DE2226405B2 - Verfahren zur Herstellung von 3-Nitro-4-amino-toluol - Google Patents
Verfahren zur Herstellung von 3-Nitro-4-amino-toluolInfo
- Publication number
- DE2226405B2 DE2226405B2 DE19722226405 DE2226405A DE2226405B2 DE 2226405 B2 DE2226405 B2 DE 2226405B2 DE 19722226405 DE19722226405 DE 19722226405 DE 2226405 A DE2226405 A DE 2226405A DE 2226405 B2 DE2226405 B2 DE 2226405B2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- nitro
- aminotoluene
- reaction
- mol
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 18
- DLURHXYXQYMPLT-UHFFFAOYSA-N 2-nitro-p-toluidine Chemical compound CC1=CC=C(N)C([N+]([O-])=O)=C1 DLURHXYXQYMPLT-UHFFFAOYSA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims 2
- 238000006396 nitration reaction Methods 0.000 claims description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- 229910017604 nitric acid Inorganic materials 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 13
- 230000000802 nitrating effect Effects 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 5
- 238000000859 sublimation Methods 0.000 claims description 4
- 238000010626 work up procedure Methods 0.000 claims description 4
- YICAMJWHIUMFDI-UHFFFAOYSA-N 4-acetamidotoluene Chemical compound CC(=O)NC1=CC=C(C)C=C1 YICAMJWHIUMFDI-UHFFFAOYSA-N 0.000 claims description 3
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 3
- 238000006193 diazotization reaction Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 238000007711 solidification Methods 0.000 claims description 3
- 230000008023 solidification Effects 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims 2
- GDIIPKWHAQGCJF-UHFFFAOYSA-N 4-Amino-2-nitrotoluene Chemical compound CC1=CC=C(N)C=C1[N+]([O-])=O GDIIPKWHAQGCJF-UHFFFAOYSA-N 0.000 claims 1
- 230000008014 freezing Effects 0.000 claims 1
- 238000007710 freezing Methods 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000000243 solution Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- -1 acet compound Chemical class 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 150000001989 diazonium salts Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 101150049168 Nisch gene Proteins 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 235000021185 dessert Nutrition 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 206010016256 fatigue Diseases 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- QFCSRGLEMDRBMN-UHFFFAOYSA-N n-(2-methylphenyl)nitramide Chemical compound CC1=CC=CC=C1N[N+]([O-])=O QFCSRGLEMDRBMN-UHFFFAOYSA-N 0.000 description 1
- AGKHYRYULQFGQA-UHFFFAOYSA-N n-(4-methylphenyl)nitramide Chemical compound CC1=CC=C(N[N+]([O-])=O)C=C1 AGKHYRYULQFGQA-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000009935 nitrosation Effects 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 108010089746 wobe Proteins 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722226405 DE2226405B2 (de) | 1972-05-31 | 1972-05-31 | Verfahren zur Herstellung von 3-Nitro-4-amino-toluol |
| NL7307335A NL7307335A (cs) | 1972-05-31 | 1973-05-25 | |
| CH765573A CH577458A5 (cs) | 1972-05-31 | 1973-05-28 | |
| AU56224/73A AU472802B2 (en) | 1972-05-31 | 1973-05-29 | Process for the preparation of 3-nitro-4-amino-toluene |
| IT2473373A IT988730B (it) | 1972-05-31 | 1973-05-29 | Procedimento per la preparazione di 3 nitro 4 amino toluene |
| FR7319701A FR2186459B1 (cs) | 1972-05-31 | 1973-05-30 | |
| BR404973A BR7304049D0 (pt) | 1972-05-31 | 1973-05-30 | Processo para a preparacao de 3-nitro-4-amino-tolueno |
| GB2565673A GB1434098A (en) | 1972-05-31 | 1973-05-30 | Preparation of 3-nitro-4-aminotoluene |
| JP5991773A JPS4948625A (cs) | 1972-05-31 | 1973-05-30 | |
| BE131809A BE800375A (fr) | 1972-05-31 | 1973-06-01 | Procede de preparation du 3-nitro-4-amino-toluene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722226405 DE2226405B2 (de) | 1972-05-31 | 1972-05-31 | Verfahren zur Herstellung von 3-Nitro-4-amino-toluol |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2226405A1 DE2226405A1 (de) | 1973-12-13 |
| DE2226405B2 true DE2226405B2 (de) | 1974-04-11 |
| DE2226405C3 DE2226405C3 (cs) | 1974-11-07 |
Family
ID=5846380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722226405 Granted DE2226405B2 (de) | 1972-05-31 | 1972-05-31 | Verfahren zur Herstellung von 3-Nitro-4-amino-toluol |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS4948625A (cs) |
| AU (1) | AU472802B2 (cs) |
| BE (1) | BE800375A (cs) |
| BR (1) | BR7304049D0 (cs) |
| CH (1) | CH577458A5 (cs) |
| DE (1) | DE2226405B2 (cs) |
| FR (1) | FR2186459B1 (cs) |
| GB (1) | GB1434098A (cs) |
| IT (1) | IT988730B (cs) |
| NL (1) | NL7307335A (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2723247C2 (de) * | 1977-05-24 | 1982-09-16 | Hoechst Ag, 6000 Frankfurt | Verfahren zur kontinuierlichen Herstellung von 3-Nitro-4-acetylaminotoluol |
| US4600797A (en) * | 1979-10-23 | 1986-07-15 | Bayer Aktiengesellschaft | Process for the preparation of nitroaminobenzenes |
| DE3038394A1 (de) * | 1980-10-10 | 1982-05-19 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von nitroaminobenzolen |
| JPS5867650A (ja) * | 1981-10-19 | 1983-04-22 | Mitsui Petrochem Ind Ltd | ｐ‐ニトロアニリンの製造法 |
| JPS5939412A (ja) * | 1982-08-27 | 1984-03-03 | Hitachi Ltd | タンデム圧延機の適応制御方法 |
-
1972
- 1972-05-31 DE DE19722226405 patent/DE2226405B2/de active Granted
-
1973
- 1973-05-25 NL NL7307335A patent/NL7307335A/xx not_active Application Discontinuation
- 1973-05-28 CH CH765573A patent/CH577458A5/xx not_active IP Right Cessation
- 1973-05-29 AU AU56224/73A patent/AU472802B2/en not_active Expired
- 1973-05-29 IT IT2473373A patent/IT988730B/it active
- 1973-05-30 GB GB2565673A patent/GB1434098A/en not_active Expired
- 1973-05-30 FR FR7319701A patent/FR2186459B1/fr not_active Expired
- 1973-05-30 JP JP5991773A patent/JPS4948625A/ja active Pending
- 1973-05-30 BR BR404973A patent/BR7304049D0/pt unknown
- 1973-06-01 BE BE131809A patent/BE800375A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2226405C3 (cs) | 1974-11-07 |
| BE800375A (fr) | 1973-12-03 |
| CH577458A5 (cs) | 1976-07-15 |
| FR2186459A1 (cs) | 1974-01-11 |
| BR7304049D0 (pt) | 1974-07-18 |
| IT988730B (it) | 1975-04-30 |
| AU472802B2 (en) | 1976-06-03 |
| NL7307335A (cs) | 1973-12-04 |
| AU5622473A (en) | 1974-12-05 |
| JPS4948625A (cs) | 1974-05-11 |
| GB1434098A (en) | 1976-04-28 |
| DE2226405A1 (de) | 1973-12-13 |
| FR2186459B1 (cs) | 1976-11-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |