Esterification Of Acid, Salt, Acid Halide Or Anhydride With Alcohol Patents (Class 560/98)
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Patent number: 11104636Abstract: The present disclosure relates to a manufacturing system and a manufacturing method which are capable of continuously manufacturing an ester-based composition, and has a technical feature of being capable of manufacturing an ether-based composition continuously, economically, and efficiently.Type: GrantFiled: April 2, 2020Date of Patent: August 31, 2021Assignee: LG Chem, Ltd.Inventors: Hyun Kyu Kim, Sung Kyu Lee, Hyoung Jun, Chan Hyu Jin, Jeong Ju Moon, Joo Ho Kim
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Patent number: 11091422Abstract: Provided is a monohydric alcohol removal method in esterification, the method including a step of reacting a carbonyl-based compound having one or more functional groups selected from the group consisting of carboxyl, ester, and acid anhydride groups with a monohydric alcohol in an esterification reactor including a liquid phase outlet line connected to a liquid phase section in the reactor, and a step of separating in a gas-liquid separation column to remove the monohydric alcohol, wherein the inflow of a liquid phase stream into the gas-liquid separation column starts at the time point between 10% and 70% of the total time required for the gas-liquid separation.Type: GrantFiled: September 5, 2018Date of Patent: August 17, 2021Assignee: LG CHEM, LTD.Inventors: Ha Na Lee, Sung Kyu Lee, Joon Ho Shin, Hyoung Jun
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Patent number: 10941039Abstract: Dihydrogen metaphosphate can be synthesized via protonation, and can react with a dehydrating agent to afford tetrametaphosphate anhydride. A monohydrogen tetrametaphosphate organic ester can be derived from the anhydride. A metal tetrametaphosphate complex can be prepared using a metal salt and a dihydrogen tetrametaphosphate.Type: GrantFiled: July 1, 2018Date of Patent: March 9, 2021Assignee: MASSACHUSETTS INSTITUTE OF TECHNOLOGYInventors: Yanfeng Jiang, Khetpakorn Chakarawet, Julia Stauber, Christopher Colin Cummins
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Patent number: 10457630Abstract: The invention relates to a method for producing a (meth)acrylic ester with improved productivity, by transesterfication of a light alkyl (meth)acrylate with a heavy alcohol. The method of the invention includes the recycling of noble products recovered after the thermal treatment of heavy fractions generated during the synthesis, said thermal treatment being carried out in the presence of a dialkyl phthalate, the alkyl chain of which corresponds to that of the light alkyl (meth)acrylate. The invention applies to the production of N,N-dimethyaminoethyl acrylate from ethyl acrylate.Type: GrantFiled: January 28, 2016Date of Patent: October 29, 2019Assignee: Arkema FranceInventors: Yves Cabon, Fanny Dubut, Benoit Riflade
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Patent number: 10017388Abstract: Dihydrogen metaphosphate can be synthesized via protonation, and can react with a dehydrating agent to afford tetrametaphosphate anhydride. A monohydrogen tetra-metaphosphate organic ester can be derived from the anhydride. A metal tetrametaphosphate complex can be prepared using a metal salt and a dihydrogen tetrametaphosphate.Type: GrantFiled: June 5, 2015Date of Patent: July 10, 2018Assignee: MASSACHUSETTS INSTITUTE OF TECHNOLOGYInventors: Yanfeng Jiang, Khetpakorn Chakarawet, Julia Megan Stauber, Christopher Colin Cummins
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Patent number: 10000588Abstract: The present invention relates to coatings for a polymer, the coating comprising a diacrylate of an aliphatic diol, a polyacrylate of an aliphatic polyol, a photoinitiator, wherein the average molecular weight between cross-links in the coating is less than 190 g/mol. The invention further relates to articles comprising the coating and a polymer.Type: GrantFiled: July 13, 2012Date of Patent: June 19, 2018Assignee: Eastman Chemical CompanyInventors: Martin Frederick Schick, Amy Lee Bolton, Jayme Leita, Alisa Annette Williams, Gary Michael Stack, Scott Ellery George
