Methods and phosphorus-containing solid catalysts for catalyzing dehydration of cyclic ethers (e.g., furans, such as 2,5-dimethylfuran) and alcohols (e.g., ethanol and isopropanol). The alcohols and cyclic ethers may be derived from biomass. One example includes a tandem Diels-Alder cycloaddition and dehydration of biomass-derived 2,5-dimethyl-furan and ethylene to renewable p-xylene. The phosphorus-containing solid catalysts are also active and selective for dehydration of alcohols to alkenes.

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.

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.

Provided is a technology for efficiently manufacturing 1,3-butadiene from 1,4-butanediol or 3-buten-1-ol in a reaction condition with a high conversion rate. A catalyst for manufacturing 1,3-butadiene, contains: ytterbium oxide as an active component for generating 1,3-butadiene from 1,4-butanediol or 3-buten-1-ol. In addition, a manufacturing method of 1,3-butadiene, includes: a step of obtaining a fluid containing 1,3-butadiene by bringing at least one of 1,4-butanediol and 3-buten-1-ol into contact with the catalyst for manufacturing 1,3-butadiene.

Provided is a technology for efficiently manufacturing 1,3-butadiene from 1,4-butanediol or 3-buten-1-ol in a reaction condition with a high conversion rate. A catalyst for manufacturing 1,3-butadiene, contains: ytterbium oxide as an active component for generating 1,3-butadiene from 1,4-butanediol or 3-buten-1-ol. In addition, a manufacturing method of 1,3-butadiene, includes: a step of obtaining a fluid containing 1,3-butadiene by bringing at least one of 1,4-butanediol and 3-buten-1-ol into contact with the catalyst for manufacturing 1,3-butadiene.

Provided is a technology for efficiently manufacturing 1,3-butadiene from 1,4-butanediol or 3-buten-1-ol in a reaction condition with a high conversion rate. A catalyst for manufacturing 1,3-butadiene, contains: ytterbium oxide as an active component for generating 1,3-butadiene from 1,4-butanediol or 3-buten-1-ol. In addition, a manufacturing method of 1,3-butadiene, includes: a step of obtaining a fluid containing 1,3-butadiene by bringing at least one of 1,4-butanediol and 3-buten-1-ol into contact with the catalyst for manufacturing 1,3-butadiene.

A method for preparing alpha-methylstyrene according to one embodiment of the present disclosure includes dehydrating a dimethylbenzyl alcohol solution in a reactor under an acid catalyst to prepare alpha-methylstyrene, where a reaction product after the dehydration reaction comprises a first reaction product including a first alpha-methylstyrene; and a second reaction product including vapor (H.sub.2O), a second alpha-methylstyrene and unreacted materials; and separating the second alpha-methylstyrene and the unreacted materials comprised in the second reaction product and recirculating the second alpha-methylstyrene and the unreacted materials to the reactor, a temperature inside the reactor during the dehydration reaction is 135° C. or higher, and a content of the acid catalyst is from 100 ppm to 1,500 ppm based on a total weight of dimethylbenzyl alcohol of the dimethylbenzyl alcohol solution.

A method for preparing alpha-methylstyrene according to one embodiment of the present disclosure includes dehydrating a dimethylbenzyl alcohol solution in a reactor under an acid catalyst to prepare alpha-methylstyrene, where a reaction product after the dehydration reaction comprises a first reaction product including a first alpha-methylstyrene; and a second reaction product including vapor (H.sub.2O), a second alpha-methylstyrene and unreacted materials; and separating the second alpha-methylstyrene and the unreacted materials comprised in the second reaction product and recirculating the second alpha-methylstyrene and the unreacted materials to the reactor, a temperature inside the reactor during the dehydration reaction is 135° C. or higher, and a content of the acid catalyst is from 100 ppm to 1,500 ppm based on a total weight of dimethylbenzyl alcohol of the dimethylbenzyl alcohol solution.

A method for preparing alpha-methylstyrene according to one embodiment of the present disclosure includes dehydrating a dimethylbenzyl alcohol solution in a reactor under an acid catalyst to prepare alpha-methylstyrene, where a reaction product after the dehydration reaction comprises a first reaction product including a first alpha-methylstyrene; and a second reaction product including vapor (H.sub.2O), a second alpha-methylstyrene and unreacted materials; and separating the second alpha-methylstyrene and the unreacted materials comprised in the second reaction product and recirculating the second alpha-methylstyrene and the unreacted materials to the reactor, a temperature inside the reactor during the dehydration reaction is 135° C. or higher, and a content of the acid catalyst is from 100 ppm to 1,500 ppm based on a total weight of dimethylbenzyl alcohol of the dimethylbenzyl alcohol solution.