Organic compounds -- part of the class 532-570 series – Organic compounds – Halogen containing
Patent
1996-11-25
1998-08-04
Siegel, Alan
Organic compounds -- part of the class 532-570 series
Organic compounds
Halogen containing
570206, C07C 2513, C07C 2200
Patent
active
057896313
ABSTRACT:
An anhydrous mixture containing a liquid phase and a solids phase formed from components comprising finely-divided sodium fluoride, hexabromobenzene, and a phosphonium catalyst, and optionally a liquid aprotic solvent/diluent, is heated at a temperature and for a time at which sodium bromide and at least one hexahalobenzene containing at least two fluorine atoms are produced. Preferably, the sodium fluoride is activated by one or more of procedures specified herein.
REFERENCES:
patent: 3064058 (1962-11-01), Duesel et al.
patent: 3240824 (1966-03-01), Boudakian et al.
patent: 3277192 (1966-10-01), Fielding et al.
patent: 3280124 (1966-10-01), Boudakian et al.
patent: 3296269 (1967-01-01), Boudakian et al.
patent: 3300537 (1967-01-01), Bennett et al.
patent: 3303197 (1967-02-01), Hazeldine et al.
patent: 3312746 (1967-04-01), Fielding
patent: 3314955 (1967-04-01), Boudakian et al.
patent: 3388174 (1968-06-01), Fielding et al.
patent: 3408412 (1968-10-01), Blackley et al.
patent: 3453337 (1969-07-01), Bennett et al.
patent: 3485839 (1969-12-01), Fuller
patent: 3574775 (1971-04-01), Fuller
patent: 3852365 (1974-12-01), Maher
patent: 3965197 (1976-06-01), Stepniczka
patent: 4069262 (1978-01-01), Kunz
patent: 4174349 (1979-11-01), Evans et al.
patent: 4209457 (1980-06-01), Fuller
patent: 4226811 (1980-10-01), Oeser et al.
patent: 4229365 (1980-10-01), Oeser et al.
patent: 4684734 (1987-08-01), Kaieda et al.
patent: 4978769 (1990-12-01), Kysela et al.
Aromatic Fluoro Derivates. VIII. Reaction of chloronitro compounds with fluorides of alkali metals; Chemical Abstract; pp. 9706 and 9707 (1962).
"Interaction of Chloroaromatic with Alkali Metal Fluorides in the Presence of Crown-Ethers", Yakobson, et al., Journal of Flourine Chemistry; vol. 28(1985), pp. 73-87.
Heterocyclic Polyfluoro-compounds. Part VI. Preparation of Pentafluoropyridine and Chlorofluoropyridines from Pentachloropydine; By: R E. Banks, et al; J. Chem. Soc., (1965) pp. 594-597.
"Preparation of Polyfluoroaromatic Compounds by the Reaction of Perhalogeno-aromatic Compounds with Potassium Fluoride in Sulpholan"; By: G. Fuller; Journal Chemical Society, (1965); pp. 6264-6267.
Solvent-free Fluorination of Partially-Chlorinated Heterocyclics: Synthesis of 2.6-Difluoropyridie from 2.6 Dichloropyridine; By: Boudakian, et al., J. Hetercyclic Chem. (1968); pp. 683-684.
"Aromatic Nucleophilic Substitution Reactions", Chem. Reviews; American Chemical Society; vol. 48(1951); pp. 273-277 and p. 405.
"Polyfluoro-heterocyclic Compounds. Part I. The Preparation of Fluoro-, Chlofluoro-, and Chlorofluorohydro-pyridines"; By: R. D. Chambers, et al; J. Chemical Society (1964); pp. 3573-3576.
"Aromatic Fluorine Compounds. XI. Replacement of Chlorine by Fluorine in Halopyridines"; By: G. C. Finger, et al; Journal of Org. Chemical (1963); vol. 28, pp. 1666-1668.
"Aromatic Fluorine Compounds. VIII. Plant Growth Regulators and Intermediates"; By: G. C. Finger, et al; Journal of American Chemical Society (1959); vol. 81, pp. 94-101.
