Patents Represented by Attorney Howard W. Haworth
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Patent number: 4233460Abstract: An extremely mild, oxidative process for converting alkoxyalkanols to the corresponding acids is disclosed which comprises reacting the alcohol with an alkali metal hydroxide and tert-butyl hydroperoxide in the presence of a catalytic amount of palladium.Type: GrantFiled: May 3, 1979Date of Patent: November 11, 1980Assignee: Shell Oil CompanyInventors: Carl L. Willis, Lynn H. Slaugh
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Patent number: 4229605Abstract: A process for preparing 1,7-octadiene by hydrodimerizing butadiene which comprises reacting the butadiene in the presence of formic acid or a salt thereof, optionally a solvent and a catalyst comprising palladium complexed with a tertiary phosphinite or phosphonite. More active catalysts are obtained with phosphinites and phosphonites than with phosphines or phosphites.Type: GrantFiled: December 13, 1978Date of Patent: October 21, 1980Assignee: Shell Oil CompanyInventor: Kenzie Nozaki
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Patent number: 4229374Abstract: Tertiary amines are produced by reacting aliphatic, cycloaliphatic or araliphatic alcohols, aldehydes or ketones with ammonia, primary or secondary amines in the presence of a catalyst having improved selectivity and stability and which comprises a mixture of copper, tin and an alkali metal supported on a suitable carrier.Type: GrantFiled: June 28, 1979Date of Patent: October 21, 1980Assignee: Shell Oil CompanyInventors: Lynn H. Slaugh, Galeon W. Schoenthal
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Patent number: 4229606Abstract: A process for preparing 1,7-octadiene by hydrodimerizing butadiene which comprises reacting the butadiene in the presence of formic acid, or a salt thereof, optionally a solvent and a catalyst comprising palladium complexed with a sterically hindered phosphine, phosphinite or phosphonite and a different ligand selected from phosphine, phosphinite, phosphonite or phosphite. Enhanced catalytic activity is obtained.Type: GrantFiled: December 13, 1978Date of Patent: October 21, 1980Assignee: Shell Oil CompanyInventor: Kenzie Nozaki
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Patent number: 4206149Abstract: Amines are produced by reacting alcohols, aldehydes or ketones with ammonia, primary or secondary amines in the presence of a catalyst having improved selectivity and stability and which comprises a mixture of copper and rhenium.Type: GrantFiled: October 30, 1978Date of Patent: June 3, 1980Assignee: Shell Oil CompanyInventor: Lynn H. Slaugh
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Patent number: 4206150Abstract: Amines are produced by reacting alcohols, aldehydes or ketones with ammonia, primary or secondary amines in the presence of a catalyst having improved selectivity and stability and which comprises a mixture of copper and molybdenum and/or tungsten supported on alumina.Type: GrantFiled: December 11, 1978Date of Patent: June 3, 1980Assignee: Shell Oil CompanyInventor: Lynn H. Slaugh
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Patent number: 4198352Abstract: Internal olefins are hydroformylated to linear aldehydes in substantial amounts by contacting the internal olefins with hydrogen, carbon monoxide and a catalyst comprising a ligand stabilized ionic platinum compound of the general formula PtCl(CO)(Ligand).sub. 2.sup.+ An.sup.- complexed with a modifying metal halide selected from tin, zinc, or germanium halides.Type: GrantFiled: November 29, 1978Date of Patent: April 15, 1980Assignee: Shell Oil CompanyInventors: Leo Kim, Sunny C. Tang
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Patent number: 4189403Abstract: 1,5-Dimethyl-1,5-cyclooctadiene and 1,4-dimethyl-4-vinyl-1-cyclohexene are prepared by contacting isoprene with a catalyst obtained by mixing a nickel compound, a reducing agent capable of reducing the nickel to zerovalent nickel, and a trihydrocarbyl phosphite, arsenite or antimonite wherein at least one of the three hydrocarbyl groups is a substituted hydrocarbyl group CF.sub.3 --(CF.sub.2).sub.n C(H)(R)--, in which n.ltoreq.O and R is an optionally substituted hydrocarbyl group. Only very small amounts of the undesired 1,6-dimethyl-1,5-cyclooctadiene are formed.Type: GrantFiled: February 16, 1979Date of Patent: February 19, 1980Assignee: Shell Oil CompanyInventors: Cornelis F. Roobeek, Petrus W. N. M. van Leeuwen
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Patent number: 4180694Abstract: Butadiene is hydrodimerized to 1,7-octadiene in high yield by contacting the butadiene with a formate of an alkali metal, alkaline earth metal or ammonia, a palladium catalyst, tertiary phosphine, a solvent selected from dialkyl sulfoxides, N,N-dialkylalkanamides, substituted and unsubstituted pyridines and sulfolanes and at least one mole of water per mole of formate salt.Type: GrantFiled: July 24, 1978Date of Patent: December 25, 1979Assignee: Shell Oil CompanyInventor: Kenzie Nozaki
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Patent number: 4179402Abstract: A composition comprising an ion exchange resin, a metal selected from the transition group of elements bound to said resin and an organic linking compound which has at least one moiety which is ionically bonded to said resin and which further has at least one moiety which is coordinately bonded to said metal.Type: GrantFiled: May 15, 1978Date of Patent: December 18, 1979Assignee: Shell Oil CompanyInventors: Leo Kim, Timm E. Paxson, Sunny C. Tang
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Patent number: 4179403Abstract: A composition comprising an ion exchange resin and an organic linking compound having at least one resin-compatible moiety ionically bound to said resin and further having at least one metal complexible moiety selected from the group consisting of trivalent nitrogen, trivalent phosphorus, trivalent arsenic, trivalent bismuth and trivalent antimony complexed to a metal selected from Group IVB, VB, VIB, VIIB, VIII and IB metals, said composition being useful in heterogeneous catalysis.Type: GrantFiled: December 19, 1977Date of Patent: December 18, 1979Assignee: Shell Oil CompanyInventors: Leo Kim, Timm E. Paxson, Sunny C. Tang
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Patent number: 4177220Abstract: Vinyl acetylene is coupled with butadiene to selectively produce 1-octen-7-yne by reacting the vinyl acetylene with butadiene in the presence of formic acid or a salt thereof, optionally a solvent and a catalyst comprising palladium complexed with tertiary organophosphorus ligand.Type: GrantFiled: November 6, 1978Date of Patent: December 4, 1979Assignee: Shell Oil CompanyInventor: Kenzie Nozaki
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Patent number: 4166076Abstract: 1,5-Dimethyl-1,5-cyclooctadiene and 1,4-dimethyl-4-vinyl-1-cyclohexene are prepared by contacting isoprene with a catalyst obtained by mixing a nickel compound, a reducing agent capable of reducing the nickel to zerovalent nickel, and a trihydrocarbyl phosphite, arsenite or antimonite wherein at least one of the three hydrocarbyl groups is a substituted hydrocarbyl group CF.sub.3 --(CF.sub.2).sub.n C(H)(R)--, in which n.gtoreq.0 and R is an optionally substituted hydrocarbyl group. Only very small amounts of the undesired 1,6-dimethyl-1,5-cyclooctadiene are formed.Type: GrantFiled: January 16, 1978Date of Patent: August 28, 1979Assignee: Shell Oil CompanyInventors: Cornelis F. Roobeek, Petrus W. N. M. VAN Leeuwen
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Patent number: 4166189Abstract: Method for the production of branched chain esters comprising contacting methanol and/or dimethyl ether and carbon monoxide with zinc iodide at a temperature of from about 180.degree. C. to 450.degree. C. Improved selectivity to methyl pivalate is obtained by incorporating ethylene, propylene and/or isobutylene into the reaction mixture.Type: GrantFiled: April 24, 1978Date of Patent: August 28, 1979Assignee: Shell Oil CompanyInventors: Milton M. Wald, Leo Kim
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Patent number: 4165440Abstract: An improved process for the low temperature preparation of ethylene glycol by the catalytic hydration of ethylene oxide using a fluorinated alkyl sulfonic acid ion exchange resin is described.Type: GrantFiled: October 3, 1977Date of Patent: August 21, 1979Assignee: Shell Oil CompanyInventor: Leo Kim
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Patent number: 4003952Abstract: An improvement in the process for producing alcohols by the direct hydration of olefins in the presence of a catalyst, where the reactor effluent is scrubbed with water in a scrubbing zone and where the olefin feed is introduced in the lower portion of the scrubbing zone to strip out the organic impurities found in the aqueous alcohol product stream.Type: GrantFiled: September 23, 1974Date of Patent: January 18, 1977Assignee: Shell Oil CompanyInventors: Elton Gordon Foster, Robert A. Golding, Delwin E. Dodd