DE3221462C2 - - Google Patents
Info
- Publication number
- DE3221462C2 DE3221462C2 DE3221462A DE3221462A DE3221462C2 DE 3221462 C2 DE3221462 C2 DE 3221462C2 DE 3221462 A DE3221462 A DE 3221462A DE 3221462 A DE3221462 A DE 3221462A DE 3221462 C2 DE3221462 C2 DE 3221462C2
- Authority
- DE
- Germany
- Prior art keywords
- trans
- phenyl
- weight
- ethyl
- cyclohexyl
- 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 - Fee Related
Links
- -1 2,2-dicyanovinyl Chemical group 0.000 claims description 140
- 239000000203 mixture Substances 0.000 claims description 103
- 150000001875 compounds Chemical class 0.000 claims description 84
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 3
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 235000010233 benzoic acid Nutrition 0.000 description 26
- 239000005711 Benzoic acid Substances 0.000 description 25
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- PRDZROBDMPYWMJ-UHFFFAOYSA-N (4-cyanophenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=C(C#N)C=C1 PRDZROBDMPYWMJ-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 239000004973 liquid crystal related substance Substances 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- DAXLJDPEGPZILX-WKILWMFISA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(CCC)N=N1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(CCC)N=N1 DAXLJDPEGPZILX-WKILWMFISA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- HJIVFZUPTYADSP-WKILWMFISA-N C1C[C@@H](CCCCC)CC[C@@H]1C(=O)OC1=CC=C(OC)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C(=O)OC1=CC=C(OC)C=C1 HJIVFZUPTYADSP-WKILWMFISA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- SPLICWLGOOXUDP-IYARVYRRSA-N C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CC=C(CCC)N=N1 Chemical compound C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CC=C(CCC)N=N1 SPLICWLGOOXUDP-IYARVYRRSA-N 0.000 description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 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 5
- WPWREPBHZDYAEY-IYARVYRRSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(CCCCC)N=N1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(CCCCC)N=N1 WPWREPBHZDYAEY-IYARVYRRSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- GNUWKHBYFSIMGT-UHFFFAOYSA-N 4-[2-(4-pentylphenyl)ethyl]cyclohexane-1-carbonitrile Chemical compound C1=CC(CCCCC)=CC=C1CCC1CCC(C#N)CC1 GNUWKHBYFSIMGT-UHFFFAOYSA-N 0.000 description 4
- KUTWIQCBCSPAKD-UHFFFAOYSA-N 4-formylcyclohexane-1-carbonitrile Chemical compound O=CC1CCC(C#N)CC1 KUTWIQCBCSPAKD-UHFFFAOYSA-N 0.000 description 4
- BRLAYTYCBMUAQV-XUTJKUGGSA-N C1=CC(CCCCC)=CC=C1C1=CC=C([C@@H]2CC[C@@H](CCC)CC2)N=N1 Chemical compound C1=CC(CCCCC)=CC=C1C1=CC=C([C@@H]2CC[C@@H](CCC)CC2)N=N1 BRLAYTYCBMUAQV-XUTJKUGGSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- BKWQKVJYXODDAC-UHFFFAOYSA-N 1,2-dihydropyridazine Chemical compound N1NC=CC=C1 BKWQKVJYXODDAC-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- HXOWMHXGHNZDFT-UHFFFAOYSA-N 1-(bromomethyl)-4-pentylcyclohexane Chemical compound CCCCCC1CCC(CBr)CC1 HXOWMHXGHNZDFT-UHFFFAOYSA-N 0.000 description 3
- FNCOVSWSZZVFBQ-UHFFFAOYSA-N 2-[(4-hydroxyphenyl)methylidene]propanedinitrile Chemical compound OC1=CC=C(C=C(C#N)C#N)C=C1 FNCOVSWSZZVFBQ-UHFFFAOYSA-N 0.000 description 3
- HKTGFQYUVIWWMT-UHFFFAOYSA-N 2-chloro-4-(4-heptylbenzoyl)oxybenzoic acid Chemical compound C1=CC(CCCCCCC)=CC=C1C(=O)OC1=CC=C(C(O)=O)C(Cl)=C1 HKTGFQYUVIWWMT-UHFFFAOYSA-N 0.000 description 3
- OJBZABCNFYYKGZ-UHFFFAOYSA-N 4-(5-heptylpyrimidin-2-yl)benzoic acid Chemical compound N1=CC(CCCCCCC)=CN=C1C1=CC=C(C(O)=O)C=C1 OJBZABCNFYYKGZ-UHFFFAOYSA-N 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- BIVMWMIMQKNFFR-HDJSIYSDSA-N C1=CC(C)=CC=C1S(=O)(=O)OC[C@@H]1CC[C@@H](C#N)CC1 Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC[C@@H]1CC[C@@H](C#N)CC1 BIVMWMIMQKNFFR-HDJSIYSDSA-N 0.000 description 3
- RXBBPIPXHBOXOU-KESTWPANSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(CCC)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(CCC)C=C1 RXBBPIPXHBOXOU-KESTWPANSA-N 0.000 description 3
- LFGDFCLIVISJSO-WGSAOQKQSA-N C1C[C@@H](CCCCC)CC[C@@H]1CCC1=CC=C(OCC)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1CCC1=CC=C(OCC)C=C1 LFGDFCLIVISJSO-WGSAOQKQSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- SYKZMDWVCYCYSN-JOCQHMNTSA-N N1=NC(CCC)=CC=C1[C@@H]1CC[C@@H](CC)CC1 Chemical compound N1=NC(CCC)=CC=C1[C@@H]1CC[C@@H](CC)CC1 SYKZMDWVCYCYSN-JOCQHMNTSA-N 0.000 description 3
- LJRRXLIAMOVWRK-IYARVYRRSA-N N1=NC(CCCCCCC)=CC=C1[C@@H]1CC[C@@H](CCC)CC1 Chemical compound N1=NC(CCCCCCC)=CC=C1[C@@H]1CC[C@@H](CCC)CC1 LJRRXLIAMOVWRK-IYARVYRRSA-N 0.000 description 3
- 239000004990 Smectic liquid crystal Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000003098 cholesteric effect Effects 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 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 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RAOQLAYIDNKQHG-UHFFFAOYSA-N (4-pentylcyclohexyl)methanol Chemical compound CCCCCC1CCC(CO)CC1 RAOQLAYIDNKQHG-UHFFFAOYSA-N 0.000 description 2
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
- ZAXPYKIVLGYIBG-UHFFFAOYSA-N 2-[1-(4-hydroxyphenyl)ethylidene]propanedinitrile Chemical compound N#CC(C#N)=C(C)C1=CC=C(O)C=C1 ZAXPYKIVLGYIBG-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
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 2
- GRPCILYSCDCPJA-UHFFFAOYSA-N 4-(hydroxymethyl)cyclohexane-1-carbonitrile Chemical compound OCC1CCC(C#N)CC1 GRPCILYSCDCPJA-UHFFFAOYSA-N 0.000 description 2
- APJYCJWBTIOXAY-UHFFFAOYSA-N 4-(methoxymethylidene)cyclohexane-1-carbonitrile Chemical compound COC=C1CCC(C#N)CC1 APJYCJWBTIOXAY-UHFFFAOYSA-N 0.000 description 2
- UUSVTNLTNQIQGN-UHFFFAOYSA-N 4-oxocyclohex-2-ene-1-carbonitrile Chemical compound O=C1CCC(C#N)C=C1 UUSVTNLTNQIQGN-UHFFFAOYSA-N 0.000 description 2
- QIWQJGMBIABGRX-UHFFFAOYSA-N 4-oxocyclohexane-1-carbonitrile Chemical compound O=C1CCC(C#N)CC1 QIWQJGMBIABGRX-UHFFFAOYSA-N 0.000 description 2
- RTJYIRMFYYDFQJ-UHFFFAOYSA-N 4-oxocyclohexene-1-carbonitrile Chemical compound O=C1CCC(C#N)=CC1 RTJYIRMFYYDFQJ-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- RZBSEGBMCJSSPZ-WGSAOQKQSA-N C1=CC(OCCCCC)=CC=C1OC(=O)[C@@H]1CC[C@@H](CCCC)CC1 Chemical compound C1=CC(OCCCCC)=CC=C1OC(=O)[C@@H]1CC[C@@H](CCCC)CC1 RZBSEGBMCJSSPZ-WGSAOQKQSA-N 0.000 description 2
- TXUSCIUQIHJDFH-AFARHQOCSA-N C1C[C@@H](CCCC)CC[C@@H]1C(=O)OC1=CC=C(C(=O)OC=2C=CC(CCCC)=CC=2)C=C1 Chemical compound C1C[C@@H](CCCC)CC[C@@H]1C(=O)OC1=CC=C(C(=O)OC=2C=CC(CCCC)=CC=2)C=C1 TXUSCIUQIHJDFH-AFARHQOCSA-N 0.000 description 2
