Patents Represented by Attorney James C. Bolding
  • Patent number: 5498624
    Abstract: Novel azolyl derivatives, ie 2'-(substituted)cycloalkyl carboxanilides, useful as fungicides, methods of using said compounds and mixtures containing them.
    Type: Grant
    Filed: May 3, 1995
    Date of Patent: March 12, 1996
    Assignee: Monsanto Company
    Inventors: Jim I. McLoughlin, Deborah A. Mischke, Marla J. Williams, Suzanne Metz
  • Patent number: 5476992
    Abstract: A process for the in-situ remediation of a contaminated heterogeneous soil region comprising: (a) introducing material for treating contaminants in a contaminated heterogeneous soil region into at least one liquid permeable region within the contaminated heterogeneous soil region to form at least one treating zone within the contaminated heterogeneous soil region, (b) transmitting direct electric current through at least one low permeability soil region within the contaminated heterogeneous soil region between a first electrode and a second electrode having opposite charge, wherein (i) the first electrode is located at a first end of the contaminated heterogeneous soil region and the second electrode is located at the opposite end of the contaminated heterogeneous soil region or (ii) the first electrode is located at a first end of each of the low permeability soil regions and the second electrode is located at the opposite end of each of the low permeability soil regions, (1) to cause an electroosmotic flow
    Type: Grant
    Filed: November 17, 1993
    Date of Patent: December 19, 1995
    Assignee: Monsanto Company
    Inventors: Sa V. Ho, Philip H. Brodsky
  • Patent number: 5457155
    Abstract: A process for preparing a controlled functional density poly(secondary amine) comprising: (a) contacting a polymer containing olefinic unsaturation with carbon monoxide in hydrogen under hydroformylation conditions in the presence of a hydroformylation catalyst to produce a controlled functional density polyaldehyde containing reactive carbon-carbon double bonds, and (b) contacting the polyaldehyde with hydrogen and a primary amine under reductive amination conditions in the presence of a ruthenium-containing imine hydrogenation catalyst or (b.sup.1) contacting the polyaldehyde with a sterically hindered aliphatic or cycloaliphatic primary amine or an aromatic primary amine under reductive amination conditions in the presence of an alkali metal borohydride to produce poly(secondary amine) having a substantially equivalent ratio of secondary amine groups to reactive carbon-carbon double bonds as the ratio of aldehyde groups to reactive carbon-carbon double bonds in the polyaldehyde.
    Type: Grant
    Filed: February 3, 1995
    Date of Patent: October 10, 1995
    Assignee: Monsanto Company
    Inventors: Martin P. McGrath, Samuel J. Tremont
  • Patent number: 5457147
    Abstract: A process for preparing a controlled functional density poly(secondary amine) comprising: (a) contacting a polymer containing olefinic unsaturation with carbon monoxide in hydrogen under hydroformylation conditions in the presence of a hydroformylation catalyst to produce a controlled functional density polyaldehyde containing reactive carbon-carbon double bonds, and (b) contacting the polyaldehyde with hydrogen and a primary amine under reductive amination conditions in the presence of a ruthenium-containing imine hydrogenation catalyst or (b.sup.1) contacting the polyaldehyde with a sterically hindered aliphatic or cycloaliphatic primary amine or an aromatic primary amine under reductive amination conditions in the presence of an alkali metal borohydride to produce poly(secondary amine) having a substantially equivalent ratio of secondary amine groups to reactive carbon-carbon double bonds as the ratio of aldehyde groups to reactive carbon-carbon double bonds in the polyaldehyde.
    Type: Grant
    Filed: February 3, 1995
    Date of Patent: October 10, 1995
    Assignee: Monsato Company
    Inventors: Martin P. McGrath, Samuel J. Tremont
  • Patent number: 5453541
    Abstract: A method of producing 4-ADPA is disclosed wherein aniline or substituted aniline derivatives and nitrobenzene are reacted under suitable conditions to produce 4-nitrodiphenylamine or substituted derivatives thereof and/or 4-nitrosodiphenylamine or substituted derivatives thereof and/or their salts, either or both of which are subsequently reduced to produce 4-ADPA or substituted derivatives thereof. The 4-ADPA or substituted derivatives thereof can be reductively alkylated to produce p-phenylenediamine products or substituted derivatives thereof which are useful as antiozonants.
    Type: Grant
    Filed: December 6, 1993
    Date of Patent: September 26, 1995
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, James K. Bashkin
  • Patent number: 5451702
    Abstract: A process for preparing substituted aromatic amines is provided which comprises contacting a nucleophilic compound and an azo containing compound in the presence of a suitable solvent system, reacting the nucleophilic compound and the azo containing compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 10.degree. C. to about 150.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1 and reducing the product of the reaction of the nucleophilic compound and the azo containing compound under conditions which produce the substituted aromatic amine. In another embodiment, the substituted aromatic amines of the invention are reductively alkylated to produce alkylated diamines or substituted derivatives thereof.
    Type: Grant
    Filed: April 26, 1993
    Date of Patent: September 19, 1995
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, Brian K-M Cheng
  • Patent number: 5451697
    Abstract: A process for preparing isocyanates comprising contacting carbon dioxide and a primary amine in the presence of an aprotic organic solvent and a base selected from the group consisting of a phosphazene compound, an organic, nitrogenous base and mixtures thereof, wherein the organic, nitrogenous base selected from the group consisting of guanidine compounds, amidine compounds, tertiary amines and mixtures thereof to produce the corresponding ammonium carbamate salt, reacting the ammonium carbamate salt with an anhydride dehydrating agent to produce a product stream comprising the corresponding isocyanate, the aprotic organic solvent and the base salt derived from the anhydride, separating the base salt from the product stream, recovering and recycling the base, and regenerating and recycling the anhydride dehydrating agent.
    Type: Grant
    Filed: December 27, 1993
    Date of Patent: September 19, 1995
    Assignee: Monsanto Company
    Inventors: William D. McGhee, Mark D. Paster, Dennis P. Riley, Kenneth W. Ruettimann, A. John Solodar, Thomas E. Waldman
  • Patent number: 5436371
    Abstract: A process for preparing p-nitroaromatic amides is provided which comprises contacting a nitrile, nitrobenzene, a suitable base and water in the presence of a suitable solvent system to form a mixture, and reacting the mixture at a suitable temperature in a confined reaction zone in the presence of a controlled amount of protic material. The p-nitroaromatic amides of the invention can be reduced to p-aminoaromatic amides. In one embodiment, the p-aminoaromatic amide is further reacted with ammonia under conditions which produce the corresponding p-aminoaromatic amine and the amide corresponding to the nitrile starting material or with water in the presence of a suitable basic or acidic catalyst under conditions which produce the corresponding p-aminoaromatic amine and the acid or salt thereof corresponding to the nitrile starting material. In another embodiment, the p-aminoaromatic amine is reductively alkylated to produce alkylated p-aminoaromatic amine.
    Type: Grant
    Filed: August 29, 1994
    Date of Patent: July 25, 1995
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, Brian K. Cheng
  • Patent number: 5434288
    Abstract: PLA.sub.2 inhibitors selected from the group consisting of ##STR1## wherein A is selected from the group consisting of ##STR2## and Z, W, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, X, X' and Y are as defined herein.
    Type: Grant
    Filed: June 14, 1994
    Date of Patent: July 18, 1995
    Assignee: Monsanto Company
    Inventor: Patrick J. Lennon
  • Patent number: 5434309
    Abstract: A process for preparing a controlled functional density poly(secondary amine) comprising:(a) contacting a polymer containing olefinic unsaturation with carbon monoxide in hydrogen under hydroformylation conditions in the presence of a hydroformylation catalyst to produce a controlled functional density polyaldehyde containing reactive carbon-carbon double bonds, and (b) contacting the polyaldehyde with hydrogen and a primary amine under reductive amination conditions in the presence of a ruthenium-containing imine hydrogenation catalyst or (b.sup.1) contacting the polyaldehyde with a sterically hindered aliphatic or cycloaliphatic primary amine or an aromatic primary amine under reductive amination conditions in the presence of an alkali metal borohydride to produce poly(secondary amine) having a substantially equivalent ratio of secondary amine groups to reactive carbon-carbon double bonds as the ratio of aldehyde groups to reactive carbon-carbon double bonds in the polyaldehyde.
    Type: Grant
    Filed: April 28, 1994
    Date of Patent: July 18, 1995
    Assignee: Monsanto Company
    Inventors: Martin P. McGrath, Samuel J. Tremont
  • Patent number: 5398756
    Abstract: A process for the in-situ remediation of contaminated soil comprising: (a) forming at least one liquid permeable region within a contaminated soil region, (b) introducing material for treating contaminants in the contaminated soil region into the liquid permeable regions to form at least one treating zone within the contaminated soil region, and (c) transmitting direct electric current through the contaminated soil region between a first electrode and a second electrode having opposite charge, wherein the first electrode is located at a first end of the contaminated soil region and the second electrode is located at the opposite end of the contaminated soil region to cause an electroosmotic flow from the second to the first electrode.
    Type: Grant
    Filed: November 17, 1993
    Date of Patent: March 21, 1995
    Assignee: Monsanto Company
    Inventors: Philip H. Brodsky, Sa V. Ho
  • Patent number: 5382691
    Abstract: A process for preparing substituted aromatic amines is provided which comprises contacting a substituted aromatic azo compound and an alcohol selected from the group consisting of aliphatic alcohols, cycloaliphatic alcohols, arylalkyl alcohols and mixtures thereof in the presence of a suitable base at a temperature of about 70.degree. C. to about 200.degree. C. In another embodiment, the substituted aromatic amines of the invention are reductively alkylated to produce alkylated diamines or substituted derivatives thereof.
    Type: Grant
    Filed: November 5, 1993
    Date of Patent: January 17, 1995
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, Brian K-M. Cheng
  • Patent number: 5380946
    Abstract: A process for preparing p-nitroaromatic amides is provided which comprises contacting a nitrile, nitrobenzene, a suitable base and water in the presence of a suitable solvent system to form a mixture, and reacting the mixture at a suitable temperature in a confined reaction zone in the presence of a controlled amount of protic material. The p-nitroaromatic amides of the invention can be reduced to p-aminoaromatic amides. In one embodiment, the p-aminoaromatic amide is further reacted with ammonia under conditions which produce the corresponding p-aminoaromatic amine and the amide corresponding to the nitrile starting material or with water in the presence of a suitable basic or acidic catalyst under conditions which produce the corresponding p-aminoaromatic amine and the acid or salt thereof corresponding to the nitrile starting material. In another embodiment, the p-aminoaromatic amine is reductively alkylated to produce alkylated p-aminoaromatic amine.
    Type: Grant
    Filed: July 30, 1993
    Date of Patent: January 10, 1995
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, Brian K. M. Cheng
  • Patent number: 5380855
    Abstract: A process for preparing N,N-substituted carbamoyl halides comprising (a) contacting carbon dioxide and a secondary amine in the presence of an aprotic organic solvent and a base selected from the group consisting of a phosphazene compound, an organic, nitrogenous base, mixtures of pyridine and a phosphazene compound or an organic, nitrogenous base, and mixtures thereof, to produce the corresponding ammonium carbamate salt, and (b) reacting the ammonium carbamate salt with a halide-containing electrophilic compound to produce the corresponding N,N-substituted carbamoyl halides. A second embodiment comprises recovering the ammonium carbamate salt of step (a) prior to reacting the ammonium carbamate salt with an halide-containing electrophilic compound in the presence of an aprotic organic solvent and a base selected from the group consisting of a phosphazene compound, an organic, nitrogenous base, mixtures of pyridine and a phosphazene compound or an organic, nitrogenous base, and mixtures thereof.
    Type: Grant
    Filed: February 4, 1994
    Date of Patent: January 10, 1995
    Assignee: Monsanto Company
    Inventors: William D. McGhee, John J. Talley
  • Patent number: 5371183
    Abstract: The present invention provides a process for preparing urethanes and carbonates from an amine or an alcohol, carbon dioxide and a hydrocarbyl halide. The amine or alcohol is reacted with carbon dioxide in a suitable solvent system and in the presence of an amidine or guanidine base, to form the ammonium carbamate or carbonate salt which is then reacted in a polar aprotic solvent with a hydrocarbyl halide. Polymer products can also be prepared utilizing this process or utilizing the resulting urethanes and carbonates under standard polymerization conditions.
    Type: Grant
    Filed: November 16, 1992
    Date of Patent: December 6, 1994
    Assignee: Monsanto Company
    Inventors: William D. McGhee, Dennis P. Riley
  • Patent number: 5349048
    Abstract: The present invention provides a process for preparing urethanes and carbonates from an amine or an alcohol, carbon dioxide and a hydrocarbyl halide. The amine or alcohol is reacted with carbon dioxide in a suitable solvent system and in the presence of an amidine or guanidine base, to form the ammonium carbamate or carbonate salt which is then reacted in a polar aprotic solvent with a hydrocarbyl halide. Polymer products can also be prepared utilizing this process or utilizing the resulting urethanes and carbonates under standard polymerization conditions.
    Type: Grant
    Filed: December 27, 1993
    Date of Patent: September 20, 1994
    Assignee: Monsanto Company
    Inventors: William D. McGhee, Dennis P. Riley
  • Patent number: 5349081
    Abstract: A process for preparing isocyanates comprising (a) contacting carbon dioxide and a primary amine in the presence of an aprotic organic solvent and a base selected from the group consisting of a phosphazene compound, an organic, nitrogenous base and mixtures thereof, wherein the organic, nitrogenous base selected from the group consisting of guanidine compounds, amidine compounds, tertiary amines, pyridine and mixtures thereof to produce the corresponding ammonium carbamate salt, and (b) reacting the ammonium carbamate salt with an electrophilic or oxophilic dehydrating agent to produce the corresponding isocyanate.
    Type: Grant
    Filed: January 21, 1993
    Date of Patent: September 20, 1994
    Assignee: Monsanto Company
    Inventor: William D. McGhee
  • Patent number: 5344934
    Abstract: The present invention provides a process for preparing urethanes and carbonates from an amine or an alcohol, carbon dioxide and a hydrocarbyl halide. The amine or alcohol is reacted with carbon dioxide in a suitable solvent system and in the presence of an amidine or guanidine base, to form the ammonium carbamate or carbonate salt which is then reacted in a polar aprotic solvent with a hydrocarbyl halide. Polymer products can also be prepared utilizing this process or utilizing the resulting urethanes and carbonates under standard polymerization conditions.
    Type: Grant
    Filed: November 16, 1992
    Date of Patent: September 6, 1994
    Assignee: Monsanto Company
    Inventors: William D. McGhee, Dennis P. Riley, John J. Talley, Barry L. Parnas
  • Patent number: 5331099
    Abstract: A process for preparing p-nitroaromatic amides is provided which comprises contacting an amide and nitrobenzene in the presence of a suitable solvent system, and reacting the amide and nitrobenzene in the presence of a suitable base and a controlled amount of protic material at a suitable temperature in a confined reaction zone. The p-nitroaromatic amides of the invention can be reduced to p-aminoaromatic amides. In one embodiment, the p-aminoaromatic amide is further reacted with ammonia under conditions which produce the corresponding p-aminoaromatic amine and the amide starting material which can be recycled or with water in the presence of a suitable basic or acidic catalyst under conditions which produce the corresponding p-aminoaromatic amine and the acid or salt thereof corresponding to the amide starting material. In another embodiment, the p-aminoaromatic amine is reductively alkylated to produce alkylated p-aminoaromatic amine.
    Type: Grant
    Filed: April 16, 1993
    Date of Patent: July 19, 1994
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, James K. Bashkin
  • Patent number: 5321153
    Abstract: This invention is selected novel chiral (essentially pure) alpha-amino phosphonates, process for the preparation which is a catalytic asymmetric hydrogenation of olefins and novel intermediates therefor. The alpha-amino phosphonates are useful as antibiotics and/or as intermediates in the preparation of phosphorus-containing analogs of peptides, i.e., phosphonopeptides or pseudopeptides having known uses, such as in antibiotics, antibiotic enhancers, or enzyme inhibitors.
    Type: Grant
    Filed: June 15, 1992
    Date of Patent: June 14, 1994
    Assignee: Monsanto Company
    Inventor: John J. Talley