US3846419A
Expired / Lapsed
US
⏱️ 0.0 years remaining
4h-5,6-dihydro-1,3-oxazines
Assignee: Huels AG
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Filing: 1972-02-15
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Granted: 1974-11-05
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Expires: 1992-02-15
Abstract
Abstract 4-Substituted-4H-5,6-dihydro-1,3-oxazines of the formula WHEREIN R is alkyl having 1-18 carbon atoms, alkenyl having 2-18 carbon atoms, or phenyl; R1 is lower alkyl, lower alkenyl, or phenyl; R2 is hydrogen or methyl, and R3 is lower alkyl of 1-8 carbon atoms or phenyl and is different from R1. These compounds, which are stabilizers for plastics and chlorinated solvents, are prepared in one stage from: (a) an aldehyde having at least two carbon atoms; (b) an olefinically unsaturated compound; (c) a carboxylic acid amide, and (d) a strong non-oxidizing acid.
Inventors
- 👤 W Seeliger
- 👤 K Hesse
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 18:54
CPC Classifications
C; C07; C07D; C07D265/00; C07D265/04; C07D265/06; C07D265/08
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
97 words
A PROCESS FOR THE PRODUCTION OF A 4H-5,6-DIHYDRO-1,3OXAZINE SUBSTITUTED IN THE 41 POSITION WHICH COMPRISES REACTING IN ONE STAGE A MIXTURE COMPRISING A. AN ALDEHYDE SELECTED FROM THE GROUP CONSISTING OF A SATURATED ALIPHATIC ALDEHYDE HAVING AT LEAST 2 CARBON ATOMS AND AN AROMATIC ALDEHYDE CONTAINING NO OLEFINIC UNSATURATION; B. AN A-OLEFIN OF 3-9 CARBON ATOMS; C. A CARBOXYLIC ACID AMINE SELECTED FROM THE GROUP CONSISTING OF ALKYL AMIDES, ALKENYL AMIDES, MONOCYCLIC ARYLAMIDES AND CYCLOALKYLAMIDES; AND D. STRONG, NON-OXIDIZING ACID, SAID REACTING BEING CONDUCTED AT A TEMPERATURE BETWEEN -10* AND 50* UNTIL AN OXAZILINE SALT IS FORMED.
Claim 2
Dependent Claim
97 words
A PROCESS FOR THE PRODUCTION OF A 4H-5,6-DIHYDRO-1,3OXAZINE SUBSTITUTED IN THE 41 POSITION WHICH COMPRISES REACTING IN ONE STAGE A MIXTURE COMPRISING A. AN ALDEHYDE SELECTED FROM THE GROUP CONSISTING OF A SATURATED ALIPHATIC ALDEHYDE HAVING AT LEAST 2 CARBON ATOMS AND AN AROMATIC ALDEHYDE CONTAINING NO OLEFINIC UNSATURATION; B. AN A-OLEFIN OF 3-9 CARBON ATOMS; C. A CARBOXYLIC ACID AMINE SELECTED FROM THE GROUP CONSISTING OF ALKYL AMIDES, ALKENYL AMIDES, MONOCYCLIC ARYLAMIDES AND CYCLOALKYLAMIDES; AND D. STRONG, NON-OXIDIZING ACID, SAID REACTING BEING CONDUCTED AT A TEMPERATURE BETWEEN -10* AND 50* UNTIL AN OXAZILINE SALT IS FORMED.
Claim 3
Dependent Claim
34 words
A process according to claim 1 wherein the carboxylic acid amide (c) is formed in situ from a corresponding member selected from the group consisting of a carboxylic acid nitrile and an Alpha -hydroxynitrile.
Claim 4
Dependent Claim
15 words
A process as defined by claim 1 wherein said amide is a lower aliphatic amide.
Claim 5
Dependent Claim
15 words
A process according to claim 1 wherein said mixture further includes a polar inert solvent.
Claim 6
Dependent Claim
24 words
A process according to claim 1 wherein said amide is selected from the group consisting of lower alkyl amides, lower alkenyl amides and benzamide.
Claim 7
Dependent Claim
31 words
A process according to claim 1 wherein said olefinically unsaturated compound is selected from the group consisting of lower alkenes, 1,3-dienes lower cycloalkenes, aromatic alkenes, lower alkylene halides and allyl esters.
Claim 8
Dependent Claim
25 words
A process according to claim 1 wherein said olefinically unsaturated compound is selected from the group consisting of styrene, Alpha -methylstyrene, isoprene and 2,3-dimethylbutadiene (1,3).
Claim 9
Dependent Claim
19 words
A process according to claim 1 wherein said aldehyde is a lower aliphatic aldehyde or a monocarboxyclic aromatic aldehyde.
Claim 10
Dependent Claim
14 words
A process according to claim 8 wherein said aldehyde is a lower alkyl aldehyde.
Claim 11
Dependent Claim
12 words
A process according to claim 1 wherein said acid is sulfuric acid.
Claim 12
Dependent Claim
18 words
A process according to claim 10 wherein said sulfuric acid has a water content of 10-30 vol. percent.
Claim 13
Dependent Claim
16 words
A process according to claim 4 wherein said polar solvent is a lower aliphatic monocarboxylic acid.
Claim 14
Dependent Claim
12 words
A process according to claim 12 wherein said acid is acetic acid.
Claim 15
Dependent Claim
12 words
A process according to claim 1 wherein the temperature is 0*-40* C.
Claim 16
Dependent Claim
19 words
A process according to claim 1 wherein said reaction mixture further comprises at least one free radical polymerization inhibitor.
Claim 17
Dependent Claim
10 words
A process according to claim 1 wherein said oxazine is
Claim 18
Dependent Claim
32 words
A process according to claim 1, further comprising liberating the free oxazine from said organic salt by the addition of alkaline agent, and isolating the free 4H-5,6-dihydro-1,3-oxazine product from the reaction mixture.
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) | 1977-11-04 | 1978-05-06 | 1978-11-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1981-11-04 | 1982-05-06 | 1982-11-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1985-11-04 | 1986-05-06 | 1986-11-05 | $7700.00 | Window Closed / Lapsed |