Patents Represented by Attorney, Agent or Law Firm Philip M. Pippenger
  • Preparation of optically active aliphatic carboxylic acids
    Patent number: 5574183
    Abstract: A process for the separation of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process comprises i) forming a diastereomeric salt by reaction comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an amount of a chiral organic base sufficient to react with one of the enantiomers of the racemic mixture; ii) precipitating from the reaction solution formed in step i) the diastereomeric salt; iii) separating said precipitated diastereomeric salt; iv) decomposing the salt into its enantiomeric component and its organic base component; and v) isolating a substantially pure enantiomer from said decomposed salt.
    Type: Grant
    Filed: January 24, 1995
    Date of Patent: November 12, 1996
    Assignee: Albemarle Corporation
    Inventors: Deepak R. Patil, Venkataraman Ramachandran
  • Synthetic paraffinic hydrocarbon drilling fluid
    Patent number: 5569642
    Abstract: An environmentally friendly invert drilling fluid comprises a water-in-oil emulsion which includes (a) at least 50 volume percent of a low toxicity base oil, and (b) at least one additive selected from the group consisting of emulsifiers, viscosifiers, weighing agents, oil wetting agents and fluid loss preventing agents, at least about 25 weight percent of the base oil content of the drilling fluid being a mixture of a linear alkane combined with a branched chain alkane, the alkanes individually having from about 14 to about 30 carbon atoms.
    Type: Grant
    Filed: February 16, 1995
    Date of Patent: October 29, 1996
    Assignee: Albemarle Corporation
    Inventor: Kaung-Far Lin
  • Polyfunctional michael addition products
    Patent number: 5569779
    Abstract: Compound mixtures varying from liquids to solids can be prepared via a Michael reaction so that (1) their molecules correspond to the formula Z--C(E)E').sub.p --Q.sub.s wherein 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 hydrocarbyl or predominantly hydrocarbyl organic groups containing up to 10 carbons, with the proviso that at least one of T, T', and T" must be hydrogen; E, E', G, and G' are independently selected from --COOR, --C(O)R', and --CN electron withdrawing groups in which R and R' represent alkyl or cycloalkyl groups of up to 10 carbons; p is zero or one; s is respectively two or one; and each of t and w represents zero or a positive integer and (2) at least 25% of the molecules contain at least three G groups.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: October 29, 1996
    Assignee: Albemarle Corporation
    Inventors: Mahmood Sabahi, Matthew L. Hurst
  • Aluminoxanate compositions
    Patent number: 5565395
    Abstract: An aluminoxanate composition which can be used as a co-catalyst with transition, lanthanide or actinide metal compounds such as metallocenes comprises the solid reaction product of an aluminoxane and an alkali metal, alkaline earth metal, ammonium, phosphonium or sulfonium salt of a Group 13 to 16 element-containing polyoxy compound such as sodium aluminate.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: October 15, 1996
    Assignee: Albemarle Corporation
    Inventors: Samuel A. Sangokoya, Milham S. Howie, Patrick G. Simms, Karl E. Wiegand
  • Alkyl-aromatic diphosphites
    Patent number: 5565600
    Abstract: Novel alkyl-aromatic diphosphites having antioxidant and flame-retarding abilities and corresponding to the formula: ##STR1## can be prepared by reacting a 2,2'-bridged bisphenol corresponding to the formula: ##STR2## with pentaerythritol dichlorophosphite at 20-150.degree. C. in the presence of a basic catalyst; R and R' in the formulas representing hydrocarbyl groups, R" being a divalent bridging group, and n being 0 or 1. These diphosphites have good hydrolytic stability per se and can be made even more resistant to hydrolysis by stabilizing them with at least 0.5% by weight of an acid scavenger, preferably before they are recovered from their synthesis reaction mixtures.
    Type: Grant
    Filed: June 26, 1995
    Date of Patent: October 15, 1996
    Assignee: Albemarle Corporation
    Inventor: Hassan Y. Elnagar
  • Olefin polymerization catalyst comprising a metallocene and an anhydrous lithium halide-treated alkylaluminoxane
    Patent number: 5565397
    Abstract: Alkylaluminoxanes having improved catalytic activity such as when they are used in combination with metallocenes for the polymerization of alpha-olefins, are prepared by treating an organic solvent solution of an alkylaluminoxane, such as methylaluminoxane, with anhydrous lithium halide.
    Type: Grant
    Filed: May 12, 1995
    Date of Patent: October 15, 1996
    Assignee: Albemarle Corporation
    Inventor: Samuel A. Sangokoya
  • Fluid mixtures of methylidene- or methyl-substituted linear hydrocarbons and derivatives thereof
    Patent number: 5563307
    Abstract: Novel fluid mixtures of specified hydrocarbons meeting an array of structural criteria are described. Linear hydrocarbons having terminal double bonds and internal segments of specified differing chain lengths separated by one or more carbon atom(s) each of which has a methylidene substituent make up one group of such compounds. Another group is alkenyl end-capped compounds of the first group. Third and fourth groups are products formed by hydrogenation of the first and second groups, respectively. The products, whether end-capped or not, and whether hydrogenated or not, have desirable lubricating properties such as suitably low pour points and/or low NOACK volatility and/or very high viscosity index and thus can be used as base oils or as components in formulating lubricants.
    Type: Grant
    Filed: May 22, 1995
    Date of Patent: October 8, 1996
    Assignee: Albemarle Corporation
    Inventors: Robert A. Schaerfl, Jr., Ali M. Dadgar, Carroll W. Lanier
  • Formulated branched chain alcohol ether sulfate compounds
    Patent number: 5562866
    Abstract: Certain double-tailed alcohol ether sulfates of specified chemical structures are formulated with a hydrotrope or a co-surfactant. The formulations are useful for various surfactant utilities including use in hard water systems.
    Type: Grant
    Filed: June 20, 1995
    Date of Patent: October 8, 1996
    Assignee: Albemarle Corporation
    Inventors: Patrick C. Hu, Raynold J. Corona
  • Enhanced synthesis of racemic metallocenes
    Patent number: 5556997
    Abstract: Chiral metallocenes are prepared by reacting a salt of an asymmetric bis(cyclopentadienyl) moiety containing ligand with a chelate diamine adduct of a transition, lanthanide, or actinide metal halide in an organic solvent medium so as to produce said chiral metallocene.
    Type: Grant
    Filed: April 24, 1995
    Date of Patent: September 17, 1996
    Assignee: Albemarle Corporation
    Inventors: Jamie R. Strickler, John M. Power
  • Ester lubricants
    Patent number: 5538661
    Abstract: An ester oil which lacks complete miscibility with fluorohydrocarbons has its miscibility with fluorohydrocarbons refrigerants improved by blending it with a second ester oil composed of molecules corresponding to the formula ROOC--CH.sub.2 CH.sub.2 -[(ROOC)CHCH.sub.2 ].sub.m --C(COOR).sub.2 --[CH.sub.2 CH(COOR)].sub.n --CH.sub.2 CH.sub.2 COOR wherein the R's represent alkyl groups of 1-30 carbons, at least 10% of which are alkyl groups of 1-4 carbons; and each of m and n represents zero or a positive integer such that the sum of m and n in a molecule is 0-30.
    Type: Grant
    Filed: August 3, 1994
    Date of Patent: July 23, 1996
    Assignee: Albemarle Corporation
    Inventors: Raymond B. Dawson, Hugh A. Fisher, Kenneth C. Lilje, Mahmood Sabahi
  • Michael addition process
    Patent number: 5536872
    Abstract: The reaction between a Michael donor corresponding to the formula Z--CH(E)(E') (e.g., a dialkyl malonate) and a Michael acceptor corresponding to the formula CTT'.dbd.CT"G (e.g., an alkyl acrylate or alkyl acrylate dimer) in the presence of a solid inorganic base catalyst is expedited by simultaneously feeding the reactants through a column of the solid inorganic base catalyst at a temperature of about 25.degree.-120.degree. C. to form an effluent containing a product corresponding to the formula Z'--C(E)(E").sub.p --Q.sub.
    Type: Grant
    Filed: August 4, 1995
    Date of Patent: July 16, 1996
    Assignee: Albemarle Corporation
    Inventors: Mahmood Sabahi, Kenneth C. Lilje
  • Process for preparing olefins
    Patent number: 5536870
    Abstract: A process for preparing olefin compounds of the formula ##STR1## where A is aryl, substituted aryl, heteroaryl, substituted heteroaryl, benzyl, substituted benzyl, vinyl or substituted vinyl and R.sub.2, R.sub.3 and R.sub.4 are hydrogen, alkyl, cycloalkyl, alkyl-substituted cycloalkyl, aryl, substituted aryl, alkoxy, alkythio, heteroaryl, substituted heteroaryl, alkanoyl, aroyl, substituted aroyl, heteroarylcarbonyl, substituted heteroarylcarbonyl, trifluoromethyl or halo, which comprises reacting an organic halide of the formula A-X where X is chloro, bromo or iodo with a vinyl or substituted vinyl compound of the formula ##STR2## where R.sub.2, R.sub.3 and R.sub.
    Type: Grant
    Filed: February 17, 1995
    Date of Patent: July 16, 1996
    Assignee: Albemarle Corporation
    Inventor: Tse-Chong Wu
  • Preparation of .alpha., .omega.-diene oligomers and derivatives thereof
    Patent number: 5516958
    Abstract: .alpha.,.omega.-Diene oligomers which are useful as synthetic lubricants are prepared by oligomerizing a .alpha.,.omega.-diene using a trialkylaluminum catalyst.
    Type: Grant
    Filed: December 14, 1993
    Date of Patent: May 14, 1996
    Assignee: Albemarle Corporation
    Inventors: Robert A. Schaerfl, Jr., Ali M. Dadgar, Carroll W. Lanier
  • Ultrasonic process
    Patent number: 5498800
    Abstract: A process is disclosed for obtaining a compound of the formulaAr-Z IIwhere Ar, R.sub.1 and R.sub.2 are defined in the specification and Z is --C(R.sub.3).dbd.CH.sub.2 or --CH(R.sub.3)CHO where R.sub.3 is defined in the specification. The process utilizes a heterogeneous mixture of the compound of formula I and an alkali or alkaline earth metal in dimethylformamide. The mixture is subjected to ultrasonic vibrations for a time and at a temperature sufficient to produce a compound of formula II: ##STR1## where Ar, R.sub.1, and R.sub.2 are defined above and X is the halo group.
    Type: Grant
    Filed: January 9, 1995
    Date of Patent: March 12, 1996
    Assignee: Albemarle Corporation
    Inventor: Thanikavelu Manimaran
  • Preparation of synthetic oils from vinylidene olefins and alpha-olefins
    Patent number: 5498815
    Abstract: A synthetic oil is made by a process comprising the steps of (a) reacting a vinylidene olefin in the presence of a catalyst to form an intermediate mixture which contains at least about 50 weight percent dimer of said vinylidene olefin, and (b) adding a vinyl olefin to said intermediate mixture and reacting said intermediate mixture and said vinyl olefin in the presence of a catalyst so as to form a product mixture which contains said dimer of said vinylidene olefin and a codimer of said added vinyl olefin with said vinylidene olefin.
    Type: Grant
    Filed: December 13, 1991
    Date of Patent: March 12, 1996
    Assignee: Albemarle Corporation
    Inventors: Robert A. Schaerfl, Jr., Ali M. Dadgar, Carroll W. Lanier
  • Process for preparation of zeolite "X"
    Patent number: 5487882
    Abstract: A method for producing crystalline synthetic faujasite of the zeolite "X" type is disclosed. The method comprises (a) separately preparing a sodium silicate solution and a sodium aluminate solution, (b) admixing the sodium silicate solution and the sodium aluminate solution at high shear until a mixture results having a ratio of sodium oxide to silica of 0.4:1 to 2:1, silica to alumina of 2.2:1 to 3.5:1, and water to sodium oxide of 20:1 to 70:1, (c) heating said mixture to a temperature of about 80.degree. to 120.degree. C. in the absence of any further mixing for a period of time sufficient to produce the desired crystalline faujasite of the zeolite "X" type, and (d) recovering said zeolite "X".
    Type: Grant
    Filed: July 19, 1994
    Date of Patent: January 30, 1996
    Assignee: Albemarle Corporation
    Inventors: Patrick C. Hu, Eric W. Liimatta
  • Mixed ligand catalyst for preparing aryl-substituted aliphatic carboxylic esters
    Patent number: 5482596
    Abstract: A new process for preparing aryl substituted aliphatic carboxylic acids and their esters is provided. A 1-aryl substituted olefinic compound is reacted with carbon monoxide in the presence of water (in aqueous conditions) or an alcohol (in anhydrous conditions) at a temperature between about 25.degree. C. and about 200.degree. C. An excess of several moles of water or of anhydrous alcohol is preferred. An acid such as hydrochloric acid may also be added. As catalyst, a mixture of a palladium compound and optionally a copper compound with a ligand mixture comprising a compound of the formula (R').sub.3 ZY and a compound of the formula (R").sub.3 Z where each R' and R" are the same or different and is alkyl, aryl or substituted aryl, and Z is any atom that has a Pauling electronegativity of between 1.9 and 2.5 and Y is a member of Group VIA of the Periodic Table of Elements.
    Type: Grant
    Filed: January 27, 1994
    Date of Patent: January 9, 1996
    Assignee: Albemarle Corporation
    Inventor: Tse-Chong Wu
  • Haloalkylation process
    Patent number: 5475170
    Abstract: An improvement in a process for the haloalkylation of a first aromatic compound having at least one free ring position with a haloalkylating reagent and in the presence of a haloalkylation catalyst, said process producing a haloalkylated first aromatic compound and a dimeric reaction by-product of said first aromatic compound having at least one free ring position, the improvement comprising treating said by-product with a second aromatic compound having at least one free ring position the same or different than said first aromatic compound in the presence of a catalytically effective amount of an acid for a time and at a temperature sufficient to cleave said diarylalkane by-product and produce thereby said first aromatic compound having at least one free ring position.
    Type: Grant
    Filed: June 27, 1994
    Date of Patent: December 12, 1995
    Assignee: Albermarle Corporation
    Inventor: Tse-Chong Wu
  • Enantiomeric resolution
    Patent number: 5442117
    Abstract: A process for obtaining a substantially pure enantiomer of an hydrocarbyl amine is described. The process utilizes first an enantiomerically enriched mixture the of hydrocarbyl amine obtained from kinetic resolution, diastereomeric crystallization or asymmetric synthesis processes. This enriched mixture is reacted with an inorganic acid producing a salt that has the following properties:1) has at least one eutectic point;2) a composition that is not at the eutectic point; and3) a eutectic composition that is closer to the racemiccomposition than is the eutectic composition of saidhydrocarbyl, or be a solid where the salt is a liquid. A substantially pure, enantiomeric salt is separated, leaving a mother liquor comprising the solvent and the hydrocarbyl amine enriched in the other enantiomer.
    Type: Grant
    Filed: December 13, 1993
    Date of Patent: August 15, 1995
    Assignee: Albemarle Corporation
    Inventors: G. Patrick Stahly, Thanikavelu Manimaran
  • Catalyst for alkene dimerization
    Patent number: 5432142
    Abstract: A catalyst composition is disclosed that is useful for the dimerization of a normal 1-alkene containing 3-8 carbons. A supported alkali metal is employed as a catalyst and is combined with about 10-100 mol %, based on the amount of alkali metal catalyst, of an oxide of sodium, potassium, rubidium, and/or cesium as a co-catalyst. In preferred embodiments of the invention, the alkali metal is potassium or a potassium or a potassium alloy, and the co-catalyst is sodium oxide.
    Type: Grant
    Filed: August 3, 1994
    Date of Patent: July 11, 1995
    Assignee: Albermarle Corporation
    Inventor: R. Scott Smith