Heavy Metal Or Aluminum Containing Catalyst Patents (Class 568/794)
  • Patent number: 4540833
    Abstract: An acetylenic end-capping agent of the general formula ##STR1## wherein R.sup.1 and R.sup.2 can be the same or different and are selected from the group consisting of hydrogen, C11 to C4 alkyl, phenyl and substituted phenyl, and wherein R.sup.1 and R.sup.2 together with the carbon atom to which they are attached form a saturated 5- or 6-membered ring. This end-capping agent is substantially free of Pd and Cu.Also provided is a method for producing this end-capping agent and a method for producing acetylene terminated compounds.
    Type: Grant
    Filed: March 21, 1984
    Date of Patent: September 10, 1985
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: J. Shield Wallace, Fred E. Arnold
  • Patent number: 4532368
    Abstract: A process for making a mixture of meta- and para-alkylphenols by contacting a mixture of phenol, ortho-alkylphenol and an alkylating agent (e.g. olefins or lower alcohols) with a zeolite having a silica:alumina ratio of at least 12:1 under alkylating conditions to obtain a mixture of ortho-, meta- and para-alkylphenols and then separating at least part of the ortho-alkylphenol which is recycled to a subsequent alkylation process carried out in the same manner.
    Type: Grant
    Filed: February 1, 1984
    Date of Patent: July 30, 1985
    Assignee: Ethyl Corporation
    Inventors: Barry J. Swanson, Ronald L. Shubkin
  • Patent number: 4528407
    Abstract: An improved catalytic process for selectively ortho-alkylating a phenolic compound which comprises reacting a phenolic compound with an alcohol, optionally in the presence of water, and a catalyst composite consisting essentially of the calcination residue obtained from heating an admixture of magnesium carbonate and/or magnesium hydroxide and a manganese compound.
    Type: Grant
    Filed: October 26, 1981
    Date of Patent: July 9, 1985
    Assignee: General Electric Company
    Inventors: William E. Smith, Richard A. Battista
  • Patent number: 4517389
    Abstract: By flowing a gaseous stream containing methanol and a phenol through a fluidized bed of particles of a highly attrition resistant catalyst comprising 10 to 80% by weight of silica and 90 to 20% by weight of a metal oxide supported on the silica and have been calcined at 500.degree. to 900.degree. C., the ortho position of the phenol is methylated with high selectivity, whereby various useful ortho-methylated phenol derivatives can be advantageously obtained.
    Type: Grant
    Filed: August 8, 1983
    Date of Patent: May 14, 1985
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Tsutomu Katsumata, Masahisa Yokota
  • Patent number: 4489212
    Abstract: Arenes are reacted with allyl chloride to produce allylarenes and 2-chloropropyl- or propenylarenes using a catalyst comprising a metal oxide substrate having tantalum (V) halide/oxide bound to the surface of the substrate.
    Type: Grant
    Filed: October 25, 1983
    Date of Patent: December 18, 1984
    Assignee: Shell Oil Company
    Inventor: Thomas H. Johnson
  • Patent number: 4484011
    Abstract: The process for preparing 4-isopropylphenol (4-IPP) from 2-isopropylphenol (2-IPP) comprising contacting phenol with 2-IPP in the presence of a catalyst system selected from: (1) the combination of sulfuric acid on comminuted acid clay and a molecular sieve; and (2) trifluoromethane sulfonic acid (TFMSA); at a temperature of from about 90.degree. C. to about 250.degree. C., preferably from about 110.degree. C. to about 200.degree. C., wherein the initial mole ratio of phenol/2-IPP is from about 6 to about 2, preferably from about 4 to about 2.5, for a sufficient period to give a mole ratio of 4-IPP/2-IPP in the reaction system of from about 0.6 to about 1.5, and preferably from about 0.8 to about 1.2, without significant meta-isopropylphenol formation, i.e., less than about 10 mole %. In the isolation procedure, distillation separates the reaction mixture into phenol, 2-IPP, and 4-IPP.
    Type: Grant
    Filed: December 2, 1983
    Date of Patent: November 20, 1984
    Assignee: Eastman Kodak Company
    Inventor: Dale E. Van Sickle
  • Patent number: 4476330
    Abstract: Conversion, e.g. dehydration of aliphatic organic oxygenates having up to about 6 carbon atoms by contact with a crystalline aluminosilicate zeolite, preferably ZSM-5, having a silica to alumina ratio substantially greater than 10, at a temperature of about 70.degree. to 1400.degree. F., depending upon the exact nature of the reactant and product.
    Type: Grant
    Filed: August 18, 1981
    Date of Patent: October 9, 1984
    Assignee: Mobil Oil Corporation
    Inventors: George T. Kerr, Charles J. Plank, Edward J. Rosinski
  • Patent number: 4476329
    Abstract: A method is provided for producing o-cresol by simultaneously alkylating phenol with methanol and transalkylating 2,6-xylenol with phenol in the same reactor.
    Type: Grant
    Filed: April 4, 1983
    Date of Patent: October 9, 1984
    Assignee: General Electric Company
    Inventors: Gregory R. Chambers, John J. Talley
  • Patent number: 4471149
    Abstract: A phenol is ortho-alkylated by reaction with an alkanol in the presence of a catalyst comprising at least 92% w/w, calculated as Fe.sub.2 O.sub.3, of an oxide of iron, and at least one other metal oxide. By way of example, phenol can thus be converted to o-cresol and/or 2,6-xylenol.
    Type: Grant
    Filed: May 11, 1983
    Date of Patent: September 11, 1984
    Assignee: Croda Synthetic Chemicals Limited
    Inventors: Kenneth A. Adey, Frank S. Yates, John H. Young
  • Patent number: 4458031
    Abstract: Disclosed are a catalyst comprising a magnesium-containing moiety, a method for preparing the catalyst, and a process for the vapor phase ortho-alkylation of phenols in the presence of the catalyst.
    Type: Grant
    Filed: March 9, 1982
    Date of Patent: July 3, 1984
    Assignee: General Electric Company
    Inventors: Richard A. Battista, James G. Bennett, Jr., John J. Kokoszka
  • Patent number: 4454357
    Abstract: A process for producing o-methylated phenols useful as raw materials for resins and medicines in high yields comprising reacting methanol with phenols in the presence of a catalyst containing at least one compound selected from the group consisting of (1) magnesium oxide, manganese oxide and iron oxide which are all pre-treated with phenols and (2) magnesium phenolate.
    Type: Grant
    Filed: August 26, 1982
    Date of Patent: June 12, 1984
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasuhiko Inoue, Tadao Nishizaki, Satoshi Taguchi
  • Patent number: 4429171
    Abstract: Manufacture of orthomethylated phenol compounds by the reaction of phenol compounds having a hydrogen atom at the ortho position and methanol is accomplished advantageously by a method which effects the reaction by use of a catalyst comprising (A) iron oxide, (B) indium oxide, and (C) at least one member selected from the group consisting of chromium oxide and silicon oxide. According to this method, the reaction permits the orthomethylated phenol compound to be produced in high yields for a long time because of the catalyst's excellent activity-retaining property. Since the ortho-position selectivity and the utilization ratio of methanol are high and, consequently, the utilization efficiency of raw materials is high, the method of this invention produces the orthomethylated phenol compound with high efficiency from the phenol compounds.
    Type: Grant
    Filed: November 10, 1981
    Date of Patent: January 31, 1984
    Assignee: Asahi-Dow Limited
    Inventors: Tokio Sakurai, Kyosuke Komiya, Yoshihiko Mori, Yoshiharu Kitahama, Isamu Iwami
  • Patent number: 4418224
    Abstract: Ortho-alkylated phenols are prepared by reacting phenol unsubstituted in at least one ortho position with an alcohol in the presence of an ortho-alkylation catalyst consisting of magnesium carbonate, magnesium hydroxide or a mixture of both. The catalyst is used in the absence of a promoter compound and with or without polymeric binder.
