US4069226A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Preparation of acylisoxazolines
Assignee: Texaco Inc
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Filing: 1976-11-05
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Granted: 1978-01-17
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Expires: 1996-11-05
Abstract
Abstract A method of preparing acylisoxazolines by contacting an alkene with dinitrogen tetroxide and oxygen in the presence of a denitrating agent and calcium oxide.
Inventors
- 👤 Mahmoud S. Kablaoui
- 👤 John M. Larkin
- 👤 Robert E. Reid
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 00:10
CPC Classifications
C; C07; C07D; C07D261/00; C07D261/02; C07D261/04
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
168 words
A method of preparing an acylisoxazoline or mixtures thereof corresponding to the formula: ##STR3## where R is an alkyl group having from 2 to 20 carbon atoms which comprises contacting a 1-alkene, or mixtures thereof, of the formula R--CH═CH 2 with dinitrogen tetroxide and oxygen in the presence of a denitrating agent that consists of one or more compounds selected from ##STR4## where R 1 , R 2 , R 6 , R 7 , R 8 , R 9 and R 10 are alkyl of from 1 to 5 carbons and R 3 , R 4 , R 5 , R 11 , R 12 , and R 13 are hydrogen or alkyl of from 1 to 5 carbons and calcium oxide at a temperature of about -10° to 40° C., wherein the mole ratio of alkene to dinitrogen tetroxide to oxygen is from about 1:0.02:0.04 to 1:0.4:30 and the mole ratio of dinitrogen tetroxide to denitrating agent to calcium oxide is from about 1:0.5:0.5 to 1:5:5.
Claim 2
Independent Claim
168 words
A method of preparing an acylisoxazoline or mixtures thereof corresponding to the formula: ##STR3## where R is an alkyl group having from 2 to 20 carbon atoms which comprises contacting a 1-alkene, or mixtures thereof, of the formula R--CH═CH 2 with dinitrogen tetroxide and oxygen in the presence of a denitrating agent that consists of one or more compounds selected from ##STR4## where R 1 , R 2 , R 6 , R 7 , R 8 , R 9 and R 10 are alkyl of from 1 to 5 carbons and R 3 , R 4 , R 5 , R 11 , R 12 , and R 13 are hydrogen or alkyl of from 1 to 5 carbons and calcium oxide at a temperature of about -10° to 40° C., wherein the mole ratio of alkene to dinitrogen tetroxide to oxygen is from about 1:0.02:0.04 to 1:0.4:30 and the mole ratio of dinitrogen tetroxide to denitrating agent to calcium oxide is from about 1:0.5:0.5 to 1:5:5.
Claim 3
Dependent Claim
19 words
A method according to claim 1 wherein said contacting is at a temperature of about 5° to 25° C.
Claim 4
Dependent Claim
39 words
A method according to claim 1 wherein the mole ratio of alkene to dinitrogen tetroxide is about 1:0.05 to 1:0.3 and the mole ratio of dinitrogen tetroxide to denitrating agent to calcium oxide is from about 1:1:1 to 1:2:2.
Claim 5
Dependent Claim
14 words
A method according to claim 1 wherein said alkene is a mixture of alkenes.
Claim 6
Dependent Claim
11 words
A method according to claim 1 wherein said alkene is 1-hexadecene.
Claim 7
Dependent Claim
11 words
A method according to claim 1 wherein said alkene is 1-tetradecene.
Claim 8
Dependent Claim
17 words
A method according to claim 1 wherein said denitrating agent is 1-methyl-2-pyrrolidinone, dimethylsulfoxide, dimethylformamide, dimethylacetamide, or tetramethylurea.
Claim 9
Dependent Claim
12 words
A method according to claim 1 wherein said denitrating agent is 1-methyl-2-pyrrolidinone.
References Cited (Backward Citations)
US2564423A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-01-16 | 1981-07-18 | 1982-01-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-01-16 | 1985-07-18 | 1986-01-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-01-16 | 1989-07-18 | 1990-01-17 | $7700.00 | Window Closed / Lapsed |