JP2005082569A - 新規な４，４”−ジアルコキシ−ｐ−ターフェニル類 - Google Patents
新規な４，４”−ジアルコキシ−ｐ−ターフェニル類 Download PDFInfo
- Publication number
- JP2005082569A JP2005082569A JP2003319460A JP2003319460A JP2005082569A JP 2005082569 A JP2005082569 A JP 2005082569A JP 2003319460 A JP2003319460 A JP 2003319460A JP 2003319460 A JP2003319460 A JP 2003319460A JP 2005082569 A JP2005082569 A JP 2005082569A
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- JP
- Japan
- Prior art keywords
- terphenyl
- dihydroxy
- terphenyls
- methyl
- isopropyl
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims abstract description 29
- 239000003513 alkali Substances 0.000 claims abstract description 7
- QHPCLQOVFLJDJH-UHFFFAOYSA-N 1-decoxy-4-[4-(4-decoxyphenyl)phenyl]-2-propan-2-ylbenzene Chemical group C1=CC(OCCCCCCCCCC)=CC=C1C1=CC=C(C=2C=C(C(OCCCCCCCCCC)=CC=2)C(C)C)C=C1 QHPCLQOVFLJDJH-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 5
- FVIAPUZAEIMEEW-UHFFFAOYSA-N 4-[4-(4-hydroxyphenyl)phenyl]phenol Chemical group C1=CC(O)=CC=C1C1=CC=C(C=2C=CC(O)=CC=2)C=C1 FVIAPUZAEIMEEW-UHFFFAOYSA-N 0.000 claims description 4
- 150000001350 alkyl halides Chemical class 0.000 abstract description 9
- 125000005036 alkoxyphenyl group Chemical group 0.000 abstract description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000013078 crystal Substances 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 24
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- -1 methylpentyl Chemical group 0.000 description 18
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 16
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 13
- 238000000034 method Methods 0.000 description 11
- 239000002994 raw material Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- UOLABWPPWJVRDF-UHFFFAOYSA-N 4-[4-(4-hydroxyphenyl)phenyl]-2-propan-2-ylphenol Chemical group C1=C(O)C(C(C)C)=CC(C=2C=CC(=CC=2)C=2C=CC(O)=CC=2)=C1 UOLABWPPWJVRDF-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- RZYVFXFNSLSXBL-UHFFFAOYSA-N 4-[4-(4-hydroxyphenyl)phenyl]-2-methylphenol Chemical group C1=C(O)C(C)=CC(C=2C=CC(=CC=2)C=2C=CC(O)=CC=2)=C1 RZYVFXFNSLSXBL-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000004455 differential thermal analysis Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 230000007704 transition Effects 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 0 *Oc(cc1)ccc1-c(cc1)ccc1-c(cc1)ccc1O* Chemical compound *Oc(cc1)ccc1-c(cc1)ccc1-c(cc1)ccc1O* 0.000 description 3
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 3
- COPAKCJSVNJXRT-UHFFFAOYSA-N 1-dodecoxy-4-[4-(4-dodecoxyphenyl)phenyl]-2-methylbenzene Chemical group C1=CC(OCCCCCCCCCCCC)=CC=C1C1=CC=C(C=2C=C(C)C(OCCCCCCCCCCCC)=CC=2)C=C1 COPAKCJSVNJXRT-UHFFFAOYSA-N 0.000 description 3
- OCXCIAZCFHZFQC-UHFFFAOYSA-N 1-octoxy-4-[4-(4-octoxyphenyl)phenyl]-2-propan-2-ylbenzene Chemical group C1=CC(OCCCCCCCC)=CC=C1C1=CC=C(C=2C=C(C(OCCCCCCCC)=CC=2)C(C)C)C=C1 OCXCIAZCFHZFQC-UHFFFAOYSA-N 0.000 description 3
- LAEQSJDGCGSVDA-UHFFFAOYSA-N C(CCCCCCCCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1)OCCCCCCCCCC)C Chemical group C(CCCCCCCCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1)OCCCCCCCCCC)C LAEQSJDGCGSVDA-UHFFFAOYSA-N 0.000 description 3
- LMVZKBLHPAMKMJ-UHFFFAOYSA-N C1=CC(OCCCCCCCCCCCC)=CC=C1C1=CC=C(C=2C=C(C(OCCCCCCCCCCCC)=CC=2)C(C)C)C=C1 Chemical group C1=CC(OCCCCCCCCCCCC)=CC=C1C1=CC=C(C=2C=C(C(OCCCCCCCCCCCC)=CC=2)C(C)C)C=C1 LMVZKBLHPAMKMJ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 2
- ZTEHOZMYMCEYRM-UHFFFAOYSA-N 1-chlorodecane Chemical compound CCCCCCCCCCCl ZTEHOZMYMCEYRM-UHFFFAOYSA-N 0.000 description 2
- CLWAXFZCVYJLLM-UHFFFAOYSA-N 1-chlorohexadecane Chemical compound CCCCCCCCCCCCCCCCCl CLWAXFZCVYJLLM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- IRXVKFABZVMSOA-UHFFFAOYSA-N 1,4-bis(4-butoxyphenyl)benzene Chemical group CCCCOC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C(C=C1)OCCCC IRXVKFABZVMSOA-UHFFFAOYSA-N 0.000 description 1
- YGFAFZMAFTWFAR-UHFFFAOYSA-N 1,4-bis(4-decoxyphenyl)benzene Chemical group C(CCCCCCCCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C(C=C1)OCCCCCCCCCC YGFAFZMAFTWFAR-UHFFFAOYSA-N 0.000 description 1
- YJCYHUOPAJOVCV-UHFFFAOYSA-N 1,4-bis(4-ethoxyphenyl)benzene Chemical group C(C)OC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C(C=C1)OCC YJCYHUOPAJOVCV-UHFFFAOYSA-N 0.000 description 1
- HKBAORISDXMQKI-UHFFFAOYSA-N 1,4-bis(4-hexadecoxyphenyl)benzene Chemical group C1=CC(OCCCCCCCCCCCCCCCC)=CC=C1C1=CC=C(C=2C=CC(OCCCCCCCCCCCCCCCC)=CC=2)C=C1 HKBAORISDXMQKI-UHFFFAOYSA-N 0.000 description 1
- WTGXCMGPTHJFEM-UHFFFAOYSA-N 1,4-bis(4-hexoxyphenyl)benzene Chemical group C1=CC(OCCCCCC)=CC=C1C1=CC=C(C=2C=CC(OCCCCCC)=CC=2)C=C1 WTGXCMGPTHJFEM-UHFFFAOYSA-N 0.000 description 1
- VBXMYYRFSXQGSU-UHFFFAOYSA-N 1,4-bis(4-methoxyphenyl)benzene Chemical group C1=CC(OC)=CC=C1C1=CC=C(C=2C=CC(OC)=CC=2)C=C1 VBXMYYRFSXQGSU-UHFFFAOYSA-N 0.000 description 1
- DKHICYYGODCMAP-UHFFFAOYSA-N 1,4-bis(4-octoxyphenyl)benzene Chemical group C1=CC(OCCCCCCCC)=CC=C1C1=CC=C(C=2C=CC(OCCCCCCCC)=CC=2)C=C1 DKHICYYGODCMAP-UHFFFAOYSA-N 0.000 description 1
- YFCWLCTTWQLKKD-UHFFFAOYSA-N 1,4-bis(4-tetradecoxyphenyl)benzene Chemical group C1=CC(OCCCCCCCCCCCCCC)=CC=C1C1=CC=C(C=2C=CC(OCCCCCCCCCCCCCC)=CC=2)C=C1 YFCWLCTTWQLKKD-UHFFFAOYSA-N 0.000 description 1
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- JEKYMVBQWWZVHO-UHFFFAOYSA-N 1-chloro-2,2-dimethylpropane Chemical compound CC(C)(C)CCl JEKYMVBQWWZVHO-UHFFFAOYSA-N 0.000 description 1
- SLBTUZZYJLBZQV-UHFFFAOYSA-N 1-chloro-2-methylpentane Chemical compound CCCC(C)CCl SLBTUZZYJLBZQV-UHFFFAOYSA-N 0.000 description 1
