Patents Represented by Attorney, Agent or Law Firm Philip M. Pippenger
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Patent number: 6268526Abstract: A mixture formed from an aromatic substituted alcohol and/or an aromatic substituted alkyl halide, and a copper-free palladium catalyst is carbonylated with carbon monoxide. Extremely high yields of the desired alpha-substituted carboxylic acid can be obtained in very short reaction periods by use of a palladium catalyst that is formed from a palladium compound with a valence of zero to two and a cycloalkyldiarylphosphine ligand, such as neomenthyldiphenylphosphine.Type: GrantFiled: December 16, 1998Date of Patent: July 31, 2001Assignee: Albemarle CorporationInventor: Tse-Chong Wu
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Patent number: 6252098Abstract: Chiral metallocenes are prepared by reacting a salt of an asymmetric bis(cyclopentadienyl)-moiety-containing ligand with a tertiary heteroaromiatic amine adduct of a transition, lanthanide, or actinide metal halide in an organic solvent or diluent so as to produce said chiral metallocene.Type: GrantFiled: June 5, 2000Date of Patent: June 26, 2001Assignee: Albemarle CorporationInventors: Uwe F. Winkler, Meng-Sheng Ao
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Patent number: 6248265Abstract: Fluoroaryl Grignard reagents are produced from a hydrocarbyl Grignard reagent and fluoroaromatic compounds via separate additions of different fluoroaromatic compounds, such that the conversion of hydrocarbyl Grignard reagent to the desired fluoroaryl Grignard reagent is essentially complete, and thus the reaction product is free or essentially free of agents that may negatively affect subsequent reactions. The fluoroaryl Grignard reagents may be further reacted with boron trihalides in order to obtain tris(fluoroaryl)boranes or tetrakis(fluoroaryl)borates.Type: GrantFiled: June 16, 2000Date of Patent: June 19, 2001Assignee: Albemarle CorporationInventors: John Y. Lee, David W. Owens, Charles R. Everly, Ronny W. Lin, John M. Power, Steven P. Diefenbach, Niomi L. Krzystowczyk
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Patent number: 6241917Abstract: Chloropentafluorobenzene or bromopentafluorobenzene is formed by heating perhalobenzene, C6FnX6-n where n is 0 to 4, and each X is, independently, a chlorine or bromine atom, with alkali metal fluoride, and an aminophosphonium catalyst (e.g., (Et2N)4PBr). The resultant chloropentafluorobenzene or bromopentafluorobenzene can be converted into a pentafluorophenyl Grignard reagent or a pentafluorophenyl alkali metal compound. This in turn can be converted into tris(pentafluorophenylborane), which can be converted into a single coordination complex comprising a labile tetra(pentafluorophenyl)boron anion (e.g., a trialkylammonium tetra(pentafluorophenyl) boron complex or an N,N-dimethylanilinium tetra(pentafluorophenyl)boron complex).Type: GrantFiled: May 21, 1999Date of Patent: June 5, 2001Assignee: Albemarle CorporationInventors: David W. Owens, John F. Balhoff
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Patent number: 6235941Abstract: An aqueous solution of basic mercaptide salt and water-soluble peroxide are mixed together in a reaction zone and maintained under reaction conditions effective to produce a vapor phase comprising organic disulfide, and concurrently vapor phase is recovered from the reaction zone. The process is highly efficient and enables production of organic disulfides in high yield and purity. Not only is the process very easy and simple to carry out, but in addition the process (i) eliminates the need for forming an organic phase of liquid organic disulfide product and conducting a separation between such product and the total aqueous phase used in the reaction, (ii) enables efficient control of a highly exothermic reaction, and (iii) minimizes alkanesulfonic acid salt formation during the reaction.Type: GrantFiled: February 13, 1998Date of Patent: May 22, 2001Assignee: Albemarle CorporationInventors: Chi Hung Cheng, Gerald M. Sulzer
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Patent number: 6225475Abstract: To form a mixture of anhydrides suitable for use as a curing agent for epoxy resins, a mixture formed from maleic anhydride and a liquid monoolefin is heated to produce a reaction mass containing a liquid phase comprised of alkenyl succinic anhydride, maleic anhydride, and monoolefin. Then a conjugated diene hydrocarbon is mixed with this reaction mass and the temperature of the resultant mixture is such as to form a reaction mass comprising tetrahydrophthalic anhydride and/or alkyl-substituted tetrahydrophthalic anhydride and alkenyl succinic anhydride.Type: GrantFiled: August 18, 2000Date of Patent: May 1, 2001Assignee: Albemarle CorporationInventors: Valerie N. Legloahec, Patrick C. Hu
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Patent number: 6225437Abstract: Provided are alkenyl and/or alkyl succinimides formed from at least one alkenyl or alkyl succinic anhydride and at least one aliphatic amine having one or two primary amino groups in the molecule. These succinimides are characterized in that each alkenyl or alkyl group thereof contains in the range of 16 to 30 carbon atoms. Such group is bifurcated on its alpha carbon atom into two branches neither of which contains less than 2 carbon atoms, one such branch being free of any side chain, and the other such branch either being free of any side chain or containing at most one methyl or methylene side chain. In addition the succinimide has a viscosity at 80° C. of less than about 100 centistokes. These succinimides are especially useful as internal and external sizing agents for paper and paper products.Type: GrantFiled: June 24, 1999Date of Patent: May 1, 2001Assignee: Albemarle CorporationInventors: Patrick C. Hu, Valerie N. LeGloahec
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Patent number: 6215032Abstract: It has been found possible to separate catalytically-active aminophosphonium catalysts from mixtures composed predominately of aminophosphonium catalyst residue(s) and heavy ends from a halogen exchange reaction conducted in an aprotic solvent/diluent by extracting such mixtures with a neutral or acidic aqueous extraction solvent medium. Various ways of isolating from the halogen exchange reaction product mixture a mixture composed predominately of aminophosphonium catalyst residue(s) and heavy ends are described. Halogen exchange processes in which the catalytically-active aminophosphonium catalysts are separated for reuse are also described. Since aminophosphonium catalysts are expensive, the present process technology fulfills a need which has existed for an effective way of recovering such catalysts in catalytically active form enabling reuse of such materials, especially as halogen exchange catalysts.Type: GrantFiled: February 10, 1998Date of Patent: April 10, 2001Assignee: Albemarle CorporationInventors: Chi Hung Cheng, John F. Balhoff, Ronny W. Lin
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Patent number: 6198003Abstract: A highly efficient method of producing alkyl mercaptan and/or dialkyl monosulfides which involves employing carbon dioxide as an internal coolant is described. Only negligible amounts of carbonyl sulfide were formed. In addition, relatively easy separation of carbon dioxide from the reaction mixture facilitates an efficient coolant recycle process, giving a simple and effective mode of temperature control.Type: GrantFiled: April 20, 1999Date of Patent: March 6, 2001Assignee: Albemarle CorporationInventors: Kaung-Far Lin, James E. Boone, Michael D. Matthews, John C. Prindle, Jr., Sharon D. Booth McGee
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Patent number: 6194340Abstract: A solution of a siloxy-aluminoxane composition formed by mixing (i) a hydrocarbylsiloxane substantially free of hydroxyl groups with (ii) an aluminoxane, in an organic solvent medium in which the molar ratio of aluminum to hydrocarbylsiloxane is from 1:1 to 1000:1, is heated under reduced pressure to form a more concentrated solution. A siloxy-aluminoxane composition having greater solution stability than the initial siloxy-aluminoxane composition is thereby produced.Type: GrantFiled: March 2, 2000Date of Patent: February 27, 2001Assignee: Albemarle CorporationInventor: Samuel A. Sangokoya
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Patent number: 6191307Abstract: A process of producing benzoic acids from phthalimides is described. The ability to dramatically reduce the reaction time in comparison to currently practiced processes by the addition of readily available compounds is demonstrated.Type: GrantFiled: April 6, 1999Date of Patent: February 20, 2001Assignee: Albemarle CorporationInventors: Tse-Chong Wu, R. Carl Herndon, Jr.
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Patent number: 6187931Abstract: Tri- or tetrafluorophthalimides are produced in a halogen-exchange reaction utilizing a metal fluoride salt and a dihydrocarbyl sulfoxide as the solvent. No phase-transfer catalyst is employed. The process has been found capable of producing the fully fluorinated phthalimide in yields of over 90% GC in reactions performed at 135-155 ° C. in reaction periods of as little as one hour even though no phase-transfer catalyst is employed.Type: GrantFiled: April 6, 1999Date of Patent: February 13, 2001Assignee: Albemarle CorporationInventors: Stephen E. Belmont, Charles R. Everly, Yunqi Liu
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Patent number: 6184415Abstract: It has been discovered that it is possible to produce enantioselectively, a chiral 2-haloalkanoic acid or salt thereof, by subjecting a 2-halo-&agr;,&bgr;-alkenoic acid or salt, e.g., a 2-haloacrylic acid or salt, to asymmetric hydrogenation in the presence of an enantiometrically-enriched (BINAP)Ru(II) catalyst. In contrast to asymmetric hydrogenation of olefinic compounds having an electron rich, electropositive substituent in the 2-position, the substituent in the 2-position is an electronegative, electron-withdrawing halide substituent. The reaction is accelerated by inclusion of an alkali metal halide or quaternary ammonium halide in the reaction mixture.Type: GrantFiled: November 1, 1999Date of Patent: February 6, 2001Assignee: Albemarle CorporationInventors: Edward G. Samsel, Christi R. Bedell
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Patent number: 6169210Abstract: A highly efficient method of producing dialkyl disulfides from mercaptans and oxygen is described which involves employing carbon dioxide as an internal coolant. Among the benefits made possible by this method are (1) an increase in the proportion of mercaptan converted to dialkyl disulfide per pass through the reactor, (2) an increased ease of separation of and recycling of carbon dioxide, (3) the ability to use a common contaminant as a coolant, and (4) the use of a simple adiabatic reactor design.Type: GrantFiled: April 20, 1999Date of Patent: January 2, 2001Inventor: Kaung-Far Lin
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Patent number: 6169208Abstract: A solution comprising a halomagnesium tetrakis(Faryl)borate in a liquid organic medium, wherein the liquid organic medium is comprised of one or more liquid dihydrocarbyl ethers, one or more liquid hydrocarbons, one or more liquid halogenated hydrocarbons, or mixtures thereof, is contacted with water. This produces magnesium di[tetrakis(Faryl)borate] in the organic phase of a two-phase water/liquid organic medium. The magnesium di[tetrakis(Faryl)borate] can be, but need not be, isolated. A protic ammonium salt, an onium salt, or a triarylmethyl salt can be reacted with the magnesium di[tetrakis(Faryl)borate] to produce the corresponding protic ammonium, onium, or triarylmethyl tetrakis(Faryl)borate. The magnesium di[tetrakis(Faryl)borate] can instead be reacted with a metal salt to form a metal tetrakis(Faryl)borate.Type: GrantFiled: December 3, 1999Date of Patent: January 2, 2001Assignee: Albemarle CorporationInventor: John Y. Lee
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Patent number: 6162950Abstract: An alkali metal fluoride is reacted with a halomagnesium tetrakis(.sup.F aryl)borate to form an alkali metal tetrakis(.sup.F aryl)borate. The alkali metal tetrakis(.sup.F aryl)borate can be isolated, or the alkali metal cation can be replaced by an organic cation.Type: GrantFiled: December 3, 1999Date of Patent: December 19, 2000Assignee: Albemarle CorporationInventors: John Y. Lee, Jamie R. Strickler
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Patent number: 6160145Abstract: Novel, highly effective catalyst compositions are described in which a low cost co-catalyst can be employed at very low aluminum loadings. Such compounds are composed of a cation derived from d-block or f-block metal compound, such as a metallocene, by loss of a leaving group, and an aluminoxate anion derived by transfer of a proton from a stable or metastable hydroxyaluminoxane to such leaving group. These catalyst compositions have extememly high catalytic activity and typically have high solubility in paraffinic solvents. Moreover they yield reduced levels of ash and result in improved clarity in polymers formed from such catalysts.Type: GrantFiled: October 23, 1998Date of Patent: December 12, 2000Assignee: Albemarle CorporationInventors: Feng-Jung Wu, Jamie R. Strickler
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Patent number: 6150560Abstract: This invention relates to methods for separating tris(aryl)boranes from tris(aryl)boranetetrahydrofuran complexes in hydrocarbon solvents via distillation.Type: GrantFiled: April 22, 1999Date of Patent: November 21, 2000Assignee: Albemarle CorporationInventors: John Y. Lee, Jamie R. Strickler
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Patent number: 6129863Abstract: Perfluoroaryl Grignard reagents are produced from a hydrocarbyl Grignard reagent and polyhaloaromatic compounds via separate additions of different polyhaloaromatic compounds, such that the conversion of hydrocarbyl Grignard reagent to the desired perfluoroaryl Grignard reagent is essentially complete, and thus the reaction product is free or essentially free of agents that may negatively affect subsequent reactions. The perfluoroaryl Grignard reagents may be further reacted with boron trihalides in order to obtain tris(perfluoroaryl)boranes or tetrakis(perfluoroaryl)borates.Type: GrantFiled: December 18, 1998Date of Patent: October 10, 2000Assignee: Albemarle CorporationInventors: John Y. Lee, David W. Owens, Charles R. Everly, Ronny W. Lin, John M. Power, Steven P. Diefenbach, Niomi L. Krzystowczyk
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Patent number: 6126863Abstract: The present invention is directed to a process for the production of agglomerates of a sterically hindered phenol antioxidant such that the agglomerates have a balanced hardness so as to resist abrasion during conveyance yet being readily dispersed in a host plastic. Such novel agglomerates are achieved through the use of a processing aid consisting of a solvent selected from the group consisting of methylene chloride, chloroform, toluene, acetone, methylethylketone, xylene, cyclohexane, styrene, methylcyclohexane and hexane having at least one gram of antioxidant dissolved therein per 100 mL of solvent and from about 20 to about 50 weight percent of an alcohol of the formula ROH wherein R is an alkyl group of 1 to 8 carbon atoms and thereafter using the resulting solution of solvent, alcohol, and antioxidant to form a paste of additional portions of the antioxidant which is thereafter agglomerated and dried.Type: GrantFiled: December 2, 1998Date of Patent: October 3, 2000Assignee: Albemarle CorporationInventor: John Semen