BE452305A - Procédé de fabrication d'alcoxy-2 nitro-5-anilines, le cas échéant en combinaison avec des alcoxy-2 nitro-4 anilines, le groupe alcoxy contenant plus de deux atomes de carbone - Google Patents
Procédé de fabrication d'alcoxy-2 nitro-5-anilines, le cas échéant en combinaison avec des alcoxy-2 nitro-4 anilines, le groupe alcoxy contenant plus de deux atomes de carboneInfo
- Publication number
- BE452305A BE452305A BE452305A BE452305A BE452305A BE 452305 A BE452305 A BE 452305A BE 452305 A BE452305 A BE 452305A BE 452305 A BE452305 A BE 452305A BE 452305 A BE452305 A BE 452305A
- Authority
- BE
- Belgium
- Prior art keywords
- nitro
- alkoxy
- aniline
- anilines
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 125000003545 alkoxy group Chemical group 0.000 title claims description 8
- 230000008569 process Effects 0.000 title claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 22
- 238000000926 separation method Methods 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- -1 AO-2 5-nitro anilines Chemical class 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 241000282320 Panthera leo Species 0.000 claims 1
- 239000000047 product Substances 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- 238000006396 nitration reaction Methods 0.000 description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 150000001448 anilines Chemical class 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- 230000005484 gravity Effects 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000001640 fractional crystallisation Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 229960001413 acetanilide Drugs 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 230000003444 anaesthetic effect Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000003589 local anesthetic agent Substances 0.000 description 2
- YSDNRZRWQPDCOJ-UHFFFAOYSA-N n-phenyl-2-propoxyacetamide Chemical compound CCCOCC(=O)NC1=CC=CC=C1 YSDNRZRWQPDCOJ-UHFFFAOYSA-N 0.000 description 2
- 230000001546 nitrifying effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZQTPOMUMEJTURV-UHFFFAOYSA-N 2-butoxy-5-nitroaniline Chemical compound CCCCOC1=CC=C([N+]([O-])=O)C=C1N ZQTPOMUMEJTURV-UHFFFAOYSA-N 0.000 description 1
- IRTONKUCLPTRNS-UHFFFAOYSA-N 2-butoxyaniline Chemical compound CCCCOC1=CC=CC=C1N IRTONKUCLPTRNS-UHFFFAOYSA-N 0.000 description 1
- WDPRBYZUUOJVBX-UHFFFAOYSA-N 2-nitro-N-propoxyaniline Chemical compound C(CC)ONC1=C(C=CC=C1)[N+](=O)[O-] WDPRBYZUUOJVBX-UHFFFAOYSA-N 0.000 description 1
- AXXYMKMFXNCXGM-UHFFFAOYSA-N 2-propoxyaniline Chemical compound CCCOC1=CC=CC=C1N AXXYMKMFXNCXGM-UHFFFAOYSA-N 0.000 description 1
- OTBQGZCBYVALOL-UHFFFAOYSA-N 4-nitro-2-phenylmethoxyaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1OCC1=CC=CC=C1 OTBQGZCBYVALOL-UHFFFAOYSA-N 0.000 description 1
- DXGYNRACFIAKQY-UHFFFAOYSA-N 4-nitro-2-propoxyaniline Chemical compound CCCOC1=CC([N+]([O-])=O)=CC=C1N DXGYNRACFIAKQY-UHFFFAOYSA-N 0.000 description 1
- RXQCEGOUSFBKPI-UHFFFAOYSA-N 5-Nitro-2-propoxyaniline Chemical compound CCCOC1=CC=C([N+]([O-])=O)C=C1N RXQCEGOUSFBKPI-UHFFFAOYSA-N 0.000 description 1
- VWLXPSZDHYNSRA-UHFFFAOYSA-N 5-nitro-2-phenylmethoxyaniline Chemical compound NC1=CC([N+]([O-])=O)=CC=C1OCC1=CC=CC=C1 VWLXPSZDHYNSRA-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-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
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- LFQULJPVXNYWAG-UHFFFAOYSA-N sodium;phenylmethanolate Chemical compound [Na]OCC1=CC=CC=C1 LFQULJPVXNYWAG-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL107895A NL57133C (enrdf_load_stackoverflow) | 1942-10-01 | 1942-10-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE452305A true BE452305A (fr) | 1943-10-30 |
Family
ID=1813567
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE452305A BE452305A (fr) | 1942-10-01 | 1943-09-14 | Procédé de fabrication d'alcoxy-2 nitro-5-anilines, le cas échéant en combinaison avec des alcoxy-2 nitro-4 anilines, le groupe alcoxy contenant plus de deux atomes de carbone |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE452305A (enrdf_load_stackoverflow) |
| CH (1) | CH249869A (enrdf_load_stackoverflow) |
| FR (1) | FR897789A (enrdf_load_stackoverflow) |
| GB (1) | GB597835A (enrdf_load_stackoverflow) |
| NL (1) | NL57133C (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3046607A1 (de) * | 1980-12-11 | 1982-07-22 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von 1-amino-2-nitro-4-alkoxybenzolen |
-
1942
- 1942-10-01 NL NL107895A patent/NL57133C/nl active
-
1943
- 1943-09-03 FR FR897789D patent/FR897789A/fr not_active Expired
- 1943-09-14 BE BE452305A patent/BE452305A/fr unknown
- 1943-09-16 CH CH249869D patent/CH249869A/de unknown
-
1945
- 1945-08-17 GB GB20996/45A patent/GB597835A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH249869A (de) | 1947-07-31 |
| GB597835A (en) | 1948-02-04 |
| FR897789A (fr) | 1945-03-30 |
| NL57133C (enrdf_load_stackoverflow) | 1944-05-15 |
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