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Patent number: 9828489Abstract: Polymeric compositions are provided that include a furan 2,5-di-ester or tetrahydrofuran 2,5-di-ester plasticizer. The plasticizer has low odor, has good compatibility with a variety of polymers such as hydrophilic polymeric materials, and can be formed from renewable resources. Further, the plasticizer can be used at temperatures often encountered during hot melt processing of polymeric compositions.Type: GrantFiled: September 8, 2014Date of Patent: November 28, 2017Assignee: 3M INNOVATIVE PROPERTIES COMPANYInventors: Kevin M. Lewandowski, Jonathan E. Janoski
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Patent number: 9725401Abstract: A process for production of C4 to C15 esters by the esterification of a carboxylic acid or anhydride with a C4 to C15 alcohol including forming a reaction mixture of the acid or anhydride and the C4 to C15 alcohol including a stoichiometric excess of the alcohol is provided.Type: GrantFiled: July 19, 2011Date of Patent: August 8, 2017Assignee: ExxonMobil Chemical Patents Inc.Inventors: Nicolaas A. De Munck, Eddy T. A. Van Driessche
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Publication number: 20150080545Abstract: In a process for producing 3,4? and/or 4,4? dimethyl-substituted biphenyl compounds, a feed comprising toluene is contacted with hydrogen in the presence of a hydroalkylation catalyst under conditions effective to produce a hydroalkylation reaction product comprising (methylcyclohexyl)toluenes. At least part of the hydroalkylation reaction product is dehydrogenated in the presence of a dehydrogenation catalyst under conditions effective to produce a dehydrogenation reaction product comprising a mixture of dimethyl-substituted biphenyl isomers. The dehydrogenation reaction product is then separated into at least a first stream containing at least 50% of 3,4? and 4,4? dimethylbiphenyl isomers by weight of the first stream and at least one second stream comprising one or more 2,x? (where x? is 2?, 3?, or 4?) and 3,3? dimethylbiphenyl isomers.Type: ApplicationFiled: September 8, 2014Publication date: March 19, 2015Inventors: Jihad M. Dakka, Lorenzo C. DeCaul, Keith H. Kuechler, Neeraj Sangar, Michael Salciccioli, Alan A. Galuska, Gary D. Mohr
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Publication number: 20150051420Abstract: Embodiments of an invention disclosed herein relate to methods to produce terephthalate esters, the methods include esterifying at least one C6-C13 alcohol with dimethyl terephthalate (DMT) in the presence of a catalyst to produce the terephthalate esters.Type: ApplicationFiled: March 8, 2013Publication date: February 19, 2015Inventor: Nicholaas A. De Munck
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Patent number: 8907118Abstract: The invention relates to a method for producing acyloxy benzoic acids of the formula (I), in which R1 is a linear or branched saturated alkyl group with 6 to 30 carbon atoms, a linear or branched mono- or polyunsaturated alkenyl group with 6 to 30 carbon atoms, or an aryl group with 6 to 30 carbon atoms. The acyloxy benzoic acids of the formula (I) are produced from para-hydroxy benzoic acid and a corresponding carboxylic acid halide in the presence of an alkali hydroxide.Type: GrantFiled: August 6, 2011Date of Patent: December 9, 2014Assignee: Clariant International Ltd.Inventors: Melanie Sajitz, Gerd Reinhardt, Isabel Scheffer, Werner Janitschek, Ina Herrgen
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Patent number: 8901343Abstract: The invention relates to a method for producing carboxylic esters by converting a carboxylic acid or a carboxylic acid anhydride or a mixture thereof with an alcohol in a reaction system comprising one or more reactors, wherein reaction water is distilled as alcohol-water-azeotrope with the vapors, the vapors are at least partially condensed, the condensate is separated into an aqueous phase and an organic phase and said organic phase is supplied at least partially back into said reaction system. Components boiling lower than the alcohol are at least partially removed from said returned organic phase such as wherein components boiling lower than alcohol are evaporated and/or distilled off. An enrichment in the reaction system of by-products boiling lower than alcohol is avoided. Alcohol losses can be minimized by discharge currents.Type: GrantFiled: December 15, 2009Date of Patent: December 2, 2014Assignee: BASF SEInventors: Walter Disteldorf, Jarren Peters, Thomas Schäfer, Katrin Friese, Christoph Übler