    Type: Grant
    Filed: September 18, 1981
    Date of Patent: November 29, 1983
    Assignee: General Electric Company
    Inventors: James G. Bennett, Freddie L. Tungate
  • Patent number: 4418223
    Abstract: Phenols may be alkylated with monosubstituted or alpha, beta-disubstituted olefins over a silica alumina composite to afford 2,4,6-tri-sec-alkylphenols in high yields. The alkylation catalyst shows high activity and high selectivity to the 2,4,6-trialkylated product while minimizing oligomerization of the olefin. Composites containing from about 40 to about 60% silica, the remainder being alumina, are especially valuable.
    Type: Grant
    Filed: March 29, 1982
    Date of Patent: November 29, 1983
    Assignee: UOP Inc.
    Inventor: Bruce E. Firth
  • Patent number: 4400557
    Abstract: This invention relates to a process for reacting phenol, mono- and di-alkyl phenols having at least one free o-position with methanol and/or dimethyl ether in the gas phase to form o-substituted phenols in the presence of a catalyst of oxides of iron, vanadium, at least one oxide of boron, aluminum, titanium, zirconium, silicon, germanium, tin and lead, and at least one oxide of an alkali metal, alkaline-earth metal, lanthanum and manganese.
    Type: Grant
    Filed: May 14, 1981
    Date of Patent: August 23, 1983
    Assignee: Braunkohlen Kraftstoff Aktiengesellschaft
    Inventors: Max Fremery, Joachim Korff
  • Patent number: 4398048
    Abstract: Substantially improved yields of 2,4,6-trialkylphenols result from alkylating a mixture of phenol and 2,6-dialkylphenol, the latter being a by-product of the alkylation reaction. This results flows from an unexpected synergistic effect accompanying transalkylation. The continuous method of making 2,4,6-trialkylphenol based on this property affords the highly desirable trialkylated phenols in high yield.
    Type: Grant
    Filed: October 21, 1981
    Date of Patent: August 9, 1983
    Assignee: UOP Inc.
    Inventor: Bruce E. Firth
  • Patent number: 4391998
    Abstract: Phenol is catalytically alkylated with an isopropanol or propylene alkylating agent to form high yields of an isopropylphenol product enriched in the para-isomer of isopropylphenol. Such an alkylation process is carried out under catalytic alkylation conditions including a temperature of from about 200.degree. C. to 300.degree. C. and contact with a crystalline zeolite catalyst having a silica to alumina molar ratio of at least about 12 and a constraint index of about 1 to 12.
    Type: Grant
    Filed: October 21, 1981
    Date of Patent: July 5, 1983
    Assignee: Mobil Oil Corporation
    Inventor: Margaret M. Wu
  • Patent number: 4388478
    Abstract: This invention relates to a process for the selective ortho-alkylation of a phenolic compound having at least one ortho-positioned hydrogen atom by catalytically reacting the phenolic compound with an alcohol in the vapor phase. In this process, the reaction of the phenolic compound with the alcohol is carried out at a temperature of from 300.degree. to 550.degree. C. in the presence of a catalyst containing manganese oxide and one or more additives selected from group (A) consisting of germanium oxide, tin oxide and lead oxide, or a catalyst containing manganese oxide, one or more additives selected from the aforesaid group (A), and one or more additives selected from group (B) consisting of alkali metal oxides and alkaline earth metal oxides. The catalyst used in this invention exhibits not only excellent catalytic activity in the selective ortho-alkylation of phenols, continuous stability of the activity, good shapeability and good mechanical strength but also effective utilization of alcohols.
    Type: Grant
    Filed: October 30, 1981
    Date of Patent: June 14, 1983
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Akihide Kudoh, Motoo Kawamata, Kazushi Ohshima, Makoto Kotani, Takeshi Tsuda, Fukuichi Aoki
  • Patent number: 4386226
    Abstract: A phenol is ortho-alkylated by reaction with an alkanol in the presence of a catalyst comprising at least 87% w/w, calculated as Fe.sub.2 O.sub.3, of an oxide of iron, and at least one other metal oxide, in which the other metal is selected from As, Cd, Co, Hg, In, Ni, Pb, lanthanide rare earths, Sc, Sn, Ti and Zr. By way of example, phenol can thus be converted to o-cresol and/or 2,6-xylenol.
    Type: Grant
    Filed: October 5, 1981
    Date of Patent: May 31, 1983
    Assignee: Croda Synthetic Chemicals Limited
    Inventors: Kenneth A. Adey, Frank S. Yates, John H. Young
  • Patent number: 4361709
    Abstract: A process for the production of alkyl phenols having at least one o-alkyl radical comprising catalytically reacting a phenolic compound having at least one o-positioned hydrogen atom with an alcohol in the vapor phase in the presence of a manganese oxide containing catalyst modified with a compound of at least one of the alkali metals.
    Type: Grant
    Filed: May 20, 1981
    Date of Patent: November 30, 1982
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Motoo Kawamata, Kazushi Ohshima, Mitsuo Onofusa, Akihide Kudoh, Makoto Kotani, Takeshi Tsuda
  • Patent number: 4329517
    Abstract: In a process for producing a mono- or di-ortho-methyl-substituted phenol which comprises methylating a phenol having one or two ortho-hydrogens with methanol in the presence of a catalytic amount of a catalyst comprising a major proportion of an oxide of iron as a first component (A) and a minor proportion of at least one oxide of metal other than iron as a second component (B), the improvement wherein said metal other than iron in component (B) is a metal selected from the group consisting of Ga, Ge, Y, Nb, Hf, Bi and Ta; and a catalyst used therefor.
    Type: Grant
    Filed: May 14, 1980
    Date of Patent: May 11, 1982
    Assignee: Mitsui Petrochemical Industries Ltd.
    Inventors: Katsuo Taniguchi, Kazunori Takahata, Yoshiaki An-Nen
  • Patent number: 4323715
    Abstract: Mono-tertiary butylhydroquinone may be prepared in a continuous method of operation by reacting hydroquinone with isobutylene in the presence of an acidic alumina catalyst. The alkylation is effected in a reaction medium which comprises an ether, and particularly a polyether such as the dimethyl ether of triethylene glycol.
    Type: Grant
    Filed: November 20, 1980
    Date of Patent: April 6, 1982
    Assignee: UOP Inc.
    Inventors: Dusan J. Engel, Thomas P. Malloy
  • Patent number: 4322566
    Abstract: Amorphorus titanium, uranium, chromium ions and zirconium together with sulfate ions are effective promoters for magnesium oxide catalysts. These catalysts are active for the ortho methylation of phenols in the vapor phase to yield 2,6-xylenol.
    Type: Grant
    Filed: November 3, 1980
    Date of Patent: March 30, 1982
    Assignee: Conoco Inc.
    Inventor: Bruce E. Leach
  • Patent number: 4283573
    Abstract: A method for producing long chain-length alkylphenols with preferential production of para-alkylphenols and placement of the phenolic moiety at the #2 position on the alkyl chain. The reaction is carried out in the presence of crystalline zeolites having a major pore dimension of about six to seven angstrom units.
    Type: Grant
    Filed: November 20, 1979
    Date of Patent: August 11, 1981
    Assignee: Mobil Oil Corporation
    Inventor: Lewis B. Young
  • Patent number: 4283574
    Abstract: Phenol is methylated over an alumina catalyst using methanol, and the reaction product therefrom is combined with additional methanol over a promoted magnesium oxide catalyst. Major reaction products are ortho-cresol, 2,6-xylenol and 2,3,6-trimethylphenol. The promoted magnesium oxide catalyst contains metal promoters selected from the group consisting of titanium, chromium, and uranium together with sulfate ions.
    Type: Grant
    Filed: January 28, 1980
    Date of Patent: August 11, 1981
    Assignee: Conoco, Inc.
    Inventor: Bruce E. Leach
  • Patent number: 4275249
    Abstract: A process for introducing a plurality of alkyl groups into the aromatic ring of a hydroxy-substituted aromatic compound comprises contacting said aromatic compound with an olefin in the presence of alumina or halided alumina as catalyst and recovering the product. When said aromatic compound is phenol, said olefin is isobutylene, and said catalyst is fluorided or chlorided alumina, 2,4-di-t-butylphenol is formed with superior selectivity.
    Type: Grant
    Filed: November 30, 1979
    Date of Patent: June 23, 1981
    Assignee: UOP Inc.
    Inventor: Bruce E. Firth
  • Patent number: 4260833
    Abstract: A process for introducing a plurality of alkyl groups into the aromatic ring of a hydroxy-substituted aromatic compound comprises contacting said aromatic compound with an olefin in the presence of a lithiated alumina as catalyst and recovering the product. When said aromatic compound is phenol, said olefin is iso-butylene, and said catalyst is lithiated alumina, 2,4-di-t-butylphenol is formed with superior selectivity.
    Type: Grant
    Filed: November 30, 1979
    Date of Patent: April 7, 1981
    Assignee: UOP Inc.
    Inventor: Bruce E. Firth
  • Patent number: 4232176
    Abstract: Method of removing aluminum-containing catalyst from phenol alkylation products comprises treating phenol alkylation products with water at a temperature of 165.degree.-250.degree. C., with water being in molar excess to aluminum in a range of 3-20. The resulting residue of meta-aluminate is easily separated by filtration.The present invention allows eliminating constant control of aluminum content in alkylation products, easily removing the catalyst therefrom and eliminating the loss of phenol alkylation products.
    Type: Grant
    Filed: June 14, 1976
    Date of Patent: November 4, 1980
    Inventors: Engel R. Adigamov, Yakov A. Gurvich, Alexandr G. Liakumovich, Igor J. Logutov, Jury I. Michurov, Alexei S. Polenov, Vladimir A. Yanshevsky
  • Patent number: 4227023
    Abstract: This invention relates to a process for the selective ortho-alkylation of a phenolic compound having at least one ortho-positioned a hydrogen atom by catalytically reacting the phenolic compound with an alcohol in the vapor phase. In this process, the reaction of the phenolic compound with the alcohol is carried out at a temperature of from 300.degree. to 550.degree. C. in the presence of a mixed oxide catalyst of manganese, silicon, and one or more additives selected from the group consisting of magnesium oxide, calcium oxide, strontium oxide, and barium oxide. The catalyst used in this invention exhibits not only excellent catalytic activity in the selective ortho-alkylation of phenols but also continuous stability of the activity, good shapability, and good mechanical strength.
    Type: Grant
    Filed: December 4, 1978
    Date of Patent: October 7, 1980
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Motoo Kawamata, Tadamitsu Kiyoura, Kazushi Ohshima, Yasuo Kogure, Akihide Kudoh, Makoto Kotani
  • Patent number: 4225732
    Abstract: The process of the invention provides a method for the selective ortho-alkylation of a phenolic compound with a lower alkane in the presence of a supported nickel oxide catalyst.
    Type: Grant
    Filed: December 22, 1977
    Date of Patent: September 30, 1980
    Assignee: General Electric Company
    Inventor: John E. Dabrowski
  • Patent number: 4208537
    Abstract: The selective alkylation of a phenolic compound having a hydrogen atom in at least one of the ortho positions is achieved by reacting the phenolic compound with an alcohol in the vapor phase in the presence of a catalyst containing mixed oxides of chromium and tin. The catalyst can additionally contain iron oxide, sulfate radical, or a combination thereof.
    Type: Grant
    Filed: November 27, 1978
    Date of Patent: June 17, 1980
    Assignee: Mitsui Toatsu Chemicals Incorporated
    Inventors: Motoo Kawamata, Kazushi Ohshima, Akihide Kudoh, Makoto Kotani
  • Patent number: 4108909
    Abstract: A method for the production of n-alkylated cresylic acids such as n-hexyl resorcinol by direct alkylation of a cresylic acid such as resorcinol under liquid phase conditions.
    Type: Grant
    Filed: November 18, 1976
    Date of Patent: August 22, 1978
    Assignee: Continental Oil Company
    Inventors: Bruce Eugene Leach, Charles M. Starks