DE2535046C3 - Biphenylcarbonsäurephenyl- bzw. Benzoesäurebiphenylester, Verfahren zu deren Herstellung und deren Verwendung in flüssigkristallinen Dielektrika - Google Patents
Biphenylcarbonsäurephenyl- bzw. Benzoesäurebiphenylester, Verfahren zu deren Herstellung und deren Verwendung in flüssigkristallinen DielektrikaInfo
- Publication number
- DE2535046C3 DE2535046C3 DE19752535046 DE2535046A DE2535046C3 DE 2535046 C3 DE2535046 C3 DE 2535046C3 DE 19752535046 DE19752535046 DE 19752535046 DE 2535046 A DE2535046 A DE 2535046A DE 2535046 C3 DE2535046 C3 DE 2535046C3
- Authority
- DE
- Germany
- Prior art keywords
- benzoic acid
- ester
- acid
- pentylphenyl
- cyano
- 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
- -1 benzoic acid biphenyl ester Chemical class 0.000 title claims description 65
- 238000000034 method Methods 0.000 title claims description 10
- 230000008569 process Effects 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000003989 dielectric material Substances 0.000 title description 18
- 150000001875 compounds Chemical class 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 5
- OLPCSEIDQQDELO-UHFFFAOYSA-N (2-phenylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1C1=CC=CC=C1 OLPCSEIDQQDELO-UHFFFAOYSA-N 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 2
- KEUYTTBDXLSWDI-UHFFFAOYSA-N phenyl 2-phenylbenzoate Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1C(=O)OC1=CC=CC=C1 KEUYTTBDXLSWDI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 description 130
- 229910052700 potassium Inorganic materials 0.000 description 104
- 150000002148 esters Chemical class 0.000 description 58
- 239000000203 mixture Substances 0.000 description 29
- VRGQQLFRUKMDSW-UHFFFAOYSA-N 4-(4-pentylphenyl)benzoic acid Chemical compound C1=CC(CCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 VRGQQLFRUKMDSW-UHFFFAOYSA-N 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000126 substance Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- ZGOWXOZNUNZPAV-UHFFFAOYSA-N 4-(4-heptylphenyl)benzonitrile Chemical group C1=CC(CCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 ZGOWXOZNUNZPAV-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- GPGGNNIMKOVSAG-UHFFFAOYSA-N 4-(4-octoxyphenyl)benzonitrile Chemical group C1=CC(OCCCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 GPGGNNIMKOVSAG-UHFFFAOYSA-N 0.000 description 9
- 239000005215 4-Cyano-4'-n-octyloxybiphenyl Substances 0.000 description 9
- HHPCNRKYVYWYAU-UHFFFAOYSA-N 4-cyano-4'-pentylbiphenyl Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C#N)C=C1 HHPCNRKYVYWYAU-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- HBQUXMZZODHFMJ-UHFFFAOYSA-N 4-hexoxybenzoic acid Chemical compound CCCCCCOC1=CC=C(C(O)=O)C=C1 HBQUXMZZODHFMJ-UHFFFAOYSA-N 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 238000005886 esterification reaction Methods 0.000 description 8
- XVROSBHWACAQRL-UHFFFAOYSA-N 4-(4-heptylphenyl)benzoic acid Chemical compound C1=CC(CCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 XVROSBHWACAQRL-UHFFFAOYSA-N 0.000 description 7
- 239000005711 Benzoic acid Substances 0.000 description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 239000004990 Smectic liquid crystal Substances 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- ROJCBWVSXWIGAL-UHFFFAOYSA-N 4-(4-hexylphenyl)benzoic acid Chemical compound C1=CC(CCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 ROJCBWVSXWIGAL-UHFFFAOYSA-N 0.000 description 4
