JP7054096B2 - フッ素化カーボネート誘導体の製造方法 - Google Patents
フッ素化カーボネート誘導体の製造方法 Download PDFInfo
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- JP7054096B2 JP7054096B2 JP2019519163A JP2019519163A JP7054096B2 JP 7054096 B2 JP7054096 B2 JP 7054096B2 JP 2019519163 A JP2019519163 A JP 2019519163A JP 2019519163 A JP2019519163 A JP 2019519163A JP 7054096 B2 JP7054096 B2 JP 7054096B2
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- fluorinated
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- 150000004649 carbonic acid derivatives Chemical class 0.000 title claims description 55
- 238000004519 manufacturing process Methods 0.000 title claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 136
- 125000001153 fluoro group Chemical group F* 0.000 claims description 46
- 150000008282 halocarbons Chemical class 0.000 claims description 46
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 42
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 42
- 229910052731 fluorine Inorganic materials 0.000 claims description 41
- 230000000269 nucleophilic effect Effects 0.000 claims description 37
- 229910052760 oxygen Inorganic materials 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 33
- 239000001301 oxygen Substances 0.000 claims description 33
- 239000002585 base Substances 0.000 claims description 28
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 27
- 239000011737 fluorine Substances 0.000 claims description 27
- -1 alkali metal hydrogen carbonate Chemical class 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 25
- 125000000524 functional group Chemical group 0.000 claims description 23
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 22
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 21
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 21
- 125000004407 fluoroaryl group Chemical group 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 150000007529 inorganic bases Chemical class 0.000 claims description 13
- 239000004417 polycarbonate Substances 0.000 claims description 11
- 229920000515 polycarbonate Polymers 0.000 claims description 11
- 125000000962 organic group Chemical group 0.000 claims description 10
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 9
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 9
- 230000001678 irradiating effect Effects 0.000 claims description 8
- 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 claims description 7
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 7
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 6
- 150000005676 cyclic carbonates Chemical class 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 150000002430 hydrocarbons Chemical class 0.000 claims description 6
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 claims description 3
- FVKFHMNJTHKMRX-UHFFFAOYSA-N 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine Chemical group C1CCN2CCCNC2=N1 FVKFHMNJTHKMRX-UHFFFAOYSA-N 0.000 claims description 3
- 101710118890 Photosystem II reaction center protein Ycf12 Proteins 0.000 claims description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- UURSXESKOOOTOV-UHFFFAOYSA-N dec-5-ene Chemical compound CCCCC=CCCCC UURSXESKOOOTOV-UHFFFAOYSA-N 0.000 claims description 3
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000005678 chain carbonates Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 115
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 20
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 18
- 229910052753 mercury Inorganic materials 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 16
- 229910001882 dioxygen Inorganic materials 0.000 description 16
- 239000000843 powder Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- 230000005587 bubbling Effects 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 150000007530 organic bases Chemical class 0.000 description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
- 239000007789 gas Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
- 150000001728 carbonyl compounds Chemical class 0.000 description 7
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000001819 mass spectrum Methods 0.000 description 7
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 6
- RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 4
- QGMGHALXLXKCBD-UHFFFAOYSA-N 4-amino-n-(2-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1N QGMGHALXLXKCBD-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 4
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 description 4
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- VWIHWVBGVWJAPL-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl hydrogen carbonate Chemical compound OC(=O)OC(C(F)(F)F)C(F)(F)F VWIHWVBGVWJAPL-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N tert-butyl alcohol Substances CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- BGPJLYIFDLICMR-UHFFFAOYSA-N 1,4,2,3-dioxadithiolan-5-one Chemical group O=C1OSSO1 BGPJLYIFDLICMR-UHFFFAOYSA-N 0.000 description 2
- NSKCTPBWPZPFHW-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluorodecane-1,10-diol Chemical compound OCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CO NSKCTPBWPZPFHW-UHFFFAOYSA-N 0.000 description 2
- XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 description 2
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 2
- CWIAFBQLWOMNFY-UHFFFAOYSA-N 2-[2-(1,1-difluoro-2-hydroxyethoxy)-1,1,2,2-tetrafluoroethoxy]-2,2-difluoroethanol Chemical compound OCC(F)(F)OC(F)(F)C(F)(F)OC(F)(F)CO CWIAFBQLWOMNFY-UHFFFAOYSA-N 0.000 description 2
