AU2005250879A1 - 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone compositions comprising a hydrofluorocarbon and uses thereof - Google Patents
1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone compositions comprising a hydrofluorocarbon and uses thereof Download PDFInfo
- Publication number
- AU2005250879A1 AU2005250879A1 AU2005250879A AU2005250879A AU2005250879A1 AU 2005250879 A1 AU2005250879 A1 AU 2005250879A1 AU 2005250879 A AU2005250879 A AU 2005250879A AU 2005250879 A AU2005250879 A AU 2005250879A AU 2005250879 A1 AU2005250879 A1 AU 2005250879A1
- Authority
- AU
- Australia
- Prior art keywords
- nonafluoro
- trifluoromethyl
- pentanone
- weight percent
- composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- RMLFHPWPTXWZNJ-UHFFFAOYSA-N novec 1230 Chemical compound FC(F)(F)C(F)(F)C(=O)C(F)(C(F)(F)F)C(F)(F)F RMLFHPWPTXWZNJ-UHFFFAOYSA-N 0.000 title claims description 149
- 239000000203 mixture Substances 0.000 title claims description 130
- -1 phenanthracenes Chemical class 0.000 claims description 97
- 239000003507 refrigerant Substances 0.000 claims description 71
- 239000002904 solvent Substances 0.000 claims description 57
- 238000005057 refrigeration Methods 0.000 claims description 53
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- 229930195733 hydrocarbon Natural products 0.000 claims description 43
- 238000004378 air conditioning Methods 0.000 claims description 41
- 239000004215 Carbon black (E152) Substances 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 125000001931 aliphatic group Chemical group 0.000 claims description 21
- 239000007850 fluorescent dye Substances 0.000 claims description 20
- 239000000975 dye Substances 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 15
- 150000002596 lactones Chemical class 0.000 claims description 15
- RIQRGMUSBYGDBL-UHFFFAOYSA-N 1,1,1,2,2,3,4,5,5,5-decafluoropentane Chemical compound FC(F)(F)C(F)C(F)C(F)(F)C(F)(F)F RIQRGMUSBYGDBL-UHFFFAOYSA-N 0.000 claims description 13
- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 claims description 12
- 238000007906 compression Methods 0.000 claims description 12
- 150000002576 ketones Chemical class 0.000 claims description 12
- XRKOOHTZZDPJNE-UHFFFAOYSA-N 1,1,1-trifluorohexane Chemical compound CCCCCC(F)(F)F XRKOOHTZZDPJNE-UHFFFAOYSA-N 0.000 claims description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 11
- 238000001704 evaporation Methods 0.000 claims description 11
- PSSHQAXMSKKIBE-UHFFFAOYSA-N 1,1-difluoropentane Chemical compound CCCCC(F)F PSSHQAXMSKKIBE-UHFFFAOYSA-N 0.000 claims description 10
- OOLOYCGJRJFTPM-UHFFFAOYSA-N 1,3-difluoropropane Chemical compound FCCCF OOLOYCGJRJFTPM-UHFFFAOYSA-N 0.000 claims description 10
- CXHPKSYTQFAXIN-UHFFFAOYSA-N 1,4-difluorobutane Chemical compound FCCCCF CXHPKSYTQFAXIN-UHFFFAOYSA-N 0.000 claims description 10
- QSWGSLWFQDIXSH-UHFFFAOYSA-N 2,2-difluoropentane Chemical compound CCCC(C)(F)F QSWGSLWFQDIXSH-UHFFFAOYSA-N 0.000 claims description 10
- GRELHMBELDGGLT-UHFFFAOYSA-N 2,3-difluorobutane Chemical compound CC(F)C(C)F GRELHMBELDGGLT-UHFFFAOYSA-N 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 10
- 239000013529 heat transfer fluid Substances 0.000 claims description 10
- 150000002825 nitriles Chemical class 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- GENRYAJRHIWOJI-UHFFFAOYSA-N 1,1,1-trifluoropentane Chemical compound CCCCC(F)(F)F GENRYAJRHIWOJI-UHFFFAOYSA-N 0.000 claims description 9
- AKQMZZOTFNLAQJ-UHFFFAOYSA-N 1,1,2,2-tetrafluorocyclobutane Chemical compound FC1(F)CCC1(F)F AKQMZZOTFNLAQJ-UHFFFAOYSA-N 0.000 claims description 9
- GQSMEOJGQJMOHA-UHFFFAOYSA-N 1,1,3-trifluoropropane Chemical compound FCCC(F)F GQSMEOJGQJMOHA-UHFFFAOYSA-N 0.000 claims description 9
- CPLSOYONVLSMGL-UHFFFAOYSA-N 1,1-difluorobutane Chemical compound CCCC(F)F CPLSOYONVLSMGL-UHFFFAOYSA-N 0.000 claims description 9
- OLURRGJWZJYRIM-UHFFFAOYSA-N 1,3-difluoro-2-methylpropane Chemical compound FCC(C)CF OLURRGJWZJYRIM-UHFFFAOYSA-N 0.000 claims description 9
- JFGBHUQZXJIATI-UHFFFAOYSA-N 1,3-difluorobutane Chemical compound CC(F)CCF JFGBHUQZXJIATI-UHFFFAOYSA-N 0.000 claims description 9
- GVEUEBXMTMZVSD-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,6-nonafluorohex-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C=C GVEUEBXMTMZVSD-UHFFFAOYSA-N 0.000 claims description 9
- CONTVCYXDSFGMN-UHFFFAOYSA-N 1,1,1-trifluoro-3-methylbutane Chemical compound CC(C)CC(F)(F)F CONTVCYXDSFGMN-UHFFFAOYSA-N 0.000 claims description 8
- VHJOGNLCVJAXFE-UHFFFAOYSA-N 1,2-difluorobutane Chemical compound CCC(F)CF VHJOGNLCVJAXFE-UHFFFAOYSA-N 0.000 claims description 8
- JKYLNUHIUDXCMN-UHFFFAOYSA-N 1,2-difluoropentane Chemical compound CCCC(F)CF JKYLNUHIUDXCMN-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 229920001774 Perfluoroether Polymers 0.000 claims description 8
- 150000008378 aryl ethers Chemical class 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 230000006835 compression Effects 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 229910052731 fluorine Chemical group 0.000 claims description 8
- 239000011737 fluorine Chemical group 0.000 claims description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims description 8
- MBPIQXLEEJZOMY-UHFFFAOYSA-N 1,2-difluoro-2-methylpropane Chemical compound CC(C)(F)CF MBPIQXLEEJZOMY-UHFFFAOYSA-N 0.000 claims description 7
- 239000000460 chlorine Chemical group 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 6
- 239000002516 radical scavenger Substances 0.000 claims description 6
- 230000000873 masking effect Effects 0.000 claims description 5
- 229920005862 polyol Polymers 0.000 claims description 5
- 150000003077 polyols Chemical class 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000003381 stabilizer Substances 0.000 claims description 4
- VWCLQNINSPFHFV-UHFFFAOYSA-N 10-oxapentacyclo[12.8.0.02,11.04,9.015,20]docosa-1(14),2(11),4,6,8,12,15,17,19,21-decaene Chemical class C1=CC=C2C3=CC=C4OC5=CC=CC=C5CC4=C3C=CC2=C1 VWCLQNINSPFHFV-UHFFFAOYSA-N 0.000 claims description 3
- OALHHIHQOFIMEF-UHFFFAOYSA-N 3',6'-dihydroxy-2',4',5',7'-tetraiodo-3h-spiro[2-benzofuran-1,9'-xanthene]-3-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 OALHHIHQOFIMEF-UHFFFAOYSA-N 0.000 claims description 3
- 150000001454 anthracenes Chemical class 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 3
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical class C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 235000001671 coumarin Nutrition 0.000 claims description 3
- 125000000332 coumarinyl group Chemical class O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 3
- 150000002979 perylenes Chemical class 0.000 claims description 3
- 150000005075 thioxanthenes Chemical class 0.000 claims description 3
- 150000003732 xanthenes Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000002443 hydroxylamines Chemical class 0.000 claims description 2
- 150000002905 orthoesters Chemical group 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 3
