Akzo Nobel N.v.

Battelle Memorial Institute

Supresta U.S. LLC

Zongchao C Zhang

Shuguang Zhang

Dale Steichen

James F Gadberry

Johnathan E Holladay

Haibo Zhao

Anantha Narayanan Desikan

Heather M Brown

Alan J Abramson

Yu Su

James Liang

Methods are described for conversion of carbohydrate polymers in ionic liquids, including cellulose, that yield value-added chemicals including, e.g., glucose and 5-hydroxylmethylfurfural (HMF) at temperatures below 120&#xb0; C. Catalyst compositions that include various mixed metal halides are described that are selective for specified products with yields, e.g., of up to about 56% in a single step process.

Method for conversion of carbohydrate polymers to value-added chemical products

Methods are described for converting carbohydrates including, e.g., monosaccharides, disaccharides, and polysaccharides in ionic liquids to value-added chemicals including furans, useful as chemical intermediates and/or feedstocks. Fructose is converted to 5-hydroxylmethylfurfural (HMF) in the presence of metal halide and acid catalysts. Glucose is effectively converted to HMF in the presence of chromium chloride catalysts. Yields of up to about 70% are achieved with low levels of impurities such as levulinic acid.

Methods for conversion of carbohydrates in ionic liquids to value-added chemicals

The present invention generally relates to a process for the arylation of unsaturated linear fatty acids and/or alkyl esters thereof to their aryl branched counterparts. Said arylation process comprises contacting said unsaturated linear fatty acids and/or alkyl esters thereof and one or more aromatic compounds with at least one metal ion exchanged solid material catalyst. The invention also relates to various derivatives prepared from the aryl branched fatty acids and/or alkyl esters prepared in accordance with the present invention.

Arylation and the skeletal isomerization of fatty acid and alkyl esters thereof using metal ion exchanged solid materials as catalyst

A branched composition can be formed by reacting a reagent containing a saturated hydrocarbon moiety in the presence of (a) a catalyst capable of activating a carbon-hydrogen bond therein and (b) a branching reagent having a moiety that binds to the carbon atom in the carbon-hydrogen bond upon extraction of the hydrogen atom from that carbon-hydrogen bond. Suitable catalysts are those that comprise a transition metal cation possessing multiple oxidation states that is embedded in an anion that is a transition metal oxide possessing a higher oxidation state for the metal therein than the metal in the cation.

Process for forming branched composition catalytically by carbon-hydrogen bond activation in a saturated moiety

The present invention generally relates to a process for the skeletal isomerization of unsaturated linear fatty acids and/or alkyl esters thereof to their branched counterparts. Said skeletal isomerization process comprises contacting said unsaturated linear fatty acids and/or alkyl esters thereof with at least one metal ion exchanged solid material catalyst. The present invention also relates to a process for the preparation of branched fatty acids and/or alkyl esters thereof from their straight chain counterparts. Finally, the invention also relates to various derivatives prepared from the branched fatty acids and/or alkyl esters prepared in accordance with the present invention.

Metal ion exchanged solid materials as catalysts for the skeletal isomerization of fatty acids and alkyl esters thereof

A process for the alkylation of triphenylphosphate by reaction of triphenylphosphate with an olefin in the presence of an effective amount of a solid acid catalyst selected from the group consisting of at least one zeolite, heteropolyacid or salt thereof, metal triflate, non-aryl group-containing metal sulfonic acid, metal halide Lewis acid, or compatible mixture of any such catalyst.

Alkylation of triphenylphosphate

The present invention relates to a process for the skeletal isomerization of unsaturated linear fatty acids to branched fatty acids which comprises contacting said unsaturated linear fatty acids with at least one large pore zeolite catalyst wherein said at least one zeolite catalyst comprises a material having a three dimensional channel structure having a pore diameter of at least 6.0 &#x212b;. In another embodiment, the invention relates to a process for the skeletal isomerization and hydrogenation of unsaturated linear fatty acids to saturated branched fatty acids which comprises contacting said unsaturated linear fatty acids in the presence of an acidic catalyst, wherein said acidic catalyst comprises a mesoporous crystalline phase having pore walls containing primary and secondary crystalline building unit structures.

Skeletal isomerization of alkyl esters and derivatives prepared therefrom

The present invention relates to a process for the skeletal isomerization of unsaturated linear fatty acids to branched fatty acids which comprises contacting said unsaturated linear fatty acids with at least one large pore zeolite catalyst wherein said at least one zeolite catalyst comprises a material having a three dimensional channel structure having a pore diameter of at least 6.0 &angst;. In another embodiment, the invention relates to a process for the skeletal isomerization and hydrogenation of unsaturated linear fatty acids to saturated branched fatty acids which comprises contacting said unsaturated linear fatty acids with at least one metal-zeolite catalyst.

Skeletal isomerization of fatty acids

A metal oxide is treated with an organophosphate, such as a trialkyl phosphate, to convert the oxide to the corresponding phosphate. The metal in the oxide can be a transition metal, such as iron, and the trialkyl phosphate preferably contains from one to about four carbon atoms in each alkyl group. The treatment can be conducted at an elevated temperature of about 250.degree. C. or greater.

Conversion of metal oxide to metal phosphate

The durability and selectivity of a supported nobel metal hydrodeclorination catalyst can be improved by treating the supported catalyst, which comprises support and catalytic noble metal, with a late transition metal halide salt, a post transition metal containing halide salt, or a combination thereof, and with an alkali metal halide, ammonium halide, or a combination thereof. Suitable late transition metal and post transition metal halides for use herein include zinc chloride, tin chloride, and cupric chloride. A suitable alkali metal halide for use herein include lithium chloride. The novel resulting supported catalyst has its noble metal component, which is in the zero valent state, predominantly residing adjacent the surface of the support in a form which is predominantly visible under a microscope having a resolution of about 5 .ANG.. The catalyst also comprises the late transition metal, the post transition metal, or combination thereof, in the presence of the alkali metal moiety, ammonium moiety, or combination thereof.

Treatment to improve the durability and selectivity of a

The durability of a supported noble metal hydrodechlorination catalyst can be improved by (1) treating the supported catalyst, which comprises support and catalytic noble metal, with a non-elemental halide compound, which is not a mineral acid (such as an alkali metal halide, an ammonium halide, an alkaline earth metal halide, and/or a halogenated hydrocarbon); and (2) then using the treated catalyst in a hydrodechlorination reaction. Suitable treatment compounds include ammonium chloride, lithium chloride, or a chlorinated hydrocarbon. The treated catalyst is a novel composition of matter comprising at least one platinum group metal supported by an oxidic support wherein the metal, which is in the zero valent state, predominantly resides adjacent the surface of the support and is predominantly visible under a microscope having a resolution of about 5 .ANG..

Treatment to improve the durability of a hydrodechlorination catalyst

Essentially mesoporous titanium oxide materials, having an average pore diameter of no more than about 100 .ANG. (e.g., from about 20 .ANG. to about 50 .ANG.) and an average surface area of no less than about 300 m.sup.2 /gm, preferably no less than about 500 m.sup.2 /gm are disclosed which optionally can contain an effective amount of at least one transition metal (e.g., a rare earth metal, iron, or the like) for stabilization. These materials can be formed by treating a titanium source, which is derived from a titanium alkoxide, in an organic-aqueous solution, with an organic structure directing agent (e.g., higher alkyl amine, optionally in the presence of an alcohol cosolvent) to form meso-sized micelles and hydrothermally treating the resulting composition.

Growing community of inventors

Norwood, NJ, United States of America

Zongchao C Zhang