KR20120123612A - 질소 함유 양이온을 포함하는 이온성 액체 - Google Patents
질소 함유 양이온을 포함하는 이온성 액체 Download PDFInfo
- Publication number
- KR20120123612A KR20120123612A KR1020127027271A KR20127027271A KR20120123612A KR 20120123612 A KR20120123612 A KR 20120123612A KR 1020127027271 A KR1020127027271 A KR 1020127027271A KR 20127027271 A KR20127027271 A KR 20127027271A KR 20120123612 A KR20120123612 A KR 20120123612A
- Authority
- KR
- South Korea
- Prior art keywords
- ammonium
- dimethylethanolammonium
- butyl diethanol
- diethanol ammonium
- butyl
- 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.)
- Withdrawn
Links
- -1 nitrogen containing cations Chemical class 0.000 title claims abstract description 72
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 66
- 150000001768 cations Chemical class 0.000 claims abstract description 29
- 150000001450 anions Chemical class 0.000 claims abstract description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 138
- 150000001875 compounds Chemical class 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 14
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 14
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 12
- 229940014662 pantothenate Drugs 0.000 claims description 11
- 235000019161 pantothenic acid Nutrition 0.000 claims description 11
- 239000011713 pantothenic acid Substances 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims description 9
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 9
- 150000002500 ions Chemical class 0.000 claims description 9
- LRMSQVBRUNSOJL-UHFFFAOYSA-M 2,2,3,3,3-pentafluoropropanoate Chemical compound [O-]C(=O)C(F)(F)C(F)(F)F LRMSQVBRUNSOJL-UHFFFAOYSA-M 0.000 claims description 8
- IONYGGJUUJFXJK-UHFFFAOYSA-N 2,3,4,5,6-pentachlorobenzoic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IONYGGJUUJFXJK-UHFFFAOYSA-N 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 8
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 claims description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 8
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical group [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
- KVSASDOGYIBWTA-UHFFFAOYSA-N chloro benzoate Chemical compound ClOC(=O)C1=CC=CC=C1 KVSASDOGYIBWTA-UHFFFAOYSA-N 0.000 claims description 8
- OSTIHFXUTPZJQL-UHFFFAOYSA-N fluoro benzoate Chemical compound FOC(=O)C1=CC=CC=C1 OSTIHFXUTPZJQL-UHFFFAOYSA-N 0.000 claims description 8
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 claims description 8
- YPJUNDFVDDCYIH-UHFFFAOYSA-N perfluorobutyric acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)F YPJUNDFVDDCYIH-UHFFFAOYSA-N 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 7
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 7
- 150000007942 carboxylates Chemical class 0.000 claims description 7
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 7
- YZERDTREOUSUHF-UHFFFAOYSA-N pentafluorobenzoic acid Chemical compound OC(=O)C1=C(F)C(F)=C(F)C(F)=C1F YZERDTREOUSUHF-UHFFFAOYSA-N 0.000 claims description 7
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 7
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 7
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 6
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 6
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims description 6
- GCAIEATUVJFSMC-UHFFFAOYSA-N benzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1C(O)=O GCAIEATUVJFSMC-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 238000006555 catalytic reaction Methods 0.000 claims description 6
- 229940071106 ethylenediaminetetraacetate Drugs 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 6
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 6
- 229940049953 phenylacetate Drugs 0.000 claims description 6
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 claims description 5
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 102000004190 Enzymes Human genes 0.000 claims description 4
- 108090000790 Enzymes Proteins 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 150000003871 sulfonates Chemical group 0.000 claims description 4
- UBKBVPONTPMQQW-UHFFFAOYSA-N azane;2-hydroxyacetic acid Chemical compound [NH4+].OCC([O-])=O UBKBVPONTPMQQW-UHFFFAOYSA-N 0.000 claims description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- KLIDOSBTXDALBI-UHFFFAOYSA-N ammonium nonanoate Chemical compound [NH4+].CCCCCCCCC([O-])=O KLIDOSBTXDALBI-UHFFFAOYSA-N 0.000 claims description 2
- PQILKFQDIYPBKI-UHFFFAOYSA-N azane;2-phenylacetic acid Chemical compound [NH4+].[O-]C(=O)CC1=CC=CC=C1 PQILKFQDIYPBKI-UHFFFAOYSA-N 0.000 claims description 2
- WZEMSIKSCALWJZ-UHFFFAOYSA-N azane;ethanol Chemical compound N.CCO.CCO WZEMSIKSCALWJZ-UHFFFAOYSA-N 0.000 claims description 2
- RXQNHIDQIJXKTK-UHFFFAOYSA-N azane;pentanoic acid Chemical compound [NH4+].CCCCC([O-])=O RXQNHIDQIJXKTK-UHFFFAOYSA-N 0.000 claims description 2
- YNTQKXBRXYIAHM-UHFFFAOYSA-N azanium;butanoate Chemical compound [NH4+].CCCC([O-])=O YNTQKXBRXYIAHM-UHFFFAOYSA-N 0.000 claims description 2
- CKKXWJDFFQPBQL-UAIGNFCESA-N diazanium;(z)-but-2-enedioate Chemical compound [NH4+].[NH4+].[O-]C(=O)\C=C/C([O-])=O CKKXWJDFFQPBQL-UAIGNFCESA-N 0.000 claims description 2
- 229940049920 malate Drugs 0.000 claims description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 150000003077 polyols Chemical group 0.000 claims description 2
- KOOLMABFSWIFCR-UHFFFAOYSA-N tetraazanium;benzene-1,2,3,4-tetracarboxylate Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].[O-]C(=O)C1=CC=C(C([O-])=O)C(C([O-])=O)=C1C([O-])=O KOOLMABFSWIFCR-UHFFFAOYSA-N 0.000 claims description 2
- GWKJQMWJVZAKJS-UHFFFAOYSA-N triazanium benzene-1,2,3-tricarboxylate Chemical compound [NH4+].[NH4+].[NH4+].[O-]C(=O)c1cccc(C([O-])=O)c1C([O-])=O GWKJQMWJVZAKJS-UHFFFAOYSA-N 0.000 claims description 2
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 claims 3
- 229940076788 pyruvate Drugs 0.000 claims 3
- 229940086735 succinate Drugs 0.000 claims 3
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims 2
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims 2
- 229940001468 citrate Drugs 0.000 claims 2
- DWLUNFAUNAHQIY-UHFFFAOYSA-N 2-(dimethylamino)ethanol;propanoic acid Chemical compound CCC([O-])=O.C[NH+](C)CCO DWLUNFAUNAHQIY-UHFFFAOYSA-N 0.000 claims 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
- AVMNFQHJOOYCAP-UHFFFAOYSA-N acetic acid;propanoic acid Chemical compound CC(O)=O.CCC(O)=O AVMNFQHJOOYCAP-UHFFFAOYSA-N 0.000 claims 1
- 235000012501 ammonium carbonate Nutrition 0.000 claims 1
- 239000001099 ammonium carbonate Substances 0.000 claims 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 150000003949 imides Chemical class 0.000 claims 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims 1
- 150000004760 silicates Chemical class 0.000 claims 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 claims 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 3
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 83
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- IBZKBSXREAQDTO-UHFFFAOYSA-N 2-methoxy-n-(2-methoxyethyl)ethanamine Chemical compound COCCNCCOC IBZKBSXREAQDTO-UHFFFAOYSA-N 0.000 description 10
- 229910019142 PO4 Inorganic materials 0.000 description 10
- 235000021317 phosphate Nutrition 0.000 description 10
- ZXVOCOLRQJZVBW-UHFFFAOYSA-N azane;ethanol Chemical compound N.CCO ZXVOCOLRQJZVBW-UHFFFAOYSA-N 0.000 description 9
- 239000010452 phosphate Substances 0.000 description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
- GHOKWGTUZJEAQD-ZETCQYMHSA-M (R)-pantothenate Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC([O-])=O GHOKWGTUZJEAQD-ZETCQYMHSA-M 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- 229930029653 phosphoenolpyruvate Natural products 0.000 description 7
- DTBNBXWJWCWCIK-UHFFFAOYSA-K phosphonatoenolpyruvate Chemical compound [O-]C(=O)C(=C)OP([O-])([O-])=O DTBNBXWJWCWCIK-UHFFFAOYSA-K 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- FEWJPZIEWOKRBE-JCYAYHJZSA-M L-tartrate(1-) Chemical compound OC(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 6
- 229960001860 salicylate Drugs 0.000 description 6
- YURNCBVQZBJDAJ-UHFFFAOYSA-N 2-heptenoic acid Chemical compound CCCCC=CC(O)=O YURNCBVQZBJDAJ-UHFFFAOYSA-N 0.000 description 5
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 5
- ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 5
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 5
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
- UDMBCSSLTHHNCD-UHFFFAOYSA-N Coenzym Q(11) Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(O)=O)C(O)C1O UDMBCSSLTHHNCD-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 5
- UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 5
- 229950006790 adenosine phosphate Drugs 0.000 description 5
- BDJRBEYXGGNYIS-UHFFFAOYSA-L azelaate(2-) Chemical compound [O-]C(=O)CCCCCCCC([O-])=O BDJRBEYXGGNYIS-UHFFFAOYSA-L 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 description 5
- JFCQEDHGNNZCLN-UHFFFAOYSA-L glutarate(2-) Chemical compound [O-]C(=O)CCCC([O-])=O JFCQEDHGNNZCLN-UHFFFAOYSA-L 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 229940001447 lactate Drugs 0.000 description 5
- YIYBQIKDCADOSF-UHFFFAOYSA-N pent-2-enoic acid Chemical compound CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 description 5
- WLJVNTCWHIRURA-UHFFFAOYSA-M pimelate(1-) Chemical compound OC(=O)CCCCCC([O-])=O WLJVNTCWHIRURA-UHFFFAOYSA-M 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 5
- NIONDZDPPYHYKY-UHFFFAOYSA-N 2-hexenoic acid Chemical compound CCCC=CC(O)=O NIONDZDPPYHYKY-UHFFFAOYSA-N 0.000 description 4
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- 239000012491 analyte Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
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- 238000003556 assay Methods 0.000 description 1
- UVHHMCQSDZMGPY-UHFFFAOYSA-N azane ethanol 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)[O-])(F)F.[NH4+].C(C)O UVHHMCQSDZMGPY-UHFFFAOYSA-N 0.000 description 1
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- HWNNFBSUGREKHS-UHFFFAOYSA-N azanium hex-2-enoate Chemical compound [NH4+].CCCC=CC([O-])=O HWNNFBSUGREKHS-UHFFFAOYSA-N 0.000 description 1
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- PXIKWDKLEXYRBD-UHFFFAOYSA-N azanium;ethanol;benzoate Chemical compound [NH4+].CCO.[O-]C(=O)C1=CC=CC=C1 PXIKWDKLEXYRBD-UHFFFAOYSA-N 0.000 description 1
- QHFIXIVFAWSLNS-UHFFFAOYSA-N azanium;ethanol;hydrogen carbonate Chemical compound [NH4+].CCO.OC([O-])=O QHFIXIVFAWSLNS-UHFFFAOYSA-N 0.000 description 1
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- 238000000746 purification Methods 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- DXWCHSWAVYOCNP-UHFFFAOYSA-N pyridine-2-carboxylate;tributylazanium Chemical compound [O-]C(=O)C1=CC=CC=N1.CCCC[NH+](CCCC)CCCC DXWCHSWAVYOCNP-UHFFFAOYSA-N 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LESFYQKBUCDEQP-UHFFFAOYSA-N tetraazanium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound N.N.N.N.OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O LESFYQKBUCDEQP-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- YGNGABUJMXJPIJ-UHFFFAOYSA-N thiatriazole Chemical class C1=NN=NS1 YGNGABUJMXJPIJ-UHFFFAOYSA-N 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 150000004886 thiomorpholines Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000004882 thiopyrans Chemical class 0.000 description 1
- YWYZEGXAUVWDED-UHFFFAOYSA-N triammonium citrate Chemical compound [NH4+].[NH4+].[NH4+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O YWYZEGXAUVWDED-UHFFFAOYSA-N 0.000 description 1
- IJUNUFZOWZUOCL-UHFFFAOYSA-N triazanium ethanol phosphate Chemical compound P(=O)([O-])([O-])[O-].[NH4+].C(C)O.[NH4+].[NH4+] IJUNUFZOWZUOCL-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ZAMCTDDIJFNXOH-UHFFFAOYSA-N tributylazanium;acetate Chemical compound CC(O)=O.CCCCN(CCCC)CCCC ZAMCTDDIJFNXOH-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- AFVLVVWMAFSXCK-UHFFFAOYSA-N α-cyano-4-hydroxycinnamic acid Chemical compound OC(=O)C(C#N)=CC1=CC=C(O)C=C1 AFVLVVWMAFSXCK-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/003—Catalysts comprising hydrides, coordination complexes or organic compounds containing enzymes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—Quaternary ammonium compounds
- C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/12—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic the nitrogen atom of the amino group being further bound to hydrocarbon groups substituted by hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/40—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton with quaternised nitrogen atoms bound to carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
- C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/24—Thiols, sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C321/28—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/19—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/077—Ionic Liquids
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Catalysts (AREA)
- Extraction Or Liquid Replacement (AREA)
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| GB0407908.3 | 2004-04-07 | ||
| GBGB0407908.3A GB0407908D0 (en) | 2004-04-07 | 2004-04-07 | Ionic liquids |
| PCT/GB2005/001364 WO2005097731A2 (en) | 2004-04-07 | 2005-04-07 | Ionic liquids comprising nitrogen containing cations |
Related Parent Applications (1)
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| KR1020067023342A Division KR101304892B1 (ko) | 2004-04-07 | 2005-04-07 | 질소 함유 양이온을 포함하는 이온성 액체 |
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| KR1020127027271A Withdrawn KR20120123612A (ko) | 2004-04-07 | 2005-04-07 | 질소 함유 양이온을 포함하는 이온성 액체 |
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| KR1020117014518A Expired - Lifetime KR101453145B1 (ko) | 2004-04-07 | 2005-04-07 | 질소 함유 양이온을 포함하는 이온성 액체 |
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Families Citing this family (108)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0407908D0 (en) * | 2004-04-07 | 2004-05-12 | Univ York | Ionic liquids |
| WO2006097931A2 (en) | 2005-03-17 | 2006-09-21 | Valtech Cardio, Ltd. | Mitral valve treatment techniques |
| US8951285B2 (en) | 2005-07-05 | 2015-02-10 | Mitralign, Inc. | Tissue anchor, anchoring system and methods of using the same |
| GB2444614A (en) * | 2005-09-30 | 2008-06-11 | Bioniqs Ltd | Alkanoyl ammonium salts as ionic liquids |
| GB0519898D0 (en) * | 2005-09-30 | 2005-11-09 | Bioniqs Ltd | Liquids |
| CA2867194C (en) | 2005-10-07 | 2016-10-04 | The University Of Alabama | Multi-functional ionic liquid compositions for overcoming polymorphism and imparting improved properties for active pharmaceutical, biological, nutritional, and energetic ingredients |
| US20070129568A1 (en) * | 2005-12-06 | 2007-06-07 | Ngimat, Co. | Ionic liquids |
| JP2008044849A (ja) * | 2006-08-10 | 2008-02-28 | Tokyo Univ Of Agriculture & Technology | 温度制御により水と可逆的に相溶/相分離を示すイオン液体 |
| US9974653B2 (en) | 2006-12-05 | 2018-05-22 | Valtech Cardio, Ltd. | Implantation of repair devices in the heart |
| US11259924B2 (en) | 2006-12-05 | 2022-03-01 | Valtech Cardio Ltd. | Implantation of repair devices in the heart |
| JP2008162899A (ja) * | 2006-12-27 | 2008-07-17 | Tokyo Univ Of Agriculture & Technology | 生体関連化合物からなるイオン液体 |
| US11660190B2 (en) | 2007-03-13 | 2023-05-30 | Edwards Lifesciences Corporation | Tissue anchors, systems and methods, and devices |
| WO2009016235A2 (en) * | 2007-08-02 | 2009-02-05 | Akzo Nobel N.V. | Chelating agent based ionic liquids, a process to prepare them, and their use |
| GB0718269D0 (en) | 2007-09-12 | 2007-10-31 | Bioniqs Ltd | Purification of organic compounds |
| SI2192117T1 (sl) | 2007-09-27 | 2014-10-30 | Toyama Chemical Co., Ltd. | Sol organskega amina in 6-fluoro-3-hidroksi-2-pirazinkarbonitrila ter postopek za izdelavo le-te |
| US8382829B1 (en) | 2008-03-10 | 2013-02-26 | Mitralign, Inc. | Method to reduce mitral regurgitation by cinching the commissure of the mitral valve |
| KR100958876B1 (ko) | 2008-04-02 | 2010-05-20 | 삼성엔지니어링 주식회사 | 다양한 극성/비극성 용매 혼화성 이온성 액체 및 그의제조방법 |
| NZ589497A (en) | 2008-06-02 | 2012-09-28 | Cipla Ltd | Process for the synthesis of arformoterol |
| CA2728078A1 (en) | 2008-06-16 | 2010-01-14 | Valtech Cardio, Ltd. | Annuloplasty devices and methods of delivery therefor |
| CN103926298B (zh) | 2008-12-01 | 2017-06-20 | Msa欧洲有限责任公司 | 具有离子液体电解质系统的电化学气体传感器 |
| DE102008044239A1 (de) * | 2008-12-01 | 2010-06-10 | Msa Auer Gmbh | Elektrochemischer Gassensor mit einer in einem Feststoff auf SiO2-Basis absorbierten ionischen Flüssigkeit als Elektrolyt mit organischen und/oder metallorganischen und/oder anorganischen Zusätzen |
| DE102008044240B4 (de) | 2008-12-01 | 2013-12-05 | Msa Auer Gmbh | Elektrochemischer Gassensor mit einer ionischen Flüssigkeit als Elektrolyt, welche mindestens ein Mono-, Di- oder Trialkylammonium-Kation enthält |
| US8545553B2 (en) | 2009-05-04 | 2013-10-01 | Valtech Cardio, Ltd. | Over-wire rotation tool |
| US8715342B2 (en) | 2009-05-07 | 2014-05-06 | Valtech Cardio, Ltd. | Annuloplasty ring with intra-ring anchoring |
| US10517719B2 (en) | 2008-12-22 | 2019-12-31 | Valtech Cardio, Ltd. | Implantation of repair devices in the heart |
| US8241351B2 (en) | 2008-12-22 | 2012-08-14 | Valtech Cardio, Ltd. | Adjustable partial annuloplasty ring and mechanism therefor |
| ES2873182T3 (es) | 2008-12-22 | 2021-11-03 | Valtech Cardio Ltd | Dispositivos de anuloplastia ajustables |
| US8353956B2 (en) | 2009-02-17 | 2013-01-15 | Valtech Cardio, Ltd. | Actively-engageable movement-restriction mechanism for use with an annuloplasty structure |
| US9968452B2 (en) | 2009-05-04 | 2018-05-15 | Valtech Cardio, Ltd. | Annuloplasty ring delivery cathethers |
| US12485010B2 (en) | 2009-05-07 | 2025-12-02 | Edwards Lifesciences Innovation (Israel) Ltd. | Multiple anchor delivery tool |
| US9180007B2 (en) | 2009-10-29 | 2015-11-10 | Valtech Cardio, Ltd. | Apparatus and method for guide-wire based advancement of an adjustable implant |
| US10098737B2 (en) | 2009-10-29 | 2018-10-16 | Valtech Cardio, Ltd. | Tissue anchor for annuloplasty device |
| US8734467B2 (en) | 2009-12-02 | 2014-05-27 | Valtech Cardio, Ltd. | Delivery tool for implantation of spool assembly coupled to a helical anchor |
| US8870950B2 (en) | 2009-12-08 | 2014-10-28 | Mitral Tech Ltd. | Rotation-based anchoring of an implant |
| US11653910B2 (en) | 2010-07-21 | 2023-05-23 | Cardiovalve Ltd. | Helical anchor implantation |
| JP5579677B2 (ja) * | 2010-08-30 | 2014-08-27 | 日本乳化剤株式会社 | イオン液体の製造方法 |
| CN102070462A (zh) * | 2011-01-20 | 2011-05-25 | 中国科学院过程工程研究所 | 一种乙二胺硝基酚类离子液体及其制备方法 |
| GB2493488A (en) | 2011-05-20 | 2013-02-13 | Innovia Films Ltd | Process for dissolving and casting non-dissolving cellulose |
| GB2493490A (en) | 2011-05-20 | 2013-02-13 | Innovia Films Ltd | Process for dissolving and casting non-dissolving cellulose |
| US10792152B2 (en) | 2011-06-23 | 2020-10-06 | Valtech Cardio, Ltd. | Closed band for percutaneous annuloplasty |
| EP3725269A1 (en) | 2011-06-23 | 2020-10-21 | Valtech Cardio, Ltd. | Closure element for use with annuloplasty structure |
| EP2760821B1 (en) * | 2011-09-02 | 2017-10-11 | Novartis AG | Choline salt of an anti-inflammatory substituted cyclobutenedione compound |
| CN103890577B (zh) | 2011-10-25 | 2016-08-24 | Msa欧洲有限责任公司 | 用于检测氨和胺的用离子液体作为电解质的电化学气体传感器 |
| US8858623B2 (en) | 2011-11-04 | 2014-10-14 | Valtech Cardio, Ltd. | Implant having multiple rotational assemblies |
| EP3656434B1 (en) | 2011-11-08 | 2021-10-20 | Valtech Cardio, Ltd. | Controlled steering functionality for implant-delivery tool |
| JP5323221B2 (ja) * | 2011-11-28 | 2013-10-23 | 日本乳化剤株式会社 | イオン性液体並びにこれを含む帯電防止剤、防曇剤、分散剤または乳化剤、潤滑剤、電解液、およびセルロース溶解剤 |
| EP2881083B1 (en) | 2011-12-12 | 2017-03-22 | David Alon | Heart valve repair device |
| WO2013158473A1 (en) * | 2012-04-16 | 2013-10-24 | Shell Oil Company | Lubricant compositions containing ionic liquids |
| WO2014052818A1 (en) | 2012-09-29 | 2014-04-03 | Mitralign, Inc. | Plication lock delivery system and method of use thereof |
| EP2911594B1 (en) | 2012-10-23 | 2018-12-05 | Valtech Cardio, Ltd. | Controlled steering functionality for implant-delivery tool |
| WO2014064695A2 (en) | 2012-10-23 | 2014-05-01 | Valtech Cardio, Ltd. | Percutaneous tissue anchor techniques |
| JP6559394B2 (ja) * | 2012-12-05 | 2019-08-14 | ミヨシ油脂株式会社 | 親水性室温イオン液体とその用途 |
| WO2014087402A1 (en) | 2012-12-06 | 2014-06-12 | Valtech Cardio, Ltd. | Techniques for guide-wire based advancement of a tool |
| ES2934670T3 (es) | 2013-01-24 | 2023-02-23 | Cardiovalve Ltd | Válvulas protésicas ancladas de forma ventricular |
| US9724084B2 (en) | 2013-02-26 | 2017-08-08 | Mitralign, Inc. | Devices and methods for percutaneous tricuspid valve repair |
| CN103178297B (zh) * | 2013-03-01 | 2015-12-09 | 广东电网公司电力科学研究院 | 锂二次电池及其电解液 |
| US10449333B2 (en) | 2013-03-14 | 2019-10-22 | Valtech Cardio, Ltd. | Guidewire feeder |
| CN105283214B (zh) | 2013-03-15 | 2018-10-16 | 北京泰德制药股份有限公司 | 平移导管、系统及其使用方法 |
| CN103274931A (zh) * | 2013-06-05 | 2013-09-04 | 中国石油大学(华东) | 一种用于分离羧酸混合物萃取精馏的溶剂 |
| US10070857B2 (en) | 2013-08-31 | 2018-09-11 | Mitralign, Inc. | Devices and methods for locating and implanting tissue anchors at mitral valve commissure |
| US10299793B2 (en) | 2013-10-23 | 2019-05-28 | Valtech Cardio, Ltd. | Anchor magazine |
| US9610162B2 (en) | 2013-12-26 | 2017-04-04 | Valtech Cardio, Ltd. | Implantation of flexible implant |
| EP3130670B1 (en) * | 2014-04-10 | 2020-10-21 | Miyoshi Oil & Fat Co., Ltd. | Biocatalyst solvent using ionic liquid, and biocatalyst solution containing biocatalyst and said solvent |
| JP6478775B2 (ja) | 2014-05-15 | 2019-03-06 | キヤノン株式会社 | アミン化合物及びイオン導電剤、導電性樹脂組成物 |
| JP6489910B2 (ja) * | 2014-05-15 | 2019-03-27 | キヤノン株式会社 | ヒドロキシ化合物、イオン導電剤、および導電性樹脂組成物 |
| US10524910B2 (en) | 2014-07-30 | 2020-01-07 | Mitraltech Ltd. 3 Ariel Sharon Avenue | Articulatable prosthetic valve |
| CN104174255A (zh) * | 2014-08-18 | 2014-12-03 | 南京信息工程大学 | 一种离子液体脱硫剂及其制备方法和应用 |
| US10119064B2 (en) * | 2014-09-22 | 2018-11-06 | Dow Global Technologies Llc | Thermally unstable ammonium carboxylates for enhanced oil recovery |
| EP4331503A3 (en) | 2014-10-14 | 2024-06-05 | Edwards Lifesciences Innovation (Israel) Ltd. | Leaflet-restraining techniques |
| JP2016083623A (ja) * | 2014-10-27 | 2016-05-19 | 国立研究開発法人産業技術総合研究所 | 酸性ガス吸収液及び酸性ガス分離回収方法 |
| EP3253333B1 (en) | 2015-02-05 | 2024-04-03 | Cardiovalve Ltd | Prosthetic valve with axially-sliding frames |
| US20160256269A1 (en) | 2015-03-05 | 2016-09-08 | Mitralign, Inc. | Devices for treating paravalvular leakage and methods use thereof |
| CN114515173B (zh) | 2015-04-30 | 2025-01-28 | 爱德华兹生命科学创新(以色列)有限公司 | 瓣膜成形术技术 |
| WO2016192829A1 (en) | 2015-05-29 | 2016-12-08 | Merck Patent Gmbh | Deep eutectic solvents and/or ionic liquids as feed media |
| EP3303555B1 (en) | 2015-05-29 | 2020-06-24 | Merck Patent GmbH | Deep eutectic solvents and/or ionic liquids in cell culture media |
| US10751182B2 (en) | 2015-12-30 | 2020-08-25 | Edwards Lifesciences Corporation | System and method for reshaping right heart |
| US10828160B2 (en) | 2015-12-30 | 2020-11-10 | Edwards Lifesciences Corporation | System and method for reducing tricuspid regurgitation |
| US10531866B2 (en) | 2016-02-16 | 2020-01-14 | Cardiovalve Ltd. | Techniques for providing a replacement valve and transseptal communication |
| US10702274B2 (en) | 2016-05-26 | 2020-07-07 | Edwards Lifesciences Corporation | Method and system for closing left atrial appendage |
| GB201611910D0 (en) | 2016-07-08 | 2016-08-24 | Valtech Cardio Ltd | Adjustable annuloplasty device with alternating peaks and troughs |
| US20190231525A1 (en) | 2016-08-01 | 2019-08-01 | Mitraltech Ltd. | Minimally-invasive delivery systems |
| EP3496664B1 (en) | 2016-08-10 | 2021-09-29 | Cardiovalve Ltd | Prosthetic valve with concentric frames |
| CN109789214B (zh) * | 2016-09-27 | 2022-06-28 | 卡姆拉斯公司 | 包含edta烷基铵盐的混合物和制剂 |
| US11045627B2 (en) | 2017-04-18 | 2021-06-29 | Edwards Lifesciences Corporation | Catheter system with linear actuation control mechanism |
| IT201700088474A1 (it) * | 2017-08-02 | 2019-02-02 | Novamont Spa | Composizioni erbicide a base di acido pelargonico |
| US12064347B2 (en) | 2017-08-03 | 2024-08-20 | Cardiovalve Ltd. | Prosthetic heart valve |
| US11793633B2 (en) | 2017-08-03 | 2023-10-24 | Cardiovalve Ltd. | Prosthetic heart valve |
| US12458493B2 (en) | 2017-09-19 | 2025-11-04 | Cardiovalve Ltd. | Prosthetic heart valve and delivery systems and methods |
| US10835221B2 (en) | 2017-11-02 | 2020-11-17 | Valtech Cardio, Ltd. | Implant-cinching devices and systems |
| US11135062B2 (en) | 2017-11-20 | 2021-10-05 | Valtech Cardio Ltd. | Cinching of dilated heart muscle |
| WO2019145947A1 (en) | 2018-01-24 | 2019-08-01 | Valtech Cardio, Ltd. | Contraction of an annuloplasty structure |
| WO2019145941A1 (en) | 2018-01-26 | 2019-08-01 | Valtech Cardio, Ltd. | Techniques for facilitating heart valve tethering and chord replacement |
| CN120000269A (zh) | 2018-07-12 | 2025-05-16 | 爱德华兹生命科学创新(以色列)有限公司 | 瓣环成形系统及其锁定工具 |
| WO2020163839A1 (en) * | 2019-02-10 | 2020-08-13 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Glyonic liquids and uses thereof |
| CN120531524A (zh) | 2019-05-29 | 2025-08-26 | 爱德华兹生命科学创新(以色列)有限公司 | 组织锚固器存取系统和方法 |
| US12364606B2 (en) | 2019-07-23 | 2025-07-22 | Edwards Lifesciences Innovation (Israel) Ltd. | Fluoroscopic visualization of heart valve anatomy |
| WO2021038560A1 (en) | 2019-08-28 | 2021-03-04 | Valtech Cardio, Ltd. | Low-profile steerable catheter |
| CA3143225A1 (en) | 2019-08-30 | 2021-03-04 | Valtech Cardio, Ltd. | Anchor channel tip |
| CA3155254A1 (en) | 2019-09-25 | 2021-04-01 | Cardiac Implants Llc | Cardiac valve annulus reduction system |
| WO2021084407A1 (en) | 2019-10-29 | 2021-05-06 | Valtech Cardio, Ltd. | Annuloplasty and tissue anchor technologies |
| CN111662193B (zh) * | 2020-05-13 | 2023-01-10 | 珠海中科先进技术研究院有限公司 | 一种醇胺脂肪酸离子液体及其制备方法和应用 |
| WO2021236634A2 (en) | 2020-05-20 | 2021-11-25 | Cardiac Implants, Llc | Reducing the diameter of a cardiac valve annulus with independent control over each of the anchors that are launched into the annulus |
| EP4167869B1 (en) | 2020-06-19 | 2025-03-26 | Edwards Lifesciences Innovation (Israel) Ltd. | Self-stopping tissue anchors |
| CN111892499B (zh) * | 2020-07-27 | 2022-06-28 | 北京中富瑞科环保科技有限公司 | 一种离子液体及其在二氧化硫吸收中的应用 |
| EP4208160A4 (en) * | 2020-09-01 | 2024-12-18 | I2O Therapeutics, Inc. | IONIC LIQUID FORMULATIONS FOR THE TREATMENT OF DIABETES |
| US12357459B2 (en) | 2020-12-03 | 2025-07-15 | Cardiovalve Ltd. | Transluminal delivery system |
| KR20230006345A (ko) * | 2021-07-02 | 2023-01-10 | 삼성전자주식회사 | 전기화학적 가스 센서용 전해질 및 이를 포함하는 전기화학적 가스 센서 |
| CN114606508B (zh) * | 2022-03-16 | 2023-06-06 | 四川大学 | 一种环保型离子液体脱脂液及其使用方法 |
Family Cites Families (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB879259A (en) | 1956-11-20 | 1961-10-11 | Riker Laboratories Inc | Acid addition salts of 2-dimethylaminoethanol and central nervous system stimulant compositions containing them |
| US3547423A (en) * | 1968-04-12 | 1970-12-15 | Gen Electric | Electrolytic capacitor and electrolyte material therefor |
| US3686156A (en) * | 1970-05-26 | 1972-08-22 | Du Pont | Curing dialkyl xanthogen disulfide-modified chloroprene sol polymers with amines |
| US3751561A (en) * | 1970-11-23 | 1973-08-07 | Monsanto Co | Stable polymer-enzyme oral hygiene compositions |
| GB1391922A (en) | 1972-03-29 | 1975-04-23 | Ppg Industries Inc | Epoxy compositions |
| US4001156A (en) * | 1972-08-03 | 1977-01-04 | Ppg Industries, Inc. | Method of producing epoxy group-containing, quaternary ammonium salt-containing resins |
| JPS5235078B2 (enExample) * | 1972-09-18 | 1977-09-07 | ||
| US3897241A (en) * | 1973-08-09 | 1975-07-29 | Taki Fertilizer Mfg Co Ltd | Ethanolamine/organic carboxylic acid composition for accelerating fruit ripening |
| DE2440209A1 (de) | 1974-08-22 | 1976-03-04 | Basf Ag | Beta-sulfo-propionsaeureverbindungen und verfahren zu ihrer herstellung |
| CA1076283A (en) * | 1974-12-20 | 1980-04-22 | Ray A. Dickie | Water-based paint with corrosion inhibitor i |
| US4191674A (en) * | 1975-07-25 | 1980-03-04 | Ppg Industries, Inc. | Zwitterion-containing compositions |
| AT348637B (de) * | 1977-04-28 | 1979-02-26 | Vianova Kunstharz Ag | Verfahren zur herstellung kationischer wasserloeslicher bindemittel fuer die elektrotauchlackierung |
| US4189761A (en) * | 1977-08-12 | 1980-02-19 | Sprague Electric Company | Non-aqueous electrolytic capacitor electrolyte |
| US4219624A (en) * | 1978-11-20 | 1980-08-26 | Olin Corporation | Stabilization of amine catalysts in a composition with halogenated polyols for use in polyurethane foam production |
| ES490557A0 (es) * | 1979-04-16 | 1981-04-16 | Lubrizol Corp | Un procedimiento para la preparacion de un carboxilato amonico soluble en agua. |
| US4377654A (en) * | 1981-11-16 | 1983-03-22 | Polaroid Corporation | Polymerization processes and polymer compositions |
| JPS6096792A (ja) * | 1983-11-01 | 1985-05-30 | Nippon Paint Co Ltd | カチオン型電着塗装方法 |
| JPS61117288A (ja) * | 1984-04-04 | 1986-06-04 | Chiyoda Kagaku Kenkyusho:Kk | 鉄系金属防錆剤 |
| US4709083A (en) * | 1986-05-19 | 1987-11-24 | The United States Of America As Represented By The Secretary Of The Army | Method of making boron analogues |
| DD262042A1 (de) | 1987-07-14 | 1988-11-16 | Staatliches Inst Fuer Immunpra | Verfahren zur herstellung partiell inaktivierter biologisch aktiver biopolymere |
| DE3904992A1 (de) * | 1989-02-18 | 1990-08-23 | Riedel De Haen Ag | Reagenz fuer die coulometrische wasserbestimmung |
| JPH03165999A (ja) | 1989-11-24 | 1991-07-17 | Nippondenso Co Ltd | はんだ付け用水溶性フラックス |
| DE69229400T2 (de) * | 1991-11-22 | 1999-09-30 | Japan Tobacco Inc., Yokohama | Neue fettsäuresalze mit herbizider wirkung |
| CZ287435B6 (en) * | 1993-11-04 | 2000-11-15 | Bayer Ag | Process for preparing foam polyurethane shaped parts without use of fluorochlorinated hydrocarbons |
| US5371166A (en) | 1993-12-22 | 1994-12-06 | The B. F. Goodrich Company | Polyurethane composition for use as a dispersing binder |
| US5824832A (en) * | 1996-07-22 | 1998-10-20 | Akzo Nobel Nv | Linear alxylbenzene formation using low temperature ionic liquid |
| US6361940B1 (en) * | 1996-09-24 | 2002-03-26 | Qiagen Genomics, Inc. | Compositions and methods for enhancing hybridization and priming specificity |
| US6521237B2 (en) * | 1998-11-12 | 2003-02-18 | Johnson & Johnson Consumer Companies, Inc. | Skin care composition |
| DE19919495A1 (de) * | 1999-04-29 | 2000-11-02 | Celanese Chem Europe Gmbh | Verfahren zur Herstellung von Aldehyden |
| US6506239B1 (en) * | 1999-09-16 | 2003-01-14 | Canon Kabushiki Kaisha | Liquid composition, ink set, recording process, ink cartridge, recording unit, process for forming multi-color image, ink-jet apparatus, process for facilitating fixing of ink to recording medium, and process for improving quality of multi-color image |
| PT1274700E (pt) * | 2000-01-03 | 2005-02-28 | Pharmacia Corp | Di-hidrobenzopiranos di-hidrobenzotiopiranos e tetra-hidroquinolinas para o tratamento de afeccoes mediadas por cox-2 |
| DE10003708A1 (de) * | 2000-01-28 | 2001-08-02 | Solvent Innovation Gmbh | Neuartige chirale ionische Flüssigkeiten und Verfahren zu ihrer Darstellung in enantiomerenreiner oder enantiomerenangereicherter Form |
| DE10018098A1 (de) * | 2000-04-12 | 2001-11-08 | Rudolf Erich Klemke | Antitumoraktivität und Induktion der Apoptose mittels wasserlöslicher Derivate der Propion- und der Buttersäure bei Krebserkrankungen |
| CA2407857C (en) | 2000-05-05 | 2009-11-17 | Curtis A. Cole | Skin care composition comprising a retinoid, an acid and 2-dimethyl amino ethanol |
| US6436268B1 (en) * | 2000-08-02 | 2002-08-20 | Kemet Electronics Corporation | Non-aqueous electrolytes for anodizing |
| GB0023706D0 (en) | 2000-09-27 | 2000-11-08 | Scionix Ltd | Ionic liquids |
| EP1205555A1 (de) * | 2000-11-08 | 2002-05-15 | Solvent Innovation GmbH | Enzymkatalyse in Gegenwart ionischer Flüssigkeiten |
| KR100823972B1 (ko) * | 2001-03-26 | 2008-04-22 | 닛신보세키 가부시키 가이샤 | 이온성 액체, 축전 디바이스용 전해질염, 축전 디바이스용전해액, 전기 2중층 캐패시터, 및 2차 전지 |
| DE10145747A1 (de) * | 2001-09-17 | 2003-04-03 | Solvent Innovation Gmbh | Ionische Flüssigkeiten |
| RU2001130402A (ru) * | 2001-11-13 | 2003-08-20 | Хальдор Топсеэ А/С (DK) | Способ изомеризации С5-С8 парафинового углеводородного сырья |
| DE10201778A1 (de) | 2002-01-17 | 2003-07-31 | Studiengesellschaft Kohle Mbh | Verfahren zur Durchführung von enzymatischen Reaktionen in ionischen Lösungsmitteln |
| DE10303931B4 (de) * | 2002-02-04 | 2013-04-18 | Institut Français du Pétrole | Katalytische Zusammensetzung zur Dimerisierung, Co-Dimerisierung, Oligomerisierung und Polymerisation der Olefine |
| FR2835447B1 (fr) | 2002-02-04 | 2005-01-07 | Inst Francais Du Petrole | Composition catalytique pour la dimerisation, la co-dimerisation et l'oligomerisation des olefines |
| DE10206808A1 (de) * | 2002-02-19 | 2003-08-28 | Oxeno Olefinchemie Gmbh | Verfahren zur Trennung von Stoffen durch Extraktion oder Wäsche mit ionischen Flüssigkeiten |
| DE10208822A1 (de) * | 2002-03-01 | 2003-09-11 | Solvent Innovation Gmbh | Halogenfreie ionische Flüssigkeiten |
| EP1354863B1 (en) * | 2002-04-18 | 2005-06-08 | Haldor Topsoe A/S | Continuous process for the removal of water from a hydrocarbon stream |
| KR100970918B1 (ko) * | 2002-04-24 | 2010-07-16 | 닛신보 홀딩스 가부시키 가이샤 | 이온성 액체 및 탈수 방법, 및 전기 이중층 커패시터, 및2차 전지 |
| DE10219227A1 (de) * | 2002-04-30 | 2003-11-13 | Bayer Ag | Ionische Flüssigkeiten |
| AU2003263889A1 (en) * | 2002-08-16 | 2004-03-03 | Sachem, Inc. | Ionic liquids containing a sulfonate anion |
| US8636992B2 (en) * | 2002-09-30 | 2014-01-28 | Johnson & Johnson Consumer France Sas | Thickener compositions comprising sclerotium gum and a copolymer |
| GB0300595D0 (en) * | 2003-01-10 | 2003-02-12 | Univ Cambridge Tech | Ionic liquids |
| DE10306617A1 (de) | 2003-02-14 | 2004-08-26 | Merck Patent Gmbh | Salze mit Cyanoborat-Anionen |
| DE10316418A1 (de) | 2003-04-10 | 2004-10-21 | Basf Ag | Verwendung einer ionischen Flüssigkeit |
| JP2007500429A (ja) * | 2003-05-01 | 2007-01-11 | アリゾナ ボード オブ リージェンツ ア ボディー コーポレート アクティング オン ビハーフ オブ アリゾナ ステイト ユニバーシティ | 燃料電池その他の高温用途のための高温安定性を備えるイオン性液体及びイオン性液体酸、製造方法及びそれを使用する電池 |
| EP1736542A4 (en) | 2004-03-23 | 2008-10-29 | Hiroyuki Ohno | SOLVENTS FOR SOLVING NUCLEIC ACID, NUCLEIC ACIDIC SOLUTION, AND METHOD FOR PRESERVING NUCLEIC ACID |
| GB0407908D0 (en) | 2004-04-07 | 2004-05-12 | Univ York | Ionic liquids |
| CA2615367A1 (en) * | 2004-07-16 | 2006-01-26 | Simon Fraser University | Phosphonium ionic liquids as recyclable solvents for solution phase chemistry |
| GB0422447D0 (en) * | 2004-10-08 | 2004-11-10 | Univ Cambridge Tech | Use of ionic liquids |
| GB0519898D0 (en) * | 2005-09-30 | 2005-11-09 | Bioniqs Ltd | Liquids |
-
2004
- 2004-04-07 GB GBGB0407908.3A patent/GB0407908D0/en not_active Ceased
-
2005
- 2005-04-07 EP EP05735988A patent/EP1805131B1/en not_active Expired - Lifetime
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- 2005-04-07 NZ NZ606385A patent/NZ606385A/en not_active IP Right Cessation
- 2005-04-07 PL PL05735988T patent/PL1805131T3/pl unknown
- 2005-04-07 CA CA2563458A patent/CA2563458C/en not_active Expired - Lifetime
- 2005-04-07 EP EP10181447.3A patent/EP2322497B1/en not_active Expired - Lifetime
- 2005-04-07 NZ NZ593785A patent/NZ593785A/xx not_active IP Right Cessation
- 2005-04-07 AT AT05735988T patent/ATE498603T1/de not_active IP Right Cessation
- 2005-04-07 ES ES05735988T patent/ES2360535T3/es not_active Expired - Lifetime
- 2005-04-07 CN CN2011101865946A patent/CN102344379A/zh active Pending
- 2005-04-07 GB GB0506984A patent/GB2412912B/en not_active Expired - Lifetime
- 2005-04-07 DE DE602005026419T patent/DE602005026419D1/de not_active Expired - Lifetime
- 2005-04-07 AU AU2005232025A patent/AU2005232025B2/en not_active Ceased
- 2005-04-07 WO PCT/GB2005/001364 patent/WO2005097731A2/en not_active Ceased
- 2005-04-07 ES ES10181447.3T patent/ES2578635T3/es not_active Expired - Lifetime
- 2005-04-07 CN CN2005800182193A patent/CN1997620B/zh not_active Expired - Fee Related
- 2005-04-07 KR KR1020117014518A patent/KR101453145B1/ko not_active Expired - Lifetime
- 2005-04-07 KR KR1020127027271A patent/KR20120123612A/ko not_active Withdrawn
- 2005-04-07 US US10/599,694 patent/US8784686B2/en not_active Expired - Lifetime
- 2005-04-07 JP JP2007506841A patent/JP2007532525A/ja active Pending
- 2005-04-07 MX MXPA06011531A patent/MXPA06011531A/es not_active Application Discontinuation
-
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- 2011-06-28 US US13/170,686 patent/US8992798B2/en active Active
- 2011-08-31 JP JP2011188535A patent/JP2012012403A/ja active Pending
-
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- 2012-09-10 JP JP2012198805A patent/JP2013028618A/ja active Pending
-
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- 2014-02-27 US US14/191,750 patent/US9328220B2/en not_active Expired - Lifetime
- 2014-05-07 JP JP2014096295A patent/JP2014193885A/ja active Pending
- 2014-12-26 JP JP2014266275A patent/JP2015110594A/ja not_active Ceased
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