Patents Represented by Attorney, Agent or Law Firm Joseph A. Schaper
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Patent number: 6818450Abstract: The present invention is directed to an analytical method for measuring the concentration of an N-(phosphonomethyl)iminodiacetic acid (“NPMIDA”) substrate, an N-(phosphonomethyl)glycine product, formaldehyde, formic acid, N-methyl-N-(phosphonomethyl)glycine (“NMG”), N-methyl-aminomethylphosphonic acid (MAMPA) or aminomethylphosphonic acid (“AMPA”)) in an aqueous mixture thereof, using infrared spectroscopy. The present invention is also directed to a process for oxidizing an N-(phosphonomethyl)iminodiacetic acid substrate to form a N-(phosphonomethyl)glycine product, and as part of the process, measuring the concentration of at least one reactant, product or byproduct of the oxidation reaction using the analytical method of the present invention and controlling the oxidation process in response to the measurement taken.Type: GrantFiled: May 17, 2002Date of Patent: November 16, 2004Assignee: Monsanto Technology LLCInventors: David R. Eaton, Walter Gavlick, Gary Klopf, Arnold Hershman, Denis Forster
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Patent number: 6809819Abstract: The present invention relates to methods for analyzing agricultural products. More particularly, the present invention relates to methods for analysis of the oil content of one or more seeds.Type: GrantFiled: September 26, 2000Date of Patent: October 26, 2004Assignee: Monsanto Technology LLCInventors: Dutt V. Vinjamoori, Pradip K. Das, John A. Long
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Patent number: 6762317Abstract: 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: September 4, 2002Date of Patent: July 13, 2004Assignee: Monsanto CompanyInventor: Thaddeus S. Franczyk, II
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Patent number: 6759549Abstract: Novel compounds, N,N′-bis(phosphonomethyl)-N,N′-bis(hydroxycarbonylmethyl)urea and N,N,N′,N′-tetrakis(hydroxycarbonylmethyl)urea, suitable for use in preparing N-acyl aminocarboxylic acids that can be readily converted to N-(phosphonomethyl)glycine are provided. The compounds may be formed by the reaction of bis-(phosophonomethyl)urea or urea respectively with carbon monoxide and formaldehyde in the presence of a carboxymethylation catalyst precursor and solvent.Type: GrantFiled: April 7, 2003Date of Patent: July 6, 2004Assignee: Monsanto Technology LLCInventors: Michael K. Stern, Todd J. Johnson
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Patent number: 6734142Abstract: A process is provided for preparing a downstream processable ammonium glyphosate paste. The process includes mixing in a reactor (i) particulate glyphosate acid, (ii) ammonia, (iii) adjuvant, and (iii) water. The reaction of glyphosate acid with ammonia causes the generation of heat resulting in the partial evaporation of the water such that an ammonium glyphosate paste is formed, having a moisture content of about 2% to about 20% by weight. The addition of the adjuvant to the reactor (i) increases the rate at which the glyphosate acid and ammonia react to form ammonium glyphosate and/or (ii) reduces the flow resistance of the reaction mass as it is being conveyed to the product discharge region of the reactor. The ammonium glyphosate paste may then be further processed to form a granular herbicidal composition.Type: GrantFiled: April 15, 2002Date of Patent: May 11, 2004Assignee: Monsanto Technology LLCInventors: Brent D. Massmann, John T. Wang, Dwane H. Campbell
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Patent number: 6730813Abstract: The invention relates to a method for producing N-(phosphonomethyl)glycine involving the following steps: (a) oxidizing N-(phosphonomethyl)iminodiacetic acid (PMIDA) with peroxides or oxygen in an aqueous medium and in the presence of a heterogeneous catalyst at a temperature ranging from 50 to 150° C.; (b) subsequently separating the solid catalyst out of the aqueous reaction suspension of step (a); (c) concentrating the clear reaction solution from step (b), especially by evaporation, and; (d) separating the N-(phosphonomethyl)glycine out of the concentrated reaction solution from step (c), especially by filtration. According to the invention, the aqueous reaction solution from step (d) (mother liquor) is returned with small amounts of N-(phosphonomethyl)glycine and byproducts to step (b) (catalyst separation) and/or to step (c) (concentration). This results in distinctly increasing the yield with a constant product purity and in noticeably reducing the amount of mother liquor.Type: GrantFiled: August 16, 2002Date of Patent: May 4, 2004Assignee: Monsanto Technology LLCInventors: Martin Hitzler, Franz Thalhammer, Benedikt Hammer
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Patent number: 6713433Abstract: A stable, liquid concentrate herbicidal composition is provided. The composition comprises a water-soluble herbicide in a continuous aqueous phase and an oil-soluble herbicide in a discontinuous oil phase.Type: GrantFiled: February 14, 2002Date of Patent: March 30, 2004Assignee: Monsanto Technology, LLCInventor: Ganiyu A. Jimoh
