A process for the ozonolysis of an alkane may comprise combining an alkane and ozone in a liquid phase medium comprising CO.sub.2 under conditions sufficient to oxidize the alkane to produce one or more non-combustion products. The liquid phase medium may be free of a super acid.

A liquid phase selective oxidation process is described. The process involves the partial oxidation of alkanes to partially oxidized products. A lower alkane, a solvent, and a soluble metal catalyst are contacted in the presence of an oxidizing agent in a reaction zone under partial oxidation conditions to produce the partially oxidized products. The partially oxidized products include one or more of lower alkyl alcohols, lower alkyl ketones, and lower alkyl acetates. The soluble metal catalyst is a soluble metal salt of cobalt, manganese, chromium, titanium, copper, nickel, vanadium, iron, molybdenum, tin, cerium, zirconium, or combinations thereof, and the promoter comprises a bromine source, an imide source, or combinations thereof.

A liquid phase selective oxidation process is described. The process involves the partial oxidation of alkanes to partially oxidized products. A lower alkane, a solvent, and a soluble metal catalyst are contacted in the presence of an oxidizing agent in a reaction zone under partial oxidation conditions to produce the partially oxidized products. The partially oxidized products include one or more of lower alkyl alcohols, lower alkyl ketones, and lower alkyl acetates. The soluble metal catalyst is a soluble metal salt of cobalt, manganese, chromium, titanium, copper, nickel, vanadium, iron, molybdenum, tin, cerium, zirconium, or combinations thereof, and the promoter comprises a bromine source, an imide source, or combinations thereof.

A method for the oxidation of C.sub.1-9-alkanes including providing a mixture of a C.sub.1-9-alkane in a liquid phase, a boron containing reagent, a free radical initiator, and a drying means, and performing an oxidation reaction at a temperature from 130 C. to 180 C. in the presence of oxygen. The drying means may be a drying agent such as a molecular sieve, or a membrane. Also a composition for oxidation of C.sub.1-9-alkanes to sec-C.sub.1-9-alcohols.

A method for the oxidation of C.sub.1-9-alkanes including providing a mixture of a C.sub.1-9-alkane in a liquid phase, a boron containing reagent, a free radical initiator, and a drying means, and performing an oxidation reaction at a temperature from 130 C. to 180 C. in the presence of oxygen. The drying means may be a drying agent such as a molecular sieve, or a membrane. Also a composition for oxidation of C.sub.1-9-alkanes to sec-C.sub.1-9-alcohols.

Disclosed herein are reaction compositions comprising an oxidation catalyst, a solvent, and a substrate that is dissolved in the solvent. The oxidation catalyst comprises a metal ion complexed with an -keto acid and a tridentate N,N,O-ligand. Also disclosed herein are methods for oxidizing a CH bond of a molecule, the methods comprising contacting the molecule with a metal complex comprising a metal ion complexed with a tridentate N,N,O-ligand in the presence of an -keto acid and a solvent. In some embodiments, the oxidation catalyst or metal complex is linked to a solid support.

Disclosed herein are reaction compositions comprising an oxidation catalyst, a solvent, and a substrate that is dissolved in the solvent. The oxidation catalyst comprises a metal ion complexed with an -keto acid and a tridentate N,N,O-ligand. Also disclosed herein are methods for oxidizing a CH bond of a molecule, the methods comprising contacting the molecule with a metal complex comprising a metal ion complexed with a tridentate N,N,O-ligand in the presence of an -keto acid and a solvent. In some embodiments, the oxidation catalyst or metal complex is linked to a solid support.

A method and a system for inexpensively producing a corresponding target ketone and/or alcohol by decomposing hydroperoxide rapidly and with high selectivity using an aqueous alkaline solution and by recovering and recycling alkali. The method includes neutralizing at least a part of a carboxylic acid in the oxidation reaction solution by contacting the oxidation reaction solution with a first alkaline solution including a carbonate of an alkali metal, and separating the reaction mixture into a first oil phase and a first water phase; decomposing the hydroperoxide and the ester compound in the first oil phase by contacting the first oil phase with a second alkaline solution having a higher pH value than the first alkaline solution, and separating the reaction mixture into a second oil phase and a second water phase; and recovering the carbonate of an alkali metal from the first water phase and recycling the carbonate of an alkali metal to the first alkaline solution.

A method and a system for inexpensively producing a corresponding target ketone and/or alcohol by decomposing hydroperoxide rapidly and with high selectivity using an aqueous alkaline solution and by recovering and recycling alkali. The method includes neutralizing at least a part of a carboxylic acid in the oxidation reaction solution by contacting the oxidation reaction solution with a first alkaline solution including a carbonate of an alkali metal, and separating the reaction mixture into a first oil phase and a first water phase; decomposing the hydroperoxide and the ester compound in the first oil phase by contacting the first oil phase with a second alkaline solution having a higher pH value than the first alkaline solution, and separating the reaction mixture into a second oil phase and a second water phase; and recovering the carbonate of an alkali metal from the first water phase and recycling the carbonate of an alkali metal to the first alkaline solution.

The present disclosure is directed to novel methods of oxidizing hydrocarbons, particularly terpenes, using ozone, compounds made according to said methods, and compositions comprising said compounds.