JP6751928B2 - モノヒドロペルフルオロアルカンを出発原料とするペルフルオロアルキル化合物の製造方法 - Google Patents
モノヒドロペルフルオロアルカンを出発原料とするペルフルオロアルキル化合物の製造方法 Download PDFInfo
- Publication number
- JP6751928B2 JP6751928B2 JP2018531732A JP2018531732A JP6751928B2 JP 6751928 B2 JP6751928 B2 JP 6751928B2 JP 2018531732 A JP2018531732 A JP 2018531732A JP 2018531732 A JP2018531732 A JP 2018531732A JP 6751928 B2 JP6751928 B2 JP 6751928B2
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- JP
- Japan
- Prior art keywords
- group
- cyclohexanone
- represented
- general formula
- piperidinone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 238000004519 manufacturing process Methods 0.000 title claims description 19
- -1 perfluoroalkyl compound Chemical class 0.000 title description 42
- 239000007858 starting material Substances 0.000 title description 5
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims description 70
- 238000006243 chemical reaction Methods 0.000 claims description 60
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 35
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 12
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 2
- 230000036571 hydration Effects 0.000 claims description 2
- 238000006703 hydration reaction Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 124
- 239000000047 product Substances 0.000 description 24
- 150000002576 ketones Chemical class 0.000 description 23
- 239000002994 raw material Substances 0.000 description 21
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 18
- 239000012965 benzophenone Substances 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 229910001868 water Inorganic materials 0.000 description 12
- 239000002904 solvent Substances 0.000 description 8
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000003905 agrochemical Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000012776 electronic material Substances 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000008204 material by function Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- JYAQYXOVOHJRCS-UHFFFAOYSA-N 1-(3-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(Br)=C1 JYAQYXOVOHJRCS-UHFFFAOYSA-N 0.000 description 3
- BAYUSCHCCGXLAY-UHFFFAOYSA-N 1-(3-methoxyphenyl)ethanone Chemical compound COC1=CC=CC(C(C)=O)=C1 BAYUSCHCCGXLAY-UHFFFAOYSA-N 0.000 description 3
- HUDYANRNMZDQGA-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]ethanone Chemical compound CN(C)C1=CC=C(C(C)=O)C=C1 HUDYANRNMZDQGA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- KYWIYKKSMDLRDC-UHFFFAOYSA-N undecan-2-one Chemical compound CCCCCCCCCC(C)=O KYWIYKKSMDLRDC-UHFFFAOYSA-N 0.000 description 3
- DWPLEOPKBWNPQV-UHFFFAOYSA-N 1-(2-methoxyphenyl)ethanone Chemical compound COC1=CC=CC=C1C(C)=O DWPLEOPKBWNPQV-UHFFFAOYSA-N 0.000 description 2
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 2
- WAFWCNFRHDIBBT-UHFFFAOYSA-N 1-butylpiperidin-3-one Chemical compound CCCCN1CCCC(=O)C1 WAFWCNFRHDIBBT-UHFFFAOYSA-N 0.000 description 2
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 2
- BHZCVJGWMAVFFI-UHFFFAOYSA-N 4-(cyclohexylamino)cyclohexan-1-one Chemical compound C1CC(=O)CCC1NC1CCCCC1 BHZCVJGWMAVFFI-UHFFFAOYSA-N 0.000 description 2
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- AIZUDZUYOGXUDV-UHFFFAOYSA-N C1(CCCCCCCCC1)NC1CCC(CC1)=O Chemical compound C1(CCCCCCCCC1)NC1CCC(CC1)=O AIZUDZUYOGXUDV-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 150000001502 aryl halides Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- WPJWIROQQFWMMK-UHFFFAOYSA-L beryllium dihydroxide Chemical compound [Be+2].[OH-].[OH-] WPJWIROQQFWMMK-UHFFFAOYSA-L 0.000 description 2
- 229910001865 beryllium hydroxide Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000006309 butyl amino group Chemical group 0.000 description 2
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- BAUZLFKYYIVGPM-UHFFFAOYSA-N cyclononanone Chemical compound O=C1CCCCCCCC1 BAUZLFKYYIVGPM-UHFFFAOYSA-N 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 2
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- BIMIJXSZMVGEJR-UHFFFAOYSA-M tetra(nonyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCC[N+](CCCCCCCCC)(CCCCCCCCC)CCCCCCCCC BIMIJXSZMVGEJR-UHFFFAOYSA-M 0.000 description 2
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 2
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 2
- ZYSDERHSJJEJDS-UHFFFAOYSA-M tetrakis-decylazanium;hydroxide Chemical compound [OH-].CCCCCCCCCC[N+](CCCCCCCCCC)(CCCCCCCCCC)CCCCCCCCCC ZYSDERHSJJEJDS-UHFFFAOYSA-M 0.000 description 2
- MYXKPFMQWULLOH-UHFFFAOYSA-M tetramethylazanium;hydroxide;pentahydrate Chemical compound O.O.O.O.O.[OH-].C[N+](C)(C)C MYXKPFMQWULLOH-UHFFFAOYSA-M 0.000 description 2
- DCFYRBLFVWYBIJ-UHFFFAOYSA-M tetraoctylazanium;hydroxide Chemical compound [OH-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC DCFYRBLFVWYBIJ-UHFFFAOYSA-M 0.000 description 2
- JVOPCCBEQRRLOJ-UHFFFAOYSA-M tetrapentylazanium;hydroxide Chemical compound [OH-].CCCCC[N+](CCCCC)(CCCCC)CCCCC JVOPCCBEQRRLOJ-UHFFFAOYSA-M 0.000 description 2
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 2
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 2
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 2
- 229940007718 zinc hydroxide Drugs 0.000 description 2
- OQZAQBGJENJMHT-UHFFFAOYSA-N 1,3-dibromo-5-methoxybenzene Chemical compound COC1=CC(Br)=CC(Br)=C1 OQZAQBGJENJMHT-UHFFFAOYSA-N 0.000 description 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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- OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000213 sulfino group Chemical group [H]OS(*)=O 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- FNSGKPBAZVBJRX-UHFFFAOYSA-M tetraheptylazanium;hydroxide Chemical compound [OH-].CCCCCCC[N+](CCCCCCC)(CCCCCCC)CCCCCCC FNSGKPBAZVBJRX-UHFFFAOYSA-M 0.000 description 1
- OVRJVKCZJCNSOW-UHFFFAOYSA-N thian-4-one Chemical compound O=C1CCSCC1 OVRJVKCZJCNSOW-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 125000005300 thiocarboxy group Chemical group C(=S)(O)* 0.000 description 1
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- DSXFPRKPFJRPIB-UHFFFAOYSA-N thiolan-3-one Chemical compound O=C1CCSC1 DSXFPRKPFJRPIB-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 238000006692 trifluoromethylation reaction Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
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- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/78—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton from carbonyl compounds, e.g. from formaldehyde, and amines having amino groups bound to carbon atoms of six-membered aromatic rings, with formation of methylene-diarylamines
