Heavy Metal Or Aluminum Containing Catalyst Patents (Class 568/794)
  • 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: 20130324760
    Abstract: A method of crystallizing a crystalline molecular sieve having a pore size in the range of from about 2 to about 19 ?, said method comprising the steps of (a) providing a mixture comprising at least one source of ions of tetravalent element (Y), at least one hydroxide source (OH?), and water, said mixture having a solid-content in the range of from about 15 wt. % to about 50 wt. %; and (b) treating said mixture to form the desired crystalline molecular sieve with stirring at crystallization conditions sufficient to obtain a weight hourly throughput from about 0.005 to about 1 hr?1, wherein said crystallization conditions comprise a temperature in the range of from about 200° C. to about 500° C. and a crystallization time less than 100 hr.
    Type: Application
    Filed: August 7, 2013
    Publication date: December 5, 2013
    Inventors: Ivy D. Johnson, Wenyih Frank Lai
  • 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
  • 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
  • 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: 7282617
    Abstract: A process for making medium and long chain alkylaromatics and alkylphenols having a high level of anti-Markovnikov addition of the alkyl group. The alkylaromatics and alkylphenols made by the process of the present invention have enhanced stability and are particularly well suited to make highly stable oil additives and enhanced oil recovery surfactants.
    Type: Grant
    Filed: March 31, 2006
    Date of Patent: October 16, 2007
    Assignee: Chevron U.S.A. Inc.
    Inventors: William L. Schinski, Curt B. Campbell
  • Patent number: 7208438
    Abstract: A method of making a catalyst comprising mixing a metal oxide precursor and a pore former to form a metal oxide precursor mixture and calcining the metal oxide precursor mixture in the presence of a flowing gas having a flow rate to form the catalyst comprising metal oxide. The catalyst comprises a first distribution of pores having a median pore diameter of 10 to 50 angstroms and a second distribution of pores having a median pore diameter of 1 to 500 angstroms. The median pore diameter of the second distribution of pores is inversely related to the flow rate of the gas.
    Type: Grant
    Filed: July 30, 2004
    Date of Patent: April 24, 2007
    Assignee: General Electric Company
    Inventors: Hugo Gerard Eduard Ingelbrecht, Sabyasachi Mandal, Ashok Menon, Pradeep Nadkarni, Rupesh Pawar, Kuppuswamy Raghunathan, Gert-Jan Schoenmakers, Sahida Sharma
  • 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
  • Patent number: 5847237
    Abstract: There is disclosed a catalyst for ortho-alkylation of phenols obtained by calcination of a catalyst precursor comprising a dry mixture of:(a) manganese oxalate;(b) phenolic resin fine particles; and(c) at least one magnesium compound selected from the group consisting of basic magnesium carbonate and magnesium hydroxide.There is further disclosed a process for producing ortho-alkylated phenols by the gas phase reaction between an alkyl alcohol and a phenol in the presence of the ortho-alkylation catalyst defined above.
    Type: Grant
    Filed: July 3, 1996
    Date of Patent: December 8, 1998
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Shunji Yago, Takashi Kakiuchi, Keiji Arimatsu, Fujihisa Matsunaga
  • 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: 5300703
    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 a heteropoly acid represented by the structure:H.sub.8-n [XM.sub.12 O.sub.40 ]where x=P or Si, M=Mo or w.sub.v and n is an integer which is 4 or 5, alone, or deposited on an inert support, 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: April 5, 1993
    Date of Patent: April 5, 1994
    Assignee: Texaco Chemical Company
    Inventor: John F. Knifton
  • 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: 5276215
    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 zeolite catalyst, preferably a dealuminated Y-zeolite, a modified Y-zeolite, or a .beta.-zeolite.
    Type: Grant
    Filed: April 9, 1993
    Date of Patent: January 4, 1994
    Assignee: Texaco Chemical Company
    Inventors: John F. Knifton, Yu-Hwa E. Sheu, Pei-Shing Dai
  • 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: 5243116
    Abstract: Alkylated benzenes such as ethylbenzene and cumene are produced by alkylation and/or transalkylation in the presence of an acidic mordenite zeolite catalyst having a silica/alumina molar ratio of at least 30:1 and a crystalline structure which is determined by X-ray diffraction to be a matrix of Cmcm symmetry having dispersed therein domains of Cmmm symmetry.
