Aldehyde Reacted With Aldehyde (e.g., Aldol Condensation, Etc.) Patents (Class 568/463)
  • Patent number: 9688599
    Abstract: A method for producing mixed aldol products from the products of hydroformylation reactions. In one embodiment, the method comprises mixing hydroformylation reaction products comprising aldehydes with a catalyst inside a reactor to create a mixture. The method also includes agitating the mixture at a temperature in a range of between about 200° F. to about 275° F. to create a reacted mixture. The reacted mixture is then cooled in the reactor to create an organic phase and an aqueous phase. The organic phase is pumped out of the reactor and may then be transferred to a distillation tower. The organic phase may be distilled until any mixed aldol products are isolated, wherein the mixed aldol products may be subsequently removed.
    Type: Grant
    Filed: April 17, 2015
    Date of Patent: June 27, 2017
    Assignee: Texmark Chemicals, Inc.
    Inventors: Rajeshwari Kannan, Rebecca L. Rosas
  • Patent number: 9492813
    Abstract: Disclosed is a method for regenerating a hydrogenation catalyst. More specifically, disclosed is a method for regenerating a hydrogenation catalyst poisoned during hydrogenation of a hydroformylation product for preparation of alcohol by stopping hydrogenation in a hydrogenation stationary phase reactor in which the hydrogenation catalyst is set and flowing hydrogen gas under a high temperature normal pressure. The method has an effect in that the poisoned hydrogenation catalyst can be efficiently recovered through a simple process.
    Type: Grant
    Filed: August 2, 2013
    Date of Patent: November 15, 2016
    Assignee: LG Chem, Ltd.
    Inventors: Dae Chul Kim, Sung Shik Eom, Dong-Hyun Ko, Moo Ho Hong, O Hak Kwon
  • Patent number: 9006496
    Abstract: The subject of the present invention is a method for separating phenolic compounds in salified form from a reaction medium comprising them. The method of the invention for separating phenolic compounds in salified form from an aqueous reaction medium resulting from the reaction of a phenolic compound and of glyoxylic acid in the presence of a base leading to a reaction medium comprising at least the excess of initial phenolic compound in salified form and the various mandelic compounds in salified form resulting from the reaction, is characterized by the fact that said reaction medium is brought into contact with a basic anion-exchange resin that leads to the selective attachment of the initial phenolic compound to said resin and to the recovery of an aqueous stream comprising the mandelic compounds in salified form resulting from the reaction, and that the phenolic compound in salified form attached to the resin is separated by a resin regeneration treatment.
    Type: Grant
    Filed: December 6, 2013
    Date of Patent: April 14, 2015
    Assignee: Rhodia Operations
    Inventor: Magali Desouhant-Massacret
  • Patent number: 8933277
    Abstract: A process is provided for recovering components from a low boiler mixture which is obtained in the distillation of hydrogenation effluents from the preparation of polymethylols, by multistage distillation of the low boiler mixture having a tertiary amine, water, methanol, a polymethylol, a methylolalkanal, an alcohol and an alkanal with a methylene group in the alpha position to the carbonyl group. A first distillation stage involves separating the low boiler mixture into a higher-boiling, predominantly water-rich fraction and into a lower-boiling aqueous organic fraction having the tertiary amine. A second distillation stage involves separating the aqueous organic fraction from the first distillation stage into a predominantly amine-containing fraction and a further amine-depleted fraction. The tertiary amine is trimethylamine or triethylamine and the bottom temperature in the second distillation stage is at least 110° C.
    Type: Grant
    Filed: January 7, 2010
    Date of Patent: January 13, 2015
    Assignee: BASF SE
    Inventors: Stephan Schlitter, Michael Steiniger, Stefan Rittinger, Tilman Sirch, Steffen Maas
  • Patent number: 8841489
    Abstract: The invention relates to a continuous method for carrying out a multiphase aldol condensation reaction to obtain mixed ?,?-unsaturated aldehydes by reacting a mixture of two aliphatic aldehydes having different numbers of carbon atoms, i.e. 2 to 5, in the molecule in a vertical tubular reactor in a concurrent flow in the presence of an aqueous solution of a basically reacting compound. In said method, the aldehyde mixture is dispersed in the aqueous phase in the form of drops, and the aqueous solution of the basically reacting compound flows through the tubular reactor as a continuous phase in laminar conditions.
