Abstract: A process is disclosed for the enantioselective hydrogenation of olefins of the formula: ##STR1## where R is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, Z is ##STR2## where R' is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, --CN, C(NH)OR" where R" is C.sub.1 to C.sub.6 linear or branched alkyl, or --C(O)NH.sub.2 ; and Ar is phenyl or naphthyl unsubstituted or substituted with benzoyl or substituted benzoyl, C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched alkoxy, halo, or carboxylic acid or C.sub.1 to C.sub.6 linear or branched alkyl ester thereof, which comprises contacting said aromatic-substituted olefin with a catalytically effective amount of a ruthenium phosphite complex.
Abstract: This invention relates to a process for obtaining dry sodium aluminum hydride from a slurry containing the production products from a sodium aluminum hydride plant.
Abstract: Conjugated diene impurities are removed from linear alpha-olefin products by contacting the linear alpha-olefin product with an acid treated montmorillonite clay which is effective to reduce the conjugated diene content of the linear alpha-olefin product, preferably to less than about 100 ppm, without substantial isomerization of the linear alpha-olefins to internal olefins.
Type:
Grant
Filed:
March 30, 1993
Date of Patent:
March 8, 1994
Assignee:
Ethyl Corporation
Inventors:
Stephen E. Belmont, Patrick G. Simms, Keith G. Anderson
Abstract: Improved method by control of excess bromine in reaction between bromine and cyclododecatriene to form hexabromocyclododecane provides increased product yield. A novel reaction mass is obtained and maintained.
Abstract: Tertiary amines corresponding to the formula Z.sub.2 Z'N in which Z is a 3,5-dihydrocarbyl-4-hydroxyphenalkyl group having the structure: ##STR1## wherein R is hydrogen or an alkyl group of 1-3 carbons; R' and R" are hydrocarbyl groups independently selected from alkyls and cycloalkyls of up to six carbons; n represents zero or one; and Z' is Z or an alkyl, alkenyl, or aralkyl group of up to 18 carbons are novel compounds having antioxidant activity in organic materials which are normally susceptible to oxidative deterioration. They are especially valuable as antioxidants for lubricants.
Abstract: A 1,3,5-trimethyl-2,4,6-tris(3,5-dialkyl-4-hydroxybenzyl)benzene is prepared in high yield by reacting a 2,6-dialkyl-4-methoxymethylphenol with mesitylene in a hydrocarbon solvent and in the presence of at least about 10 mol %, based on the amount of mesitylene, of a hydrocarbon-soluble acid (e.g., an alkylbenzenesulfonic acid having 12-18 carbons in the alkyl group, a carboxylic acid, or a dialkylsulfosuccinate) as a catalyst or co-catalyst while distilling methanol by-product out of the reaction mixture as it is formed. The process may be conducted so as to provide a substantially pure product or a product, such as 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)benzene, having fairly high purity (e.g., about 98-98%) and a melting point much lower than would be expected of a product having such high purity.
Abstract: Novel perhydrates having utility as surfactants and bleaching agents are obtained by reacting an anhydrous amine oxide or an amine oxide monohydrate with hydrogen peroxide in such proportions as to provide a compound corresponding to the formula RR'R"NO.multidot.xH.sub.2 O.multidot.yH.sub.2 O.sub.2 in which R is a primary alkyl group containing 8-24 carbons; R' is methyl, ethyl, or 2-hydroxyethyl; R" is independently selected from methyl, ethyl, 2-hydroxyethyl, and primary alkyl groups containing 8-24 carbons; x is 0 or 1; y is 1 or 2; and x+y is .ltoreq.2.
Type:
Grant
Filed:
June 22, 1992
Date of Patent:
March 8, 1994
Assignee:
Ethyl Corporation
Inventors:
Kim R. Smith, James E. Borland, Joe D. Sauer
Abstract: A pourable amine oxide composition which is suitable for use in detergent compositions is obtained by reacting a tert-amine with aqueous hydrogen peroxide in a nonionic surfactant as the sole organic solvent, at least a portion of the nonionic surfactant being an alkylphenol ethoxylate or other compound corresponding to the formula Z[OC(Z')HCH.sub.2 ].sub.m OH in which Z is an alkylphenyl group wherein the alkyl group contains 4-30 carbons, Z' is hydrogen or an alkyl or hydroxyalkyl group containing 1-3 carbons, and m is an integer of 1-100. When the composition has a low water content, it is suitable for use in water-sensitive formulations, such as bar soaps and detergent concentrates.
Type:
Grant
Filed:
December 17, 1990
Date of Patent:
March 8, 1994
Assignee:
Ethyl Corporation
Inventors:
James E. Borland, Joe D. Sauer, Kim R. Smith
Abstract: Non-solvated hydridomagnesium chloride is prepared in high yield under moderate conditions by reacting magnesium hydride and magnesium chloride in a hydrocarbon solvent and in the presence of a trialkylaluminum catalyst.
Abstract: Neopolyol derivatives in which at least one of the hydroxyl groups is replaced with a substituent that corresponds to the formula --O--R--C(O)--OR' wherein R is an alkylene group containing 2-5 carbons and R' is a hydrocarbyl or predominantly hydrocarbyl group containing 1-30 carbons are oils which have utility as lubricants. Those in which R' is a hydrocarbyl group of 1-10 carbons are completely miscible with 1,1,1,2 -tetrafluoroethane (R-134a), a refrigerant.
Abstract: This invention relates to a process for preparing a white bisimide product which principally contains N,N'-alkylene-bis(tetrabromophthalimide) or N,N'-bis(tetrabromophthalimide). The process features: providing, in a reaction vessel, a solution containing tetrabromophthalic anhydride and a solvent which contains at least about 15 weight percent of a mono-, di- or tri- carboxylic acid having a dissociation constant not higher than 1.0.times.10.sup.-3 at 25.degree. C.; forming a reaction mass by adding to the solution a diamine or a diamine salt formed by the partial or total diamine neutralization of a mono-, di- or tri- carboxylic acid having a dissociation constant not higher than 1.0.times.10.sup.-3 at 25.degree. C.
Type:
Grant
Filed:
August 11, 1992
Date of Patent:
March 1, 1994
Assignee:
Ethyl Corporation
Inventors:
Ranjit K. Roy, Ali M. Dadgar, Donald O. Hutchinson, Keith G. Anderson
Abstract: Improved process for separating ethylsilane from silane by selective adsorption onto an effectively treated carbon bed and method of treatment of such carbon bed to enhance the selective adsorption of ethylsilane.
Type:
Grant
Filed:
April 24, 1992
Date of Patent:
March 1, 1994
Assignee:
Ethyl Corporation
Inventors:
Andrew O. Wikman, Won S. Park, Charles R. Everly
Abstract: This invention relates to an improvement in a process for preparing tetrabromophthalic anhydride whereby there is a substantial recovery of reactants such as halogen and SO.sub.3 from a vent stream exiting the reaction vessel. The improvement comprises contacting the vent stream with a fluid having a first oleum concentration and recovering a halogen stream and a second stream, having a second oleum concentration wherein the second oleum concentration is greater than the first oleum concentration.
Type:
Grant
Filed:
September 28, 1992
Date of Patent:
February 22, 1994
Assignee:
Ethyl Corporation
Inventors:
Scott A. Bottelberghe, Bonnie G. McKinnie, Steven G. Miller, David E. Raposa
Abstract: A friction-reducing lubricating oil composition and a method for reducing the fuel consumption of an internal combustion engine are disclosed. The lubricating oil composition comprises (a) a major amount of an oil having lubrication viscosity; (b) a minor amount of a friction-modifying, polar and surface-active compound; (c) a minor amount of a Group IA alkoli metal containing compound and (d) a minor amount of a transition element metal in a hydrocarbon-soluble or dispersible compound. The method for reducing fuel consumption of a spark-ignited internal combustion engine comprises utilizing an embodiment of the lubricating oil composition in the crankcase of the engine.
Abstract: A synthetic oil is made by a process comprising (a) isomerizing at least a portion of a vinylidene olefin feed to form an intermediate which contains tri-substituted olefin and (b) reacting said intermediate and at least one vinyl olefin in the presence of a catalyst to form a synthetic oil which comprises a co-dimer of said vinylidene olefin and said vinyl olefin.
Type:
Grant
Filed:
August 28, 1992
Date of Patent:
February 8, 1994
Assignee:
Ethyl Corporation
Inventors:
Robert A. Schaerl, Jr., Ali M. Dadgar, Carroll W. Lanier
Abstract: This invention relates to a process for preparing a flame retardant product predominant in tetrabromobisphenol-A. The process comprises: (a) dissolving bisphenol-A in a methanol solvent containing up to about 5 weight percent water, wherein the ratio of methanol to bisphenol-A ranges from about 25 to about 43 moles of methanol per mole of bisphenol-A based on the total amount of methanol used and the total amount of bisphenol-A to be brominated; (b) adding to the solution in (a) from about 3.9 to about 4.2 moles of bromine per mole of bisphenol-A to be brominated while maintaining a reaction temperature in the range of from about 0.degree. to about 40.degree. C.; (c) after the bromination is substantially complete, adding water to precipitate the tetrabromobisphenol-A thus formed; and (d) purifying the precipitated tetrabromobisphenol-A so as to obtain a product predominant in tetrabromobisphenol-A containing less than about 20 ppm total ionic impurity.
Type:
Grant
Filed:
December 15, 1992
Date of Patent:
February 1, 1994
Assignee:
Ethyl Corporation
Inventors:
Bonnie G. McKinnie, Gary L. Sharp, Robert E. Williams
Abstract: A process for the carbonylation of substituted metal coordination compounds in the presence of carbon monoxide at a pressure in excess of 400 psig to produce optionally substituted cyclopentadienyl metallic carbonyls, particularly methylcyclopentadienyl manganese tricarbonyl in a thin-film-producing reactor.
Type:
Grant
Filed:
June 4, 1992
Date of Patent:
January 25, 1994
Assignee:
Ethyl Corporation
Inventors:
Carl O. Inabinet, Fred H. Gregory, David M. Marchand, Robert B. Agee
Abstract: The impact strength of articles made from a flame-retarded formulated ABS resin containing an impact modifier is increased by forming a concentrate or masterbatch containing the flame retardant and impact modifier, blending the concentrate with ABS resin and extruding the resultant blend.
Type:
Grant
Filed:
August 3, 1992
Date of Patent:
January 25, 1994
Assignee:
Ethyl Corporation
Inventors:
David K. Doucet, Janet F. Jones, Susan D. Landry, F. Alexander Pettigrew, Jon S. Reed, James E. Torres
Abstract: This invention relates to a method for increasing the ultraviolet light stability of articles made from macromolecular materials comprising: forming a flame-retarded formulation containing macromolecular material and a mixture of (i) a first alkylenebis(tetrabromophthalimide) flame retardant having a yellowness index (YI) value ranging from about 20 to about 40 as determined by ASTM D-1925; and (ii) a second alkylenebis-(tetrabromophthalimide) flame retardant having a yellowness index (YI) value (ASTM D-1925) ranging from about 2 to about 15 whereby the uv stability of a test plaque made from the flame-retarded formulation is greater than the arithmetic average of the uv stabilities of a test plaque made from a flame-retarded formulation containing (i) but not (ii) and of a test plaque made from a flame-retarded formulation containing (ii) but not (i).
Type:
Grant
Filed:
February 9, 1993
Date of Patent:
January 18, 1994
Assignee:
Ethyl Corporation
Inventors:
Susan D. Landry, Jon S. Reed, F. Alexander Pettigrew
Abstract: A method for racemizing an optically active aliphatic carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.2 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid, ester or salt thereof at a temperature of from about 100.degree. C. to about 400.degree. C.