- GNPQRJZTDYNOBB-UBBSCCEASA-N C1C[C@@H](CCCCC)CC[C@@H]1CC[C@@H]1CC[C@@H](C#N)CC1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1CC[C@@H]1CC[C@@H](C#N)CC1 GNPQRJZTDYNOBB-UBBSCCEASA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 238000000023 Kugelrohr distillation Methods 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 238000006828 Rosenmund reduction reaction Methods 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 150000005378 cyclohexanecarboxylic acids Chemical class 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 150000004892 pyridazines Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 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 2
- 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 2
- LZTRWDSEEVEZTN-POYBYMJQSA-N (1s,2r)-2-methoxy-4-oxocyclohexane-1-carbonitrile Chemical compound CO[C@@H]1CC(=O)CC[C@H]1C#N LZTRWDSEEVEZTN-POYBYMJQSA-N 0.000 description 1
- OMBJMCFSJDBCRP-UHFFFAOYSA-M (4-pentylphenyl)methyl-triphenylphosphanium;bromide Chemical compound [Br-].C1=CC(CCCCC)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 OMBJMCFSJDBCRP-UHFFFAOYSA-M 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- GDNOYVMHHMSZJV-UHFFFAOYSA-M 2-(3,4-dimethyl-1,3-thiazol-3-ium-5-yl)ethanol;iodide Chemical compound [I-].CC1=C(CCO)SC=[N+]1C GDNOYVMHHMSZJV-UHFFFAOYSA-M 0.000 description 1
- IWSVLBKHBJGMAA-UHFFFAOYSA-M 2-(3-benzyl-4-methyl-1,3-thiazol-3-ium-5-yl)ethanol;chloride Chemical compound [Cl-].CC1=C(CCO)SC=[N+]1CC1=CC=CC=C1 IWSVLBKHBJGMAA-UHFFFAOYSA-M 0.000 description 1
- ZMOMCILMBYEGLD-UHFFFAOYSA-N 2-chloro-4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(Cl)=C1 ZMOMCILMBYEGLD-UHFFFAOYSA-N 0.000 description 1
- JXPDNDHCMMOJPC-UHFFFAOYSA-N 2-hydroxybutanedinitrile Chemical compound N#CC(O)CC#N JXPDNDHCMMOJPC-UHFFFAOYSA-N 0.000 description 1
- LZJLXDNGANKYIE-UHFFFAOYSA-N 3,4-diphenylpyridazine Chemical class C1=CC=CC=C1C1=CC=NN=C1C1=CC=CC=C1 LZJLXDNGANKYIE-UHFFFAOYSA-N 0.000 description 1
- PLKROHNMZPCGLD-UHFFFAOYSA-N 3-cyclohexylpyridazine Chemical class C1CCCCC1C1=CC=CN=N1 PLKROHNMZPCGLD-UHFFFAOYSA-N 0.000 description 1
- MHTXWJCQNDZURB-UHFFFAOYSA-N 3-pentoxy-6-(4-pentylphenyl)pyridazine Chemical compound N1=NC(OCCCCC)=CC=C1C1=CC=C(CCCCC)C=C1 MHTXWJCQNDZURB-UHFFFAOYSA-N 0.000 description 1
- CTCUIHCUKJFRII-UHFFFAOYSA-N 3-pentyl-6-(4-pentylphenyl)pyridazine Chemical compound C1=CC(CCCCC)=CC=C1C1=CC=C(CCCCC)N=N1 CTCUIHCUKJFRII-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VSUKEWPHURLYTK-UHFFFAOYSA-N 4-heptylbenzoic acid Chemical compound CCCCCCCC1=CC=C(C(O)=O)C=C1 VSUKEWPHURLYTK-UHFFFAOYSA-N 0.000 description 1
- RVLAXPQGTRTHEV-UHFFFAOYSA-N 4-pentylcyclohexane-1-carboxylic acid Chemical compound CCCCCC1CCC(C(O)=O)CC1 RVLAXPQGTRTHEV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- JANRHXLLKXCCGY-WRNSKWPRSA-N C(CC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCC Chemical compound C(CC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCC JANRHXLLKXCCGY-WRNSKWPRSA-N 0.000 description 1
- WQNSXVUICWVBMB-KZIAUGABSA-N C(CCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCC Chemical compound C(CCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCC WQNSXVUICWVBMB-KZIAUGABSA-N 0.000 description 1
- IFXJYQZJBCOECG-WGSAOQKQSA-N C1=CC(CCCCC)=CC=C1CC[C@@H]1CC[C@@H](C(O)=O)CC1 Chemical compound C1=CC(CCCCC)=CC=C1CC[C@@H]1CC[C@@H](C(O)=O)CC1 IFXJYQZJBCOECG-WGSAOQKQSA-N 0.000 description 1
- APBBCFNZHALDSW-QAQDUYKDSA-N C1C[C@@H](CCC)CC[C@@H]1CCC1=CC=C(OCC)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1CCC1=CC=C(OCC)C=C1 APBBCFNZHALDSW-QAQDUYKDSA-N 0.000 description 1
- LSBXJRCCLBEZEV-OPMHRUBESA-N C1C[C@@H](CCC)CC[C@@H]1OC(=O)[C@@H]1CC[C@@H](CCC)CC1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1OC(=O)[C@@H]1CC[C@@H](CCC)CC1 LSBXJRCCLBEZEV-OPMHRUBESA-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
- RXNHJSWEUSIGAN-VVPTUSLJSA-N C1C[C@@H](CCCCC)CC[C@@H]1CC[C@@H]1CC[C@@H](C(O)=O)CC1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1CC[C@@H]1CC[C@@H](C(O)=O)CC1 RXNHJSWEUSIGAN-VVPTUSLJSA-N 0.000 description 1
- PQOKZHAEHJWKHB-MXVIHJGJSA-N C1C[C@@H](CCCCCCC)CC[C@@H]1CCC1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCCCCC)CC[C@@H]1CCC1=CC=C(C#N)C=C1 PQOKZHAEHJWKHB-MXVIHJGJSA-N 0.000 description 1
- MYSLYAVECCLXQN-WGSAOQKQSA-N C1C[C@@H](CCCCCCC)CC[C@@H]1CCC1=CC=C(C(O)=O)C=C1 Chemical compound C1C[C@@H](CCCCCCC)CC[C@@H]1CCC1=CC=C(C(O)=O)C=C1 MYSLYAVECCLXQN-WGSAOQKQSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000006214 Clemmensen reduction reaction Methods 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 239000003810 Jones reagent Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 101100400378 Mus musculus Marveld2 gene Proteins 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 241001474977 Palla Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000006856 Wolf-Kishner-Huang Minlon reduction reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000005224 alkoxybenzenes Chemical class 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 125000003118 aryl group Chemical group 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
- 150000001559 benzoic acids Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 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
- 210000002858 crystal cell Anatomy 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 description 1
- SHALBPKEGDBVKK-VOTSOKGWSA-N danishefsky's diene Chemical compound CO\C=C\C(=C)O[Si](C)(C)C SHALBPKEGDBVKK-VOTSOKGWSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJFNDMHZXCUXSA-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SJFNDMHZXCUXSA-UHFFFAOYSA-M 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000007070 tosylation reaction Methods 0.000 description 1
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing 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
- 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
- C09K19/02—Liquid crystal materials characterised by optical, electrical or physical properties of the components, in general
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH4038/81A CH647230A5 (en) | 1981-06-18 | 1981-06-18 | Phenyl esters, and the use thereof as components of liquid-crystalline mixtures |
| CH188382A CH649094A5 (en) | 1982-03-26 | 1982-03-26 | Liquid-crystalline mixture |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3221462A1 DE3221462A1 (de) | 1983-01-05 |
| DE3221462C2 true DE3221462C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-11-28 |
Family
ID=25688909
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823221462 Granted DE3221462A1 (de) | 1981-06-18 | 1982-06-07 | Fluessigkristallines gemisch |
Country Status (4)
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3221462A1 (de) * | 1981-06-18 | 1983-01-05 | F. Hoffmann-La Roche & Co AG, 4002 Basel | Fluessigkristallines gemisch |
| US4583826A (en) * | 1981-10-14 | 1986-04-22 | Hoffmann-La Roche Inc. | Phenylethanes |
| US4528114A (en) * | 1981-12-18 | 1985-07-09 | Hoffmann-La Roche Inc. | Acetylenes |
| US4729639A (en) * | 1982-03-29 | 1988-03-08 | Tektronix, Inc. | Dual frequency addressable liquid crystals and methods of use |
| EP0103681B1 (de) * | 1982-07-28 | 1986-07-30 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Tetra- und pentacyclische Monoester |
| US4550981A (en) * | 1982-09-30 | 1985-11-05 | Hoffmann-La Roche Inc. | Liquid crystalline esters and mixtures |
| DE3365687D1 (de) * | 1982-10-21 | 1986-10-02 | Hoffmann La Roche | Dicyanobenzenes |
| GB2132612B (en) * | 1982-10-30 | 1986-01-22 | Dainippon Ink & Chemicals | Nematic liquid crystalline cyclohexyl esters |
| EP0111695A3 (de) * | 1982-11-19 | 1985-08-21 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Pyridazinderivate |
| DE3374875D1 (en) * | 1982-11-29 | 1988-01-21 | Hoffmann La Roche | Coloured liquid crystal mixtures containing phenyl ethanes |
| EP0122389B1 (de) * | 1983-03-16 | 1987-08-05 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Flüssigkristallkomponenten mit einer Alkenylseitenkette |
| US4565425A (en) * | 1983-03-16 | 1986-01-21 | Hoffmann-La Roche Inc. | Liquid crystals |
| GB8314077D0 (en) * | 1983-05-20 | 1983-06-29 | Secr Defence | Disubstituted ethanes |
| DE3332691A1 (de) * | 1983-09-10 | 1985-03-28 | Merck Patent Gmbh, 6100 Darmstadt | Anisotrope verbindungen und fluessigkristallmischungen |
| DE3401320A1 (de) * | 1984-01-17 | 1985-07-25 | Merck Patent Gmbh, 6100 Darmstadt | Ethanderivate |
| JPH0670020B2 (ja) * | 1984-04-03 | 1994-09-07 | チッソ株式会社 | 置換ピリダジン類 |
| EP0167912B1 (de) * | 1984-07-12 | 1990-01-03 | F. Hoffmann-La Roche Ag | Flüssigkristalline Gemische enthaltend Komponenten mit einer 4-Alkenyl- oder 2Z-Alkenyl-Seitenkette |
| US4759870A (en) * | 1984-08-14 | 1988-07-26 | Casio Computer Co., Ltd. | Liquid crystal composition |
| DE3518734A1 (de) * | 1985-05-24 | 1986-11-27 | Merck Patent Gmbh, 6100 Darmstadt | Smektische fluessigkristalline phasen |
| US4740328A (en) * | 1986-02-14 | 1988-04-26 | Casio Computer Co., Ltd. | Liquid crystal composition |
| EP0261614A3 (de) * | 1986-09-26 | 1989-07-12 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Flüssigkristallanzeigezelle |
| CA1336441C (en) * | 1987-12-28 | 1995-07-25 | Manabu Uchida | Liquid crystal composition |
| ATE110764T1 (de) * | 1988-06-24 | 1994-09-15 | Canon Kk | Ferroelektrische chirale smektische flüssigkristallzusammensetzung und vorrichtung mit dieser zusammensetzung. |
| US5250217A (en) * | 1988-06-24 | 1993-10-05 | Canon Kabushiki Kaisha | Ferroelectric chiral smectic liquid crystal composition and liquid crystal device using same |
| US6004479A (en) | 1988-07-13 | 1999-12-21 | Merck Kgaa | Matrix liquid crystal display |
| DE3923044B4 (de) * | 1988-10-20 | 2005-09-08 | Merck Patent Gmbh | Flüssigkristallmischung |
| ES2058433T3 (es) * | 1988-10-20 | 1994-11-01 | Merck Patent Gmbh | Indicador matriz de cristal liquido. |
| DE3927674A1 (de) * | 1989-08-22 | 1991-02-28 | Merck Patent Gmbh | Matrix - fluessigkristallanzeige |
| EP0528542B1 (en) * | 1991-07-19 | 1998-09-16 | SHARP Corporation | Optical modulating element and apparatuses using it |
| KR101541138B1 (ko) | 2008-12-16 | 2015-08-03 | 주식회사 동진쎄미켐 | 액정 화합물 및 그 제조방법 |
| CN104062765B (zh) * | 2014-07-11 | 2016-11-23 | 张家港康得新光电材料有限公司 | 2d与3d影像切换显示设备和柱状透镜元件 |
| KR102656729B1 (ko) * | 2015-09-08 | 2024-04-15 | 메르크 파텐트 게엠베하 | 광 변조 소자 |
Family Cites Families (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3915883A (en) * | 1972-04-26 | 1975-10-28 | Eastman Kodak Co | Liquid crystalline compounds and compositions |
| US4009934A (en) * | 1974-01-11 | 1977-03-01 | Eastman Kodak Company | Electro-optic display devices and methods |
| JPS5298687A (en) * | 1976-02-13 | 1977-08-18 | Omron Tateisi Electronics Co | Liquid crystal composites |
| US4113647A (en) * | 1976-08-13 | 1978-09-12 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Liquid crystalline materials |
| GB2009219B (en) * | 1977-11-02 | 1982-04-28 | Secr Defence | Liquid ctystal material mixtures and devices incorporating such mixtures |
| GB2013014B (en) * | 1977-12-27 | 1982-06-30 | Suwa Seikosha Kk | Liquid crystal display device |
| GB2020075A (en) * | 1978-03-01 | 1979-11-07 | Suwa Seikosha Kk | Liquid crystal display systems |
| JPS5521429A (en) * | 1978-07-31 | 1980-02-15 | Seiko Epson Corp | Liquid crystal composition |
| US4293434A (en) * | 1978-08-08 | 1981-10-06 | VEB Werk fur Fernsehelektronik Berlin im VEB Kombinat Mikroelektronik | Liquid crystal compounds |
| JPS5529545A (en) * | 1978-08-22 | 1980-03-01 | Seiko Epson Corp | Liquid crystal composition |
| GB2031010B (en) * | 1978-09-13 | 1983-02-09 | Secr Defence | Liquid crystal materials |
| JPS5566556A (en) * | 1978-11-15 | 1980-05-20 | Chisso Corp | 3-pentyloxy-6-cyclohexanecarboxy-phthalonitrile |
| US4279770A (en) * | 1978-09-20 | 1981-07-21 | Chisso Corporation | Liquid crystal 2,3-dicyano-hydroquinone derivatives |
| JPS5584385A (en) * | 1978-12-20 | 1980-06-25 | Seiko Epson Corp | Liquid crystal composition |
| GB2046731B (en) * | 1979-01-26 | 1983-04-20 | Suwa Seikosha Kk | (2'-cyano-4'-alkyl-)phenyl 3-chloro-4alkoxybenzoates theirpreparation and use in liquid crystal compositions |
| GB2053193B (en) * | 1979-05-01 | 1983-05-05 | Suwa Seikosha Kk | 2'-cyano-4'-n-alkylphenyl 3-cyano-4-n-alkoxybenzoates |
| EP0019665B2 (de) * | 1979-05-28 | 1987-12-16 | MERCK PATENT GmbH | Flüssigkristalline Verbindungen |
| DE2933563A1 (de) * | 1979-07-18 | 1981-02-05 | Bbc Brown Boveri & Cie | Anisotrope verbindungen mit negativer dk-anisotropie |
| FR2461697A1 (fr) * | 1979-07-20 | 1981-02-06 | Suwa Seikosha Kk | 3-cyano-4-alcoxybenzoate de 2-chloro-4-alcoylphenyle et son utilisation dans une composition de cristaux liquides |
| JPS5624481A (en) * | 1979-08-03 | 1981-03-09 | Seiko Epson Corp | Liquid crystal composition |
| DE3063497D1 (en) * | 1979-08-20 | 1983-07-07 | Werk Fernsehelektronik Veb | Nematic crystalline-liquid 5-alkyl-2-(4-acyloxyphenyl)-pyrimidines for opto-electronic arrangements and process for their preparation |
| JPS5636567A (en) * | 1979-08-31 | 1981-04-09 | Seiko Epson Corp | Liquid crystal composition |
| DE2939782A1 (de) * | 1979-09-07 | 1981-04-02 | BBC AG Brown, Boveri & Cie., Baden, Aargau | Aromatische verbindungen mit negativer dk-anisotropie |
| WO1981000853A1 (en) * | 1979-09-28 | 1981-04-02 | M Barnik | Liquid crystal material with low value of optical anisotropy and method of making it |
| US4363767A (en) * | 1980-01-11 | 1982-12-14 | VEB Werk fur Fernsehelektronik Berlin im VEB Kombinat Mikroelektronik | Esters of 4-[2,2-dicyano-ethenyl]-phenols |
| JPS56122885A (en) * | 1980-02-29 | 1981-09-26 | Sharp Corp | Liquid crystal display apparatus |
| JPS574960A (en) * | 1980-06-09 | 1982-01-11 | Chisso Corp | 4'''-cyanobiphenyl trans-4-(trans-4'-alkylcyclohexyl)- cyclohexanecarboxylate |
| JPS575781A (en) * | 1980-06-16 | 1982-01-12 | Seiko Epson Corp | Liquid crystal composition |
| JPS575782A (en) * | 1980-06-16 | 1982-01-12 | Seiko Epson Corp | Liquid crystal composition |
| JPS575780A (en) * | 1980-06-16 | 1982-01-12 | Seiko Epson Corp | Liquid crystal composition |
| JPS579742A (en) * | 1980-06-20 | 1982-01-19 | Chisso Corp | 4'-(trans-4"-alkylcyclohexyl)4-biphenylcarboxylic acid ester |
| JPS5716087A (en) * | 1980-07-04 | 1982-01-27 | Hitachi Ltd | Liquid crystal display device |
| JPS5721359A (en) * | 1980-07-15 | 1982-02-04 | Chisso Corp | 4'''-cyano-4"-biphenylyl 4-(trans-4'-alkylcyclohexyl)benzoate |
| JPS5734176A (en) * | 1980-08-08 | 1982-02-24 | Hitachi Ltd | Liquid crystal composition |
| GB2094311A (en) * | 1980-08-22 | 1982-09-15 | Ivaschenko Aleksandr Vasilevic | New derivatives of phenic acid method of obtaining them liquid crystal material with negative dielectric anisotropy method of obtaining that liquid crystal material liquid crystal material with low frequency in version of sign of dielectric anisotropy and method of obtaining that liquid crystal material |
| EP0050023B1 (en) * | 1980-10-13 | 1984-07-11 | The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and | Liquid crystal devices |
| JPS5770851A (en) * | 1980-10-21 | 1982-05-01 | Asahi Glass Co Ltd | Cinnamoyl nitrile |
| JPS5788151A (en) * | 1980-11-21 | 1982-06-01 | Asahi Glass Co Ltd | 4'-substituted phenyl 2-fluoro-4-(trans-4"- alkylcyclohexylcarbonyloxy)benzoate |
| DE3201721A1 (de) * | 1981-01-30 | 1982-08-19 | F. Hoffmann-La Roche & Co. AG, 4002 Basel | Disubstituierte aethane |
| GB2093057B (en) * | 1981-02-13 | 1985-10-16 | Secr Defence | Liquid crystal composition comprising a component of low dielectric anisotropy one of high clearing point and a low melting nematic component |
| US4406814A (en) * | 1981-04-10 | 1983-09-27 | Eaton Corporation | Liquid crystalline materials and optical displays utilizing same |
| DE3221462A1 (de) * | 1981-06-18 | 1983-01-05 | F. Hoffmann-La Roche & Co AG, 4002 Basel | Fluessigkristallines gemisch |
| CH651025A5 (de) * | 1982-05-14 | 1985-08-30 | Hoffmann La Roche | Pyridazine und ihre verwendung als komponenten fluessigkristalliner gemische. |
| US4452718A (en) * | 1981-07-31 | 1984-06-05 | Hoffmann-La Roche Inc. | Pyridazines |
| JPS5829876A (ja) * | 1981-08-17 | 1983-02-22 | Seiko Epson Corp | 液晶組成物 |
| US4583826A (en) * | 1981-10-14 | 1986-04-22 | Hoffmann-La Roche Inc. | Phenylethanes |
| JPS58118886A (ja) * | 1982-01-06 | 1983-07-15 | Hitachi Ltd | 液晶表示素子 |
| DE3270906D1 (en) * | 1982-01-14 | 1986-06-05 | Merck Patent Gmbh | Liquid crystal mixtures |
| JPS58142959A (ja) * | 1982-02-18 | 1983-08-25 | Seiko Epson Corp | 液晶組成物 |
| GB2114994B (en) * | 1982-02-18 | 1984-10-10 | Suwa Seikosha Kk | Liquid crystal compositions |
| JPS58142961A (ja) * | 1982-02-18 | 1983-08-25 | Seiko Epson Corp | 液晶組成物 |
| DE3206269A1 (de) * | 1982-02-20 | 1983-09-01 | Merck Patent Gmbh, 6100 Darmstadt | Bicyclohexylderivate |
| DE3208089A1 (de) * | 1982-03-06 | 1983-09-08 | Merck Patent Gmbh, 6100 Darmstadt | Halogenbiphenylderivate |
| DE3211601A1 (de) * | 1982-03-30 | 1983-10-06 | Merck Patent Gmbh | Hydroterphenyle |
| EP0090671B1 (en) * | 1982-03-31 | 1985-06-19 | Chisso Corporation | Carbocylic esters having liquid-crystal properties at high temperatures |
| JPS58194972A (ja) * | 1982-05-07 | 1983-11-14 | Chisso Corp | 液晶組成物 |
