HU185214B - Process for preparing chlorinated - in position meta - derivatives of anfiline - Google Patents
Process for preparing chlorinated - in position meta - derivatives of anfiline Download PDFInfo
- Publication number
- HU185214B HU185214B HU80337A HU33780A HU185214B HU 185214 B HU185214 B HU 185214B HU 80337 A HU80337 A HU 80337A HU 33780 A HU33780 A HU 33780A HU 185214 B HU185214 B HU 185214B
- Authority
- HU
- Hungary
- Prior art keywords
- hydrogen
- dichloro
- chlorine
- chloride
- chloro
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 39
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000007791 liquid phase Substances 0.000 claims abstract description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 17
- -1 chlorine-substituted benzene Chemical class 0.000 claims description 17
- 239000003054 catalyst Substances 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 150000002500 ions Chemical class 0.000 claims description 7
- 229910052763 palladium Inorganic materials 0.000 claims description 7
- 150000001875 compounds Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Chemical group 0.000 claims description 2
- 229910052760 oxygen Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 239000010970 precious metal Substances 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 150000001448 anilines Chemical class 0.000 abstract description 7
- 238000006298 dechlorination reaction Methods 0.000 abstract 1
- 150000005181 nitrobenzenes Chemical class 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 5
- UQRLKWGPEVNVHT-UHFFFAOYSA-N 3,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC(Cl)=C1 UQRLKWGPEVNVHT-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- GBKZRUCVLTWAML-UHFFFAOYSA-N 2,3,4,5-tetrachloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C(Cl)=C1Cl GBKZRUCVLTWAML-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- BRPSAOUFIJSKOT-UHFFFAOYSA-N 2,3-dichloroaniline Chemical class NC1=CC=CC(Cl)=C1Cl BRPSAOUFIJSKOT-UHFFFAOYSA-N 0.000 description 2
- XOGYQVITULCUGU-UHFFFAOYSA-N 3,4,5-trichloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C(Cl)=C1 XOGYQVITULCUGU-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 229910052786 argon Inorganic materials 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 2
- DQNOIKMHTBFYTD-UHFFFAOYSA-N n,n,2,3-tetrachloroaniline Chemical compound ClN(Cl)C1=CC=CC(Cl)=C1Cl DQNOIKMHTBFYTD-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910052715 tantalum Inorganic materials 0.000 description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CWEVPIBZXIZFLU-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5-nitro-6-phenoxybenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1OC1=CC=CC=C1 CWEVPIBZXIZFLU-UHFFFAOYSA-N 0.000 description 1
- MTBYTWZDRVOMBR-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=C(Cl)C(Cl)=C1Cl MTBYTWZDRVOMBR-UHFFFAOYSA-N 0.000 description 1
- NQEKOOGCLIIIKC-UHFFFAOYSA-N 1,2,3-trichloro-4-methoxy-5-nitrobenzene Chemical compound COC1=C(Cl)C(Cl)=C(Cl)C=C1[N+]([O-])=O NQEKOOGCLIIIKC-UHFFFAOYSA-N 0.000 description 1
- BGKIECJVXXHLDP-UHFFFAOYSA-N 1,2,3-trichloro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(Cl)=C1Cl BGKIECJVXXHLDP-UHFFFAOYSA-N 0.000 description 1
- WDIKVKQUYUJSQS-UHFFFAOYSA-N 1,2,3-trichloro-5-methyl-4-nitrobenzene Chemical compound CC1=CC(Cl)=C(Cl)C(Cl)=C1[N+]([O-])=O WDIKVKQUYUJSQS-UHFFFAOYSA-N 0.000 description 1
- QLRPRUKUFBCCOG-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-methyl-6-nitrobenzene Chemical compound CC1=C(Cl)C(Cl)=C([N+]([O-])=O)C(Cl)=C1Cl QLRPRUKUFBCCOG-UHFFFAOYSA-N 0.000 description 1
- WELCXTXFMAVVKR-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-nitro-6-phenoxybenzene Chemical compound ClC1=C(Cl)C([N+](=O)[O-])=C(Cl)C(Cl)=C1OC1=CC=CC=C1 WELCXTXFMAVVKR-UHFFFAOYSA-N 0.000 description 1
- UDEAXERKYRDHTE-UHFFFAOYSA-N 1,2,4-trichloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C=CC(Cl)=C1Cl UDEAXERKYRDHTE-UHFFFAOYSA-N 0.000 description 1
- YBCSBMLIXWHLQI-UHFFFAOYSA-N 1,2-dichloro-3-methoxy-4-nitrobenzene Chemical compound COC1=C(Cl)C(Cl)=CC=C1[N+]([O-])=O YBCSBMLIXWHLQI-UHFFFAOYSA-N 0.000 description 1
- CMVQZRLQEOAYSW-UHFFFAOYSA-N 1,2-dichloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1Cl CMVQZRLQEOAYSW-UHFFFAOYSA-N 0.000 description 1
- QFQSBAMTGUKFKS-UHFFFAOYSA-N 1,2-dichloro-4-methoxy-5-nitrobenzene Chemical compound COC1=CC(Cl)=C(Cl)C=C1[N+]([O-])=O QFQSBAMTGUKFKS-UHFFFAOYSA-N 0.000 description 1
- LBKQVYCKFHARBV-UHFFFAOYSA-N 1,2-dichloro-4-nitro-5-phenoxybenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=C(Cl)C=C1OC1=CC=CC=C1 LBKQVYCKFHARBV-UHFFFAOYSA-N 0.000 description 1
- NTBYINQTYWZXLH-UHFFFAOYSA-N 1,2-dichloro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(Cl)=C1 NTBYINQTYWZXLH-UHFFFAOYSA-N 0.000 description 1
- KTPPCTQPGJFQHB-UHFFFAOYSA-N 1,2-dichloro-5-methoxy-3-nitrobenzene Chemical compound COC1=CC(Cl)=C(Cl)C([N+]([O-])=O)=C1 KTPPCTQPGJFQHB-UHFFFAOYSA-N 0.000 description 1
- WRSWHUVIGGFTNU-UHFFFAOYSA-N 1,3,4-trichloro-2-methoxy-5-nitrobenzene Chemical compound COC1=C(Cl)C=C([N+]([O-])=O)C(Cl)=C1Cl WRSWHUVIGGFTNU-UHFFFAOYSA-N 0.000 description 1
- DVGWQGRGSAQPQJ-UHFFFAOYSA-N 1,4-dichloro-2-methoxy-5-nitrobenzene Chemical compound COC1=CC(Cl)=C([N+]([O-])=O)C=C1Cl DVGWQGRGSAQPQJ-UHFFFAOYSA-N 0.000 description 1
- ZZHOGSARBSKHBZ-UHFFFAOYSA-N 1,4-dichloro-2-nitro-5-phenoxybenzene Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(Cl)=C1OC1=CC=CC=C1 ZZHOGSARBSKHBZ-UHFFFAOYSA-N 0.000 description 1
- IIHRBBRFSOLMCD-UHFFFAOYSA-N 1,4-dichloro-2-nitro-5-propylbenzene Chemical compound CCCC1=CC(Cl)=C([N+]([O-])=O)C=C1Cl IIHRBBRFSOLMCD-UHFFFAOYSA-N 0.000 description 1
- RZKKOBGFCAHLCZ-UHFFFAOYSA-N 1,4-dichloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1Cl RZKKOBGFCAHLCZ-UHFFFAOYSA-N 0.000 description 1
- KHCZSJXTDDHLGJ-UHFFFAOYSA-N 2,3,4,5,6-pentachloroaniline Chemical compound NC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl KHCZSJXTDDHLGJ-UHFFFAOYSA-N 0.000 description 1
- AMKZKITUPXRCRX-UHFFFAOYSA-N 2,3,4,6-tetrachloro-5-phenoxyaniline Chemical compound NC1=C(Cl)C(Cl)=C(Cl)C(OC=2C=CC=CC=2)=C1Cl AMKZKITUPXRCRX-UHFFFAOYSA-N 0.000 description 1
- FBHJFDRYHRDILH-UHFFFAOYSA-N 2,3,4-trichloro-6-methylaniline Chemical compound CC1=CC(Cl)=C(Cl)C(Cl)=C1N FBHJFDRYHRDILH-UHFFFAOYSA-N 0.000 description 1
- RRJUYQOFOMFVQS-UHFFFAOYSA-N 2,3,4-trichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1Cl RRJUYQOFOMFVQS-UHFFFAOYSA-N 0.000 description 1
- MVLQHKBMRKTIOB-UHFFFAOYSA-N 2,3,5-trichloro-4-methoxyaniline Chemical compound COC1=C(Cl)C=C(N)C(Cl)=C1Cl MVLQHKBMRKTIOB-UHFFFAOYSA-N 0.000 description 1
- GMXFJTFHFYKUQF-UHFFFAOYSA-N 2,3,6-trichloro-4-methoxyaniline Chemical compound COC1=CC(Cl)=C(N)C(Cl)=C1Cl GMXFJTFHFYKUQF-UHFFFAOYSA-N 0.000 description 1
- LZYMHTVWOMZPEO-UHFFFAOYSA-N 2,3-dichloro-4-methoxyaniline Chemical compound COC1=CC=C(N)C(Cl)=C1Cl LZYMHTVWOMZPEO-UHFFFAOYSA-N 0.000 description 1
- NJZMXYAVRVWZAS-UHFFFAOYSA-N 2,5-dichloro-1-methoxy-3-nitrobenzene Chemical compound COC1=CC(Cl)=CC([N+]([O-])=O)=C1Cl NJZMXYAVRVWZAS-UHFFFAOYSA-N 0.000 description 1
- MRDOLSVLOGGRAE-UHFFFAOYSA-N 2,5-dichloro-3,4-dimethylaniline Chemical compound CC1=C(C)C(Cl)=C(N)C=C1Cl MRDOLSVLOGGRAE-UHFFFAOYSA-N 0.000 description 1
- DKLUBYIAONUMRE-UHFFFAOYSA-N 2,5-dichloro-4-ethylaniline Chemical compound CCC1=CC(Cl)=C(N)C=C1Cl DKLUBYIAONUMRE-UHFFFAOYSA-N 0.000 description 1
- PLVBBUUBVVJOIB-UHFFFAOYSA-N 2,5-dichloro-4-methylaniline Chemical compound CC1=CC(Cl)=C(N)C=C1Cl PLVBBUUBVVJOIB-UHFFFAOYSA-N 0.000 description 1
- QXDILMJTDWNTAV-UHFFFAOYSA-N 2,5-dichloro-4-phenoxyaniline Chemical compound C1=C(Cl)C(N)=CC(Cl)=C1OC1=CC=CC=C1 QXDILMJTDWNTAV-UHFFFAOYSA-N 0.000 description 1
- YCJWTHYCBOTYAL-UHFFFAOYSA-N 2,5-dichloro-4-propylaniline Chemical compound CCCC1=CC(Cl)=C(N)C=C1Cl YCJWTHYCBOTYAL-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- SBXPKMDRNSXSJZ-UHFFFAOYSA-N 2-benzyl-3,4,6-trichloroaniline Chemical compound NC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=CC=CC=C1 SBXPKMDRNSXSJZ-UHFFFAOYSA-N 0.000 description 1
- ZDDBBMFYYJXISB-UHFFFAOYSA-N 3,4,5-trichloro-2-methoxyaniline Chemical compound COC1=C(N)C=C(Cl)C(Cl)=C1Cl ZDDBBMFYYJXISB-UHFFFAOYSA-N 0.000 description 1
- YNMZQQXVRYHMKT-UHFFFAOYSA-N 3,4-dichloro-2-methoxyaniline Chemical compound COC1=C(N)C=CC(Cl)=C1Cl YNMZQQXVRYHMKT-UHFFFAOYSA-N 0.000 description 1
- RLTUJGIRWIFRLO-UHFFFAOYSA-N 3,4-dichloro-5-methoxyaniline Chemical compound COC1=CC(N)=CC(Cl)=C1Cl RLTUJGIRWIFRLO-UHFFFAOYSA-N 0.000 description 1
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 1