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/45—Monoamines
- C07C211/48—N-alkylated amines
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
- C07C233/15—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/125—Monohydroxylic acyclic alcohols containing five to twenty-two carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/34—Halogenated alcohols
- C07C31/40—Halogenated alcohols perhalogenated
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
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- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
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- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
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- C07C2601/14—The ring being saturated
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- Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
一般式[1]:
で示されるカルボニル化合物と、一般式[2]:
M(OH)x [2]
[式中、Mは元素周期律表におけるI族、II族、III族、IV族、V族、VI族、VII族、VIII族、IX族、X族、XI族、XII族、及びXIII族に属する金属あるいは無置換若しくは炭素数1から10のアルキル基を置換基として有しても良いアンモニウムであり、それらは単独であっても、複数の物質の混合物であっても良く、xはMであらわされる物質の酸化数に一致する]
で示される水酸化物、及び一般式[3]:
RFH [3]
[式中、RFは炭素数1〜2の直鎖あるいは炭素数3〜10の直鎖、分岐あるいは環状構造を有することもあるアルキル基であり、炭素上の水素が全てフッ素で置換されたペルフルオロアルキル基を表す]
で示されるモノヒドロペルフルオロアルカンを有機溶媒中で反応させることを特徴とする、一般式[4]:
一般式[3]で示されるRFHがトリフルオロメタンであることを特徴とする、(1)に記載の方法。
一般式[3]で示されるRFHがペンタフルオロエタンであることを特徴とする、(1)に記載の方法。
一般式[2]で示されるM(OH)xが水酸化カリウムであることを特徴とする、(1)に記載の方法。
一般式[2]で示されるM(OH)xが水酸化ナトリウムであることを特徴とする、(1)に記載の方法。
一般式[2]で示されるM(OH)xが水酸化テトラメチルアンモニウムまたはその水和物であることを特徴とする、(1)に記載の方法。
一般式[2]で示されるM(OH)xが、粉末状で反応系に添加されることを特徴とする、(1)〜(6)のいずれかに記載の方法。
有機溶媒がジメチルスルホキシド、ジメチルホルムアミド、N−メチルピロリドン、テトラヒドロフラン、ジグライム、アセトニトリル、又はこれらの組み合わせであることを特徴とする、(1)〜(7)のいずれかに記載の製造方法。
モノヒドロペルフルオロアルカンが気体の状態で反応液と接触することを特徴とする、(1)〜(8)のいずれかに記載の製造方法。
モノヒドロペルフルオロアルカンを液体あるいは固体の状態で反応液と混合させることを特徴とする、(1)〜(8)のいずれかに記載の製造方法。
本発明の方法は、実験的に見出されたものであり、本発明者らのこれまでの検討によれば、一般式[2]で示される水酸化物が、一般式[3]で示されるモノヒドロペルフルオロアルカンから水素原子(プロトン)を引き抜き、その結果生じたペルフルオロアルキルアニオンが一般式[1]で示されるカルボニル化合物のカルボニル基の炭素に求核的に攻撃し、カルボニル基が水酸基となり、一般式[4]で示されるペルフルオロアルキルアルコールが形成されるものと考えられる。先行技術においては、モノヒドロペルフルオロアルカンから水素原子(プロトン)を引き抜く過程が特殊な強塩基を用いなければ起こらないと考えられていたので、一般式[2]で示される水酸化物を使用することにより、本発明の方法が実施できることは驚くべきことであった。
