Preparing By Catalytic Alkylation Patents (Class 568/790)
  • Patent number: 10549263
    Abstract: 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: Grant
    Filed: November 9, 2016
    Date of Patent: February 4, 2020
    Assignee: RGF ENVIRONMENTAL GROUP, INC.
    Inventors: Walter B. Ellis, Ronald G. Fink
  • Patent number: 9109198
    Abstract: 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: Grant
    Filed: April 29, 2011
    Date of Patent: August 18, 2015
    Assignee: General Electric Company
    Inventors: Zaeem Ashraf Khan, Aaron Joseph Dulgar-Tulloch, Stefan Rakuff, Philip Alexander Shoemaker, Erik Leeming Kvam, Xiaohui Chen, Jaydeep Roy
  • Patent number: 8993813
    Abstract: The present invention relates to a process for the preparation of 4-isopropyl-3-methylphenol (p-thymol) from distillation residues of thymol production.
    Type: Grant
    Filed: May 18, 2012
    Date of Patent: March 31, 2015
    Assignee: LANXESS Deutschland GmbH
    Inventors: Uwe Boeger, Lutz Heuer, Michael Herzhoff
  • Patent number: 8704006
    Abstract: 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: Grant
    Filed: December 10, 2010
    Date of Patent: April 22, 2014
    Assignee: Chevron Oronite Company LLC
    Inventors: Curtis Bay Campbell, Cedrick Mahieux
  • Publication number: 20130150607
    Abstract: 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: Application
    Filed: December 7, 2011
    Publication date: June 13, 2013
    Inventor: Beth A. WINSETT
  • Publication number: 20130150608
    Abstract: 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: Application
    Filed: December 13, 2011
    Publication date: June 13, 2013
    Inventors: Beth A. Winsett, James I. Arnett, II, Kenwyn M. Leger, Brady A. Compton
  • Patent number: 8247621
    Abstract: 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: Grant
    Filed: October 12, 2009
    Date of Patent: August 21, 2012
    Assignee: Invista North America S.A.R.L.
    Inventors: Joachim C. Ritter, James Michael Garner
  • Patent number: 8207380
    Abstract: 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: Grant
    Filed: April 27, 2007
    Date of Patent: June 26, 2012
    Assignee: Chevron Oronite LLC
    Inventors: Curt B. Campbell, James J. Harrison
  • Publication number: 20100269406
    Abstract: 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: Application
    Filed: November 13, 2008
    Publication date: October 28, 2010
    Applicant: The Lubrizol Corporation
    Inventors: David J. Moreton, Antonio Mastrangelo, Malcolm MacDuff
  • Patent number: 7750193
    Abstract: 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: Grant
    Filed: February 1, 2005
    Date of Patent: July 6, 2010
    Assignee: BASF Aktiengesellschaft
    Inventors: Arno Lange, Helmut Mach, Hans Peter Rath, Dietmar Posselt, Anja Vinckier
  • Publication number: 20090176998
    Abstract: 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: Application
    Filed: March 6, 2009
    Publication date: July 9, 2009
    Inventors: Werner Bonrath, Yann Foricher, Thomas Netscher, Angela Wildermann
  • Patent number: 7435273
    Abstract: 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: Grant
    Filed: January 22, 2002
    Date of Patent: October 14, 2008
    Assignee: Basf Aktiengesellschaft
    Inventors: Arno Lange, Hans Peter Rath, Marc Walter
  • Publication number: 20080114192
    Abstract: 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: Application
    Filed: September 26, 2007
    Publication date: May 15, 2008
    Applicant: Secretary, Department of Science and Technology
    Inventors: Anjali Uday Patel, Nikunj Bhagwatiprasad Bhatt
  • Patent number: 7288683
    Abstract: 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: Grant
    Filed: June 16, 2006
    Date of Patent: October 30, 2007
    Assignee: General Electric Company
    Inventors: Hugo G. E. Ingelbrecht, David Parrillo, Mukund Parthasarathy, Gert-Jan Schoenmakers, Geuch Zijlma
  • Patent number: 6914163
    Abstract: 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: Grant
    Filed: September 27, 2001
    Date of Patent: July 5, 2005
    Assignee: BASF AG
    Inventors: Arno Lange, Hans Peter Rath
  • Patent number: 6875897
    Abstract: 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: Grant
    Filed: September 27, 2001
    Date of Patent: April 5, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Arno Lange, Hans Peter Rath
  • Publication number: 20040118673
    Abstract: 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: Application
    Filed: March 7, 2003
    Publication date: June 24, 2004
    Applicant: Council of Scientific & Industrial Research
    Inventors: Arun Kumar Sinha, Bhupendra Prasad Joshi, Anuj Sharma
  • Patent number: 6670513
    Abstract: 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: Grant
    Filed: December 3, 1999
    Date of Patent: December 30, 2003
    Assignees: Chevron Oronite Company, LLC, Chevron Oronite S.A.
    Inventors: Curtis Bay Campbell, Jean Louis Le Coënt
  • Patent number: 6617476
    Abstract: 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: Grant
    Filed: December 13, 2000
    Date of Patent: September 9, 2003
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tomoyuki Suzuki, Fumisato Goto, Kozo Tanaka
  • Patent number: 6417410
    Abstract: 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: Grant
    Filed: April 18, 2001
    Date of Patent: July 9, 2002
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tomoyuki Suzuki, Fumisato Goto
  • Patent number: 6274777
    Abstract: 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: Grant
    Filed: December 30, 1999
    Date of Patent: August 14, 2001
    Assignees: Chevron Chemical Company LLC, Chevron Chemical S.A.
    Inventors: James A. Gray, Thierry Triconnet
  • Publication number: 20010004674
    Abstract: A process for producing an aromatic ring alkylated phenols, wherein said process comprises reacting phenols represented by the general formula (1): 1
    Type: Application
    Filed: December 13, 2000
    Publication date: June 21, 2001
    Inventors: Tomoyuki Suzuki, Fumisato Goto, Kozo Tanaka
  • Patent number: 6232485
    Abstract: 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: Grant
    Filed: November 26, 1999
    Date of Patent: May 15, 2001
    Assignee: Great Lakes Chemical Corporation
    Inventors: Tracy Anne Derbyshire, Hazel May Farrow, Jonathan Simon Hill
  • Patent number: 6191317
    Abstract: 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: Grant
    Filed: August 31, 1999
    Date of Patent: February 20, 2001
    Assignee: Huntsman Petrochemical Corporation
    Inventor: Wei-Yang Su
  • Patent number: 5663457
    Abstract: Conventional low vinylidene polyolefins are condensed with hydroxyaromatics under the influence of macroreticular ion exchange resins in acid form to yield alkylated hydroxyaromatics.
    Type: Grant
    Filed: February 16, 1996
    Date of Patent: September 2, 1997
    Assignee: The Lubrizol Corporation
    Inventor: Christopher Jay Kolp
  • Patent number: 5633411
    Abstract: 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: Grant
    Filed: May 28, 1996
    Date of Patent: May 27, 1997
    Assignee: Loctite Corporation
    Inventors: John G. Woods, Maria Masterson
  • Patent number: 5583268
    Abstract: 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: Grant
    Filed: December 15, 1995
    Date of Patent: December 10, 1996
    Assignee: The Dow Chemical Company
    Inventors: Guo-shuh J. Lee, Juan M. Garces, Dennis A. Hucul, Tracy L. Young, Kenneth A. Burdett
  • 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: 5345002
    Abstract: 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: Grant
    Filed: October 9, 1992
    Date of Patent: September 6, 1994
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Won R. Song, Robert D. Lundberg, Antonio Gutierrez, Robert A. Kleist
  • Patent number: 5334775
    Abstract: 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: Grant
    Filed: June 2, 1993
    Date of Patent: August 2, 1994
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Antonio Gutierrez, Stuart L. Soled, Jose A. Paes
  • 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: 5300701
    Abstract: 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: Grant
    Filed: December 28, 1992
    Date of Patent: April 5, 1994
    Assignee: Chevron Research and Technology Company
    Inventor: Richard E. Cherpeck
  • Patent number: 5292970
    Abstract: 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: Grant
    Filed: November 30, 1992
    Date of Patent: March 8, 1994
    Assignee: Huels Aktiengesellschaft
    Inventors: Friedrich-Wilhelm Kupper, Wolfgang Muller
  • Patent number: 5245089
    Abstract: 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: Grant
    Filed: October 23, 1992
    Date of Patent: September 14, 1993
    Assignee: Eastman Kodak Company
    Inventors: Gether Irick, Jr., Leslie S. LaForce
  • Patent number: 5243115
    Abstract: 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: Grant
    Filed: April 22, 1991
    Date of Patent: September 7, 1993
    Assignee: Chemical Research & Licensing Company
    Inventors: Lawrence A. Smith, Jr., Robert P. Arganbright, Dennis Hearn
  • Patent number: 5175377
    Abstract: 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: Grant
    Filed: December 30, 1991
    Date of Patent: December 29, 1992
    Assignee: China Technical Consultants, Inc.
    Inventors: Ling-Wen Ho, Trong-Goang Lin, Yung-Chu Peng
  • Patent number: 5171896
    Abstract: 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: Grant
    Filed: March 5, 1992
    Date of Patent: December 15, 1992
    Assignee: Texaco Chemical Company
    Inventors: John F. Knifton, Yu-Hwa E. Sheu
  • Patent number: 5144082
    Abstract: 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: Grant
    Filed: April 17, 1991
    Date of Patent: September 1, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Thomas R. Forbus, Bruce P. Pelrine
  • Patent number: 5118875
    Abstract: 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: Grant
    Filed: October 10, 1990
    Date of Patent: June 2, 1992
    Assignee: Exxon Chemical Patents Inc.
    Inventors: David J. Martella, John J. Jaruzelski, Frank J. Chen
  • Patent number: 5087772
    Abstract: 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: Grant
    Filed: November 16, 1990
    Date of Patent: February 11, 1992
    Assignee: Hoechst Celanese Corporation
    Inventors: Michael T. Sheehan, Lan Shen
  • Patent number: 5072054
    Abstract: 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: Grant
    Filed: July 31, 1990
    Date of Patent: December 10, 1991
    Assignee: Mobil Oil Corp.
    Inventors: David O. Marler, John P. McWilliams, Charles M. Smith
  • Patent number: 5059727
    Abstract: 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: Grant
    Filed: August 21, 1990
    Date of Patent: October 22, 1991
    Assignee: Mitsubishi Gas Chemical Co., Inc.
    Inventor: Muneo Ito
  • Patent number: 4973764
    Abstract: 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: Grant
    Filed: November 13, 1989
    Date of Patent: November 27, 1990
    Assignee: Exxon Research and Engineering Company
    Inventors: Alexis A. Oswald, Ram N. Bhatia, Edmund J. Mozeleski, Darrell W. Brownawell, Thomas L. Ashcraft
  • Patent number: 4954475
    Abstract: 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: Grant
    Filed: November 30, 1987
    Date of Patent: September 4, 1990
    Assignee: General Electric Company
    Inventors: James G. Bennett, Jr., Gregory R. Chambers
  • Patent number: 4950810
    Abstract: 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: Grant
    Filed: March 29, 1989
    Date of Patent: August 21, 1990
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Ryoichi Kinishi, Shuichi Wakamatsu, Tetsuji Ike
  • Patent number: 4933509
    Abstract: 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: Grant
    Filed: April 28, 1989
    Date of Patent: June 12, 1990
    Assignee: General Electric Company
    Inventor: Gregory L. Warner
  • Patent number: 4927979
    Abstract: 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: Grant
    Filed: December 6, 1988
    Date of Patent: May 22, 1990
    Assignee: Maruzen Petrochemical Co., Ltd.
    Inventors: Takanori Yamagishi, Tsutomu Idai, Eiji Takahashi
  • Patent number: 4914246
    Abstract: 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: Grant
    Filed: October 26, 1987
    Date of Patent: April 3, 1990
    Assignee: Exxon Research & Engineering Company
    Inventors: Alexis A. Oswald, Ram N. Bhatia, Edmund J. Mozeleski, Darrell W. Brownawell, Thomas L. Ashcraft
  • Patent number: 4912264
    Abstract: 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: Grant
    Filed: June 3, 1987
    Date of Patent: March 27, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Akira Takeshita, Shinzaburo Masaki, Takeo Fujii, Tooru Tokumaru, Akira Murakami
  • Patent number: RE34076
    Abstract: 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: Grant
    Filed: July 15, 1991
    Date of Patent: September 22, 1992
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Akira Takeshita, Shinzaburo Masaki, Takeo Fujii, Tooru Tokumaru, Akira Murakami