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 2
- BEKFRNOZJSYWKZ-UHFFFAOYSA-N 4-[2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]aniline Chemical compound C1=CC(N)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(N)C=C1 BEKFRNOZJSYWKZ-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 229950005228 bromoform Drugs 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 229920006351 engineering plastic Polymers 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910001416 lithium ion Inorganic materials 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- POJPQMDDRCILHJ-UHFFFAOYSA-N 1,1,1,2,2,2-hexabromoethane Chemical compound BrC(Br)(Br)C(Br)(Br)Br POJPQMDDRCILHJ-UHFFFAOYSA-N 0.000 description 1
- QVLAWKAXOMEXPM-UHFFFAOYSA-N 1,1,1,2-tetrachloroethane Chemical compound ClCC(Cl)(Cl)Cl QVLAWKAXOMEXPM-UHFFFAOYSA-N 0.000 description 1
- JXOIMJFRROBTTE-UHFFFAOYSA-N 1,3-bis(2,3,4,5,6-pentafluorophenyl)urea Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1NC(=O)NC1=C(F)C(F)=C(F)C(F)=C1F JXOIMJFRROBTTE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- NOXLGCOSAFGMDV-UHFFFAOYSA-N 2,3,4,5,6-pentafluoroaniline Chemical compound NC1=C(F)C(F)=C(F)C(F)=C1F NOXLGCOSAFGMDV-UHFFFAOYSA-N 0.000 description 1
- PBYIIRLNRCVTMQ-UHFFFAOYSA-N 2,3,5,6-tetrafluorophenol Chemical compound OC1=C(F)C(F)=CC(F)=C1F PBYIIRLNRCVTMQ-UHFFFAOYSA-N 0.000 description 1
- CKKOVFGIBXCEIJ-UHFFFAOYSA-N 2,6-difluorophenol Chemical compound OC1=C(F)C=CC=C1F CKKOVFGIBXCEIJ-UHFFFAOYSA-N 0.000 description 1
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 1
- HDBGBTNNPRCVND-UHFFFAOYSA-N 3,3,3-trifluoropropan-1-ol Chemical compound OCCC(F)(F)F HDBGBTNNPRCVND-UHFFFAOYSA-N 0.000 description 1
- NIDAYXQNTRODPA-UHFFFAOYSA-N 3,3,3-trifluoropropyl hydrogen carbonate Chemical compound OC(=O)OCCC(F)(F)F NIDAYXQNTRODPA-UHFFFAOYSA-N 0.000 description 1
- PWRBCZZQRRPXAB-UHFFFAOYSA-N 3-chloropyridine Chemical compound ClC1=CC=CN=C1 PWRBCZZQRRPXAB-UHFFFAOYSA-N 0.000 description 1
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 1
- PVMNPAUTCMBOMO-UHFFFAOYSA-N 4-chloropyridine Chemical compound ClC1=CC=NC=C1 PVMNPAUTCMBOMO-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical class CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- JOHCVVJGGSABQY-UHFFFAOYSA-N carbon tetraiodide Chemical compound IC(I)(I)I JOHCVVJGGSABQY-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- PKAUVIXBZJUYRV-UHFFFAOYSA-N methane;hydroiodide Chemical compound C.I PKAUVIXBZJUYRV-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000005809 transesterification reaction 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
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Description
一方、本発明者は、酸素存在下、クロロホルムに光照射してホスゲンを含有する混合物を得る工程、ホスゲンを単離することなくアルコールを前記混合物と反応させる工程を具備するハロゲン化ギ酸エステルの製造方法を開発している(特許文献1)。
以下、本発明を示す。
塩素原子、臭素原子およびヨウ素原子からなる群から選択される1種以上のハロゲン原子を有するC1-4ハロゲン化炭化水素、求核性官能基を有する含フッ素化合物、および塩基を含む組成物に酸素存在下で光照射し、
前記含フッ素化合物が下式(i)で表される化合物であり且つ前記フッ素化カーボネート誘導体が下式(I)で表されるフッ素化カーボネート誘導体であるか、または、
前記含フッ素化合物が下式(ii)で表される化合物であり且つ前記フッ素化カーボネート誘導体が下式(II-1)で表される単位を含むフッ素化ポリカーボネート誘導体もしくは下式(II-2)で表されるフッ素化環状カーボネート誘導体である、フッ素化カーボネート誘導体の製造方法。
(i) RF1-A-H
(ii) H-A-RF2-A-H
(I) RF1-A-C(=O)-A-RF1
(II-1) [-A-RF2-A-C(=O)-]
Aは、O、SまたはNHであり、
RF1はフッ素原子を有する反応不活性な1価有機基であり、
RF2はフッ素原子を有する反応不活性な2価有機基である。]
(i-1) RF11CH2-A-H
(i-2) (RF12)2CH-A-H
(i-3) (RF13)3C-A-H
(I-1) RF11CH2-A-C(=O)-A-CH2-RF11
(I-2) (RF12)2CH-A-C(=O)-A-CH(RF12)2
(I-3) (RF13)3C-A-C(=O)-A-C(RF13)3
[式中、
Aは前述したものと同義を示し、
RF11は、C1-10フルオロアルキル基、C6-14フルオロアリール基、C4-14フルオロヘテロアリール基またはC2-24フルオロ(アルキルポリオキシアルキレン)基であり、2個のRF12は、それぞれ独立にC1-10アルキル基、C1-10フルオロアルキル基、C6-14アリール基、C6-14フルオロアリール基、C4-14ヘテロアリール基、C4-14フルオロヘテロアリール基、C2-24アルキルポリオキシアルキレン基またはC2-24フルオロ(アルキルポリオキシアルキレン)基であり、1個または2個のRF12が、C1-10フルオロアルキル基、C6-14フルオロアリール基、C4-14フルオロヘテロアリール基またはC2-24フルオロ(アルキルポリオキシアルキレン)基であるか、または、共同してC2-6フルオロアルキレン基または1,2-フルオロアリーレン基を形成し、
3個のRF13は、それぞれ独立にC1-10アルキル基、C1-10フルオロアルキル基、C6-14アリール基、C6-14フルオロアリール基、C4-14ヘテロアリール基、C4-14フルオロヘテロアリール基、C2-24アルキルポリオキシアルキレン基またはC2-24フルオロ(アルキルポリオキシアルキレン)基であり、1個、2個または3個のRF13が、C1-10フルオロアルキル基、C6-14フルオロアリール基、C4-14フルオロヘテロアリール基またはC2-24フルオロ(アルキルポリオキシアルキレン)基である。]
(i) RF1-A-H
(ii) H-A-RF2-A-H
(I) RF1-A-C(=O)-A-RF1
(II-1) [-A-RF2-A-C(=O)-]
(i-1) RF11CH2-A-H
(i-2) (RF12)2CH-A-H
(i-3) (RF13)3C-A-H
(I-1) RF11CH2-A-C(=O)-A-CH2-RF11
(I-2) (RF12)2CH-A-C(=O)-A-CH(RF12)2
(I-3) (RF13)3C-A-C(=O)-A-C(RF13)3
式中、Aは前述したものと同義を示し、RF11は、C1-10フルオロアルキル基、C6-14フルオロアリール基、C4-14フルオロヘテロアリール基またはC2-24フルオロ(アルキルポリオキシアルキレン)基である。
2,2,2-トリフルオロエタノールの代わりにヘキサフルオロイソプロパノール(1.04mL,10mmol)を用い、ピリジンの使用量をヘキサフルオロイソプロパノールに対して3.5倍モルに調整した以外は上記実施例1と同様にして、反応を行った。反応液を1H-NMRと19F-NMRで直接分析し、収率70%で目的化合物の炭酸ビス(ヘキサフルオロイソプロピル)の生成を確認した。なお、反応終了時、反応液は、ピリジン塩酸塩を含む上層と、目的化合物のクロロホルム溶液である下層の二層に分離した。
有機塩基としてピリジンの代わりにヘキサフルオロイソプロパノールに対して3.5倍モルのトリエチルアミン(4.9mL)を用い、反応時間を3時間とした以外は上記実施例3(1)と同様にして、反応を行った。反応後、反応液を減圧蒸留し、液体窒素にてトラップした留分を1H-NMRと19F-NMRで分析したところ、収率約20%で目的化合物である炭酸ヘキサフルオロイソプロピルが生成していることが確認された。おそらくはトリエチルアミンが反応中に分解し、ギ酸エステルなどの副生物が生成した分、収率が低下したと考えられる。
有機塩基としてピリジンの代わりにヘキサフルオロイソプロパノールに対して3.5倍モルの2,6-ルチジン(4.05mL)を用い、反応時間を0.5時間とした以外は上記実施例3(1)と同様にして、反応を行った。反応液を1H-NMRと19F-NMRで直接分析したところ、収率約50%で目的化合物である炭酸ビス(ヘキサフルオロイソプロピル)が生成していることが確認された。2,6-ルチジンはその塩基性がピリジンよりも強く、生成するHClと塩酸塩を形成する能力が強いため、原料が残留して収率が比較的低下したと考えられる。なお、反応終了時、反応液は、上記実施例3(1)と同様に二層に分離した。
有機塩基を用いず、反応時間を3時間とした以外は上記実施例3(1)と同様にして反応を行ったが、目的化合物である炭酸ヘキサフルオロイソプロピルは全く生成しなかった。
上記反応容器内に精製したクロロホルム(20mL)、ノナフルオロ-t-ブタノール(0.694g,5mmol)、ノナフルオロ-t-ブタノールに対して5倍モルのピリジン(2mL)を入れ、攪拌混合した。当該反応液を攪拌しつつ、20℃で0.5L/minの酸素ガスをバブリングで吹き込み、上記低圧水銀ランプを照射した。1時間後、反応液を19F-NMRで直接分析したところ、収率22%で目的化合物である炭酸ノナフルオロ-t-ブチルが生成していることが確認された。
有機塩基としてピリジンの代わりにノナフルオロ-t-ブタノールに対して.5倍モルの2,6-ルチジン(2.9mL)を用いた以外は上記実施例4(1)と同様にして、収率35%で目的化合物である炭酸ノナフルオロ-t-ブチルが生成していることを確認した。
また、得られたポリ炭酸4,4’-(ヘキサフルオロイソプロピリデン)ビスフェノールを下記の条件のゲル浸透クロマトグラフィー(GPC)で分析し、分子量を求めた。結果を表1に示す。
装置: 高速GPC装置(「HLC-8320GPC」東ソー社製)
カラム: 超高分子用カラム(「TSKgel GMHHR-H×2」東ソー社製)
移動相: クロロホルム 流速: 1.0mL/min
オーブン温度: 40℃ 濃度: 0.3w/v%
注入量: 100μL 分子量標準: ポリスチレン
検出器: RI
また、得られた共重合体の分子量を、上記実施例6と同様に求めた。結果を表2に示す。
4: 撹拌子, 5: 熱媒または冷媒, 6: 筒状反応容器
Claims (12)
- フッ素化カーボネート誘導体を製造するための方法であって、
塩素原子、臭素原子およびヨウ素原子からなる群から選択される1種以上のハロゲン原子を有するC1-4ハロゲン化炭化水素、求核性官能基を有する含フッ素化合物、および塩基を含む組成物に酸素存在下で光照射し、
前記含フッ素化合物が下式(i)で表される化合物であり且つ前記フッ素化カーボネート誘導体が下式(I)で表されるフッ素化カーボネート誘導体であるか、または、
前記含フッ素化合物が下式(ii)で表される化合物であり且つ前記フッ素化カーボネート誘導体が下式(II-1)で表される単位を含むフッ素化ポリカーボネート誘導体もしくは下式(II-2)で表されるフッ素化環状カーボネート誘導体である、フッ素化カーボネート誘導体の製造方法。
(i) RF1-A-H
(ii) H-A-RF2-A-H
(I) RF1-A-C(=O)-A-RF1
(II-1) [-A-RF2-A-C(=O)-]
Aは、O、SまたはNHであり、
RF1はフッ素原子を有する反応不活性な1価有機基であり、
RF2はフッ素原子を有する反応不活性な2価有機基である。] - 前記含フッ素化合物が下式(i-1)で表される化合物であり且つ前記フッ素化カーボネート誘導体が下式(I-1)で表されるフッ素化カーボネート誘導体であるか、前記含フッ素化合物が下式(i-2)で表される化合物であり且つ前記フッ素化カーボネート誘導体が下式(I-2)で表されるフッ素化カーボネート誘導体であるか、または、前記含フッ素化合物が下式(i-3)で表される化合物であり且つ前記フッ素化カーボネート誘導体が下式(I-3)で表されるフッ素化カーボネート誘導体である、請求項1に記載の製造方法。
(i-1) RF11CH2-A-H
(i-2) (RF12)2CH-A-H
(i-3) (RF13)3C-A-H
(I-1) RF11CH2-A-C(=O)-A-CH2-RF11
(I-2) (RF12)2CH-A-C(=O)-A-CH(RF12)2
(I-3) (RF13)3C-A-C(=O)-A-C(RF13)3
[式中、
Aは前述したものと同義を示し、
RF11は、C1-10フルオロアルキル基、C6-14フルオロアリール基、C4-14フルオロヘテロアリール基またはC2-24フルオロ(アルキルポリオキシアルキレン)基であり、
2個のRF12は、それぞれ独立にC1-10アルキル基、C1-10フルオロアルキル基、C6-14アリール基、C6-14フルオロアリール基、C4-14ヘテロアリール基、C4-14フルオロヘテロアリール基、C2-24アルキルポリオキシアルキレン基またはC2-24フルオロ(アルキルポリオキシアルキレン)基であり、1個または2個のRF12が、C1-10フルオロアルキル基、C6-14フルオロアリール基、C4-14フルオロヘテロアリール基またはC2-24フルオロ(アルキルポリオキシアルキレン)基であるか、または、共同してC2-6フルオロアルキレン基または1,2-フルオロアリーレン基を形成し、
3個のRF13は、それぞれ独立にC1-10アルキル基、C1-10フルオロアルキル基、C6-14アリール基、C6-14フルオロアリール基、C4-14ヘテロアリール基、C4-14フルオロヘテロアリール基、C2-24アルキルポリオキシアルキレン基またはC2-24フルオロ(アルキルポリオキシアルキレン)基であり、1個、2個または3個のRF13が、C1-10フルオロアルキル基、C6-14フルオロアリール基、C4-14フルオロヘテロアリール基またはC2-24フルオロ(アルキルポリオキシアルキレン)基である。] - 前記C1-4ハロゲン化炭化水素がC1-4ポリハロゲン化炭化水素である請求項1~3のいずれかに記載の製造方法。
- 前記C1-4ハロゲン化炭化水素がクロロホルムである請求項1~3のいずれかに記載の製造方法。
- 前記塩基として、複素環式芳香族アミン、非求核性強塩基、および無機塩基から実質的になる群より選択される1以上の塩基を用いる請求項1~5のいずれかに記載の製造方法。
- 前記複素環式芳香族アミンが、ピリジン、ピコリンまたはルチジンである請求項6に記載の製造方法。
- 前記非求核性強塩基が、1,5,7-トリアザビシクロ[4.4.0]デカ-5-エン、7-メチル-1,5,7-トリアザビシクロ[4.4.0]デカ-5-エン、1,8-ジアザビシクロ[5.4.0]ウンデカ-7-エン、1,5-ジアザビシクロ[4.3.0]ノナ-5-エンまたは1,1,3,3-テトラメチルグアニジンである請求項6に記載の製造方法。
- 前記無機塩基が、アルカリ金属水酸化物、アルカリ金属炭酸水素塩またはアルカリ金属炭酸塩である請求項6に記載の製造方法。
- 前記C1-4ハロゲン化炭化水素に対して0.001倍モル以上1倍モル以下の前記含フッ素化合物を用いる請求項1~9のいずれかに記載の製造方法。
- 前記含フッ素化合物に対して1.5倍モル以上10倍モル以下の前記塩基を用いる請求項1~10のいずれかに記載の製造方法。
- 前記組成物に照射する光が180nm以上500nm以下の波長の光である、請求項1~11のいずれかに記載の製造方法。
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