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Patent number: 8901344Abstract: The invention relates to a method for producing carboxylic acid esters by reacting a reaction mixture, comprising a carboxylic acid and/or a carboxylic acid anhydride, and an alcohol in a reaction system having one or more reactors, wherein reaction water is distilled off as an alcohol/water azeotrope with the exhaust vapor. In addition, the reaction mixture is treated with superheated alcohol vapor. The method allows the production of esters having a low acid number.Type: GrantFiled: December 15, 2009Date of Patent: December 2, 2014Assignee: BASF SEInventors: Jarren Peters, Walter Disteldorf, Katrin Friese, Thomas Schäfer, Oliver Bey
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Patent number: 8901342Abstract: The invention relates to a method for producing acyloxy benzoic acids of the formula (I), in which R1 is a linear or branched saturated alkyl group with 6 to 30 carbon atoms, a linear or branched mono- or polyunsaturated alkenyl group with 6 to 30 carbon atoms, or an aryl group with 6 to 30 carbon atoms. The acyloxy benzoic acids of the formula (I) are produced from para-hydroxy benzoic acid and a corresponding carboxylic acid halogenide in the presence of a base and are advantageously suitable for use as activators for hydrogen peroxide.Type: GrantFiled: August 6, 2011Date of Patent: December 2, 2014Assignee: Clariant International LtdInventors: Melanie Sajitz, Isabel Scheffer, Werner Janitschek
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Patent number: 8815992Abstract: Tetraesters of a C4-C5 aliphatic tetracarboxylic acid and OXO-alcohols and plasticized compositions containing said tetraesters are provided.Type: GrantFiled: April 13, 2011Date of Patent: August 26, 2014Assignee: ExxonMobil Research and Engineering CompanyInventors: Lisa Saunders Baugh, Enock Berluche, Karla Schall Colle, Manika Varma-Nair, Ramzi Yanni Saleh, Jon Edmond Randolph Stanat, Stephen Zushma, Victor DeFlorio
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Publication number: 20140212666Abstract: Provided are compounds of the following: wherein R1 is a saturated or unsaturated cyclic hydrocarbon optionally substituted with an alkyl and/or an OXO-ester, and R2 is a C4 to C14 hydrocarbyl, preferably the residue of a C4 to C14 OXO-alcohol. Also provided are processes for making the compounds and plasticized polymer compositions containing said compounds.Type: ApplicationFiled: January 27, 2014Publication date: July 31, 2014Inventors: Jihad M. Dakka, Lorenzo C. DeCaul, Christine A. Costello, Edmund J. Mozeleski, Pierre Osterrieth, Stephen Zushma, Allen D. Goodwin, Diana Smirnova, Catherine A. Faler, Victor Deflorio, Didier Naert
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Patent number: 8759565Abstract: Disclosed are processes to prepare monocarboxylic acid esters (mono- and/or diesters) of polytrimethylene ether glycol that are substantially free of residues from the catalyst used to produce the polytrimethylene ether glycol esters, as well as methods for their preparation and end uses thereof. The esters, such as the bis-2-ethylhexanoate esters, have uses as functional fluids.Type: GrantFiled: June 23, 2010Date of Patent: June 24, 2014Assignee: E I du Pont de Nemours and CompanyInventors: Hari Babu Sunkara, Raja Hari Poladi, Gyorgyi Fenyvesi
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Patent number: 8729292Abstract: The invention relates to a raw ester of an esterification reaction catalyzed by a metal-containing esterification catalyst generated by a) mixing the raw ester at a temperature T of more than 100° C. under a pressure p that is equal to or greater than the vapor pressure of water at the temperature T with an aqueous base, b) relaxing the ester-base mixture and evaporating water, c) mixing the obtained fluid phase with water forming a water-in-oil emulsion, d) distilling water out of said emulsion and e) filtering the ester. Said method results in esters having low acid value and residues accrue in easily filterable form in the solid catalyst residues.Type: GrantFiled: December 15, 2009Date of Patent: May 20, 2014Assignee: BASF SEInventors: Katrin Friese, Walter Disteldorf, Jarren Peters, Günther Golfier
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Patent number: 8592623Abstract: Polyester polyols are produced from at least one carboxylic acid hydride and diethylene glycol by a process in which the formation of 1,4-dioxane is suppressed. These polyester polyols are useful for producing polyurethane (PUR) and polyisocyanurate (PIR) foams and metal composite elements containing these PUR or PIR foams.Type: GrantFiled: November 3, 2009Date of Patent: November 26, 2013Assignee: Bayer MaterialScience AGInventors: Rolf Roers, Hartmut Nefzger, Erika Bauer, Johannes Van De Braak, Torsten Heinemann, Jürgen Schloβmacher
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Publication number: 20130303796Abstract: A method for continuously preparing a carboxylic acid ester is disclosed. In the method of the present invention, a vertical reactor is filled with a solid catalyst, a carboxylic acid and an alcohol are introduced into a lower part of the vertical reactor, esterification is performed to form an esterized mixture, the esterized mixture is output from an upper part of the vertical reactor, and distillation is performed to isolate the carboxylic acid ester. The method of the present invention is simple, easily controlled and environmental friendly, and has significantly high conversion rate and selectivity.Type: ApplicationFiled: October 15, 2012Publication date: November 14, 2013Applicant: China Petrochemical Development Corporation, Taipei (Taiwan)Inventors: Jih-Dar Hwang, Yung-Shun Kung, Yao-Ching Tsai
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Patent number: 8524938Abstract: The present invention relates to a process for lightening the color of polyol esters by reacting polyols with linear or branched aliphatic monocarboxylic acids having 3 to 20 carbon atoms, wherein the reaction product is worked up without using adsorbents and comprises a treatment with ozone or ozone-containing gases and an immediately subsequent steam treatment with subsequent drying.Type: GrantFiled: October 6, 2010Date of Patent: September 3, 2013Assignee: Oxea GmbHInventors: Guido D. Frey, Thorsten Kreickmann, Heinz Strutz
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Patent number: 8524937Abstract: The present invention relates to a process for preparing polyol esters by reacting polyols with linear or branched aliphatic monocarboxylic acids having 3 to 20 carbon atoms by partial recycling of the aliphatic monocarboxylic acid removed into the esterification reaction or into subsequent esterification batches.Type: GrantFiled: October 6, 2010Date of Patent: September 3, 2013Assignee: Oxea GmbHInventors: Michael Adamzik, Thomas Müller, Willy Schulz, Heyko Jürgen Schultz
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Publication number: 20130225851Abstract: The liquid volume resistivity of plasticiser esters is improved by purifying the ester with an adsorbent having a pH in the range 6 to 11. It is preferable to use a mixture of a filtration aid and an adsorbent. A plasticiser having a desirable combination of high liquid volume resistivity, low amount of light ends and low carbonyl number is obtained.Type: ApplicationFiled: October 3, 2012Publication date: August 29, 2013Applicant: ExxonMobil Chemical Patents Inc.Inventor: ExxonMobil Chemical Patents Inc.
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Publication number: 20130217911Abstract: The invention relates to a method for producing acyloxy benzoic acids of the formula (I), in which R1 is a linear or branched saturated alkyl group with 6 to 30 carbon atoms, a linear or branched mono- or polyunsaturated alkenyl group with 6 to 30 carbon atoms, or an aryl group with 6 to 30 carbon atoms. The acyloxy benzoic acids of the formula (I) are produced from para-hydroxy benzoic acid and a corresponding carboxylic acid halide in the presence of an alkali hydroxide.Type: ApplicationFiled: August 6, 2011Publication date: August 22, 2013Applicant: CLARIANT FINANCE (BVI) LIMITEDInventors: Melanie Sajitz, Gerd Reinhardt, Isabel Scheffer, Werner Janitschek, Ina Herrgen
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Publication number: 20130190525Abstract: According to some aspects, the present disclosure pertains to methods of forming dimethyl 5-tert-butylisophthalate which comprise comprising converting 5-tert-butylisophthalic acid into dimethyl 5-tert-butylisophthalate in synthesis procedures that comprises methanol and a dehydrating agent as chemical reagents. In other aspects, the present disclosure pertains to methods of forming 5-tert-butyl-1,3-bis(1-methoxy-1-methylethyl)benzene that comprise deprotonating 5-tert-butyl-1,3-bis(1-hydroxy-1-methylethyl)benzene with a Brønsted-Lowry superbase and methylating the deprotonated 5-tert-butyl-1,3-bis(1-hydroxy-1-methylethyl)benzene to form the 5-tert-butyl-1,3-bis(1-methoxy-1-methylethyl)benzene.Type: ApplicationFiled: January 23, 2013Publication date: July 25, 2013Applicant: BOSTON SCIENTIFIC SCIMED, INC.Inventor: Boston Scientific Scimed, Inc.
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Patent number: 8481606Abstract: The invention relates to the production and use of polyester polyols, formed from at least one carboxylic acid anhydride and ethylene glycol, wherein a specialized reaction control substantially suppresses the formation of 1,4-dioxane from diethylene glycol.Type: GrantFiled: October 24, 2009Date of Patent: July 9, 2013Assignee: Bayer MaterialScience AGInventors: Hartmut Nefzger, Erika Bauer, Johannes Van de Braak, Jürgen Schloβmacher
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Patent number: 8344174Abstract: The efficiency of catalyzed batch esterification reactions is improved by the use of a particular temperature and pressure profile during the reaction cycle. In particular elevated pressure is maintained to prevent alcohol boil off during initial mixing and reaction of the reactants prior to any catalyst addition, and preferably the pressure is reduced rapidly after the desired reaction temperature has been reached.Type: GrantFiled: March 7, 2008Date of Patent: January 1, 2013Assignee: ExxonMobil Chemical Patents Inc.Inventors: Nicolaas Anthony De Munck, Klaas Bandstra, Raphael Frans Caers, Brady Compton, John Lyford, IV, Aad Gerrit Oskam, Berend Jan Van Der Veen
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Patent number: 8344175Abstract: The invention relates to compounds of Formula (I): The invention further relates to liquid crystal compositions comprising compounds of Formula (I); compositions further comprising one or more chiral compounds; and polymer networks derived from the polymerization of the liquid crystal compositions. Another embodiment relates to processes for providing compounds of Formula (I).Type: GrantFiled: January 25, 2011Date of Patent: January 1, 2013Assignee: E I du Pont de Nemours and CompanyInventors: Marc B. Goldfinger, Jose Manuel Rodriguez-Parada, Lee A. Silverman
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Patent number: 8334393Abstract: The invention relates to compounds of formula (I): wherein R1 and R2 are each independently selected from the group: H, F, Cl and CH3; n1 and n2 are each independently integers 3 to 20; q and r are each independently integers 0, 1 or 2, with the proviso that q+r is ?1; D is a divalent chiral radical selected from the group: wherein R3 is a C1 to C6 straight or branched chain alkyl group; and each B1 and B2 is a divalent radical independently selected from the group: R4-substituted-1,4-phenyl, wherein R4 is H, —CH3 or —OCH3; 2,6-naphthyl; and 4,4?-biphenyl; with the provisos that when q+r=3, at least one of B1 and B2 is R4-substituted-1,4-phenyl; and when q+r=4, at least two of B1 and B2 are R4-substituted-1,4-phenyl. The invention further relates to liquid crystal compositions comprising compounds of formula (I) and polymer networks derived from the polymerization of the liquid crystal compositions.Type: GrantFiled: March 17, 2011Date of Patent: December 18, 2012Assignee: E I du Pont de Nemours and CompanyInventors: Marc B. Goldfinger, Jose Manuel Rodriguez-Parada, Lee A. Silverman, Kai Qi
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Publication number: 20120289636Abstract: A method for preparation of secondary alcohols with a high proportion of hydroxyl group at the C2 position is disclosed. Alkyl carboxylates, high in alpha-methylcarboxylate content, are produced via reaction of an alpha-olefin and a carboxylic acid in the presence of a cerium catalyst. The resultant alkyl carboxylate is hydrolyzed to yield a secondary alcohol with a high 2-hydroxyl content. The secondary alcohol may be used to prepare esters, especially phthalate esters or cyclohexanoate diesters, which are useful as plasticizers. These esters are more effective as plasticizers than esters derived from other secondary alcohols due to their high C2 point of attachment.Type: ApplicationFiled: November 16, 2010Publication date: November 15, 2012Inventors: Karla S. Colle, Allen D. Godwin
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Publication number: 20110282092Abstract: Nitrogen-containing Lewis bases act as poisons for molecular sieve catalysts used in oligomerisation reactions. Lowering their presence in the feed prior to the contacting thereof with the molecular sieve brings a significant extension of catalyst life. Thus, processes that are directed to the lowering of these poisons are provided.Type: ApplicationFiled: June 24, 2011Publication date: November 17, 2011Inventors: John Stephen Godsmark, George Marie Karel Mathys, Hubertus Joseph Beckers, Charles Morris Yarbrough, Stephen Harold Brown, Yeo-Meng Lim
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Patent number: 8034970Abstract: Methods and systems for the production of phthalic acid diesters are described herein. The methods and systems incorporate the novel use of a high shear device to promote dispersion and mixing of a phthalic acid derivative with alcohol. The high shear device may allow for lower reaction temperatures and pressures and may also reduce reaction time with existing catalysts.Type: GrantFiled: June 23, 2008Date of Patent: October 11, 2011Assignee: H R D CorporationInventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Publication number: 20110196159Abstract: A system for mixing ortho-xylene with an oxygen-containing gas such as air comprises an evaporator vessel fed with the gas and having a lance projecting into the gas. The lance is provided with a metal spray nozzle for injecting droplets of hot liquid ortho-xylene into the gas stream, concurrently with the direction of flow of the gas. The metal at the surface of the spray nozzle, that in use is in contact with the liquid ortho-xylene, has a high surface hardness to resist erosion, particularly by cavitation. The system is useful in the production of phthalic anhydride by the oxidation of ortho-xylene with air, whereby the risk for deflagrations is reduced. A soft metal seal is the preferred gasket between the spray nozzle and the lance.Type: ApplicationFiled: September 9, 2008Publication date: August 11, 2011Inventors: Nicolaas Anthony De Munck, Aad Gerrit Oskam, Johnny Jozef Houben, Evert C. Klein
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Patent number: 7910782Abstract: In a hydroformylation reaction, the circulation and recovery of cobalt carbonyl in a cobalt catalyst cycle using carbonylate as an intermediate and acidification thereof, is improved by supplying an aqueous sulfuric acid solution containing less than 16% wt of sulfuric acid to the carbonylate to control sulfuric acid concentration in the carbonylate/acid mixture, before accounting for any acid consuming reaction, to a value of from 2% to 10% by weight. Single step and multistage liquid/liquid extraction techniques as well as vapor/liquid extraction techniques followed by the absorption of cobalt from the vapor in an organic liquid both benefit from this improvement.Type: GrantFiled: March 28, 2008Date of Patent: March 22, 2011Assignee: ExxonMobil Chemical Patents Inc.Inventors: Eddy T. A. Van Driessche, Arie Van Vliet, Raphael Frans Caers, Hubertus Joseph Beckers, Ronald Dean Garton, Bertrand Raymond Da Cruz, Michel J. P. Lepagnol, Edwin Kooke
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Patent number: 7906082Abstract: Method and apparatus for producing biodiesel fuel, i.e., alkyl ester, from vegetable and/or animal oil. A transesterification catalyst is prepared in a base catalyst tank by spraying alkyl alcohol under pressure through jets at metal hydroxide pellets until the pellets have fully reacted with the alcohol. The oil is heated and transesterified in the presence of alkyl alcohol and the transesterification catalyst in a closed, recirculating transesterification flow system under slight cavitation to yield product alkyl ester and product glycerol. Cavitation is achieved by permitting air to enter the transesterification flow system through an adjustable air inlet valve. When permitted to stand, product alkyl ester forms an upper layer that is decanted and subjected to purification steps, to remove particulates and alkyl alcohol from the product alkyl ester, and a lower layer of product glycerol is drained away.Type: GrantFiled: March 23, 2009Date of Patent: March 15, 2011Inventor: Michael F. Pelly
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Patent number: 7834109Abstract: A polyester production facility capable of producing an esterified product stream having a low impurity concentration relative to product streams produced in conventional polyester production facilities.Type: GrantFiled: December 7, 2007Date of Patent: November 16, 2010Assignee: Eastman Chemical CompanyInventors: Bruce Roger DeBruin, Richard Gill Bonner
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Patent number: 7799942Abstract: Disclosed is a process for the preparation of a terephthalic acid di-ester by the esterification of terephthalic acid with an alcohol at elevated and normal temperature and pressure while the water of the reaction is removed from the reaction mixture via an inert gas or a column.Type: GrantFiled: January 30, 2007Date of Patent: September 21, 2010Assignee: Eastman Chemical CompanyInventors: Vickie Haygood Osborne, Phillip Wayne Turner, Steven Leroy Cook
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Publication number: 20100228046Abstract: In a hydroformylation reaction, the circulation and recovery of cobalt carbonyl in a cobalt catalyst cycle using carbonylate as an intermediate and acidification thereof, is improved by supplying an aqueous sulfuric acid solution containing less than 16% wt of sulfuric acid to the carbonylate to control sulfuric acid concentration in the carbonylate/acid mixture, before accounting for any acid consuming reaction, to a value of from 2% to 10% by weight. Single step and multistage liquid/liquid extraction techniques as well as vapour/liquid extraction techniques followed by the absorption of cobalt from the vapour in an organic liquid both benefit from this improvement.Type: ApplicationFiled: March 28, 2008Publication date: September 9, 2010Inventors: Eddy T.A. Van Driessche, Arie Van Vliet, Raphael Frans Caers, Hubertus Joseph Beckers, Ronald Dean Garton, Bertrand Raymond Da Cruz, Michel J.P. Lepagnol, Edwin Kooke
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Patent number: 7741509Abstract: Disclosed is a process for the preparation of di-n-butyl terephthalate by the esterification of terephthalic acid with n-butanol in the presence of a strong acid while employing a fractionating column.Type: GrantFiled: April 3, 2007Date of Patent: June 22, 2010Assignee: Eastman Chemical CompanyInventors: Steven Leroy Cook, Phillip Wayne Turner, Vickie Haygood Osborne
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Patent number: 7737315Abstract: The invention relates to the use of isobutene-containing olefin feedstock in oligomerization reactions, particularly in the production of octenes as feedstock for the manufacture of plasticizer alcohols, the process comprising contacting a feed comprising isobutene with a molecular sieve at a temperature in excess of 240° C. to produce a product low in triple-branched octenes.Type: GrantFiled: January 28, 2009Date of Patent: June 15, 2010Assignee: ExxonMobil Chemical Patents Inc.Inventors: Stephen Harold Brown, Georges Marie Mathys
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Publication number: 20100137631Abstract: The efficiency of catalysed batch esterification reactions is improved by the use of a particular temperature and pressure profile during the reaction cycle. In particular elevated pressure is maintained to prevent alcohol boil off during initial mixing and reaction of the reactants prior to any catalyst addition, and preferably the pressure is reduced rapidly after the desired reaction temperature has been reached.Type: ApplicationFiled: March 7, 2008Publication date: June 3, 2010Inventors: Nicolaas Anthony De Munck, Klaas Bandstra, Raphael Frans Caers, Brady Compton, John Lyford, IV, Aad Gerrit Oskam, Berend Jan Van Der Veen
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Publication number: 20100130767Abstract: A process for producing esters comprises esterifying an acid or anhydride with an excess of an alcohol to produce a crude ester, recovering excess alcohol from the crude ester and recycling recovered excess alcohol to the esterification reaction together with fresh alcohol. The process is improved by controlling the ratio of the amount of recycled alcohol and the amount of fresh alcohol in dependence on the level of impurities in the recycle alcohol. Further improvements come from feed forwarding fresh alcohol analysis results and from preheating the alcohol before loading into the reactor. Preferably, ester product quality is improved by stripping the alcohol for oxygen removal prior to esterification.Type: ApplicationFiled: March 7, 2008Publication date: May 27, 2010Inventors: Nicolaas Anthony De Munck, Brady Compton, John Lyford, IV, Aad Gerrit Oskam
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Publication number: 20100108940Abstract: A method for performing a flying grade switch in an ester production process, which preferably is operated in semi-continuous mode, maximises plant equipment productivity while minimizing product cross-contamination. Mixed ester products of the process containing a C9-C11 alkyl or isodecyl benzoate together with a higher molecular weight di-alkyl phthalate or cyclohexanoate, bring performance advantages such as improved permanence in plasticised PVC articles or improved processability in manufacturing these articles.Type: ApplicationFiled: March 7, 2008Publication date: May 6, 2010Inventors: Nicolaas Anthony De Munck, Allen David Godwin, Thomas Marshall Larson, Paul H. Daniels, Didier Naert
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Publication number: 20090105496Abstract: A pyridine-free esterification reagent for anhydride method to determine the hydroxyl number of polyols is provided. The reagent includes an anhydride, an oxometallic complex having a formula of MOmLn, and a neutral or slightly acidic solvent, wherein M includes transition metals of IVB, VB, or VIB group, L includes (OTf), X, and m and n are an integer greater than or equal to 1, wherein X is halogen, and R, R?, R?, and R??, independently, are alkyl, aryl, or heterocyclic groups containing nitrogen, oxygen, phosphorus, or sulfur heteroatoms. The invention also provides a method to determine the hydroxyl number of polyols.Type: ApplicationFiled: April 22, 2008Publication date: April 23, 2009Applicant: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTEInventors: Chih-Chien Lin, Chien-Tien Chen
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Patent number: 7501548Abstract: The invention relates to the use of isobutene-containing olefin feedstock in oligomerization reactions, particularly in the production of octenes as feedstock for the manufacture of plasticizer alcohols, the process comprising contacting a feed comprising isobutene with a molecular sieve at a temperature in excess of 240° C. to produce a product low in triple-branched octenes.Type: GrantFiled: March 10, 2006Date of Patent: March 10, 2009Assignee: ExxonMobil Chemical Patents Inc.Inventors: Stephen Harold Brown, Georges Marie Mathys
