The Nitrogen Is Bonded To An Additional Acyclic Carbon Or Acyclic Carbon Chain, To Which A -c(=x)x- Group Is Bonded Directly, Wherein The X's Are The Same Or Diverse Chalcogen Patents (Class 562/17)
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Patent number: 10109875Abstract: One embodiment of the present invention is a unique fuel cell system. Another embodiment is a unique desulfurization system. Yet another embodiment is a method of operating a fuel cell system. Other embodiments include apparatuses, systems, devices, hardware, methods, and combinations for fuel cell systems and desulfurization systems. Further embodiments, forms, features, aspects, benefits, and advantages of the present application will become apparent from the description and figures provided herewith.Type: GrantFiled: May 1, 2017Date of Patent: October 23, 2018Assignee: LG FUEL CELL SYSTEMS INC.Inventor: John R. Budge
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Patent number: 9944667Abstract: Generally, the present invention relates to improvements in metal utilization in supported, metal-containing catalysts. For example, the present invention relates to methods for directing and/or controlling metal deposition onto surfaces of porous substrates. The present invention also relates to methods for preparing catalysts in which a first metal is deposited onto a support (e.g., a porous carbon support) to provide one or more regions of a first metal at the surface of the support, and a second metal is deposited at the surface of the one or more regions of the first metal. Generally, the electropositivity of the first metal (e.g., copper or iron) is greater than the electropositivity of the second metal (e.g., a noble metal such as platinum) and the second metal is deposited at the surface of the one or more regions of the first metal by displacement of the first metal. The present invention further relates to treated substrates, catalyst precursor structures and catalysts prepared by these methods.Type: GrantFiled: September 9, 2015Date of Patent: April 17, 2018Assignee: Monsanto Technology LLCInventor: Kam-To Wan
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Patent number: 9929453Abstract: A lithium-air battery cathode catalyst includes core-shell nanoparticles on a carbon support, wherein: a core of the core-shell nanoparticles is platinum metal; and a shell of the core-shell nanoparticles is copper metal; wherein: the core-shell nanoparticles have a weight ratio of the copper metal to the platinum metal from about 4% to about 6% copper to from about 2% to about 12% platinum, with a remaining percentage being the carbon support.Type: GrantFiled: August 4, 2014Date of Patent: March 27, 2018Assignee: UCHICAGO ARGONNE, LLCInventors: Jun Lu, Khalil Amine, Xiaoping Wang, Xiangyi Luo, Deborah J. Myers
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Patent number: 9364003Abstract: This invention relates generally to improved methods and herbicidal glyphosate compositions for use in controlling the growth of weeds and unwanted vegetation, and particularly for use in controlling weeds in a crop of transgenic glyphosate-tolerant cotton plants by over-the-top, foliar application of a herbicidal glyphosate formulation.Type: GrantFiled: February 10, 2012Date of Patent: June 14, 2016Assignee: Monsanto Technology LLCInventors: Stephen D. Prosch, Michael E. Seitz, David R. Eaton, David Z. Becher
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Patent number: 9346736Abstract: A process utilizing nitric acid and oxygen as co-oxidants to oxidize aldehydes, alcohols, polyols, preferably carbohydrates, specifically reducing sugars to produce the corresponding carboxylic acids.Type: GrantFiled: March 12, 2014Date of Patent: May 24, 2016Assignee: Rivertop Renewables, Inc.Inventors: Steven Donen, Kirk Hash, Tyler Smith
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Patent number: 9315528Abstract: An improved method for the manufacture of phosphonoalkyl iminodiacetic acid M2PO3—X—N—(CH2COOM)2 wherein X is a C1-6 linear or branched alkyl group; and M is selected from hydrogen, alkali, earth-alkali, ammonium and protonated amine is disclosed. The iminodiacetic acid starting material is reacted with a substantially stoichiometric amount of phosphorous acid, in the presence of a large excess of phosphoric acid to thereby yield a reaction medium insoluble reaction product (PAI-DA) which can be separated from the reaction medium. In a particularly preferred approach, the phosphorous acid is prepared in situ starting from liquid P4O6.Type: GrantFiled: October 27, 2010Date of Patent: April 19, 2016Assignee: Straitmark Holding AGInventors: Patrick Notté, David Lemin, Cedric Nicolas Pirard
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Patent number: 9114376Abstract: Provided are catalysts comprising a small pore molecular sieve embedded with platinum group metal (PGM) and methods for treating lean burn exhaust gas using the same.Type: GrantFiled: June 5, 2012Date of Patent: August 25, 2015Assignee: Johnson Matthey Public Limited CompanyInventors: Joseph Michael Fedeyko, Hai-Ying Chen, Paul Joseph Andersen
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Publication number: 20140309419Abstract: This invention relates to a method for enhancing the thermal stability of ionic compounds including ionic liquids, by immobilization on porous solid support materials having a pore diameter of between about 20-200 ?, wherein the solid support does not have a pore size of 90 ?.Type: ApplicationFiled: August 30, 2012Publication date: October 16, 2014Applicants: Danmarks Tekniske Universite, The Board of Trustees of the University of Alabama for and on behalf of the University of AlabamaInventors: Anders Riisager, Rasmus Fermann, Robin D. Rogers, Gabriela Gurau
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Publication number: 20140234196Abstract: The present invention generally relates to processes for recovery of phosphorus values and salt impurities from aqueous waste streams. In particular, the present invention relates to processes for recovery of phosphorus values and salt impurities from aqueous waste streams generated in the manufacture of phospho-herbicides, including N-(phosphonomethyl)glycine and glufosinate.Type: ApplicationFiled: January 21, 2014Publication date: August 21, 2014Applicant: Monsanto Technology LLCInventors: Chil Y. Choi, Gregory A. Hartmann, Peng Lei, William Poncez, Peter E. Rogers, William A. Scholle, Lowell Smith, Robert B. Weisenfeld, Fuchen Liu, Chen-Hsyong Yang
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Publication number: 20140173780Abstract: A method is disclosed for the Agrobacterium-mediated germline transformation of soybean, comprising infecting split soybean seeds, with a portion of the embryonic axis, with Agrobacterium tumefaciens containing a transgene. The method can further comprise regenerating the explants produced from the transformation of the split soybean seeds comprising a portion of embryonic axis in vitro on selection medium.Type: ApplicationFiled: December 18, 2013Publication date: June 19, 2014Inventors: Dayakar Pareddy, Sivarama R. Chennareddy, Tatyana Minnicks, Olga Karpova, David Griffin, Jayakumar P. Samuel, Kelley A. Smith, Rodrigo Sarria-Millan, Tejinder Kumar Mall
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Patent number: 8703639Abstract: This invention relates to the field of heterogeneous catalysis, and more particularly to oxidation catalysts including carbon supports having deposited thereon a noble metal and one or more optional promoters and to methods for their preparation. The invention further relates to the field of heterogeneous catalytic oxidation reactions, including the preparation of secondary amines by the catalytic oxidation of tertiary amines, such as the oxidation of an N-(phosphonomethyl)iminodiacetic acid to produce an N-(phosphonomethyl)glycine product.Type: GrantFiled: September 15, 2005Date of Patent: April 22, 2014Assignee: Monsanto Technology LLCInventors: Kam-To Wan, Mark A. Leiber
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Publication number: 20130102808Abstract: An improved method for the manufacture of phosphonoalkyl iminodiacetic acid M2PO3—X—N—(CH2COOM)2 wherein X is a C1-6 linear or branched alkyl group; and M is selected from hydrogen, alkali, earth-alkali, ammonium and protonated amine is disclosed. The iminodiacetic acid starting material is reacted with a substantially stoichiometric amount of phosphorous acid, in the presence of a large excess of phosphoric acid to thereby yield a reaction medium insoluble reaction product (PAI-DA) which can be separated from the reaction medium. In a particularly preferred approach, the phosphorous acid is prepared in situ starting from liquid P4O6.Type: ApplicationFiled: October 27, 2010Publication date: April 25, 2013Applicant: STRAITMARK HOLDING AGInventors: Patrick Notté, David Lemin, Cedric Nicolas Pirard
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Publication number: 20130023405Abstract: An activated carbon having a high catalytic activity as an oxidation catalyst or a decomposition catalyst, and use therefor are provided. The activated carbon has (a) an oxygen content in a range from 1.40 to 4.30% by mass, (b) a nitrogen content in a range from 0.90 to 2.30% by mass, (c) a sulfur content in a range from 0.50 to 1.20% by mass, and (d) a hydrogen content in a range from 0.40 to 0.65% by mass. The activated carbon may have at least one characteristic of (e) an amount of an acidic surface functional group of 0.10 to 0.36 meq/g, (f) an amount of a basic surface functional group of 0.50 to 1.30 meq/g, and (g) a benzene adsorption capacity of 25 to 50%. The activated carbon catalyzes an oxidation reaction of N-(phosphonomethyl) iminodiacetic acid with a peroxide (e.g., hydrogen peroxide) and achieves an efficient production of N-(phosphonomethyl)glycine even after repetitive use. The activated carbon also efficiently decomposes a chloramine.Type: ApplicationFiled: March 24, 2011Publication date: January 24, 2013Applicant: Kuraray Chemical Co., Ltd.Inventors: Mitsunori Hitomi, Takayuki Yoshikawa, Takayuki Yamada
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Patent number: 8252953Abstract: Generally, the present invention relates to improvements in metal utilization in supported, metal-containing catalysts. For example, the present invention relates to methods for directing and/or controlling metal deposition onto surfaces of porous substrates. The present invention also relates to methods for preparing catalysts in which a first metal is deposited onto a support (e.g., a porous carbon support) to provide one or more regions of a first metal at the surface of the support, and a second metal is deposited at the surface of the one or more regions of the first metal. Generally, the electropositivity of the first metal (e.g., copper or iron) is greater than the electropositivity of the second metal (e.g., a noble metal such as platinum) and the second metal is deposited at the surface of the one or more regions of the first metal by displacement of the first metal. The present invention further relates to treated substrates, catalyst precursor structures and catalysts prepared by these methods.Type: GrantFiled: May 1, 2009Date of Patent: August 28, 2012Assignee: Monsanto Technology LLCInventor: Kam-To Wan
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Publication number: 20120184434Abstract: The present invention relates to a salt comprising an anionic pesticide and a cationic polyamine of the formula (A) or (B) as described in the description. The invention further relates to an agrochemical composition comprising said salt. It also relates to a method for preparing said salt comprising combining the pesticide in its neutral form or as salt, and the polyamine in its neutral form or as salt. In addition, the invention relates to a method of combating harmful insects and/or phytopathogenic fungi. It also relates to a method of controlling undesired vegetation. Finally, the invention relates to seed comprising said salt.Type: ApplicationFiled: September 28, 2010Publication date: July 19, 2012Applicant: BASF SEInventors: Wen Xu, Paul Ch. Kierkus, Steven Brunt, Steven Bowe, Adam Hixson, Terrance M. Cannan
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Publication number: 20120172220Abstract: The present invention provides N-phosphonomethylglycine guanidine salts. The N-phosphonomethylglycine guanidine salts have improved herbicidal efficacy over glyphosate alone. The present invention also provides guanidine compounds and salts thereof.Type: ApplicationFiled: June 24, 2010Publication date: July 5, 2012Applicants: FLAMEL TECHNOLOGIES S.A., MONSANTO TECHNOLOGY LLCInventors: Ronald J. Brinker, Olivier Soula, Alain Lemercier
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Publication number: 20120130120Abstract: An improved method for the manufacture of phosphonoalkyl iminodiacetic acid (PAIDA) is disclosed. The iminodiacetic acid starting material is reacted with a considerable amount, in excess of stoichiometric requirements, of phosphorous acid to thereby yield a reaction medium insoluble reaction product which can be separated from the reaction medium. In a particularly preferred approach, the phosphorous acid is prepared in situ starting from liquid P4O6.Type: ApplicationFiled: May 28, 2010Publication date: May 24, 2012Applicant: STRAITMARK HOLDING AGInventors: Patrick Notté, Cedric Nicolas Pirard, David Lemin
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Publication number: 20120100051Abstract: The present invention generally relates to processes for recovery of phosphorus values and salt impurities from aqueous waste streams. In particular, the present invention relates to processes for recovery of phosphorus values and salt impurities from aqueous waste streams generated in the manufacture of phospho-herbicides, including N-(phosphonomethyl)glycine and glufosinate.Type: ApplicationFiled: May 13, 2010Publication date: April 26, 2012Applicant: MONSANTO TECHNOLOGY LLCInventors: Chil Y. Choi, Gregory A. Hartmann, Peng Lei, Fuchen Liu, William Poncez, Peter E. Rogers, William A. Scholle, Lowell Smith, Robert B. Weisenfeld, Chen-Hsyong Yang
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Patent number: 8143441Abstract: This invention relates to an improved catalyst, comprising a carbon support having a noble metal at its surface, for use in catalyzing liquid phase oxidation reactions, especially in an acidic oxidative environment and in the presence of solvents, reactants, intermediates, or products which solubilize noble metals; a process for the preparation of the improved catalyst; a liquid phase oxidation process using such a catalyst wherein the catalyst exhibits improved resistance to noble metal leaching, particularly in acidic oxidative environments and in the presence of solvents, reactants, intermediates, or products which solubilize noble metals; and a liquid phase oxidation process in which N-(phosphonomethyl)iminodiacetic acid (i.e., “PMIDA”) or a salt thereof is oxidized to form N-(phosphonomethyl)glycine (i.e., “glyphosate”) or a salt thereof using such a catalyst wherein the oxidation of the formaldehyde and formic acid by-products into carbon dioxide and water is increased.Type: GrantFiled: June 5, 2006Date of Patent: March 27, 2012Assignee: Monsanto Technology LLCInventors: Jerry R. Ebner, Mark A. Leiber, Kam-To Wan, Anthony Woods, Peter E. Rogers
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Publication number: 20110301381Abstract: This invention relates to the field of heterogeneous catalysis, and more particularly to catalysts including carbon supports having formed thereon compositions which comprise a transition metal in combination with nitrogen and/or carbon. The invention further relates to the fields of catalytic oxidation and dehydrogenation reactions, including the preparation of secondary amines by the catalytic oxidation of tertiary amines and the preparation of carboxylic acids by the catalytic dehydrogenation of alcohols.Type: ApplicationFiled: March 16, 2011Publication date: December 8, 2011Applicant: MONSANTO TECHNOLOGY LLCInventors: James P. Coleman, Martin P. McGrath, Fuchen Liu, Juan Arhancet
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Patent number: 8026389Abstract: The present invention provides active ingredients and herbicide formulations, as well as the production processes therefor. The active ingredient of the invention is a dry, solid ammonium salt of glyphosate, having high purity (95 to 100%) and low humidity (<1.0% m/m), and is useful as “technical salt” for the preparation of dry, solid, and water-soluble herbicide formulations of the invention. The production process of said active ingredient comprises a solid/liquid/solid reaction between a solid ammonium salt and solid glyphosate acid, both solid being dispersed in an organic liquid medium. The products of the invention are highly water-soluble and are useful for controlling crop weeds.Type: GrantFiled: December 17, 2007Date of Patent: September 27, 2011Inventor: Ricardo Amaral Remer
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Publication number: 20100247463Abstract: The present invention relates to an N-(phosphonoalkyl)-amino acid, a related compound or a derivative thereof, the N-(phosphonoalkyl)-amino acid, related compound or derivative thereof being in a form as a free acid, salt, partial salt, lactone, amide or ester, or in stereoisomeric or non-stereoisomeric form, other than N-(phosphonomethyl)-glycine or N,N-bis(phosphonomethyl)-glycine. Also included is a composition including an N-(phosphonoalkyl)-amino acid, a related compound or a derivative thereof in a form as a free acid, salt, partial salt, lactone, amide or ester, or in stereoisomeric or non-stereoisomeric form, and a cosmetically or pharmaceutically acceptable vehicle for topical or systemic administration to a mammalian subject, as well as a method of administering an effective amount of such a composition for alleviating or improving a condition, disorder, symptom or syndrome associated with at least one of a nervous, vascular, musculoskeletal or cutaneous system.Type: ApplicationFiled: June 16, 2010Publication date: September 30, 2010Inventors: Ruey J. Yu, Eugene J. Van Scott
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Patent number: 7799571Abstract: This invention relates to the preparation of N-(phosphonomethyl)glycine (“glyphosate”) from N-(phosphonomethyl)iminodiacetic acid (“PMIDA”), and more particularly to methods for control of the conversion of PMIDA, for the identification of reaction end points relating to PMIDA conversion and the preparation of glyphosate products having controlled PMIDA content.Type: GrantFiled: April 3, 2006Date of Patent: September 21, 2010Assignee: Monsanto Technology LLCInventors: Donald D. Soleta, David R. Eaton, Peter E. Rogers, Eduardo A. Casanova, John Wagenknecht, Leonard Aynardi, David Z. Becher, Robert E. Byrd, James P. Coleman, Walter K. Gavlick, Eric A. Haupfear, Oliver Lerch, Carl Mumford, Alfredo Oba, Stephen D. Prosch, Bart Roose, Mark D. Scaia, Lowell R. Smith
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Patent number: 7750180Abstract: N-phosphonomethylamines are produced by reaction of an amine substrate with a halomethylphosphonic acid or salt thereof, a hydroxymethylphosphonic acid or salt thereof, or a dehydrated self-ester dimer, trimer or oligomer of hydroxymethylphosphonic acid. Among the products that may be prepared according to the process are N-phosphonomethylaminocarboxylic acids such as (e.g.) glyphosate, N-phosphonomethylaminoalkanols such as (e.g.) hydroxyethlaminomethylphosphonic acid, and N-acylaminomethylphosphonic acids such as (e.g.) N-carbamylaminomethylphosphonic acid. Certain reactions are conducted with a substantial excess of amine reactant in order to drive the conversion while avoiding excessive formation of bis(N-phosphonomethyl)amine by-products.Type: GrantFiled: August 23, 2004Date of Patent: July 6, 2010Assignee: Monsanto Technology LLCInventors: James P. Coleman, Jerry R. Ebner, Eric A. Haupfear, Patrick J. Lennon, Joseph A. Schaper, Samuel J. Tremont, Serge G. Wolfson, Philip H. Brodsky
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Patent number: 7745660Abstract: An improved process for recovering a crystalline product (particularly an N-(phosphonomethyl)glycine product) from a solution comprising both a product subject to crystallization and undesired impurities is provided.Type: GrantFiled: February 13, 2007Date of Patent: June 29, 2010Assignee: Monsanto Technology LLCInventors: Eric A. Haupfear, Eduardo A. Casanova, Kenneth S. Meyer, Henry H. Chien
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Publication number: 20100130774Abstract: This invention relates to the field of heterogeneous catalysis, and more particularly to oxidation catalysts including carbon supports having deposited thereon a noble metal and one or more optional promoters and to methods for their preparation. The invention further relates to the field of heterogeneous catalytic oxidation reactions, including the preparation of secondary amines by the catalytic oxidation of tertiary amines, such as the oxidation of an N-(phosphonomethyl)iminodiacetic acid to produce an N-(phosphonomethyl)glycine product.Type: ApplicationFiled: September 15, 2005Publication date: May 27, 2010Applicant: MONSANTO TECHNOLOGY LLCInventors: Kam-To Wan, Mark A. Leiber, Kerry Brethauer, Jingyue Liu
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Patent number: 7705178Abstract: Improved processes for preparing and crystallizing N-(phosphonomethyl)iminodiacetic acid are provided. The processes include adding N-(phosphonomethyl)iminodiacetic acid seed crystals to N-(phosphonomethyl)iminodiacetic acid reaction solutions. Provided are beds of crystallized N-(phosphonomethyl)iminodiacetic acid having improved permeability and filtration rate and reduced impurities.Type: GrantFiled: April 25, 2006Date of Patent: April 27, 2010Assignee: Monsanto Technology LLCInventors: Sunder S. Rangachari, Todd C. Friedman, Sherrol Lee Baysdon, David Z. Becher
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Patent number: 7687663Abstract: This invention generally relates to processes for recovering solubilized noble metals from aqueous process streams, in particular, aqueous process streams generated in the preparation of an N-(phosphonomethyl)glycine product, for example, by noble metal-catalyzed oxidation of an N-(phosphonomethyl)iminodiacetic acid substrate. The process includes contacting the aqueous process stream with a noble metal adsorption media such as an ion exchange resin to remove solubilized noble metal from the process stream.Type: GrantFiled: November 14, 2005Date of Patent: March 30, 2010Assignee: Monsanto Technology LLCInventors: Mark D. Scaia, David R. Eaton, Roger J. Hoekstra, Eric A. Haupfear
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Patent number: 7683207Abstract: The present invention is a process for the purification of glyphosate (PMG) comprising: 1) dissolving or suspending a material comprising PMG in water, in the presence of a base, to produce a composition comprising a PMG salt in an aqueous base, 2) contacting the composition with an acid, such that the PMG salt is neutralized, forming a precipitate of PMG, and 3) isolating the precipitate of PMG, with the proviso that the composition of step 1) is not concentrated or filtered using a nanofiltration membrane.Type: GrantFiled: May 20, 2005Date of Patent: March 23, 2010Assignee: Dow AgroSciences LLCInventors: Jimmy Jui Tai, Herbert Nathan Praay, James William Ringer, Mark Victor Michael Emonds
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Publication number: 20090326262Abstract: Generally, the present invention relates to improvements in metal utilization in supported, metal-containing catalysts. For example, the present invention relates to methods for directing and/or controlling metal deposition onto surfaces of porous substrates. The present invention also relates to methods for preparing catalysts in which a first metal is deposited onto a support (e.g., a porous carbon support) to provide one or more regions of a first metal at the surface of the support, and a second metal is deposited at the surface of the one or more regions of the first metal. Generally, the electropositivity of the first metal (e.g., copper or iron) is greater than the electropositivity of the second metal (e.g., a noble metal such as platinum) and the second metal is deposited at the surface of the one or more regions of the first metal by displacement of the first metal. The present invention further relates to treated substrates, catalyst precursor structures and catalysts prepared by these methods.Type: ApplicationFiled: May 1, 2009Publication date: December 31, 2009Applicant: MONSANTO TECHNOLOGY LLCInventor: Kam-To Wan
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Publication number: 20090259068Abstract: This invention generally relates to liquid phase oxidation processes for making N-(phosphonomethyl)glycine (also known in the agricultural chemical industry as glyphosate) and related compounds. This invention, for example, particularly relates to processes wherein an N-(phosphonomethyl)iminodiacetic acid (NPMIDA) substrate (i.e., N-(phosphonomethyl)iminodiacetic acid, a salt of N-(phosphonomethyl)iminodiacetic acid, or an ester of N-(phosphonomethyl)iminodiacetic acid) is continuously oxidized to form an N-(phosphonomethyl)glycine product (i.e., N-(phosphonomethyl)glycine, a salt of N-(phosphonomethyl)glycine, or an ester of N-(phosphonomethyl)glycine). This invention also, for example, particularly relates to processes wherein an N-(phosphonomethyl)iminodiacetic acid substrate is oxidized to form an N-(phosphonomethyl)glycine product, which, in turn, is crystallized (at least in part) in an adiabatic crystallizer.Type: ApplicationFiled: February 4, 2009Publication date: October 15, 2009Applicant: MONSANTO TECHNOLOGY LLCInventors: Eric Haupfear, Jerald D. Heise, Amy L. Jorgenson, Michael Rogers, Henry Chien, Eduardo Casanova, William Hooper, William Scholle, Juan Arhancet, Mark A. Leiber, Kent Wittler, Karen A. Wittler
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Publication number: 20090208499Abstract: The present invention relates to an N-(phosphonoalkyl)-amino acid, a related compound or a derivative thereof, the N-(phosphonoalkyl)-amino acid, related compound or derivative thereof being in a form as a free acid, salt, partial salt, lactone, amide or ester, or in stereoisomeric or non-stereoisomeric form, other than N-(phosphonomethyl)-glycine or N,N-bis(phosphonomethyl)-glycine. Also included is a composition including an N-(phosphonoalkyl)-amino acid, a related compound or a derivative thereof in a form as a free acid, salt, partial salt, lactone, amide or ester, or in stereoisomeric or non-stereoisomeric form, and a cosmetically or pharmaceutically acceptable vehicle for topical or systemic administration to a mammalian subject, as well as a method of administering an effective amount of such a composition for alleviating or improving a condition, disorder, symptom or syndrome associated with at least one of a nervous, vascular, musculoskeletal or cutaneous system.Type: ApplicationFiled: April 23, 2009Publication date: August 20, 2009Inventors: Ruey J. Yu, Eugene J. Van Scott
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Patent number: 7527733Abstract: The present invention provides for Troika acids attached to a macroporous resin and Methods of preparing the same, including direct attachment of a Troika acid, and attachment of a Troika acid precursor followed by generation of the Troika acid in situ. Methods of functionalizing a resin to facilitate attachment are also described. Multiple Troika acids, comprising a pair of Troika acids joined together are described. Synthetic routes to both microporous and macroporous resins modified by introduction of a suitable Troika-type acid have been designed and validated. In a preferred embodiment, a macroporous Troika resin removes Cu2+ and Ni2+ from aqueous solution with high affinity, and is selective against Mg2+ or Ca2+. The materials of the present invention have advantages for metal removal from power plant waste water.Type: GrantFiled: September 30, 2004Date of Patent: May 5, 2009Assignee: The University of Southern CaliforniaInventors: Charles E. McKenna, Boris A Kashemirov, Isabelle Favier, Thomas D. Wolfe
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Patent number: 7504534Abstract: This invention generally relates to liquid phase oxidation processes for making N-(phosphonomethyl)glycine (also known in the agricultural chemical industry as glyphosate) and related compounds. This invention, for example, particularly relates to processes wherein an N-(phosphonomethyl)iminodiacetic acid (NPMIDA) substrate (i.e., N-(phosphonomethyl)iminodiacetic acid, a salt of N-(phosphonomethyl)iminodiacetic acid, or an ester of N-(phosphonomethyl)iminodiacetic acid) is continuously oxidized to form an N-(phosphonomethyl)glycine product (i.e., N-(phosphonomethyl)glycine, a salt of N-(phosphonomethyl)glycine, or an ester of N-(phosphonomethyl)glycine). This invention also, for example, particularly relates to processes wherein an N-(phosphonomethyl)iminodiacetic acid substrate is oxidized to form an N-(phosphonomethyl)glycine product, which, in turn, is crystallized (at least in part) in an adiabatic crystallizer.Type: GrantFiled: November 22, 2005Date of Patent: March 17, 2009Assignee: Monsanto Technology LLCInventors: Eric A. Haupfear, Henry Chien, Eduardo Casanova, William B. Hooper
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Publication number: 20080317700Abstract: The present invention holds forth improvements in the field of herbicide synthesis, their application, and methods of plant and weed control and antifouling. The present invention includes the synthesis of new acrylate and methacrylate derivatives of a glyphosate. Two isomers resulting from a hindered rotation around the amide CN bond are observed for both acrylic and methacrylic analogs and barriers for internal rotation are obtained. Biological activity tests indicate that functionalized glyphosates possess herbicidal activity similar to the parent compound.Type: ApplicationFiled: December 21, 2007Publication date: December 25, 2008Applicant: Bowling Green State UniversityInventors: Douglas C. Neckers, Aneta Bogdanova, Andrei V. Fedorov
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Patent number: 7435847Abstract: A method of preparing ammonium glyphosate suitable for preparation of water-soluble solid ammonium glyphosate formulation by an extraction with organic solvent in a gas-liquid-solid phase system, which comprises adding glyphosate and water into a reactor with a stirer, introducing ammonia to carry out the reaction, an aqueous solution of ammonium glyphosate is formed after the reaction is completed; adding a water-soluble organic solvent such as methanol and/or ethanol and/or methylal to decrease the solubility of the ammonium glyphosate in the system, thereby crystallizing out ammonium glyphosate; and filtering in suction or further oven-drying to obtain the solid ammonium glyphosate. The organic solvent may be recovered and reused by rectifying or distilling, the remainder residue may be returned to the reaction procedure or used in the preparation of the aqueous formulation of ammonium glyphosate.Type: GrantFiled: September 4, 2003Date of Patent: October 14, 2008Assignee: Zhejiang Xin'Inventors: Wei Wang, Bufan Ren, Shuguang Zhou, Min Bao, Hongchao Zheng, Baiqing Zhang, Jiang Li
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Publication number: 20080183008Abstract: An improved process for recovering a crystalline product (particularly an N-(phosphonomethyl)glycine product) from a solution comprising both a product subject to crystallization and undesired impurities is provided.Type: ApplicationFiled: February 13, 2007Publication date: July 31, 2008Applicant: MONSANTO TECHNOLOGY LLCInventors: Eric A. Haupfear, Eduardo A. Casanova, Kenneth S. Meyer, Henry H. Chien
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Patent number: 7390920Abstract: This invention relates to the field of heterogeneous catalysis, and more particularly to catalysts including carbon supports having formed thereon compositions which comprise a transition metal in combination with nitrogen and/or carbon. The invention further relates to the fields of catalytic oxidation, including the preparation of secondary amines by the catalytic oxidation of tertiary amines.Type: GrantFiled: August 20, 2004Date of Patent: June 24, 2008Assignee: Monsanto Technology LLCInventors: James P. Coleman, Martin P. McGrath, Fuchen Liu, Juan Arhancet
