromethyl-1,1,3,3,3-tetrafluoro-1-propene may then be hydrogenated to form 2-difluoromethyl-1,1,1,3,3-pentafluoropropane.

As another example, the 2-difluoromethyl-1,1,3,3-tetrafluoropropane may be prepared by fluorinating commercially available 1,1,3-trichloro-2-propanone to form 1,1,3-trifluoro-2-propanone which may then be reacted with CF.sub.2 carbene to form 2-fluoromethyl-1,1,3,3-tetrafluoro-1-propene. The 2-fluoromethyl-1,1,3,3-tetrafluoro-1-propene may then be hydrogenated to form 2-fluoromethyl-1,1,3,3-tetrafluoropropane. The 2-fluoromethyl-1,1,3,3-tetrafluoropropane may then be dehydrogenated to form 2-difluoromethyl-1,3,3-trifluoro-1-propene which may then be reacted with hydrogen fluoride to form 2-difluoromethyl-1,1,3,3-tetrafluoropropane.

As another example, 2-fluoromethyl-1,1,3,3-tetrafluoropropane may be prepared by fluorinating commercially available 1,1,3-trichloro-2-propanone to form 1,1,3-trifluoro-2-propanone which may then be reacted with CF.sub.2 carbene to form 2-fluoromethyl-1,1,3,3-tetrafluoro-1-propene. The 2-fluoromethyl-1,1,3,3-tetrafluoro-1-propene may then be hydrogenated to form 2-fluoromethyl-1,1,3,3-tetrafluoropropane.

As another example, 2-methyl-1,1,3,3-tetrafluoropropane may be prepared by fluorinating commercially available 1,1-dichloro-2-propanone to form 1,1-difluoro-2-propanone which may then be reacted with CF.sub.2 carbene to form 2-methyl-1,1,3,3-tetrafluoro-1-propene. The 2-methyl-1,1,3,3-tetrafluoro-1-propene may then be hydrogenated to form 2-methyl-1,1,3,3-tetrafluoropropane.

As another example, the 2-fluoromethyl-1,1,3-trifluoropropane may be prepared by oxidizing commercially available 1,3-difluoro-2-propanol to 1,3-difluoro-2-propanone which may then be reacted with a CF.sub.2 carbene to form 2-fluoromethyl-1,1,3-trifluoro-1-propene. The 2-fluoromethyl-1,1,3-trifluoro-1-propene may then be hydrogenated to form 2-fluoromethyl-1,1,3-trifluoropropane.

As another example, the 2-fluoromethyl-1,3-difluoropropane may be prepared by oxidizinq commercially available 1,3-difluoro-2-propanol to 1,3-difluoro-2-propanone which may then be reacted with a CF.sub.2 carbene to form 2-fluoromethyl-1,1,3-trifluoro-1-propene. The 2-fluoromethyl-1,1,3-trifluoro-1-propene may then be hydrogenated to form 2-fluoromethyl-1,1,3-trifluoropropane. The 2-fluoromethyl-1,1,3-trifluoropropane may then be dehydrohalogenated to form 2-fluoromethyl-1,3-difluoro-1-propene which may then be hydrogenated to form 2-fluoromethyl-1,3-difluoropropane.

As another example, the 3-trifluoromethyl-2,2,4,4-tetrafluoropentane may be prepared by fluorinating commercially available 2,4-pentanedione to form 2,2,4,4-tetrafluoropentane which may then be dehydrohalogenated to form 2,4,4-trifluoro-2-pentene. The 2,4,4-trifluoro-2-pentene may then be reacted with CF.sub.3 to form 3-trifluoromethyl-2,2,4,4-tetrafluoropentane.

The boiling point of 2-difluoromethyl-1,1,3,3-tetrafluoropropane is calculated to be about 61.degree. C. while the boiling point of 2-fluoromethyl-1,3-difluoropropane is calculated to be about 51.degree. C. The boiling point of 3-trifluoromethyl-2,2,4,4-tetrafluoropentane is calculated to be about 52.degree. C.

Because of its boiling point, 2-difluoromethyl-1,1,3,3-tetrafluoropropane would be particularly useful as a solvent substitute for chloroform. Because of their boiling points, 2-fluoromethyl-1,3-difluoropropane and 3-trifluoromethyl-2,2,4,4-tetrafluoropentane would be particularly useful as solvent substitutes for CFC-113

More preferably, each R in the Formula above is CF.sub.3. When R' is CF.sub.3 CF.sub.2 CHF-, the compound is 2-trifluoromethyl-1,1,1,3,4,4,5,5,5-nonafluoropentane. To prepare 2-trifluoromethyl-1,1,1,3,4,4,5,5,5-nonafluoropentane, commercially available hexafluoropropene may be oligomerized with commercially available trimethylamine in a dipolar aprotic solvent such as commercially available tetrahydrofuran to provide (CF.sub.3).sub.2 C:CFCF.sub.2 CH.sub.3 as taught by W. Brunskill et al., "Anionic Oligomerisation of Hexafluoropropene: Fission of a Carbon-Carbon Bond by Fluoride Ion", Chemical Communications, 1444 (1970); the (CF.sub.3).sub.2 C:CFCF.sub.2 CF.sub.3 may then be hydrogenated to form 2-trifluoromethyl-1,1,1,3,4,4,5,5,5-nonafluoropentane.

Most preferably, each R is CF.sub.3 and R' is selected from the group consisting of CHF.sub.2, CH.sub.3, CF.sub.3 CHF-, CF.sub.3 CH.sub.2 -, CHF.sub.2 CH.sub.2 -, CH.sub.3 CF.sub.2 -, CH.sub.3 (CF.sub.2).sub.2 -, CH.sub.3 CH.sub.2 CF.sub.2 -, and CH.sub.3 CH.sub.2 CF.sub.2 CF.sub.2 -. The names of the preceding preferred hydrofluorocarbons are 2-difluoromethyl-1,1,1,3,3,3-hexafluoropropane; 2-methyl-1,1,1,3,3,3-hexafluoropropane; 2-trifluoromethyl-1,1,1,3,4,4,4-heptafluorobutane; 2-trifluoromethyl-1,1,1,4,4,4-hexafluorobutane; 2-trifluoromethyl-1,1,1,4,4-pentafluorobutane; 2-trifluoromethyl-1,1,1,3,3-pentafluorobutane; 2-trifluoromethyl-1,1,1,3,3,4,4-heptafluoropentane; 2-trifluoromethyl-1,1,1,3,3-pentafluoropentane; and 2-trifluoromethyl-1,1,1,3,3,4,4-heptafluorohexane.

The present novel compounds may be prepared by adapting known methods for preparing hydrofluorocarbons. For example, 2-difluoromethyl-1,1,1,3,3,3-hexafluoropropane may be prepared by treating commercially available hexafluoropropene with hydrogen fluoride as taught by commonly assigned U.K. Patent 902,590 to form 1,1,1,2,3,3,3-hexafluoropropane. The 1,1,1,2,3,3,3-hexafluoropropane may then be heated at 475-700.degree. C. in the presence of activated carbon as taught by commonly assigned U.S. Pat. No. 2,981,763 which is incorporated herein by reference to form 2-trifluoromethyl-1,1,1,3,3,3-hexafluoropropane or nonafluoroisobutane. The nonafluoroisobutane may then be treated with commercially available benzoyl chloride in the presence of commercially available triethylamine as taught by B. L. Dyatkin et al., "The Perfluoro-t-butyl Anion in the Synthesis of Organofluorine Compounds", Russian Chemical Reviews 45(7) 607 (1976) to form perfluoroisobutene. The perfluoroisobutene may then by hydrogenated to form 2-difluoromethyl-1,1,1,3,3,3-hexafluoropropane.

As another example, 2-methyl-1,1,1,3,3,3-hexafluoropropane may be prepared by reacting commercially available hexafluoropropene with elemental sulfur and commercially available potassium fluoride in commercially available dimethylformamide under substantially atmospheric pressure and at temperatures between 25-100.degree. C. as taught by commonly assigned U.S. Pat. No. 4,326,068 which is incorporated herein by reference to form hexafluorothioacetone dimer. The hexafluorothioacetone dimer may then be reacted with commercially available formaldehyde as taught by commonly assigned U.S. Pat. No. 4,367,349 which is incorporated herein by reference to form hexafluoroisobutylene. The hexafluoroisobutylene may then be hydrogenated to form 2-methyl-1,1,1,3,3,3-hexafluoropropane.

As another example, 2-trifluoromethyl-1,1,1,3,4,4,4-heptafluorobutane may be prepared by reacting commercially available 1,1-difluoroethylene according to the procedure of George L. Fleming et al., "Addition of Free Radicals to Unsaturated Systems. Part XX. The Direction of Radical Addition of Heptafluoro-2-iodopropane to Vinyl Fluoride, Trifluoroethylene, and Hexafluoropropene", J.C.S. Perkin I, 574 (1973) to form a product which may then be fluorinated to form 2-trifluoromethyl-1,1,1,2,3,4,4,4-octafluorobutane. The 2-trifluoromethyl-1,1,1,2,3,4,4,4-octafluorobutane may then be dehydrohalogenated and then hydrogenated to form 2-trifluoromethyl-1,1,1,3,4,4,4-heptafluorobutane.

As another example, 2-trifluoromethyl-1,1,1,4,4,4-hexafluorobutane may be prepared by reacting commercially available 1,1-difluoroethylene according to the procedure of George L. Fleming et al., supra, to form a product which may then be reacted with hydrogen fluoride to form 2-trifluoromethyl-1,1,1,2,4,4,4-hexafluorobutane which may then be dehydrohalogenated and then hydrogenated to form 2-trifluoromethyl-1,1,1,4,4,4-hexafluorobutane.

As another example, 2-trifluoromethyl-1,1,1,4,4-pentafluorobutane may be prepared by reacting commercially available 1,1-difluoroethylene according to the procedure of George L. Fleming et al., supra, to form a product which may then be hydrogenated to form 2-trifluoromethyl-1,1,1,2,4,4-hexafluorobutane which may then be dehydrohalogenated and then hydrogenated to form 2-trifluoromethyl-1,1,1,4,4-pentafluorobutane

As another example, 2-trifluoromethyl-1,1,1,3,3-pentafluorobutane may be prepared by fluorinating commercially available 2-butanone to form 2,2-difluorobutane which may then be dehydrogenated to form 3,3-difluoro-1-butene. CF.sub.3 may then be added to the 3,3-difluoro-1-butene to form 2-trifluoromethyl-1,3,3-trifluorobutane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3-trifluoro-1-butene. The 2-trifluoromethyl-1,3,3-trifluoro-1-butene may then be reacted with hydrogen fluoride to form 2-difluoromethyl-1,1,1,3,3,3-hexafluorobutane which may then be dehyrogenated to form 2-trifluoromethyl-1,1,3,3-tetrafluoro-1-butene which may then be reacted with hydrogen fluoride to form 2-trifluoromethyl-1,1,1,3,3-pentafluorobutane.

As another example, 2-trifluoromethyl-1,1,1,3,3,4,4-heptafluoropentane may be prepared by fluorinating commercially available 2,3-pentanedione to form 2,2,3,3-tetrafluoropentane which may then be dehydrogenated to form

3,3,4,4-tetrafluoro-1-pentene. CF.sub.3 may then be added to the 3,3,4,4-tetrafluoro-1-pentene to form 2-trifluoromethyl-1,3,3,4,4-pentafluoropentane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-pentene. The 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-pentene may then be reacted with hydrogen fluoride to form 2-trifluoromethyl-1,1,3,3,4,4-hexafluoropentane which may then be dehydrogenated to form 2-trifluoromethyl-1,1,3,3,4,4-hexafluoro-1-pentene which may then be reacted with hydrogen fluoride to form 2-trifluoromethyl-1,1,1,3,3,4,4-heptafluoropentane.

As another example, 2-trifluoromethyl-1,1,1,3,3-pentafluoropentane may be prepared by fluorinating 3-pentanone to form 3,3-difluoropentane which may then be dehydrogenated to form 3,3-difluoro-1-pentene. CF.sub.3 may then be reacted with the 3,3-difluoro-1-pentene to form 2-trifluoromethyl-1,3,3-trifluoropentane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3-trifluoro-1-pentene. The 2-trifluoromethyl-1,3,3-trifluoro-1-pentene may then be reacted with hydrogen fluoride to form 2-trifluoromethyl-1,1,3,3-tetrafluoropentane which may then be dehydrogenated to form 2-trifluoromethyl-1,1,3,3-tetrafluoro-1-pentene which may then be reacted with hydrogen fluoride to form 2-trifluoromethyl-1,1,1,3,3-pentafluoropentane.

As another example, 2-trifluoromethyl-1,1,1,3,3,4,4-heptafluorohexane may be prepared by fluorinating commercially available 3,4-hexanedione to form 3,3,4,4-tetrafluorohexane which may then be dehydrogenated to form 3,3,4,4-tetrafluoro-1-hexene. CF.sub.3 may then be added to the 3,3,4,4-tetrafluoro-1-hexene to form 2-trifluoromethyl-1,3,3,4,4-pentafluorohexane which may then be dehydrogenated to form 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-hexene. The 2-trifluoromethyl-1,3,3,4,4-pentafluoro-1-hexene may then be reacted with hydrogen fluoride to form 2-trifluoromethyl-1,1,3,3,4,4-hexafluorohexane which may then be dehydrogenated to form 2-trifluoromethyl-1,1,3,3,4,4-hexafluoro-1-hexene which may then be reacted with hydrogen fluoride to form 2-trifluoromethyl-1,1,1,3,3,4,4-heptafluorohexane.

The boiling point of 2-difluoromethyl-1,1,1,3,3,3-hexafluoropropane is calculated to be about 38.degree. C. while the boiling point of 2-methyl-1,1,1,3,3,3-hexafluoropropane is calculated to be about 30.degree. C. The boiling point of 2-trifluoromethyl-1,1,1,4,4,4-hexafluorobutane is calculated to be about 75.degree. C. The boiling point of 2-trifluoromethyl-1,1,1,3,3-pentafluoropentane is calculated to be about 38.degree. C. while the boiling point of 2-trifluoromethyl-1,1,1,3,3,4,4-heptafluorohexane is calculated to be about 55.degree. C.

The present novel compounds are useful as solvents in a variety of vapor degreasing, cold cleaning, and solvent cleaning applications including defluxing and dry cleaning. Because of their boiling points, 2-difluoromethyl-1,1,1,3,3,3-hexafluoropropane, 2-methyl-1,1,1,3,3,3-hexafluoropropane, 2-trifluoromethyl-1,1,1,3,3-pentafluoropentane, and 2-trifluoromethyl-1,1,1,3,3,4,4-heptafluorohexane would be useful as solvent substitutes for CFC-113. Because of its boiling point, 2-trifluoromethyl-1,1,1,4,4,4-hexafluorobutane would be particularly useful as a solvent substitute for chloroform and perchloroethylene.

The present invention also provides a method of cleaning a solid surface which comprises treating the surface with a compound having the Formula: ##STR3## wherein each R is the same or different and is selected from the group consisting of CF.sub.3, CHF.sub.2, CH.sub.2 F, and CH.sub.3 CF.sub.2, and R' is an alkyl or fluoroalkyl group having 1 to 6 carbon atoms.

Preferably, R' in the Formula above is selected from the group consisting of CF.sub.3, CHF.sub.2, CH.sub.2 F, CH.sub.3, CF.sub.3 (CF.sub.2).sub.n -, CF.sub.3 CF.sub.2 CHF-, CF.sub.3 CF.sub.2 CH.sub.2 -, CF.sub.3 (CHF).sub.n -, CF.sub.3 CHFCF.sub.2 -, CF.sub.3 CHFCH.sub.2 -, CF.sub.3 (CH.sub.2).sub.n -, CF.sub.3 CH.sub.2 CF.sub.2 -, CF.sub.3 CH.sub.2 CHF-, CHF.sub.2 (CF.sub.2).sub.n -, CHF.sub.2 CF.sub.2 CHF-, CHF.sub.2 CF.sub.2 CH.sub.2 -, CHF.sub.2 (CHF).sub.n -, CHF.sub.2 CHFCF.sub.2 -, CHF.sub.2 CHFCH.sub.2 -, CHF.sub.2 (CH.sub.2).sub.n -, CHF.sub.2 CH.sub.2, CF.sub.2 -, CHF.sub.2 CH.sub.2 CHF-, CH.sub.2 F(CF.sub.2).sub.n -, CH.sub.2 FCF.sub.2 CHF-, CH.sub.2 FCF.sub.2 CH.sub.2 -, CH.sub.2 F(CHF).sub.n -, CH.sub.2 FCHFCF.sub.2 -, CH.sub.2 FCHFCH.sub.2 -, CH.sub.2 F(CH.sub.2).sub.n -, CH.sub.2 FCH.sub.2 CF.sub.2 -, CH.sub.2 FCH.sub.2 CHF-, CH.sub.3 (CF.sub.2).sub.n -, CH.sub.3,CF.sub.2 CH-, CH.sub. 3 CF.sub.2 CH.sub.2 -, CH.sub.3 (CHF).sub.n -, CH.sub.3 CHFCF.sub.2 -, CH.sub.3 CHFCH.sub.2 -, and CH.sub.3 (CH.sub.2)m(CF.sub.2)n, and m is 1 to 3, and n is 1 or 2.

Preferably, each R in the Formula above is the same and more preferably, each R in the Formula above is CF.sub.3.

When R' is CF.sub.3 CF.sub.2 CF.sub.2 -, the compound is 2-trifluoromethyl-1,1,1,3,3,4,4,5,5,5-decafluoropentane. To prepare 2-trifluoromethyl-1,1,1,3,3,4,4,5,5,5-decafluoropentane, any method known in the art may be used. For example, commercially available hexafluoropropene may be oligomerized with commercially available trimethylamine in a dipolar aprotic solvent such as commercially available tetrahydrofuran to provide (CF.sub.3).sub.2 C:CFCF.sub.2 CF.sub.3 which is then reacted with commercially available hydrogen fluoride to yield 2-trifluoromethyl-1,1,1,3,3,4,4,5,5,5-decafluoropentane as taught by W. Brunskill et al., "Anionic Oligomerisation of Hexafluoropropene: Fission of a Carbon-Carbon Bond by Fluoride Ion", Chemical Communications, 1444 (1970).

When R' is CF.sub.3 CF.sub.2 -, the compound is 2-trifluoromethyl-1,1,1,3,3,4,4,4-octafluorobutane. To prepare 2-trifluoromethyl-1,1,1,3,3,4,4,4-octafluorobutane any method known in the art may be used. For example, 2-trifluoromethyl-1,1,1,3,3,4,4,4-octafluorobutane may be prepared by reacting caesium fluoride and perfluoro-3-methylbut-1-ene in moist sulpholan as taught by Robert N. Haszeldine et al., "Fluoro-olefin Chemistry. Part II. Some Reactions of Perfluoro-3-methylbut-1-ene under Ionic and Free-radical Conditions", J. Chem. Soc. 565 (1979).

When R' is CF.sub.3, the compound is 2-trifluoromethyl-1,1,1,3,3,3-hexafluoropropane. To prepare 2-trifluoromethyl-1,1,1,3,3,3-hexafluoropropane, any method known in the art may be used. For example, commercially available hexafluoropropene may be reacted with hydrogen fluoride to form 1,1,1,2,3,3,3-heptafluoropropane which may then be heated at about 475-700.degree. C. in the presence of activated carbon to form 2-trifluoromethyl-1,1,1,3,3,3-hexafluoropropane as taught by commonly assigned U.S. Pat. No. 2,981,763 which is incorporated herein by reference.

The boiling point of 2-trifluoromethyl-1,1,1,3,3,4,4,4-octafluorobutane is calculated to be about 47.degree. C. Because of its boiling point, 2-trifluoromethyl-1,1,1,3,3,4,4,4-octafluorobutane would be particularly useful as a solvent substitute for CFC-113.

In the process embodiment of the invention, the compositions may be used to clean solid surfaces by treating the surface with the compounds in any manner well known to the art such as by dipping or spraying or use of conventional degreasing apparatus.

When the novel compounds are used to clean solid surfaces by spraying the surfaces with the compounds, preferably, the novel compounds are sprayed onto the surfaces by using a propellant. Preferably, the propellant is selected from the group consisting of hydrochlorofluorocarbon, hydrofluorocarbon, and mixtures thereof. Useful hydrochlorofluorocarbon propellants include dichlorofluoromethane (known in the art as HCFC-21), chlorodifluoromethane (known in the art as HCFC-22)1,1-dichloro-2,2-difluoroethane (known in the art as HCFC-132a), 1-chloro-2,2,2-trifluoroethane (known in the art as HCFC-133), and 1-chloro-1,1-difluoroethane (known in the art as HCFC-142b); commercially available HCFC-21, HCFC-22, and HCFC-142b may be used in the present invention. Useful hydrofluorocarbon propellants include trifluoromethane (known in the art as HFC-23), 1,1,1,2-tetrafluoroethane (known in the art as HFC-134a), and 1,1-difluoroethane (known in the art as HFC-152a); commercially available HFC-23and HFC-152a may be used in the present invention. Until HFC-134a becomes available in commercial quantities, HFC-134a may be made by a known method such as that disclosed by U.S. Pat. No. 4,851,595. Preferred propellants include chlorodifluoromethane and 1,1,1,2-tetrafluoroethane.

The present partially fluorinated alkanes may also be used as blowing agents for preparing foam as disclosed in commonly assigned concurrently filed patent application U.S. Ser. No. 07,546,173 which is incorporated herein by reference.

The present invention is more fully illustrated by the following non-limiting Examples.

EXAMPLES 1-540

For each example, the novel compound of the Formula above having the R and R' groups as indicated in Table I below is made.

TABLE I______________________________________Example R R'______________________________________ 1 CF.sub.3, CHF.sub.2 CF.sub.3 2 CF.sub.3, CHF.sub.2 CHF.sub.2 3 CF.sub.3, CHF.sub.2 CH.sub.2 F 4 CF.sub.3, CHF.sub.2 CH.sub.3 5 CF.sub.3, CHF.sub.2 CF.sub.3 CF.sub.2 6 CF.sub.3, CHF.sub.2 CF.sub.3 (CF.sub.2).sub.2 7 CF.sub.3, CHF.sub.2 CF.sub.3 CF.sub.2 CHF 8 CF.sub.3, CHF.sub.2 CF.sub.3 CF.sub.2 CH.sub.2 9 CF.sub.3, CHF.sub.2 CF.sub.3 CHF 10 CF.sub.3, CHF.sub.2 CF.sub.3 (CHF).sub.2 11 CF.sub.3, CHF.sub.2 CF.sub.3 CHFCF.sub.2 12 CF.sub.3, CHF.sub.2 CF.sub.3 CHFCH.sub.2 13 CF.sub.3, CHF.sub.2 CF.sub.3 CH.sub.2 14 CF.sub.3, CHF.sub.2 CF.sub.3 (CH.sub.2).sub.2 15 CF.sub.3, CHF.sub.2 CF.sub.3 CH.sub.2 CF.sub.2 16 CF.sub.3, CHF.sub.2 CF.sub.3 CH.sub.2 CHF 17 CF.sub.3, CHF.sub.2 CHF.sub. 2 CF.sub.2 18 CF.sub.3, CHF.sub.2 CHF.sub.2 (CF.sub.2).sub.2 19 CF.sub.3, CHF.sub.2 CHF.sub.2 CF.sub.2 CHF 20 CF.sub.3, CHF.sub.2 CHF.sub.2 CF.sub.2 CH.sub.2 21 CF.sub.3, CHF.sub.2 CHF.sub.2 CHF 22 CF.sub.3, CHF.sub.2 CHF.sub.2 (CHF).sub.2 23 CF.sub.3, CHF.sub.2 CHF.sub.2 CHFCF.sub.2 24 CF.sub.3, CHF.sub.2 CHF.sub.2 CHFCH.sub.2 25 CF.sub.3, CHF.sub.2 CHF.sub.2 CH.sub.2 26 CF.sub.3, CHF.sub.2 CHF.sub.2 (CH.sub.2).sub.2 27 CF.sub.3, CHF.sub.2 CHF.sub.2 CH.sub.2 CF.sub.2 28 CF.sub.3, CHF.sub.2 CHF.sub.2 CH.sub.2 CHF 29 CF.sub.3, CHF.sub.2 CH.sub.2 FCF.sub.2 30 CF.sub.3, CHF.sub.2 CH.sub.2 F(CF.sub.2).sub.2 31 CF.sub.3, CHF.sub.2 CH.sub.2 FCF.sub.2 CHF 32 CF.sub.3, CHF.sub.2 CH.sub.2 FCF.sub.2 CH.sub.2 33 CF.sub.3, CHF.sub.2 CH.sub.2 FCHF 34 CF.sub.3, CHF.sub.2 CH.sub. 2 F(CHF).sub.2 35 CF.sub.3, CHF.sub.2 CH.sub.2 FCHFCF.sub.2 36 CF.sub.3, CHF.sub.2 CH.sub.2 FCHFCH.sub.2 37 CF.sub.3, CHF.sub.2 CH.sub.2 FCH.sub.2 38 CF.sub.3, CHF.sub.2 CH.sub.2 F(CH.sub.2).sub.2 39 CF.sub.3, CHF.sub.2 CH.sub.2 FCH.sub.2 CF.sub.2 40 CF.sub.3, CHF.sub.2 CH.sub.2 FCH.sub.2 CHF 41 CF.sub.3, CHF.sub.2 CH.sub.3 CF.sub.2 42 CF.sub.3, CHF.sub.2 CH.sub.3 (CF.sub.2).sub.2 43 CF.sub.3, CHF.sub.2 CH.sub.3 CF.sub.2 CHF 44 CF.sub.3, CHF.sub.2 CH.sub.3 CF.sub.2 CH.sub.2 45 CF.sub.3, CHF.sub.2 CH.sub.3 CHF 46 CF.sub.3, CHF.sub.2 CH.sub.3 (CHF).sub.2 47 CF.sub.3, CHF.sub.2 CH.sub.3 CHFCF.sub.2 48 CF.sub.3, CHF.sub.2 CH.sub.3 CHFCH.sub.2 49 CF.sub.3, CHF.sub.2 CH.sub.3 CH.sub.2 CF.sub.2 50 CF.sub.3, CHF.sub.2 CH.sub.3 CH.sub.2 (CF.sub.2).sub.2 51 CF.sub.3, CHF.sub. 2 CH.sub.3 (CH.sub.2).sub.2 CF.sub.2 52 CF.sub.3, CHF.sub.2 CH.sub.3 (CH.sub.2).sub.2 (CF.sub.2).sub.2 53 CF.sub.3, CHF.sub.2 CH.sub.3 (CH.sub.2).sub.3 CF.sub.2 54 CF.sub.3, CHF.sub.2 CH.sub.3 (CH.sub.2).sub.3 (CF.sub.2).sub.2 55 CF.sub.3, CH.sub.2 F CF.sub.3 56 CF.sub.3, CH.sub.2 F CHF.sub.2 57 CF.sub.3, CH.sub.2 F CH.sub.2 F 58 CF.sub.3, CH.sub.2 F CH.sub.3 59 CF.sub.3, CH.sub.2 F CF.sub.3 CF.sub.2 60 CF.sub.3, CH.sub.2 F CF.sub.3 (CF.sub.2).sub.2 61 CF.sub.3, CH.sub.2 F CF.sub.3 CF.sub.2 CHF 62 CF.sub.3, CH.sub.2 F CF.sub.3 CF.sub.2 CH.sub.2 63 CF.sub.3, CH.sub.2 F CF.sub.3 CHF 64 CF.sub.3, CH.sub.2 F CF.sub.3 (CHF).sub.2 65 CF.sub.3, CH.sub.2 F CF.sub.3 CHFCF.sub.2 66 CF.sub.3, CH.sub.2 F CF.sub.3 CHFCH.sub.2 67 CF.sub.3, CH.sub.2 F CF.sub.3 CH.sub.2 68 CF.sub.3, CH.sub.2 F CF.sub.3 (CH.sub.2).sub.2 69 CF.sub.3, CH.sub.2 F CF.sub.3 CH.sub.2 CF.sub.2 70 CF.sub.3, CH.sub.2 F CF.sub.3 CH.sub.2 CHF 71 CF.sub.3, CH.sub.2 F CHF.sub.2 CF.sub.2 72 CF.sub.3, CH.sub.2 F CHF.sub.2 (CF.sub.2).sub.2 73 CF.sub.3, CH.sub.2 F CHF.sub.2 CF.sub.2 CHF 74 CF.sub.3, CH.sub.2 F CHF.sub.2 CF.sub.2 CH.sub.2 75 CF.sub.3, CH.sub.2 F CHF.sub.2 CHF 76 CF.sub.3, CH.sub.2 F CHF.sub.2 (CHF).sub.2 77 CF.sub.3, CH.sub.2 F CHF.sub.2 CHFCF.sub.2 78 CF.sub.3, CH.sub.2 F CHF.sub.2 CHFCH.sub.2 79 CF.sub.3, CH.sub.2 F CHF.sub.2 CH.sub.2 80 CF.sub.3, CH.sub.2 F CHF.sub.2 (CH.sub.2).sub.2 81 CF.sub.3, CH.sub.2 F CHF.sub.2 CH.sub.2 CF.sub.2 82 CF.sub.3, CH.sub.2 F CHF.sub.2 CH.sub.2 CHF 83 CF.sub.3, CH.sub.2 F CH.sub.2 FCF.sub.2 84 CF.sub.3, CH.sub.2 F CH.sub.2 F(CF.sub.2).sub.2 85 CF.sub.3, CH.sub.2 F CH.sub.2 FCF.sub.2 CHF 86 CF.sub.3, CH.sub.2 F CH.sub.2 FCF.sub.2 CH.sub.2 87 CF.sub.3, CH.sub.2 F CH.sub.2 FCHF 88 CF.sub.3, CH.sub.2 F CH.sub.2 F(CHF).sub.2 89 CF.sub.3, CH.sub.2 F CH.sub.2 FCHFCF.sub.2 90 CF.sub.3, CH.sub.2 F CH.sub.2 FCHFCH.sub.2 91 CF.sub.3, CH.sub.2 F CH.sub.2 FCH.sub.2 92 CF.sub.3, CH.sub.2 F CH.sub.2 F(CH.sub.2).sub.2 93 CF.sub.3, CH.sub.2 F CH.sub.2 FCH.sub.2 CF.sub.2 94 CF.sub.3, CH.sub.2 F CH.sub.2 FCH.sub.2 CHF 