CH648539A5 - Phenylethanes and use thereof in liquid-crystalline mixtures - Google Patents
Phenylethanes and use thereof in liquid-crystalline mixtures Download PDFInfo
- Publication number
- CH648539A5 CH648539A5 CH6572/81A CH657281A CH648539A5 CH 648539 A5 CH648539 A5 CH 648539A5 CH 6572/81 A CH6572/81 A CH 6572/81A CH 657281 A CH657281 A CH 657281A CH 648539 A5 CH648539 A5 CH 648539A5
- Authority
- CH
- Switzerland
- Prior art keywords
- trans
- alkylcyclohexyl
- ethyl
- phenyl
- compounds
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 47
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical class CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 title claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 69
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 24
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 12
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- -1 pentylcyclohexyl Chemical group 0.000 claims description 22
- 235000010290 biphenyl Nutrition 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 239000003989 dielectric material Substances 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 239000004990 Smectic liquid crystal Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 210000004027 cell Anatomy 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 230000004044 response Effects 0.000 claims description 4
- 230000003098 cholesteric effect Effects 0.000 claims description 3
- 230000007704 transition Effects 0.000 claims description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 2
- WLNDDIWESXCXHM-UHFFFAOYSA-N 2-phenyl-1,4-dioxane Chemical compound C1OCCOC1C1=CC=CC=C1 WLNDDIWESXCXHM-UHFFFAOYSA-N 0.000 claims description 2
- BWRMZQGIDWILAU-UHFFFAOYSA-N 4,6-diphenylpyrimidine Chemical class C1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=NC=N1 BWRMZQGIDWILAU-UHFFFAOYSA-N 0.000 claims description 2
- BOOGLODHTHQEQO-UHFFFAOYSA-N 4-cyclohexyl-2-phenylpyrimidine Chemical class C1CCCCC1C1=CC=NC(C=2C=CC=CC=2)=N1 BOOGLODHTHQEQO-UHFFFAOYSA-N 0.000 claims description 2
- 239000002262 Schiff base Substances 0.000 claims description 2
- 150000004753 Schiff bases Chemical class 0.000 claims description 2
- 150000004074 biphenyls Chemical class 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000001851 cinnamic acid derivatives Chemical class 0.000 claims description 2
- 230000008094 contradictory effect Effects 0.000 claims description 2
- 210000002858 crystal cell Anatomy 0.000 claims description 2
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical class C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 claims description 2
- 230000007613 environmental effect Effects 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 150000001564 phenyl benzoates Chemical class 0.000 claims description 2
- OPYYWWIJPHKUDZ-UHFFFAOYSA-N phenyl cyclohexanecarboxylate Chemical class C1CCCCC1C(=O)OC1=CC=CC=C1 OPYYWWIJPHKUDZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000001911 terphenyls Chemical class 0.000 claims description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 2
- HYYFAYFMSHAWFA-UHFFFAOYSA-N 2-cyclohexylethylbenzene Chemical compound C1CCCCC1CCC1=CC=CC=C1 HYYFAYFMSHAWFA-UHFFFAOYSA-N 0.000 claims 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 34
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 239000004305 biphenyl Substances 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 229910052740 iodine Inorganic materials 0.000 description 15
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000012071 phase Substances 0.000 description 7
- 238000006277 sulfonation reaction Methods 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- RVLAXPQGTRTHEV-UHFFFAOYSA-N 4-pentylcyclohexane-1-carboxylic acid Chemical compound CCCCCC1CCC(C(O)=O)CC1 RVLAXPQGTRTHEV-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- HMUGRILXVBKBID-UHFFFAOYSA-N 1-(bromomethyl)-4-[4-(bromomethyl)phenyl]benzene Chemical group C1=CC(CBr)=CC=C1C1=CC=C(CBr)C=C1 HMUGRILXVBKBID-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZXWKTUCBAYGXJD-JFQKCFOJSA-N C(CCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCCCC Chemical group C(CCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCCCC ZXWKTUCBAYGXJD-JFQKCFOJSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Chemical group 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VSNGFYYRBATOTN-UHFFFAOYSA-N 4-(5-heptylpyrimidin-2-yl)benzonitrile Chemical compound N1=CC(CCCCCCC)=CN=C1C1=CC=C(C#N)C=C1 VSNGFYYRBATOTN-UHFFFAOYSA-N 0.000 description 3
- RGONNDWSVOCREF-UHFFFAOYSA-N 4-(5-pentylpyrimidin-2-yl)benzonitrile Chemical compound N1=CC(CCCCC)=CN=C1C1=CC=C(C#N)C=C1 RGONNDWSVOCREF-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical compound C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OESYGYCCZCPEGL-HZCBDIJESA-N BrCC1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCCCC Chemical group BrCC1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCCCC OESYGYCCZCPEGL-HZCBDIJESA-N 0.000 description 2
- GHYIAIJFCWKIDL-IXFIMZJLSA-N C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)C=C[C@@H]1CC[C@H](CC1)CCCCC Chemical group C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)C=C[C@@H]1CC[C@H](CC1)CCCCC GHYIAIJFCWKIDL-IXFIMZJLSA-N 0.000 description 2
- PXJYLNDQCJSKJO-XUTJKUGGSA-N C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)C=O Chemical compound C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)C=O PXJYLNDQCJSKJO-XUTJKUGGSA-N 0.000 description 2
- BITDTKIPCQRBNA-XUTJKUGGSA-N C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CO Chemical compound C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CO BITDTKIPCQRBNA-XUTJKUGGSA-N 0.000 description 2
- YAZXDRDFNUEKBH-KOMQPUFPSA-N C1C[C@@H](CC)CC[C@@H]1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 Chemical compound C1C[C@@H](CC)CC[C@@H]1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 YAZXDRDFNUEKBH-KOMQPUFPSA-N 0.000 description 2
- PAOGJHSCNSVUMN-AFMUELSESA-N CCCCC[C@H]1CC[C@@H](CC1)c1ccc(CC[C@H]2CC[C@H](CCCC)CC2)cc1 Chemical compound CCCCC[C@H]1CC[C@@H](CC1)c1ccc(CC[C@H]2CC[C@H](CCCC)CC2)cc1 PAOGJHSCNSVUMN-AFMUELSESA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- RVHSTXJKKZWWDQ-UHFFFAOYSA-N 1,1,1,2-tetrabromoethane Chemical compound BrCC(Br)(Br)Br RVHSTXJKKZWWDQ-UHFFFAOYSA-N 0.000 description 1
- HXOWMHXGHNZDFT-UHFFFAOYSA-N 1-(bromomethyl)-4-pentylcyclohexane Chemical compound CCCCCC1CCC(CBr)CC1 HXOWMHXGHNZDFT-UHFFFAOYSA-N 0.000 description 1
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 1
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 1
- QKEBUASRTJNJJS-UHFFFAOYSA-N 4-[4-(4-pentylcyclohexyl)phenyl]benzonitrile Chemical compound C1CC(CCCCC)CCC1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 QKEBUASRTJNJJS-UHFFFAOYSA-N 0.000 description 1
- JFKUBRAOUZEZSL-UHFFFAOYSA-N 4-butylbenzoic acid Chemical compound CCCCC1=CC=C(C(O)=O)C=C1 JFKUBRAOUZEZSL-UHFFFAOYSA-N 0.000 description 1
- QFFSAGSUDNLFFK-UHFFFAOYSA-N 4-pentylcyclohexane-1-carbaldehyde Chemical compound CCCCCC1CCC(C=O)CC1 QFFSAGSUDNLFFK-UHFFFAOYSA-N 0.000 description 1
- QCNUKEGGHOLBES-UHFFFAOYSA-N 4-propylcyclohexane-1-carboxylic acid Chemical compound CCCC1CCC(C(O)=O)CC1 QCNUKEGGHOLBES-UHFFFAOYSA-N 0.000 description 1
- CGLZXGSKGSEIAR-XUTJKUGGSA-N BrCC1=CC=C(C=C1)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCCC Chemical group BrCC1=CC=C(C=C1)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCCC CGLZXGSKGSEIAR-XUTJKUGGSA-N 0.000 description 1
- ZPZFJQQZHCLTQB-AFMUELSESA-N C(C)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC Chemical group C(C)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC ZPZFJQQZHCLTQB-AFMUELSESA-N 0.000 description 1
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- SPRYHIIFIRLRMZ-IXFIMZJLSA-N C(CCCCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC Chemical group C(CCCCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC SPRYHIIFIRLRMZ-IXFIMZJLSA-N 0.000 description 1
- NQWDXAHOPDKHEN-PBVHZTIHSA-N C(CCCCCC)[C@@H]1CC[C@H](CC1)CC(O)C1=CC=C(C=C1)OCC Chemical compound C(CCCCCC)[C@@H]1CC[C@H](CC1)CC(O)C1=CC=C(C=C1)OCC NQWDXAHOPDKHEN-PBVHZTIHSA-N 0.000 description 1
- BXRJUPMACUZOBJ-ZWGSZDQZSA-N C(C[C@@H]1CC[C@H](CC1)CCCCC)[C@@H]1CC[C@H](CC1)CCCCC Chemical compound C(C[C@@H]1CC[C@H](CC1)CCCCC)[C@@H]1CC[C@H](CC1)CCCCC BXRJUPMACUZOBJ-ZWGSZDQZSA-N 0.000 description 1
- LPKGMNAEGKACDO-DALKXGRXSA-N C1=CC(CCCCC)=CC=C1[C@@H]1CC[C@@H](C(=O)O[C@@H]2CC[C@@H](CCC)CC2)CC1 Chemical compound C1=CC(CCCCC)=CC=C1[C@@H]1CC[C@@H](C(=O)O[C@@H]2CC[C@@H](CCC)CC2)CC1 LPKGMNAEGKACDO-DALKXGRXSA-N 0.000 description 1
- JAYBMJPZPJBTQZ-WKILWMFISA-N C1C[C@@H](CCCC)CC[C@@H]1C(=O)OC1=CC=C(OCC)C=C1 Chemical compound C1C[C@@H](CCCC)CC[C@@H]1C(=O)OC1=CC=C(OCC)C=C1 JAYBMJPZPJBTQZ-WKILWMFISA-N 0.000 description 1
- CNOSQBDQVXWGOJ-KZIAUGABSA-N C1C[C@@H](CCCCC)CC[C@@H]1C(C=C1)=CC=C1CCC(C=C1)=CC=C1CC[C@@H]1CC[C@@H](CCCC)CC1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C(C=C1)=CC=C1CCC(C=C1)=CC=C1CC[C@@H]1CC[C@@H](CCCC)CC1 CNOSQBDQVXWGOJ-KZIAUGABSA-N 0.000 description 1
- OMXWVWDCNNMTTN-CQXGVVMCSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C=2C=CC(CC[C@@H]3CC[C@@H](CCCC)CC3)=CC=2)C=C1 Chemical group C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C=2C=CC(CC[C@@H]3CC[C@@H](CCCC)CC3)=CC=2)C=C1 OMXWVWDCNNMTTN-CQXGVVMCSA-N 0.000 description 1
- XIXOFKHADLKBQN-UAPYVXQJSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 XIXOFKHADLKBQN-UAPYVXQJSA-N 0.000 description 1
- CECDPADATRVQLC-OZIXAUCHSA-N CCCCC[C@H]1CC[C@H](CCC(C=C2)=CC=C2C(C=C2)=CC=C2C2=CC=C(CCCCC)C=C2)CC1 Chemical group CCCCC[C@H]1CC[C@H](CCC(C=C2)=CC=C2C(C=C2)=CC=C2C2=CC=C(CCCCC)C=C2)CC1 CECDPADATRVQLC-OZIXAUCHSA-N 0.000 description 1
- GDHWEYVFLSGWMT-YROJFRDXSA-N CCC[C@H]1CC[C@H](CCC2=CC=C(CC[C@H]3CC[C@H](CC)CC3)C=C2)CC1 Chemical compound CCC[C@H]1CC[C@H](CCC2=CC=C(CC[C@H]3CC[C@H](CC)CC3)C=C2)CC1 GDHWEYVFLSGWMT-YROJFRDXSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 238000006828 Rosenmund reduction reaction Methods 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- SFHGONLFTNHXDX-UHFFFAOYSA-N [4-[4-(hydroxymethyl)phenyl]phenyl]methanol Chemical group C1=CC(CO)=CC=C1C1=CC=C(CO)C=C1 SFHGONLFTNHXDX-UHFFFAOYSA-N 0.000 description 1
