Patents Represented by Attorney, Agent or Law Firm Philip M. Pippenger
  • Patent number: 5763495
    Abstract: Described are .omega.,.omega.'-?.alpha.,.omega.-alkanediylbis(alkylimino)!bis(alkanolpol yethoxylates) in which (i) the alkane group has in the range of 4 to 12 carbon atoms, (ii) the alkyl groups can be the same or different and contain up to about 24 carbon atoms each, and (iii) the number of ethyleneoxy groups in each polyethoxylate group is in the range of 2 to about 50. These compounds are effective adjuvants for use with pesticides, especially herbicides and plant growth regulants, such as glyphosate.
    Type: Grant
    Filed: September 30, 1996
    Date of Patent: June 9, 1998
    Assignee: Albemarle Corporation
    Inventors: Ralph W. Magin, Joe D. Sauer
  • Patent number: 5760243
    Abstract: (a) An alkali metal base (hydroxide, oxide, carbonate, bicarbonate or sesquicarbonate), an acid addition salt of N-methylhydroxylamine, and (iii) water are mixed together to form a reaction mixture in which the acid of the acid addition salt has been neutralized. (b) Reaction mixture from (a) and formaldehyde or formalin are mixed together and the resultant mixture is subjected to reaction conditions that produce a reaction mixture in which N-methylnitrone has been formed. (c) Reaction mixture from (b) and styrene are mixed and the resultant mixture to subjected to reaction conditions that produce a reaction mixture in which 2-methyl-5-phenylisoxazolidine has been formed. Preferably, 2-methyl-5-phenylisoxazolidine formed in (c) is hydrogenated such that N-methyl-3-phenyl-3-hydroxypropylamine is formed, which in turn is reacted with 4-halobenzotrifluoride such that N-methyl-3-phenyl-3-?4-trifluoromethyl)phenoxy!propylamine is formed.
    Type: Grant
    Filed: July 25, 1997
    Date of Patent: June 2, 1998
    Assignee: Albemarle Corporation
    Inventor: Kevin J. Theriot
  • Patent number: 5760262
    Abstract: The reaction between a hafnium tetrahalide-diamine adduct and a metallated bis(cyclopentadienyl-moiety containing) ligand, offers great promise as a way of producing racemic hafnocenes, but involves a number of complications. Tetrahydrofuran, a commonly-used solvent/diluent for such reactions, when present in substantial portions in the liquid reaction medium containing the reactants and/or reaction product(s) has been found to cause a substantial reduction in yields of chiral hafnocenes. Apparently the presence of a substantial amount of THF causes or at least results in the formation of increased amounts of the undesirable meso isomer, tends to cause or result in tar formation, and results in a product having poor filterability. Thus large amounts of THF if fed to the reactor with the reactant(s) are purged to a suitably low level, replaced by a liquid aromatic hydrocarbon, and then the reaction mixture is heated to a higher reaction temperature.
    Type: Grant
    Filed: June 17, 1997
    Date of Patent: June 2, 1998
    Assignee: Albemarle Corporation
    Inventors: Troy E. DeSoto, Ronny W. Lin, John F. Balhoff
  • Patent number: 5741938
    Abstract: The process forms an alkyl aralkyl ketone from an aralkenyl secondary alcohol having an allylic double bond relative to the hydroxycarbinyl group, and having the allylic double bond positioned between the aryl moiety and the hydroxycarbinyl group. This is accomplished by heating the alcohol in a chemically indifferent organic liquid medium to which a catalytic quantity of an iron polycarbonyl has been added, so that an internal rearrangement occurs. Among the ketones that can be efficiently produced in this manner is non-steroidal antiinflammatory agent, 4-(6'-methoxy-2'-naphthyl)-butan-2-one, generally known as nabumetone.
    Type: Grant
    Filed: February 21, 1997
    Date of Patent: April 21, 1998
    Assignee: Albemarle Corporation
    Inventor: Stephen E. Belmont
  • Patent number: 5739368
    Abstract: Alumoxane, and especially methylalumoxane, which provide supported metallocene and/or transition metal catalyst compositions having increased activity are prepared by heating the alumoxane prior to placing it on the support.
    Type: Grant
    Filed: May 10, 1996
    Date of Patent: April 14, 1998
    Assignee: Albemarle Corporation
    Inventors: Niomi L. Krzystowczyk, Steven P. Diefenbach, Edward A. Burt
  • Patent number: 5731442
    Abstract: N-?4-(cyanoethylthiomethyl)-2-thiazolyl!guanidine--a key intermediate for preparing the pharmaceutical, famotidine--is produced by mixing in a liquid medium formed from a chemically indifferent organic solvent and water, and under an inert atmosphere, (i) a 2-guanidino-4-halomethylthiazole or a hydrohalide complex thereof, (ii) an S-(2-cyanoethyl)isothiourea or a hydrohalide complex thereof, and (iii) a strong alkali metal base. In lieu of (ii), an alkali metal salt of 2-cyanoethyl-1-thiol can be used, and in such case use of (iii) is optional, but preferable.
    Type: Grant
    Filed: March 11, 1997
    Date of Patent: March 24, 1998
    Assignee: Albemarle Corporation
    Inventors: Arcelio J. Malcolm, Tse-Chong Wu
  • Patent number: 5731253
    Abstract: Siloxy-aluminoxane compositions which are the reaction products of hydrocarbylsiloxanes substantially-free of Si--OH groups, and aluminoxanes and which have improved solubility and stability in solution even at up to 60 weight percent when compared to the original aluminoxane. The compositions in combination with metallocenes of transition lanithanide and actinide metals form catalysts which can be used in the polymerization of olefins such as ethylene.
    Type: Grant
    Filed: July 27, 1995
    Date of Patent: March 24, 1998
    Assignee: Albemarle Corporation
    Inventor: Samuel A. Sangokoya
  • Patent number: 5731480
    Abstract: A process is described for coproducing vinylidene alcohol and vinylidene olefin. The process involves dimerizing one or more vinylolefins with an alkyl aluminum catalyst to form a first product mixture comprising at least vinylidene olefin and alkyl aluminum compound. The vinylidene olefin is then reacted with the alkyl aluminum compound under displacement conditions to form 1-olefin while concurrently removing the 1-olefin from the displacement reaction mixture to form a second product mixture comprising at least beta-branched alkyl aluminum compound. The second product mixture is treated with air or oxygen under mild oxidation conditions to form a third product mixture comprising at least beta-branched aluminum alkoxide. The beta-branched aluminum alkoxide is then hydrolyzed to form vinylidene alcohol. The process makes effective use of the alkyl aluminum catalyst both as a catalyst and as a reactant, and requires only a relatively small amount of reaction equipment.
    Type: Grant
    Filed: November 3, 1995
    Date of Patent: March 24, 1998
    Assignee: Albemarle Corporation
    Inventor: Kaung-Far Lin
  • Patent number: 5710104
    Abstract: Glyphosate formulations which are effective even when employed at dosages below the dosage currently recommended for post-emergent herbicidal or plant growth regulant use are described. They are formulated as water solutions or powders or granules of (a) one or more agriculturally acceptable amine, alkali metal, alkylsulfonium, alkylphosphonium, sulfonylamine, and/or aminoguanidine salts of glyphosate; and (b) one or more water-soluble polyethoxylated monohydric primary alcohol having a .beta.-branched alkyl group which has a total of at least about 10 carbon atoms and at least about 3 carbon atoms in the branch on the .beta.-carbon atom or agriculturally acceptable salt or ester thereof.
    Type: Grant
    Filed: April 3, 1996
    Date of Patent: January 20, 1998
    Assignee: Albemarle Corporation
    Inventors: Ralph W. Magin, Joe D. Sauer, John R. Maloney
  • Patent number: 5710103
    Abstract: Glyphosate formulations which are effective even when employed at dosages below the dosage currently recommended for post-emergent herbicidal or plant growth regulant use are described. They are formulated as water solutions or powders or granules of (a) one or more agriculturally acceptable amine, alkali metal, alkylsulfonium, alkylphosphonium, sulfonylamine, and/or aminoguanidine salts of glyphosate; (b) at least one water-soluble long chain aliphatic hydrocarbyl dimethyl amine oxide in which the hydrocarbyl group is a linear or substantially linear saturated or olefinically unsaturated aliphatic group having in the range of about 8 to about 22 carbon atoms; and (c) at least one water-soluble quaternary ammonium halide having in the range of about 8 to about 40 carbon atoms in the molecule.
    Type: Grant
    Filed: April 3, 1996
    Date of Patent: January 20, 1998
    Assignee: Albemarle Corporation
    Inventors: Ralph W. Magin, Joe D. Sauer, Dru L. DeLaet, Deborah A. Quebedeaux
  • Patent number: 5710299
    Abstract: Bridged metallocene compounds are produced by a process of promising commercial utility for plant-sized operations. The overall process involves the direct conversion of benzoindanones to benzoindanols which, without isolation, are converted to benzoindenes. Thereupon the benzoindenes are bridged by deprotonating the benzoindenes with a strong base such as butyllithium and reacting the resultant deprotonated product with a suitable silicon-, germanium- or tin-containing bridging reactant such as dichlorodimethylsilane. The resultant bridged product is deprotonated with a strong base such as butyllithium and reacted with a suitable Group IV, V, or VI metal-containing reactant such as ZrCl.sub.4 to provide a silicon-, germanium- or tin-bridged Group IV, V, or VI metal complex, such as a dihydrocarbylsilyl-bridged zirconocene complex.
    Type: Grant
    Filed: June 27, 1996
    Date of Patent: January 20, 1998
    Assignee: Albemarle Corporation
    Inventors: Meng-Sheng Ao, Hassan Y. Elnagar, Arcelio J. Malcolm, Jamie R. Strickler
  • Patent number: 5710340
    Abstract: Phosphines having two aryl groups and one alkyl-substituted cycloalkyl group bonded to a phosphorus atom are formed by reacting an alkali metal diarylphosphide with a monoalkyl- or polyalkyl-substituted cycloalkyl mesylate or tosylate in which an alkyl group is in the 2-position, in a liquid reaction medium in which these reactants are soluble. This process avoids complications associated with prior known process technology for producing such phosphines. The phosphines are useful as ligands for making noble metal catalysts.
    Type: Grant
    Filed: April 29, 1996
    Date of Patent: January 20, 1998
    Assignee: Albemarle Corporation
    Inventor: K. Pushpananda A. Senaratne
  • Patent number: 5705039
    Abstract: Impure 2,6-diisopropylphenol (DIP) is purified by use of a distillation process in which a single distillation column is used. The process comprises: (a) subjecting the impure DIP to a first continuous distillation in the column in an inert environment to distill off lower boiling components and produce first column bottoms enriched in DIP; (b) collecting, cooling and storing the first column bottoms while continuously maintaining them in an inert environment; (c) discontinuing the first continuous distillation; (d) subjecting the first column bottoms to a second continuous distillation in an inert environment in the same column to produce a second overhead distillate composed of purified DIP. The process avoids the formation in the distilling mixtures of dose boiling impurities due to seepage of air through standard pipe flanges and fittings and consequent oxidation reactions which occur under the conditions needed for batch distillations conducted in typical industrial distillation facilities.
    Type: Grant
    Filed: October 13, 1995
    Date of Patent: January 6, 1998
    Assignee: Albemarle Corporation
    Inventors: Sam F. Clarke, Venkataraman Ramachandran, J. Steve Staton, Paul L. Wiggins
  • Patent number: 5703016
    Abstract: Glyphosate formulations which are effective even when employed at dosages below the dosage currently recommended for post-emergent herbicidal or plant growth regulant use are described.
    Type: Grant
    Filed: September 30, 1996
    Date of Patent: December 30, 1997
    Assignee: Albemarle Corporation
    Inventors: Ralph W. Magin, Joe D. Sauer
  • Patent number: 5700760
    Abstract: Glyphosate formulations which are effective even when employed at dosages below the dosage currently recommended for post-emergent herbicidal or plant growth regulant use are described. They are formulated as water solutions or as powders or granules of (a) one or more agriculturally acceptable amine, alkali metal, alkylsulfonium, alkylphosphonium, sulfonylamine, and/or aminoguanidine salts of glyphosate as the only herbicide or plant growth regulant used in forming said composition; and (b) a trihydrocarbyl amine oxide surfactant as the only surface active component used in forming said composition.
    Type: Grant
    Filed: April 3, 1996
    Date of Patent: December 23, 1997
    Assignee: Albemarle Corporation
    Inventors: Ralph W. Magin, Joe D. Sauer, Deborah A. Quebedeaux
  • Patent number: 5696286
    Abstract: A process for the preparation of aromatic substituted carboxylic acids is disclosed. The process comprisesi) forming an aromatic-substituted acrylonitrile by dehydrating a cyanohydrin of the formula ##STR1## where Ar is C.sub.6 to C.sub.10 aryl unsubstituted or substituted with C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched alkoxy, halo, amino, amino mono- or disubstituted with C.sub.1 to C.sub.6 linear or branched alkyl or carboxylic acid or the alkyl esters thereof; and R is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl;ii) catalytically reducing the aromatic-substituted acrylonitrile when not more than 10% of the cyanohydrin is converted to said acrylonitrile to form a first reaction solution comprising an aromatic substituted aliphatic nitrile;iii) hydrolyzing the aromatic-substituted aliphatic nitrile.
    Type: Grant
    Filed: August 9, 1993
    Date of Patent: December 9, 1997
    Assignee: Albemarle Corporation
    Inventors: Deepak R. Patil, George A. Knesel, Patricia Pringle
  • Patent number: 5693861
    Abstract: A highly pure, white, solid amine oxide is prepared in high yield with minimal decomposition of the solvent by (A) reacting a tert-amine with a 15-20% stoichiometric excess of concentrated hydrogen peroxide at 50.degree.-55.degree. C. in the presence of controlled amounts of carbon dioxide and ethyl acetate until the reaction mixture contains 35-45 % by weight of ethyl acetate and less than 0.8% by weight of unreacted amine, (B) catalytically decomposing residual hydrogen peroxide, (C) separating the reaction mixture from the decomposition catalyst, (D) cooling the reaction mixture to 0.degree. C. to form a slurry, (E) centrifuging the slurry to separate the amine oxide, and (F) vacuum drying the amine oxide at ambient temperature--the reaction mixture being diluted to an amine oxide content of 25-30% by weight with additional ethyl acetate or a mixture thereof with a co-solvent, such as a low-boiling n-alkane, after the completion of Step A and prior to the beginning of Step D.
    Type: Grant
    Filed: June 21, 1993
    Date of Patent: December 2, 1997
    Assignee: Albemarle Corporation
    Inventors: Rebecca F. Smith, Y.-D. Mark Chen, R. Woodrow Wilson, Jr., Mayur P. Shah, Kim R. Smith, Sharon B. McGee
  • Patent number: 5693838
    Abstract: A aluminoxane product is prepared by reacting water which contains a stabilizing agent, such as a lithium halide, with a hydrocarbyl aluminum compound, such as trimethylaluminum, in an organic solvent.
    Type: Grant
    Filed: November 13, 1995
    Date of Patent: December 2, 1997
    Assignee: Albemarle Corporation
    Inventors: Samuel A. Sangokoya, Lawrence H. Shepherd, Jr., Edward A. Burt
  • Patent number: 5693261
    Abstract: Pentafluorophenylmagnesium halides are prepared by a Grignard exchange reaction of hydrocarbylmagnesium halide with pentafluorochlorobenzene. The pentafluorophenylmagnesium halides are converted to pentafluorophenyl metal or metalloid derivatives by reacting them with metal or metalloid halides such as BF.sub.3.
    Type: Grant
    Filed: August 9, 1995
    Date of Patent: December 2, 1997
    Assignee: Albemarle Corporation
    Inventors: Niomi L. Krzystowczyk, Steven P. Diefenbach, Wendy L. Lemoine
  • Patent number: 5690141
    Abstract: Described are improved valve covers on containers adapted for use in shipping and/or storing transportable chemicals. In one device of the invention, a hinge connects a lid to a rim and is displaced from the container's center line at a first preselected angle, is free-floating to permit horizontal self-alignment with the rim upon contact therewith, and is equipped with stop means for preventing the lid from swinging open more than a second preselected angle from a plane occupied by the sealing surface of the rim. The invention provides valve covers, and containers with valve covers, having significantly improved sealing capability to provide better protection of container valves and container content from external elements, contaminants and/or reactants, while employing a configuration which makes access to the valves and container contents easier and safer.
    Type: Grant
    Filed: May 17, 1996
    Date of Patent: November 25, 1997
    Assignee: Albemarle Corporation
    Inventor: St. George Creaghe