CA2597199A1 - Absorption cycle utilizing ionic liquid as working fluid - Google Patents
Absorption cycle utilizing ionic liquid as working fluid Download PDFInfo
- Publication number
- CA2597199A1 CA2597199A1 CA002597199A CA2597199A CA2597199A1 CA 2597199 A1 CA2597199 A1 CA 2597199A1 CA 002597199 A CA002597199 A CA 002597199A CA 2597199 A CA2597199 A CA 2597199A CA 2597199 A1 CA2597199 A1 CA 2597199A1
- Authority
- CA
- Canada
- Prior art keywords
- hfc
- composition
- ionic liquid
- group
- refrigerant
- 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
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 175
- 238000010521 absorption reaction Methods 0.000 title claims abstract description 55
- 239000012530 fluid Substances 0.000 title description 10
- 239000003507 refrigerant Substances 0.000 claims abstract description 191
- 238000000034 method Methods 0.000 claims abstract description 43
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims abstract description 25
- 238000001816 cooling Methods 0.000 claims abstract description 16
- 238000010438 heat treatment Methods 0.000 claims abstract description 16
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 claims description 256
- 239000000203 mixture Substances 0.000 claims description 205
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 claims description 97
- 150000001450 anions Chemical class 0.000 claims description 68
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 59
- -1 cyclic alkenes Chemical class 0.000 claims description 54
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 claims description 51
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 claims description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 48
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 claims description 45
- 150000001768 cations Chemical class 0.000 claims description 38
- 239000007788 liquid Substances 0.000 claims description 36
- WXGNWUVNYMJENI-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)F WXGNWUVNYMJENI-UHFFFAOYSA-N 0.000 claims description 35
- 229910052799 carbon Inorganic materials 0.000 claims description 33
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 30
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 26
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 26
- 238000005057 refrigeration Methods 0.000 claims description 25
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 24
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 23
- 235000019404 dichlorodifluoromethane Nutrition 0.000 claims description 23
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 claims description 23
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 239000006096 absorbing agent Substances 0.000 claims description 20
- 229930195733 hydrocarbon Natural products 0.000 claims description 20
- 150000002430 hydrocarbons Chemical class 0.000 claims description 20
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 claims description 18
- 239000004215 Carbon black (E152) Substances 0.000 claims description 17
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 claims description 17
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 16
- 150000001924 cycloalkanes Chemical class 0.000 claims description 16
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 16
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 15
- 239000001273 butane Substances 0.000 claims description 14
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 14
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 13
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 13
- 239000001294 propane Substances 0.000 claims description 13
