Patents Represented by Attorney Kenneth D. Goetz
  • 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: 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: 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: 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: 5302717
    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 a base selected from the group consisting of a phosphazene compound and a mixture of a phosphazene compound and an organic, nitrogenous 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: October 15, 1992
    Date of Patent: April 12, 1994
    Assignee: Monsanto Company
    Inventors: William D. McGhee, John J. Talley
  • Patent number: 5298651
    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 phosphazene compound or a mixture of a phosphazene compound and an 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. A second embodiment comprises recovering the ammonium carbamate salt of step (a) prior to reacting the ammonium carbamate salt with an electrophilic or oxophilic dehydrating agent in the presence of an aprotic organic solvent and a phosphazene compound or a mixture of a phosphazene compound and an organic, nitrogenous base selected from the group consisting of guanidine compounds, amidine compounds, tertiary amines, pyridine and mixtures thereof.
    Type: Grant
    Filed: October 15, 1992
    Date of Patent: March 29, 1994
    Assignee: Monsanto Company
    Inventors: William D. McGhee, Thomas E. Waldman
  • Patent number: 5273981
    Abstract: Novel compounds represented by the formula: ##STR1## wherein R represents hydrogen, alkyl radicals having from 1 to about 10 carbon atoms, alkenyl radicals having from 1 to about 10 carbon atoms, aryl, alkaryl and aralkyl radicals having from about 6 to about 16 carbon atoms and acyl and acyloxy radicals having from about 1 to about 10 carbon atoms, manifest glycosidase inhibition activity.
    Type: Grant
    Filed: April 16, 1992
    Date of Patent: December 28, 1993
    Assignee: Monsanto Company
    Inventors: Daniel P. Getman, Gary A. DeCrescenzo
  • Patent number: 5260473
    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: November 9, 1993
    Assignee: Monsanto Company
    Inventors: William D. McGhee, Dennis P. Riley
  • Patent number: 5252737
    Abstract: A process for preparing N-aliphatic substituted p-phenylenediamine intermediates is provided which comprises contacting an aliphatic amine or substituted aliphatic amine derivative and nitrobenzene in the presence of a suitable solvent system, and reacting the aliphatic amine or substituted aliphatic amine derivative 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. In one embodiment, the N-aliphatic substituted p-phenylenediamine intermediates are reduced to N-aliphatic substituted p-phenylenediamines and the N-aliphatic substituted p-phenylenediamines can be reductively alkylated to N'-alkylated, N-aliphatic substituted p-phenylenediamines. In another embodiment of the invention, N-aliphatic substituted p-phenylenediamine intermediates are reductively alkylated to N'-alkylated, N-aliphatic substituted p-phenylenediamines.
    Type: Grant
    Filed: May 22, 1992
    Date of Patent: October 12, 1993
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, Brian K. Cheng
  • Patent number: 5233010
    Abstract: A process for preparing an isocyanate having at least two --N.dbd.C.dbd.O groups is provided which comprises preparing a substituted aromatic amine having at least two --NH.sub.2 groups, recovering the substituted aromatic amine having at least two --NH.sub.2 groups, and preparing an isocyanate from the substituted aromatic amine having at least two --NH.sub.2 groups by (1) contacting the substituted aromatic amine with CO.sub.2 under conditions sufficient to produce the corresponding ammonium carbamate salt, and reacting the ammonium carbamate salt with an electrophilic or oxophilic dehydrating agent under conditions sufficient to produce the corresponding isocyanate, or (2) contacting the substituted aromatic amine with CO.sub.
    Type: Grant
    Filed: October 15, 1992
    Date of Patent: August 3, 1993
    Assignee: Monsanto Company
    Inventors: William D. McGhee, Michael K. Stern, Thomas E. Waldman
  • Patent number: 5232989
    Abstract: Functionalized polymers manifesting exceptional stress-strain properties are prepared from polyols having terminal and nonterminal hydroxyl groups.
    Type: Grant
    Filed: March 4, 1991
    Date of Patent: August 3, 1993
    Assignee: Monsanto Company
    Inventors: Denis Forster, Samuel J. Tremont, Martin P. McGrath, Erik D. Sall
  • Patent number: 5233084
    Abstract: Process for preparing .alpha.-arylpropionic acids by catalytically asymmetrically hydrogenating .alpha.-arylpropenoic acids prepared from .alpha.-aryl ketones.
    Type: Grant
    Filed: December 3, 1990
    Date of Patent: August 3, 1993
    Assignee: Monsanto Company
    Inventor: Albert S. C. Chan
  • Patent number: 5223638
    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: April 29, 1991
    Date of Patent: June 29, 1993
    Assignee: Monsanto Company
    Inventors: William D. McGhee, Barry L. Parnas, Dennis P. Riley, John J. Talley
  • Patent number: 5202474
    Abstract: Process for preparing .alpha.-arylpropionic acids by catalytically asymmetrically hydrogenating .alpha.-arylpropenoic acids utilizing an asymmetric hydrogenation catalyst at low temperatures and, optionally, at high pressures.
    Type: Grant
    Filed: March 2, 1990
    Date of Patent: April 13, 1993
    Assignee: Monsanto Company
    Inventor: Albert S. C. Chan
  • Patent number: 5202473
    Abstract: A ruthenium-phosphine complex represented by the formula:[RuXY(BINAP].sub.nwherein n is an integer of from 1 to about 10; and X and Y independently represent nonchelating anionic ligands.
    Type: Grant
    Filed: July 23, 1992
    Date of Patent: April 13, 1993
    Assignee: Monsanto Company
    Inventors: Albert S. C. Chan, Scott A. Laneman
  • Patent number: 5200547
    Abstract: The present invention provides a process for preparing urethanes and carbonates from an amine or an alcohol, carbon dioxide and an allyl halide. The amine or alcohol is reacted with carbon dioxide to form the ammonium carbamate or carbonate salt which is then reacted with a palladium tertiary phosphine catalyst complex of an allyl halide. Polymer products can also be prepared utilizing this process or utilizing the resulting urethanes and carbonates under standard polymerization conditions.
    Type: Grant
    Filed: September 4, 1990
    Date of Patent: April 6, 1993
    Assignee: Monsanto Company
    Inventors: Dennis P. Riley, William D. McGhee