DE10145747A1 - Ionische Flüssigkeiten - Google Patents
Ionische FlüssigkeitenInfo
- Publication number
- DE10145747A1 DE10145747A1 DE10145747A DE10145747A DE10145747A1 DE 10145747 A1 DE10145747 A1 DE 10145747A1 DE 10145747 A DE10145747 A DE 10145747A DE 10145747 A DE10145747 A DE 10145747A DE 10145747 A1 DE10145747 A1 DE 10145747A1
- Authority
- DE
- Germany
- Prior art keywords
- ionic liquid
- aryl
- group
- alkyl groups
- alkyl
- 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- Withdrawn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
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 45
- -1 anionic sulfate ester Chemical class 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 8
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 8
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 8
- 239000000654 additive Substances 0.000 claims abstract description 7
- 150000001768 cations Chemical class 0.000 claims abstract description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 3
- 150000001450 anions Chemical class 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 2
- 238000007037 hydroformylation reaction Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 230000000996 additive effect Effects 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 150000005840 aryl radicals Chemical class 0.000 claims 3
- 102000004190 Enzymes Human genes 0.000 claims 2
- 108090000790 Enzymes Proteins 0.000 claims 2
- 238000010976 amide bond formation reaction Methods 0.000 claims 2
- 230000032050 esterification Effects 0.000 claims 2
- 238000005886 esterification reaction Methods 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 238000006317 isomerization reaction Methods 0.000 claims 2
- 238000006384 oligomerization reaction Methods 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000003444 phase transfer catalyst Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 238000010485 C−C bond formation reaction Methods 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000011942 biocatalyst Substances 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 150000002460 imidazoles Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 150000003217 pyrazoles Chemical class 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 229910052723 transition metal Inorganic materials 0.000 claims 1
- 150000003624 transition metals Chemical class 0.000 claims 1
- 150000003852 triazoles Chemical group 0.000 claims 1
- 230000008018 melting Effects 0.000 abstract description 7
- 238000002844 melting Methods 0.000 abstract description 7
- 150000008040 ionic compounds Chemical class 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000000969 carrier Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- KIDIBVPFLKLKAH-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;octyl sulfate Chemical compound CCCCN1C=C[N+](C)=C1.CCCCCCCCOS([O-])(=O)=O KIDIBVPFLKLKAH-UHFFFAOYSA-M 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001447 alkali salts Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000010865 sewage Substances 0.000 description 3
- 229940067741 sodium octyl sulfate Drugs 0.000 description 3
- WFRKJMRGXGWHBM-UHFFFAOYSA-M sodium;octyl sulfate Chemical compound [Na+].CCCCCCCCOS([O-])(=O)=O WFRKJMRGXGWHBM-UHFFFAOYSA-M 0.000 description 3
- FHDQNOXQSTVAIC-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;chloride Chemical compound [Cl-].CCCCN1C=C[N+](C)=C1 FHDQNOXQSTVAIC-UHFFFAOYSA-M 0.000 description 2
- MEMNKNZDROKJHP-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;methyl sulfate Chemical compound COS([O-])(=O)=O.CCCCN1C=C[N+](C)=C1 MEMNKNZDROKJHP-UHFFFAOYSA-M 0.000 description 2
- VRFOKYHDLYBVAL-UHFFFAOYSA-M 1-ethyl-3-methylimidazol-3-ium;ethyl sulfate Chemical compound CCOS([O-])(=O)=O.CCN1C=C[N+](C)=C1 VRFOKYHDLYBVAL-UHFFFAOYSA-M 0.000 description 2
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000000567 combustion gas Substances 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical class C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- IIJSFQFJZAEKHB-UHFFFAOYSA-M 1,3-dimethylimidazol-1-ium;chloride Chemical compound [Cl-].CN1C=C[N+](C)=C1 IIJSFQFJZAEKHB-UHFFFAOYSA-M 0.000 description 1
- QBAMBHADIFOVQP-UHFFFAOYSA-M 1,3-dimethylimidazol-1-ium;octyl sulfate Chemical compound CN1C=C[N+](C)=C1.CCCCCCCCOS([O-])(=O)=O QBAMBHADIFOVQP-UHFFFAOYSA-M 0.000 description 1
- RLFUBODSGBPSLK-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;dodecyl sulfate Chemical compound CCCC[N+]=1C=CN(C)C=1.CCCCCCCCCCCCOS([O-])(=O)=O RLFUBODSGBPSLK-UHFFFAOYSA-M 0.000 description 1
- 229910016467 AlCl 4 Inorganic materials 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- YGVHKCBKEKMJIE-UHFFFAOYSA-J S(=O)(=O)(OCCCCCCCCCCCC)[O-].C(CCC)[N+]1=CN(C=C1)C.S(=O)(=O)(OCC(CCCC)CC)[O-].C(CCC)[N+]1=CN(C=C1)C.S(=O)(=O)(OCCCCCCCC)[O-].C(CCC)[N+]1=CN(C=C1)C.S(=O)(=O)(OCCCC)[O-].C(CCC)[N+]1=CN(C=C1)C Chemical compound S(=O)(=O)(OCCCCCCCCCCCC)[O-].C(CCC)[N+]1=CN(C=C1)C.S(=O)(=O)(OCC(CCCC)CC)[O-].C(CCC)[N+]1=CN(C=C1)C.S(=O)(=O)(OCCCCCCCC)[O-].C(CCC)[N+]1=CN(C=C1)C.S(=O)(=O)(OCCCC)[O-].C(CCC)[N+]1=CN(C=C1)C YGVHKCBKEKMJIE-UHFFFAOYSA-J 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 238000006065 biodegradation reaction Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical class [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000723 toxicological property Toxicity 0.000 description 1
- PYVOHVLEZJMINC-UHFFFAOYSA-N trihexyl(tetradecyl)phosphanium Chemical compound CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC PYVOHVLEZJMINC-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10145747A DE10145747A1 (de) | 2001-09-17 | 2001-09-17 | Ionische Flüssigkeiten |
| AT02797984T ATE387427T1 (de) | 2001-09-17 | 2002-09-11 | Organische sulfate als ionische flüssigkeiten |
| PCT/EP2002/010206 WO2003022812A1 (de) | 2001-09-12 | 2002-09-11 | Organische sulfate als ionische flüssigkeiten |
| EP02797984A EP1425268B2 (de) | 2001-09-17 | 2002-09-11 | Organische sulfate als ionische flüssigkeiten |
| JP2003526888A JP4698945B2 (ja) | 2001-09-17 | 2002-09-11 | イオン液体 |
| DE50211793T DE50211793D1 (enExample) | 2001-09-17 | 2002-09-11 | |
| US10/798,796 US7252791B2 (en) | 2001-09-17 | 2004-03-11 | Ionic liquids |
| US11/833,529 US7544807B2 (en) | 2001-09-17 | 2007-08-03 | Ionic liquids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10145747A DE10145747A1 (de) | 2001-09-17 | 2001-09-17 | Ionische Flüssigkeiten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10145747A1 true DE10145747A1 (de) | 2003-04-03 |
Family
ID=7699290
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10145747A Withdrawn DE10145747A1 (de) | 2001-09-12 | 2001-09-17 | Ionische Flüssigkeiten |
| DE50211793T Expired - Lifetime DE50211793D1 (enExample) | 2001-09-17 | 2002-09-11 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50211793T Expired - Lifetime DE50211793D1 (enExample) | 2001-09-17 | 2002-09-11 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7252791B2 (enExample) |
| EP (1) | EP1425268B2 (enExample) |
| JP (1) | JP4698945B2 (enExample) |
| AT (1) | ATE387427T1 (enExample) |
| DE (2) | DE10145747A1 (enExample) |
| WO (1) | WO2003022812A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10240098A1 (de) * | 2002-08-30 | 2004-03-18 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Verfahren zur Synthese und selektiven biokatalytischen Modifizierung von Peptiden, Peptidmimetika und Proteinen |
| DE10243446A1 (de) * | 2002-09-19 | 2004-04-01 | Celanese Chemicals Europe Gmbh | Verfahren zur Herstellung von Aldehyden |
| WO2004090066A1 (de) * | 2003-04-10 | 2004-10-21 | Basf Aktiengesellschaft | Verwendung einer ionischen flüssigkeit |
| DE102005008104A1 (de) * | 2005-02-21 | 2006-09-21 | Behr Gmbh & Co. Kg | Wärmeübertragungssystem |
Families Citing this family (76)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10145747A1 (de) * | 2001-09-17 | 2003-04-03 | Solvent Innovation Gmbh | Ionische Flüssigkeiten |
| WO2005007657A2 (de) * | 2003-07-11 | 2005-01-27 | Solvay Fluor Gmbh | Verwendung von dbn und dbu-salzen als ionische flüssigkeiten |
| BRPI0414005A (pt) * | 2003-08-26 | 2006-10-24 | Ecole Polytech | lìquidos iÈnicos baseados em sais de imidazólio que incorporam uma funcionalidade nitrila |
| EP2295398B1 (de) * | 2003-08-27 | 2016-04-13 | proionic GmbH & Co KG | Verfahren zur Herstellung ionischer Flüssigkeiten, ionischer Feststoffe oder Gemische derselben |
| GB0407908D0 (en) * | 2004-04-07 | 2004-05-12 | Univ York | Ionic liquids |
| JP4732704B2 (ja) * | 2004-04-30 | 2011-07-27 | 株式会社カネカ | イオン性液体およびその製造方法 |
| US7563308B2 (en) * | 2004-09-23 | 2009-07-21 | Air Products And Chemicals, Inc. | Ionic liquid based mixtures for gas storage and delivery |
| GB0422447D0 (en) * | 2004-10-08 | 2004-11-10 | Univ Cambridge Tech | Use of ionic liquids |
| GB0500028D0 (en) * | 2005-01-04 | 2005-02-09 | Univ Belfast | Base stable ionic liquids |
| GB0505064D0 (en) * | 2005-03-11 | 2005-04-20 | Univ Belfast | Production of bio-diesel |
| WO2006111712A2 (en) * | 2005-04-20 | 2006-10-26 | The Queen's University Of Belfast | Ionic liquids and uses thereof |
| US7763715B2 (en) * | 2005-04-22 | 2010-07-27 | The Procter & Gamble Company | Extracting biopolymers from a biomass using ionic liquids |
| DE102005028533A1 (de) * | 2005-06-18 | 2006-12-21 | Basf Ag | Pyrazolium Alkylsulfate |
| US7464580B2 (en) * | 2005-09-26 | 2008-12-16 | Oakland University | Ionic liquid high temperature gas sensors |
| US8936719B2 (en) * | 2006-03-22 | 2015-01-20 | Ultraclean Fuel Pty Ltd. | Process for removing sulphur from liquid hydrocarbons |
| US8375768B2 (en) * | 2006-03-30 | 2013-02-19 | Oakland University | Ionic liquid thin layer sensor for electrochemical and/or piezoelectric measurements |
| US7886577B2 (en) | 2006-03-30 | 2011-02-15 | Oakland University | Devices with surface bound ionic liquids and method of use thereof |
| US8394483B2 (en) | 2007-01-24 | 2013-03-12 | Micron Technology, Inc. | Two-dimensional arrays of holes with sub-lithographic diameters formed by block copolymer self-assembly |
| US9834516B2 (en) * | 2007-02-14 | 2017-12-05 | Eastman Chemical Company | Regioselectively substituted cellulose esters produced in a carboxylated ionic liquid process and products produced therefrom |
| US10174129B2 (en) | 2007-02-14 | 2019-01-08 | Eastman Chemical Company | Regioselectively substituted cellulose esters produced in a carboxylated ionic liquid process and products produced therefrom |
| US8153782B2 (en) * | 2007-02-14 | 2012-04-10 | Eastman Chemical Company | Reformation of ionic liquids |
| US8083953B2 (en) | 2007-03-06 | 2011-12-27 | Micron Technology, Inc. | Registered structure formation via the application of directed thermal energy to diblock copolymer films |
| US8557128B2 (en) | 2007-03-22 | 2013-10-15 | Micron Technology, Inc. | Sub-10 nm line features via rapid graphoepitaxial self-assembly of amphiphilic monolayers |
| DE102007017872A1 (de) * | 2007-04-13 | 2008-10-16 | Linde Ag | Verfahren zur Inertisierung eines sauerstoffempfindlichen Katalysators |
| US8097175B2 (en) | 2008-10-28 | 2012-01-17 | Micron Technology, Inc. | Method for selectively permeating a self-assembled block copolymer, method for forming metal oxide structures, method for forming a metal oxide pattern, and method for patterning a semiconductor structure |
| US8294139B2 (en) | 2007-06-21 | 2012-10-23 | Micron Technology, Inc. | Multilayer antireflection coatings, structures and devices including the same and methods of making the same |
| US7959975B2 (en) | 2007-04-18 | 2011-06-14 | Micron Technology, Inc. | Methods of patterning a substrate |
| US8372295B2 (en) | 2007-04-20 | 2013-02-12 | Micron Technology, Inc. | Extensions of self-assembled structures to increased dimensions via a “bootstrap” self-templating method |
| US8404124B2 (en) | 2007-06-12 | 2013-03-26 | Micron Technology, Inc. | Alternating self-assembling morphologies of diblock copolymers controlled by variations in surfaces |
| US8080615B2 (en) | 2007-06-19 | 2011-12-20 | Micron Technology, Inc. | Crosslinkable graft polymer non-preferentially wetted by polystyrene and polyethylene oxide |
| CN101918368B (zh) * | 2007-12-14 | 2013-04-24 | 巴斯夫欧洲公司 | 改善离子液体的水解稳定性的方法 |
| WO2009095012A1 (de) * | 2008-01-30 | 2009-08-06 | Technische Universität Dresden | Salze mit aryl-alkyl-substituierten imidazolium- und triazoliumkationen als ionische flüssigkeiten |
| US8999492B2 (en) | 2008-02-05 | 2015-04-07 | Micron Technology, Inc. | Method to produce nanometer-sized features with directed assembly of block copolymers |
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-
2001
- 2001-09-17 DE DE10145747A patent/DE10145747A1/de not_active Withdrawn
-
2002
- 2002-09-11 WO PCT/EP2002/010206 patent/WO2003022812A1/de not_active Ceased
- 2002-09-11 JP JP2003526888A patent/JP4698945B2/ja not_active Expired - Fee Related
- 2002-09-11 EP EP02797984A patent/EP1425268B2/de not_active Expired - Lifetime
- 2002-09-11 AT AT02797984T patent/ATE387427T1/de active
- 2002-09-11 DE DE50211793T patent/DE50211793D1/de not_active Expired - Lifetime
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2004
- 2004-03-11 US US10/798,796 patent/US7252791B2/en not_active Expired - Lifetime
-
2007
- 2007-08-03 US US11/833,529 patent/US7544807B2/en not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10240098A1 (de) * | 2002-08-30 | 2004-03-18 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Verfahren zur Synthese und selektiven biokatalytischen Modifizierung von Peptiden, Peptidmimetika und Proteinen |
| DE10240098B4 (de) * | 2002-08-30 | 2006-04-06 | Roche Diagnostics Gmbh | Verfahren zur Synthese und selektiven biokatalytischen Modifizierung von Peptiden, Peptidmimetika und Proteinen |
| DE10243446A1 (de) * | 2002-09-19 | 2004-04-01 | Celanese Chemicals Europe Gmbh | Verfahren zur Herstellung von Aldehyden |
| DE10243446B4 (de) * | 2002-09-19 | 2005-12-15 | Celanese Chemicals Europe Gmbh | Verfahren zur Herstellung von Aldehyden |
| WO2004090066A1 (de) * | 2003-04-10 | 2004-10-21 | Basf Aktiengesellschaft | Verwendung einer ionischen flüssigkeit |
| DE102005008104A1 (de) * | 2005-02-21 | 2006-09-21 | Behr Gmbh & Co. Kg | Wärmeübertragungssystem |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE387427T1 (de) | 2008-03-15 |
| US7544807B2 (en) | 2009-06-09 |
| US20080033178A1 (en) | 2008-02-07 |
| JP2005515168A (ja) | 2005-05-26 |
| WO2003022812A1 (de) | 2003-03-20 |
| EP1425268B2 (de) | 2011-03-16 |
| EP1425268B1 (de) | 2008-02-27 |
| EP1425268A1 (de) | 2004-06-09 |
| US20040262578A1 (en) | 2004-12-30 |
| DE50211793D1 (enExample) | 2008-04-10 |
| JP4698945B2 (ja) | 2011-06-08 |
| US7252791B2 (en) | 2007-08-07 |
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