NO124268B - - Google Patents
Download PDFInfo
- Publication number
- NO124268B NO124268B NO36469A NO36469A NO124268B NO 124268 B NO124268 B NO 124268B NO 36469 A NO36469 A NO 36469A NO 36469 A NO36469 A NO 36469A NO 124268 B NO124268 B NO 124268B
- Authority
- NO
- Norway
- Prior art keywords
- oxy
- coumarin
- phenyl
- carbinol
- parts
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 238000002844 melting Methods 0.000 description 48
- 230000008018 melting Effects 0.000 description 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 40
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 229960000583 acetic acid Drugs 0.000 description 19
- 239000007795 chemical reaction product Substances 0.000 description 17
- 239000012362 glacial acetic acid Substances 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
- 239000000155 melt Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- 238000009833 condensation Methods 0.000 description 7
- 230000005494 condensation Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
- -1 aryl-alkyl ketones Chemical class 0.000 description 6
- 229950009195 phenylpropanol Drugs 0.000 description 6
- 239000006286 aqueous extract Substances 0.000 description 5
- 229940058172 ethylbenzene Drugs 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- DYUQAZSOFZSPHD-UHFFFAOYSA-N Phenylpropanol Chemical compound CCC(O)C1=CC=CC=C1 DYUQAZSOFZSPHD-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- IBNWKIKUJJNBKG-UHFFFAOYSA-N [methoxy(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(OC)C1=CC=CC=C1 IBNWKIKUJJNBKG-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Substances C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- MVOSNPUNXINWAD-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanol Chemical compound CC(O)C1=CC=C(Cl)C=C1 MVOSNPUNXINWAD-UHFFFAOYSA-N 0.000 description 2
- TXAWBKBMGZKBNN-UHFFFAOYSA-N 1-(4-chlorophenyl)propan-1-ol Chemical compound CCC(O)C1=CC=C(Cl)C=C1 TXAWBKBMGZKBNN-UHFFFAOYSA-N 0.000 description 2
- NTTBDWAXCRRVJY-UHFFFAOYSA-N 1-(4-ethylphenyl)propan-1-ol Chemical compound CCC(O)C1=CC=C(CC)C=C1 NTTBDWAXCRRVJY-UHFFFAOYSA-N 0.000 description 2
- RELLLNVFFUWXHI-UHFFFAOYSA-N 1-(4-methoxyphenyl)propan-1-ol Chemical compound CCC(O)C1=CC=C(OC)C=C1 RELLLNVFFUWXHI-UHFFFAOYSA-N 0.000 description 2
- ZBDUWPZEVMGAMD-UHFFFAOYSA-N 1-(4-methylphenyl)propan-1-ol Chemical compound CCC(O)C1=CC=C(C)C=C1 ZBDUWPZEVMGAMD-UHFFFAOYSA-N 0.000 description 2
- HQRWWHIETAKIMO-UHFFFAOYSA-N 1-phenylbutan-1-ol Chemical compound CCCC(O)C1=CC=CC=C1 HQRWWHIETAKIMO-UHFFFAOYSA-N 0.000 description 2
- GMDYDZMQHRTHJA-UHFFFAOYSA-N 2-methyl-1-phenylpropan-1-ol Chemical compound CC(C)C(O)C1=CC=CC=C1 GMDYDZMQHRTHJA-UHFFFAOYSA-N 0.000 description 2
- NJIRMTSCELFREO-UHFFFAOYSA-N 3-(4-methylphenyl)propan-1-ol Chemical compound CC1=CC=C(CCCO)C=C1 NJIRMTSCELFREO-UHFFFAOYSA-N 0.000 description 2
