CA1241665A - Process for the preparation of chloro-o-nitroanilines - Google Patents
Process for the preparation of chloro-o-nitroanilinesInfo
- Publication number
- CA1241665A CA1241665A CA000489641A CA489641A CA1241665A CA 1241665 A CA1241665 A CA 1241665A CA 000489641 A CA000489641 A CA 000489641A CA 489641 A CA489641 A CA 489641A CA 1241665 A CA1241665 A CA 1241665A
- Authority
- CA
- Canada
- Prior art keywords
- chloro
- formula
- ammonia
- reaction
- temperatures
- 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
- 238000000034 method Methods 0.000 title claims abstract description 24
- 230000008569 process Effects 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- AWZRAQWGIUYTOH-UHFFFAOYSA-N n-chloro-2-nitroaniline Chemical class [O-][N+](=O)C1=CC=CC=C1NCl AWZRAQWGIUYTOH-UHFFFAOYSA-N 0.000 title claims abstract description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 31
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 10
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 239000008096 xylene Substances 0.000 claims description 5
- 150000003738 xylenes Chemical class 0.000 claims description 3
- 230000036647 reaction Effects 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 description 9
- 150000002430 hydrocarbons Chemical class 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- QUIMTLZDMCNYGY-UHFFFAOYSA-N 2,4-dichloro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1Cl QUIMTLZDMCNYGY-UHFFFAOYSA-N 0.000 description 3
- ZCWXYZBQDNFULS-UHFFFAOYSA-N 5-chloro-2-nitroaniline Chemical compound NC1=CC(Cl)=CC=C1[N+]([O-])=O ZCWXYZBQDNFULS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- -1 gLycol ethers Chemical class 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- IOCXBXZBNOYTLQ-UHFFFAOYSA-N 3-nitrobenzene-1,2-diamine Chemical class NC1=CC=CC([N+]([O-])=O)=C1N IOCXBXZBNOYTLQ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001256 steam distillation Methods 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
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/10—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3431827.5 | 1984-08-30 | ||
| DE19843431827 DE3431827A1 (de) | 1984-08-30 | 1984-08-30 | Verfahren zur herstellung von chlor-o-nitroanilinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1241665A true CA1241665A (en) | 1988-09-06 |
Family
ID=6244230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000489641A Expired CA1241665A (en) | 1984-08-30 | 1985-08-29 | Process for the preparation of chloro-o-nitroanilines |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0173202B1 (enrdf_load_stackoverflow) |
| JP (1) | JPS6160637A (enrdf_load_stackoverflow) |
| BR (1) | BR8504162A (enrdf_load_stackoverflow) |
| CA (1) | CA1241665A (enrdf_load_stackoverflow) |
| DD (1) | DD236520A5 (enrdf_load_stackoverflow) |
| DE (2) | DE3431827A1 (enrdf_load_stackoverflow) |
| MX (1) | MX159907A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6479703B1 (en) | 1998-12-17 | 2002-11-12 | Aventis Cropscience Sa | Method for preparing polyhalogenated paratrifluoromethylanilines |
| US6552230B1 (en) | 1998-07-01 | 2003-04-22 | Bayer Aktiengesellschaft | Method for preparing 2-nitro-5-(phenylthio)-anilines |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3922036A1 (de) * | 1989-07-05 | 1991-01-31 | Hoechst Ag | Verfahren zur herstellung von 4,5-dichlor-2-nitro-anilin |
| JP4945840B2 (ja) * | 2000-11-29 | 2012-06-06 | 井関農機株式会社 | コンバイン |
| CN102531923A (zh) * | 2012-02-21 | 2012-07-04 | 南通市东昌化工有限公司 | 5-氯-2-硝基苯胺的生产方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2305573A (en) * | 1941-07-07 | 1942-12-15 | American Cyanamid Co | Preparation of nitrophenyl amines |
| US3002998A (en) * | 1959-05-13 | 1961-10-03 | Lloyd A Kaplan | Preparation of 1,3,5-triamino-2,4,6-trinitrobenzene |
| DE3104310A1 (de) * | 1981-02-07 | 1982-08-19 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 5-chlor-2-nitroanilin |
-
1984
- 1984-08-30 DE DE19843431827 patent/DE3431827A1/de not_active Withdrawn
-
1985
- 1985-08-19 DE DE8585110345T patent/DE3576816D1/de not_active Expired - Fee Related
- 1985-08-19 EP EP85110345A patent/EP0173202B1/de not_active Expired - Lifetime
- 1985-08-29 JP JP60188733A patent/JPS6160637A/ja active Granted
- 1985-08-29 DD DD85280119A patent/DD236520A5/de not_active IP Right Cessation
- 1985-08-29 BR BR8504162A patent/BR8504162A/pt not_active IP Right Cessation
- 1985-08-29 MX MX206458A patent/MX159907A/es unknown
- 1985-08-29 CA CA000489641A patent/CA1241665A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6552230B1 (en) | 1998-07-01 | 2003-04-22 | Bayer Aktiengesellschaft | Method for preparing 2-nitro-5-(phenylthio)-anilines |
| US6479703B1 (en) | 1998-12-17 | 2002-11-12 | Aventis Cropscience Sa | Method for preparing polyhalogenated paratrifluoromethylanilines |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0173202A3 (en) | 1986-12-03 |
| DE3431827A1 (de) | 1986-03-13 |
| BR8504162A (pt) | 1986-06-24 |
| EP0173202B1 (de) | 1990-03-28 |
| DE3576816D1 (de) | 1990-05-03 |
| JPS6160637A (ja) | 1986-03-28 |
| DD236520A5 (de) | 1986-06-11 |
| JPH0580464B2 (enrdf_load_stackoverflow) | 1993-11-09 |
| EP0173202A2 (de) | 1986-03-05 |
| MX159907A (es) | 1989-09-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |