Oxidation op petroleum cyclohexane

Claim 1

A PROCESS FOR MANUFACTURING PARTIAL OXIDATION PRODUCTS OF CYCLOHEXANE, INCLUDING CYCLOHEXANOL AND CYCLOHEXANONE, WHICH COMPRISES REACTING A PETROLEUM CYCLOHEXANE CRUDE, SAID CRUDE CONTAINING AT LEAST 0.1% OF BENZENE, IN THE LIQUID PHASE WITH GASEOUS OXYGEN AT A TEMPERATURE OF 75* TO 200* C. UNDER A PRESSURE OF 50 TO 500 POUNDS PER SQUARE INCH IN THE PRESENCE OF A CATALYTIC QUANTITY OF A HYDROCARBON-SOLUBLE COMPOUND OF COBALT, SAID PETROLEUM CYCLOHEXANE CRUDE HAVING INITIALLY A SUFFICIENTLY HIGH CONTENT OF ORGANIC SULFUR COMPOUNDS TO POISON A NICKEL HYDROGENATION CATALYST WHEN AN ATTEMPT IS MADE TO CONVERT THE BENZENE IN THE SAID CRUDE TO CYCLOHEXANE BY HYDROGENATION OF THE CRUDE IN THE PRESENCE OF THE SAID CATALYST, CONTINUING THE OXIDATION WHILE SEPARATING WATER FROM THE OXIDATION MIXTURE SUBSTANTIALLY AS RAPIDALY AS THE SAID WATER IS FORMED BY THE OXIDATION REACTION, UNTIL FROM 5% TO 30% OF THE HYDROCARBON IN THE PETROLEUM CYCLOHEXANE CRUDE HAS BECOME OXIDIZED, ADMIXING WATER WITH THE RESULTING OXIDATION MIXTURE, DISTILLING THE RESULTING MIXTURE AND THEREBY SEPARATING THEREFROM AN AZEOTROPIC DISTILLATE CONTAINING BENZENE AND CYCLOHEXANE, SAID DISTILLATE HAVING A SUFFICIENTLY LOW CONTENT OF ORGANIC SULFUR COMPOUNDS THAT THE BENZENE CONTAINED THEREIN CAN BE READILY CONVERTED TO CYCLOHEXANE BY HYDROGENATION OF THE AZETROPIC DISTILLATE IN THE PRESENCE OF A NICKEL CATALYST, CONTINUING THE SAID DISTILLATION AND THEREBY SEPARATING ALSO A CYCLOHEXANE FRACTION HAVING A SMALLER BENZENE:CYCLOHEXANE RATIO THAN THE BENZENE:CYCLOHEXANE RATIO IN THE SAID OXIDATION MIXTURE IMMEDIATELY PRIOR TO THE SAID DISTILLATION, RECYCLING THE SAID CYCLOHEXANE FRACTION BACK TO THE OXIDIZER, HYDROGENATING THE SAID AZETROPIC DISTILLATE AND RETURNING THE RESULTING HYDROGENATION PRODUCT TO THE OXIDIZER, RECOVERING THE PORTION OF THE OXIDATION MIXTURE WHICH IS LESS VOLATILE THAN CYCLOHEXANE, SAID PORTION BEING RICH IN CYCLOHEXANOL AND CYCLOHEXANONE, AND CONTINUING THE SAID OXIDATION IN THE PRESENCE OF A CATALYTIC QUANTITY OF A HYDROCARBON-SOLUBLE COMPOUND OF COBALT, WITH MAKE-UP PETROLEUM CYCLOHEXANE CRUDE.