IL43738A - Process for the production of 3-halophenols and 3,5-dihalophenols - Google Patents
Process for the production of 3-halophenols and 3,5-dihalophenolsInfo
- Publication number
- IL43738A IL43738A IL43738A IL4373873A IL43738A IL 43738 A IL43738 A IL 43738A IL 43738 A IL43738 A IL 43738A IL 4373873 A IL4373873 A IL 4373873A IL 43738 A IL43738 A IL 43738A
- Authority
- IL
- Israel
- Prior art keywords
- catalyst
- halogen
- sulphur
- reaction
- carried out
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 66
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000003054 catalyst Substances 0.000 claims description 94
- 239000001257 hydrogen Substances 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 49
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 31
- 239000005864 Sulphur Substances 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 24
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 22
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- 229920001021 polysulfide Polymers 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 229910000510 noble metal Inorganic materials 0.000 claims description 19
- -1 sulphur compound Chemical class 0.000 claims description 19
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 17
- 229910052751 metal Inorganic materials 0.000 claims description 17
- 239000002184 metal Substances 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical group 0.000 claims description 13
- 229910052742 iron Inorganic materials 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 239000007858 starting material Substances 0.000 claims description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 10
- 229910052759 nickel Inorganic materials 0.000 claims description 10
- 150000002739 metals Chemical class 0.000 claims description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 7
- 150000003568 thioethers Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 229910052976 metal sulfide Inorganic materials 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
- INKDAKMSOSCDGL-UHFFFAOYSA-N [O].OC1=CC=CC=C1 Chemical group [O].OC1=CC=CC=C1 INKDAKMSOSCDGL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 150000002366 halogen compounds Chemical class 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
- 238000005984 hydrogenation reaction Methods 0.000 description 28
- 239000000243 solution Substances 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000012043 crude product Substances 0.000 description 20
- 150000003839 salts Chemical class 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 12
- 230000008018 melting Effects 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- RANCECPPZPIPNO-UHFFFAOYSA-N 2,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC=C1Cl RANCECPPZPIPNO-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 8
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000005695 dehalogenation reaction Methods 0.000 description 6
- 150000002823 nitrates Chemical class 0.000 description 6
