JP6302157B2 - ヒンダードフェノールの製造方法 - Google Patents
ヒンダードフェノールの製造方法 Download PDFInfo
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- JP6302157B2 JP6302157B2 JP2012242720A JP2012242720A JP6302157B2 JP 6302157 B2 JP6302157 B2 JP 6302157B2 JP 2012242720 A JP2012242720 A JP 2012242720A JP 2012242720 A JP2012242720 A JP 2012242720A JP 6302157 B2 JP6302157 B2 JP 6302157B2
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- carboxylic acid
- phenol
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- anhydride
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- 238000004519 manufacturing process Methods 0.000 title claims description 41
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 88
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 48
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 28
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 25
- 239000003960 organic solvent Substances 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 20
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 9
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 6
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 26
- 239000002904 solvent Substances 0.000 description 21
- 239000000463 material Substances 0.000 description 18
- -1 pharmaceutical Substances 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- 125000001309 chloro group Chemical group Cl* 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 8
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 125000004093 cyano group Chemical group *C#N 0.000 description 8
- 239000012535 impurity Substances 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 239000003963 antioxidant agent Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- UKDOTCFNLHHKOF-FGRDZWBJSA-N (z)-1-chloroprop-1-ene;(z)-1,2-dichloroethene Chemical group C\C=C/Cl.Cl\C=C/Cl UKDOTCFNLHHKOF-FGRDZWBJSA-N 0.000 description 4
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 4
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 229950011008 tetrachloroethylene Drugs 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 3
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 0 CC(C)c1c(C(C)(C)C(C)=*)cccc1C(C)(C)C Chemical compound CC(C)c1c(C(C)(C)C(C)=*)cccc1C(C)(C)C 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000001293 FEMA 3089 Substances 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N Methyl ethyl ketone Natural products CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000011280 coal tar Substances 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000003502 gasoline Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241000219289 Silene Species 0.000 description 1
- GWKHPDRLCGHCKJ-UHFFFAOYSA-N [CH2-]C(CC)C(C)CC1CCC(CCCCC)CC1 Chemical compound [CH2-]C(CC)C(C)CC1CCC(CCCCC)CC1 GWKHPDRLCGHCKJ-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- 229940117955 isoamyl acetate Drugs 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- KCXYZMFPZHYUFO-UHFFFAOYSA-N n-methyl-n-phosphanylmethanamine Chemical compound CN(C)P KCXYZMFPZHYUFO-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229940074411 xylene Drugs 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Liquid Crystal Substances (AREA)
Description
また、カルボン酸(B)が、下記一般式(II)で表される化合物であることが好ましい。
さらに一般式(I)で表される化合物は合成の容易さ、反応効率及び、液晶材料に使用する場合には液晶材料との相溶性の観点から、Y1が炭素原子数1から8のアルキル基である場合が好ましく、Y1及びY5が炭素原子数1から8のアルキル基である場合がより好ましく、Y1がイソプロピル基又はtert−ブチル基で、Y5が炭素原子数1から8のアルキル基である場合がさらに好ましく、Y1がイソプロピル基又はtert−ブチル基で、Y5が炭素原子数1から8のアルキル基で、Y3が水素原子を表す場合がさらにより好ましく、Y1及びY5がイソプロピル基又はtert−ブチル基で、Y3が水素原子を表す場合がさらに好ましく、Y1及びY5がイソプロピル基又はtert−ブチル基で、Y2、Y3及びY4が水素原子を表す場合がさらにより好ましく、Y1及びY5がtert−ブチル基で、Y2、Y3及びY4が水素原子を表す場合が特に好ましい。
mは1から3の整数を表す場合が好ましく、1又は2を表す場合がより好ましい。
(GC分析条件)
カラム:Agilent Technologies,J&W Column DB−1HT,15m×0.25mm×0.10μm
温度プログラム:100℃(1分間)−(20℃/分間)−250℃−(10℃/分間)−380℃−(7℃/分間)−400℃(2.64分間)
注入口温度:350℃
検出器温度:400℃
(UPLC分析条件)
カラム:Waters ACQUITY UPLC BEH C18,2.1×100mm,1.7μm
溶出溶媒:アセトニトリル/水(90:10)
流速:0.5mL/min
検出器:UV,210nm
カラムオーブン:40℃
(実施例1)式(I−1)で表される化合物の製造
1H NMR(CDCl3)δ 1.45(m,40H),1.75(quin,4H),2.92(t,4H),5.70(s,2H),7.85(s,4H)ppm.
13C NMR(CDCl3)δ 24.6,29.4,30.1,34.3,38.0,125.7,128.9,135.6,158.2,199.9ppm.
融点 172℃
LRMS(EI)m/z 550
(比較例1)式(I−1C)で表される化合物の製造
1H NMR(CDCl3)δ 1.45(m,40H),1.75(quin,4H),2.92(t,4H),5.70(s,2H),7.85(s,4H)ppm.
13C NMR(CDCl3)δ 24.6,29.4,30.1,34.3,38.0,125.7,128.9,135.6,158.2,199.9ppm.
融点 172℃
LRMS(EI)m/z 550
(実施例2)式(I−2)で表される化合物の製造
1H NMR(CDCl3)δ 1.47(s,36H),2.92(t,4H),5.70(s,2H),7.85(s,4H)ppm.
13C NMR(CDCl3)δ 30.1,38.0,125.7,128.9,135.6,158.2,199.9ppm.
LRMS(EI)m/z 494
(比較例2)式(I−2C)で表される化合物の製造
1H NMR(CDCl3)δ 1.47(s,36H),2.92(t,4H),5.70(s,2H),7.85(s,4H)ppm.
13C NMR(CDCl3)δ 30.1,38.0,125.7,128.9,135.6,158.2,199.9ppm.
LRMS(EI)m/z 494
(実施例3)式(I−3)で表される化合物の製造
1H NMR(CDCl3)δ 0.89(t,3H),1.38(m,8H),1.47(s,18H),2.92(t,2H),5.70(s,1H),7.85(s,2H)ppm.
13C NMR(CDCl3)δ 14.1,22.7,29.4,29.6,30.1,34.3,38.0,125.7,128.9,135.6,158.2,199.9ppm.
LRMS(EI)m/z 318
(比較例3)式(I−3C)で表される化合物の製造
1H NMR(CDCl3)δ 0.89(t,3H),1.38(m,8H),1.47(s,18H),2.92(t,2H),5.70(s,1H),7.85(s,2H)ppm.
13C NMR(CDCl3)δ 14.1,22.7,29.4,29.6,30.1,34.3,38.0,125.7,128.9,135.6,158.2,199.9ppm.
LRMS(EI)m/z 318
(実施例4)式(I−4)で表される化合物の製造
LRMS(EI)m/z 400
(比較例4)式(I−4C)で表される化合物の製造
LRMS(EI)m/z 400
(実施例5)式(I−5)で表される化合物の製造
LRMS(EI)m/z 298
(比較例5)式(I−5C)で表される化合物の製造
LRMS(EI)m/z 298
(実施例6)式(I−6)で表される化合物の製造
LRMS(EI)m/z 230
(比較例6)式(I−6C)で表される化合物の製造
LRMS(EI)m/z 230
(実施例7〜12及び比較例7〜12)
下記化合物によって構成される液晶組成物を調製し、母体液晶(X)とした。
測定装置は東陽テクニカ社製の多チャンネル液晶表示装置「Model6254」を使用した。測定温度25℃、±1Vの矩形波からなるソース電圧を液晶デバイスに64マイクロ秒印加したのち遮断し、16.67m秒間中の電圧の減衰量を測定し、減衰が全くない場合を100%とした場合の、これに対する面積比率をそれぞれ電圧保持率(VHR(初期)(%))として算出した。また、表示素子を80℃で2時間加熱した後に測定した電圧保持率をVHR(加熱)(%)、ウシオ電機社製超高圧水銀ランプUSH−500Dで30分間UV照射した後に測定した電圧保持率をVHR(UV)(%)とした。結果を下表に示す。
Claims (7)
- フェノール(A)、カルボン酸(B)及びカルボン酸無水物(C)を使用するアシルフェノール(D)の製造方法において、フェノール(A)、カルボン酸(B)及びカルボン酸無水物(C)から選ばれる2種の混合物(E)及び有機溶媒に、フェノール(A)、カルボン酸(B)及びカルボン酸無水物(C)のうち混合物(E)の成分となっていない1種を加えるか、又は、フェノール(A)、カルボン酸(B)及びカルボン酸無水物(C)から選ばれる1種である化合物(F)及び有機溶媒に、フェノール(A)、カルボン酸(B)及びカルボン酸無水物(C)のうち化合物(F)以外の2種を加えて、フェノール(A)、カルボン酸(B)及びカルボン酸無水物(C)が反応する際に有機溶媒を存在させ、
フェノール(A)が、下記一般式(I)
カルボン酸(B)が、下記一般式(II)
複数存在するRは同一であっても異なっていてもよい。)で表される化合物であり、
カルボン酸無水物(C)がトリフルオロ酢酸無水物であり、
有機溶媒がクロロホルム、ジクロロメタン、1,2−ジクロロエタン、1,1,1−トリクロロエタン、ヘキサン、ペンタン、シクロヘキサン、ヘプタンから選ばれる1種又は2種以上の有機溶媒である製造方法。 - フェノール(A)、カルボン酸(B)及び有機溶媒に対し、カルボン酸無水物(C)を加えることによる請求項1記載の製造方法。
- フェノール(A)、カルボン酸無水物(C)及び有機溶媒に対し、カルボン酸(B)を加えることによる請求項1記載の製造方法。
- カルボン酸(B)、カルボン酸無水物(C)及び有機溶媒に対し、フェノール(A)を加えることによる請求項1記載の製造方法。
- 反応温度が−100℃から200℃である請求項1から請求項4のいずれか1項に記載の製造方法。
- 反応温度が−20℃から100℃である請求項1から請求項4のいずれか1項に記載の製造方法。
- 反応温度が0℃から60℃である請求項1から請求項4のいずれか1項に記載の製造方法。
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