    Type: Grant
    Filed: February 9, 2012
    Date of Patent: September 23, 2014
    Assignee: Oxea GmbH
    Inventors: Dirk Bermann, Guido D. Frey, Norman Nowotny, Kurt Schalapski, Heinz Strutz
  • Patent number: 8581008
    Abstract: The invention relates to a method for continuously producing ?,?-unsaturated C10-aldehydes from aliphatic C5-aldehydes, comprising the following steps: aldol-condensing aliphatic C5-aldehydes into ?,?-unsaturated C10-aldehydes in the presence of an aqueous base in a tube reactor; phase separating the output of the tube reactor into an aqueous catalyst phase and an organic product phase; separating the organic product phase into ?,?-unsaturated C10-aldehydes, aliphatic C5-aldehydes, and auxiliary products; discharging a part of the aqueous catalyst phase to remove the reaction water and supplementing said part with liquor solution and subsequently returning said part to the tube reactor. The task of the invention is to improve a method of said kind in a way such that it requires lower energy input. This is achieved in that the aliphatic C5-aldehydes and/or the ?,?-unsaturated C10-aldehydes are dispersed in the aqueous base as drops, wherein the average Sauter diameter of the drops is between 0.2 mm and 2 mm.
    Type: Grant
    Filed: February 23, 2010
    Date of Patent: November 12, 2013
    Assignee: Evonik Oxeno GmbH
    Inventors: Alfred Kaizik, Dirk Fridag, Hans-Gerd Lueken, Wilfried Bueschken
  • Publication number: 20120123169
    Abstract: The invention relates to a method for continuously producing ?,?-unsaturated C10-aldehydes from aliphatic C5-aldehydes, comprising the following steps: aldol-condensing aliphatic C5-aldehydes into ?,?-unsaturated C10-aldehydes in the presence of an aqueous base in a tube reactor; phase separating the output of the tube reactor into an aqueous catalyst phase and an organic product phase; separating the organic product phase into ?,?-unsaturated C10-aldehydes, aliphatic C5-aldehydes, and auxiliary products; discharging a part of the aqueous catalyst phase to remove the reaction water and supplementing said part with liquor solution and subsequently returning said part to the tube reactor. The task of the invention is to improve a method of said kind in a way such that it requires lower energy input. This is achieved in that the aliphatic C5-aldehydes and/or the ?,?-unsaturated C10-aldehydes are dispersed in the aqueous base as drops, wherein the average Sauter diameter of the drops is between 0.2 mm and 2 mm.
    Type: Application
    Filed: February 23, 2010
    Publication date: May 17, 2012
    Applicant: Evonik Oxeno GmbH
    Inventors: Alfred Kaizik, Dirk Fridag, Hans-Gerd Lueken, Wilfried Bueschken
  • Patent number: 7943047
    Abstract: Process for the treatment of wastewater from an aldolization process which is contaminated with water-soluble and/or dispersed organic impurities by means of single-stage or multistage extraction with an organic liquid of the aldolization process wastewater which has been set to a pH of from 0 to 6, in which an organic liquid obtained by stripping of the acidified aldolization process wastewater or of the acidified and extracted aldolization process wastewater, condensation of the stripped compounds and phase separation of the condensate is used as extractant for the extraction of organic impurities from the acidified aldolization process wastewater and wastewater having a lower content of organic impurities than the aldolization process wastewater fed to the extraction is taken off from the stripping apparatus.
    Type: Grant
    Filed: September 25, 2006
    Date of Patent: May 17, 2011
    Assignee: BASF SE
    Inventors: Siegmar Maassen, Roland Krokoszinski, Detlef Kratz
  • Publication number: 20110021845
    Abstract: Alcohols are prepared from aldehydes employing a bifunctional catalyst; the aldehydes are first condensed and the products of condensation thereof are then converted into alcohols by hydrogenation.
    Type: Application
    Filed: December 10, 2008
    Publication date: January 27, 2011
    Inventors: Danilo Zim, Philippe Marion
  • Patent number: 7855311
    Abstract: Aldehyde and ketone reactants are converted to hydroxyaldehydes, polyhydroxyaldehydes, hydroxyketones and/or polyhydroxyketones in liquid phase by an aldol condensation process where a selected product carbon chain length is produced using specific concentrations of soluble inorganic base at sub-ambient temperature.
    Type: Grant
    Filed: March 10, 2009
    Date of Patent: December 21, 2010
    Inventor: Melvin K. Carter
  • Patent number: 7850841
    Abstract: The invention relates to a process for producing high-quality hydrocarbon base oil particularly of biological origin. The process of the invention comprises aldol condensation, hydrodeoxygenation, and isomerization steps. Aldehydes and/or ketones, preferably of biological origin are used as the feedstock.
    Type: Grant
    Filed: December 12, 2006
    Date of Patent: December 14, 2010
    Assignee: Neste Oil Oyj
    Inventors: Eija Koivusalmi, Ilkka Kilpeläinen, Pirkko Karhunen, Jorma Matikainen
  • Patent number: 7767865
    Abstract: The preparation of hydroxypivalaldehyde is effected by aldolizing isobutyraldehyde with formaldehyde and subsequently working up the resulting reaction effluent by distillation, wherein the reaction effluent is fed to a distillation column which is operated at a top pressure in the range from 0.5 to 1.5 bar and in which a two-stage condensation is provided in the top region, in which the vapors are first conducted into a partial condenser operated at a temperature in the range from 50 to 80° C., whose condensate is recycled at least partly into the distillation column, and in which the vapors uncondensed in the partial condenser are fed to a downstream condenser operated at a temperature in the range from ?40 to +30° C., whose condensate is at least partly discharged.
    Type: Grant
    Filed: February 25, 2008
    Date of Patent: August 3, 2010
    Assignee: BASF SE
    Inventors: Tilman Sirch, Michael Steiniger, Steffen Maas, Stefan Rittinger, Stephan Schlitter
  • Patent number: 7732644
    Abstract: The present invention relates to processes for producing ?,?-unsaturated aldehyde compounds and unsaturated alcohols with a good yield. There is provided a process for producing and ?,?-unsaturated aldehyde compound including the step of subjecting a raw aldehyde compound to an intermolecular condensation reaction in the presence of an amine and a protonic acid having 4 to 20 carbon atoms or a salt thereof; and a process for producing an unsaturated alcohol including the step of subjecting the ?,?-unsaturated aldehyde compound to a reduction reaction.
    Type: Grant
    Filed: November 8, 2006
    Date of Patent: June 8, 2010
    Assignee: Kao Corporation
    Inventors: Kosaku Ishida, Shigeyoshi Tanaka, Takahiro Asada
  • Patent number: 7498469
    Abstract: Glycoaldehyde (GA) is prepared via self condensation of formaldehyde in the presence of a n-heterocyclic carbene to generate GA and glyceraldehyde (GlyAld) with selectivity toward forming the GA. The carbene is generated in situ by the addition of a base to the salt form of the catalyst. Selectivity is controlled by tuning the active site of the catalyst, either sterically and/or electronically.
    Type: Grant
    Filed: November 7, 2007
    Date of Patent: March 3, 2009
    Assignee: Eastman Chemical Company
    Inventors: Andrew James Vetter, Mesfin Ejerssa Janka, Joseph Robert Zoeller
  • Patent number: 7439406
    Abstract: Disclosed is a method for the catalytic hydrogenation of methylol alkanals of general formula (I), where R1 and R2 independently represent an additional methylol group or an alkyl group having with 1 to 22 carbon atoms, or an alkyl group with 1 to 22 C atoms, or an aryl group or aralkyl group with 6 to 33 carbon atoms, in the liquid phase on a hydrogenation catalyst. The inventive method is characterized in that a pH value ranging between 6.3 and 7.
    Type: Grant
    Filed: April 14, 2004
    Date of Patent: October 21, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Alexander Wartini, Matthias Dernbach, Steffen Maas
  • Patent number: 7294745
    Abstract: The present invention provides a novel eco-friendly multi-functional catalyst system useful to obtain C2(n+1) aldol-derivative from Cn-alkenes where n ranges from 2 to 10 in a single step under hydroformylation reaction conditions and adol formation conditions.
    Type: Grant
    Filed: December 30, 2004
    Date of Patent: November 13, 2007
    Assignee: Council of Scientific and Industrial Research
    Inventors: Raksh V. Jasra, Vivek K. Srivastava, Ram S. Shukla, Hari C. Bajaj, Sharad D. Bhatt
  • Patent number: 7098366
    Abstract: A supported catalyst is proposed comprising one or more metal oxides as active component on a catalyst support for carrying out an aldol condensation, with the catalyst support being ?-aluminum oxide, the active component comprising one or more oxides of the elements having atomic numbers 39 or from 57 to 71 and the concentration of the active component being in the range from 5 to 12% by weight, based on the weight of the catalyst support.
    Type: Grant
    Filed: December 2, 2002
    Date of Patent: August 29, 2006
    Inventors: Marcus Sigl, Christian Miller, Walter Dobler, Mathias Haake
  • Patent number: 6900357
    Abstract: Nonmetallic, chiral organic catalysts are used to catalyze an enantioselective aldol coupling reaction between aldehyde substrates. The reaction may be carried out with a single enolizable aldehyde, resulting in dimerization to give a ?-hydroxy aldehyde, or trimerization to give a dihydroxy tetrahydropyran. The reaction may also conducted with an enolizable aldehyde and a second aldehyde, which may or may not be enolizable, so that the coupling is a cross-aldol reaction in which the ?-carbon of the enolizable aldehyde adds to the carbonyl carbon of the second aldehyde in an enantioselective fashion. Reaction systems composed of at least one enolizable aldehyde, an optional additional aldehyde, and the nonmetallic chiral organic catalyst are also provided, as are methods of implementing the enantioselective aldol reaction in the synthesis of sugars.
    Type: Grant
    Filed: April 21, 2003
    Date of Patent: May 31, 2005
    Assignee: California Institute of Technology
    Inventors: David W. C. MacMillan, Alan B. Northrup
  • Patent number: 6586636
    Abstract: 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: Grant
    Filed: May 22, 2001
    Date of Patent: July 1, 2003
    Assignee: Imperial Chemical Industries PLC
    Inventor: Gordon James Kelly
  • Patent number: 6555716
    Abstract: Aldehydes are prepared in a hydroformylation apparatus by the multiphase hydroformylation reaction of one or more olefins with hydrogen and carbon monoxide, where the continuous phase contains a solvent mixture and the hydroformylation catalyst is present in the continuous phase, at least one olefin is present in the dispersed phase, and the loading factor of the tube reactor is greater than or equal to 0.8.
    Type: Grant
    Filed: November 30, 2000
    Date of Patent: April 29, 2003
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Guido Protzmann, Klaus-Diether Wiese, Wilfried Büschken, Dirk Röttger
  • Patent number: 6552232
    Abstract: The present invention is related to a method for forming aldol condensation products, comprising reacting at least one aldehyde starting material in the presence of an ionic liquid medium and a basic catalyst at a temperature range of from about −20° C. to about 300° C. and at a pressure range of from about 1 atm to about 1000 atm for a sufficient time to form the aldol condensation products. The invention is also directed to a method for forming aldol condensation products, comprising reacting at least one aldehyde starting material in the presence of a basic ionic liquid medium at the same parameters specified above. The advantage of the instant invention is the increased selectivity and productivity of the resulting aldol condensation products formed in ionic liquid media, along with the ability to recycle the ionic liquid for use in producing additional aldol condensation products.
    Type: Grant
    Filed: June 26, 2001
    Date of Patent: April 22, 2003
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Christian Peter Mehnert, Nicholas Charles Dispenziere, Richard Henry Schlosberg
  • Patent number: 6525227
    Abstract: A reaction method by a novel Lewis acid catalyst stable in water for organic synthesis by using a metal compound stable in water and functioning as a Lewis acid catalyst and using water as apart or all of a solvent, the metal ion of the metal compound having a hydrolysis constant (pKh) of: 4.3≦pKh≦10.1 and a water exchange rate constant (WERC) of 3.2×106M−1sec−1 or more.
    Type: Grant
    Filed: April 4, 2001
    Date of Patent: February 25, 2003
    Assignee: Japan Science and Technology Corporation
    Inventor: Shu Kobayashi
  • Patent number: 6433230
    Abstract: &agr;,&bgr;-Unsaturated keto compounds are prepared by base-catalyzed aldol condensation of aldehydes and/or ketones having from 1 to 15 carbon atoms, comprising: reacting the aldehydes and/or ketones with an aqueous catalyst solution under adiabatic reaction conditions; and separating the reaction mixture obtained by rapid distillation into a top product comprising water, aldehyde and/or ketone and a bottom product comprising &agr;,&bgr;-unsaturated keto compounds and aqueous catalyst phase.
    Type: Grant
    Filed: November 22, 2000
    Date of Patent: August 13, 2002
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Wilfried Bueschken, Klaus-Diether Wiese, Guido Protzmann
  • Patent number: 6380438
    Abstract: A process for producing 3-hydroxypropanal includes reacting formaldehyde and acetaldehyde to form an aqueous solution of acrolein; and hydrating the aqueous solution of acrolein to form 3-hydroxypropanal, wherein the aqueous solution of acrolein is capable of being hydrated to 3-hydroxypropanal without having to remove excess formaldehyde or acetaldehyde.
    Type: Grant
    Filed: July 13, 2000
    Date of Patent: April 30, 2002
    Assignee: TTC Labs, Inc.
    Inventor: George Robert Winter
  • Patent number: 6380443
    Abstract: A process for preparing 1,3-diols having 6 or more carbon atoms comprises a) provision of at least one alkanal having at least three carbon atoms; b) thermal treatment of the alkanal in the absence of a basic catalyst; c) hydrogenation of the aldol addition product formed in step b); and d) isolation of the 1,3-diol obtained. The process of the present invention makes it possible to prepare 1,3-diols simply and inexpensively.
    Type: Grant
    Filed: October 3, 2000
    Date of Patent: April 30, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Detlef Kratz, Harald Rust, Roland Krokoszinski, Volker Helf
  • Patent number: 6340778
    Abstract: The invention relates to a process for the catalytic aldol condensation of aldehydes by means of a multiphase reaction in a tube reactor, wherein the catalyst is present in the continuous phase and at least one aldehyde is present in a dispersed phase and the loading factor B of the tube reactor is equal to or greater than 0.8; the aldol condensation products obtained in this way can be used for preparing alcohols or carboxylic acids.
    Type: Grant
    Filed: October 24, 2000
    Date of Patent: January 22, 2002
    Assignee: Oxeno Olefinchemie GmbH
    Inventors: Wilfried Bueschken, Klaus-Diether Wiese, Guido Protzmann, Juergen Koch
  • Patent number: 6303549
    Abstract: Aerosol compositions containing fluorinated oils are disclosed. At least one fluorinated component compatible with the fluorinated oil and a propellant are included in the aerosol composition. Fluorinated oil-containing non-aerosol compositions are also disclosed. In a particularly desirable form, the compositions are single-phase.
    Type: Grant
    Filed: March 26, 2001
    Date of Patent: October 16, 2001
    Assignee: Loctite Corporation
    Inventors: Matthew P. Burdzy, Sandra C. Adams
  • Patent number: 6069261
    Abstract: A process carried out in a reaction column for the chemical reaction of substances the reaction of which is affected by an unfavorable equilibrium position of the main reaction or a preceding equilibrium, wherein during the reaction one or more substances to be separated are continuously removed from the reaction mixture by one or more auxiliaries.
    Type: Grant
    Filed: May 4, 1998
    Date of Patent: May 30, 2000
    Assignee: RWE-DEA Aktiengesellschaft fur Mineraloel und Chemie
    Inventors: Ulrich Hoffmann, Ulrich Kunz
  • Patent number: 6060626
    Abstract: A novel fluorine-containing compound having functions corresponding to those of fluorine is provided, which is stable under various conditions, excellent in compatibility with other solvents, and can be widely utilized as solvents, cosmetics, detergents, emulsifiers, surface finishing agents, lubricants, as well as lubricants or oils in the field of semiconductor/electronics.That is, the present invention provides fluorine-containing ether compounds represented by the general formula (1):Rf--(CH.sub.2).sub.n --O--R.sup.1 (1)(wherein, Rf represents a straight or branched C.sub.1-20 perfluoroalkyl or fluoroalkyl group, R.sup.1 represents a straight or branched C.sub.3-9 alkyl or a C.sub.3-9 cycloalkyl group, n is a number from 1 to 8).
    Type: Grant
    Filed: April 9, 1998
    Date of Patent: May 9, 2000
    Assignee: Kao Corporation
    Inventors: Yasuyuki Fujii, Eiko Tamura, Shinji Yano, Hisakazu Furugaki
  • Patent number: 6046366
    Abstract: The invention relates to the use of compounds of formula:[M(II).sub.1-x M*(III).sub.x (OH).sub.2+x ].mH.sub.2 O (I)in which M(II) represents a divalent cation chosen from the group consisting of nickel, zinc, cobalt, magnesium or the mixture of two or more of the abovementioned metals; M(III) represents a trivalent cation, such as aluminum, gallium, iron or chromium, with the exception of the compound of formula (I) in which M(II) is magnesium and M(III) is aluminum, x is between 0.20 and 0.33 and m.ltoreq.1; in the preparation of .beta.-hydroxycarbonyl and/or .alpha.,.beta.-unsaturated carbonyl compounds.
    Type: Grant
    Filed: December 7, 1998
    Date of Patent: April 4, 2000
    Assignee: Elf Atochem S.A.
    Inventors: Remy Teissier, Didier Tichit
  • Patent number: 5936131
    Abstract: The present invention relates to a process for obtaining .beta.-hydroxy carbonyl compounds and/or .alpha.,.beta.-unsaturated carbonyl compounds, characterized in that at least one aldehyde or one ketone is brought into contact with a solid catalyst of general formula (I):?(Mg.sup.2+).sub.1-x (Al.sup.3+).sub.x (OH.sup.-).sub.2 !.sup.x+ ?(OH.sup.-).sub.x !.sup.x- (H.sub.2 O).sub.n (I)with 0.20.ltoreq.x.ltoreq.0.33 and n<1.
    Type: Grant
    Filed: February 28, 1997
    Date of Patent: August 10, 1999
    Assignee: ELF Atochem S,A
    Inventors: Remy Teissier, Maurice Fournier
  • Patent number: 5872263
    Abstract: A process for separating a gaseous reaction mixture in the preparation of trioxane is described, in which a) the gaseous mixture leaving the reactor is scrubbed in countercurrent with an organic solvent whose boiling point is above 135.degree. C. in which the trioxane predominantly dissolves and which leaves the formaldehyde predominantly in the gas phase which is returned to the reactor, b) the trioxane together with residual formaldehyde is stripped from the solvent by distillation via a column, the overhead product being partially condensed in the temperature range from 62.degree. to 100.degree. C. c) some of the resulting condensate is applied to the column as reflux and some is taken off as product and d) the non-condensed portion is returned to the scrubbing step a).
    Type: Grant
    Filed: April 28, 1995
    Date of Patent: February 16, 1999
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Michael Hoffmockel, Karl-Friedrich Muck, Gunter Sextro
  • Patent number: 5831097
    Abstract: A process for the preparation of acyloins of the general formula I ##STR1## in which R.sup.a and R.sup.b are the same or different and stand for hydrogen or an optionally substituted C.sub.1 -C.sub.20 alkyl, an optionally substituted C.sub.6 -C.sub.10 aryl, an optionally substituted C.sub.7 -C.sub.12 aralkyl, an optionally substituted heteroaryl, or an optionally substituted heterocycloalkyl group, except for autocondensation products of formaldehyde, wherein an aldehyde of the formula IIR.sup.a CHO, (II)is reacted, in the presence of a catalyst, with an aldehyde of the formula IIIR.sup.b CHO, (III)in whichR.sup.a and R.sup.b have the above meanings and at least one of the radicals R.sup.a and R.sup.
    Type: Grant
    Filed: January 21, 1997
    Date of Patent: November 3, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Ebel, Regina Schneider, Johann-Peter Melder, Joaquim Henrique Teles
  • Patent number: 5801292
    Abstract: 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: Grant
    Filed: March 28, 1996
    Date of Patent: September 1, 1998
    Assignee: Eastman Chemical Company
    Inventors: Thomas J. Kwok, Windell C. Watkins
  • Patent number: 5770762
    Abstract: 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: Grant
    Filed: April 22, 1997
    Date of Patent: June 23, 1998
    Assignee: Kuraray Co., Ltd.
    Inventors: Hideharu Iwasaki, Takashi Onishi
  • Patent number: 5434313
    Abstract: An aldolisation-dehydration process is disclosed for converting an aldehyde, e.g. n-valeraldehyde, to a substituted acrolein, e.g. propyl butyl acrolein (2-propylhept-2-enal). Aldolisation and dehydration are effected in a stirred tank reactor (16; 111) using an alkali catalyst, such as sodium hydroxide. A reaction product stream (23; 113) containing both organic and aqueous phases is distilled (in column 25; 123) to yield a heterogeneous azeotrope containing water and aldehyde. On condensation and phase separation the lower water layer (34; 150) can be discharged from the plant without the need for neutralisation. From the bottom of the distillation zone a mixture (36;157) of substituted acrolein and alkali catalyst solution is obtained. The substituted acrolein is recovered as product (45;173), while the catalyst solution (47;175) is recycled to the aldolisation reactor. Part (49; 181) of the catalyst solution is purged to control the level of Cannizzaro reaction products.
    Type: Grant
    Filed: October 6, 1994
    Date of Patent: July 18, 1995
    Assignee: Davy McKee (London) Limited
    Inventors: George E. Harrison, Arthur J. Reason, Alan J. Dennis, Mohammad Sharif
  • Patent number: 5386062
    Abstract: A process for the catalytical preparation of condensation products of formaldehyde, in which formaldehyde or a formaldehyde-forming compound is caused to undergo reaction using a catalyst which has been produced, in the presence of an auxiliary base, from a triazolium salt of formula I ##STR1## in which R.sup.1 and R.sup.3 are the same or different and stand for aliphatic groups having from 1 to 30 carbon atoms, optionally substituted aryl groups, optionally substituted aralkyl groups, and/or optionally substituted heteroaryl groups,R.sup.2 represents hydrogen, the hydroxymethylene group --CH.sub.2 OH or the hydroxy-hydroxymethylene-methylidyne group --CH(OH)(CH.sub.2 OH), andR.sup.4 denotes hydrogen, a halogen atom, a nitro or cyano group, an aliphatic group having from 1 to 30 carbon atoms, an optionally substituted aryl group, an optionally substituted aralkyl group, an optionally substituted heteroaryl group, an alkoxy group --OR.sup.5, a thioether group --SR.sup.6, an amino group --NR.sup.7R R.sup.
    Type: Grant
    Filed: September 7, 1993
    Date of Patent: January 31, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Joaquim H. Teles, Johann-Peter Melder, Eugen Gehrer, Wolfgang Harder, Klaus Ebel, Carsten Groening, Regina Meyer
  • Patent number: 5382716
    Abstract: Mixtures of isomeric decyl alcohols obtained by hydroformylation of butadiene to produce aldehyde mixtures, condensation of the aldehyde mixtures, isolated from the reaction product, to form an aldol mixture, and isolation and hydrogenation of the aldol mixture. The mixture of isomeric decyl alcohols, esterified using phthalic acid, gives a mixture of isomeric decyl phthalates which are plasticizers having excellent cold properties.
    Type: Grant
    Filed: March 23, 1993
    Date of Patent: January 17, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Bahrmann, Wolfgang Greb, Peter Heymanns, Peter Lappe, Jurgen Szameitat, Thomas Muller, Ernst Wiebus
  • Patent number: 5382700
    Abstract: 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: Grant
    Filed: May 24, 1993
    Date of Patent: January 17, 1995
    Assignee: Eastman Chemical Company
    Inventor: William A. Beavers
  • Patent number: 5371299
    Abstract: Preparation of diethers of the formula ##STR1## wherein R is an alkyl, cycloalkyl, aryl, or aralkyl radical, by formation of an unsaturated aldehyde of the formula ##STR2## wherein R is as defined above, by means of an aldol condensation reaction, reduction of said aldehyde to form the corresponding saturated compound, transformation of the saturated compound into the corresponding diol, and consequent methylation of the diol into diether.
    Type: Grant
    Filed: February 9, 1993
    Date of Patent: December 6, 1994
    Assignee: Himont Incorporated
    Inventor: Giampietro Borsotti
  • Patent number: 5334770
    Abstract: A process of aldol condensation of an active hydrogen-containing compound by a gas-phase reaction by feeding a gaseous active hydrogen-containing compound to a reactor provided with a fixed bed solid catalyst, which process is characterized in that an indirect heat transfer type, non-isothermal reactor is used to perform the aldol condensation efficiently in a commercial scale.
    Type: Grant
    Filed: June 23, 1993
    Date of Patent: August 2, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroshi Ueda, Tamotsu Takamoto, Koji Okada
  • Patent number: 5298668
    Abstract: Arycolaldehyde, glyceraldehyde, C.sub.4 - and C.sub.5 -sugars or mixtures thereof are prepared in a self-condensation of formaldehyde by reacting formaldehyde or a formaldehyde donor in the presence of a mesoionic catalyst of the formula ##STR1## wherein X is nitrogen or CR.sup.3, Y is sulfur or selenium or NR.sup.4, and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 can be identical or different and each can represent an aliphatic, aryl, aralkyl or heteroaryl group which is unsubstituted or which bears substituents which have only a negligible effect on the catalytic activity of said mesoionic catalyst, with the proviso that R.sup.2 together with R.sup.4 can form a C.sub.2 -C.sub.5 -alkylene or alkenylene bridge or a C.sub.6 -C.sub.14 -arylene bridge, and wherein R.sup.5 is hydrogen, the hydroxymethyl group -CH.sub.2 OH or the hydroxymethylhydroxymethyl group --CH(OH)(CH.sub.2 OH).
