Preparing By Methylation Patents (Class 568/804)
  • Patent number: 11007508
    Abstract: A phenol alkylation catalyst exhibiting a desirable combination of activity, selectivity, and regenerability is prepared from a catalyst precursor that includes specific amounts of magnesium oxide, copper oxide or a copper oxide precursor, a hydrous magnesium aluminosilicate-containing binder, a pore-former, a lubricant, and water. Methods of forming and regenerating the catalyst, as well as a phenol alkylation method, are described.
    Type: Grant
    Filed: July 28, 2017
    Date of Patent: May 18, 2021
    Assignee: SHPP GLOBAL TECHNOLOGIES B.V.
    Inventors: James Kauffman, Gary Mell Bates, Douglas Henry Lenz, Kenchaiah Lohith, Vivek Chandra Gyani, Omoyemen E. Ofoegbu, Robin Woodbury, Xin Li, Xiankuan Zhang
  • Patent number: 9012697
    Abstract: A process is proposed for preparing hydroxyaromatics by heterogeneous catalytic reaction of hydroxyaromatics with C1-C4-alkanols in a microreactor (10), comprising the steps of: a) introducing the hydroxyaromatic and at least one compound selected from the group consisting of C1-C4-alkanols as reactants into at least one inlet orifice (22) of the microreactor (10) comprising at least one microreactor unit (18), b) passing the reactants through at least one microreactor unit (18) of the microreactor (10), said unit comprising a multitude of microchannels (28), said microchannels (28) having a lateral extent of less than 1 mm, and a heterogeneous catalyst being incorporated in the microchannels (28) for conversion of the reactants, c) passing the hydroxyaromatics prepared out through at least one outlet orifice (24) of the microreactor (10).
    Type: Grant
    Filed: March 7, 2012
    Date of Patent: April 21, 2015
    Assignee: Elantas GmbH
    Inventors: Oliver Bleifuβ, Simon Rost, Klaus-Wilhelm Lienert, Hans-Ulrich Moritz
  • Patent number: 8999013
    Abstract: Methods for producing alcohols and oligomers contemporaneously from a hydrocarbon feed containing mixed butenes using an acid based catalyst are provided. Additionally, methods for producing fuel compositions having alcohols and oligomers prepared from mixed olefins are also provided as embodiments of the present invention. In certain embodiments, the catalyst can include a dual phase catalyst system that includes a water soluble acid catalyst and a solid acid catalyst.
    Type: Grant
    Filed: October 31, 2012
    Date of Patent: April 7, 2015
    Assignee: Saudi Arabian Oil Company
    Inventors: Wei Xu, Thamer Mohammad, Kareemuddin M. Shaik, Aadesh Harale
  • Publication number: 20120238783
    Abstract: A process is proposed for preparing hydroxyaromatics by heterogeneous catalytic reaction of hydroxyaromatics with C1-C4-alkanols in a microreactor (10), comprising the steps of: a) introducing the hydroxyaromatic and at least one compound selected from the group consisting of C1-C4-alkanols as reactants into at least one inlet orifice (22) of the microreactor (10) comprising at least one microreactor unit (18), b) passing the reactants through at least one microreactor unit (18) of the microreactor (10), said unit comprising a multitude of microchannels (28), said microchannels (28) having a lateral extent of less than 1 mm, and a heterogeneous catalyst being incorporated in the microchannels (28) for conversion of the reactants, c) passing the hydroxyaromatics prepared out through at least one outlet orifice (24) of the microreactor (10).
    Type: Application
    Filed: March 7, 2012
    Publication date: September 20, 2012
    Applicant: ELANTAS GmbH
    Inventors: Oliver BLEIFUSS, Simon ROST, Klaus-Wilhelm LIENERT, Hans-Ulrich MORITZ
  • 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: 7087705
    Abstract: A continuous process comprising: contacting a mixture comprising dihydroxy aromatic compound, water and an alkylating agent with a catalyst system in the presence of a flowing carrier gas, to form a mono alkylated dihydroxy aromatic compound, wherein the catalyst system is obtained by the calcination of a catalyst precursor system comprising a metal oxide precursor, a transition metal element and a pore former.
    Type: Grant
    Filed: March 31, 2004
    Date of Patent: August 8, 2006
    Assignee: General Electric Company
    Inventors: Sunil Ashtekar, Pramod Kumbhar, Rathinam Jothi Mahalingam, Jegadeesh Thampi
  • Patent number: 7081432
    Abstract: An alkylation catalyst comprises a metal oxide wherein the catalyst has a surface area to volume ratio of about 950 m2/m3 to about 4000 m2/m3.