| JPS58203942A (ja) * | 1982-05-21 | 1983-11-28 | Dainippon Ink & Chem Inc | 新規ネマチツク液晶化合物 |
| US4472592A (en) * | 1982-07-09 | 1984-09-18 | Dainippon Ink And Chemicals, Inc. | Nematic liquid crystalline compounds |
-
1982
- 1982-06-07 DE DE19823221462 patent/DE3221462A1/de active Granted
- 1982-06-10 US US06/387,108 patent/US4460770A/en not_active Expired - Fee Related
- 1982-06-17 GB GB08217517A patent/GB2105740B/en not_active Expired
-
1983
- 1983-01-19 GB GB08301476A patent/GB2115808B/en not_active Expired
-
1986
- 1986-03-20 HK HK185/86A patent/HK18586A/xx unknown
-
1987
- 1987-05-20 US US07/053,601 patent/US4783280A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| GB8301476D0 (en) | 1983-02-23 |
| GB2115808A (en) | 1983-09-14 |
| US4783280A (en) | 1988-11-08 |
| GB2115808B (en) | 1985-12-04 |
| GB2105740B (en) | 1985-08-07 |
| DE3221462A1 (de) | 1983-01-05 |
| GB2105740A (en) | 1983-03-30 |
| HK18586A (en) | 1986-03-27 |
| US4460770A (en) | 1984-07-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3221462C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE3335550C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE3237367C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| EP0122389B1 (de) | Flüssigkristallkomponenten mit einer Alkenylseitenkette | |
| EP0103681B1 (de) | Tetra- und pentacyclische Monoester | |
| EP0125563B1 (de) | Bicyclohexylethane | |
| EP0172360B1 (de) | Cyclohexancarbonitrile und deren Verwendung als Komponenten für flüssigkristalline Gemische | |
| EP0022183B1 (de) | Cyclohexylbiphenyle, Verfahren zu ihrer Herstellung, diese enthaltende Dielektrika und elektrooptisches Anzeigeelement | |
| EP0056113B1 (de) | Cyclohexylcarbonitrilderivate, diese enthaltende Dielektrika und elektrooptisches Anzeigeelement | |
| EP0047817A2 (de) | Hydrierte Naphthaline, deren Herstellung und Verwendung sowie derartige Naphthaline enthaltende Gemische | |
| DE2701591B2 (de) | Hexahydroterphenylderivate und deren Verwendung in fliissigkristallinen Dielektrika | |
| EP0209622A1 (de) | Hydroterphenyle | |
| EP0247466B1 (de) | Flüssigkristalline Derivate von Phenylbenzoat | |
| DE3140868A1 (de) | Disubstituierte pyrimidine | |
| DE69303648T2 (de) | Polycyclische Dienderivat | |
| DD208167A5 (de) | Decaline | |
| EP0107116B1 (de) | Dicyanobenzole | |
| EP0154849B1 (de) | Cyclohexanderivate | |
| EP0111695A2 (de) | Pyridazinderivate | |
| DE69614038T2 (de) | Alkenylcyclohexanderivate und flüssigkristalline Zusammensetzungen | |
| EP0242716B1 (de) | Flüssigkristalline Pyridinderivate | |
| DE3228350A1 (de) | Pyridazine | |
| CH651025A5 (de) | Pyridazine und ihre verwendung als komponenten fluessigkristalliner gemische. | |
| CH648338A5 (en) | Polycyclic acetylene derivatives and the use thereof as components of liquid-crystalline mixtures | |
| DE3226051A1 (de) | Nitrile |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8101 | Request for examination as to novelty | ||
| 8105 | Search report available | ||
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: LEDERER, F., DIPL.-CHEM. DR., PAT.-ANW., 8000 MUEN |
|
| 8125 | Change of the main classification |
Ipc: C07C121/70 |
|
| 8127 | New person/name/address of the applicant |
Owner name: F. HOFFMANN-LA ROCHE AG, BASEL, CH |
|
| 8128 | New person/name/address of the agent |
Representative=s name: LEDERER, F., DIPL.-CHEM. DR., 8000 MUENCHEN RIEDER |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |