Richard T Pederson

6696597, Feb 24, 2004

Apr 10, 2001

09/833018

Richard L. Pederson - San Gabriel CA
Robert H. Grubbs - South Pasadena CA

TillieChem, Inc. - San Gabriel CA

C07C 6704

560247, 560231

The present invention relates to metathesis syntheses for insect sex-attractant pheromones or their components, such as E-5-decenyl acetate, the major component of the Peach Twig Borer pheromone; (5R,6S)-6-acetoxy-5-hexadecanolide, the mosquito oviposition attractant pheromone; E9,Z11-hexadecadienal, the pecan nut casebearer moth pheromone; 9-tetradecenyl formate, an analog of the Diamondback Moth (DBM) pheromone; 11-tetradecenyl acetate, the Omnivorous Leafroller (OLR) pheromone; E-4-tridecenyl acetate, the major component of the Tomato Pinworm (TPW) pheromone; E,E-8,10-dodecadienol, the Codling Moth (CM) pheromone. The syntheses preferably employ a Class I-IV metathesis catalyst, entail few reaction steps, use generally commercially available starting materials, and have relatively short process times. These syntheses produce good yields without the need for expensive or sophisticated equipment. The invention also provides an inexpensive route for producing omega-haloalkenols by cross-metathesizing alpha-omega-diacetoxy alkenes and alpha-omega-dihalides to yield omega-haloalkenols, which are easily converted into omega-haloalkanols under traditional hydrogenation methods.

6900347, May 31, 2005

May 24, 2002

10/155854

Basil P. Paulson - Los Angeles CA, US
Richard L Pederson - San Gabriel CA, US

Tilliechem, Inc. - San Gabriel CA

C07C067/02

560261, 560263

Reaction mixtures and methods using catalysts and reaction conditions to produce significantly improved yields (and thereby higher purity) of olefin metathesis products, with greatly reduced amounts of impurities. These techniques include in one instance reduction in temperature of reaction, and in another, the use of chemical compounds that act as reaction inhibitors of unwanted reactions to minimize or prevent formation of unwanted impurities.

7026495, Apr 11, 2006

Sep 16, 2003

10/665734

Richard L. Pederson - San Gabriel CA, US
Jason K. Woertink - Pasadena CA, US
Christopher M. Haar - Pasadena CA, US
David E. Gindelberger - South Pasadena CA, US
Yann Schrodi - Los Angeles CA, US

Materia, Inc. - Pasadena CA

C07F 15/00
C07F 9/00
B01J 31/00

556 21, 556 22, 556136, 548101, 502152, 502162, 502167

Chelating ligand precursors for the preparation of olefin metathesis catalysts are disclosed. The resulting catalysts are air stable monomeric species capable of promoting various metathesis reactions efficiently, which can be recovered from the reaction mixture and reused. Internal olefin compounds, specifically beta-substituted styrenes, are used as ligand precursors. Compared to terminal olefin compounds such as unsubstituted styrenes, the beta-substituted styrenes are easier and less costly to prepare, and more stable since they are less prone to spontaneous polymerization. Methods of preparing chelating-carbene metathesis catalysts without the use of CuCl are disclosed. This eliminates the need for CuCl by replacing it with organic acids, mineral acids, mild oxidants or even water, resulting in high yields of Hoveyda-type metathesis catalysts. The invention provides an efficient method for preparing chelating-carbene metathesis catalysts by reacting a suitable ruthenium complex in high concentrations of the ligand precursors followed by crystallization from an organic solvent.

7507854, Mar 24, 2009

Aug 23, 2004

10/924743

Choon Woo Lee - La Canada CA, US
Soon Hyeok Hong - Pasadena CA, US
Daniel P. Sanders - Pasadena CA, US
Robert H. Grubbs - South Pasadena CA, US
Richard L. Pederson - San Gabriel CA, US

Materia, Inc. - Pasadena CA

C07C 69/52

560205

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.

7820843, Oct 26, 2010

Dec 11, 2008

12/333125

Richard L. Pederson - San Gabriel CA, US
Jason K. Woertink - Pasadena CA, US
Christopher M. Haar - Pasadena CA, US
David E. Gindelberger - South Pasadena CA, US
Yann Schrodi - Los Angeles CA, US

Materia, Inc. - Pasadena CA

C07F 15/00
B01J 31/00

556 22, 556136, 549 3, 549209, 546 4, 546103, 544181

Chelating ligand precursors for the preparation of olefin methathesis catalysts are disclosed. The resulting catalysts are air stable monomeric species capable of promoting various methathesis reactions efficiently, which can be recovered from the reaction mixture and reused. Internal olefin compounds, specifically beta-substituted styrenes, are used as ligand precursors. Compared to terminal olefin compounds such as unsubstituted styrenes, the beta-substituted styrenes are easier and less costly to prepare, and more stable since they are less prone to spontaneous polymerization. Methods of preparing chelating-carbene methathesis catalysts without the use of CuCl are disclosed. This eliminates the need for CuCl by replacing it with organic acids, mineral acids, mild oxidants or even water, resulting in high yields of Hoveyda-type methathesis catalysts. The invention provides an efficient method for preparing chelating-carbene metathesis catalysts by reacting a suitable ruthenium complex in high concentrations of the ligand precursors followed by crystallization from an organic solvent.

8569560, Oct 29, 2013

Sep 19, 2012

13/622613

Richard L. Pederson - San Gabriel CA, US
Hiroki Kaido - Eden Praire MN, US
Michael J. Tupy - Crystal MN, US

Elevance Renewable Sciences, Inc. - Woodridge IL

C07C 1/00
C07C 6/00

585639, 585643

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.

7268242, Sep 11, 2007

Jan 31, 2006

11/344637

Richard L. Pederson - San Gabriel CA, US
Jason K. Woertink - Pasadena CA, US
Christopher M. Haar - Pasadena CA, US
David E. Gindelberger - South Pasadena CA, US
Yann Schrodi - Los Angeles CA, US

Materia, Inc. - Pasadena CA

C07F 15/00
C07F 9/02
C07C 39/00

556 21, 556 22, 556136, 548101, 568 17, 568 67, 568308, 568626, 568716

Chelating ligand precursors for the preparation of olefin metathesis catalysts are disclosed. The resulting catalysts are air stable monomeric species capable of promoting various metathesis reactions efficiently, which can be recovered from the reaction mixture and reused. Internal olefin compounds, specifically beta-substituted styrenes, are used as ligand precursors. Compared to terminal olefin compounds such as unsubstituted styrenes, the beta-substituted styrenes are easier and less costly to prepare, and more stable since they are less prone to spontaneous polymerization. Methods of preparing chelating-carbene metathesis catalysts without the use of CuCl are disclosed. This eliminates the need for CuCl by replacing it with organic acids, mineral acids, mild oxidants or even water, resulting in high yields of Hoveyda-type metathesis catalysts. The invention provides an efficient method for preparing chelating-carbene metathesis catalysts by reacting a suitable ruthenium complex in high concentrations of the ligand precursors followed by crystallization from an organic solvent.

20080108841, May 8, 2008

Sep 11, 2007

11/853598

Richard Pederson - San Gabriel CA, US
Jason Woertink - Pasadena CA, US
Christopher Haar - Pasadena CA, US
David Gindelberger - South Pasadena CA, US
Yann Schrodi - Los Angeles CA, US

MATERIA, INC. - Pasadena CA

C07F 15/00

556137000, 556136000

Chelating ligand precursors for the preparation of olefin metathesis catalysts are disclosed. The resulting catalysts are air stable monomeric species capable of promoting various metathesis reactions efficiently, which can be recovered from the reaction mixture and reused. Internal olefin compounds, specifically beta-substituted styrenes, are used as ligand precursors. Compared to terminal olefin compounds such as unsubstituted styrenes, the beta-substituted styrenes are easier and less costly to prepare, and more stable since they are less prone to spontaneous polymerization. Methods of preparing chelating-carbene metathesis catalysts without the use of CuCl are disclosed. This eliminates the need for CuCl by replacing it with organic acids, mineral acids, mild oxidants or even water, resulting in high yields of Hoveyda-type metathesis catalysts. The invention provides an efficient method for preparing chelating-carbene metathesis catalysts by reacting a suitable ruthenium complex in high concentrations of the ligand precursors followed by crystallization from an organic solvent.