Battelle Memorial Institute

Archer Daniels Midland Company

Other

Michigan State University

Todd A Werpy

John G Frye

Alan H Zacher

Yong Wang

Johnathan E Holladay

James F White

Dennis J Miller

Michael A Lilga

Bruce F Monzyk

Jianli Hu

Satya P Chauhan

Kevin Lynn Simmons

Charles Abbas

Thomas Peterson

Chi-Cheng Ma

Michel J Gray

Gary G Neuenschwander

William D Samuels

Andrew J Schmidt

Kyle E Beery

James A Franz

Rick J Orth

H Nicholas Conkle

Anne M Rammelsberg

Mikhail S Alnajjar

Sara F Kuczek

Eric V Alderson

Catherine J Kim

James E Jackson

Douglas Charles Elliott

Richard T Hallen

John L Fulton

Dean W Matson

John C Linehan

Shubham P Chopade

Roger M Bean

Xinjie Zhang

John G Darab

Carlos Gustavo Dassori

Douglas C Elliot

Thomas D Brewer

John G Frey, Jr

Nicholas H Conkle

A process is described for improving the performance of certain multiphase reaction systems including a solid catalyst, one or more reactants in the gas phase and one or more reactants in the liquid phase, wherein a targeted maximum concentration of a reactant in the liquid phase is identified for providing improved value in terms of byproduct formation, catalyst deactivation and yields of desired products, and this targeted concentration is closely approached and preferably achieved, but not substantially exceeded, downstream in a continuous process or later in time from the initiation of a batch in a semibatch mode of operation of such processes.

Multiphase low mixing processes

An improved process for making bioderived propylene glycol from a feed composition including at least one of lactic acid, glycerol, a five carbon sugar, a five carbon sugar alcohol, a six carbon sugar and a six carbon sugar alcohol, wherein production of four carbon and higher diols is reduced by adding base after the initiation of the reaction. In preferred embodiments, the process pH and other process conditions are initially established at targeted values for obtaining the highest conversion for a given catalyst consistent with the production of substantially no pentanediol byproducts in the product mixture, and base is added thereafter to control the process pH proximate to the initially targeted value.

Process of making bioderived propylene glycol

The invention includes methods of processing an initial di-carbonyl compound by conversion to a cyclic compound. The cyclic compound is reacted with an alkylating agent to form a derivative having an alkylated ring nitrogen. The invention encompasses a method of producing an N-alkyl product. Ammonia content of a solution is adjusted to produce a ratio of ammonia to di-carboxylate compound of from about 1:1 to about 1.5:1. An alkylating agent is added and the initial compound is alkylated and cyclized. The invention includes methods of making N-methyl pyrrolidinone (NMP). Aqueous ammonia and succinate is introduced into a vessel and ammonia is adjusted to provide a ratio of ammonia to succinate of less than 2:1. A methylating agent is reacted with succinate at a temperature of from greater than 100&#xb0; C. to about 400&#xb0; C. to produce N-methyl succinimide which is purified and hydrogenated to form NMP.

Process for producing cyclic compounds

A method of reducing hydroxymethylfurfural (HMF) where a starting material containing HMF in a solvent comprising water is provided. His provided into the reactor and the starting material is contacted with a catalyst containing at least one metal selected from Ni, Co, Cu, Pd, Pt, Ru, Ir, Re and Rh, at a temperature of less than or equal to 250&#xb0; C. A method of hydrogenating HMF includes providing an aqueous solution containing HMF and fructose. Hand a hydrogenation catalyst are provided. The HMF is selectively hydrogenated relative to the fructose at a temperature at or above 30&#xb0; C. A method of producing tetrahydrofuran dimethanol (THFDM) includes providing a continuous flow reactor having first and second catalysts and providing a feed comprising HMF into the reactor. The feed is contacted with the first catalyst to produce furan dimethanol (FDM) which is contacted with the second catalyst to produce THFDM.

Hydroxymethylfurfural reduction methods and methods of producing furandimethanol

The invention includes methods of processing an initial di-carbonyl compound by conversion to a cyclic compound. The cyclic compound is reacted with an alkylating agent to form a derivative having an alkylated ring nitrogen. The invention encompasses a method of producing an N-alkyl product. Ammonia content of a solution is adjusted to produce a ratio of ammonia to di-carboxylate compound of from about 1:1 to about 1.5:1. An alkylating agent is added and the initial compound is alkylated and cyclized. The invention includes methods of making N-methylpyrrolidinone (NMP). Aqueous ammonia and succinate is introduced into a vessel and ammonia is adjusted to provide a ratio of ammonia to succinate of less than 2:1. A methylating agent is reacted with succinate at a temperature of from greater than 100&#xb0; C. to about 400&#xb0; C. to produce N-methyl succinimide which is purified and hydrogenated to form NMP.

Chemical production processes are provided that can include exposing a reactant composition to a catalyst composition to form a product composition. Catalyst compositions are also provided that can include metal phosphate compositions, metal phosphorous compositions, and/or solid support compositions with the solid support compositions including one or more of F&#x2014;AlO, ZrO&#x2014;CO, SiO&#x2014;AlO&#x2014;CO, SiOAlO, Alundum, and Silica such as Ludox AS-30.

Chemical production processes, systems, and catalyst compositions

Chemical production processes are provided that can include exposing a reactant composition to a catalyst composition to form a product composition. The reactant composition can include a multihydric alcohol compound and the product composition can include a carbonyl compound. The catalyst composition can include a metal effective to facilitate catalyst activation. Processes disclosed also include supplementing a dehydration catalyst with a promoter, and activating the supplemented catalyst in the presence of oxygen. Processes also include providing a supplemented dehydration catalyst to within a reactor, and exposing a multihydric alcohol compound to the dehydration catalyst, with the exposing forming coke within the reactor. Oxygen can be provided to the reactor to remove at least a portion of the coke.

A textured catalyst having a hydrothermally-stable support, a metal oxide and a catalyst component is described. Methods of conducting aqueous phase reactions that are catalyzed by a textured catalyst are also described. The invention also provides methods of making textured catalysts and methods of making chemical products using a textured catalyst.

Methods of making textured catalysts

The invention includes methods of processing plant material by adding water to form a mixture, heating the mixture, and separating a liquid component from a solid-comprising component. At least one of the liquid component and the solid-comprising component undergoes additional processing. Processing of the solid-comprising component produces oils, and processing of the liquid component produces one or more of glycerol, ethylene glycol, lactic acid and propylene glycol. The invention includes a process of forming glycerol, ethylene glycol, lactic acid and propylene glycol from plant matter by adding water, heating and filtering the plant matter. The filtrate containing starch, starch fragments, hemicellulose and fragments of hemicellulose is treated to form linear poly-alcohols which are then cleaved to produce one or more of glycerol, ethylene glycol, lactic acid and propylene glycol. The invention also includes a method of producing free and/or complexed sterols and stanols from plant material.

Methods of producing compounds from plant materials

The invention includes methods of producing dianhydrosugars. A polyol is reacted in the presence of a first catalyst to form a monocyclic sugar. The monocyclic sugar is transferred to a second reactor where it is converted to a dianhydrosugar alcohol in the presence of a second catalyst. The invention includes a process of forming isosorbide. An initial reaction is conducted at a first temperature in the presence of a solid acid catalyst. The initial reaction involves reacting sorbitol to produce 1,4-sorbitan, 3,6-sorbitan, 2,5-mannitan and 2,5-iditan. Utilizing a second temperature, the 1,4-sorbitan and 3,6-sorbitan are converted to isosorbide. The invention includes a method of purifying isosorbide from a mixture containing isosorbide and at least one additional component. A first distillation removes a first portion of the isosorbide from the mixture. A second distillation is then conducted at a higher temperature to remove a second portion of isosorbide from the mixture.

Method of forming a dianhydrosugar alcohol

The invention includes methods for producing dianhydrosugar alcohol by providing an acid catalyst within a reactor and passing a starting material through the reactor at a first temperature. At least a portion of the staring material is converted to a monoanhydrosugar isomer during the passing through the column. The monoanhydrosugar is subjected to a second temperature which is greater than the first to produce a dianhydrosugar. The invention includes a method of producing isosorbide. An initial feed stream containing sorbitol is fed into a continuous reactor containing an acid catalyst at a temperature of less than 120&#xb0; C. The residence time for the reactor is less than or equal to about 30 minutes. Sorbitol converted to 1,4-sorbitan in the continuous reactor is subsequently provided to a second reactor and is dehydrated at a temperature of at least 120&#xb0; C. to produce isosorbide.

Two-stage dehydration of sugars

Textured catalysts and methods of making textured catalysts

A nontoxic deicing/anti-icing fluid includes a biobased freezing point depressant, a surfactant, an antioxidant, and water. The fluid has an LDgreater than about 10,000 mg/L. Another deicing/anti-icing fluid includes a biobased freezing point depressant, a vinylpyrrolidone polymer having a molecular weight between about 10,000 and about 700,000, and water. Another deicing/anti-icing fluid includes a biobased freezing point depressant, a nonionic surfactant selected from the polyoxyalkylene ethers, an antioxidant, and water. Another deicing/anti-icing fluid includes a biobased freezing point depressant, a surfactant, a food grade material that functions as an antioxidant, and water. A further deicing/anti-icing fluid includes a biobased freezing point depressant, a material that functions as both a buffer and a freezing point depressant, and water.

Biobased deicing/anti-icing fluids

Growing community of inventors

West Richland, WA, United States of America

Todd A Werpy