US4351777A
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Preparation of fluorobenzonitriles
Assignee: Rhone Poulenc Industries SA
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Filing: 1981-09-22
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Granted: 1982-09-28
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Expires: 2001-09-22
Abstract
Abstract Fluorobenzonitriles are prepared by reacting their corresponding chlorobenzonitriles with at least one alkali metal fluoride, in an aprotic solvent reaction medium, in the presence of at least one tertiary amine sequestering agent having the structural formula: N--CHR.sub.1 --CHR.sub.2 --O--(CHR.sub.2 --CHR.sub.4 --O).sub.n R.sub.5 ] 3 .
Inventors
- 👤 R. Ramanadin
- 👤 Alain Roustan
- 👤 Gerard Soula
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 19:58
CPC Classifications
C; C07; C07C; C07C255/00; C07C255/49
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
154 words
A process for the preparation of a fluorobenzonitrile, comprising reacting the chlorobenzonitrile corresponding thereto with at least one alkali metal fluoride, in an aprotic solvent reaction medium, in the presence of an effective amount of at least one tertiary amine sequestering agent having the structural formula: N--CHR.sub.1 --CHR.sub.2 --O--(CHR.sub.2 --O).sub.n R.sub.5 ].sub.3 (I) wherein n is a number greater than or equal to 0 and less than or equal to about 10, R 1 , R 2 , R 3 , R 4 , which may be identical or different, each represents a hydrogen atom or an alkyl radical having from 1 to 4 carbon atoms and R 5 represents an alkyl or cycloalkyl radical having from 1 to 12 carbon atoms, a phenyl radical or a radical of the formula --C m H 2m --φ, or C m H 2m+1 --φ--, with m ranging from 1 to about 12 and φ being phenyl.
Claim 2
Dependent Claim
154 words
A process for the preparation of a fluorobenzonitrile, comprising reacting the chlorobenzonitrile corresponding thereto with at least one alkali metal fluoride, in an aprotic solvent reaction medium, in the presence of an effective amount of at least one tertiary amine sequestering agent having the structural formula: N--CHR.sub.1 --CHR.sub.2 --O--(CHR.sub.2 --O).sub.n R.sub.5 ].sub.3 (I) wherein n is a number greater than or equal to 0 and less than or equal to about 10, R 1 , R 2 , R 3 , R 4 , which may be identical or different, each represents a hydrogen atom or an alkyl radical having from 1 to 4 carbon atoms and R 5 represents an alkyl or cycloalkyl radical having from 1 to 12 carbon atoms, a phenyl radical or a radical of the formula --C m H 2m --φ, or C m H 2m+1 --φ--, with m ranging from 1 to about 12 and φ being phenyl.
Claim 3
Dependent Claim
27 words
The process as defined by claim 1, wherein the formula (I), R 1 , R 2 , R 3 and R 4 are each hydrogen or methyl.
Claim 4
Dependent Claim
32 words
The process as defined by claims 1 or 2, wherein the formula (I), n is an integer which is greater than or equal to 0 and less than or equal to 6.
Claim 5
Dependent Claim
26 words
The process as defined by claims 1 or 2, wherein the formula (I), R 5 is an alkyl radical having from 1 to 4 carbon atoms.
Claim 6
Dependent Claim
68 words
The process as defined by claims 1 or 2, wherein the formula (I), R 1 , R 2 , R 3 and R 4 , which are identical or different, are each hydrogen or methyl, n is an integer which is greater than or equal to 0 and less than or equal to 6 and R 5 is an alkyl radical having from 1 to 4 carbon atoms.
Claim 7
Dependent Claim
27 words
The process as defined by claim 5, wherein the tertiary amine of the formula (I) is tris-(3,6,9-trioxadecyl)-amine of the formula: N--(CH.sub.2 --CH.sub.2 --O--CH.sub.2 --CH.sub.2 --O--CH.sub.2 --CH.sub.2 --O--CH.sub.3).sub.3.
Claim 8
Dependent Claim
28 words
The process as defined by claim 5, wherein the tertiary amine of the formula (I) is tris-(3,6,9-trioxaundecyl)-amine of the formula: N--(CH.sub.2 --CH.sub.2 --O--CH.sub.2 --CH.sub.2 --O--CH.sub.2 --CH.sub.2 --O--C.sub.2 H.sub.5).sub.3.
Claim 9
Dependent Claim
36 words
The process as defined by claim 1, wherein the tertiary amine of the formula (I) is selected from the group consisting of tris-(3-oxabutyl)-amine, tris-(3,6-dioxaheptyl)-amine, tris-(3,6,9-trioxadecyl)-amine, tris-(3,6-dioxaoctyl)-amine, tris-(3,6,9-trioxaundecyl)-amine, tris-(3,6-dioxanonyl)-amine, tris-(3,6,9-trioxadodecyl)-amine, tris-(3,6-dioxadecyl)-amine, tris-(3,6,9-trioxatridecyl)-amine, tris-(3,6,9,12-tetraoxatridecyl)-amine, tris-(3,6,9,12,15,18-hexaoxanonadecyl)-amine, tris-(3,6-dioxa-4-methylheptyl)-amine, and tris-(3,6-dioxa-2,4-dimethylheptyl)-amine.
Claim 10
Dependent Claim
23 words
The process as defined by claim 1, wherein the at least one alkali metal fluoride is potassium fluoride, cesium fluoride and/or rubidium fluoride.
Claim 11
Dependent Claim
16 words
The process as defined by claim 1, said aprotic solvent being N-methylpyrrolidone, dimethylsulfoxide, dimethylformamide, or sulfolane.
Claim 12
Dependent Claim
24 words
The process as defined by claim 1, the molar ratio of sequestering agent to alkali metal fluoride ranging from about 0.005 to about 0.2.
Claim 13
Dependent Claim
16 words
The process as defined by claim 11, said ratio ranging from about 0.01 to about 0.1.
Claim 14
Dependent Claim
26 words
The process as defined by claim 1, the product fluorobenzonitrile having the structural formula: ##STR5## wherein n and m are integers ranging from 1 to 5.
References Cited (Backward Citations)
US3290353A
Cited
US4229365A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-09-27 | 1986-03-29 | 1986-09-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-09-27 | 1990-03-29 | 1990-09-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-09-27 | 1994-03-29 | 1994-09-28 | $7700.00 | Window Closed / Lapsed |