Archer Daniels Midland Company

Washington State University

Kevin J Martin

Padmesh Venkitasubramanian

Yong Wang

Changjun Liu

Junming Sun

Chi-Cheng Ma

Josh Terrian

Colin Smith

Erik Christopher Hagberg

Paul D Bloom

Kenneth Stensrud

Brennan Alexander Smith

Joshua Terrian

Bethanie Platt

Jerome Le Notre

Daniel Stephan Van Es

Jan Van Ee

Leandra Vircks

A process is described for producing 1,3-butanediol, wherein an ester of poly-(R)-3-hydroxybutyrate such as formed by transesterification with an alcohol is reduced by hydrogenation in the presence of a skeletal copper-based catalyst to provide 1,3-butanediol. The 1,3-butanediol may be transesterified by reaction with additional poly-(R)-3-hydroxybutyrate ester to produce (R)-3-hydroxybutyl (R)-3-hydroxybutyrate.

Process for producing 1,3-butanediol and for optionally further producing (R)-3-hydroxybutyl (R)-3-hydroxybutyrate

Wholly biobased MTBE and ETBE fuel additive materials are described, together with fuel compositions including such additives and processes for making the wholly biobased MTBE and ETBE using isobutene prepared from acetic acid in the presence of a ZnZrOmixed oxide catalyst.

Process for making biobased fuel additives

Copper-containing, multimetallic catalysts with either a zirconia or carbon support are described which have improved utility for the hydrogenolysis of a glycerol or glycerol-containing feedstock to provide a biobased 1,2-propanediol product. specially, improved carbon-supported examples of such catalysts are described for this reaction as well as for other processes wherein hydrogen is used, with methods for maintaining the activity of these catalysts. Related treatment methods in the preparation of these improved catalysts enable the use of carbons with a desired mechanical strength but which previously lacked activity, for example, for the conversion of a glycerol or glycerol-containing feed to produce 1,2-propanediol, so that copper-containing, multi-metallic catalysts may be employed for making a biobased propylene glycol using carbon supports that previously would have not been suitable.

Copper-containing multimetallic catalysts, and method for using the same to make biobased 1,2-propanediol

Disclosed herein are methods for synthesizing 1,2,5,6-hexanetetrol (HTO), 1,6 hexanediol (HDO) and other reduced polyols from C5 and C6 sugar alcohols or R glycosides. The methods include contacting the sugar alcohol or R-glycoside with a copper catalyst, most desirably a Raney copper catalyst with hydrogen for a time, temperature and pressure sufficient to form reduced polyols having 2 to 3 fewer hydoxy groups than the starting material. When the starting compound is a C6 sugar alcohol such as sorbitol or R-glycoside of a C6 sugar such as methyl glucoside, the predominant product is HTO. The same catalyst can be used to further reduce the HTO to HDO.

Synthesis of R-glucosides, sugar alcohols, reduced sugar alcohols, and furan derivatives of reduced sugar alcohols

Processes are described for making biobased isoprene, wherein a biobased isobutene prepared from acetic acid in the presence of a catalyst is combined with a formaldehyde source to form a reaction mixture, and the reaction mixture is reacted to yield biobased isoprene. In certain embodiments, methyl-tert-butyl ether prepared by reacting the same biobased isobutene with methanol serves as a formaldehyde source, being oxidatively cracked to produce formaldehyde as well as isobutene for being converted to the biobased isoprene.

Process for making biobased isoprene

Processes are described for making methacrylic acid via methacrolein from a biobased isobutene, wherein the biobased isobutene is prepared from ethanol or from acetic acid in the presence of a ZnZrOmixed oxide catalyst, the biobased isobutene is oxidized to methacrolein and the methacrolein is further oxidized to methacrylic acid.

Processes for making methacrylic acid

A process is disclosed for converting acetic acid to isobutene in the presence of a catalyst. In certain embodiments, a ZnZrOmixed oxide catalyst is used for carrying out a gas phase process for converting acetic acid to isobutene. In some embodiments, a ZnZrOmixed oxide catalyst made by an incipient wetness impregnation method is used and is indicated to be very stable for carrying out the conversion.

Process and catalyst for conversion of acetic acid to isobutene

A process is disclosed for converting acetic acid to propylene and isobutene as the principal hydrocarbon products made, in the presence of a catalyst and in the further presence of hydrogen. In certain embodiments, a ZnZrOmixed oxide catalyst is used for carrying out a gas phase process, and propylene is produced preferentially to isobutene by using at least a certain amount of hydrogen in the process. In some embodiments, a ZnZrOmixed oxide catalyst made by an incipient wetness impregnation method is used and is indicated to be very stable for carrying out the conversion.

Process and catalyst for conversion of acetic acid to isobutene and propylene

A process is described for making renewable para-xylene, comprising converting acetic acid to isobutene in the presence of a catalyst then converting the acetic acid-derived isobutene to a product composition including para-xylene. The catalyst can be a ZnZrOmixed oxide catalyst.

Renewable para-xylene from acetic acid

A process is described for making renewable isobutene and renewable isoprene, comprising converting a mixed acid feed including acetic acid and propionic acid to a product mixture including isobutene and at least one or both of 2-methyl-1-butene and 2-methyl-2-butene in the presence of a catalyst, separating isobutene from the product mixture and dehydrogenating either or both of the 2-methyl-1-butene and 2-methyl-2-butene in the remainder to provide isoprene.

Renewable isobutene and isoprene from a mixture of acetic acid and propionic acid

Disclosed is a process for the preparation of isoidide from isosorbide. An aqueous solution of isosorbide is subjected to epimerization in the presence of hydrogen under the influence of a catalyst comprising ruthenium on a support, preferably a carbon support. The process of the invention can be conducted using a relatively low hydrogen pressure, and leads to a desired distribution of epimers, favoring isoidide over isomannide and isosorbide.

Method of making isoidide

A hydrogenation catalyst comprising nickel, rhenium, and cadmium is disclosed. Process of using hydrogenation catalyst for producing propylene glycol from polyol feedstock are also disclosed. The present invention relates generally to catalysts and more particularly, to catalysts having an enhanced ability to produce propylene glycol from sugar alcohols while reducing the production of by-products.

Hydrogenolysis catalysts and uses thereof

A process is described for making a product mixture including isobutene, propylene, 1-butene, 2-butene, 2-methyl-1-butene and 2-methyl-2-butene from a mixture of acetic acid and propionic and through reaction in the presence of a source of hydrogen and of a mixed oxide catalyst, for example, a ZnZrOmixed oxide catalyst. A variety of commercially valuable products may be made in turn from the various C, Cand Cconstituents of the product mixture.

Renewable olefins from a mixture of acetic acid and propionic acid

Processes are described for improved utilization of the byproduct acetic acid universally produced in various oxidative processes for making acrylic acid and methacrylic acid, wherein at least a portion of the byproduct acetic acid is converted to isobutene and optionally to one or more further value-added products which may be prepared from isobutene.

Growing community of inventors

Mt. Zion, IL, United States of America

Kevin J Martin