- KNJOQRFTJUYXTB-KBRNKZTISA-M [Br-].C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [Br-].C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 KNJOQRFTJUYXTB-KBRNKZTISA-M 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- HCJWWBBBSCXJMS-UHFFFAOYSA-J copper;dilithium;tetrachloride Chemical compound [Li+].[Li+].[Cl-].[Cl-].[Cl-].[Cl-].[Cu+2] HCJWWBBBSCXJMS-UHFFFAOYSA-J 0.000 description 1
- 238000005859 coupling reaction Methods 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
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
- C07C1/325—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a metal atom
- C07C1/326—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a metal atom the hetero-atom being a magnesium atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
- C07C1/34—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen reacting phosphines with aldehydes or ketones, e.g. Wittig reaction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/44—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reduction and hydrolysis of nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5456—Arylalkanephosphonium compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3028—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6572/81A CH648539A5 (en) | 1981-10-14 | 1981-10-14 | Phenylethanes and use thereof in liquid-crystalline mixtures |
| US06/432,212 US4583826A (en) | 1981-10-14 | 1982-10-01 | Phenylethanes |
| DE19823237367 DE3237367A1 (de) | 1981-10-14 | 1982-10-08 | Phenylaethane |
| JP57177726A JPS5872528A (ja) | 1981-10-14 | 1982-10-12 | フエニルエタン類 |
| GB08229191A GB2107733B (en) | 1981-10-14 | 1982-10-13 | Phenylethanes |
| HK553/86A HK55386A (en) | 1981-10-14 | 1986-07-24 | Phenylethanes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6572/81A CH648539A5 (en) | 1981-10-14 | 1981-10-14 | Phenylethanes and use thereof in liquid-crystalline mixtures |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH648539A5 true CH648539A5 (en) | 1985-03-29 |
Family
ID=4311709
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH6572/81A CH648539A5 (en) | 1981-10-14 | 1981-10-14 | Phenylethanes and use thereof in liquid-crystalline mixtures |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5872528A (ja) |
| CH (1) | CH648539A5 (ja) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH646675A5 (en) * | 1981-01-30 | 1984-12-14 | Hoffmann La Roche | Disubstituted ethanes |
| JPS6033411B2 (ja) * | 1981-03-06 | 1985-08-02 | 大日本インキ化学工業株式会社 | １−シクロヘキシル−２−シクロヘキシルフエニルエタン誘導体 |
| JPS5933565B2 (ja) * | 1981-07-09 | 1984-08-16 | 大日本インキ化学工業株式会社 | １−シクロヘキシル−２−シクロヘキシルビフエニルエタン誘導体 |
| JPS588023A (ja) * | 1981-07-09 | 1983-01-18 | Dainippon Ink & Chem Inc | １，２−ジ−（シクロヘキシルフエニル）エタン誘導体 |
| JPS5933566B2 (ja) * | 1981-07-09 | 1984-08-16 | 大日本インキ化学工業株式会社 | １，４−ジ−（シクロヘキシルエチル）ビフエニル誘導体 |
-
1981
- 1981-10-14 CH CH6572/81A patent/CH648539A5/de not_active IP Right Cessation
-
1982
- 1982-10-12 JP JP57177726A patent/JPS5872528A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0329050B2 (ja) | 1991-04-23 |
| JPS5872528A (ja) | 1983-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUE | Assignment |
Owner name: F. HOFFMANN-LA ROCHE AG |
|
| PL | Patent ceased |