- CPEPWESLFZVUEP-UHFFFAOYSA-N 4-hexylbenzoic acid Chemical compound CCCCCCC1=CC=C(C(O)=O)C=C1 CPEPWESLFZVUEP-UHFFFAOYSA-N 0.000 description 4
- CWYNKKGQJYAHQG-UHFFFAOYSA-N 4-pentylbenzoic acid Chemical compound CCCCCC1=CC=C(C(O)=O)C=C1 CWYNKKGQJYAHQG-UHFFFAOYSA-N 0.000 description 4
- GDFUWFOCYZZGQU-UHFFFAOYSA-N 4-propoxybenzoic acid Chemical compound CCCOC1=CC=C(C(O)=O)C=C1 GDFUWFOCYZZGQU-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 229940071248 anisate Drugs 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- SVHOVVJFOWGYJO-UHFFFAOYSA-N pentabromophenol Chemical compound OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br SVHOVVJFOWGYJO-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- HXBKPYIEQLLNBK-UHFFFAOYSA-N 4-(4-octylphenyl)benzoic acid Chemical compound C1=CC(CCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 HXBKPYIEQLLNBK-UHFFFAOYSA-N 0.000 description 3
- RDISTOCQRJJICR-UHFFFAOYSA-N 4-(4-pentoxyphenyl)benzonitrile Chemical group C1=CC(OCCCCC)=CC=C1C1=CC=C(C#N)C=C1 RDISTOCQRJJICR-UHFFFAOYSA-N 0.000 description 3
- HCPBURTZSXRGBN-UHFFFAOYSA-N 4-(4-propylphenyl)benzoic acid Chemical compound C1=CC(CCC)=CC=C1C1=CC=C(C(O)=O)C=C1 HCPBURTZSXRGBN-UHFFFAOYSA-N 0.000 description 3
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000002178 crystalline material Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- ZZXUPXUHQHTUNH-UHFFFAOYSA-N 3-[(2-methylpropan-2-yl)oxycarbonylamino]pyridine-4-carboxylic acid Chemical compound CC(C)(C)OC(=O)NC1=CN=CC=C1C(O)=O ZZXUPXUHQHTUNH-UHFFFAOYSA-N 0.000 description 2
- SRZLTIGDPRQGMM-UHFFFAOYSA-N 4-(2-pentylphenyl)benzoic acid Chemical compound CCCCCC1=CC=CC=C1C1=CC=C(C(O)=O)C=C1 SRZLTIGDPRQGMM-UHFFFAOYSA-N 0.000 description 2
- BDDYPNQQJHNKSC-UHFFFAOYSA-N 4-(4-heptoxyphenyl)benzoic acid Chemical compound C1=CC(OCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 BDDYPNQQJHNKSC-UHFFFAOYSA-N 0.000 description 2
- JPBFKTCKZLMJED-UHFFFAOYSA-N 4-(4-heptoxyphenyl)benzonitrile Chemical group C1=CC(OCCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 JPBFKTCKZLMJED-UHFFFAOYSA-N 0.000 description 2
- FDPKGXQCDURRBM-UHFFFAOYSA-N 4-(4-methoxyphenyl)benzoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C(O)=O)C=C1 FDPKGXQCDURRBM-UHFFFAOYSA-N 0.000 description 2
- ACCMUAPHRVODJN-UHFFFAOYSA-N 4-(4-propoxyphenyl)benzoic acid Chemical compound C1=CC(OCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 ACCMUAPHRVODJN-UHFFFAOYSA-N 0.000 description 2
- ZRVIYEJYXIDATJ-UHFFFAOYSA-N 4-Heptyloxybenzoic acid Chemical compound CCCCCCCOC1=CC=C(C(O)=O)C=C1 ZRVIYEJYXIDATJ-UHFFFAOYSA-N 0.000 description 2
- CCLVGHDFLATNLC-UHFFFAOYSA-N 4-[4-(2-methylbutyl)phenyl]benzoic acid Chemical compound C1=CC(CC(C)CC)=CC=C1C1=CC=C(C(O)=O)C=C1 CCLVGHDFLATNLC-UHFFFAOYSA-N 0.000 description 2
- LAUFPZPAKULAGB-UHFFFAOYSA-N 4-butoxybenzoic acid Chemical compound CCCCOC1=CC=C(C(O)=O)C=C1 LAUFPZPAKULAGB-UHFFFAOYSA-N 0.000 description 2
- VSUKEWPHURLYTK-UHFFFAOYSA-N 4-heptylbenzoic acid Chemical compound CCCCCCCC1=CC=C(C(O)=O)C=C1 VSUKEWPHURLYTK-UHFFFAOYSA-N 0.000 description 2
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 230000003098 cholesteric effect Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- PPQAGRXNKROYIP-UHFFFAOYSA-N 1-methyl-2-phenyl-3-propylindole Chemical compound CN1C2=CC=CC=C2C(CCC)=C1C1=CC=CC=C1 PPQAGRXNKROYIP-UHFFFAOYSA-N 0.000 description 1
- WCJUJMPIFZMWOZ-UHFFFAOYSA-N 1-pentyl-4-phenylcyclohexa-2,4-diene-1-carbonitrile Chemical group C1=CC(CCCCC)(C#N)CC=C1C1=CC=CC=C1 WCJUJMPIFZMWOZ-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- NLHZIBRSZUFDFU-UHFFFAOYSA-N 4-(4-ethoxyphenyl)benzoic acid Chemical compound C1=CC(OCC)=CC=C1C1=CC=C(C(O)=O)C=C1 NLHZIBRSZUFDFU-UHFFFAOYSA-N 0.000 description 1
- VQLWORYWCJWAAP-UHFFFAOYSA-N 4-(4-hexoxybenzoyl)oxybenzoic acid Chemical compound C1=CC(OCCCCCC)=CC=C1C(=O)OC1=CC=C(C(O)=O)C=C1 VQLWORYWCJWAAP-UHFFFAOYSA-N 0.000 description 1
- RZOCCLOTCXINRG-UHFFFAOYSA-N 4-(4-methylphenyl)benzoic acid Chemical compound C1=CC(C)=CC=C1C1=CC=C(C(O)=O)C=C1 RZOCCLOTCXINRG-UHFFFAOYSA-N 0.000 description 1
- YNBBQLUKHHSKPW-UHFFFAOYSA-N 4-(4-octoxyphenyl)benzoic acid Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 YNBBQLUKHHSKPW-UHFFFAOYSA-N 0.000 description 1
- RBJMVQVMVYPYED-UHFFFAOYSA-N 4-(4-pentoxyphenyl)benzoic acid Chemical compound C1=CC(OCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 RBJMVQVMVYPYED-UHFFFAOYSA-N 0.000 description 1
- PAXFBGZCRAEDBM-UHFFFAOYSA-N 4-(4-pentylphenyl)benzoyl chloride Chemical compound C1=CC(CCCCC)=CC=C1C1=CC=C(C(Cl)=O)C=C1 PAXFBGZCRAEDBM-UHFFFAOYSA-N 0.000 description 1
- HTSCPVPNXMPNQZ-UHFFFAOYSA-N 4-(4-pentylphenyl)phenol Chemical compound C1=CC(CCCCC)=CC=C1C1=CC=C(O)C=C1 HTSCPVPNXMPNQZ-UHFFFAOYSA-N 0.000 description 1
- OUXLUHHXKDPSOZ-UHFFFAOYSA-N 4-(4-propylphenyl)phenol Chemical compound C1=CC(CCC)=CC=C1C1=CC=C(O)C=C1 OUXLUHHXKDPSOZ-UHFFFAOYSA-N 0.000 description 1
- ZQVKTHRQIXSMGY-UHFFFAOYSA-N 4-Ethylbenzoic acid Chemical compound CCC1=CC=C(C(O)=O)C=C1 ZQVKTHRQIXSMGY-UHFFFAOYSA-N 0.000 description 1
- UITQHXNDEYNVID-UHFFFAOYSA-N 4-[4-(2-ethylhexyl)phenyl]benzoic acid Chemical compound C1=CC(CC(CC)CCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 UITQHXNDEYNVID-UHFFFAOYSA-N 0.000 description 1
- PIDQWZNCEQHGEY-UHFFFAOYSA-N 4-[4-(3-methylbutyl)phenyl]benzoic acid Chemical compound C1=CC(CCC(C)C)=CC=C1C1=CC=C(C(O)=O)C=C1 PIDQWZNCEQHGEY-UHFFFAOYSA-N 0.000 description 1
- OUOWCSJYDCPVDM-UHFFFAOYSA-N 4-butylbenzoyl chloride Chemical compound CCCCC1=CC=C(C(Cl)=O)C=C1 OUOWCSJYDCPVDM-UHFFFAOYSA-N 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- ZNPSUQQXTRRSBM-UHFFFAOYSA-N 4-n-Pentylphenol Chemical compound CCCCCC1=CC=C(O)C=C1 ZNPSUQQXTRRSBM-UHFFFAOYSA-N 0.000 description 1
- ZQLDNJKHLQOJGE-UHFFFAOYSA-N 4-octylbenzoic acid Chemical compound CCCCCCCCC1=CC=C(C(O)=O)C=C1 ZQLDNJKHLQOJGE-UHFFFAOYSA-N 0.000 description 1
- OZPPUPJQRJYTNY-UHFFFAOYSA-N 4-pentoxybenzoic acid Chemical compound CCCCCOC1=CC=C(C(O)=O)C=C1 OZPPUPJQRJYTNY-UHFFFAOYSA-N 0.000 description 1
- ATZHGRNFEFVDDJ-UHFFFAOYSA-N 4-propylbenzoic acid Chemical compound CCCC1=CC=C(C(O)=O)C=C1 ATZHGRNFEFVDDJ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical group C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- MTICSNMNULXOAO-UHFFFAOYSA-N carbonic acid;1,2-diphenylbenzene Chemical compound OC(O)=O.C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 MTICSNMNULXOAO-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid group Chemical class C(C=CC1=CC=CC=C1)(=O)O WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- FEIWNULTQYHCDN-UHFFFAOYSA-N mbba Chemical compound C1=CC(CCCC)=CC=C1N=CC1=CC=C(OC)C=C1 FEIWNULTQYHCDN-UHFFFAOYSA-N 0.000 description 1
- 230000003446 memory effect Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DBOAVDSSZWDGTH-UHFFFAOYSA-N n-(4-butylphenyl)-1-(4-ethoxyphenyl)methanimine Chemical compound C1=CC(CCCC)=CC=C1N=CC1=CC=C(OCC)C=C1 DBOAVDSSZWDGTH-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000001564 phenyl benzoates Chemical class 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 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
