Amino- and hydrodefluorination of polyfluoroaromatic amines with aqueous ammonia in a steel autoclave. Synthesis of highly pure tetrafluorophenylenediamines

Amino- and hydrodefluorination of polyfluoroaromatic amines with aqueous ammonia in a steel autoclave. Synthesis of highly pure tetrafluorophenylenediamines Full article

Journal

Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171

Output data

Year: 2009, Volume: 58, Number: 4, Pages: 823-827 Pages count : DOI: 10.1007/s11172-009-0101-8

Tags

polyfluoroarenes; hexafluorobenzene; amines; ammonia; aminodefluorination; nucleophilic substitution; hydrodefluorination; organofluorine compounds

Authors

Kusov S. Z. ¹ , Rodionov V. I. ¹ , Vaganova T. A. ¹ , Shundrina I. K. ¹ , Malykhin E. V. ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia

The action of aqueous ammonia on hexafluorobenzene in a steel autoclave at 180-220 A degrees C yields a mixture of isomeric tetrafluorophenylenediamines and 2,4,5-trifluorophenylene-1,3-diamine. The content of the hydrodefluorination product significantly depends on the reaction temperature and time. Tetrafluorophenylene-1,3-diamine undergoes hydrodefluorination with aqueous ammonia in a steel autoclave at 200 A degrees C to give 2,4,5-trifluorophenylene-1,3-diamine; when the additives of NH4F and/or FeCl3 are present, 2,5-difluorophenylene-1,3-diamine is additionally formed. The hydrodefluorination products are not formed during bis-aminodefluorination of hexafluorobenzene with aqueous ammonia in a glass reactor or with anhydrous ammonia (in a mixture with aprotic solvent) in a steel autoclave.

Kusov S.Z. , Rodionov V.I. , Vaganova T.A. , Shundrina I.K. , Malykhin E.V.
Amino- and hydrodefluorination of polyfluoroaromatic amines with aqueous ammonia in a steel autoclave. Synthesis of highly pure tetrafluorophenylenediamines
Russian Chemical Bulletin. 2009. V.58. N4. P.823-827. DOI: 10.1007/s11172-009-0101-8 WOS Scopus РИНЦ

Published print:	Apr 1, 2009
Published online:	Apr 18, 2010

Web of science	WOS:000276774300026
Scopus	2-s2.0-77953553526
Elibrary	15300992
OpenAlex	W2084753000