    Type: Grant
    Filed: December 22, 1989
    Date of Patent: September 7, 1993
    Assignee: The Dow Chemical Company
    Inventors: Guo-shuh J. Lee, Juan M. Garces, Garmt R. Meima, Matheus J. M. van der Aalst
  • Patent number: 5198595
    Abstract: Monoalkylated benzene such as ethylbenzene and cumene or monoalkylated substituted benzene are produced by alkylation in the presence of an acidic mordenite zeolite catalyst having a silica/alumina molar ratio of at least 40:1, preferably 160:1. In a subsequent, optional process, the polyalkylated benzene or polyalkylated substituted benzene produced in the alkylation is transalkylated in the presence of an acidic mordenite zeolite catalyst.
    Type: Grant
    Filed: June 21, 1991
    Date of Patent: March 30, 1993
    Assignee: The Dow Chemical Company
    Inventors: Guo-shuh J. Lee, Juan M. Garces, Garmt R. Meima, Matheus J. M. van der Aalst
  • Patent number: 5175375
    Abstract: The invention relates to producing ortho isopropyl phenol catalytically by contacting phenol with isopropanol or propylene, at a temperature of from about 200.degree. C. to about 300.degree. C., with ZSM-12 and zeolite Beta; and recovering ortho isopropyl phenol.
    Type: Grant
    Filed: October 11, 1991
    Date of Patent: December 29, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Clarence D. Chang, Stuart D. Hellring
  • 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: 5098945
    Abstract: A composition containing a) a polystyrene, substituted polystyrene, copolymer or terpolymer of styrene or of a substituted styrene, polycarbonate, polyester-carbonate, polyurethane, polyamide copolyamide, polyacetyl or polyphenylene oxide and b) at least one compound of the formula I ##STR1## in which R.sub.1 is methyl or ethyl and R.sub.2 is C.sub.2 -C.sub.30 alkyl.Compounds of the formula I in which R.sub.2 is C.sub.8 -C.sub.30 alkyl are novel and are suitable for stabilizing organic materials against thermal, oxidative and actinic degradation.
    Type: Grant
    Filed: February 11, 1991
    Date of Patent: March 24, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Rita Pitteloud, Paul Dubs
  • Patent number: 5097079
    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: July 6, 1990
    Date of Patent: March 17, 1992
    Assignee: General Electric Company
    Inventors: James G. Bennett, Jr., Gregory R. Chambers
  • Patent number: 5091594
    Abstract: For producing 2,6-di-tert-butylphenol and products therefrom, utilizing small quantities of aluminum tris-(2-tert-butylphenolate as a catalyst by reaction of 2-tert-butylphenol with isobutene in the liquid phase, the reaction is performed in the presence of diluents such as liquid saturated aliphatic or cycloaliphatic hydrocarbons, C.sub.5 -C.sub.16 alkenes of formula R.sub.1 --CH.dbd.CH.sub.2 or R.sub.2 --CH.dbd.CH--R.sub.3, C.sub.5 to C.sub.12 cycloalkenes, which contain no branching on the C.dbd.C-bond, excess isobutene or mixtures thereof, at temperatures of 0.degree. C. to 80.degree. C., pressures of 0.1 to 11 bars and catalyst amounts of 0.005 to 5 mol %, based on 2-tert-butylphenol. High conversions are obtained with few undesirable trialkylated products.
    Type: Grant
    Filed: December 11, 1990
    Date of Patent: February 25, 1992
    Assignee: Huels Aktiengesellschaft
    Inventors: Friedrich-Wilhelm Kupper, Wolfgang H. E. Muller, Alfred Oberholz
  • 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: 5030770
    Abstract: Thymol can be prepared by reaction of m-cresol with propene at elevated temperature and at atmospheric to superatmospheric pressure by using wide- and medium-pored zeolites which have a pore diameter of at least 5 .ANG. as heterogeneous catalysts.
    Type: Grant
    Filed: July 5, 1989
    Date of Patent: July 9, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Wimmer, Hans-Josef Buysch, Lothar Puppe
  • 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: 4954663
    Abstract: Long chain alkyl phenols are prepared by alkylating an alkylatable phenolic compound with a long chain alkylating agent under alkylation reaction conditions in the presence of catalyst comprising a synthetic porous crystalline material characterized by an X-ray diffraction pattern including interplanar d-spacings at 12.36.+-.0.4, 11.03.+-.0.2, 8.83.+-.0.14, 6.18.+-.0.12, 6.00.+-.0.10, 4.06.+-.0.07; 3.91.+-.0.07 and 3.42.+-.0.06 Angstroms.
