Patents by Inventor Karl L. Krumel

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

  • Patent number: 6211403
    Abstract: 1-Halo-2-chloro-3-alkoxy-4-alkylsulfonylbenzene and 1-halo-2,3-dichloro-4-alkylsulfonylbenzene compounds were converted to compounds having hydroxycarbonyl or alkoxycarbonyl substituents in place of the 1-halo substituent by reaction with carbon monoxide and water or an alcohol respectively, in the presence of a palladium II salt: trihydrocarbylphosphine complex type catalyst.
    Type: Grant
    Filed: November 15, 1999
    Date of Patent: April 3, 2001
    Assignee: Dow AgroSciences LLC
    Inventors: Thomas L. Siddall, Karl L. Krumel, Mark V. M. Emonds, Jennifer M. Schomaker, Mark W. Zettler
  • Patent number: 6015911
    Abstract: Herbicidal 1-alkyl-4-(2-chloro-3-alkoxy-4-alkylsulfonylbenzoyl)-5-hydroxypyrazole compounds, as well as 1-halo-2-chloro-3-alkoxy-4-alkylsulfonylbenzene compounds and 2-chloro-3-alkoxy-4-alkylsulfonylbenzoic acid compounds, were prepared in good yield by the reaction of the corresponding 3-chloro compound with an alkali metal alkoxide compound. 1-Halo-2-chloro-3-alkoxy-4-alkylsulfonylbenzene and 1-halo-2,3-dichloro-4-alkylsulfonylbenzene compounds were converted to compounds having hydroxycarbonyl, alkoxycarbonyl, or 1-alkyl-5-hydroxypyrazole-4-carbonyl substituents in place of the 1-halo substituent by reaction with carbon monoxide and water, an alcohol, or a 1-alkyl-5-hydroxypyrazole compound, respectively, in the presence of a palladium II salt:trihydrocarbylphosphine complex type catalyst.
    Type: Grant
    Filed: March 24, 1998
    Date of Patent: January 18, 2000
    Assignee: Dow AgroSciences LLC
    Inventors: Thomas L. Siddall, Mark V. M. Emonds, Karl L. Krumel, Jennifer M. Schomaker, Mark W. Zettler
  • Patent number: 5973153
    Abstract: The present invention relates to a new improved, simplified process for the preparation of halo-4-phenoxyquinolines, whereby thionyl chloride is used as the chlorinating agent to prepare the corresponding chloroquinoline intermediate prior to the final coupling reaction, and a single, inert high boiling polyether solvent is used throughout the entire reaction procedure.
    Type: Grant
    Filed: January 15, 1998
    Date of Patent: October 26, 1999
    Inventors: Tim J. Adaway, Jeff T. Budd, Ian R. King, Karl L. Krumel, Larry D. Kershner, Julie L. Maurer, Thomas A. Olmstead, Gary A. Roth, Jimmy J. Tai, Mark A. Hadd
  • Patent number: 5214150
    Abstract: Larger (C.sub.6 -C.sub.12) esters of substituted 2-pyridinyloxyalkanoic acids, such as 1-methylheptyl (4-amino-3,5-dichloro-6-fluoro-2-pyridinyloxy)acetate, are prepared in high yield and purity by first preparing the methyl or ethyl ester and then transesterifying with a C.sub.6 -C.sub.12 alcohol. The methyl or ethyl ester can be prepared by alkylation of an alkali metal salt of 4-amino-3,5-dichloro-6-fluoro-2-pyridinol with methyl or ethyl chloroacetate and the transesterification can be carried out in the presence of a tetraalkyl titanate catalyst.
    Type: Grant
    Filed: July 2, 1991
    Date of Patent: May 25, 1993
    Assignee: DowElanco
    Inventors: Ian R. King, Karl L. Krumel, Simon C. Lee
  • Patent number: 5214144
    Abstract: 4-Haloquinazolines can be prepared by the halogenation of the corresponding 4-hydroxyquinazolines with a phosphoryl, thionyl or carbonyl halide in the presence of a catalytically effective amount of a N,N-dialkylformamide. The reaction is catalyzed by the addition of soluble organic halide salts.
    Type: Grant
    Filed: October 7, 1991
    Date of Patent: May 25, 1993
    Assignee: DowElanco
    Inventors: Jimmy J. Tai, James W. Ringer, Karl L. Krumel, Richard C. Krauss
  • Patent number: 4994252
    Abstract: Finely divided potassium chloride is removed from mixtures with polar, aprotic solvents, such as N-methyl-2-pyrrolidinone, by combining the mixture with sufficient water to dissolve a significant portion, but not all of the potassium chloride present, removing the added water by distillation, and subsequently separating the larger crystals of the salt that form by filtration or centrifugation. The amount of water employed is in the same general range as the amount of polar, aprotic solvent present.
    Type: Grant
    Filed: February 9, 1990
    Date of Patent: February 19, 1991
    Assignee: DowElanco
    Inventors: Karl L. Krumel, Charles A. Wilson, Thad S. Hormel
  • Patent number: 4814448
    Abstract: Certain phenyl and N-heterocyclic phosphorothioates and phosphates are prepared by the reaction of an appropriate alkali metal or alkaline earth metal -O-phenyl or N-heterocyclic compound with an appropriate phosphorochloridate or phosphorochloridothioate under alkaline conditions in a liquid reaction medium and in the presence of a tertiary amine catalyst and a nonionic surfactant having a HLB Value of from about 2.5 to about 20 or more.
    Type: Grant
    Filed: March 6, 1987
    Date of Patent: March 21, 1989
    Assignee: The Dow Chemical Company
    Inventors: Sterling C. Gatling, Karl L. Krumel
  • Patent number: 4084012
    Abstract: Improved aqueous edible oil emulsions are obtained by using about 1-20 wt.% of certain water-soluble hydroxy-propylmethyl cellulose ethers as the emulsion stabilizer. These ethers have a thermal gel point of at least 70.degree. C as a 2% aqueous solution, a methoxyl degree of substitution of about 1.12-1.56, a hydroxypropoxyl molar substitution of about 0.10-0.29, and a 2% aqueous solution viscosity of 2-15 cps at 20.degree.C. They are particularly effective in stabilizing homogenized emulsions of citrus flavoring oils used in soft carbonated beverages.
    Type: Grant
    Filed: November 3, 1975
    Date of Patent: April 11, 1978
    Assignee: The Dow Chemical Company
    Inventors: Karl L. Krumel, Trudy L. Krasnoff, Terry H. Fiero
  • Patent number: 4080358
    Abstract: A water-dispersible, low-dusting, free-flowing composition made of acrylamide polymer, an antidusting agent selected from lower aliphatic polyols and polyalkylene glycols of up to about 6000 molecular weight and a particulate free-flow aid is disclosed.
    Type: Grant
    Filed: August 9, 1976
    Date of Patent: March 21, 1978
    Assignee: The Dow Chemical Company
    Inventors: Karl L. Krumel, Albert B. Savage
  • Patent number: 3960736
    Abstract: Viscous aqueous solutions are prepared which maintain a certain viscosity range over a predetermined period of time (i.e., induction period) and which thereafter break, i.e., decrease in viscosity over a very short period of time. The viscous aqueous solution comprises a polysaccharide having an ability to thicken water and dispersed or dissolved in the aqueous solution an effective quantity of an organic ester which, at a temperature at which it is desired to break the viscous solution, hydrolyzes over a delayed period of time to form an acid which degrades the polysaccharide, thus causing a splitting of the polysaccharide chain and a decrease in the viscosity of the solution.
    Type: Grant
    Filed: June 3, 1974
    Date of Patent: June 1, 1976
    Assignee: The Dow Chemical Company
    Inventors: Dustin L. Free, Karl L. Krumel, Travis C. Snyder