本発明の一般式[1]で示されるカルボニル化合物は、特に限定されず、R1、R2で表される置換基としては、水素原子の他に、炭素数1〜2の直鎖あるいは炭素数3〜26、特に炭素数3〜10の直鎖、分岐あるいは環状構造を有することもあるアルキル基、アリール基、ヘテロアリール基、アラルキル基、アルケニル基またはアルキニル基をあらわし、具体的には、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ターシャリーブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、シクロオクチル基、シクロノニル基、シクロデシル基、フェニル基、ナフチル基、アントラニル基、ナフタセニル基、ペンタセニル基、ヘキサセニル基、コロニル基、ピロリル基、フリル基、チエニル基、ピリジル基、ピリミジル基、ピラジル基、ピリダジル基、ピラゾリル基、イミダゾリル基、オキサゾリル基、チアゾリル基、インドリル基、ベンゾフリル基、ベンゾチエニル基、キノリル基、イソキノリル基、キノキサリル基、フタラジル基、キナゾリル基、ナフチリジル基、シンノリル基、ベンゾイミダゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、ベンジル基、フェネチル基、ビニル基、アリル基、プレニル基、プロパギル基などであり、それらの炭素原子上には水素原子以外の原子、例えば窒素、酸素、ケイ素、リン、硫黄、フッ素、塩素、臭素、ヨウ素等が置換された状態でも良く、また、水素原子以外の置換基、例えば、アルキル基、アリール基、ヘテロアリール基、アラルキル基、アルケニル基、アルキニル基、ヒドロキシ基、ヒドロペルオキシ基、ジオキシ基、カルボキシル基、チオカルボキシ基、ジチオカルボキシ基、カルボニル基、チオカルボニル基、オキシカルボニル基、ハロホルミル基、カルバモイル基、メトキシ基、エトキシ基等のアルコキシ基、ジメチルアミノ基、アセトアミノ基(AcHN−)等のアミノ基、イミノ基、ヒドラジノ基、トリフルオロメチル基、ジフルオロメチル基、トリクロロメチル等のハロゲン置換アルキル基、スルファニル基、アルキルスルフィニル基、アルキルスルホニル基、スルホ基、スルフィノ基、シアノ基、イソシアノ基、シアナト基、イソシアナト基、チオシアナト基、イソチオシアナト基、ニトロ基、ニトロソ基、ジアゾ基、アジド基、アミジノ基、ホルミル基、チオホルミル基等が置換された状態でもよい。具体的には、ベンゾフェノン、アセトフェノン、ウンデカン−2−オン、4’−メトキシアセトフェノン、3’−メトキシアセトフェノン、2’−メトキシアセトフェノン、4’−ジメチルアミノアセトフェノン、4’−アセトアミドアセトフェノン、4’−フルオロアセトフェノン、4’−クロロアセトフェノン、3’−ブロモアセトフェノン、ピバルアルデヒド、ベンズアルデヒド、アセトアルデヒド、ホルムアルデヒドなどが挙げられる。
(ジシクロノニルアミノ)シクロヘキサノン、4−(シクロデシルアミノ)シクロヘキサノン、4−(ジフェニルアミノ)シクロヘキサノン、4−(ジナフチルアミノ)シクロヘキサノン、4−(ジアントラニルアミノ)シクロヘキサノン、4−(ジナフタセニルアミノ)シクロヘキサノン、4−(ジペンタセニルアミノ)シクロヘキサノン、4−(ジヘキサセニルアミノ)シクロヘキサノン、4−(ジコロニルアミノ)シクロヘキサノン、4−(ジピロリルアミノ)シクロヘキサノン、4−(ジフリルアミノ)シクロヘキサノン、4−(ジチエニルアミノ)シクロヘキサノン、4−(ジピリジルアミノ)シクロヘキサノン、4−(ジピリミジルアミノ)シクロヘキサノン、4−(ジピラジルアミノ)シクロヘキサノン、4−(ジピリダジルアミノ)シクロヘキサノン、4−(ジピラゾリルアミノ)シクロヘキサノン、4−(ジイミダゾリルアミノ)シクロヘキサノン、4−(ジオキサゾリルアミノ)シクロヘキサノン、4−(ジチアゾリルアミノ)シクロヘキサノン、4−(ジインドリルアミノ)シクロヘキサノン、4−(ジベンゾフリルアミノ)シクロヘキサノン、4−(ジベンゾチエニルアミノ)シクロヘキサノン、4−(ジキノリルアミノ)シクロヘキサノン、4−(ジイソキノリルアミノ)シクロヘキサノン、4−(ジキノキサリルアミノ)シクロヘキサノン、4−(ジフタラジルアミノ)シクロヘキサノン、4−(ジキナゾリルアミノ)シクロヘキサノン、4−(ジナフチリジルアミノ)シクロヘキサノン、4−(ジシンノリルアミノ)シクロヘキサノン、4−(ジベンゾイミダゾリルアミノ)シクロヘキサノン、4−(ジベンゾオキサゾリルアミノ)シクロヘキサノン、4−(ジベンゾチアゾリルアミノ)シクロヘキサノン、4−(ジベンジルアミノ)シクロヘキサノン、4−(ジフェネチルアミノ)シクロヘキサノン、4−(ジビニルアミノ)シクロヘキサノン、4−(ジアリルアミノ)シクロヘキサノン、4−(ジプレニルアミノ)シクロヘキサノン、4−(ジプロパギルアミノ)シクロヘキサノン、4−ヒドロキシシクロヘキサノン、4−(メトキシ)シクロヘキサノン、4−(エトキシ)シクロヘキサノン、4−(プロポキシ)シクロヘキサノン、4−(イソプロポキシ)シクロヘキサノン、4−(ブトキシ)シクロヘキサノン、4−(イソブトキシ)シクロヘキサノン、4−(ターシャリーブトキシ)シクロヘキサノン、4−(ペンチルオキシ)シクロヘキサノン、4−(ヘキシルオキシ)シクロヘキサノン、4−(ヘプチルオキシ)シクロヘキサノン、4−(オクチルオキシ)シクロヘキサノン、4−(ノニルオキシ)シクロヘキサノン、4−(デシルオキシ)シクロヘキサノン、4−(シクロプロポキシ)シクロヘキサノン、4−(シクロブトキシ)シクロヘキサノン、4−(シクロペンチルオキシ)シクロヘキサノン、4−(シクロヘキシルオキシ)シクロヘキサノン、4−(シクロヘプチルオキシ)シクロヘキサノン、4−(シクロオクチルオキシ)シクロヘキサノン、4−(シクロノニルオキシ)シクロヘキサノン、4−(シクロデシルオキシ)シクロヘキサノン、4−(フェノキシ)シクロヘキサノン、4−(ナフトキシ)シクロヘキサノン、4−(アントラセニルオキシ)シクロヘキサノン、4−(ナフタセニルオキシ)シクロヘキサノン、4−(ペンタセニルオキシ)シクロヘキサノン、4−(ヘキサセニルオキシ)シクロヘキサノン、4−(コロニルオキシ)シクロヘキサノン、4−(ピロリルオキシ)シクロヘキサノン、4−(フリルオキシ)シクロヘキサノン、4−(チエニルオキシ)シクロヘキサノン、4−(ピリジルオキシ)シクロヘキサノン、4−(ピリミジルオキシ)シクロヘキサノン、4−(ピラジルオキシ)シクロヘキサノン、4−(ピリダジルオキシ)シクロヘキサノン、4−(ピラゾリルオキシ)シクロヘキサノン、4−(イミダゾリルオキシ)シクロヘキサノン、4−(オキサゾリルオキシ)シクロヘキサノン、4−(チアゾリルオキシ)シクロヘキサノン、4−(インドリルオキシ)シクロヘキサノン、4−(ベンゾフリルオキシ)シクロヘキサノン、4−(ベンゾチエニルオキシ)シクロヘキサノン、4−(キノリルオキシ)シクロヘキサノン、4−(イソキノリルオキシ)シクロヘキサノン、4−(キノキサリルオキシ)シクロヘキサノン、4−(フタラジルオキシ)シクロヘキサノン、4−(キナゾリルオキシ)シクロヘキサノン、4−(ナフチリジルオキシ)シクロヘキサノン、4−(シンノリルオキシ)シクロヘキサノン、4−(ベンゾイミダゾリルオキシ)シクロヘキサノン、4−(ベンゾオキサゾリルオキシ)シクロヘキサノン、4−(ベンゾチアゾリルオキシ)シクロヘキサノン、4−(ベンジルオキシ)シクロヘキサノン、4−(フェネチルオキシ)シクロヘキサノン、4−(ビニルオキシ)シクロヘキサノン、4−(アリルオキシ)シクロヘキサノン、4−(プレニルオキシ)シクロヘキサノン、4−(プロパギルオキシ)シクロヘキサノン、4−メルカプトシクロヘキサノン、4−(メチルチオ)シクロヘキサノン、4−(エチルチオ)シクロヘキサノン、4−(プロピルチオ)シクロヘキサノン、4−(イソプロピルチオ)シクロヘキサノン、4−(ブチルチオ)シクロヘキサノン、4−(イソブチルチオ)シクロヘキサノン、4−(ターシャリーブチルチオ)シクロヘキサノン、4−(ペンチルチオ)シクロヘキサノン、4−(ヘキシルチオ)シクロヘキサノン、4−(ヘプチルチオ)シクロヘキサノン、4−(オクチルチオ)シクロヘキサノン、4−(ノニルチオ)シクロヘキサノン、4−(デシルチオ)シクロヘキサノン、4−(シクロプロピルチオ)シクロヘキサノン、4−(シクロブチルチオ)シクロヘキサノン、4−(シクロペンチルチオ)シクロヘキサノン、4−(シクロヘキシルチオ)シクロヘキサノン、4−(シクロヘプチルチオ)シクロヘキサノン、4−(シクロオクチルチオ)シクロヘキサノン、4−(シクロノニルチオ)シクロヘキサノン、4−(シクロデシルチオ)シクロヘキサノン、4−(フェニルチオ)シクロヘキサノン、4−(ナフチルチオ)シクロヘキサノン、4−(アントラニルチオ)シクロヘキサノン、4−(ナフタセニルチオ)シクロヘキサノン、4−(ペンタセニルチオ)シクロヘキサノン、4−(ヘキサセニルチオ)シクロヘキサノン、4−(コロニルチオ)シクロヘキサノン、4−(ピロリルチオ)シクロヘキサノン、4−(フリルチオ)シクロヘキサノン、4−(チエニルチオ)シクロヘキサノン、4−(ピリジルチオ)シクロヘキサノン、4−(ピリミジルチオ)シクロヘキサノン、4−(ピラジルチオ)シクロヘキサノン、4−(ピリダジルチオ)シクロヘキサノン、4−(ピラゾリルチオ)シクロヘキサノン、4−(イミダゾリルチオ)シクロヘキサノン、4−(オキサゾリルチオ)シクロヘキサノン、4−(チアゾリルチオ)シクロヘキサノン、4−(インドリルチオ)シクロヘキサノン、4−(ベンゾフリルチオ)シクロヘキサノン、4−(ベンゾチエニルチオ)シクロヘキサノン、4−(キノリルチオ)シクロヘキサノン、4−(イソキノリルチオ)シクロヘキサノン、4−(キノキサリルチオ)シクロヘキサノン、4−(フタラジルチオ)シクロヘキサノン、4−(キナゾリルチオ)シクロヘキサノン、4−(ナフチリジルチオ)シクロヘキサノン、4−(シンノリルチオ)シクロヘキサノン、4−(ベンゾイミダゾリルチオ)シクロヘキサノン、4−(ベンゾオキサゾリルチオ)シクロヘキサノン、4−(ベンゾチアゾリルチオ)シクロヘキサノン、4−(ベンジルチオ)シクロヘキサノン、4−(フェネチルチオ)シクロヘキサノン、4−(ビニルチオ)シクロヘキサノン、4−(アリルチオ)シクロヘキサノン、4−(プレニルチオ)シクロヘキサノン、4−(プロパギルチオ)シクロヘキサノン、4−フルオロシクロヘキサノン、4−クロロシクロヘキサノン、4−ブロモシクロヘキサノン、4−ヨードシクロヘキサノン、などが挙げられる。
本発明における一般式[2]で表される水酸化物は、特に限定されず、Mで表される物質としては、主にI族、II族、III族、IV族、V族、VI族、VII族、VIII族、IX族、X族、XI族、XII族、及びXIII族の金属あるいは無置換若しくは炭素数1から10のアルキル基を置換基として有しても良いアンモニウムの水酸化物をあらわし、具体的には水酸化リチウム、水酸化ナトリウム、水酸化カリウム、水酸化ルビジウム、水酸化セシウム、水酸化ベリリウム、水酸化マグネシウム、水酸化カルシウム、水酸化ストロンチウム、水酸化バリウム、オキシ水酸化鉄、水酸化銅、水酸化亜鉛、水酸化アルミニウム、水酸化アンモニウム、水酸化テトラメチルアンモニウム、水酸化テトラエチルアンモニウム、水酸化テトラプロピルアンモニウム、水酸化テトラブチルアンモニウム、水酸化テトラペンチルアンモニウム、水酸化テトラヘキシルアンモニウム、水酸化テトラヘプチルアンモニウム、水酸化テトラオクチルアンモニウム、水酸化テトラノニルアンモニウム、水酸化テトラデシルアンモニウムなどである。なお、アンモニウム塩を形成している窒素原子上の4つのアルキル基は全て同じであっても良く、全てが異なっていても良く、あるいはアルキル基の1〜4つが水素で置換されていても良く、無水物あるいは水和物(1水和物から20水和物)が使用できる。一般式[2]で表される水酸化物は、好ましくは1価の陽イオンと1個の水酸化物イオンの組み合わせ、より好ましくは水酸化ナトリウム、水酸化カリウム、水酸化テトラメチルアンモニウムまたはその水和物(特に、5水和物)である。
本発明における一般式[3]で示されるモノヒドロペルフルオロアルカンは、特に限定されず、RFで表される物質としては炭素数1〜2の直鎖あるいは3〜26、特に炭素数3〜10の直鎖、分岐あるいは環状構造を有することもあるアルキル基であり、炭素上の水素が全てフッ素で置換されたペルフルオロアルキル基を表し、具体的にはトリフルオロメチル基、ペンタフルオロエチル基、ヘプタフルオロプロピル基、ヘプタフルオロイソプロピル基、ペンタフルオロシクロプロピル基、ノナフルオロブチル基、ノナフルオロイソブチル基、ノナフルオロターシャリーブチル基、ヘプタフルオロシクロブチル基、ウンデカフルオロペンチル基、ノナフルオロシクロペンチル基、トリデカフルオロヘキシル基、ウンデカフルオロシクロヘキシル基、ペンタデカフルオロヘプチル基、トリデカフルオロシクロヘプチル基、ヘプタデカフルオロオクチル基、ペンタデカシクロオクチル基、ノナデカフルオロノニル基、ヘプタデカフルオロシクロノニル基、ヘンイコサフルオロデセニル基、ノナデカフルオロシクロデセニル基などを表す。安価で大量に入手できる点から、一般式[3]で示されるモノヒドロペルフルオロアルカンとしては、好ましくはトリフルオロメタン、ペンタフルオロエタンであり、より好ましくはトリフルオロメタンである。
本発明における一般式[4]で示されるペルフルオロアルキルアルコールは、それぞれ一般式[1]のR1、R2と同じ置換基R1、R2を持つ、対応するペルフルオロアルキルアルコールである。
次に、本発明における反応方法について詳細に説明する。
1H NMR (400 MHz, CDCl3) δ: 2.86 (s, 1H), 7.35−7.37 (m, 6H), 7.48 (d, J = 4.8 Hz, 4H).
19F NMR (376 MHz, CDCl3) δ: 87.5 (s, 3F).
GC−MS m/z (%): 252 (M+, 10), 183 (100), 105 (94), 77 (50).
1H NMR (400 MHz, CDCl3) δ: 1.79 (d, J = 0.8 Hz, 3H), 2.40 (s, 1H), 7.35−7.43 (m, 3H), 7.58 (d, J = 7.6 Hz, 2H).
19F NMR (376 MHz, CDCl3) δ: 80.7 (s, 3F).
GC−MS m/z (%): 121 (100), 105 (33), 77 (74), 69 (22), 51 (17).
1H NMR (400 MHz, CDCl3) δ: 0.88 (t, J = 6.8 Hz, 3H), 1.27−1.31 (m, 12H), 1.34 (s, 1H), 1.38−1.49 (m, 2H), 1.62−1.67 (m, 2H), 1.81 (s, 1H).
19F NMR (376 MHz, CDCl3) δ: 78.6 (s, 3F).
GC−MS m/z (%): 171 (15), 112 (25), 97 (39), 83 (80), 70 (100), 56 (85).
1H NMR (400 MHz, CDCl3) δ: 1.54−1.78 (m, 11H).
19F NMR (376 MHz, CDCl3) δ: 76.7 (s, 3F).
GC−MS m/z (%): 99 (100), 81 (87), 55 (30).