    Type: Grant
    Filed: January 25, 1990
    Date of Patent: September 4, 1990
    Assignee: Mobil Oil Corp.
    Inventors: David O. Marler, John P. McWilliams
  • 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: 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: 4906793
    Abstract: Crystalline silica-titania catalyst compositions, optionally containing magnesium, are disclosed; the titanium is introduced through the use of organo-titanate chelates wherein the titanium has a coordination number of at least 5. The compositions are used in acid-catalyzed reactions such as alkylation reactions.
    Type: Grant
    Filed: November 17, 1988
    Date of Patent: March 6, 1990
    Assignee: Aristech Chemical Corporation
    Inventors: Leonard A. Cullo, Francis J. Shiring, III
  • Patent number: 4870216
    Abstract: Phenols are selectively orthoalkylated in higher yields by the reverse addition of a phenol-aluminum phenoxide mixture to an olefin at alkylation temperature and under pressure sufficient to maintain a liquid olefin phase.
    Type: Grant
    Filed: June 24, 1988
    Date of Patent: September 26, 1989
    Assignee: Ethyl Corporation
    Inventors: Jeffrey F. King, Charles W. Matthews, Eric S. Batman
  • Patent number: 4870215
    Abstract: Phenol is di-orthoalkylated in high yield by reacting, in a first stage, phenol containing only 1 mole of an aluminum phenoxide for each 100-800 moles of phenol with an olefin at 85.degree.-175.degree. C. until the reaction mixture contains 3 wt percent or less phenol and then, in a second stage, continuing the reaction at 25.degree.-80.degree. C. until the mixture contains a substantial amount of 2,6-di-alkylphenol.
    Type: Grant
    Filed: June 24, 1988
    Date of Patent: September 26, 1989
    Assignee: Ethyl Corporation
    Inventors: Steven L. Wiker, Charles W Matthews, Jeffrey F. King
  • Patent number: 4851591
    Abstract: A catalyst precursor comprising a magnesium compound or material, optionally also containing other metal compounds, is activated for use by calcining at an elevated temperature in the presence of air or nitrogen, or under vacuum. The active catalyst which results may be used in processes for the ortho-alkylation of phenolic compounds, with good yields of and selectivity to the ortho-alkylated end product.
    Type: Grant
    Filed: December 16, 1987
    Date of Patent: July 25, 1989
    Assignee: General Electric Company
    Inventors: Richard A. Battista, James G. Bennett, Jr., John J. Kokoszka, Freddie L. Tungate
  • Patent number: 4731492
    Abstract: A process of ortho-alkylating arylhydroxides, e.g., phenol, by passing a mixture of arylhydroxide, olefin and an inert hydrocarbon diluent in the liquid phase through a bed of activated alumina at an elevated temperature and pressure. Conversion and selectivity is improved over that obtained without the diluent.
    Type: Grant
    Filed: March 4, 1987
    Date of Patent: March 15, 1988
    Assignee: Ethyl Corporation
    Inventors: Steven L. Wiker, S. Wendell Holmes, Jr., Dixie E. Goins
  • Patent number: 4677089
    Abstract: A catalyst precursor comprised of a dry admixture of manganese carbonate and at least one material selected from among magnesium carbonate, basic magnesium carbonate and magnesium hydroxide. The precursor is calcinable at elevated temperatures to an activated catalyst which may be used in a process for the ortho-alkylation of phenolic compounds.
    Type: Grant
    Filed: June 23, 1986
    Date of Patent: June 30, 1987
    Assignee: General Electric Company
    Inventors: James G. Bennett, Jr., Freddie L. Tungate
  • Patent number: 4665238
    Abstract: Alkylaromatic compounds may be synthesized by reacting an aromatic compound with an alkylating agent comprising a mixture of gases, including carbon monoxide and hydrogen at alkylation conditions in the presence of a dual-function-catalyst. The catalyst system which is employed for this reaction will comprise (1) a composite of oxides of copper and chromium and (2) an aluminosilicate which may be either in crystalline or amorphous form.
    Type: Grant
    Filed: September 9, 1985
    Date of Patent: May 12, 1987
    Assignee: UOP Inc.
    Inventors: Tamotsu Imai, Paul T. Barger
  • Patent number: 4661638
    Abstract: A catalyst precursor prepared by precipitating manganese hydroxide from caustic solution and then mixing the precipitate with a magnesium-containing material is described. The catalyst precursor can be calcined to an active form, and the resulting catalyst can be used to effect or facilitate the ortho-alkylation of phenolic compounds in vapor phase reactions. Superiority of performance is demonstrated with respect to a catalyst derived from a precursor in which manganese hydroxide is precipitated (sometimes referred to as "co-precipitation") in the presence of a magnesium compound, rather than formed separately.
    Type: Grant
    Filed: September 16, 1985
    Date of Patent: April 28, 1987
    Assignee: General Electric Company
    Inventors: Richard A. Battista, James G. Bennett, Jr., John J. Kokoszka, Freddie L. Tungate
  • Patent number: 4599465
    Abstract: A process for producing an orthoalkylphenol which comprises reacting phenol with an olefin in a liquid phase in the presence of an alumina catalyst, characterized in that the water content in the liquid phase of the reaction system is maintained at a level of not higher than 250 ppm.
    Type: Grant
    Filed: June 5, 1985
    Date of Patent: July 8, 1986
    Assignee: Mitsubishi Chemical Industries, Ltd.
    Inventors: Akio Tamaru, Yoshiaki Izumisawa, Hidekichi Hashimoto, Kiyoji Kuma, Takashi Komaya, Masanobu Minagawa
  • Patent number: 4594460
    Abstract: Substituted phenols of formula ##STR1## in which R.sub.1 is in an ortho or para position relative to the phenol function and denotes ##STR2## R.sub.2 denotes an acyclic radical optionally substituted by alkyl, hydroxy, alkoxycarbonyl, cyano or formyl, or a phenyl or naphthyl radical, and R denotes hydrogen or 1 to 4 substituents chosen from halogen, OH optionally in the form of ether or ester, alkyl, NO.sub.2, CHO optionally in the form of acetal, CH.sub.3 CO--, C.sub.6 H.sub.5 CO--, NH.sub.2, alkylamino, dialkylamino or alkoxycarbonyl, it being understood that 2 symbols R may form with the phenyl nucleus a condensed aromatic ring, which comprises reacting a butadiene of formula ##STR3## with a phenol for formula ##STR4## in water in the presence of a rhodium-based catalyst, a water-soluble phosphine and optionally an inorganic or organic base. The products of formula (I) are intermediates for the synthesis of vitamin E, antioxidants, perfumes or insecticides.
    Type: Grant
    Filed: March 19, 1985
    Date of Patent: June 10, 1986
    Assignee: Rhone-Poulenc Sante
    Inventors: Gerard Mignani, Didier Morel
  • Patent number: 4590306
    Abstract: The instant invention relates to a process for the conversion of meta/para-cresol mixtures by catalytically methylating the meta/para-cresol mixtures in their ortho-positions, separating the 2,3,6- and 2,4,6-trimethylphenols formed and converting subsequently the 2,4,6-trimethylphenol in the presence of iron oxide(s) or catalysts which contain iron oxide(s) and at least one additional oxide, to a mixture of methyl phenols, which is essentially free from meta-substituted methylphenols.
    Type: Grant
    Filed: February 19, 1985
    Date of Patent: May 20, 1986
    Assignee: Union Rheinische Braunkohlen Kraftstoff Aktiengesellschaft
    Inventors: Joachim Korff, Karl-Heinz Keim
  • Patent number: 4568662
    Abstract: Preparation of alkylation catalysts containing iron oxide and/or chromium oxide, by means of a process which comprises:(a) precipitating hydrate oxides of iron and/or chromium from an aqueous solution of soluble compounds of said elements;(b) separating the thus obtained precipitate, and washing said precipitate;(c) granulating the washed precipitate, and drying the granules so obtained;(d) calcining said dried granules at high temperature;in which an organic carboxylic acid salt of iron and/or chromium is added to and homogenized with the washed precipitate from stage (b), and/or the dried granules from stage (c) are impregnated with an aqueous solution of an organic carboxylic acid salt of iron and/or chromium.The catalysts obtained by means of the above process are mechanically strong, and highly active in the production process of 2,6-xylenol by means of the alkylation of phenol or o-cresol with methanol.