- FCNJFFUXQXCKFS-UHFFFAOYSA-N 3,5-dichloro-2-methoxyaniline Chemical compound COC1=C(N)C=C(Cl)C=C1Cl FCNJFFUXQXCKFS-UHFFFAOYSA-N 0.000 description 1
- RLECPRVZOAXLMK-UHFFFAOYSA-N 3,5-dichloro-2-phenoxyaniline Chemical compound NC1=CC(Cl)=CC(Cl)=C1OC1=CC=CC=C1 RLECPRVZOAXLMK-UHFFFAOYSA-N 0.000 description 1
- KFAAKHZTICEVTO-UHFFFAOYSA-N 3,5-dichloro-4-phenoxyaniline Chemical compound ClC1=CC(N)=CC(Cl)=C1OC1=CC=CC=C1 KFAAKHZTICEVTO-UHFFFAOYSA-N 0.000 description 1
- DSTYKCDGDXOVOZ-UHFFFAOYSA-N 3,6-dichloro-2-methoxyaniline Chemical compound COC1=C(N)C(Cl)=CC=C1Cl DSTYKCDGDXOVOZ-UHFFFAOYSA-N 0.000 description 1
- LTKJFXIFJLXFNJ-UHFFFAOYSA-N 3-benzyl-1,2,5-trichloro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C=C(Cl)C(Cl)=C1CC1=CC=CC=C1 LTKJFXIFJLXFNJ-UHFFFAOYSA-N 0.000 description 1
- LVFXXXPXOSABGF-UHFFFAOYSA-N 3-chloro-2-phenoxyaniline Chemical compound NC1=CC=CC(Cl)=C1OC1=CC=CC=C1 LVFXXXPXOSABGF-UHFFFAOYSA-N 0.000 description 1
- XLAVBRTYEPFKSD-UHFFFAOYSA-N 3-chloro-5-methoxyaniline Chemical compound COC1=CC(N)=CC(Cl)=C1 XLAVBRTYEPFKSD-UHFFFAOYSA-N 0.000 description 1
- PDOWROQDIXWGIV-UHFFFAOYSA-N 4,5-dichloro-2-phenoxyaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1OC1=CC=CC=C1 PDOWROQDIXWGIV-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical class NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical compound COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 description 1
- SXEBHIMOUHBBOS-UHFFFAOYSA-N 5-chloro-2-phenoxyaniline Chemical compound NC1=CC(Cl)=CC=C1OC1=CC=CC=C1 SXEBHIMOUHBBOS-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- MMCPOSDMTGQNKG-UJZMCJRSSA-N aniline;hydrochloride Chemical class Cl.N[14C]1=[14CH][14CH]=[14CH][14CH]=[14CH]1 MMCPOSDMTGQNKG-UJZMCJRSSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000010908 decantation Methods 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
- 150000002431 hydrogen Chemical class 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
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 239000002917 insecticide 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
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- GYNAVKULVOETAD-UHFFFAOYSA-N n-phenoxyaniline Chemical compound C=1C=CC=CC=1NOC1=CC=CC=C1 GYNAVKULVOETAD-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 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
- 125000003431 oxalo group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000376 reactant Substances 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
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C215/76—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7904483A FR2449077A2 (fr) | 1979-02-15 | 1979-02-15 | Procede de preparation d'anilines metachlorees |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU185214B true HU185214B (en) | 1984-12-28 |
Family
