Patents by Inventor Robert H. Grubbs

Robert H. Grubbs has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Publication number: 20170088563
    Abstract: The present invention is directed to a mild, efficient, and general direct C(sp)-H bond silylation. Various embodiments includes methods, each method comprising or consisting essentially of contacting at least one organic substrate comprising a terminal alkynyl C—H bond, with a mixture of at least one organosilane and an alkali metal hydroxide, alkali metal alkoxide, or alkali metal hydride under conditions sufficient to form a silylated terminal alkynyl moiety. The methods are operable in the presence or substantially absence of transition-metal compounds. The systems associated with these methods are also disclosed.
    Type: Application
    Filed: December 12, 2016
    Publication date: March 30, 2017
    Inventors: ANTON TOUTOV, KERRY BETZ, BRIAN M. STOLTZ, WENBO LIU, ROBERT H. GRUBBS
  • Patent number: 9593425
    Abstract: A CO2 reduction electrode includes an active layer on an electrode base. The active layer includes a polymer that includes one or more reaction components selected from a group consisting of a CO2 reduction catalyst and an activator that bonds CO2 so as to form a CO2 reduction intermediate.
    Type: Grant
    Filed: January 22, 2015
    Date of Patent: March 14, 2017
    Assignee: California Institute of Technology
    Inventors: Oana R. Luca, Raymond Weitekamp, Robert H. Grubbs, Harry A. Atwater, Slobodan Mitrovic
  • Patent number: 9586883
    Abstract: This disclosure is directed to methods of preparing organic aldehydes, each method comprising contacting a terminal olefin with an oxidizing mixture comprising: (a) a dichloro-palladium complex; (b) a copper complex; (c) a source of nitrite; under aerobic reaction conditions sufficient to convert at least a portion of the terminal olefin to an aldehyde.
    Type: Grant
    Filed: April 17, 2014
    Date of Patent: March 7, 2017
    Assignee: California Institute of Technology
    Inventors: Zachary K. Wickens, Bill Morandi, Robert H. Grubbs, Kacper Skakuj, Sarah M. Bronner
  • Patent number: 9586981
    Abstract: A novel chelated ruthenium-based metathesis catalyst bearing an N-2,6-diisopropylphenyl group is reported and displays near-perfect selectivity for the Z-olefin (>95%), as well as unparalleled TONs of up to 7,400, in a variety of homodimerization and industrially relevant metathesis reactions. This derivative and other new catalytically-active species were synthesized using an improved method employing sodium carboxylates to induce the salt metathesis and C—H activation of these chelated complexes. All of these new ruthenium-based catalysts are highly Z-selective in the homodimerization of terminal olefins.
    Type: Grant
    Filed: December 12, 2013
    Date of Patent: March 7, 2017
    Assignee: CALIFORNIA INSTITUTE OF TECHNOLOGY
    Inventors: Lauren E. Rosebrugh, Myles B. Herbert, Vanessa M. Marx, Benjamin K. Keitz, Robert H. Grubbs
  • Publication number: 20170062874
    Abstract: Electrolyte solutions including at least one anhydrous fluoride salt and at least one non-aqueous solvent are presented. The fluoride salt includes an organic cation having a charge center (e.g., N, P, S, or O) that does not possess a carbon in the ?-position or does not possess a carbon in the ?-position having a bound hydrogen. This salt structure facilitates its ability to be made anhydrous without decomposition. Example anhydrous fluoride salts include (2,2-dimethylpropyl)trimethylammonium fluoride and bis(2,2-dimethylpropyl)dimethylammonium fluoride. Combining these fluoride salts with at least one fluorine-containing non-aqueous solvent (e.g., bis(2,2,2-trifluoroethyl)ether; (BTFE)) promotes solubility of the salt within the non-aqueous solvents. The solvent may be a mixture of at least one non-aqueous, fluorine-containing solvent and at least one other non-aqueous, fluorine or non-fluorine containing solvent (e.g., BTFE and propionitrile or dimethoxyethane).
    Type: Application
    Filed: August 4, 2016
    Publication date: March 2, 2017
    Inventors: Simon C. JONES, Victoria K. DAVIS, Christopher M. BATES, Nebojsa MOMCILOVIC, Brett M. SAVOIE, Michael A. WEBB, Thomas F. MILLER, III, Robert H. GRUBBS, Christopher BROOKS, Kaoru OMICHI
  • Publication number: 20170057908
    Abstract: Processes and reaction mixtures including non-aqueous solvent mixtures are presented. Non-aqueous solvent mixtures including fluoride salt and non-aqueous solvent combinations are provided that possess high fluoride ion concentrations useful for a range of applications, including organic synthesis. Further non-aqueous solvent mixtures are provided including a salt possessing a non-fluoride anion and a non-aqueous solvent that, when contacted with aqueous fluoride-containing reagents, extract fluoride ions to form non-aqueous fluoride-ion solutions possessing high fluoride-ion concentrations. The salts include an organic cation that does not possess a carbon in the ?-position or does not possess a carbon in the ?-position having a bound hydrogen. This salt structure facilitates its ability to be made anhydrous without decomposition. Example anhydrous fluoride salts include (2,2-dimethylpropyl)trimethylammonium fluoride and bis(2,2-dimethylpropyl)dimethylammonium fluoride.
