Preparing By Reduction Or Dehydrogenation (e.g., By Hydrogenation, Etc.) Patents (Class 568/799)
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Patent number: 4475001Abstract: Ortho- or para-monoalkylated phenols or 2,4- or 2,6-dialkylphenols can be produced from phenolic compounds in good yields and in the absence of isomers. The starting phenol which has at least two available ortho or para positions unsubstituted is converted to a t-alkylated phenol having at least one ortho or para position unsubstituted. The desired t-alkylated phenolic compound is reacted with an aldehyde having one to four carbon atoms and a secondary aliphatic or alicyclic amine. The reaction is conducted in the liquid phase with a stoichiometric amount of the phenolic compound and stoichiometric or excess of stoichiometric amounts of the aldehyde and the secondary amine. The reaction is conducted at a temperature in the range of about 0.degree. C., to about 100.degree. C. and the reaction produces an aminoalkylated t-alkylated phenol. The aminoalkylated phenol is contacted with hydrogen in the presence of a metal catalyst at a temperature of about 100.degree. C. to about 175.degree. C.Type: GrantFiled: March 17, 1983Date of Patent: October 2, 1984Assignee: Koppers Company, Inc.Inventor: Gerd Leston
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Patent number: 4453025Abstract: Isophorone is converted to 3,5-xylenol in the vapor phase in the presence of a heterogeneous catalyst comprising a particular combination of multiple rare earth metals on an alumina support or one or more rare earth metals in combination with one or more transition metals and/or one or more alkali or alkaline earth metals. Particularly good results are obtained with a catalyst comprising a naturally-occurring mixture of rare earth metals known as didymium in combination with potassium and cobalt promoters.Type: GrantFiled: November 23, 1982Date of Patent: June 5, 1984Assignee: Shell Oil CompanyInventors: Antonius J. C. Van Seters, Freddy Wattimena
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Patent number: 4431849Abstract: A process for preparing a methyl phenol from a tertiary hydroperoxide in an oxidation product of an alkylbenzene of the general structural formula ##STR1## wherein R is a secondary alkyl group and n is an integer of 1 to 3, which comprises hydrogenating the oxidation product in the presence of a mineral acid medium with a hydrogenation catalyst.Type: GrantFiled: October 21, 1981Date of Patent: February 14, 1984Assignee: The Goodyear Tire & Rubber CompanyInventor: Howard A. Colvin
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Patent number: 4431850Abstract: A process for thermal dealkylation of alkylated phenols feedstocks, which comprises reacting a feed mixture containing mono and poly-alkylated phenols and gaseous hydrogen at temperature ranging from about 900.degree. to about 1100.degree. F. at hydrogen partial pressure of 300 to 1600 psig, and space velocity of 0.2 to 3.0 volume feed/hr/volume of reactor to produce a phenol-containing product at increased selectivity and yield of phenol. For feedstream mixtures containing more than about 10 W % phenols, a prior distillation step is preferably used to remove the excessive phenol as product and thus avoid undesired dehydroxylation reactions in the hydrodealkylation step to which the feed phenol concentration is usually about 2-8 W %.Type: GrantFiled: November 9, 1981Date of Patent: February 14, 1984Assignee: HRI, Inc.Inventors: Derk T. A. Huibers, Cheng-Yih Jenq
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Patent number: 4420644Abstract: A lignin-containing feed material in particulate form is mixed with a process-derived slurrying oil and fed into an ebullated catalyst bed hydrocracking reactor. Reaction conditions are maintained at 650.degree.-850.degree. F. temperature, 500-2500 psig hydrogen partial pressure and space velocity of 1.0-10 wt. lignin/hr./wt. catalyst. The reaction products are phase separated to recover hydrogen and slurrying oil, and the resulting liquid stream is passed to a thermal hydrodealkylation step. The reacted stream is fractionated to produce phenol and benzene products, along with a heavy alkylated material which is recycled to the hydrodealkylation step to increase the yield of phenol and benzene.Type: GrantFiled: August 24, 1981Date of Patent: December 13, 1983Assignee: Hydrocarbon Research, Inc.Inventors: Derk T. A. Huibers, Hugh J. Parkhurst, Jr.
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Patent number: 4419529Abstract: A 2-alkylphenol is prepared by reduction of a 2-acylphenol in the presence of a metallic catalyst. The reaction is carried out at a temperature of 80.degree. to 200.degree. C. and under a pressure of 10 to 100 bars, and a base metal, in particular copper, is used as a catalyst. It is particularly advantageous to use the catalyst in combination with a support. The hydrogenation of the acylphenol is advantageously carried out in the presence of an inert solvent. The process can be carried out continuously or discontinuously. The alkylphenols obtained are suitable for use in the synthesis of active substances having biocidal properties.Type: GrantFiled: March 3, 1982Date of Patent: December 6, 1983Assignee: Riedel-de Haen AktiengesellschaftInventor: Arthur Steinmetz
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Patent number: 4417076Abstract: A catalyst for dehydrogenation of oxygen-containing derivatives of the cyclohexane series of the general formula: ##STR1## wherein R.sub.1 is hydrogen or a C.sub.1 -C.sub.4 alkyl;R.sub.2 and R.sub.3 are radicals having the same or different meanings: --H, --OH, .dbd.O, provided that R.sub.2 and R.sub.3 are not simultaneously hydrogen and R.sub.1, R.sub.2 and R.sub.3 are attached to different carbon atoms of the cycle,into corresponding cyclic ketones and/or phenols containing the following components, percent by weight:______________________________________ nickel 15 to 55 promotor-germanium and/or lead 0.2 to 8.0 inert carrier 84.8 to 37.0 ______________________________________and an atomic ratio of nickel to the promotor is within the range of from 15:1 to 410:1 respectively. The catalyst can additionally contain a salt of an alkali metal and a mineral acid in an amount of from 0.01 to 1.0% by weight.Type: GrantFiled: August 9, 1982Date of Patent: November 22, 1983Inventors: Alexandr Y. Rozovsky, Valentin D. Stytsenko, Svetlana A. Nizova, Petr S. Belov, Alexandr J. Dyakonov
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Patent number: 4415477Abstract: The herein-proposed catalyst for dehydrogenation oxygen-containing derivatives of the cyclohexane series having the following general formula ##STR1## where R.sub.1 is either hydrogen or alkyl C.sub.1 -C.sub.4,R.sub.2 and R.sub.3 are radicals having either the same or different values --H, --OH, .dbd.O, provided that R.sub.2 and R.sub.3 are not hydrogen atoms both at a time,R.sub.1, R.sub.2, R.sub.3 being linked to different carbon atoms of the ring to form the corresponding cyclic ketones and/or phenols, comprises the following components (wt. %):nickel--15 to 55tin--0.2 to 1.95inert carrier--84.8 to 43.05,while the atomic ratio of nickel and tin lies within 15:1 and 410:1, respectively, and may contain additionally an alkali salt of a mineral acid in an amount of 0.01 to 1.0 wt. %.Type: GrantFiled: December 22, 1980Date of Patent: November 15, 1983Inventors: Alexandr Y. Rozovsky, Valentin D. Stytsenko, Svetlana A. Nizova, Petr S. Belov, Alexandr J. Dyakonov
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Patent number: 4346240Abstract: A novel class of heterogeneous catalysts, containing Group VIII transition metals in combination with alkali organic compounds is prepared, such as potassium naphthalene on ruthenium on carbon. The catalysts are useful as heterogeneous catalysts in the hydrogenation of carboxylic acid esters. A process for producing the materials is described. The catalysts permit the process of the hydrogenation of carboxylic acid esters to primary alcohols to be conducted with the ester in the liquid phase at a temperature not exceeding about 150.degree. C. with high selectivity. Catalysts of Group VIII transition metals and alkali metal on carbon are also useful in such processes.Type: GrantFiled: September 29, 1981Date of Patent: August 24, 1982Assignee: Allied CorporationInventors: Roger A. Grey, Guido P. Pez
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Patent number: 4319054Abstract: There is disclosed a process for producing pyrogallol by dehydrogenation of cyclohexane-1,2,3-triol in the presence of a platinum group metal catalyst in an inert gas stream. The catalyst contains, as modifier, (a) at least one alkali metal salt and/or (b) at least one member selected from the group consisting of gold, tellurium, silver, arsenic, selenium, indium, antimony, bismuth, copper and zinc, with the Pd-Te catalyst being preferred. The catalyst ingredients are supported on a carrier. The process gives high selectivity of pyrogallol.Type: GrantFiled: December 8, 1980Date of Patent: March 9, 1982Assignee: Mitsubishi Chemical Industries LimitedInventors: Takao Maki, Kenji Murayama
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Patent number: 4273944Abstract: A novel method for the selective preparation of the cis isomer of a disubstituted ethylenically unsaturated compound is proposed in which a disubstituted acetylenically unsaturated compound is partially hydrogenated in the presence of, in place of a conventional Lindlar catalyst or a combination of a Lindlar catalyst with an amine, a palladium catalyst borne on an alumina carrier in combination with water and a hydroxide or a basic salt of an alkali metal or an alkaline earth metal. The inventive method is advantageous over conventional methods by the unnecessity of the use of an amine compound which is definitely undesirable when the product is directed to the application in perfumery and by the easiness in handling of the catalyst which can be easily separated from the reaction mixture after completion of the reaction.Type: GrantFiled: October 30, 1979Date of Patent: June 16, 1981Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Shigeru Ohno, Haruya Tezuka, Toshinobu Ishihara
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Patent number: 4271091Abstract: Cyclohexanone and/or cyclohexanol can be oxidized in the vapor phase to phenol by contacting the cyclohexanone and/or cyclohexanol with a suitable oxidation catalyst in the presence of molecular oxygen. Suitable catalysts are solids comprising Mo, W, Sb and/or V oxides or complexes thereof. The catalysts may be promoted with additional elements.Type: GrantFiled: June 17, 1978Date of Patent: June 2, 1981Assignee: Standard Oil CompanyInventors: Robert K. Grasselli, Dev D. Suresh
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Patent number: 4258268Abstract: At least one of a polycyclic phenol, a polycyclic alcohol and a polycyclic ketone is produced under hydrogenation conditions using a nickel oxide/manganese oxide/magnesium oxide catalyst by subjecting at least one of a monocyclic ketone, a monocyclic alcohol and a monocyclic phenol to said conditions and said catalyst.Type: GrantFiled: August 27, 1979Date of Patent: March 24, 1981Assignee: Phillips Petroleum CompanyInventor: Geir Bjornson
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Patent number: 4258221Abstract: Alkylenebisphenols are converted or cleaved to phenols and alkyl- and/or alkenyl-substituted phenols in good yields by contacting with hydrogen in the presence of a nickel oxide/manganese oxide/metal oxide supported catalyst. In a specific embodiment, bisphenol A is converted to isopropylphenol at high selectivity and high conversion by contacting with hydrogen in the presence of a nickel oxide/manganese oxide/magnesium oxide catalyst.Type: GrantFiled: April 11, 1979Date of Patent: March 24, 1981Assignee: Phillips Petroleum CompanyInventors: Ronald D. Knudsen, Geir Bjornson
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Patent number: 4225414Abstract: A process is disclosed for hydrocracking coal or other carbonaceous material to produce various aromatic hydrocarbons including benzene, toluene, xylene, ethylbenzene, phenol and cresols in variable relative concentrations while maintaining a near constant maximum temperature. Variations in relative aromatic concentrations are achieved by changing the kinetic severity of the hydrocracking reaction by altering the temperature profile up to and quenching from the final hydrocracking temperature. The relative concentration of benzene to the alkyl and hydroxyl aromatics is increased by imposing increased kinetic severity above that corresponding to constant heating rate followed by immediate quenching at about the same rate to below the temperature at which dehydroxylation and dealkylation reactions appreciably occur.Type: GrantFiled: February 26, 1979Date of Patent: September 30, 1980Assignee: The United States of America as represented by the United States Department of EnergyInventor: Dennis A. Duncan
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Patent number: 4215229Abstract: Ortho- and para-monoalkylated phenols and 2,4- and 2,6-dialkylphenols can be produced from phenolic compounds in good yields. The phenolic compound is reacted with an aldehyde having one to ten carbon atoms and a secondary aliphatic amine having a basic dissociation constant, pK.sub.b, of less than about 3.6 measured at 25.degree. C. The reaction is conducted in the liquid phase with at least a stoichiometric amount of the phenolic compound, the aldehyde and the secondary amine, or with an excess of the phenolic compound with the stoichiometric amounts of the aldehyde and the secondary amine. The reaction is conducted at a temperature in the range of around 0.degree. C. to about 25.degree. C., and the reaction produces an aminoalkylated phenol. The aminoalkylated phenol is contacted with hydrogen in the presence of a metal catalyst at a temperature of about 120.degree. C. to about 140.degree. C.Type: GrantFiled: June 15, 1978Date of Patent: July 29, 1980Assignee: Koppers Company, Inc.Inventor: Nicholas P. Greco
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Patent number: 4188497Abstract: A process is described for the removal of halogen residues from a reaction mixture containing 3,5-xylenol and halogen residues, produced via the heating of isophorone at a temperature of about 450.degree. C. to about 650.degree. C. in the presence of a homogeneous halogen-containing catalyst, said removal being accomplished by contacting the reaction mixture with a metal selected from the group consisting of zinc, iron, magnesium, cadmium, cobalt and nickel.Type: GrantFiled: January 25, 1978Date of Patent: February 12, 1980Assignee: Shell Oil CompanyInventors: Leendert Huizer, Dirk J. Van Namen, Pieter J. D. Oranje
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Patent number: 4146581Abstract: A process for the manufacture of higher ketones by reacting an aldehyde with a ketone in the presence of hydrogen over a catalyst system which contains, firstly, oxides or salts of the rare earth metals and, secondly, metals of group VIII of the periodic table of the elements. The process gives numerous higher ketones, required, for example, as solvents for surface coatings, or as scents, with high conversions and good selectivities, and therefore more simply and more economically than conventional methods.Type: GrantFiled: March 30, 1977Date of Patent: March 27, 1979Assignee: BASF AktiengesellschaftInventors: Axel Nissen, Otto Woerz, Gerd Heilen, Werner Fliege, Arnold Wittwer
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Patent number: 4128728Abstract: A process for the production of 2,3,6-trimethylphenol in which diethyl ketone is reacted in the presence of a basic reagent with crotonaldehyde or methyl vinyl ketone (or a compound which in the presence of a basic reagent is converted into crotonaldehyde or methyl vinyl ketone) and the 2,5,6-trimethyl-2-cyclohexen-1-one or 2,3,6-trimethyl-2-cyclohexen-1-one formed is dehydrogenated.Type: GrantFiled: March 4, 1969Date of Patent: December 5, 1978Assignee: Badische Anilin- & Soda-Fabrik AktiengesellschaftInventors: Lothar Arnold, Heinrich Pasedach, Horst Pommer
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Patent number: 4117244Abstract: A method of producing 2,6-ditertbutyl-4-methylphenol comprises hydrogenolysis of N,N-dimethyl-(3,5-ditertbutyl-4-hydroxybenzyl)-amine in the presence of a fused catalyst, containing Ni, Al, Ti, in the medium of a solvent, namely 2,6-ditertbutyl-4-methylphenol solvent medium.The invention allows improving the quality of the product and obtaining it with a high yield.Type: GrantFiled: June 11, 1976Date of Patent: September 26, 1978Inventors: Ivan Egorovich Abramov, Felix Borisovich Gershanov, Vladimir Romanovich Dolidze, Nina Vasilievna Zakharova, Alexandr Grigorievich Liakumovich, Jury Ivanovich Michurov, Vasily Dmitrievich Popov, Grigory Iosifovich Rutman, Zoya Stepanovna Shalimova
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Patent number: 4094909Abstract: A process for the decarboxylation-oxidation of a substituted or unsubstituted benzoic acid compound including heating the benzoic acid compound and forming a liquid phase, passing molecular oxygen in the presence of a copper catalyst through the hot liquid phase to form a substituted or unsubstituted phenol compound and a viscous tar-like product, and hydrogenating the viscous tar-like compound to form at least one low-boiling organic compound.Type: GrantFiled: February 28, 1977Date of Patent: June 13, 1978Assignee: Stamicarbon, B.V.Inventor: Johan P. H. Von den Hoff
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Patent number: 4088666Abstract: This invention relates to the use of chelated lithium hydridoaluminates or hydridoborates in hydride reductions of organic and inorganic substrates. Novel or improved reductions are obtained at increased rates or selectivities in hydrocarbon media.Type: GrantFiled: May 17, 1977Date of Patent: May 9, 1978Assignee: Exxon Research & Engineering Co.Inventors: Arthur W. Langer, Jr., Thomas A. Whitney
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Patent number: 4088700Abstract: An improved process for the hydrogenolysis of acetals and ketals of organic hydrocarbons is described. The improvement resides in using a catalyst system including a halide of a Group III A element and a supported platinum or rhodium hydrogenation catalyst or combination thereof, thus enabling the process to be practiced at a temperature of from about -15.degree. C. to about 125.degree. C. and a pressure of from about 50 psia to about 2000 psia. The preferred Group III A halides are boron trifluoride and aluminum trichloride.Type: GrantFiled: September 27, 1976Date of Patent: May 9, 1978Assignee: Texaco Development CorporationInventor: Lewis W. Watts, Jr.