- 229910052979 sodium sulfide Inorganic materials 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 229910017052 cobalt Inorganic materials 0.000 description 5
- 239000010941 cobalt Substances 0.000 description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 239000011261 inert gas Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 5
- YZZVKLJKDFFSFL-UHFFFAOYSA-N 2,3,4,5-tetrachloro-6-methoxyphenol Chemical compound COC1=C(O)C(Cl)=C(Cl)C(Cl)=C1Cl YZZVKLJKDFFSFL-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000013256 coordination polymer Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000012433 hydrogen halide Substances 0.000 description 4
- 229910000039 hydrogen halide Inorganic materials 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 3
- MNOJRWOWILAHAV-UHFFFAOYSA-N 3-bromophenol Chemical compound OC1=CC=CC(Br)=C1 MNOJRWOWILAHAV-UHFFFAOYSA-N 0.000 description 3
- BQMOUSPMWQFEPF-UHFFFAOYSA-N 3-chloro-2,4-dimethylphenol Chemical compound CC1=CC=C(O)C(C)=C1Cl BQMOUSPMWQFEPF-UHFFFAOYSA-N 0.000 description 3
- CYUGXXDSGNFQDT-UHFFFAOYSA-N 3-chloro-4-methylsulfanylphenol Chemical compound CSC1=CC=C(O)C=C1Cl CYUGXXDSGNFQDT-UHFFFAOYSA-N 0.000 description 3
- ZVTLRRZWZYDDLD-UHFFFAOYSA-N 5-chloro-2-phenoxyphenol Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=CC=C1 ZVTLRRZWZYDDLD-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000000370 acceptor Substances 0.000 description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- XIWJLPHQDBDOAN-UHFFFAOYSA-N 2,3,5,6-tetrachloro-4-methoxyphenol Chemical compound COC1=C(Cl)C(Cl)=C(O)C(Cl)=C1Cl XIWJLPHQDBDOAN-UHFFFAOYSA-N 0.000 description 2
- CBVQIDQDYSVVIS-UHFFFAOYSA-N 2,3,6-tribromo-4-chlorophenol Chemical compound OC1=C(Br)C(Br)=C(Cl)C=C1Br CBVQIDQDYSVVIS-UHFFFAOYSA-N 0.000 description 2
- LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-UHFFFAOYSA-N 0.000 description 2
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 2
- GUXWVUVLXIJHQF-UHFFFAOYSA-N 2,5-dibromophenol Chemical compound OC1=CC(Br)=CC=C1Br GUXWVUVLXIJHQF-UHFFFAOYSA-N 0.000 description 2
- FOYWCEUVVIHJKD-UHFFFAOYSA-N 2-methyl-5-(1h-pyrazol-5-yl)pyridine Chemical compound C1=NC(C)=CC=C1C1=CC=NN1 FOYWCEUVVIHJKD-UHFFFAOYSA-N 0.000 description 2
- YFKQRZRAQLZDAZ-UHFFFAOYSA-N 3,5-dichloro-2-methoxyphenol Chemical compound COC1=C(O)C=C(Cl)C=C1Cl YFKQRZRAQLZDAZ-UHFFFAOYSA-N 0.000 description 2
- VPOMSPZBQMDLTM-UHFFFAOYSA-N 3,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC(Cl)=C1 VPOMSPZBQMDLTM-UHFFFAOYSA-N 0.000 description 2
- WADQOGCINABPRT-UHFFFAOYSA-N 3-chloro-2-methylphenol Chemical compound CC1=C(O)C=CC=C1Cl WADQOGCINABPRT-UHFFFAOYSA-N 0.000 description 2
- OAUYXMVYBZXTRF-UHFFFAOYSA-N 4,5-dichloro-2-phenoxyphenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1OC1=CC=CC=C1 OAUYXMVYBZXTRF-UHFFFAOYSA-N 0.000 description 2
- KKFPXGXMSBBNJI-UHFFFAOYSA-N 5-chloro-2-methylphenol Chemical compound CC1=CC=C(Cl)C=C1O KKFPXGXMSBBNJI-UHFFFAOYSA-N 0.000 description 2
- FQVLOBQILLZLJA-UHFFFAOYSA-N 5-chlorobenzene-1,3-diol Chemical compound OC1=CC(O)=CC(Cl)=C1 FQVLOBQILLZLJA-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 125000005366 cycloalkylthio group Chemical group 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 150000003891 oxalate salts Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WWNBZGLDODTKEM-UHFFFAOYSA-N sulfanylidenenickel Chemical compound [Ni]=S WWNBZGLDODTKEM-UHFFFAOYSA-N 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- JAHJITLFJSDRCG-UHFFFAOYSA-N 1,2,3,4,5-pentachloro-6-(2,3,4-trichlorophenyl)benzene Chemical group ClC1=C(Cl)C(Cl)=CC=C1C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl JAHJITLFJSDRCG-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- RYAVVQHFTYJNNF-UHFFFAOYSA-N 2,3,4,5-tetrachloro-6-methylphenol Chemical compound CC1=C(O)C(Cl)=C(Cl)C(Cl)=C1Cl RYAVVQHFTYJNNF-UHFFFAOYSA-N 0.000 description 1
- HCMRJWIKQAJMJZ-UHFFFAOYSA-N 2,3,4,5-tetrachloro-6-phenoxyphenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1OC1=CC=CC=C1 HCMRJWIKQAJMJZ-UHFFFAOYSA-N 0.000 description 1
- ZGWPUIZMCCUZOK-UHFFFAOYSA-N 2,3,4,6-tetrachloro-5-methylphenol Chemical compound CC1=C(Cl)C(O)=C(Cl)C(Cl)=C1Cl ZGWPUIZMCCUZOK-UHFFFAOYSA-N 0.000 description 1
- YOMYXRHJAVTWRN-UHFFFAOYSA-N 2,3,5,6-tetrachloro-4-phenoxyphenol Chemical compound ClC1=C(Cl)C(O)=C(Cl)C(Cl)=C1OC1=CC=CC=C1 YOMYXRHJAVTWRN-UHFFFAOYSA-N 0.000 description 1
- BYWBHISPYQEIBT-UHFFFAOYSA-N 2,3,5-trichloro-4-methoxyphenol Chemical compound COC1=C(Cl)C=C(O)C(Cl)=C1Cl BYWBHISPYQEIBT-UHFFFAOYSA-N 0.000 description 1
- WIISWCJUGKFBMI-UHFFFAOYSA-N 2,3-dichloro-4-methoxyphenol Chemical compound COC1=CC=C(O)C(Cl)=C1Cl WIISWCJUGKFBMI-UHFFFAOYSA-N 0.000 description 1
- HPJJNGSXKRZHMO-UHFFFAOYSA-N 2,3-dichloro-6-methoxyphenol Chemical compound COC1=CC=C(Cl)C(Cl)=C1O HPJJNGSXKRZHMO-UHFFFAOYSA-N 0.000 description 1
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical compound OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 1
- SBQZVLLSNGZXLX-UHFFFAOYSA-N 2,4,5,6-tetrachlorobenzene-1,3-diol Chemical compound OC1=C(Cl)C(O)=C(Cl)C(Cl)=C1Cl SBQZVLLSNGZXLX-UHFFFAOYSA-N 0.000 description 1
- LSWDGWUKYMCEEA-UHFFFAOYSA-N 2,4,5-tribromo-3,6-dimethylphenol Chemical compound CC1=C(O)C(Br)=C(C)C(Br)=C1Br LSWDGWUKYMCEEA-UHFFFAOYSA-N 0.000 description 1
- KDKMSHFGQLWAQW-UHFFFAOYSA-N 2,5-dichloro-3-methoxyphenol Chemical compound COC1=CC(Cl)=CC(O)=C1Cl KDKMSHFGQLWAQW-UHFFFAOYSA-N 0.000 description 1
- GARRNRUXZPMBNK-UHFFFAOYSA-N 2,5-dichloro-4-ethylphenol Chemical compound CCC1=CC(Cl)=C(O)C=C1Cl GARRNRUXZPMBNK-UHFFFAOYSA-N 0.000 description 1
- JXKFAPUUGWQXHX-UHFFFAOYSA-N 2,5-dichloro-4-methoxyphenol Chemical compound COC1=CC(Cl)=C(O)C=C1Cl JXKFAPUUGWQXHX-UHFFFAOYSA-N 0.000 description 1
- YGFPFLRARVYKBZ-UHFFFAOYSA-N 2,5-dichloro-4-methylsulfanylphenol Chemical compound CSC1=CC(Cl)=C(O)C=C1Cl YGFPFLRARVYKBZ-UHFFFAOYSA-N 0.000 description 1
- CHEGJXYORGIREQ-UHFFFAOYSA-N 2,5-dichloro-4-phenoxyphenol Chemical compound C1=C(Cl)C(O)=CC(Cl)=C1OC1=CC=CC=C1 CHEGJXYORGIREQ-UHFFFAOYSA-N 0.000 description 1
