JP2008133262A - アルコキシカルボニルフルオロアルカンスルホン酸塩類の製造方法 - Google Patents
アルコキシカルボニルフルオロアルカンスルホン酸塩類の製造方法 Download PDFInfo
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- JP2008133262A JP2008133262A JP2007271988A JP2007271988A JP2008133262A JP 2008133262 A JP2008133262 A JP 2008133262A JP 2007271988 A JP2007271988 A JP 2007271988A JP 2007271988 A JP2007271988 A JP 2007271988A JP 2008133262 A JP2008133262 A JP 2008133262A
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- 238000000034 method Methods 0.000 title claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 55
- 150000003839 salts Chemical class 0.000 claims abstract description 41
- 238000004519 manufacturing process Methods 0.000 claims abstract description 20
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 15
- 150000002148 esters Chemical class 0.000 claims abstract description 14
- -1 sulfonium cation Chemical class 0.000 claims description 172
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 150000001768 cations Chemical class 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- 238000005886 esterification reaction Methods 0.000 claims description 10
- 150000002430 hydrocarbons Chemical group 0.000 claims description 10
- 239000007800 oxidant agent Substances 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 230000032050 esterification Effects 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000000468 ketone group Chemical group 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims description 4
- 229930194542 Keto Natural products 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910021645 metal ion Inorganic materials 0.000 claims description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 44
- 230000005855 radiation Effects 0.000 abstract description 5
- 239000007858 starting material Substances 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 abstract description 4
- 239000000543 intermediate Substances 0.000 abstract description 3
- 238000000206 photolithography Methods 0.000 abstract description 3
- 239000004065 semiconductor Substances 0.000 abstract description 3
- 229920002120 photoresistant polymer Polymers 0.000 abstract description 2
- 239000002699 waste material Substances 0.000 abstract description 2
- 230000003321 amplification Effects 0.000 abstract 1
- 238000003199 nucleic acid amplification method Methods 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 150000002500 ions Chemical class 0.000 description 23
- 239000003960 organic solvent Substances 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000007529 inorganic bases Chemical class 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000003158 alcohol group Chemical group 0.000 description 7
- 238000005342 ion exchange Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000007810 chemical reaction solvent Substances 0.000 description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- LYJKGSALBRSKNL-UHFFFAOYSA-N bromodifluoroacetyl chloride Chemical compound FC(F)(Br)C(Cl)=O LYJKGSALBRSKNL-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 4
- 150000004673 fluoride salts Chemical class 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- 150000003624 transition metals Chemical class 0.000 description 4
- ZFEAYIKULRXTAR-UHFFFAOYSA-M triphenylsulfanium;chloride Chemical compound [Cl-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 ZFEAYIKULRXTAR-UHFFFAOYSA-M 0.000 description 4
- QCBDDIHRXCJILE-UHFFFAOYSA-N (2-bromo-2,2-difluoroacetyl) 2-bromo-2,2-difluoroacetate Chemical compound FC(F)(Br)C(=O)OC(=O)C(F)(F)Br QCBDDIHRXCJILE-UHFFFAOYSA-N 0.000 description 3
- SKPCYTSLRGWTQH-UHFFFAOYSA-N 1-adamantylmethyl 2-bromo-2,2-difluoroacetate Chemical compound C1C(C2)CC3CC2CC1(COC(=O)C(F)(Br)F)C3 SKPCYTSLRGWTQH-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LZCMQBRCQWOSHZ-UHFFFAOYSA-N 2-bromo-2,2-difluoroacetic acid Chemical compound OC(=O)C(F)(F)Br LZCMQBRCQWOSHZ-UHFFFAOYSA-N 0.000 description 3
- LYEISECDEKRQHL-UHFFFAOYSA-N 2-bromo-2,3,3,3-tetrafluoropropanoyl chloride Chemical compound FC(F)(F)C(F)(Br)C(Cl)=O LYEISECDEKRQHL-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- 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 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000001459 lithography Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- YFSUTJLHUFNCNZ-UHFFFAOYSA-N perfluorooctane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- WZNFNNOGQKRPEL-UHFFFAOYSA-N (2-bromo-2,3,3,3-tetrafluoropropanoyl) 2-bromo-2,3,3,3-tetrafluoropropanoate Chemical compound FC(F)(F)C(F)(Br)C(=O)OC(=O)C(F)(Br)C(F)(F)F WZNFNNOGQKRPEL-UHFFFAOYSA-N 0.000 description 2
- VBJIFLOSOQGDRZ-UHFFFAOYSA-N (2-chloro-2,2-difluoroacetyl) 2-chloro-2,2-difluoroacetate Chemical compound FC(F)(Cl)C(=O)OC(=O)C(F)(F)Cl VBJIFLOSOQGDRZ-UHFFFAOYSA-N 0.000 description 2
- PLZIELSZQLNLPD-UHFFFAOYSA-N 2,3,3,3-tetrafluoro-2-iodopropanoic acid Chemical compound OC(=O)C(F)(I)C(F)(F)F PLZIELSZQLNLPD-UHFFFAOYSA-N 0.000 description 2
- QUWQIQACQOVGDT-UHFFFAOYSA-N 2-bromo-2,3,3,3-tetrafluoropropanoic acid Chemical compound OC(=O)C(F)(Br)C(F)(F)F QUWQIQACQOVGDT-UHFFFAOYSA-N 0.000 description 2
- SMCNZLDHTZESTK-UHFFFAOYSA-N 2-chloro-1,1,1,2-tetrafluoropropane Chemical compound CC(F)(Cl)C(F)(F)F SMCNZLDHTZESTK-UHFFFAOYSA-N 0.000 description 2
- OAWAZQITIZDJRB-UHFFFAOYSA-N 2-chloro-2,2-difluoroacetic acid Chemical compound OC(=O)C(F)(F)Cl OAWAZQITIZDJRB-UHFFFAOYSA-N 0.000 description 2
