CN102307855A - N-取代的吡咯烷酮*离子液体 - Google Patents
N-取代的吡咯烷酮*离子液体 Download PDFInfo
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- CN102307855A CN102307855A CN2009801561138A CN200980156113A CN102307855A CN 102307855 A CN102307855 A CN 102307855A CN 2009801561138 A CN2009801561138 A CN 2009801561138A CN 200980156113 A CN200980156113 A CN 200980156113A CN 102307855 A CN102307855 A CN 102307855A
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- 239000002608 ionic liquid Substances 0.000 title abstract description 23
- -1 N-substituted pyrrolidonium Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 229940058352 levulinate Drugs 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- JOOXCMJARBKPKM-UHFFFAOYSA-M 4-oxopentanoate Chemical compound CC(=O)CCC([O-])=O JOOXCMJARBKPKM-UHFFFAOYSA-M 0.000 claims description 8
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 abstract description 25
- 150000004040 pyrrolidinones Chemical class 0.000 abstract description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 34
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 28
- 239000003054 catalyst Substances 0.000 description 28
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 20
- 150000002500 ions Chemical class 0.000 description 20
- 229910052751 metal Inorganic materials 0.000 description 20
- 239000002184 metal Substances 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 17
- 229940040102 levulinic acid Drugs 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229910052763 palladium Inorganic materials 0.000 description 11
- 239000002028 Biomass Substances 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 229910052697 platinum Inorganic materials 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 229910052703 rhodium Inorganic materials 0.000 description 8
- 239000010948 rhodium Substances 0.000 description 8
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229910052707 ruthenium Inorganic materials 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 229960001866 silicon dioxide Drugs 0.000 description 7
- 235000012239 silicon dioxide Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000005349 anion exchange Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- 229950007655 esilate Drugs 0.000 description 5
- 229910052741 iridium Inorganic materials 0.000 description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 5
- 229910052702 rhenium Inorganic materials 0.000 description 5
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
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- 238000002360 preparation method Methods 0.000 description 4
- 229910000108 silver(I,III) oxide Inorganic materials 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- GMEONFUTDYJSNV-UHFFFAOYSA-N Ethyl levulinate Chemical compound CCOC(=O)CCC(C)=O GMEONFUTDYJSNV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 3
- 239000010813 municipal solid waste Substances 0.000 description 3
- 229910052762 osmium Inorganic materials 0.000 description 3
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 229910010413 TiO 2 Inorganic materials 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 150000003841 chloride salts Chemical class 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 2
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- DHERNFAJQNHYBM-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1.O=C1CCCN1 DHERNFAJQNHYBM-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
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- 229910052709 silver Inorganic materials 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000010902 straw Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000609240 Ambelania acida Species 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241001520808 Panicum virgatum Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 244000046109 Sorghum vulgare var. nervosum Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 229920002522 Wood fibre Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000003082 abrasive agent Substances 0.000 description 1
- LPQOADBMXVRBNX-UHFFFAOYSA-N ac1ldcw0 Chemical compound Cl.C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN3CCSC1=C32 LPQOADBMXVRBNX-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- DCRIQAAPAFMPKP-UHFFFAOYSA-N aluminum oxygen(2-) titanium(4+) Chemical compound [O-2].[O-2].[Al+3].[Ti+4] DCRIQAAPAFMPKP-UHFFFAOYSA-N 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
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- 230000005540 biological transmission Effects 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
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- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- BDAGIHXWWSANSR-NJFSPNSNSA-N hydroxyformaldehyde Chemical compound O[14CH]=O BDAGIHXWWSANSR-NJFSPNSNSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000010893 paper waste Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000010908 plant waste Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(IV) oxide Inorganic materials O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 229910000018 strontium carbonate Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/328057 | 2008-12-04 | ||
| US12/328,057 US8138354B2 (en) | 2008-12-04 | 2008-12-04 | N-substituted pyrrolidonium ionic liquids |
| PCT/US2009/066712 WO2010065816A1 (en) | 2008-12-04 | 2009-12-04 | N-substituted pyrrolidonium ionic liquids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102307855A true CN102307855A (zh) | 2012-01-04 |
Family
ID=41559529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| CN2009801561138A Pending CN102307855A (zh) | 2008-12-04 | 2009-12-04 | N-取代的吡咯烷酮*离子液体 |
Country Status (6)
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| US (1) | US8138354B2 (enExample) |
| EP (1) | EP2358671A1 (enExample) |
| JP (1) | JP2012511013A (enExample) |
| KR (1) | KR20110091800A (enExample) |
| CN (1) | CN102307855A (enExample) |
| WO (1) | WO2010065816A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8715521B2 (en) | 2005-02-04 | 2014-05-06 | E I Du Pont De Nemours And Company | Absorption cycle utilizing ionic liquid as working fluid |
| AR058054A1 (es) | 2005-09-22 | 2008-01-23 | Du Pont | Utilizacion de liquidos ionicos para la separacion de hidrofluorocarburos |
| US8506839B2 (en) * | 2005-12-14 | 2013-08-13 | E I Du Pont De Nemours And Company | Absorption cycle utilizing ionic liquids and water as working fluids |
| CA2649048A1 (en) * | 2006-05-31 | 2007-12-13 | E.I. Du Pont De Nemours And Company | Vapor compression utilizing ionic liquid as compressor lubricant |
| KR20090077976A (ko) | 2006-11-08 | 2009-07-16 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 이온성 액체를 이용한 이산화탄소로부터의 테트라플루오로에틸렌의 분리 방법 |
| 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 |
| US8350056B2 (en) * | 2008-12-04 | 2013-01-08 | E I Du Pont De Nemours And Company | Functionalized 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 |
| US9067953B2 (en) * | 2010-03-12 | 2015-06-30 | E I Du Pont De Nemours And Company | Systems for carbon dioxide and sulfur dioxide removal |
| US9017455B2 (en) | 2010-06-03 | 2015-04-28 | E I Du Pont De Nemours And Company | Sulfur compounds for carbon dioxide and sulfur dioxide removal |
| US9939187B2 (en) | 2013-10-04 | 2018-04-10 | Lg Electronics Inc. | Refrigerator |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2913496A (en) * | 1957-06-07 | 1959-11-17 | Du Pont | N-(2-hydroxyethyl)-n'-pentenyl-ethylenediamine |
| US4820672A (en) * | 1987-06-25 | 1989-04-11 | Lithium Corporation Of America | Hydrocarbon soluble and insoluble organo magnesium chloride complexes, processes and uses |
| US5608105A (en) * | 1995-06-07 | 1997-03-04 | Biofine Incorporated | Production of levulinic acid from carbohydrate-containing materials |
| US6136586A (en) * | 1995-08-29 | 2000-10-24 | Vi Technologies, Inc. | Methods for the selective modification of viral nucleic acids |
| US5859263A (en) * | 1996-05-22 | 1999-01-12 | Board Of Regents University Of Nebraska Lincoln | Method and apparatus for production of levulinic acid via reactive extrusion |
| US5892107A (en) * | 1996-11-08 | 1999-04-06 | Arkenol, Inc. | Method for the production of levulinic acid |
| US6276671B1 (en) | 1998-10-29 | 2001-08-21 | Avon Vibration Management Systems Limited | Hydraulically damped mounting device |
| BE1013103A7 (nl) | 1999-10-04 | 2001-09-04 | Aquasystems Internat N V | Menger-beluchter in gecombineerde vorm. |
| ES2231699T3 (es) * | 2001-03-20 | 2005-05-16 | Basf Aktiengesellschaft | Liquidos ionicos como aditivos selectivos para la separacion de mezclas con un intervalo estrecho de ebullicion o azeotropicas. |
| US6579343B2 (en) * | 2001-03-30 | 2003-06-17 | University Of Notre Dame Du Lac | Purification of gas with liquid ionic compounds |
| JP2005511666A (ja) | 2001-12-04 | 2005-04-28 | ディーエスエム アイピー アセッツ ビー．ブイ． | イオン性液体の製造 |
| KR20040105819A (ko) * | 2002-04-01 | 2004-12-16 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 생물 자원 및 올레핀으로부터 레불린산 에스테르 및포름산 에스테르의 제조 방법 |
| AU2003237797B2 (en) * | 2002-04-05 | 2009-02-26 | University Of South Alabama | Functionalized ionic liquids, and methods of use thereof |
| US6900337B2 (en) * | 2003-03-24 | 2005-05-31 | E. I. Du Pont De Nemours And Company | Production of 5-methyl-1-hydrocarbyl-2-pyrrolidone by reductive amination of levulinic acid |
| US6818593B2 (en) * | 2003-03-24 | 2004-11-16 | E. I. Du Pont De Nemours And Company | Production of 5-Methyl-N-aryl-2-pyrrolidone and 5-methyl-N-alkyl-2-pyrrolidone by reductive amination of levulinic acid with nitro compounds |
| DE102004024967A1 (de) * | 2004-05-21 | 2005-12-08 | Basf Ag | Neue Absorptionsmedien für Absorptionswärmepumpen, Absorptionskältemaschinen und Wärmetransformatoren |
| US8715521B2 (en) * | 2005-02-04 | 2014-05-06 | E I Du Pont De Nemours And Company | Absorption cycle utilizing ionic liquid as working fluid |
| US7314962B2 (en) * | 2005-04-15 | 2008-01-01 | E. I. Du Pont De Nemours & Co. | Alkylation of aromatic compounds |
| US7157588B2 (en) * | 2005-04-15 | 2007-01-02 | E. I. Du Pont De Nemours And Company | Ionic liquids |
| CA2608542A1 (en) * | 2005-05-18 | 2006-11-23 | E.I. Dupont De Nemours And Company | Hybrid vapor compression-absorption cycle |
| US7834209B2 (en) * | 2005-06-07 | 2010-11-16 | E.I. Du Pont De Nemours And Company | Hydrofluoroalkanesulfonic acids from fluorovinyl ethers |
| US7683209B2 (en) * | 2005-06-07 | 2010-03-23 | E.I. Du Pont De Nemours And Company | Manufacture of hydrofluoroalkanesulfonic acids |
| US7625941B2 (en) * | 2005-09-22 | 2009-12-01 | E.I. Du Pont De Nemours And Company | Ionic liquids |
| US7544813B2 (en) * | 2005-09-22 | 2009-06-09 | E.I. Du Pont De Nemours And Company | Ionic liquids |
| US8119818B2 (en) * | 2008-12-04 | 2012-02-21 | E. I. Du Pont De Nemours And Company | Functionalized N-substituted pyrrolidonium ionic liquids |
| CN102307856A (zh) | 2008-12-04 | 2012-01-04 | 纳幕尔杜邦公司 | 带有膨胀连接子的n-取代的吡咯烷酮*离子液体 |
| 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 |
| US9224260B2 (en) | 2012-04-12 | 2015-12-29 | Patent Investment & Licensing Company | Method of apparatus for communicating information about networked gaming machines to prospective players |
| US10699328B2 (en) | 2017-04-17 | 2020-06-30 | Walmart Apollo, Llc | Systems to fulfill a picked sales order and related methods therefor |
-
2008
- 2008-12-04 US US12/328,057 patent/US8138354B2/en not_active Expired - Fee Related
-
2009
- 2009-12-04 CN CN2009801561138A patent/CN102307855A/zh active Pending
- 2009-12-04 WO PCT/US2009/066712 patent/WO2010065816A1/en not_active Ceased
- 2009-12-04 KR KR1020117015263A patent/KR20110091800A/ko not_active Withdrawn
- 2009-12-04 EP EP09768288A patent/EP2358671A1/en not_active Withdrawn
- 2009-12-04 JP JP2011539719A patent/JP2012511013A/ja not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP2358671A1 (en) | 2011-08-24 |
| WO2010065816A1 (en) | 2010-06-10 |
| JP2012511013A (ja) | 2012-05-17 |
| US20100145073A1 (en) | 2010-06-10 |
| KR20110091800A (ko) | 2011-08-12 |
| US8138354B2 (en) | 2012-03-20 |
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Application publication date: 20120104 |