JPS5848540B2 - 塩素でメタ置換されたアニリンの製造方法 - Google Patents
塩素でメタ置換されたアニリンの製造方法Info
- Publication number
- JPS5848540B2 JPS5848540B2 JP51006384A JP638476A JPS5848540B2 JP S5848540 B2 JPS5848540 B2 JP S5848540B2 JP 51006384 A JP51006384 A JP 51006384A JP 638476 A JP638476 A JP 638476A JP S5848540 B2 JPS5848540 B2 JP S5848540B2
- Authority
- JP
- Japan
- Prior art keywords
- chlorine
- carried out
- hydrogen
- reaction
- group
- 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
- 239000000460 chlorine Substances 0.000 title claims description 27
- 229910052801 chlorine Inorganic materials 0.000 title claims description 27
- 125000001309 chloro group Chemical group Cl* 0.000 title claims description 14
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- UQRLKWGPEVNVHT-UHFFFAOYSA-N 3,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC(Cl)=C1 UQRLKWGPEVNVHT-UHFFFAOYSA-N 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 claims description 13
- 229910000510 noble metal Inorganic materials 0.000 claims description 13
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical group 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000000010 aprotic solvent Substances 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000003586 protic polar solvent Substances 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- -1 phthyl Chemical group 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 150000001448 anilines Chemical class 0.000 description 7
- 238000006298 dechlorination reaction Methods 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000004508 fractional distillation Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 229910052715 tantalum Inorganic materials 0.000 description 4
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 4
- AMROFTJFMUYVTB-UHFFFAOYSA-N 2,3,5,6-tetrachloro-4-methylaniline Chemical compound CC1=C(Cl)C(Cl)=C(N)C(Cl)=C1Cl AMROFTJFMUYVTB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 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 2
- YTDHEFNWWHSXSU-UHFFFAOYSA-N 2,3,5,6-tetrachloroaniline Chemical compound NC1=C(Cl)C(Cl)=CC(Cl)=C1Cl YTDHEFNWWHSXSU-UHFFFAOYSA-N 0.000 description 2
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000000217 alkyl 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
- 239000000969 carrier Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000005695 dehalogenation reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- RNABGKOKSBUFHW-UHFFFAOYSA-N 1,3-dichloro-5-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(Cl)=C1 RNABGKOKSBUFHW-UHFFFAOYSA-N 0.000 description 1
- ONRFSTKRXHVKTI-UHFFFAOYSA-N 2,3,4,5-tetrachloro-6-methoxyaniline Chemical compound COC1=C(N)C(Cl)=C(Cl)C(Cl)=C1Cl ONRFSTKRXHVKTI-UHFFFAOYSA-N 0.000 description 1
- ZUMRAASOHVUGRC-UHFFFAOYSA-N 2,3,4,5-tetrachloro-6-phenoxyaniline Chemical compound NC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1OC1=CC=CC=C1 ZUMRAASOHVUGRC-UHFFFAOYSA-N 0.000 description 1
- GBKZRUCVLTWAML-UHFFFAOYSA-N 2,3,4,5-tetrachloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C(Cl)=C1Cl GBKZRUCVLTWAML-UHFFFAOYSA-N 0.000 description 1
- QDRIOLWGEOQJCP-UHFFFAOYSA-N 2,3,4,6-tetrachloro-5-methoxyaniline Chemical compound COC1=C(Cl)C(N)=C(Cl)C(Cl)=C1Cl QDRIOLWGEOQJCP-UHFFFAOYSA-N 0.000 description 1
- LXCLPHJRGDTDDB-UHFFFAOYSA-N 2,3,4,6-tetrachloroaniline Chemical compound NC1=C(Cl)C=C(Cl)C(Cl)=C1Cl LXCLPHJRGDTDDB-UHFFFAOYSA-N 0.000 description 1
- WUIMAOZZLPNIMF-UHFFFAOYSA-N 2,3,4-trichloro-5-methoxyaniline Chemical compound COC1=CC(N)=C(Cl)C(Cl)=C1Cl WUIMAOZZLPNIMF-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
