US3944575A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Aryl ether compounds and their synthesis
Assignee: United States Department of the Air Force
•
Filing: 1974-05-30
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Granted: 1976-03-16
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Expires: 1994-05-30
Abstract
Abstract Tetranitro aryl ether compounds are prepared by aromatic nucleophilic substitution of various aryl diols with 4-fluoro-1,2-dinitrobenzene. By reducing the nitro moieties of the tetranitro compounds, tetraamino aryl ether compounds are obtained. These latter compounds are useful as monomers in preparing thermally stable polymers having good solubility parameters.
Inventors
- 👤 Frank W. Villaescusa
- 👤 John G. Breland
- 👤 Fred E. Arnold
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 01:29
CPC Classifications
C; C07; C07C; C07C205/00; C07C205/27; C07C205/35; C07C205/36; C07C205/38; C07C217/00; C07C217/78; C07C217/80; C07C217/82; C07C217/90; C07C317/00; C07C317/14; C07C317/26; C07C317/32
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
31 words
As a new composition of matter, an arylene-oxy compound having the following formula: ##SPC5## where R is NO 2 , NH 2 or NH 3 Cl, and wherein Ar is ##SPC6##
Claim 2
Dependent Claim
31 words
As a new composition of matter, an arylene-oxy compound having the following formula: ##SPC5## where R is NO 2 , NH 2 or NH 3 Cl, and wherein Ar is ##SPC6##
Claim 3
Dependent Claim
12 words
The composition of claim 1 in which R is NO 2 .
Claim 4
Dependent Claim
12 words
The composition of claim 1 in which R is NH 2 .
Claim 5
Dependent Claim
12 words
The composition of claim 1 in which R is NH 3 Cl.
Claim 6
Dependent Claim
10 words
The composition of claim 1 in which Ar is ##SPC7##
Claim 7
Dependent Claim
10 words
The composition of claim 1 in which Ar is ##SPC8##
Claim 8
Dependent Claim
10 words
The composition of claim 1 in which Ar is ##SPC9##
Claim 9
Dependent Claim
10 words
The composition of claim 1 in which Ar is ##SPC10##
Claim 10
Dependent Claim
10 words
The composition of claim 1 in which Ar is ##SPC11##
Claim 11
Dependent Claim
54 words
A process for preparing a tetranitro aryl ether compound which comprises reacting 4-fluoro-1,2-dinitrobenzene with an aryl diol having the following formula: HO-Ar-OH, wherein Ar is ##SPC12## the reaction being conducted in a solvent under an inert atmosphere and in the presence of an organic or inorganic base; and recovering the tetranitro aryl ether compound.
Claim 12
Dependent Claim
54 words
A process for preparing a tetranitro aryl ether compound which comprises reacting 4-fluoro-1,2-dinitrobenzene with an aryl diol having the following formula: HO-Ar-OH, wherein Ar is ##SPC12## the reaction being conducted in a solvent under an inert atmosphere and in the presence of an organic or inorganic base; and recovering the tetranitro aryl ether compound.
Claim 13
Dependent Claim
73 words
The process according to claim 10 in which the mol ratio of 4-fluoro-1,2-dinitrobenzene to the aryl diol is in the range of about 2 to 5 to 1; the mol ratio of the base to the aryl diol is in the range of about 1.0 to 1.5 to 1; and the reaction is conducted at a temperature ranging from about -5°C to 150°C for a period ranging from about 1 to 24 hours.
Claim 14
Dependent Claim
77 words
The process according to claim 11 in which the tetranitro aryl ether compound is dissolved in a solvent; a catalyst and hydrazine or hydrazine hydrate are added to the resulting solution, said catalyst consisting essentially of palladium, platinum or Raney nickel on a charcoal support; and the solution is heated in an inert atmosphere under reflux conditions for a period of about 2 to 24 hours, thereby providing a reaction mixture containing a tetraamino aryl ether compound.
Claim 15
Dependent Claim
24 words
The process according to claim 12 in which the solvent is evaporated from the reaction mixture, thereby providing a solid tetraamino aryl ether compound.
Claim 16
Dependent Claim
76 words
The process according to claim 12 in which the reaction mixture is cooled; the cooled reaction mixture is mixed with concentrated hydrochloric acid, thereby precipitating hydrazine hydrochloride and a tetraamine hydrochloride aryl ether compound; the precipitate is dissolved in water; to the resulting solution a concentrated solution of ammonium hydroxide, sodium hydroxide, sodium carbonate or sodium bicarbonate is added, thereby precipitating a tetraamino aryl ether compound; and the tetraamino aryl ether compound is separated and dried.
References Cited (Backward Citations)
US3654364A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-03-16 | 1979-09-15 | 1980-03-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-03-16 | 1983-09-15 | 1984-03-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-03-16 | 1987-09-15 | 1988-03-16 | $7700.00 | Window Closed / Lapsed |