CA1152107A - Process for the preparation of 4-nitroso- diphenyl-amine - Google Patents

Process for the preparation of 4-nitroso- diphenyl-amine

Info

Publication number: CA1152107A
Authority: CA; Canada
Prior art keywords: nitroso; diphenylamine; hydrochloric acid; process according; weight
Prior art date: 1979-09-05
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

Application number

CA000359796A

Other languages

English (en)

French (fr)

Inventor

Karlfried Wedemeyer

Lutz Kienitz

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date 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 date listed.)

1979-09-05

Filing date

1980-09-03

Publication date

1983-08-16

1980-09-03 Application filed by Bayer AG filed Critical Bayer AG

1983-08-16 Application granted granted Critical

1983-08-16 Publication of CA1152107A publication Critical patent/CA1152107A/en

Status Expired legal-status Critical Current

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)

CA000359796A 1979-09-05 1980-09-03 Process for the preparation of 4-nitroso- diphenyl-amine Expired CA1152107A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19792935775 DE2935775A1 (de)	1979-09-05	1979-09-05	Verfahren zur herstellung von 4-nitroso-diphenylamin
DEP2935775.3		1979-09-05

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 (2)
EP (1)	EP0026316B1 (2)
JP (1)	JPS5640654A (2)
CA (1)	CA1152107A (2)
DE (2)	DE2935775A1 (2)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE69313420T2 (de) *	1992-12-15	1998-01-02	Sumitomo Chemical Co	Verfahren zur Herstellung von 4-Nitrosodiphenylamin oder dessen Salzen
RU2139274C1 (ru) *	1998-07-14	1999-10-10	Сибирский государственный технологический университет	Способ синтеза замещенных n-алкил-п-нитрозодифениламинов

Family Cites Families (6)

* Cited by examiner, † Cited by third party
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 EP EP80104894A patent/EP0026316B1/de not_active Expired
- 1980-08-16 DE DE8080104894T patent/DE3060470D1/de not_active Expired
- 1980-09-02 US US06/183,202 patent/US4324913A/en not_active Expired - Lifetime
- 1980-09-03 CA CA000359796A patent/CA1152107A/en not_active Expired
- 1980-09-03 JP JP12127080A patent/JPS5640654A/ja active Granted

Also Published As

Publication number	Publication date
JPS5640654A (en)	1981-04-16
EP0026316A1 (de)	1981-04-08
EP0026316B1 (de)	1982-05-26
DE2935775A1 (de)	1981-04-02
JPS6332061B2 (2)	1988-06-28
DE3060470D1 (en)	1982-07-15
US4324913A (en)	1982-04-13

Legal Events

Date	Code	Title	Description
2000-08-16	MKEX	Expiry

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