- CZHLPWNZCJEPJB-UHFFFAOYSA-N 1-chloro-3-methylbutane Chemical compound CC(C)CCCl CZHLPWNZCJEPJB-UHFFFAOYSA-N 0.000 description 1
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 1
- VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical compound CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
- CNDHHGUSRIZDSL-UHFFFAOYSA-N 1-chlorooctane Chemical compound CCCCCCCCCl CNDHHGUSRIZDSL-UHFFFAOYSA-N 0.000 description 1
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 1
- RNHWYOLIEJIAMV-UHFFFAOYSA-N 1-chlorotetradecane Chemical compound CCCCCCCCCCCCCCCl RNHWYOLIEJIAMV-UHFFFAOYSA-N 0.000 description 1
- TZRAQOHLHVRMRY-UHFFFAOYSA-N 1-methoxy-4-[4-(4-methoxyphenyl)phenyl]-2-methylbenzene Chemical group C1=CC(OC)=CC=C1C1=CC=C(C=2C=C(C)C(OC)=CC=2)C=C1 TZRAQOHLHVRMRY-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- GNAKLBILTGUBJD-UHFFFAOYSA-N 2,6-ditert-butyl-4-[4-(4-hydroxyphenyl)phenyl]phenol Chemical group CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C=2C=CC(=CC=2)C=2C=CC(O)=CC=2)=C1 GNAKLBILTGUBJD-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- SVVVEBTZLJSJQB-UHFFFAOYSA-N 2-butyl-4-[4-(4-hydroxyphenyl)phenyl]phenol Chemical group C1=C(O)C(CCCC)=CC(C=2C=CC(=CC=2)C=2C=CC(O)=CC=2)=C1 SVVVEBTZLJSJQB-UHFFFAOYSA-N 0.000 description 1
- GLCIPJOIEVLTPR-UHFFFAOYSA-N 2-chlorohexane Chemical compound CCCCC(C)Cl GLCIPJOIEVLTPR-UHFFFAOYSA-N 0.000 description 1
- SLSMTKQEQKYHDB-UHFFFAOYSA-N 2-ethyl-4-[4-(4-hydroxyphenyl)phenyl]phenol Chemical group C1=C(O)C(CC)=CC(C=2C=CC(=CC=2)C=2C=CC(O)=CC=2)=C1 SLSMTKQEQKYHDB-UHFFFAOYSA-N 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- RJRGYADDZSASSW-UHFFFAOYSA-N 2-tert-butyl-4-[4-(4-hydroxyphenyl)phenyl]-5-methylphenol Chemical group CC1=CC(O)=C(C(C)(C)C)C=C1C1=CC=C(C=2C=CC(O)=CC=2)C=C1 RJRGYADDZSASSW-UHFFFAOYSA-N 0.000 description 1
- CBEDKBOKMYYLQT-UHFFFAOYSA-N 2-tert-butyl-4-[4-(4-hydroxyphenyl)phenyl]-6-methylphenol Chemical group CC(C)(C)C1=C(O)C(C)=CC(C=2C=CC(=CC=2)C=2C=CC(O)=CC=2)=C1 CBEDKBOKMYYLQT-UHFFFAOYSA-N 0.000 description 1
- QKYTYQNTKGWLQK-UHFFFAOYSA-N 2-tert-butyl-4-[4-(4-hydroxyphenyl)phenyl]phenol Chemical group C1=C(O)C(C(C)(C)C)=CC(C=2C=CC(=CC=2)C=2C=CC(O)=CC=2)=C1 QKYTYQNTKGWLQK-UHFFFAOYSA-N 0.000 description 1
- MQCZCCPLHDHRCI-UHFFFAOYSA-N 3-butyl-4-[4-(4-hydroxyphenyl)phenyl]phenol Chemical group CCCCC1=CC(O)=CC=C1C1=CC=C(C=2C=CC(O)=CC=2)C=C1 MQCZCCPLHDHRCI-UHFFFAOYSA-N 0.000 description 1
- MUTSPBSQJNZQFL-UHFFFAOYSA-N 3-ethyl-4-[4-(4-hydroxyphenyl)phenyl]phenol Chemical group CCC1=CC(O)=CC=C1C1=CC=C(C=2C=CC(O)=CC=2)C=C1 MUTSPBSQJNZQFL-UHFFFAOYSA-N 0.000 description 1
- NGYGJWPJGJATDA-UHFFFAOYSA-N 3-tert-butyl-4-[4-(4-hydroxyphenyl)phenyl]phenol Chemical group CC(C)(C)C1=CC(O)=CC=C1C1=CC=C(C=2C=CC(O)=CC=2)C=C1 NGYGJWPJGJATDA-UHFFFAOYSA-N 0.000 description 1
- MJDLFSNKVCFRDJ-UHFFFAOYSA-N 4-[4-(4-hydroxyphenyl)phenyl]-2,3,5-trimethylphenol Chemical group CC1=CC(O)=C(C)C(C)=C1C1=CC=C(C=2C=CC(O)=CC=2)C=C1 MJDLFSNKVCFRDJ-UHFFFAOYSA-N 0.000 description 1
- RTMTYRMBMPJKLP-UHFFFAOYSA-N 4-[4-(4-hydroxyphenyl)phenyl]-2,3,6-trimethylphenol Chemical group CC1=C(O)C(C)=CC(C=2C=CC(=CC=2)C=2C=CC(O)=CC=2)=C1C RTMTYRMBMPJKLP-UHFFFAOYSA-N 0.000 description 1
- GCPOVWUIAOWZSF-UHFFFAOYSA-N 4-[4-(4-hydroxyphenyl)phenyl]-2,5-dimethylphenol Chemical group C1=C(O)C(C)=CC(C=2C=CC(=CC=2)C=2C=CC(O)=CC=2)=C1C GCPOVWUIAOWZSF-UHFFFAOYSA-N 0.000 description 1
- IQGLAGPGUMLNPL-UHFFFAOYSA-N 4-[4-(4-hydroxyphenyl)phenyl]-2,6-dimethylphenol Chemical group CC1=C(O)C(C)=CC(C=2C=CC(=CC=2)C=2C=CC(O)=CC=2)=C1 IQGLAGPGUMLNPL-UHFFFAOYSA-N 0.000 description 1
- JLGSXEBHETUFSJ-UHFFFAOYSA-N 4-[4-(4-hydroxyphenyl)phenyl]-2-(2-methylpropyl)phenol Chemical group C1=C(O)C(CC(C)C)=CC(C=2C=CC(=CC=2)C=2C=CC(O)=CC=2)=C1 JLGSXEBHETUFSJ-UHFFFAOYSA-N 0.000 description 1
- PNYUGQDGUXIJNA-UHFFFAOYSA-N 4-[4-(4-hydroxyphenyl)phenyl]-2-propylphenol Chemical group C1=C(O)C(CCC)=CC(C=2C=CC(=CC=2)C=2C=CC(O)=CC=2)=C1 PNYUGQDGUXIJNA-UHFFFAOYSA-N 0.000 description 1
- PIXPOILKNXUZDD-UHFFFAOYSA-N 4-[4-(4-hydroxyphenyl)phenyl]-3-(2-methylpropyl)phenol Chemical group CC(C)CC1=CC(O)=CC=C1C1=CC=C(C=2C=CC(O)=CC=2)C=C1 PIXPOILKNXUZDD-UHFFFAOYSA-N 0.000 description 1
- IMLJWONRDPNAKO-UHFFFAOYSA-N 4-[4-(4-hydroxyphenyl)phenyl]-3-methylphenol Chemical group CC1=CC(O)=CC=C1C1=CC=C(C=2C=CC(O)=CC=2)C=C1 IMLJWONRDPNAKO-UHFFFAOYSA-N 0.000 description 1
- CPDMAHWDMSYMBF-UHFFFAOYSA-N 4-[4-(4-hydroxyphenyl)phenyl]-3-propan-2-ylphenol Chemical group CC(C)C1=CC(O)=CC=C1C1=CC=C(C=2C=CC(O)=CC=2)C=C1 CPDMAHWDMSYMBF-UHFFFAOYSA-N 0.000 description 1
- MNAUYCAQOGSBGQ-UHFFFAOYSA-N 4-[4-(4-hydroxyphenyl)phenyl]-3-propylphenol Chemical group CCCC1=CC(O)=CC=C1C1=CC=C(C=2C=CC(O)=CC=2)C=C1 MNAUYCAQOGSBGQ-UHFFFAOYSA-N 0.000 description 1
- YPWWZMCRPVJJGI-UHFFFAOYSA-N 4-[4-(4-hydroxyphenyl)phenyl]-5-methyl-2-propan-2-ylphenol Chemical group C1=C(O)C(C(C)C)=CC(C=2C=CC(=CC=2)C=2C=CC(O)=CC=2)=C1C YPWWZMCRPVJJGI-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
- WPCURPBJJCVQOD-UHFFFAOYSA-N C(C)OC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1)OCC)C Chemical group C(C)OC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1)OCC)C WPCURPBJJCVQOD-UHFFFAOYSA-N 0.000 description 1
- UGMYZHYJONHFAR-UHFFFAOYSA-N C(CCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1)OCCCC)C Chemical group C(CCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1)OCCCC)C UGMYZHYJONHFAR-UHFFFAOYSA-N 0.000 description 1
- ZDSMYLLITNVFDL-UHFFFAOYSA-N C(CCCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C(C=C1)OCCCCC Chemical group C(CCCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C(C=C1)OCCCCC ZDSMYLLITNVFDL-UHFFFAOYSA-N 0.000 description 1
- BIJBXIBPORMDLB-UHFFFAOYSA-N C(CCCCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1)OCCCCCC)C Chemical group C(CCCCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1)OCCCCCC)C BIJBXIBPORMDLB-UHFFFAOYSA-N 0.000 description 1
- JZJOSPIJOWLPLX-UHFFFAOYSA-N C(CCCCCCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1)OCCCCCCCC)C Chemical group C(CCCCCCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1)OCCCCCCCC)C JZJOSPIJOWLPLX-UHFFFAOYSA-N 0.000 description 1
- GJIKNQBWCZDKCL-UHFFFAOYSA-N C(CCCCCCCCCCCCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1)OCCCCCCCCCCCCCC)C Chemical group C(CCCCCCCCCCCCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1)OCCCCCCCCCCCCCC)C GJIKNQBWCZDKCL-UHFFFAOYSA-N 0.000 description 1
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- DCMSMGOMUHJWRL-UHFFFAOYSA-N COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=C(C=C(C=C1)OC)C(C)(C)C Chemical group COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=C(C=C(C=C1)OC)C(C)(C)C DCMSMGOMUHJWRL-UHFFFAOYSA-N 0.000 description 1
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- XNQZOCHPZUAPJA-UHFFFAOYSA-N COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=C(C=C(C=C1)OC)CCC Chemical group COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=C(C=C(C=C1)OC)CCC XNQZOCHPZUAPJA-UHFFFAOYSA-N 0.000 description 1
- TVKLOVBWCPCGOQ-UHFFFAOYSA-N COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=C(C=C(C=C1)OC)CCCC Chemical group COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=C(C=C(C=C1)OC)CCCC TVKLOVBWCPCGOQ-UHFFFAOYSA-N 0.000 description 1
- IITFXZJYNQOLBM-UHFFFAOYSA-N COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C(=C1)C(C)(C)C)OC)C(C)(C)C Chemical group COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C(=C1)C(C)(C)C)OC)C(C)(C)C IITFXZJYNQOLBM-UHFFFAOYSA-N 0.000 description 1
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- CGJLVGWRUBWNPP-UHFFFAOYSA-N COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C(=C1)C)OC)C(C)(C)C Chemical group COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C(=C1)C)OC)C(C)(C)C CGJLVGWRUBWNPP-UHFFFAOYSA-N 0.000 description 1
- UHQMMUPJEAHHRS-UHFFFAOYSA-N COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1)OC)C(C)(C)C Chemical group COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1)OC)C(C)(C)C UHQMMUPJEAHHRS-UHFFFAOYSA-N 0.000 description 1
- HAVBWNULXUVVHC-UHFFFAOYSA-N COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1)OC)C(C)C Chemical group COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1)OC)C(C)C HAVBWNULXUVVHC-UHFFFAOYSA-N 0.000 description 1
- NLCIFMKTAWNODH-UHFFFAOYSA-N COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1)OC)CC Chemical group COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1)OC)CC NLCIFMKTAWNODH-UHFFFAOYSA-N 0.000 description 1