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- XPAUZCCAJQKCKF-UHFFFAOYSA-M potassium;4-butylphenolate Chemical compound [K+].CCCCC1=CC=C([O-])C=C1 XPAUZCCAJQKCKF-UHFFFAOYSA-M 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000008096 xylene Substances 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
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752535046 DE2535046C3 (de) | 1975-08-06 | 1975-08-06 | Biphenylcarbonsäurephenyl- bzw. Benzoesäurebiphenylester, Verfahren zu deren Herstellung und deren Verwendung in flüssigkristallinen Dielektrika |
| DD188949A DD123757A5 (enExample) | 1974-10-22 | 1975-10-20 | |
| FR7531983A FR2288732A1 (fr) | 1974-10-22 | 1975-10-20 | Nouveaux esters biphenyliques, procede pour leur preparation et application comme constituants de cristaux liquides |
| GB4291575A GB1456359A (en) | 1974-10-22 | 1975-10-20 | Biphenyl carboxylic esters |
| US05/624,400 US4065489A (en) | 1974-10-22 | 1975-10-21 | Biphenyl esters and liquid crystalline mixtures comprising them |
| CH1361775A CH614460A5 (enExample) | 1974-10-22 | 1975-10-21 | |
| AT801875A AT341016B (de) | 1974-10-22 | 1975-10-21 | Flussigkristallines dielektrikum |
| JP50127860A JPS6031237B2 (ja) | 1974-10-22 | 1975-10-22 | ネマチックまたはカイラル−ネマチック液晶組成物 |
| NL7512370A NL7512370A (nl) | 1974-10-22 | 1975-10-22 | Bifenylesters. |
| JP141176A JPS5219641A (en) | 1975-08-06 | 1976-01-01 | Biphenyl esters |
| US05/840,946 US4136053A (en) | 1974-10-22 | 1977-10-11 | Biphenyl esters and liquid crystalline mixtures comprising them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752535046 DE2535046C3 (de) | 1975-08-06 | 1975-08-06 | Biphenylcarbonsäurephenyl- bzw. Benzoesäurebiphenylester, Verfahren zu deren Herstellung und deren Verwendung in flüssigkristallinen Dielektrika |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2535046A1 DE2535046A1 (de) | 1977-02-24 |
| DE2535046B2 DE2535046B2 (de) | 1979-05-03 |
| DE2535046C3 true DE2535046C3 (de) | 1979-12-13 |
Family
ID=5953323
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752535046 Expired DE2535046C3 (de) | 1974-10-22 | 1975-08-06 | Biphenylcarbonsäurephenyl- bzw. Benzoesäurebiphenylester, Verfahren zu deren Herstellung und deren Verwendung in flüssigkristallinen Dielektrika |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5219641A (enExample) |
| DE (1) | DE2535046C3 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5822466B2 (ja) * | 1976-09-06 | 1983-05-09 | チッソ株式会社 | コレステリツク化合物 |
| JPS6051147A (ja) * | 1983-07-28 | 1985-03-22 | Chisso Corp | 液晶物質及び液晶組成物 |
| DE3600052A1 (de) | 1986-01-03 | 1987-07-09 | Merck Patent Gmbh | Heterocyclische verbindungen |
| EP1907347A2 (en) * | 2005-07-12 | 2008-04-09 | Arcadia Pharmaceuticals Inc. | Compounds with activity at retinoic acid receptors |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2288732A1 (fr) * | 1974-10-22 | 1976-05-21 | Merck Patent Gmbh | Nouveaux esters biphenyliques, procede pour leur preparation et application comme constituants de cristaux liquides |
-
1975
- 1975-08-06 DE DE19752535046 patent/DE2535046C3/de not_active Expired
-
1976
- 1976-01-01 JP JP141176A patent/JPS5219641A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2535046A1 (de) | 1977-02-24 |
| JPS5219641A (en) | 1977-02-15 |
| DE2535046B2 (de) | 1979-05-03 |
| JPS57301B2 (enExample) | 1982-01-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |