JPS6234020B2 - - Google Patents

Info

Publication number

JPS6234020B2

JPS6234020B2 JP7475180A JP7475180A JPS6234020B2 JP S6234020 B2 JPS6234020 B2 JP S6234020B2 JP 7475180 A JP7475180 A JP 7475180A JP 7475180 A JP7475180 A JP 7475180A JP S6234020 B2 JPS6234020 B2 JP S6234020B2

Authority

JP

Japan

Prior art keywords

liquid crystal

cyclohexane

trans

compound

viscosity

Prior art date

1980-06-03

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

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• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 5
• 125000000217 alkyl group Chemical group 0.000 claims description 5
• 125000004432 carbon atom Chemical group C* 0.000 claims description 4
• 239000004973 liquid crystal related substance Substances 0.000 description 22
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 15
• 239000000203 mixture Substances 0.000 description 15
• 150000001875 compounds Chemical class 0.000 description 11
• 239000000126 substance Substances 0.000 description 6
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
• 238000002844 melting Methods 0.000 description 5
• 230000008018 melting Effects 0.000 description 5
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
• 238000004519 manufacturing process Methods 0.000 description 3
• 239000000463 material Substances 0.000 description 3
• 230000003287 optical effect Effects 0.000 description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 239000003054 catalyst Substances 0.000 description 2
• 238000001816 cooling Methods 0.000 description 2
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
• 229910052739 hydrogen Inorganic materials 0.000 description 2
• 239000001257 hydrogen Substances 0.000 description 2
• 229910052749 magnesium Inorganic materials 0.000 description 2
• 239000011777 magnesium Substances 0.000 description 2
• 238000000034 method Methods 0.000 description 2
• 229910052757 nitrogen Inorganic materials 0.000 description 2
• CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 2
• 229910000343 potassium bisulfate Inorganic materials 0.000 description 2
• 238000006722 reduction reaction Methods 0.000 description 2
• NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
• DEGRSLVEIAAFJY-UHFFFAOYSA-N 1-chloro-4-(4-heptylcyclohexyl)benzene Chemical compound C1CC(CCCCCCC)CCC1C1=CC=C(Cl)C=C1 DEGRSLVEIAAFJY-UHFFFAOYSA-N 0.000 description 1
• QWHCPRHASHNSDA-UHFFFAOYSA-N 4-heptylcyclohexan-1-one Chemical compound CCCCCCCC1CCC(=O)CC1 QWHCPRHASHNSDA-UHFFFAOYSA-N 0.000 description 1
• XXUSEPRYHRDKFV-CTYIDZIISA-N C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(C#N)C=C1 XXUSEPRYHRDKFV-CTYIDZIISA-N 0.000 description 1
• FURZYCFZFBYJBT-JCNLHEQBSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 FURZYCFZFBYJBT-JCNLHEQBSA-N 0.000 description 1
• GITNUDHCNOVRFM-SHTZXODSSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(Cl)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(Cl)C=C1 GITNUDHCNOVRFM-SHTZXODSSA-N 0.000 description 1
• NSGMZTNTQKRAFA-UAPYVXQJSA-N C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CC=C(C#N)C=C1 NSGMZTNTQKRAFA-UAPYVXQJSA-N 0.000 description 1
• DEGRSLVEIAAFJY-QAQDUYKDSA-N C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CC=C(Cl)C=C1 Chemical compound C1C[C@@H](CCCCCCC)CC[C@@H]1C1=CC=C(Cl)C=C1 DEGRSLVEIAAFJY-QAQDUYKDSA-N 0.000 description 1
• CDEMHJCJMMOFMB-UHFFFAOYSA-M ClC1=CC=C([Mg]Br)C=C1 Chemical compound ClC1=CC=C([Mg]Br)C=C1 CDEMHJCJMMOFMB-UHFFFAOYSA-M 0.000 description 1
• 239000007818 Grignard reagent Substances 0.000 description 1
• ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 239000008186 active pharmaceutical agent Substances 0.000 description 1
• YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
• 235000010290 biphenyl Nutrition 0.000 description 1
• 239000004305 biphenyl Substances 0.000 description 1
• 238000010531 catalytic reduction reaction Methods 0.000 description 1
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
• WWMCURUJBADGMN-UHFFFAOYSA-N chlorobenzene;hydrobromide Chemical compound Br.ClC1=CC=CC=C1 WWMCURUJBADGMN-UHFFFAOYSA-N 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
• 150000002148 esters Chemical class 0.000 description 1
• 150000004795 grignard reagents Chemical class 0.000 description 1
• 239000012456 homogeneous solution Substances 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• PESJIPUCTXESJH-UHFFFAOYSA-L magnesium chlorobenzene dibromide Chemical compound [Br-].[Mg+2].C1(=CC=CC=C1)Cl.[Br-] PESJIPUCTXESJH-UHFFFAOYSA-L 0.000 description 1
• 230000007935 neutral effect Effects 0.000 description 1
• MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
• 229910003446 platinum oxide Inorganic materials 0.000 description 1
• OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
• 229910052939 potassium sulfate Inorganic materials 0.000 description 1
• 235000011151 potassium sulphates Nutrition 0.000 description 1
• 239000002994 raw material Substances 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1