- FYSHWSDNGMKYCY-UHFFFAOYSA-N COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1)OC)CC(C)C Chemical group COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1)OC)CC(C)C FYSHWSDNGMKYCY-UHFFFAOYSA-N 0.000 description 1
- IOLGKAATKHDYJF-UHFFFAOYSA-N COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1)OC)CCC Chemical group COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1)OC)CCC IOLGKAATKHDYJF-UHFFFAOYSA-N 0.000 description 1
- BWUZWFAJDUFUCD-UHFFFAOYSA-N COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1C)OC)C Chemical group COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1C)OC)C BWUZWFAJDUFUCD-UHFFFAOYSA-N 0.000 description 1
- MTDDKSPDUDORBN-UHFFFAOYSA-N COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1C)OC)C(C)(C)C Chemical group COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1C)OC)C(C)(C)C MTDDKSPDUDORBN-UHFFFAOYSA-N 0.000 description 1
- GDYFDEFHIAKOAQ-UHFFFAOYSA-N COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1C)OC)C(C)C Chemical group COC1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC(=C(C=C1C)OC)C(C)C GDYFDEFHIAKOAQ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 150000007514 bases Chemical class 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
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 235000012254 magnesium hydroxide Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007291093A (ja) * | 2006-03-31 | 2007-11-08 | Dainippon Ink & Chem Inc | ジフルオロベンゼン誘導体の製造方法 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03162484A (ja) * | 1989-11-20 | 1991-07-12 | Pioneer Electron Corp | 電界発光素子 |
| JP2002234856A (ja) * | 2001-02-08 | 2002-08-23 | Honshu Chem Ind Co Ltd | ４，４”−ジヒドロキシ−ｐ−ターフェニル類の製造方法 |
| JP2002308808A (ja) * | 2001-02-08 | 2002-10-23 | Honshu Chem Ind Co Ltd | 新規な４，４”−ジヒドロキシ−ｐ−ターフェニル類 |
| JP2004006754A (ja) * | 2002-03-26 | 2004-01-08 | Dainippon Printing Co Ltd | 有機半導体材料、有機半導体構造物、および、有機半導体装置 |
| JP2004235277A (ja) * | 2003-01-28 | 2004-08-19 | Dainippon Printing Co Ltd | 有機半導体素子、有機半導体装置、有機エレクトロルミネッセンス素子および有機エレクトロルミネッセンス装置 |
-
2003
- 2003-09-11 JP JP2003319460A patent/JP2005082569A/ja active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03162484A (ja) * | 1989-11-20 | 1991-07-12 | Pioneer Electron Corp | 電界発光素子 |
| JP2002234856A (ja) * | 2001-02-08 | 2002-08-23 | Honshu Chem Ind Co Ltd | ４，４”−ジヒドロキシ−ｐ−ターフェニル類の製造方法 |
| JP2002308808A (ja) * | 2001-02-08 | 2002-10-23 | Honshu Chem Ind Co Ltd | 新規な４，４”−ジヒドロキシ−ｐ−ターフェニル類 |
| JP2004006754A (ja) * | 2002-03-26 | 2004-01-08 | Dainippon Printing Co Ltd | 有機半導体材料、有機半導体構造物、および、有機半導体装置 |
| JP2004235277A (ja) * | 2003-01-28 | 2004-08-19 | Dainippon Printing Co Ltd | 有機半導体素子、有機半導体装置、有機エレクトロルミネッセンス素子および有機エレクトロルミネッセンス装置 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007291093A (ja) * | 2006-03-31 | 2007-11-08 | Dainippon Ink & Chem Inc | ジフルオロベンゼン誘導体の製造方法 |
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