Patents Represented by Attorney Ralph M. Pritchett
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Patent number: 5001259Abstract: An alcohol such as methanol is reacted with carbon monoxide in a liquid reaction medium containing a rhodium catalyst stabilized with an iodide salt, especially lithium iodide, along with alkyl iodide such as methyl iodide and alkyl acetate such as methyl acetate in specified proportions. With a finite concentration of water in the reaction medium the product is the carboxylic acid instead of, for example, the anhydride. The present reaction system not only provides an acid product of unusually low water content at unexpectedly favorable reaction rates but also, whether the water content is low or, as in the case of prior-art acetic acid technology, relatively high, is characterized by unexpectedly high catalyst stability; i.e., it is resistant to catalyst precipitation out of the reaction medium.Type: GrantFiled: June 3, 1986Date of Patent: March 19, 1991Assignee: Hoechst Celanese CorporationInventors: Brad L. Smith, G. Paull Torrence, Adolfo Aguilo', James S. Alder
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Patent number: 4450301Abstract: In a process for oxidizing methanol to formaldehyde which comprises passing the methanol with molecular oxygen through two sequential silver-based catalysts, with the second of said catalysts being a bed of particulate silver such as, specifically, silver crystals, the process efficiency, and especially the efficiency of the reaction taking place in the second catalyst bed, is improved by controlling (a) the ratio of formaldehyde to methanol in the reactant gases entering the second catalyst bed and (b) the specific reaction rate in said second bed. The specific reaction rate is defined as the quantity of methanol converted in said second bed per unit time per unit of cross-sectional area of the bed.Type: GrantFiled: October 21, 1982Date of Patent: May 22, 1984Assignee: Celanese CorporationInventors: William P. McMillan, Charles C. Hobbs, Jr., H. Robert Gerberich, Michael L. Junker
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Patent number: 4394355Abstract: The solid oxalate of a catalytic metal such as cobalt, typically formed as an undesired and useless by-product during the liquid-phase oxidation of an organic compound, typically a hydrocarbon, in the presence of a homogeneous catalyst comprising said metal, is treated to convert the metal moiety to a reusable form by a process comprising leaching the metal oxalate with an aqueous solution of a soluble salt of ethylenediaminetetraacetic acid (EDTA). The resulting solution of EDTA-metal complex or chelate is then mixed with a soluble calcium salt to precipitate the oxalate moiety as insoluble calcium oxalate leaving the metal-EDTA complex in solution. After removing the resulting solid calcium oxalate, the remaining filtrate is acidified to convert the metal moiety to a simple salt which can be recycled to the liquid-phase oxidation, while the EDTA is precipitated as a solid which can also be recovered and re-used in the complexation step of the process.Type: GrantFiled: March 2, 1982Date of Patent: July 19, 1983Assignee: Celanese CorporationInventor: James D. Fruge'
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Patent number: 4351729Abstract: A biological filter apparatus, and process for using the same, wherein organic pollutants in a waste water stream may be biologically degraded by a biomass of suitable microorganisms located on the surface of a packing. The filter comprises a sealed vessel in which the packing having the biomass thereon is located, and the waste water, mixed with several volumes of liquid recycle, is allowed to trickle downwardly through the packing countercurrently to ascending gases, effluent liquid is removed from the bottom of the vessel at a rate sufficient to maintain the level of effluent liquid below the packing in order to prevent the packing from being submerged in liquid. The apparatus and process are applicable to the anaerobic methanogenic processes wherein methane is produced as a product; and are also applicable to non-methanogenic processes which are conducted in the absence of added molecular oxygen wherein combined nitrogen is converted to molecular nitrogen.Type: GrantFiled: February 6, 1980Date of Patent: September 28, 1982Assignee: Celanese CorporationInventor: Enrique R. Witt
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Patent number: 4338196Abstract: In the treatment of a waste water containing formaldehyde by a method which involves introducing the waste water into a biological digestor into which there is also introduced another stream comprising a nitrogen-containing compound, especially ammonia or an ammonium salt, process difficulty caused by the formation of refractory adducts of the formaldehyde with the nitrogen compound (especially hexamethylenetetramine) is minimized by introducing the waste water and the nitrogen compound into the digestor in two separate streams instead of allowing the two streams to mix in the digestor feed line or in a preliminary holding pond. The method is especially applicable in systems in which ammonia or some other source of ammonium ions is introduced into the digestor as a nutrient for the contained biomass.Type: GrantFiled: July 5, 1979Date of Patent: July 6, 1982Assignee: Celanese CorporationInventor: Leanne Mayerle