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000001282 iso-butane Substances 0.000 claims description 12
- 125000001425 triazolyl group Chemical group 0.000 claims description 12
- 229910052698 phosphorus Inorganic materials 0.000 claims description 11
- WXMVWUBWIHZLMQ-UHFFFAOYSA-N 3-methyl-1-octylimidazolium Chemical compound CCCCCCCCN1C=C[N+](C)=C1 WXMVWUBWIHZLMQ-UHFFFAOYSA-N 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 9
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 9
- 150000001336 alkenes Chemical class 0.000 claims description 9
- WMIYKQLTONQJES-UHFFFAOYSA-N hexafluoroethane Chemical compound FC(F)(F)C(F)(F)F WMIYKQLTONQJES-UHFFFAOYSA-N 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 239000004338 Dichlorodifluoromethane Substances 0.000 claims description 6
- 239000000470 constituent Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- JWPAOAULUAPZTP-UHFFFAOYSA-N 1,3-dioctylimidazol-1-ium Chemical compound CCCCCCCCN1C=C[N+](CCCCCCCC)=C1 JWPAOAULUAPZTP-UHFFFAOYSA-N 0.000 claims description 5
- 101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910021592 Copper(II) chloride Inorganic materials 0.000 claims 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims 2
- WGZYQOSEVSXDNI-UHFFFAOYSA-N 1,1,2-trifluoroethane Chemical compound FCC(F)F WGZYQOSEVSXDNI-UHFFFAOYSA-N 0.000 claims 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims 1
- 239000007789 gas Substances 0.000 abstract description 53
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 106
- 239000000243 solution Substances 0.000 description 68
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 64
- 229910001868 water Inorganic materials 0.000 description 62
- 238000009792 diffusion process Methods 0.000 description 38
- 238000004458 analytical method Methods 0.000 description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 31
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 30
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 27
- 239000002250 absorbent Substances 0.000 description 26
- 239000003921 oil Substances 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 23
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 description 22
- 230000002745 absorbent Effects 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 21
- 239000002244 precipitate Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 238000004364 calculation method Methods 0.000 description 19
- 229910002092 carbon dioxide Inorganic materials 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 18
- 239000007787 solid Substances 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 16
- 239000008367 deionised water Substances 0.000 description 16
- 229910021641 deionized water Inorganic materials 0.000 description 16
- 241000894007 species Species 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 14
- 239000003153 chemical reaction reagent Substances 0.000 description 13
- 239000011521 glass Substances 0.000 description 13
- 238000004448 titration Methods 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
- 238000009835 boiling Methods 0.000 description 12
- MLGFOYVBHZGRBK-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-2-hydroxy-n-methyl-2-phenyl-2-thiophen-2-ylacetamide;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(O)(C(=O)N(C)CCN(C)C)C1=CC=CS1 MLGFOYVBHZGRBK-UHFFFAOYSA-N 0.000 description 12
- 238000004293 19F NMR spectroscopy Methods 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- WTKZEGDFNFYCGP-UHFFFAOYSA-O Pyrazolium Chemical compound C1=CN[NH+]=C1 WTKZEGDFNFYCGP-UHFFFAOYSA-O 0.000 description 10
- 238000007906 compression Methods 0.000 description 10
- 238000010586 diagram Methods 0.000 description 10
