JPWO2007061024A1 - フッ素化アルキルフルオロリン酸スルホニウムの製造方法 - Google Patents
フッ素化アルキルフルオロリン酸スルホニウムの製造方法 Download PDFInfo
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- JPWO2007061024A1 JPWO2007061024A1 JP2007546486A JP2007546486A JPWO2007061024A1 JP WO2007061024 A1 JPWO2007061024 A1 JP WO2007061024A1 JP 2007546486 A JP2007546486 A JP 2007546486A JP 2007546486 A JP2007546486 A JP 2007546486A JP WO2007061024 A1 JPWO2007061024 A1 JP WO2007061024A1
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- Prior art keywords
- group
- aryl
- compound
- carbon atoms
- fluorinated alkyl
- Prior art date
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- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 40
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 35
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 title description 14
- DWYMPOCYEZONEA-UHFFFAOYSA-L fluoridophosphate Chemical compound [O-]P([O-])(F)=O DWYMPOCYEZONEA-UHFFFAOYSA-L 0.000 title description 3
- -1 aryl compound Chemical class 0.000 claims abstract description 197
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 54
- 239000012024 dehydrating agents Substances 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 19
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 51
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 35
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 33
- 239000002904 solvent Substances 0.000 claims description 21
- 229910052783 alkali metal Inorganic materials 0.000 claims description 12
- 150000001340 alkali metals Chemical class 0.000 claims description 11
- 125000005110 aryl thio group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 150000002500 ions Chemical class 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 14
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 125000000041 C6-C10 aryl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 239000007983 Tris buffer Substances 0.000 description 24
- 150000003839 salts Chemical class 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- JFZKOODUSFUFIZ-UHFFFAOYSA-N trifluoro phosphate Chemical compound FOP(=O)(OF)OF JFZKOODUSFUFIZ-UHFFFAOYSA-N 0.000 description 19
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 11
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
- OWZDULOODZHVCQ-UHFFFAOYSA-N diphenyl-(4-phenylsulfanylphenyl)sulfanium Chemical compound C=1C=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1SC1=CC=CC=C1 OWZDULOODZHVCQ-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 150000007524 organic acids Chemical class 0.000 description 10
- 235000011121 sodium hydroxide Nutrition 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- 150000002367 halogens Chemical group 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000003505 polymerization initiator Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 150000003462 sulfoxides Chemical class 0.000 description 8
- JJHHIJFTHRNPIK-UHFFFAOYSA-N Diphenyl sulfoxide Chemical compound C=1C=CC=CC=1S(=O)C1=CC=CC=C1 JJHHIJFTHRNPIK-UHFFFAOYSA-N 0.000 description 7
