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 relates to methods of controlling hydroformylation processes for producing normal (N) and iso (I) aldehydes at a N:I ratio. In one aspect, a method of controlling a hydroformylation process comprises contacting an olefin with carbon monoxide, hydrogen and a catalyst, the catalyst comprising (A) a transition metal, (B) a monophosphine, and (C) a tetraphosphine having the structure described herein, the contacting conducted in one or more reaction zones and at hydroformylation conditions to produce a blend of normal (N) and iso (I) aldehydes at a N:I ratio, the method comprising at least one of increasing the N:I ratio by adding additional tetraphosphine to a reaction zone; decreasing the N:I ratio by adding additional monophosphine to a reaction zone; or increasing the N:I ratio by volatilization of the free monophosphine.

The present invention relates to methods of controlling hydroformylation processes for producing normal (N) and iso (I) aldehydes at a N:I ratio. In one aspect, a method of controlling a hydroformylation process comprises contacting an olefin with carbon monoxide, hydrogen and a catalyst, the catalyst comprising (A) a transition metal, (B) a monophosphine, and (C) a tetraphosphine having the structure described herein, the contacting conducted in one or more reaction zones and at hydroformylation conditions to produce a blend of normal (N) and iso (I) aldehydes at a N:I ratio, the method comprising at least one of increasing the N:I ratio by adding additional tetraphosphine to a reaction zone; decreasing the N:I ratio by adding additional monophosphine to a reaction zone; or increasing the N:I ratio by volatilization of the free monophosphine.

This invention relates to a method for the conversion of lignocellulosic biomass into ethyl esters of carboxylic acids. Said method consists of treating the biomass material with an oxidizing agent that is incorporated in an solution comprising one or more acids, one or more alcohols and water, and subsequently performing a catalytic reaction at a higher temperature using the same acidic solution into which a larger volume of alcohol is added, in such a way that the catalytic conversion occurs in a medium with a much higher concentration of alcohol, i.e. with a much higher alcohol-to-water wt ratio. Such a method results in relatively high yields of ethyl esters, such as ethyl esters of formic, acetic, and levulinic acids, while producing a low yield of dialkyl ethers, which are unwanted by-products. The concentration of the oxidizing agent in the pre-treatment step is preferably higher than 6.0 wt %. The oxidizing agent is preferably a Fenton or Fenton-type reagent, and most preferably hydrogen peroxide activated by Fe (II), and/or Ti (IV) ions. The alcohol is preferably ethanol, and when ethanol is used, diethyl ether is formed as the unwanted dialkyl ether by-product. Preferably, the biomass material is pelleted before treatment.

This invention relates to a method for the conversion of lignocellulosic biomass into ethyl esters of carboxylic acids. Said method consists of treating the biomass material with an oxidizing agent that is incorporated in an solution comprising one or more acids, one or more alcohols and water, and subsequently performing a catalytic reaction at a higher temperature using the same acidic solution into which a larger volume of alcohol is added, in such a way that the catalytic conversion occurs in a medium with a much higher concentration of alcohol, i.e. with a much higher alcohol-to-water wt ratio. Such a method results in relatively high yields of ethyl esters, such as ethyl esters of formic, acetic, and levulinic acids, while producing a low yield of dialkyl ethers, which are unwanted by-products. The concentration of the oxidizing agent in the pre-treatment step is preferably higher than 6.0 wt %. The oxidizing agent is preferably a Fenton or Fenton-type reagent, and most preferably hydrogen peroxide activated by Fe (II), and/or Ti (IV) ions. The alcohol is preferably ethanol, and when ethanol is used, diethyl ether is formed as the unwanted dialkyl ether by-product. Preferably, the biomass material is pelleted before treatment.

A process for producing levulinic acid includes a step of catalytic conversion of a pentose (in particular xylose or arabinose) into furfural in an organic solvent having a boiling temperature from 60° C. to 220° C., followed by a step of reduction of furfural to furfuryl alcohol, in the presence of a Lewis acid as catalyst and a protic solvent. Eventually, furfuryl alcohol is converted into levulinic acid directly or indirectly, by preliminary conversion into a levulinic acid ester and its subsequent hydrolysis. This process has a reduced environmental impact and guarantees satisfactory process yields on an industrial scale. In particular, the process allows to reduce as much as possible the formation of humins, which require complex and costly purification processes and involve a considerable reduction in the levulinic acid yields.

A process for producing levulinic acid includes a step of catalytic conversion of a pentose (in particular xylose or arabinose) into furfural in an organic solvent having a boiling temperature from 60° C. to 220° C., followed by a step of reduction of furfural to furfuryl alcohol, in the presence of a Lewis acid as catalyst and a protic solvent. Eventually, furfuryl alcohol is converted into levulinic acid directly or indirectly, by preliminary conversion into a levulinic acid ester and its subsequent hydrolysis. This process has a reduced environmental impact and guarantees satisfactory process yields on an industrial scale. In particular, the process allows to reduce as much as possible the formation of humins, which require complex and costly purification processes and involve a considerable reduction in the levulinic acid yields.

An object of the present invention is to provide a method for producing a propionic acid derivative with high productivity. The object can be achieved by a method for producing a compound represented by formula (1):

##STR00001##

wherein R.sup.1 is a halogen atom or the like, R.sup.2 and R.sup.3 are each independently a hydrogen atom, a halogen atom, or an organic group, X is an oxygen atom or a sulfur atom, R.sup.4 and R.sup.5 are each independently a hydrogen atom, a halogen atom, or a hydrocarbon group optionally having one or more substituents, R.sup.E is a hydrocarbon group optionally having one or more substituents; the method comprising step A of reacting a compound represented by formula (2):

##STR00002##

with a compound represented by formula (3):
M(R.sup.1).sub.n, wherein M is a cation, n is an integer corresponding to the valence of M, and a compound represented by formula (4):
R.sup.6—X—H; and
step B of separating, by filtration, the compound represented by formula (5): MF.sub.n from the mixture obtained by the above reaction.

An object of the present invention is to provide a method for producing a propionic acid derivative with high productivity. The object can be achieved by a method for producing a compound represented by formula (1):

##STR00001##

wherein R.sup.1 is a halogen atom or the like, R.sup.2 and R.sup.3 are each independently a hydrogen atom, a halogen atom, or an organic group, X is an oxygen atom or a sulfur atom, R.sup.4 and R.sup.5 are each independently a hydrogen atom, a halogen atom, or a hydrocarbon group optionally having one or more substituents, R.sup.E is a hydrocarbon group optionally having one or more substituents; the method comprising step A of reacting a compound represented by formula (2):

##STR00002##

with a compound represented by formula (3):
M(R.sup.1).sub.n, wherein M is a cation, n is an integer corresponding to the valence of M, and a compound represented by formula (4):
R.sup.6—X—H; and
step B of separating, by filtration, the compound represented by formula (5): MF.sub.n from the mixture obtained by the above reaction.

A catalyst for catalytic oxidation of furfural to prepare maleic acid is composed of a carbon nitride doped with a potassium salt. A method for preparing the catalyst includes mixing the potassium salt, a precursor of the carbon nitride and a solvent to obtain a mixture, and drying and calcining the mixture to obtain the catalyst. A use of the catalyst in catalytic oxidation of furfural to prepare maleic acid, wherein the maleic acid is prepared by the step of oxidizing furfural in a solvent in the presence of the catalyst. The invention has the advantages that by using the method provided by the invention to prepare maleic acid, the conversion rate of furfural can be 99% or more and the yield of maleic acid can be up to 70.40%.