The Dow Chemical Company

Micromidas, Inc.

Dow Agrosciences LLC

Dennis A. Hucul

Dennis A Hucul

Makoto Nathanael Masuno

Ryan L Smith

Dimitri A Hirsch-Weil

John Bissell

Alex Benjamin Wood

Daniel Randolph Henton

Patrick B Smith

Katherine Brune

Stephen F Hahn

Robert Joseph Araiza

Edmund J Stark

Craig B Murchison

Shawn M Browning

John Albert Bissell, Ii

Douglas Cannon

Robert T Klun

Richard E Campbell, Jr

David Craig Molzahn

Juan M Garces

Paul C Vosejpka

Guo-shuh J Lee

Kenneth A Burdett

Rex R Stevens

James William Ringer

Edward M Calverley

Robert M Campbell

Gregory F Schmidt

Larry N Ito

Bob R Maughon

Avani Maulik Patel

Jonathan H Siddall

Kathryn A Eickholt

Tracy L Young

Adina Dumitrascu

John A Bissell

Provided herein are methods of producing dialkylfurans, such as 2,5-dimethylfuran, and other alkyl furans, such as 2-methylfuran. For example, 2,5-dimethylfuran may be produced by reducing (5-methylfuran-2-yl)methanol or 2-(chloromethyl)-5-methylfuran.

Methods of producing alkylfurans

The present disclosure provides methods to produce para-xylene, toluene, and other compounds from renewable sources (e.g., cellulose, hemicellulose, starch, sugar) and ethylene in the presence of a catalyst. For example, cellulose and/or hemicellulose may be converted into 2,5-dimethylfuran (DMF), which may be converted into para-xylene by cycloaddition of ethylene to DMF. Para-xylene can then be oxidized to form terephthalic acid.

Methods of producing para-xylene and terephthalic acid

The present disclosure provides methods to produce para-xylene, toluene, and other compounds from renewable sources (e.g., cellulose, hemicellulose) and ethylene in the presence of an acid, such as a Lewis acid. For example, cellulose and/or hemicellulose may be converted into 2,5-dimethylfuran (DMF) and 2-methylfuran, which may be converted into para-xylene and toluene, respectively. In particular, para-xylene can then be oxidized to form terephthalic acid.

Provided herein are methods of producing dialkylfurans, such as 2,5-dimethylfuran, and other alkyl furans, such as 2-methylfuran. For example, 2,5-dimethylfuran may be produced by hydrogenation of (5-methylfuran-2-yl) methanol or 2-(chloromethyl)-5-methylfuran in the presence of a solid supported metal catalyst having an excess of either basic or acidic sites (as determined by chemisorption of CO2 or NH3). The process could further include a urea reagent (TMU, DMPU, TMI) and an alkyl benzene.

Methods of producing para-xylene

A hydrogenation catalyst and a process for hydrogenating an unsaturated polymer comprising contacting the unsaturated polymer with a hydrogenating agent in the presence of a mixed hydrogenation catalyst, characterized in that the mixed hydrogenation catalyst comprises a Group VIII metal component and at least one component selected from the group consisting of a rhenium, molybdenum, tungsten, tantalum and niobium component.

Process for hydrogenating unsaturated polymers

The present invention is a continuous process for hydrogenating an unsaturated polymer comprising: contacting the unsaturated polymer with a hydrogenating agent in a fixed bed reactor, wherein the reactor is packed with a hydrogenation catalyst characterized in that the hydrogenation catalyst comprises a Group VIII metal component and at least one deactivation resistant component.

The present invention is directed to a hydrogenation catalyst and a process for hydrogenating an aromatic polymer having a number average molecular weight (Mn) of from 40,000 to less than 120,000 comprising contacting the aromatic polymer with a hydrogenating agent in the presence of a silica supported metal hydrogenation catalyst, characterized in that the silica has a pore size distribution such that at least 95 percent of the pore volume is defined by pores having diameter from 300 to 1000 angstroms, less than 4 percent of the pore volume is defined by pores having a diameter of 200 angstroms or less and at least 80 percent aromatic hydrogenation is achieved.

Process for hydrogenating aromatic polymers

A process for making 2,3-dihalopropanol including reacting 2,3-dihalopropanal with a hydrogenating agent in the presence of an iridium and a second transition metal mixed metal catalyst where the second transition metal is selected from the group comprising ruthenium, iron, molybdenum, tungsten, rhenium, osmium, manganese or vanadium, under conditions such that 2,3-dihalopropanol is formed. The 2,3-dihalopropanol is particularly useful in a process for making epihalohydrin.

Process for making 2,3-dihalopropanols

Aliphatic primary alcohols, including aliphatic primary alcohols possessing one or more oxygen, nitrogen and/or phosphorus heteroatoms that may be atoms substituting for carbon atoms in the alkyl group or component atoms of substituents on the alkyl group, were converted into salts of carboxylic acids by contacting an alkaline aqueous solution of the primary alcohol with a catalyst comprising cobalt, copper, and at least one of cerium, iron, zinc, and zirconium. Diethanolamine, for example, was converted to sodium iminodiacetate by treatment in an aqueous medium containing sodium hydroxide with a catalyst that was obtained by reducing a mixture of cobalt, copper, and zirconium oxides with hydrogen.

Process for preparing carboxylic acids

The present invention is a process of hydrogenating high molecular weight aromatic polymers comprising hydrogenating the high molecular weight aromatic polymer in the presence of a silica supported metal hydrogenation catalyst, characterized in that the silica has a pore size distribution such that at least 98 percent of the pore volume is defined by pores having diameter of greater than 600 angstroms.

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Midland, MI, United States of America

Dennis A Hucul