The Alkylating Agent Is An Olefin Patents (Class 562/94)
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Publication number: 20150126770Abstract: A process for increasing the production of monoalkylbenzenes is presented. The process includes utilizing a transalkylation process to convert dialkylbenzenes to monoalkylbenzenes. The feed to the transalkylation process has alkylated toluenes and alkylated ethylbenzenes and other alkylated aromatics having small alkyl groups with less than 8 carbons removed to improve the efficiency of the transalkylation process. The recycled dialkylbenzenes and a portion of the recycled benzene are converted to monoalkylbenzenes.Type: ApplicationFiled: November 1, 2013Publication date: May 7, 2015Applicant: UOP LLCInventors: Stephen W. Sohn, Mark G. Riley, Michael A. Moore
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Publication number: 20150072916Abstract: The production of linear alkylbenzene from a natural oil is provided. A method comprises the step of deoxygenating the natural oils to form a stream comprising paraffins. The paraffins are dehydrogenated to provide mono-olefins. Then, benzene is alkylated with the mono-olefins under alkylation conditions to provide an alkylation effluent comprising alkylbenzenes and benzene. Thereafter, the alkylbenzenes are isolated to provide the alkylbenzene product.Type: ApplicationFiled: June 6, 2014Publication date: March 12, 2015Applicant: UOP LLCInventors: Stanley J. Frey, Daniel L. Ellig, Andrea G. Bozzano, Geoffrey W. Fichtl, Debarshi Majumder
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Publication number: 20140081043Abstract: Disclosed is a method for improving filtration in the preparation of an alkaline earth metal alkyltoluene sulfonate concentrate by selectively controlling the meta, ortho, para isomer distribution of the alkyl group of the alkyltoluene produced by the process comprising alkylating toluene with at least one isomerized normal alpha olefin, having from about 18 to about 30 carbon atoms and having from 20% to 100% branching in an alkylation process which includes monitoring % isomer formation and adjusting an alkylation process parameter in order to provide a target specified isomer content of less than 38% meta-isomer content; and thereafter sulfonating and neutralizing to produce a low base number sulfonated alkyltoluene concentrate having a Base Number of about 2 to 60 (ASTM D 2896).Type: ApplicationFiled: March 30, 2011Publication date: March 20, 2014Inventors: Pierre Téqui, Curt B. Campbell, Gilles P. Sinquin, Christine Boemare Gandon, Kyle J. Frederic, Eugene E. Spala
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Publication number: 20120214724Abstract: The invention is directed to mixtures comprising C10-C13 alkylphenyl sulfonates having alkyl groups in a particular distribution (e.g., bimodal, peaked, and skewed). These C10-C13 alkylphenyl sulfonates are optionally renewable and unexpectedly provide superior results when used in consumer product cleaning and personal care compositions (e.g., dishcare, laundry, hard surface cleaners, shampoos, conditioners, and soaps). The invention is further directed to a method of making a mixture of partially or wholly renewable C10-C13 alkylphenyl sulfonates having a particular alkyl group distribution.Type: ApplicationFiled: February 17, 2012Publication date: August 23, 2012Inventors: Jeffrey John Scheibel, Phillip Richard Green, Jiten Odhavji Dihora, Phillip Kyle Vinson, Stephanie Ann Urbin, Dimitris Ioannis Collias
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Publication number: 20120213726Abstract: The invention is directed to mixtures comprising C10-C14 linear alkylphenyl sulfonates with alkyl groups having a biobased content of at least 50%. These C10-C14 linear alkylphenyl sulfonates are used in consumer product cleaning and personal care compositions (e.g., dishcare, laundry, hard surface cleaners, shampoos, conditioners, and soaps). The invention is further directed to a method of making a mixture of partially or wholly bio-based C10-C14 linear alkylphenyl sulfonates with alkyl groups having a particular bio-based content.Type: ApplicationFiled: February 17, 2012Publication date: August 23, 2012Inventors: Phillip Richard Green, Jeffrey John Scheibel, Dimitris Ioannis Collias
