Patents Represented by Attorney Ralph M. Pritchett
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Patent number: 4139565Abstract: In hydroformylating an ethylenically-unsaturated compound to produce a formyl-substituted derivative using as catalyst rhodium hydrido carbonyl in complex combination with a disphosphino ligand, a high ratio of the normal aldehyde to the iso-aldehyde in the product can be obtained even at very low ratios of ligand to rhodium in the catalyst mixture by using as the ligand a cyclic compound having in the ring two adjacent carbon atoms between the trans position of which the minimum and maximum attainable dihedral angels are, respectively, at least about 90.degree. and not more than about 180.degree., each of these adjacent carbon atoms being substituted with a phosphinomethyl group, the phosphinomethyl groups being in trans relationship to one another. If there are maintained in the reaction zone at least about 1.5 moles of the ligand per atom of rhodium, the desired results are obtained and higher ligand:rhodium ratios are not necessary.Type: GrantFiled: March 31, 1977Date of Patent: February 13, 1979Assignee: Celanese CorporationInventors: Jerry D. Unruh, Leslie E. Wade
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Patent number: 4138420Abstract: An organo metallic complex catalyst, useful in the hydroformylation of an olefin, e.g., an alkene, to yield an aldehyde product in which the normal aldehyde isomer predominates over branch-chain isomers, which has the structure: ##STR1## wherein capital M is a Group VIII metal (preferably rhodium); Q is phosphorus, arsenic, or antimony (preferably phosphorus); and R is phenyl or a lower alkyl group.In the process employing the new catalytic complex it is not necessary to employ an excess of any ligand, and moderate reaction conditions are adequate. The catalyst can be prepared ex situ or in situ from a suitable source of rhodium or the Group VIII metal and a suitable derivative of ferrocene.Type: GrantFiled: September 23, 1977Date of Patent: February 6, 1979Assignee: Celanese CorporationInventors: Jerry D. Unruh, William J. Wells, III
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Patent number: 4110298Abstract: In a process for the manufacture of trioxane by the distillation of aqueous formaldehyde solutions which are intimately mixed with an immiscible, non-volatile, oily liquid phase, the improvement comprising using a monoalkyl ether of a polyoxyalkylene glycol as the oily phase.Type: GrantFiled: May 31, 1977Date of Patent: August 29, 1978Assignee: Celanese CorporationInventors: William J. Wells, III, Adin L. Stautzenberger
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Patent number: 4105701Abstract: A liquid contaminated with a carbonyl compound, especially an aldehyde, is purified by being contacted with a bed of solid polyvinyl alcohol particles or fibers. The carbonyl compound is adsorbed or chemisorbed onto the solid polyvinyl alcohol surface with resulting reaction in the carbonyl content of the liquid.Type: GrantFiled: April 28, 1975Date of Patent: August 8, 1978Assignee: Celanese CorporationInventor: Donald R. Larkin
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Patent number: 4089886Abstract: Impure methanol may be treated to remove iron pentacarbonyl impurities by adding a source of hypochlorite ions to the impure methanol whereby the iron of the iron pentacarbonyl will be oxidized to the ferrous or ferric state. The impure methanol is then subjected to distillation to remove iron compounds as heavy ends.Type: GrantFiled: July 21, 1977Date of Patent: May 16, 1978Assignee: Celanese CorporationInventors: Anthony J. Branecky, David W. Harris
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Patent number: 4054590Abstract: A process for producing fatty acids from C.sub.12 to C.sub.35 normal alkanes by air oxidizing the alkanes, followed by nitric acid oxidation of the air oxidation product.Type: GrantFiled: September 17, 1976Date of Patent: October 18, 1977Assignee: Celanese CorporationInventor: Harold Robert Gerberich, Jr.
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Patent number: 4029636Abstract: In high-temperature vapor-phase reaction systems in which there are employed molybdenum-containing catalysts, contamination and/or blockage of downstream processing equipment has been found to be a problem as a result of vaporization of molybdenum trioxide into the hot gases passing through the catalytic reactor. The present invention comprises a method for alleviating the problem, preferably by passing the reactor effluent vapor through a bed or array of cooled solids upon which molybdenum trioxide is deposited and so removed from the reactor effluent gases.Type: GrantFiled: November 12, 1974Date of Patent: June 14, 1977Assignee: Celanese CorporationInventors: Richard P. Lowry, Joseph D. Chase, Paul A. C. Cook
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Patent number: 4011252Abstract: A process for producing fatty acids from C.sub.20 to C.sub.30 normal alkanes by air oxidizing the alkanes, followed by hydrogenating the product of the air oxidation and then oxidizing the hydrogenated product by nitric acid oxidation. The crude fatty acid product may be purified by a second hydrogenation to convert nitrogen impurities to amines and removal of the amines.Type: GrantFiled: August 20, 1975Date of Patent: March 8, 1977Assignee: Celanese CorporationInventors: Harold Robert Gerberich, Jr., Edward F. Dougherty
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Patent number: 4008279Abstract: A process for dehalogenation of alpha halogenated carbonyl compounds and/or the prevention of the formation of such. The process for dehalogenation generally comprises causing there to be in solution the halogenated compound, cuprous ions (such as from cuprous chloride) and hydrogen ions (such as from hydrochloric acid), the process to be conducted in the absence of molecular oxygen, or, if molecular oxygen is present, there being an excess of cuprous ions sufficient to completely react with the molecular oxygen present. Such can also be used to suppress formation of halogenated carbonyl compounds in processes where conditions exist which favor such formation.Type: GrantFiled: August 15, 1974Date of Patent: February 15, 1977Assignee: Celanese CorporationInventor: Jorge A. Blay
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Patent number: 3983208Abstract: An aqueous nitric acid solution derived from an adipic acid process containing copper and vanadium catalyst values and alkyl dicarboxylic acids is treated to remove the nitric acid and water therefrom so as to obtain a substantially dry, molten-type residue. This residue is mixed with a dialkyl ketone solvent which dissolves the dicarboxylic acids and leaves the catalyst metal values as solids.Type: GrantFiled: January 27, 1975Date of Patent: September 28, 1976Assignee: Celanese CorporationInventor: Jorge A. Blay
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Patent number: 3976595Abstract: Sulfonic acid catalysts useful in, for example, esterification reactions and which contain an admixture of any of several phosphorus compounds including specifically ortho-phosphoric acid are much less corrosive toward metal processing equipment than are sulfonic acid catalysts without the phosphoric admixture.Type: GrantFiled: March 17, 1975Date of Patent: August 24, 1976Assignee: Celanese CorporationInventors: Robert H. Scott, Dan L. Gaulding
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Patent number: 3972946Abstract: In converting an alkene such as ethylene to a carbonyl derivative such as acetaldehyde by a process which comprises passing the alkene through a tubular reactor along with an aqueous acidic catalyst solution comprising a noble metal such as palladium together with a cupric chloride redox agent, followed by separating the carbonyl product from the depleted catalyst solution which is then reoxidized with a source of molecular oxygen such as air prior to being returned to the reactor, continuous depletion of the chloride content of the catalyst solution takes place as a result of the formation of chlorinated reaction by-products. This necessitates replenishment of the chloride content of the catalyst solution by adding hydrochloric acid into a catalyst regeneration zone preceding the catalyst reoxidation step of the process.Type: GrantFiled: September 22, 1971Date of Patent: August 3, 1976Assignee: Celanese CorporationInventors: Shinya Ochiai, Leonard Griffith
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Patent number: 3965166Abstract: Process for the oxidation of olefins to the corresponding unsaturated aldehydes and acids, e.g. propylene to acrolein and acrylic acid, by reacting the olefin with oxygen in the presence of a catalyst of the empirical formula Mo.sub.x Cr.sub.y Te.sub.z O.sub.n. When x is 100, y is 10-50, z is 0.1-10, and n is 300-500.Type: GrantFiled: February 24, 1969Date of Patent: June 22, 1976Assignee: Celanese CorporationInventor: Leon B. Levy
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Patent number: 3965164Abstract: In a process for the production of adipic acid by nitric acid oxidation of cyclohexanol and/or cyclohexanone wherein copper and vanadium values are recovered by ion exchange means, the improvement which comprises utilizing the off-gas from the nitric acid oxidation to treat the solution being passed to the ion exchange zone.Type: GrantFiled: January 27, 1975Date of Patent: June 22, 1976Assignee: Celanese CorporationInventor: Jorge A. Blay
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Patent number: 3962350Abstract: Phenolic compounds, such as phenol itself, are formed by oxidizing the corresponding aromatic aldehyde precursors, in the vapor phase, with molecular oxygen, the gaseous oxidation product being cooled in the presence of an inert diluent to prevent formation of tarry condensation products. In a particular embodiment a mixture of toluene and benzaldehyde is reacted with oxygen to convert the benzaldehyde to phenol while a portion of the toluene is oxidized to benzaldehyde which is recycled. The products are separated by solvent extraction.Type: GrantFiled: August 26, 1974Date of Patent: June 8, 1976Assignee: Celanese CorporationInventors: Theodore Horlenko, James Henry George
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Patent number: 3951756Abstract: A distillation process for removing light ends impurities from alkyl esters of carboxylic acids wherein a purified ester is removed as residue, and wherein an inert gas and water are added to the overhead vapors from the distillation so as to facilitate separation of the light ends therefrom.Type: GrantFiled: November 8, 1974Date of Patent: April 20, 1976Assignee: Celanese CorporationInventors: Jerald Edson Dirks, Gene Jordan Fisher
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Patent number: 3947563Abstract: Process for hydrogenolysis of an alkali metal or an alkaline earth metal salt of formic acid so as to produce methanol and a metal hydroxide corresponding to the formic acid salt wherein a catalyst of cobalt, rhenium, ruthenium, palladium, platinum or mixtures thereof is used.Type: GrantFiled: October 7, 1974Date of Patent: March 30, 1976Assignee: Celanese CorporationInventor: Edward F. Dougherty
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Patent number: 3933930Abstract: In the production of 1,6-hexanediol by oxidation of cyclohexane to produce an acidic oxidation product comprising adipic acid, followed by esterification of the acidic oxidation product and a subsequent hydrogenolysis of the ester, the improvement which comprises a prehydrogenation of the acidic oxidation product prior to esterification thereof.Type: GrantFiled: March 6, 1975Date of Patent: January 20, 1976Assignee: Celanese CorporationInventors: Edward F. Dougherty, Charles C. Hobbs, Jr.
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Patent number: 3931249Abstract: A process for the epoxidation of ethylenically unsaturated compounds with organic hydroperoxides using metal-free phthalocyanines or metal phthalocyanines as catalysts. Suitable metals include those of the metals Ni, Cu, Ag, Ti, V, Zr, Mo. Re, or U.Type: GrantFiled: February 13, 1974Date of Patent: January 6, 1976Assignee: Celanese CorporationInventor: Adin Lee Stautzenberger