95 CF.sub.3, CH.sub.2 F CH.sub.3 CF.sub.2 96 CF.sub.3, CH.sub.2 F CH.sub.3 (CF.sub.2).sub.2 97 CF.sub.3, CH.sub.2 F CH.sub.3 CF.sub.2 CHF 98 CF.sub.3, CH.sub.2 F CH.sub.3 CF.sub.2 CH.sub.2 99 CF.sub.3, CH.sub.2 F CH.sub.3 CHF100 CF.sub.3, CH.sub.2 F CH.sub.3 (CHF).sub.2101 CF.sub.3, CH.sub.2 F CH.sub.3 CHFCF.sub.2102 CF.sub.3, CH.sub.2 F CH.sub.3 CHFCH.sub.2103 CF.sub.3, CH.sub.2 F CH.sub.3 CH.sub.2 CF.sub.2104 CF.sub.3, CH.sub.2 F CH.sub.3 CH.sub.2 (CF.sub.2).sub.2105 CF.sub.3, CH.sub.2 F CH.sub.3 (CH.sub.2).sub.2 CF.sub.2106 CF.sub.3, CH.sub.2 F CH.sub.3 (CH.sub.2).sub.2 (CF.sub.2).sub.2107 CF.sub.3, CH.sub.2 F CH.sub.3 (CH.sub.2).sub.3 CF.sub.2108 CF.sub.3, CH.sub.2 F CH.sub.3 (CH.sub.2).sub.3 (CF.sub.2).sub.2109 CF.sub.3, CH.sub.3 CF.sub.2 CF.sub.3110 CF.sub.3, CH.sub.3 CF.sub.2 CHF.sub.2111 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.2 F112 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.3113 CF.sub.3, CH.sub.3 CF.sub.2 CF.sub.3 CF.sub. 2114 CF.sub.3, CH.sub.3 CF.sub.2 CF.sub.3 (CF.sub.2).sub.2115 CF.sub.3, CH.sub.3 CF.sub.2 CF.sub.3 CF.sub.2 CHF116 CF.sub.3, CH.sub.3 CF.sub.2 CF.sub.3 CF.sub.2 CH.sub.2117 CF.sub.3, CH.sub.3 CF.sub.2 CF.sub.3 CHF118 CF.sub.3, CH.sub.3 CF.sub.2 CF.sub.3 (CHF).sub.2119 CF.sub.3, CH.sub.3 CF.sub.2 CF.sub.3 CHFCF.sub.2120 CF.sub.3, CF.sub.3 CF.sub.2 CF.sub.3 CHFCH.sub.2121 CF.sub.3, CH.sub.3 CF.sub.2 CF.sub.3 CH.sub.2122 CF.sub.3, CH.sub.3 CF.sub.2 CF.sub.3 (CH.sub.2).sub.2123 CF.sub.3, CH.sub.3 CF.sub.2 CF.sub.3 CH.sub.2 CF.sub.2124 CF.sub.3, CH.sub.3 CF.sub.2 CF.sub.3 CH.sub.2 CHF125 CF.sub.3, CH.sub.3 CF.sub.2 CHF.sub.2 CF.sub.2126 CF.sub.3, CH.sub.3 CF.sub.2 CHF.sub.2 (CF.sub.2).sub.2127 CF.sub.3, CH.sub.3 CF.sub.2 CHF.sub.2 CF.sub.2 CHF128 CF.sub.3, CH.sub.3 CF.sub.2 CHF.sub.2 CF.sub.2 CH.sub.2129 CF.sub.3, CH.sub. 3 CF.sub.2 CHF.sub.2 CHF130 CF.sub.3, CH.sub.3 CF.sub.2 CHF.sub.2 (CHF).sub.2131 CF.sub.3, CH.sub.3 CF.sub.2 CHF.sub.2 CHFCF.sub.2132 CF.sub.3, CH.sub.3 CF.sub.2 CHF.sub.2 CHFCH.sub.2133 CF.sub.3, CH.sub.3 CF.sub.2 CHF.sub.2 CH.sub.2134 CF.sub.3, CH.sub.3 CF.sub.2 CHF.sub.2 (CH.sub.2).sub.2135 CF.sub.3, CH.sub.3 CF.sub.2 CHF.sub.2 CH.sub.2 CF.sub.2136 CF.sub.3, CH.sub.3 CF.sub.2 CHF.sub.2 CH.sub.2 CHF137 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.2 FCF.sub.2138 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.2 F(CF.sub.2).sub.2139 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.2 FCF.sub.2 CHF140 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.2 FCF.sub.2 CH.sub.2141 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.2 FCHF142 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.2 F(CHF).sub.2143 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.2 FCHFCF.sub.2144 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.2 FCHFCH.sub.2145 CF.sub.3, CH.sub. 3 CF.sub.2 CH.sub.2 FCH.sub.2146 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.2 F(CH.sub.2).sub.2147 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.2 FCH.sub.2 CF.sub.2148 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.2 FCH.sub.2 CHF149 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.3 CF.sub.2150 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.3 (CF.sub.2).sub.2151 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.3 CF.sub.2 CHF152 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.3 CF.sub.2 CH.sub.2153 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.3 CHF154 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.3 (CHF).sub.2155 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.3 CHFCF.sub.2156 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.3 CHFCH.sub.2157 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.3 CH.sub.2 CF.sub.2158 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.3 CH.sub.2 (CF.sub.2).sub.2159 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.3 (CH.sub.2).sub.2 CF.sub.2160 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.3 (CH.sub.2).sub.2 (CF.sub.2).sub.2161 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.3 (CH.sub.2).sub.3 CF.sub.2162 CF.sub.3, CH.sub.3 CF.sub.2 CH.sub.3 (CH.sub.2).sub.3 (CF.sub.2).sub.2163 CHF.sub.2, CH.sub.2 F CF.sub.3164 CHF.sub.2, CH.sub.2 F CHF.sub.2165 CHF.sub.2, CH.sub.2 F CH.sub.2 F166 CHF.sub.2, CH.sub.2 F CH.sub.3167 CHF.sub.2, CH.sub.2 F CF.sub.3 CF.sub.2168 CHF.sub.2, CH.sub.2 F CF.sub.3 (CF.sub.2).sub.2169 CHF.sub.2, CH.sub.2 F CF.sub.3 CF.sub.2 CHF170 CHF.sub.2, CH.sub.2 F CF.sub.3 CF.sub.2 CH.sub.2171 CHF.sub.2, CH.sub.2 F CF.sub.3 CHF172 CHF.sub.2, CH.sub.2 F CF.sub.3 (CHF).sub.2173 CHF.sub.2, CH.sub.2 F CF.sub.3 CHFCF.sub.2174 CHF.sub.2, CH.sub.2 F CF.sub.3 CHFCH.sub.2175 CHF.sub.2, CH.sub.2 F CF.sub.3 CH.sub.2176 CHF.sub.2, CH.sub.2 F CF.sub.3 (CH.sub.2).sub.2177 CHF.sub.2, CH.sub.2 F CF.sub.3 CH.sub.2 CF.sub.2178 CHF.sub.2, CH.sub.2 F CF.sub.3 CH.sub.2 CHF179 CHF.sub.2, CH.sub.2 F CHF.sub.2 CF.sub.2180 CHF.sub.2, CH.sub.2 F CHF.sub.2 (CF.sub.2).sub.2181 CHF.sub.2, CH.sub.2 F CHF.sub.2 CF.sub.2 CHF182 CHF.sub.2, CH.sub.2 F CHF.sub.2 CF.sub.2 CH.sub.2183 CHF.sub.2, CH.sub.2 F CHF.sub.2 CHF184 CHF.sub.2, 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CH.sub.3 (CH.sub.2).sub.3 CF.sub.2378 CF.sub.3, CF.sub.3 CH.sub.3 (CH.sub.2).sub.3 (CF.sub.2).sub.2379 CHF.sub.2, CHF.sub.2 CF.sub.3380 CHF.sub.2, CHF.sub.2 CHF.sub.2381 CHF.sub.2, CHF.sub.2 CH.sub.2 F382 CHF.sub.2, CHF.sub.2 CH.sub.3383 CHF.sub.2, CHF.sub.2 CF.sub.3 CF.sub.2384 CHF.sub.2, CHF.sub.2 CF.sub.3 (CF.sub.2).sub.2385 CHF.sub.2, CHF.sub.2 CF.sub.3 CF.sub.2 CHF386 CHF.sub.2, CHF.sub.2 CF.sub.3 CF.sub.2 CH.sub.2387 CHF.sub.2, CHF.sub.2 CF.sub.3 CHF388 CHF.sub.2, CHF.sub.2 CF.sub.3 (CHF).sub.2389 CHF.sub.2, CHF.sub.2 CF.sub.3 CHFCF.sub.2390 CHF.sub.2, CHF.sub.2 CF.sub.3 CHFCH.sub.2391 CHF.sub.2, CHF.sub.2 CF.sub. 3 CH.sub.2392 CHF.sub.2, CHF.sub.2 CF.sub.3 (CH.sub.2).sub.2393 CHF.sub.2, CHF.sub.2 CF.sub.3 CH.sub.2 CF.sub.2394 CHF.sub.2, CHF.sub.2 CF.sub.3 CH.sub.2 CHF395 CHF.sub.2, CHF.sub.2 CHF.sub.2 CF.sub.2396 CHF.sub.2, CHF.sub.2 CHF.sub.2 (CF.sub.2).sub.2397 CHF.sub.2, CHF.sub.2 CHF.sub.2 CF.sub.2 CHF398 CHF.sub.2, CHF.sub.2 CHF.sub.2 CF.sub.2 CH.sub.2399 CHF.sub.2, CHF.sub.2 CHF.sub.2 CHF400 CHF.sub.2, CHF.sub.2 CHF.sub.2 (CHF).sub.2401 CHF.sub.2, CHF.sub.2 CHF.sub.2 CHFCF.sub.2402 CHF.sub.2, CHF.sub.2 CHF.sub.2 CHFCH.sub.2403 CHF.sub.2, CHF.sub.2 CHF.sub.2 CH.sub.2404 CHF.sub.2, CHF.sub.2 CHF.sub.2 (CH.sub.2).sub.2405 CHF.sub.2, CHF.sub.2 CHF.sub.2 CH.sub.2 CF.sub.2406 CHF.sub.2, CHF.sub.2 CHF.sub.2 CH.sub.2 CHF407 CHF.sub.2, CHF.sub.2 CH.sub.2 FCF.sub.2408 CHF.sub.2, CHF.sub.2 CH.sub.2 F(CF.sub.2).sub.2409 CHF.sub.2, CHF.sub.2 CH.sub.2 FCF.sub.2 CHF410 CHF.sub.2, CHF.sub.2 CH.sub.2 FCF.sub.2 CH.sub.2411 CHF.sub.2, CHF.sub.2 CH.sub.2 FCHF412 CHF.sub.2, CHF.sub.2 CH.sub.2 F(CHF).sub.2413 CHF.sub.2, CHF.sub.2 CH.sub.2 FCHFCF.sub.2414 CHF.sub.2, CHF.sub.2 CH.sub.2 FCHFCH.sub.2415 CHF.sub.2, CHF.sub.2 CH.sub.2 FCH.sub.2416 CHF.sub.2, CHF.sub.2 CH.sub.2 F(CH.sub.2).sub.2417 CHF.sub.2, CHF.sub.2 CH.sub.2 FCH.sub.2 CF.sub.2418 CHF.sub.2, CHF.sub.2 CH.sub.2 FCH.sub.2 CHF419 CHF.sub.2, CHF.sub.2 CH.sub.3 CF.sub.2420 CHF.sub.2, CHF.sub.2 CH.sub.3 (CF.sub.2).sub.2421 CHF.sub.2, CHF.sub.2 CH.sub.3 CF.sub.2 CHF422 CHF.sub.2, CHF.sub.2 CH.sub.3 CF.sub.2 CH.sub.2423 CHF.sub.2, CHF.sub.2 CH.sub.3 CHF424 CHF.sub.2, CHF.sub.2 CH.sub.3 (CHF).sub.2425 CHF.sub.2, CHF.sub.2 CH.sub.3 CHFCF.sub.2426 CHF.sub.2, CHF.sub.2 CH.sub.3 CHFCH.sub.2427 CHF.sub.2, CHF.sub.2 CH.sub.3 CH.sub.2 CF.sub.2428 CHF.sub.2, CHF.sub.2 CH.sub.3 CH.sub.2 (CF.sub.2).sub.2429 CHF.sub.2, CHF.sub.2 CH.sub.3 (CH.sub.2).sub.2 CF.sub.2430 CHF.sub.2, CHF.sub.2 CH.sub.3 (CH.sub.2).sub.2 (CF.sub.2).sub.2431 CHF.sub.2, CHF.sub.2 CH.sub.3 (CH.sub.2).sub.3 CF.sub.2432 CHF.sub.2, CHF.sub.2 CH.sub.3 (CH.sub.2).sub.3 (CF.sub.2).sub.2433 CH.sub.2 F, CH.sub.2 F CF.sub.3434 CH.sub.2 F, CH.sub.2 F CHF.sub.2435 CH.sub.2 F, CH.sub.2 F CH.sub.2 F436 CH.sub.2 F, CH.sub.2 F CH.sub.3437 CH.sub.2 F, CH.sub.2 F CF.sub.3 CF.sub.2438 CH.sub.2 F, CH.sub.2 F CF.sub.3 (CF.sub.2).sub.2439 CH.sub.2 F, CH.sub.2 F CF.sub.3 CF.sub.2 CHF440 CH.sub.2 F, CH.sub.2 F CF.sub.3 CF.sub.2 CH.sub.2441 CH.sub.2 F, CH.sub.2 F CF.sub.3 CHF442 CH.sub.2 F, CH.sub.2 F CF.sub.3 (CHF).sub.2443 CH.sub.2 F, CH.sub.2 F CF.sub.3 CHFCF.sub.2444 CH.sub.2 F, CH.sub.2 F CF.sub.3 CHFCH.sub.2445 CH.sub.2 F, CH.sub. 2 F CF.sub.3 CH.sub.2446 CH.sub.2 F, CH.sub.2 F CF.sub.3 (CH.sub.2).sub.2447 CH.sub.2 F, CH.sub.2 F CF.sub.3 CH.sub.2 CF.sub.2448 CH.sub.2 F, CH.sub.2 F CF.sub.3 CH.sub.2 CHF449 CH.sub.2 F, CH.sub.2 F CHF.sub.2 CF.sub.2450 CH.sub.2 F, CH.sub.2 F CHF.sub.2 (CF.sub.2).sub.2451 CH.sub.2 F, CH.sub.2 F CHF.sub.2 CF.sub.2 CHF452 CH.sub.2 F, CH.sub.2 F CHF.sub.2 CF.sub.2 CH.sub.2453 CH.sub.2 F, CH.sub.2 F CHF.sub.2 CHF454 CH.sub.2 F, CH.sub.2 F CHF.sub.2 (CHF).sub.2455 CH.sub.2 F, CH.sub.2 F CHF.sub.2 CHFCF.sub.2456 CH.sub.2 F, CH.sub.2 F CHF.sub.2 CHFCH.sub.2457 CH.sub.2 F, CH.sub.2 F CHF.sub.2 CH.sub.2458 CH.sub.2 F, CH.sub.2 F CHF.sub.2 (CH.sub.2).sub.2459 CH.sub.2 F, CH.sub.2 F CHF.sub.2 CH.sub.2 CF.sub.2460 CH.sub.2 F, CH.sub.2 F CHF.sub.2 CH.sub.2 CHF461 CH.sub.2 F, CH.sub.2 F CH.sub.2 FCF.sub.2462 CH.sub.2 F, CH.sub.2 F CH.sub.2 F(CF.sub.2).sub.2463 CH.sub.2 F, CH.sub.2 F CH.sub.2 FCF.sub.2 CHF464 CH.sub.2 F, CH.sub.2 F CH.sub.2 FCF.sub.2 CH.sub.2465 CH.sub.2 F, CH.sub.2 F CH.sub.2 FCHF466 CH.sub.2 F, CH.sub.2 F CH.sub.2 F(CHF).sub.2467 CH.sub.2 F, CH.sub.2 F CH.sub.2 FCHFCF.sub.2468 CH.sub.2 F, CH.sub.2 F CH.sub.2 FCHFCH.sub.2469 CH.sub.2 F, CH.sub.2 F CH.sub.2 FCH.sub.2470 CH.sub.2 F, CH.sub.2 F CH.sub.2 F(CH.sub.2).sub.2471 CH.sub.2 F, CH.sub.2 F CH.sub.2 FCH.sub.2 CF.sub.2472 CH.sub.2 F, CH.sub.2 F CH.sub.2 FCH.sub.2 CHF473 CH.sub.2 F, CH.sub.2 F