CA1152107A - Process for the preparation of 4-nitroso- diphenyl-amine - Google Patents
Process for the preparation of 4-nitroso- diphenyl-amineInfo
- Publication number
- CA1152107A CA1152107A CA000359796A CA359796A CA1152107A CA 1152107 A CA1152107 A CA 1152107A CA 000359796 A CA000359796 A CA 000359796A CA 359796 A CA359796 A CA 359796A CA 1152107 A CA1152107 A CA 1152107A
- Authority
- CA
- Canada
- Prior art keywords
- nitroso
- diphenylamine
- hydrochloric acid
- process according
- weight
- 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 26
- 230000008569 process Effects 0.000 title claims abstract description 20
- OIJHFHYPXWSVPF-UHFFFAOYSA-N para-Nitrosodiphenylamine Chemical compound C1=CC(N=O)=CC=C1NC1=CC=CC=C1 OIJHFHYPXWSVPF-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 34
- UBUCNCOMADRQHX-UHFFFAOYSA-N N-Nitrosodiphenylamine Chemical compound C=1C=CC=CC=1N(N=O)C1=CC=CC=C1 UBUCNCOMADRQHX-UHFFFAOYSA-N 0.000 claims abstract description 25
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000000725 suspension Substances 0.000 claims abstract description 12
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 9
- 238000005929 Fischer-Hepp rearrangement reaction Methods 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- 230000008707 rearrangement Effects 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 3
- 230000009471 action Effects 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 239000012047 saturated solution Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 230000000694 effects Effects 0.000 abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 13
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 8
- 235000011167 hydrochloric acid Nutrition 0.000 description 8
- 229960000443 hydrochloric acid Drugs 0.000 description 8
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 7
- 229960002415 trichloroethylene Drugs 0.000 description 7
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 229940035422 diphenylamine Drugs 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 239000001117 sulphuric acid Substances 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 230000000711 cancerogenic effect Effects 0.000 description 2
- 231100000315 carcinogenic Toxicity 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000007034 nitrosation reaction Methods 0.000 description 2
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000006462 rearrangement reaction Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 1
- 150000004008 N-nitroso compounds Chemical class 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- -1 benzene and toluene Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 235000005583 doda Nutrition 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- GTEKJZBPMPCYNB-UHFFFAOYSA-N n,n-diphenylnitrous amide;lead Chemical compound [Pb].C=1C=CC=CC=1N(N=O)C1=CC=CC=C1 GTEKJZBPMPCYNB-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 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
- C07C209/54—Preparation of compounds containing amino groups bound to a carbon skeleton by rearrangement reactions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2935775.3 | 1979-09-05 | ||
| DE19792935775 DE2935775A1 (de) | 1979-09-05 | 1979-09-05 | Verfahren zur herstellung von 4-nitroso-diphenylamin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1152107A true CA1152107A (en) | 1983-08-16 |
Family
ID=6080065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000359796A Expired CA1152107A (en) | 1979-09-05 | 1980-09-03 | Process for the preparation of 4-nitroso- diphenyl-amine |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4324913A (en, 2012) |
| EP (1) | EP0026316B1 (en, 2012) |
| JP (1) | JPS5640654A (en, 2012) |
| CA (1) | CA1152107A (en, 2012) |
| DE (2) | DE2935775A1 (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0602616B1 (en) * | 1992-12-15 | 1997-08-27 | Sumitomo Chemical Company Limited | Process for producing 4-nitrosodiphenylamines or their salts |
| RU2139274C1 (ru) * | 1998-07-14 | 1999-10-10 | Сибирский государственный технологический университет | Способ синтеза замещенных n-алкил-п-нитрозодифениламинов |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB773236A (en) * | 1954-01-08 | 1957-04-24 | Cfmc | Improvements in the preparation of c-nitrosodiarylamines |
| US2782235A (en) * | 1955-01-04 | 1957-02-19 | Cfmc | Preparation of c-nitrosodiarylamines |
| DE2211341A1 (de) * | 1972-03-09 | 1973-09-13 | Bayer Ag | Verfahren zur herstellung von 4nitroso-diphenylamin |
| DE2654936C3 (de) * | 1976-12-03 | 1980-03-06 | Aldan Aleksandrovitsch Usvjacov | Verfahren zur Herstellung von 4-Nitrosodiphenylamin |
| US4102926A (en) * | 1977-01-06 | 1978-07-25 | Aldan Alexandrovich Usvyatsov | Method for producing 4-nitrosodiphenylamine |
| JPS543019A (en) * | 1977-06-07 | 1979-01-11 | Toyo Soda Mfg Co Ltd | Preparation of 4-nitrosodiphenylamine hydrochliride |
-
1979
- 1979-09-05 DE DE19792935775 patent/DE2935775A1/de not_active Withdrawn
-
1980
- 1980-08-16 DE DE8080104894T patent/DE3060470D1/de not_active Expired
- 1980-08-16 EP EP80104894A patent/EP0026316B1/de not_active Expired
- 1980-09-02 US US06/183,202 patent/US4324913A/en not_active Expired - Lifetime
- 1980-09-03 JP JP12127080A patent/JPS5640654A/ja active Granted
- 1980-09-03 CA CA000359796A patent/CA1152107A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0026316A1 (de) | 1981-04-08 |
| DE3060470D1 (en) | 1982-07-15 |
| JPS6332061B2 (en, 2012) | 1988-06-28 |
| JPS5640654A (en) | 1981-04-16 |
| US4324913A (en) | 1982-04-13 |
| DE2935775A1 (de) | 1981-04-02 |
| EP0026316B1 (de) | 1982-05-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |