Aldehyde Reacted With Aldehyde (e.g., Aldol Condensation, Etc.) Patents (Class 568/463)
  • Patent number: 5177267
    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: May 22, 1992
    Date of Patent: January 5, 1993
    Assignee: Eastman Kodak Company
    Inventors: Don L. Morris, William A. Beavers, William E. Choate
  • Patent number: 5146012
    Abstract: Neopentyl glycol is made from isobutyraldehyde and paraformaldehyde; the aldol reaction product is directly mixed with a lower alcohol for hydrogenolysis.
    Type: Grant
    Filed: June 28, 1991
    Date of Patent: September 8, 1992
    Assignee: Aristech Chemical Corporation
    Inventors: Jeffrey S. Salek, Joseph Pugach, Carole L. Elias, Leonard A. Cullo
  • Patent number: 5146004
    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: July 25, 1991
    Date of Patent: September 8, 1992
    Assignee: Eastman Kodak Company
    Inventors: Don L. Morris, William A. Beavers, William E. Choate
  • Patent number: 5144089
    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 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: Grant
    Filed: October 21, 1991
    Date of Patent: September 1, 1992
    Assignee: UOP
    Inventors: Blaise J. Arena, Jennifer S. Holmgren
  • Patent number: 5144088
    Abstract: Neopentyl glycol is made by reacting isobutyraldehyde with paraformaldehyde in the presence of a tertiary amine and one or more oxides of elements of Groups IB, IVA, IVB, VA, VB, VIB and VIII of the periodic table; then hydrogenating the resulting hydroxypivaldehyde-containing product.
    Type: Grant
    Filed: April 26, 1991
    Date of Patent: September 1, 1992
    Assignee: Aristech Chemical Corporation
    Inventors: Jeffrey S. Salek, Joseph Pugach
  • Patent number: 5026919
    Abstract: Basic intermediate or large pore zeolites having a Constraint Index less than 12 are useful as catalysts in the dehydrogenation-aromatization of cyclie dienes, in the isomerization of olefins and in the aldol condensation, and particularly in the cyclization of acetonylacetone to 3-methyl-2-cyclopenten-1-one.
    Type: Grant
    Filed: December 20, 1985
    Date of Patent: June 25, 1991
    Assignee: Mobil Oil Corporation
    Inventor: Ralph M. Dessau
  • Patent number: 5026920
    Abstract: Alkanals having a 2-alkyl branch are obtained from mixtures which contain the alkanals having a 2-alkyl branch in addition to n-alkanals, 3-alkylalkanals and/or further isomers by a process in whicha) the alkanal mixture is reacted with an aqueous formaldehyde solution in the presence of a secondary amine and of a carboxylic acid as a catalyst,b) the aqueous phase containing the catalyst and any unconverted excess formaldehyde is separated off andc) the alkanals having a 2-alkyl branch are isolated by distillation from the condensates of the other alkanals with formaldehyde.
    Type: Grant
    Filed: November 8, 1989
    Date of Patent: June 25, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Roeper, Franz Merger, Joerg Liebe, Armin V. Grenacher, Edgar Hahl
  • Patent number: 4943663
    Abstract: A process for the preparation of alpha-alkylacroleins from aldehydes and formaldehyde. The reaction takes place in the presence of a secondary amine and a carboxylic acid having up to 5 carbon atoms, and is performed in two stages so that, in the first stage, part of the carboxylic acid is added to the reaction mixture and, in the second stage, the remaining carboxylic acid is added.
    Type: Grant
    Filed: November 22, 1988
    Date of Patent: July 24, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhard Diekhaus, Harald Kappesser
  • Patent number: 4935538
    Abstract: The process for the production of high molecular weight oxygenates by condensing low molecular weight oxygenates in the presence of CO and a catalyst having the general formula A.sub.a CuM.sub.c X.sub.d O.sub.x. In addition, a novel condensation catalyst comprising A.sub.a CuM.sub.c Bi.sub.d O.sub.x is disclosed for use in this process.
    Type: Grant
    Filed: April 23, 1987
    Date of Patent: June 19, 1990
    Assignee: The Standard Oil Company
    Inventors: John R. Budge, Senja V. Compton
  • Patent number: 4716249
    Abstract: Described is a process for preparing natural benzaldehyde and acetaldehyde and compositions of matter containing natural benzaldehyde and acetaldehyde as well as products produced thereby and organoleptic utilities thereof, which process comprises the step of contacting with base naturally occurring cinnamaldehyde or a natural product rich in cinnamaldehyde such as Ceylon oil of cinnamon, Ceylon cinnamon bark, Saigon cinnamon bark, cassia oil, Ceylon cinnamon quills, cinnamon leaf oil, oil of cinnamon Madagascar or the like according to the reaction: ##STR1## the reaction taking place in the absence of any other reagents except inert solvent and ionic surfactant or emulsifier.
    Type: Grant
    Filed: October 31, 1986
    Date of Patent: December 29, 1987
    Assignee: International Flavors & Fragrances Inc.
    Inventor: Alan O. Pittet
  • Patent number: 4714784
    Abstract: The invention relates to a method for removing n-butyraldehyde from gas streams. It is characterized by washing with dilute aqueous alkali in a mass transfer apparatus. According to the invention, n-butyraldehyde can be removed from gas streams in the proportion of >90%, with operation at 0.degree.-40.degree. C. in the absence of added solubilizing agents.
    Type: Grant
    Filed: July 16, 1986
    Date of Patent: December 22, 1987
    Assignee: Huls Aktiengesellschaft
    Inventors: Eckhard Moeller, Wolfgang H. E. Mueller, Manfred Z. Hausen
  • Patent number: 4683342
    Abstract: Described is a process for preparing natural benzaldehyde and acetaldehyde and compositions of matter containing natural benzaldehyde and acetaldehyde as well as products produced thereby and organoleptic utilities thereof, which process comprises the step of contacting with base naturally occurring cinnamaldehyde or a natural product rich in cinnemaldehyde such as Ceylon oil of cinnamon, Ceylon cinnamon bark, Saigon cinnamon bark, cassia oil, Ceylon cinnamon quills, Cinnamon leaf oil, oil of cinnamon Madagascar or the like according to the reaction: ##STR1## the reaction taking place in aqueous media and in the presence of a food grade or natural nonionic emulisifier, preferably a nonionic sorbitan derivative emulsifying agent and in the absence of any other reagents.
    Type: Grant
    Filed: August 13, 1986
    Date of Patent: July 28, 1987
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan O. Pittet, Ranya Muralidhara, Arthur L. Liberman
  • Patent number: 4617419
    Abstract: Described is a process for preparing natural benzaldehyde and acetaldehyde and compositions of matter containing natural benzaldehyde and acetaldehyde as well as products produced thereby and organoleptic utilities therefor, which process comprises the step of contacting with base naturally occurring cinnamaldehyde or a natural product rich in cinnamaldehyde such as Ceylon oil of cinnamon, Ceylon cinnamon bark, Saigon cinnamon bark, cassia oil, Ceylon cinnamon quills, cinnamon leaf oil, oil of cinnamon Madagascar or the like according to the reaction: ##STR1## the reaction taking place in the absence of any other reagents except inert solvent.
    Type: Grant
    Filed: September 26, 1985
    Date of Patent: October 14, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Charles Wiener, Alan O. Pittet
  • Patent number: 4598162
    Abstract: Novel, liquid mixtures of isomeric aldehydes and alcohols are described in the C.sub.11 -C.sub.16 carbon range, the compounds being characterized by a main carbon branched at the position and moderate additional branching in most isomers; the aldehyde mixtures are prepared by an economic route from olefins involving oxo and aldol reaction with the reaction conducted in such a way as to give a high percentage of aldolable product, and preferably with a base catalyzed aldol reaction conducted under conditions to make high conversions attainable. The aldehyde mixtures can be hydrogenated to alcohols and converted to novel ethoxylates or sulfate compositions suitable for use as biodegradable detergents; or hydrogenated and oxidized to novel carboxylic acid compositions also suitable for detergent use.
    Type: Grant
    Filed: November 4, 1983
    Date of Patent: July 1, 1986
    Assignee: Monsanto Company
    Inventors: Denis Forster, George F. Schaefer, George E. Barker
  • Patent number: 4552985
    Abstract: Novel ether-aldols of the general formula (I) ##STR1## where R.sup.1 and R.sup.2 are each alkyl, can be prepared by reacting a 2-alkylacrolein (H.sub.2 C.dbd.CHR.sup.2 --CHO), an alcohol (R.sup.1 OH) and formaldehyde, preferably aqueous formaldehyde, in the presence of a tertiary amine.
    Type: Grant
    Filed: June 14, 1984
    Date of Patent: November 12, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Peter Hettinger, Arno Lange
  • Patent number: 4528405
    Abstract: A process is disclosed for the aldol condensation of enolizable aldehydes to alpha, beta-unsaturated aldehydes, at high selectivities, employing a metal carboxylate catalyst.
    Type: Grant
    Filed: December 30, 1983
    Date of Patent: July 9, 1985
    Assignee: Union Carbide Corporation
    Inventor: Anthony J. Papa
  • Patent number: 4526884
    Abstract: Catalyst composition and process are provided for the dimerization of acrylic compounds. An acrylic compound may be dimerized in the liquid phase by contacting an acrylic compound with a catalyst in the presence of hydrogen, at a pressure of least about 1 psi and a temperature of at least about 50.degree. C., wherein the catalyst comprises an organic polymer catalyst support, trivalent pendant atoms covalently bonded to the support, ruthenium complexed with said trivalent pendant atoms, and a second metal which is at least one of Pb and the Group VIII metals other than Ru and Pd and is disposed on the organic polymer catalyst support.
    Type: Grant
    Filed: December 27, 1982
    Date of Patent: July 2, 1985
    Assignee: The Standard Oil Company
    Inventors: Dean T. Tsou, James D. Burrington, Elizabeth A. Maher, Robert K. Grasselli
  • Patent number: 4519954
    Abstract: A catalyst and a liquid phase process are provided for the dimerization of acrylic compounds. The process includes contacting an acrylic compound with the catalyst in the presence of hydrogen, wherein the catalyst comprises an inorganic oxide catalyst support, trivalent pendant atoms covalently bonded to the support and ruthenium complexed with said trivalent pendant atoms.
    Type: Grant
    Filed: December 29, 1982
    Date of Patent: May 28, 1985
    Assignee: The Standard Oil Company
    Inventors: James D. Burrington, Fred A. Pesa, Elizabeth A. Maher, Robert K. Grasselli
  • Patent number: 4496770
    Abstract: .alpha.-Alkylacroleins are prepared by a process wherein an alkanal is reacted with formaldehyde in the presence of a secondary amine and in the presence or absence, of an acid, in the liquid phase, under superatmospheric pressure and at above 150.degree. C., for not more than 25 minutes.The .alpha.-alkylacroleins obtainable by the process are useful starting materials for dyes, drugs and pesticides.
    Type: Grant
    Filed: March 28, 1983
    Date of Patent: January 29, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Duembgen, Gerd Fouquet, Richard Krabetz, Ekhart Lucas, Franz Merger, Friedbert Nees
  • Patent number: 4465833
    Abstract: A novel ethynylation process is disclosed which provides an expanded series of novel ethylnyl-terminated aromatic compounds having base sensitive substituents and which facilitates the economic preparation of prior art ethynyl-substituted aromatic compounds.
    Type: Grant
    Filed: October 15, 1980
    Date of Patent: August 14, 1984
    Assignees: Hughes Aircraft Company, Hughes Aircraft Company
    Inventors: Kreisler S. Y. Lau, Robert H. Boschan
  • Patent number: 4433174
    Abstract: Alpha, beta-unsaturated aldehydes are prepared by reacting formaldehyde and a reactant aldehyde of formula RCH.sub.2 CHO wherein R is a member of the class consisting of -H, -alkyl, -aryl, -aralkyl, -cycloalkyl, and -alkylaryl radicals in the presence of AMS-1B borosilicate crystalline molecular sieve catalyst. Metacrolein is prepared from propionaldehyde and formaldehyde.
    Type: Grant
    Filed: July 26, 1982
    Date of Patent: February 21, 1984
    Assignee: Standard Oil Company (Indiana)
    Inventor: Gary P. Hagen
  • Patent number: 4426542
    Abstract: A preparation of a plasticizer alcohol, consisting of predominantly 2-propylheptanol, from linear butenes is described in which oxo product of the butenes is aldoled to condense n-pentaldehyde therein with very little cross-aldolization followed by hydrogenation to obtain the 2-propylheptanol with very small 2-propyl-4-methyl hexanol content. The alcohol product as phthalate ester has excellent plasticizer properties. Also processes are described for converting other olefins to alcohols by oxo, aldol and hydrogenation reactions, with particular attention to converting hexenes obtained by propylene dimerization to C.sub.14 alcohols suitable for preparation of detergents.
    Type: Grant
    Filed: June 11, 1981
    Date of Patent: January 17, 1984
    Assignee: Monsanto Company
    Inventors: George E. Barker, Denis Forster
  • Patent number: 4408079
    Abstract: .alpha.-Alkylacroleins are prepared by reacting an alkanal with formaldehyde and a secondary amine in the presence of a carboxylic, dicarboxylic or polycarboxylic acid in certain molar ratios within a pH range of from 2.5 to 7 and at from 0.degree. to 150.degree. C.The .alpha.-alkylacroleins which can be prepared by the process described are valuable starting materials for dyes, drugs and pest control agents.
    Type: Grant
    Filed: January 15, 1982
    Date of Patent: October 4, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Hans-Juergen Foerster
  • Patent number: 4358619
    Abstract: The instant invention relates to an improved process for the production of formose from formaldehyde. The improvement resides in using relatively small quanities of basic lead compounds as catalysts for the condensation reaction of the formaldehyde and, at the same time, for controlling the pH-value. By following this technique, organic or inorganic bases which, hitherto, have normally been used for this purpose are no longer needed.
    Type: Grant
    Filed: February 22, 1979
    Date of Patent: November 9, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ingo Stemmler, Hanns P. Muller, Kuno Wagner
  • Patent number: 4346239
    Abstract: A process for the preparation of 2-methylene aldehydes is disclosed wherein formaldehyde is reacted with an aldehyde of the general formula R--CH.sub.2 CHO, where R stands for a substituted or unsubstituted organic radical having from 2 to 12 carbon atoms. The reaction takes place in the presence of a mixture of a secondary amine and an organic carboxylic acid having up to 5 carbon atoms.
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: August 24, 1982
    Assignee: Ruhrchemie AG
    Inventors: Hanswilhelm Bach, Eike Brundin, Wilhelm Gick
  • Patent number: 4326086
    Abstract: This invention relates to an improved process for the preparation of formose by the condensation of aqueous formaldehyde. In the process according to this invention, tertiary amines which contain an electrophilic hetero atom in the .beta.-position to the tertiary nitrogen atom are used for controlling the pH instead of the inorganic bases which have previously been used for this purpose.
    Type: Grant
    Filed: August 17, 1978
    Date of Patent: April 20, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Edgar Mohring, Hanns P. Muller, Kuno Wagner
  • Patent number: 4316990
    Abstract: In the present invention aliphatic aldehydes are condensed to form .alpha.,.beta.-unsaturated aldehydes by use of a heterogeneous catalyst. Such process uses an anatase titanium dioxide catalyst in a fixed bed process under mild temperature conditions to yield high conversions and high yields, and which also eliminates the catalyst removal steps required by conventional processes.
    Type: Grant
    Filed: October 29, 1980
    Date of Patent: February 23, 1982
    Assignee: Eastman Kodak Company
    Inventor: Don L. Morris
  • Patent number: 4301310
    Abstract: This invention relates to an improved process for the preparation of a mixture of various low molecular weight hydroxyaldehydes, hydroxyketones and polyhydric alcohols by the condensation of formaldehyde with itself. The essential feature of the improvement is that unpurified synthesis gases of the kind obtained from the large scale industrial production of formaldehyde can be used directly as the source of formaldehyde.
    Type: Grant
    Filed: February 20, 1980
    Date of Patent: November 17, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventor: Kuno Wagner
  • Patent number: 4275251
    Abstract: Described are substituted tricyclodecane derivatives having the generic structure: ##STR1## wherein Y is a moiety having a structure selected from the group consisting of: ##STR2## wherein one of the dashed lines represents a carbon-carbon single bond and the other of the dashed lines represents a carbon-carbon double bond; wherein R.sub.1 and R.sub.2 represent hydrogen or methyl with the proviso that one of R.sub.1 and R.sub.2 is hydrogen and the other of R.sub.1 and R.sub.2 is methyl; wherein R.sub.3 is hydrogen, C.sub.1 -C.sub.3 acyl, C.sub.3 or C.sub.4 alkyl or C.sub.3 or C.sub.4 alkenyl; wherein R.sub.4, R.sub.5 and R.sub.6 represent hydrogen or methyl with the additional proviso that one of R.sub.4, R.sub.5 and R.sub.6 is methyl and the other two of R.sub.4, R.sub.5 and R.sub.6 is hydrogen.
    Type: Grant
    Filed: April 29, 1980
    Date of Patent: June 23, 1981
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, John B. Hall
  • Patent number: 4275242
    Abstract: A process for preparing 2-methylenealdehydes by reacting aldehydes with formaldehyde in the presence of enamines is disclosed.
    Type: Grant
    Filed: December 21, 1979
    Date of Patent: June 23, 1981
    Assignee: Ruhrchemie Aktiengesellschaft
    Inventors: Jurgen Weber, Wolfgang Bernhagen, Helmut Springer
  • Patent number: 4273934
    Abstract: 3-Hydroxy-2,2,4-trimethylpentyl isobutyrate is prepared by reaction of isobutyraldehyde in the presence of an alkaline earth metal hydroxide and of carboxylic acids or the corresponding salts, under specific conditions in respect of reaction time and proportion and concentration of the hydroxide suspension. The product is a starting material for the preparation of dyes, pesticides, adhesives and surface coatings.
    Type: Grant
    Filed: April 17, 1979
    Date of Patent: June 16, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Hans-Juergen Foerster
  • Patent number: 4270006
    Abstract: Aliphatic carbonyl compounds are prepared by an aldol condensation of carbonyl compounds R.sup.1 --CH.sub.2 --CO--R.sup.2 (I; R.sup.1 and R.sup.2 =H or C.sub.1 -C.sub.8 -alkyl) in the presence of hydrogen and of a catalyst which has both condensing and hydrogenating properties, by using a catalyst system wherein the active components are from 1 to 90 percent by weight of a noble metal of group VIII of the periodic table and from 10 to 99 percent by weight of an oxide or salt of a rare earth metal, or of a mixture of different oxides and/or salts of rare earth metals.
    Type: Grant
    Filed: December 27, 1979
    Date of Patent: May 26, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Heilen, Axel Nissen, Otto Woerz
  • Patent number: 4247653
    Abstract: A process is disclosed for preparing mixtures of low molecular weight polyhydroxyl compounds and hydroxyaldehydes and hydroxyketones by condensing formaldehyde hydrate with itself in the presence of (I) as catalyst a soluble or insoluble compound of a metal of the first to eighth sub-group or second to fourth main group of the Periodic System of Elements, optionally bound to a high molecular weight carrier, and (II) more than 10% by weight, based on formaldehyde, of one or more dihydric or higher hydric low molecular weight alcohols and/or higher molecular weight polyhydroxyl compounds. The pH of the reaction mixture is held at 5.5 to 9.0 until 5-40% conversion has occurred and is then lowered to between 4.5 and 8.0 (0.5-2.0 pH units lower). The reaction is then stopped by inactivating the catalyst.
    Type: Grant
    Filed: August 30, 1977
    Date of Patent: January 27, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventor: Kuno Wagner
  • Patent number: 4219508
    Abstract: This invention relates to an improved process for the preparation of a mixture of various low molecular weight hydroxyaldehydes, hydroxyketones and polyhydric alcohols by the condensation of formaldehyde with itself. The essential feature of the improvement is that unpurified synthesis gases of the kind obtained from the large scale industrial production of formaldehyde can be used directly as the source of formaldehyde.
    Type: Grant
    Filed: August 30, 1977
    Date of Patent: August 26, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventor: Kuno Wagner
  • Patent number: 4215076
    Abstract: Chemical control of aldol reactions has been achieved by employing a combination of inorganic base-cationic or neutral surfactant catalysts with organic carbonyl compounds.
    Type: Grant
    Filed: April 23, 1976
    Date of Patent: July 29, 1980
    Assignee: Union Carbide Corporation
    Inventors: Kenneth C. Stueben, Mary L. Deem