Patents Represented by Attorney Joseph D. Odenweller
  • Patent number: 4564697
    Abstract: Haze-free reactive flame retardant halo polyols are made by reacting (a) a halogen containing cyclic acid anhydride (e.g. tetrabromophthalic anhydride), (b) an aliphatic polyol, e.g. diethylene glycol, and (c) an epoxide, e.g. propylene oxide, and including potassium salt of fatty acids (e.g. potassium acetate) in the reaction mixture in an amount at least sufficient to neutralize residual sulfuric acid that is usually present in the halogen containing cyclic acid anhydride.
    Type: Grant
    Filed: November 29, 1984
    Date of Patent: January 14, 1986
    Assignee: Ethyl Corporation
    Inventor: Burton J. Sutker
  • Patent number: 4551317
    Abstract: Halophosphazene polymers such as linear phosphonitrilic chloride polymers are prepared in two stages by (i) heating a nitrogen source (e.g., NH.sub.3 ; NH.sub.4 Cl; etc.) with an excess of a phosphorus source (e.g., PCl.sub.5 ; PCl.sub.3 +Cl.sub.2 ; P+Cl.sub.2 ; etc.) so that hydrogen halide is evolved and halophosphazene is formed, and (ii) heating at least a portion of the halophosphazene with at least a stoichiometric amount (preferably an excess) of a nitrogen source (e.g., NH.sub.3 ; NH.sub.4 Cl; etc.) so that hydrogen halide is evolved and halophosphazene polymer of higher molecular weight is formed. Preferably, a third stage is utilized wherein the resultant halophosphazene polymer is then heated, most preferably in an inert solvent or diluent which enhances the fluidity of the reaction mixture, to increase the molecular weight of the polymer.
    Type: Grant
    Filed: April 28, 1983
    Date of Patent: November 5, 1985
    Assignee: Ethyl Corporation
    Inventor: Hsueh M. Li
  • Patent number: 4544503
    Abstract: A method of preparing alkali metal salts or alkaline earth metal salts of acyloxybenzenesulfonate by reacting an alkali metal salt or an alkaline earth metal salt of hydroxybenzenesulfonic acid with an organic compound containing olefinic unsaturation and carbon monoxide at elevated temperature and elevated pressure in the presence of a catalytic amount of a metal carbonyl compound and a promoter selected from pyridine, non-ortho-substituted alkylpyridine or mixtures thereof.
    Type: Grant
    Filed: September 1, 1983
    Date of Patent: October 1, 1985
    Assignee: Ethyl Corporation
    Inventor: C. Bernard Berry
  • Patent number: 4537755
    Abstract: To prepare halophosphazene oligomer enriched in cyclic trimer, a two-stage process is used. In the first stage halogen halide and ammonia are concurrently introduced into an agitated liquid reaction medium in which halophosphazene oligomer is soluble, these materials being proportioned so as to form a reaction system composed of a dilute slurry of finely divided ammonium halide particles. In the second stage phosphorus trihalide and halogen are concurrently introduced into the slurried reaction system from the first stage heated to a temperature of about 80.degree. to about 180.degree. C. In the process the quantities of the reactants introduced into the reaction medium are proportioned such that the ammonium halide:phosphorus trihalide molar ratio is between about 1:1 and about 3:1, and the phosphorus trihalide:halogen molar ratio is kept above about 0.
    Type: Grant
    Filed: December 5, 1983
    Date of Patent: August 27, 1985
    Assignee: Ethyl Corporation
    Inventor: Hsueh M. Li
  • Patent number: 4537724
    Abstract: An alkali metal or an alkaline earth metal salt of an acyloxybenzenesulfonate of the formula: ##STR1## wherein R is a hydrocarbyl group containing up to 30 carbon atoms selected from alkyl, alkenyl, cycloalkyl, aryl, aralkyl and M is an alkali metal or an alkaline earth metal is prepared by reacting at elevated temperature the corresponding hydroxybenzene sulfonate salt of the formula: ##STR2## with an aryl ester of the formula: ##STR3## wherein R is as defined above.
    Type: Grant
    Filed: May 11, 1983
    Date of Patent: August 27, 1985
    Assignee: Ethyl Corporation
    Inventors: Bonnie G. McKinnie, Gene C. Robinson
  • Patent number: 4536520
    Abstract: Foamed polyphosphazene articles having consistent appearance and physical properties are made by masticating a mixture of high molecular weight linear polyphosphazene, a curing agent (e.g., sulfur), an accelerator, a blowing agent and optionally fillers, processing aids and the like until the temperature of the composition rises to a pre-determined level. Mixing is stopped and the composition is shaped, heated to pre-cure and then heated to activate the blowing agent and complete the cure.
    Type: Grant
    Filed: June 11, 1984
    Date of Patent: August 20, 1985
    Assignee: Ethyl Corporation
    Inventor: Warren B. Mueller
  • Patent number: 4532368
    Abstract: A process for making a mixture of meta- and para-alkylphenols by contacting a mixture of phenol, ortho-alkylphenol and an alkylating agent (e.g. olefins or lower alcohols) with a zeolite having a silica:alumina ratio of at least 12:1 under alkylating conditions to obtain a mixture of ortho-, meta- and para-alkylphenols and then separating at least part of the ortho-alkylphenol which is recycled to a subsequent alkylation process carried out in the same manner.