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Publication number: 20090005587Abstract: Methods and systems for the production of phthalic acid diesters are described herein. The methods and systems incorporate the novel use of a high shear device to promote dispersion and mixing of a phthalic acid derivative with alcohol. The high shear device may allow for lower reaction temperatures and pressures and may also reduce reaction time with existing catalysts.Type: ApplicationFiled: June 23, 2008Publication date: January 1, 2009Applicant: H R D CORPORATIONInventors: Abbas HASSAN, Ebrahim BAGHERZADEH, Rayford G. ANTHONY, Gregory BORSINGER, Aziz HASSAN
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Patent number: 7381354Abstract: Flame retardant formulations comprised of at least one bromine-containing polyol are produced by a process which comprises: A) heating a mixture formed from components comprised of (i) tetrabromophthalic anhydride, (ii) at least one aliphatic polyol, and (iii) at least one liquid straight chain aliphatic diester of a straight-chain alkane dicarboxylic acid to form an intermediate composition; and B) contacting all or a portion of the intermediate composition one or more times with (iv) at least one alkylene oxide that results in the formation of a liquid product formulation, and optionally, removing any excess alkylene oxide present; the amounts of (i), (ii), (iii), and (iv) used being proportioned to form a formulation having a bromine content of at least about 40 wt %, a viscosity at 25° C. of about 20,000 cps or less, and an acid number as determinable by aqueous sodium hydroxide titration and expressed in terms of potassium hydroxide, of less than about 1 milligram of KOH per gram of the formulation.Type: GrantFiled: May 21, 2007Date of Patent: June 3, 2008Assignee: Albemarle CorporationInventors: Elbert F. Feske, Nelson E. Clark, Arthur G. Mack, Jeffrey Todd Aplin
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Patent number: 7323586Abstract: Mixtures of isomeric dialkyl phthalates that have a desired viscosity are prepared by esterifying phthalic acid or phthalic anhydride with a mixture of isomeric alkyl alcohols having a certain carbon number of carbon atoms, where the molar fraction of each alkyl alcohol isomer of the isomeric alcohol mixture is determined, and where the viscosity parameter of each alkyl alcohol isomer of the alcohol mixture, which, upon reacting with phthalic acid or phthalic anhydride, results in a mixed isomer dialkyl phalate ester product having a specific desired viscosity, is determined in accordance with formula (I): ln(?)=??i*ln(?i) ??(I) where ?=the calculated viscosity of a dialkyl phthalate mixture, ?i=the molar fraction of an isomerically pure alcohol (i), and ?i=the viscosity parameter of isomerically pure alcohol (i).Type: GrantFiled: September 20, 2002Date of Patent: January 29, 2008Assignee: Oxeno Olefinchemie GmbHInventors: Klaus-Diether Wiese, Michael Grass, Wilfried Bueschken
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Patent number: 7307183Abstract: A method for preparing tetrabromobenzoate ester from a tetrabromophthalic anhydride including the steps of reacting the tetrabromophthalic anhydride with a catalyst and an alcohol at a temperature that favors partial esterification over complete esterification of the tetrabromophthalic anhydride to form a tetrabromophthalate half-ester reaction mixture; and feeding the half-ester reaction mixture to at least one reactor having and maintaining a temperature that favors decarboxylation over esterification to produce a tetrabromobenzoate ester-containing product. The temperature favoring partial esterification of the tetrabromophthalic anhydride is between about 70° C. and 130° C. The temperature favoring decarboxylation over esterification is between about 190° C. and 205° C. The tetrabromobenzoate ester-containing product comprises at least about 85% tetrabromobenzoate ester. The at least one reactor may include two or more reactors connected to one another in series.Type: GrantFiled: July 29, 2003Date of Patent: December 11, 2007Assignee: Great Lakes Chemical CorporationInventors: David W. Bartley, James D. Siebecker, Stephen B. Falloon
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Patent number: 7265238Abstract: An advantageous process is provided for preparing methyl 4-(aminomethyl)benzoate by esterifying 4-(aminomethyl)benzoic acid and subsequently obtaining the methyl 4-(aminomethyl)benzoate, this process proceeding under specific pH and temperature control and isolation of the hydrochloride of methyl 4-(aminomethyl)benzoate formed as an intermediate being avoidable.Type: GrantFiled: September 22, 2006Date of Patent: September 4, 2007Assignee: Saltigo GmbHInventors: Michael Dockner, Torsten Neugebauer