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Patent number: 6706662Abstract: This invention is directed to a process for dehydrogenating primary alcohols to make salts of carboxylic acids. The process comprises contacting a catalyst, preferably a metal support coated with copper or silver, with an alkaline mixture comprising a primary alcohol. The invention further provides for novel copper-containing and silver-containing catalysts which may be used, for example, in the above process as well as processes for making such catalysts.Type: GrantFiled: February 28, 2002Date of Patent: March 16, 2004Assignee: 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: 6689719Abstract: A stable, liquid concentrate herbicidal microemulsion composition is provided. The composition comprises N-(phosphonomethyl)glycine or a salt thereof in a continuous aqueous phase and carfentrazone-ethyl in a discontinuous oil phase.Type: GrantFiled: February 14, 2002Date of Patent: February 10, 2004Assignees: Monsanto Technology LLC, FMC CorporationInventor: Ganiyu A. Jimoh
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Patent number: 6605568Abstract: A process is provided for preparing a downstream processable ammonium glyphosate paste, comprising mixing in a suitable vessel (i) particulate glyphosate acid, (ii) ammonia in an amount of about 0.8 to about 1.25 moles per mole of the glyphosate acid, and (iii) water in an amount of about 10% to about 25% by weight of all materials being mixed in the vessel, thereby causing a reaction of the glyphosate acid and ammonia that generates heat causing partial evaporation of the water, and forms an ammonium glyphosate paste having a moisture content of about 5% to about 20% by weight.Type: GrantFiled: July 27, 2000Date of Patent: August 12, 2003Assignees: Monsanto Technology LLC, Monsanto Europe, S.A.Inventors: Brent D. Massmann, Richard M. Kramer, John T. Wang, Marc Emile Toussaint
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Patent number: 6603039Abstract: 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: August 5, 2003Assignee: Monsanto Technology LLCInventors: Jerry R. Ebner, Mark A. Leiber, Kam-To Wan, Peter E. Rogers, Jingyue Liu, Anthony Woods
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Patent number: 6599858Abstract: A process is provided for preparing ammonium glyphosate flakes, comprising (a) mixing (i) solid particulate glyphosate acid, (ii) water in an amount of about 0.5 to about 3 parts by weight per part by weight of glyphosate acid, and (iii) a base that supplies ammonium cations, in an amount of about 0.8 to about 1.25 mole equivalents of ammonia per mole of glyphosate acid, to form an aqueous reaction medium; (b) allowing the glyphosate acid to react with the base in the reaction medium to form a reaction product comprising a concentrated aqueous solution of ammonium glyphosate; (c) drying the reaction product by contact thereof with a heated surface to form, primarily by evaporation of water, a solid deposit on the heated surface; and (d) scraping the solid deposit off the heated surface to recover dry flakes of ammonium glyphosate.Type: GrantFiled: July 25, 2000Date of Patent: July 29, 2003Assignee: Monsanto Technology LLCInventor: Richard M. Kramer
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Patent number: 6586621Abstract: 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.Type: GrantFiled: December 21, 2000Date of Patent: July 1, 2003Assignee: Monsanto Technology LLCInventors: Mark A. Leiber, Jerry R. Ebner, Kam-To Wan, Anthony Woods, Peter Rogers
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Patent number: 6569809Abstract: A concentrate package-mix composition comprising a water-soluble pesticide or plant growth regulator, for example a salt of the herbicide glyphosate, and a solid water-insoluble pesticide or plant growth regulator, for example the herbicide flumioxazin, is provided. The water-soluble pesticide or plant growth regulator is dissolved in a continuous aqueous phase of the composition and solid particles of the water-insoluble pesticide or plant growth regulator are suspended in the aqueous phase. These solid particles, individually or plurally, are intimately surrounded by a barrier layer, which comprises either one or both of a water-immiscible organic solvent or an emulsifying agent that has a hydrophile-lipophile balance (HLB) not greater than about 15. Optionally the composition further comprises a viscosity modifying agent, such as colloidal hydrophilic silica, dispersed in the aqueous phase.Type: GrantFiled: September 27, 2000Date of Patent: May 27, 2003Assignee: Monsanto CompanyInventors: Tatsuo Sato, Masus Kuchikata
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Patent number: 6544930Abstract: A storage and shipping system for glyphosate herbicide is provided, comprising a container having a capacity of about 0.1 to about 100,000 liters or more, substantially filled with an aqueous solution of glyphosate, predominantly in the form of one or a mixture of the potassium and monoethanolammonium salts thereof, the solution having a glyphosate acid equivalent concentration of at least about 30 percent by weight. The storage and shipping system, by virtue of the relatively high specific gravity of the glyphosate salt solution, holds a greater weight of glyphosate than a system comprising an identical container substantially filled with an aqueous solution of the isopropylammonium salt of glyphosate at the same glyphosate concentration by weight. Alternatively, the container of the storage and shipping system can be smaller than that of a container holding the same weight of glyphosate in the form of the isopropylammonium salt.Type: GrantFiled: November 16, 2001Date of Patent: April 8, 2003Assignee: Monsanto Technology LLCInventor: Daniel R. Wright
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Patent number: 6500783Abstract: A plant treatment composition for application of an anionic exogenous chemical substance such as glyphosate to foliage of a plant is provided.Type: GrantFiled: November 30, 1999Date of Patent: December 31, 2002Assignee: Monsanto Technology LLCInventors: Nathan J. Bryson, Olivier Soula, Alain J. L. Lemercier, Rémi Meyrueix, Gérard G. Soula
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Patent number: 6476256Abstract: A process for the preparation of an oxyacid of phosphorus comprising contacting elemental phosphorus with water in the presence of a catalyst effective to promote oxidation of phosphorus by reaction with water. The use of a noble metal catalyst such as Pd under moderate agitation and low severity conditions is effective for the preparation of P(III) oxyacid in high selectivity. Other suitable catalysts may comprise, for example, other Group VIII metals (particularly other platinum metals); oxides, salts, phosphides, and/or coordination compounds of Group VIII metals; Group IB metals; and/or oxides, salts, phosphides, and/or coordination is compounds of Group IB metals. Various apparatus and process schemes for the preparation of phosphoric and phosphorous acid are also disclosed.Type: GrantFiled: May 29, 2001Date of Patent: November 5, 2002Assignee: Monsanto CompanyInventors: Jerald D. Heise, Erik D. Sall, Martin P. McGrath
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Patent number: 6475953Abstract: A composition is disclosed for application to a plant that comprises glyphosate, an aqueous diluent, and an excipient substance that is amphiphilic. The weight/weight ratio of the excipient substance to the exogenous chemical is between about 1:3 and about 1:100. The aqueous composition forms anisotropic aggregates on a wax layer, and the presence of the anisotropic aggregates can be detected by a test described herein. Compositions of the present invention, when applied to plants, provide enhanced biological activity per unit amount of glyphosate, as compared to otherwise similar compositions containing surfactants that do not form anisotropic aggregates. Without being bound by theory, it is presently believed that this enhanced biological activity results from the formation or enlargement of hydrophilic channels through the epicuticular wax of the plant.Type: GrantFiled: March 24, 2000Date of Patent: November 5, 2002Assignee: Monsanto Technology LLCInventors: Anthony J. I. Ward, Jisheng Ge, Jane L. Gillespie, Joseph J. Sandbrink, Xiaodong C. Xu
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Patent number: 6461997Abstract: New herbicidal compounds are provided having the formula wherein Y is oxygen or sulfur; R1 and R2 are each independently a C1-4 hydrocarbyl group, unsubstituted or substituted with one or more halogen, haloalkyl, hydroxy, alkoxy, carboxy, amido, cyano or amino groups; or R1 and R2, together with the carbamoyl nitrogen atom to which they are attached, form a nitrogen-containing five or six membered ring, the ring being optionally interrupted by an ethereal oxygen atom and unsubstituted or substituted with one or more hydroxy, amido, cyano, amino or C1-8 alkyl, alkenyl, alkynyl, cycloalkyl, arylalkyl, alkoxy, aminoalkyl or haloalkyl groups; and R3 is hydrogen, halogen, or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, cycloalkylalkenyl, aryl, arylalkyl, alkylthio or arylalkylthio group that is unsubstituted or substituted with one or more halo, hydroxy, alkoxy, acetyloxy, benzoyloxy, alkoxycarbonyl, silyl or alkylsilyl groups; or an agronomically acceptable acid addition salt or metal complex ofType: GrantFiled: January 13, 2000Date of Patent: October 8, 2002Assignee: Monsanto Technology LLCInventors: Shridhar G. Hegde, Martin D. Mahoney
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Patent number: 6455473Abstract: A herbicidal composition is provided comprising an aqueous solution of N-phosphonomethylglycine, predominantly in the form of the monoethanolammonium salt thereof, at a concentration of about 30% to about 48% N-phosphonomethylglycine acid equivalent by weight. In a particular embodiment, a herbicidal composition comprises water; N-phosphonomethylglycine predominantly in the form of the monoethanolammonium salt thereof in solution in the water in an amount of about 360 to about 570 g a.e./l of the composition; and a surfactant component in solution or stable dispersion in the water, comprising one or more surfactants in a total amount of about 20 to about 200 g/l of the composition, this surfactant component being selected such that the composition has a cloud point not lower than about 50° C.Type: GrantFiled: April 3, 2001Date of Patent: September 24, 2002Assignee: Monsanto Technology LLCInventor: Daniel R. Wright