    Type: Grant
    Filed: July 10, 2003
    Date of Patent: July 25, 2006
    Assignee: General Electric Company
    Inventors: Hugo G. E. Ingelbrecht, David Parillo, Mukund Parthasarathy, Gert-Jan Schoenmakers, Geuch Zijlma
  • Patent number: 6951966
    Abstract: The orthoalkylation catalyst for phenols of the invention is one produced by calcining a catalyst precursor comprising basic magnesium carbonate (a) and magnesium oxide (b) optionally together with manganese oxalate (c), the basic magnesium carbonate (a) and magnesium oxide (b) being mixed together at a weight ratio ((a)/(b)) of 20/80 to 80/20. The process for producing an orthoalkylated phenol according to the invention comprises performing a vapor phase reaction of a phenol with an alkyl alcohol in the presence of the above orthoalkylation catalyst so that an orthoalkylated phenol is obtained. The invention enables obtaining an orthoalkylation catalyst for phenols which has high activity and high selectivity, has long catalytic life and exhibits more stable catalytic life than those of conventional orthoalkylation catalysts for phenols.
    Type: Grant
    Filed: September 28, 1999
    Date of Patent: October 4, 2005
    Assignee: Honshu Chemical Industry Co., Ltd.
    Inventors: Mitsuhiro Higashi, Masamitsu Tanaka, Kenji Ekawa
  • Patent number: 6846962
    Abstract: In a method for the production of o-alkyl phenols by conversion of phenol with an alkanol at elevated temperature in the gas phase in the presence of a metal catalyst, the conversion takes place in at least two stages wherein the alkanol/phenol molar ratio in each reaction stage is set to a value of approximately ?0.4; a clear increase in the selectivity for the o-alkyl phenol is obtained.
    Type: Grant
    Filed: November 15, 2002
    Date of Patent: January 25, 2005
    Assignee: Rutgers Chemicals AG
    Inventors: Jörg Talbiersky, Edgar Fuhrmann, Wolfgang Brüggemann
  • Publication number: 20040158104
    Abstract: In a method for the production of o-alkyl phenols by conversion of phenol with an alkanol at elevated temperature in the gas phase in the presence of a metal catalyst, the conversion takes place in at least two stages wherein the alkanol/phenol molar ratio in each reaction stage is set to a value of approximately ≦0.4; a clear increase in the selectivity for the o-alkyl phenol is obtained.
    Type: Application
    Filed: December 11, 2003
    Publication date: August 12, 2004
    Inventors: Jorg Talbiersky, Edgar Fuhrmann, Wolfgang Bruggemann
  • Publication number: 20040034256
    Abstract: A method for producing phenol is disclosed which includes oxidizing cumene to form cumene hydroperoxide and acid cleavage to form cumene, phenol, acetone, and various byproducts, including alpha methylstyrene, followed by a subsequent hydrogenation of at least a part of the acetone and substantially all of the alpha methylstyrene.
    Type: Application
    Filed: February 28, 2003
    Publication date: February 19, 2004
    Inventors: Kevin J. Fallon, Chung-Ming Chi, Frank A. Demers, Henry Y. Hwang
  • 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: 6593501
    Abstract: A process for producing an aromatic hydroxyl compound alkylated at the ortho position in high yield by subjecting an aromatic hydroxyl compound and an alkyl alcohol to a gas phase catalytic reaction in the presence of a metal oxide catalyst. The aromatic hydroxyl compound is a mixture of a phenol and ortho cresol, and the amount of ortho cresol in the mixture is 0.6 mole or less per 1 mole of phenol.
    Type: Grant
    Filed: September 10, 2001
    Date of Patent: July 15, 2003
    Assignee: Asahi Kasei Kabushiki Kaisha
    Inventors: Hitoshi Ota, Masaru Aga
  • 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
  • Publication number: 20020013502
    Abstract: A cumene process of producing phenol and acetone comprises the joint oxidation of aldehydes and dimethylbenzene alcohol by aqueous hydrogen peroxide solutions in presence of 16 wt % to 94 wt % of cumene hydroperoxide by contacting of mutually insoluble phases of the organic products from a cumene oxidation stage and hydrogen peroxide containing water with optional addition of acidic catalysts in a conversion reactor for the purpose of conversion of aldehydes into organic acids and dimethylbenzene alcohol into cumene hydroperoxide and therefore significantly simplifying the process of fractionation of organic conversion products into high quality product phenol and product acetone.
    Type: Application
    Filed: February 28, 2001
    Publication date: January 31, 2002
    Inventor: Vladimir Mikhailovitch Zakoshansky
  • Patent number: 6303801
    Abstract: A process for producing an alkyl-substituted hydroquinone, wherein said process comprises reacting a hydroquinone compound represented by the general formula (1) wherein R1 and R2 independently represent a hydrogen atom or a straight or branched chain alkyl group having 1 to 10 carbon atoms, R independently represent a straight or branched chain alkyl group having 1 to 10 carbon atoms and n represents an integer of 0 to 2, with a monohydric or dihydric alcohol in the presence of a catalyst and under the condition in which said alcohol is in a supercritical state by substitution of at least one hydrogen atom on the aromatic ring in said hydroquinone compound.
    Type: Grant
    Filed: March 2, 2000
    Date of Patent: October 16, 2001
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tomoyuki Suzuki, Toshio Sasaki
  • Patent number: 6291724
    Abstract: Selective catalytic reduction of the formation of alkylated phenols by transalkylation of ortho- and para-positions of alkylated phenols is accomplished by reacting ortho- and/or para-alkylated phenols with unreacted alkylated phenols in the presence of a metal oxide selected from the group consisting of Mg, Zn, Fe, V, Ce, Cs, Mn, or combinations thereof. This invention can be easily executed by recycling the alkylated phenols into the normal feed stream of the alkylation reactor.
    Type: Grant
    Filed: September 24, 1997
    Date of Patent: September 18, 2001
    Assignee: General Electric Company
    Inventor: Adrianus J. F. M. Braat
  • Publication number: 20010005769
    Abstract: The present invention relates to a process for the preparation of mixture of alkyl phenols preferably of 2, 6 xylenol and o-cresol using an ortho selective catalyst comprises contacting a catalyst with a feed consisting of an alcohol and a phenolic compound at a temperature ranging between 250 to 400 ° C., at a pressure in the range of ambient to 150 psi and collecting the products at a temperature ranging between −5 to +5° C.
    Type: Application
    Filed: October 26, 1998
    Publication date: June 28, 2001
    Inventors: BOLLAPRAGADA S. RAO, KURUNGOT SREEKUMAR, TUNDI MADATHIL JYOTHI
  • 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: 6239317
    Abstract: There is described a four step process for the production of halogeno-o-hydroxydiphenyl compounds having the formula in which X is —O—or —CH2—; m is 1 to 3; and n is 1 or 2; wherein in the first step, a diphenyl compound is chlorinated; in a second step the chlorinated compound is acylated in a Friedel-Crafts reaction and optionally again chlorinated after the acylation; in a third step the acyl compound is oxidised; and in a fourth step the oxidized compound is hydrolyzed. The compounds of formula (1) are useful for the protection of organic materials against microorganisms.
    Type: Grant
    Filed: February 5, 1998
    Date of Patent: May 29, 2001
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Surendra Umesh Kulkarni, Vadiraj Subbanna Ekkundi, Pradeep Jeevaji Nadkarni, Chandrasekhar Dayal Mudaliar, Kishore Ramachandra Nivalkar
  • 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: 5817886
    Abstract: The present invention provides a process for producing an alkyl ether of a phenol from a phenol and an alcohol at a selectivity and a yield higher than in conventional processes, stably over a long period of time. The process is characterized by alkyl-etherifying a phenol with an alcohol in the presence of an oxide catalyst comprising an alkali metal as a constituent element.
    Type: Grant
    Filed: December 24, 1996
    Date of Patent: October 6, 1998
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Kimio Ariyoshi, Yuuichi Satoh, Noboru Saito
  • 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: 5488173
    Abstract: A cyclohexanone having at least one ortho-hydrogen is selectively methylated in the ortho-position in the vapor phase. High conversion of the selected cyclohexanone and high selectivity in the ortho-position are obtained. The reaction products include 2-methylcyclohexanone, 2,6-dimethylcyclohexanone and 2,6-xylenol.
    Type: Grant
    Filed: August 3, 1994
    Date of Patent: January 30, 1996
    Inventor: Fey-Long Wang
  • Patent number: 5371306
    Abstract: The present invention relates to a novel oxide catalyst, more specifically, a novel modified magnesium oxide catalyst which is highly active and selective for ortho-alkylation of phenol.The catalysts for phenol alkylation of the invention are represented as Mg.sub.a Mn.sub.b L.sub.c T.sub.d Q.sub.e O.sub.x .wherein:L is vanadium or chromium;T is alkali metal, alkali earth metal, lead, bisumth, cobalt, aluminum, silicon., gallium, germanium or molybdenum;Q is antimony, cesium or iron;b/a=0 to 0.35(atomic molar ratio);c/a=0.01 to 0.35(atomic molar ratio);d/a=0 to 0.35(atomic molar ratio);e/c=0.1 to 10(atomic molar ratio); and,x is determined by oxidation state of each component.
    Type: Grant
    Filed: December 29, 1993
    Date of Patent: December 6, 1994
    Assignees: Korea Advanced Institute of Science and Technology, Lucky Ltd.
    Inventors: Seong-Ihl Woo, Won-Choon Choi, Kwang-Ho Park, Jin-Do Kim
  • 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: 5274174
    Abstract: A method for producing 4-acetoxystyrene by heating 4-acetoxyphenylmethylcarbinol, with an acid catalyst, at a temperature of from about 85.degree. C. to about 300.degree. C. under a pressure of from about 0.1 mm HgA to about 760 mm HgA for from about 0.2 minutes to about 10 minutes. The process also provides for the solventless (neat) hydrogenation of 4-acetoxyacetophenone to produce 4-acetoxyphenylmethylcarbinol. The reaction proceeds by heating at 54.degree. C. to 120.degree. C. with an excess of hydrogen in the presence of a Pd/C or activated nickel such as Raney Nickel catalyst in the absence of a solvent. The 4-acetoxyphenylmethylcarbinol may then be dehydrated to 4-acetoxystyrene. The later may be polymerized to poly(4-acetoxystyrene) and hydrolyzed to poly(4-hydroxystyrene).
    Type: Grant
    Filed: June 10, 1993
    Date of Patent: December 28, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Bakulesh N. Shah, Dung Q. Tran, Donna L. Keene
  • Patent number: 5256809
    Abstract: 4-Acetoxystyrene is reacted with a base in a solvent to form a salt of 4-hydroxystyrene via saponification. Alternatively, 4-hydroxystyrene is reacted with a base to form a salt of 4-hydroxystyrene. In the latter case, the 4-hydroxystyrene is prepared by the transesterification of 4-acetoxystyrene. Subsequently or simultaneously, the salt of 4-hydroxystyrene is reacted, preferably in situ. with di-tertiary-butyl-dicarbonate to form 4-tertiary-butoxycarbonyloxystyrene.
    Type: Grant
    Filed: September 3, 1992
    Date of Patent: October 26, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: George Kvakoyszky, James H. Rea, Michael T. Sheehan, Brad L. Smith
  • 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: 5132468
    Abstract: The alkyl hydroquinones, e.g., methyl hydroquinone (a useful intermediate in the preparation of the monomer methyl hydroquinone diacetate, itself used for the synthesis of thermotropic polymers), are prepared by reacting (C-alkylating) hydroquinone or a monoether thereof with a lower alkanal, in the vapor phase, with a catalytically effective amount of at least one solid metal oxide.
    Type: Grant
    Filed: January 18, 1991
    Date of Patent: July 21, 1992
    Assignee: Rhone-Poulenc Chimie
    Inventors: Claude Doussain, Michel Gubelmann, Philippe-Jean Tirel
  • Patent number: 5105029
    Abstract: A lower alcohol, for example, ethyl alcohol, is recovered from a reaction mixture resulted from a reaction of catechol with a lower alcohol in such a manner that the reaction mixture is distilled and separated into a distilled light vapor fraction comprising non-reacted lower alcohol and water and a residual fraction comprising a reaction product and non-reacted catechol; the distilled light vapor fraction is further distilled and separated into a distilled vapor fraction comprising the lower alcohol in an increased concentration and a residual water fraction; the distilled vapor fraction is fed to a gas-separating membrane module which allows water vapor to selectively permeate therethrough, and separated into a non-permeated fraction which comprises the lower alcohol in a high concentration, which is left in the feed side of the membrane, and a permeated fraction which comprises water in a high concentration, which is returned from the delivery side of the membrane to the further distilling step, and the no
    Type: Grant
    Filed: July 2, 1991
    Date of Patent: April 14, 1992
    Assignee: Ube Industries, Inc.
    Inventors: Kohei Ninomiya, Kanji Nakagawa, Yoichi Nishida
  • 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: 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: 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: 5041641
    Abstract: Pentafluorophenyl derivatives are expressed by the formula (I): ##STR1## where X represents an alkyl group having from 1 to 4 carbon atoms or a halogen atom; Y represents any group of --CH.sub.2 OH, --COOH, --COCl, --CON.sup.1 R.sup.2, or --OSO.sub.2 R.sup.3 ; R.sup.1, R.sup.2 and R.sup.3 represent an alkyl group which may have a substituted group, an aryl group which may have a substituted group, or a hydrogen atom except for R.sup.3. However, when X to a halogen atom, Y is the aforementioned groups other than --OSO.sub.2 R.sup.3. A racemate and/or an optical active form of the pentafluorophenyl derivatives can be used suitably as derivatizing agents for electron capture detection and optical resolution for analysis and as intermediates for medicines, agricultural chemicals, functional polymers, etc. The pentafluorophenyl derivatives are produced from pentafluorostyrene oxide.
    Type: Grant
    Filed: April 11, 1989
    Date of Patent: August 20, 1991
    Assignee: Nippon Mining Company Limited
    Inventors: Osamu Takahashi, Keizo Furuhashi, Junko Umezawa
  • 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: 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: 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: 4876398
    Abstract: A process for preparing an ortho-alkylated phenol is conducted by a vapor phase catalytic reaction at 200.degree.-500.degree. C. by reacting a vapor phenol compound selected from phenol, ortho-cresol and a mixture of phenol mixed with ortho-cresol with a vapor alcohol selected from methanol, in the presence of a catalyst containing magnesium oxide and manganese oxide, wherein the catalyst is prepared by treating an alkali in an aqueous solution having soluble magnesium ion and manganese ion to obtain coprecipitate of magnesium and manganese salt with respect to the alkali added, and the coprecipitate is then filtered, water-washed and calcined at 250.degree.-600.degree. C. for 1-4 hours for forming the catalyst consisting of magnesium oxide and manganese oxide having an atomic ratio of Mg/Mn of 1:1 to 100:1.
    Type: Grant
    Filed: June 10, 1988
    Date of Patent: October 24, 1989
    Assignee: China Petrochemical Development Corporation
    Inventors: Trong-Goang Lin, Ling-Wen Ho, An-Nan Ko, Yeong-Ju Perng
  • 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: 4814531
    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: July 27, 1987
    Date of Patent: March 21, 1989
    Assignee: Aristech Chemical Corporation
    Inventors: Leonard A. Cullo, Francis J. Shiring, III
  • Patent number: 4753913
    Abstract: The proposed catalyst for the gas-phase alkylation of phenols is based on magnesium oxide, contains up to 0.4% by weight of alkali metal oxide and is mechanically stabilized with from 1 to 8% by weight, based on the total weight of the catalyst, of graphite, molded and then heated.
    Type: Grant
    Filed: July 8, 1986
    Date of Patent: June 28, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Heinrich Lenz, Eckhard Roske, Karl Baer
  • 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: 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: 4644086
    Abstract: A process and catalyst for the orthomethylation of phenols having at least one free ortho position, wherein the phenols are reacted with methanol in a molar ratio of about 1:1 to 1:10 at about 250.degree.-340.degree. C. in the gaseous phase under a pressure of about 1-4 bar absolute and with rates per unit volume (LHSV) of about 0.05-3 h.sup.-1 in the presence of an iron oxide catalyst. This catalyst consists essentially of (a) iron oxide, (b) molybdenum oxide or tungsten oxide (c) one or several oxides of the elementsmagnesium, calcium, barium, lanthanum, cerium or manganese in a metal-atomic ratio of about (a):(b):(c): of 100:0.2- 10:0.2- 10.
    Type: Grant
    Filed: August 19, 1985
    Date of Patent: February 17, 1987
    Assignee: Huels Aktiengesellschaft
    Inventors: Heinz-Werner Voges, Arno Siegmar Schmidt
  • 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: 4590307
    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: April 4, 1985
    Date of Patent: May 20, 1986
    Assignee: General Electric Company
    Inventors: James G. Bennett, Jr., Freddie L. Tungate
  • 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: 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