Preparation of quinacridonequinones and substituted derivatives of same
A process for by oxidizing a quinacridone in a liquid medium with a non-metal oxidant producing a quinacridonequinone.
1. A process for preparing a quinacridonequinone of the formula
wherein each R substituent is independently selected from hydrogen, halogen, a C 1 –C 10 -alkoxy, a C 1 –C 10 -alkyl, a substituted phenyl, and unsubstituted phenyl; comprising oxidizing, in the presence of a liquid medium and an oxidant selected from the group consisting of persulfuric acid, persulfuric acid salts, persulfuric acid derivatives, and combinations thereof, a quinacridone of the formula
wherein each R substituent is independently selected from hydrogen, halogen, a C 1 –C 10 -alkoxy, a C 1 –C 10 -alkyl, a substituted phenyl and unsubstituted phenyl.
2. The process of claim 1 , wherein each R substituent is a methyl group.
3. The process of claim 1 , wherein each R substituent is a methoxy group.
4. The process of claim 1 , wherein each R substituent is hydrogen.
5. The process of claim 1 , wherein each R substituent is chlorine.
6. The process of claim 1 , wherein said liquid medium is selected from the group consisting of water, organic solvents, inorganic solvents, and combinations thereof.
7. The process of claim 6 , wherein said liquid medium is water.
8. The process of claim 6 , wherein said liquid medium is sulfuric acid.
9. The process of claim 1 , wherein said oxidant is selected from the group consisting of persulfuric acids, persulfuric acid salts, and combinations thereof.
10. The process of claim 9 , wherein said oxidant is persulfuric acid.
11. The process of claim 9 , wherein said oxidant is a persulfuric acid salt.
12. The process of claim 11 wherein said persulfuric acid salt is a peroxydisulfuric acid salt.
13. The process of claim 12 , wherein said peroxydisulfuric acid salt is selected from the group consisting of sodium peroxydisulfate, potassium peroxydisulfate, ammonium peroxydisulfate, and combinations thereof.
14. The process of claim 13 , wherein said peroxydisulfuric acid salt is sodium peroxydisulfate.
15. The process of claim 1 further comprising oxidizing the quinacridone at temperatures ranging from about room temperature to about 85° C.
16. The process of claim 15 , wherein the temperature ranges from about 40° C. to about 85° C.
17. The process of claim 15 , wherein the temperature ranges from about 55° C. to about 65° C.
18. The process of claim 15 wherein the quinacridone is of the formula
wherein each R substituent is independently selected from hydrogen, halogen, a C 1 –C 10 -alkoxy, a C 1 –C 10 -alkyl, a substituted phenyl and unsubstituted phenyl; the oxidant is sodium peroxydisulfate; and oxidizing temperature ranges from about 55° C. to about 65° C.
19. The process of claim 15 wherein the quinacridone is of the formula
wherein each R substituent is independently selected from hydrogen, halogen, a C 1 –C 10 -alkoxy, a C 1 –C 10 -alkyl, a substituted phenyl and unsubstituted phenyl; the oxidant is sodium peroxydisulfate; and oxidizing temperature ranges from about 55° C. to about 65° C.
20. The process of claim 15 wherein the quinacridone is of the formula
wherein each R substituent is independently selected from hydrogen, halogen, a C 1 –C 10 -alkoxy, a C 1 –C 10 -alkyl, a substituted phenyl and unsubstituted phenyl; the oxidant is sodium peroxydisulfate; and oxidizing temperature ranges from about 55° C. to about 65° C.
21. The process of claim 15 wherein the quinacridone is of the formula
wherein each R substituent is independently selected from hydrogen, halogen, a C 1 –C 10 -alkoxy, a C 1 –C 10 -alkyl, a substituted phenyl and unsubstituted phenyl; the oxidant is sodium peroxydisulfate; and oxidizing temperature ranges from about 55° C. to about 65° C.
22. A quinacridonequinone prepared by the process of claim 1 .
23. A quinacridonequinone prepared by the process of claim 15 .
24. A process for improving purity of a quinacridonequinone of the formula
wherein each R substituent is independently selected from hydrogen, halogen, a C 1 –C 10 -alkoxy, a C 1 –C 10 -alkyl, a substituted phenyl, and unsubstituted phenyl; comprising oxidizing, in the presence of a liquid medium and an oxidant, selected from the group consisting of persulfuric acid, persulfuric acid salts, persulfuric acid derivatives, and combinations thereof, a quinacridone of the formula
wherein each R substituent is independently selected from hydrogen, halogen, a C 1 –C 10 -alkoxy, a C 1 –C 10 -alkyl, a substituted phenyl and unsubstituted phenyl.
25. The process of claim 6 , wherein the inorganic solvents are selected from the group consisting of polyphosphoric acid, phosphoric acid, acetic acid, and combinations thereof.