Patents Represented by Attorney, Agent or Law Firm M. Susan Spiering
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Patent number: 6494996Abstract: A process for separating water from methanol in an aqueous methanol initial mixture, including subjecting said mixture to azeotropic distillation in the presence of sufficient added methyl acrylate to form an azeotrope with most of the methanol in said initial mixture such that a substantial proportion of methanol in the initial mixture is removed as an azeotrope of methanol and methyl acrylate in the overhead vapors resulting from said distillation and a major proportion of water in said initial mixture is removed in the liquid residue of said distillation.Type: GrantFiled: January 22, 2001Date of Patent: December 17, 2002Assignee: Celanese International CorporationInventors: Benjamin A. Gilbert, Jeffrey R. Kirkpatrick, John C. McCall, Kenneth A. Windhorst
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Patent number: 6485609Abstract: This invention relates to an improvement in coatings particularly suited for the preparation of paper products having an ink jet coating applied thereto and to the resulting paper products. The improvement in ink jet coatings resides in the incorporation of a primary amine functional polyvinyl alcohol (PVOH/PVNH2) as a polymeric binder. One form of an amine functional polyvinyl alcohol is produced by the hydrolysis of a copolymer of vinyl acetate and N-vinylformamide or vinyl acetate and allyl amine. Another is the polyvinyl butyral derivative of polyvinyl alcohol which typically is formed by the reaction of a 4-amino alkyl aldehyde dialkyl acetal, such as 4-aminobutyraldehyde dimethyl acetal with polyvinyl alcohol.Type: GrantFiled: March 8, 2001Date of Patent: November 26, 2002Assignee: Celanese International CorporationInventor: John Richard Boylan
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Patent number: 6486093Abstract: A catalyst for the production of vinyl acetate by reaction of ethylene, oxygen and acetic acid comprising a porous support on the porous surfaces of which is deposited catalytically effective amounts of metallic palladium and gold, said catalyst having been prepared by steps comprising impregnating a porous support, the porous surfaces of which contain a catalytically effective amount of a prereduced metallic palladium, with a solution of potassium aurate, and reducing the potassium aurate to a catalytically effective amount of metallic gold. Alternate embodiments are also disclosed.Type: GrantFiled: August 20, 2001Date of Patent: November 26, 2002Assignee: Celanese International CorporationInventors: Tao Wang, Jerry A. Broussard
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Patent number: 6458995Abstract: An improvement to methanol carbonylation processes utilizing a homogeneous iridium catalyst system comprises adding a rate-promoting amount of an insoluble pyridine ring-containing polymer. Typically, polyvinylpyridine is added to the reactor in amounts of up to about 2 wt. percent.Type: GrantFiled: March 31, 2000Date of Patent: October 1, 2002Assignee: Celanese International CorporationInventors: Hung-Cheun Cheung, Elaine C. Sibrel, G. Paul Torrence
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Patent number: 6444842Abstract: The present invention provides an improved method for the preparation of carboxylic acid esters of alkylene glycol monoalkyl ethers by the acid catalyzed esterification of the monoalkyl ether with a carboxylic acid. In a preferred embodiment of the invention, the carboxylic acid and alcohol are reacted in a reactor/column and the resulting ester product is distilled into an overhead decanter/extractor as a single phase. A small amount of solvent, preferably a hydrocarbon is added to the mixture causing the resulting distillate to separate into two phases, one phase containing the desired product, the other containing primarily water. The process described is applicable to both batch and continuous operation and is not constrained by the difficulty of separating closely boiling azeotropes and results in substantially higher production rates than achieved by current processes.Type: GrantFiled: April 19, 2000Date of Patent: September 3, 2002Assignee: Celanese International CorporationInventors: H. Robert Gerberich, R. Jay Warner