CH.sub.3 CF.sub.2474 CH.sub.2 F, CH.sub.2 F CH.sub.3 (CF.sub.2).sub.2475 CH.sub.2 F, CH.sub.2 F CH.sub.3 CF.sub.2 CHF476 CH.sub.2 F, CH.sub.2 F CH.sub.3 CF.sub.2 CH.sub.2477 CH.sub.2 F, CH.sub.2 F CH.sub.3 CHF478 CH.sub.2 F, CH.sub.2 F CH.sub.3 (CHF).sub.2479 CH.sub.2 F, CH.sub.2 F CH.sub.3 CHFCF.sub.2480 CH.sub.2 F, CH.sub.2 F CH.sub.3 CHFCH.sub.2481 CH.sub.2 F, CH.sub.2 F CH.sub.3 CH.sub.2 CF.sub.2482 CH.sub.2 F, CH.sub.2 F CH.sub.3 CH.sub.2 (CF.sub.2).sub.2483 CH.sub.2 F, CH.sub.2 F CH.sub.3 (CH.sub.2).sub.2 CF.sub.2484 CH.sub.2 F, CH.sub.2 F CH.sub.3 (CH.sub.2).sub.2 (CF.sub.2).sub.2485 CH.sub.2 F, CH.sub.2 F CH.sub.3 (CH.sub.2).sub.3 CF.sub.2486 CH.sub.2 F, CH.sub.2 F CH.sub.3 (CH.sub.2).sub.3 (CF.sub.2).sub.2487 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CF.sub.3488 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CHF.sub.2489 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.2 F490 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.3491 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CF.sub.3 CF.sub.2492 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CF.sub.3 (CF.sub.2).sub.2493 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CF.sub.3 CF.sub.2 CHF494 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CF.sub.3 CF.sub.2 CH.sub.2495 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CF.sub.3 CHF496 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CF.sub.3 (CHF).sub.2497 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CF.sub.3 CHFCF.sub.2498 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CF.sub.3 CHFCH.sub.2499 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CF.sub.3 CH.sub.2500 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CF.sub.3 (CH.sub.2).sub.2501 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CF.sub.3 CH.sub.2 CF.sub.2502 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CF.sub.3 CH.sub.2 CHF503 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CHF.sub.2 CF.sub.2504 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CHF.sub.2 (CF.sub.2).sub.2505 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CHF.sub.2 CF.sub.2 CHF506 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CHF.sub.2 CF.sub.2 CH.sub.2507 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CHF.sub.2 CHF508 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CHF.sub.2 (CHF).sub.2509 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CHF.sub.2 CHFCF.sub.2510 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CHF.sub.2 CHFCH.sub.2511 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CHF.sub.2 CH.sub.2512 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CHF.sub.2 (CH.sub.2).sub.2513 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CHF.sub.2 CH.sub.2 CF.sub.2514 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CHF.sub.2 CH.sub.2 CHF515 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.2 FCF.sub.2516 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.2 F(CF.sub.2).sub.2517 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.2 FCF.sub.2 CHF518 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.2 FCF.sub.2 CH.sub.2519 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.2 FCHF520 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.2 F(CHF).sub.2521 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.2 FCHFCF.sub.2522 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.2 FCHFCH.sub.2523 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.2 FCH.sub.2524 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.2 F(CH.sub.2).sub.2525 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.2 FCH.sub.2 CF.sub.2526 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.2 FCH.sub.2 CHF527 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.3 CF.sub.2528 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.3 (CF.sub.2).sub.2529 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.3 CF.sub.2 CHF530 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.3 CF.sub.2 CH.sub.2531 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.3 CHF532 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.3 (CHF).sub.2533 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.3 CHFCF.sub.2534 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.3 CHFCH.sub.2535 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.3 CH.sub.2 CF.sub.2536 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.3 CH.sub.2 (CF.sub.2).sub.2537 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub. 3 (CH.sub.2).sub.2 CF.sub.2538 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.3 (CH.sub.2).sub.2 (CF.sub.2).sub.2539 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.3 (CH.sub.2).sub.3 CF.sub.2540 CH.sub.3 CF.sub.2,CH.sub.3 CF.sub.2 CH.sub.3 (CH.sub.2).sub.3 (CF.sub.2).sub.2______________________________________

