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US4683086A
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Azido derivatives of pentaerythritol
Assignee: Boeing North American Inc
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Filing: 1985-08-19
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Granted: 1987-07-28
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Expires: 2005-08-19
Abstract
Abstract Diazido derivatives of pentaerythritol are prepared by reacting 3,3-bis(azidomethyl) oxetane with inorganic acids such as hydrobromic or nitric acid. The resulting diazido monobromide can be reacted with sodium azide to produce pentaerythritol triazide which can be subsequently nitrated to pentaerythritol triazido mononitrate. The pentaerythritol diazido mononitrate produced by the reaction of nitric acid with the above oxetane can be further nitrated with nitric acid to produce pentaerythritol diazido dinitrate. These diazido and triazido derivatives of pentaerythritol can be utilized as energetic azido plasticizers per se or can serve as intermediates for the production of such plasticizers.
Inventors
- 👤 Milton B. Frankel
- 👤 Edgar R. Wilson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 13:28
CPC Classifications
C; C07; C07C; C07C247/00; C06; C06B; C06B45/00; C06B45/04; C06B45/06; C06B45/10; C06B45/105
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
41 words
An azido derivative of pentearythritol having the general structural formula: ##STR5## wherein Y is selected from the group consisting of halogen, ONO 2 and N 3 , and Z is selected from the group consisting of OH and ONO 2 .
Claim 2
Dependent Claim
41 words
An azido derivative of pentearythritol having the general structural formula: ##STR5## wherein Y is selected from the group consisting of halogen, ONO 2 and N 3 , and Z is selected from the group consisting of OH and ONO 2 .
Claim 3
Dependent Claim
13 words
The compound of claim 1, wherein Y is halogen and Z is OH.
Claim 4
Dependent Claim
9 words
The compound of claim 2, wherein Y is Br.
Claim 5
Dependent Claim
14 words
The compound of claim 1, wherein Y is ONO 2 and Z is OH.
Claim 6
Dependent Claim
14 words
The compound of claim 1, wherein Y is N 3 and Z is OH.
Claim 7
Dependent Claim
16 words
The compound of claim 1, wherein Y is N 3 and Z is ONO 2 .
Claim 8
Dependent Claim
16 words
The compound of claim 1, wherein Y is ONO 2 and Z is ONO 2 .
Claim 9
Dependent Claim
90 words
A process for producing an azido derivative of pentaerythritol having the structural formula: ##STR6## comprising the sequential steps of: (1) reacting 3,3-bis(azidomethyl)oxetane with a mixture of hydrobromic acid and methylene chloride to produce pentaerythritol diazido monobromide; (2) reacting the product of step (1) with sodium azide and dimethylsulfoxide to produce pentearythritol triazide; (3) further reacting the pentaerythritol triazide of step (2) with a solution of acetic anhydride, methylene chloride and nitric acid; and (4) recovering the reaction product of step (3), pentaerythritol triazido mononitrate, having the structural formula shown above.
Claim 10
Dependent Claim
90 words
A process for producing an azido derivative of pentaerythritol having the structural formula: ##STR6## comprising the sequential steps of: (1) reacting 3,3-bis(azidomethyl)oxetane with a mixture of hydrobromic acid and methylene chloride to produce pentaerythritol diazido monobromide; (2) reacting the product of step (1) with sodium azide and dimethylsulfoxide to produce pentearythritol triazide; (3) further reacting the pentaerythritol triazide of step (2) with a solution of acetic anhydride, methylene chloride and nitric acid; and (4) recovering the reaction product of step (3), pentaerythritol triazido mononitrate, having the structural formula shown above.
Claim 11
Dependent Claim
69 words
A process for producing an azido derivative of pentaerythritol having the structural formula: ##STR7## comprising the sequential steps of: (1) reacting 3,3-bis(azidomethyl)oxetane in methylene chloride with nitric acid to product pentaerythritol diazido monoitrate; (2) reacting the product of step (1) with a mixture of acetic anhydride, methylene chloride, and nitric acid; and (3) recovering the reaction product of step (2), pentaerythritol diazido dinitrate, having the structural formula shown above.
Claim 12
Dependent Claim
69 words
A process for producing an azido derivative of pentaerythritol having the structural formula: ##STR7## comprising the sequential steps of: (1) reacting 3,3-bis(azidomethyl)oxetane in methylene chloride with nitric acid to product pentaerythritol diazido monoitrate; (2) reacting the product of step (1) with a mixture of acetic anhydride, methylene chloride, and nitric acid; and (3) recovering the reaction product of step (2), pentaerythritol diazido dinitrate, having the structural formula shown above.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-07-27 | 1991-01-26 | 1991-07-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-07-27 | 1995-01-26 | 1995-07-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-07-27 | 1999-01-26 | 1999-07-28 | $7700.00 | Window Closed / Lapsed |