ID=9222292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU80337A HU185214B (en) | 1979-02-15 | 1980-02-14 | Process for preparing chlorinated - in position meta - derivatives of anfiline |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4324914A (en, 2012) |
| JP (1) | JPS5928544B2 (en, 2012) |
| AT (1) | AT372370B (en, 2012) |
| BE (1) | BE881754A (en, 2012) |
| BR (1) | BR8000910A (en, 2012) |
| CA (1) | CA1139313A (en, 2012) |
| CH (1) | CH642049A5 (en, 2012) |
| DD (1) | DD149060A5 (en, 2012) |
| DE (1) | DE3003960A1 (en, 2012) |
| DK (1) | DK153392C (en, 2012) |
| ES (1) | ES488572A1 (en, 2012) |
| FR (1) | FR2449077A2 (en, 2012) |
| GB (1) | GB2042542B (en, 2012) |
| HU (1) | HU185214B (en, 2012) |
| IE (1) | IE49393B1 (en, 2012) |
| IL (1) | IL59190A (en, 2012) |
| IT (1) | IT1127360B (en, 2012) |
| LU (1) | LU82167A1 (en, 2012) |
| NL (1) | NL8000620A (en, 2012) |
| SE (1) | SE447897B (en, 2012) |
| SU (1) | SU1082316A3 (en, 2012) |
| YU (1) | YU42323B (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3127026A1 (de) * | 1981-07-09 | 1983-01-20 | Bayer Ag, 5090 Leverkusen | Verrfahren zur herstellung von m-chlorsubstituiertenanilinen |
| FR2521132A1 (fr) * | 1982-02-05 | 1983-08-12 | Rhone Poulenc Agrochimie | Procede de preparation de metahalogeno-anilines |
| US4888425A (en) * | 1982-04-30 | 1989-12-19 | Union Carbide Chemicals And Plastics Company Inc. | Preparation of polyalkylene polyamines |
| JPS5955855A (ja) * | 1982-09-27 | 1984-03-31 | Mitsui Toatsu Chem Inc | ３，３′−ジアミノジフエニルメタンの製造方法 |
| JPS62132400U (en, 2012) * | 1986-02-14 | 1987-08-20 | ||
| USRE34745E (en) * | 1986-10-30 | 1994-09-27 | The Dow Chemical Company | High purity process for the preparation of 4,6-diamino-1,3-benzenediol |
| US5001279A (en) * | 1989-11-17 | 1991-03-19 | The Dow Chemical Company | Aqueous synthesis of 2-halo-4,6-dinitroresorcinol and 4,6-diaminoresorcinol |
| US5294742A (en) * | 1992-03-21 | 1994-03-15 | Hoechst Atkiengesellschaft | Process for preparing 3,5-difluoroaniline |
| WO2009111306A2 (en) * | 2008-02-29 | 2009-09-11 | Cook Biotech Incorporated | Coated embolization device |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3148217A (en) * | 1961-11-16 | 1964-09-08 | Gen Aniline & Film Corp | Catalytic hydrogenation of halonitrobenzene compounds |
| DE2032565A1 (de) * | 1970-07-01 | 1972-01-05 | Farbwerke Hoechst AG, vormals Meister Lucius & Bruning, 6000 Frankfurt | Verfahren zur Herstellung von 3 Difluorchlormethylanihn |
| DE2036313C3 (de) * | 1970-07-22 | 1982-03-25 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Halogen-substituiertenaromatischen Aminen |
| CS188122B2 (en) * | 1971-02-08 | 1979-02-28 | Kurt Habig | Method of production the sulfide catalysts with the platinum on coal |
| DE2503187C3 (de) * | 1975-01-27 | 1979-05-31 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung durch Chlor meta-substituierte Aniline |