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Patent number: 4329511Abstract: In hydroformylating an olefinic compound to produce an aldehyde derivative thereof employing as catalyst a complex of a Group VIII metal and an organic ligand dissolved in an inert liquid reaction solvent with the aldehyde product being continuously stripped out of the solvent, stripping is facilitated while by-product formation is kept at a minimum by using a solvent of specially-chosen high molecular weight while also controlling the degree of stripping as desired to maintain in the reaction medium a controlled molar concentration of the aldehyde hydroformylation product.Type: GrantFiled: June 23, 1980Date of Patent: May 11, 1982Assignee: Celanese CorporationInventors: Edward B. Hackman, Larry D. Zeagler, James S. McLaughlin, Carl M. Peabody
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Patent number: 4301298Abstract: A normally liquid hydrocarbon having a minimum boiling point of about 425.degree. F. is utilized to provide the liquid seal in a vacuum pump which intakes a gaseous light ends stream resulting from a process for the production of ethyl acrylate by the reaction of ethylene with acrylic acid in the presence of a sulfuric acid catalyst. Upon contact in the vacuum pump, the gaseous light ends are partially absorbed into the normally liquid hydrocarbon, with the normally liquid hydrocarbon being recovered by fractionation.Type: GrantFiled: May 23, 1980Date of Patent: November 17, 1981Assignee: Celanese CorporationInventors: Theodore Horlenko, James L. Paul, James W. Gordon
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Patent number: 4289912Abstract: The tendency of liquid paraformaldehyde containing water and paraformaldehyde in, for example, approximately 80% to approximately 90% concentration to precipitate solid paraformaldehyde therefrom is retarded by the incorporation thereinto of an effective amount of a moderator or stabilizer selected from the group consisting of polyacrylic acid, tartaric acid, dl-malic acid, ethylenediaminetetraacetic acid, and citric acid. The prior-art stabilizers known and used for lower-concentration formaldehyde solutions of, for example, about 50% strength are not effective. Conversely, the present moderators are not effective in the lower-concentration solutions.Type: GrantFiled: May 2, 1980Date of Patent: September 15, 1981Assignee: Celanese CorporationInventors: Marvin E. Harris, Jr., Hubert H. Thigpen
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Patent number: 4257921Abstract: A butene may be oxidized in the vapor phase at elevated temperatures to produce acetic acid by reacting the butene with molecular oxygen in the presence of a catalyst comprising a composition of the empirical formula:V.sub.f Sb.sub.g X.sub.h Me.sub.i O.sub.jwherein V is vanadium, Sb is antimony, and O is oxygen, wherein X represents a metal which is one or more of Bi, Nb, Co, Nd, Sm, Zn, Zr or Cr, and wherein Me represents a metal which is one or more of Al, Fe or Sn, the metal represented by Me being optionally present.Type: GrantFiled: November 23, 1979Date of Patent: March 24, 1981Assignee: Celanese CorporationInventors: William E. Slinkard, Anthony B. Baylis
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Patent number: 4221744Abstract: An improved process for hydroformylating an ethylenically-unsaturated compound to form an aldehyde derivative thereof in the presence of rhodium hydridocarbonyl in complex combination with an organic ligand, characterized by employing as said organic ligand a compound having two phosphino moieties, one being of the formula: ##STR1## and the other being of the formula: ##STR2## wherein R.sub.1, R.sub.2, R.sub.1 ', and R.sub.2 ' are organic radicals at least one of which contains an electronegative substituent moiety. The presence of the electronegative substituent in the ligand leads to an increased ratio of linear aldehyde to branched-chain aldehyde in the hydroformylation reaction product.Type: GrantFiled: December 1, 1978Date of Patent: September 9, 1980Assignee: Celanese CorporationInventor: Jerry D. Unruh
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Patent number: 4219671Abstract: A butene may be oxidized in the vapor phase at elevated temperatures to produce acetic acid by reacting the butene with molecular oxygen in the presence of a catalyst comprising a composition of the empirical formula:V.sub.f Sb.sub.g X.sub.h Me.sub.i O.sub.Jwherein V is vanadium, Sb is antimony, and O is oxygen, wherein X represents a metal which is one or more of Bi, Nb, Co, Nd, Sm, Zn, Zr or Cr, and wherein Me represents a metal which is one or more of Al, Fe or Sn, the metal represented by Me being optionally present.Type: GrantFiled: August 29, 1977Date of Patent: August 26, 1980Assignee: Celanese CorporationInventors: William E. Slinkard, Anthony B. Baylis
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Patent number: 4201868Abstract: A process for the reacting of methanol with carbon monoxide and hydrogen to produce increased amounts of methyl acetate, acetaldehyde and dimethyl acetal utilizing a catalyst comprising a cobalt carbonyl in complex with an organic nitrogen ligand.Type: GrantFiled: February 25, 1977Date of Patent: May 6, 1980Assignee: Celanese CorporationInventor: William E. Slinkard
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Patent number: 4198351Abstract: An improvement in the process for production of formaldehyde wherein a vapor phase mixture of methanol and air are passed over a silver catalyst, comprising the incorporation of a small amount of a halogen-containing compound into the mixture.Type: GrantFiled: April 15, 1977Date of Patent: April 15, 1980Assignee: Celanese CorporationInventors: Anthony J. Branecky, David W. Harris
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Patent number: 4193943Abstract: 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 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: April 24, 1978Date of Patent: March 18, 1980Assignee: Celanese CorporationInventors: Jerry D. Unruh, William J. Wells, III
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Patent number: 4190606Abstract: 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. The present method can also be used to suppress formation of halogenated carbonyl compounds in processes where conditions exist which favor such formation.Type: GrantFiled: October 17, 1977Date of Patent: February 26, 1980Assignee: Celanese CorporationInventor: George A. Blay
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Patent number: 4168391Abstract: An improvement in the process wherein carbon monoxide and hydrogen are reacted in the liquid phase in the presence of a cobalt carbonyl catalyst whereby increased amounts of ethanol may be produced, which improvement comprises conducting the reaction in the presence of a non-polar, substantially inert, oxygenated hydrocarbon solvent.Type: GrantFiled: December 5, 1977Date of Patent: September 18, 1979Assignee: Celanese CorporationInventors: William E. Slinkard, Anthony B. Baylis
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Patent number: 4156633Abstract: Acrolein and other light ends are removed from the effluent of a process for the production of acrylic acid by the vapor phase catalytic oxidation of acrolein or an acrolein precursor, such as propylene, by passing the effluent to the base of a fractionation tower and contacting such with the descending stream of liquid within the tower so as to partially condense the condensibles in the effluent, a portion of the liquid bottoms being recycled to the upper portions of the tower and a portion withdrawn as crude acrylic acid product. Acrolein is removed overhead.Type: GrantFiled: July 29, 1976Date of Patent: May 29, 1979Assignee: Celanese CorporationInventors: Theodore Horlenko, Gene J. Fisher
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Patent number: 4152344Abstract: An improved process for hydroformylating an ethylenically-unsaturated compound to form an aldehyde derivative thereof in the presence of rhodium hydridocarbonyl in complex combination with an organic ligand, characterized by employing as said organic ligand a compound having two phosphino moieties, one being of the formula: ##STR1## and the other being of the formula: ##STR2## wherein R.sub.1, R.sub.2, R.sub.1 ', and R.sub.2 ' are organic radicals at least one of which contains an electronegative substituent moiety. The presence of the electronegative substituent in the ligand leads to an increased ratio of linear aldehyde to branched-chain aldehyde in the hydroformylation reaction product.Type: GrantFiled: August 8, 1977Date of Patent: May 1, 1979Assignee: Celanese CorporationInventor: Jerry D. Unruh
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Patent number: 4151209Abstract: In a process for hydroformylating an olefin in the presence of a catalyst comprising rhodium in complex combination with carbon monoxide and a triorganophosphorus ligand, progressive deactivation of the catalyst, as well as loss of the ligand species through by-product formation, are reduced by continuously stripping the liquid reaction medium to a degree such that the content of high-boiling organophosphorus by-products therein is maintained at a low level such that the ratio of phosphorus contained in said high-boiling by-products to phosphorus contained in the ligand present in the reaction medium does not exceed about 0.2.Type: GrantFiled: October 28, 1977Date of Patent: April 24, 1979Assignee: Celanese CorporationInventors: James L. Paul, Wendell L. Pieper, Leslie E. Wade
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Patent number: 4146734Abstract: A butene may be oxidized in the vapor phase at elevated temperatures to produce acetic acid by reacting the butene with molecular oxygen in the presence of a catalyst comprising a composition of the empirical formula:V.sub.a X.sub.b Ce.sub.c Me.sub.d O.sub.ewherein V is vanadium, Ce is cerium, and O ix oxygen, wherein X represents a metal which is one or more of Y, La, Pr, Nd, Sm, Eu, Gd, Dy and Yb, and wherein Me represents a metal which is one or more of Bi, Ti, Zn and Sn or mixtures thereof, Ce and Me being optionally present.Type: GrantFiled: August 8, 1977Date of Patent: March 27, 1979Assignee: Celanese CorporationInventor: William E. Slinkard