JPH0148890B2 - - Google Patents
Info
- Publication number
- JPH0148890B2 JPH0148890B2 JP14137681A JP14137681A JPH0148890B2 JP H0148890 B2 JPH0148890 B2 JP H0148890B2 JP 14137681 A JP14137681 A JP 14137681A JP 14137681 A JP14137681 A JP 14137681A JP H0148890 B2 JPH0148890 B2 JP H0148890B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- water
- add
- toluene
- reaction
- 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
- 239000004973 liquid crystal related substance Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- BPMBNLJJRKCCRT-UHFFFAOYSA-N 4-phenylbenzonitrile Chemical group C1=CC(C#N)=CC=C1C1=CC=CC=C1 BPMBNLJJRKCCRT-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- 150000001875 compounds Chemical class 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RZUNISKALBYPKC-UHFFFAOYSA-N 1-iodo-4-[4-(2-methoxyethyl)phenyl]benzene Chemical group C1=CC(CCOC)=CC=C1C1=CC=C(I)C=C1 RZUNISKALBYPKC-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- TZXJJSAQSRHKCZ-UHFFFAOYSA-N 2-methoxyethyl 4-methylbenzenesulfonate Chemical compound COCCOS(=O)(=O)C1=CC=C(C)C=C1 TZXJJSAQSRHKCZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CMCIDGQZPJNNTL-UHFFFAOYSA-N 4-[4-(2-methoxyethyl)phenyl]benzonitrile Chemical group C1=CC(CCOC)=CC=C1C1=CC=C(C#N)C=C1 CMCIDGQZPJNNTL-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- -1 β-ethyloxyethyl P-toluenesulfonate Chemical compound 0.000 description 2
- DTLLPCRDFWPUGS-UHFFFAOYSA-N 1-(2-ethoxyethyl)-4-(4-iodophenyl)benzene Chemical group C1=CC(CCOCC)=CC=C1C1=CC=C(I)C=C1 DTLLPCRDFWPUGS-UHFFFAOYSA-N 0.000 description 1
- VRFZYLKAQMPIHT-UHFFFAOYSA-N 1-(2-methoxyethyl)-4-phenylbenzene Chemical group C1=CC(CCOC)=CC=C1C1=CC=CC=C1 VRFZYLKAQMPIHT-UHFFFAOYSA-N 0.000 description 1
- KTADSLDAUJLZGL-UHFFFAOYSA-N 1-bromo-2-phenylbenzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1 KTADSLDAUJLZGL-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- KPFVDLWVGFWQGU-UHFFFAOYSA-N 4-[4-(2-ethoxyethyl)phenyl]benzonitrile Chemical group C1=CC(CCOCC)=CC=C1C1=CC=C(C#N)C=C1 KPFVDLWVGFWQGU-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- MCYYJHPHBOPLMH-UHFFFAOYSA-L disodium;dioxido-oxo-sulfanylidene-$l^{6}-sulfane;hydrate Chemical compound O.[Na+].[Na+].[O-]S([O-])(=O)=S MCYYJHPHBOPLMH-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Landscapes
- Liquid Crystal (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14137681A JPS5841854A (ja) | 1981-09-08 | 1981-09-08 | ４′−（β−アルキルオキシエチル）−４−シアノビフエニル |
| US06/369,111 US4431564A (en) | 1981-05-01 | 1982-04-16 | Liquid-crystalline biphenyl or terphenyl derivatives |
| CH2608/82A CH649283A5 (de) | 1981-05-01 | 1982-04-29 | Fluessigkristalline biphenyl- oder terphenylderivate. |
| DE3216281A DE3216281C2 (de) | 1981-05-01 | 1982-04-30 | Flüssig-kristalline Biphenyl- oder Terphenyl-Derivate, Verfahren zu deren Herstellung sowie deren Verwendung |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14137681A JPS5841854A (ja) | 1981-09-08 | 1981-09-08 | ４′−（β−アルキルオキシエチル）−４−シアノビフエニル |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5841854A JPS5841854A (ja) | 1983-03-11 |
| JPH0148890B2 true JPH0148890B2 (en, 2012) | 1989-10-20 |
Family
ID=15290554
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14137681A Granted JPS5841854A (ja) | 1981-05-01 | 1981-09-08 | ４′−（β−アルキルオキシエチル）−４−シアノビフエニル |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5841854A (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63182274A (ja) * | 1987-01-20 | 1988-07-27 | 住友化学工業株式会社 | 表面に粒子層を有するセラミツク成形体の製造方法 |
| JPS6485644A (en) * | 1987-09-28 | 1989-03-30 | Asahi Optical Co Ltd | Preparation of ceramics composite |
-
1981
- 1981-09-08 JP JP14137681A patent/JPS5841854A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5841854A (ja) | 1983-03-11 |
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