Preparing Esters By Esterification Or Carbonylation Patents (Class 560/204)
-
Patent number: 6825379Abstract: The present invention relates to a method for recovering and producing C4-C6 dicarboxylates from an alkaline waste solution generated in a caprolactam preparation process, in which the alkaline waste solution is treated with sulfuric acid to separate into an aqueous phase and an organic phase, allowing valuable substances contained in the organic phase to be firstly oxidized and converted into dicarboxylic acids. The dicarboxylic acids then undergo concentration, esterification and distillation processes, so as to obtain desirable C4-C6 dicarboxylates with high purity. This therefore provides an efficient and improved method for effectively recovering most valuable substances from the alkaline waste solution, so that economic benefits in recovery are greatly raised.Type: GrantFiled: January 14, 2002Date of Patent: November 30, 2004Assignee: Chemaxz International CorporationInventors: Sien-Chun Chou, Edward K. S. Wang, Chung Ho Wu, Yaw Jong Liu, Ping Chiang
-
Patent number: 6737542Abstract: The present invention relates to a process for the carbonylation of conjugated dienes, whereby a conjugated diene is reacted with carbon monoxide and a hydroxyl group containing compound in the presence of a catalyst system including: (a) a source of palladium cations, (b) a phosphorus-containing ligand, (c) a source of anions, wherein the phosphorus-containing ligand is a ligand having the general formula (I): X1—R—X2 wherein X1 and X2 represent a substituted or non-substituted cyclic group with at least 5 ring atoms, of which one is a phosphorus atom, and R represents a bivalent organic bridging group, connecting both phosphorus atoms, containing from 1 to 4 atoms in the bridge, whereby the carbonylation process can be performed batch wise, semi-continuously or continuously.Type: GrantFiled: September 20, 2001Date of Patent: May 18, 2004Assignee: Shell Oil CompanyInventors: Eit Drent, Willem Wabe Jager
-
Patent number: 6706912Abstract: Process for the carbonylation of ethylenically unsaturated compounds having 3 or more carbon atoms by reaction with carbon monoxide and an hydroxyl group containing compound in the presence of a catalyst system. The catalyst system includes (a) a source of palladium cations; (b) a bidentate diphosphine of formula I, R1R2>P—R3—R—R4—P<R5R6 (I) wherein P represents a phosphorus atom; R1, R2, R5 and R6 independently represent the same or different optionally substituted organic groups containing a tertiary carbon atom through which the group is linked to the phosphorus atom; R3 and R4 independently represent optionally substituted alkylene groups and R represents an optionally substituted aromatic group; (c) a source of anions derived from an acid having a pKa less than 3, as measured at 18° C. in an aqueous solution. The process is carried out in the presence of an aprotic solvent.Type: GrantFiled: March 13, 2001Date of Patent: March 16, 2004Assignee: Shell Oil CompanyInventors: Eit Drent, Willem Wabe Jager
-
Patent number: 6664413Abstract: A process for producing an ester comprises the steps of: (a) feeding to a first vessel a feed that comprises organic acid, alcohol, and water, whereby organic acid and alcohol react to form monomeric ester and water, and whereby a first liquid effluent is produced that comprises as its components at least some ester, alcohol, and water, the components of the first liquid effluent being substantially in reaction equilibrium; and (b) feeding the first liquid effluent to a second vessel, whereby a vapor product stream and a second liquid effluent stream are produced, the vapor stream comprising ester, alcohol, and water, wherein the second vessel is maintained substantially at vapor-liquid equilibrium but not substantially at reaction equilibrium.Type: GrantFiled: November 19, 1998Date of Patent: December 16, 2003Assignee: A. E. Staley Manufacturing Co.Inventor: Michael Charles Milner Cockrem
-
Patent number: 6639091Abstract: Bidentate ligand of formula II, R1R2M1—R—M2R3R4 (II) wherein M1 and M2 are independently P, As or Sb; R1, R2, R3 and R4 independently represent tertiary alkyl groups, or R1 and R2 together and/or R3 and R4 together represent an optionally substituted bivalent cycloaliphatic group whereby the two free valencies are linked to M1 or M2, and R represents a bivalent aliphatic bridging group containing from 2 to 6 atoms in the bridge, which is substituted with two or more substituents. A catalyst system comprising: a) a source of group VIII metal cations; b) a source of such a bidentate ligand; and c) a source of anions, and use of such a catalyst system in a process for the carbonylation of optionally substituted ethylenically or acetylenically unsaturated compounds by reaction with carbon monoxide and a coreactant is provided.Type: GrantFiled: May 17, 2001Date of Patent: October 28, 2003Assignee: Shell Oil CompanyInventors: Eit Drent, Michael Rolf Eberhard, Paul Gerard Pringle
-
Patent number: 6617469Abstract: A process for preparing malonic diesters by carbonylation of haloacetic esters and reaction with monohydric alcohols and a base in the presence of a transition metal catalyst, preferably a catalytic cobalt carbonyl complex, using a stirred reactor with one or more internal heat exchangers. The stirred reactor preferably contains a sparging stirrer.Type: GrantFiled: December 1, 2000Date of Patent: September 9, 2003Assignee: Degussa AGInventors: Frank Bauer, Wilfried Latz, Uwe Prange, Christoph Theis
-
Patent number: 6580003Abstract: The present invention relates to methods for the synthesis of chiral non-racemic products, e.g., enantiomerically-enriched hemiesters, from prochiral starting materials, e.g., meso anhydrides. The present invention also relates to catalysts for the aforementioned methods, and methods for synthesizing these catalysts.Type: GrantFiled: April 3, 2001Date of Patent: June 17, 2003Assignee: Brandeis UniversityInventors: Li Deng, Yonggang Chen, Shikai Tian
-
Patent number: 6555703Abstract: The invention relates to a process for forming a carboxylic benzyl ester comprising reacting a dibenzyl ether with a carboxylic acid in the presence of a heteropolyacid and forming a carboxylic acid benzyl ester.Type: GrantFiled: August 31, 2001Date of Patent: April 29, 2003Assignee: Bayer AktiengesellschaftInventors: Pieter Ooms, Bernd-Ulrich Schenke
-
Patent number: 6476254Abstract: Fatty alkoxylated esters consisting of diesters of aliphatic or aromatic dicarboxylic acids, formed by reacting the acid with a stoichiometric excess of one or more polyalkoxylated fatty alcohols. Non-aqueous compositions for topical application are also disclosed including one or more active ingredients, and an emollient agent of the fatty alkoxylated esters of the present invention.Type: GrantFiled: October 1, 1999Date of Patent: November 5, 2002Assignee: Croda Inc.Inventors: Abel G. Pereira, Patrick Obukowho
-
Patent number: 6472555Abstract: The present invention relates to a process for the preparation of esters from alcohols using acetic acid as acetylating agent and clays as catalysts, which comprises the preparation of esters in a single step from the reaction of aliphatic, acyclic, cyclic, heterocyclic, &agr;,&bgr;-unsaturated and aromatic alcohols with carbon atoms in the range of C1 to C10 with acetic acid in a molar ratio of 1:3 to 11 using reusable natural montmorillonite/metal ion-exchanged clay catalysts in the solvent medium of aliphatic, aromatic, or chlorinated hydrocarbons at 30-140° C. for a period in the range of 0.02 to 3.0 hrs, and recovering the corresponding esters by simple work-up procedure.Type: GrantFiled: February 12, 1999Date of Patent: October 29, 2002Assignee: Council of Scientific and Industrial ResearchInventors: Boyapati Manoranjan Choudary, Veldurthy Bhaskar, Mannepalli Lakshmi Kantam, Kottapalli Koteswara Rao, Kondapuram Vijaya Raghavan
-
Patent number: 6437170Abstract: The mixture described is a mixture of isomeric nonanol diesters of a dicarboxylic acid, selected from the class consisting of a mixture of diesters of adipic acid in the 1H NMR spectrum of which, observed in CDCl3, the ratio of the area under the resonance signals at chemical shifts in the range from 1.0 to 2.0 ppm with respect to TMS to the area under the resonance signals at chemical shifts in the range from 0.5 to 1.0 ppm with respect to TMS is from 1.20 to 5.00 and a mixture of diesters of phthalic acid, in the 1H NMR spectrum of which, observed in CDCl3, the ratio of the area under the resonance signals at chemical shifts in the range from 1.1 to 3.0 ppm with respect to TMS to the area under the resonance signals at chemical shifts in the range from 0.5 to 1.1 ppm with respect to TMS is from 1.00 to 4.00.Type: GrantFiled: November 26, 1999Date of Patent: August 20, 2002Assignee: BASF AktiengesellschaftInventors: Lucien Thil, Boris Breitscheidel, Walter Disteldorf, Edgar Zeller, Marc Walter, Bernd Morsbach, Knut Dornik
-
Patent number: 6423868Abstract: Process for the production of an aqueous monoester peroxycarboxylic acid solution by reaction of a peroxygen compound with at least one dicarboxylic acid and with at least one alcohol optionally in the presence of an acid catalyst. Aqueous monoester peroxycarboxylic acid solution obtainable by this process. Use of the aqueous monoester peroxycarboxylic acid solution as disinfectant.Type: GrantFiled: February 26, 2001Date of Patent: July 23, 2002Assignee: Solvay (Societe Anonyme)Inventors: Graham Carr, Alun P. James
-
Patent number: 6384228Abstract: The present invention relates to a method for synthesis of an optically active halopyridyl-azacyclo-pentane derivative and the intermediate thereof which comprises preparing an optically active allene-1,3-dicarboxylic acid ester derivative from an optically active acetonedicarboxylic acid ester derivative and then proceeding through a 7-azabicyclo[2.2.1]heptane derivative to obtain the objective product.Type: GrantFiled: January 7, 2000Date of Patent: May 7, 2002Assignee: Nihon Medi-Physics Co., Ltd.Inventors: Manabu Node, Daisaku Nakamura, Toshio Fujiwara, Shogo Ichihashi
-
Publication number: 20020038048Abstract: The present invention relates to methods for the synthesis of chiral non-racemic products, e.g., enantiomerically-enriched hemiesters, from prochiral starting materials, e.g., meso anhydrides. The present invention also relates to catalysts for the aforementioned methods, and methods for synthesizing these catalysts.Type: ApplicationFiled: April 3, 2001Publication date: March 28, 2002Inventors: Li Deng, Yonggang Chen, Shikai Tian
-
Publication number: 20020035290Abstract: A process for preparing a malonic acid monoester or &bgr;-ketoester from an epoxide includes the steps of reacting an epoxide with carbon monoxide and an alcohol in the presence of a catalytic amount of a cobalt compound and at least one promoter to produce a &bgr;-hydroxyester, separating the &bgr;-hydroxyester from the cobalt compound and the promoter, and oxidizing the &bgr;-hydroxyester to produce a malonic acid monoester or &bgr;-ketoester.Type: ApplicationFiled: June 20, 2001Publication date: March 21, 2002Applicant: Samsung Electronics Co., Ltd.Inventors: Byeong No Lee, In-Sun Jung, Eun Joo Jang
-
Patent number: 6355829Abstract: The present invention relates to aspartate-terminated urea/urethane prepolymers that are based on the reaction products of NCO prepolymers with compounds corresponding to the formula wherein X represents an organic group which has a valency of n and is inert towards isocyanate groups at a temperature of 100° C. or less, R1 and R2 may be identical or different and represent organic groups which are inert towards isocyanate groups at a temperature of 100° C. or less, R3 and R4 may be identical or different and represent hydrogen or organic groups which are inert towards isocyanate groups at a temperature of 100° C. or less and n represents an integer with a value of at least 2, at an equivalent ratio of aspartate groups to isocyanate groups of 1.5:1 to 20:1. The present invention also relates to coating compositions containing the aspartate-terminated urea/urethane prepolymers and a polyisocyanate.Type: GrantFiled: September 2, 1999Date of Patent: March 12, 2002Assignee: Bayer CorporationInventors: Richard R. Roesler, Lyubov K. Gindin, P. Richard Hergenrother
-
Publication number: 20020028963Abstract: Carboxylic esters are prepared by a process, which comprises reacting dicarboxylic or polycarboxylic acids or their anhydrides with alcohols in a liquid medium with the concomitant removal of water formed by the esterification reaction by azeotropic distillation together with the alcohol in the medium, wherein the amount of liquid removed from the reaction medium by azeotropic distillation is replaced in whole or in part with the alcohol.Type: ApplicationFiled: September 5, 2001Publication date: March 7, 2002Applicant: OXENO OLEFINCHEMIE GMBHInventors: Dietmar Gubisch, Uwe Ernst, Wilfried Bueschken
-
Publication number: 20020026070Abstract: An improved process for the production of dimethylesters by reacting dicarboxylic acids or anhydrides, typically maleic anhydride or phthalic anhydrides, with methanol. The process uses an alkylbenzene sulfonic acid with an alkyl radical containing from 8 to 16 carbon atoms, preferably from 10 to 13 carbon atoms as esterification catalyst.Type: ApplicationFiled: January 21, 2000Publication date: February 28, 2002Inventors: ALDO BERTOLA, MYRIAM HOBE
-
Patent number: 6350898Abstract: Malonic esters of the general formula where R is C1-10-alkyl, C3-10-alkenyl or aryl-C1-4-alkyl, are prepared by reacting an alkali metal salt of malonic acid with a halide of the general formula R—X (II), where R is as defined above and X is chlorine, bromine or iodine, in the presence of water and a phase-transfer catalyst.Type: GrantFiled: January 10, 2000Date of Patent: February 26, 2002Assignee: Lonza AGInventors: Stefan Hildbrand, Paul Hanselmann
-
Patent number: 6333430Abstract: A process for preparing a tert-alkyl carboxylic acid ester represented by the formula (III): wherein R1 is an organic group; and each of R2 and R3 is independently an alkyl group having 1 to 4 carbon atoms, comprising reacting a carboxylic acid represented by the formula (I): R1—COOH (I) wherein R1 is as defined above, with a vinylidene compound represented by the formula (II): wherein R2 and R3 are as defined above, in the presence of a phosphorus halide. The tert-alkyl carboxylic acid ester can be used as intermediates for pharmaceuticals such as antibiotics.Type: GrantFiled: May 2, 2000Date of Patent: December 25, 2001Assignee: Sumika Fine Chemicals Co., Ltd.Inventors: Tetsuya Shintaku, Kiyoshi Sugi, Tadashi Katsura, Nobushige Itaya
-
Patent number: 6310003Abstract: The invention relates to a composition and procedure for manipulating the behavior of the orange wheat blossom midge, Sitodiplosis mosellana. More importantly, this invention relates to the preparation and use of 2,7-nonanediyl dibutyrate or stereoisomers thereof for manipulating the behavior of S. mosellana.Type: GrantFiled: November 29, 2000Date of Patent: October 30, 2001Assignees: Simon Fraser University, Agriculture and Agri-Food CanadaInventors: Regine Gries, Gerhard Gries, Khaskin Grigori, Olfert Owen, Lori-Ann Kaminski
-
Patent number: 6310235Abstract: The invention relates to an improved method for producing ester plasticizers by reacting di- or polycarboxylic acids or their anhydrides with alcohols in the presence of metal catalysts.Type: GrantFiled: November 17, 1999Date of Patent: October 30, 2001Assignee: Celanese GmbHInventor: Wilhelm Gick
-
Patent number: 6288268Abstract: A catalyst for the bisalkoxycarbonylation of olefins comprising a noble metal compound and a phosphine chalcogenide of the following formula (1): wherein each of R1, R2 and R3 is, independently, an alkyl group or an aryl group each of which may have a substituent, and A is a Group 16 element of the Periodic Table; and R1, R2 or R3 may be combined, directly or through a bridging group, with one another where the groups to be combined may be attached either to an identical phosphorus atom or to different phosphorus atoms. Element A includes oxygen, sulfur and selenium atoms. The noble metal compound includes palladium(II) halides and other palladium compounds. The catalyst may further include a copper(I) halide or other copper compound as a co-catalyst. The use of this catalyst can provide the bisalkoxycarbonylation of olefins with efficiency.Type: GrantFiled: September 13, 2000Date of Patent: September 11, 2001Assignee: Daicel Chemical Industries, Ltd.Inventors: Kazuhiko Saigo, Yukihiko Hashimoto, Minoru Hayashi
-
Publication number: 20010018540Abstract: A process for preparing malonic diesters by carbonylation of haloacetic esters and reaction with monohydric alcohols and a base in the presence of a transition metal catalyst, preferably a catalytic cobalt carbonyl complex, using a stirred reactor with one or more internal heat exchangers. The stirred reactor preferably contains a sparging stirrer.Type: ApplicationFiled: December 1, 2000Publication date: August 30, 2001Inventors: Frank Bauer, Wilfried Latz, Uwe Prange, Christoph Theis
-
Patent number: 6153783Abstract: A two-step process for producing a difunctional organic compound is provided which comprises:a) reacting a cycloalkanone with a 2-substituted-1-alkene in the presence of an enamine catalyst to produce the corresponding substituted cycloalkanone intermediate and,b) subjecting the intermediate reaction product to ultraviolet radiation in the presence of a solvent to form the difunctional organic compound of the general formula: ##STR1## wherein R4 is derived from the solvent and is hydroxyl, --NH.sub.2 or OR.sup.5, andwherein R, R1, R2, R4, R.sup.5, and x are as defined in the specification.Type: GrantFiled: January 6, 2000Date of Patent: November 28, 2000Assignee: Cognis CorporationInventors: Louis Rebrovic, Michael Staley
-
Patent number: 6153792Abstract: A process for the production of a carboxylic acid in the presence of solid catalyst particles that employs a flash step with a liquid wash is disclosed. This process helps prevent the buildup of deposits of solid catalyst particles, attrited solid catalyst particles, and heavy by-products in the flash zone. This invention is useful for the production of carboxylic acids, especially acetic acid.Type: GrantFiled: December 18, 1998Date of Patent: November 28, 2000Assignee: UOP LLCInventors: William A. Leet, Santi Kulprathipanja
-
Patent number: 6114576Abstract: A process for the production of a carboxylic acid in the presence of solid catalyst particles that uses the exothermic heat of reaction with high efficiency in recovering the carboxylic acid product is disclosed. This process uses indirect heat exchange to transfer the heat of reaction to another stream, without the need for an additional heat transfer fluid such as steam. This invention is especially applicable to the production of acetic acid.Type: GrantFiled: December 18, 1998Date of Patent: September 5, 2000Assignee: UOP LLCInventors: William A. Leet, Santi Kulprathipanja, Bruce A. Briggs
-
Patent number: 6087528Abstract: A process for producing hydroxyalkyl monoacrylate of the present invention, comprises the steps of: reacting acrylic acid or an acrylic acid derivative with alkane diol for esterification and/or transesterification therebetween in the presence of a reaction catalyst comprising a stannoxane compound; recovering said reaction catalyst from a liquid reaction product by extraction; and recycling the recovered reaction catalyst to a reaction system for said esterification and/or transesterification. The process of the present invention is an industrially useful process for producing hydroxyalkyl monoacrylate, which is excellent in reactivity, selectivity for an aimed product, stability of a reaction catalyst used and stability of a reaction substrate and product, and is improved so as to effectively recover and reuse the reaction catalyst.Type: GrantFiled: May 26, 1998Date of Patent: July 11, 2000Assignee: Mitsubishi Chemical CorporationInventors: Toshiharu Yokoyama, Yuuji Kawaragi, Kouya Murai
-
Patent number: 6011171Abstract: The present invention provides a process for synthesizing tertiary carboxylic acids or the esters thereof having one or two more carbon atoms than the raw material has, comprising reacting in a strong acid (e.g., sulfuric acid, sulfuric acid-phosphoric acid, hydrogen fluoride, fluorosulfuric acid, boron trifluoride.water complex and trifluoromethanesulfonic acid) a raw material compound (i.e., olefin, alcohol, diene, diol or saturated hydrocarbon) with carbon monoxide in the presence of a specific metal carbonyl catalyst (i.e., platinum carbonyl catalyst, palladium carbonyl catalyst and gold dicarbonyl catalyst).The metal carbonyl catalyst is formed by reacting in a strong acid at least one specific metal compounds (e.g., platinum compound such as platinum (II, IV) oxide, platinum (II, IV) hydroxide, a platinum powder, etc.; palladium compound such as palladium (II, III, IV) oxide, palladium (II) hydroxide, palladium (II) sulfate, palladium (II) carboxylate, a palladium powder, etc.Type: GrantFiled: November 4, 1997Date of Patent: January 4, 2000Assignee: Jiro Hiraishi, Director-General, Agency of Industrial Science and TechnologyInventors: Qiang Xu, Yoshie Souma
-
Patent number: 5922900Abstract: A process for producing carboxylic acid esters by the following steps:a) preparation of a reaction mixture containing an alcohol and a carboxylic acid and/or a carboxylic anhydride and/or a carboxylic acid ester and or a partially esterified carboxylic acid,b) heating of this mixture to the suitable reaction temperature in the presence of a solid polysiloxane insoluble in the reaction medium and having sulphonic acid groups with intensive thorough mixing accompanied by continuous separation of the reaction water which forms, wherein the polysiloxane used as the catalyst in modified by treatment with a soluble aluminum, titanium or zirconium compound, and the spherical particles thereof have a diameter of 0.01 to 3 mm, a specific surface of 0.1 to 1200 m.sup.2 /g, a specific pore volume of 0.01 to 6.0 ml/g and a bulk density of 50 to 1000 g/l.Type: GrantFiled: September 3, 1997Date of Patent: July 13, 1999Assignee: Degussa AktiengesellschaftInventors: Stefan Wieland, Peter Panster
-
Patent number: 5914426Abstract: A process for the preparation of di-tert-butyl succinate of formula ##STR1## by proton-catalysed esterification of succinic acid with isobutene, which comprises reacting succinic acid or succinic acid anhydride, or mixtures thereof, with isobutene in the presence of a water-containing acid esterification catalyst, with the proviso that sulfuric acid is used in a concentration of not more than 95% by weight.By this process it is possible to prepare di-tert-butyl succinate by reacting succinic acid or succinic acid anhydride, or corresponding mixtures of succinic acid and succinic acid anhydride, with isobutene butene with reduced evolution of heat and at the same time with increased yield and improved purity of the end product.Type: GrantFiled: April 15, 1998Date of Patent: June 22, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Martin Kudschus, Olof Wallquist
-
Patent number: 5869729Abstract: An ester compound, for example, carbonic acid ester or succinic acid ester, is produced by catalytically reacting, in gas phase, carbon monoxide with a nitrous acid ester and optionally an olefin in the presence of a catalyst and in the presence of a chlorine-containing substance, bringing the reaction product-containing mixed gas into contact with a solid catalyst such as activated carbon or inorganic oxide to reduce the content of the chlorine-containing substance, cool-condensing the resultant mixed gas, and collecting the target ester compound from the condensed liquid.Type: GrantFiled: June 27, 1996Date of Patent: February 9, 1999Assignee: Ube Industries, Ltd.Inventors: Keigo Nishihira, Shuji Tanaka, Yuki Nishida, Noriaki Manada, Toshio Kurafuji, Masato Murakami
-
Patent number: 5866710Abstract: A process for the preparation of an ester comprises carrying out an esterification in the presence of a catalyst comprising the reaction product of an orthoester or a condensed orthoester of titanium or zirconium, an alcohol containing at least two hydroxyl groups, a 2-hydroxy acid and a base. The process can be a direct esterification or a transesterification and can be a polyesterification. The catalyst can effectively produce esters without leading to a haze in the final product and there is a reduced amount of yellowing of polyesters in comparison to known catalysts.Type: GrantFiled: June 5, 1997Date of Patent: February 2, 1999Assignee: Tioxide Specialties LimitedInventors: John Ridland, Iain Wesley Hepplewhite, Brian Steven Jolly
-
Patent number: 5786502Abstract: A process is provided for preparing diesters of higher .alpha.,.omega.-dicarboxylic acids from cycloaliphatic ketones and carbonic diesters in the presence of a strongly basic agent, which involves continuously feeding a cycloaliphatic ketone having 8 to 20 ring members, at least an equimolar amount of a carbonic diester and a catalytic amount of a strongly basic agent to a reaction zone in which condensation occurs between the cycloaliphatic ketone and the carbonic diester to give the corresponding cyclic .beta.-keto acid ester enolate, which is then ring-opened by the released alcohol to give the .alpha.,.omega.-dicarboxylic diester and from which reaction mixture is continuously taken off.Type: GrantFiled: June 9, 1997Date of Patent: July 28, 1998Assignee: Huels AktiengesellschaftInventors: Guenther Koehler, Josef Metz
-
Patent number: 5744636Abstract: This invention relates to a process for producing ethylidene diacetate by the reaction of dimethyl ether, acetic acid, hydrogen and carbon monoxide at elevated temperatures and pressures in the presence of an alkyl halide and a heterogeneous, bifunctional catalyst that is stable to hydrogenation and comprises an insoluble polymer having pendant quaternized heteroatoms, some of which heteroatoms are ionically bonded to anionic Group VIII metal complexes, the remainder of the heteroatoms being bonded to iodide. In contrast to prior art processes, no accelerator (promoter) is necessary to achieve the catalytic reaction and the products are easily separated from the catalyst by filtration. The catalyst can be recycled for 3 consecutive runs without loss in activity.Type: GrantFiled: May 21, 1996Date of Patent: April 28, 1998Assignee: Air Products and Chemicals, Inc.Inventors: Dorai Ramprasad, Francis Joseph Waller
-
Patent number: 5710323Abstract: A process for producing a monocarboxylic acid and/or a dicarboxylic acid by the reaction of a starting compound selected from among saturated hydrocarbons, .alpha.-olefins of 6 to 20 carbon atoms, saturated monocarboxylic acids and esters of the acids either with both of carbon monoxide and water at the same time or first with carbon monoxide and then with water, wherein the reaction of the starting compound either with both of carbon monoxide and water or with carbon monoxide alone is conducted in a strong acid solution containing a trifluoromethane-sulfonic acid catalyst and an alcohol and/or an olefin of 3 to 5 carbon atoms.Type: GrantFiled: March 27, 1997Date of Patent: January 20, 1998Assignee: Idemitsu Petrochemical Co., Ltd.Inventors: Ryoichi Okuda, Tadashi Kato, Yoshio Okada
-
Patent number: 5698722Abstract: A Koch functionalized product which is the reaction product of at least one polymer having a number average molecular weight of at least 500 and at least ethylenic double bond per polymer chain, with carbon monoxide and a nucleophilic trapping agent. The invention includes functionalized polymer, derivatives thereof and methods of making the same.Type: GrantFiled: June 6, 1995Date of Patent: December 16, 1997Assignee: Exxon Chemical Patents Inc.Inventors: Joseph Victor Cusumano, William Daniel Diana, Jacob Emert, Keith Raymond Gorda, Richard H. Schlosberg, David A. Young, William Bernard Eckstrom, Edris Eileen Manry, Michael John Keenan
-
Patent number: 5693316Abstract: Fatty alkoxylate esters consisting of diesters of aliphatic or aromatic dicarboxylic acids, formed by reacting the acid with a stoichiometric excess of one or more polyalkoxylated fatty alcohols having fatty moieties containing from 14 to 22 carbon atoms. Non-aqueous compositions for topical application are also disclosed including one or more active ingredients, and an emollient agent of the fatty alkoxylate esters of the present invention.Type: GrantFiled: August 26, 1996Date of Patent: December 2, 1997Assignee: Croda, Inc.Inventors: Abel G. Pereira, Kevin F. Gallagher, Phillip G. Abend, John C. Carson, Jr.
-
Patent number: 5679831Abstract: Process for the preparation of a terminal ester by carbonylation of an internally unsaturated organic compound in the presence of an alcohol, carbon monoxide, palladium, an acid with a pK.sub.a of less than 2 (measured at 18.degree. C. in an aqueous solution) and a bidentate organic phosphorus, antimony or arsenic ligand compound having a bridging group, wherein the bridging group comprises a bis(.eta.-cyclopentadienyl) coordination group of a transition metal.Type: GrantFiled: January 5, 1995Date of Patent: October 21, 1997Assignees: DSM N.V., E. I. Du Pont de Nemours and CompanyInventor: Otto E. Sielcken
-
Patent number: 5670701Abstract: The alkyl adipates are prepared by reacting admixture consisting essentially of alkyl 3-pentenoate and alkyl 2-pentenoate with carbon monoxide and an alcohol, at elevated temperature, under superatmospheric pressure and in the presence of a catalytically effective amount of cobalt or a cobalt compound and a nitrogenous heterocyclic base.Type: GrantFiled: February 18, 1994Date of Patent: September 23, 1997Assignee: Rhone-Poulenc ChimieInventors: Philippe Denis, Jean-Michel Grosselin, Jean Jenck, Francois Metz, Paul Rouyer
-
Patent number: 5650536Abstract: A continuous process for functionalizing olefins, especially polymer olefins in a CSTR or pipe reactor. Esters are preferably produced by continuous reaction of the olefin with carbon monoxide and a nucleophilic trapping agent. The liquid-filled pipe reactor operates in plug flow with static mixers and the CSTR is operated in the substantial absence of air at constant liquid level.Type: GrantFiled: June 17, 1994Date of Patent: July 22, 1997Assignee: Exxon Chemical Patents Inc.Inventors: David C. Dankworth, William H. Cross, Joseph V. Cusumano, William D. Diana, William B. Eckstrom, Jacob I. Emert, Keith R. Gorda, Robert M. Koros, Harold W. Margo, Jon E. Stanat
-
Patent number: 5646332Abstract: A rapid, batch Koch carbonylation/functionalization reaction of at least one polymer olefin, carbon monoxide, and an aliphatic or aryl alcohol in the presence of an acid catalyst with either an alcohol:polymer olefin mole ratio .gtoreq.1:1, or an acid catalyst:polymer olefin mole ratio .gtoreq.0.9:1, or both, and recovering at least 80% functionalized polymer which is predominantly ester.Type: GrantFiled: June 17, 1994Date of Patent: July 8, 1997Assignee: Exxon Chemical Patents Inc.Inventors: Joseph V. Cusumano, David C. Dankworth, William D. Diana, William B. Eckstrom, Jacob I. Emert, Keith R. Gorda
-
Patent number: 5639859Abstract: Carboxylate protective groups, a process for their preparation, their coupling to a funcitonal group, and their useCarboxylates of polar, hydrophilic alcohols of the formula ##STR1## in which R is an unbranched or branched organic radical which contains, as polar members between aliphatic or araliphatic hydrocarbon bridges, ether oxygens, amine nitrogen groups or a mixture of ether and amine groups which can be incorporated into a cyclic structure, where the total length does not exceed 20 members and where, in the case of polyethylene glycol [(CH.sub.2 --CH.sub.2 --O).sub.n ], n indicates the number of the members and is defined as any integer, andR' is an aliphatic or araliphatic radical which has at least one functional group,are suitable as protective groups since they can be introduced selectively into functional groups of organic compounds and eliminated specifically by lipases.Type: GrantFiled: May 15, 1995Date of Patent: June 17, 1997Assignee: Hoechst AktiengesellschaftInventors: Horst Kunz, Gunther Braum, Peter Braun
-
Patent number: 5597555Abstract: Fatty alkoxylate esters consisting of diesters of aliphatic or aromatic dicarboxylic acids, formed by reacting the acid with a stoichiometric excess of one or more polyalkoxylated fatty alcohols having fatty moieties containing from 14 to 22 carbon atoms. Non-aqueous compositions for topical application are also disclosed including one or more active ingredients, and an emollient agent of the fatty alkoxylate esters of the present invention.Type: GrantFiled: April 12, 1994Date of Patent: January 28, 1997Assignee: Croda, Inc.Inventors: Abel G. Pereira, Kevin F. Gallagher, Phillip G. Abend, John C. Carson, Jr.
-
Patent number: 5571938Abstract: The present invention provides for an esterification process comprising a catalyst source of stannous tin and an alkali metal aluminate. In one preferred embodiment the catalyst comprises about 92 parts sand, about 5 parts stannous oxalate, and about 3 parts of a sodium aluminate, by weight, dry basis. This catalyst is particularly useful in making phthalates, adipates, sebacates and azelates which esters are chiefly used plasticizers.Type: GrantFiled: July 31, 1995Date of Patent: November 5, 1996Inventor: Stan Jakubowycz
-
Patent number: 5536872Abstract: The reaction between a Michael donor corresponding to the formula Z--CH(E)(E') (e.g., a dialkyl malonate) and a Michael acceptor corresponding to the formula CTT'.dbd.CT"G (e.g., an alkyl acrylate or alkyl acrylate dimer) in the presence of a solid inorganic base catalyst is expedited by simultaneously feeding the reactants through a column of the solid inorganic base catalyst at a temperature of about 25.degree.-120.degree. C. to form an effluent containing a product corresponding to the formula Z'--C(E)(E").sub.p --Q.sub.Type: GrantFiled: August 4, 1995Date of Patent: July 16, 1996Assignee: Albemarle CorporationInventors: Mahmood Sabahi, Kenneth C. Lilje
-
Patent number: 5532405Abstract: A process for the esterification of acids or anhydrides with alcohols or a polyhydroxy compound wherein the lower boiling point reactant is added to the reaction vessel in stages such that it is present in an amount of at least about 5% of the stoichiometric requirements of the total lower boiling point reactant required to react with the limiting reagent, and wherein the concentration of the lower boiling point reactant is monitored so that additional reactant having the lower boiling point can be subsequently added in stages to the reaction mixture in order to maintain a certain predetermined concentration of the lower boiling point reactant.Type: GrantFiled: April 29, 1994Date of Patent: July 2, 1996Assignee: Exxon Chemical Patents Inc.Inventor: John Lyford, IV
-
Patent number: 5502240Abstract: A liquid phase esterification process is described wherein the esterification catalyst is a titanium zeolite.Type: GrantFiled: June 9, 1995Date of Patent: March 26, 1996Assignee: Aristech Chemical CorporationInventors: Joseph Pugach, Thomas W. Smeal, Howard S. Karp
-
Patent number: 5464549Abstract: The dispersants are formed by reacting (a) at least one dispersant having at least one primary or secondary amino group and/or at least one hydroxyl group, with (b) at least one polyolefinic compound substituted at each terminal position by a succinic group. Suitable substances for use as reactant (b) include compounds derived from at least one telechelic compound having up to 5000 carbon atoms and at least two terminal methylene groups by reaction with maleic anhydride or the like. The products are deemed to be effective dispersant/detergents for use in fuels and lubricants. In fuels the products are deemed to exhibit the property of inhibiting and/or reducing deposit formation such as intake valve deposits. In crankcase lubricants, the products are deemed to provide desirable viscosity index improving properties.Type: GrantFiled: December 12, 1991Date of Patent: November 7, 1995Assignee: Ethyl CorporationInventor: John F. Sieberth
-
Patent number: 5455025Abstract: Non-aqueous compositions for topical application comprising one or more active ingredients and a fatty alkoxylate ester emollient agent comprising a diester or triester of an aliphatic or aromatic tricarboxylic acid formed by reacting the acid with a stoichiometric excess of one or more polyalkoxylated fatty alcohols.Type: GrantFiled: April 12, 1994Date of Patent: October 3, 1995Assignee: Croda, Inc.Inventors: Abel G. Pereira, Kevin F. Gallagher, Phillip G. Abend, John C. Carson, Jr.