- LZYMHTVWOMZPEO-UHFFFAOYSA-N 2,3-dichloro-4-methoxyaniline Chemical compound COC1=CC=C(N)C(Cl)=C1Cl LZYMHTVWOMZPEO-UHFFFAOYSA-N 0.000 description 1
- CNMBMHIFTUIKLJ-UHFFFAOYSA-N 2,3-dichloro-5-methoxyaniline Chemical compound COC1=CC(N)=C(Cl)C(Cl)=C1 CNMBMHIFTUIKLJ-UHFFFAOYSA-N 0.000 description 1
- NGQZFSHSIJZJNX-UHFFFAOYSA-N 2,3-dichloro-6-methoxyaniline Chemical compound COC1=CC=C(Cl)C(Cl)=C1N NGQZFSHSIJZJNX-UHFFFAOYSA-N 0.000 description 1
- BRPSAOUFIJSKOT-UHFFFAOYSA-N 2,3-dichloroaniline Chemical compound NC1=CC=CC(Cl)=C1Cl BRPSAOUFIJSKOT-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
- JHZWCHORDSEJQD-UHFFFAOYSA-N 2,5-dichloro-3-methoxyaniline Chemical compound COC1=CC(Cl)=CC(N)=C1Cl JHZWCHORDSEJQD-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
- VCMXIPGKIUDONN-UHFFFAOYSA-N 2,5-dichloro-4-methoxyaniline Chemical compound COC1=CC(Cl)=C(N)C=C1Cl VCMXIPGKIUDONN-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
- 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
- XOGYQVITULCUGU-UHFFFAOYSA-N 3,4,5-trichloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C(Cl)=C1 XOGYQVITULCUGU-UHFFFAOYSA-N 0.000 description 1
- FBKQCRAVAOUMHN-UHFFFAOYSA-N 3,4,6-trichloro-2-methoxyaniline Chemical compound COC1=C(N)C(Cl)=CC(Cl)=C1Cl FBKQCRAVAOUMHN-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
- GNFMBCBDTFAEHM-UHFFFAOYSA-N 3,5-dichloro-4-methoxyaniline Chemical compound COC1=C(Cl)C=C(N)C=C1Cl GNFMBCBDTFAEHM-UHFFFAOYSA-N 0.000 description 1
- GTEUMCIATAHZFK-UHFFFAOYSA-N 3,5-dichloro-4-methylaniline Chemical compound CC1=C(Cl)C=C(N)C=C1Cl GTEUMCIATAHZFK-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
- VPZJHTWLWKFPQW-UHFFFAOYSA-N 3-chloro-2-methoxyaniline Chemical compound COC1=C(N)C=CC=C1Cl VPZJHTWLWKFPQW-UHFFFAOYSA-N 0.000 description 1
- KWTAEBKYISVYFB-UHFFFAOYSA-N 3-chloro-4,5-dimethylaniline Chemical compound CC1=CC(N)=CC(Cl)=C1C KWTAEBKYISVYFB-UHFFFAOYSA-N 0.000 description 1
- XQVCBOLNTSUFGD-UHFFFAOYSA-N 3-chloro-4-methoxyaniline Chemical compound COC1=CC=C(N)C=C1Cl XQVCBOLNTSUFGD-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
- XUZCJDBXXYJXDD-UHFFFAOYSA-N 3-chloro-5-methylaniline Chemical compound CC1=CC(N)=CC(Cl)=C1 XUZCJDBXXYJXDD-UHFFFAOYSA-N 0.000 description 1
- OMUPQCXITFAUCB-UHFFFAOYSA-N 4,5-dichloro-2-methoxyaniline Chemical compound COC1=CC(Cl)=C(Cl)C=C1N OMUPQCXITFAUCB-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
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- WRZOMWDJOLIVQP-UHFFFAOYSA-N 5-Chloro-ortho-toluidine Chemical compound CC1=CC=C(Cl)C=C1N WRZOMWDJOLIVQP-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001555 benzenes Chemical class 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
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- BIXZHMJUSMUDOQ-UHFFFAOYSA-N dichloran Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl BIXZHMJUSMUDOQ-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000013067 intermediate product 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 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
- 235000019260 propionic acid Nutrition 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
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035484 reaction time Effects 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
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (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 |
|---|---|---|---|
| DE2503187A DE2503187C3 (de) | 1975-01-27 | 1975-01-27 | Verfahren zur Herstellung durch Chlor meta-substituierte Aniline |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51125328A JPS51125328A (en) | 1976-11-01 |
| JPS5848540B2 true JPS5848540B2 (ja) | 1983-10-28 |
Family
ID=5937382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51006384A Expired JPS5848540B2 (ja) | 1975-01-27 | 1976-01-24 | 塩素でメタ置換されたアニリンの製造方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4085141A (index.php) |
| JP (1) | JPS5848540B2 (index.php) |
| BE (1) | BE837923A (index.php) |
| DE (1) | DE2503187C3 (index.php) |
| FR (1) | FR2298531A1 (index.php) |
| GB (1) | GB1477988A (index.php) |
| NL (1) | NL7600773A (index.php) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH609959A5 (index.php) * | 1976-12-17 | 1979-03-30 | Basf Ag | |
| FR2403990A1 (fr) * | 1977-09-22 | 1979-04-20 | Philagro Sa | Procede de deshalogenation d'amines aromatiques halogenees |
| FR2403991A1 (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 |
| FR2449077A2 (fr) * | 1979-02-15 | 1980-09-12 | Rhone Poulenc Agrochimie | Procede de preparation d'anilines metachlorees |
| FR2449075A1 (fr) * | 1979-02-15 | 1980-09-12 | Rhone Poulenc Agrochimie | Procede de preparation d'anilines metachlorees |
| FR2449076A2 (fr) * | 1979-02-15 | 1980-09-12 | Rhone Poulenc Agrochimie | Procede de preparation d'anilines metachlorees |
| US4282380A (en) * | 1979-07-05 | 1981-08-04 | American Cyanamid Company | Reductive alkylation and dehalogenation of m-nitrobenzyl halides |
| DE3017542A1 (de) * | 1980-05-08 | 1981-11-12 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 2-trifluormethylanilin |
| IL63297A (en) * | 1980-08-01 | 1984-05-31 | Rhone Poulenc Agrochimie | Selective preparation of meta-chloroanilines |
| FR2487824A1 (fr) * | 1980-08-01 | 1982-02-05 | Rhone Poulenc Agrochimie | Procede de preparation selective d'anilines metachlorees |
| 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 |
| FR2532305A1 (fr) * | 1982-08-24 | 1984-03-02 | Rhone Poulenc Agrochimie | Procede de preparation d'anilines metachlorees |
| JPS59172441A (ja) * | 1983-03-23 | 1984-09-29 | Mitsui Toatsu Chem Inc | ３，３′−または３，４′−ジアミノベンゾフエノンの製造方法 |
| JPH0565250A (ja) * | 1991-01-28 | 1993-03-19 | Ishihara Sangyo Kaisha Ltd | ３，５−ジフルオロアニリンの製造方法 |
| US5089653A (en) * | 1991-04-04 | 1992-02-18 | Dow Elanco | Process for the selective reduction of the 4-halogen in 2,4-dihaloanilines |
| JPH0535677U (ja) * | 1991-05-14 | 1993-05-14 | バンドー化学株式会社 | ゴム製袋体の口金取付構造 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE792080A (fr) * | 1971-11-30 | 1973-05-29 | Rhone Progil | Procede de deshalogenation de composes aromatiques polyhalogenes |
| US3912783A (en) * | 1972-12-05 | 1975-10-14 | Bayer Ag | Process and catalyst for preparing of 3-halogen-and 3,5-dihalogen-phenols |
| GB1458633A (en) * | 1974-09-17 | 1976-12-15 | Ici Ltd | Process for dehalogenating aromatic compounds |
-
1975
- 1975-01-27 DE DE2503187A patent/DE2503187C3/de not_active Expired
-
1976
- 1976-01-09 US US05/647,967 patent/US4085141A/en not_active Expired - Lifetime
- 1976-01-24 JP JP51006384A patent/JPS5848540B2/ja not_active Expired
- 1976-01-26 NL NL7600773A patent/NL7600773A/xx not_active Application Discontinuation
- 1976-01-26 GB GB284976A patent/GB1477988A/en not_active Expired
- 1976-01-27 BE BE2054777A patent/BE837923A/xx not_active IP Right Cessation
- 1976-01-27 FR FR7602150A patent/FR2298531A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2298531A1 (fr) | 1976-08-20 |
| FR2298531B1 (index.php) | 1979-05-18 |
| DE2503187A1 (de) | 1976-07-29 |
| JPS51125328A (en) | 1976-11-01 |
| BE837923A (fr) | 1976-07-27 |
| DE2503187C3 (de) | 1979-05-31 |
| GB1477988A (en) | 1977-06-29 |
| DE2503187B2 (de) | 1978-10-05 |
| US4085141A (en) | 1978-04-18 |
| NL7600773A (nl) | 1976-07-29 |
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