Preparing By Catalytic Alkylation Patents (Class 568/790)
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Patent number: 10549263Abstract: The present invention relates generally to an advanced oxidation process for providing advanced oxidation products to an environment. More particularly, the present invention provides a wick structure and hydrophilic granules for use in an advanced oxidation process, and methods of making the same. The wick structure and hydrophilic granules may be configured to collect and concentrate water vapor, so that the water vapor may subsequently be used to generate advanced oxidation products that react with and neutralize compounds in an environment, including microbes, odor causing chemicals, and other organic and inorganic chemicals.Type: GrantFiled: November 9, 2016Date of Patent: February 4, 2020Assignee: RGF ENVIRONMENTAL GROUP, INC.Inventors: Walter B. Ellis, Ronald G. Fink
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Patent number: 9109198Abstract: A method of processing an adipose tissue to collect adipose derived regenerative cells is provided, wherein the method comprises providing a vessel comprising a fluid jet mixer; introducing the adipose tissue into the vessel; introducing a buffer solution into the vessel; washing the adipose tissue using the fluid jet mixer; introducing an enzyme solution into the vessel; initiating jet mixing into the vessel comprising the adipose tissue, the enzyme solution, and the buffer solution using the fluid jet mixer to digest the adipose tissue to form a digestion product; phase-separating the digestion product into a digested buoyant fat layer and a non-buoyant aqueous layer; and collecting the non-buoyant aqueous layer comprising the adipose derived regenerative cells. A system of processing an adipose tissue to collect adipose derived regenerative cells is also provided.Type: GrantFiled: April 29, 2011Date of Patent: August 18, 2015Assignee: General Electric CompanyInventors: Zaeem Ashraf Khan, Aaron Joseph Dulgar-Tulloch, Stefan Rakuff, Philip Alexander Shoemaker, Erik Leeming Kvam, Xiaohui Chen, Jaydeep Roy
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Patent number: 8993813Abstract: The present invention relates to a process for the preparation of 4-isopropyl-3-methylphenol (p-thymol) from distillation residues of thymol production.Type: GrantFiled: May 18, 2012Date of Patent: March 31, 2015Assignee: LANXESS Deutschland GmbHInventors: Uwe Boeger, Lutz Heuer, Michael Herzhoff
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Patent number: 8704006Abstract: A process for preparing an alkylated hydroxyl aromatic compound comprising reacting (a) a hydroxyl aromatic compound (I), having the following structure; wherein n 1, 2 or 3; m is 0, 1, 2, or 3 and R1 is Hydrogen or hydrocarbyl group; and (b) at least one ?-branched primary alcohol component in the presence of an alkylating catalyst thereby producing an alkylated hydroxyl aromatic compound.Type: GrantFiled: December 10, 2010Date of Patent: April 22, 2014Assignee: Chevron Oronite Company LLCInventors: Curtis Bay Campbell, Cedrick Mahieux
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Publication number: 20130150607Abstract: This invention is directed to a new process for making an alkylaromatic compound. In an embodiment of this invention, the process is directed to selective synthesizing an alkylaromatic compound comprising a high amount of dialkylate product. In general, this process involves contacting at least one alkylatable aromatic compound with an alkylating agent and a catalyst under suitable reaction conditions such that the resulting reactor effluent prior to any stripping step may be characterized by a dialkylate product content of at least 44 wt % and a trialkylate and higher polyalkylate product content of no more than 20 wt %. The alkylaromatic compounds produced have excellent thermal and oxidative stabilities, good additive solvency, and improved seal compatibility while maintaining good VI and low temperature properties. They are useful as lubricant basestocks and lubricant additives.Type: ApplicationFiled: December 7, 2011Publication date: June 13, 2013Inventor: Beth A. WINSETT
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Publication number: 20130150608Abstract: This invention is directed to an improvement in the process for the production of alkylaromatic compounds that results in lower levels of residual unreacted materials in the final product. This invention comprises: 1) alkylation of an aromatic compound with an alkylating agent and a catalyst to produce an effluent stream comprising an alkylaromatic compound and unreacted materials; 2) heating the effluent stream; 3) stripping the effluent stream in a stripping device in the presence of steam; 4) separating a stripping stream from the stripping device, the stripping stream rich in unreacted materials; and 5) separating a product stream from the stripping device, the product stream rich in alkylated aromatic compound.Type: ApplicationFiled: December 13, 2011Publication date: June 13, 2013Inventors: Beth A. Winsett, James I. Arnett, II, Kenwyn M. Leger, Brady A. Compton
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Patent number: 8247621Abstract: The invention relates to the preparation of alkylated phenols. More specifically, the invention relates to an improved process for the manufacture of 2-secondary-alkyl-4,5-di-normal-alkylphenols.Type: GrantFiled: October 12, 2009Date of Patent: August 21, 2012Assignee: Invista North America S.A.R.L.Inventors: Joachim C. Ritter, James Michael Garner
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Patent number: 8207380Abstract: An alkylated hydroxyaromatic compound prepared by reacting at least one hydroxyaromatic compound with a branched olefinic oligomer having from about 20 to about 80 carbon atoms in the presence of a acid catalyst. The alkylated hydroxyaromatic compound has been determined to be substantially free of endocrine disruptive chemicals when the effects were quantified on pubertal development and thyroid function in the intact juvenile female rat.Type: GrantFiled: April 27, 2007Date of Patent: June 26, 2012Assignee: Chevron Oronite LLCInventors: Curt B. Campbell, James J. Harrison
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Publication number: 20100269406Abstract: Paraffin-containing liquid pour point depressants comprising the reaction product of a hydrocarbyl-substituted phenol and an aldehyde wherein: the olefin used in the preparation of the hydrocarbyl-substituted phenol has a high vinylidene content; the reaction between the hydrocarbyl-substituted phenol and the aldehyde is acid or base catalyzed; and/or the reaction further comprises phenol, are particularly useful for treating crude oils which have an initial pour point of 4° C. or higher, decreasing the fluid's pour point and improving the fluid's low temperature handling properties.Type: ApplicationFiled: November 13, 2008Publication date: October 28, 2010Applicant: The Lubrizol CorporationInventors: David J. Moreton, Antonio Mastrangelo, Malcolm MacDuff
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Patent number: 7750193Abstract: The present invention relates to a process for preparing 2-alkylpolyisobutenylphenols and their Mannich adducts, to compositions obtainable by this process and to their use.Type: GrantFiled: February 1, 2005Date of Patent: July 6, 2010Assignee: BASF AktiengesellschaftInventors: Arno Lange, Helmut Mach, Hans Peter Rath, Dietmar Posselt, Anja Vinckier
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Publication number: 20090176998Abstract: The present invention relates to novel processes for the manufacture of chroman derivatives such as ?-tocopherol (TCP) and alkanoates thereof, especially ?-tocopheryl acetate (TCPA), whereby at least one step of the processes is carried out in the presence of a Lewis acid or a mixture of a Lewis acid with a Bronsted acid as the catalyst under pressure, preferably at an absolute pressure of at least 1.1 bar. As starting materials for the manufacture of TCP and its alkanoates either a mixture of 2,3,5-trimethylhydroquinone (TMHQ) or 2,3,6-trimethylhydroquinone-1-alkanoate (TMHQA) and a compound selected from the group consisting of phytol (PH), isophytol (IP) and (iso)phytol derivatives or 2-phytyl-3,5,6-trimethyl-hydroquinone (PTMHQ)/3-phytyl-2,5,6-trimethylhydroquinone-1-alkanoate (PTMHQA) and/or an isomer thereof are used. Suitable Lewis acids are indium(III) salts and scandium(III) salts. Suitable acid mixtures are iron/iron(II) chloride/hydrogen chloride and zinc(II) chloride/hydrogen chloride.Type: ApplicationFiled: March 6, 2009Publication date: July 9, 2009Inventors: Werner Bonrath, Yann Foricher, Thomas Netscher, Angela Wildermann
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Patent number: 7435273Abstract: Alkoxylated alkylphenols which have at least one long-chain alkyl radical having at least one tertiary or quaternary carbon atom are prepared and are used as fuel or lubricant additives in fuel and lubricant compositions.Type: GrantFiled: January 22, 2002Date of Patent: October 14, 2008Assignee: Basf AktiengesellschaftInventors: Arno Lange, Hans Peter Rath, Marc Walter
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Publication number: 20080114192Abstract: The present invention relates to an improved process for the selective alkylation of phenols using heteropolyacid catalyst supported onto zirconia under mild conditions. The process is economically viable since the catalyst regenerated after the initial reaction on further use gives the product in high yield.Type: ApplicationFiled: September 26, 2007Publication date: May 15, 2008Applicant: Secretary, Department of Science and TechnologyInventors: Anjali Uday Patel, Nikunj Bhagwatiprasad Bhatt
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Patent number: 7288683Abstract: An alkylation method comprises reacting a hydroxy aromatic compound with an alkyl alcohol in the presence of an alkylation catalyst comprising a metal oxide wherein the alkylation catalyst, has a surface area to volume ratio of about 950 to about 4,000 m2/m3, an aspect ratio of about 0.7 to about 1.0 or a combination of the foregoing.Type: GrantFiled: June 16, 2006Date of Patent: October 30, 2007Assignee: General Electric CompanyInventors: Hugo G. E. Ingelbrecht, David Parrillo, Mukund Parthasarathy, Gert-Jan Schoenmakers, Geuch Zijlma
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Patent number: 6914163Abstract: Polyisobutenylphenols are prepared by alkylating an aromatic hydroxy compound with substantially monoethylenically unsaturated and substantially homopolymeric polyisobutenes in the presence of a Lewis acid alkylation catalyst by a process in which the polyisobutenes have a ? double bond content of at least 35 mol %.Type: GrantFiled: September 27, 2001Date of Patent: July 5, 2005Assignee: BASF AGInventors: Arno Lange, Hans Peter Rath
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Patent number: 6875897Abstract: Polyisobutenylphenols are prepared by alkylating an aromatic hydroxy compound with substantially monoethylenically unsaturated and substantially homopolymeric polyisobutenes in the presence of a Lewis acid alkylation catalyst by a process in which an ether is additionally used as a cocatalyst, the ether having a molecular weight of at least 102 g/mol in the case of BF3 as the Lewis acid.Type: GrantFiled: September 27, 2001Date of Patent: April 5, 2005Assignee: BASF AktiengesellschaftInventors: Arno Lange, Hans Peter Rath
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Publication number: 20040118673Abstract: The present invention relates to “a microwave induced process for the preparation of 4-vinylphenols or its derivatives” in which commercially important FEMA GRAS approved perfumery and flavouring vinylphenols (i.e. hydroxystyrenes) namely 4-vinylguaiacol (FEMA GRAS No. 2675) and 4-vinylphenol (FEMA GRAS No. 3739) as well as other useful vinylphenols such as 2,6-dimethoxy-4-vinylphenol, 2-hydroxy-4-vinylphenol, 3-hydroxy-4-vinylphenol etc. by condensation of malonic acid and 4-hydroxyphenylaldehydes or its derivatives.Type: ApplicationFiled: March 7, 2003Publication date: June 24, 2004Applicant: Council of Scientific & Industrial ResearchInventors: Arun Kumar Sinha, Bhupendra Prasad Joshi, Anuj Sharma
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Patent number: 6670513Abstract: An alkylated hydroxyl-containing aromatic compound is produced by isomerizing a normal alpha-olefin having from about 16 to about 30 carbon atoms in the presence of a first solid, acidic catalyst capable of inducing both olefin isomerization and skeletal isomerization to produce a mixture of isomerized olefin, then alkylating an hydroxyl-containing aromatic compound with the mixture of isomerized olefins in the presence of a second solid, acidic catalyst. The first solid, acidic catalyst can be SM-3, MAPO-11, SAPO-11, SSZ-32, ZSM-23, MAPO-39, SAPO-39, ZSM-22, SSZ-20, ZSM-35, SUZ-4, NU-23, NU-87, natural ferrierite or synthetic ferrierite. The second solid, acidic catalyst can be a sulfonic acid anionic ion exchange resin catalyst or an acidic clay.Type: GrantFiled: December 3, 1999Date of Patent: December 30, 2003Assignees: Chevron Oronite Company, LLC, Chevron Oronite S.A.Inventors: Curtis Bay Campbell, Jean Louis Le Coënt
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Patent number: 6617476Abstract: A process for producing an aromatic ring alkylated phenols, wherein said process comprises reacting phenols represented by the general formula (1): wherein, each of R1, R2, R3, R4 and R5 independently represents a hydrogen atom, or a linear or branched alkyl group having 1 to 10 carbon atoms; with monohydric or dihydric alcohol in the presence of a hydroxide of a metal, an alkoxide of a metal, or a hydroxide of a metal and an alkoxide of a metal under a supercritical state of the alcohol.Type: GrantFiled: December 13, 2000Date of Patent: September 9, 2003Assignee: Sumitomo Chemical Company, LimitedInventors: Tomoyuki Suzuki, Fumisato Goto, Kozo Tanaka
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Patent number: 6417410Abstract: A method for producing ortho-alkylated phenols comprising reacting phenols represented by the general formula (1) with monohydric or dihydric alcohol in the presence of germanium oxide under conditions in which said alcohol is in the supercritical condition, wherein each of R1, R2, R3, R4 and R5 independently represents a hydrogen atom, or a linear or branched alkyl group having 1 to 10 carbon atoms.Type: GrantFiled: April 18, 2001Date of Patent: July 9, 2002Assignee: Sumitomo Chemical Company, LimitedInventors: Tomoyuki Suzuki, Fumisato Goto
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Patent number: 6274777Abstract: A method for removing boron from a boron trifluoride-catalyzed polyalkyl hydroxyaromatic reaction product which comprises: (a) diluting the polyalkyl hydroxyaromatic reaction product with an inert solvent to give a polyalkyl hydroxyaromatic reaction product concentration in the range of about 40 to about 80 weight percent; (b) filtering the diluted polyalkyl hydroxyaromatic reaction product in the presence of a filter aid in combination with (1) magnesium silicate, (2) water or (3) a mixture of magnesium silicate and water; wherein the water is present during filtration at a concentration of about 100 to 1,500 ppm, based on the diluted polyalkyl hydroxyaromatic reaction product; with the proviso that when water is used in the absence of magnesium silicate, the filter aid is diatomaceous earth; and (c) recovering a filtrate containing the diluted polyalkyl hydroxyaromatic reaction product having less than about 10 ppm of boron present.Type: GrantFiled: December 30, 1999Date of Patent: August 14, 2001Assignees: Chevron Chemical Company LLC, Chevron Chemical S.A.Inventors: James A. Gray, Thierry Triconnet
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Publication number: 20010004674Abstract: A process for producing an aromatic ring alkylated phenols, wherein said process comprises reacting phenols represented by the general formula (1): 1Type: ApplicationFiled: December 13, 2000Publication date: June 21, 2001Inventors: Tomoyuki Suzuki, Fumisato Goto, Kozo Tanaka
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Patent number: 6232485Abstract: A process for the production of liquid meta-rich triaryl phosphate esters having low triphenyl phosphate content and low viscosity comprises (a) an alkylation stage wherein a phenol is reacted with an olefin having 2 to 12 carbon atoms in the presence of a strong acid catalyst to give a reaction product comprising a mixture of meta and para alkylated phenols; and (b) a transalkylation stage wherein the mixture of alkylated phenols from the alkylation stage is heated in the presence of a strong acid catalyst to increase the meta isomer content of the mixture to at least 25% whilst maintaining a phenol level below 22%; and (c) a phosphorylation stage wherein the mixture of alkylated phenols from the transalkylation stage is reacted with a phosphorylating agent; and wherein the strong acid catalyst used in stages (a) and (b) is a Bronsted acid having an acid strength of less than zero. Preferred catalysts are activated clays such as bentonite, montmorillonite or Fullers Earth clay.Type: GrantFiled: November 26, 1999Date of Patent: May 15, 2001Assignee: Great Lakes Chemical CorporationInventors: Tracy Anne Derbyshire, Hazel May Farrow, Jonathan Simon Hill
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Patent number: 6191317Abstract: Polyalkyl hydroxyaromatics may be prepared from polyalkylenes and hydroxyaromatics in the presence of an acid catalyst and an organic solvent having a boiling point range with an initial boiling point value of below or about the boiling point of the selected hydroxyaromatic reactants and final boiling point of above or equal to about the boiling point of alkylhydroxyaromatic by-product of the reaction. Using this method, accumulation of undesirable alkylhydroxyaromatic by-product/s in a reaction vessel may be minimized, and/or viscosity of polyalkyl hydroxyaromatic product reduced, allowing for increased ease of transfer and transportation.Type: GrantFiled: August 31, 1999Date of Patent: February 20, 2001Assignee: Huntsman Petrochemical CorporationInventor: Wei-Yang Su
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Patent number: 5663457Abstract: Conventional low vinylidene polyolefins are condensed with hydroxyaromatics under the influence of macroreticular ion exchange resins in acid form to yield alkylated hydroxyaromatics.Type: GrantFiled: February 16, 1996Date of Patent: September 2, 1997Assignee: The Lubrizol CorporationInventor: Christopher Jay Kolp
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Patent number: 5633411Abstract: Allylic styrene ether compounds of the formula: ##STR1## where R.sup.1 is an optionally substituted allylic or propargyl hydrocarbon group, and R.sup.2, R.sup.3, and R.sup.4 are independently H, C.sub.1-6 hydrocarbon or C.sub.1-6 hydrocarbonoxy groups, are prepared in a single pot reaction from relatively low cost materials. The method includes the steps of reacting a 4-acyloxystyrene of the formula ##STR2## where R is an acyl group, with at least one mole of a base which can readily saponify or hydrolyze the phenolic ester bond per mole of acyloxystyrene, and then adding to the reaction mixture an alloylating agent of the formula R.sup.1 X, where R.sup.1 is as previously defined and X is chloride, bromide, iodide, a sulfonic ester or a hydrocarbon sulfate group, to form said allylic styrene ether compound. The method may be employed to prepare mono-styryl functional compounds or di-styryl functional compounds such as 1,4-bis(4'-vinylphenoxy)but-2-ene.Type: GrantFiled: May 28, 1996Date of Patent: May 27, 1997Assignee: Loctite CorporationInventors: John G. Woods, Maria Masterson
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Patent number: 5583268Abstract: A process of catalytically reacting a 3-18 carbon mono-olefin such as cyclohexene with an arylhydroxide such as phenol in the liquid phase forming an ortho-alkylated arylhydroxide which is subsequently catalytically dehydrogentated to form an ortho-alkenylarylhydroxide or ortho-arylarylhydroxide such as ortho-phenylphenol.Type: GrantFiled: December 15, 1995Date of Patent: December 10, 1996Assignee: The Dow Chemical CompanyInventors: Guo-shuh J. Lee, Juan M. Garces, Dennis A. Hucul, Tracy L. Young, Kenneth A. Burdett
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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: 5345002Abstract: The present invention is directed to oil-soluble lubricating oil additives comprising Mannich Base condensates of an alkyl substituted hydroxy aromatic compound with formaldehyde and an amine, wherein the alkyl-moiety of the aromatic compounds is derived from at least one ethylene alpha-olefin copolymer of 300 to 20,000 number average molecular weight, wherein at least about 30% of the polymer's chains contain terminal ethenylidene unsaturation. The Mannich Base condensates of this invention are useful as dispersants.Type: GrantFiled: October 9, 1992Date of Patent: September 6, 1994Assignee: Exxon Chemical Patents Inc.Inventors: Won R. Song, Robert D. Lundberg, Antonio Gutierrez, Robert A. Kleist
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Patent number: 5334775Abstract: A process for alkylating hydroxyaromatic compounds with a terminally unsaturated polymer in the presence of a partially or completely dehydrated heteropoly catalyst. The alkylated hydroxyaromatic compounds so formed are useful as precursors for the production of fuel and lubricant additives.Type: GrantFiled: June 2, 1993Date of Patent: August 2, 1994Assignee: Exxon Chemical Patents Inc.Inventors: Antonio Gutierrez, Stuart L. Soled, Jose A. Paes
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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: 5300701Abstract: A process for the preparation of a polyisobutyl hydroxyaromatic compound which comprises alkylating a hydroxyaromatic compound in the presence of an acidic alkylation catalyst with a polyisobutene having a number average molecular weight in the range of about 300 to 5,000 and wherein the polyisobutene contains at least about 70% of a methylvinylidene isomer.Type: GrantFiled: December 28, 1992Date of Patent: April 5, 1994Assignee: Chevron Research and Technology CompanyInventor: Richard E. Cherpeck
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Patent number: 5292970Abstract: A method of manufacturing orthosubstituted alkylphenols, employing a catalyst of increased activity, by reacting phenol or 2-alkylphenols with 2-alkyl-1-alkenes and/or 2-aryl-1-alkenes in the liquid phase, optionally in the presence of inert diluents and/or an excess of the alkene, wherein the reaction is carried out in the presence of modified aluminum-containing catalysts obtained by adding small amounts of polyhalophenols, each having at least 3 like or unlike halogen substituents from the group of the elements fluorine, chlorine, and bromine, serving as cocatalysts, to known aluminum trisphenolate catalysts, wherein the molar ratio between the cocatalysts and the aluminum compound is in the range 0.5:1-8:1.The invention also relates to the catalyst for manufacturing the ortho-alkylated phenols, which catalyst is comprised of the (2-alkyl)phenol undergoing alkylation, an organoaluminum compound, and a polyhalophenol as the (or a) cocatalyst.Type: GrantFiled: November 30, 1992Date of Patent: March 8, 1994Assignee: Huels AktiengesellschaftInventors: Friedrich-Wilhelm Kupper, Wolfgang Muller
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Patent number: 5245089Abstract: Provided is a process for alkylating aromatic compounds in the presence of mixed oxides of titanium and gallium which have been found to be highly active catalysts for the alkylation of aromatics with alkyl esters, alcohols, olefins and ethers. When the alkyl acceptor is a phenol, the catalysts provide high reaction rates and high selectivity for ortho alkylated products.Type: GrantFiled: October 23, 1992Date of Patent: September 14, 1993Assignee: Eastman Kodak CompanyInventors: Gether Irick, Jr., Leslie S. LaForce
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Patent number: 5243115Abstract: Aromatic compounds are alkylated in a catalytic distillation, wherein the catalyst structure also serves as a distillation component by contacting the aromatic compound with a C.sub.2 to C.sub.10 olefin in the catalyst bed under 0.25 to 50 atmospheres of pressure and at temperatures in the range of 80.degree. C. to 500.degree. C., using as the catalyst a mole sieve characterized as acidic or an acidic cation exchange resin. For example, ethyl benzene is produced by feeding ethylene to about the mid point of the catalyst bed while benzene is conveniently added through the reflux in molar excess to that required to react with ethylene, thereby reacting substantially all of the ethylene and recovering benzene as the principal overhead and ethyl benzene in the bottoms.Type: GrantFiled: April 22, 1991Date of Patent: September 7, 1993Assignee: Chemical Research & Licensing CompanyInventors: Lawrence A. Smith, Jr., Robert P. Arganbright, Dennis Hearn
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Patent number: 5175377Abstract: The present invention provides an improved process for the production of ortho-alkyl phenols by vapor phase reaction of a phenol having at least one ortho-hydrogen with an alcohol, the improvement comprises soaking manganic oxide in an aqueous solution of alkali metal salt, separating the soaked manganic oxide from the solution, drying and calcining the soaked manganic oxide at a temperature of 300.degree.-600.degree. C. for a period of 1-3 hours to form an alkali metal oxide thereon, wherein the weight ratio of the alkali metal oxide to the manganic oxide is 0.5-0.0001 wt %, preferably 0.1-0.001 wt %.Type: GrantFiled: December 30, 1991Date of Patent: December 29, 1992Assignee: China Technical Consultants, Inc.Inventors: Ling-Wen Ho, Trong-Goang Lin, Yung-Chu Peng
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Patent number: 5171896Abstract: Disclosed is a one step method for synthesis of alkylphenols which comprises reacting phenol with the corresponding olefin under adiabatic conditions in the presence of a catalyst comprising an acidic montmorillonite clay having the structure:M.sub.x/n.sup.n+ .multidot.yH.sub.2 O(Al.sub.4-x Mg.sub.x)(Si.sub.8)O.sub.20 (OH).sub.4where M represent the interlamellar (balancing cation, normally sodium or lithium) and x, y and n are integers, wherein the acidic clay has been pretreated with an acid and optionally has deposited thereon an acid selected from the group consisting hydrogen fluoride, a fluorosulfonic acid or a mineral acid, at a temperature of from 60.degree. C. to 250.degree. C. and a pressure of from near atmospheric to about 500 psi.Type: GrantFiled: March 5, 1992Date of Patent: December 15, 1992Assignee: Texaco Chemical CompanyInventors: John F. Knifton, Yu-Hwa E. Sheu
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Patent number: 5144082Abstract: It is disclosed that aromatic compounds can be alkylated with mono-olefinic HVI-PAO dimer in contact with an acidic catalyst to produce novel alkylated aromatic compositions. It has been found that the novel HVI-PAO dimer alkylated aromatic compositions exhibit an extraordinary combination of properties relating to low viscosity with high viscosity index and low pour point which renders them very useful as lubricant basestock. Further, it has been found that the novel alkylaromatic compositions of the present invention show improved oxidative stability. Depending upon the substituent groups on the aromatic nucleus, useful lubricant additives can be prepared for improved antiwear, antioxidant and other properties. HVI-PAO dimer is prepared as a product or by-product from 1-alkene oligomerization using reduced chromium oxide on solid support. Particularly disclosed are the alkylphenols prepared by the process of alkylation a phenol at the aromatic nucleus with the novel oligomer.Type: GrantFiled: April 17, 1991Date of Patent: September 1, 1992Assignee: Mobil Oil CorporationInventors: Thomas R. Forbus, Bruce P. Pelrine
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Patent number: 5118875Abstract: Additives of improving the low temperature flow properties and oxidative stability of hydrocarbon oils are disclosed, which comprise the alkylation of a phenol in the presence of a polar aprotic cosolvent to produce an essentially linear alkylated phenol which is condensed with an aldehyde to produce the low temperature flow improver wherein:(a) the polymer composition has a number average molecular weight of at least about 3,000 and a molecular weight distribution of at least about 1.5;(b) in the alkylated phenol reactant the alkyl groups (i) are essentially linear; (ii) have between 6 and 50 carbon atoms; and (iii) have an average number of carbon atoms between about 12 and 26; and(c) not more than about 10 mole percent of the alkyl groups on the alkylated phenol have less than 12 carbon atoms and not more than about 10 mole percent of the alkyl groups on the alkylated phenol have more than 26 carbon atoms.Type: GrantFiled: October 10, 1990Date of Patent: June 2, 1992Assignee: Exxon Chemical Patents Inc.Inventors: David J. Martella, John J. Jaruzelski, Frank J. Chen
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Patent number: 5087772Abstract: A method for preparing 4-hydroxystyrene is disclosed. The method comprises reacting 4-acetoxystyrene with a suitable alcohol in the presence of a catalytic amount of a suitable base.Type: GrantFiled: November 16, 1990Date of Patent: February 11, 1992Assignee: Hoechst Celanese CorporationInventors: Michael T. Sheehan, Lan Shen
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Patent number: 5072054Abstract: Short-chain alkyl phenols are prepared by reacting an alkylatable phenolic compound with an alkylating agent having one or more available alkylating aliphatic groups of from one to five carbon atoms. The reaction is carried out under alkylation conditions with a zeolite catalyst characterized by x-ray diffraction values as set forth in Tables A to D, infra.Type: GrantFiled: July 31, 1990Date of Patent: December 10, 1991Assignee: Mobil Oil Corp.Inventors: David O. Marler, John P. McWilliams, Charles M. Smith
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Patent number: 5059727Abstract: A method of alkylating phenols which comprises reacting phenols having a hydrogen atom in at least one of the ortho-positions with regard to the hydroxyl group with an alcohol in a gaseous phase under heat in the presence of a catalyst comprising iron oxide, silica, chromium oxide, germanium oxide and an alkali metal compound. The catalyst exhibits a long catalytic activity duration and decreases frequency of regeneration and replacement of catalysts.Type: GrantFiled: August 21, 1990Date of Patent: October 22, 1991Assignee: Mitsubishi Gas Chemical Co., Inc.Inventor: Muneo Ito
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Patent number: 4973764Abstract: There are disclosed novel compositions of matter comprising monoalkylphenols prepared by selectively alkylating the olefin component of a thermally cracked sulfur-containing petroleum distillate derived from residua. The monoalkylphenols have certain ortho to para ratios and may be used to prepare a number of useful derivatives such as ethoxylated and propoxylated surfactants, sulfoalkylated products, sulfurized antioxidants, overbased phenates, dithiophosphate derivatives, formaldehyde reaction products and similar methylene bridged products which are useful demulsifiers.Type: GrantFiled: November 13, 1989Date of Patent: November 27, 1990Assignee: Exxon Research and Engineering CompanyInventors: Alexis A. Oswald, Ram N. Bhatia, Edmund J. Mozeleski, Darrell W. Brownawell, Thomas L. Ashcraft
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Patent number: 4954475Abstract: Catalyst precursor compositions comprising a mixture of magnesium oxide or a source of magnesium oxide and a water insoluble zinc compound are described. The compositions are calcinable to a catalyst that is useful in reactions for the ortho-alkylation of phenols.Type: GrantFiled: November 30, 1987Date of Patent: September 4, 1990Assignee: General Electric CompanyInventors: James G. Bennett, Jr., Gregory R. Chambers
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Patent number: 4950810Abstract: A selective process for preparing a 2,4- or 3,6-di-substituted phenol compound which comprises reacting an olefin compound of the formula: ##STR1## wherein R.sup.1 is hydrogen, halogen, alkyl, halogen substituted alkyl, aryl, halogen substituted-aryl or alkyl substituted-aryl; and R.sup.2, R.sup.3 and R.sup.4 are the same or different and each is hydrogen, halogen, alkyl, halogen substituted-alkyl or aralkyl; with a phenol compound of the formula: ##STR2## wherein R.sup.5 is hydrogen, hydroxy, halogen, alkyl, halogen substituted-alkyl, alkoxy or --C(R.sup.6)(R.sup.7)CH(R.sup.8)(R.sup.9) (wherein R.sup.6 is hydrogen, halogen, alkyl, halogen substituted-alkyl, aryl, halogen substituted-aryl or alkyl substituted-aryl; and R.sup.7, R.sup.8 and R.sup.9 are the same or different and each is hydrogen, halogen, alkyl, halogen substituted-alkyl or aralkyl), in the presence of a phosphorus compound and a carboxylic acid compound as catalysts.Type: GrantFiled: March 29, 1989Date of Patent: August 21, 1990Assignee: Yoshitomi Pharmaceutical Industries, Ltd.Inventors: Ryoichi Kinishi, Shuichi Wakamatsu, Tetsuji Ike
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Patent number: 4933509Abstract: A method is provided for ortho-alkylating phenol by passing a mixture of phenol and methanol through a heated magnesium oxide catalyst. The magnesium oxide catalyst is made by calcining magnesium carbonate and thereafter further heating the calcined product in the presence of steam.Type: GrantFiled: April 28, 1989Date of Patent: June 12, 1990Assignee: General Electric CompanyInventor: Gregory L. Warner
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Patent number: 4927979Abstract: A very simple process for preparing p-ethylphenol is disclosed. It is only necessary to contact phenol with an ethylating agent in vapor phase in the presence of a specific catalyst. The catalyst can be obtained by incorporating one or more alkoxysilanes to a crystalline aluminosilicte with a constraint index of 1-15 having a silica/alumina molar ratio of 20-400, wherein the amount of said alkoxysilanes to be incorporated is not less than 1.4 wt % calculated as silicon based on the amount of said crystalline aluminosilicate. Because the specific catalyst has the narrowed or restricted entrances of the micro pores of the crystalline aluminosilicate by the alkoxysilane treatment, it is possible to prepare p-ethylphenol in a high selectivity. The product contains only a very small amount of m-ethylphenol.Type: GrantFiled: December 6, 1988Date of Patent: May 22, 1990Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Takanori Yamagishi, Tsutomu Idai, Eiji Takahashi
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Patent number: 4914246Abstract: There are disclosed novel compositions of matter comprising monoalkylphenols prepared by selectively alkylating the olefin component of a thermally cracked sulfur-containing petroleum distillate derived from residua. The monoalkylphenols have certain ortho to para ratios and may be used to prepare a number of useful derivatives such as ethoxylated and propoxylated surfactants, sulfoalkylated products, sulfurized antioxidants, overbased phenates, dithiophosphate derivatives, formaldehyde reaction products and similar methylene bridged products which are useful demulsifiers.Type: GrantFiled: October 26, 1987Date of Patent: April 3, 1990Assignee: Exxon Research & Engineering CompanyInventors: Alexis A. Oswald, Ram N. Bhatia, Edmund J. Mozeleski, Darrell W. Brownawell, Thomas L. Ashcraft
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Patent number: 4912264Abstract: Process for producing hydroxy-containing alkylated aromatic compounds by the liquid phase reaction of an aromatic compound having at least one hydroxyl group with an alkylating agent in the presence of a heteropoly acid and water.Type: GrantFiled: June 3, 1987Date of Patent: March 27, 1990Assignee: Sumitomo Chemical Company, LimitedInventors: Akira Takeshita, Shinzaburo Masaki, Takeo Fujii, Tooru Tokumaru, Akira Murakami
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Patent number: RE34076Abstract: Process for producing hydroxy-containing alkylated aromatic compounds by the liquid phase reaction of an aromatic compound having at least one hydroxyl group with an alkylating agent in the presence of a heteropoly acid and water.Type: GrantFiled: July 15, 1991Date of Patent: September 22, 1992Assignee: Sumitomo Chemical Company LimitedInventors: Akira Takeshita, Shinzaburo Masaki, Takeo Fujii, Tooru Tokumaru, Akira Murakami