NO321962B1 - Fremgangsmate til utforelse av en mikrobolgeassistert kjemisk omdannelse, samt fremgangsmate til fremstilling av ioniske vaesker i mikrobolgeassisterte kjemiske omdannelser - Google Patents
Fremgangsmate til utforelse av en mikrobolgeassistert kjemisk omdannelse, samt fremgangsmate til fremstilling av ioniske vaesker i mikrobolgeassisterte kjemiske omdannelser Download PDFInfo
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- NO321962B1 NO321962B1 NO20015578A NO20015578A NO321962B1 NO 321962 B1 NO321962 B1 NO 321962B1 NO 20015578 A NO20015578 A NO 20015578A NO 20015578 A NO20015578 A NO 20015578A NO 321962 B1 NO321962 B1 NO 321962B1
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- Prior art keywords
- microwave
- ionic liquid
- accordance
- cation
- alkyl
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 102
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 85
- 238000000034 method Methods 0.000 title claims abstract description 50
- 239000000126 substance Substances 0.000 title claims description 36
- 230000008569 process Effects 0.000 title description 2
- 239000002904 solvent Substances 0.000 claims abstract description 45
- 239000003960 organic solvent Substances 0.000 claims abstract description 21
- 239000000654 additive Substances 0.000 claims abstract description 12
- 230000000996 additive effect Effects 0.000 claims abstract description 10
- -1 thiazolium Chemical compound 0.000 claims description 22
- 150000001768 cations Chemical class 0.000 claims description 20
- 150000001450 anions Chemical class 0.000 claims description 19
- 239000000376 reactant Substances 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- 150000002892 organic cations Chemical class 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 238000002844 melting Methods 0.000 claims description 8
- 230000008018 melting Effects 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000012298 atmosphere Substances 0.000 claims description 7
- 150000002390 heteroarenes Chemical class 0.000 claims description 6
- 230000005855 radiation Effects 0.000 claims description 6
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- 125000002091 cationic group Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 229940095064 tartrate Drugs 0.000 claims description 4
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 150000002894 organic compounds Chemical class 0.000 claims description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-O Pyrazolium Chemical compound C1=CN[NH+]=C1 WTKZEGDFNFYCGP-UHFFFAOYSA-O 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-O hydron;1,2-oxazole Chemical compound C=1C=[NH+]OC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-O 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-O hydron;1,3-oxazole Chemical compound C1=COC=[NH+]1 ZCQWOFVYLHDMMC-UHFFFAOYSA-O 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-O hydron;pyrimidine Chemical compound C1=CN=C[NH+]=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-O 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 229910017048 AsF6 Inorganic materials 0.000 claims 1
- 150000002460 imidazoles Chemical class 0.000 claims 1
- 230000035484 reaction time Effects 0.000 abstract description 12
- 239000006184 cosolvent Substances 0.000 abstract description 8
- 238000005804 alkylation reaction Methods 0.000 abstract description 5
- 239000012454 non-polar solvent Substances 0.000 abstract description 5
- 238000010438 heat treatment Methods 0.000 abstract description 4
- 239000007788 liquid Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 7
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 150000001449 anionic compounds Chemical class 0.000 description 5
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 230000006870 function Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 229910001412 inorganic anion Inorganic materials 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229950011260 betanaphthol Drugs 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000013626 chemical specie Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002891 organic anions Chemical class 0.000 description 3
- 238000006053 organic reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000001349 alkyl fluorides Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 150000001983 dialkylethers Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000000622 liquid--liquid extraction Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000007144 microwave assisted synthesis reaction Methods 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000003495 polar organic solvent Substances 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- 238000007341 Heck reaction Methods 0.000 description 1
- 239000004992 Ionic Liquid Crystal Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- BXILREUWHCQFES-UHFFFAOYSA-K aluminum;trichloride;hydrochloride Chemical compound [Al+3].Cl.[Cl-].[Cl-].[Cl-] BXILREUWHCQFES-UHFFFAOYSA-K 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 238000005902 aminomethylation reaction Methods 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 238000007074 heterocyclization reaction Methods 0.000 description 1
- 238000006197 hydroboration reaction Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000010656 hydrometalation reaction Methods 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 150000002843 nonmetals Chemical group 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000002601 radiography Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000011829 room temperature ionic liquid solvent Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000006561 solvent free reaction Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 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
- 238000010555 transalkylation reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003852 triazoles Chemical class 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
-
- 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
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
-
- 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
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
- B01J19/12—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electromagnetic waves
- B01J19/122—Incoherent waves
- B01J19/126—Microwaves
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B39/00—Halogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- 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
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA199900734 | 1999-05-26 | ||
| PCT/IB2000/000719 WO2000072956A1 (en) | 1999-05-26 | 2000-05-26 | Preparation and use of ionic liquids in microwave-assisted chemical transformations |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20015578D0 NO20015578D0 (no) | 2001-11-15 |
| NO20015578L NO20015578L (no) | 2002-01-24 |
| NO321962B1 true NO321962B1 (no) | 2006-07-31 |
Family
ID=8096936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20015578A NO321962B1 (no) | 1999-05-26 | 2001-11-15 | Fremgangsmate til utforelse av en mikrobolgeassistert kjemisk omdannelse, samt fremgangsmate til fremstilling av ioniske vaesker i mikrobolgeassisterte kjemiske omdannelser |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6596130B2 (de) |
| EP (1) | EP1194227B1 (de) |
| JP (1) | JP2003500460A (de) |
| CN (1) | CN1188211C (de) |
| AT (1) | ATE276043T1 (de) |
| AU (1) | AU774290B2 (de) |
| CA (1) | CA2374251C (de) |
| DE (1) | DE60013832T2 (de) |
| ES (1) | ES2228518T3 (de) |
| NO (1) | NO321962B1 (de) |
| WO (1) | WO2000072956A1 (de) |
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| US7112450B2 (en) | 2000-05-08 | 2006-09-26 | Personal Chemistry I Uppsala Ab | Method for performing multiple chemical reactions and a kit and system therefor |
| US7253289B2 (en) | 2001-01-22 | 2007-08-07 | Covalent Associates, Inc. | One-step process for the preparation of halide-free hydrophobic salts |
| FI116142B (fi) * | 2003-09-11 | 2005-09-30 | Kemira Oyj | Esteröintimenetelmä |
| FI116140B (fi) * | 2003-12-03 | 2005-09-30 | Kemira Oyj | Eetteröintimenetelmä |
| EP1577281A1 (de) * | 2004-03-19 | 2005-09-21 | Bayer CropScience GmbH | Verfahren zur Herstellung kombonatorischer Bibiotheken |
| KR100739452B1 (ko) | 2004-04-29 | 2007-07-18 | 인하대학교 산학협력단 | α-알킬피롤 화합물의 제조방법 |
| JP2006035078A (ja) * | 2004-07-26 | 2006-02-09 | National Institute Of Advanced Industrial & Technology | マイクロ波照射による超臨界流体抽出分離方法及びその装置 |
| DE102004040016A1 (de) * | 2004-08-16 | 2006-02-23 | Friedrich-Schiller-Universität Jena | Verfahren zur Herstellung ionischer Flüssigkeiten |
| GB0500028D0 (en) * | 2005-01-04 | 2005-02-09 | Univ Belfast | Base stable ionic liquids |
| US20070101824A1 (en) * | 2005-06-10 | 2007-05-10 | Board Of Trustees Of Michigan State University | Method for producing compositions of nanoparticles on solid surfaces |
| FI120265B (fi) * | 2005-07-14 | 2009-08-31 | Kemira Oyj | Tärkkelyksen eetteröintimenetelmä |
| US20070129568A1 (en) * | 2005-12-06 | 2007-06-07 | Ngimat, Co. | Ionic liquids |
| CN100443157C (zh) * | 2006-11-16 | 2008-12-17 | 中国科学院长春应用化学研究所 | 一种微波连续反应设备的应用 |
| CN1958574B (zh) * | 2006-11-16 | 2012-05-02 | 中国科学院长春应用化学研究所 | 一种离子液体的制备方法 |
| CN100455584C (zh) * | 2006-12-13 | 2009-01-28 | 辽宁大学 | 微波辅助离子液体中合成四苯基卟啉的方法 |
| EP1950196A1 (de) * | 2007-01-29 | 2008-07-30 | Boehringer Ingelheim Pharma GmbH & Co. KG | Verfahren zur Herstellung von Ammoniumhexafluorophosphaten |
| 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 |
| 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 |
| US8153782B2 (en) * | 2007-02-14 | 2012-04-10 | Eastman Chemical Company | Reformation of ionic liquids |
| US9018321B2 (en) | 2007-07-26 | 2015-04-28 | Ajinomoto Co., Inc. | Resin composition |
| US8354525B2 (en) * | 2008-02-13 | 2013-01-15 | Eastman Chemical Company | Regioselectively substituted cellulose esters produced in a halogenated ionic liquid process and products produced therefrom |
| US9777074B2 (en) | 2008-02-13 | 2017-10-03 | Eastman Chemical Company | Regioselectively substituted cellulose esters produced in a halogenated ionic liquid process and products produced therefrom |
| US8158777B2 (en) | 2008-02-13 | 2012-04-17 | Eastman Chemical Company | Cellulose esters and their production in halogenated ionic liquids |
| US8188267B2 (en) | 2008-02-13 | 2012-05-29 | Eastman Chemical Company | Treatment of cellulose esters |
| KR100970480B1 (ko) * | 2008-09-03 | 2010-07-16 | 삼성전자주식회사 | 마이크로파와 음이온을 이용한 액체 매질 가열방법, 음이온이 첨가된 생물학적 분석장치 및 액체 매질 가열용 용액 |
| MX2008006731A (es) * | 2008-05-26 | 2009-11-26 | Mexicano Inst Petrol | Liquidos ionicos en la desulfuracion de hidrocarburos y procedimiento de obtencion. |
| CA2754888A1 (en) * | 2009-03-13 | 2010-09-16 | University Of Utah Research Foundation | Fluid-sparged helical channel reactor and associated methods |
| US8524887B2 (en) | 2009-04-15 | 2013-09-03 | Eastman Chemical Company | Regioselectively substituted cellulose esters produced in a tetraalkylammonium alkylphosphate ionic liquid process and products produced therefrom |
| CN102477044A (zh) * | 2010-11-26 | 2012-05-30 | 苏州凯达生物医药技术有限公司 | 导电高分子聚3，4-乙烯二氧噻吩(pedot)的单体3，4-乙烯二氧噻吩(edot)的合成方法 |
| US9096691B2 (en) | 2011-04-13 | 2015-08-04 | Eastman Chemical Company | Cellulose ester optical films |
| US8563463B1 (en) | 2012-06-29 | 2013-10-22 | Nissan North America, Inc. | Rapid synthesis of fuel cell catalyst using controlled microwave heating |
| US9683309B2 (en) * | 2012-07-24 | 2017-06-20 | Board Of Trustees Of The University Of Alabama | Process for electrospinning chitin fibers from chitinous biomass solution |
| ES2906062T3 (es) | 2013-11-29 | 2022-04-13 | Proionic Gmbh | Procedimiento para la unión de un material termoplástico por medio de radiación de microondas |
| KR101679478B1 (ko) * | 2013-12-30 | 2016-11-24 | 부산대학교 산학협력단 | 트리알킬 오르소에스테르를 이용한 무수 이온성 액체 직접 합성법 개발 |
| US10100131B2 (en) | 2014-08-27 | 2018-10-16 | The Board Of Trustees Of The University Of Alabama | Chemical pulping of chitinous biomass for chitin |
| US10927191B2 (en) | 2017-01-06 | 2021-02-23 | The Board Of Trustees Of The University Of Alabama | Coagulation of chitin from ionic liquid solutions using kosmotropic salts |
| US10941258B2 (en) | 2017-03-24 | 2021-03-09 | The Board Of Trustees Of The University Of Alabama | Metal particle-chitin composite materials and methods of making thereof |
| CN108620428B (zh) * | 2018-04-08 | 2020-12-18 | 王微静 | 一种基于离子液体的土壤重金属淋洗液及其制备方法 |
| CN112724154B (zh) * | 2019-10-28 | 2022-06-07 | 中国石油化工股份有限公司 | 一种异山梨醇酯增塑剂及其制备方法 |
| CN114656354B (zh) * | 2022-04-28 | 2023-12-29 | 河北科技大学 | 一种醋酸正丁胺离子液体的制备方法 |
| WO2023242335A2 (en) | 2022-06-16 | 2023-12-21 | Fundación Centro De Investigación Cooperativa De Energías Alternativas Cic Energigune Fundazioa | Catalytic system containing ionic liquids and a process for producing hydrogen from plastic materials using said catalytic system |
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| JP2784789B2 (ja) * | 1989-03-27 | 1998-08-06 | 山本化成株式会社 | ２―アルキルアントラキノンの製造方法 |
| FR2663933B1 (fr) * | 1990-06-27 | 1994-06-17 | Beghin Say Sa | Nouveau procede de preparation du 5-hydroxymethylfurfural a partir de saccharides. |
| US5883349A (en) * | 1993-09-24 | 1999-03-16 | Duquesne University Of The Holy Ghost | Method and apparatus for microwave assisted chemical reactions |
| CA2159479A1 (en) * | 1994-02-10 | 1995-08-17 | Ala'a K. Abdul-Sada | Ionic liquids |
| GB9402612D0 (en) * | 1994-02-10 | 1994-04-06 | British Petroleum Co Plc | Ionic liquids |
| US5827602A (en) | 1995-06-30 | 1998-10-27 | Covalent Associates Incorporated | Hydrophobic ionic liquids |
| SE509731C2 (sv) * | 1996-05-14 | 1999-03-01 | Labwell Ab | Metod för palladium-katalyserade organiska reaktioner innefattande ett uppvärmningssteg utfört med mikrovågsenergi |
| US5731101A (en) | 1996-07-22 | 1998-03-24 | Akzo Nobel Nv | Low temperature ionic liquids |
| JP3069677B2 (ja) * | 1996-07-25 | 2000-07-24 | 工業技術院長 | 有機カルボン酸エステル化合物の製造方法 |
| FR2751961B1 (fr) * | 1996-08-01 | 1998-09-11 | Rhone Poulenc Chimie | Procede pour la synthese de derives organiques oxysulfures et fluores |
| BR9710796A (pt) * | 1996-08-01 | 2000-01-11 | Rhodia Chimie Sa | Processo para enxertar um grupamento difluorometila substituìdo. |
| EP0925271B1 (de) * | 1996-08-16 | 2002-02-06 | Unichema Chemie B.V. | Verfahren zur herstellung von fettsäuren |
| WO1999019288A1 (en) * | 1997-10-13 | 1999-04-22 | Quest International B.V. | Improvements in or relating to friedel-crafts reactions |
-
2000
- 2000-05-26 ES ES00927660T patent/ES2228518T3/es not_active Expired - Lifetime
- 2000-05-26 EP EP00927660A patent/EP1194227B1/de not_active Expired - Lifetime
- 2000-05-26 AU AU46046/00A patent/AU774290B2/en not_active Ceased
- 2000-05-26 DE DE60013832T patent/DE60013832T2/de not_active Expired - Lifetime
- 2000-05-26 WO PCT/IB2000/000719 patent/WO2000072956A1/en active IP Right Grant
- 2000-05-26 JP JP2000621059A patent/JP2003500460A/ja active Pending
- 2000-05-26 CA CA002374251A patent/CA2374251C/en not_active Expired - Fee Related
- 2000-05-26 CN CNB008106762A patent/CN1188211C/zh not_active Expired - Fee Related
- 2000-05-26 AT AT00927660T patent/ATE276043T1/de not_active IP Right Cessation
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2001
- 2001-11-15 NO NO20015578A patent/NO321962B1/no not_active IP Right Cessation
- 2001-11-26 US US09/991,730 patent/US6596130B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2003500460A (ja) | 2003-01-07 |
| AU774290B2 (en) | 2004-06-24 |
| DE60013832D1 (de) | 2004-10-21 |
| US20020056633A1 (en) | 2002-05-16 |
| DE60013832T2 (de) | 2005-09-29 |
| CA2374251C (en) | 2007-11-27 |
| ATE276043T1 (de) | 2004-10-15 |
| EP1194227B1 (de) | 2004-09-15 |
| WO2000072956A1 (en) | 2000-12-07 |
| ES2228518T3 (es) | 2005-04-16 |
| NO20015578L (no) | 2002-01-24 |
| EP1194227A1 (de) | 2002-04-10 |
| CN1361716A (zh) | 2002-07-31 |
| AU4604600A (en) | 2000-12-18 |
| CA2374251A1 (en) | 2000-12-07 |
| CN1188211C (zh) | 2005-02-09 |
| US6596130B2 (en) | 2003-07-22 |
| NO20015578D0 (no) | 2001-11-15 |
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