The present invention concerns a method of oxidizing a cycloalkane to form a product mixture containing a corresponding alcohol and ketone, said method comprising contacting a cycloalkane with a hydroperoxide compound in the presence of a catalytic effective amount of a cerium oxide based catalyst.

The present invention provides a method for the preparation of a sex pheromone of Obsucure Mealy bug (OMB), (plus/minus) (2,3,4,4-tetramethycyclopentyl)methyl acetate. The method comprises a step of subjecting alpha-halotetramethylcyclohexanone to a Favorskii rearrangement to obtain a 2,3,4,4-tetramethylcyclopentane compound (2), a step of subjecting said compound (2) to reduction to obtain (2,3,4,4-tetramethylcyclopentyl)methanol (3) and a step of subjection said compound (3) to acylation to obtain a (2,3,4,4-tetramethylcyclopentyl)methyl carboxylate compound (4).

The present invention provides a method for the preparation of a sex pheromone of Obsucure Mealy bug (OMB), (plus/minus) (2,3,4,4-tetramethycyclopentyl)methyl acetate. The method comprises a step of subjecting alpha-halotetramethylcyclohexanone to a Favorskii rearrangement to obtain a 2,3,4,4-tetramethylcyclopentane compound (2), a step of subjecting said compound (2) to reduction to obtain (2,3,4,4-tetramethylcyclopentyl)methanol (3) and a step of subjection said compound (3) to acylation to obtain a (2,3,4,4-tetramethylcyclopentyl)methyl carboxylate compound (4).

A metal organic framework comprising zinc (II) ions and second metal ions, such as iron (II) ions, cobalt (II) ions, and copper (II) ions as nodes or clusters and coordinated 1,3,5-benzenetricarboxylic acid struts or linkers between them forming a porous coordination network in the form of polyhedral crystals that are isostructural to HKUST-1. Transmetallation processes for producing the metal organic frameworks, as well as methods for applications of the metal organic frameworks as catalysts, specifically catalysts for the oxidation of cyclic hydrocarbons, such as toluene, cyclohexane, and methylcyclohexane.

A metal organic framework comprising zinc (II) ions and second metal ions, such as iron (II) ions, cobalt (II) ions, and copper (II) ions as nodes or clusters and coordinated 1,3,5-benzenetricarboxylic acid struts or linkers between them forming a porous coordination network in the form of polyhedral crystals that are isostructural to HKUST-1. Transmetallation processes for producing the metal organic frameworks, as well as methods for applications of the metal organic frameworks as catalysts, specifically catalysts for the oxidation of cyclic hydrocarbons, such as toluene, cyclohexane, and methylcyclohexane.

This invention provides producing having an objective ketone and/or alcohol by decomposing of a hydrocarbon compound rapidly and selectively having a same number of carbon atoms as a hydrocarbon compound by decomposing a hydroperoxide in a reaction solution obtained from oxidizing the hydrocarbon compound using molecular oxygen of this invention involves, a hydroperoxide decomposition step for decomposing the hydroperoxide into the ketone and/or alcohol by contacting the reaction solution with an aqueous solution containing a carbonate of an alkaline earth metal or a carbonate of an alkali metal and a transition metal compound, a separation step for separating into an oil phase comprising the ketone and/or alcohol, and a water phase comprising the carbonate of an alkaline earth metal or carbonate of an alkali metal and the transition metal compound, a recovery step for recovering the carbonate of an alkali metal or carbonate of an alkaline earth metal and the transition metal compound by combusting the water phase, and a recycling step for recycling to the hydroperoxide decomposition step by dissolving at least the carbonate of the alkali metal or the carbonate of the alkaline earth metal among the recovered substances obtained from the recovery step in water.

A process for the synthesis of trans-fused γ-lactones having Formula (IV) from substituted cyclic ketones having Formula (I). A diastereoselective synthesis of (±)-epianastrephin (1) (wherein: R.sup.1 is ethenyl, R.sup.2 and R.sup.3 is methyl, and n is 1), (±)-anastrephin (2) (wherein: R.sup.2 is ethenyl, R.sup.1 and R.sup.3 is methyl and n is 1), and analogs thereof (wherein: R.sup.1 is H, C.sub.1-5 alkyl, C.sub.2-6 alkenyl or C.sub.2-6 alkynyl, R.sup.2 is H, C.sub.1-5 alkyl, C.sub.2-6 alkenyl or C.sub.2-6 alkynyl, R.sup.1 and R.sup.2 together with the carbon atom they are attached form a C.sub.3-6 cycloalkyl ring, R.sup.3 is C.sub.1-5 alkyl and n is 0-2):

##STR00001##

A process for the synthesis of trans-fused γ-lactones having Formula (IV) from substituted cyclic ketones having Formula (I). A diastereoselective synthesis of (±)-epianastrephin (1) (wherein: R.sup.1 is ethenyl, R.sup.2 and R.sup.3 is methyl, and n is 1), (±)-anastrephin (2) (wherein: R.sup.2 is ethenyl, R.sup.1 and R.sup.3 is methyl and n is 1), and analogs thereof (wherein: R.sup.1 is H, C.sub.1-5 alkyl, C.sub.2-6 alkenyl or C.sub.2-6 alkynyl, R.sup.2 is H, C.sub.1-5 alkyl, C.sub.2-6 alkenyl or C.sub.2-6 alkynyl, R.sup.1 and R.sup.2 together with the carbon atom they are attached form a C.sub.3-6 cycloalkyl ring, R.sup.3 is C.sub.1-5 alkyl and n is 0-2):

##STR00001##

Disclosed are processes and systems for making cyclohexanone from a mixture comprising phenol, cyclohexanone, and cyclohexylbenzene, comprising a step of or a device for subjecting at least a portion of the mixture to hydrogenation and a step of or a device for distilling a phenol/cyclohexanone/cyclohexylbenzene mixture to obtain an effluent rich in cyclohexanone.

Disclosed are processes and systems for making cyclohexanone from a mixture comprising phenol, cyclohexanone, and cyclohexylbenzene, comprising a step of or a device for subjecting at least a portion of the mixture to hydrogenation and a step of or a device for distilling a phenol/cyclohexanone/cyclohexylbenzene mixture to obtain an effluent rich in cyclohexanone.