The present invention provides a method for producing indancarbaldehyde, including a step of reacting indan with carbon monoxide in the presence of hydrogen fluoride and boron trifluoride to obtain a reaction liquid including indancarbaldehyde, wherein the indan includes an amine, and a content of the amine is less than 1000 ppm by mass.

Provided is a process for preparing methacrolein which maximizes capture of methanol. Also provided are processes for producing methacrylic acid and methyl methacrylate.

The catalyst solution used in a hydroformylation process is prepared for storage by first reducing its acid concentration and/or water content, and then storing the solution under a blanket of syngas and/or an inert gas. Alternatively, or in addition to, the catalyst solution can be stored with an aqueous buffer comprising materials that will neutralize and/or absorb the acid species within the catalyst solution.

An object of the present invention is to provide a method for producing 2,4-dialkylbenzaldehyde with excellent conversion rate and yield, and excellent regioselectivity for formylation, by allowing carbon monoxide to react on a starting material containing a specific m-dialkylbenzene in the presence of hydrogen fluoride and boron trifluoride. The method for producing 2,4-dialkylbenzaldehyde according to the present invention comprises a step of allowing carbon monoxide to react on a starting material containing m-dialkylbenzene represented by formula (1) in the presence of hydrogen fluoride and boron trifluoride for formylation at least at a position (a), wherein the starting material is a dialkylbenzene containing more than 90 mol % of m-dialkylbenzene represented by formula (1), and the number of moles of boron trifluoride relative to 1 mole of m-dialkylbenzene represented by formula (1) is 0.7 mol or more and 3.0 mol or less:

##STR00001## a wherein R.sup.1 represents an alkyl group having 1 or more and 3 or less carbon atoms, and R.sup.2represents a chain or cyclic alkyl group having 2 or more and 7 or less carbon atoms, with a secondary or tertiary carbon at the benzylic position, provided that the number of carbons of R.sup.2 is larger than the number of carbons of R.sup.1.

An object of the present invention is to provide a method for producing 2,4-dialkylbenzaldehyde with excellent conversion rate and yield, and excellent regioselectivity for formylation, by allowing carbon monoxide to react on a starting material containing a specific m-dialkylbenzene in the presence of hydrogen fluoride and boron trifluoride. The method for producing 2,4-dialkylbenzaldehyde according to the present invention comprises a step of allowing carbon monoxide to react on a starting material containing m-dialkylbenzene represented by formula (1) in the presence of hydrogen fluoride and boron trifluoride for formylation at least at a position (a), wherein the starting material is a dialkylbenzene containing more than 90 mol % of m-dialkylbenzene represented by formula (1), and the number of moles of boron trifluoride relative to 1 mole of m-dialkylbenzene represented by formula (1) is 0.7 mol or more and 3.0 mol or less:

##STR00001## a wherein R.sup.1 represents an alkyl group having 1 or more and 3 or less carbon atoms, and R.sup.2represents a chain or cyclic alkyl group having 2 or more and 7 or less carbon atoms, with a secondary or tertiary carbon at the benzylic position, provided that the number of carbons of R.sup.2 is larger than the number of carbons of R.sup.1.

An object of the present invention is to provide a method for producing 2,4-dialkylbenzaldehyde with excellent conversion rate and yield, and excellent regioselectivity for formylation, by allowing carbon monoxide to react on a starting material containing a specific m-dialkylbenzene in the presence of hydrogen fluoride and boron trifluoride. The method for producing 2,4-dialkylbenzaldehyde according to the present invention comprises a step of allowing carbon monoxide to react on a starting material containing m-dialkylbenzene represented by formula (1) in the presence of hydrogen fluoride and boron trifluoride for formylation at least at a position (a), wherein the starting material is a dialkylbenzene containing more than 90 mol % of m-dialkylbenzene represented by formula (1), and the number of moles of boron trifluoride relative to 1 mole of m-dialkylbenzene represented by formula (1) is 0.7 mol or more and 3.0 mol or less:

##STR00001## a wherein R.sup.1 represents an alkyl group having 1 or more and 3 or less carbon atoms, and R.sup.2represents a chain or cyclic alkyl group having 2 or more and 7 or less carbon atoms, with a secondary or tertiary carbon at the benzylic position, provided that the number of carbons of R.sup.2 is larger than the number of carbons of R.sup.1.

The invention relates to methods of hydrodeoxygenation of oxygenated compounds into compounds with unsaturated carbon-carbon bonds, comprising the steps of: a) providing a reaction mixture comprising, an oxygenated compound containing one or more of a hydroxyl, keto or aldehyde group, an ionic liquid, a homogeneous metal catalyst, and carbon monoxide or a carbon monoxide releasing compound, b) reacting said reaction mixture under a H2 atmosphere at acidic conditions at a temperature between 180 and 250? C. and a pressure between 10 and 200 bar.

The invention relates to methods of hydrodeoxygenation of oxygenated compounds into compounds with unsaturated carbon-carbon bonds, comprising the steps of: a) providing a reaction mixture comprising, an oxygenated compound containing one or more of a hydroxyl, keto or aldehyde group, an ionic liquid, a homogeneous metal catalyst, and carbon monoxide or a carbon monoxide releasing compound, b) reacting said reaction mixture under a H2 atmosphere at acidic conditions at a temperature between 180 and 250? C. and a pressure between 10 and 200 bar.

Nickel-based catalysts comprising silicon modified nickel (nickel silicate) are provided, as are methods for using the catalysts to i) convert methane to CO and H.sub.2 (e.g. for use in synthetic chemical compound production); or to ii) convert methane to oxygenated hydrocarbons e.g. one or more of methanol, acetone, formaldehyde, and dimethyl ether. The catalysts are bifunctional and comprise both Ni metallic catalytic sites and acidic nickel-silicon catalytic sites, and the conversions are performed under moderate reaction conditions.

Nickel-based catalysts comprising silicon modified nickel (nickel silicate) are provided, as are methods for using the catalysts to i) convert methane to CO and H.sub.2 (e.g. for use in synthetic chemical compound production); or to ii) convert methane to oxygenated hydrocarbons e.g. one or more of methanol, acetone, formaldehyde, and dimethyl ether. The catalysts are bifunctional and comprise both Ni metallic catalytic sites and acidic nickel-silicon catalytic sites, and the conversions are performed under moderate reaction conditions.