Preparing By Oxidation Patents (Class 568/910)
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Patent number: 4910349Abstract: Tertiary butyl alcohol is prepared by the catalytic decomposition of tertiary butyl hydroperoxide, preferably in solution in tertiary butyl alcohol, in the presence of a metal phthalocyanine catalyst promoted with a rhenium compound, such as a phthalocyanine of a metal of Group IB, Group VIIB or Group VIIIB of the Periodic Table (e.g., chloroferric phthalocyanine and rhenium heptoxide-p-dioxane or oxotrichloro-bis-(triphenylphosphine) rhenium V).Type: GrantFiled: September 8, 1987Date of Patent: March 20, 1990Assignee: Texaco Inc.Inventors: John R. Sanderson, John F. Knifton, Edward T. Marquis
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Patent number: 4900871Abstract: Hydrocarbons, and particularly lower molecular weight alkanes and cycloalkanes, may readily be oxidized with air or O.sub.2 to form such products as alcohols, ketones, and the like selectively high yields when there is employed as the catalyst a coordination complex containing an iron center and a halogenated ligand having the structure ##STR1## where Fe is iron; " .circle. " is a ligand; X is a halogen substituent of the ligand; and A is an anion.Type: GrantFiled: June 26, 1987Date of Patent: February 13, 1990Assignee: Sun Refining and Marketing CompanyInventors: Paul E. Ellis, Jr., James E. Lyons, Harry K. Myers, Jr.
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Patent number: 4898989Abstract: Alkanes are catalytically oxidized using site-specific framework substituted heteropolyacid or a polyoxoanion thereof.Type: GrantFiled: October 7, 1988Date of Patent: February 6, 1990Assignee: Sun Refining and Marketing CompanyInventors: Paul E. Ellis, Jr., James E. Lyons
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Patent number: 4895682Abstract: Hydrocarbons, and particularly lower molecular weight alkanes and cycloalkanes, may readily be oxidixed with air or O.sub.2 to form such products as alcohols, ketones, and the like selectively in high yields when there is employed as the catalyst a highly active azide-activated metal coordination complex having the structure ##STR1## where M is a transition metal; " " is a ligand; and X is azide. The invention is also directed to certain novel azide-activated metal coordination complex catalysts per se.Type: GrantFiled: January 2, 1987Date of Patent: January 23, 1990Assignee: Sun Refining and Marketing CopanyInventors: Paul E. Ellis, Jr., James E. Lyons, Harry K. Myers, Jr.
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Patent number: 4895680Abstract: Hydrocarbon, and particularly lower molecular weight alkanes and cycloalkanes, may readily be oxidized with air or O.sub.2 to form such products as alcohols, ketones, and the like in high yields when there is employed as the catalyst a highly active nitride-activated metal coordination complex having the structure ##STR1## where M is a transition metal; " " is a ligand; and X is a nitride. Certain dimeric forms of the above catalyst are also employed herein. It has also been discovered that Group IV through VIII transition metal nitrides are also highly effective oxidation catalysts for lower molecular weight hydrocarbons such as alkanes.Type: GrantFiled: January 2, 1987Date of Patent: January 23, 1990Assignee: Sun Refining and Marketing CompanyInventors: Paul E. Ellis, Jr., James E. Lyons, Harry K. Myers, Jr.