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Patent number: 6441076Abstract: Production of a paper coating composition having improved low shear viscosity at a high solids level of fine particle size calcium carbonate. The improvement in low shear viscosity is achieved by dissolving a fine particle size, partially hydrolyzed, low molecular weight poly(vinyl alcohol) powder in an aqueous slurry of pigment particles containing predominantly fine particle size calcium carbonate. Dissolution of the poly(vinyl alcohol) is achieved without external heating or adding water to the slurry. The slurry can then be formulated with other components to produce the ink jet paper coating composition which, when applied to a paper substrate, provides excellent ink jet printability.Type: GrantFiled: September 20, 2001Date of Patent: August 27, 2002Assignee: Celanese International CorporationInventor: John Richard Boylan
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Patent number: 6414065Abstract: Production of a paper coating composition having improved low shear viscosity at a high solids level of fine particle size calcium carbonate. The improvement in low shear viscosity is achieved by dissolving a fine particle size, partially hydrolyzed, low molecular weight poly(vinyl alcohol) powder in an aqueous slurry of pigment particles containing predominantly fine particle size calcium carbonate. Dissolution of the poly(vinyl alcohol) is achieved without external heating or adding water to the slurry. The slurry can then be formulated with other components to produce the ink jet paper coating composition which, when applied to a paper substrate, provides excellent ink jet printability.Type: GrantFiled: November 5, 1999Date of Patent: July 2, 2002Assignee: Celanese International CorporationInventor: John Richard Boylan
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Patent number: 6410817Abstract: Ethylene is a commodity chemical used as a reactant in the production of vinyl acetate. Ethylene is relatively expensive thus making its recovery and re-use in the process encouraged. The present invention provides a method for the recovery of ethylene from the inert gas purge stream from the reactor loop in a vapor-phase process for making vinyl acetate. The method of the present invention includes the steps of contacting the inert gas purge stream containing ethylene with acetic acid in an absorption vessel; discharging a stream containing acetic acid and ethylene from one aspect of the absorption vessel; separating the ethylene from the acetic acid in the stream by contacting the stream with ethylene gas in a scrubber column; and recovering ethylene from a top portion of the scrubber column. The method may also include the step of recycling the recovered ethylene to the reactor loop for further use.Type: GrantFiled: June 29, 1999Date of Patent: June 25, 2002Assignee: Celanese International CorporationInventors: Philip M. Colling, Raul A. Hauser Luna
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Patent number: 6391992Abstract: Oligomers of vinyl esters, preferably of vinyl acetate, are provided in which the molecules contain a single terminal sulfonate group, thereby making these products useful as surface-active agents. These oligomers can be converted by hydrolysis to sulfonate-terminated vinyl alcohol oligomer which is also a surface-active agent. The number average molecular weight of the vinyl ester oligomer is not over 17,000 and not over 7,500 for the vinyl alcohol oligomer. These products are made by polymerizing the vinyl ester in the presence of a bisulfite chain transfer agent in water, preferably with a cosolvent such as methanol. The vinyl ester is delay fed to the polymerization, molecular weight is controlled with the bisulfite, and the system is maintained in a virtual single phase with any organic phase present swollen with water or water and cosolvent.Type: GrantFiled: September 18, 1998Date of Patent: May 21, 2002Assignee: Celanese International CorporationInventors: Robert Krantz Pinschmidt, Jr., Khalil Yacoub
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Patent number: 6350900Abstract: A catalyst for the production of vinyl acetate by reaction of ethylene, oxygen and acetic acid comprising a porous support on the porous surfaces of which is deposited catalytically effective amounts of metallic palladium and gold, said catalyst having been prepared by steps comprising impregnating a porous support, the porous surfaces of which contain a catalytically effective amount of a prereduced metallic palladium, with a solution of potassium aurate, and reducing the potassium aurate to a catalytically effective amount of metallic gold. Alternate embodiments are also disclosed.Type: GrantFiled: June 2, 1998Date of Patent: February 26, 2002Assignee: Celanese International CorporationInventors: Tao Wang, Jerry A. Broussard
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Patent number: 6348256Abstract: Improved ink jet paper coatings which impart high optical density images and excellent water resistance to paper and a process for making an improved ink jet recording paper. The coating formulation comprises an inorganic pigment, preferably silica, and an amine modified poly(vinyl alcohol) composition in which the poly(vinyl alcohol) is graft polymerized with an ethylenically unsaturated monomers containing primary, secondary, tertiary, or quaternary amine functionality.Type: GrantFiled: September 29, 1998Date of Patent: February 19, 2002Assignee: Celanese International CorporationInventors: John Joseph Rabasco, Eric Howard Klingenberg, John Richard Boylan
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Patent number: 6339171Abstract: Disclosed is a method to manufacture high purity acetic acid. Although described in relation to that produced by a low water carbonylation process the present invention is applicable to other mechanisms for production of acetic acid which results in formation of permanganate reducing compounds such as acetaldehyde and its derivatives, and alkyl iodide impurities in intermediate process streams. It has been found that permanganate reducing compounds and alkyl iodides may be conveniently removed from a light phase of an intermediate stream in the reaction process by employing a multiple distillation process coupled with an optional post extraction of acetaldehyde. The distillation process involves first distilling a light phase to concentrate the permanganate reducing compounds, and in particular the acetaldehyde, and then separating the permanganate reducing compounds and alkyl iodides in a second distillation tower.Type: GrantFiled: May 3, 1999Date of Patent: January 15, 2002Assignee: Celanese International CorporationInventors: Madan Singh, George A. Blay, Michael L. Karnilaw, Melchior A. Meilchen, Robin Suzanne Tanke, G. Paull Torrence
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Patent number: 6323364Abstract: The method of the present invention provides an improvement upon prior art methanol carbonylation methods which substantially reduces the production of carbonyl impurities. The production of carbonyl impurities, particularly acetaldehyde, crotonaldehyde, and 2-ethyl crotonaldehyde, in methanol carbonylation reactions has been found to decrease by maintaining less than about 4.5 wt % methyl iodide in the reaction medium during the course of the reaction.Type: GrantFiled: August 31, 1999Date of Patent: November 27, 2001Assignee: Celanese International CorporationInventors: Pramod Agrawal, Hung-Cheun Cheung, Darrell A. Fisher, Valerie Santillan, Mark O. Scates, Elaine C. Sibrel, G. Paul Torrence
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Patent number: 6316679Abstract: A process for treating a composition containing a substantial proportion of trimethyflolpropane bis-monolinear formal (TMP-BMLF) or trimethylolethane bis-monolinear formal (TME-BMLF), e.g., a heavy ends residue obtained from the purification of a crude trimethylolpropane (TMP) or trimethylolethane (TME) product, wherein the composition is contacted at an elevated temperature with a strong acid catalyst, e.g., methanesulfonic acid, to produce a composition containing significantly increased amounts of TMP and trimethylolpropane monocyclic formal (TMP-MCF) or TME and trimethylolethane monocyclic formal (TME-MCF) respectively. Also disclosed is a process for reacting TMP-MCF or TME-MCF, either in substantially pure form or as present in the light ends overhead stream obtained in a finishing treatment of crude TMP or TME, with a monohydric or dihydric alcohol, e.g., ethylene glycol, in the presence of a strong acid catalyst to obtain additional TMP or TME and an acetal by-product, e.g.Type: GrantFiled: May 26, 2000Date of Patent: November 13, 2001Assignee: Celanese International CorporationInventors: Carolyn Supplee, Jerry A. Broussard, Tobin J. Marks, William E. Slinkard, Edwards G. Zey
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Patent number: 6303813Abstract: The method of the present invention provides an improvement upon prior art methanol carbonylation methods which substantially reduces the production of carbonyl impurities. The production of carbonyl impurities, particularly acetaldehyde, crotonaldehyde, and 2-ethyl crotonaldehyde, in methanol carbonylation reactions has been found to decrease by maintaining a partial pressure of hydrogen between about 0.1 and 4 psia at reaction total pressure of from about 15 to about 40 atmospheres total reaction pressure.Type: GrantFiled: August 31, 1999Date of Patent: October 16, 2001Assignee: Celanese International CorporationInventors: Mark O. Scates, Valerie Santillan, Pramod Agrawal, G. Paull Torrence, R. Jay Warner
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Patent number: 6299736Abstract: Gamma-Butyrolactone (GBL) is recovered from a mixture containing GBL and other heavy organics by a process of azeotropic distillation in the presence of a C8-C 10 hydrocarbon as an azeotroping agent, wherein an azeotrope of GBL and the hydrocarbon is obtained as a distillate, which forms immiscible GBL-rich and hydrocarbon-rich phases, and the hydrocarbon-rich phase is decanted or isolated from the GBL-rich phase. By this process GBL can be efficiently separated from a large proportion of various compounds having boiling points close to that of GBL, e.g., the methyl-&ggr;-butyrolactones (MeGBL's).Type: GrantFiled: June 15, 1999Date of Patent: October 9, 2001Assignee: Celanese International CorporationInventors: Kenneth A. Windhorst, H. Robert Gerberich, Deborah A. Sitz, Nicole Garrett-Wallace, R. Jay Warner
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Patent number: 6274531Abstract: A catalyst for the production of vinyl acetate by reaction of ethylene, oxygen and acetic acid comprising a porous support on the porous surfaces of which is deposited catalytically effective amounts of metallic palladium and gold, and cupric acetate. Use of this catalyst results in a reaction having a relatively low selectivity to carbon dioxide.Type: GrantFiled: June 23, 1999Date of Patent: August 14, 2001Assignee: Celanese International CorporationInventors: Ioan Nicolau, Jerry A. Broussard, Philip M. Colling
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Patent number: 6251256Abstract: A process for electrochemical oxidation of aldehydes to esters is provided. The invention includes electrooxidation at a pH where an intermediate hemiacetal is favored, thereby providing for maximum selectivity to the desired ester and for maximum reaction efficiency. In particular, the invention provides for the electrooxidation of acetaldehyde to methyl acetate. The invention is illustrated with reference reactants native to the carbonylation process for the manufacture of acetic acid. Processes described herein are readily adapted to an industrial scale, particularly for the removal of acetaldehyde from process streams.Type: GrantFiled: February 4, 1999Date of Patent: June 26, 2001Assignee: Celanese International CorporationInventors: George A. Blay, Ricardo E. Borjas
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Patent number: 6211405Abstract: The present invention provides a process for the carbonylation of an alcohol, ether or ester to products comprising a carboxylic acid, the anhydride thereof or coproduction of the carboxylic acid and anhydride. More particularly, the present invention provides a process for the carbonylation of methanol to produce acetic acid by reacting methanol with carbon monoxide in a liquid reaction medium containing a catalyst comprising rhodium, iridium, iodide ion, and said reaction medium further comprising water, acetic acid, methyl iodide, and methyl acetate and subsequently recovering acetic acid from the resulting reaction product.Type: GrantFiled: October 23, 1998Date of Patent: April 3, 2001Assignee: Celanese International CorporationInventors: Hung-Cheun Cheung, Elaine C. Sibrel, Robin S. Tanke, G. Paull Torrence
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Patent number: 6207859Abstract: A process for inhibiting free-radical polymerization of an alpha,beta-unsaturated (&agr;,&bgr;-unsaturated) carboxylic acid, and for providing desired grade &agr;,&bgr;-unsaturated carboxylic acid for use following storage and transport is described herein. In particular, bulk storage and shipment such as with overseas transport is described. The process comprises combining the &agr;,&bgr;-unsaturated carboxylic acid with a phenolic inhibitor and a coinhibitor to form an inhibited mixture, storing the inhibited mixture, transporting the inhibited mixture, and removing the coinhibitor to provide the desired grade &agr;,&bgr;-unsaturated carboxylic acid for use. In preferred embodiments, the &agr;,&bgr;-unsaturated carboxylic acid is acrylic acid, the phenolic inhibitor is p-methoxyphenol, the coinhibitor is manganese cation, and removal of the coinhibitor is carried out using an ion exchange resin.Type: GrantFiled: September 23, 1999Date of Patent: March 27, 2001Assignee: Celanese International CorporationInventors: Leon B. Levy, Edward F. Dougherty, Charles C. Hobbs, Jr., Jerome F. Perez, Mark O. Scates, Madan Singh