- KDWQLICBSFIDRM-UHFFFAOYSA-N 1,1,1-trifluoropropane Chemical compound CCC(F)(F)F KDWQLICBSFIDRM-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- LYGJENNIWJXYER-BJUDXGSMSA-N nitromethane Chemical group [11CH3][N+]([O-])=O LYGJENNIWJXYER-BJUDXGSMSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 22
- 150000003254 radicals Chemical class 0.000 description 13
- 239000000654 additive Substances 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 239000012530 fluid Substances 0.000 description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- 238000006073 displacement reaction Methods 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 4
- 101150065749 Churc1 gene Proteins 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 102100038239 Protein Churchill Human genes 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 description 4
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 4
- LKLFXAVIFCLZQS-UHFFFAOYSA-N 1,1,2,2,3,3,4,4-octafluorobutane Chemical compound FC(F)C(F)(F)C(F)(F)C(F)F LKLFXAVIFCLZQS-UHFFFAOYSA-N 0.000 description 3
- AWTOFSDLNREIFS-UHFFFAOYSA-N 1,1,2,2,3-pentafluoropropane Chemical compound FCC(F)(F)C(F)F AWTOFSDLNREIFS-UHFFFAOYSA-N 0.000 description 3
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- 230000033228 biological regulation Effects 0.000 description 3
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 description 3
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 3
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 description 3
- ZAJNGDIORYACQU-UHFFFAOYSA-N decan-2-one Chemical compound CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- 125000005023 xylyl group Chemical group 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- OALYTRUKMRCXNH-UHFFFAOYSA-N 5-pentyloxolan-2-one Chemical compound CCCCCC1CCC(=O)O1 OALYTRUKMRCXNH-UHFFFAOYSA-N 0.000 description 2
- GHBSPIPJMLAMEP-UHFFFAOYSA-N 6-pentyloxan-2-one Chemical compound CCCCCC1CCCC(=O)O1 GHBSPIPJMLAMEP-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- 229940123457 Free radical scavenger Drugs 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
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- MCSINKKTEDDPNK-UHFFFAOYSA-N propyl propionate Chemical compound CCCOC(=O)CC MCSINKKTEDDPNK-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- ULIAPOFMBCCSPE-UHFFFAOYSA-N tridecan-7-one Chemical compound CCCCCCC(=O)CCCCCC ULIAPOFMBCCSPE-UHFFFAOYSA-N 0.000 description 1
- WKJHMKQSIBMURP-UHFFFAOYSA-N tridecanenitrile Chemical compound CCCCCCCCCCCCC#N WKJHMKQSIBMURP-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical group CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical group COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical class C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- SZKKNEOUHLFYNA-UHFFFAOYSA-N undecanenitrile Chemical compound CCCCCCCCCCC#N SZKKNEOUHLFYNA-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
- C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
- C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
- C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/16—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
- C07C49/167—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen containing only fluorine as halogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
- F25D—REFRIGERATORS; COLD ROOMS; ICE-BOXES; COOLING OR FREEZING APPARATUS NOT OTHERWISE PROVIDED FOR
- F25D1/00—Devices using naturally cold air or cold water