- 150000001342 alkaline earth metals Chemical class 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 150000001450 anions Chemical class 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 239000002699 waste material Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- 108010000020 Platelet Factor 3 Proteins 0.000 description 6
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 description 6
- 125000004104 aryloxy group Chemical group 0.000 description 6
- 238000010538 cationic polymerization reaction Methods 0.000 description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 6
- 230000000977 initiatory effect Effects 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 238000000862 absorption spectrum Methods 0.000 description 5
- 235000011054 acetic acid Nutrition 0.000 description 5
- 125000004423 acyloxy group Chemical group 0.000 description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 229910052787 antimony Inorganic materials 0.000 description 5
- 229910052785 arsenic Inorganic materials 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 150000007522 mineralic acids Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229910018286 SbF 6 Inorganic materials 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000005529 alkyleneoxy group Chemical group 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 4
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 4
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 4
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 3
- 229910017008 AsF 6 Inorganic materials 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- OUSHJSZZJRZPOM-UHFFFAOYSA-N P(=O)(F)(F)F.FC(C(F)(F)F)(F)[K] Chemical compound P(=O)(F)(F)F.FC(C(F)(F)F)(F)[K] OUSHJSZZJRZPOM-UHFFFAOYSA-N 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 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 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 125000006343 heptafluoro propyl group Chemical group 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000002347 octyl 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])[H] 0.000 description 3
- GJSGGHOYGKMUPT-UHFFFAOYSA-N phenoxathiine Chemical compound C1=CC=C2OC3=CC=CC=C3SC2=C1 GJSGGHOYGKMUPT-UHFFFAOYSA-N 0.000 description 3
- QQBDOJUNCZSRGA-UHFFFAOYSA-N phenyl-(4-phenylsulfanylphenyl)methanone Chemical compound C=1C=C(SC=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 QQBDOJUNCZSRGA-UHFFFAOYSA-N 0.000 description 3
- 239000003495 polar organic solvent Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 3
- 231100000701 toxic element Toxicity 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- OVIAOYLSBJBPSY-UHFFFAOYSA-N (3-chloro-4-phenylsulfanylphenyl)-phenylmethanone Chemical compound ClC1=CC(C(=O)C=2C=CC=CC=2)=CC=C1SC1=CC=CC=C1 OVIAOYLSBJBPSY-UHFFFAOYSA-N 0.000 description 2
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 description 2
- WGBYOWIYAKVOLO-UHFFFAOYSA-N 1,4-bis(phenylsulfanyl)benzene Chemical compound C=1C=C(SC=2C=CC=CC=2)C=CC=1SC1=CC=CC=C1 WGBYOWIYAKVOLO-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- RKMZTRDJSKGOCM-UHFFFAOYSA-N 1-chloro-4-phenylsulfanylbenzene Chemical compound C1=CC(Cl)=CC=C1SC1=CC=CC=C1 RKMZTRDJSKGOCM-UHFFFAOYSA-N 0.000 description 2
- GVYKABJIEOOUOX-UHFFFAOYSA-N 1-fluoro-4-(4-fluorophenyl)sulfinylbenzene Chemical compound C1=CC(F)=CC=C1S(=O)C1=CC=C(F)C=C1 GVYKABJIEOOUOX-UHFFFAOYSA-N 0.000 description 2
- LEDPSBGADKSDKI-UHFFFAOYSA-N 1-methoxy-4-(4-methoxyphenyl)sulfinylbenzene Chemical compound C1=CC(OC)=CC=C1S(=O)C1=CC=C(OC)C=C1 LEDPSBGADKSDKI-UHFFFAOYSA-N 0.000 description 2
- NQMUGNMMFTYOHK-UHFFFAOYSA-N 1-methoxynaphthalene Chemical compound C1=CC=C2C(OC)=CC=CC2=C1 NQMUGNMMFTYOHK-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- AZTMYBHDPKCGQE-UHFFFAOYSA-N 1-phenylsulfanyl-4-(4-phenylsulfanylphenyl)benzene Chemical group C=1C=C(C=2C=CC(SC=3C=CC=CC=3)=CC=2)C=CC=1SC1=CC=CC=C1 AZTMYBHDPKCGQE-UHFFFAOYSA-N 0.000 description 2
- YEZOVIIHKKPUOS-UHFFFAOYSA-N 10-oxothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3S(=O)C2=C1 YEZOVIIHKKPUOS-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 2
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
- QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- TURIHPLQSRVWHU-UHFFFAOYSA-N 2-phenylnaphthalene Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=C1 TURIHPLQSRVWHU-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
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- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
- RHFUXPCCELGMFC-UHFFFAOYSA-N n-(6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl)-n-phenylmethoxyacetamide Chemical compound OC1C(C)(C)OC2=CC=C(C#N)C=C2C1N(C(=O)C)OCC1=CC=CC=C1 RHFUXPCCELGMFC-UHFFFAOYSA-N 0.000 description 1
- GMQJJPFDTXFVJG-UHFFFAOYSA-N naphthalene;naphthalen-1-ol Chemical class C1=CC=CC2=CC=CC=C21.C1=CC=C2C(O)=CC=CC2=C1 GMQJJPFDTXFVJG-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004932 phenoxathinyl group Chemical group 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- BOTNYLSAWDQNEX-UHFFFAOYSA-N phenoxymethylbenzene Chemical compound C=1C=CC=CC=1COC1=CC=CC=C1 BOTNYLSAWDQNEX-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])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
- 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
- 238000003860 storage Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- SPJZSTLXABSXII-UHFFFAOYSA-N tert-butyl(trimethyl)azanium Chemical compound CC(C)(C)[N+](C)(C)C SPJZSTLXABSXII-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- SEACXNRNJAXIBM-UHFFFAOYSA-N triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC SEACXNRNJAXIBM-UHFFFAOYSA-N 0.000 description 1
- COOSQAXLLKTSQO-UHFFFAOYSA-N trimethyl(2-methylpropyl)azanium Chemical compound CC(C)C[N+](C)(C)C COOSQAXLLKTSQO-UHFFFAOYSA-N 0.000 description 1
- BMTHNVMASXVELE-UHFFFAOYSA-N trimethyl(propan-2-yl)azanium Chemical compound CC(C)[N+](C)(C)C BMTHNVMASXVELE-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/12—Sulfonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/14—Esters of phosphoric acids containing P(=O)-halide groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/535—Organo-phosphoranes
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
(2)アリール化合物(A)が、置換されていてもよい少なくとも1個のアリールチオ基を有するものである、上記1の製造方法。
(3)式(1)中、R1およびR2が、置換されていてもよいフェニル基である、上記1または2の製造方法。
(4)フッ素化アルキルフルオロリン酸(C)が、H[(CF3CF2)3PF3]、H[(CF3CF2CF2)3PF3]、H[((CF3)2CFCF2)3PF3]及びH[((CF3)2CFCF2)2PF4]よりなる群より選ばれるものである、上記1ないし3のいずれかの製造方法。
(5)脱水剤(D)が無水酢酸である、上記1ないし4のいずれかの製造方法。
(6)フッ素化アルキルフルオロリン酸(C)が、該アリール化合物(A)、該スルホキシド化合物(B)、該脱水剤(D)及び溶媒の少なくとも1種を含んでなる反応系に、アルカリ金属またはアルカリ土類金属のフッ素化アルキルフルオロリン酸塩と硫酸とを添加することによって該反応系内で発生させられるものである、上記1ないし5のいずれかの製造方法。
(7)該フッ素化アルキルフルオロリン酸塩が、Li、K及びNaよりなる群より選ばれる少なくとも1種のアルカリ金属のフッ素化アルキルフルオロリン酸塩である、上記6の製造方法。
Rfとしては、CF3CF2、(CF3)2CF、CF3CF2CF2、CF3CF2CF2CF2、(CF3)2CFCF2が特に好ましい。
フッ素化アルキルホスホランとフッ化水素の反応モル比は、通常、1:(0.8〜1.2)、好ましくは1:1である。
この反応における反応温度は、通常、0〜80℃、好ましくは、20〜60℃である。
フッ素化アルキルフルオロリン酸(C)を反応系内で発生させる場合は、たとえば溶媒を仕込んだ後に、まずフッ素化アルキルフルオロリン酸(C)を発生させる反応を行い、ついでこの溶液にスルホキシド化合物(B)を投入して混合溶解し、脱水剤(D)とアリール化合物(A)を仕込んでもよく、あるいは、脱水剤(D)、必要により溶媒を仕込み、アリール化合物(A)、スルホキシド化合物(B)を仕込んだ後に、フッ素化アルキルフルオロリン酸(C)を発生させる原料を仕込んでもよい。
これらを回収する際の温度は、通常、40〜120℃、好ましくは50〜80℃である。温度が120℃を超えると、目的のスルホニウム塩が分解する恐れがある。回収した脱水剤や溶媒は再使用することができる。
100mlの反応容器に、アセトニトリル14.6gとトリス(ペンタフルオロエチル)ジフルオロホスホラン14.5g(34.0mmol)を仕込み、均一に混合した後、0〜5℃でフッ化水素0.68g(34.0mmol)を滴下した。この溶液に、あらかじめ、アセトニトリル10.3gにジフェニルスルホキシド6.2g(30.7mmol)、ジフェニルスルフィド5.7g(30.5mmol)、無水酢酸9.7g(95.0mmol)を溶解した溶液を、10〜20℃で滴下し、30分攪拌した。その後40℃で7時間反応させた後、反応液を室温まで冷却し、30gのジクロロメタンを加えて混合した。この溶液を60gの水で洗浄した後、有機層を水20gでさらに3回洗浄した。ついでジクロロメタンを溜去して、淡黄色の固形物25.9gを得た。
得られた固形物は、19F−NMR、1H−NMRと赤外吸収スペクトルから、目的の[4−(フェニルチオフェニル)]ジフェニルスルホニウムトリス(ペンタフルオロエチル) トリフルオロリン酸塩および微量の原料を含んでいた。HPLCの分析結果から、純度は94%であった(収率:97%)。
洗浄後に回収された水層を中和したところ23.6gの40%水酸化ナトリウム水溶液を要した。
100mlの反応容器に、トリス(ペンタフルオロエチル) トリフルオロリン酸カリウム 18.3g(37.8mmol)、アセトニトリル14.1g仕込み、攪拌混合した後に、濃硫酸3.8g(38.7mmol)を滴下し、30分間攪拌した。
この溶液に、ジフェニルスルホキシド6.2g(30.7mmol)と無水酢酸9.7g(95.0mmol)を予め均一に溶解しておいた溶液を室温で投入し、次いでジフェニルスルフィド5.9g(31.7mmol)を滴下した。45℃で6時間反応させた後、反応液を室温まで冷却し、30gのジクロロメタンを加えて混合した。この溶液を60gの水で洗浄した後、有機層を水20gでさらに3回洗浄した。ついでジクロロメタンを溜去して、淡黄色の固形物24.8gを得た。
得られた固形物は、19F−NMR、1H−NMRと赤外吸収スペクトルから、目的の(4−フェニルチオフェニル)ジフェニルスルホニウムトリス(ペンタフルオロエチル) トリフルオロリン酸塩であることが確認され、高速液体クロマトグラフィー(HPLC)の分析結果から、純度は96%であった(収率95%)。
洗浄後に回収された水層を中和したところ23.8gの40%水酸化ナトリウム水溶液を要した。
100mlの反応容器に、ジフェニルスルフィド5.9g(31.7mmol)、ジフェニルスルホキシド6.2g(30.7mmol)、アセトニトリル14.1g、無水酢酸9.7g(95.0mmol)、トリス(ペンタフルオロエチル) トリフルオロリン酸カリウム 18.3g(37.8mmol)を仕込み、30分間攪拌混合した。この溶液に、液温が45℃以下になるように調節しながら濃硫酸3.8g(38.7mmol)を滴下した。45℃で6時間反応させた後、反応液を室温まで冷却し、30gのジクロロメタンを加えて混合した。この溶液を60gの水で洗浄した後、有機層を水20gでさらに3回洗浄した。ついでジクロロメタンを溜去して、淡黄色の固形物25.1gを得た。
得られた固形物は、19F−NMR、1H−NMRと赤外吸収スペクトルから、目的の[4−(フェニルチオ)フェニル]ジフェニルスルホニウムトリス(ペンタフルオロエチル) トリフルオロリン酸塩および微量の原料を含んでいた。HPLCの分析結果から、純度は96%であった(収率:96%)。
この固形物にトルエン40gを加えて溶解させ、ヘキサン370g を加えて10℃まで冷却したところ、結晶が析出した。結晶をろ別し、ヘキサンにてかけ洗いを行った後、減圧乾燥して21.3gの目的物の白色結晶を得た(純度:98%以上)。
洗浄後に回収された水層を中和したところ23.5gの40%水酸化ナトリウム水溶液を要した。
トリス(ペンタフルオロエチル) トリフルオロリン酸カリウム18.3gをトリス(ヘプタフルオロプロピル) トリフルオロリン酸カリウム24.0g(37.8mmol)、ジクロロメタン30gを酢酸エチル30gとした以外は実施例3と同様にして、[4−(フェニルチオ)フェニル]ジフェニルスルホニウムトリス(ヘプタフルオロプロピル)トリフルオロリン酸塩28.5gを得た(収率94%、純度98%)。
洗浄後に回収された水層を中和したところ23.7gの40%水酸化ナトリウム水溶液を要した。
ジフェニルスルフィド5.9gをアニソール3.4gとした以外は実施例3と同様にして、4−メトキシフェニルジフェニルスルホニウムトリス(ペンタフルオロエチル)トリフルオロリン酸塩22.0gを得た(収率93%、純度98%)。
洗浄後に回収された水層を中和したところ23.7gの40%水酸化ナトリウム水溶液を要した。
ジフェニルスルフィド5.9gをジベンゾチオフェン5.8gとした以外は実施例3と同様にして、4−ジベンゾチエニルジフェニルスルホニウムスルホニウムトリス(ペンタフルオロエチル)トリフルオロリン酸塩24.7gを得た(収率94%、純度96%)。
洗浄後に回収された水層を中和したところ23.6gの40%水酸化ナトリウム水溶液を要した。
ジフェニルスルフィド5.9gを2−イソプロピルチオキサントン16.1g、ジクロロメタン30gを50g、有機層洗浄用水20gを25gとした以外は実施例3と同様にして、7−(2−イソプロピル)チオキサントニルジフェニルスルホニウムトリス(ペンタフルオロエチル)トリフルオロリン酸塩として34.2gを得た(混合物として収率93%、純度95%)。
洗浄後に回収された水層を中和したところ23.6gの40%水酸化ナトリウム水溶液を要した。
100mlの反応容器に、ジフェニルスルホキシド7.7g(38.1mmol)、ジフェニルスルフィド5.9g(31.7mmol)、メタンスルホン酸27.3g(284.1mmol)を仕込み、均一に混合した後、無水酢酸5.0g(49.0mmol)を滴下した。40〜50℃で5時間反応後、室温まで冷却した。この反応溶液をトリス(ペンタフルオロエチル) トリフルオロリン酸カリウムの20%水溶液79.0g(32.6mmol)の入った容器に滴下し、室温で1時間よく攪拌した。析出した茶色のやや粘調な固形物をろ過し、これを45mlの水で3回洗浄した後、減圧乾燥して茶色の固形物23.9gを得た(収率60%)。
得られた固形物は、19F−NMR、1H−NMRと赤外吸収スペクトルから、主成分は(4−フェニルチオフェニル)ジフェニルスルホニウムトリス(ペンタフルオロエチル)トリフルオロリン酸塩であり、その他ビススルホニウム塩、未反応原料および多種類の構造不明の化合物を含有していた。またHPLCの分析結果から、純度は65%であった。
反応および洗浄後に回収された水層を中和したところ34.4gの40%水酸化ナトリウム水溶液を要した。
100mlの反応容器に濃硫酸36.8g(375.2mmol)とジフェニルスルホキシド2.05g(10.1mmol)を加えて溶解し、この溶液に氷で冷却しながらジフェニルスルフィド1.80g(9.7mmol)をゆっくり滴下し、室温で1時間攪拌した。
次にトリス(ペンタフルオロエチル) トリフルオロリン酸カリウム4.94g(10.2mmol)を水60gに溶解した溶液中に氷60gを加え、これに反応液を氷水で冷却しながら徐々に投入したところ、白色の固体が析出した。これをろ過し、18gの水で4回洗浄後、減圧乾燥して、白色粉末5.4gを得た。
得られた白色粉末を、19F−NMR、1H−NMRと赤外吸収スペクトルから、予想したスルホニオ基を1固有する(4−フェニルチオフェニル)ジフェニルスルホニウムトリス(ペンタフルオロエチル) トリフルオロリン酸塩ではなく、主成分はスルホニオ基を2固有するビススルホニウム体であり、少量の原料および構造不明の化合物を含有していた。HPLCの分析結果から、ビススルホニウム体の純度は85%であった。
また、上記の濾過で分離した際の濾液を分析したところ、ジフェニルスルフィドのスルホン化物が含まれていることが確認された。
反応および洗浄後に回収された水層を中和したところ74.1gの40%水酸化ナトリウム水溶液を要した。
Claims (7)
- 少なくとも1つの炭素原子に水素が結合しているアリール化合物Ar−H(A)と、次式(1)、
[式(1)中、R1、R2は、それらの各々が、互いに同一若しくは異なって、置換されてもよい炭化水素基若しくは置換されてもよいヘテロ環基を表すか、又は双方が直接若しくは−O−、−S−、−SO−、−SO2−、−NH−、−NR’−、−CO−、−COO−、−CONH−、炭素数1〜3のアルキレン基若しくはフェニレン基を介して結合して、置換されていてもよい環構造を形成しており、ここに、R’は炭素数1〜5のアルキル基又は炭素数6〜10のアリール基を表す。]で示されるスルホキシド化合物(B)とを、次式(2)、
[式(2)中、Rfは水素原子の80%以上がフッ素原子で置換されたアルキル基を、aはその個数を表し、1〜5の整数であり、ここに、a個のRfは相互にそれぞれ同一であっても異なっていてもよい。]で表されるフッ素化アルキルフルオロリン酸(C)と脱水剤(D)の存在下に反応させることを特徴とする次式(3)、
[式(3)中のR1、R2 は上記定義に同じであり、Arは少なくとも1つの炭素原子に水素が結合している前記アリール化合物Ar−H(A)から水素が脱離したアリール基を表し、Rf及びaは上記定義に同じである。]で示されるフッ素化アルキルフルオロリン酸アニオンを対イオンとして有するスルホニウム塩の製造方法。 - アリール化合物(A)が、置換されていてもよい少なくとも1個のアリールチオ基を有するものである、請求項1の製造方法。
- 式(1)中、R1およびR2が、置換されていてもよいフェニル基である、請求項1または2の製造方法。
- フッ素化アルキルフルオロリン酸(C)が、H[(CF3CF2)3PF3]、H[(CF3CF2CF2)3PF3]、H[((CF3)2CFCF2)3PF3]及びH[((CF3)2CFCF2)2PF4]よりなる群より選ばれるものである、請求項1ないし3のいずれかの製造方法。
- 脱水剤(D)が無水酢酸である、請求項1ないし4のいずれかの製造方法。
- フッ素化アルキルフルオロリン酸(C)が、該アリール化合物(A)、該スルホキシド化合物(B)、該脱水剤(D)及び溶媒の少なくとも1種を含んでなる反応系に、アルカリ金属またはアルカリ土類金属のフッ素化アルキルフルオロリン酸塩と硫酸とを添加することによって該反応系内で発生させられるものである、請求項1ないし5のいずれかの製造方法。
- 該フッ素化アルキルフルオロリン酸塩が、Li、K及びNaよりなる群より選ばれる少なくとも1種のアルカリ金属のフッ素化アルキルフルオロリン酸塩である、請求項6の製造方法。
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