Air Or Molecular Oxygen Utilized Patents (Class 549/532)
-
Patent number: 6326502Abstract: The present invention provides a process for the epoxidation of alkenes of the formula (1) where R1, R2, R3 and R4 are, independently of one another, hydrogen, C1-C20-alkyl, C1-C12-alkoxy, C6-C10-aryl, —CHOH—CH3, —CH—NH2—CH3 or carboxy, using air or oxygen over a catalyst comprising compounds of the formula (2) MoxOy(L)z (2) where x is 1, 2 or 3, y is an integer from 0 to 2x+1, z is an integer from 1 to 2x, where the ligand L is a compound of the formula (3) or (4) where X is a nitrogen, oxygen or sulfur atom, Y is hydrogen, C1-C8-alkyl, C1-C8-alkoxy, F, Cl, Br, I, COOCH3, C6-C14-aryl or C3-C8-cycloalkyl, R7 and R8 form a ring containing from 4 to 8 carbon atoms onto which one or two aromatic rings may be fused, R5 and R6 are hydrogen, branched or straight-chain C1-C12-alkyl or branched or straight-chain C1-C12-haloalkyl which are substituents on the ring formed by R7 and R8 and/or the rings fused onto this ring, or tType: GrantFiled: January 7, 2000Date of Patent: December 4, 2001Assignee: Aventis Research & Technologies GmbH & Co. KGInventors: Rolf Peter Schulz, Uwe Dingerdissen, Wolfgang Anton Herrmann, Gerhard Lobmaier
-
Patent number: 6323350Abstract: The present invention relates to a liquid phase process for preparing an olefin oxide from an olefin in a cascade of two or more reactors, in a baffled tank reactor or in a plug flow reactor which process comprises the steps of a) contacting the olefin in a solvent with oxygen or an oxygen-containing gas in a first reactor of the reactor cascade or in a first stage of the baffled tank reactor or of the plug flow reactor, thereby producing a mixture comprising olefin oxide, non-converted olefin, solvent and by-products and b) transferring at least a portion of the mixture obtained in step a) to a second reactor of the reactor cascade or to a second stage of the baffled tank reactor or plug flow reactor, adding an additional amount of i) oxygen or an oxygen-containing gas and/or ii) olefin to the mixture and continuing the reaction.Type: GrantFiled: June 21, 2000Date of Patent: November 27, 2001Assignee: The Dow Chemical CompanyInventors: Joerg Lindner, Wolfgang Taeuber, Hans-Juergen Wertgen
-
Patent number: 6310224Abstract: In a process for the production of an oxirane compound by reaction of olefins, oxygen and hydrogen using a noble metal on titanium or vanadium silicalite catalyst the improvement wherein the catalyst is doped with a substantially non-reduced metal dopand.Type: GrantFiled: January 19, 2001Date of Patent: October 30, 2001Assignee: ARCO Chemical Technology, L.P.Inventor: Roger A. Grey
-
Patent number: 6307073Abstract: A catalyst mixture containing a titanium zeolite and a supported gold-containing catalyst is highly selective and productive for transforming olefins to epoxides in the liquid-phase reaction of an olefin, hydrogen, and oxygen. This is particularly surprising because neither titanium zeolite nor the supported gold-containing catalyst alone is effective in olefin epoxidation.Type: GrantFiled: July 25, 2000Date of Patent: October 23, 2001Assignee: ARCO Chemical Technology, L.P.Inventor: C. Andrew Jones
-
Patent number: 6303800Abstract: Process for preparing propene oxide, in which a mixture of propene and oxygen or an oxygen-containing gas is reacted at a temperature in the range from 150 to 500° C., in the presence or absence of a catalyst, in a reactor, wherein all or part of the interior of the reactor is lined with inert materials. The inert material used is at least one of the materials of the following group: one or more noble metals of transition group VIII of the Periodic Table, in particular gold, titanium and tantalum, glass, enamel, quartz, ceramic and Teflon. The selectivity to propene oxide is >60%.Type: GrantFiled: July 14, 2000Date of Patent: October 16, 2001Assignee: Aventis Research & Technologies GmbH & Co KGInventors: Uwe Dingerdissen, Holger Orzesek, Wilhelm Maier, Rolf Schulz
-
Patent number: 6281369Abstract: The stability of a noble metal/titanium zeolite catalyst is improved by elevated temperature calcination with an oxygen containing gas; the catalyst is useful in epoxidation involving the reaction of olefin, oxygen and hydrogen.Type: GrantFiled: December 7, 2000Date of Patent: August 28, 2001Assignee: Arco Chemical Technology, L.P.Inventors: Bernard Cooker, Jennifer D. Jewson, Wilson H. Onimus
-
Patent number: 6255499Abstract: A process and catalyst for the hydro-oxidation of an olefin having three or more carbon atoms, such as propylene, to form an olefin oxide, such as propylene oxide. The process involves contacting the olefin with oxygen under reaction conditions in the presence of hydrogen and a catalyst. The catalyst contains oxidized gold dispersed on a titanium-containing support, preferably, a support having a plurality of titanium coordination environments, for example, titanium grafted onto a titanosilicate. Selectivity to olefin oxide is high at good conversion of the olefin. The catalyst uses hydrogen efficiently and exhibits a long lifetime.Type: GrantFiled: April 7, 2000Date of Patent: July 3, 2001Assignee: The Dow Chemical CompanyInventors: Alex Kuperman, Robert G. Bowman, Howard W. Clark, George E. Hartwell, Brian J. Schoeman, Hendrik E. Tuinstra, Garmt R. Meima
-
Patent number: 6063942Abstract: An epoxidation catalyst is prepared by contacting a vanadium or titanium silicalite slurry with an ion exchangeable noble metal complex, and the catalyst is used without drying or calcining for olefin epoxidation by contact with 0.sub.2, H.sub.2 and olefin.Type: GrantFiled: September 27, 1999Date of Patent: May 16, 2000Assignee: Arco Chemical Technology, L.P.Inventor: Roger A. Grey
-
Patent number: 5973209Abstract: A method is disclosed for preparing 3,3-dimethylbutyraldehyde by using silica gel to isomerize 3,3-dimethyl-1,2-epoxybutane, which in turn may be prepared by oxidation of dimethylbutene. Also disclosed is a method for oxidizing dimethylbutene with dimethyldioxirane to form 3,3-dimethyl-1,2-epoxybutane. The methods provide an economical means of preparing 3,3-dimethylbutyraldehyde.Type: GrantFiled: July 11, 1997Date of Patent: October 26, 1999Assignee: The NutraSweet CompanyInventors: Indra Prakash, Marie-Christine D. Chapeau
-
Patent number: 5973171Abstract: An integrated process is provided for the production of propylene oxide from propane wherein propane is dehydrogenated to propylene and hydrogen and the resulting propylene, propane, and hydrogen mixture together with added oxygen is reacted over a palladium on titanium silicilite catalyst to form propylene oxide, the molar ratio of oxygen to hydrogen in the reaction feed being at least about 2/1.Type: GrantFiled: October 7, 1998Date of Patent: October 26, 1999Assignee: ARCO Chemical Technology, LPInventors: Robert N. Cochran, John C. Jubin, Jr., Mark A. Liepa, Robert Nedwick, Rangasamy Pitchai, W. Wayne Wentzheimer
-
Patent number: 5892066Abstract: Propylene is oxidized with molecular oxygen in the liquid phase to form products including propylene oxide, propylene glycol, propylene glycol esters, allyl alcohol, acrolein and acetal, the acrolein is hydrogenated to allyl alcohol, the acetol is hydrogenated to propylene glycol, the propylene glycol esters are hydrolyzed to propylene glycol, and propylene oxide, propylene glycol and allyl alcohol are recovered as products.Type: GrantFiled: December 12, 1997Date of Patent: April 6, 1999Assignee: ARCO Chemical Technology, L.P.Inventor: Roger A. Grey
-
Patent number: 5856533Abstract: Heterogeneous vapor phase oxidation and other reactions are carried out at the surface of a solid catalyst, with both gaseous reactants and the solid catalyst being dispersed in a recirculating liquid solvent. Reaction and product absorption are combined into a single processing step, with enhanced catalyst performance, and product selectivity and product yields, enhanced mass and heat transfer characteristics and reduced risk of forming explosive mixtures in the course of a particular reaction.Type: GrantFiled: December 28, 1995Date of Patent: January 5, 1999Assignee: Praxair Technology, Inc.Inventors: Joshua Brien Sweeney, Roger William Day, Deepak Lumba
-
Patent number: 5808132Abstract: Heptafluoroisobutenyl methyl ether having the following formula: ##STR1## is oxidized with ozone to produce perfluoro(2-methyl-1,2-epoxy-propyl) methyl ether. The resulting intermediate compound is allowed to react with an aromatic compound ArH to produce .alpha.,.alpha.-bis(trifluoromethyl)arylacetic acid methyl ester having the following formula: ##STR2## By hydrolysis, decarboxylation and further hydrolysis of the ester compound, .alpha.,.alpha.-bis(trifluoromethyl)arylacetic acid for use as raw materials for medicines, agricultural chemicals, liquid crystals, etc. or reagents for determining an optical purity can be obtained.Type: GrantFiled: March 12, 1996Date of Patent: September 15, 1998Assignee: Nippon Mektron, LimitedInventors: Takehiro Sonoi, Toshimasa Sagawa, Futoshi Masaki, Toshio Kubota
-
Patent number: 5760254Abstract: Oxirane compounds are produced by molecular oxygen oxidation of an olefin in the presence of a nitrogen oxide catalyst.Type: GrantFiled: July 18, 1996Date of Patent: June 2, 1998Assignee: Arco Chemical Technology, L.P.Inventor: Roger A. Grey
-
Patent number: 5756779Abstract: Disclosed are improved processes for the recovery of 3,4-epoxy-1-butene (epoxybutene) from an epoxidation effluent comprising epoxybutane, butadiene, oxygen and an inert diluent obtained by the selective epoxidation of butadiene with an oxygen-containing gas in the presence of a catalyst and an inert gas. Epoxybutene is separated from the effluent by means of an absorption process using an extractant comprising liquid butadiene and, optionally, a hydrocarbon diluent. The formation of butenediols, by the reaction of epoxybutene and water, in the recovery process is inhibited by the addition of a base, preferably an alkali metal base, to the recovery system.Type: GrantFiled: September 29, 1997Date of Patent: May 26, 1998Assignee: Eastman Chemical CompanyInventor: Jerome Leonard Stavinoha, Jr.
-
Patent number: 5229425Abstract: A process for producing a stable, bactericidal and fungicidal composition which consists essentially of bubbling air or oxygen into limonene, to produce an oxidized limonene having a rapid bactericidal activity as evidenced by the capability of killing substantially all of the bacteria in a suitable culture medium inoculated with 10.sup.6 colony forming units of Staphylococcus aureus ATCC 25923 per ml. of said broth, containing not more than 0.06 ml of said oxidized limonene per ml. of said broth and incubated at 37.degree. C. in air for 60 minutes.Type: GrantFiled: May 29, 1992Date of Patent: July 20, 1993Assignee: Doyle E. ChastainInventors: Doyle E. Chastain, W. E. Sanders, Jr., Christine C. Sanders
-
Patent number: 5153229Abstract: A process for producing a stable, bactericidal and fungicidal composition which consists essentially of bubbling air or oxygen into limonene, to produce an oxidized limonene having a rapid bactericidal activity as evidenced by the capability of killing at least 99.99% of the bacteria in a suitable culture medium inoculated with 10.sup.6 colony forming units of Staphylococcus aureus ATCC 25923 per ml.Type: GrantFiled: June 1, 1990Date of Patent: October 6, 1992Assignee: Doyle E. ChastainInventors: Doyle E. Chastain, W. Eugene Sanders, Jr., Christine C. Sanders
-
Patent number: 5149842Abstract: A process is disclosed for preparing peroxidic perfluoropolyethers comprising perfluoroalkylenoxy units having at least two carbon atoms, characterized in that one or more perfluoroolefins, except tetrafluoroethylene used alone, are reacted with oxygen in the liquid phase at a temperature not exceeding 50.degree. C. and in the presence of one or more compounds having one or more F-X bonds, in which X is selected from the group consisting of F, O and Cl.Type: GrantFiled: October 31, 1990Date of Patent: September 22, 1992Assignee: AUSTIMONT S.r.l.Inventors: Dario Sianesi, Antonio Marraccini, Giuseppe Marchionni
-
Patent number: 5142070Abstract: Described herein is a process for the direct oxidation of propylene to propylene oxide in conditions such that propylene is above its critical temperature and pressure.Type: GrantFiled: December 3, 1990Date of Patent: August 25, 1992Assignee: Olin CorporationInventors: Michael C. Fullington, Buford T. Pennington
-
Patent number: 5068366Abstract: A process for the preparation of isobutylene oxide and isobutyric acid from isobutylene and isobutyraldehyde, respectively, by a co-oxidation process conducted in the presence of oxygen and a cobalt salt catalyst at a temperature of about 20.degree. to about 180.degree. C. is disclosed.Type: GrantFiled: August 6, 1990Date of Patent: November 26, 1991Assignee: Texaco Chemical CompanyInventors: John R. Sanderson, Edward T. Marquis
-
Patent number: 5008414Abstract: An improved process is provided for the production of oxides from hydrocarbons by reaction with oxygen, air or a gas enriched in oxygen relative to air, preferably the latter in the presence of an oxidation catalyst. An alkane, e.g. propane, is converted to an alkene in a catalytic dehydrogenator. The product stream is introduced into an oxidation reactor. The product formed therein is recovered in a conventional quench tower. The gaseous effluent from the quench tower is treated in a separator to produce an adsorbed stream, an oxygen-enriched stream, a waste stream and, if desired, a hydrogen-enriched stream. The oxygen-enriched stream may be recycled to the oxidation reactor depending on the nitrogen content thereof. The adsorbed stream plus at least a portion of the hydrogen-enriched stream is introduced into a selective oxidation unit to remove the remaining oxygen and then recycled to the dehydrogenator. The remainder of the hydrogen-enriched stream, if any, may be taken as product or vented.Type: GrantFiled: September 21, 1989Date of Patent: April 16, 1991Assignee: The BOC Group, Inc.Inventors: Ramakrishnan Ramachandran, Donald L. MacLean, Donald P. Satchell, Jr., Virginia A. Malik
-
Patent number: 4992567Abstract: A continuous process for the vapor phase oxidation of an alkane or olefin in molten salt catalyst to produce alkylene oxides in increased yields while reducing or substantially eliminating the formation of aldehyde by-products. The process involves the continuous separation and recirculation of aldehydes, normally formed in the oxidation reaction, back into the vapor phase oxidation reaction for co-oxidation to form carbon-oxygen gases while increasing the olefin selectivity to alkylene oxide.Type: GrantFiled: June 7, 1989Date of Patent: February 12, 1991Assignee: Olin CorporationInventors: James L. Meyer, Pennington, B. Timothy
-
Patent number: 4959486Abstract: A process for producing an alkylene oxide or mixture of alkylene oxides by a reaction which comprises reacting an alkane or alkylaromatic compound mixture thereof with an oxygen-containing gas in the presence of at least one molten nitrate salt catalyst.Type: GrantFiled: August 3, 1989Date of Patent: September 25, 1990Assignee: Olin CorporationInventor: B. Timothy Pennington
-
Patent number: 4943643Abstract: A process for the vapor phase oxidation of olefins in molten salt catalyst to produce alkylene oxides in increased molar selectivity and per-pass yields while reducing the molar selectivity of aldehyde by-products. The process involves the use of molten nitrate salt catalyst compositions which comprise lithium nitrate and which are heated and operated at a low temperature within the range of about 180.degree. C. up to about 250.degree. C., more preferably 200.degree. C. to 250.degree. C.Type: GrantFiled: June 7, 1989Date of Patent: July 24, 1990Assignee: Olin CorporationInventors: B. Timothy Pennington, Michael C. Fullington
-
Patent number: 4885374Abstract: A process for producing an alkylene oxide or mixture of alkylene oxides by a reaction which comprises reacting an alkane or alkylaromatic compound mixture thereof with an oxygen-containing gas in the presence of at least one molten nitrate salt catalyst.Type: GrantFiled: August 31, 1988Date of Patent: December 5, 1989Assignee: Olin CorporationInventor: B. Timothy Pennington
-
Patent number: 4883889Abstract: A process for producing an alkylene oxide or mixture of alkylene oxides by a reaction which comprises reacting an olefin or mixture thereof with an oxygen-containing gas in the presence of at least one molten nitrate salt and a co-catalyst.Type: GrantFiled: April 18, 1988Date of Patent: November 28, 1989Assignee: Olin CorporationInventor: B. Timothy Pennington
-
Patent number: 4882443Abstract: A process for producing an alkylene oxide or mixture of alkylene oxides by a reaction which comprises reacting a C7 to C22 olefin or mixture thereof with an oxygen-containing gas in the presence of at least one molten nitrate salt.Type: GrantFiled: August 31, 1988Date of Patent: November 21, 1989Assignee: Olin CorporationInventor: B. Timothy Pennington
-
Patent number: 4785123Abstract: A process for producing an alkylene oxide or mixture of alkylene oxides by a reaction which comprises reacting an alkane, an alkylene, or mixture thereof with an oxygen-containing gas in the presence of at least one molten nitrate salt.Type: GrantFiled: November 12, 1986Date of Patent: November 15, 1988Assignee: Olin CorporationInventor: B. Timothy Pennington
-
Patent number: 4491674Abstract: A process for the safe supply of molecular oxygen or gas containing molecular oxygen to an oxidation of hydrocarbons in the liquid phase, wherein, immediately before the point of entry into the liquid hydrocarbon, the oxygen, or gas containing oxygen, to be supplied is at least 20.degree. C. colder than the hydrocarbon, and wherein, as soon as the oxygen, or gas containing oxygen, which is to be supplied exceeds the predetermined temperature at the supply orifice, the supply ceases.Type: GrantFiled: December 8, 1980Date of Patent: January 1, 1985Assignee: BASF AktiengesellschaftInventors: Norbert Rieber, Hans Hellbach, Gerhard Hunziker, Guenter Mueller
-
Patent number: 4469880Abstract: A process for the production of cycloalkane epoxides from cycloalkenes in the presence of a boron-containing catalyst, oxygen and a carboxylate ion source via air oxidation is described. Alkali metal borates, alkali earth metal borates, rare earth borates and transition metal borates are useful catalysts. The boron catalyst may contain many different cations including lithium, sodium, strontium, barium, cerium, zirconium, vanadium, niobium, iron, cobalt, nickel, copper, zinc, and mixtures thereof. The reaction is conducted at a temperature in the range of 50.degree. to 150.degree. C. and a pressure of one atmosphere or greater. Cycloalkane epoxides are useful in the preparation of resins, plasticizers, etc.Type: GrantFiled: September 23, 1982Date of Patent: September 4, 1984Assignee: Texaco Inc.Inventors: John R. Sanderson, Lewis W. Watts, Jr., Terry L. Renken, Steven H. Vanderpool
-
Patent number: 4469887Abstract: To produce methacrylic acid, firstly, isobutyraldehyde is acetalized. The resultant acetal is cleaved into the isobutenyl ether and alcohol. The isobutenyl ether is oxidized with molecular oxygen or an oxygen-containing gaseous mixture in the presence of an alkaline solution at temperatures of 30.degree.-70.degree. C. to obtain the epoxide. This epoxide is hydrolyzed to the .alpha.-hydroxyisobutyraldehyde. The latter is then oxidized with concentrated or fuming nitric acid at temperatures of 20.degree.-110.degree. C. to produce .alpha.-hydroxyisobutyric acid, and methacrylic acid is obtained therefrom by splitting off water.Type: GrantFiled: October 26, 1982Date of Patent: September 4, 1984Assignee: Chemische Werke Huels, AGInventors: Rudolf Brockhaus, Hans-Jurgen Franke
-
Patent number: 4403098Abstract: A process for producing a 3,3-dimethyl-2-alkoxyoxirane comprises oxidizing a 1-alkoxy-2-methylpropene with molecular oxygen in the liquid phase, at a temperature of 25.degree.-70.degree. C., optionally in the presence of an alkaline compound.Type: GrantFiled: March 11, 1982Date of Patent: September 6, 1983Assignee: Chemische Werke Huls AktiengesellschaftInventors: Rudolf Brockhaus, Hans-Jurgen Franke
-
Patent number: 4400558Abstract: The present invention provides a novel method for recovering 2-phenylethanol which is produced as a by-product of non-catalytic air oxidation of ethylbenzene, and as a by-product, in the ethylbenzene hydroperoxide epoxidation of an olefinically unsaturated compound, e.g., propylene, to the corresponding alkylene oxide, e.g., propylene oxide. In such processes, 2-phenylethanol accumulates in a process stream typically comprising major proportions of methylbenzyl alcohol, ethylbenzene, alkylene oxide and acetophenone. Conventional distillation-separation procedures may remove most of the alkylene oxide and ethylbenzene, leaving a process stream which is eventually used for styrene monomer production which contains minor amounts, i.e., less than about 20 weight percent, of 2-phenylethanol.Type: GrantFiled: April 17, 1981Date of Patent: August 23, 1983Assignee: Atlantic Richfield CompanyInventors: Margaret I. Nemet-Mavrodin, John F. White
-
Patent number: 4384128Abstract: Perfluoroglycidyl ethers of the formula ##STR1## are prepared by epoxidation of a perfluoroallyl ether of the formulaCF.sub.2 .dbd.CFCF.sub.2 OR.sub.F.The glycidyl ethers are useful as monomers for preparing polymers which are useful as stable oils and greases. Polymers containing functional moieties which provide crosslinking or cure sites are stable elastomeric materials useful as sealants, caulks, and fabricated objects.Type: GrantFiled: January 25, 1982Date of Patent: May 17, 1983Assignee: E. I. Du Pont de Nemours and CompanyInventors: Carl G. Krespan, Alicia P. King
-
Patent number: 4380659Abstract: An olefinically unsaturated compound containing from 3 up to about 18 carbon atoms per molecule and having the formula ##STR1## wherein each R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is independently selected from a group consisting of hydrogen, alkyl, and cycloalkyl radicals and wherein there is at least one hydrogen attached to a carbon atom adjacent to the olefinic group is oxidized in a liquid reaction medium containing methyl formate. In a preferred embodiment of the invention propylene is oxidized in the presence of methyl formate solvent.Type: GrantFiled: January 12, 1979Date of Patent: April 19, 1983Assignee: Phillips Petroleum CompanyInventor: Paul W. Solomon
-
Patent number: 4377705Abstract: Perfluoroglycidyl ethers of the formula ##STR1## are prepared by epoxidation of a perfluorodiallyl ether of the formulaCF.sub.2 =CFCF.sub.2 OR.sub.F.The glycidyl ethers are useful as monomers for preparing polymers which provide crosslinking or cure sites and are stable elastomeric materials useful as sealants, caulks, and fabricated objects.Type: GrantFiled: January 25, 1982Date of Patent: March 22, 1983Assignee: E. I. Du Pont de Nemours and CompanyInventors: Carl G. Krespan, Thomas R. Darling