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Patent number: 4859798Abstract: Alkanes are oxidized in the liquid phase at relatively low temperatures using heteropolyacids or polyoxoanions promoted with azide or certain metals. Such azide catalysts are also part of the invention.Type: GrantFiled: June 24, 1988Date of Patent: August 22, 1989Assignee: Sun Refining and Marketing CompanyInventors: James E. Lyons, Paul E. Ellis, Jr., Harry K. Myers, Jr., George Suld, Wayne A. Langdale
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Patent number: 4803305Abstract: The oxidation of isobutane in the presence of a novel, soluble catalyst of the formula Fe.sub.3 O(Pivalate).sub.6 (MeOH).sub.3 Cl is disclosed. Tertiary-Butyl alcohol, tertiary-butyl hydroperoxide, and acetone are produced. A significant increase in isobutane conversion is obtained without a large decrease in selectivity to tertiary-butyl alcohol and tertiary-butyl hydroperoxide using a small amount of catalyst. Tertiary-butyl alcohol is useful as a gasoline additive and tertiary-butyl hydroperoxide is used for the production of propylene oxide. Acetone has a variety of uses as well.Type: GrantFiled: November 27, 1987Date of Patent: February 7, 1989Assignee: Texaco Inc.Inventors: John R. Sanderson, Edward T. Marquis, Jiang-Jen Lin
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Patent number: 4803187Abstract: Heteropolyacids or polyoxoanions promoted with azide, such as K.sub.6 PW.sub.11 VO.sub.40 N.sub.3, useful in the liquid phase oxidation of alkanes.Type: GrantFiled: July 20, 1987Date of Patent: February 7, 1989Assignee: Sun Refining and Marketing CompanyInventors: James E. Lyons, Paul E. Ellis, Jr., Harry K. Myers, Jr., George Suld, Wayne A. Langdale
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Patent number: 4801755Abstract: The oxidation of isobutane in the presence of a novel, soluble propylene glycol/vanadium catalyst is disclosed. Tertiary-butyl alcohol, tertiary-butyl hydroperoxide, and acetone are produced. A significant increase in isobutane conversion is obtained without a large decrease in selectivity to tertiary-butyl alcohol and tertiary-butyl hydroperoxide using a small amount of catalyst. Tertiary-butyl alcohol is useful as a gasoline additive and tertiary-butyl hydroperoxide is used for the production of propylene oxide. Acetone has a variety of uses as well.Type: GrantFiled: November 27, 1987Date of Patent: January 31, 1989Assignee: Texaco Inc.Inventors: John R. Sanderson, Edward T. Marquis
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Patent number: 4785134Abstract: A novel process for producing allyl alcohol and, more specifically, to a process which utilizes a molten nitrate salt catalyst.Type: GrantFiled: January 28, 1988Date of Patent: November 15, 1988Assignee: Olin CorporationInventor: B. Timothy Pennington
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Patent number: 4760210Abstract: Method and apparatus for partial oxidation of hydrocarbonaceous gases, wherein a hydrocarbonaceous gas is preheated, reacted with oxygen, and quenched by means of a rotating matrix comprising glassy ceramic fibers. Such a rotating matrix may be constructed and compartmented by a method and apparatus which utilizes the inherent tensile strength properties of the fibers to provide strength to the compartment walls. Such partial oxidation method and apparatus is especially useful in a direct, integrated process for the production of tert-butyl ethers, wherein the product of partially oxidizing methane and isobutane are caused to be methanol and isobutylene, which intermediates are directly recovered and combined to form methyl tert-butyl ether by method and apparatus of the invention. Furthermore, by-products of such partial oxidation may also be converted to useful tert-butyl ethers.Type: GrantFiled: December 21, 1984Date of Patent: July 26, 1988Inventor: Maxwell P. Sweeney
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Patent number: 4659829Abstract: The invention concerns peroxide complexes of metals complying with the general formula LnMXpY, wherein M is a metal selected from groups VIII, IB and VIIB, particularly cobalt, X is an anionic group, for example carboxylate, R is an alkyl, cycloalkyl or arylalkyl group, n=1 or 2, p=0 or 1 and n+p=2.L is a tridentated ligand from the group of 1,3 bis (2-pyridylimino) isoindolines.These complexes are obtained by reaction of a hydroperoxide ROOH with a complex of formula LnMXp. They can be used in oxidizing hydrocarbons to a mixture of alcohols and ketones, either as reactants or as catalysts.They are particularly useful to prepare tert-butanol by oxidation of isobutane in liquid phase, by means of an oxygen-containing gas such as air.Type: GrantFiled: January 31, 1985Date of Patent: April 21, 1987Assignee: Institut Francais du PetroleInventors: Lucien Saussine, Alain Robine, Hubert Mimoun
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Patent number: 4618732Abstract: A process of directly converting natural gas to methanol employs controlled oxidation. The reaction takes place in an inert reactor, i.e. one having internal surfaces which do not affect the reaction, in the absence of a catalyst. The natural gas is intimately mixed with air or oxygen prior to introduction of the mixed gases into the reactor. Reaction takes place at an elevated temperature of 300.degree. to 500.degree. C. and at an elevated pressure of 10 to 100 atmospheres. The percentage of oxygen in the mixture of reactant gases is kept below 20% by volume and is preferably 2 to 10% by volume. Apparatus for carrying out the method is also provided.Type: GrantFiled: May 20, 1985Date of Patent: October 21, 1986Inventors: Hyman D. Gesser, Norman R. Hunter, Lawrence Morton
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Patent number: 4609763Abstract: A process for the oxidation of alkanes or alkenes is described. The process uses a hydrocarbyl hydroperoxide as an oxidizing agent in combination with a ruthenium catalyst and optionally a hydrogen bromide or hydrobromide acid promoter. The products of the oxidation are alcohols, ketones or a mixture of both.Type: GrantFiled: September 3, 1985Date of Patent: September 2, 1986Assignee: The British Petroleum Company P.L.C.Inventors: Colin G. Griggs, Anthony R. Middleton
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Patent number: 4530826Abstract: In a process for producing chemical substances comprising steps of cooling, condensing and solvent-absorbing the reaction product gas having a high temperature formed in a reactor, an absorption type refrigerator or an absorption type heat pump is driven by using, as the driving source, a heat source having such a temperature as not to be advantageous for the heat exchange in the process, which heat source has been taken out of the steps of cooling the reaction product gas, condensing it or solvent-absorbing it to obtain a refrigerant or a hot water having a temperature higher than the temperature of the heat source, and the refrigerant or the hot water is used as a cooling source or a heating source in the steps comprised in said process for producing chemical substances.Type: GrantFiled: August 29, 1983Date of Patent: July 23, 1985Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hiroyuki Ohashi, Shoichi Miyamoto, Shigeru Kurihara
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Patent number: 4523043Abstract: Organosulfur compounds containing a C-S bond are decomposed by reaction with a reagent made from an alkali metal, a polyglycol or a monoalkyl ether thereof and oxygen, which effects decomposition by cleavage of the C-S bond.Type: GrantFiled: January 18, 1984Date of Patent: June 11, 1985Assignee: The Franklin InstituteInventors: Louis L. Pytlewski, Kenneth Krevitz, Arthur B. Smith
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Patent number: 4499301Abstract: Vapor phase process for the preparation of unsaturated aldehydes, carboxylic acids and mixtures thereof which comprises contacting a gaseous mixture of an open-chain olefin of from 3 to 8 carbon atoms, water and oxygen at an elevated temperature up to about 250.degree. with a solid catalyst comprising a catalytically effective amount of noble metal promoted by a solid acid consisting of mixed metal oxides.Type: GrantFiled: May 14, 1982Date of Patent: February 12, 1985Assignee: National Distillers and Chemical CorporationInventor: Jawad H. Murib
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Patent number: 4481373Abstract: The invention relates to a method for the manufacture of ketones which comprises oxidizing an n-olefin in the presence of a catalyst containing palladium, copper, a halogen, and at least one of specific tertiary amines.Type: GrantFiled: September 24, 1982Date of Patent: November 6, 1984Assignee: Toa Nenryo Kogyo Kabushiki KaishaInventors: Yoshiharu Okumura, Tadamori Sakakibara, Katsumi Kaneko
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Patent number: 4472314Abstract: Mixed oxides of bismuth with other metals of the perovskite structure and having vacant lattice sites in the same lattice positions occupied by bismuth are disclosed as partial oxidation and ammoxidation catalysts. Such oxides are used as catalysts in the improved method of oxidizing an acyclic hydrocarbon of 1-10 carbons having at most one olefinic unsaturation by reacting the acyclic hydrocarbon in the vapor phase with oxygen in the presence of the solid catalyst to form products having carbon, hydrogen and oxygen.Type: GrantFiled: May 27, 1980Date of Patent: September 18, 1984Assignee: Allied CorporationInventors: William C. Conner, Jr., Stuart L. Soled, Anthony J. Signorelli, Bruce A. DeRites
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Patent number: 4459427Abstract: A mixture of the alcohol and ketone derivatives of alkanes is produced by reacting the alkane with a hydrocarbyl hydroperoxide, eg t-butyl hydroperoxide, at ambient or elevated temperature and pressure in the presence as catalyst of an iron or manganese square planar complex having heterocyclic nitrogen-donor ligands, e.g. a porphyrin or phthalocyanine complex, which complex has either no axial ligands, eg the lower valency or cationic complex, or an axial ligand which is non-coordinating or weakly-coordinating.Type: GrantFiled: October 26, 1982Date of Patent: July 10, 1984Assignee: The British Petroleum Company p.l.c.Inventors: Anthony R. Middleton, David J. H. Smith
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Patent number: 4430444Abstract: A process for producing methanol from solid carbonaceous material comprisingproviding a gasifier means and a methanol formation means connected to said gasifier means, said gasifier means comprising a gasification chamber defined by a gasification chamber wall having an upper and a lower portion, an upper chamber wall inlet means for feeding said solid carbonaceous material into said gasification chamber, a lower chamber wall gas injection means for introducing gas into said gasification chamber, andan upper chamber wall gas outlet means, said gas outlet being connected to a gas product conduit,said methanol formation means comprising a methanol formation reactor means, reactor output conduit means, condensor means, and condensor output conduit means, said reactor conduit means being connected to said lower chamber wall gas injection means, said condenser output conduit means being connected to said condenser means and to said methanol formation reactor means,said gas product conduit being connected to said cType: GrantFiled: March 8, 1982Date of Patent: February 7, 1984Assignee: Conoco Inc.Inventor: Eric H. Reichl
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Patent number: 4374288Abstract: An electromagnetic methanol reactor system which includes an enclosed reactor chamber having a pair of electrodes positioned in the chamber and spaced from the walls thereof. An electromagnetic field is generated across the electrodes wherein the field has sufficient strength to atomize oxygen. Methane is continuously supplied to the chamber and oxygen is supplied to the chamber between the electrodes so that the oxygen is atomized. The oxygen combines with the methane to form methanol.Type: GrantFiled: December 17, 1980Date of Patent: February 15, 1983Inventor: Robert L. Scragg
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Patent number: 4302610Abstract: Compositions having a host phase of a niobate or tantalate of a divalent or trivalent metal and containing vanadium from one atom present to the limit of solid solubility in the host phase. Host phases of the rutile, columbite and trirutile structure are disclosed. The compositions are useful in the partial oxidation and ammoxidation of lower alkanes.Type: GrantFiled: May 27, 1980Date of Patent: November 24, 1981Assignee: Allied CorporationInventors: William C. Conner, Jr., Stuart L. Soled, Anthony J. Signorelli, Bruce A. DeRites
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Patent number: 4296263Abstract: A liquid mixture of normal butane and isobutane is catalytically oxidized at 15-45% conversion of the isobutane per pass at conditions favoring selective oxidation of the isobutane with minimized oxidation of the normal butane, thereby eliminating the need for superfractionation for ultrapurification of the isobutane prior to the oxidation step. Conditions include 260.degree.-340.degree. F., 200-1000 psig, 1-10 hour residence time, 1-500 ppm of catalyst selected from distributable (e.g. soluble) forms of chromium, cobalt, nickel, manganese, molybdenum, and mixtures thereof.Type: GrantFiled: September 19, 1980Date of Patent: October 20, 1981Assignee: Atlantic Richfield CompanyInventor: G. Richard Worrell
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Patent number: 4296262Abstract: Isobutane is injected into a liquid mixture concurrently with the injection of an oxygen-containing gas. Molybdenum catalyst is present. The oxidation is selective for the formation of tertiary butyl alcohol (TBA) so that the proportions of tertiary butyl hydroperoxide (TBHP), acetone, methanol, carbon dioxide or other less desirable products are relatively low. The tertiary butyl hydroperoxide produced by the reaction and/or the di-tertiary butyl peroxide in the reaction mixture remain in the reaction mixture while continuously distilling a product stream rich in tertiary butyl alcohol and those components boiling below TBA. After appropriate processing, such product stream is utilized as a blending component for gasoline.Type: GrantFiled: February 25, 1980Date of Patent: October 20, 1981Assignee: Atlantic Richfield CompanyInventors: Henry R. Grane, John C. Jubin, Jr., G. Richard Worrell
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Patent number: 4294999Abstract: Isobutane is oxidized in a pressurized reactor in the presence of a solubilized molybdenum catalyst to produce a mixture of tertiary butyl alcohol, tertiary butyl hydroperoxide, methanol, acetone, and other oxygen containing compounds. Unreacted isobutane is recycled. Streams of normally gaseous components, comprising carbon dioxide and carbon monoxide are withdrawn from the effluent streams. A liquid stream withdrawn from the reactor, after being debutanized, is subjected to a thermal decomposition zone under several atmospheres pressure at about 280.degree. F. for from 2 to about 8 hours to reduce the concentration of tertiary butyl hydroperoxide.The liquid derived from the decomposition zone is distilled to provide a distillate stream comprising predominantly tertiary butyl alcohol and a minor proportion of methanol. Said distillate stream is heat treated to destroy residual TBHP and then transferred to a gasoline blending zone in which it is added to hydrocarbons.Type: GrantFiled: February 25, 1980Date of Patent: October 13, 1981Assignee: Atlantic Richfield CompanyInventors: Henry R. Grane, John C. Jubin, Jr., G. Richard Worrell
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Process for the manufacture of mixtures of formaldehyde and methanol by partial oxidation of methane
Patent number: 4243613Abstract: A continuous process for the partial oxidation of methane to produce mixtures of formaldehyde and methanol wherein methane and an oxidizing gas are reacted in a reaction zone in the form of a flame and the resulting reaction mixture is cooled followed by separation of the resulting products, is further improved by controlling the velocity of the oxidizing gas so that it is 50 to 300 meters per second higher than the methane gas with the methane gas being introduced in a velocity of from 1 to 15 meters per second. Also, the stream of methane gas has a volume that is 3 to 100 times greater than the volume of the stream of oxidizing gas introduced into the reaction zone.Type: GrantFiled: September 25, 1978Date of Patent: January 6, 1981Assignee: Chemische Werke Huls AktiengesellschaftInventors: Rudolf Brockhaus, Hans-Jurgen Franke -
Patent number: 4239926Abstract: Isobutane is oxidized to provide a debutanized oxidate comprising tertiary butyl alcohol, acetone, water and other byproducts including high boiling products. Water is removed by extractive distillation using a combination of water and xylene as the extractant. The molar amount of recycled water is greater than the amount of water to be removed from the oxidate. By thus recirculating water through the decantation zone the acetone is satisfactorily coextracted from the butyl alcohol in such a manner that a stream of acetone and a stream of water, as well as the desired dry stream of tertiary butyl alcohol can be withdrawn. If the water is not recycled, the acetone will concentrate in the upper section of the distillation zone and reduce the volatility of water, thereby inhibiting the water removal from the tertiary butyl alcohol.Type: GrantFiled: June 25, 1979Date of Patent: December 16, 1980Assignee: Atlantic Richfield CompanyInventors: Henry R. Grane, John C. Jubin, Jr., G. Richard Worrell
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Patent number: 4220604Abstract: An isoolefin is converted to a ketone, e.g., isobutylene to methyl ethyl ketone, by an oxidative rearrangement in a two-phase diluent system in the presence of free oxygen, a suitable surfactant, and a catalyst system comprising palladium, copper, and an alkali or alkaline earth metal chloride.Type: GrantFiled: July 14, 1978Date of Patent: September 2, 1980Assignee: Phillips Petroleum CompanyInventor: Paul R. Stapp
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Patent number: 4131742Abstract: A process for the liquid phase oxidation of hydrocarbons with a molecular oxygen-containing gas in the presence of a dissolved cobalt salt catalyst characterized in that the oxidation is carried out in the substantial absence of chromium in the reaction medium i.e. a concentration of chromium in the liquid phase of not greater than 400 ppm.Type: GrantFiled: November 3, 1976Date of Patent: December 26, 1978Assignee: BP Chemicals LimitedInventor: Barry Hudson
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Patent number: 4131741Abstract: In a process for the production of oxygenated organic compounds including a substantial proportion of acetic acid by oxidizing a C.sub.3 to C.sub.7 saturated aliphatic hydrocarbon in the liquid phase with molecular oxygen in the presence of an inert reaction medium and a cobalt catalyst, between 5 and 90% in a continuous reaction and 11 and 90% in a batch reaction of the cobalt being introduced in the +3 oxidation state, the improvement comprising separating the catalyst solution fraction from the fraction comprising oxygen-containing compounds and water by distillation while limiting the residence time of the catalyst solution fraction in the distillation zone so that it is the minimum consistent with substantially complete separation of the fractions thereby minimizing the reduction of Co.sup.+3 to Co.sup.+2.Type: GrantFiled: December 29, 1976Date of Patent: December 26, 1978Assignee: BP Chemicals LimitedInventors: John S. Bartlett, Barry Hudson