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Patent number: 8158819Abstract: The present invention refers to a process to obtain a highly soluble linear alkylbenzene sulfonate (LAS). Specifically it comprises the addition, prior or after sulfonation of linear alkylbenzene and/or neutralization of linear alkylbenzene sulfonic acid of an hydrotropic composition. It also refers to a hydrotropic composition, to a highly soluble linear alkylbenzene sulfonate, to the use of the hydrotropic composition for making said linear alkylbenzene sulfonate highly soluble and to a cleaning composition comprising said linear alkylbenzene sulfonate.Type: GrantFiled: April 12, 2005Date of Patent: April 17, 2012Assignee: Cepsa Quimica S.A.Inventors: José Luis Berna Tejero, José Luis Goncalvez De Almeida, Ignacio López Serrano
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Patent number: 8034973Abstract: The present invention relates to a process for obtaining a highly soluble linear alkylbenzene sulfonate with an adjustable 2-phenyl isomer content and an extremely low sulfonation color, in which a catalytic system based on highly stable solid catalysts and with a high selectivity for linear monoalkylated compounds is used.Type: GrantFiled: March 16, 2006Date of Patent: October 11, 2011Assignee: Cepsa Quimica, S.A.Inventors: José Luis Goncalvez De Almeida, José Luis Berna Tejero
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Patent number: 7449596Abstract: A process for preparing a synthetic petroleum sulfonate comprising (a) reacting at least one aromatic compound with a mixture of olefins selected from olefins having from about 8 to about 100 carbon atoms, in the presence of an acidic ionic liquid catalyst, wherein the resulting product comprises at least about 50 weight percent of a 1,2,4 tri-substituted aromatic compound or a 1,2,3 tri-substituted aromatic compound or mixtures thereof; (b) reacting the product of (a) with sulfur trioxide, which has been diluted with air; and (c) neutralizing the product of (b) with an alkali or alkaline earth metal hydroxide.Type: GrantFiled: December 21, 2005Date of Patent: November 11, 2008Assignee: Chevron Oronite Company LLCInventors: Curt B. Campbell, Thomas V. Harris, Gilles Sinquin
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Patent number: 7148388Abstract: In a process for preparing an olefinic hydrocarbon mixture comprising at least 5% by weight of mono-olefin oligomers of the empirical formula: CnH2n where n is greater than or equal to 6, a feedstock comprising n-butene and propylene in a molar ratio of about 1:0.01 to about 1:0.49 is contacted under oligomerization conditions with surface deactivated ZSM-23. The resultant mono-olefin oligomers comprise at least 20 percent by weight of olefins having at least 12 carbon atoms, wherein said olefins having at least 12 carbon atoms have an average of from about 0.8 to about 2.0 C1–C3 alkyl branches per carbon chain.Type: GrantFiled: March 28, 2003Date of Patent: December 12, 2006Assignee: ExxonMobil Chemical Patents Inc.Inventors: Stephen W. Beadle, Cesar M. Cheng-Guajardo, Carolyn B. Duncan, David Wayne Turner, Ramzi Y. Saleh
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Patent number: 7060852Abstract: The invention relates to a process for the preparation of alkylarylsulfonates by a) reaction of a C4-olefin mixture over a metathesis catalyst for the preparation of an olefin mixture comprising 2-pentene and/or 3-hexene, and optional removal of 2-pentene and/or 3-hexene, b) dimerization of the 2-pentene and/or 3-hexene obtained in stage a) over a dimerization catalyst to give a mixture containing C10-12-olefins, and optional removal of the C10-12-olefins, c) reaction of the C10-12-olefin mixtures obtained in stage b) with an aromatic hydrocarbon in the presence of an alkylating catalyst to form alkylaromatic compounds, where, prior to the reaction, additional linear olefins may be added, d) sulfonation of the alkylaromatic compounds obtained in stage c), and neutralization to give alkylarylsulfonates, where, prior to the sulfonation, linear alkylbenzenes may additionally be added, e) optional mixing of the alkylarylsulfonates obtained in stage d) with linear alkylarylsulfonates.Type: GrantFiled: August 10, 2001Date of Patent: June 13, 2006Assignee: BASF AktiengesellschaftInventors: Heiko Maas, Thomas Narbeshuber, Michael Roeper
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Patent number: 6906230Abstract: The invention describes a process for the preparation of surfactant alcohols and surfactant alcohol ethers which are, inter alia, highly suitable as surfactants or for the preparation of surfactants. The process, starting from olefin mixtures having a defined minimum content of linear hexenes, gives mixtures having a predominant fraction of branched dodecenes, which are subsequently derivatized to give surfactant alcohols and then optionally alkoxylated. The surfactant alcohol mixture obtained in the process has a degree of branching of from 2.0 to 3.0 and in particular exhibits advantageous properties as regards ecotoxicity and biodegradability. A description is also given of the use of the surfactant alcohols and surfactant alcohol ethers as surfactants by glycosidation or polyglycosidation, sulfation or phosphation.Type: GrantFiled: March 17, 2000Date of Patent: June 14, 2005Assignee: BASF AktiengesellschaftInventors: Heiko Maas, Michael Röper, Marc Walter, Ralf Schulz, Jürgen Tropsch, Hans-Ulrich Jäger
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Publication number: 20040010161Abstract: The invention relates to a process for the preparation of alkylarylsulfonates byType: ApplicationFiled: February 10, 2003Publication date: January 15, 2004Inventors: Heiko Maas, Thomas Narbeshuber, Michael Roper
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Patent number: 6673961Abstract: Processes for making particularly branched, especially monomethyl-branched or nongeminal dimethyl-branched surfactants used in cleaning products; preferred processes comprising particular combinations of two or more adsorptive separation steps and, more preferably, particular alkylation steps; products of such processes, including certain modified alkylbenzenes, modified alkylbenzenesulfonate surfactants, and consumer cleaning products, especially laundry detergents, containing them. Preferred processes herein more specifically use specific, unconventional sequences of sorptive separation steps to secure certain branched hydrocarbon fractions which are used in further process steps as alkylating agents for arenes or for other useful surfactant-making purposes. Surprisingly, such fractions can even be derived from effluents from current linear alkylbenzene manufacture.Type: GrantFiled: November 26, 2002Date of Patent: January 6, 2004Assignee: The Procter & Gamble CompanyInventors: Daniel Stedman Connor, Jeffrey John Scheibel, James Charles Theophile Roger Burckett-St. Laurent, Thomas Anthony Cripe, Kevin Lee Kott, Phillip Kyle Vinson
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Patent number: 6617481Abstract: The present invention is a process for producing phenyl-alkanes by paraffin adsorptive separation followed by paraffin dehydrogenation and then by alkylation of a phenyl compound by a lightly branched olefin. The adsorptive separation step employs a silicalite adsorbent and, as the desorbent, a C5-C8 linear paraffin, a C5-C8 cycloparaffin, a branched paraffin such as isooctane, or mixtures thereof. The effluent of the alkylation zone comprises paraffins that are recycled to the adsorptive separation step or to the dehydrogenation step. This invention is also a process that sulfonates phenyl-alkanes having lightly branched aliphatic alkyl groups that to produce modified alkylbenzene sulfonates. In addition, this invention is the compositions produced by these processes, which can be used as detergents having improved cleaning effectiveness in hard and/or cold water while also having biodegradability comparable to that of linear alkylbenzene sulfonates, as lubricants, and as lubricant additives.Type: GrantFiled: August 29, 2000Date of Patent: September 9, 2003Assignee: UOP LLCInventors: Santi Kulprathipanja, Richard E. Marinangeli, Stephen W. Sohn, Thomas R. Fritsch, R. Joe Lawson
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Patent number: 6515169Abstract: The present invention is a process for producing aryl-alkanes by paraffin isomerization followed by paraffin dehydrogenation and then by alkylation of an aryl compound by a lightly branched olefin. The effluent of the alkylation zone comprises paraffins that are recycled to the isomerization step or to the dehydrogenation step. This invention is also a process that that sulfonates phenyl-alkanes having lightly branched aliphatic alkyl groups that to produce modified alkylbenzene sulfonates. In addition, this invention is the compositions produced by these processes, which can be used as detergents having improved cleaning effectiveness in hard and/or cold water while also having biodegradability comparable to that of linear alkylbenzene sulfonates, as lubricants, and as lubricant additives. This invention is moreover the use of compositions produced by these processes as lubricants and lubricant additives.Type: GrantFiled: July 25, 2002Date of Patent: February 4, 2003Assignee: UOP LLCInventors: Richard E. Marinangeli, R. Joe Lawson, Leonid B. Galperin, Thomas R. Fritsch
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Patent number: 5929003Abstract: Salts of sulphonic acids of high molecular weight with alkyl groups derived from normal olefins, preferably normal C.sub.3 to C.sub.6 olefins and more preferably normal butene are used as emulsifiers in oil water systems particularly in oil in water emulsions such as microemulsions and white or milky emulsions.Type: GrantFiled: December 19, 1997Date of Patent: July 27, 1999Assignee: Exxon Chemical Patents Inc.Inventor: George de Villardi De Montlaur
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Patent number: 5468407Abstract: A composition comprising a mixture of dialkylbenzene monosulfonic acids or salts thereof containing greater than about 60 weight percent of the para dialkylbenzene isomer and greater than about 80 weight percent of the combined di(2-alkyl)benzene and di(3-alkyl)benzene isomers. The composition exhibits improved properties as a mineral collector in ore flotation.Type: GrantFiled: November 3, 1994Date of Patent: November 21, 1995Assignee: The Dow Chemical CompanyInventors: Kevin A. Frazier, Juan M. Garces, Guo-shuh J. Lee
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Patent number: 5344967Abstract: The present invention describes treating an organic sulfonic acid with an olefin to obtain an improvement in color of the resultant salts and to lessen the amount of inactive components in the composition.Type: GrantFiled: June 28, 1991Date of Patent: September 6, 1994Assignee: The Lubrizol CorporationInventors: Eric R. Schnur, David L. Westfall
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Patent number: 5344997Abstract: A fluorided silica-alumina catalyst, particularly one with a silica:alumina ratio in the range of 1:1-9:1 containing from 1 to 6 weight percent fluoride, is particularly effective in the liquid phase alkylation of benzene by linear olefins to produce linear alkyl benzenes at temperatures no greater than 140.degree. C. These catalysts also are effective in the liquid phase alkylation of alkylatable aromatics generally with a variety of alkylating agents, including olefins, alcohols, and alkyl halides.Type: GrantFiled: December 14, 1992Date of Patent: September 6, 1994Assignee: UOPInventor: Joseph A. Kocal
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Patent number: 5302732Abstract: Silica-aluminas having a sodium content less than about 0.1 weight percent show increased stability when used as a catalyst for the alkylation of aromatic compounds. Where such silica-aluminas are used as the catalyst in detergent alkylation their increased stability permits continuous alkylation to be performed at lower temperatures, as a result of which the detergent alkylate product shows an incrementally higher linearity. Fluorided silica-aluminas having a sodium content of under 0.05 weight percent are particularly advantageous.Type: GrantFiled: September 14, 1992Date of Patent: April 12, 1994Assignee: UOPInventors: Karl Z. Steigleder, Christine M. Conway, David M. Baldwin, Diane C. Dierking
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Patent number: 5196574Abstract: A fluorided silca-alumina catalyst, particularly one with a silica:alumina ratio in the range of 1:1-9:1 containing from 1 to 6 weight percent fluoride, is particularly effective in the liquid phase alkylation of benzene to produce linear alkyl benzenes at temperatures no greater than 140.degree. C. Conversions in excess of 98% with selectivity exceeding 85% and linearity exceeding 90% may be achieved readily.Type: GrantFiled: December 23, 1991Date of Patent: March 23, 1993Assignee: UOPInventor: Joseph A. Kocal
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Patent number: 4959491Abstract: A two-step dimerization process for producing semi-linear C.sub.12 olefins using homogeneous dimerization catalysts and new C.sub.12 olefins mixtures. The C.sub.12 product is especially useful for the production of biodegradable sulfonated alkylaryl detergents and intermediates therefor.Type: GrantFiled: March 11, 1987Date of Patent: September 25, 1990Assignee: Chevron Research CompanyInventor: Richard S. Threlkel