San Diego State University Research Foundation

Douglas Grotjahn

David Howard Combs

Casey Larsen

Erik Paulson

Erik Wiener

Gulin Erdogan

The invention provides novel catalysts and methods of using catalysts for controlling the position of a double bond and cis/trans-selectivity in isomerization of terminal alkenes to their 2-isomers. Catalysts such as (pentamethylcyclopentadienyl)Ru formulas 1 and 3 having a bifunctional phosphine can be used in the methods. A catalyst loading of 1 mol % of formulas 1+3 can be employed for the production of (E)-2-alkenes at 40-70&#xb0; C.; lower temperatures can be used with higher catalyst loading. Acetonitrile-free catalysts can be used at lower loadings, room temperature, and in less than a day to accomplish the same results as catalysts 1+3. The novel catalyst systems minimize thermodynamic equilibration of alkene isomers, so that the trans-2-alkenes of both non-functionalized and functionalized alkenes can be generated.

Terminal alkene monoisomerization catalysts and methods

The invention provides ruthenium-comprising catalysts, and methods of making and using them, for conjugating double bonds in polyunsaturated hydrocarbons, including polyunsaturated fatty acid derivatives, such as natural fats and oils which comprise (contain) more than one carbon to carbon double bond&#x2014;where the double bonds are separated by, e.g., a methylene, ethylene or propylene or longer group. The invention provides compositions and methods for treating fats and oils comprising 'interrupted' (e.g., 'methylene-, ethylene- or propylene-interrupted') double bonds to generate isomers with &#x201c;conjugated&#x201d; double bonds. The invention also provides compositions, and methods of making and using them, for making catalysts on a solid support. In one aspect, these catalysts are for alkene isomerization or exchange of alkene hydrogens for other isotopes. The invention provides heterocyclic resin-based compositions, and methods of using them, for making catalysts for alkene isomerization and exchange of hydrogens for deuterium or tritium isotopes.

Catalysts for alkene isomerization and conjugating double bonds in polyunsaturated fats and oils

The present invention relates to a method for preparing a bifunctional chelator for lanthanide. The method comprises the steps of providing a starting material which has an amino and carboxyl group; protecting the amino with an amino protecting group and the carboxyl with a carboxyl protecting group to produce a protected compound; reacting the protected compound with cyclen to generate a monoalkylated cyclen; reacting the monoalkylated cyclone with an activated compound to generated tetra-alkylated cyclone; removing the amino protecting group with a first protecting group removal reagent; and removing the carboxyl protecting groups with a second protecting group removal reagent to yield a bifunctional chelator having three more carboxyl groups and one or more amino groups.

Bifunctional chelators for sequestering lanthanides

Compositions and methods are described for hydrating terminal alkynes catalytically in anti-Markovnikov fashion. The compositions comprise a transition metal complex including at least one organic ligand having at least two heteroatoms, wherein the heteroatoms are directly bonded or located one atom away. Preferably, at least one of the heteroatoms is nitrogen, which is typically provided as part of a heterocyclic ring. Other preferred heteroatoms include S, P, N, As or Se. A particularly preferred catalyst employs a P-linked imidazole ligand bound to Ru. Such complexes have a controlled adaptable proton transfer ability and/or a hydrogen bonding ability making them particularly useful as chemical reaction facilitators.

Compositions and methods for hydration of terminal alkynes

Compositions including at least one organic ligand including a first hetero atom and a second hetero atom directly bonded to the first hetero atom or located one carbon atom away from the first hetero atom, with at least one of the hetero atoms being nitrogen, and a transition metal moiety partially complexes by the organic ligand are provided. Such complexes have a controlled adaptable proton transfer ability and/or a hydrogen bonding ability which makes such compositions particularly useful as chemical reaction facilitators. Examples of chemical reactions facilitated by such compositions include hydrolysis reactions and carbon dioxide conversion reactions.

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San Diego, CA, United States of America

Douglas Grotjahn