- OVGORFFCBUIFIA-UHFFFAOYSA-N Fenipentol Chemical compound CCCCC(O)C1=CC=CC=C1 OVGORFFCBUIFIA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LYWASOZKZYKPQR-UHFFFAOYSA-N [ethoxy(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(OCC)C1=CC=CC=C1 LYWASOZKZYKPQR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N alpha-methylbenzylalcohol Natural products CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- QBKMWJRMLACRJD-UHFFFAOYSA-N benzhydryl acetate Chemical compound C=1C=CC=CC=1C(OC(=O)C)C1=CC=CC=C1 QBKMWJRMLACRJD-UHFFFAOYSA-N 0.000 description 2
- OQROAIRCEOBYJA-UHFFFAOYSA-N bromodiphenylmethane Chemical compound C=1C=CC=CC=1C(Br)C1=CC=CC=C1 OQROAIRCEOBYJA-UHFFFAOYSA-N 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 150000004775 coumarins Chemical class 0.000 description 2
- QDYKZBKCLHBUHU-UHFFFAOYSA-N cyclohexyl(phenyl)methanol Chemical compound C=1C=CC=CC=1C(O)C1CCCCC1 QDYKZBKCLHBUHU-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 229960005035 fenipentol Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- YVRQODFKFKHCPI-UHFFFAOYSA-N 1,3-diphenylpropan-1-ol Chemical compound C=1C=CC=CC=1C(O)CCC1=CC=CC=C1 YVRQODFKFKHCPI-UHFFFAOYSA-N 0.000 description 1
- SZWQHGDPILROHA-UHFFFAOYSA-N 1-(1-methoxypropyl)-4-methylbenzene Chemical compound CCC(OC)C1=CC=C(C)C=C1 SZWQHGDPILROHA-UHFFFAOYSA-N 0.000 description 1
- CYQOCEDBJWGLAP-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-ol Chemical compound CCC(O)C1=CC=C(C)C=C1C CYQOCEDBJWGLAP-UHFFFAOYSA-N 0.000 description 1
- UBOFXBQTRQSKMY-UHFFFAOYSA-N 1-(2-chlorophenyl)propan-1-ol Chemical compound CCC(O)C1=CC=CC=C1Cl UBOFXBQTRQSKMY-UHFFFAOYSA-N 0.000 description 1
- WTTSQZZOTXFJJG-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)ethanol Chemical compound CC(O)C1=CC=C(C)C(C)=C1 WTTSQZZOTXFJJG-UHFFFAOYSA-N 0.000 description 1
- APYGJPRINQKIQF-UHFFFAOYSA-N 1-(3-chlorophenyl)propan-1-ol Chemical compound CCC(O)C1=CC=CC(Cl)=C1 APYGJPRINQKIQF-UHFFFAOYSA-N 0.000 description 1
- SKBBQSLSGRSQAJ-UHFFFAOYSA-N 1-(4-acetylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C(C)=O)C=C1 SKBBQSLSGRSQAJ-UHFFFAOYSA-N 0.000 description 1
- XDWKHOYVNAYRQX-UHFFFAOYSA-N 1-(4-chlorophenyl)propyl acetate Chemical compound CC(=O)OC(CC)C1=CC=C(Cl)C=C1 XDWKHOYVNAYRQX-UHFFFAOYSA-N 0.000 description 1
- CYEIZTMWVNXOQH-UHFFFAOYSA-N 1-(4-cyclohexylphenyl)ethanol Chemical compound C1=CC(C(O)C)=CC=C1C1CCCCC1 CYEIZTMWVNXOQH-UHFFFAOYSA-N 0.000 description 1
- BJTFSJALTYYMKU-UHFFFAOYSA-N 1-(4-ethoxyphenyl)propan-1-ol Chemical compound CCOC1=CC=C(C(O)CC)C=C1 BJTFSJALTYYMKU-UHFFFAOYSA-N 0.000 description 1
- HZFBZEOPUXCNHK-UHFFFAOYSA-N 1-(4-ethylphenyl)ethanol Chemical compound CCC1=CC=C(C(C)O)C=C1 HZFBZEOPUXCNHK-UHFFFAOYSA-N 0.000 description 1
- PSDSORRYQPTKSV-UHFFFAOYSA-N 1-(4-fluorophenyl)ethanol Chemical compound CC(O)C1=CC=C(F)C=C1 PSDSORRYQPTKSV-UHFFFAOYSA-N 0.000 description 1
