DE3200308A1 - Verfahren zur herstellung von 5-nitro-2-aminotoluol - Google Patents
Verfahren zur herstellung von 5-nitro-2-aminotoluolInfo
- Publication number
- DE3200308A1 DE3200308A1 DE19823200308 DE3200308A DE3200308A1 DE 3200308 A1 DE3200308 A1 DE 3200308A1 DE 19823200308 DE19823200308 DE 19823200308 DE 3200308 A DE3200308 A DE 3200308A DE 3200308 A1 DE3200308 A1 DE 3200308A1
- Authority
- DE
- Germany
- Prior art keywords
- nitro
- nitrotoluene
- reaction
- ammonia
- aminotoluene
- 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.)
- Withdrawn
Links
- XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-UHFFFAOYSA-N 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 10
- BGDCQZFFNFXYQC-UHFFFAOYSA-N 1-chloro-2-methyl-4-nitrobenzene Chemical compound CC1=CC([N+]([O-])=O)=CC=C1Cl BGDCQZFFNFXYQC-UHFFFAOYSA-N 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 239000005749 Copper compound Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 150000001880 copper compounds Chemical class 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000000047 product Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- CXNVOWPRHWWCQR-UHFFFAOYSA-N 4-Chloro-ortho-toluidine Chemical compound CC1=CC(Cl)=CC=C1N CXNVOWPRHWWCQR-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 1
- XCSNRORTQRKCHB-UHFFFAOYSA-N 2-chloro-6-nitrotoluene Chemical compound CC1=C(Cl)C=CC=C1[N+]([O-])=O XCSNRORTQRKCHB-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-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
- 229910000831 Steel Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940116318 copper carbonate Drugs 0.000 description 1
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- BIZZAMCVUWYVCZ-UHFFFAOYSA-N n-(2-methylphenyl)benzenesulfonamide Chemical compound CC1=CC=CC=C1NS(=O)(=O)C1=CC=CC=C1 BIZZAMCVUWYVCZ-UHFFFAOYSA-N 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
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction 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)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823200308 DE3200308A1 (de) | 1982-01-08 | 1982-01-08 | Verfahren zur herstellung von 5-nitro-2-aminotoluol |
| US06/453,510 US4443630A (en) | 1982-01-08 | 1982-12-27 | Process for preparing 2-amino-5-nitrotoluene |
| EP83100032A EP0083924B1 (de) | 1982-01-08 | 1983-01-04 | Verfahren zur Herstellung von 2-Amino-5-nitrotoluol |
| DE8383100032T DE3374304D1 (en) | 1982-01-08 | 1983-01-04 | Process for the preparation of 2-amino-5 nitrotoluene |
| JP58000536A JPS58126843A (ja) | 1982-01-08 | 1983-01-07 | ２−アミノ−５−ニトロトルオ−ルの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823200308 DE3200308A1 (de) | 1982-01-08 | 1982-01-08 | Verfahren zur herstellung von 5-nitro-2-aminotoluol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3200308A1 true DE3200308A1 (de) | 1983-07-21 |
Family
ID=6152731
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823200308 Withdrawn DE3200308A1 (de) | 1982-01-08 | 1982-01-08 | Verfahren zur herstellung von 5-nitro-2-aminotoluol |
| DE8383100032T Expired DE3374304D1 (en) | 1982-01-08 | 1983-01-04 | Process for the preparation of 2-amino-5 nitrotoluene |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8383100032T Expired DE3374304D1 (en) | 1982-01-08 | 1983-01-04 | Process for the preparation of 2-amino-5 nitrotoluene |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4443630A (enExample) |
| EP (1) | EP0083924B1 (enExample) |
| JP (1) | JPS58126843A (enExample) |
| DE (2) | DE3200308A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3924092C1 (enExample) * | 1989-07-20 | 1990-11-29 | Hoechst Ag, 6230 Frankfurt, De |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4521622A (en) * | 1983-02-15 | 1985-06-04 | Japan Synthetic Rubber Co., Ltd. | Process for producing aromatic amine |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2459002A (en) * | 1944-09-26 | 1949-01-11 | American Cyanamid Co | Preparation of acyl-nitroarylides |
| US3313854A (en) * | 1961-11-20 | 1967-04-11 | Universal Oil Prod Co | Preparation of para-nitrodiphenylamines utilizing a copper oxide catalyst |
| US3277175A (en) * | 1963-11-26 | 1966-10-04 | Eastman Kodak Co | Preparation of p-nitrodiphenylamines |
| DE2633811C2 (de) * | 1976-07-28 | 1983-11-10 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Nitrodiphenylaminen |
| DE2720316C2 (de) * | 1977-05-06 | 1982-04-01 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von 3,5-Dihalogenanilinen |
| DE2814860A1 (de) * | 1978-04-06 | 1979-10-11 | Bayer Ag | Verfahren zur herstellung von aromatischen aminen |
-
1982
- 1982-01-08 DE DE19823200308 patent/DE3200308A1/de not_active Withdrawn
- 1982-12-27 US US06/453,510 patent/US4443630A/en not_active Expired - Fee Related
-
1983
- 1983-01-04 EP EP83100032A patent/EP0083924B1/de not_active Expired
- 1983-01-04 DE DE8383100032T patent/DE3374304D1/de not_active Expired
- 1983-01-07 JP JP58000536A patent/JPS58126843A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3924092C1 (enExample) * | 1989-07-20 | 1990-11-29 | Hoechst Ag, 6230 Frankfurt, De |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58126843A (ja) | 1983-07-28 |
| EP0083924A3 (en) | 1984-12-12 |
| DE3374304D1 (en) | 1987-12-10 |
| US4443630A (en) | 1984-04-17 |
| EP0083924B1 (de) | 1987-11-04 |
| JPH0359896B2 (enExample) | 1991-09-12 |
| EP0083924A2 (de) | 1983-07-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |