Patents by Inventor Herbert E. Fried
Herbert E. Fried has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 5166409Abstract: The present invention relates to a process for the preparation of higher alkyl acrylic acid esters which comprises contacting and reacting under ene reaction conditions one or more olefins with one or more alkyl acrylic acid esters in the presence of a catalytically effective amount of a mixture of aluminum chloride and ethylaluminum dichloride.Type: GrantFiled: November 25, 1991Date of Patent: November 24, 1992Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 5166422Abstract: A process for the preparation of an alkanoic acid which comprises reacting the corresponding alkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, and an alkali metal nitrosodisulfonate in the presence of an oxidant at a temperature in the range of from about -10.degree. C. to about 60.degree. C. and thereafter separating out the alkanoic acid.Type: GrantFiled: August 30, 1991Date of Patent: November 24, 1992Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 5162579Abstract: A process for the preparation of an alkoxyalkanoic acid of the formulaRO(CH.sub.2 CHR'O).sub.n CH.sub.2 CO.sub.2 Hwherein R is an alkyl group of from 1 to about 22 carbon atoms, R' is hydrogen or methyl or mixtures thereof (on the individual molecule) and n is an integer of from 1 to about 12, which comprises reacting the corresponding alkoxyalkanol with a stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, and nitric acid in the presence of an oxidant at a temperature in the range of from about 0.degree. C. to about 100.degree. C. and thereafter separating out the alkoxyalkanoic acid.Type: GrantFiled: August 30, 1991Date of Patent: November 10, 1992Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 5155279Abstract: A process for the preparation of an aldehyde which comprises reacting the corresponding alkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, nitric acid and a solvent, in the absence of an oxidant at a temperature in the range of from about -10.degree. C. to about 60.degree. C. and thereafter separating out the aldehyde.Type: GrantFiled: October 18, 1991Date of Patent: October 13, 1992Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 5155278Abstract: A process for the preparation of an aldehyde which comprises reacting the corresponding alkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, nitric acid and a non-basic polar solvent, in the presence of an oxidant, for about eight hours or less at a temperature in the range of from about -10.degree. C. to about 25.degree. C., and thereafter separating out the aldehyde.Type: GrantFiled: September 30, 1991Date of Patent: October 13, 1992Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 5155280Abstract: A process for the preparation of an aldehyde which comprises reacting the corresponding alkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, an alkali metal nitrosodisulfonate, a non-basic polar solvent and an oxidant, for about eight hours or less at a temperature in the range of from about 10.degree. C. to about 20.degree. C. and thereafter separating out the aldehyde.Type: GrantFiled: September 30, 1991Date of Patent: October 13, 1992Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 5136103Abstract: A process for the preparation of a ketone which comprises reacting the corresponding secondary alkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, and nitric acid in the presence of an oxidant at a temperature in the range of from about -10.degree. C. to about 80.degree. C. and thereafter separating out the ketone.Type: GrantFiled: September 30, 1991Date of Patent: August 4, 1992Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 5136102Abstract: A process for the preparation of a ketone which comprises reacting the corresponding secondary alkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, nitric acid, and a bromide ion-containing compound in the presence of an oxidant at a temperature in the range of from about -10.degree. C. to about 60.degree. C. and thereafter separating out the ketone.Type: GrantFiled: October 18, 1991Date of Patent: August 4, 1992Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 5136101Abstract: A process for the preparation of a ketone which comprises reacting the corresponding secondary alkanol with a solubilized stable free radical nitroxide having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is an alkyl, aryl or heteroatom substituted alkyl group having 1 to about 15 carbon atoms and each of R.sub.5 and R.sub.6 is alkyl, hydrogen, aryl or a substituted heteroatom, and an alkali metal nitrosodisulfonate in the presence of an oxidant at a temperature in the range of from about -10.degree. C. to about 80.degree. C. and thereafter separating out the ketone.Type: GrantFiled: September 30, 1991Date of Patent: August 4, 1992Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 5114624Abstract: In a process for the preparation of higher alkyl acrylic acid esters which comprises reacting one or more C.sub.10+ olefins with one or more alkyl acrylic acid esters in the presence of a halogen containing catalyst, the invention is the improvement which comprises contacting the reaction product mixture with an aqueous acid solution to extract catalyst residues therefrom and distilling the extracted product mixture to remove unreacted olefin.Type: GrantFiled: April 17, 1990Date of Patent: May 19, 1992Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 5066829Abstract: A process for the preparation of higher alkyl acrylic acid esters which comprises the addition reaction of olefins to alkyl acrylic acid esters catalyzed by tantalum pentachloride.Type: GrantFiled: April 17, 1990Date of Patent: November 19, 1991Assignee: Shell Oil CompanyInventors: Herbert E. Fried, Thomas H. Johnson
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Patent number: 4931205Abstract: Certain mixtures of the ethylene oxide adducts of higher carbon number tertiary thiols, having a reduced content of free thiols and lower (i.e., 1 to 3 mol) ethylene oxide adducts, exhibit improved detergency performance, particularly in high temperature laundry applications.Type: GrantFiled: August 9, 1988Date of Patent: June 5, 1990Assignee: Shell Oil CompanyInventors: Charles L. Edwards, Herbert E. Fried, Werner Lilienthal
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Patent number: 4879394Abstract: Olefinically unsaturated hydrocarbons are reacted with maleic anhydride to form the corresponding succinic anhydride in the presence of an alkoxide of zinc or dialkyl zinc which prevents side-reactions. These products are used for the preparation of anticorrosive agents.Type: GrantFiled: May 4, 1988Date of Patent: November 7, 1989Assignee: Shell Oil CompanyInventors: Herbert E. Fried, Charles L. Edwards
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Patent number: 4822911Abstract: A process for the selective separation of certain vinylidene olefins from their mixtures with linear olefins and for the preparation of valuable alkyl esters of acrylic acid, which comprises steps for(a) contacting and reacting a liquid phase C.sub.6 to C.sub.30 olefin feedstock mixture containing both one or more ethyl- and higher alkyl-branched vinylidene olefins and one or more linear olefins with one or more reactive agents selected from the group consisting of alkyl esters of acrylic acid at a temperature of between about 40.degree. and 200.degree. C. and in the presence of a catalytically effective amount of one or more ene reaction catalysts, to selectively convert all or part of the ethyl- and higher alkyl-branched vinylidene olefins of said feedstock mixture to higher carbon number acrylic acid esters and to produce a product mixture comprising the resulting higher acrylic acid esters and unreacted olefins, and(b) terminating step (a) and separating the unreacted olefins from said product mixture.Type: GrantFiled: September 25, 1987Date of Patent: April 18, 1989Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 4761488Abstract: Olefinically unsaturated hydrocarbons are reacted with maleic anhydride to form the corresponding succinic anhydride, in the presence of an additive, aluminum acetylacetonate, which prevents side reactions. These products are used for the preparation of anticorrosive agents.Type: GrantFiled: November 13, 1987Date of Patent: August 2, 1988Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 4721819Abstract: In a process for the preparation of allylic ethers which comprises contacting and reacting an allylic alcohol reactant comprising one or more C.sub.6 to C.sub.20 allylic alcohols with a glycol reactant comprises one or more C.sub.2 or C.sub.3 alkylene glycols and their polyalkylene glycols in the presence of a cuprous salt catalyst and an acidic co-catalyst, the invention is the improvement which comprises contacting the allylic alcohol and alkylene glycol reactants in an agitated reaction mixture containing a solvent for the allylic alcohol reactant and the ether product which is substantially immiscible with the alkylene glycol reactant, said solvent being present in the reaction mixture in a quantity by weight which is at least about three times the weight of the allylic alcohol reactant. The improvement of the invention substantially increases the selectivity of the process for the production of the allylic ethers.Type: GrantFiled: December 30, 1986Date of Patent: January 26, 1988Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 4638093Abstract: A process is disclosed for the preparation of secondary thiols by the addition of H.sub.2 S to C.sub.10 to C.sub.30 linear olefins in the presence of certain zeolite catalysts. The process achieves high selectivity to the secondary thiol and minimizes formation of dialkyl sulfide by-products. The secondary thiol products are of particular advantage for use as intermediates in the preparation of surfactant chemicals.Type: GrantFiled: April 2, 1985Date of Patent: January 20, 1987Assignee: Shell Oil CompanyInventor: Herbert E. Fried
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Patent number: 4618400Abstract: A method for the deinking of wastepaper which comprises converting the wastepaper to a pulp, contacting the pulp with an aqueous medium of alkaline pH containing between about 0.2 and 2 percent by weight, calculated on dry weight of the pulp, of a deinking agent which is one or a mixture of certain thiol ethoxylate compounds, and treating the resulting pulp-containing medium to remove suspended or dispersed ink. The use of a thiol ethoxylate deinking agent offers a high level of performance in such a deinking process, both from the standpoint of the overall brightness and dirt count of paper prepared from the deinked pulp. In certain specific embodiments, the invention further comprises a step for treating thiol ethoxylate containing process streams and effluents to convert the surface active deinking agent to low-foaming sulfonyl derivatives, or to degrade the deinking agent to non-surface-active matter.Type: GrantFiled: January 10, 1986Date of Patent: October 21, 1986Assignee: Shell Oil CompanyInventors: Donald L. Wood, Herbert E. Fried