- ARRSWKWGQREELC-UHFFFAOYSA-N 1-(4-methoxyphenyl)butan-2-ol Chemical compound CCC(O)CC1=CC=C(OC)C=C1 ARRSWKWGQREELC-UHFFFAOYSA-N 0.000 description 1
- OEUXAZRVDHRZSV-UHFFFAOYSA-N 1-(4-methoxyphenyl)pentan-2-ol Chemical compound CCCC(O)CC1=CC=C(OC)C=C1 OEUXAZRVDHRZSV-UHFFFAOYSA-N 0.000 description 1
- QTJVYHSODWHIMO-UHFFFAOYSA-N 1-(4-methylphenyl)butan-1-ol Chemical compound CCCC(O)C1=CC=C(C)C=C1 QTJVYHSODWHIMO-UHFFFAOYSA-N 0.000 description 1
- BAHVSNRQBUCEGZ-UHFFFAOYSA-N 1-(4-methylphenyl)pentan-1-ol Chemical compound CCCCC(O)C1=CC=C(C)C=C1 BAHVSNRQBUCEGZ-UHFFFAOYSA-N 0.000 description 1
- HCIFMENZOKGFEI-UHFFFAOYSA-N 1-(4-phenoxyphenyl)ethanol Chemical compound C1=CC(C(O)C)=CC=C1OC1=CC=CC=C1 HCIFMENZOKGFEI-UHFFFAOYSA-N 0.000 description 1
- LPWMXVJCBUKVQH-UHFFFAOYSA-N 1-(4-propan-2-ylphenyl)ethanol Chemical compound CC(C)C1=CC=C(C(C)O)C=C1 LPWMXVJCBUKVQH-UHFFFAOYSA-N 0.000 description 1
- NUNYALSGVAYXDW-UHFFFAOYSA-N 1-(4-propan-2-ylphenyl)propan-1-ol Chemical compound CCC(O)C1=CC=C(C(C)C)C=C1 NUNYALSGVAYXDW-UHFFFAOYSA-N 0.000 description 1
- AWOFDBUEQBAWBO-UHFFFAOYSA-N 1-(4-propylphenyl)ethanol Chemical compound CCCC1=CC=C(C(C)O)C=C1 AWOFDBUEQBAWBO-UHFFFAOYSA-N 0.000 description 1
- FJQGKCRAZXIDNI-UHFFFAOYSA-N 1-(4-propylphenyl)propan-1-ol Chemical compound CCCC1=CC=C(C(O)CC)C=C1 FJQGKCRAZXIDNI-UHFFFAOYSA-N 0.000 description 1
- QUMXDOLUJCHOAY-UHFFFAOYSA-N 1-Phenylethyl acetate Chemical compound CC(=O)OC(C)C1=CC=CC=C1 QUMXDOLUJCHOAY-UHFFFAOYSA-N 0.000 description 1
- KPUCACGWLYWKKD-UHFFFAOYSA-N 1-Phenylpropyl acetate Chemical compound CC(=O)OC(CC)C1=CC=CC=C1 KPUCACGWLYWKKD-UHFFFAOYSA-N 0.000 description 1
- XJSUFXFSUACKAT-UHFFFAOYSA-N 1-bromopropylbenzene Chemical compound CCC(Br)C1=CC=CC=C1 XJSUFXFSUACKAT-UHFFFAOYSA-N 0.000 description 1
- CEJVQEAKGWJHNK-UHFFFAOYSA-N 1-chloro-4-[(4-chlorophenyl)-methoxymethyl]benzene Chemical compound C=1C=C(Cl)C=CC=1C(OC)C1=CC=C(Cl)C=C1 CEJVQEAKGWJHNK-UHFFFAOYSA-N 0.000 description 1
- DZJXIQWBKRNKOI-UHFFFAOYSA-N 1-methoxybutylbenzene Chemical compound CCCC(OC)C1=CC=CC=C1 DZJXIQWBKRNKOI-UHFFFAOYSA-N 0.000 description 1
- PLKSMSKTENNPEJ-UHFFFAOYSA-N 1-methoxyethylbenzene Chemical compound COC(C)C1=CC=CC=C1 PLKSMSKTENNPEJ-UHFFFAOYSA-N 0.000 description 1
- ANKVSZOYVTWLQO-UHFFFAOYSA-N 1-methoxypropylbenzene Chemical compound CCC(OC)C1=CC=CC=C1 ANKVSZOYVTWLQO-UHFFFAOYSA-N 0.000 description 1
- SVCRDVHXRDRHCP-UHFFFAOYSA-N 1-phenylhexan-1-ol Chemical compound CCCCCC(O)C1=CC=CC=C1 SVCRDVHXRDRHCP-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- FJARXZBBVNLZDX-UHFFFAOYSA-N 3-(2,5-dimethylphenyl)propan-1-ol Chemical compound CC1=CC=C(C)C(CCCO)=C1 FJARXZBBVNLZDX-UHFFFAOYSA-N 0.000 description 1
- IUUULXXWNYKJSL-UHFFFAOYSA-N 4-methoxy-alpha-methylbenzyl alcohol Chemical compound COC1=CC=C(C(C)O)C=C1 IUUULXXWNYKJSL-UHFFFAOYSA-N 0.000 description 1
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JMMYXBGUFXFIFW-UHFFFAOYSA-N C1CC2=C(C=CC3=CC=CC1=C23)C(O)C Chemical compound C1CC2=C(C=CC3=CC=CC1=C23)C(O)C JMMYXBGUFXFIFW-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- ZDVDCDLBOLSVGM-UHFFFAOYSA-N [chloro(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(Cl)C1=CC=CC=C1 ZDVDCDLBOLSVGM-UHFFFAOYSA-N 0.000 description 1
- 125000005011 alkyl ether group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 230000002429 anti-coagulating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- MRDOPPZMPMSASQ-UHFFFAOYSA-N benzhydryloxymethylbenzene Chemical compound C=1C=CC=CC=1COC(C=1C=CC=CC=1)C1=CC=CC=C1 MRDOPPZMPMSASQ-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VGHPXXXQUPPGLI-UHFFFAOYSA-N bis(4-chlorophenyl)methyl acetate Chemical compound C=1C=C(Cl)C=CC=1C(OC(=O)C)C1=CC=C(Cl)C=C1 VGHPXXXQUPPGLI-UHFFFAOYSA-N 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 150000004651 carbonic acid esters Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C21—METALLURGY OF IRON
- C21B—MANUFACTURE OF IRON OR STEEL
- C21B13/00—Making spongy iron or liquid steel, by direct processes
- C21B13/08—Making spongy iron or liquid steel, by direct processes in rotary furnaces
-
- C—CHEMISTRY; METALLURGY
- C21—METALLURGY OF IRON
- C21B—MANUFACTURE OF IRON OR STEEL
- C21B13/00—Making spongy iron or liquid steel, by direct processes
- C21B13/0086—Conditioning, transformation of reduced iron ores
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Metallurgy (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Geochemistry & Mineralogy (AREA)
- Geology (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Environmental & Geological Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Manufacture And Refinement Of Metals (AREA)
- Manufacture Of Iron (AREA)
- Muffle Furnaces And Rotary Kilns (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681583954 DE1583954B2 (de) | 1968-02-08 | 1968-02-08 | Verfahren zur direktreduktion von eisenoxydhaltigen materialien im drehrohrofen im gleichstromverfahren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO124268B true NO124268B (zh) | 1972-03-27 |
Family
ID=5679588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO36469A NO124268B (zh) | 1968-02-08 | 1969-01-30 |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS514929B1 (zh) |
| AT (1) | AT291319B (zh) |
| BE (1) | BE728153A (zh) |
| ES (1) | ES363307A1 (zh) |
| FR (1) | FR2001568A1 (zh) |
| GB (1) | GB1203532A (zh) |
| NO (1) | NO124268B (zh) |
| PL (1) | PL76027B1 (zh) |
| SE (1) | SE356313B (zh) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7167534B2 (ja) * | 2018-08-06 | 2022-11-09 | 住友金属鉱山株式会社 | 酸化鉱石の製錬方法 |
| JP7196461B2 (ja) * | 2018-08-21 | 2022-12-27 | 住友金属鉱山株式会社 | 酸化鉱石の製錬方法 |
-
1969
- 1969-01-27 JP JP627269A patent/JPS514929B1/ja active Pending
- 1969-01-28 AT AT85169A patent/AT291319B/de not_active IP Right Cessation
- 1969-01-30 NO NO36469A patent/NO124268B/no unknown
- 1969-01-30 GB GB525469A patent/GB1203532A/en not_active Expired
- 1969-02-04 PL PL13153769A patent/PL76027B1/pl unknown
- 1969-02-07 FR FR6902891A patent/FR2001568A1/fr not_active Withdrawn
- 1969-02-07 SE SE168669A patent/SE356313B/xx unknown
- 1969-02-07 BE BE728153D patent/BE728153A/xx unknown
-
1970
- 1970-02-05 ES ES363307A patent/ES363307A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES363307A1 (es) | 1970-12-16 |
| PL76027B1 (zh) | 1975-02-28 |
| SE356313B (zh) | 1973-05-21 |
| FR2001568A1 (zh) | 1969-09-26 |
| JPS514929B1 (zh) | 1976-02-16 |
| BE728153A (zh) | 1969-07-16 |
| GB1203532A (en) | 1970-08-26 |
| AT291319B (de) | 1971-07-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Kuehne et al. | Reactions of ynamines | |
| Gilman et al. | Metalation of thiophene by n-butyllithium | |
| NO174506B (no) | Analogifremgangsmaate ved fremstilling av terapeutisk aktive forbindelser | |
| US3132147A (en) | ||
| DE1770460A1 (de) | Verfahren zur Herstellung von neuen Indolderivaten | |
| NO137694B (no) | Analogifremgangsm}te for fremstilling av terapeutisk aktive benzomorfaner | |
| NO142865B (no) | Analogifremgangsmaate ved fremstilling av nye terapeutisk aktive karbazoler | |
| Szantay et al. | Synthesis of substituted octahydroindolo [2, 3-a]-quinolizines. The formation of a new type of ring system | |
| NO124268B (zh) | ||
| Drummond et al. | Alkaloids of the Australian Rutaceae: Acronychia baueri. III. The structure of acronycine | |
| Kiang et al. | 268. The action of acyl cyanides on 2-and 1: 2-substituted indoles. Part II. Derivatives of 2-o-aminophenylindole | |
| Adams et al. | The Reaction of 2-Aminopyridine with α-Halo Ketones | |
| Leonard et al. | Reactions of Quinolinium Compounds with Phenylacetonitrile and Its Homologs | |
| King et al. | The Preparation of 2-Substituted Vinyl Quaternary Salts | |
| US3423409A (en) | Triazines | |
| Bailey et al. | 282. Synthetical experiments in the chelidonine–sanguinarine group of the alkaloids. Part II | |
| US2806034A (en) | 3-(heterocyclic-substituted alkyl) thianaphthenes and salts thereof | |
| Eck et al. | The Synthesis of Bis-2, 2'-(1, 3-diphenylindenol-3). A Contribution to the Rubrene Problem | |
| Potts et al. | Synthesis of sempervirine | |
| JPH0325423B2 (zh) | ||
| US2809199A (en) | Process and intermediates for preparing rauwolscine and derivatives | |
| US2707187A (en) | Chemical process | |
| DE1810341A1 (de) | Verfahren zur Herstellung von Tetrahydroisochinolin-Derivaten | |
| Bader et al. | Synthetic Oxytocics. I. Synthesis and Reactions of 3-Indolyl-2'-pyridylcarbinols and of 2, 3-(2', 3'-Indolo)-hexahydroquinolizines | |
| Lauer et al. | 5-Bromo-6-methoxy-8-aminoquinoline and its Transformation to 7-Bromo-6-methoxy-8-aminoquinoline1 |