JPS5921846B2 - 新規な１，１，３，３−置換されたヒドロキシインダンの製造方法 - Google Patents
新規な１，１，３，３−置換されたヒドロキシインダンの製造方法Info
- Publication number
- JPS5921846B2 JPS5921846B2 JP49129660A JP12966074A JPS5921846B2 JP S5921846 B2 JPS5921846 B2 JP S5921846B2 JP 49129660 A JP49129660 A JP 49129660A JP 12966074 A JP12966074 A JP 12966074A JP S5921846 B2 JPS5921846 B2 JP S5921846B2
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- tert
- mol
- hours
- methyl
- 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.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- YIAPLDFPUUJILH-UHFFFAOYSA-N indan-1-ol Chemical class C1=CC=C2C(O)CCC2=C1 YIAPLDFPUUJILH-UHFFFAOYSA-N 0.000 title description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- -1 3-substituted hydroxyindan Chemical class 0.000 claims description 22
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 claims description 18
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 18
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 claims description 10
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 10
- WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical compound CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 claims description 8
- 125000002723 alicyclic group Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 5
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical compound CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 claims description 4
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 claims description 4
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 claims description 4
- CYEKUDPFXBLGHH-UHFFFAOYSA-N 3-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC(O)=C1 CYEKUDPFXBLGHH-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- OWWIWYDDISJUMY-UHFFFAOYSA-N 2,3-dimethylbut-1-ene Chemical compound CC(C)C(C)=C OWWIWYDDISJUMY-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- LAAVYEUJEMRIGF-UHFFFAOYSA-N 2,4,4-trimethylpent-2-ene Chemical compound CC(C)=CC(C)(C)C LAAVYEUJEMRIGF-UHFFFAOYSA-N 0.000 claims 1
- ZDWSNKPLZUXBPE-UHFFFAOYSA-N 3,5-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(O)=CC(C(C)(C)C)=C1 ZDWSNKPLZUXBPE-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 49
- 238000000034 method Methods 0.000 description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 239000003054 catalyst Substances 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 36
- 239000000203 mixture Substances 0.000 description 33
- 239000011541 reaction mixture Substances 0.000 description 30
- 239000002253 acid Substances 0.000 description 27
- 150000001336 alkenes Chemical group 0.000 description 27
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 23
- 238000003756 stirring Methods 0.000 description 21
- 239000002904 solvent Substances 0.000 description 18
- 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 17
- JAGRUUPXPPLSRX-UHFFFAOYSA-N 4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=C(O)C=C1 JAGRUUPXPPLSRX-UHFFFAOYSA-N 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 238000009835 boiling Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000004927 clay Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 239000012442 inert solvent Substances 0.000 description 10
- OJCRKGPORQMMRN-UHFFFAOYSA-N 1,1,3,3-tetramethyl-2h-inden-5-ol Chemical compound OC1=CC=C2C(C)(C)CC(C)(C)C2=C1 OJCRKGPORQMMRN-UHFFFAOYSA-N 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000003377 acid catalyst Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 238000004508 fractional distillation Methods 0.000 description 7
- 238000011065 in-situ storage Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 150000002989 phenols Chemical class 0.000 description 7
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 239000001294 propane Substances 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 description 3
- PMNVVCYFXVWMON-UHFFFAOYSA-N 6-tert-butyl-1,1,3,3-tetramethyl-2h-inden-5-ol Chemical compound C1=C(O)C(C(C)(C)C)=CC2=C1C(C)(C)CC2(C)C PMNVVCYFXVWMON-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 125000000542 sulfonic acid group Chemical group 0.000 description 3
- ZWXLWYJXJMJPSB-UHFFFAOYSA-N 1-ethyl-1,3,3-trimethyl-2h-inden-5-ol Chemical compound OC1=CC=C2C(CC)(C)CC(C)(C)C2=C1 ZWXLWYJXJMJPSB-UHFFFAOYSA-N 0.000 description 2
- ZDRSNHRWLQQICP-UHFFFAOYSA-N 2-tert-butyl-4-[2-(3-tert-butyl-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C1=C(O)C(C(C)(C)C)=CC(C(C)(C)C=2C=C(C(O)=CC=2)C(C)(C)C)=C1 ZDRSNHRWLQQICP-UHFFFAOYSA-N 0.000 description 2
- WBEOVNLNRQDXIJ-UHFFFAOYSA-N 3-(2,2-dimethylpropyl)-1,1,3-trimethyl-2h-inden-5-ol Chemical compound C1=C(O)C=C2C(CC(C)(C)C)(C)CC(C)(C)C2=C1 WBEOVNLNRQDXIJ-UHFFFAOYSA-N 0.000 description 2
- PMZXHWXCHFTBFZ-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)phenol Chemical compound CC(C)(O)C1=CC=C(O)C=C1 PMZXHWXCHFTBFZ-UHFFFAOYSA-N 0.000 description 2
- HTVITOHKHWFJKO-UHFFFAOYSA-N Bisphenol B Chemical compound C=1C=C(O)C=CC=1C(C)(CC)C1=CC=C(O)C=C1 HTVITOHKHWFJKO-UHFFFAOYSA-N 0.000 description 2
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical group CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- OAZWKUSHEIWQKO-UHFFFAOYSA-N 1,1,2,3,3-pentamethyl-2h-inden-5-ol Chemical compound C1=C(O)C=C2C(C)(C)C(C)C(C)(C)C2=C1 OAZWKUSHEIWQKO-UHFFFAOYSA-N 0.000 description 1
- VYKUVTAOOOEUBM-UHFFFAOYSA-N 1,1-dimethyl-4,6-di(propan-2-yl)-2,3-dihydroinden-5-ol Chemical compound CC(C)C1=C(O)C(C(C)C)=CC2=C1CCC2(C)C VYKUVTAOOOEUBM-UHFFFAOYSA-N 0.000 description 1
- LEBBCUICCMXSMS-UHFFFAOYSA-N 1,2,3,3,4,6-hexamethyl-1,2-dihydroinden-5-ol Chemical compound C1=C(C)C(O)=C(C)C2=C1C(C)C(C)C2(C)C LEBBCUICCMXSMS-UHFFFAOYSA-N 0.000 description 1
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- DPHNJPUOMLRELT-UHFFFAOYSA-N 2,3-dihydro-1h-inden-4-ol Chemical class OC1=CC=CC2=C1CCC2 DPHNJPUOMLRELT-UHFFFAOYSA-N 0.000 description 1
- XRQYDLXBZRPDCH-UHFFFAOYSA-N 2,6-dichloro-4-(2-hydroxypropan-2-yl)phenol Chemical compound CC(C)(O)C1=CC(Cl)=C(O)C(Cl)=C1 XRQYDLXBZRPDCH-UHFFFAOYSA-N 0.000 description 1
- KNEFGIUPHCGYAA-UHFFFAOYSA-N 2,6-dichloro-4-(2-methoxypropan-2-yl)phenol Chemical compound COC(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KNEFGIUPHCGYAA-UHFFFAOYSA-N 0.000 description 1
- ADWNMLOJOWWQAZ-UHFFFAOYSA-N 2,6-dichloro-4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC(Cl)=C(O)C(Cl)=C1 ADWNMLOJOWWQAZ-UHFFFAOYSA-N 0.000 description 1
- MSMMRZUNVSWUEI-UHFFFAOYSA-N 2,6-dimethyl-4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC(C)=C(O)C(C)=C1 MSMMRZUNVSWUEI-UHFFFAOYSA-N 0.000 description 1
- DZZHBSWENNHOLF-UHFFFAOYSA-N 2,6-ditert-butyl-4-(2-hydroxypropan-2-yl)phenol Chemical compound CC(C)(C)C1=CC(C(C)(C)O)=CC(C(C)(C)C)=C1O DZZHBSWENNHOLF-UHFFFAOYSA-N 0.000 description 1
- YANMXXZMTZMIIT-UHFFFAOYSA-N 2,6-ditert-butyl-4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 YANMXXZMTZMIIT-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- OKECGUSGCAIPNZ-UHFFFAOYSA-N 2-chloro-4-(2-hydroxypropan-2-yl)phenol Chemical compound CC(C)(O)C1=CC=C(O)C(Cl)=C1 OKECGUSGCAIPNZ-UHFFFAOYSA-N 0.000 description 1
- XBQRPFBBTWXIFI-UHFFFAOYSA-N 2-chloro-4-[2-(3-chloro-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=C(O)C(Cl)=CC=1C(C)(C)C1=CC=C(O)C(Cl)=C1 XBQRPFBBTWXIFI-UHFFFAOYSA-N 0.000 description 1
- UWLARYUTZFXZMD-UHFFFAOYSA-N 2-chloro-4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=C(O)C(Cl)=C1 UWLARYUTZFXZMD-UHFFFAOYSA-N 0.000 description 1
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical class OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 1
- UITUMGKYHZMNKN-UHFFFAOYSA-N 2-methyl-4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=C(O)C(C)=C1 UITUMGKYHZMNKN-UHFFFAOYSA-N 0.000 description 1
- GFJUOMJGSXRJJY-UHFFFAOYSA-N 2-methylprop-1-ene Chemical group CC(C)=C.CC(C)=C GFJUOMJGSXRJJY-UHFFFAOYSA-N 0.000 description 1
