Sulfonation Processes Patents (Class 562/95)
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Patent number: 9540319Abstract: The present invention relates to an improved method for purifying a sulfonated aromatic monomer. The method is an economical method capable of providing a highly pure sulfonated aromatic monomer, in which a salt precipitation step and a recrystallization step are simplified while maintaining the reaction conditions used in a conventional method for synthesizing the sulfonated aromatic monomer, and a purification process is carried out using an easily available and stable chemical substance. The sulfonated aromatic monomer obtained by the purification method will be useful for the preparation of a polymer for a polymer electrolyte membrane and will be advantageous to synthesize polymer with high molecular weight.Type: GrantFiled: November 14, 2011Date of Patent: January 10, 2017Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGYInventors: Young Taik Hong, Seog Je Kim, Ji Young Park, Dong Hyun Lee
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Publication number: 20150148561Abstract: A linear alkyl benzene product and production of linear alkylbenzene from a natural oil are 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: May 28, 2015Inventors: Stanley J. Frey, Daniel L. Ellig, Andrea G. Bozzano, Geoffrey W. Fichtl, Debarshi Majumder
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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: 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: 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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Publication number: 20030105352Abstract: This invention relates new and improved processes for the preparation of arylalkylsulfonic acids derived from aromatic or substituted aromatic molecules and AOS acid (generally a mixture of alkenesulfonic acid and sultones, produced from the sulfonation of alpha olefins). The invention involves the use of a superacid catalyst to effectuate the conversion of AOS acid and aromatic reactants to arylalkylsulfonic acid under substantially anhydrous conditions, whereby a substantial improvement in the rate of conversion of the reactants to arylalkylsulfonic acid and/or improvement in mono-alkylation selectivity is realized, as compared to methods of preparation previously disclosed. Also useful as an alkylation promoter is the arylalkylsulfonic acid reaction product itself, produced in situ or from a previous reaction (i.e., a self-catalyst heel).Type: ApplicationFiled: August 3, 2001Publication date: June 5, 2003Inventors: Gregory P. Dado, Randal J. Bernhardt
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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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Publication number: 20020161255Abstract: A process for producing organic sulfur acid or a salt thereof of the present invention allows an organic substrate to react with a sulfur oxide in the presence of a metallic compound catalyst and in the absence of N-hydroxy and N-oxo cyclic imide compounds and thereby yields a corresponding organic sulfur acid or a salt thereof. Such organic substrates include, for example, (a) homocyclic or heterocyclic compounds having a methylene group, (b) compounds having a methine carbon atom, (c) compounds having a methyl group or methylene group at the adjacent position to an unsaturated bond, (d) non-aromatic heterocyclic compounds having a carbon-hydrogen bond at the adjacent position to a hetero atom, and (e) straight-chain alkanes. The sulfur oxide includes, for example, sulfur dioxide. This production process can efficiently produce an organic sulfur acid or a salt thereof under mild conditions.Type: ApplicationFiled: November 2, 2001Publication date: October 31, 2002Inventors: Yasutaka Ishii, Tatsuya Nakano
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Patent number: 6087529Abstract: To improve color and odor characteristics of sulfonic acids and their derivatives while maintaining sludge and sulfuric acid reduction and good thermal stability, they are treated with at least one unsaturated hydrocarbon, each having at most 36 carbon atoms and having defined substitution characteristics.Type: GrantFiled: September 1, 1998Date of Patent: July 11, 2000Assignee: Exxon Chemical Patents Inc.Inventors: Edouard Mathieu, Dominique Moulin, Jean Michel Legac, Olivier Letailleur
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Patent number: 5936106Abstract: An process for forming a product which may be in a liquid phase is disclosed wherein a first reactant, preferably a liquid reactant, is directly fed into a reaction zone containing mixing elements and which comprises a first compartment of a reactor. A second reactant, which is maintained at a higher pressure, is fed into a second compartment of the reactor separated from the first compartment by a porous wall. The second reactant passes through this porous wall into the reaction zone to react with the first reactant. The process thereby controls rates of the reactions and the exothermic heats generated by the reactions. Pulsatile flow in one or both reaction compartments improves mixing. An evaporator for a portion of the product improves product quality and permits higher reaction temperatures in the reactor.Type: GrantFiled: December 6, 1996Date of Patent: August 10, 1999Assignee: SRI InternationalInventors: William J. Asher, Daryl L. Roberts, Jerry L. Jones, Douglas E. Gottschlich
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Patent number: 5922903Abstract: An arrangement for a falling film type reactor uses corrugated plates to improve the distribution and dispersion of the gaseous reactant into the liquid. Corrugated plates introduce increased turbulence for promoting better distribution and dispersion of the gas. Corrugation angles can be varied to suit the fluid flow properties of the liquid reactant. The reactor arrangement can also include heat transfer channels defined by the corrugated plates in an alternate arrangement of heat transfer channels and gas liquid contacting channels. The corrugations may also be varied to suit the particular heat transfer requirements of the reactions. The corrugated plates are spaced apart in the contacting channels to prevent localized film contact and placed in contact in the heat exchange portion to stabilize the plate elements defining the corrugations.Type: GrantFiled: November 10, 1997Date of Patent: July 13, 1999Assignee: UOP LLCInventor: Peter R. Pujado
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Patent number: 5814110Abstract: Distillate fuel is treated with additives whose structure match the crystal planes of the wax which crystallizes from the fuel to produce crystals below 4000 nanometres in size, suitable additive include novel sulpho-carboxylic materials particularly their esters and amine derivatives such as the amine salts and/or amides of ortho-sulpho benzoic acid.Type: GrantFiled: November 23, 1994Date of Patent: September 29, 1998Assignee: Exxon Chemical Patents Inc.Inventors: Kenneth William Bartz, Jacqueline Dawn Bland, David Paul Gillingham, Richard Dix Kerwood, Edwin William Lehmann, Kenneth Lewtas, John Edward Maddox, Albert Rossi, Robert Dryden Tack
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Patent number: 5596128Abstract: A sulfonating agent represented by the general formula ##STR1## wherein the groups R.sup.1 are the same or different and are each a lower alkyl group having 1 to 3 carbon atoms, n is an integer of 3, 4 or 5, m is an integer of 1 or 2, and n+m.ltoreq.6, and a process for sulfonating an aromatic compound with use of the sulfonating agent.Type: GrantFiled: September 6, 1994Date of Patent: January 21, 1997Assignee: Konishi Chemical Ind. Co., Ltd.Inventors: Eiji Ogata, Norio Yanase, Takayuki Kitahara
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Patent number: 5583240Abstract: An exothermic process for forming a product which may be in a liquid phase is disclosed wherein a first reactant, preferably a liquid reactant, is directly fed into a reaction zone containing mixing elements and which comprises a first compartment of a reactor. A second reactant, which is maintained at a higher pressure, is fed into a second compartment of the reactor separated from the first compartment by a porous wall. The second reactant passes through this porous wall into the reaction zone to react with the first reactant. The process thereby controls rates of the reactions and the exothermic heats generated by the reactions. Pulsatile flow in one or both reaction compartments improves mixing. An evaporator for a portion of the product improves product quality and permits higher reaction temperatures in the reactor.Type: GrantFiled: March 2, 1994Date of Patent: December 10, 1996Assignee: SRI InternationalInventors: William J. Asher, Daryl L. Roberts, Jerry L. Jones, Douglas E. Gottschlich
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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: 5243099Abstract: Organic polymer additive containing polar functional groups enhances the stability of palladium-containing catalysts for the telomerization of conjugated diolefins in the presence of active hydrogen-containing telomerization agent to produce alpha-substituted alkadienes.Type: GrantFiled: September 9, 1992Date of Patent: September 7, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Diane L. Packett
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Patent number: 5233081Abstract: A method for preparing a sulfonated compound with minimal or no waste products using a porous inorganic material absorber. The absorber is saturated with a compound to be sulfonated and then contacted with a sulfonating gas mixture to form a sulfonated product. After forming the sulfonated product, excess sulfonating gas is removed by contacting the sulfonated product with warm air. The sulfonated product is then neutralized and the product is removed with water from the inorganic material absorber. The absorber is then dried with hot air so that it may be reused for future sulfonation processes. The process results in preparation of a sulfonated compound having inorganic salts present in an amount less than about 1.0 percent by weight based on total sulfonated product weight. The process results in highly effective sulfonation of a compound with formation of little or no waste materials, particularly waste materials such as solvents and undesirable inorganic salts.Type: GrantFiled: March 30, 1992Date of Patent: August 3, 1993Inventor: Wilhelm E. Walles
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Patent number: 5169981Abstract: Organic polymer additive containing polar functional groups enhances the stability of palladium-containing catalysts for the telomerization of conjugated diolefins in the presence of active hydrogen-containing telomerization agent to produce alpha-substituted alkadienes.Type: GrantFiled: December 6, 1991Date of Patent: December 8, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Diane L. Packett
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Patent number: 5026933Abstract: A process for producing substantially linear hydrocarbons by oligomerizing a lower olefin at elevated temperature and pressure which comprises contacting the lower olefin under oligomerization/polymerization conditions with siliceous acidic ZSM-23 zeolite having Bronsted acid activity; wherein the zeolite has acidic pore activity and wherein the zeolite surface is rendered substantially inactive for acidic reactions. The zeolite surface can be neutralized by a bulky pyridine compound having an effective cross-section larger than the zeolite pore. The preferred deactivating agent is 2,4,6-collidine, which may be applied to the zeolite as a pretreatment or added with olefin feed in a continuous process. The olefin oligomers may be used as alkylating agents to prepare biodegradable alkylbenzenes and alkylphenylsulfonates. A preferred catalyst for this alkylation reaction is dealuminized mordenite.Type: GrantFiled: July 18, 1989Date of Patent: June 25, 1991Assignee: Mobil Oil CorporationInventors: David A. Blain, Nancy M. Page, Lewis B. Young
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Patent number: 4973686Abstract: The invention relates to the use of selected carboxylic acid esters which are liquid under reaction conditions and correspond to general formula (I)X--COOR.sup.1 (I)in which R.sup.1 is an alkyl radical unbranched in the .alpha.-position and X is hydrogen or a group corresponding to general formula (II) ##STR1## in which R.sup.2, R.sup.3 and R.sup.4 represent fluorine and/or chlorine and one of these substituents may also be hydrogen or one or two of these substituents may also be lower alkyl, as reaction medium for the sulfonation and/or sulfatization or organic components with SO.sub.3 to light-colored reaction products.Type: GrantFiled: September 2, 1988Date of Patent: November 27, 1990Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Josef Kretschmann, Franz-Josef Carduck, Willi Wuest, Hubert Harth, Dirk Springer
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Patent number: 4943656Abstract: This invention relates to novel processes for the production of enhanced yields of polyalkylaromatic polysulfonic acids. More particularly, the invention pertains to processes for sulfonating polyalkylaromatic compounds employing sulfuric acid treatment and recovering the polyalkylaromatic polysulfonic acid produced thereby after formation of a three phase system by the addition of controlled amounts of water, causing the polysulfonic acid to accumulate in the bottom layer, with which it is readily separated.Type: GrantFiled: July 19, 1984Date of Patent: July 24, 1990Assignee: King Industries, Inc.Inventors: Lawrence V. Gallacher, Harry N. Condos