US5214166A
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Method of synthesizing nitrato alkyl oxetanes
Assignee: NAVY United States, AS REPRESENTED BY DEPARTMENT OF
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Filing: 1989-07-10
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Granted: 1993-05-25
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Expires: 2009-07-10
Abstract
Abstract Nitrato alkyl oxetanes are synthesized directly from the corresponding hyxy alkyl oxetanes by nitrating the hydroxy alkyl oxetane under non-acidic anhydrous conditions. A hydroxy alkyl oxetane is reacted with an anhydrous nitrate ester of a carboxylic acid at temperatures below about 10° C. The product of the method, nitrato alkyl oxetane, is produced in relatively high yield without opening of the oxetane ring.
Inventors
- 👤 Gerald E. Manser
- 👤 Robert M. Hajik
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 12:37
CPC Classifications
C; C07; C07D; C07D305/00; C07D305/02; C07D305/04; C07D305/06
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
95 words
A method of synthesizing a nitrato alkyl oxetane comprising: nitrating a hydroxy alkyl oxetane of the general formula ##STR2## wherein at least one of R 1 -R 2 is --(CH 2 ) n --CHOH--A, wherein n is one or greater and A is selected from the group comprising H and alkyl groups and the remainder of R 1 -R 6 are selected from the group comprising H and alkyl, under non-acidic anhydrous conditions with an anhydrous nitrate ester of a carboxylic acid of the general formula R--COOH wherein R is an alkyl or aryl moiety.
Claim 2
Independent Claim
95 words
A method of synthesizing a nitrato alkyl oxetane comprising: nitrating a hydroxy alkyl oxetane of the general formula ##STR2## wherein at least one of R 1 -R 2 is --(CH 2 ) n --CHOH--A, wherein n is one or greater and A is selected from the group comprising H and alkyl groups and the remainder of R 1 -R 6 are selected from the group comprising H and alkyl, under non-acidic anhydrous conditions with an anhydrous nitrate ester of a carboxylic acid of the general formula R--COOH wherein R is an alkyl or aryl moiety.
Claim 3
Dependent Claim
11 words
A method as described in claim 1 wherein A is H.
Claim 4
Dependent Claim
14 words
A method as described in claim 2 wherein n is between one and three.
Claim 5
Dependent Claim
14 words
A method as described in claim 3 wherein the hydroxy alkyl oxetane is 3,3-bis(hydroxymethyl)oxetane.
Claim 6
Dependent Claim
14 words
A method as described in claim 3 wherein the hydroxy alkyl oxetane is 3-hydroxymethyl-3-methyloxetane.
Claim 7
Dependent Claim
14 words
A method as described in claim 1 wherein said carboxylic acid is acetic acid.
Claim 8
Dependent Claim
21 words
A method as described in claim 1 wherein said nitration is carried out at a temperature of below about 10° C.
Claim 9
Dependent Claim
23 words
A method as described in claim 7 wherein said nitration is carried out at a temperature of between about 10° and -20° C.
Claim 10
Dependent Claim
20 words
A method as described in claim 8 wherein said nitration is carried out at a temperature of about 0° C.
Claim 11
Dependent Claim
19 words
A method as described in claim 1 wherein said nitration is carried out in a non-reactive, non-hygroscopic organic solvent.
Claim 12
Dependent Claim
15 words
A method as described in claim 9 wherein the solvent is chloroform or methylene chloride.
Claim 13
Dependent Claim
26 words
A method as described in claim 1 wherein the anhydrous nitrate ester is formed by reacting a nitrate-containing compound with an anhydride of the carboxylic acid.
Claim 14
Dependent Claim
19 words
A method as described in claim 12 wherein the nitrate-containing compound is between about 90% and 100% nitric acid.
Claim 15
Dependent Claim
16 words
A method as described in claim 13 wherein the nitrate-containing compound is about 90% nitric acid.
References Cited (Backward Citations)
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1996-05-24 | 1996-11-23 | 1997-05-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-05-24 | 2000-11-23 | 2001-05-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-05-24 | 2004-11-23 | 2005-05-25 | $7700.00 | Window Closed / Lapsed |