Michigan State University

The Coca-cola Company

Christopher M Saffron

James E Jackson

Dennis J Miller

Mikhail Y Redko

Chun Ho Lam

Thomas J Pinnavaia

Robert M Kriegel

Shantanu Kelkar

Leo Lacivita

Kyle Matthew Kilponen

Zhenglong Li

A method for hydrolyzing cellulosic material includes combining the cellulosic material with a sulfonated polyaromatic catalyst in water to at least partially hydrolyze the cellulosic material and to form a monosaccharide hydrolysis product, thereby forming a reaction mixture including (i) an aqueous phase with the monosaccharide hydrolysis product in solution therein, and (ii) a dispersed phase including the sulfonated polyaromatic catalyst as well as any non-hydrolyzed cellulosic material. The sulfonated polyaromatic catalyst includes a mixture of partially sulfonated polycyclic aromatic hydrocarbons that is substantially insoluble in the aqueous phase, thus providing it with an affinity for the water-insoluble cellulosic substrate where it preferentially exhibits its catalytic hydrolytic activity. The monosaccharide hydrolysis product can be recovered from the aqueous phase of the reaction mixture.

Methods for cellulose hydrolysis using sulfonated polyaromatic catalysts

The disclosure relates to methods for extracting lignin from lignocellulosic biomass using volatile trialkylamines. A lignocellulosic biomass is combined with an aqueous extraction solution including the trialkylamine and water to provide a biomass extraction mixture that can at least partially extract lignin from the lignocellulosic biomass. The method further includes removing the trialkylamine from the biomass extraction mixture. The method further relates to the utilization of the resulting materials. For example, the lignin extract can be used to make carbon fibers, carbon-carbon materials, or polyamines. The delignified biomass can be used as feed for animals, fungi and/or bacteria. Also, the cellulosic or carbohydrate components of the delignified biomass can be hydrolyzed into pentoses and/or hexoses, which can be used as a feed or starting material for the subsequent conversion into other products. Acetic acid, removed from the biomass in form of trialkylammonium acetate, can be recovered from the mixture for further use or conversion into other chemicals.

Lignin extraction with volatile trialkylamines

The disclosure relates to methods for electrochemical reductive carboxylation of an unsaturated organic substrate to form a dicarboxylic organic product. The unsaturated organic substrate is electrochemically reduced with a carbon dioxide reactant in an ionically conductive, water-immiscible reactant medium to form the dicarboxylic organic product. The dicarboxylic organic product is recovered in an aqueous product medium. Example dicarboxylic organic products include phthalic acid, naphthalenedicarboxylic acid, furan-2,5-dicarboxylic acid, thiophene-2,5-dicarboxylic acid, pyrrole-2,5-dicarboxylic acid, adipic acid, suberic acid, sebacic acid, and 1,12-dodecanedioic acid.

Electrochemical reductive carboxylation of unsaturated organic substrates in ionically conductive mediums

The disclosure relates to methods of forming a dihydrochalcone using electrocatalytic dehydrogenation. In particular, the disclosure relates to methods of forming a dihydrochalcone electrocatalytically hydrogenating (ECH) a reactant compound over a catalytic cathode in a reaction medium having a non-alkaline pH value, thereby forming a dihydrochalcone product; wherein the reactant compound has a structure according to Formula (I). The method can be used to prepare dihydrochalcone sweeteners, such as, for example, naringin dihydrochalcone and neohesperidin dihydrochalcone.

Electrocatalytic synthesis of dihydrochalcones

The disclosure relates to an electrolyzer reactor suitable for the reduction of organic compounds. The reactor includes a membrane electrode assembly with freestanding metallic meshes which serve both as metallic electrode structures for electron transport as well as catalytic surfaces for electron generation and organic compound reduction. Suitable organic compounds for reduction include oxygenated and/or unsaturated hydrocarbon compounds, in particular those characteristic of bio-oil (e.g., alone or a multicomponent mixtures). The reactor and related methods provide a resource- and energy-efficient approach to organic compound reduction, in particular for bio-oil mixtures which can be conveniently upgraded at or near their point of production with minimal or no transportation.

Electrolyzer reactor and related methods

A process and related electrode composition are disclosed for the electrocatalytic hydrogenation and/or hydrodeoxygenation of biomass-derived bio-oil components by the production of hydrogen atoms on a catalyst surface followed by the reaction of the hydrogen atoms with the organic compounds in bio-oil. The catalyst is a metal supported on a monolithic high surface area material such as activated carbon cloth. Electrocatalytic hydrogenation and/or hydrodeoxygenation stabilizes the bio-oil under mild conditions to reduce coke formation and catalyst deactivation. The process converts oxygen-containing functionalities and unsaturated bonds into chemically reduced forms with an increased hydrogen content. The process is operated at mild conditions, which enables it to be a good means for stabilizing bio-oil to a form that can be stored and transported using metal containers and pipes.

Electrocatalytic hydrogenation and hydrodeoxygenation of oxygenated and unsaturated organic compounds

The invention relates to a novel zeolite catalysts, methods of producing the zeolite catalysts and a methods of using such catalyst, including for production of BTEX with improved yield, product selectivity and reduced char production. The present invention relates to novel mesoporous zeolite catalysts, as well as methods of producing the same. The present invention also relates to methods of producing renewable aromatic hydrocarbons using such catalysts.

Mesoporous MFI-zeolite catalysts, methods of preparing the same and uses

A process and related electrode composition are disclosed for the electrocatalytic hydrogenation and/or hydrodeoxygenation of organic substrates such as biomass-derived bio-oil components by the production of hydrogen atoms on a catalyst surface followed by the reaction of the hydrogen atoms with the organic reactants. Biomass fast pyrolysis-derived bio-oil is a liquid mixture containing hundreds of organic compounds with chemical functionalities that are corrosive to container materials and are prone to polymerization. A high surface area skeletal metal catalyst material such as Raney Nickel can be used as the cathode. Electrocatalytic hydrogenation and/or hydrodeoxygenation convert the organic substrates under mild conditions to reduce coke formation and catalyst deactivation. The process converts oxygen-containing functionalities and unsaturated bonds into chemically reduced forms with an increased hydrogen content. The process is operated at mild conditions, which enables it to be a good means for stabilizing bio-oil to a form that can be stored and transported using metal containers and pipes.

Growing community of inventors

Okemos, MI, United States of America

Christopher M Saffron