JPS6050773B2 - メタクロルフエノ−ルの製造法 - Google Patents
メタクロルフエノ−ルの製造法Info
- Publication number
- JPS6050773B2 JPS6050773B2 JP56203771A JP20377181A JPS6050773B2 JP S6050773 B2 JPS6050773 B2 JP S6050773B2 JP 56203771 A JP56203771 A JP 56203771A JP 20377181 A JP20377181 A JP 20377181A JP S6050773 B2 JPS6050773 B2 JP S6050773B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- polychlorophenol
- formula
- group containing
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 42
- 239000003054 catalyst Substances 0.000 claims description 20
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 20
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 18
- 239000002841 Lewis acid Substances 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 150000007517 lewis acids Chemical class 0.000 claims description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- -1 aluminum halide Chemical class 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- VGVRPFIJEJYOFN-UHFFFAOYSA-N 2,3,4,6-tetrachlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1Cl VGVRPFIJEJYOFN-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 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 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910000510 noble metal Inorganic materials 0.000 claims description 6
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 claims description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical group ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 claims description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical group ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 150000001649 bromium compounds Chemical class 0.000 claims description 2
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- 229940117389 dichlorobenzene Drugs 0.000 claims description 2
- 150000004694 iodide salts Chemical class 0.000 claims description 2
- 239000012074 organic phase Substances 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 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 1
- 239000003960 organic solvent Substances 0.000 claims 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical group CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 claims 1
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 230000035484 reaction time Effects 0.000 description 9
- VPOMSPZBQMDLTM-UHFFFAOYSA-N 3,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC(Cl)=C1 VPOMSPZBQMDLTM-UHFFFAOYSA-N 0.000 description 8
- 235000013824 polyphenols Nutrition 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- RULKYXXCCZZKDZ-UHFFFAOYSA-N 2,3,4,5-tetrachlorophenol Chemical class OC1=CC(Cl)=C(Cl)C(Cl)=C1Cl RULKYXXCCZZKDZ-UHFFFAOYSA-N 0.000 description 5
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- WWGQHTJIFOQAOC-UHFFFAOYSA-N 2,3,5-trichlorophenol Chemical compound OC1=CC(Cl)=CC(Cl)=C1Cl WWGQHTJIFOQAOC-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- HSQFVBWFPBKHEB-UHFFFAOYSA-N 2,3,4-trichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1Cl HSQFVBWFPBKHEB-UHFFFAOYSA-N 0.000 description 3
- KEWNKZNZRIAIAK-UHFFFAOYSA-N 2,3,5,6-tetrachlorophenol Chemical compound OC1=C(Cl)C(Cl)=CC(Cl)=C1Cl KEWNKZNZRIAIAK-UHFFFAOYSA-N 0.000 description 3
- MCCTUAKNFRUXLR-UHFFFAOYSA-N 2,3-dichloro-4-methylphenol Chemical compound CC1=CC=C(O)C(Cl)=C1Cl MCCTUAKNFRUXLR-UHFFFAOYSA-N 0.000 description 3
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical compound OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000006298 dechlorination reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-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
- RANCECPPZPIPNO-UHFFFAOYSA-N 2,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC=C1Cl RANCECPPZPIPNO-UHFFFAOYSA-N 0.000 description 2
- HOLHYSJJBXSLMV-UHFFFAOYSA-N 2,6-dichlorophenol Chemical compound OC1=C(Cl)C=CC=C1Cl HOLHYSJJBXSLMV-UHFFFAOYSA-N 0.000 description 2
- VQZRLBWPEHFGCD-UHFFFAOYSA-N 3-chloro-4-methylphenol Chemical compound CC1=CC=C(O)C=C1Cl VQZRLBWPEHFGCD-UHFFFAOYSA-N 0.000 description 2
- AQJFATAFTQCRGC-UHFFFAOYSA-N 3-chloro-4-methylphenol Natural products CC1=CC=C(O)C(Cl)=C1 AQJFATAFTQCRGC-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
- ZVTLRRZWZYDDLD-UHFFFAOYSA-N 5-chloro-2-phenoxyphenol Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=CC=C1 ZVTLRRZWZYDDLD-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229960001867 guaiacol Drugs 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZSUXOVNWDZTCFN-UHFFFAOYSA-L tin(ii) bromide Chemical compound Br[Sn]Br ZSUXOVNWDZTCFN-UHFFFAOYSA-L 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 2
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
- 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 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
- UEOISBCKSXPPKK-UHFFFAOYSA-N 2,3,5,6-tetrachloro-4-methylphenol Chemical compound CC1=C(Cl)C(Cl)=C(O)C(Cl)=C1Cl UEOISBCKSXPPKK-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
- XGCHAIDDPMFRLJ-UHFFFAOYSA-N 2,3,6-trichlorophenol Chemical compound OC1=C(Cl)C=CC(Cl)=C1Cl XGCHAIDDPMFRLJ-UHFFFAOYSA-N 0.000 description 1
- HWICZHMCJUGGDF-UHFFFAOYSA-N 2,3-dichloro-5-methoxyphenol Chemical compound COC1=CC(O)=C(Cl)C(Cl)=C1 HWICZHMCJUGGDF-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
- FDWNKORATHTORU-UHFFFAOYSA-N 2,3-dichloro-6-methylphenol Chemical compound CC1=CC=C(Cl)C(Cl)=C1O FDWNKORATHTORU-UHFFFAOYSA-N 0.000 description 1
- CGZXREWRVNAVSY-UHFFFAOYSA-N 2,5-dichloro-3,4-dimethylphenol Chemical compound CC1=C(C)C(Cl)=C(O)C=C1Cl CGZXREWRVNAVSY-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
- FFAZPGVGIGOTGH-UHFFFAOYSA-N 2,5-dichloro-4-propylphenol Chemical compound CCCC1=CC(Cl)=C(O)C=C1Cl FFAZPGVGIGOTGH-UHFFFAOYSA-N 0.000 description 1
- ZAMOVMHWSVVCQD-UHFFFAOYSA-N 2-benzyl-3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1CC1=CC=CC=C1 ZAMOVMHWSVVCQD-UHFFFAOYSA-N 0.000 description 1
- 229940061334 2-phenylphenol Drugs 0.000 description 1
- GBNHEBQXJVDXSW-UHFFFAOYSA-N 3,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C(Cl)=C1 GBNHEBQXJVDXSW-UHFFFAOYSA-N 0.000 description 1
- WDNBURPWRNALGP-UHFFFAOYSA-N 3,4-Dichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1 WDNBURPWRNALGP-UHFFFAOYSA-N 0.000 description 1
- FSZOOIPIXZDPRT-UHFFFAOYSA-N 3,4-dichloro-2-ethoxyphenol Chemical compound CCOC1=C(O)C=CC(Cl)=C1Cl FSZOOIPIXZDPRT-UHFFFAOYSA-N 0.000 description 1
- YQDGZRGOCDIQJQ-UHFFFAOYSA-N 3,4-dichloro-2-methoxyphenol Chemical compound COC1=C(O)C=CC(Cl)=C1Cl YQDGZRGOCDIQJQ-UHFFFAOYSA-N 0.000 description 1
- OBAQODNMTCJDSX-UHFFFAOYSA-N 3,4-dichloro-2-phenylphenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1C1=CC=CC=C1 OBAQODNMTCJDSX-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
- YFKQRZRAQLZDAZ-UHFFFAOYSA-N 3,5-dichloro-2-methoxyphenol Chemical compound COC1=C(O)C=C(Cl)C=C1Cl YFKQRZRAQLZDAZ-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
- HKSIKNWFLXKKPJ-UHFFFAOYSA-N 3,5-dichloro-4-ethylphenol Chemical compound CCC1=C(Cl)C=C(O)C=C1Cl HKSIKNWFLXKKPJ-UHFFFAOYSA-N 0.000 description 1
- VVHKBMKBOORWSQ-UHFFFAOYSA-N 3,5-dichloro-4-methylphenol Chemical compound CC1=C(Cl)C=C(O)C=C1Cl VVHKBMKBOORWSQ-UHFFFAOYSA-N 0.000 description 1
- KVJVTSGIASNWFB-UHFFFAOYSA-N 3,5-dichloro-4-propylphenol Chemical compound CCCC1=C(Cl)C=C(O)C=C1Cl KVJVTSGIASNWFB-UHFFFAOYSA-N 0.000 description 1
- OBRQSFBOZCMSTK-UHFFFAOYSA-N 3,6-dichloro-2-methoxyphenol Chemical compound COC1=C(O)C(Cl)=CC=C1Cl OBRQSFBOZCMSTK-UHFFFAOYSA-N 0.000 description 1
- ZGNADFSJWDMFOS-UHFFFAOYSA-N 3-chloro-2-ethoxyphenol Chemical compound CCOC1=C(O)C=CC=C1Cl ZGNADFSJWDMFOS-UHFFFAOYSA-N 0.000 description 1
- JMRPFKGSKYTUSD-UHFFFAOYSA-N 3-chloro-2-methoxyphenol Chemical compound COC1=C(O)C=CC=C1Cl JMRPFKGSKYTUSD-UHFFFAOYSA-N 0.000 description 1
- KPFPEXKMIDAQNO-UHFFFAOYSA-N 3-chloro-2-phenylphenol Chemical compound OC1=CC=CC(Cl)=C1C1=CC=CC=C1 KPFPEXKMIDAQNO-UHFFFAOYSA-N 0.000 description 1
- PNFOXSBXYSADIB-UHFFFAOYSA-N 3-chloro-4,5-dimethylphenol Chemical compound CC1=CC(O)=CC(Cl)=C1C PNFOXSBXYSADIB-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
- QXHZLCYUCTZZNL-UHFFFAOYSA-N 3-chloro-5-methylphenol Chemical compound CC1=CC(O)=CC(Cl)=C1 QXHZLCYUCTZZNL-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
- UBLDZSSBAAKNKN-UHFFFAOYSA-N 4-tert-butyl-2,5-dichlorophenol Chemical compound CC(C)(C)C1=CC(Cl)=C(O)C=C1Cl UBLDZSSBAAKNKN-UHFFFAOYSA-N 0.000 description 1
- XSRHPFUALWIDQA-UHFFFAOYSA-N 4-tert-butyl-3,5-dichlorophenol Chemical compound CC(C)(C)C1=C(Cl)C=C(O)C=C1Cl XSRHPFUALWIDQA-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
