Patents Represented by Attorney, Agent or Law Firm Philip M. Pippenger
  • Patent number: 5686640
    Abstract: Processes are described for the production and use of tri-(beta-branched alkyl)aluminum compounds. In a preferred embodiment, a process of this invention involves dimerizing one or more vinylolefin monomers with an alkyl aluminum catalyst to form a first product mixture comprising at least vinylolefin monomer, trialkylaluminum in which each alkyl group has the same number of carbon atoms and skeletal structure as said vinylolefin monomer, and vinylidene olefin. The vinylolefin monomer is then removed while concurrently the trialkylaluminum and vinylidene olefin are converted to tri-(beta-branched alkyl)aluminum by reactive distillation. Reactive distillation effects a shift of the chemical equilibrium away from the trialkylaluminum compound and toward the production of tri-(beta-branched alkyl)aluminum. compound.
    Type: Grant
    Filed: August 30, 1996
    Date of Patent: November 11, 1997
    Assignee: Albemarle Corporation
    Inventor: Kaung-Far Lin
  • Patent number: 5683618
    Abstract: Lubricants having a viscosity suitable for a refrigeration lubricant as well as good miscibility with common refrigerants (including R-134a) comprise at least one oil corresponding to the formula Z--C(E)(E').sub.p --Q.sub.s in which Z is alkyl, cycloalkyl, or --(CTT'--CT"G).sub.w --CTT'--CHT"G; Q is --(CTT'--CT"G).sub.t --CTT'--CHT"G; T, T', and T" are independently selected from hydrogen G', and organic groups containing up to 20 carbons; E, E', G, and G' are independently selected from --COOR, --C(O)R', and --CN electron withdrawing groups wherein R and R' represent hydrocarbyls containing 1-30 carbons, with the proviso that at least about 50% of the electron withdrawing groups are --COOR; p is zero or one; s is respectively two or one; and each of t and w represents zero or a positive integer.
    Type: Grant
    Filed: February 1, 1996
    Date of Patent: November 4, 1997
    Assignee: Albemarle Corporation
    Inventor: Mahmood Sabahi
  • Patent number: 5679620
    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 as the only herbicide(s) used in the forming composition; and (b) one or more water-soluble particular types of aliphatic hydrocarbyl sulfonic acid or agriculturally acceptable salt or ester thereof as the only surfactants used in forming the composition. The hydrocarbyl group of the sulfonate is a saturated aliphatic group having in the range of about 10 to about 18 carbon atoms and is terminally substituted by the foregoing functionality.
    Type: Grant
    Filed: April 3, 1996
    Date of Patent: October 21, 1997
    Assignee: Albemarle Corporation
    Inventors: Ralph W. Magin, Joe D. Sauer, John R. Maloney
  • Patent number: 5679814
    Abstract: Metallocenes, such as silicon bridged ansa-metallocenes, are purified by heating a slurry of the metallocene at elevated temperature in an aprotic, polar solvent so as to extract impurities from the metallocene into the solvent and then separating the impurity containing solvent from the metallocene.
    Type: Grant
    Filed: December 11, 1995
    Date of Patent: October 21, 1997
    Assignee: Albemarle Corporation
    Inventors: Jamie R. Strickler, John M. Power
  • Patent number: 5679621
    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 long chain monoalkyl sulfate or agriculturally acceptable salt or short chain ester thereof in which the long chain group is an alkyl group having in the range of about 10 to about 18 carbon atoms and is terminally substituted by such functionality.
    Type: Grant
    Filed: April 3, 1996
    Date of Patent: October 21, 1997
    Assignee: Albemarle Corporation
    Inventors: Ralph W. Magin, Joe D. Sauer, John R. Maloney
  • Patent number: 5672749
    Abstract: The yield of acetyl chloride from the reaction between acetic anhydride and hydrogen chloride is increased by withdrawing acetyl chloride, optionally together with at least some of the acetic acid by-product, from the reaction mixture as the reaction proceeds and recycling the remainder of the reaction mixture to the reactor for reaction with additional hydrogen chloride.
    Type: Grant
    Filed: April 9, 1996
    Date of Patent: September 30, 1997
    Assignee: Albemarle Corporation
    Inventors: W. Bryan Waites, Robert E. Young, Phillip R. DeVrou
  • Patent number: 5670682
    Abstract: Stable liquid clathrate aluminoxane compositions are obtained by the reaction, in aromatic solvents, of aluminoxanes such as, methylaluminoxane, with organic, inorganic or organometallic compounds, such as salts, which can dissociate or partially dissociate into cationic and anionic species (M-X species).
    Type: Grant
    Filed: October 19, 1995
    Date of Patent: September 23, 1997
    Assignee: Albemarle Corporation
    Inventor: Samuel A. Sangokoya
  • Patent number: 5663394
    Abstract: Water, hydrocarbylaluminum such as trimethylaluminum, and organic solvent such as toluene are fed to a reactor in controlled proportions and under temperature control to form a dilute reaction product mixture of specified composition and concentration. This solution is then processed so as to form at least two product mixtures, one of which is essentially aluminoxane-free hydrocarbylaluminum dissolved in organic solvent, and another of which is a concentrated solution of organoaluminum compounds composed in essence of hydrocarbylaluminum (e.g. trimethylaluminum) and hydrocarbylaluminoxane (e.g., methylaluminoxane) in organic solvent in which the amount aluminoxane far exceeds the amount of hydrocarbylaluminum. The process fulfills the need for practical, commercially-feasible process technology capable of producing concentrated aluminoxane solutions with no significant yield losses, and by process technology that can be applied both to batch and to continuous modes of operation.
    Type: Grant
    Filed: July 15, 1996
    Date of Patent: September 2, 1997
    Assignee: Albemarle Corporation
    Inventors: John K. Roberg, Edward A. Burt
  • Patent number: 5654485
    Abstract: By reacting certain partially sterically-hindered chloro-substituted cycloalkanes with sodium and/or potassium diarylphosphides in an ether reaction medium, not only are useful cycloalkyldiarylphosphines produced, but in addition the chloro-substituted cycloalkane does not undergo any appreciable reaction with the coproduced aryl sodium and/or aryl potassium as it is formed. Moreover, the process makes it possible to avoid or at least to greatly reduce interaction with or cleavage of cyclic ether reaction media such as tetrahydrofuran. Thus the process makes possible improvements both in yield and quality of the cycloalkyldiarylphosphite product. A two-stage process conducted in an ether reaction medium is also described. In the first stage the sodium and/or potassium diarylphosphine reactant is produced by reaction between sodium and/or potassium and triarylphosphine.
    Type: Grant
    Filed: March 25, 1996
    Date of Patent: August 5, 1997
    Assignee: Albemarle Corporation
    Inventors: K. Pushpananda A. Senaratne, Arcelio J. Malcolm, Felix M. Orihuela, Hassan Y. Elnagar
  • Patent number: 5654486
    Abstract: Partially sterically-hindered cycloalkyl chlorides are reacted with lithium diarylphosphides in inert liquid hydrocarbon reaction media to form cycloalkyldiarylphosphines. Aryl lithium is coproduced. The process makes it possible to avoid, or at least substantially eliminate, the interaction with or cleavage of cyclic ether reaction media such as tetrahydrofuran, previously the solvent of choice for conducting this type of reaction. Also during the conduct of the present process the chloro-substituted cycloalkane does not undergo any appreciable reaction with the coproduced aryl lithium as it is formed. Thus improvements both in yield and quality of the cycloalkyldiarylphosphine product are made possible. A comprehensive three-step process for converting triarylphosphine to cycloalkyldiarylphosphine is also described.
    Type: Grant
    Filed: March 25, 1996
    Date of Patent: August 5, 1997
    Assignee: Albemarle Corporation
    Inventors: K. Pushpananda A. Senaratne, Arcelio J. Malcolm, Felix M. Orihuela, Hassan Y. Elnagar
  • Patent number: 5648578
    Abstract: A process for preparing tetraalkylated cyclopentadienes comprises (a) pyrolyzing an isobornyl carboxylate so as to form a mixture of 1,2,3- and 1,2,4-trimethylcyclopentadienes, (b) alkylating said mixture with an alkylating agent so as to form a mixture of alkyltrimethylcyclopentadiene isomers including 1,2,3,4-alkyltrimethylcyclopentadiene and, (c) thermally isomerizing the mixture of isomers obtained in step (b) so as to increase the proportion of 1,2,3,4-alkyltrimethylcyclopentadiene in said mixture of isomers.
    Type: Grant
    Filed: April 26, 1995
    Date of Patent: July 15, 1997
    Assignee: Albemarle Corporation
    Inventors: William J. Layman, Gene C. Robinson
  • Patent number: 5648583
    Abstract: Exo-isomers of polyalkylcyclopentadienes are converted to endo-isomers by contacting the exo-isomers with an acid such as aqueous HCl.
    Type: Grant
    Filed: April 27, 1995
    Date of Patent: July 15, 1997
    Assignee: Albemarle Corporation
    Inventors: John Y. Lee, Meng-Sheng Ao, Stephen E. Belmont, Lawrence H. Shepherd, Jr.
  • Patent number: 5648308
    Abstract: Inorganic and organic impurities are removed from a metallocene catalyst compound comprising the steps of (a) separating inorganic impurities from said compound by forming a solution of said compound in an organic solvent medium which is substantially a non-solvent for said inorganic impurities, (b) treating the solution of said compound with a particulate absorbing material so as to absorb and remove organic impurities from said solution, and (c) separating the solid material, including said particulate absorbing material, from said solution. Optionally, water can be removed by adding a drying agent.
    Type: Grant
    Filed: August 10, 1995
    Date of Patent: July 15, 1997
    Assignee: Albemarle Corporation
    Inventors: John Y. Lee, Steven P. Diefenbach
  • Patent number: 5648018
    Abstract: Hydrogenated oligomers of C.sub.4 -C.sub.20 .alpha.-olefins are used in minor amounts to improve the lubricity of ester oils corresponding to the formula ROOC--CH.sub.2 CH.sub.2 --(ROOC--CHCH.sub.2).sub.m --C(COOR).sub.2 --(CH.sub.2 CHCOOR).sub.n --CH.sub.2 CH.sub.2 COOR in which the R's represent alkyl groups of 1-30 carbons, each of m and n is zero or a positive integer, and the sum of m and n in the molecules is an average of 0-30. The improved ester oils are particularly valuable for use as lubricants in refrigeration compositions containing fluorohydrocarbon refrigerants.
    Type: Grant
    Filed: November 13, 1995
    Date of Patent: July 15, 1997
    Assignee: Albemarle Corporation
    Inventor: Mahmood Sabahi
  • Patent number: 5606087
    Abstract: An improved process for making aluminoxanes by the addition of water to a solvent solution of a hydrocarbylaluminum compound and/or an aluminoxane feeds the water through an orifice which is surrounded by a flow of solvent which carries the water into the solvent solution of hydrocarbylaluminum compound and/or aluminoxane.
    Type: Grant
    Filed: April 19, 1996
    Date of Patent: February 25, 1997
    Assignee: Albemarle Corporation
    Inventors: John K. Roberg, Robert E. Farritor, Edward A. Burt
  • Patent number: 5599964
    Abstract: Aluminoxane is made by feeding water, hydrocarbylaluminum and organic solvent to a loop recycle reactor under conditions so as to react the water and hydrocarbylaluminum to form a hydrocarbylaluminoxane, removing a portion of the solvent and hydrocarbylaluminoxane from said reactor and recirculating the remaining portion of the reactor contents through a reaction zone where the water initially contacts the hydrocarbylaluminum. The feed rates of water, hydrocarbylaluminum and solvent to the reactor and the withdrawal rate of solvent and hydrocarbylaluminoxane from the reactor can be adjusted to produce a substantially steady state reaction.
    Type: Grant
    Filed: April 19, 1996
    Date of Patent: February 4, 1997
    Assignee: Albemarle Corporation
    Inventors: John K. Roberg, Robert E. Farritor, Edward A. Burt
  • Patent number: 5599990
    Abstract: A quaternary ammonium halide is prepared by reacting a substituted or unsubstituted haloalkane with a tert-amine in a mol ratio not higher than 1.1/1 in the absence of a solvent and at a temperature such as to maintain the reaction mixture liquid.
    Type: Grant
    Filed: October 27, 1995
    Date of Patent: February 4, 1997
    Assignee: Albemarle Corporation
    Inventors: Joseph H. Miller, Joe D. Sauer, Dru L. DeLaet
  • Patent number: 5600004
    Abstract: An improved process for recovering pentafluorophenyl metal or metalloid compounds prepared by reacting pentafluoromagnesium halides with a metal or metalloid halide in ether solutions uses a precipitating agent such as an ether to precipitate the by-products from the reaction mixture.
    Type: Grant
    Filed: February 21, 1995
    Date of Patent: February 4, 1997
    Assignee: Albemarle Corporation
    Inventor: Steven P. Diefenbach
  • Patent number: 5597937
    Abstract: A deep olefin internal olefin is reacted with a C.sub.3-4 primary alkyl aluminum chloride in the liquid phase in the presence of a catalyst system formed from (i) a dicyclopentadienyl dihalide or halohydride of zirconium or hafnium and (ii) a hydridic co-catalyst component. Unlike prior art procedures, negligible quantities of by-product paraffins are formed in the process.
    Type: Grant
    Filed: May 11, 1995
    Date of Patent: January 28, 1997
    Assignee: Albemarle Corporation
    Inventor: Edward G. Samsel
  • Patent number: 5591311
    Abstract: A process for purifying impure 2,6-diisopropylphenol (DIP) mixtures having lower and higher boiling phenolic impurities is described. The process involves washing the mixture with aqueous alkali metal hydroxide solution in an inert atmosphere and separating the aqueous and organic phases, washing the resulting organic phase with water, and then subjecting the water-washed organic phase to distillation in an inert environment to recover purified DIP. Since only one distillation is required rather than two, the development of impurities in the DIP caused by in situ oxidation reactions at elevated temperatures due to the inevitable presence of traces of air in commercial distillation facilities is reduced to acceptable levels.
    Type: Grant
    Filed: October 26, 1995
    Date of Patent: January 7, 1997
    Assignee: Albemarle Corporation
    Inventor: Venkataraman Ramachandran