The Standard Oil Company

Archer Daniels Midland Company

Ineos Europe Ag

Ineos USA LLC

Bp Chemicals Limited

The Standard Oil Company (ohio)

James F Brazdil

Linda C Glaeser

Mark A Toft

Robert K Grasselli

Michael J Seely

Dev D Suresh

Charles James Besecker

Andrew T Guttmann

Joseph Peter Bartek

Raymond G Teller

Chi-Cheng Ma

Robert A Gustaferro

Frances I Ratka

Muin S Haddad

Michael D Ward

Donald Rogness

Alakananda A Bhattacharyya

Christos Paparizos

Bruce I Rosen

Bhagya Chandra Sutradhar

Stephen T McKenna

Richard J George

Ann M Brussee

Steven Alan Cohen

James D Burrington

Maria Strada Friedrich

Claus G Lugmair

Thomas G Attig

Karl O Albrecht

Gerry W Zajac

Chi Cheng Ma

Josh Terrian

William A Marritt

Joseph B Hazen

David A Orndoff

James A Kaduk

Ian R Little

Andrew J Ingram

Steven S Trail

Charles S Lynch

Richard E Hildebrand

John S Hattenberger

Kevin Martin

William J Collins

Sean S-y Lin

Charles J Besecker

Various processes for the pyrolysis of carbohydrates to prepare products such as glycolaldehyde are described. Also, various catalysts and processes for preparing catalysts useful for carbohydrate pyrolysis are described.

Processes for the pyrolysis of carbohydrates

Processes are disclosed for the synthesis of a cracked product or an end product, from a starting compound or substrate having a carbonyl functional group (C═O), with hydroxy-substituted carbon atoms at alpha (α) and beta (β) positions, relative to the carbonyl functional group. According a particular embodiment, an α-, β-dihydroxy carboxylic acid or carboxylate is dehydrated to form a dicarbonyl intermediate by transformation of the α-hydroxy group to a second carbonyl group and removal of the β-hydroxy group. The dicarbonyl intermediate is cracked to form the cracked product, in which the first and second carbonyl groups are preserved. Either or both of (i) the cracked product and (ii) a second cracked product generated from cleavage of a carbon-carbon bond of the dicarbonyl intermediate, may be further converted (e.g., by hydrogenation) to one or more end products, which, like the cracked product(s), also having fewer carbon atoms relative to the dicarbonyl intermediate and substrate.

Dehydration and cracking of alpha-, beta-dihydroxy carbonyl compounds to lactic acid and other products

Improvements in catalyst systems and associated processes for the conversion of glycolaldehyde to monoethanolamine are disclosed. The catalyst systems exhibit improved selectivity to this desired product and consequently reduced selectivity to byproducts such as diethanolamine and ethylene glycol. These beneficial effects are achieved through the use of acids, and particularly Lewis acids, as co-catalysts of the reductive amination reaction, in conjunction with a hydrogenation catalyst.

Processes and catalyst systems for producing monoethanolamine from glycolaldehyde

An integrated, co-product capable process is provided for producing taurine in particular with optionally one or both of monoethanolamine and diethanolamine from one or more sugars, comprising pyrolyzing one or more sugars to produce a crude pyrolysis product mixture including glycolaldehyde and formaldehyde; optionally removing formaldehyde from the crude pyrolysis product mixture, then combining the crude pyrolysis product mixture with an aminating agent in the presence of hydrogen and further in the presence of a catalyst to produce at least monoethanolamine from the crude pyrolysis product mixture; optionally recovering diethanolamine from the crude reductive amination product, sulfating at least a portion to all of the monoethanolamine product to produce 2-aminoethyl hydrogen sulfate ester; and sulfonating the 2-aminoethyl hydrogen sulfate ester to produce taurine.

Process for making biobased products from sugars

Various processes for preparing aldaric acids, aldonic acids, uronic acids, and/or lactone(s) thereof are described. For example, processes for preparing a C-Caldaric acid and/or lactone(s) thereof by the catalytic oxidation of a C-Caldonic acid and/or lactone(s) thereof and/or a C-Caldose are described.

Processes for preparing aldaric, aldonic, and uronic acids

Selective hydrogenation processes are disclosed that can upgrade impure feeds, such as those obtained from biomass and containing a number of small (e.g., 2-6 carbon atom) molecules having aldehyde and/or ketone carbon atoms. For example, whereas glycolaldehyde and its methylated derivative, hydroxyacetone (acetol) are both high value intermediates for certain downstream processing reactions, they are normally recovered in a condensate from pyrolysis of carbohydrates (e.g., aldose-containing sugars) together with glyoxal and its methylated derivative, pyruvaldehyde. The selective hydrogenation of these compounds bearing two carbonyl carbon atoms, without over-hydrogenation to ethylene glycol and propylene glycol, can increase the concentration of the desired intermediates. These beneficial effects of selective hydrogenation may be achieved through the use of a hydrogenation catalyst comprising noble metals such as Ru and Pt.

Processes and catalysts for the selective hydrogenation of compounds having carbonyl carbon atoms

Processes are disclosed for the synthesis of 2-substituted furan derivatives, such as furan dicarboxylic acid (FDCA), from a starting compound or substrate having a carbonyl functional group (C&#x2550;O), with hydroxy-substituted carbon atoms at alpha (&#x3b1;) and beta (&#x3b2;) positions, relative to the carbonyl functional group. According a particular embodiment, an &#x3b1;-, &#x3b2;-dihydroxy carboxylate is dehydrated to form a dicarbonyl intermediate by transformation of the &#x3b1;-hydroxy group to a second carbonyl group and removal of the &#x3b2;-hydroxy group. The dicarbonyl intermediate undergoes cyclization and dehydration, to produce the 2-substituted furan derivative. Optionally, a further step of oxidation may be carried out, for example to convert a hydroxymethyl group, as a 5-substituted about the furan ring, to a carboxy group of FDCA.

Dehydration and cyclization of &#x3b1;-, &#x3b2;-dihydroxy carbonyl compounds to 2-substituted furan derivatives

Processes are disclosed for the synthesis of an &#x3b1;-amino acid or &#x3b1;-amino acid derivative, from a starting compound or substrate having a carbonyl functional group (C&#x2550;O), with hydroxy-substituted carbon atoms at alpha (&#x3b1;) and beta (&#x3b2;) positions, relative to the carbonyl functional group. According a particular embodiment, an &#x3b1;-, &#x3b2;-dihydroxy carboxylic acid or carboxylate is dehydrated to form a dicarbonyl intermediate by transformation of the &#x3b1;-hydroxy group to a second carbonyl group (adjacent a carbonyl group of the starting compound) and removal of the &#x3b2;-hydroxy group. The dicarbonyl intermediate is optionally cracked to form a second, in this case cracked, dicarbonyl intermediate having fewer carbon atoms relative to the dicarbonyl intermediate but preserving the first and second carbonyl groups. Either or both of the dicarbonyl intermediate and the cracked dicarbonyl intermediate may be aminated to convert the second carbonyl group to an amino (&#x2014;NH) group, for producing the corresponding &#x3b1;-amino acid(s).

Dehydration and amination of alpha-, beta-dihydroxy carbonyl compounds to alpha-amino acids

A hydrogenolysis process is disclosed for directly converting a sugar feed comprised of a high fructose feedstock, a high sucrose feedstock, or a combination of these to a mixed lower polyols product including both propylene glycol and ethylene glycol. The process provides greater propylene glycol selectivity than ethylene glycol selectivity such that the propylene glycol is present to a greater extent than the ethylene glycol in the mixed lower polyols product. The sugar feed and a source of hydrogen are supplied to a reaction vessel and reacted in the presence of a hydrogenolysis catalyst comprising molybdenum (Mo) and ruthenium (Ru).

Sugar hydrogenolysis with molybdenum co-catalyst selective for producing glycols

A catalytic composition useful for the conversion of an olefin selected from the group consisting of propylene, isobutylene or mixtures thereof, to acrylonitrile, methacrylonitrile, and mixtures thereof. The catalytic composition comprises a complex of metal oxides comprising bismuth, molybdenum, iron, cerium and other promoters, with a desirable composition.

Selective ammoxidation catalysts

A catalytic composition and process useful for the conversion of an olefin selected from the group consisting of propylene, isobutylene or mixtures thereof, to acrylonitrile, methacrylonitrile, hydrogen cyanide and acetonitrile and mixtures thereof, wherein the catalyst exhibiting increased selectivity to hydrogen cyanide compared to prior art catalysts.

Ammoxidation catalyst with selective co-product HCN production

A catalytic composition useful for the conversion of an olefin selected from the group consisting of propylene, isobutylene or mixtures thereof, to acrylonitrile, methacrylonitrile, and mixtures thereof. The catalytic composition comprises a complex of metal oxides comprising rubidium, bismuth, cerium, molybdenum, iron and other promoters, with a desirable composition.

Mixed metal oxide ammoxidation catalysts

A promoted VPO catalyst for the oxidation of n-butane to maleic anhydride wherein the catalyst comprises the mixed oxides of vanadium and phosphorus, niobium and at least one of antimony and bismuth, wherein the catalyst may be produced in a process comprising impregnating a VPO catalyst with a metal source compound of niobium and a metal source compound of at least one of antimony and bismuth, to form a metal impregnated VPO catalyst, and then drying the metal impregnated VPO catalyst to form the promoted VPO catalyst.

Catalyst for n-butane oxidation to maleic anhydride

Catalytic compositions are provided that are effective for providing increased acrylonitrile product without a significant decrease in hydrogen cyanide and/or acetonitrile production and provide an overall increase in production of acrylonitrile, hydrogen cyanide and acetonitrile. The catalytic compositions include a complex of metal oxides and include at least about 15% m-phase plus t-phase by weight and have a weight ratio of m-phase to m-phase plus t-phase of 0.45 or greater.

Mixed metal oxide catalysts

Growing community of inventors

Mayfield Village, OH, United States of America

James F Brazdil