- KKFPXGXMSBBNJI-UHFFFAOYSA-N 5-chloro-2-methylphenol Chemical compound CC1=CC=C(Cl)C=C1O KKFPXGXMSBBNJI-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910021623 Tin(IV) bromide Inorganic materials 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 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
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- CECABOMBVQNBEC-UHFFFAOYSA-K aluminium iodide Chemical compound I[Al](I)I CECABOMBVQNBEC-UHFFFAOYSA-K 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
- 238000004458 analytical method Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 230000000382 dechlorinating effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 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
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 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
- 150000002989 phenols Chemical class 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010926 purge Methods 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
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR80/27938 | 1980-12-24 | ||
| FR8027938A FR2496641A1 (fr) | 1980-12-24 | 1980-12-24 | Procede de preparation de phenols metachlores |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57123133A JPS57123133A (en) | 1982-07-31 |
| JPS6050773B2 true JPS6050773B2 (ja) | 1985-11-11 |
Family
ID=9249719
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56203771A Expired JPS6050773B2 (ja) | 1980-12-24 | 1981-12-18 | メタクロルフエノ−ルの製造法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4410739A (enExample) |
| EP (1) | EP0055198B1 (enExample) |
| JP (1) | JPS6050773B2 (enExample) |
| DE (1) | DE3162998D1 (enExample) |
| DK (1) | DK151622C (enExample) |
| FR (1) | FR2496641A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2541992B3 (fr) * | 1983-03-02 | 1985-11-29 | Rhone Poulenc Spec Chim | Procede de preparation de phenols metachlores |
| US5051030A (en) * | 1990-06-05 | 1991-09-24 | Roy F. Weston, Inc. | Chemical detoxification process for treatment of soils contaminated with halogenated organic compounds |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2725402A (en) * | 1951-12-24 | 1955-11-29 | Dow Chemical Co | Selective reduction of chlorobromophenols |
| US2803669A (en) * | 1955-12-27 | 1957-08-20 | Dow Chemical Co | Method of reducing the halogen content of halophenols |
| DE2344926C3 (de) * | 1973-09-06 | 1981-05-07 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von 3-Halogen- bzw. 3,5-Dihalogen-phenolen |
| GB1419603A (en) * | 1972-12-05 | 1975-12-31 | Bayer Ag | Process for the producition of 3-halogen-and 3,5-dihalogen phenols |
| US3912783A (en) * | 1972-12-05 | 1975-10-14 | Bayer Ag | Process and catalyst for preparing of 3-halogen-and 3,5-dihalogen-phenols |
| DE2331712A1 (de) * | 1973-06-22 | 1975-01-23 | Celamerck Gmbh & Co Kg | Verfahren zur herstellung von 2methoxy-3,6-dichlorbenzoesaeure |
| DE2443152C3 (de) * | 1974-09-10 | 1981-05-21 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von durch Halogen meta-substituierten Phenolen |
| GB1458633A (en) * | 1974-09-17 | 1976-12-15 | Ici Ltd | Process for dehalogenating aromatic compounds |
| US4285971A (en) * | 1978-08-08 | 1981-08-25 | Ciba-Geigy Corporation | Novel halogenated phenol esters, antimicrobial compositions containing them and their use |
-
1980
- 1980-12-24 FR FR8027938A patent/FR2496641A1/fr active Granted
-
1981
- 1981-12-18 EP EP81420187A patent/EP0055198B1/fr not_active Expired
- 1981-12-18 JP JP56203771A patent/JPS6050773B2/ja not_active Expired
- 1981-12-18 DE DE8181420187T patent/DE3162998D1/de not_active Expired
- 1981-12-21 US US06/332,846 patent/US4410739A/en not_active Expired - Fee Related
- 1981-12-23 DK DK574381A patent/DK151622C/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0055198A1 (fr) | 1982-06-30 |
| DK574381A (da) | 1982-06-25 |
| DK151622B (da) | 1987-12-21 |
| US4410739A (en) | 1983-10-18 |
| JPS57123133A (en) | 1982-07-31 |
| FR2496641A1 (fr) | 1982-06-25 |
| EP0055198B1 (fr) | 1984-04-04 |
| FR2496641B1 (enExample) | 1983-03-11 |
| DK151622C (da) | 1988-06-20 |
| DE3162998D1 (en) | 1984-05-10 |
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