Carbon To Carbon Unsaturation In The Aldehyde Prepared Patents (Class 568/459)
-
Patent number: 9975837Abstract: The present invention relates to a process for the preparation of an optically active carbonyl compound by asymmetric hydrogenation of a prochiral ?,?-unsaturated carbonyl compound with hydrogen in the presence of at least one optically active transition metal catalyst that is soluble in the reaction mixture and which has rhodium as catalytically active transition metal and a chiral, bidentate bisphosphine ligand, wherein the reaction mixture during the hydrogenation of the prochiral ?,?-unsaturated carbonyl compound additionally comprises at least one compound of the general formula (I): in which R1, R2: are identical or different and are C6- to C10-aryl which is unsubstituted or carries one or more, e.g. 1, 2, 3, 4 or 5, substituents which are selected from C1- to C6-alkyl, C3- to C6-cycloalkyl, C6- to C10-aryl, C1- to C6-alkoxy and amino; Z is a group CHR3R4 or aryl which is unsubstituted or carries one or more, e.g.Type: GrantFiled: December 18, 2015Date of Patent: May 22, 2018Assignee: BASF SEInventors: Mathias Schelwies, Rocco Paciello, Gunnar Heydrich, Günter Wegner, Gerd-Dieter Tebben, Martin Haubner, Andreas Keller, Oliver Bey, Stephanie Renz, Georg Seeber
-
Patent number: 9714205Abstract: The subject matter of the present invention is a process for direct synthesis of (meth)acrolein from a reactive mixture comprising at least one compound chosen from ethers, acetals or hemiacetals derived from linear alcohols comprising from 1 to 3 carbon atoms. Examples of compounds are dimethyl ether, diethyl ether, methyl ethyl ether, dimethoxymethane, diethoxymethane, dipropoxymethane, 1,1-dimethoxyethane or 1,1-diethoxyethane. The process of the invention comprises two successive phases: oxidation then aldol condensation, which can be carried out in the presence of a solid oxidation catalyst chosen from molybdenum-based catalysts and optionally of an aldol condensation catalyst. These two phases are carried out in a reaction system comprising a single reactor or optionally two reactors in cascade.Type: GrantFiled: March 26, 2015Date of Patent: July 25, 2017Assignee: Arkema FranceInventor: Jean-Luc Dubois
-
Patent number: 8871982Abstract: The present invention relates to the field of catalytic hydrogenation and, more particularly, to a process for the reduction by hydrogenation, using molecular H2, of a C6-C20 conjugated dienal into the corresponding deconjugated enal, characterized in that said process is carried out in the presence of a catalytic system comprising at least a base and at least one complex in the form of a rhodium complex comprising a C34-C60 bidentate diphosphine ligand (L2) coordinating the rhodium.Type: GrantFiled: February 17, 2012Date of Patent: October 28, 2014Assignee: Firmenich SAInventors: Lionel Saudan, Michel Alfred Joseph Saudan, Sylvia Joyeuse Adélaïde Ada Saudan
-
Publication number: 20140316149Abstract: This disclosure is directed to methods of preparing organic aldehydes, each method comprising contacting a terminal olefin with an oxidizing mixture comprising: (a) a dichloro-palladium complex; (b) a copper complex; (c) a source of nitrite; under aerobic reaction conditions sufficient to convert at least a portion of the terminal olefin to an aldehyde.Type: ApplicationFiled: April 17, 2014Publication date: October 23, 2014Applicant: CALIFORNIA INSTITUTE OF TECHNOLOGYInventors: ZACHARY K. WICKENS, BILL MORANDI, ROBERT H. GRUBBS, KACPER SKAKUJ, SARAH BRONNER
-
Patent number: 8742177Abstract: A continuous process and system for preparing branched aldehydes by reacting aldehyde with an acid polymeric catalyst absent any metal from Group VIII to produce a product having about 10 to 99.99% by weight branched unsaturated aldehyde and at least 92% selectivity of reaction to the branched aldehyde and recycling a portion of the product.Type: GrantFiled: December 7, 2012Date of Patent: June 3, 2014Assignees: Rohm and Haas Company, Dow Global Technologies LLCInventors: Michael C. Becker, Robert J. Olsen, James F. Tate, Jose Antonio Trejo-O'Reilly
-
Publication number: 20140128622Abstract: A process for the oxidation of an organic carbonyl compound comprising reacting the organic carbonyl compound, optionally in the presence of a solvent, with hydrogen peroxide in the presence of a catalyst comprising a tin-containing zeolitic material having an MWW-type framework structure.Type: ApplicationFiled: November 5, 2013Publication date: May 8, 2014Applicant: BASF SEInventors: Nicolas Vautravers, Joaquim Henrique Teles, Andrei-Nicolae Parvulescu, Ulrich Müller
-
Patent number: 8674144Abstract: The present invention provides a catalyst used for manufacturing an optically active carbonyl compound by selective asymmetric hydrogenation of an ?,?-unsaturated carbonyl compound, which is insoluble in a reaction mixture, and a method for manufacturing the corresponding optically active carbonyl compound. Particularly, the invention provides a catalyst for obtaining an optically active citronellal useful as a flavor or fragrance, by selective asymmetric hydrogenation of citral, geranial or neral. The invention relates to a catalyst for asymmetric hydrogenation of an ?,?-unsaturated carbonyl compound, which comprises: a powder of at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table, or a metal-supported substance in which the at least one metal is supported on a support; an optically active peptide compound; and an acid, and also relates to a method for manufacturing an optically active carbonyl compound using the same.Type: GrantFiled: November 28, 2011Date of Patent: March 18, 2014Assignee: Takasago International CorporationInventors: Shinya Yamada, Hironori Maeda, Yoji Hori
-
Publication number: 20130331611Abstract: The present invention relates to the field of catalytic hydrogenation and, more particularly, to a process for the reduction by hydrogenation, using molecular H2, of a C6-C20 conjugated dienal into the corresponding deconjugated enal, characterized in that said process is carried out in the presence of a catalytic system comprising at least a base and at least one complex in the form of a rhodium complex comprising a C34-C60 bidentate diphosphine ligand (L2) coordinating the rhodium.Type: ApplicationFiled: February 17, 2012Publication date: December 12, 2013Applicant: FIRMENICH SAInventors: Michel Alfred Joseph SAUDAN, Sylvia Joyeuse Adélaïde Ada SAUDAN
-
Publication number: 20130172626Abstract: A continuous process and system for preparing branched aldehydes by reacting aldehyde with an acid polymeric catalyst absent any metal from Group VIII to produce a product having about 10 to 99.99% by weight branched unsaturated aldehyde and at least 92% selectivity of reaction to the branched aldehyde and recycling a portion of the product.Type: ApplicationFiled: December 7, 2012Publication date: July 4, 2013Applicants: DOW GLOBAL TECHNOLOGIES LLC, ROHM AND HAAS COMPANYInventors: Rohm and Haas Company, Dow Global Technologies LLC
-
Patent number: 8455698Abstract: The invention relates to a method for producing a mixture containing hydroxy- and aldehyde functional compounds by a cross-metathesis reaction of at least one at least monounsaturated fatty acid or at least one at least monounsaturated fatty acid derivative with an olefinic compound having at least one hydroxy group and at least one C—C double bond, in the presence of a metathesis catalyst at a maximum temperature of 180° C.Type: GrantFiled: December 30, 2009Date of Patent: June 4, 2013Assignee: Evonik Degussa GmbHInventors: Michael A. R. Meier, Anastasiya Rybak, Dominik Geisker
-
Patent number: 8394996Abstract: The invention relates to a method for producing aldehyde functional compounds by a cross-metathesis reaction of an olefinic compound having at least one hydroxy group and at least one C—C double bond with at least one at least monounsaturated fatty acid or at least one at least monounsaturated fatty acid derivative, in the presence of a metathesis catalyst at a maximum temperature of 180° C. and in the presence of at least one reagent that acts as a protective group-forming compound in relation to the aldehyde group of the aldehyde functional compounds.Type: GrantFiled: January 12, 2010Date of Patent: March 12, 2013Assignee: Evonik Degussa GmbHInventors: Michael A. R. Meier, Anastasiya Rybak, Dominik Geisker, Peter Hannen, Martin Roos
-
Patent number: 8389775Abstract: The invention relates to a process for preparing polyether alcohols, which comprises the steps a) reaction of an unsaturated natural oil or fat with a mixture of carbon monoxide and hydrogen, b) reaction of the mixture from step a) with hydrogen, c) reaction of the product from step b) with an alkylene oxide in the presence of a catalyst.Type: GrantFiled: January 26, 2009Date of Patent: March 5, 2013Assignee: BASF SEInventors: Darijo Mijolovic, Andrea Haunert, Andreas Kunst, Stephan Bauer, Qiang Miao, Berend Eling
-
Publication number: 20120136176Abstract: The present invention provides a catalyst used for manufacturing an optically active carbonyl compound by selective asymmetric hydrogenation of an ?,?-unsaturated carbonyl compound, which is insoluble in a reaction mixture, and a method for manufacturing the corresponding optically active carbonyl compound. Particularly, the invention provides a catalyst for obtaining an optically active citronellal useful as a flavor or fragrance, by selective asymmetric hydrogenation of citral, geranial or neral. The invention relates to a catalyst for asymmetric hydrogenation of an ?,?-unsaturated carbonyl compound, which comprises: a powder of at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table, or a metal-supported substance in which the at least one metal is supported on a support; an optically active peptide compound; and an acid, and also relates to a method for manufacturing an optically active carbonyl compound using the same.Type: ApplicationFiled: November 28, 2011Publication date: May 31, 2012Applicant: TAKASAGO INTERNATIONAL CORPORATIONInventors: Shinya YAMADA, Hironori MAEDA, Yoji HORI
-
Patent number: 7973198Abstract: The present invention relates to a process for preparing optically active carbonyl compounds by asymmetrically hydrogenating ?,?-unsaturated carbonyl compounds in the presence of optically active transition metal catalysts which are soluble in the reaction mixture and have at least one carbon monoxide ligand, the optically active catalyst which has at least one carbon monoxide ligand and is to be used in each case being prepared by pretreating a catalyst precursor with a gas mixture comprising carbon monoxide and hydrogen and the asymmetric hydrogenation being performed in the presence of carbon monoxide supplied additionally to the reaction mixture.Type: GrantFiled: April 17, 2008Date of Patent: July 5, 2011Assignee: BASF SEInventors: Joachim Schmidt-Leithoff, Christoph Jäkel, Rocco Paciello
-
Publication number: 20110098508Abstract: One or more embodiments of the invention are directed to the synthetic methods for making lepidopteran pheromones including navel orangeworm pheromones. The synthetic methods involve novel, efficient, and environmentally benign steps and procedures.Type: ApplicationFiled: April 20, 2010Publication date: April 28, 2011Inventors: Andrew Thompson, Shawn Zhang, Lonnie Robarge
-
Publication number: 20100152494Abstract: The present invention relates to a process for preparing optically active carbonyl compounds by asymmetrically hydrogenating ?,?-unsaturated carbonyl compounds in the presence of optically active transition metal catalysts which are soluble in the reaction mixture and have at least one carbon monoxide ligand, the optically active catalyst which has at least one carbon monoxide ligand and is to be used in each case being prepared by pretreating a catalyst precursor with a gas mixture comprising carbon monoxide and hydrogen and the asymmetric hydrogenation being performed in the presence of carbon monoxide supplied additionally to the reaction mixture.Type: ApplicationFiled: April 17, 2008Publication date: June 17, 2010Applicant: BASF SEInventors: Joachim Schmidt-Leithoff, Christoph Jäkel, Rocco Paciello
-
Patent number: 7683191Abstract: The invention relates to a method for producing chiral organic compounds by asymmetric catalysis, using ionic catalysts comprising a chiral catalyst anion. The claimed method is suitable for reactions which are carried out over cationic intermediate stages, such as iminium ions or acyl pyridinium ions. The invention enables the production of chiral compounds with high ee values, that until now could only be obtained by means of costly purification methods.Type: GrantFiled: February 27, 2007Date of Patent: March 23, 2010Assignee: Studiangesellschaft Kohle mbHInventors: Benjamin List, Sonja Mayer, Martin Nolwenn, Wang Xingwang
-
Patent number: 7632973Abstract: Methods for preparing self-aldol condensation products of prenyl aldehyde (3-methyl-2-butenal) by use of an amine catalyst under weakly acidic conditions at temperatures of 10° C. or higher are disclosed. Methods are disclosed for the selective formation of ?-1,2-adducts and ?-1,2-adducts of prenyl aldehyde, and for the formation of specialty compositions useful in the flavor and fragrance industries.Type: GrantFiled: April 24, 2008Date of Patent: December 15, 2009Assignee: Loyola University of ChicagoInventor: James H. Babler
-
Publication number: 20090186976Abstract: The invention provides a method of preparing a crosslinked polymer, which method comprises polymerising branched polyunsaturated monomers by a metathesis polymerisation reaction, wherein the branched polyunsaturated monomers contain acyclic ethylenically unsaturated groups that are capable of undergoing polymerization by a metathesis reaction such that the metathesis polymerisation produces a crosslinked polymer and substantially no non-volatile ethylenically unsaturated by-products.Type: ApplicationFiled: June 30, 2006Publication date: July 23, 2009Inventors: Christopher Henry Such, Jim Patel, William Roy Jackson, Andrea Jane Robinson, Algirdas Kazimieras Serelis
-
Patent number: 7399879Abstract: A process for the preparation of a monoalkylidene substituted 1,4-dions derivatives of formula (Ia) or (Ib) or a mixture of (Ia) and (Ib): wherein: R1, R2 and R3, equal to or different from each other, are hydrogen atoms or C1–C20 hydrocarbon groups: T1 and T2, equal to or different from each other, are OR4, R4, NR42, SR4 or PR42; or T1 and T2 can be fused in an oxygen atom or a NR4 group; said process comprises the step of reacting a compound of formula (II) with a compound of formula (IIIa) or (IIIb) in the presence of at least one equivalent with respect to the compound of formula (IIIa) or (IIIb) of a carbonate of metal M or of a compound of formula MTj such as K2CO3 or KHCO3Type: GrantFiled: July 25, 2003Date of Patent: July 15, 2008Assignee: Basell Poliolefine Italia S.p.A.Inventors: Yuri V. Gulevich, Giampiero Morini
-
Patent number: 7285685Abstract: Process for preparing alpha, beta-unsaturated acyclic or cyclic carbonyl compounds by dehydrogenation of the corresponding saturated carbonyl compounds in the gas phase over a heterogeneous dehydrogenation catalyst comprising platinum and/or palladium and tin on an oxidic support.Type: GrantFiled: July 22, 2004Date of Patent: October 23, 2007Assignee: BASF AktiengesellschaftInventors: Christian Walsdorff, Beatrice Rössler, Götz-Peter Schindler, Joaquim H. Teles, Klaus Harth
-
Patent number: 7173139Abstract: Nonmetallic, chiral organic catalysts are used to catalyze the 1,4-addition of an aromatic nucleophile to an ?,?-unsaturated aldehyde. The aromatic nucleophile may be an N,N-disubstituted aniline compound, or an analog thereof. The reaction is efficient and enantioselective, and proceeds with a variety of substituted and unsubstituted aromatic nucleophiles and aldehydes. The invention also provides a method for the deamination of aromatic N,N-disubstituted amines such as those resulting from the 1,4-addition of an aromatic nucleophile to an ?,?-unsaturated aldehyde.Type: GrantFiled: March 21, 2003Date of Patent: February 6, 2007Assignee: California Institute of TechnologyInventors: David W. C. MacMillan, Nick A. Paras
-
Patent number: 7074955Abstract: A continuously operated heterogeneously catalyzed gas-phase partial oxidation of at least one organic compound in an oxidation reactor is operated safely by a process in which an explosion diagram for the feed gas mixture is deposited as the basis of a cut-out mechanism in a computer.Type: GrantFiled: June 12, 2003Date of Patent: July 11, 2006Assignee: BASF AktiengesellschaftInventors: Ulrich Hammon, Jochen Meschke, Ulrich Rauh, Klaus Joachim Müller-Engel, Peter Schlemmer, Volker Schliephake
-
Patent number: 6784323Abstract: Nonmetallic organic catalysts are provided that facilitate the enantioselective reaction of &agr;,&bgr;-unsaturated aldehydes. The catalysts are chiral imidazolidinone compounds having the structure of formula (IIA) or (IIB) or are acid addition salts thereof, wherein, in one preferred embodiment, R1 is C1-C6 alkyl, R2 is tri(C1-C6 alkyl)-substituted methyl, R3 and R4 are hydrogen, and R5 is phenyl optionally substituted with 1 or 2 substituents selected from the group consisting of halo, hydroxyl, and C1-C6 alkyl. The chiral imidazolidinones are useful in catalyzing a wide variety of reactions, including cycloaddition reactions, Friedel-Crafts alkylation reactions, and Michael additions.Type: GrantFiled: July 1, 2002Date of Patent: August 31, 2004Assignee: California Institute of TechnologyInventor: David W. C. MacMillan
-
Publication number: 20040082818Abstract: The invention relates to a process for the preparation, in a single step, of enones by an aldol condensation of a ketone, such as a gem-dimethyl cyclohexylethanone or gemdimethyl cyclohexenylethanone derivative, with an aldehyde in the presence of a novel catalytic system and a co-ingredient, such as a carboxylic acid anhydride or an anhydrous salt, and without the pre-formation of an enolate. The catalytic system is a metal complex, such as a [(Cl)n(alkoxy)4−nTi] or [(Cl)n(alkoxy)4−nZr] complex where n is 1 to 3.Type: ApplicationFiled: October 17, 2003Publication date: April 29, 2004Inventor: Denis Jacoby
-
Patent number: 6660812Abstract: Disclosed is a system of making an olefin derivative from a dilute olefin feed. Dilute olefin is sent to an olefin reaction unit to form an olefin derivative product. The olefin derivative product is recovered from the reaction unit while a vent stream is also removed. Olefin is separated from the vent stream, and the olefin is sent to the olefin reaction unit for additional processing.Type: GrantFiled: June 15, 2001Date of Patent: December 9, 2003Assignee: ExxonMobil Chemical Patents Inc.Inventors: Keith H. Kuechler, Minquan Cheng, Marc L. DeChellis, David R. Lumgair, Jr., Russell D. Sellen, Gary F. Janda
-
Patent number: 6586636Abstract: Production of unsaturated aldehydes by the aldol condensation of straight chain aldehydes, e.g. butyraldehyde, by contacting the aldehyde in the vapour phase with a particulate catalyst comprising at least one basic alkali metal compound supported on an inert substrate at a temperature above 175° C.Type: GrantFiled: May 22, 2001Date of Patent: July 1, 2003Assignee: Imperial Chemical Industries PLCInventor: Gordon James Kelly
-
Patent number: 6518453Abstract: In a process for stabilizing chemical compounds having at least one ethylenically unsaturated bond to undesired free radical polymerization, a nitroxyl radical and a chemical compound containing phosphorus in chemically bonded form are added to the unsaturated compound present as pure substance or as a component of a mixture.Type: GrantFiled: July 3, 2001Date of Patent: February 11, 2003Assignee: BASF AktiengesellschaftInventors: Heinz Friedrich Sutoris, Gerhard Wagenblast, Volker Schliephake, Jürgen Schröder, Klaus Joachim Müller-Engel, Harald Keller, Thomas Jaworek
-
Patent number: 6506944Abstract: C6 compounds of the formula (I) E—CH2—CH═CH—CH2—E1 (I) are prepared by self metathesis or cross metathesis of compounds of the formulae (II) and/or (III) R—CH═CH—CH2—E (II) R1—CH═CH—CH2—E1 (III) where E, E1 are independently —CHO, —COOH, —COOR2, —C(O)NR3R4, —CN, R, R1 are independently H, C1-12-alkyl, C6-12-aryl or C7-13-alkylaryl and R2, R3, R4 are independently H, C1-12-alkyl, C7-13-aralkyl, in the presence of a homogeneous catalyst comprising ruthenium compounds or ruthenium complexes.Type: GrantFiled: February 17, 2000Date of Patent: January 14, 2003Assignee: BASF AktiengesellschaftInventors: Peter Schwab, Michael Schulz
-
Patent number: 6403838Abstract: A process for making 2,7-dimethyl-2,4,6-octatrien-1,8-dial starting form an allylic halide is described. The process steps include aldehyde protection, conversion to a sulfide, oxidation to an allylic sulfone followed by a Ramberg-Backlund reaction and hydrolysis.Type: GrantFiled: September 27, 2001Date of Patent: June 11, 2002Inventors: Sangho Koo, Hojin Choi, Minsoo Park, Minkoo Ji
-
Patent number: 6369277Abstract: An &agr;,&bgr;-unsaturated carbonyl compound of formula (I) where R1 is saturated C1-40-hydrocarbyl or a substituted or unsubstituted aromatic radical containing moiety, and R2, R3 and R4, independently of one another, are hydrogen or a C1- to C4-alkyl group, is selectively hydrogenated in the liquid phase to a saturated carbonyl compound of formula (II) with hydrogen in the presence of a pulverulent palladium and/or rhodium catalyst and in the presence of an organic base, by conducting the hydrogenation in a packed bubble column reactor in which product is recycled and hydrogen gas is recirculated.Type: GrantFiled: August 25, 2000Date of Patent: April 9, 2002Assignee: BASF AktiengesellschaftInventors: Franz Josef Broecker, Gerd Kaibel, Werner Aquila, Hartwig Fuchs, Guenter Wegner, Manfred Stroezel
-
Patent number: 6326519Abstract: Diallylic sulfides represented by Formula I wherein: R1 and R2 are independently chosen from the group consisting of —CHO, —CH2Cl, —CH2Br, —CH2I, —CH2OH, CH2OSO2CF3, —CH2OSO2Ph, —CH2OSO2C6H4CH3 and —CH2OSO2CH3 and processes for making the same.Type: GrantFiled: June 4, 2001Date of Patent: December 4, 2001Inventors: Sangho Koo, Hojin Choi, Minsoo Park, Minkoo Ji
-
Publication number: 20010044558Abstract: Production of unsaturated aldehydes by the aldol condensation of straight chain aldehydes, e.g. butyraldehyde, by contacting the aldehyde in the vapour phase with a particulate catalyst comprising at least one basic alkali metal compound supported on an inert substrate at a temperature above 175° C.Type: ApplicationFiled: May 22, 2001Publication date: November 22, 2001Applicant: Imperial Chemical Industries PLCInventor: Gordon James Kelly
-
Patent number: 6175044Abstract: 3,7-Dimethyl-2,6-octadien-1-al of formula I is prepared continuously by: thermally cleaving, in the presence or absence of an acid catalyst, 3-methyl-2-buten-1-al diprenyl acetal of formula II: thereby eliminating 3-methyl-2-buten-1-ol of formula III and yielding cis/trans-prenyl 3-methylbutadienyl ether of formula IV: thermally rearranging the resultant butadienyl ether of formula IV thereby yielding 2,4,4-trimethyl-3-formyl-1,5-hexadiene of formula V: subsequently rearranging intermediate (V) thereby yielding citral product of formula I, which comprises: as the reaction proceeds, continuously distilling the reaction mixture thereby continuously removing prenol, which is formed by degradation of acetal II, and the intermediates of formula IV and V and any citral product which is formed during the reaction; and thermally rearranging said intermediates of formula IV and V at a temperature of 100-200° C.Type: GrantFiled: September 24, 1999Date of Patent: January 16, 2001Assignee: BASF AktiengesellschaftInventors: Jörg Therre, Gerd Kaibel, Werner Aquila, G{umlaut over (u)}nter Wegner, Hartwig Fuchs
-
Patent number: 5929288Abstract: To manufacture polyene aldehydes and polyene dialdehydes a polyene O,O-dialkyl acetal or polyene di(O,O-dialkyl acetal) is reacted with a 1-alkoxy-1,3-diene in the presence of a Lewis acid or a Bronsted acid. The reaction mixture is then hydrolyzed and the alcohol is cleaved under basic conditions from the polyene derivative produced by the reacting. Those intermediates in this process from which the alcohol is to be cleaved are novel. The final products are primarily carotenoids which can be used as colorants and pigments for foodstuffs, animal products, and the like.Type: GrantFiled: May 29, 1997Date of Patent: July 27, 1999Assignee: Roche Vitamins Inc.Inventor: August Ruttimann
-
Patent number: 5888923Abstract: The present invention relates to a modified Raney nickel catalyst which can serves as hydrogenation catalyst for hydroxy aldehydes, such as 4-hydroxy-butanal, and 2-methyl-3-hydroxypropanal and hydroxy cyclic ethers such as 2-hydroxy-tetrahydrofuran. Further, a process for preparing diols by using the modified Raney nickel catalyst is provided.Type: GrantFiled: April 15, 1996Date of Patent: March 30, 1999Assignee: Dairen Chemical CorporationInventors: Shien Chang Chen, C. C. Chu, F. S. Lin, J. Y. Chou, C. C. Huang
-
Patent number: 5801292Abstract: A process for condensing aldehydes where an aldehyde having an a hydrogen and having the formula R.sub.1 CHO, wherein R.sub.1 is selected from alkyl having one to twelve carbon atoms and aralkyl having one to fourteen carbon atoms, is combined with hydrated MgO to form a reaction product comprising an aldol of said aldehyde, the unsaturated aldehyde derived by dehydration of said aldol, or mixtures thereof. In a second embodiment, a first composition selected from aldehydes containing an a hydrogen and having the formula R.sub.1 CHO, wherein R.sub.1 is as defined above, is combined with a second composition selected from aldehydes having the formula R.sub.2 CHO, wherein R.sub.2 is selected from H, alkyl having one to twelve carbon atoms, and aralkyl having one to fourteen carbon atoms, and with hydrated MgO, to form a reaction product mixture comprising an aldol of said aldehyde, the unsaturated aldehyde derived by dehydration of said aldol, or mixtures thereof.Type: GrantFiled: March 28, 1996Date of Patent: September 1, 1998Assignee: Eastman Chemical CompanyInventors: Thomas J. Kwok, Windell C. Watkins
-
Patent number: 5770762Abstract: Described is a process for producing a 4-substituted-2-butenal represented by the following formula (1); ##STR1## (wherein X represents an acyloxy group or halogen atom; R represents hydrogen atom, an aliphatic hydrocarbon group or an aromatic hydrocarbon group; and these hydrocarbon groups can be substituted with hydroxyl group, an alkoxy group, an aryloxy group, an acyl group or an alkoxycarbonyl group), which is useful as synthetic intermediates of phormaceutieals, agricultural chemicals and the like,comprising subjecting a substituted acetaldehyde represented by the following formula (2);X--CH.sub.2 --CHO (2)(wherein X has the same meaning as defined above), with an aldehyde represented by the following formula (3);R--CH.sub.2 --CHO (3)(wherein R has the same meaning as defined above) in the presence of an amino carboxylic acid.Type: GrantFiled: April 22, 1997Date of Patent: June 23, 1998Assignee: Kuraray Co., Ltd.Inventors: Hideharu Iwasaki, Takashi Onishi
-
Patent number: 5471005Abstract: A procedure for forming methylmalonaldehyde from propionaldehyde, an alkyl formate and a sodium alkoxide, utilizing a crossed-Claisen condensation is disclosed. The procedure avoids the formation of aldol condensation products. Also disclosed are processes for preparing 3-alkoxy-2-methylpropenals such as 2-methyl-3-(2-methyl-2-propenoxy)propenal from methylmalonaldehyde. The latter products are useful in the synthesis of carotenoids.Type: GrantFiled: November 18, 1994Date of Patent: November 28, 1995Assignee: Loyola University of ChicagoInventor: James H. Babler
-
Patent number: 5442095Abstract: Catalysts based on rhodium and water-soluble phosphine obtained by using rhodium perchlorate as the precursor rhodim salt. Also, processes for the preparation of these catalysts and to their use are provided.Type: GrantFiled: April 14, 1993Date of Patent: August 15, 1995Assignee: Rhone-Poulenc Nutrition AnimaleInventor: Patrick Auvray
-
Patent number: 5382700Abstract: A process for producing dimeric unsaturated aldehydes from alpha, beta unsaturated aldehyde is disclosed. This process is conducted by contacting the alpha, beta unsaturated aldehyde with a copper (II) catalyst and a complexing amine catalyst in a medium with a relatively high dielectric constant in substantially anhydrous and aprotic conditions.Type: GrantFiled: May 24, 1993Date of Patent: January 17, 1995Assignee: Eastman Chemical CompanyInventor: William A. Beavers
-
Patent number: 5254743Abstract: Solid solutions of a class of divalent metal oxides and a class of trivalent metal oxides resulting from calcination of layered double hydroxides related to hydrotalcite have been prepared with a surface area in excess of 150 m.sup.2 /g. Such high surface area materials are found to be quite effective in the aldol condensation of aldehydes and ketones, and in particular in the conversion of n-butyraldehyde to 2-ethyl-2-hexenal in high yield and with good selectivity in a liquid phase reaction at temperatures under about 200.degree. C. Variants can be devised where the aldol condensation product, an .alpha.,.beta.-unsaturated aldehyde or ketone, is concurrently reduced to the saturated alcohol under process conditions.Type: GrantFiled: December 9, 1992Date of Patent: October 19, 1993Assignee: UOPInventors: Jennifer S. Holmgren, Blaise J. Arena
-
Patent number: 5254742Abstract: A process for preparing 2-hexene-1,6-dial comprising dimerizing 2-propenal in the presence of an organometallic compound of the group VIII metal. The desired compound can be obtained under mild conditions with industrial advantages.Type: GrantFiled: October 8, 1992Date of Patent: October 19, 1993Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Yuji Ohgomori, Shuji Ichikawa, Takahiro Yoneyama, Naoko Sumitani
-
Patent number: 5243082Abstract: Acrolein is prepared by the heating of 3,4-dihydro-2H-pyran-2-carboxaldehyde. The process provides acrolein in very high yields and with few impurities. The process is advantageously employed to produce acrolein at the point of use.Type: GrantFiled: September 22, 1992Date of Patent: September 7, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: William G. Etzkorn, William D. Neilsen
-
Patent number: 5177265Abstract: An improved method for preparing citral in liquid phase from prenol and prenal, wherein, in a single reaction enclosure, the prenol and prenal are condensed in the presence of a mineral acid at a concentration of about 5.10.sup.-3 mole for one mole of prenal, 90 to 95% of the acid is neutralized, and once excess prenal and prenol is eliminated, the citral is distilled.Type: GrantFiled: October 31, 1991Date of Patent: January 5, 1993Assignee: Rhone-Poulenc SanteInventors: Pierre Chabardes, Jacques Chazal
-
Patent number: 5177266Abstract: There is provided a process for the manufacture of 2-alkoxymethylacrolein compounds via the reaction of an appropriate alcohol and acrolein in the presence of an acid and a trisubstituted amine to form an intermediate and the subsequent reaction of the intermediate with formaldehyde in the presence of an acid and a disubstituted amine.Type: GrantFiled: December 20, 1991Date of Patent: January 5, 1993Assignee: American Cyanamid CompanyInventor: Henry L. Strong
-
Patent number: 5144089Abstract: Solid solutions of magnesium oxide-aluminum oxide related to hydrotalcite and what previously has been referred to as synthetic hydrotalcites, have been prepared with a surface area in excess of 250 m.sup.2 lg, especially at low Mg/Al atom ratios. Such high surface area materials are found to be quite effective in the aldol condensation of aldehydes, and in particular in the conversion of n-butyraldehyde to 2-ethyl-2-hexenal in high yield and with good selectivity in a liquid phase reaction at temperatures under about 200.degree. C.Type: GrantFiled: October 21, 1991Date of Patent: September 1, 1992Assignee: UOPInventors: Blaise J. Arena, Jennifer S. Holmgren
-
Patent number: 5053552Abstract: The present invention provides a novel process for producing .alpha.,.beta.-unsaturated aldehydes including industrial important fragrances such as citral and sinensal, starting materials for preparing pharmaceutical drugs such as senecioaldehyde, farnesal, 8-acetoxy-2,6-dimethyl-2,6-octadienal and the like, directly and in high yield, from formic acid esters of allylic alcohols in the presence of a catalytic amount of aluminum alkoxide by the oxidation of the corresponding alehyde.Type: GrantFiled: June 14, 1990Date of Patent: October 1, 1991Assignee: Kuraray Company, Ltd.Inventors: Toshiki Mori, Shigeaki Suzuki, Takashi Onishi, Kazuo Yamamoto
-
Patent number: 4987252Abstract: In order to recover methacrolein and/or methacrylic acid by quenching a reaction product gas obtained by catalytic oxidation of isobutylene or the like, the reaction product gas is charged into a quench column through a double-wall pipe and is then brought into contact with a condensate as a cooling medium. Deposition of terephthalic acid and the like inside the column is prevented by controlling the temperature of a bottom in the quench column and that of an overhead gas of a quench column unit. An aromatic carboxylic acid, aromatic aldehyde, metal powder is added to an aqueous solution of methacrylic acid, which contains terephthalic acid and the like, so that the terephthalic acid and the like are caused to precipitate for their removal.Type: GrantFiled: June 27, 1988Date of Patent: January 22, 1991Assignees: Mitsui Toatsu Chemicals, Incorporated, Kyowa Gas Chemical Industry Co., Ltd.Inventors: Morimasa Kuragano, Kozo Iwasaki, Takeshi Isobe, Isao Fukada, Minoru Koshibe, Yoshihiro Sezaki, Hirozo Segawa, Katsuji Yoguchi
-
Patent number: 4820858Abstract: The invention relates to a process for the preparation of 2-(hydroxyalkyl)acrylic compounds having the formula ##STR1## wherein X represents a --CN group, a --COOR.sub.3 group, a --COR.sub.4 group or a --CONR.sub.4 R.sub.5 group wherein R.sub.3 is an alkyl group containing 1-4 C atoms and R.sub.4 and R.sub.5 independently represent an H atom or R.sub.3, andwherein R.sub.1 and R.sub.2 independently represent an H atom or an alkyl group with 1-4 C atoms or an (hetero) aryl group, or R.sub.1 and R.sub.2 together represent a cyclic compound with 5-12 C atomsby contacting an acrylic compound H.sub.2 C.dbd.CH--X with a carbonyl compound of the formula ##STR2## wherein X, R.sub.1 and R.sub.2 denote the same as in the above, this being effected in the liquid phase in the presence of a tertiary amine, characterized in that the reaction is carried out at a pressure in excess of 500 bar in excess of 500 bar, advantageously 1,500-18,000 bar.Type: GrantFiled: March 18, 1988Date of Patent: April 11, 1989Assignee: Stamicarbon B.V.Inventors: Neil S. Isaacs, Jonathan Hill