The Alkylating Agent Is An Olefin Patents (Class 562/94)
  • Publication number: 20150126770
    Abstract: 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: Application
    Filed: November 1, 2013
    Publication date: May 7, 2015
    Applicant: UOP LLC
    Inventors: Stephen W. Sohn, Mark G. Riley, Michael A. Moore
  • Publication number: 20150072916
    Abstract: 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: Application
    Filed: June 6, 2014
    Publication date: March 12, 2015
    Applicant: UOP LLC
    Inventors: Stanley J. Frey, Daniel L. Ellig, Andrea G. Bozzano, Geoffrey W. Fichtl, Debarshi Majumder
  • Publication number: 20140081043
    Abstract: 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: Application
    Filed: March 30, 2011
    Publication date: March 20, 2014
    Inventors: Pierre Téqui, Curt B. Campbell, Gilles P. Sinquin, Christine Boemare Gandon, Kyle J. Frederic, Eugene E. Spala
  • Publication number: 20120214724
    Abstract: 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: Application
    Filed: February 17, 2012
    Publication date: August 23, 2012
    Inventors: Jeffrey John Scheibel, Phillip Richard Green, Jiten Odhavji Dihora, Phillip Kyle Vinson, Stephanie Ann Urbin, Dimitris Ioannis Collias
  • Publication number: 20120213726
    Abstract: 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: Application
    Filed: February 17, 2012
    Publication date: August 23, 2012
    Inventors: Phillip Richard Green, Jeffrey John Scheibel, Dimitris Ioannis Collias
  • Patent number: 8158819
    Abstract: 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: Grant
    Filed: April 12, 2005
    Date of Patent: April 17, 2012
    Assignee: Cepsa Quimica S.A.
    Inventors: José Luis Berna Tejero, José Luis Goncalvez De Almeida, Ignacio López Serrano
  • Patent number: 8034973
    Abstract: 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: Grant
    Filed: March 16, 2006
    Date of Patent: October 11, 2011
    Assignee: Cepsa Quimica, S.A.
    Inventors: José Luis Goncalvez De Almeida, José Luis Berna Tejero
  • Patent number: 7449596
    Abstract: 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: Grant
    Filed: December 21, 2005
    Date of Patent: November 11, 2008
    Assignee: Chevron Oronite Company LLC
    Inventors: Curt B. Campbell, Thomas V. Harris, Gilles Sinquin
  • Patent number: 7148388
    Abstract: 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: Grant
    Filed: March 28, 2003
    Date of Patent: December 12, 2006
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Stephen W. Beadle, Cesar M. Cheng-Guajardo, Carolyn B. Duncan, David Wayne Turner, Ramzi Y. Saleh
  • Patent number: 7060852
    Abstract: 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: Grant
    Filed: August 10, 2001
    Date of Patent: June 13, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Heiko Maas, Thomas Narbeshuber, Michael Roeper
  • Patent number: 6906230
    Abstract: 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: Grant
    Filed: March 17, 2000
    Date of Patent: June 14, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Heiko Maas, Michael Röper, Marc Walter, Ralf Schulz, Jürgen Tropsch, Hans-Ulrich Jäger
  • Publication number: 20040010161
    Abstract: The invention relates to a process for the preparation of alkylarylsulfonates by
    Type: Application
    Filed: February 10, 2003
    Publication date: January 15, 2004
    Inventors: Heiko Maas, Thomas Narbeshuber, Michael Roper
  • Patent number: 6673961
    Abstract: 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: Grant
    Filed: November 26, 2002
    Date of Patent: January 6, 2004
    Assignee: The Procter & Gamble Company
    Inventors: Daniel Stedman Connor, Jeffrey John Scheibel, James Charles Theophile Roger Burckett-St. Laurent, Thomas Anthony Cripe, Kevin Lee Kott, Phillip Kyle Vinson
  • Patent number: 6617481
    Abstract: 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: Grant
    Filed: August 29, 2000
    Date of Patent: September 9, 2003
    Assignee: UOP LLC
    Inventors: Santi Kulprathipanja, Richard E. Marinangeli, Stephen W. Sohn, Thomas R. Fritsch, R. Joe Lawson
  • Patent number: 6515169
    Abstract: 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: Grant
    Filed: July 25, 2002
    Date of Patent: February 4, 2003
    Assignee: UOP LLC
    Inventors: Richard E. Marinangeli, R. Joe Lawson, Leonid B. Galperin, Thomas R. Fritsch
  • Patent number: 5929003
    Abstract: 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: Grant
    Filed: December 19, 1997
    Date of Patent: July 27, 1999
    Assignee: Exxon Chemical Patents Inc.
    Inventor: George de Villardi De Montlaur
  • Patent number: 5468407
    Abstract: 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: Grant
    Filed: November 3, 1994
    Date of Patent: November 21, 1995
    Assignee: The Dow Chemical Company
    Inventors: Kevin A. Frazier, Juan M. Garces, Guo-shuh J. Lee
  • Patent number: 5344967
    Abstract: 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: Grant
    Filed: June 28, 1991
    Date of Patent: September 6, 1994
    Assignee: The Lubrizol Corporation
    Inventors: Eric R. Schnur, David L. Westfall
  • Patent number: 5344997
    Abstract: 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: Grant
    Filed: December 14, 1992
    Date of Patent: September 6, 1994
    Assignee: UOP
    Inventor: Joseph A. Kocal
  • Patent number: 5302732
    Abstract: 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: Grant
    Filed: September 14, 1992
    Date of Patent: April 12, 1994
    Assignee: UOP
    Inventors: Karl Z. Steigleder, Christine M. Conway, David M. Baldwin, Diane C. Dierking
  • Patent number: 5196574
    Abstract: 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: Grant
    Filed: December 23, 1991
    Date of Patent: March 23, 1993
    Assignee: UOP
    Inventor: Joseph A. Kocal
  • Patent number: 4959491
    Abstract: 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: Grant
    Filed: March 11, 1987
    Date of Patent: September 25, 1990
    Assignee: Chevron Research Company
    Inventor: Richard S. Threlkel