1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone refrigerant compositions comprising a hydrocarbon and uses thereof

Abstract

Disclosed herein are refrigerant and heat transfer fluid compositions comprising 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and at least one hydrocarbon. These compositions are useful in refrigeration and air conditioning systems that employ a centrifugal compressor. Also disclosed herein are azeotropic or near azeotropic refrigerant and heat transfer fluid compositions comprising 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and at least one hydrocarbon.

1 . A composition selected from the group consisting of: 
 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 2,2-dimethylbutane;    1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 2,3-dimethylbutane;    1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 2,3-dimethylpentane; 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 3-methylhexane;    1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 2-methylpentane;    1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 3-ethylpentane;    1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 3-methylpentane;    1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and cyclohexane;    1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and cyclopentane;    1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and methylcyclopentane; and    1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and n-pentane.    
     
     
         2 . A composition as in  claim 1  wherein the composition is a refrigerant or heat transfer fluid composition suitable for use in refrigeration or air conditioning apparatus employing (i) centrifugal compressor, or (ii) multi-stage centrifugal compressor, or (iii) a single slab/single pass heat exchanger, and said composition is selected from the group consisting of: 
 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 2,2-dimethylbutane;    1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 2,3-dimethylbutane;    1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 2,3-dimethylpentane;    1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 3-methylhexane;    1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 2-methylpentane;    1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 3-ethylpentane;    1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 3-methylpentane;    1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and cyclohexane;    1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and cyclopentane;    1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and methylcyclopentane; and    1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and n-pentane.    
     
     
         3 . A composition as in  claim 1 , wherein the composition is an azeotropic or near-azeotropic composition selected from the group consisting of: 
 about 52 to about 89 weight percent 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and about 48 to about 11 weight percent 2,2-dimethylbutane;    about 60 to about 92 weight percent 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and about 40 to about 8 weight percent 2,3-dimethylbutane;    about 71 to about 99 weight percent 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and about 29 to about 1 weight percent 2,3-dimethylpentane;    about 71 to about 99 weight percent 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and about 29 to about 1 weight percent 3-methylhexane;    about 60 to about 93 weight percent 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and about 40 to about 7 weight percent 2-methylpentane;    about 72 to about 99 weight percent 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and about 28 to about 1 weight percent 3-ethylpentane;    about 62 to about 95 weight percent 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and about 38 to about 5 weight percent 3-methylpentane;    about 68 to about 99 weight percent 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and about 32 to about 1 weight percent cyclohexane;    about 51 to about 92 weight percent 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and about 49 to about 8 weight percent cyclopentane;    about 65 to about 99 weight percent 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and about 35 to about 1 weight percent methylcyclopentane; and    about 42 to about 84 weight percent 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and about 58 to about 16 weight percent n-pentane.    
     
     
         4 . A composition as in  claim 1  wherein the composition is an azeotropic composition selected from the group consisting of: 
 75.0 weight percent 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 25.0 weight percent 2,2-dimethylbutane having a vapor pressure of about 14.7 psia (101 kPa) at a temperature of about 34.1° C.;    81.4 weight percent 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 18.6 weight percent 2,3-dimethylbutane having a vapor pressure of about 14.7 psia (101 kPa) at a temperature of about 37.2° C.;    93.8 weight percent 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 6.2 weight percent 2,3-dimethylpentane having a vapor pressure of about 14.7 psia (101 kPa) at a temperature of about 46.7° C.;    93.8 weight percent 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 6.2 weight percent 3-methylhexane having a vapor pressure of about 14.7 psia (101 kPa) at a temperature of about 46.7° C.;    82.4 weight percent 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 17.6 weight percent 2-methylpentane having a vapor pressure of about 14.7 psia (101 kPa) at a temperature of about 39.5° C.;    96.2 weight percent 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 3.8 weight percent 3-ethylpentane having a vapor pressure of about 14.7 psia (101 kPa) at a temperature of about 48.2° C.;    84.2 weight percent 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 15.8 weight percent 3-methylpentane having a vapor pressure of about 14.7 psia (101 kPa) at a temperature of about 40.7° C.;    92.4 weight percent 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 7.6 weight percent cyclohexane having a vapor pressure of about 14.7 psia (101 kPa) at a temperature of about 46.5° C.;    75.7 weight percent 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 24.3 weight percent cyclopentane having a vapor pressure of about 14.7 psia (101 kPa) at a temperature of about 36.8° C.;    88.9 weight percent 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 11.1 weight percent methylcyclopentane having a vapor pressure of about 14.7 psia (101 kPa) at a temperature of about 44.7° C.; and    64.3 weight percent 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone and 35.7 weight percent n-pentane having a vapor pressure of about 14.7 psia (101 kPa) at a temperature of about 26.6° C.    
     
     
         5 . A process for producing refrigeration, said process comprising evaporating the refrigerant composition of  claim 2 , in the vicinity of a body to be cooled, and thereafter condensing said composition.  
     
     
         6 . A process for producing heat, said process comprising condensing the heat transfer composition of  claim 2  in the vicinity of a body to be heated, and thereafter evaporating said composition.  
     
     
         7 . A process for transferring heat, said process comprising transferring the composition of  claim 1  from the vicinity of a heat source to a heat sink.  
     
     
         8 . The composition of  claim 1 , further comprising at least one ultra-violet fluorescent dye selected from the group consisting of naphthalimides, perylenes, coumarins, anthracenes, phenanthracenes, xanthenes, thioxanthenes, naphthoxanthenes, fluoresceins, derivatives of said dye and combinations thereof.  
     
     
         9 . The composition of  claim 8 , further comprising at least one solubilizing agent selected from the group consisting of hydrocarbons, dimethylether, polyoxyalkylene glycol ethers, amides, ketones, nitriles, chlorocarbons, esters, lactones, aryl ethers, hydrofluoroethers, and 1,1,1-trifluoroalkanes; and wherein the refrigerant and solubilizing agent are not the same compound.  
     
     
         10 . The composition of  claim 9 , wherein said solubilizing agent is selected from the group consisting of: 
 a) polyoxyalkylene glycol ethers represented by the formula R 1 [(OR 2 ) x OR 3 ] y , wherein: x is an integer from 1 to 3; y is an integer from 1 to 4; R 1  is selected from hydrogen and aliphatic hydrocarbon radicals having 1 to 6 carbon atoms and y bonding sites; R 2  is selected from aliphatic hydrocarbylene radicals having from 2 to 4 carbon atoms; R 3  is selected from hydrogen, and aliphatic and alicyclic hydrocarbon radicals having from 1 to 6 carbon atoms; at least one of R 1  and R 3  is selected from said hydrocarbon radicals; and wherein said polyoxyalkylene glycol ethers have a molecular weight of from about 100 to about 300 atomic mass units;    b) amides represented by the formulae R 1 CONR 2 R 3  and cyclo-[R 4 CON(R 5 )—], wherein R 1 , R 2 , R 3  and R 5  are independently selected from aliphatic and alicyclic hydrocarbon radicals having from 1 to 12 carbon atoms, and at most one aromatic radical having from 6 to 12 carbon atoms; R 4  is selected from aliphatic hydrocarbylene radicals having from 3 to 12 carbon atoms; and wherein said amides have a molecular weight of from about 100 to about 300 atomic mass units;    c) ketones represented by the formula R 1 COR 2 , wherein R 1  and R 2  are independently selected from aliphatic, alicyclic and aryl hydrocarbon radicals having from 1 to 12 carbon atoms, and wherein said ketones have a molecular weight of from about 70 to about 300 atomic mass units;    d) nitriles represented by the formula R 1 CN, wherein R 1  is selected from aliphatic, alicyclic or aryl hydrocarbon radicals having from 5 to 12 carbon atoms, and wherein said nitriles have a molecular weight of from about 90 to about 200 atomic mass units;    e) chlorocarbons represented by the formula RCl x , wherein; x is selected from the integers 1 or 2; R is selected from aliphatic and alicyclic hydrocarbon radicals having from 1 to 12 carbon atoms; and wherein said chlorocarbons have a molecular weight of from about 100 to about 200 atomic mass units;    f) aryl ethers represented by the formula R 1 OR 2 , wherein: R 1  is selected from aryl hydrocarbon radicals having from 6 to 12 carbon atoms; R 2  is selected from aliphatic hydrocarbon radicals having from 1 to 4 carbon atoms; and wherein said aryl ethers have a molecular weight of from about 100 to about 150 atomic mass units;    g) 1,1,1-trifluoroalkanes represented by the formula CF 3 R 1 , wherein R 1  is selected from aliphatic and alicyclic hydrocarbon radicals having from about 5 to about 15 carbon atoms;    i) fluoroethers represented by the formula R 1 OCF 2 CF 2 H, wherein R 1  is selected from aliphatic and alicyclic hydrocarbon radicals having from about 5 to about 15 carbon atoms; or wherein said fluoroethers are derived from fluoro-olefins and polyols, wherein said fluoro-olefins are of the type CF 2 ═CXY, wherein X is hydrogen, chlorine or fluorine, and Y is chlorine, fluorine, CF 3  or OR f , wherein R f  is CF 3 , C 2 F 5 , or C 3 F 7 ; and said polyols are of the type HOCH 2 CRR′(CH 2 )z(CHOH) x CH 2 (CH 2 OH) y , wherein R and R′ are hydrogen, CH 3  or C 2 H 5 , x is an integer from 0-4, y is an integer from 0-3 and z is either zero or 1; and    j) lactones represented by structures [B], [α], and [D]:                           wherein, R 1  through R 8  are independently selected from hydrogen, linear, branched, cyclic, bicyclic, saturated and unsaturated hydrocarbyl radicals; and the molecular weight is from about 100 to about 300 atomic mass units; and    k) esters represented by the general formula R 1 CO 2 R 2 , wherein R 1  and R 2  are independently selected from linear and cyclic, saturated and unsaturated, alkyl and aryl radicals; and wherein said esters have a molecular weight of from about 80 to about 550 atomic mass units.    
     
     
         11 . A process for detecting a leak at or in the vicinity of a refrigeration or air conditioning apparatus, said process comprising: providing a composition of  claim 8  into said apparatus, and providing a suitable means for detecting said composition at a leak point or in the vicinity of said apparatus.  
     
     
         12 . A method as in  claim 5  wherein the refrigerant composition further comprises at least one ultra-violet fluorescent dye selected from the group consisting of naphthalimides, perylenes, coumarins, anthracenes, phenanthracenes, xanthenes, thioxanthenes, naphthoxanthenes, fluoresceins, derivatives of said dye and combinations thereof.  
     
     
         13 . A method as in  claim 6  wherein the heat transfer composition further comprises at least one ultra-violet fluorescent dye selected from the group consisting of naphthalimides, perylenes, coumarins, anthracenes, phenanthracenes, xanthenes, thioxanthenes, naphthoxanthenes, fluoresceins, derivatives of said dye and combinations thereof.  
     
     
         14 . A method as in  claim 12 , wherein the refrigerant composition further comprises at least one solubilizing agent selected from the group consisting of hydrocarbons, dimethylether, polyoxyalkylene glycol ethers, amides, ketones, nitriles, chlorocarbons, esters, lactones, aryl ethers, hydrofluoroethers, and 1,1,1-trifluoroalkanes; and wherein the refrigerant and solubilizing agent are not the same compound.  
     
     
         15 . A method as in  claim 14  wherein the refrigerant composition is introduced into a compression refrigeration or air conditioning apparatus by (i) dissolving the ultraviolet fluorescent dye in the refrigerant composition or heat transfer fluid in the presence of the solubilizing agent, and introducing the combination into said compression refrigeration or air conditioning apparatus or (ii), combining solubilizing agent and UV fluorescent dye and introducing said combination into said compression refrigeration or air conditioning apparatus containing refrigerant and/or heat transfer fluid.  
     
     
         16 . The composition of  claim 1  further comprising a stabilizer, water scavenger, or odor masking agent.  
     
     
         17 . The composition of  claim 16  wherein said stabilizer is selected from the group consisting of nitromethane, hindered phenols, hydroxylamines, thiols, phosphites and lactones.  
     
     
         18 . The composition of  claim 16  wherein said water scavenger is an ortho ester.