- ZCQWOFVYLHDMMC-UHFFFAOYSA-O hydron;1,3-oxazole Chemical compound C1=COC=[NH+]1 ZCQWOFVYLHDMMC-UHFFFAOYSA-O 0.000 description 10
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- BMQZYMYBQZGEEY-UHFFFAOYSA-M 1-ethyl-3-methylimidazolium chloride Chemical compound [Cl-].CCN1C=C[N+](C)=C1 BMQZYMYBQZGEEY-UHFFFAOYSA-M 0.000 description 9
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000006835 compression Effects 0.000 description 9
- CZPWVGJYEJSRLH-UHFFFAOYSA-O hydron;pyrimidine Chemical compound C1=CN=C[NH+]=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-O 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 230000003993 interaction Effects 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- MEUAVGJWGDPTLF-UHFFFAOYSA-N 4-(5-benzenesulfonylamino-1-methyl-1h-benzoimidazol-2-ylmethyl)-benzamidine Chemical compound N=1C2=CC(NS(=O)(=O)C=3C=CC=CC=3)=CC=C2N(C)C=1CC1=CC=C(C(N)=N)C=C1 MEUAVGJWGDPTLF-UHFFFAOYSA-N 0.000 description 8
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 238000012937 correction Methods 0.000 description 7
- 239000010432 diamond Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- BVZFTIYNEUGOHK-UHFFFAOYSA-M potassium;1,1,2,2-tetrafluoroethanesulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)F BVZFTIYNEUGOHK-UHFFFAOYSA-M 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- FXJMBXFCCFVKKI-UHFFFAOYSA-M 1,3-dioctylimidazol-1-ium;iodide Chemical compound [I-].CCCCCCCCN1C=C[N+](CCCCCCCC)=C1 FXJMBXFCCFVKKI-UHFFFAOYSA-M 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- 238000000967 suction filtration Methods 0.000 description 5
- ZIPFNZZMKGEBFU-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;1,1,2-trifluoro-2-(1,1,2,2,2-pentafluoroethoxy)ethanesulfonate Chemical compound CCCC[N+]=1C=CN(C)C=1.[O-]S(=O)(=O)C(F)(F)C(F)OC(F)(F)C(F)(F)F ZIPFNZZMKGEBFU-UHFFFAOYSA-M 0.000 description 4
- FHDQNOXQSTVAIC-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;chloride Chemical compound [Cl-].CCCCN1C=C[N+](C)=C1 FHDQNOXQSTVAIC-UHFFFAOYSA-M 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- RWPGFSMJFRPDDP-UHFFFAOYSA-L potassium metabisulfite Chemical compound [K+].[K+].[O-]S(=O)S([O-])(=O)=O RWPGFSMJFRPDDP-UHFFFAOYSA-L 0.000 description 4
- 229940043349 potassium metabisulfite Drugs 0.000 description 4
- 235000010263 potassium metabisulphite Nutrition 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- 230000003068 static effect Effects 0.000 description 4
- MXDXOYOYMBHGQD-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;1,1,2,3,3,3-hexafluoropropane-1-sulfonate Chemical compound CCCC[N+]=1C=CN(C)C=1.[O-]S(=O)(=O)C(F)(F)C(F)C(F)(F)F MXDXOYOYMBHGQD-UHFFFAOYSA-M 0.000 description 3
- KRLZUNVVBLGDJV-UHFFFAOYSA-M 1-methyl-3-octylimidazol-1-ium;iodide Chemical compound [I-].CCCCCCCC[N+]=1C=CN(C)C=1 KRLZUNVVBLGDJV-UHFFFAOYSA-M 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 241001541138 Cypho Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000004378 air conditioning Methods 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- SUDHVXIPIDQEIT-UHFFFAOYSA-N bis(1,1,2,2,2-pentafluoroethylsulfonyl)azanide;1-ethyl-3-methylimidazol-3-ium Chemical compound CCN1C=C[N+](C)=C1.FC(F)(F)C(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)C(F)(F)F SUDHVXIPIDQEIT-UHFFFAOYSA-N 0.000 description 3
- LUWJQOLQUXTUGM-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)methylsulfonyl-trifluoromethane;1,2-dimethyl-3-propylimidazol-1-ium Chemical compound CCCN1C=C[N+](C)=C1C.FC(F)(F)S(=O)(=O)[C-](S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F LUWJQOLQUXTUGM-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 150000001923 cyclic compounds Chemical class 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- IUIPTNGBJURBMZ-UHFFFAOYSA-L dipotassium;sulfite;hydrate Chemical compound O.[K+].[K+].[O-]S([O-])=O IUIPTNGBJURBMZ-UHFFFAOYSA-L 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 3
- 229910000856 hastalloy Inorganic materials 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- HOYITZNTNKOLOY-UHFFFAOYSA-M potassium;1,1,2-trifluoro-2-(trifluoromethoxy)ethanesulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)OC(F)(F)F HOYITZNTNKOLOY-UHFFFAOYSA-M 0.000 description 3
- 238000005086 pumping Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000036962 time dependent Effects 0.000 description 3
- YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 description 2
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 2
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- YSVWBTSHQPOIJE-UHFFFAOYSA-M 1,1,2-trifluoro-2-(1,1,2,2,2-pentafluoroethoxy)ethanesulfonate;trihexyl(tetradecyl)phosphanium Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)OC(F)(F)C(F)(F)F.CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC YSVWBTSHQPOIJE-UHFFFAOYSA-M 0.000 description 1
- WJTASHROPQRUQG-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,1,2,2,2-pentafluoroethoxy)ethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)OC(F)(F)C(F)(F)F WJTASHROPQRUQG-UHFFFAOYSA-N 0.000 description 1
- MLDUNXBSSZEACC-UHFFFAOYSA-M 1,1,2-trifluoro-2-(trifluoromethoxy)ethanesulfonate;trihexyl(tetradecyl)phosphanium Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)OC(F)(F)F.CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC MLDUNXBSSZEACC-UHFFFAOYSA-M 0.000 description 1
- BLTXWCKMNMYXEA-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethoxy)ethene Chemical compound FC(F)=C(F)OC(F)(F)F BLTXWCKMNMYXEA-UHFFFAOYSA-N 0.000 description 1
- HVVRUQBMAZRKPJ-UHFFFAOYSA-N 1,3-dimethylimidazolium Chemical compound CN1C=C[N+](C)=C1 HVVRUQBMAZRKPJ-UHFFFAOYSA-N 0.000 description 1
- FWCNCCLDVGDQAB-UHFFFAOYSA-N 1-(1,1,2,2-tetrafluoroethyl)imidazole Chemical compound FC(F)C(F)(F)N1C=CN=C1 FWCNCCLDVGDQAB-UHFFFAOYSA-N 0.000 description 1
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- HIKOQOQWZDKNLH-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;1,1,2,2-tetrafluoro-2-(1,2,2,2-tetrafluoroethoxy)ethanesulfonate Chemical compound CCCC[N+]=1C=CN(C)C=1.[O-]S(=O)(=O)C(F)(F)C(F)(F)OC(F)C(F)(F)F HIKOQOQWZDKNLH-UHFFFAOYSA-M 0.000 description 1
- KUWPEQAOGNPMOP-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;1,1,2,2-tetrafluoroethanesulfonate Chemical compound CCCC[N+]=1C=CN(C)C=1.[O-]S(=O)(=O)C(F)(F)C(F)F KUWPEQAOGNPMOP-UHFFFAOYSA-M 0.000 description 1
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- OPXNHKQUEXEWAM-UHFFFAOYSA-M 1-dodecyl-3-methylimidazol-3-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCCN1C=C[N+](C)=C1 OPXNHKQUEXEWAM-UHFFFAOYSA-M 0.000 description 1
- SEGKWNUGNNFXPC-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;1,1,2,3,3,3-hexafluoropropane-1-sulfonate Chemical compound CC[N+]=1C=CN(C)C=1.[O-]S(=O)(=O)C(F)(F)C(F)C(F)(F)F SEGKWNUGNNFXPC-UHFFFAOYSA-M 0.000 description 1
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- DCLKMMFVIGOXQN-UHFFFAOYSA-N 1-hexadecyl-3-methylimidazol-3-ium Chemical compound CCCCCCCCCCCCCCCCN1C=C[N+](C)=C1 DCLKMMFVIGOXQN-UHFFFAOYSA-N 0.000 description 1
- CCVJDXYTHLIIKO-UHFFFAOYSA-L 1-hexyl-3-methylimidazol-3-ium 1,1,2,2-tetrafluoroethanesulfonate chloride Chemical compound [Cl-].C(CCCCC)[N+]1=CN(C=C1)C.FC(C(F)F)(S(=O)(=O)[O-])F.C(CCCCC)[N+]1=CN(C=C1)C CCVJDXYTHLIIKO-UHFFFAOYSA-L 0.000 description 1
- RVEJOWGVUQQIIZ-UHFFFAOYSA-N 1-hexyl-3-methylimidazolium Chemical compound CCCCCCN1C=C[N+](C)=C1 RVEJOWGVUQQIIZ-UHFFFAOYSA-N 0.000 description 1
- NKRASMXHSQKLHA-UHFFFAOYSA-M 1-hexyl-3-methylimidazolium chloride Chemical compound [Cl-].CCCCCCN1C=C[N+](C)=C1 NKRASMXHSQKLHA-UHFFFAOYSA-M 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- MMJMYYUZGLJBST-UHFFFAOYSA-N 1-methyl-3-octadecylimidazol-1-ium Chemical compound CCCCCCCCCCCCCCCCCCN1C=C[N+](C)=C1 MMJMYYUZGLJBST-UHFFFAOYSA-N 0.000 description 1
- LCXGSWXECDJESI-UHFFFAOYSA-M 1-methyl-3-octadecylimidazol-1-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCN1C=C[N+](C)=C1 LCXGSWXECDJESI-UHFFFAOYSA-M 0.000 description 1
- ACVAUFCPHXVLQA-UHFFFAOYSA-N 1h-imidazole;1h-pyrazole Chemical compound C=1C=NNC=1.C1=CNC=N1 ACVAUFCPHXVLQA-UHFFFAOYSA-N 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
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- LRESCJAINPKJTO-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-ethyl-3-methylimidazol-3-ium Chemical compound CCN1C=C[N+](C)=C1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F LRESCJAINPKJTO-UHFFFAOYSA-N 0.000 description 1
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- 230000002596 correlated effect Effects 0.000 description 1
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- 239000000975 dye Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
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- 238000004108 freeze drying Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
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- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229960004065 perflutren Drugs 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- IWVSKNFJIVKXHH-UHFFFAOYSA-N pyrazine;pyrimidine Chemical compound C1=CN=CN=C1.C1=CN=CC=N1 IWVSKNFJIVKXHH-UHFFFAOYSA-N 0.000 description 1
- LDEZROSHPJRREZ-UHFFFAOYSA-N pyridazine;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NN=C1 LDEZROSHPJRREZ-UHFFFAOYSA-N 0.000 description 1
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- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- AKUNSPZHHSNFFX-UHFFFAOYSA-M tributyl(tetradecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC AKUNSPZHHSNFFX-UHFFFAOYSA-M 0.000 description 1
- PYVOHVLEZJMINC-UHFFFAOYSA-N trihexyl(tetradecyl)phosphanium Chemical compound CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC PYVOHVLEZJMINC-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
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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
- C09K5/047—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for absorption-type refrigeration systems
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- 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
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- Combustion & Propulsion (AREA)
- Thermal Sciences (AREA)
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- Organic Chemistry (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65033005P | 2005-02-04 | 2005-02-04 | |
| US60/650,330 | 2005-02-04 | ||
| PCT/US2006/004230 WO2006084262A1 (en) | 2005-02-04 | 2006-02-03 | Absorption cycle utilizing ionic liquid as working fluid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2597199A1 true CA2597199A1 (en) | 2006-08-10 |
Family
ID=36424606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002597199A Abandoned CA2597199A1 (en) | 2005-02-04 | 2006-02-03 | Absorption cycle utilizing ionic liquid as working fluid |
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| US (1) | US8715521B2 (enExample) |
| EP (2) | EP1846535B1 (enExample) |
| JP (1) | JP2008530275A (enExample) |
| KR (1) | KR101314419B1 (enExample) |
| CN (1) | CN101155893B (enExample) |
| AT (1) | ATE533826T1 (enExample) |
| AU (1) | AU2006210403B2 (enExample) |
| BR (1) | BRPI0606828A2 (enExample) |
| CA (1) | CA2597199A1 (enExample) |
| ES (1) | ES2377439T3 (enExample) |
| NO (1) | NO20074471L (enExample) |
| RU (1) | RU2007133099A (enExample) |
| WO (1) | WO2006084262A1 (enExample) |
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| WO2008124087A1 (en) | 2007-04-03 | 2008-10-16 | E. I. Du Pont De Nemours And Company | Heat transfer systems using mixtures of polyols and ionic liquids |
| US8075777B2 (en) | 2007-05-16 | 2011-12-13 | E. I. Du Pont De Nemours And Company | Process for the separation of diastereomers |
| US7964760B2 (en) | 2007-05-25 | 2011-06-21 | E.I. Du Pont De Nemours And Company | Process for the separation of fluorocarbons using ionic liquids |
| KR20100087296A (ko) | 2007-09-28 | 2010-08-04 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 이온성 액체 안정화제 조성물 |
| JP2011527720A (ja) | 2008-07-08 | 2011-11-04 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | イオン性液体およびフルオロオレフィンを含む組成物、ならびに、吸収サイクルシステムにおけるその使用 |
| WO2010054230A2 (en) | 2008-11-07 | 2010-05-14 | E. I. Du Pont De Nemours And Company | Absorption cycle utilizing ionic compounds and/or non-ionic absorbents as working fluids |
| WO2010065873A2 (en) | 2008-12-04 | 2010-06-10 | E. I. Du Pont De Nemours And Company | Carbon dioxide removal and ionic liquid compounds useful therein |
| US8138354B2 (en) | 2008-12-04 | 2012-03-20 | E. I. Du Pont De Nemours And Company | N-substituted pyrrolidonium ionic liquids |
| US8119818B2 (en) | 2008-12-04 | 2012-02-21 | E. I. Du Pont De Nemours And Company | Functionalized N-substituted pyrrolidonium ionic liquids |
| WO2011060067A2 (en) | 2009-11-11 | 2011-05-19 | E. I. Du Pont De Nemours And Company | Refrigerant storage in secondary loop refrigeration systems |
-
2006
- 2006-02-02 US US11/346,028 patent/US8715521B2/en not_active Expired - Fee Related
- 2006-02-03 CA CA002597199A patent/CA2597199A1/en not_active Abandoned
- 2006-02-03 EP EP06734482A patent/EP1846535B1/en not_active Not-in-force
- 2006-02-03 EP EP10010397A patent/EP2258787A3/en not_active Withdrawn
- 2006-02-03 AT AT06734482T patent/ATE533826T1/de active
- 2006-02-03 CN CN2006800109987A patent/CN101155893B/zh not_active Expired - Fee Related
- 2006-02-03 BR BRPI0606828-6A patent/BRPI0606828A2/pt not_active IP Right Cessation
- 2006-02-03 RU RU2007133099/04A patent/RU2007133099A/ru not_active Application Discontinuation
- 2006-02-03 AU AU2006210403A patent/AU2006210403B2/en not_active Ceased
- 2006-02-03 WO PCT/US2006/004230 patent/WO2006084262A1/en not_active Ceased
- 2006-02-03 JP JP2007554312A patent/JP2008530275A/ja not_active Ceased
- 2006-02-03 ES ES06734482T patent/ES2377439T3/es active Active
- 2006-02-03 KR KR1020077020068A patent/KR101314419B1/ko not_active Expired - Fee Related
-
2007
- 2007-09-03 NO NO20074471A patent/NO20074471L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2006210403A1 (en) | 2006-08-10 |
| CN101155893B (zh) | 2012-07-04 |
| ATE533826T1 (de) | 2011-12-15 |
| US20060197053A1 (en) | 2006-09-07 |
| JP2008530275A (ja) | 2008-08-07 |
| RU2007133099A (ru) | 2009-03-10 |
| AU2006210403B2 (en) | 2011-09-22 |
| EP1846535A1 (en) | 2007-10-24 |
| EP1846535B1 (en) | 2011-11-16 |
| EP2258787A3 (en) | 2012-05-23 |
| US8715521B2 (en) | 2014-05-06 |
| ES2377439T3 (es) | 2012-03-27 |
| WO2006084262A1 (en) | 2006-08-10 |
| CN101155893A (zh) | 2008-04-02 |
| EP2258787A2 (en) | 2010-12-08 |
| KR20070103763A (ko) | 2007-10-24 |
| KR101314419B1 (ko) | 2013-10-10 |
| BRPI0606828A2 (pt) | 2009-07-21 |
| NO20074471L (no) | 2007-10-19 |
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