EXAMPLES 541-1,080

Metal coupons are soiled with various types of oil. The soiled metal coupons are immersed in the novel solvents of Table I above for a period of 15 seconds to 2 minutes, removed, and allowed to air dry. Upon visual inspection, the soil appears to be substantially removed.

EXAMPLES 1,081-1,620

Metal coupons are soiled with various types of oil. The soiled metal coupons are wiped with the novel solvents of Table I above and allowed to air dry. Upon visual inspection, the soil appears to be substantially removed.

Having described the invention in detail and by reference to preferred embodiments thereof, it will be apparent that modifications and variations are possible without departing from the scope of the invention defined in the appended claims.

Claims

1. A compound having the formula ##STR4## wherein each R is the same or different and is selected from the group consisting of CF.sub.3, CHF.sub.2, CH.sub.2 F, and CH.sub.3 CF.sub.2, and R' is an alkyl or fluoroalkyl group having 1 to 6 carbon atoms with the proviso that when each R is CF.sub.3, R' is not CF.sub.3 (CF.sub.2).sub.3 CF.sub.3 (CF.sub.2).sub.2 -, or CF.sub.3 CF.sub.2 -, or CF.sub.3.

2. The compound of claim 1 wherein said R' is selected from the group consisting of CF.sub.3, CHF.sub.2, CH.sub.2 F, CH.sub.3, CF.sub.3 (CF.sub.2).sub.n -, CF.sub.3 CF.sub.2 CHF-, CF.sub.3 CF.sub.2 CH.sub.2 -, CF.sub.3 (CHF).sub.n -, CF.sub.3 CHFCF.sub.2 -, CF.sub.3 CHFCH.sub.2 -, CF.sub.3 (CH.sub.2).sub.n -, CF.sub.3 CH.sub.2 CF.sub.2 -, CF.sub.3 CH.sub.2 CHF-, CHF.sub.2 (CF.sub.2).sub.n -, CHF.sub.2 CF.sub.2 CHF-, CHF.sub.2 CF.sub.2 CH.sub.2 -, CHF.sub.2 (CHF).sub.n -, CHF.sub.2 CHFCF.sub.2 -, CHF.sub.2 CHFCH.sub.2 -, CHF.sub.2 (CH.sub.2).sub.n -, CHF.sub.2 CH.sub.2 CF.sub.2 -, CHF.sub.2 CH.sub.2 CHF-, CH.sub.2 F(CF.sub.2).sub.n -, CH.sub.2 FCF.sub.2 CHF-, CH.sub.2 FCF.sub.2 CH.sub.2 -, CH.sub.2 F(CHF).sub.n -, CH.sub.2 FCHFCF.sub.2 -, CH.sub.2 FCHFCH.sub.2 -, CH.sub.2 F(CH.sub.2).sub.n -, CH.sub.2 FCH.sub.2 CF.sub.2 -, CH.sub.2 FCH.sub.2 CHF-, CH.sub.3 (CF.sub.2).sub.n -, CH.sub.3 CF.sub.2 CHF-, CH.sub.3 CF.sub.2 CH.sub.2 -, CH.sub.3 (CHF).sub.n -, CH.sub.3 CHFCF.sub.2 -, CH.sub.3 CHFCH.sub.2 -, and CH.sub.3 (CH.sub.2).sub.n, and m is 1 to 3, and n is 1 or 2 with the proviso that when each R is CF.sub.3, R' is not CF.sub.3, CF.sub.3 CF.sub.2 -, or CF.sub.3 (CF.sub.2).sub.2 -.

3. The compound of claim 2 wherein each of said R is the same.

4. The compound of claim 1 wherein said compound is selected from the group consisting of 2-difluoromethyl-1,1,3,3-tetrafluoropropane, 2-fluoromethyl-1,3-difluoropropane, and 3-trifluoromethyl-2,2,4,4-tetrafluoropentane.

5. The compound of claim 3 wherein each of said R is CF.sub.3 .

6. The compound of claim 5 wherein said R' is selected from the group consisting of CHF.sub.2, CH.sub.3, and CF.sub.3 CH.sub.2 -.

7. The compound of claim 5 wherein said R' is CHF.sub.2 .

8. The compound of claim 5 wherein said R' is CH.sub.3 .

9. The compound of claim 5 wherein said R' is CF.sub.3 CH.sub.2 -.

10. The compound of claim 5 wherein said R' is selected from the group consisting of CH.sub.3 CF.sub.2 -, CH.sub.3 (CF.sub.2).sub.2 -, and CH.sub.3 CH.sub.2 CF.sub.2 -.

11. The compound of claim 5 wherein said R' is CH.sub.3 CF.sub.2 -.

12. The compound of claim 5 wherein said R' is CH.sub.3 (CF.sub.2).sub.2 -.

13. The compound of claim 5 wherein said R' is CH.sub.3 CH.sub.2 CF.sub.2 -.