DE2020043A1 - Verfahren zur Herstellung von Nitrosophenylhydroxylaminen - Google Patents
Verfahren zur Herstellung von NitrosophenylhydroxylaminenInfo
- Publication number
- DE2020043A1 DE2020043A1 DE19702020043 DE2020043A DE2020043A1 DE 2020043 A1 DE2020043 A1 DE 2020043A1 DE 19702020043 DE19702020043 DE 19702020043 DE 2020043 A DE2020043 A DE 2020043A DE 2020043 A1 DE2020043 A1 DE 2020043A1
- Authority
- DE
- Germany
- Prior art keywords
- sulfuric acid
- organic liquid
- water
- product
- layer
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 18
- DAHPIMYBWVSMKQ-UHFFFAOYSA-N n-hydroxy-n-phenylnitrous amide Chemical class O=NN(O)C1=CC=CC=C1 DAHPIMYBWVSMKQ-UHFFFAOYSA-N 0.000 title description 2
- 238000002360 preparation method Methods 0.000 title description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 95
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 239000007788 liquid Substances 0.000 claims description 22
- 239000010410 layer Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- -1 aromatic nitro compound Chemical class 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- 150000002832 nitroso derivatives Chemical class 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000012044 organic layer Substances 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- JAMGZOIOVGVZOI-UHFFFAOYSA-N (n-phenylanilino) nitrite Chemical compound C=1C=CC=CC=1N(ON=O)C1=CC=CC=C1 JAMGZOIOVGVZOI-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 description 25
- 239000000243 solution Substances 0.000 description 16
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- NLRKCXQQSUWLCH-UHFFFAOYSA-N nitrosobenzene Chemical compound O=NC1=CC=CC=C1 NLRKCXQQSUWLCH-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000002198 insoluble material Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 230000000447 dimerizing effect Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- ICYPOGVRNGUWNP-UHFFFAOYSA-N 1,3-dichloro-2-nitrosobenzene Chemical compound ClC1=CC=CC(Cl)=C1N=O ICYPOGVRNGUWNP-UHFFFAOYSA-N 0.000 description 1
- OFQRRUGDGASXKM-UHFFFAOYSA-N 1,3-dimethyl-2-nitrosobenzene Chemical compound CC1=CC=CC(C)=C1N=O OFQRRUGDGASXKM-UHFFFAOYSA-N 0.000 description 1
- AYGXDXVGROLVJK-UHFFFAOYSA-N 1-chloro-2-nitrosobenzene Chemical compound ClC1=CC=CC=C1N=O AYGXDXVGROLVJK-UHFFFAOYSA-N 0.000 description 1
- ZNTJGNOQDHOIIX-UHFFFAOYSA-N 1-chloro-3-nitrosobenzene Chemical compound ClC1=CC=CC(N=O)=C1 ZNTJGNOQDHOIIX-UHFFFAOYSA-N 0.000 description 1
- RBKIPVPBQBMGNJ-UHFFFAOYSA-N 1-methoxy-2-nitrosobenzene Chemical compound COC1=CC=CC=C1N=O RBKIPVPBQBMGNJ-UHFFFAOYSA-N 0.000 description 1
- TWLBRQVYXPMCFK-UHFFFAOYSA-N 1-methyl-2-nitrosobenzene Chemical compound CC1=CC=CC=C1N=O TWLBRQVYXPMCFK-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 241000272814 Anser sp. Species 0.000 description 1
- 241000283074 Equus asinus Species 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- WJSUQVIHYHQLJG-UHFFFAOYSA-N O[ClH](CC[ClH](O)(=O)=O)(=O)=O Chemical compound O[ClH](CC[ClH](O)(=O)=O)(=O)=O WJSUQVIHYHQLJG-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- TWYVVGMYFLAQMU-UHFFFAOYSA-N gelgreen Chemical compound [I-].[I-].C1=C(N(C)C)C=C2[N+](CCCCCC(=O)NCCCOCCOCCOCCCNC(=O)CCCCC[N+]3=C4C=C(C=CC4=CC4=CC=C(C=C43)N(C)C)N(C)C)=C(C=C(C=C3)N(C)C)C3=CC2=C1 TWYVVGMYFLAQMU-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- VWLFQZQXGSXBKM-UHFFFAOYSA-N n-(4-nitrosophenyl)-n-phenylhydroxylamine Chemical compound C=1C=C(N=O)C=CC=1N(O)C1=CC=CC=C1 VWLFQZQXGSXBKM-UHFFFAOYSA-N 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 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 |
|---|---|---|---|
| GB2105669 | 1969-04-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2020043A1 true DE2020043A1 (de) | 1970-10-29 |
Family
ID=10156451
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702020043 Pending DE2020043A1 (de) | 1969-04-24 | 1970-04-24 | Verfahren zur Herstellung von Nitrosophenylhydroxylaminen |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE2020043A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2039445A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1257984A (enrdf_load_stackoverflow) |
| NL (1) | NL7005808A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4129740A (en) * | 1977-01-31 | 1978-12-12 | Akzona Incorporated | Process for the preparation of para-nitroso-diphenylhydroxylamines |
| EP0009267A1 (en) * | 1978-08-18 | 1980-04-02 | Akzo N.V. | Process for the preparation of p-nitroso-diphenylhydroxylamines |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19922405A1 (de) * | 1999-05-14 | 2000-11-16 | Bayer Ag | Verfahren zur Herstellung von (4-Nitrosophenyl)phenylhydroxylamin |
-
1969
- 1969-04-24 GB GB1257984D patent/GB1257984A/en not_active Expired
-
1970
- 1970-04-22 NL NL7005808A patent/NL7005808A/xx unknown
- 1970-04-23 FR FR7014922A patent/FR2039445A1/fr not_active Withdrawn
- 1970-04-24 DE DE19702020043 patent/DE2020043A1/de active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4129740A (en) * | 1977-01-31 | 1978-12-12 | Akzona Incorporated | Process for the preparation of para-nitroso-diphenylhydroxylamines |
| EP0009267A1 (en) * | 1978-08-18 | 1980-04-02 | Akzo N.V. | Process for the preparation of p-nitroso-diphenylhydroxylamines |
| US4242523A (en) * | 1978-08-18 | 1980-12-30 | Akzona Incorporated | Process for the preparation of para-nitroso-diphenyl-hydroxylamines |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2039445A1 (enrdf_load_stackoverflow) | 1971-01-15 |
| NL7005808A (enrdf_load_stackoverflow) | 1970-10-27 |
| GB1257984A (enrdf_load_stackoverflow) | 1971-12-22 |
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