JP2016533351A - フルオロアルキルスルホネート塩の合成方法 - Google Patents
フルオロアルキルスルホネート塩の合成方法 Download PDFInfo
- Publication number
- JP2016533351A JP2016533351A JP2016519774A JP2016519774A JP2016533351A JP 2016533351 A JP2016533351 A JP 2016533351A JP 2016519774 A JP2016519774 A JP 2016519774A JP 2016519774 A JP2016519774 A JP 2016519774A JP 2016533351 A JP2016533351 A JP 2016533351A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- optionally substituted
- organic base
- branched
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 51
- 150000003839 salts Chemical class 0.000 title claims description 8
- 230000002194 synthesizing effect Effects 0.000 title description 2
- -1 fluoroalkyl sulfonate salt Chemical class 0.000 claims abstract description 29
- 150000007530 organic bases Chemical class 0.000 claims abstract description 24
- 150000001409 amidines Chemical class 0.000 claims abstract description 20
- 150000002357 guanidines Chemical class 0.000 claims abstract description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 15
- 150000003222 pyridines Chemical class 0.000 claims abstract description 13
- 150000004820 halides Chemical class 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 150000001336 alkenes Chemical class 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 claims description 3
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical class [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- 230000014509 gene expression Effects 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 abstract description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 8
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000006166 lysate Substances 0.000 abstract 1
- GKNWQHIXXANPTN-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)F GKNWQHIXXANPTN-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 230000004580 weight loss Effects 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000002608 ionic liquid Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- IRSPIQIRIUYUGF-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-2-(1,1,2,2,2-pentafluoroethoxy)ethanesulfonyl fluoride Chemical compound FC(F)(F)C(F)(F)OC(F)(F)C(F)(F)S(F)(=O)=O IRSPIQIRIUYUGF-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- LNIYNESXCOYFPW-UHFFFAOYSA-N dibenzyl(dimethyl)azanium Chemical compound C=1C=CC=CC=1C[N+](C)(C)CC1=CC=CC=C1 LNIYNESXCOYFPW-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 150000003053 piperidines Chemical class 0.000 description 3
- 150000003235 pyrrolidines Chemical class 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 3
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 2
- VYAXQANIOQMUHV-UHFFFAOYSA-N 1,2,4,6-tetramethylpyridin-1-ium Chemical compound CC1=CC(C)=[N+](C)C(C)=C1 VYAXQANIOQMUHV-UHFFFAOYSA-N 0.000 description 2
- LINDOXZENKYESA-UHFFFAOYSA-N 1,2-dimethylguanidine Chemical compound CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 2
- OEBXWWBYZJNKRK-UHFFFAOYSA-N 1-methyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2N(C)CCCN21 OEBXWWBYZJNKRK-UHFFFAOYSA-N 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 2
- FVKFHMNJTHKMRX-UHFFFAOYSA-N 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine Chemical compound C1CCN2CCCNC2=N1 FVKFHMNJTHKMRX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- UURSXESKOOOTOV-UHFFFAOYSA-N dec-5-ene Chemical compound CCCCC=CCCCC UURSXESKOOOTOV-UHFFFAOYSA-N 0.000 description 2
- 238000004070 electrodeposition Methods 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical class FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical class OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- NQOFYFRKWDXGJP-UHFFFAOYSA-N 1,1,2-trimethylguanidine Chemical compound CN=C(N)N(C)C NQOFYFRKWDXGJP-UHFFFAOYSA-N 0.000 description 1
- FTWMCSGJSZWKCR-UHFFFAOYSA-N 1,2,3-tricyclohexylguanidine Chemical compound C1CCCCC1NC(NC1CCCCC1)=NC1CCCCC1 FTWMCSGJSZWKCR-UHFFFAOYSA-N 0.000 description 1
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HLLMKZXNMQWDJX-UHFFFAOYSA-N 1-butyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2N(CCCC)CCCN21 HLLMKZXNMQWDJX-UHFFFAOYSA-N 0.000 description 1
- BYIJEWQQOZJZMN-UHFFFAOYSA-N 1-cyclohexyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCCCC1N1C2=NCCCN2CCC1 BYIJEWQQOZJZMN-UHFFFAOYSA-N 0.000 description 1
- AAPJUEKLMYSSCH-UHFFFAOYSA-N 1-ethyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2N(CC)CCCN21 AAPJUEKLMYSSCH-UHFFFAOYSA-N 0.000 description 1
- CFJZKUSFRPUSGV-UHFFFAOYSA-M 1-ethylpyridin-1-ium;trifluoromethanesulfonate Chemical compound CC[N+]1=CC=CC=C1.[O-]S(=O)(=O)C(F)(F)F CFJZKUSFRPUSGV-UHFFFAOYSA-M 0.000 description 1
- BBXRDNWEEDIWSP-UHFFFAOYSA-N 1-octyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2N(CCCCCCCC)CCCN21 BBXRDNWEEDIWSP-UHFFFAOYSA-N 0.000 description 1
- JDOPFDYBTLWCOD-UHFFFAOYSA-N 1-propyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2N(CCC)CCCN21 JDOPFDYBTLWCOD-UHFFFAOYSA-N 0.000 description 1
- MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 description 1
- AJGAPBXTFUSKNJ-UHFFFAOYSA-N 2-cyclohexylguanidine Chemical compound NC(=N)NC1CCCCC1 AJGAPBXTFUSKNJ-UHFFFAOYSA-N 0.000 description 1
- KEWLVUBYGUZFKX-UHFFFAOYSA-N 2-ethylguanidine Chemical compound CCNC(N)=N KEWLVUBYGUZFKX-UHFFFAOYSA-N 0.000 description 1
- QRJZGVVKGFIGLI-UHFFFAOYSA-N 2-phenylguanidine Chemical compound NC(=N)NC1=CC=CC=C1 QRJZGVVKGFIGLI-UHFFFAOYSA-N 0.000 description 1
- RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical group NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
- UBMSWBZWCYJRLF-UHFFFAOYSA-N N,N-bis(4-bromophenyl)-4-[(3-methylimidazol-3-ium-1-yl)methyl]aniline Chemical compound BrC1=CC=C(C=C1)N(C1=CC=C(C[N+]2=CN(C=C2)C)C=C1)C1=CC=C(C=C1)Br UBMSWBZWCYJRLF-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- ZTQQEWDFCLNKIW-UHFFFAOYSA-M benzyl(triethyl)azanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CC[N+](CC)(CC)CC1=CC=CC=C1 ZTQQEWDFCLNKIW-UHFFFAOYSA-M 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 1
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 1
- ZRZKFGDGIPLXIB-UHFFFAOYSA-N fluoroform;sulfuric acid Chemical class FC(F)F.OS(O)(=O)=O ZRZKFGDGIPLXIB-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- SEACXNRNJAXIBM-UHFFFAOYSA-N triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC SEACXNRNJAXIBM-UHFFFAOYSA-N 0.000 description 1
- SLVAEVYIJHDKRO-UHFFFAOYSA-N trifluoromethanesulfonyl fluoride Chemical compound FC(F)(F)S(F)(=O)=O SLVAEVYIJHDKRO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
-
- 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
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—Quaternary ammonium compounds
- C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C277/08—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of substituted guanidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/06—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/06—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing halogen atoms, or nitro or nitroso groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
- C07C309/09—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton
- C07C309/10—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton with the oxygen atom of at least one of the etherified hydroxy groups further bound to an acyclic carbon atom
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
本出願は、2013年10月4日出願の欧州特許出願第13187325.9号に対する優先権を主張するものであり、この出願の全内容は、あらゆる目的のために参照により本明細書に援用される。
[R1R2R3R4N] + [RfSO3] −
(式中:
− R1〜R4は、アルキル、アルケニル、シクロアルキルもしくはアルリールアルキルを表すか、またはN原子とそれらは結合して複素環を形成し、
− Rfは、C1〜C12の過フッ素化直鎖または分岐アルキルを表す)
のアンモニウム塩の合成を開示している。これらの塩は、第三級アミン、フッ化過フッ素化スルホニルおよびシランエステルの反応によって製造される。反応は、エーテル、クロロホルムまたはアセトニトリルのような、極性の不活性溶媒の存在下に実施することができる。
− 4−[ビス(4−ブロモフェニル)アミノ]ベンジルトリエチルアンモニウムのトリフルオロメタンスルホネート塩および:
1−{4−[ビス(4−ブロモフェニル)アミノ]ベンジル}−3−メチル−イミダゾリウムのトリフルオロメタンスルホネート塩
の合成方法を開示している。
RfSO2X (I)
(式中、Xは、F、ClおよびBrから選択される、好ましくはXは、FおよびClから選択され、より好ましくはXはFである)
で表され得る。
NR1R2R3 (II)
(式中、R1、R2およびR3は、互いに独立して、C1〜C25、好ましくはC2〜C20の、直鎖、分岐または環状の、任意選択的に置換された、アルカンまたはアルケン、およびC6〜C25の、任意選択的に置換された、アリールまたはヘテロアリールからなる群から選択される)
のものの中で選択される。
(式中、R4、R5、R6、R7およびR8のそれぞれは独立して、H、ハロゲン、C1〜C25、好ましくはC1〜C20の、直鎖、分岐または環状の、任意選択的に置換された、アルカンまたはアルケン、およびC6〜C25の、任意選択的に置換された、アリールまたはヘテロアリールからなる群から選択される)
のものの中で選択されてもよい。好ましくは、R4、R5、R6、R7およびR8のそれぞれは独立して、H、およびC1〜C25、好ましくはC1〜C20の、直鎖、分岐または環状の、任意選択的に置換された、アルカンからなる群から選択される。好適なピリジン類の注目すべき例は、例えば、式中:R4、R5、R6、R7およびR8がすべてHである;R4=R8=CH3およびR5=R6=R7=Hである;R4=R6=R8=CH3およびR5=R7=Hである;そしてR4=R6=CH3およびR5=R7=R8=Hである式(III)に従うものである。
(式中、R9、R10、R11およびR12は、互いに独立して、H,ヘテロ原子を任意選択的に含有する、C1〜C25、好ましくはC1〜C20の、直鎖、分岐または環状の、任意選択的に置換された、アルカンまたはアルケンであり;式中、R9、R10、R11およびR12の最大4つまでは、単結合または二重結合によって対で互いに結合していてもよい)
のアミジン類の中から選択されてもよい。好ましくは、R9、R10、R11およびR12がすべて同時にHであることはない。
(式中、R13、R14、R15、R16およびR17は、互いに独立して、H、ヘテロ原子を任意選択的に含有する、C1〜C25、好ましくはC1〜C20の、直鎖、分岐または環状の、任意選択的に置換された、アルカンまたはアルケンからなる群から選択され;式中、R13、R14、R15、R16およびR17の最大4つまでは、単結合または二重結合によって対で互いに結合していてもよい)
のグアニジン類の中で選択されてもよい。好ましくは、R13、R14、R15、R16およびR17は、同時にHであることはない。しかし、R13、R14、R15、R16およびR17の少なくとも1つはHであることが好ましい。
(式中、Rf、R1〜R12のそれぞれは、上に定義された通りであり、R’は、追加の−OH基を任意選択的に含有するC1〜C20の直鎖、分岐または環状の、任意選択的に置換された、アルキル、およびC6〜C20の任意選択的に置換されたアリールまたはヘテロアリールからなる群から選択される)
に従って、式(II)のアミン、式(III)のピリジン類および式(IV)のアミジン類から本発明の方法で得られる。
(ここで、式(IX)においてRfおよびR13〜R17のそれぞれは、上に定義された通りである)
に従ってグアニジニウムフルオロアルキルスルホネートの製造に特に好適であることが分かった。
温度計および攪拌を備えた3つ口丸底フラスコに、CH2Cl2(60mL)およびCF3CF2OCF2CF2SO2F(10g)を添加した。混合物の温度を0℃にした。トリエチルアミン(8.76mL)を添加し、混合物を30分間0℃で攪拌させた。メタノール(2.01g)を滴加した。混合物の温度を室温に戻らせた。2時間後に反応は完了した。液相を、真空下に蒸発によって除去した。白色固体を、CH2Cl2(50mL)に再溶解させ、水性NaOH溶液(70mL)で抽出した。有機相を水相から分離した。水相をNa2SO4で処理し、生成物を、真空下での蒸発によって回収した。メチル−トリエチルアンモニウム2−(パーフルオロエトキシ)パーフルオルエタンスルホネート(実施例1、11.7g)を87%収率で白色固体として単離した(融点 154℃;1%減量:312℃)。
19F NMR(HFMX基準):−84.1ppm(m;2F;−OCF 2CF2−);−88.2ppm(s;3F;−CF 3);−90.1ppm(m;2F;CF3CF 2O−);−120.1ppm(s;2F;−CF 2SO3 −).1H NMR(TMS基準):+3.26ppm(q;6H;−NCH 2CH3);+2.88ppm(s;3H;CH 3−N−);+1.22ppm(m;9H;−NCH2CH 3).
19F NMR(HFMX基準):−84.1ppm(m;2F;−OCF 2CF2−);−88.2ppm(s;3F;−CF 3);−90.1ppm(m;2F;CF3CF 2O−);−120.1ppm(s;2F;−CF 2SO3 −).1H NMR(TMS基準):+3.14ppm(m;8H;NCH 2−);+1.55ppm(m;8H;NCH2CH 2−);+1.28ppm(m;8H;−CH 2CH3);+0.90ppm(t;12H;−CH2CH 3).
19F NMR(HFMX基準):−84.1ppm(m;2F;−OCF 2CF2−);−88.2ppm(s;3F;−CF 3);−90.1ppm(m;2F;CF3CF 2O−);−120.1ppm(s;2F;−CF 2SO3 −).1H NMR(TMS基準):+7.55ppm(m;10H;Ph−);+4.58ppm(s;4H;−NCH 2Ph);+2.84ppm(s;6H;−NCH 3).
実施例1について記載されたものと同様な手順に従って、CF3CF2OCF2CF2SO2F(20g)を、室温でCH2Cl2(80mL)中メタノール(4.03g)の存在下で2,4,6−トリメチルピリジン(15.24g)と反応させた。N−メチル−2,4,6−トリメチル−ピリジニウム2−(パーフルオロエトキシ)パーフルオルエタンスルホネート(融点 83.2℃、1%減量:323℃)が、87%収率で白色固体として単離された。
19F NMR(HFMX基準):−84.1ppm(m;2F;−OCF 2CF2−);−88.2ppm(s;3F;−CF 3);−90.1ppm(m;2F;CF3CF 2O−);−120.1ppm(s;2F;−CF 2SO3 −).1H NMR(TMS基準):+7.70ppm(s;2H;メタ−H);+3.96ppm(s;3H;NCH 3);+2.72ppm(s;6H;オルト−CH 3);+2.47ppm(s;3H;パラ−CH 3).
実施例1について記載されたものと同様な手順に従って、CF3CF2OCF2CF2SO2F(27g)を、室温においてCH2Cl2中メタノール(5.44g)の存在下で1,8−ジアザビシクロ[5.4.0]ウンデカ−7−エン(16.80g)と反応させた。N−メチル−1,8−ジアザビシクロ[5.4.0]ウンデカ−7−エニウム2−(パーフルオロエトキシ)パーフルオルエタンスルホネートと1,8−ジアザビシクロ[5.4.0]ウンデカ−7−エニウム2−(パーフルオロエトキシ)パーフルオルエタンスルホネートとの混合物(混合物の融点 −60℃)が72.8%収率で黄色オイルとして単離された。
CH2Cl2(305g)および1,5,7−トリアザビシクロ[4.4.0]−デカ−5−エン(55.55g)を含有する温度計および攪拌を備えた3つ口丸底フラスコに、水中におけるK2CO3の溶液(4M)を添加し、引き続きCF2ClCFClOCF2CF2SO2F(140.05g)を滴加した。混合物の温度を室温に保った。2時間後に反応は完了した。二相系が得られた。有機相を水相から分離し、水で洗浄し、MgSO4で処理し、いかなる固体も濾別した。生成物を、84%収率で真空下での蒸発によって回収した。(融点 67℃;1%減量:304℃)。
19F NMR(HFMX基準):−70.9ppm(d;2F;ClCF 2−);−76.5ppm(m;1F;−CFClO−);−83.3ppm(m;2F;−OCF 2CF2−);−118.5ppm(s;2F;−CF 2SO3 −).1H NMR(TMS基準):+3.30ppm(m;8H;−NCH 2−);+2.00ppm(m;4H;−CH 2−).
19F NMR(HFMX基準):−70.9ppm(d;2F;ClCF 2−);−76.5ppm(m;1F;−CFClO−);−83.3ppm(m;2F;−OCF 2CF2−);−118.5ppm(s;2F;−CF 2SO3 −).1H NMR(TMS基準):+2.95ppm(s;12H;CH 3N−).
Claims (10)
- 有機塩基のフルオロアルキルスルホネート塩の調製方法であって、前記方法が、ハロゲン化フルオロアルキルスルホニルを、ピリジン類、アミジン類及びグアニジン類からなる群から選択される有機塩基と反応させる工程を含む、方法。
- ハロゲン化フルオロアルキルスルホニルが、式(I)RfSO2X(式中、Xは、F、ClおよびBrから選択され;Rfは、任意選択的に置換されたならびに/または鎖中にO、NおよびSからなる群から選択されるヘテロ原子を任意選択的に含む、C1〜C25の直鎖、分岐または環状のフッ素化アルキルまたはアルケニルからなる群から選択される)のフルオロアルキルスルホネートからなる群から選択される、請求項1に記載の方法。
- 有機塩基が、式(III):
(式中、R4、R5、R6、R7およびR8のそれぞれは独立して、H、ハロゲン、C1〜C25、好ましくはC1〜C20の、直鎖、分岐または環状の、任意選択的に置換された、アルカンまたはアルケン、およびC6〜C25の、任意選択的に置換された、アリールまたはヘテロアリールからなる群から選択される)
のものの中で選択されるピリジン類;式(IV):
(式中、R9、R10、R11およびR12は、互いに独立して、H、ヘテロ原子を任意選択的に含有する、C1〜C25、好ましくはC1〜C20の、直鎖、分岐または環状の、任意選択的に置換された、アルカンまたはアルケンからなる群から選択され;式中、R9、R10、R11およびR12の最大4つまでは、単結合または二重結合によって対で互いに結合していてもよい)
のものの中で選択されるアミジン類;ならびに式(V):
(式中、R13、R14、R15、R16およびR17は、互いに独立して、H、ヘテロ原子を任意選択的に含有する、C1〜C25、好ましくはC1〜C20の、直鎖、分岐または環状の、任意選択的に置換された、アルカンまたはアルケンからなる群から選択され;式中、R13、R14、R15、R16およびR17の最大4つまでは、単結合または二重結合によって対で互いに結合していてもよい)
のものの中で選択されるグアニジン類からなる群から選択される、請求項1または2に記載の方法。 - ハロゲン化フルオロアルキルスルホニルが、アルコールの存在下で有機塩基と反応させられる、請求項1〜3のいずれか一項に記載の方法。
- 有機塩基が、ピリジン類およびアミジン類からなる群から選択される請求項4に記載の方法。
- 式(VII)および(VIII)のフルオロアルキルスルホネート:
(式中、Rf、R4〜R12のそれぞれは、請求項2および3に定義された通りであり、R’は、追加の−OH基を任意選択的に含有するC1〜C20の直鎖、分岐または環状の、任意選択的に置換された、アルキル、およびC6〜C20の任意選択的に置換されたアリールまたはヘテロアリールからなる群から選択される)
が、式(I)のフルオロアルキルスルホネートを式(III)のピリジン類および式(IV)のアミジン類、ならびにR’OHのアルコールと反応させることによって製造される、請求項4または5に記載の方法。 - ハロゲン化フルオロアルキルスルホニルが、塩基性条件下、水の存在下で有機塩基と反応させられる、請求項1〜3のいずれか一項に記載の方法。
- 有機塩基がグアニジンである、請求項7に記載の方法。
- 式(IX):
(式中、Rf、R13〜R17のそれぞれは、請求項2および3に定義された通りである)
のグアニジニウムフルオロアルキルスルホネートが得られる、請求項7または8に記載の方法。 - RfがCF2CF2OCFClCF2Clである、請求項6に定義されたような式(VII)および(VIII)の、ならびに請求項9に定義されたような式(IX)のフルオロアルキルスルホネート塩。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP13187325 | 2013-10-04 | ||
EP13187325.9 | 2013-10-04 | ||
PCT/EP2014/070952 WO2015049239A1 (en) | 2013-10-04 | 2014-09-30 | Process for the synthesis of fluoralkyl sulfonate salts |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2016533351A true JP2016533351A (ja) | 2016-10-27 |
JP6688729B2 JP6688729B2 (ja) | 2020-04-28 |
Family
ID=49322233
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2016519774A Expired - Fee Related JP6688729B2 (ja) | 2013-10-04 | 2014-09-30 | フルオロアルキルスルホネート塩の合成方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US9944593B2 (ja) |
EP (1) | EP3052474A1 (ja) |
JP (1) | JP6688729B2 (ja) |
KR (1) | KR20160067900A (ja) |
CN (1) | CN105593208A (ja) |
WO (1) | WO2015049239A1 (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR102487719B1 (ko) * | 2016-10-28 | 2023-01-16 | 솔베이 스페셜티 폴리머스 이태리 에스.피.에이. | 중합체의 가교 방법 |
CN108003033A (zh) * | 2017-12-05 | 2018-05-08 | 常州大学 | 一种超级电容器用季铵盐的制备方法 |
CN108976152B (zh) * | 2018-09-10 | 2020-10-23 | 江汉大学 | 一种烷基醚类磺酰氟化合物及其合成方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1966931A1 (de) * | 1969-06-11 | 1975-05-28 | Bayer Ag | Perfluoralkylsubstituierte, quartaere ammoniumsalze |
JPH0399047A (ja) * | 1989-09-04 | 1991-04-24 | F Hoffmann La Roche Ag | アミノ酸誘導体 |
JPH08245546A (ja) * | 1995-02-08 | 1996-09-24 | Haldor Topsoee As | フッ素化スルホニルフルオリドを加水分解する方法 |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3919295A (en) | 1973-04-16 | 1975-11-11 | Bayer Ag | Preparation of inorganic fluoride-free perfluoroalkane sulphonates |
DE2658560C2 (de) | 1976-12-23 | 1979-02-01 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Tetraäthylammoniumperfluoralkylsulfonaten |
US4873020A (en) | 1988-10-04 | 1989-10-10 | Minnesota Mining And Manufacturing Company | Fluorochemical surfactants and process for preparing same |
JP2974540B2 (ja) * | 1993-04-19 | 1999-11-10 | セントラル硝子株式会社 | フルオロアルキルスルホン酸の精製方法 |
US5488147A (en) * | 1994-07-21 | 1996-01-30 | Minnesota Mining And Manufacturing Company | Diaryliodonium fluoroalkyl sulfonate salts and a method of making |
JP3250777B2 (ja) * | 1995-02-13 | 2002-01-28 | セントラル硝子株式会社 | イミド類、その塩類およびそれらの製造法 |
US6743947B1 (en) | 1999-05-10 | 2004-06-01 | The United States Of America As Represented By The Secretary Of The Army | Electrochemically stable onium salts and electrolytes containing such for electrochemical capacitors |
DE10325051A1 (de) | 2003-06-02 | 2004-12-23 | Merck Patent Gmbh | Ionische Flüssigkeiten mit Guanidinium-Kationen |
DE102004005404A1 (de) | 2004-02-03 | 2005-08-25 | Merck Patent Gmbh | Verfahren zur Herstellung von Guanidinium-Salzen |
AR058054A1 (es) | 2005-09-22 | 2008-01-23 | Du Pont | Utilizacion de liquidos ionicos para la separacion de hidrofluorocarburos |
US20070100184A1 (en) | 2005-10-27 | 2007-05-03 | Harmer Mark A | Alkylation of aromatic compounds |
DE102007028427A1 (de) | 2007-06-20 | 2008-12-24 | KLüBER LUBRICATION MüNCHEN KG | Verwendung von ionischen Flüssigkeiten zur Verbesserung der Eigenschaften von Schmierstoffzusammensetzungen |
US20100204521A1 (en) | 2007-09-05 | 2010-08-12 | Mark Harmer | Processes for making dibutyl ethers from 2-butanol |
WO2012156540A2 (en) | 2012-03-08 | 2012-11-22 | Lonza Ltd | Method for preparation of mononitrated aromatic compounds |
-
2014
- 2014-09-30 CN CN201480054647.0A patent/CN105593208A/zh active Pending
- 2014-09-30 JP JP2016519774A patent/JP6688729B2/ja not_active Expired - Fee Related
- 2014-09-30 EP EP14777606.6A patent/EP3052474A1/en active Pending
- 2014-09-30 WO PCT/EP2014/070952 patent/WO2015049239A1/en active Application Filing
- 2014-09-30 KR KR1020167011435A patent/KR20160067900A/ko not_active Application Discontinuation
- 2014-09-30 US US15/027,167 patent/US9944593B2/en not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1966931A1 (de) * | 1969-06-11 | 1975-05-28 | Bayer Ag | Perfluoralkylsubstituierte, quartaere ammoniumsalze |
JPH0399047A (ja) * | 1989-09-04 | 1991-04-24 | F Hoffmann La Roche Ag | アミノ酸誘導体 |
JPH08245546A (ja) * | 1995-02-08 | 1996-09-24 | Haldor Topsoee As | フッ素化スルホニルフルオリドを加水分解する方法 |
Non-Patent Citations (3)
Title |
---|
B. BENNUA-SKALMOWSKI, ET AL.: "The reaction of perfluorobutanesulfonyl fluoride with alcohols in the presence of 4-dialkylaminopyri", BULLETIN DES SOCIETES CHIMIQUES BELGES, vol. Vol.103, No.7-8, JPN6018018229, 1994, pages 453 - 461 * |
J. BURDON, ET AL.: "Trifluoromethanesulphonate esters and their alkylating properties", TETRAHEDRON, vol. Vol.21, JPN6018018224, 1965, pages 1 - 4, XP000569521, DOI: doi:10.1016/S0040-4020(01)82194-3 * |
K. TAKAHASHI, ET AL.: "Development of triarylamine mediator having ionic-tag and its application to electrocatalytic reacti", ELECTROCHIMICA ACTA, vol. Vol. 77, JPN6018018226, 2012, pages 47 - 53, XP028404691, DOI: doi:10.1016/j.electacta.2012.05.049 * |
Also Published As
Publication number | Publication date |
---|---|
WO2015049239A1 (en) | 2015-04-09 |
EP3052474A1 (en) | 2016-08-10 |
CN105593208A (zh) | 2016-05-18 |
KR20160067900A (ko) | 2016-06-14 |
JP6688729B2 (ja) | 2020-04-28 |
US20160237028A1 (en) | 2016-08-18 |
US9944593B2 (en) | 2018-04-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2014196303A (ja) | 含フッ素n−アルキルスルホニルイミド化合物の製造方法およびイオン性化合物の製造方法 | |
JP4322004B2 (ja) | オニウム塩 | |
JP2016533351A (ja) | フルオロアルキルスルホネート塩の合成方法 | |
JP4822269B2 (ja) | 新規なオニウム塩 | |
WO2008056776A1 (en) | Mesoionic compound, ionic liquid composed of mesoionic compound, and method for producing mesoionic compound | |
Jagadeeswara Rao et al. | Thermochemical properties of some bis (trifluoromethyl-sulfonyl) imide based room temperature ionic liquids | |
US10889537B2 (en) | Method for producing fluorine-containing dialkyl carbonate compounds | |
JP2021165294A (ja) | 新規スルファミン酸リチウム | |
WO2017090346A1 (ja) | ケイ素含有スルホン酸塩 | |
US10065936B2 (en) | Synthesis of sulfur containing ammonium and phosphonium borates | |
JPWO2009025246A1 (ja) | 精製された含フッ素ビススルホニルイミドのアンモニウム塩の製造方法 | |
EP2910558B1 (en) | Ionic liquid | |
WO2011148971A1 (ja) | 含フッ素スルホニルイミド化合物の製造方法 | |
JP2013166698A (ja) | イミド化合物の製造方法 | |
WO2010113492A1 (ja) | 含フッ素n-アルキルスルホニルイミド化合物及びその製造方法、並びにイオン性化合物の製造方法 | |
JP2004175668A (ja) | オニウム塩 | |
JP5518573B2 (ja) | フッ素化スルホンイミド化合物の製造方法 | |
US20120184763A1 (en) | Method for producing perfluorosulfonic acid having ether structure and derivative thereof, and surfactant containing fluorine-containing ether sulfonic acid compound and derivative thereof | |
US20100222580A1 (en) | Process For The Preparation Of Onium Alkylsulfates Having A Low Halide Content | |
JP7304554B2 (ja) | シリルエーテル含有スルホン酸塩 | |
JP7230274B2 (ja) | 含フッ素ピリミジン化合物およびその製造方法 | |
TWI438183B (zh) | Compounds | |
JP2010265237A (ja) | 第四級ホスホニウム塩及びそれを含有してなる電解質 | |
CZ20097A3 (cs) | Fluorové iontové kapaliny na bázi imidazoliových solí s vysokou fluorofilitou | |
JP2016212947A (ja) | ジスルホニルアミド塩およびその製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20170830 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20180508 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20180529 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20180822 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20181026 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20181122 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20190129 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190131 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20190521 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20190820 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20191018 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20200310 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20200406 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6688729 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
LAPS | Cancellation because of no payment of annual fees |