Archer Daniels Midland Company

Dupont Industrial Biosciences Usa, LLC

Archer Daniels Wudland Company

E. I. Du Pont De Nemours

Alexandra Sanborn

Stephen J Howard

Paul D Bloom

Erik Christopher Hagberg

Brennan Alexander Smith

Erin Rockafellow

Stephen Howard

Kevin M Moore

Erik Hagberg

Kenneth Stensrud

Kristina Ann Kreutzer

Bhuma Rajagopalan

Eric R Sacia

Erin M Rockafellow

Joshua Terrian

Thomas P Binder

Ahmad K Hilaly

John Glenn Soper

Mark W Empie

Mitchell J Schultz

William Chris Hoffman

Pam Anklam

John G Soper

A process is provided for making esters of FDCA, in which an aqueous feed comprising glucaric acid is first reacted with a high boiling first alcohol in the presence of an acid catalyst and with removing water during the reaction, to form a first product mixture comprising a first ester of FDCA and the high boiling first alcohol, then unreacted high boiling first alcohol is removed from the first product mixture. The first ester of FDCA and the high boiling first alcohol is then transesterified with a lower boiling second alcohol selected from the group consisting of methanol, ethanol, isopropanol and n-propanol, to form a second product mixture comprising a second ester of FDCA with the lower boiling second alcohol, and the second ester of FDCA with the lower boiling second alcohol is recovered.

Process for making esters of 2,5-furandicarboxylic acid

An integrated process is useful for producing 2,5-furandicarboxylic acid (FDCA) and/or a derivative thereof from a six-carbon sugar-containing feed. The process includes a) dehydrating a feed containing a six-carbon sugar unit, in the presence of a bromine source and of a solvent, to generate an oxidation feed that contains at least one of 5-hydroxymethylfurfural (HMF) and/or a derivative or derivatives of HMF in the solvent, together with at least one bromine containing species; b) contacting the oxidation feed from step (a) with a metal catalyst and with an oxygen source under oxidation conditions to produce an oxidation product mixture of at least FDCA and/or a derivative thereof, the solvent, and a residual catalyst; c) purifying and separating the mixture obtained in step (b) to obtain FDCA and/or a derivative thereof and the solvent; and d) recycling at least a portion of the solvent obtained in step (c) to step (a).

Processes for producing 2,5-furandicarboxylic acid and derivatives thereof and polymers made therefrom

An integrated process is useful for producing 2,5-furandicarboxylic acid (FDCA) and/or a derivative thereof from a six-carbon sugar-containing feed. The process includes a) dehydrating a feed containing a six-carbon sugar unit, in the presence of a bromine source and of a solvent, to generate an oxidation feed that contains at least one of 5-hydroxymethylfurfural (HMF) and/or a derivative or derivatives of HMF in the solvent, together with at least one bromine containing species; b) contacting the oxidation feed from step (a) with a metal catalyst and with an oxygen source under oxidation conditions to produce an oxidation product mixture of at least FDCA and/or a derivative thereof, the solvent, and a residual catalyst: c) purifying and separating the mixture obtained in step (b) to obtain FDCA and/or a derivative thereof and the solvent; and d) recycling at least a portion of the solvent obtained in step (c) to step (a).

An integrated process is described for producing 2,5-furandicarboxylic acid and/or a derivative thereof from a six carbon sugar-containing feed, comprising: a) dehydrating a feed comprising a six-carbon sugar unit, in the presence of a bromine source and of a solvent, to generate an oxidation feed comprised of at least one of 5-hydroxymethylfurfural and/or a derivative or derivatives of 5-hydroxymethylfurfural in the solvent, together with at least one bromine containing species; b) contacting the oxidation feed from step (a) with a metal catalyst and with an oxygen source under oxidation conditions to produce an oxidation product mixture comprising 2,5-furandicarboxylic acid (FDCA) and/or a derivative thereof, the solvent, and a residual catalyst; c) purifying and separating the mixture obtained in step (b) to obtain FDCA and/or a derivative thereof and the solvent; and d) recycling at least a portion of the solvent obtained in step (c) to step (a).

A process is described for converting hydroxymethylfurfural to furanic products inclusive of 2,5-furandicarboxylic acid, comprising combining a quantity of hydroxymethylfurfural with water to provide an aqueous solution containing at least about five percent by weight of hydroxymethylfurfural, and combining the aqueous solution with an oxygen source in the presence of a heterogeneous ruthenium-based catalyst and under conditions which are effective for oxidizing hydroxymethylfurfural to furanic oxidation products inclusive of 2,5-furandicarboxylic acid, but in the substantial absence of any solvent for either hydroxymethylfurfural or 2,5-furandicarboxylic acid other than water.

Catalyst and process for producing 2,5-furandicarboxylic acid from hydroxymethylfurfural in water

A process for preparing cyclic dehydration products from sugar alcohols is described. The process involve using a mixed-acid catalyst reaction mixture containing a reducing acid, having a pKa of about 1.0-1.5, and at least a strong Br&#xf8;nsted acid or a Lewis acid, having a pKa&#x2266;0, or both acids in a solution to dehydrate and ring close said sugar alcohol. Synergistically, the mixed-acid catalysis can produce greater amounts of the desired product at similar levels of compositional accountability than either of the component acid catalysts acting alone.

Phosphonic acid catalyst in dehydrative cyclization of 5 and 6 carbon polyols with improved color and product accountability

Methods of making reduced derivatives of hydroxymethyl furfural using metal catalysts are described. The derivatives may have tetrahydrofuran or furan nucleus with alkoxymethyl ether or ester moieties on the 5' carbon and methanol on the 2&#x2032; carbon. Suitable metal catalyst include Raney nickel, a nickel catalyst with a zirconium promoter, a chromite catalyst with a barium, a palladium catalyst, such as palladium on carbon, or a ruthenium catalyst. Also provided are a new class of compounds, which are n-alkoxy hexane diols (i.e., 1,2 or 1,5 hexane diol ethers) and methods of making the same by reduction of furan or tetrahydrofuran derivatives.

Reduction of HMF ethers with metal catalyst

Disclosed is a process for making HMF or a derivative of HMF by dehydrating one or more hexose sugars in a reduced oxygen environment. In another, related aspect, a method for improving the stability and resistance to degradation of an HMF product involves adding one or more antioxidants to the HMF product.

Process for making HMF from sugars with reduced byproduct formation, and improved stability HMF compositions

A process is described for converting HMF to FDCA, comprising dissolving a quantity of HMF in water to form an aqueous solution including HMF, combining the aqueous solution including HMF with an oxygen source in the presence of a homogeneous metal salt catalyst, but in the substantial absence of any solvent for the HMF and the homogeneous metal salt catalyst other than water, and under conditions which are effective for oxidizing HMF in the presence of the catalyst to form FDCA, and then recovering an FDCA precipitate.

Process for making 2,5-furandicarboxylic acid

Disclosed is a process for making HMF' or a derivative of HMF by dehydrating one or more hexose sugars in a reduced oxygen environment, in another, related aspect, a method for improving the stability and resistance to degradation of an HMF product Involves adding one or more antioxidants to the HMF product.

A process is described for producing an isohexide wherein an hexitol or a combination of hexitols is continuously dehydrated in the presence of an acid catalyst under vacuum using a thin film evaporator.

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Lincoln, IL, United States of America

Alexandra Sanborn