1H NMR (400 MHz, CDCl3) δ: 2.85 (s, 1H), 7.32−7.37 (m, 6H), 7.55 (d, J = 6.8 Hz, 4H).
19F NMR (376 MHz, CDCl3) δ: 45.3 (s, 2F), 84.7 (s, 3F).
GC−MS m/z (%): 183 (63), 105 (100), 77 (53), 51 (17).
1H NMR (400 MHz, CDCl3) δ: 1.82 (s, 3H), 2.39 (s, 1H), 7.36−7.42 (m, 3H), 7.56 (d, J = 7.6 Hz, 2H).
19F NMR (376 MHz, CDCl3) δ: 38.7 (d, J = 277 Hz, 1F), 40.2 (d, J = 277 Hz, 1F), 83.8 (s, 3F).
GC−MS m/z (%): 240 (M+, 8), 121 (100), 86 (24), 84 (36).
1H NMR (400 MHz, アセトン−d6) δ: 1.76 (s, 3H), 2.09(s,3H), 5.49(s, 1H), 7.57 (d, J = 9.0 Hz, 2H), 7.67 (d, J = 9.0 Hz, 2H), 9.23(s, 1H).
19F NMR (376 MHz, アセトン−d6) δ: 83.1 (s, 3F).
GC−MS m/z (%): 247 (M+, 2), 178 (48), 136 (100), 120 (13), 94 (69), 77(14), 69 (5), 65 (25).
Claims (10)
- 一般式[1]:
で示されるカルボニル化合物と、一般式[2]:
M(OH)x [2]
[式中、Mは元素周期律表におけるI族、II族、III族、IV族、V族、VI族、VII族、VIII族、IX族、X族、XI族、XII族、及びXIII族に属する金属あるいは無置換若しくは炭素数1から10のアルキル基を置換基として有しても良いアンモニウムであり、それらは単独であっても、複数の物質の混合物であっても良く、xはMであらわされる物質の酸化数に一致する]
で示される水酸化物、及び一般式[3]:
RFH [3]
[式中、RFは炭素数1〜2の直鎖あるいは炭素数3〜10の直鎖、分岐あるいは環状構造を有することもあるアルキル基であり、炭素上の水素が全てフッ素で置換されたペルフルオロアルキル基を表す]
で示されるモノヒドロペルフルオロアルカンを有機溶媒中で反応させることを特徴とする、一般式[4]:
で示されるペルフルオロアルキル基を有するアルコールの製造方法であって、前記一般式[2]で示されるM(OH) x が水酸化カリウム、水酸化ナトリウム、または、水酸化テトラメチルアンモニウムまたはその水和物から選ばれる化合物であることを特徴とする、前記方法。 - 一般式[3]で示されるRFHがトリフルオロメタンであることを特徴とする、請求項1に記載の方法。
- 一般式[3]で示されるRFHがペンタフルオロエタンであることを特徴とする、請求項1に記載の方法。
- 一般式[2]で示されるM(OH)xが水酸化カリウムであることを特徴とする、請求項1に記載の方法。
- 一般式[2]で示されるM(OH)xが水酸化ナトリウムであることを特徴とする、請求項1に記載の方法。
- 一般式[2]で示されるM(OH)xが水酸化テトラメチルアンモニウムまたはその水和物であることを特徴とする、請求項1に記載の方法。
- 一般式[2]で示されるM(OH)xが、粉末状で反応系に添加されることを特徴とする、請求項1〜6のいずれかに記載の方法。
- 有機溶媒がジメチルスルホキシド、ジメチルホルムアミド、N−メチルピロリドン、テトラヒドロフラン、ジグライム、アセトニトリル、又はこれらの組み合わせであることを特徴とする、請求項1〜7のいずれかに記載の製造方法。
- モノヒドロペルフルオロアルカンが気体の状態で反応液と接触することを特徴とする、請求項1〜8のいずれかに記載の製造方法。
- モノヒドロペルフルオロアルカンを液体あるいは固体の状態で反応液と混合させることを特徴とする、請求項1〜8のいずれかに記載の製造方法。
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