Petroleum Sulfonic Acids Patents (Class 562/33)
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Patent number: 11661543Abstract: Methods can include introducing a cleaning fluid into a near-wellbore zone of an injection well penetrating a subterranean formation, wherein the cleaning fluid includes: 0.5 wt % to about 5 wt % of a surfactant blend comprising an alkoxy carbonate surfactant and an internal olefin sulfonate surfactant; salt water having a total dissolved solids (TDS) of about 15,000 mg/L or greater; and 0 wt % to about 0.05 wt % of an organic acid; and dispersing a hydrocarbon from the near-wellbore zone in the cleaning fluid. Compositions for cleaning a near-wellbore zone of a subterranean formation can include 0.5 wt % to about 5 wt % of a surfactant blend comprising an alkoxy carbonate surfactant and an internal olefin sulfonate surfactant; salt water having a total dissolved solids (TDS) of about 15,000 mg/L or greater; and 0 wt % to about 0.05 wt % of an organic acid.Type: GrantFiled: February 4, 2021Date of Patent: May 30, 2023Assignee: Baker Hughes Oilfield Operations LLCInventors: Lirio Quintero, Jeffrey A. Russek
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Patent number: 8283491Abstract: The present invention is directed to an isomerized alpha olefin sulfonate and a method of making the same wherein the isomerized alpha olefin sulfonate is derived from sulfonating an isomerized alpha olefin with sulfur trioxide in the presence of air thereby producing an isomerized alpha olefin sulfonic acid, wherein the isomerized alpha olefin is derived from the isomerization of C12-C40 normal alpha olefins; and neutralizing the isomerized alpha olefin sulfonic acid with a source of a mono-valent cation.Type: GrantFiled: October 23, 2008Date of Patent: October 9, 2012Assignee: Chevron Oronite Company LLCInventors: Curtis Bay Campbell, Theresa Ann Denslow
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Patent number: 7776111Abstract: The invention provides compositions comprising at least one alkylphenol-aldehyde resin (constituent I) and, based on the alkylphenol resin, from 0.005 to 10% by weight of at least one oil-soluble organic ammonium sulfonate (constituent II).Type: GrantFiled: July 20, 2005Date of Patent: August 17, 2010Assignee: Clariant Produkte (Deutschland) GmbHInventors: Matthias Krull, Carsten Cohrs, Hildegard Freundl, Stefan Lorenz
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Patent number: 7732387Abstract: A method for the preparation of a stream rich in aromatic polysulfonic acid compounds from light catalytic cycle oil. The preparation involves the polysulfonation of the light catalytic cycle oil using more than a stoichiometric amount of sulfuric acid. The aromatic polysulfonic acid compositions are preferably aromatic polynuclear compositions.Type: GrantFiled: May 12, 2005Date of Patent: June 8, 2010Assignee: ExxonMobil Research and Engineering CompanyInventors: Ramesh Varadaraj, Cornellus H. Brons
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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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Publication number: 20070142665Abstract: 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: ApplicationFiled: December 21, 2005Publication date: June 21, 2007Inventors: Curt B. Campbell, Thomas V. Harris, Gilles Sinquin
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Patent number: 7094922Abstract: The invention relates to a process for the preparation of a low-base number calcium sulfonate that is essentially chloride free. The process involves preparing a sulfonic acid solution by adding a solvent to a sulfonic acid, optionally removing dissolved or entrained SO2 or SO3, mixing the solution with a specific amount of water and calcium hydroxide, heating the mixture, separating out excess calcium hydroxide from the mixture, removing the solvent and recovering the calcium sulfonate product in oil.Type: GrantFiled: April 15, 2004Date of Patent: August 22, 2006Assignee: Shell Oil CompanyInventors: Abraham Robert De Kraker, Steven Allen Holmes, Krishna Rangraj Kaushik
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Publication number: 20040133037Abstract: A process for preparing branched olefins comprising 0.5% or less quaternary aliphatic carbon atoms, which process comprises dehydrogenating an isoparaffinic composition over a suitable catalyst which isoparaffinic composition comprises paraffins having a carbon number in the range of from 7 to 35, of which paraffins at least a portion of the molecules is branched, the average number of branches per paraffin molecule being at least 0.7 and the branching comprising methyl and optionally ethyl branches, and which isoparaffinic composition may be obtained by hydrocracking and hydroisomerization of a paraffinic wax; a method of using olefins for making an anionic surfactant, a nonionic surfactant or a cationic surfactant, in particular a surfactant sulfate or sulfonate, comprising converting the branched olefins into the surfactant; and an anionic surfactant, a nonionic surfactant or a cationic surfactant which is obtainable by the method of use.Type: ApplicationFiled: December 17, 2003Publication date: July 8, 2004Inventors: Laurent Alain Michel Fenouil, Brendan Dermot Murray, Paul Marie Ayoub
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Publication number: 20020183567Abstract: A process for preparing branched olefins comprising 0.5% or less quaternary aliphatic carbon atoms, which process comprises dehydrogenating an isoparaffinic composition over a suitable catalyst which isoparaffinic composition comprises paraffins having a carbon number in the range of from 7 to 35, of which paraffins at least a portion of the molecules is branched, the average number of branches per paraffin molecule being at least 0.7 and the branching comprising methyl and optionally ethyl branches, and which isoparaffinic composition may be obtained by hydrocracking and hydroisomerization of a paraffinic wax; a method of using olefins for making an anionic surfactant, a nonionic surfactant or a cationic surfactant, in particular a surfactant sulfate or sulfonate, comprising converting the branched olefins into the surfactant; and an anionic surfactant, a nonionic surfactant or a cationic surfactant which is obtainable by the method of use.Type: ApplicationFiled: February 14, 2002Publication date: December 5, 2002Inventors: Laurent Alain Michel Fenouil, Brendan Dermot Murray, Paul Marie Ayoub
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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: 5162555Abstract: The invention relates to a process for preparing a solution of a non-ferrous metal sulphonate by reacting a non-ferrous metal with a sulphonic acid, the non-ferrous metal being brought into contact with a sulphonic acid at a temperature of from 20.degree. to 120.degree. C. in the presence of oxygen or oxygen-containing gases.Type: GrantFiled: December 10, 1990Date of Patent: November 10, 1992Assignee: Cassella AktiengesellschaftInventors: Graalf Remmers, Horst Lieker
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Patent number: 5055610Abstract: The mixture from which sulphuric acid must be separated according to the present invention are those which derive from the sulphoxidation of (C.sub.12 -C.sub.8)-n-paraffins with SO.sub.2 and O.sub.2 in the presence of water and of U.V. light at a temperature comprised within the range of from 25 to 50.degree. C., after the removal of n-paraffins, which separate spontaneously, and of SO.sub.2 excess. In order to remove said sulphuric acid, the refined mixture, possibly diluted with water, is mixed with one or more halogenated solvents, the separation being obtained of water and sulphuric acid from the refined mixture, to the total mixture (with the two phases) a cosolvent is added, which is constituted by alcohols or ethers, with the separation being obtained of a phase constituted by H.sub.2 O and H.sub.2 SO.sub.4, which is removed. The residual organic phase, practically free from sulphuric acid, is submitted to the removal of solvents and cosolvents by means of conventional techniques.Type: GrantFiled: June 28, 1990Date of Patent: October 8, 1991Assignees: Eniricerche S.p.A., Enichem Augusta S.p.A.Inventors: Enrico Borgarello, Lucio Faggian, Edoardo Platone, Cosimo Franco
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Patent number: 5047580Abstract: The purpose of the process of the present invention is to remove excess sulfuric acid from a mixture of paraffin-sulfonic acids free or substantially free, from paraffins.In order to remove said sulfuric acid, according to the process of the present invention, the paraffin-sulfonic acid mixture is mixed with one or more halogenated solvent(s), possibly in mixture with sulfuric acid to form a two phase mixture consisting of an organic phase containing paraffin-sulfonic acids dissolved therein and an aqueous phase substantially containing sulfuric acid. The organic phase is then treated with sulfuric acid and the organic phase and aqueous phase are then separated and the organic phase is submitted to evaporation, for the removal of the halogenated solvent(s), and with the concentrated paraffin-sulfonic acids being obtained.Type: GrantFiled: March 22, 1990Date of Patent: September 10, 1991Assignees: Eniricerche S.p.A., Enichem Augusta S.p.A.Inventors: Lucio Faggian, Enrico Borgarello, Cosimo Franco, Gerardo Carrillo
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Patent number: 4847018Abstract: A petroleum sulfonate is prepared by (a) separately sulfonating each of two or more different petroleum fractions boiling substantially above 700.degree. F. by contact with sulfur trioxide under reaction conditions wherein the ratio of milliliters of sulfur trioxide to grams of aromatic components is adjusted so as to produce from each separate fraction a reaction product capable of producing upon neutralization a sulfonate having a sulfonate requirement in microemulsion below about 20 grams per 100 milliliters of microemulsion; (b) separately neutralizing the sulfonated fractions; and (c) blending the hydrocarbon sulfonates produced from two or more of the fractions in proportions sufficient to yield a product petroleum sulfonate blend useful for enhanced oil recovery.Type: GrantFiled: April 15, 1988Date of Patent: July 11, 1989Assignee: Union Oil Company of CaliforniaInventors: Jeffery W. Koepke, Wen-Ching Hsieh, June M. Bostich