US4001291A
Expired / Lapsed
US
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2,2,2-fluorodinitroethanethiol and method of preparation
Assignee: United States Department of the Navy
•
Filing: 1976-03-11
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Granted: 1977-01-04
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Expires: 1996-03-11
Abstract
Abstract Novel thiols of the formula CX (NO.sub.2).sub.2 CH.sub.2 SH wherein X is nitro, fluoro, chloro, bromo, or lower alkyl of from 1 to 4 bon atoms, are prepared by contacting triflates of the formula ##STR1## to form thioacetals of the formula ##STR2## which are then isolated from the reaction mixture and subjected to acid hydrolysis to form the thiols. The energy content of unsaturated propellant and explosive binders can be increased by the free radical addition of the nitro and halonitro thiols of this invention to the binders.
Inventors
- 👤 Horst G. Adolph
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 14:55
CPC Classifications
C; C07; C07C; C07C327/00; C06; C06B; C06B45/00; C06B45/04; C06B45/06; C06B45/10; C06B45/105; C07C323/00
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
29 words
A compound of the formula ##STR8## wherein X is selected from the group consisting of nitro, fluoro, chloro, bromo, and lower alkyl of from 1 to 4 carbon atoms.
Claim 2
Dependent Claim
29 words
A compound of the formula ##STR8## wherein X is selected from the group consisting of nitro, fluoro, chloro, bromo, and lower alkyl of from 1 to 4 carbon atoms.
Claim 3
Dependent Claim
18 words
The compound of claim 1 wherein X is selected from the group consisting of fluoro, chloro, and bromo.
Claim 4
Dependent Claim
17 words
The compound of claim 2 wherein X is selected from the group consisting of fluoro and chloro.
Claim 5
Dependent Claim
9 words
The compound of claim 3 wherein X is fluoro.
Claim 6
Dependent Claim
18 words
The compound of claim 1 wherein X is a lower alkyl of from 1 to 4 carbon atoms.
Claim 7
Dependent Claim
9 words
The compound of claim 5 wherein X is methyl.
Claim 8
Dependent Claim
9 words
The compound of claim 1 wherein X is nitro.
Claim 9
Dependent Claim
31 words
A compound of the formula CX(NO.sub.2).sub.2 CH.sub.2 SH wherein X is selected from the group consisting of nitro, fluoro, chloro, bromo, and lower alkyl of from 1 to 4 carbon atoms.
Claim 10
Dependent Claim
31 words
A compound of the formula CX(NO.sub.2).sub.2 CH.sub.2 SH wherein X is selected from the group consisting of nitro, fluoro, chloro, bromo, and lower alkyl of from 1 to 4 carbon atoms.
Claim 11
Dependent Claim
18 words
The compound of claim 8 wherein X is selected from the group consisting of fluoro, chloro, and bromo.
Claim 12
Dependent Claim
17 words
The compound of claim 9 wherein X is selected from the group consisting of fluoro and chloro.
Claim 13
Dependent Claim
9 words
The compound of claim 10 wherein X is fluoro.
Claim 14
Dependent Claim
18 words
The compound of claim 8 wherein X is a lower alkyl of from 1 to 4 carbon atoms.
Claim 15
Dependent Claim
9 words
The compound of claim 12 wherein X is methyl.
Claim 16
Dependent Claim
9 words
The compound of claim 8 wherein X is nitro.
Claim 17
Dependent Claim
81 words
A process for making nitro and halonitro thiols comprising: a. contacting a triflate of the formula CX(NO.sub.2).sub.2 CH.sub.2 OSO.sub.2 CF.sub.3 with ##STR9## to produce a thioacetate of the formula ##STR10## b. isolating the thioacetate from the reaction mixture; and then c. subjecting the thioacetate to normal acid hydrolysis to produce a thiol of the formula CX(NO.sub.2).sub.2 CH.sub.2 SH, wherein X is selected from the group consisting of nitro, fluoro, chloro, bromo, or lower alkyl of from 1 to 4 carbon atoms.
Claim 18
Dependent Claim
81 words
A process for making nitro and halonitro thiols comprising: a. contacting a triflate of the formula CX(NO.sub.2).sub.2 CH.sub.2 OSO.sub.2 CF.sub.3 with ##STR9## to produce a thioacetate of the formula ##STR10## b. isolating the thioacetate from the reaction mixture; and then c. subjecting the thioacetate to normal acid hydrolysis to produce a thiol of the formula CX(NO.sub.2).sub.2 CH.sub.2 SH, wherein X is selected from the group consisting of nitro, fluoro, chloro, bromo, or lower alkyl of from 1 to 4 carbon atoms.
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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) | 1980-01-04 | 1980-07-05 | 1981-01-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-01-04 | 1984-07-05 | 1985-01-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-01-04 | 1988-07-05 | 1989-01-04 | $7700.00 | Window Closed / Lapsed |