    Type: Grant
    Filed: December 3, 1984
    Date of Patent: February 4, 1986
    Assignee: Enichimica S.p.A.
    Inventors: Jan Bialy, Irena Penczek, Nikuca Kopytowska, Josef Wrzyszcz, Jolanta Cmielowska, Hanna Grabowska, Wlodzimierz Kaczmarczyk, Kazimierz Mazur, Wlodzimierz Mista
  • Patent number: 4560809
    Abstract: A process for the production of a 2,6-dialkylphenol in high yield wherein the alkyl groups are secondary or tertiary with a reduced overall production of 4-alkylphenol by-products by the aluminum phenoxide catalyzed pressure reaction of isobutylene with phenol and a mixture of 2,4-dialkylphenol and 2,4,6-trialkylphenol which may be obtained, in a cyclic process, as a bottom stream from the distillation of the reaction mixture to obtain the 2,6-dialkylphenol product.
    Type: Grant
    Filed: October 9, 1984
    Date of Patent: December 24, 1985
    Assignee: Ethyl Corporation
    Inventors: Dixie E. Goins, Harold V. Huggins, Edward A. Burt, Silas W. Holmes
  • Patent number: 4554388
    Abstract: This invention relates to a process for isomerization and transalkylation of alkylphenols and for phenol-derivatives in the presence of a catalyst comprising ironoxide (s) and at least one additional oxide and in the case of 2,4,6-trimethylphenol and 2,4-dimethylphenol as alkylphenol feed, of ironoxide (s) or of a catalyst comprising ironoxide (s) and at least one additional oxide.
    Type: Grant
    Filed: February 7, 1984
    Date of Patent: November 19, 1985
    Assignee: Rheinische Braunkohlenwerke Aktiengesellschaft
    Inventors: Karl-Heinz Keim, Joachim Korff
  • Patent number: 4554267
    Abstract: Hydroxyaromatic compounds such as phenol are alkylated with alkanols such as methanol in the presence of a catalyst comprising magnesium oxide with up to about 0.1% by weight of copper deposited thereon in a layer of submicroscopic thickness. The catalyst is prepared by preparing a slurry of a substantially water-insoluble magnesium reagent such as magnesium hydroxide or magnesium carbonate in an aqueous solution of at least one copper salt, removing and drying the solid phase, and calcining the same at a temperature within the range of about 350.degree.-550.degree. C. The catalyst promotes ortho-alkylation of the hydroxyaromatic compound in high yield, minimizes decomposition of the alkanol, and has long life.
    Type: Grant
    Filed: June 3, 1983
    Date of Patent: November 19, 1985
    Assignee: General Electric Company
    Inventors: Gregory R. Chambers, James G. Bennett, Jr.
  • Patent number: 4554266
    Abstract: Hydroxyaromatic compounds such as phenol are alkylated with alkanols such as methanol in the presence of a catalyst comprising an intimate blend of magnesium oxide and copper, the latter being present in an amount up to about 2% by weight, based on said magnesium oxide. The catalyst is prepared by blending a magnesium reagent and copper in elemental or (preferably) chemically combined form and calcining the same at a temperature within the range of about 350.degree.-550.degree. C. The catalyst promotes ortho-alkylation of the hydroxyaromatic compound in high yield, minimizes decomposition of the alkanol, and has long life.
    Type: Grant
    Filed: June 3, 1983
    Date of Patent: November 19, 1985
    Assignee: General Electric Company
    Inventors: James G. Bennett, Gregory R. Chambers
  • Patent number: 4547480
    Abstract: A catalyst precursor comprised of a dry admixture of manganese carbonate and at least one material selected from among magnesium carbonate, basic magnesium carbonate and magnesium hydroxide. The precursor is calcinable at elevated temperatures to an activated catalyst which may be used in a process for the ortho-alkylation of phenolic compounds.
    Type: Grant
    Filed: December 20, 1983
    Date of Patent: October 15, 1985
    Assignee: General Electric Company
    Inventors: James G. Bennett, Jr., Freddie L. Tungate
  • 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