Synthesis of fine and specialty chemicals involving heterogeneous catalysts is discussed according to the type of reactions (e.g., hydrogenation, oxidation, isomerization, etc.) for various biomass derived feedstocks (carbohydrates, lignans, phenols, flavonoids, tannins, and stilbenes, tall oil, and fatty acids).

Recent Progress in Synthesis of Fine and Specialty Chemicals from Wood and Other Biomass by Heterogeneous Catalytic Processes

This disclosure relates generally to olefin metathesis, and more particularly relates to the synthesis of terminal alkenes from internal alkenes using a cross-metathesis reaction catalyzed by an olefin metathesis catalyst. According to one aspect, for example, a method is provided for synthesizing a terminal olefin, the method comprising contacting, in the presence of a ruthenium alkylidene metathesis catalyst, an olefinic substrate comprised of at least one internal olefin with a cross metathesis partner comprised of an alpha olefinic reactant, under reaction conditions effective to allow cross-metathesis to occur, wherein the reaction conditions include a reaction temperature of at least 35° C. The methods, compositions, reactions and reaction systems herein disclosed have utility in the fields of catalysis, organic synthesis, and industrial chemistry.

Synthesis of terminal alkenes from internal alkenes via olefin metathesis

Disclosed are petrolatum-like compositions that comprise metathesized unsaturated polyol esters. Also disclosed are emulsions comprising metathesized unsaturated polyol esters. The petrolatum-like compositions may be used as substitutes for petroleum-based petrolatum. The emulsions may be water-in-oil or oil-in-water emulsions and may be suitable for a variety of end uses.

Compositions comprising metathesized unsaturated polyol esters

Described are methods of making organic compounds by metathesis chemistry. The methods of the invention are particularly useful for making industrially-important organic compounds beginning with starting compositions derived from renewable feedstocks, such as natural oils. The methods make use of a cross-metathesis step with an olefin compound to produce functionalized alkene intermediates having a pre-determined double bond position. Once isolated, the functionalized alkene intermediate can be self-metathesized or cross-metathesized (e.g., with a second functionalized alkene) to produce the desired organic compound or a precursor thereto. The method may be used to make bifunctional organic compounds, such as diacids, diesters, dicarboxylate salts, acid/esters, acid/amines, acid/alcohols, acid/aldehydes, acid/ketones, acid/halides, acid/nitriles, ester/amines, ester/alcohols, ester/aldehydes, ester/ketones, ester/halides, ester/nitriles, and the like.

Methods of Making Organic Compounds by Metathesis

This invention relates generally to olefin metathesis, and more particularly relates to the synthesis of terminal alkenes from internal alkenes using a cross-metathesis reaction catalyzed by a selected olefin metathesis catalyst. In one embodiment of the invention, for example, a method is provided for synthesizing a terminal olefin, the method comprising contacting an olefinic substrate comprised of at least one internal olefin with ethylene, in the presence of a metathesis catalyst, wherein the catalyst is present in an amount that is less than about 1000 ppm relative to the olefinic substrate, and wherein the metathesis catalyst has the structure of formula (II), wherein the various substituents are as defined herein. The invention has utility, for example, in the fields of catalysis, organic synthesis, and industrial chemistry.

Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis

The present disclosure provides low trans-fatty acid fat compositions, methods of hydrogenating unsaturated feedstocks (e.g., oils), and hydrogenation catalyst compositions. One exemplary method involves producing a catalyst composition by heating a nickel-based catalyst to a first temperature of at least about 85° C in the presence of hydrogen and a fat component. An unsaturated feedstock may be contacted with the catalyst composition and hydrogenated by sustaining a hydrogenation reaction at a second temperature of no greater than about 700 C. Some specific implementations of the invention permit the production of partially hydrogenated seed oils with low trans-fatty acid contents.

Gijsbertus Johannes Van Rossum

Papers

Low trans-fatty acid fat compositions; low-temperature hydrogenation, e.g., of edible oils