California Institute of Technology

Elevance Renewable Sciences, Inc.

University of Southern California

Materia, Inc.

Wilmar Trading Pte Ltd.

Choon Woo Lee

Robert H Grubbs

Richard L Pederson

Timothy Walter Abraham

Yann Schrodi

Michael John Tupy

Hiroki Kaido

Mark Salman Humayun

Michael Stephen Starch

Brian Jeffery Swanton

Tae-Lim Choi

Monika Mujkic

Deidra Cade

Tonia S Ahmed

Daniel P Sanders

T Patrick Montgomery

Hyunjin M Kim

Pablo E Guzman

Alexandre A Pletnev

Soon Hyeok Hong

Isaac M Rutenberg

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

Wax compositions derived from metathesized natural oils and amines and methods of making wax compositions from metathesized natural oils and amines are provided. The wax compositions comprise amidated metathesized natural oils formed from a metathesized natural oil and at least one amine. The methods comprise providing an amine and providing a metathesized natural oil. The methods further comprise mixing the amine and the metathesized natural oil in the presence of a basic catalyst or heat, causing a reaction between the amine and metathesized natural oil, therein forming the amidated metathesized natural oil.

Waxes derived from metathesized natural oils and amines and methods of making

This invention relates generally to olefin metathesis catalyst compounds, to the preparation of such compounds, and the use of such catalysts in the metathesis of olefins and olefin compounds, more particularly, in the use of such catalysts in (E)-selective olefin metathesis reactions. The invention has utility in the fields of catalysis, organic synthesis, polymer chemistry, and industrial and fine chemicals chemistry.

Catalysts for (E)-selective olefin metathesis

Compositions derived from metathesized natural oils and amines and methods of making

The disclosure provides methods and materials suitable for preparing coating layers on substrates. The coatings comprise quaternary amine groups and therefore impart anti-bacterial properties to the substrate. in one embodiment, for example, there is provided a quaternary amine-containing polymeric coating comprising propylene and ethylene repeat units.

Antimicrobial materials

The invention is directed to methods of making organic compounds by metathesis and hydrocyanation. The method of the invention may be used, for example, to make industrial important organic compounds such as diacids, diesters, acid-amines, acid-alcohols, acid-nitriles, ester-amines, ester-alcohols, and ester-nitriles.

Methods of making organic compounds by metathesis and hydrocyanation

The disclosure provides methods and materials suitable for preparing coating layers on substrates. The coatings comprise quaternary amine groups and therefore impart anti-bacterial properties to the substrate. In one embodiment, for example, there is provided a quaternary amine-containing polymeric coating comprising propylene and ethylene repeat units.

This invention relates generally to olefin metathesis, and more particularly relates to the ring-opening, ring insertion cross-metathesis of cyclic olefins with internal olefins such as seed oils and the like. In one embodiment, a method is provided for carrying out a catalytic ring-opening cross-metathesis reaction, comprising contacting at least one olefinic substrate with at least one cyclic olefin as a cross metathesis partner, in the presence of a ruthenium alkylidene olefin metathesis catalyst under conditions effective to allow ring insertion cross metathesis whereby the cyclic olefin is simultaneously opened and inserted into the olefinic substrate. The invention has utility in the fields of catalysis, organic synthesis, and industrial chemistry.

Ring opening cross-metathesis reaction of cyclic olefins with seed oils and the like

The present invention relates to the use of isomerization inhibitors in olefin metathesis reactions. The inhibitors are low molecular weight organic acids such as formic acid, acetic acid, benzoic acid, and the like.

Impurity reduction in Olefin metathesis reactions

This invention relates generally to synthetic procedures that include the step of ring-opening metathesis of cyclic olefins and reaction with an acyclic diene co-reactant to produce olefin macrocycles by ring expansion, or alternatively. The ring expansion of the cyclic olefin is provided by three types of sequential olefin metathesis (ring-opening, cross, and ring-closing olefin metathesis). More particularly, the invention pertains to synthesis of olefin macrocycles via olefin metathesis reactions using a Group 8 transition metal complex as the metathesis catalyst. Macrocycles provided herein have a variety of uses in the pharmaceutical, biomedical, organic synthesis and chemical industries, such as the production of crown ethers that are useful as metal complexing species.

Ring-expansion of cyclic olefins metathesis reactions with an acyclic diene

This invention relates generally to synthetic procedures that include the step of ring-opening metathesis of cyclic olefins and reaction with an acyclic diene co-reactant to produce regularly repeating A,B-alternating olefin polymers. The A,B-alternating polymers are produced by varying reaction conditions and/or reactant proportions and using only two types of olefin metathesis (ring-opening and cross) to provide regularly repeating ABAB . . . etc. polymers via ring-opening metathesis polymerization (ROMP). More particularly, the invention pertains to synthesis of A,B-alternating olefin polymers via olefin metathesis reactions using a Group 8 transition metal complex as the metathesis catalyst. Polymers provided herein have utility in a variety of fields, including not only polymer chemistry per se, but also in the pharmaceutical, biomedical, and packaging industries where the structure and properties of polymers need to be tightly controlled.

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La Canada, CA, United States of America

Choon Woo Lee