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/22—All components of a mixture being fluoro compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Combustion & Propulsion (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57503704P | 2004-05-26 | 2004-05-26 | |
| US60/575,037 | 2004-05-26 | ||
| US11/063,203 US7153448B2 (en) | 2004-05-26 | 2005-02-22 | 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone compositions comprising a hydrofluorocarbon and uses thereof |
| US11/063,203 | 2005-02-22 | ||
| PCT/US2005/018886 WO2005119143A2 (en) | 2004-05-26 | 2005-05-25 | 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone compositions comprising a hydrofluorocarbon and uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2005250879A1 true AU2005250879A1 (en) | 2005-12-15 |
Family
ID=35463509
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2005250879A Abandoned AU2005250879A1 (en) | 2004-05-26 | 2005-05-25 | 1,1,1,2,2,4,5,5,5-nonafluoro-4-(trifluoromethyl)-3-pentanone compositions comprising a hydrofluorocarbon and uses thereof |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP1751247A2 (https=) |
| JP (1) | JP2008500437A (https=) |
| KR (1) | KR20070015594A (https=) |
| AR (1) | AR050665A1 (https=) |
| AU (1) | AU2005250879A1 (https=) |
| BR (1) | BRPI0510839A (https=) |
| CA (1) | CA2564168A1 (https=) |
| MX (1) | MXPA06013548A (https=) |
| NO (1) | NO20066032L (https=) |
| WO (1) | WO2005119143A2 (https=) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2642570T3 (es) * | 2006-02-28 | 2017-11-16 | The Chemours Company Fc, Llc | Composiciones azeotrópicas que comprenden compuestos fluorados para aplicaciones de limpieza |
| CN101522850A (zh) * | 2006-09-01 | 2009-09-02 | 纳幕尔杜邦公司 | 氟烯烃用的硫醇和硫醚稳定剂 |
| WO2008027514A1 (en) | 2006-09-01 | 2008-03-06 | E. I. Du Pont De Nemours And Company | Terpene, terpenoid, and fullerene stabilizers for fluoroolefins |
| ES2705488T3 (es) | 2006-09-01 | 2019-03-25 | Chemours Co Fc Llc | Estabilizadores que contienen fósforo para fluoroolefinas |
| CN104017544B (zh) | 2006-09-01 | 2017-04-12 | 纳幕尔杜邦公司 | 氟烯烃用的环氧化物和氟化环氧化物稳定剂 |
| WO2008027594A2 (en) * | 2006-09-01 | 2008-03-06 | E. I. Du Pont De Nemours And Company | Phenol stabilizers for fluoroolefins |
| WO2008027516A1 (en) * | 2006-09-01 | 2008-03-06 | E. I. Du Pont De Nemours And Company | Lactones for fluoroolefins |
| WO2008027596A2 (en) * | 2006-09-01 | 2008-03-06 | E. I. Du Pont De Nemours And Company | Benzophenone derivative stabilizers for fluoroolefins |
| EP2057246A1 (en) * | 2006-09-01 | 2009-05-13 | E.I. Du Pont De Nemours And Company | Thiol and thioether stabilizers for fluoroolefins |
| CN101517032B (zh) | 2006-09-01 | 2013-04-24 | 纳幕尔杜邦公司 | 氟烯烃用的抗坏血酸、对苯二甲酸酯或硝基甲烷稳定剂 |
| US20090053210A1 (en) * | 2006-09-01 | 2009-02-26 | Roland Buelow | Enhanced expression of human or humanized immunoglobulin in non-human transgenic animals |
| WO2008027519A1 (en) * | 2006-09-01 | 2008-03-06 | E. I. Du Pont De Nemours And Company | Oxetane stabilizers for fluoroolefins |
| WO2008042066A1 (en) * | 2006-09-01 | 2008-04-10 | E.I. Du Pont De Nemours And Company | Amine stabilizers for fluoroolefins |
| WO2008027595A1 (en) * | 2006-09-01 | 2008-03-06 | E. I. Du Pont De Nemours And Company | Alkyl silane stabilizers for fluoroolefins |
| EP2711407B1 (en) | 2011-05-19 | 2018-11-07 | AGC Inc. | Working medium and heat-cycle system |
| CN105542720B (zh) | 2011-05-19 | 2020-01-24 | Ａｇｃ株式会社 | 热循环用工作介质及含工作介质的组合物 |
| WO2012157764A1 (ja) | 2011-05-19 | 2012-11-22 | 旭硝子株式会社 | 作動媒体および熱サイクルシステム |
| JPWO2013015201A1 (ja) | 2011-07-22 | 2015-02-23 | 旭硝子株式会社 | 熱サイクル用作動媒体および熱サイクルシステム |
| JP6402630B2 (ja) | 2013-02-05 | 2018-10-10 | Ａｇｃ株式会社 | ヒートポンプ用作動媒体およびヒートポンプシステム |
| DE112014003256T5 (de) | 2013-07-12 | 2016-03-31 | Asahi Glass Company, Ltd. | Arbeitsfluid für einen Wärmekreisprozess, Zusammensetzung für ein Wärmekreisprozesssystem und Wärmekreisprozesssystem |
| WO2015115550A1 (ja) | 2014-01-31 | 2015-08-06 | 旭硝子株式会社 | 熱サイクル用作動媒体、熱サイクルシステム用組成物および熱サイクルシステム |
| JP6657957B2 (ja) | 2014-01-31 | 2020-03-04 | Ａｇｃ株式会社 | 熱サイクル用作動媒体、熱サイクルシステム用組成物および熱サイクルシステム |
| JP6614128B2 (ja) | 2014-02-20 | 2019-12-04 | Ａｇｃ株式会社 | 熱サイクルシステム用組成物および熱サイクルシステム |
| EP3109291B1 (en) | 2014-02-20 | 2023-01-11 | AGC Inc. | Composition for heat cycle system, and heat cycle system |
| JP6455506B2 (ja) | 2014-02-24 | 2019-01-23 | Ａｇｃ株式会社 | 熱サイクルシステム用組成物および熱サイクルシステム |
| EP3257913B1 (en) | 2015-02-09 | 2021-01-27 | AGC Inc. | Use of a working fluid as air conditioner working medium for electric car |
| EP4628559A3 (en) | 2015-06-01 | 2025-12-17 | AGC Inc. | Working fluid for heat cycle, composition for heat cycle system and heat cycle system |
| CN109563399A (zh) | 2016-07-29 | 2019-04-02 | Ａｇｃ株式会社 | 热循环用工作介质 |
| CN109689831B (zh) | 2016-09-07 | 2022-04-29 | Ａｇｃ株式会社 | 热循环用工作介质、热循环系统用组合物以及热循环系统 |
| JPWO2018168776A1 (ja) | 2017-03-14 | 2020-05-14 | Ａｇｃ株式会社 | 熱サイクルシステム |
| JP7108599B2 (ja) | 2017-03-17 | 2022-07-28 | Ａｇｃ株式会社 | 熱サイクルシステム用組成物および熱サイクルシステム |
| WO2018193974A1 (ja) | 2017-04-20 | 2018-10-25 | Ａｇｃ株式会社 | 熱サイクルシステム |
| EP3862408B1 (en) | 2018-10-01 | 2024-07-31 | Agc Inc. | Composition for heat cycle system, and heat cycle system |
| JPWO2024090169A1 (https=) | 2022-10-26 | 2024-05-02 | ||
| JPWO2024090387A1 (https=) | 2022-10-27 | 2024-05-02 | ||
| WO2024090386A1 (ja) | 2022-10-27 | 2024-05-02 | Ａｇｃ株式会社 | 熱サイクル用作動媒体及び熱サイクルシステム用組成物 |
| CN120659857A (zh) | 2023-01-30 | 2025-09-16 | Ａｇｃ株式会社 | 工作介质、热循环系统用组合物、热循环装置和热循环方法 |
| JPWO2024162224A1 (https=) | 2023-01-31 | 2024-08-08 | ||
| WO2024262102A1 (ja) | 2023-06-19 | 2024-12-26 | Ａｇｃ株式会社 | 作動媒体、熱サイクルシステム用組成物、熱サイクルシステム、及び熱サイクル方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6688118B1 (en) * | 1996-03-01 | 2004-02-10 | E. I. Du Pont De Nemours And Company | Azeotropic compositions of cyclopentane |
| US6423673B1 (en) * | 2001-09-07 | 2002-07-23 | 3M Innovation Properties Company | Azeotrope-like compositions and their use |
-
2005
- 2005-05-25 AU AU2005250879A patent/AU2005250879A1/en not_active Abandoned
- 2005-05-25 KR KR1020067024693A patent/KR20070015594A/ko not_active Withdrawn
- 2005-05-25 EP EP05756077A patent/EP1751247A2/en not_active Withdrawn
- 2005-05-25 WO PCT/US2005/018886 patent/WO2005119143A2/en not_active Ceased
- 2005-05-25 CA CA002564168A patent/CA2564168A1/en not_active Abandoned
- 2005-05-25 JP JP2007515434A patent/JP2008500437A/ja not_active Withdrawn
- 2005-05-25 BR BRPI0510839-0A patent/BRPI0510839A/pt not_active Application Discontinuation
- 2005-05-25 MX MXPA06013548A patent/MXPA06013548A/es unknown
- 2005-05-26 AR ARP050102165A patent/AR050665A1/es unknown
-
2006
- 2006-12-27 NO NO20066032A patent/NO20066032L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005119143A3 (en) | 2006-11-30 |
| AR050665A1 (es) | 2006-11-15 |
| KR20070015594A (ko) | 2007-02-05 |
| BRPI0510839A (pt) | 2007-11-27 |
| EP1751247A2 (en) | 2007-02-14 |
| CA2564168A1 (en) | 2005-12-15 |
| NO20066032L (no) | 2007-02-19 |
| JP2008500437A (ja) | 2008-01-10 |
| MXPA06013548A (es) | 2007-01-26 |
| WO2005119143A2 (en) | 2005-12-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |