Ximo Ag

Verbio Vereinigte Bioenergie Ag

Elevance Renewable Sciences, Inc.

Georg Emil Frater

Levente Ondi

Jeno Varga

Florian Toth

Krisztian Lorincz

Agota Bucsai

Emmanuel Robe

Csaba Hegedus

Christophe Coperet

Victor Mougel

Gabor Eros

Steven Alan Cohen

Keith Michael Wampler

Matthew P Conley

Compound of formula 4 or formula 5 whereinL is a neutral ligand, preferably a nitrogen-containing heterocyclic carbene (NHC) such as carbene containing at least two nitrogen atoms, a cyclic aminoalkyl carbene (CAAC) or a bicyclic aminoalkyl carbene (BICAAC);R, R, R, R, R, R, R, R, Rand Rare, independently, H, unbranched or branched Calkyl, Ccycloalkyl, unbranched or branched Calkoxy, optionally bearing one or more halogen atoms, respectively; or aryl, optionally substituted with one or more of unbranched or branched Calkyl, Ccycloalkyl, unbranched or branched Calkoxy, aryl, aryloxy, unbranched or branched Calkylcarbonyl, arylcarbonyl, unbranched or branched Calkoxycarbonyl, aryloxycarbonyl, heteroaryl, carboxyl, cyano, nitro, amido, aminosulfonyl, N-heteroarylsulfonyl, unbranched or branched Calkylsulfonyl, arylsulfonyl, unbranched or branched Calkylsulfinyl, arylsulfinyl, unbranched or branched Calkylthio, arylthio, sulfonamide, halogen or N(R)(R), wherein Rand Rare independently selected from H and Calkyl:Ris H, unbranched or branched Calkyl.

Ruthenium complexes useful for catalyzing metathesis reactions

Method of making a second olefin using a first olefin, comprising steps (A) and (B): (A) performing a metathesis reaction with the first olefin in the presence of a metal complex configured to catalyse said metathesis reaction; (B) epoxidizing an olefin contained in the reaction mixture obtained in step (A) to form an epoxide; and deoxygenizing said epoxide to form said second olefin.

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The disclosure provides Group 6 complexes, which, in some embodiments, are useful for catalyzing olefin metathesis reactions. In some embodiments, the compounds are compounds of the following formula: wherein:

Compounds and the use thereof in metathesis reactions

The invention relates to a method of forming an olefin from a first olefin and a second olefin in a metathesis reaction, comprising step (i): 

Metathesis catalysts and reactions using the catalysts

Compound of formula (4) or formula (5), wherein L is a neutral ligand, preferably a nitrogen-containing heterocyclic carbene (NHC) such as carbene containing at least two nitrogen atoms, a cyclic aminoalkyl carbene (CAAC) or a bicyclic aminoalkyl carbene (BICAAC); R, R, R, R, R, R, R, R, Rand Rare, independently, H, unbranched or branched Calkyl, Ccycloalkyl, unbranched or branched Calkoxy, optionally bearing one or more halogen atoms, respectively; or aryl, optionally substituted with one or more of unbranched or branched Calkyl, Ccycloalkyl, unbranched or branched Calkoxy, aryl, aryloxy, unbranched or branched Calkylcarbonyl, arylcarbonyl, unbranched or branched Calkoxycarbonyl, aryloxycarbonyl, heteroaryl, carboxyl, cyano, nitro, amido, aminosulfonyl, N-heteroarylsulfonyl, unbranched or branched Calkylsulfonyl, arylsulfonyl, unbranched or branched Calkylsulfinyl, arylsulfinyl, unbranched or branched Calkylthio, arylthio, sulfonamide, halogen or N(R)(R), wherein Rand Rare independently selected from H and Calkyl: Ris H, unbranched or branched Calkyl. 

Method of making an immobilized tungsten catalyst comprising or consisting of (&#x2261;SiO)W(&#x2550;O)(&#x2550;CRR)(Ror R)(L), comprising at least the following step (i): (i) reacting silica (Si02) with a tungsten oxo alkylidene complex comprising or consisting of (R)(R)W(&#x2550;O)(&#x2550;CRR)(L), preferably wherein &#x2550;CRRis selected from &#x2550;CHC(CH)or &#x2550;CH(C(CH))CHand Rand Rare independently selected from pyrrol-1-yl, 2,5-dimethylpyrrol-1-yl, or 2,5-diphenylpyrrol-1-yl, or &#x2014;OR, wherein R is a six membered or 10 membered aryl ring, optionally substituted.

Immobilized metathesis tungsten oxo alkylidene catalysts and use thereof in olefin metathesis

A method is provided of forming an olefin from a first olefin and a second olefin in a metathesis reaction, comprising reacting the first olefin with the second olefin in the presence of a compound that catalyzes the metathesis reaction such that the molar ratio of the compound to the first or the second olefin is from 1:500 or less, and the conversion of the first or the second olefin to the olefin is at least 30%.

The disclosure provides Group 6 complexes, which, in some embodiments, are useful for catalyzing olefin metathesis reactions. In some embodiments, the compounds are compounds of the following formula (I) wherein: M is a Group 6 metal atom; X is an oxygen atom, &#x2550;N&#x2014;R, &#x2550;N&#x2014;N(R)(R) or &#x2550;N&#x2014;O&#x2014;R, Rand Rindependently being various substituents, such as aryl or heteroaryl, each optionally substituted; n is 0 or 1; Ris a neutral ligand; Ris hydrogen or an organic substituent; Ris an aryl or heteroaryl group, each optionally substituted; Ris an anionic ligand; and Ris an anionic ligand, such as a pyrrolide, a pyrazolide, an imidazolide, an indolide, an azaindolide, or an indazolide, each optionally substituted. 

Method of forming an olefin from a first olefin and a second olefin in a metathesis reaction, comprising step (i): (i) reacting the first olefin with the second olefin in the presence of a silica supported Mo- or W-alkylidene catalyst, wherein the first olefin and the second olefin are different from one another.

Use of immobilized molybdenum- and tungsten-containing catalysts in olefin cross metathesis

The invention relates to a method of forming an olefin from a first olefin and a second olefin in a metathesis reaction, comprising step (i): (i) reacting the first olefin with the second olefin in the presence of a compound that catalyzes said metathesis reaction such that the molar ratio of said compound to the first or the second olefin is from 1:500 or less, and the conversion of the first or the second olefin to said olefin is at least 50%, characterized in that as compound that catalyzes said metathesis reaction a compound of formula (A) is used: wherein M is Mo or W; Ris aryl, heteroaryl, alkyl, or heteroalkyl; optionally substituted; Rand Rcan be the same or different and are hydrogen, alkyl, alkenyl, heteroalkyl, heteroalkenyl, aryl, or heteroaryl; optionally substituted; Ris alkyl, alkoxy, heteroalkyl, aryl, heteroaryl, silylalkyl, silyloxy, optionally substituted; and Ris a residue R&#x2014;X&#x2014;, wherein X&#x2550;O and Ris aryl, optionally substituted; or X&#x2550;S and Ris aryl, optionally substituted; or X&#x2550;O and Ris (R, R, R)Si; wherein R, R, Rare alkyl or phenyl, optionally substituted; or X&#x2550;O and Ris (R, R, R)C, wherein R, R, Rare independently selected from phenyl, alkyl; optionally substituted; and to the catalysts used in the method. 

A method for treating a substrate prior to a metathesis reaction includes treating the substrate with a first agent configured to mitigate potentially adverse effects of one or more contaminants in the substrate on a catalyst used to catalyze the metathesis reaction. The treating reduces a level of the one or more contaminants by an amount sufficient to enable the metathesis reaction to proceed at a substrate-to-catalyst molar ratio of at least about 7,500 to 1. Methods for metathesizing substrates are described.

Growing community of inventors

Ebnat-Kappel, Switzerland

Georg Emil Frater