| FR2403990A1 (fr) * | 1977-09-22 | 1979-04-20 | Philagro Sa | Procede de deshalogenation d'amines aromatiques halogenees |
| DE2758111A1 (de) * | 1977-12-24 | 1979-07-05 | Basf Ag | Verfahren zur herstellung von halogenanilinen |
-
1979
- 1979-02-15 FR FR7904483A patent/FR2449077A2/fr active Granted
-
1980
- 1980-01-22 IL IL59190A patent/IL59190A/xx unknown
- 1980-01-23 US US06/114,651 patent/US4324914A/en not_active Expired - Lifetime
- 1980-01-31 NL NL8000620A patent/NL8000620A/nl not_active Application Discontinuation
- 1980-02-04 DE DE19803003960 patent/DE3003960A1/de active Granted
- 1980-02-13 DD DD80219034A patent/DD149060A5/de not_active IP Right Cessation
- 1980-02-13 YU YU378/80A patent/YU42323B/xx unknown
- 1980-02-13 CA CA000345561A patent/CA1139313A/en not_active Expired
- 1980-02-13 GB GB8004746A patent/GB2042542B/en not_active Expired
- 1980-02-13 IT IT47892/80A patent/IT1127360B/it active
- 1980-02-13 IE IE277/80A patent/IE49393B1/en unknown
- 1980-02-14 SE SE8001166A patent/SE447897B/sv not_active IP Right Cessation
- 1980-02-14 SU SU802882799A patent/SU1082316A3/ru active
- 1980-02-14 LU LU82167A patent/LU82167A1/fr unknown
- 1980-02-14 HU HU80337A patent/HU185214B/hu unknown
- 1980-02-14 BR BR8000910A patent/BR8000910A/pt unknown
- 1980-02-14 ES ES488572A patent/ES488572A1/es not_active Expired
- 1980-02-14 JP JP55017165A patent/JPS5928544B2/ja not_active Expired
- 1980-02-14 DK DK062880A patent/DK153392C/da active
- 1980-02-14 CH CH123780A patent/CH642049A5/fr not_active IP Right Cessation
- 1980-02-15 BE BE0/199423A patent/BE881754A/fr unknown
- 1980-02-15 AT AT0085480A patent/AT372370B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES488572A1 (es) | 1980-10-01 |
| IE800277L (en) | 1980-08-15 |
| IL59190A (en) | 1983-06-15 |
| DK153392C (da) | 1988-11-28 |
| GB2042542B (en) | 1983-05-05 |
| GB2042542A (en) | 1980-09-24 |
| FR2449077B2 (en, 2012) | 1983-04-29 |
| JPS55149229A (en) | 1980-11-20 |
| DD149060A5 (de) | 1981-06-24 |
| LU82167A1 (fr) | 1981-09-10 |
| IT8047892A0 (it) | 1980-02-13 |
| IE49393B1 (en) | 1985-10-02 |
| CA1139313A (en) | 1983-01-11 |
| YU42323B (en) | 1988-08-31 |
| NL8000620A (nl) | 1980-08-19 |
| SE447897B (sv) | 1986-12-22 |
| BE881754A (fr) | 1980-08-18 |
| DK62880A (da) | 1980-08-16 |
| SE8001166L (sv) | 1980-08-16 |
| DK153392B (da) | 1988-07-11 |
| ATA85480A (de) | 1983-02-15 |
| IT1127360B (it) | 1986-05-21 |
| YU37880A (en) | 1983-01-21 |
| US4324914A (en) | 1982-04-13 |
| FR2449077A2 (fr) | 1980-09-12 |
| IL59190A0 (en) | 1980-05-30 |
| AT372370B (de) | 1983-09-26 |
| DE3003960A1 (de) | 1980-08-28 |
| JPS5928544B2 (ja) | 1984-07-13 |
| DE3003960C2 (en, 2012) | 1990-07-05 |
| BR8000910A (pt) | 1980-10-29 |
| CH642049A5 (fr) | 1984-03-30 |
| SU1082316A3 (ru) | 1984-03-23 |
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