WO2015005513A1 - 마이크로리엑터를 사용한 카르복실산 음이온을 갖는 이온성 액체의 제조방법 - Google Patents
마이크로리엑터를 사용한 카르복실산 음이온을 갖는 이온성 액체의 제조방법 Download PDFInfo
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- WO2015005513A1 WO2015005513A1 PCT/KR2013/006213 KR2013006213W WO2015005513A1 WO 2015005513 A1 WO2015005513 A1 WO 2015005513A1 KR 2013006213 W KR2013006213 W KR 2013006213W WO 2015005513 A1 WO2015005513 A1 WO 2015005513A1
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- WIPO (PCT)
- Prior art keywords
- ionic liquid
- microreactor
- sodium
- alkyl
- butanoate
- Prior art date
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 40
- -1 carboxylic acid anion Chemical class 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims abstract description 13
- 150000004820 halides Chemical class 0.000 claims abstract description 27
- MFBOGIVSZKQAPD-UHFFFAOYSA-M sodium butyrate Chemical compound [Na+].CCCC([O-])=O MFBOGIVSZKQAPD-UHFFFAOYSA-M 0.000 claims abstract description 12
- BYKRNSHANADUFY-UHFFFAOYSA-M sodium octanoate Chemical compound [Na+].CCCCCCCC([O-])=O BYKRNSHANADUFY-UHFFFAOYSA-M 0.000 claims abstract description 11
- 238000006467 substitution reaction Methods 0.000 claims abstract description 11
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 claims abstract description 9
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 claims abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 150000001450 anions Chemical group 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000003792 electrolyte Substances 0.000 abstract description 4
- 150000001768 cations Chemical class 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 6
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 3
- 230000035484 reaction time Effects 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
- SQRZXYFGDFMDJO-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;octanoate Chemical compound CCCCCCCC([O-])=O.CCCCN1C=C[N+](C)=C1 SQRZXYFGDFMDJO-UHFFFAOYSA-M 0.000 description 2
- VCWAYQXBXUSWAE-UHFFFAOYSA-M 1-butyl-3-methylpyridin-1-ium octanoate Chemical compound CCCCCCCC([O-])=O.CCCC[n+]1cccc(C)c1 VCWAYQXBXUSWAE-UHFFFAOYSA-M 0.000 description 2
- PHCASOSWUQOQAG-UHFFFAOYSA-M 1-butyl-3-methylpyridin-1-ium;chloride Chemical compound [Cl-].CCCC[N+]1=CC=CC(C)=C1 PHCASOSWUQOQAG-UHFFFAOYSA-M 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- AYCPWULCTAQDNZ-UHFFFAOYSA-M 2-ethylhexanoate;tetramethylazanium Chemical compound C[N+](C)(C)C.CCCCC(CC)C([O-])=O AYCPWULCTAQDNZ-UHFFFAOYSA-M 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 2
- ZACXAFASMJJYOP-UHFFFAOYSA-M butanoate 1-butyl-2,3-dimethylimidazol-3-ium Chemical compound CCCC([O-])=O.CCCCn1cc[n+](C)c1C ZACXAFASMJJYOP-UHFFFAOYSA-M 0.000 description 2
- AAKPXTLRYGNRKI-UHFFFAOYSA-M butanoate 1-butyl-3-methylpyridin-1-ium Chemical compound CCCC([O-])=O.CCCC[n+]1cccc(C)c1 AAKPXTLRYGNRKI-UHFFFAOYSA-M 0.000 description 2
- YYTMWCSQXPHEFG-UHFFFAOYSA-M butanoate;1-butyl-3-methylimidazol-3-ium Chemical compound CCCC([O-])=O.CCCC[N+]=1C=CN(C)C=1 YYTMWCSQXPHEFG-UHFFFAOYSA-M 0.000 description 2
- OYGSFKZFXQKZDS-UHFFFAOYSA-M butanoate;tetramethylazanium Chemical compound C[N+](C)(C)C.CCCC([O-])=O OYGSFKZFXQKZDS-UHFFFAOYSA-M 0.000 description 2
- 239000003990 capacitor Substances 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- DMYOTDXFCYFGEK-UHFFFAOYSA-M octanoate;tetramethylazanium Chemical compound C[N+](C)(C)C.CCCCCCCC([O-])=O DMYOTDXFCYFGEK-UHFFFAOYSA-M 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- YUCVYVCYVDQICM-UHFFFAOYSA-M 1-butyl-2,3-dimethylimidazol-3-ium;iodide Chemical compound [I-].CCCC[N+]=1C=CN(C)C=1C YUCVYVCYVDQICM-UHFFFAOYSA-M 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- GZWQBESNJNYOOI-UHFFFAOYSA-M 1-ethyl-2,3-dimethylimidazol-3-ium octanoate Chemical compound CCn1cc[n+](C)c1C.CCCCCCCC([O-])=O GZWQBESNJNYOOI-UHFFFAOYSA-M 0.000 description 1
- GITMVCYKHULLDM-UHFFFAOYSA-M 1-ethyl-2,3-dimethylimidazol-3-ium;bromide Chemical compound [Br-].CCN1C=C[N+](C)=C1C GITMVCYKHULLDM-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 101100481033 Arabidopsis thaliana TGA7 gene Proteins 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000003487 electrochemical reaction Methods 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000002739 metals 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/004—Details
