Heavy Metal Or Aluminum Containing Catalyst Patents (Class 568/794)
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Patent number: 4540833Abstract: 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: GrantFiled: March 21, 1984Date of Patent: September 10, 1985Assignee: The United States of America as represented by the Secretary of the Air ForceInventors: J. Shield Wallace, Fred E. Arnold
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Patent number: 4532368Abstract: 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: GrantFiled: February 1, 1984Date of Patent: July 30, 1985Assignee: Ethyl CorporationInventors: Barry J. Swanson, Ronald L. Shubkin
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Patent number: 4528407Abstract: 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: GrantFiled: October 26, 1981Date of Patent: July 9, 1985Assignee: General Electric CompanyInventors: William E. Smith, Richard A. Battista
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Patent number: 4517389Abstract: 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: GrantFiled: August 8, 1983Date of Patent: May 14, 1985Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Tsutomu Katsumata, Masahisa Yokota
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Patent number: 4489212Abstract: 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: GrantFiled: October 25, 1983Date of Patent: December 18, 1984Assignee: Shell Oil CompanyInventor: Thomas H. Johnson
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Patent number: 4484011Abstract: 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: GrantFiled: December 2, 1983Date of Patent: November 20, 1984Assignee: Eastman Kodak CompanyInventor: Dale E. Van Sickle
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Patent number: 4476329Abstract: 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: GrantFiled: April 4, 1983Date of Patent: October 9, 1984Assignee: General Electric CompanyInventors: Gregory R. Chambers, John J. Talley
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Patent number: 4476330Abstract: 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: GrantFiled: August 18, 1981Date of Patent: October 9, 1984Assignee: Mobil Oil CorporationInventors: George T. Kerr, Charles J. Plank, Edward J. Rosinski
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Patent number: 4471149Abstract: 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: GrantFiled: May 11, 1983Date of Patent: September 11, 1984Assignee: Croda Synthetic Chemicals LimitedInventors: Kenneth A. Adey, Frank S. Yates, John H. Young
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Patent number: 4458031Abstract: 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: GrantFiled: March 9, 1982Date of Patent: July 3, 1984Assignee: General Electric CompanyInventors: Richard A. Battista, James G. Bennett, Jr., John J. Kokoszka
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Patent number: 4454357Abstract: 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: GrantFiled: August 26, 1982Date of Patent: June 12, 1984Assignee: Sumitomo Chemical Company, LimitedInventors: Yasuhiko Inoue, Tadao Nishizaki, Satoshi Taguchi
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Patent number: 4429171Abstract: 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: GrantFiled: November 10, 1981Date of Patent: January 31, 1984Assignee: Asahi-Dow LimitedInventors: Tokio Sakurai, Kyosuke Komiya, Yoshihiko Mori, Yoshiharu Kitahama, Isamu Iwami
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Patent number: 4418224Abstract: 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: GrantFiled: September 18, 1981Date of Patent: November 29, 1983Assignee: General Electric CompanyInventors: James G. Bennett, Freddie L. Tungate
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Patent number: 4418223Abstract: 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: GrantFiled: March 29, 1982Date of Patent: November 29, 1983Assignee: UOP Inc.Inventor: Bruce E. Firth
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Patent number: 4400557Abstract: 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: GrantFiled: May 14, 1981Date of Patent: August 23, 1983Assignee: Braunkohlen Kraftstoff AktiengesellschaftInventors: Max Fremery, Joachim Korff
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Patent number: 4398048Abstract: 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: GrantFiled: October 21, 1981Date of Patent: August 9, 1983Assignee: UOP Inc.Inventor: Bruce E. Firth
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Patent number: 4391998Abstract: 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: GrantFiled: October 21, 1981Date of Patent: July 5, 1983Assignee: Mobil Oil CorporationInventor: Margaret M. Wu
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Patent number: 4388478Abstract: 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: GrantFiled: October 30, 1981Date of Patent: June 14, 1983Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Akihide Kudoh, Motoo Kawamata, Kazushi Ohshima, Makoto Kotani, Takeshi Tsuda, Fukuichi Aoki
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Patent number: 4386226Abstract: 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: GrantFiled: October 5, 1981Date of Patent: May 31, 1983Assignee: Croda Synthetic Chemicals LimitedInventors: Kenneth A. Adey, Frank S. Yates, John H. Young
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Patent number: 4361709Abstract: 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: GrantFiled: May 20, 1981Date of Patent: November 30, 1982Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Motoo Kawamata, Kazushi Ohshima, Mitsuo Onofusa, Akihide Kudoh, Makoto Kotani, Takeshi Tsuda
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Patent number: 4329517Abstract: 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: GrantFiled: May 14, 1980Date of Patent: May 11, 1982Assignee: Mitsui Petrochemical Industries Ltd.Inventors: Katsuo Taniguchi, Kazunori Takahata, Yoshiaki An-Nen
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Patent number: 4323715Abstract: 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: GrantFiled: November 20, 1980Date of Patent: April 6, 1982Assignee: UOP Inc.Inventors: Dusan J. Engel, Thomas P. Malloy
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Patent number: 4322566Abstract: 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: GrantFiled: November 3, 1980Date of Patent: March 30, 1982Assignee: Conoco Inc.Inventor: Bruce E. Leach
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Patent number: 4283573Abstract: 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: GrantFiled: November 20, 1979Date of Patent: August 11, 1981Assignee: Mobil Oil CorporationInventor: Lewis B. Young
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Patent number: 4283574Abstract: 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: GrantFiled: January 28, 1980Date of Patent: August 11, 1981Assignee: Conoco, Inc.Inventor: Bruce E. Leach
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Patent number: 4275249Abstract: 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: GrantFiled: November 30, 1979Date of Patent: June 23, 1981Assignee: UOP Inc.Inventor: Bruce E. Firth
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Patent number: 4260833Abstract: 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: GrantFiled: November 30, 1979Date of Patent: April 7, 1981Assignee: UOP Inc.Inventor: Bruce E. Firth
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Patent number: 4232176Abstract: 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: GrantFiled: June 14, 1976Date of Patent: November 4, 1980Inventors: Engel R. Adigamov, Yakov A. Gurvich, Alexandr G. Liakumovich, Igor J. Logutov, Jury I. Michurov, Alexei S. Polenov, Vladimir A. Yanshevsky
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Patent number: 4227023Abstract: 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: GrantFiled: December 4, 1978Date of Patent: October 7, 1980Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Motoo Kawamata, Tadamitsu Kiyoura, Kazushi Ohshima, Yasuo Kogure, Akihide Kudoh, Makoto Kotani
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Patent number: 4225732Abstract: 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: GrantFiled: December 22, 1977Date of Patent: September 30, 1980Assignee: General Electric CompanyInventor: John E. Dabrowski
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Patent number: 4208537Abstract: 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: GrantFiled: November 27, 1978Date of Patent: June 17, 1980Assignee: Mitsui Toatsu Chemicals IncorporatedInventors: Motoo Kawamata, Kazushi Ohshima, Akihide Kudoh, Makoto Kotani
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Patent number: 4108909Abstract: 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: GrantFiled: November 18, 1976Date of Patent: August 22, 1978Assignee: Continental Oil CompanyInventors: Bruce Eugene Leach, Charles M. Starks