Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1999-07-13
2000-04-04
Siegel, Alan
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C07F 902
Patent
active
060463589
ABSTRACT:
Impure tetra(dihydrocarbylamino)phosphonium halide is contacted with a liquid cyclic ether to dissolve the phosphonium halide and leave at least a portion of the impurities comprising at least quaternary ammonium halide or an amidophosphoxide remaining in the solid state. The solids and the liquid phase are separated from each other, an anhydrous non-solvent for the tetra(dihydrocarbylamino)phosphonium halide is mixed with the separated liquid phase to precipitate the tetra(dihydrocarbylamino)phosphonium halide, which is then separated from the liquid phase. The so-treated tetra(dihydrocarbylamino)phosphonium halide is more efficient as a catalyst for halogen exchange reactions than the original untreated tetra(dihydrocarbylamino)phosphonium halide.
REFERENCES:
patent: 3064058 (1962-11-01), Duesel et al.
patent: 3231625 (1966-01-01), Nyman
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), Haszeldine et al.
patent: 3312746 (1967-04-01), Fielding
patent: 3314955 (1967-04-01), Boudakian et al.
patent: 3334150 (1967-08-01), Pierce et al.
patent: 3388174 (1968-06-01), Fielding et al.
patent: 3408412 (1968-10-01), Blackley et al.
patent: 3429935 (1969-02-01), Wall 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: 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: 4287374 (1981-09-01), North
patent: 4543217 (1985-09-01), Erpenbach et al.
patent: 4684734 (1987-08-01), Kaieda et al.
patent: 4937397 (1990-06-01), Pews et al.
patent: 4978769 (1990-12-01), Kysela et al.
patent: 5315043 (1994-05-01), Fernandez et al.
patent: 5476976 (1995-12-01), Schach et al.
patent: 5789631 (1998-08-01), Balhoff et al.
patent: 5824827 (1998-10-01), Bildinov et al.
"Dimethyl Sulphone as a Reaction Solvent for the Preparation of Aromatic Fluorides"; By L. D. Starr et al; Chemistry and Industry Jul. 21, (1962); pp. 1328-1329.
"No. 163 Preparation de derives perhalogenes aromatiques polyfluores par reaction d'echange d'halogene, utilisant une phase sel fondu"; By: J. Hitzke et al; Bulletin de la Societe Chimique De France (1974); No. 5-6; pp. 811-814.
"La Fluoration De L'Hexachlorobenzene Et De LA Pentachloropyridine En Milieu De Fluorure De Potassium Solide"; By: J. Hitzke; Journal of Fluorine Chemistry (1980); vol. 16, pp. 103-128.
"Hlaex fluorination of 1,2,4,5-tetrachlorobenzene in a pressure reactor"; By: Yoshikazu Kimura et al, (1992); Journal of Fluorine Chemistry, vol. 59, pp. 289-291.
Tetraphenylphosphonium bromide-catalyzed `Halex` fluorination of chloroaryl sulfonyl chlorides; By: Suzuki et al., Journal of Fluorine Chemistry, (1991); vol. 55, pp. 335-337.
"Halex Fluorination of Chlorinated Benzaldehydes and Benzoyl Chlorides"; By: R. Eric Banks et al., 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. Hitzke; Journal of Fluorine Chemistry (1981); vol. 18, pp. 101-115.
Lundin, et al., "Investigation of Methods of Preparing Polyfluoroaromatic Compounds", Trudy Instituta Khimii, vol. 16, 1968, pp. 67-73, translated pp. 1-14.
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. Translated pp. 1-2.
Aromatic Fluorine Compounds. VII. Replacement of Aromatic-Cl and -NO 2 Groups by -F 1,2; By: G. C. Finger et al., (1956); Contributed from the Illinois State Geological Survey; vol. 78, pp. 6034-6036.
Aromatic fluoro derivatives. VIII. Reaction of chloronitro compounds with fluorides of alkali metals; Chemical Abstract, v.57,(1962) cols. h 9706-b 9707.
"Interaction of Chloroaromatic Compounds with Alkali Metal Fluorides in the Presence of Crown-Ethers"; Aksenov, et al., Journal of Fluorine Chemistry; vol. 28 (1985), pp. 73-87.
Heterocyclic Polyfluoro-compounds. Part VI. Preparation of Pentafluoropyridine and Chlorofluoropyridines from Pentachloropyridine; 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-Difluoropyridine from 2,6 Dichloropyridine; By: Boudakian, et al., J. Heterocyclic Chem., vol. 5, (1968); pp. 683-684.
"Aromatic Nucleophilic Substitution Reactions"; Chem. Reviews; American Society; vol. 48 (1951); pp. 273-277 and p. 405.
"Polyfluoro-heterocyclic Compounds. Part I. The Preparation of Fluoro-, Chlorofluoro-, 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"; G. C. Finger, et al; Journal of Org. Chemical (1963); vol. 28, 1963, 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.
"Some Properties of Phosphorimidic Triamides", by Koidan et al., Institute of Organic Chemistry, Academy of Sciences of the Ukraninian SSR. Translated from Zhurnal Obshchei Khimii, vol. 52, No. 9, pp. 2001-2011, Sep. 1982. Translated pp. 1779-1787.
"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. Maynard; J. Org. Chem. (1963); vol. 28, pp. 112-115.
The Synthesis of Pentafluorobenzoic Acid and a New Purification of Chloropentafluorobenzene; By D. E. Pearson et al.; Georg Thieme Publishers (1978); p. 127.
The Chemistry of `Naked` Anions. I. Reactions of the 18-Crown-6 Complex of Potassium Fluoride with Organic Substrates in Aprotic Organic Solvents1; Journal of the Amiercan Chemical Soc.; vol. 96(7), (1974) p. 2250-2252.
Polyfluoroarenes. Part XVI. A Convenient Synthesis of Pentafluorobenzonitrile; By: J. M. Birchall et al.; Journal Chemistry Society (1971); pp. 1341-1342.
"Inexpensive, Active KF for Nucleophilic Aromatic Displacement Reactions", Tetrahedron, vol. 51, No. 22, 1995, pp. 6363-6376, Smyth et al.
Berris Bruce C.
Cheng Chi-Hung
Albemarle Corporation
Pippenger Philip M.
Siegel Alan
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