Esterification Of Acid, Salt, Acid Halide Or Anhydride With Alcohol Patents (Class 560/98)
  • Patent number: 10457630
    Abstract: 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: Grant
    Filed: January 28, 2016
    Date of Patent: October 29, 2019
    Assignee: Arkema France
    Inventors: Yves Cabon, Fanny Dubut, Benoit Riflade
  • Patent number: 10017388
    Abstract: 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: Grant
    Filed: June 5, 2015
    Date of Patent: July 10, 2018
    Assignee: MASSACHUSETTS INSTITUTE OF TECHNOLOGY
    Inventors: Yanfeng Jiang, Khetpakorn Chakarawet, Julia Megan Stauber, Christopher Colin Cummins
  • Patent number: 10000588
    Abstract: 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: Grant
    Filed: July 13, 2012
    Date of Patent: June 19, 2018
    Assignee: Eastman Chemical Company
    Inventors: Martin Frederick Schick, Amy Lee Bolton, Jayme Leita, Alisa Annette Williams, Gary Michael Stack, Scott Ellery George
  • Patent number: 9828489
    Abstract: 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: Grant
    Filed: September 8, 2014
    Date of Patent: November 28, 2017
    Assignee: 3M INNOVATIVE PROPERTIES COMPANY
    Inventors: Kevin M. Lewandowski, Jonathan E. Janoski
  • Patent number: 9725401
    Abstract: 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: Grant
    Filed: July 19, 2011
    Date of Patent: August 8, 2017
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Nicolaas A. De Munck, Eddy T. A. Van Driessche
  • Publication number: 20150080545
    Abstract: 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: Application
    Filed: September 8, 2014
    Publication date: March 19, 2015
    Inventors: Jihad M. Dakka, Lorenzo C. DeCaul, Keith H. Kuechler, Neeraj Sangar, Michael Salciccioli, Alan A. Galuska, Gary D. Mohr
  • Publication number: 20150051420
    Abstract: 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: Application
    Filed: March 8, 2013
    Publication date: February 19, 2015
    Inventor: Nicholaas A. De Munck
  • Patent number: 8907118
    Abstract: 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: Grant
    Filed: August 6, 2011
    Date of Patent: December 9, 2014
    Assignee: Clariant International Ltd.
    Inventors: Melanie Sajitz, Gerd Reinhardt, Isabel Scheffer, Werner Janitschek, Ina Herrgen
  • Patent number: 8901342
    Abstract: 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: Grant
    Filed: August 6, 2011
    Date of Patent: December 2, 2014
    Assignee: Clariant International Ltd
    Inventors: Melanie Sajitz, Isabel Scheffer, Werner Janitschek
  • Patent number: 8901343
    Abstract: 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: Grant
    Filed: December 15, 2009
    Date of Patent: December 2, 2014
    Assignee: BASF SE
    Inventors: Walter Disteldorf, Jarren Peters, Thomas Schäfer, Katrin Friese, Christoph Übler
  • Patent number: 8901344
    Abstract: 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: Grant
    Filed: December 15, 2009
    Date of Patent: December 2, 2014
    Assignee: BASF SE
    Inventors: Jarren Peters, Walter Disteldorf, Katrin Friese, Thomas Schäfer, Oliver Bey
  • Patent number: 8815992
    Abstract: Tetraesters of a C4-C5 aliphatic tetracarboxylic acid and OXO-alcohols and plasticized compositions containing said tetraesters are provided.
    Type: Grant
    Filed: April 13, 2011
    Date of Patent: August 26, 2014
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Lisa Saunders Baugh, Enock Berluche, Karla Schall Colle, Manika Varma-Nair, Ramzi Yanni Saleh, Jon Edmond Randolph Stanat, Stephen Zushma, Victor DeFlorio
  • Publication number: 20140212666
    Abstract: 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: Application
    Filed: January 27, 2014
    Publication date: July 31, 2014
    Inventors: 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
  • Patent number: 8759565
    Abstract: 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: Grant
    Filed: June 23, 2010
    Date of Patent: June 24, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Hari Babu Sunkara, Raja Hari Poladi, Gyorgyi Fenyvesi
  • Patent number: 8729292
    Abstract: 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: Grant
    Filed: December 15, 2009
    Date of Patent: May 20, 2014
    Assignee: BASF SE
    Inventors: Katrin Friese, Walter Disteldorf, Jarren Peters, Günther Golfier
  • Patent number: 8592623
    Abstract: 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: Grant
    Filed: November 3, 2009
    Date of Patent: November 26, 2013
    Assignee: Bayer MaterialScience AG
    Inventors: Rolf Roers, Hartmut Nefzger, Erika Bauer, Johannes Van De Braak, Torsten Heinemann, Jürgen Schloβmacher
  • Publication number: 20130303796
    Abstract: 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: Application
    Filed: October 15, 2012
    Publication date: November 14, 2013
    Applicant: China Petrochemical Development Corporation, Taipei (Taiwan)
    Inventors: Jih-Dar Hwang, Yung-Shun Kung, Yao-Ching Tsai
  • Patent number: 8524938
    Abstract: 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: Grant
    Filed: October 6, 2010
    Date of Patent: September 3, 2013
    Assignee: Oxea GmbH
    Inventors: Guido D. Frey, Thorsten Kreickmann, Heinz Strutz
  • Patent number: 8524937
    Abstract: 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: Grant
    Filed: October 6, 2010
    Date of Patent: September 3, 2013
    Assignee: Oxea GmbH
    Inventors: Michael Adamzik, Thomas Müller, Willy Schulz, Heyko Jürgen Schultz
  • Publication number: 20130225851
    Abstract: 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: Application
    Filed: October 3, 2012
    Publication date: August 29, 2013
    Applicant: ExxonMobil Chemical Patents Inc.
    Inventor: ExxonMobil Chemical Patents Inc.
  • Publication number: 20130217911
    Abstract: 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: Application
    Filed: August 6, 2011
    Publication date: August 22, 2013
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Melanie Sajitz, Gerd Reinhardt, Isabel Scheffer, Werner Janitschek, Ina Herrgen
  • Publication number: 20130190525
    Abstract: 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: Application
    Filed: January 23, 2013
    Publication date: July 25, 2013
    Applicant: BOSTON SCIENTIFIC SCIMED, INC.
    Inventor: Boston Scientific Scimed, Inc.
  • Patent number: 8481606
    Abstract: 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: Grant
    Filed: October 24, 2009
    Date of Patent: July 9, 2013
    Assignee: Bayer MaterialScience AG
    Inventors: Hartmut Nefzger, Erika Bauer, Johannes Van de Braak, Jürgen Schloβmacher
  • Patent number: 8344174
    Abstract: 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: Grant
    Filed: March 7, 2008
    Date of Patent: January 1, 2013
    Assignee: 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
  • Patent number: 8344175
    Abstract: 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: Grant
    Filed: January 25, 2011
    Date of Patent: January 1, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventors: Marc B. Goldfinger, Jose Manuel Rodriguez-Parada, Lee A. Silverman
  • Patent number: 8334393
    Abstract: 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: Grant
    Filed: March 17, 2011
    Date of Patent: December 18, 2012
    Assignee: E I du Pont de Nemours and Company
    Inventors: Marc B. Goldfinger, Jose Manuel Rodriguez-Parada, Lee A. Silverman, Kai Qi
  • Publication number: 20120289636
    Abstract: 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: Application
    Filed: November 16, 2010
    Publication date: November 15, 2012
    Inventors: Karla S. Colle, Allen D. Godwin
  • Publication number: 20110282092
    Abstract: 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: Application
    Filed: June 24, 2011
    Publication date: November 17, 2011
    Inventors: John Stephen Godsmark, George Marie Karel Mathys, Hubertus Joseph Beckers, Charles Morris Yarbrough, Stephen Harold Brown, Yeo-Meng Lim
  • Patent number: 8034970
    Abstract: 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: Grant
    Filed: June 23, 2008
    Date of Patent: October 11, 2011
    Assignee: H R D Corporation
    Inventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
  • Publication number: 20110196159
    Abstract: 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: Application
    Filed: September 9, 2008
    Publication date: August 11, 2011
    Inventors: Nicolaas Anthony De Munck, Aad Gerrit Oskam, Johnny Jozef Houben, Evert C. Klein
  • Patent number: 7910782
    Abstract: 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: Grant
    Filed: March 28, 2008
    Date of Patent: March 22, 2011
    Assignee: 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
  • Patent number: 7906082
    Abstract: 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: Grant
    Filed: March 23, 2009
    Date of Patent: March 15, 2011
    Inventor: Michael F. Pelly
  • Patent number: 7834109
    Abstract: 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: Grant
    Filed: December 7, 2007
    Date of Patent: November 16, 2010
    Assignee: Eastman Chemical Company
    Inventors: Bruce Roger DeBruin, Richard Gill Bonner
  • Patent number: 7799942
    Abstract: 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: Grant
    Filed: January 30, 2007
    Date of Patent: September 21, 2010
    Assignee: Eastman Chemical Company
    Inventors: Vickie Haygood Osborne, Phillip Wayne Turner, Steven Leroy Cook
  • Publication number: 20100228046
    Abstract: 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: Application
    Filed: March 28, 2008
    Publication date: September 9, 2010
    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
  • Patent number: 7741509
    Abstract: 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: Grant
    Filed: April 3, 2007
    Date of Patent: June 22, 2010
    Assignee: Eastman Chemical Company
    Inventors: Steven Leroy Cook, Phillip Wayne Turner, Vickie Haygood Osborne
  • Patent number: 7737315
    Abstract: 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: Grant
    Filed: January 28, 2009
    Date of Patent: June 15, 2010
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Stephen Harold Brown, Georges Marie Mathys
  • Publication number: 20100137631
    Abstract: 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: Application
    Filed: March 7, 2008
    Publication date: June 3, 2010
    Inventors: Nicolaas Anthony De Munck, Klaas Bandstra, Raphael Frans Caers, Brady Compton, John Lyford, IV, Aad Gerrit Oskam, Berend Jan Van Der Veen
  • Publication number: 20100130767
    Abstract: 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: Application
    Filed: March 7, 2008
    Publication date: May 27, 2010
    Inventors: Nicolaas Anthony De Munck, Brady Compton, John Lyford, IV, Aad Gerrit Oskam
  • Publication number: 20100108940
    Abstract: 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: Application
    Filed: March 7, 2008
    Publication date: May 6, 2010
    Inventors: Nicolaas Anthony De Munck, Allen David Godwin, Thomas Marshall Larson, Paul H. Daniels, Didier Naert
  • Publication number: 20090105496
    Abstract: 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: Application
    Filed: April 22, 2008
    Publication date: April 23, 2009
    Applicant: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE
    Inventors: Chih-Chien Lin, Chien-Tien Chen
  • Patent number: 7501548
    Abstract: 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: Grant
    Filed: March 10, 2006
    Date of Patent: March 10, 2009
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Stephen Harold Brown, Georges Marie Mathys
  • Publication number: 20090005587
    Abstract: 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: Application
    Filed: June 23, 2008
    Publication date: January 1, 2009
    Applicant: H R D CORPORATION
    Inventors: Abbas HASSAN, Ebrahim BAGHERZADEH, Rayford G. ANTHONY, Gregory BORSINGER, Aziz HASSAN
  • Patent number: 7381354
    Abstract: 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: Grant
    Filed: May 21, 2007
    Date of Patent: June 3, 2008
    Assignee: Albemarle Corporation
    Inventors: Elbert F. Feske, Nelson E. Clark, Arthur G. Mack, Jeffrey Todd Aplin
  • Patent number: 7323586
    Abstract: 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: Grant
    Filed: September 20, 2002
    Date of Patent: January 29, 2008
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Klaus-Diether Wiese, Michael Grass, Wilfried Bueschken
  • Patent number: 7307183
    Abstract: 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: Grant
    Filed: July 29, 2003
    Date of Patent: December 11, 2007
    Assignee: Great Lakes Chemical Corporation
    Inventors: David W. Bartley, James D. Siebecker, Stephen B. Falloon
  • Patent number: 7265238
    Abstract: 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: Grant
    Filed: September 22, 2006
    Date of Patent: September 4, 2007
    Assignee: Saltigo GmbH
    Inventors: Michael Dockner, Torsten Neugebauer
  • Patent number: 7258823
    Abstract: 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: Grant
    Filed: May 20, 2004
    Date of Patent: August 21, 2007
    Assignee: Albemarle Corporation
    Inventors: Elbert F. Feske, Nelson E. Clark, Arthur G. Mack, Jeffrey Todd Aplin
  • Patent number: 7247740
    Abstract: The present invention relates to a process for the preparation of perfluoroalkanesulfonic acid esters and to the further conversion thereof into salts, and to the use of the resultant compounds in electrolytes and in batteries, capacitors, supercapacitors and electrochemical cells.
    Type: Grant
    Filed: November 25, 2002
    Date of Patent: July 24, 2007
    Assignee: Merck Patent GmbH
    Inventors: Michael Schmidt, Nicolai Ignatyev, Udo Heider, Peter Sartori, Andrij Kucheryna
  • Patent number: 7247742
    Abstract: A process for preparing a dialkylester of a naphthalenedicarboxylic acid comprising directing a liquid phase reaction mixture comprising a low molecular weight alcohol, a naphthalenedicarboxylic acid, a dialkylester of a naphthalenedicarboxylic acid, and a polyethylene naphthalate containing material, at a given temperature and pressure through series arranged reaction zones and subsequently removing a product comprising a dialkylester formed by the reaction of the naphthalenedicarboxylic acid and the polyethylene naphthalate containing material with the low molecular weight alcohol from a reaction zone. This invention is also directed to a process for preparing a purified dialkylester of a naphthalenedicarboxylic acid comprising a series of crystallization and distillation steps, and combinations thereof.
    Type: Grant
    Filed: May 20, 2004
    Date of Patent: July 24, 2007
    Assignee: BP Corporation North America Inc.
    Inventors: Rosemary F. McMahon, John A. Macek, Gregory P. Hussmann, Michael J. Panzer, Raymond J. Eifert, David A. Young, Allen B. Mossman, J. Deven Cleckler