- WUQYBSRMWWRFQH-UHFFFAOYSA-N 2-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC=C1O WUQYBSRMWWRFQH-UHFFFAOYSA-N 0.000 description 1
- WHGXZPQWZJUGEP-UHFFFAOYSA-N 2-prop-1-enylphenol Chemical compound CC=CC1=CC=CC=C1O WHGXZPQWZJUGEP-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- TXYRFLUDJODGTP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(3-tert-butyl-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound C1=C(O)C(C(C)(C)C)=CC(C2(CCCCC2)C=2C=C(C(O)=CC=2)C(C)(C)C)=C1 TXYRFLUDJODGTP-UHFFFAOYSA-N 0.000 description 1
- UBLXHWUFCQEDJH-UHFFFAOYSA-N 2-tert-butyl-4-[1-(3-tert-butyl-4-hydroxyphenyl)cyclopentyl]phenol Chemical compound C1=C(O)C(C(C)(C)C)=CC(C2(CCCC2)C=2C=C(C(O)=CC=2)C(C)(C)C)=C1 UBLXHWUFCQEDJH-UHFFFAOYSA-N 0.000 description 1
- UHSLAFBDUFODHO-UHFFFAOYSA-N 2-tert-butyl-4-[2-(3-tert-butyl-4-hydroxy-5-methylphenyl)propan-2-yl]-6-methylphenol Chemical compound CC(C)(C)C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 UHSLAFBDUFODHO-UHFFFAOYSA-N 0.000 description 1
- ZUVOHEFSXJRQRO-UHFFFAOYSA-N 2-tert-butyl-4-[2-(3-tert-butyl-4-hydroxyphenyl)butan-2-yl]phenol Chemical compound C=1C=C(O)C(C(C)(C)C)=CC=1C(C)(CC)C1=CC=C(O)C(C(C)(C)C)=C1 ZUVOHEFSXJRQRO-UHFFFAOYSA-N 0.000 description 1
- MMQGELDTLCOILM-UHFFFAOYSA-N 2-tert-butyl-4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=C(O)C(C(C)(C)C)=C1 MMQGELDTLCOILM-UHFFFAOYSA-N 0.000 description 1
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 1
- QINGGXJSOCDZPS-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-2-methylphenol Chemical compound CC1=CC(C(C)(C)O)=CC=C1O QINGGXJSOCDZPS-UHFFFAOYSA-N 0.000 description 1
- UOMUYBXJIYHKMK-UHFFFAOYSA-N 4-(2-methoxypropan-2-yl)-2,6-dimethylphenol Chemical compound COC(C)(C)C1=CC(C)=C(O)C(C)=C1 UOMUYBXJIYHKMK-UHFFFAOYSA-N 0.000 description 1
- UGZYVEVAQNFHBK-UHFFFAOYSA-N 4-(2-methoxypropan-2-yl)-2-methylphenol Chemical compound COC(C)(C)C1=CC=C(O)C(C)=C1 UGZYVEVAQNFHBK-UHFFFAOYSA-N 0.000 description 1
- QQMZQUNIZSADNR-UHFFFAOYSA-N 4-(2-methoxypropan-2-yl)phenol Chemical compound COC(C)(C)C1=CC=C(O)C=C1 QQMZQUNIZSADNR-UHFFFAOYSA-N 0.000 description 1
- KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 description 1
- OVVCSFQRAXVPGT-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)cyclopentyl]phenol Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCC1 OVVCSFQRAXVPGT-UHFFFAOYSA-N 0.000 description 1
- PMWJZWDTSSMFEP-UHFFFAOYSA-N 6-chloro-1,1,3,3-tetramethyl-2h-inden-5-ol Chemical compound ClC1=C(O)C=C2C(C)(C)CC(C)(C)C2=C1 PMWJZWDTSSMFEP-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical class F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- BULOCEWDRJUMEL-UHFFFAOYSA-N benzene formaldehyde Chemical compound C=O.C1=CC=CC=C1.C=O BULOCEWDRJUMEL-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical class [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000002221 fluorine Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical class FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229930015698 phenylpropene Natural products 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229940100890 silver compound Drugs 0.000 description 1
- 150000003379 silver compounds Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010555 transalkylation reaction Methods 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/24—Halogenated derivatives
- C07C39/42—Halogenated derivatives containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2356813A DE2356813C2 (de) | 1973-11-14 | 1973-11-14 | Verfahren zur Herstellung von 1,1,3,3-substituierten 5-Hydroxyindanen |
| DE2356813 | 1973-11-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5082050A JPS5082050A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-07-03 |
| JPS5921846B2 true JPS5921846B2 (ja) | 1984-05-22 |
Family
ID=5898080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP49129660A Expired JPS5921846B2 (ja) | 1973-11-14 | 1974-11-12 | 新規な１，１，３，３−置換されたヒドロキシインダンの製造方法 |
Country Status (11)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3954889A (en) * | 1973-01-31 | 1976-05-04 | Bayer Aktiengesellschaft | Process for the production of 1,1,3,3-substituted hydroxyindanes |
| ZA796150B (en) * | 1978-12-07 | 1980-10-29 | Ici Ltd | Chlorination process |
| US4257857A (en) * | 1979-01-22 | 1981-03-24 | Imperial Chemical Industries Limited | Liquid phase preparation of 2-chloro-5-trifluoromethylpyridine and 2-chloro-5-perchlorofluoromethylpyridine |
| US4418220A (en) * | 1979-11-26 | 1983-11-29 | Mitsui Toatsu Chemicals Inc. | Novel indene compound and novel process for producing indene compounds |
| US4366328A (en) * | 1979-11-26 | 1982-12-28 | Mitsui Toatsu Chemicals, Inc. | Indene compound and novel process for producing indene compounds |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1972599A (en) * | 1932-07-22 | 1934-09-04 | Dow Chemical Co | Method of making tertiary alkyl phenols |
| US2109015A (en) * | 1935-07-05 | 1938-02-22 | Joseph B Niederl | Polycyclic phenolic condensation products |
| US2091565A (en) * | 1935-07-15 | 1937-08-31 | Dow Chemical Co | Preparation of tertiary butyl phenol |
| US2265583A (en) * | 1940-06-26 | 1941-12-09 | Gulf Research Development Co | Production of tertiary olefins |
| DE1004168B (de) * | 1953-09-05 | 1957-03-14 | Distillers Co Yeast Ltd | Verfahren zur Herstellung von dimeren m-Isopropenylphenolen |
| GB788747A (en) * | 1954-07-16 | 1958-01-08 | American Cyanamid Co | New dihydric phenols and resinous products prepared therefrom |
| US2948704A (en) * | 1956-09-10 | 1960-08-09 | Goodrich Co B F | Alkylated indanols as deterioration retarders for rubbers |
| US3057929A (en) * | 1959-09-28 | 1962-10-09 | Universal Oil Prod Co | Preparation of indanols |
| DE1138042B (de) * | 1959-11-25 | 1962-10-18 | Ciba Geigy | Verfahren zur Herstellung von 1, 3, 3-Trimethyl-1-(p-hydroxyphenyl)-indanol-(6) |
| US3644540A (en) * | 1967-10-10 | 1972-02-22 | Givaudan Corp | 5 7 - diisopropyl-1 1-dimethyl-6-hydroxyindan and process for preparing same |
| DE2304588A1 (de) * | 1973-01-31 | 1974-08-01 | Bayer Ag | Verfahren zur herstellung von hydroxyindanen |
| US3954889A (en) * | 1973-01-31 | 1976-05-04 | Bayer Aktiengesellschaft | Process for the production of 1,1,3,3-substituted hydroxyindanes |
-
1973
- 1973-11-14 DE DE2356813A patent/DE2356813C2/de not_active Expired
-
1974
- 1974-10-22 US US05/516,945 patent/US4045499A/en not_active Expired - Lifetime
- 1974-11-11 GB GB4868874A patent/GB1431248A/en not_active Expired
- 1974-11-12 IT IT53989/74A patent/IT1023214B/it active
- 1974-11-12 JP JP49129660A patent/JPS5921846B2/ja not_active Expired
- 1974-11-12 LU LU71275A patent/LU71275A1/xx unknown
- 1974-11-13 IE IE2333/74A patent/IE40208B1/xx unknown
- 1974-11-13 DK DK590874A patent/DK590874A/da unknown
- 1974-11-13 BE BE150443A patent/BE822124A/xx not_active IP Right Cessation
- 1974-11-14 NL NL7414885A patent/NL7414885A/xx not_active Application Discontinuation
- 1974-11-14 FR FR7437591A patent/FR2250733B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2356813A1 (de) | 1975-05-15 |
| LU71275A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-08-20 |
| BE822124A (fr) | 1975-05-13 |
| FR2250733B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-07-04 |
| IE40208B1 (en) | 1979-04-11 |
| FR2250733A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-06-06 |
| DK590874A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-07-14 |
| US4045499A (en) | 1977-08-30 |
| IE40208L (en) | 1975-05-14 |
| JPS5082050A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-07-03 |
| IT1023214B (it) | 1978-05-10 |
| NL7414885A (nl) | 1975-05-16 |
| DE2356813C2 (de) | 1983-03-03 |
| GB1431248A (en) | 1976-04-07 |
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