US4174349A
Expired / Lapsed
US
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Preparation of fluoroorganic compounds with calcium fluoride
Assignee: Honeywell International Inc
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Filing: 1978-10-30
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Granted: 1979-11-13
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Expires: 1998-10-30
Abstract
Abstract Fluoroorganic compounds are prepared by reacting a haloorganic starting material in which at least one halo atom is replaceable with a fluorine atom by metathetical exchange, with calcium fluoride in the presence of a crown ether and an anhydrous, polar, basic organic solvent which complexes with the calcium ion and contains no -OH groups, at a temperature and for a period of time adequate to effect fluorination.
Inventors
- 👤 Francis E. Evans
- 👤 Morris B. Berenbaum
- 👤 Richard E. Eibeck
- 👤 Martin A. Robinson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 18:14
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/61; C07C45/63; C07C17/00; C07C17/093; C07C17/20; C07C17/202; C07C17/208; C07C51/00; C07C51/58
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
71 words
The method which comprises reacting a haloorganic starting material in which at least one halo atom is replaceable with a fluorine atom by metathetical exchange, with calcium fluoride in the presence of a cage compound and an anhydrous polar, basic organic solvent which contains no --OH groups and which solubilizes the cage compound, starting material and calcium fluoride, at a temperature and for a period of time adequate to effect fluorination.
Claim 2
Independent Claim
71 words
The method which comprises reacting a haloorganic starting material in which at least one halo atom is replaceable with a fluorine atom by metathetical exchange, with calcium fluoride in the presence of a cage compound and an anhydrous polar, basic organic solvent which contains no --OH groups and which solubilizes the cage compound, starting material and calcium fluoride, at a temperature and for a period of time adequate to effect fluorination.
Claim 3
Dependent Claim
33 words
The method according to claim 1 in which the haloorganic starting material is selected from the group consisting of alkyl halides, acyl halides, haloacyl halides, haloethers, haloketones, haloaldehydes, aryl halides and aralkyl halides.
Claim 4
Dependent Claim
16 words
The method according to claim 1 in which the haloorganic starting material is an alkyl chloride.
Claim 5
Dependent Claim
16 words
The method according to claim 1 in which the haloorganic starting material is an acyl chloride.
Claim 6
Dependent Claim
16 words
The method according to claim 1 in which the haloorganic starting material is a haloacyl chloride.
Claim 7
Dependent Claim
15 words
The method according to claim 1 in which the haloorganic starting material is a chloroether.
Claim 8
Dependent Claim
15 words
The method according to claim 1 in which the haloorganic starting material is a chloroketone.
Claim 9
Dependent Claim
15 words
The method according to claim 1 in which the haloorganic starting material is a chloroaldehyde.
Claim 10
Dependent Claim
16 words
The method according to claim 1 in which the haloorganic starting material is an aryl chloride.
Claim 11
Dependent Claim
16 words
The method according to claim 1 in which the haloorganic starting material is an arylalkyl chloride.
Claim 12
Dependent Claim
15 words
The method according to claim 1 in which the cage compound is a crypt compound.
Claim 13
Dependent Claim
15 words
The method according to claim 1 in which the cage compound is a crown compound.
Claim 14
Dependent Claim
13 words
The method according to claim 12 in which the crown compound is 1,4,7,10,13,16-hexaoxacyclooctadecane.
Claim 15
Dependent Claim
13 words
The method according to claim 11 in which the crypt compound is 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8.]-hexacosane.
Claim 16
Dependent Claim
12 words
The method according to claim 16 in which the solvent is formamide.
Claim 17
Dependent Claim
19 words
The method according to claim 1 in which the solvent contains a basic nitrogen with no hydrogen attached thereto.
Claim 18
Dependent Claim
12 words
The method according to claim 16 in which the solvent is dimethylformamide.
Claim 19
Dependent Claim
12 words
The method according to claim 16 in which the solvent is dimethylacetamide.
Claim 20
Dependent Claim
12 words
The method according to claim 16 in which the solvent is triethylamine.
Claim 21
Dependent Claim
12 words
The method according to claim 16 in which the solvent is trimethylamine.
Claim 22
Dependent Claim
12 words
The method according to claim 16 in which the solvent is dimethylacetamide.
Claim 23
Dependent Claim
19 words
The method according to claim 1 which is carried out at about 70°-130° C. for at least two hours.
Claim 24
Dependent Claim
18 words
The method according to claim 1 wherein the solvent is dimethyl formamide and the cage compound is 1,4,7,10,13,16-hexaoxacyclooctadecane.
Claim 25
Dependent Claim
18 words
The method according to claim 1 wherein the solvent is dimethyl formamide and the cage compound is 4,7,13,15,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]-hexacosane.
Claim 26
Dependent Claim
18 words
The method according to claim 1 wherein the solvent is dimethyl formamide and the cage compound is 4,7,13,16,21-pentaoxa-1,10-diazabicyclo[8.8.5]-tricosane.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-11-12 | 1983-05-14 | 1983-11-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-11-12 | 1987-05-14 | 1987-11-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-11-12 | 1991-05-14 | 1991-11-13 | $7700.00 | Window Closed / Lapsed |