- H01G9/022—Electrolytes; Absorbents
- H01G9/035—Liquid electrolytes, e.g. impregnating materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
-
- 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/06—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 no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/18—Salts thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/20—Quaternary compounds thereof
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- 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
- C07D233/58—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 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/54—Electrolytes
- H01G11/58—Liquid electrolytes
- H01G11/62—Liquid electrolytes characterised by the solute, e.g. salts, anions or cations therein
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0566—Liquid materials
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2300/00—Electrolytes
- H01M2300/0017—Non-aqueous electrolytes
- H01M2300/0025—Organic electrolyte
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/13—Energy storage using capacitors
Definitions
- the present invention relates to a method for producing an ionic liquid having a carboxylic acid anion using a microreactor. More specifically, the present invention is sodium butanoate, sodium 2-ethylhexanoate, sodium octanoate and cation 1-alkyl-3-methylimidazolium, 1,1-alkylmethylpyrrolidinium, 1, The present invention relates to a method for efficiently producing an ionic liquid having a carboxylic acid anion as shown in Fig. 1 by substitution with 2-dimethyl-3-alkylimidazolium, 1-alkyl-3-methylpyridinium and tetramethylammonium. .
- R 1 is an alkyl group having 1 to 12 carbon atoms.
- Ionic liquids are high in heat resistance, nonflammable, and have low solubility in water, unlike those having common ions, and high in solubility in organic solvents. In addition, the movement of electrons is very active, and the conductivity is very excellent.
- ionic liquids are widely used as clean solvents and lithium secondary batteries, organic solar cells, and electrolytes for capacitors in various fields including organic synthesis, electrochemistry, biotechnology, chemical engineering, and separation processes.
- impurities and purity are very important factors. Impurities include residual halides, starting materials remaining after the reaction, decomposition products, and water, which generally lead to increased resistance during the course of the electrochemical reaction.
- the importance of high-purity ionic liquids is particularly important because residual halides interfere with the reaction when used with liquid hydrogen or when the Suzuki reaction proceeds.
- the reaction using alkyl halide is not an effective and economical method because of the high cost and difficulty in mass production.
- Other methods of removing halides include the use of silver acetate to remove halogen ions with insoluble silver halides and the use of lead salts to remove insoluble lead halides, but metal salts are expensive and contain harmful metals. It is not an efficient way to generate waste.
- An object of the present invention is a cation 1-alkyl-3-methylimidazolium, 1,1-alkylmethylpyrrolidinium, 1,2-dimethyl-3-alkylimidazolium, 1-alkyl-3-methylpyridinium It is to provide a method for producing a high purity ionic liquid having a carboxylic acid anion with high efficiency by using sodium butanoate, sodium 2-ethylhexanoate and sodium octanoate in tetramethylammonium.
- Preparation of the ionic liquid using a carboxylic acid anion is 1-alkyl-3-methylimidazolium, 1,1-alkylmethylpyrrolidinium, 1,2-dimethyl-3-alkylimidazolium, 1-alkyl
- a halogen salt of -3-methylpyridinium or tetramethylammonium is used as a starting material, and sodium butanoate, sodium 2-ethylhexanoate or sodium octanoate is reacted with the anion of the starting material, butanoate, Synthesis was performed by substitution with hexanoate or octanoate.
- the alkyl group of 1-alkyl-3-methylimidazolium, 1,1-alkylmethylpyrrolidinium, 1,2-dimethyl-3-alkylimidazolium, 1-alkyl-3-methylpyridinium has 1 to Twelve and halogen is fluorine, chlorine, bromine, or iodine.
- the substitution reaction is carried out using a bench reaction or a microreactor.
- Synthetic yield, halide content, electrical conductivity and thermal stability (TGA) were measured as an evaluation item of technology development according to the preparation of the compound.
- the method for preparing an ionic liquid according to the present invention is environmentally friendly because the solvent can be used as water in an anion substitution reaction by using carboxylic acid anions sodium butanoate, sodium 2-ethylhexanoate and sodium octanoate.
- the substitution reaction time can also be shortened to 1 hour or less.
- a high purity ionic liquid having a residual halide of less than 20 ppm can be prepared. Therefore, the method of preparing the ionic liquid of the present invention has an advantage of maximizing efficiency and economy since there are very few residual halides to be removed.
- the compound including butanoate, hexanoate and octanoate according to the present invention has stable physical properties, and the reaction time of anion substitution reaction is shorter (within 1 hour or less) compared to the conventional intermediate production method (more than 24 hours). Economical.
- the ionic liquid prepared according to the present invention has a high purity containing less than 10 ppm of residual halides, and can be used for electrolytes and capacitors due to its high electrical conductivity.
- Figure 1 shows the overall arrangement of the microreactor synthesis apparatus.
- FIG. 2 is a synthetic circuit diagram illustrating a process of becoming reagents through a micro mixer when reagents A and B are flowed through a cylinder pump to a microreactor.
- FIG. 3 shows Y type, Helix type and Static type, which are types of micromixers.
- a high purity ionic liquid having a carboxylic acid anion is prepared.
- the preparation method is 1-alkyl-3-methylimidazolium, 1,1-alkylmethylpyrrolidinium, 1,2-dimethyl-3-alkylimidazolium, 1-alkyl-3-methylpyridinium, or tetramethyl
- a halogen salt of ammonium is used as a starting material, and sodium butanoate, sodium 2-ethylhexanoate or sodium octanoate is reacted to replace anions of the starting material with butanoate, hexanoate or octanoate. Steps.
- alkyl groups of the 1-alkyl-3-methylimidazolium, 1,1-alkylmethylpyrrolidinium, 1,2-dimethyl-3-alkylimidazolium and 1-alkyl-3-methylpyridinium have carbon atoms.
- halogen is fluorine, chlorine, bromine or iodine and the substitution reaction can be carried out using a bench reaction or a microreactor.
- microreactor used Keychem L of YMC, Japan, and MRSY04-40 for the cylinder pump, and the Helix type for the micromixer, which is excellent in heat exchange and organic synthesis.
- PERKIN ELMER TGA7 was used as a model.
- the analysis conditions were measured by the Korea Institute of Industrial Technology at 30 °C (5min) ⁇ 10 °C / min ⁇ 800 °C under nitrogen stream.
- 0.2 g (0.0009 mol) of 1,1-butylmethylpyrrolidinium bromide is dissolved in 15 g of water to 150 ⁇ l / min, and 0.15 g (0.0011 mol) of sodium 2-ethylhexanoate is dissolved in 15 g of water to 150 ⁇ l / min.
- the solution passed through the microreactor was collected and concentrated under reduced pressure to obtain 0.215 g (93%) of 1,1-butylmethylpyrrolidinium 2-ethylhexanoate as a pale yellow solid.
- the analysis results of the obtained ionic liquid are as follows.
- 0.2 g (0.002 mol) of tetramethylammonium chloride was dissolved in 10 g of water to 150 ⁇ l / min, and 0.30 g (0.002 mol) of sodium 2-ethylhexanoate was dissolved in 10 g of water to 150 ⁇ l / min, adjusted to 70 ° C.
- Flow through the cylinder pump to the microreactor The solution passed through the microreactor was collected and concentrated under reduced pressure to obtain 0.335 g (98%) of tetramethylammonium 2-ethylhexanoate as a white solid.
- the analysis results of the obtained ionic liquid are as follows.
- 0.2 g (0.001 mol) of 1,1-butylmethylpyrrolidinium chloride was dissolved in 10 g of water to 150 ⁇ l / min, and 0.17 g (0.001 mol) of sodium 2-octanoate was dissolved in 10 g of water to 150 ⁇ l / min.
- the solution that passed through the microreactor was collected and concentrated under reduced pressure to obtain 0.265 g (94%) of 1,1-butylmethylpyrrolidinium octanoate as a white solid.
- the analysis results of the obtained ionic liquid are as follows.
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Abstract
Description
Claims (5)
- 카르복실산 음이온을 갖는 고순도의 이온성 액체의 제조방법으로,1-알킬-3-메틸이미다졸리움, 1,1-알킬메틸피롤리디늄, 1,2-디메틸-3-알킬이미다졸리움, 1-알킬-3-메틸피리디늄, 또는 테트라메틸암모늄의 할로겐 염을 출발물질로 하여 여기에 소듐부타노에이트, 소듐2-에틸헥사노에이트 또는 소듐옥타노에이트를 반응시켜 출발물질의 음이온이 부타노에이트, 헥사노에이트 또는 옥타노에이트로 치환되는 단계를 포함하고,상기 1-알킬-3-메틸이미다졸리움, 1,1-알킬메틸피롤리디늄, 1,2-디메틸-3-알킬이미다졸리움, 1-알킬-3-메틸피리디늄의 알킬기는 탄소수 1내지 12개이고, 할로겐은 플루오르, 염소, 브롬, 또는 요오드인, 이온성 액체의 제조 방법.
- 제1항에 있어서, 치환 반응의 용매로 물을 사용하는 이온성 액체의 제조 방법.
- 제1항 또는 제2항에 있어서, 치환 반응이 1시간 내에 수행되는 것을 특징으로 하는 이온성 액체의 제조 방법.
- 제1항 또는 제2항에 있어서, 상기 제조된 이온성 액체의 잔류 할라이드는 20ppm 미만인 것을 특징으로 하는 이온성 액체의 제조 방법.
- 제1항 또는 제2항에 있어서, 치환 반응이 벤치(bench) 반응 또는 마이크로리엑터(microreactor)를 이용하여 수행되는 이온성 액체의 제조 방법.
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US14/904,427 US20160254098A1 (en) | 2013-07-11 | 2013-07-11 | Method for preparing ionic liquid having carboxylic acid anion using microreactor |
PCT/KR2013/006213 WO2015005513A1 (ko) | 2013-07-11 | 2013-07-11 | 마이크로리엑터를 사용한 카르복실산 음이온을 갖는 이온성 액체의 제조방법 |
KR1020167000645A KR101800638B1 (ko) | 2013-07-11 | 2013-07-11 | 마이크로리엑터를 사용한 카르복실산 음이온을 갖는 이온성 액체의 제조방법 |
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US20080194834A1 (en) * | 2007-02-14 | 2008-08-14 | Eastman Chemical Company | Production of ionic liquids |
KR101279607B1 (ko) * | 2010-11-11 | 2013-06-27 | 주식회사 씨트리 | 마이크로리엑터를 사용한 메탈프리의 카르복실산 음이온을 갖는 이온성 액체의 합성 |
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2013
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- 2013-07-11 KR KR1020167000645A patent/KR101800638B1/ko active IP Right Grant
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US20080194834A1 (en) * | 2007-02-14 | 2008-08-14 | Eastman Chemical Company | Production of ionic liquids |
KR101279607B1 (ko) * | 2010-11-11 | 2013-06-27 | 주식회사 씨트리 | 마이크로리엑터를 사용한 메탈프리의 카르복실산 음이온을 갖는 이온성 액체의 합성 |
Non-Patent Citations (3)
Title |
---|
CASSOL, C. C. ET AL.: "A Simple and Practical Method for the Preparation and Purity Determination of Halide-Free Imidazolium Ionic Liquids.", ADVANCED SYNTHESIS & CATALYSIS, vol. 348, 19 January 2006 (2006-01-19), pages 243 - 248 * |
GREEN, M. D. ET AL.: "Designing Imidazole-Based Ionic Liquids and Ionic Liquid Monomers for Emerging Technologies.", JOURNAL OF MACROMOLECULAR SCIENCE , PART C: POLYMER REVIEW, vol. 49, 3 November 2009 (2009-11-03), pages 291 - 314 * |
RENKEN, A. ET AL.: "Ionic liquid synthesis in a microstructured reactor for process intensification.", CHEMICAL ENGINEERING AND PROCESSING, vol. 46, 15 June 2007 (2007-06-15), pages 840 - 845 * |
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KR101800638B1 (ko) | 2017-11-23 |
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