- FFAZPGVGIGOTGH-UHFFFAOYSA-N 2,5-dichloro-4-propylphenol Chemical compound CCCC1=CC(Cl)=C(O)C=C1Cl FFAZPGVGIGOTGH-UHFFFAOYSA-N 0.000 description 1
- SOOARYARZPXNAL-UHFFFAOYSA-N 2-(Methylthio)phenol Chemical compound CSC1=CC=CC=C1O SOOARYARZPXNAL-UHFFFAOYSA-N 0.000 description 1
- SJFAAIBDKRBLMN-UHFFFAOYSA-N 2-bromo-3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1Br SJFAAIBDKRBLMN-UHFFFAOYSA-N 0.000 description 1
- FMRKYXVZQWHGDA-UHFFFAOYSA-N 2-bromo-5-chlorophenol Chemical compound OC1=CC(Cl)=CC=C1Br FMRKYXVZQWHGDA-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- TZALXFCHDRHZMO-UHFFFAOYSA-N 2-chloro-6-methoxyphenol Chemical compound COC1=CC=CC(Cl)=C1O TZALXFCHDRHZMO-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- NVQZOERLEJLIEJ-UHFFFAOYSA-N 3,4,5-tribromo-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=C(Br)C(Br)=C1Br NVQZOERLEJLIEJ-UHFFFAOYSA-N 0.000 description 1
- URLRZIAWIDPGHD-UHFFFAOYSA-N 3,4,6-trichloro-2-[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=C(O)C(Cl)=CC(Cl)=C1Cl URLRZIAWIDPGHD-UHFFFAOYSA-N 0.000 description 1
- GNDIVIKZOWZSHY-UHFFFAOYSA-N 3,4-dibromo-2,6-dimethylphenol Chemical compound CC1=CC(Br)=C(Br)C(C)=C1O GNDIVIKZOWZSHY-UHFFFAOYSA-N 0.000 description 1
- VLVWNAYQOZYPNB-UHFFFAOYSA-N 3,4-dichloro-5-methoxyphenol Chemical compound COC1=CC(O)=CC(Cl)=C1Cl VLVWNAYQOZYPNB-UHFFFAOYSA-N 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- HUMNEMSNYHSJQD-UHFFFAOYSA-N 3,5-dibromo-4-chloro-2,6-dimethylphenol Chemical compound BrC1=C(C(=C(C(=C1Cl)Br)C)O)C HUMNEMSNYHSJQD-UHFFFAOYSA-N 0.000 description 1
- LGLFKDKRTJTTJL-UHFFFAOYSA-N 3,5-dichloro-2-methylphenol Chemical compound CC1=C(O)C=C(Cl)C=C1Cl LGLFKDKRTJTTJL-UHFFFAOYSA-N 0.000 description 1
- RIQLAEXANKCQDV-UHFFFAOYSA-N 3,5-dichloro-2-phenoxyphenol Chemical compound OC1=CC(Cl)=CC(Cl)=C1OC1=CC=CC=C1 RIQLAEXANKCQDV-UHFFFAOYSA-N 0.000 description 1
- CUBQDFRSSGBHPM-UHFFFAOYSA-N 3,5-dichloro-4-(2,6-dichloro-4-hydroxyphenyl)phenol Chemical group ClC1=CC(O)=CC(Cl)=C1C1=C(Cl)C=C(O)C=C1Cl CUBQDFRSSGBHPM-UHFFFAOYSA-N 0.000 description 1
- TWXPEKCXBROKDD-UHFFFAOYSA-N 3,5-dichloro-4-methoxyphenol Chemical compound COC1=C(Cl)C=C(O)C=C1Cl TWXPEKCXBROKDD-UHFFFAOYSA-N 0.000 description 1
- HFIYZRHLHRSXEG-UHFFFAOYSA-N 3,6-dichloro-2,4-bis[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=C(Cl)C(CN(C)C)=C(O)C(Cl)=C1 HFIYZRHLHRSXEG-UHFFFAOYSA-N 0.000 description 1
- NQNPJJAAWMJMGS-UHFFFAOYSA-N 3,6-dichloro-2-[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=C(Cl)C=CC(Cl)=C1O NQNPJJAAWMJMGS-UHFFFAOYSA-N 0.000 description 1
- DUKKNDLIWRYBCT-UHFFFAOYSA-N 3-bromo-2-chlorophenol Chemical compound OC1=CC=CC(Br)=C1Cl DUKKNDLIWRYBCT-UHFFFAOYSA-N 0.000 description 1
- JQPIACUMBBGKSM-UHFFFAOYSA-N 3-bromo-4-chloro-2,6-dimethylphenol Chemical compound CC1=CC(Cl)=C(Br)C(C)=C1O JQPIACUMBBGKSM-UHFFFAOYSA-N 0.000 description 1
- JLFFHIKASCUQRL-UHFFFAOYSA-N 3-bromo-4-chlorophenol Chemical compound OC1=CC=C(Cl)C(Br)=C1 JLFFHIKASCUQRL-UHFFFAOYSA-N 0.000 description 1
- FCPHOVHDDYCNCK-UHFFFAOYSA-N 3-chloro-2-phenoxyphenol Chemical compound OC1=CC=CC(Cl)=C1OC1=CC=CC=C1 FCPHOVHDDYCNCK-UHFFFAOYSA-N 0.000 description 1
- LZVYZZFCAMPFOQ-UHFFFAOYSA-N 3-chloro-5-methoxyphenol Chemical compound COC1=CC(O)=CC(Cl)=C1 LZVYZZFCAMPFOQ-UHFFFAOYSA-N 0.000 description 1
- FRZDBARVMIGNGI-UHFFFAOYSA-N 3-chloro-5-phenoxyphenol Chemical compound OC1=CC(Cl)=CC(OC=2C=CC=CC=2)=C1 FRZDBARVMIGNGI-UHFFFAOYSA-N 0.000 description 1
- HAAFFTHBNFBVKY-UHFFFAOYSA-N 4,5-dichloro-2-methoxyphenol Chemical compound COC1=CC(Cl)=C(Cl)C=C1O HAAFFTHBNFBVKY-UHFFFAOYSA-N 0.000 description 1
- YPWZTDHXTALQBZ-UHFFFAOYSA-N 4,5-dichloro-2-methylphenol Chemical compound CC1=CC(Cl)=C(Cl)C=C1O YPWZTDHXTALQBZ-UHFFFAOYSA-N 0.000 description 1
- KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 description 1
- HWWKEEKUMAZJLL-UHFFFAOYSA-N 4-bromo-2,5-dichlorophenol Chemical compound OC1=CC(Cl)=C(Br)C=C1Cl HWWKEEKUMAZJLL-UHFFFAOYSA-N 0.000 description 1
- FQEYHIPPYOSPLF-UHFFFAOYSA-N 4-bromo-3-chlorophenol Chemical compound OC1=CC=C(Br)C(Cl)=C1 FQEYHIPPYOSPLF-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- GNSPWPOHVBPSDX-UHFFFAOYSA-N 4-ethylphenol Chemical compound [CH2]CC1=CC=C(O)C=C1 GNSPWPOHVBPSDX-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- UEVFFMZHGNYDKM-UHFFFAOYSA-N 5-bromo-2-chlorophenol Chemical compound OC1=CC(Br)=CC=C1Cl UEVFFMZHGNYDKM-UHFFFAOYSA-N 0.000 description 1
- HIWHLFQMDDWLRB-UHFFFAOYSA-N 5-chloro-2-methoxyphenol Chemical compound COC1=CC=C(Cl)C=C1O HIWHLFQMDDWLRB-UHFFFAOYSA-N 0.000 description 1
- LMUKIFZFZRTUIY-UHFFFAOYSA-N 5-chloro-2-phenylphenol Chemical group OC1=CC(Cl)=CC=C1C1=CC=CC=C1 LMUKIFZFZRTUIY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- AGVJBLHVMNHENQ-UHFFFAOYSA-N Calcium sulfide Chemical compound [S-2].[Ca+2] AGVJBLHVMNHENQ-UHFFFAOYSA-N 0.000 description 1
- FUOXSPWKESDXAQ-UHFFFAOYSA-N ClC1=C(C(=C(C(=C1OC1=CC=CC=C1)Cl)Cl)Cl)O Chemical compound ClC1=C(C(=C(C(=C1OC1=CC=CC=C1)Cl)Cl)Cl)O FUOXSPWKESDXAQ-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- VVNCNSJFMMFHPL-VKHMYHEASA-N D-penicillamine Chemical class CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 description 1
- MBMLMWLHJBBADN-UHFFFAOYSA-N Ferrous sulfide Chemical compound [Fe]=S MBMLMWLHJBBADN-UHFFFAOYSA-N 0.000 description 1
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 1
- 101100309040 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) lea-1 gene Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 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
- 150000001448 anilines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- CJOBVZJTOIVNNF-UHFFFAOYSA-N cadmium sulfide Chemical compound [Cd]=S CJOBVZJTOIVNNF-UHFFFAOYSA-N 0.000 description 1
- 229910052980 cadmium sulfide Inorganic materials 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
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- BWFPGXWASODCHM-UHFFFAOYSA-N copper monosulfide Chemical compound [Cu]=S BWFPGXWASODCHM-UHFFFAOYSA-N 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000009937 cyclo 3 Substances 0.000 description 1
- 229940075911 depen Drugs 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002023 dithiocarboxylic acids Chemical class 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- ACGUYXCXAPNIKK-UHFFFAOYSA-N hexachlorophene Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl ACGUYXCXAPNIKK-UHFFFAOYSA-N 0.000 description 1
- 229960004068 hexachlorophene Drugs 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XCAUINMIESBTBL-UHFFFAOYSA-N lead(ii) sulfide Chemical compound [Pb]=S XCAUINMIESBTBL-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
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- HXDOZKJGKXYMEW-UHFFFAOYSA-N para-ethyl phenol Natural products CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- DPLVEEXVKBWGHE-UHFFFAOYSA-N potassium sulfide Chemical compound [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N pyrocatechol monomethyl ether Natural products COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(I) nitrate Inorganic materials [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- YPMOSINXXHVZIL-UHFFFAOYSA-N sulfanylideneantimony Chemical compound [Sb]=S YPMOSINXXHVZIL-UHFFFAOYSA-N 0.000 description 1
- VRRFSFYSLSPWQY-UHFFFAOYSA-N sulfanylidenecobalt Chemical compound [Co]=S VRRFSFYSLSPWQY-UHFFFAOYSA-N 0.000 description 1
- CADICXFYUNYKGD-UHFFFAOYSA-N sulfanylidenemanganese Chemical compound [Mn]=S CADICXFYUNYKGD-UHFFFAOYSA-N 0.000 description 1
- PGWMQVQLSMAHHO-UHFFFAOYSA-N sulfanylidenesilver Chemical compound [Ag]=S PGWMQVQLSMAHHO-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 125000005323 thioketone group Chemical group 0.000 description 1
- 150000004764 thiosulfuric acid derivatives Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/24—Preparation of ethers by reactions not forming ether-oxygen bonds by elimination of halogens, e.g. elimination of HCl
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
- B01J27/04—Sulfides
- B01J27/043—Sulfides with iron group metals or platinum group metals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/20—Sulfiding
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722259433 DE2259433A1 (de) | 1972-12-05 | 1972-12-05 | Verfahren zur herstellung von 3-halogen- und 3,5-dihalogen-phenolen |
| DE19732344925 DE2344925C3 (de) | 1973-09-06 | 1973-09-06 | Verfahren zur Herstellung von 3-Halogen- und 3,5-Dihalogenphenolen |
| DE2344926A DE2344926C3 (de) | 1973-09-06 | 1973-09-06 | Verfahren zur Herstellung von 3-Halogen- bzw. 3,5-Dihalogen-phenolen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL43738A0 IL43738A0 (en) | 1974-03-14 |
| IL43738A true IL43738A (en) | 1977-03-31 |
Family
ID=27184885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL43738A IL43738A (en) | 1972-12-05 | 1973-12-03 | Process for the production of 3-halophenols and 3,5-dihalophenols |
Country Status (13)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2443152C3 (de) * | 1974-09-10 | 1981-05-21 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von durch Halogen meta-substituierten Phenolen |
| DE2607349A1 (de) * | 1976-02-24 | 1977-08-25 | Bayer Ag | Mikrobizide meta-chlorphenole |
| US4215229A (en) * | 1978-06-15 | 1980-07-29 | Koppers Company, Inc. | Process for alkylating phenolic compounds to produce ortho- and para-monoalkylated phenols and 2,4- and 2,6-dialkylated phenols |
| SU877836A1 (ru) * | 1978-11-23 | 1984-01-30 | Предприятие П/Я Р-6913 | Катализатор дл деалкилировани алкилбензолов с вод ным паром |
| FR2496639A1 (fr) * | 1980-12-24 | 1982-06-25 | Rhone Poulenc Ind | Procede de preparation de phenols metachlores |
| FR2496641A1 (fr) * | 1980-12-24 | 1982-06-25 | Rhone Poulenc Ind | Procede de preparation de phenols metachlores |
| FR2496640A1 (fr) * | 1980-12-24 | 1982-06-25 | Rhone Poulenc Ind | Procede de preparation de phenols metachlores |
| JPS60115543A (ja) * | 1983-11-26 | 1985-06-22 | Dai Ichi Kogyo Seiyaku Co Ltd | 臭素化−ｐ−フエニルフエノ−ル |
| FR2647032B1 (fr) * | 1989-04-07 | 1993-12-10 | Atochem | Procede et catalyseur de deshalogenation d'acides carboxyliques alphahalogenes |
| FR2645531B1 (fr) * | 1989-04-07 | 1991-06-07 | Atochem | Procede et catalyseur de deshalogenation d'acides carboxyliques alphahalogenes |
-
1973
- 1973-11-28 GB GB5509373A patent/GB1419603A/en not_active Expired
- 1973-12-03 IT IT54051/73A patent/IT1000182B/it active
- 1973-12-03 AT AT1009773A patent/AT329023B/de not_active IP Right Cessation
- 1973-12-03 CH CH1697173A patent/CH592592A5/xx not_active IP Right Cessation
- 1973-12-03 NL NL7316527A patent/NL7316527A/xx not_active Application Discontinuation
- 1973-12-03 CA CA187,162A patent/CA1023766A/en not_active Expired
- 1973-12-03 IL IL43738A patent/IL43738A/en unknown
- 1973-12-03 LU LU68921A patent/LU68921A1/xx unknown
- 1973-12-04 ES ES421137A patent/ES421137A1/es not_active Expired
- 1973-12-04 IE IE02188/73A patent/IE38873B1/xx unknown
- 1973-12-04 JP JP48134962A patent/JPS5745727B2/ja not_active Expired
- 1973-12-04 DK DK655173A patent/DK143226C/da active
- 1973-12-05 FR FR7343484A patent/FR2209738B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA1023766A (en) | 1978-01-03 |
| FR2209738B1 (enrdf_load_stackoverflow) | 1977-08-05 |
| IE38873L (en) | 1974-06-05 |
| FR2209738A1 (enrdf_load_stackoverflow) | 1974-07-05 |
| JPS4993330A (enrdf_load_stackoverflow) | 1974-09-05 |
| LU68921A1 (enrdf_load_stackoverflow) | 1974-02-11 |
| AT329023B (de) | 1976-04-26 |
| ATA1009773A (de) | 1975-07-15 |
| NL7316527A (enrdf_load_stackoverflow) | 1974-06-07 |
| DK143226B (da) | 1981-07-27 |
| IE38873B1 (en) | 1978-06-21 |
| IL43738A0 (en) | 1974-03-14 |
| IT1000182B (it) | 1976-03-30 |
| CH592592A5 (enrdf_load_stackoverflow) | 1977-10-31 |
| DK143226C (da) | 1981-12-07 |
| ES421137A1 (es) | 1976-07-01 |
| JPS5745727B2 (enrdf_load_stackoverflow) | 1982-09-29 |
| GB1419603A (en) | 1975-12-31 |
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