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Patent number: 7329778Abstract: This invention is directed to a process for making a salt of a carboxylic acid. The process comprises contacting a catalyst with an alkaline mixture comprising a primary alcohol. In one embodiment, for example, the catalyst comprises a metal support (preferably a metal sponge support) having a copper-containing active phase at the surface thereof. The support is resistant to deformation under the conditions of the dehydrogenation reaction. In another embodiment, the catalyst comprises a metal sponge having a copper-containing active phase at the surface thereof and a supporting structure containing at least 10% non-copper metal. This invention is also directed to copper-containing catalysts which may, for example, be used in the above process. This invention is further directed to processes for making such catalysts.Type: GrantFiled: April 11, 2001Date of Patent: February 12, 2008Assignee: Monsanto Technology LLCInventors: David A. Morgenstern, Juan P. Arhancet, Howard C. Berk, William L. Moench, Jr., James C. Peterson
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Patent number: 7297657Abstract: This invention is directed to an improved process for the preparation of N-(phosphonomethyl)glycine (i.e., “glyphosate”), a salt of N-(phosphonomethyl)glycine, or an ester of N-(phosphonomethyl)glycine. The process comprises combining an N-substituted N-(phosphonomethyl)glycine reactant with oxygen in the presence of a noble metal catalyst. The N-substituted N-(phosphonomethyl)glycine reactant has formula (V): wherein R1 and R2 are independently selected from the group consisting of hydrogen, halogen, —PO3R12R13, —SO3R14, —NO2, hydrocarbyl, and substituted hydrocarbyl other than —CO2R15; and R7, R8, R9, R12, R13, R14 and R15 are independently selected from the group consisting of hydrogen, hydrocarbyl, substituted hydrocarbyl, and an agronomically acceptable cation.Type: GrantFiled: May 20, 2003Date of Patent: November 20, 2007Assignee: Monsanto Technology LLCInventor: David A. Morgenstern
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Patent number: 7294733Abstract: An improved process for the manufacture of formylphosphonic acid derivatives is reported. An aminomethylphosphonic acid substrate is contacted with a reagent selected from the group consisting of water, an alcohol, a phenol compound, and mixtures thereof and an oxidizing gas in the presence of a catalyst to form a reaction product mixture containing a formylphosphonic acid derivative and the conditions under which said contacting is carried out are controlled so that no more than 50% of the formylphosphonic acid derivative formed in the reaction product mixture is consumed by reaction with the reagent.Type: GrantFiled: June 5, 2006Date of Patent: November 13, 2007Assignee: Monsanto Technology LLCInventor: Thaddeus S. Franczyk, II
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Patent number: 7291751Abstract: This invention relates to the use of a supplemental promoter in conjunction with a noble-metal-containing catalyst comprising a carbon support in catalyzing liquid phase oxidation reactions, a process for making of an improved catalyst comprising such a supplemental promoter, and an improved catalyst comprising such a supplemental promoter. In a particularly preferred embodiment, a supplemental promoter (most preferably bismuth or tellurium) is used in conjunction with a noble-metal-containing catalyst comprising a carbon support in a liquid phase oxidation process wherein N-(phosphonomethyl)iminodiacetic acid (i.e., “PMIDA”) or a salt thereof is oxidized to form N-(phosphonomethyl)glycine (i.e., “glyphosate”) or a salt thereof. The benefits of such a process include increased oxidation of the formaldehyde and formic acid by-products, and, consequently, decreased final concentrations of those by-products as well as other undesirable by-products, most notably N-methyl-N-(phosphonomethyl)glycine (i.e.Type: GrantFiled: January 10, 2007Date of Patent: November 6, 2007Assignee: Monsanto Technology LLCInventors: Mark A. Leiber, Kam-To Wan
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Patent number: 7193107Abstract: This invention relates to the use of a promoter in conjunction with a noble-metal-containing catalyst comprising a carbon support in catalyzing liquid phase oxidation reactions. In a particularly preferred embodiment, the catalyst comprises a carbon support having a noble metal and tellurium at a surface of the carbon support and is used in a liquid phase oxidation process wherein N-(phosphonomethyl)iminodiacetic acid (i.e., “PMIDA”) or a salt thereof is oxidized to form N-(phosphonomethyl)glycine (i.e., “glyphosate”) or a salt thereof.Type: GrantFiled: August 22, 2005Date of Patent: March 20, 2007Assignee: Monsanto Technology LLCInventor: Mark A. Leiber
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Patent number: 7179936Abstract: An improved process for recovering a crystalline product (particularly an N-(phosphonomethyl)glycine product) from a solution comprising both a product subject to crystallization and undesired impurities is provided.Type: GrantFiled: September 17, 2004Date of Patent: February 20, 2007Assignee: Monsanto Technology LLCInventors: Eric A. Haupfear, Eduardo A. Casanova, Kenneth S. Meyer, Henry H. Chien
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Patent number: 7145034Abstract: The invention relates to a process for preparing N-phosphono-methylglycine by reacting a hexahydrotriazine compound with a triacyl phosphite in an organic solvent, hydrolyzing the resulting phosphono compound after prior extraction into an aqueous phase and separation from the organic phase. The process avoids decomposition of the organic solvent during hydrolysis.Type: GrantFiled: June 21, 2002Date of Patent: December 5, 2006Assignee: BASF AktiengesellschaftInventors: Christian Wulff, Stefan Orsten, Alfred Oftring, Peter Zehner
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Patent number: 7129373Abstract: An oxidation catalyst is prepared by pyrolyzing a source of iron and a source of nitrogen on a carbon support. Preferably, a noble metal is deposited over the modified support which comprises iron and nitrogen bound to the carbon support. The catalyst is effective for oxidation reactions such as the oxidative cleavage of tertiary amines to produce secondary amines, especially the oxidation of N-(phosphonomethyl)iminodiacetic acid to N-(phosphonomethyl)glycine.Type: GrantFiled: February 14, 2003Date of Patent: October 31, 2006Assignee: Monsanto Technology LLCInventors: James P. Coleman, Martin P. McGrath
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Patent number: 7091376Abstract: An improved process for the manufacture of formylphosphonic acid derivatives is reported. An aminomethylphosphonic acid substrate is contacted with a reagent selected from the group consisting of water, an alcohol, a phenol compound, and mixtures thereof and an oxidizing gas in the presence of a catalyst to form a reaction product mixture containing a formylphosphonic acid derivative and the conditions under which said contacting is carried out are controlled so that no more than 50% of the formylphosphonic acid derivative formed in the reaction product mixture is consumed by reaction with the reagent.Type: GrantFiled: June 15, 2004Date of Patent: August 15, 2006Assignee: Monsanto Technology LLCInventor: Thaddeus S. Franczyk, II
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Patent number: 7084298Abstract: The present invention relates to a process for the preparation of N-phosphonomethyliminodiacetic acid by reacting an alkali metal salt of iminodiacetic acid with phosphorus trichloride in aqueous solution with formation of the hydrochloride of iminodiacetic acid, phosphorous acid and of the corresponding alkali metal chloride, followed by reaction with a formaldehyde source and, if desired, recovery of the N-phosphonomethyliminodiacetic acid from the reaction mixture, in which water, which may comprise HCl, is removed from the reaction mixture during and/or after reacting the alkali metal salt of iminodiacetic acid with phosphorus trichloride until the concentration of iminodiacetic acid hydrochloride is at least 40% by weight, based on the weight of the reaction mixture minus the weight of alkali metal chloride. The process makes possible the preparation of N-phosphonomethyliminodiacetic acid in a simple fashion and in high yield.Type: GrantFiled: January 11, 2002Date of Patent: August 1, 2006Assignee: BASF AktiengesellschaftInventors: Matthias Maase, Michael Drögemüller
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Patent number: 7071354Abstract: The present invention relates to a process for the recovery of N-phosphonomethylglycine from an aqueous mixture which contains N-phosphonomethylglycine, ammonium halides, and alkali metal or alkaline earth metal halides and optionally organic impurities in dissolved form, where (a) the pH of the mixture is adjusted to a value in the range from 2 to 8, (b) a separation of the mixture on a selective nanofiltration membrane is performed, a retentate which is richer in N-phosphonomethylglycine and poorer in halides and a permeate which is richer in halides and poorer in N-phosphonomethylglycine being obtained, and (c) the N-phosphonomethylglycine is recovered from the retentate. The process according to the invention makes possible the recovery of the N-phosphonomethylglycine with simultaneous separation of the halide salts.Type: GrantFiled: June 21, 2002Date of Patent: July 4, 2006Assignee: BASF AktiengesellschaftInventors: Hugues Vandenmersch, Hartwig Voss, Stefan Orsten, Christian Wulff
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Patent number: 7067693Abstract: This invention relates to an improved catalyst, comprising a carbon support having a noble metal at its surface, for use in catalyzing liquid phase oxidation reactions, especially in an acidic oxidative environment and in the presence of solvents, reactants, intermediates, or products which solubilize noble metals; a process for the preparation of the improved catalyst; a liquid phase oxidation process using such a catalyst wherein the catalyst exhibits improved resistance to noble metal leaching, particularly in acidic oxidative environments and in the presence of solvents, reactants, intermediates, or products which solubilize noble metals; and a liquid phase oxidation process in which N-(phosphonomethyl)iminodiacetic acid (i.e., “PMIDA”) or a salt thereof is oxidized to form N-(phosphonomethyl) glycine (i.e., “glyphosate”) or a salt thereof using such a catalyst wherein the oxidation of the formaldehyde and formic acid by-products into carbon dioxide and water is increased.Type: GrantFiled: September 29, 1999Date of Patent: June 27, 2006Assignee: Monsanto Technology LLCInventors: Jerry R. Ebner, Mark A. Leiber, Kam-To Wan, Anthony Woods, Peter E. Rogers, Jingye Liu, William A. Scholle