    Type: Grant
    Filed: March 26, 1993
    Date of Patent: March 29, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Eugen Gehrer, Wolfgang Harder, Klaus Ebel, Johann-Peter Melder, Joaquim H. Teles
  • Patent number: 5258558
    Abstract: 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 /g, 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: Grant
    Filed: May 18, 1992
    Date of Patent: November 2, 1993
    Assignee: UOP
    Inventors: Blaise J. Arena, Jennifer S. Holmgren
  • Patent number: 5254743
    Abstract: 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: Grant
    Filed: December 9, 1992
    Date of Patent: October 19, 1993
    Assignee: UOP
    Inventors: Jennifer S. Holmgren, Blaise J. Arena
  • Patent number: 5254742
    Abstract: 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: Grant
    Filed: October 8, 1992
    Date of Patent: October 19, 1993
    Assignee: Mitsubishi Petrochemical Co., Ltd.
    Inventors: Yuji Ohgomori, Shuji Ichikawa, Takahiro Yoneyama, Naoko Sumitani
  • Patent number: 5250710
    Abstract: The present invention relates to dihydropyran derivatives, processes for preparing, and processes of using the derivatives. The derivatives are prepared by condensation of lithium dienolate of prenal with an aldehyde or a ketone.The pyran derivative prepared from .beta.-ionylideneacetaldehyde when treated in the presence of a catalyst directly forms retinal.
    Type: Grant
    Filed: May 7, 1992
    Date of Patent: October 5, 1993
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Pierre F. Chabardes, Lucette Duhamel, Pierre Duhamel, Jerome Guillemont, Jean-Marie Poirier
  • Patent number: 5243081
    Abstract: The present invention provides an aldol condensation dehydration catalyst, a process for preparing the same comprising reacting an aluminium salt with at least one magnesium compound selected from the group consisting of magnesium oxide and magnesium hydroxide to support thereon an aluminium compound and heating said supported product at a temperature in the range from 350.degree. to 700.degree. C., and a process for preparing an aldol condensation dehydrate by using the process.
    Type: Grant
    Filed: May 15, 1992
    Date of Patent: September 7, 1993
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masaru Ishino, Masami Fukao, Kazuaki Sasaki, Gohfu Suzukamo, Masao Sasaki
  • Patent number: 5237107
    Abstract: Magnesium.aluminium complex compound useful for aldol condensation dehydration is prepared by allowing a solution of magnesium salts and a solution of aluminium salts to react with ammonia and then heating the thus obtained precipitate at a temperature of 400.degree.-700.degree. C.
    Type: Grant
    Filed: May 7, 1992
    Date of Patent: August 17, 1993
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masaru Ishino, Masami Fukao, Kazuaki Sasaki, Gohfu Suzukamo, Masao Sasaki
  • Patent number: 5235118
    Abstract: Disclosed is a continuous process for the manufacture of 2-ethyl-2-(hydroxymethyl)hexanal wherein 2-ethylhexanal, formaldehyde and a tertiary amine are continuously fed to a reaction zone and crude product comprising an aqueous phase and an organic phase containing 2-ethyl-2-(hydroxymethyl)hexanal and 2-ethylhexanal is continuously removed from the reaction zone Also disclosed are processes for (1) the azeotropic distillation of the organic phase of the crude product whereby unreacted 2-ethylhexanal is recovered and (2) the catalytic hydrogenation of the refined, organic phase of the crude product to produce 2-butyl-2-ethyl-1,3-propanediol.
    Type: Grant
    Filed: August 31, 1992
    Date of Patent: August 10, 1993
    Assignee: Eastman Kodak Company
    Inventors: Don L. Morris, William A. Beavers, William E. Choate
  • Patent number: 5185478
    Abstract: Neopentyl glycol is made by reacting isobutyraldehyde with paraformaldehyde in the presence of a tertiary amine and cadmium or yttrium oxide; then hydrogenating the resulting reaction mixture containing hydroxypivaldehyde and at least about 20% 3-hydroxy-2,2-dimethylpropylhydroxypivalate.
    Type: Grant
    Filed: April 16, 1992
    Date of Patent: February 9, 1993
    Assignee: Aristech Chemical Corporation
    Inventors: Jeffrey S. Salek, Joseph Pugach