    Type: Grant
    Filed: February 1, 1984
    Date of Patent: July 30, 1985
    Assignee: Ethyl Corporation
    Inventors: Barry J. Swanson, Ronald L. Shubkin
  • Patent number: 4522798
    Abstract: A mixture of compounds of the formulas:[X--(PX.sub.2 .dbd.N).sub.n --PX.sub.3 ].sup.+ [R].sup.-andX--(PX.sub.2 .dbd.N).sub.n --POX.sub.2wherein X is a halogen atom, R is X or PX.sub.6 or both of them, and n is an integer, usually below about 15, is heated either with no other reactant or with a suitable phosphorus reactant such as PX.sub.5 ; PX.sub.3 +X.sub.2 ; P+X.sub.2 ; or a mixture of two or more such phosphorus reactants so that a halophosphazene having a --PX.sub.3.sup.+ end group is formed as one of the co-products of the reaction. This co-product is a substance having the general formula[X--(PX.sub.2 .dbd.N).sub.n --PX.sub.3 ].sup.+ [R].sup.-wherein X, R and n are as defined above. The other co-product is phosphoryl trihalide, POX.sub.3. In a second stage the resultant reaction product is heated with at least a stoichiometric amount (preferably, an excess) of a nitrogen source (e.g., NH.sub.3 ; NH.sub.4 Cl; etc.
    Type: Grant
    Filed: September 8, 1983
    Date of Patent: June 11, 1985
    Assignee: Ethyl Corporation
    Inventors: Genevieve S. Lum, Hsueh M. Li, F. Alexander Pettigrew
  • Patent number: 4522795
    Abstract: Linear phosphonitrilic chloride polymers are produced from phosphonitrilic chloride oligomers by means of a two-stage process. In the first stage a mixture of phosphonitrilic chloride oligomers enriched in linear oligomer is heated with at least a stoichiometric amount (and preferably an excess) of ammonia or ammonium chloride while concurrently removing hydrogen chloride to produce an intermediate reaction product. In the second stage the molecular weight of the reaction product is increased by heating the product to a higher temperature than the average temperature used in the first stage. Cyclic phosphonitrilic chloride oligomer may be present in the initial oligomer. Preferably, cyclic phosphonitrilic chloride oligomer is recovered from the reaction mixture after the start of the second stage. Most preferably it is recovered after completion of the second stage. At least a portion of the recovered cyclic oligomer may be used in a subsequent first stage reaction.
    Type: Grant
    Filed: April 22, 1983
    Date of Patent: June 11, 1985
    Assignee: Ethyl Corporation
    Inventor: Hsueh M. Li
  • Patent number: 4522797
    Abstract: One or a mixture of compounds of the formula:X--(PX.sub.2 .dbd.N).sub.n --POX.sub.2wherein X is a halogen atom and n is an integer, usually below about 15 is heated with a suitable phosphorus reactant such as PX.sub.5 ; PX.sub.3 +X.sub.2 ; P+X.sub.2 ; or oligomer of the formula[X--(PX.sub.2 .dbd.N).sub.n --PX.sub.3 ].sup.+ [R].sup.-wherein X is a halogen atom, R is PX.sub.6 or X, and n is an integer usually below about 15; or a mixture of two or more such phosphorus reactants so that a halophosphazene having a --PX.sub.3.sup.+ end group is formed as one of the co-products of the reaction. This co-product is a substance having the general formula[X--(PX.sub.2 .dbd.N).sub.n --PX.sub.3 ].sup.+ [R].sup.-wherein X, R and n are as defined above. The other co-product is phosphoryl trihalide, POX.sub.3. In a second stage the resultant reaction product is heated with at least a stoichiometric amount (preferably, an excess) of a nitrogen source (e.g., NH.sub.3 ; NH.sub.4 Cl; etc.
    Type: Grant
    Filed: September 8, 1983
    Date of Patent: June 11, 1985
    Assignee: Ethyl Corporation
    Inventors: F. Alexander Pettigrew, Hsueh M. Li, Genevieve S. Lum
  • Patent number: 4522796
    Abstract: Linear phosphonitrilic chloride polymers are produced from phosphonitrilic chloride oligomers by means of an improved process wherein a mixture of phosphonitrilic chloride oligomers enriched in linear oligomer is heated with at least a stoichiometric amount (and preferably an excess) of ammonia or ammonium chloride while concurrently removing hydrogen chloride to produce a higher molecular weight polyphosphonitrilic chloride product. Cyclic phosphonitrilic chloride oligomer may be and preferably is present in the initial oligomer. Preferably, cyclic phosphonitrilic chloride oligomer is recovered from the reaction mixture during (but more preferably after) completion of the polymerization reaction. At least a portion of the recovered cyclic oligomer may be used in a subsequent polymerization reaction.
    Type: Grant
    Filed: April 22, 1983
    Date of Patent: June 11, 1985
    Assignee: Ethyl Corporation
    Inventor: Hsueh M. Li
  • Patent number: 4514550
    Abstract: Phosphonitrilic chloride polymers are substituted with aryloxide or alkoxide groups by reaction with an alkali metal aryloxide or alkoxide in a single liquid hydrocarbon reaction medium, e.g. cyclohexane, toluene and the like, in which the aryloxides or alkoxides are essentially insoluble and in which the substituted product is soluble.
    Type: Grant
    Filed: May 9, 1984
    Date of Patent: April 30, 1985
    Assignee: Ethyl Corporation
    Inventor: Harold R. Penton
  • Patent number: 4511753
    Abstract: Vinylidene olefins are selectively removed from a mixture of olefins containing vinylidene olefins by reacting the mixture with either hydrogen sulfide or a hydrocarbyl mercaptan and then distilling the resultant mixture to obtain a substantially vinylidene olefin-free product.
    Type: Grant
    Filed: January 16, 1984
    Date of Patent: April 16, 1985
    Assignee: Ethyl Corporation
    Inventors: R. Scott Smith, Gerald Z. Smith, Jr.
  • Patent number: 4483374
    Abstract: A method is provided for packing a high pressure liquid chromatographic column to obtain increased efficiency by suspending the packing in an alcohol medium between a lower liquid phase (e.g. carbon tetrachloride) and an upper liquid phase (e.g. isooctane) and passing the liquids under high pressure through an unpacked column lower layer first. The packing is retained in the column.
    Type: Grant
    Filed: November 1, 1982
    Date of Patent: November 20, 1984
    Assignee: Ethyl Corporation
    Inventor: Chester C. Siemion
  • Patent number: 4479905
    Abstract: A mixture of aliphatic primary monohydric alcohol and alkoxyalkanol is continuously nitrated by reaction with a nitric-sulfuric acid mixture at -10.degree. to 15.degree. C. to yield an organic nitrate mixture containing substantial amounts of alkoxyalkyl nitrate useful as a cetane improver in diesel fuel.
    Type: Grant
    Filed: September 19, 1983
    Date of Patent: October 30, 1984
    Assignee: Ethyl Corporation
    Inventors: Gordon G. Knapp, Marguerite S. Baylerian, Paul D. Seemuth
  • Patent number: 4473378
    Abstract: Compounds that are themselves effective cetane improvers in diesel fuel but are considered too explosion sensitive for safe handling can be rendered relatively nonsensitive by blending with C.sub.5 to C.sub.12 alkyl nitrates and the resulting blend is an effective cetane improver. An example is a 50--50 blend of 2-methyl-2-nitropropyl nitrate, a shock-sensitive compound, with isooctyl nitrate to give a relatively insensitive but very effective cetane improver.
    Type: Grant
    Filed: March 28, 1983
    Date of Patent: September 25, 1984
    Assignee: Ethyl Corporation
    Inventors: John V. Hanlon, James B. Hinkamp
  • Patent number: 4459419
    Abstract: Zeolite-ruthenium catalysts in which the ruthenium is in the form of a cation are very effective in catalyzing the hydrogenation of a broad range of organic compounds.
    Type: Grant
    Filed: September 2, 1982
    Date of Patent: July 10, 1984
    Assignee: Ethyl Corporation
    Inventor: Paul D. Seemuth
  • Patent number: 4457763
    Abstract: Cetane rating of diesel fuel is increased by adding a dioxane nitrate such as m-dioxan-5-ol nitrate and 1,3-dioxolane-4-methanol nitrate.
    Type: Grant
    Filed: November 7, 1983
    Date of Patent: July 3, 1984
    Assignee: Ethyl Corporation
    Inventor: Paul D. Seemuth
  • Patent number: 4448586
    Abstract: Liquid fuels having anti-corrosion properties for use in internal combustion engines comprising (i) a major fraction of a monohydroxy alkanol having from 1 to about 5 carbon atoms, and (ii) a corrosion inhibiting amount of a mixture of (a) from about 5 to 95 parts of an alkyl or alkenyl succinic acid and an ester formed from that acid, or from a related alkyl or alkenyl succinic acid, and a glycol of 2 to 4 carbon atoms wherein the alkyl or alkenyl groups in the acid and in the ester each contain about 8 to 30 carbon atoms, and (b) from about 95 to 5 parts of at least one polymerized unsaturated aliphatic monocarboxylic acid having about 16 to 18 carbon atoms per molecule.
    Type: Grant
    Filed: November 2, 1981
    Date of Patent: May 15, 1984
    Assignee: Ethyl Corporation
    Inventor: Charles F. Weidig
  • Patent number: 4448974
    Abstract: A lubricating oil dispersant made by reacting an aldehyde (e.g. isobutyraldehyde) with an amine (e.g. tetraethylenepentamine) under conditions to form a Schiff base which is then reacted with a hydrocarbon-substituted succinic acid, anhydride or lower alkyl ester.
    Type: Grant
    Filed: March 24, 1982
    Date of Patent: May 15, 1984
    Assignee: Edwin Cooper, Inc.
    Inventors: Joseph P. O'Brien, Andrew G. Papay