"Dimethyl Sulphone as a Reaction Solvent for the Preparation of Aromatic Fluorides"; By: L. D. Starr; Chemistry and Industry (1962); pp. 1328-1329.
"Preparation de derives perhalogenes aromatiques polyfluores par reaction d'echange d'halogene, utilisant une phase sel fondu"; By: J. Hitzke; Bulletin de la Societe Chimique De Franc (1974); No. 5-6; pp. 811-814.
"LaFluoration De L'Hexachlorobenzene Et De LA Pentachloropyridine En Milieu De Potassium Solide"; By: J. Hitzke; Journal of Fluorine Chemistry (1980); vol. 16, pp. 103-128.
"Halex Fluorination of 1,2,4,5-tetrachlorobenzene in a pressure reactor"; By: Yoshikazu Kimura (1992); Journal of Fluorine Chemistry, vol. 59, pp. 289-291.
Tetraphenylphosphonium bromide-catalyzed 'Halex'fluorination of chloroaryl sulfonyl chlorides; By: Yoshikazu Kimura; Journal of Fluorine Chemistry, (1991); vol. 55, pp. 335-337.
"Halex Fluorination of Chlorinated Benzaldehydes and Benzoyl Chlorides"; By: R. Eric Banks; Journal of Fluorine Chemistry (1990); vol. 46, pp. 529-537.
La Fluoration par kf de Perhalogenes Organiques Aromatiques en Presence de Faibles Quantites de Sulfolane ou D'Eau. Spectres de Masses des Melanges Obtenus en Serie Benzenique; By: J. Hitxke; Journal of Flourine Chemistry (1981); vol. 18, pp. 101-115.
Aromatic Fluorine Compounds. VII. Replacement of Aromatic -Cl and -NO 2 Groups by -F 1,2; By: G. C. Finger (1956); Contributed from the Illinois State Geological Survey; vol. 78, pp. 6034-6036.
"The Replacement of Chlorine by Fluorine in Organic Compounds"; By: Hans Gottlieb; Journal American Chemical Society (1936); vol. 58, pp. 532-533.
Preparation of 3-Fluorophthalic Anhydride; By: Adam Heller; J. Org. Chem. (1960); vol. 25, pp. 834-835.
"Fluorination of Perhalobenzenes with Potassium Fluoride in Polar Solvents"; By: G. W. Holbrook, et al; J. Org. Chem. (1966), vol. 31, pp. 1259-1261.
The Synthesis of Highly Fluorinated Compounds by Use of Potassium Fluoride in Polar Solvents; By: John T. Naynard; J. Org. Chem. (1963); vol. 28, pp. 112-115.
The Synthesis of Pentafluorobenzoic Acid and a New Prification of Chloropentafluorobenzene; By D. E. Pearson; Georg Thieme Publishers (1978); p. 127.
The Chemistry of 'Naked'Anions. I Reactions of the 18-Crown-6 Complex of Potassium Fluoride with Organic Sustrates in Aprotic Organic Solvents1; Journal of the Amiercan Chemical Soc.; (1974) pp. 2250-2252.
"The Cyclohexylation of Touluene and Ethylbenene using Ethylaluminium Halides"; By: I. V. Nicolescu, et al; Chemistry and Industry (1962), p. 1329.
Polyfluoroarenes. Part XVI. A Convenient Synthesis of Pentafluorobenzonitrile; By: J. M. Birchall; Journal Chemistry Society (1971); pp. 1341-1342.
Lundin, et al., "Investigation of Methods of Preparing Polyfluoroaromatic Compounds", Trudy Instituta Khimii, vol. 16, 1968, pp. 67-73.
Vorozhtsov, et al., "Formation of Chloroheptafluorotoluenes in the Reaction of Hexachlorobenzene With Potassium Flouride", Zhurnal Vsesoyuznoe Khimicheskoe Obschestvo im. D.I. Medeleeva, vol. 14,(1), 1969, p. 114.
Balhoff John F.
Lin Ronny W.
Albemarle Corporation
Pippenger Philip M.
Siegel Alan
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