Claims
- 1. A process for making a quinoxaline which comprises the steps of:
- (a) reacting a phosphorane with an acid halide of a polyoxy perfluoro-alkylene oxide wherein the perfluoro-oxyalkylene group has 2 or 3 carbon atoms and the number of perfluoro-oxyalkylene units is in the range of 2 to 20, to form a keto-ylid;
- (b) chlorinating said keto-ylid to form a polychloroketone;
- (c) hydrolyzing said polychloroketone to form the corresponding polyketone have one or two ##STR13## groups therein; and (d) reacting said polyketone with an o-arylene diamine to form the corresponding quinoxaline.
- 2. A process as defined in claim 1 in which the phosphorane is benzyl triphenyl phosphorane.
- 3. A process as defined in claim 1 wherein the perfluoro-oxyalkylene group has two carbon atoms.
- 4. A process as defined in claim 1 wherein the polyoxy-perfluoroalkylene oxide is derived from tetrafluoroethylene oxide.
- 5. A process as defined in claim 1 wherein the keto-ylid is a bis-keto-ylid and the polychloroketone is a bis(alpha, alpha-dichloroketone).
- 6. A process as defined in claim 5 wherein the polyketone has two ##STR14## groups therein.
- 7. A process as defined in claim 1 wherein the quinoxaline is a bis-quinoxaline.
- 8. A process as defined in claim 1 wherein the perfluoro-oxyalkylene group has three carbon atoms.
- 9. A process as defined in claim 1 wherein the polyoxy-perfluoro-alkylene oxide is derived from hexafluoro-propylene oxide.
- 10. A process as defined in claim 1 wherein the keto-ylid is a monoketo-ylid and the polychloroketone is an alpha, alpha-dichloroketone.
- 11. A process as defined in claim 10 wherein the polyketone has one ##STR15## group therein.
- 12. A process as defined in claim 1 wherein the acid halide is the acid chloride.
- 13. A process as defined in claim 1 wherein the chlorinating agent is elemental chlorine.
- 14. A process as defined in claim 1 wherein the chlorinating agent is thionyl chloride.
- 15. A process as defined in claim 1 wherein the dechlorinating agent is silver trifluoroacetate.
- 16. A process as defined in claim 1 wherein the o-arylene diamine is o-phenylene diamine.
- 17. A process for making a polychloroketone which comprises the steps of:
- (a) reacting benzyl triphenyl phosphorane with an acid halide of a polyoxy-perfluoro-alkylene oxide wherein the perfluoro-oxyalkylene group contains 2 or 3 carbon atoms and the number of perfluoro-oxyalkylene units is in the range of from 2 to 20, to form a keto-ylid; and
- (b) and chlorinating said keto-ylid to form a polychloroketone.
- 18. A process as defined in claim 17 wherein the perfluoro-oxyalkylene group contains two carbon atoms.
- 19. A process as defined in claim 17 wherein the polyoxy-perfluoroalkylene oxide is derived from tetrafluoro-ethylene oxide.
- 20. A process as defined in claim 17 wherein the keto-ylid is a bis-keto-ylid and the polychloroketone is a bis(alpha, alpha-dichloroketone).
- 21. A process as defined in claim 20 wherein the polyketone has two ##STR16## groups therein.
- 22. A process as defined in claim 17 wherein the perfluoro-oxyalkylene group contains three carbon atoms.
- 23. A process as defined in claim 17 wherein the polyoxy-perfluoroalkylene oxide is derived from hexafluoro-propylene oxide.
- 24. A process as defined in claim 17 wherein the keto-ylid is a mono-keto-ylid and the polychloroketone is an alpha, alpha-dichloroketone.
- 25. A process as defined in claim 17 wherein the acid halide is the acid chloride.
- 26. A process as defined in claim 17 wherein the chlorinating agent is elemental chlorine.
- 27. A process as defined in claim 17 wherein the chlorinating agent is thionyl chloride.
- 28. A process for producing a perfluoro-1,2-diketone which comprises the steps of hydrolyzing a perfluoro-poly-chloroketone, with water and silver trifluoroacetate and recovering the 1,2-diketone.
Government Interests
The U.S. Government has a paid-up license in this invention and the right in limited circumstances to require the patent owner to license others on reasonable terms as provided for by the terms of Contract No. F33615-80-C-5129 awarded by Elastomers and Coatings Branch Nonmetallic Materials Division, Air Force Materials Laboratory, Wright-Patterson AFB.
US Referenced Citations (6)
Non-Patent Literature Citations (1)
Entry |
House, "Modern Synthetic Reactions, 2nd Ed", p. 692. |