- AZPWOLJQERBBBM-UHFFFAOYSA-N 2-chloro-2,2-difluoroacetyl chloride Chemical compound FC(F)(Cl)C(Cl)=O AZPWOLJQERBBBM-UHFFFAOYSA-N 0.000 description 2
- UNATUTDSNCSLAP-UHFFFAOYSA-N 2-chloro-2,3,3,3-tetrafluoropropanoyl chloride Chemical compound FC(F)(F)C(F)(Cl)C(Cl)=O UNATUTDSNCSLAP-UHFFFAOYSA-N 0.000 description 2
- QFABNUVNDKOIEH-UHFFFAOYSA-N 2-methylsulfanylcyclohexan-1-one Chemical compound CSC1CCCCC1=O QFABNUVNDKOIEH-UHFFFAOYSA-N 0.000 description 2
- QXMXPBDJGXQNPD-UHFFFAOYSA-N 3,3,3-trifluoro-2-iodo-2-(trifluoromethyl)propanoic acid Chemical compound OC(=O)C(I)(C(F)(F)F)C(F)(F)F QXMXPBDJGXQNPD-UHFFFAOYSA-N 0.000 description 2
- XRIYEOBBIBEEMW-UHFFFAOYSA-N 3-bicyclo[2.2.1]heptanyl-methyl-(2-oxocyclohexyl)sulfanium Chemical compound C1C(C2)CCC2C1[S+](C)C1CCCCC1=O XRIYEOBBIBEEMW-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- HTRUNICFOWYISW-UHFFFAOYSA-N dimethyl-(2-oxocyclohexyl)sulfanium Chemical compound C[S+](C)C1CCCCC1=O HTRUNICFOWYISW-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 2
- 229910052808 lithium carbonate Inorganic materials 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229960003975 potassium Drugs 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- HEZHYQDYRPUXNJ-UHFFFAOYSA-L potassium dithionite Chemical compound [K+].[K+].[O-]S(=O)S([O-])=O HEZHYQDYRPUXNJ-UHFFFAOYSA-L 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 2
- IDXMRTSGPHLLSP-UHFFFAOYSA-M potassium;2-bromo-2,2-difluoroacetate Chemical compound [K+].[O-]C(=O)C(F)(F)Br IDXMRTSGPHLLSP-UHFFFAOYSA-M 0.000 description 2
- WHDIYMPUKRQQEC-UHFFFAOYSA-M potassium;2-bromo-2,3,3,3-tetrafluoropropanoate Chemical compound [K+].[O-]C(=O)C(F)(Br)C(F)(F)F WHDIYMPUKRQQEC-UHFFFAOYSA-M 0.000 description 2
- PYQRMDHLMKGZJP-UHFFFAOYSA-M potassium;2-chloro-2,2-difluoroacetate Chemical compound [K+].[O-]C(=O)C(F)(F)Cl PYQRMDHLMKGZJP-UHFFFAOYSA-M 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 238000004904 shortening Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 2
- SHSMOFBEEONVEW-UHFFFAOYSA-M sodium;1,1-difluoro-2-methoxy-2-oxoethanesulfonate Chemical compound [Na+].COC(=O)C(F)(F)S([O-])(=O)=O SHSMOFBEEONVEW-UHFFFAOYSA-M 0.000 description 2
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- PXWYRCBSNGDJQZ-UHFFFAOYSA-N 3,3,3-trifluoro-2-iodo-2-(trifluoromethyl)propanoyl chloride Chemical compound FC(F)(F)C(I)(C(Cl)=O)C(F)(F)F PXWYRCBSNGDJQZ-UHFFFAOYSA-N 0.000 description 1
- PTJCCXUALFLYSW-UHFFFAOYSA-N 3,3,3-trifluoro-2-iodo-2-(trifluoromethyl)propanoyl fluoride Chemical compound FC(=O)C(I)(C(F)(F)F)C(F)(F)F PTJCCXUALFLYSW-UHFFFAOYSA-N 0.000 description 1
- JIJDMZLZTMMIQZ-UHFFFAOYSA-N 3,3,3-trifluoro-2-iodo-2-(trifluoromethyl)propanoyl iodide Chemical compound FC(F)(F)C(I)(C(I)=O)C(F)(F)F JIJDMZLZTMMIQZ-UHFFFAOYSA-N 0.000 description 1
- KSNKQSPJFRQSEI-UHFFFAOYSA-N 3,3,3-trifluoropropanoic acid Chemical compound OC(=O)CC(F)(F)F KSNKQSPJFRQSEI-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- BCZXFFBUYPCTSJ-UHFFFAOYSA-L Calcium propionate Chemical compound [Ca+2].CCC([O-])=O.CCC([O-])=O BCZXFFBUYPCTSJ-UHFFFAOYSA-L 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910020366 ClO 4 Inorganic materials 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
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- JKZRQYDDXKVCHF-UHFFFAOYSA-N O.O.[W+6].[Na+] Chemical compound O.O.[W+6].[Na+] JKZRQYDDXKVCHF-UHFFFAOYSA-N 0.000 description 1
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- 229910018286 SbF 6 Inorganic materials 0.000 description 1
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- 239000005708 Sodium hypochlorite Substances 0.000 description 1
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- LTFRXHHSJQFQPU-UHFFFAOYSA-N [2-bromo-3,3,3-trifluoro-2-(trifluoromethyl)propanoyl] 2-bromo-3,3,3-trifluoro-2-(trifluoromethyl)propanoate Chemical compound FC(F)(F)C(Br)(C(F)(F)F)C(=O)OC(=O)C(Br)(C(F)(F)F)C(F)(F)F LTFRXHHSJQFQPU-UHFFFAOYSA-N 0.000 description 1
- KSLSXSAGGOWPBY-UHFFFAOYSA-N [2-chloro-3,3,3-trifluoro-2-(trifluoromethyl)propanoyl] 2-chloro-3,3,3-trifluoro-2-(trifluoromethyl)propanoate Chemical compound FC(F)(F)C(Cl)(C(F)(F)F)C(=O)OC(=O)C(Cl)(C(F)(F)F)C(F)(F)F KSLSXSAGGOWPBY-UHFFFAOYSA-N 0.000 description 1
- FCMLFBCCCKHRED-UHFFFAOYSA-N [3,3,3-trifluoro-2-(trifluoromethyl)propanoyl] 3,3,3-trifluoro-2-(trifluoromethyl)propanoate Chemical compound FC(F)(F)C(C(F)(F)F)C(=O)OC(=O)C(C(F)(F)F)C(F)(F)F FCMLFBCCCKHRED-UHFFFAOYSA-N 0.000 description 1
- OUGQXRWUVHFNLK-UHFFFAOYSA-N [Ca].OC(=O)C(Br)(C(F)(F)F)C(F)(F)F Chemical compound [Ca].OC(=O)C(Br)(C(F)(F)F)C(F)(F)F OUGQXRWUVHFNLK-UHFFFAOYSA-N 0.000 description 1
- HVCHCZYBQLOVGX-UHFFFAOYSA-N [Ca].OC(=O)C(I)(C(F)(F)F)C(F)(F)F Chemical compound [Ca].OC(=O)C(I)(C(F)(F)F)C(F)(F)F HVCHCZYBQLOVGX-UHFFFAOYSA-N 0.000 description 1
- XRZCZQUCDBWELQ-UHFFFAOYSA-L [Li+].[Li+].[O-]S(=O)S([O-])=O Chemical compound [Li+].[Li+].[O-]S(=O)S([O-])=O XRZCZQUCDBWELQ-UHFFFAOYSA-L 0.000 description 1
- RCTSGVBRFSSKSO-UHFFFAOYSA-N [Mg].OC(=O)C(Br)(C(F)(F)F)C(F)(F)F Chemical compound [Mg].OC(=O)C(Br)(C(F)(F)F)C(F)(F)F RCTSGVBRFSSKSO-UHFFFAOYSA-N 0.000 description 1
- ZIGXDNIMGAOLBQ-UHFFFAOYSA-N [Mg].OC(=O)C(Cl)(C(F)(F)F)C(F)(F)F Chemical compound [Mg].OC(=O)C(Cl)(C(F)(F)F)C(F)(F)F ZIGXDNIMGAOLBQ-UHFFFAOYSA-N 0.000 description 1
- RFAVYPPLCZNNEW-UHFFFAOYSA-N [Mg].OC(=O)C(F)(I)C(F)(F)F Chemical compound [Mg].OC(=O)C(F)(I)C(F)(F)F RFAVYPPLCZNNEW-UHFFFAOYSA-N 0.000 description 1
- FCMYSEXCLRFWBP-UHFFFAOYSA-N [NH4+].[NH4+].[O-]S(=O)S([O-])=O Chemical compound [NH4+].[NH4+].[O-]S(=O)S([O-])=O FCMYSEXCLRFWBP-UHFFFAOYSA-N 0.000 description 1
- ZBIKORITPGTTGI-UHFFFAOYSA-N [acetyloxy(phenyl)-$l^{3}-iodanyl] acetate Chemical compound CC(=O)OI(OC(C)=O)C1=CC=CC=C1 ZBIKORITPGTTGI-UHFFFAOYSA-N 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000010331 calcium propionate Nutrition 0.000 description 1
- GORZAQZCTBIJRI-UHFFFAOYSA-L calcium;2,2-difluoro-2-iodoacetate Chemical compound [Ca+2].[O-]C(=O)C(F)(F)I.[O-]C(=O)C(F)(F)I GORZAQZCTBIJRI-UHFFFAOYSA-L 0.000 description 1
- LRUQAKDHRHSXON-UHFFFAOYSA-L calcium;2,3,3,3-tetrafluoro-2-iodopropanoate Chemical compound [Ca+2].[O-]C(=O)C(F)(I)C(F)(F)F.[O-]C(=O)C(F)(I)C(F)(F)F LRUQAKDHRHSXON-UHFFFAOYSA-L 0.000 description 1
- FXTDIAHJMBTTSO-UHFFFAOYSA-L calcium;2-bromo-2,2-difluoroacetate Chemical compound [Ca+2].[O-]C(=O)C(F)(F)Br.[O-]C(=O)C(F)(F)Br FXTDIAHJMBTTSO-UHFFFAOYSA-L 0.000 description 1
- SIUKEFONIKGCRW-UHFFFAOYSA-L calcium;2-chloro-2,2-difluoroacetate Chemical compound [Ca+2].[O-]C(=O)C(F)(F)Cl.[O-]C(=O)C(F)(F)Cl SIUKEFONIKGCRW-UHFFFAOYSA-L 0.000 description 1
- KHRQCUDDNVHGAY-UHFFFAOYSA-L calcium;2-chloro-3,3,3-trifluoro-2-(trifluoromethyl)propanoate Chemical compound [Ca+2].[O-]C(=O)C(Cl)(C(F)(F)F)C(F)(F)F.[O-]C(=O)C(Cl)(C(F)(F)F)C(F)(F)F KHRQCUDDNVHGAY-UHFFFAOYSA-L 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- PBWZKZYHONABLN-UHFFFAOYSA-N difluoroacetic acid Chemical class OC(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- JZBWUTVDIDNCMW-UHFFFAOYSA-L dipotassium;oxido sulfate Chemical compound [K+].[K+].[O-]OS([O-])(=O)=O JZBWUTVDIDNCMW-UHFFFAOYSA-L 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 238000000671 immersion lithography Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- KSRHWBLHVZJTKV-UHFFFAOYSA-N iodobenzene dichloride Chemical compound ClI(Cl)C1=CC=CC=C1 KSRHWBLHVZJTKV-UHFFFAOYSA-N 0.000 description 1
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229910000032 lithium hydrogen carbonate Inorganic materials 0.000 description 1
- HQRPHMAXFVUBJX-UHFFFAOYSA-M lithium;hydrogen carbonate Chemical compound [Li+].OC([O-])=O HQRPHMAXFVUBJX-UHFFFAOYSA-M 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- DSMYTAFLKXMNDZ-UHFFFAOYSA-L magnesium;2,2-difluoro-2-iodoacetate Chemical compound [Mg+2].[O-]C(=O)C(F)(F)I.[O-]C(=O)C(F)(F)I DSMYTAFLKXMNDZ-UHFFFAOYSA-L 0.000 description 1
- ZPJVVQJKOMYJTE-UHFFFAOYSA-L magnesium;2-bromo-2,3,3,3-tetrafluoropropanoate Chemical compound [Mg+2].[O-]C(=O)C(F)(Br)C(F)(F)F.[O-]C(=O)C(F)(Br)C(F)(F)F ZPJVVQJKOMYJTE-UHFFFAOYSA-L 0.000 description 1
- VQJXAYDKZFFGBP-UHFFFAOYSA-L magnesium;2-chloro-2,2-difluoroacetate Chemical compound [Mg+2].[O-]C(=O)C(F)(F)Cl.[O-]C(=O)C(F)(F)Cl VQJXAYDKZFFGBP-UHFFFAOYSA-L 0.000 description 1
- GHPUXWBQXGVVBW-UHFFFAOYSA-L magnesium;2-chloro-2,3,3,3-tetrafluoropropanoate Chemical compound [Mg+2].[O-]C(=O)C(F)(Cl)C(F)(F)F.[O-]C(=O)C(F)(Cl)C(F)(F)F GHPUXWBQXGVVBW-UHFFFAOYSA-L 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 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
- CSSYKHYGURSRAZ-UHFFFAOYSA-N methyl 2,2-difluoroacetate Chemical compound COC(=O)C(F)F CSSYKHYGURSRAZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical group C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910000487 osmium oxide Inorganic materials 0.000 description 1
- KBQNBXKLWZDDMP-UHFFFAOYSA-N oxathietane 2,2-dioxide Chemical compound O=S1(=O)CCO1 KBQNBXKLWZDDMP-UHFFFAOYSA-N 0.000 description 1
- JIWAALDUIFCBLV-UHFFFAOYSA-N oxoosmium Chemical compound [Os]=O JIWAALDUIFCBLV-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- VNDQDKJEBFEYHX-UHFFFAOYSA-M potassium;2-chloro-2,3,3,3-tetrafluoropropanoate Chemical compound [K+].[O-]C(=O)C(F)(Cl)C(F)(F)F VNDQDKJEBFEYHX-UHFFFAOYSA-M 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- BNKKDSJOMZEKDK-UHFFFAOYSA-M sodium;2,2-difluoro-2-iodoacetate Chemical compound [Na+].[O-]C(=O)C(F)(F)I BNKKDSJOMZEKDK-UHFFFAOYSA-M 0.000 description 1
- HSTXUSBJDADVNN-UHFFFAOYSA-M sodium;2,3,3,3-tetrafluoro-2-iodopropanoate Chemical compound [Na+].[O-]C(=O)C(F)(I)C(F)(F)F HSTXUSBJDADVNN-UHFFFAOYSA-M 0.000 description 1
- OLRKQYZZMBOCQN-UHFFFAOYSA-M sodium;2-bromo-3,3,3-trifluoro-2-(trifluoromethyl)propanoate Chemical compound [Na+].[O-]C(=O)C(Br)(C(F)(F)F)C(F)(F)F OLRKQYZZMBOCQN-UHFFFAOYSA-M 0.000 description 1
- WRUGUVACAUAMPJ-UHFFFAOYSA-M sodium;2-chloro-2,3,3,3-tetrafluoropropanoate Chemical compound [Na+].[O-]C(=O)C(F)(Cl)C(F)(F)F WRUGUVACAUAMPJ-UHFFFAOYSA-M 0.000 description 1
- CTEGORMZMNTCFV-UHFFFAOYSA-M sodium;3,3,3-trifluoropropanoate Chemical compound [Na+].[O-]C(=O)CC(F)(F)F CTEGORMZMNTCFV-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- MBAHHEXPHSAXQO-UHFFFAOYSA-N tris(2-acetyloxyphenyl)sulfanium Chemical compound CC(=O)OC1=CC=CC=C1[S+](C=1C(=CC=CC=1)OC(C)=O)C1=CC=CC=C1OC(C)=O MBAHHEXPHSAXQO-UHFFFAOYSA-N 0.000 description 1
- ZHHRYQXXYWVTPZ-UHFFFAOYSA-N tris(2-chlorophenyl)sulfanium Chemical compound ClC1=CC=CC=C1[S+](C=1C(=CC=CC=1)Cl)C1=CC=CC=C1Cl ZHHRYQXXYWVTPZ-UHFFFAOYSA-N 0.000 description 1
- NFEAPFABNXPJMP-UHFFFAOYSA-N tris(2-fluorophenyl)sulfanium Chemical compound FC1=CC=CC=C1[S+](C=1C(=CC=CC=1)F)C1=CC=CC=C1F NFEAPFABNXPJMP-UHFFFAOYSA-N 0.000 description 1
- PUNLMWKEFPBDHE-UHFFFAOYSA-O tris(2-hydroxyphenyl)sulfanium Chemical compound OC1=CC=CC=C1[S+](C=1C(=CC=CC=1)O)C1=CC=CC=C1O PUNLMWKEFPBDHE-UHFFFAOYSA-O 0.000 description 1
- YWTDARPOMXBETA-UHFFFAOYSA-N tris(2-methoxyphenyl)sulfanium Chemical compound COC1=CC=CC=C1[S+](C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC YWTDARPOMXBETA-UHFFFAOYSA-N 0.000 description 1
- FACJZVSKOIMXOB-UHFFFAOYSA-N tris(2-octylphenyl)sulfanium Chemical compound CCCCCCCCC1=CC=CC=C1[S+](C=1C(=CC=CC=1)CCCCCCCC)C1=CC=CC=C1CCCCCCCC FACJZVSKOIMXOB-UHFFFAOYSA-N 0.000 description 1
- UTCOSYZEYALTGJ-UHFFFAOYSA-N tris(2-tert-butylphenyl)sulfanium Chemical compound CC(C)(C)C1=CC=CC=C1[S+](C=1C(=CC=CC=1)C(C)(C)C)C1=CC=CC=C1C(C)(C)C UTCOSYZEYALTGJ-UHFFFAOYSA-N 0.000 description 1
- RTQVAMOEFSZTDV-UHFFFAOYSA-N tris[2-(trifluoromethyl)phenyl]sulfanium Chemical compound FC(F)(F)C1=CC=CC=C1[S+](C=1C(=CC=CC=1)C(F)(F)F)C1=CC=CC=C1C(F)(F)F RTQVAMOEFSZTDV-UHFFFAOYSA-N 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- CAAIULQYGCAMCD-UHFFFAOYSA-L zinc;hydroxymethanesulfinate Chemical compound [Zn+2].OCS([O-])=O.OCS([O-])=O CAAIULQYGCAMCD-UHFFFAOYSA-L 0.000 description 1
Images
Abstract
【解決手段】安価で入手容易なハロフルオロアルカン酸誘導体から誘導されるハロフルオロアルカン酸エステル類を出発原料に用いて、これをスルフィン化(第1工程)した後、酸化(第2工程)することによって目的とするアルコキシカルボニルフルオロアルカンスルホン酸塩を得る。さらにはこれを塩交換(第3工程)することによって、光酸発生剤として有用なアルコキシカルボニルフルオロアルカンスルホン酸オニウム塩を得る。
【選択図】図1
Description
(特許文献1および特許文献4)。
第1工程:一般式[2]で示されるハロフルオロアルカン酸エステル類
第2工程:一般式[3]で示されるアルコキシカルボニルフルオロアルカンスルフィン酸塩類を酸化剤と反応させ、一般式[1]で示されるアルコキシカルボニルフルオロアルカンスルホン酸塩類を得る工程。
(一般式[1]中、Rは炭素数1〜25の直鎖、分岐鎖あるいは環状のアルキル基(ここで該アルキル基の水素原子の一部または全てはフッ素もしくはヒドロキシル基で置換されていても良く、該アルキル基を構成する炭素上の2つの水素原子は1つの酸素原子で置換されケト基となっていても良い)、炭素数2〜25の直鎖、分岐鎖あるいは環状のアルケニル基(ここで該アルケニル基の水素原子の一部または全てはフッ素もしくはヒドロキシル基で置換されていても良く、該アルケニル基中のメチレン炭素上の2つの水素原子は1つの酸素原子で置換されケト基となっていても良い。)R1およびR2は、それぞれ独立にフッ素原子もしくは炭素数1〜6の直鎖、分岐鎖あるいは環状のパーフルオロアルキル基を示す。Mn+は対カチオンを示し、nは正の整数を示す。一般式[2]中、Xは塩素原子、臭素原子もしくはヨウ素原子を示し、R、R1およびR2は一般式[1]に同じ。一般式[3]中、R、R1、R2、Mn+およびnは一般式[1]に同じ。)
〔発明2〕次の3工程によりなる、一般式[4]で示されるアルコキシカルボニルフルオロアルカンスルホン酸オニウム塩類
第1工程:一般式[2]で示されるハロフルオロアルカン酸エステル類をスルフィン化剤の存在下で反応させ、一般式[3]で示されるアルコキシカルボニルフルオロアルカンスルフィン酸塩類を得る工程。
第2工程:一般式[3]で示されるアルコキシカルボニルフルオロアルカンスルフィン酸塩類を酸化剤と反応させ、一般式[1]で示されるアルコキシカルボニルフルオロアルカンスルホン酸塩類を得る工程。
第3工程:一般式[1]で示されるアルコキシカルボニルフルオロアルカンスルホン酸塩類を、一般式[5]で示される一価のオニウム塩
〔一般式[4]中、R、R1、R2は一般式[1]と同義であり、Q+は、下記一般式[6]で表されるスルホニウムカチオン
〔発明3〕一般式[2]で示されるハロフルオロアルカン酸エステル類が、一般式[8]、一般式[9]もしくは一般式[10]で示されるハロフルオロ酢酸誘導体
(一般式[8]中、Zはヒドロキシル基、フッ素、塩素、臭素、ヨウ素を表す。R1およびR2は一般式[1]に同じ。Xは一般式[2]に同じ。一般式[9]中、Tp+は金属イオンの対カチオンを示し、pは整数を示す。R1およびR2は一般式[1]に同じ。Xは一般式[2]に同じ。一般式[10]中、R1およびR2は一般式[1]に同じ。Xは一般式[2]に同じ。)である。
200mLの3つ口フラスコに1−アダマンタンメタノール 4.76g(31.8mmol,1.11当量)とジエチルエーテル 55gを入れた後、攪拌して懸濁させ、その中にブロモジフルオロ酢酸クロリド 6.15g(28.6mmol,1.0当量)を添加した。この懸濁液を氷浴を用いて0℃まで冷却し、次いでトリエチルアミン 5.78g(57.2mmol,2.0当量)をゆっくり滴下した。この反応液を攪拌しながら室温になるまで放置し、さらに室温で1時間攪拌した。その後、水 50gを加えて反応液を洗浄し、得られた有機層を飽和炭酸水素ナトリウム 50g、飽和食塩水50g、水50gの順で洗浄した。次いで硫酸マグネシウムを用いて乾燥した後、溶媒を留去し、目的とするブロモジフルオロ酢酸アダマンタン−1−イルメチルを8.78g(収率95%,純度100%)得た。
200mLの3つ口フラスコ中、ブロモジフルオロ酢酸アダマンタン−1−イルメチル9.55g(29.6mmol,1.0当量)をアセトニトリル 40gに溶解し、炭酸水素ナトリウム 4.96g(59.0mmol,2.0当量)、亜ジチオン酸ナトリウム 7.72g(44.3mmol,1.5当量)を加え、次いで水 40gを加えて攪拌した。反応系内を窒素雰囲気とし、反応液を50℃まで昇温して8時間攪拌した。反応後、二層分離している反応液のうち、有機層を回収し、残った水層をアセトニトリル 50gで抽出した。有機層を合わせ、溶媒を留去し、残渣に対してジイソプロピルエーテル 50gを加えて懸濁させ、30分室温で攪拌した。この液を濾過し、濾液から溶媒を留去し、目的とする(アダマンタン−1−イルメチル)オキシカルボニルジフルオロメタンスルフィン酸ナトリウムを含有する固体 12.4gを得た。NMRを用いてこの固体中の(アダマンタン−1−イルメチル)オキシカルボニルジフルオロメタンスルフィン酸ナトリウムの含量を分析したところ、重量換算で6.36g(収率65%)含有していると測定された。
200mLの3つ口フラスコ中、第1工程で得られた(アダマンタン−1−イルメチル)オキシカルボニルジフルオロメタンスルフィン酸ナトリウムを含有する固体12.4g(内、(アダマンタン−1−イルメチル)オキシカルボニルジフルオロメタンスルフィン酸ナトリウムとして6.36g(19.3mmol,1.0当量))を水 120mlに溶解し、30%濃度の過酸化水素水 5.03g(44.4mmol,2.3当量)とタングステン(VI)酸ナトリウム二水和物15mg(0.045mmol,0.0024当量)を加え、室温で1.5時間攪拌した。反応液から水を留去し、乾燥して、目的とする(アダマンタン−1−イルメチル)オキシカルボニルジフルオロメタンスルホン酸ナトリウムを含有する固体 9.84gを得た。NMRを用いてこの固体中の(アダマンタン−1−イルメチル)オキシカルボニルジフルオロメタンスルホン酸ナトリウムの含量を分析したところ、重量換算で6.49g(収率97%)含有していると測定された。
200mLの3つ口フラスコ中、第2工程で得られた(アダマンタン−1−イルメチル)オキシカルボニルジフルオロメタンスルホン酸ナトリウムを含有する固体8.86g(内、(アダマンタン−1−イルメチル)オキシカルボニルジフルオロメタンスルホン酸ナトリウムとして5.85g(16.9mmol,1.0当量))を水 83gに加え、攪拌して懸濁させ、80℃まで昇温した。80℃で均一な溶液となった。この中に、トリフェニルスルホニウムクロリド 5.51g(18.43mmol,1.1当量)と水 60gからなる水溶液を加えたところ、ただちに白色固体が沈降した。固体を濾過し、漏斗上の固体を80℃の水 50gとジイソプロピルエーテル 30gでかけ洗いした後乾燥し、目的とするトリフェニルスルホニウム (アダマンタン−1−イルメチル)オキシカルボニルジフルオロメタンスルホナートを9.91g(収率100%、純度97%)得た。 本工程で得られた廃水からはいずれもフッ素イオン(F−)は検出されなかった。
2Lの3つ口フラスコ中、水 500gに炭酸水素ナトリウム 25.2g(300mmol,3.0当量)を溶解させ、室温で2−(フルオロスルホニル)ジフルオロ酢酸メチル19.2g(100mmol,1.0当量)を滴下し、室温のまま2時間攪拌した。その後、水を留去して、目的とするメトキシカルボニルジフルオロメタンスルホン酸ナトリウムを含有する固体 46.5gを得た。
反応終了後の反応液からフッ素イオン(F−)が3500ppm検出された。この水溶液からガラス製フラスコを用いて水を留去したため、ガラス製フラスコは白く失透してしまった。
Claims (3)
- 次の2工程によりなる、一般式[1]で示されるアルコキシカルボニルフルオロアルカンスルホン酸塩類
第1工程:一般式[2]で示されるハロフルオロアルカン酸エステル類
第2工程:一般式[3]で示されるアルコキシカルボニルフルオロアルカンスルフィン酸塩類を酸化剤と反応させ、一般式[1]で示されるアルコキシカルボニルフルオロアルカンスルホン酸塩類を得る工程。
(一般式[1]中、Rは炭素数1〜25の直鎖、分岐鎖あるいは環状のアルキル基(ここで該アルキル基の水素原子の一部または全てはフッ素もしくはヒドロキシル基で置換されていても良く、該アルキル基を構成する炭素上の2つの水素原子は1つの酸素原子で置換されケト基となっていても良い)、炭素数2〜25の直鎖、分岐鎖あるいは環状のアルケニル基(ここで該アルケニル基の水素原子の一部または全てはフッ素もしくはヒドロキシル基で置換されていても良く、該アルケニル基中のメチレン炭素上の2つの水素原子は1つの酸素原子で置換されケト基となっていても良い。)R1およびR2は、それぞれ独立にフッ素原子もしくは炭素数1〜6の直鎖、分岐鎖あるいは環状のパーフルオロアルキル基を示す。Mn+は対カチオンを示し、nは正の整数を示す。一般式[2]中、Xは塩素原子、臭素原子もしくはヨウ素原子を示し、R、R1およびR2は一般式[1]に同じ。一般式[3]中、R、R1、R2、Mn+およびnは一般式[1]に同じ。) - 次の3工程によりなる、一般式[4]で示されるアルコキシカルボニルフルオロアルカンスルホン酸オニウム塩類
第1工程:一般式[2]で示されるハロフルオロアルカン酸エステル類をスルフィン化剤の存在下で反応させ、一般式[3]で示されるアルコキシカルボニルフルオロアルカンスルフィン酸塩類を得る工程。
第2工程:一般式[3]で示されるアルコキシカルボニルフルオロアルカンスルフィン酸塩類を酸化剤と反応させ、一般式[1]で示されるアルコキシカルボニルフルオロアルカンスルホン酸塩類を得る工程。
第3工程:一般式[1]で示されるアルコキシカルボニルフルオロアルカンスルホン酸塩類を、一般式[5]で示される一価のオニウム塩
〔一般式[4]中、R、R1、R2は一般式[1]と同義であり、Q+は、下記一般式[6]で表されるスルホニウムカチオン
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Free format text: JAPANESE INTERMEDIATE CODE: R250 |