    Type: Application
    Filed: August 4, 2016
    Publication date: March 2, 2017
    Inventors: Simon C. JONES, Victoria K. DAVIS, Christopher M. BATES, Nebojsa MOMCILOVIC, Brett M. SAVOIE, Michael A. WEBB, Thomas F. MILLER, III, Robert H. GRUBBS, Jennifer M. MURPHY
  • Patent number: 9580451
    Abstract: The present invention is directed to sulfonic esters of metal oxides including those of formulas I and II:
    Type: Grant
    Filed: January 26, 2015
    Date of Patent: February 28, 2017
    Assignees: California Institute of Technology, Children's Hospital of Los Angeles
    Inventors: Carl M. Blumenfeld, Harry B. Gray, Robert H. Grubbs, Karn Sorasaenee
  • Patent number: 9575212
    Abstract: Described herein are copolymers constructed from chiral, non-racemic monomers, which self-assemble to photonic crystals. The difficulty of incorporating chiral elements into photonic crystals has limited the ability to generate unique bandstructures for different circular polarizations of light. The materials and methods described herein relate to easily, predictably fabricating chiral photonic crystals having desirable optical properties.
    Type: Grant
    Filed: February 25, 2014
    Date of Patent: February 21, 2017
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, Garret M. Miyake, Raymond Weitekamp, Victoria Piunova
  • Patent number: 9573125
    Abstract: An efficient method for the preparation of backbone-substituted imidazolinium salts for use as N-heterocyclic carbene ligands, e.g., for organometallic catalysts is provided. These functionalized N-heterocyclic carbene ligands are used to prepare solid-supported catalysts, e.g., for olefin metathesis.
    Type: Grant
    Filed: June 26, 2013
    Date of Patent: February 21, 2017
    Assignee: California Institute of Technology
    Inventors: Raymond Weitekamp, Robert H. Grubbs
  • Publication number: 20170029447
    Abstract: The present disclosure is directed to methods for dehydrogenatively coupled hydrosilanes and alcohols, the methods comprising contacting an organic substrate having at least one organic alcohol moiety with a mixture of at least one hydrosilane and sodium and/or potassium hydroxide, the contacting resulting in the formation of a dehydrogenatively coupled silyl ether. The disclosure further described associated compositions and methods of using the formed products.
    Type: Application
    Filed: July 26, 2016
    Publication date: February 2, 2017
    Inventors: ANTON TOUTOV, KERRY BETZ, ANDREW M. ROMINE, ROBERT H. GRUBBS
  • Patent number: 9556080
    Abstract: The present invention describes chemical systems and methods for silylating heteroaromatic organic substrates, said system consisting essentially of a mixture of (a) at least one organodisilane and (b) at least alkoxide base, preferably a potassium alkoxide base, and said methods comprising contacting a quantity of the organic substrate with a mixture consisting essentially of (a) at least one organodisilane and (b) at least one alkoxide base, preferably a potassium alkoxide, under conditions sufficient to silylate the heteroaromatic substrate.
    Type: Grant
    Filed: December 17, 2015
    Date of Patent: January 31, 2017
    Assignee: California Institute of Technology
    Inventors: Anton Toutov, Wenbo Liu, Brian M. Stoltz, Robert H. Grubbs, Kerry Betz, David P. Schuman
  • Patent number: 9556206
    Abstract: The present invention is directed to a mild, efficient, and general direct C(sp)-H bond silylation. Various embodiments includes methods, each method comprising or consisting essentially of contacting at least one organic substrate comprising a terminal alkynyl C—H bond, with a mixture of at least one organosilane and an alkali metal hydroxide, under conditions sufficient to form a silylated terminal alkynyl moiety. The methods are operable in the substantially absence of transition-metal compounds. The systems associated with these methods are also disclosed.
    Type: Grant
    Filed: September 1, 2015
    Date of Patent: January 31, 2017
    Assignee: California Institute of Technology
    Inventors: Anton Toutov, Kerry Betz, Brian M. Stoltz, Wenbo Liu, Robert H. Grubbs
  • Publication number: 20170022231
    Abstract: 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.
    Type: Application
    Filed: March 18, 2016
    Publication date: January 26, 2017
    Inventors: Choon Woo LEE, Robert H. GRUBBS, Pablo E. GUZMAN, Tonia S. AHMED, T. Patrick MONTGOMERY
  • Publication number: 20170020658
    Abstract: The invention relates to novel optical elements having improved UV protection. The optical element comprises a light adjustable optical element with a UV absorbent layer applied to at least one surface of the optical element. The invention is particularly useful in light adjustable intraocular lenses.
    Type: Application
    Filed: July 20, 2015
    Publication date: January 26, 2017
    Applicant: Calhoun Vision, Inc,
    Inventors: Robert H. Grubbs, Shiao H. Chang
  • Publication number: 20170018801
    Abstract: Provided herein are copolymer electrolytes and electrocatalyst platforms, including brush block copolymers, triblock brush copolymers and pentablock brush copolymers. The copolymers described have beneficial chemical, physical and electrical properties including high ionic conductivity and mechanical strength. In embodiments, for example, the provided copolymer electrolytes and electrocatalyst platforms are doped with lithium salts or mixed with ionic liquids to form ion gels. In some embodiments, the copolymers provided herein self-assemble into physically cross-linked polymer networks with additional useful properties. The provided copolymers have low dispersity in the polymer side chains and do not require post-polymerization modifications.
    Type: Application
    Filed: March 9, 2016
    Publication date: January 19, 2017
    Inventors: Robert H. GRUBBS, Christopher M. BATES, Alice CHANG, Brendon MCNICHOLAS, Simon C. JONES
  • Patent number: 9533928
    Abstract: The disclosure provides a dual-catalysis system for direct conversion of olefins to alcohols. The cooperative catalytic system contains one oxidizing catalyst and one transfer-hydrogenation catalyst. A wide variety of olefins, including aromatic and aliphatic olefins, can be used as the reactant. The transformation proceeds with anti-Markovnikov selectivity, and in some aspects provides primary alcohols as major products. The disclosure further provides a system for oxidation of olefins with anti-Markovnikov selectivity.
    Type: Grant
    Filed: July 1, 2015
    Date of Patent: January 3, 2017
    Assignee: California Institute of Technology
    Inventors: Guangbin Dong, Robert H. Grubbs, Peili Teo, Zachary K. Wickens
  • Publication number: 20160367669
    Abstract: This invention related to manufactured microbubbles, as well as methods of using manufactured microbubbles, for example, in medicinal applications. The invention pertains to the physical structure and materials of the microbubbles, as well as to methods for manufacturing microbubbles, methods for targeting microbubbles for specific medicinal applications, and methods for delivering microbubbles in medical treatment.
    Type: Application
    Filed: June 30, 2016
    Publication date: December 22, 2016
    Inventors: Robert H. Grubbs, Marshall L. Stoller, Hoyong Chung, Alissa M. Fitzgerald, Thomas W. Kenny, Renee M. Thomas
  • Publication number: 20160356923
    Abstract: The invention provides a class of block copolymers having a plurality of chemically different blocks, at least a portion of which incorporating polymer side chain groups having a helical secondary structure. The invention also provides structures generated by self-assembly of polymer blends including at least one block copolymer component, such as a brush block polymer or wedge-type block polymer. The invention provides, for example, periodic nanostructures and microstructures generated by self-assembly of block copolymers and polymer blends comprising a mixture of at least one block copolymer component, such as a brush block copolymer, and at least a second component.
    Type: Application
    Filed: August 22, 2016
    Publication date: December 8, 2016
    Applicant: California Institute of Technology
    Inventors: Garret M. MIYAKE, Raymond WEITEKAMP, Robert H. GRUBBS, Victoria PIUNOVA
  • Publication number: 20160347776
    Abstract: The present invention is directed to a mild, efficient, and general direct C(sp2)-H bond silylation of terminal olefins. Various embodiments includes methods, each method comprising or consisting essentially of contacting at least one organic substrate comprising a terminal olefinic C—H bond, with a mixture of at least one organosilane, organosilane, or mixture thereof and an alkali metal alkoxide or alkali metal hydroxide, such that the contacting results in the formation of a silylated olefinic product. The systems associated with these methods are also disclosed.
    Type: Application
    Filed: May 27, 2016
    Publication date: December 1, 2016
    Inventors: ANTON TOUTOV, WENBO LIU, KERRY BETZ, ALEXEY FEDOROV, BRIAN M. STOLTZ, ROBERT H. GRUBBS
  • Publication number: 20160339657
    Abstract: A method for adjusting a light adjustable lens in an optical system includes providing a light adjustable lens in an optical system; providing an ultraviolet light source to generate an ultraviolet light; and irradiating the generated ultraviolet light with a light delivery system onto the light adjustable lens with a center wavelength and with a spatial irradiance profile to change a dioptric power of the light adjustable lens by changing a refraction of the light adjustable lens in a refraction-change zone, thereby causing a wavefront sag, defined as half of a product of the change of the dioptric power and the square of a radius of the refraction-change zone, to be within 10% of its maximum over an ultraviolet spectrum.
    Type: Application
    Filed: May 20, 2016
    Publication date: November 24, 2016
    Applicant: Calhoun Vision, Inc.
    Inventors: Robert H. Grubbs, Christian A. Sandstedt