Aldehyde Reacted With Diverse Aldehyde Patents (Class 568/464)
  • Patent number: 9006495
    Abstract: The present invention relates to a process for the catalytic aldol condensation of aldehydes, in particular for preparing ?,?-unsaturated aldehydes, in a multiphase reactor.
    Type: Grant
    Filed: November 27, 2013
    Date of Patent: April 14, 2015
    Assignee: BASF SE
    Inventors: Roland Krokoszinski, Steffen Oehlenschläger, Rainer Papp, Jens Rudolph, Armin Ulonska
  • 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
  • Publication number: 20140213827
    Abstract: An improved process for preparing hydroxy aldehydes, such as hydroxypivaldehyde, is provided. Specifically, the process employs an alkaline additive for separating by-product amine salts from a hydroxy aldehyde and other reaction products formed in the process of preparing a hydroxy aldehyde using an amine catalyst.
    Type: Application
    Filed: January 31, 2013
    Publication date: July 31, 2014
    Applicant: Eastman Chemical Company
    Inventors: Kenneth Wayne Hampton, JR., Eugene H. Brown
  • Publication number: 20140155656
    Abstract: The present invention relates to a process for the catalytic aldol condensation of aldehydes, in particular for preparing ?,?-unsaturated aldehydes, in a multiphase reactor.
    Type: Application
    Filed: November 27, 2013
    Publication date: June 5, 2014
    Applicant: BASF SE
    Inventors: Roland Krokoszinski, Steffen Oehlenschläger, Rainer Papp, Jens Rudolph, Armin Ulonska
  • Publication number: 20130217901
    Abstract: The invention relates to a method of producing optically active 4-chloro-3-hydroxybutanal compound (2) by reacting chloroacetaldehyde with aldehyde compound (1) in the presence of optically active pyrrolidine compound (5). wherein each symbol is as defined in the specification.
    Type: Application
    Filed: October 19, 2011
    Publication date: August 22, 2013
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventor: Yujiro Hayashi
  • Publication number: 20120271029
    Abstract: The present invention relates to a process for preparing hydroxypivalaldehyde (HPA), which comprises in a first stage reacting isobutyraldehyde with formaldehyde in the presence of a tertiary amine and in a second stage introducing the reaction output obtained from the first stage into a stripping column. The present application further relates to a process for preparing neopentyl glycol (NPG) by hydrogenating the hydroxypivalaldehyde prepared in accordance with the invention and the further conversion of the NPG thus obtained to polyester resins, unsaturated polyester resins, lubricants or plasticizers.
    Type: Application
    Filed: April 13, 2012
    Publication date: October 25, 2012
    Applicant: BASF SE
    Inventors: Helmut Kronemayer, Michael Steiniger, Eva Kretzschmar, Norbert Asprion, Marcus Bechtel
  • 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
  • Publication number: 20100113836
    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: Application
    Filed: February 25, 2008
    Publication date: May 6, 2010
    Inventors: Tilman Sirch, Michael Steiniger, Steffen Maas, Stefan Rittinger, Stephan Schlitter
  • Publication number: 20090048411
    Abstract: A method for producing a mixture of ethylene and carbon monoxide by contacting ethane and an oxygen source at a temperature of at least 500° C. to produce ethylene and carbon monoxide. A method for producing an alkyl propionate by steps of: (a) contacting ethane and an oxygen source at a temperature of at least 500° C. to produce ethylene; (b) contacting an alcohol, ethylene and carbon monoxide with an ethylene carbonylation catalyst to produce the alkyl propionate; and (c) separating the alkyl propionate from byproducts and starting materials. The method further comprises condensing the alkyl propionate with formaldehyde to produce an alkyl methacrylate.
    Type: Application
    Filed: August 5, 2008
    Publication date: February 19, 2009
    Inventors: Abraham Benderly, Scott Han, Mark Anthony Silvano, Donald Lee Zolotorofe
  • 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: 7247755
    Abstract: The present invention provides a process for producing an ?,?-bis(hydroxymethyl)alkanal represented by Formula (II): (wherein R represents an alkyl group, a cycloalkyl group, or an aryl group) which comprises reacting an aldehyde represented by Formula (I): R—CH2—CHO ??(I) (wherein R has the same meaning as defined above) with formaldehyde in the presence of a basic catalyst and a phase-transfer catalyst.
    Type: Grant
    Filed: July 22, 2004
    Date of Patent: July 24, 2007
    Assignee: Kyowa Hakko Chemical Co., Ltd.
    Inventors: Shinichi Konishi, Shingo Nakayama, Yukihiro Isogai, Tokuyuki Yoshimoto
  • 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
  • Publication number: 20020198411
    Abstract: Allyl alcohols are converted into corresponding aldehydes or ketones in a high yield under a mild condition by using an inexpensive aluminum alkoxide as an Oppenauer oxidation catalyst and a hydride acceptor. Thus, there is provided an industrially useful method for converting allyl alcohols to corresponding aldehydes or ketones.
    Type: Application
    Filed: May 21, 2002
    Publication date: December 26, 2002
    Applicant: NIKKEN CHEMICALS CO., LTD.
    Inventors: Shin Tanikawa, Sou Matsubayashi, Michika Tanikawa, Toshiya Komatsu
  • 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: 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: 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: 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: 6187971
    Abstract: Methylolalkanal of the formula II (R=CH2OH, C1-C22-alkyl, aryl or C6-C22-aralkyl) is prepared spe-wise by a) reacting a C2-C24-aldehyde with formaldehyde in the presence of a tertiary amine, b) separating the reaction mixture i) into a bottom fraction comprising the compound of formula II and an incompletely methylolated compound of the formula III and a distillate stream comprising unconverted or partially converted starting materials, or ii) into an aqueous phase and an organic phase, and recycling the distillate stream or the organic phase to a), and c) subjecting the bottom fraction or the aqueous phase i) to a catalytic or thermal reaction to convert the compound of formula III to the compound of formula II and to a corresponding methylene compound of formula IV (R′=H or R) and ii) separating the reaction product into an overhead stream comprising the compound of formula IV and unconverted formaldehyde which is recycled to a
    Type: Grant
    Filed: June 21, 1999
    Date of Patent: February 13, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Detlef Kratz, Achim Stammer, Gerhard Schulz, Guido Voit
  • Patent number: 6018074
    Abstract: A process for the preparation of polyalcohols comprises the stages:(a) Reaction of an alkanal or ketone with formaldehyde in aqueous solution in the presence of a tertiary amine, to form a formates containing polyalcohol product mixture,(b) removal of water, excess tertiary amine, excess formaldehyde(c) heating of remaining mixture from (b) with removal of further formaldehyde and tertiary amine with formation of the formates of the polyalcohol,(d) transfer of tertiary amine removed from stage (b) and/or from stage (c), to synthesis stage (a) and/or to the subsequent transesterification stage (e),(e) transesterification of the resulting formates of the polyalcohol from stage (c) with an alcohol of the formula ROH in the presence of a transesterification catalyst to give polyalcohols and formates of the formula ##STR1## where R is a hydrocarbon radical, preferably alkyl of 1-6, particularly preferably 1-2, carbon atoms, and(f) isolation of the polyalcohols.
    Type: Grant
    Filed: October 5, 1998
    Date of Patent: January 25, 2000
    Assignee: BASF Aktiengesellshcaft
    Inventors: Detlef Kratz, Achim Stammer, Tom Witzel, Martin Brudermuller
  • Patent number: 5994592
    Abstract: The present invention relates to a process for producing 2,2'-bis(hydroxymethyl)alkanal and 2,2'-bis(hydroxymethyl)alkanoic acid as raw materials for dimethylol alkanoic acids or trimethylol alkanes, which are useful for the production of polyesters, polyurethanes, alkyd resins and the like, in an industrially advantageous manner.
    Type: Grant
    Filed: February 12, 1998
    Date of Patent: November 30, 1999
    Assignee: Nippon Kasei Chemical Company Limited
    Inventors: Toshiharu Yokoyama, Kouji Maeda
  • 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: 5532417
    Abstract: Neopentyl glycol is made from isobutyraldehyde and formaldehyde. The formaldehyde may be in the form of paraformaldehyde or aqueous formaldehyde. The aldol reaction product is mixed with a lower alcohol prior to hydrogenation to promote hydrogenolysis and allow recovery of high purity product by simple distillation. In a less preferred mode, the alcohol may be added after hydrogenation, resulting in a smaller improvement over previous processes.
    Type: Grant
    Filed: August 2, 1993
    Date of Patent: July 2, 1996
    Assignee: Aristech Chemical Corporation
    Inventors: Jeffrey S. Salek, Joseph Pugach, Carole L. Elias, Leonard A. Cullo
  • 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: 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: 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: 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: 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
  • 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: 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: 4740639
    Abstract: The invention relates to a process for the preparation of 2,4-disubstituted-1,5-pentanediols from formaldehyde and at least one simple aldehyde of the formula RCH.sub.2 CHO. More particularly the invention relates to a reaction to produce a 2,4-disubstituted glutaraldehyde wherein the reactant mole ratio of aldehyde/formaldehyde is between 1 and 8. The reaction is carried out in the presence of a secondary amine or secondary amine salt catalyst and leads to higher yields of the 2,4-disubstituted glutaraldehyde. The invention also relates to the production of 2,4-disubstituted-1,5-pentanediols by hydrogenation of the 2,4-disubstituted glutaraldehydes.
    Type: Grant
    Filed: June 12, 1987
    Date of Patent: April 26, 1988
    Assignee: Eastman Kodak Company
    Inventor: William A. Beavers
  • Patent number: 4727197
    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 aqueous media and in the presence of a food grade or natural nonionic emulsifier, preferably a nonionic sorbitan derivative emulsifying agent and in the absence of any other reagents.
    Type: Grant
    Filed: February 6, 1987
    Date of Patent: February 23, 1988
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan O. Pittet, Ranya Muralidhara, Arthur L. Liberman
  • Patent number: 4727058
    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 aqueous media and in the presence of a food grade or natural nonionic emulsifier, preferably a nonionic sorbitan derivative emulsifying agent and in the absence of any other reagents.
    Type: Grant
    Filed: June 29, 1987
    Date of Patent: February 23, 1988
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan O. Pittet, Ranya Muralidhara, Arthur L. Liberman
  • 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: 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: 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: 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: 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: 4247485
    Abstract: A process for the preparation of 2,2-dimethylolalkanals is disclosed wherein formaldehyde is reacted with an aldehyde of the formulaRCH.sub.2 CHO (I)whereinR denotes a straight-chain or branched alkyl radical with up to 12 carbon atoms where the radical can be substituted by an alkyl or alkoxy group with 1 to 3 carbon atoms in each case wherein the molar ratio of aldehyde of formula I to formaldehyde is 1:8 to 20, the reaction being carried out at a temperature in the range of 5.degree. to 100.degree. C. in the presence of 0.01 to 0.5 mol (per mol of aldehyde of formula (I)) of a catalyst consisting essentially of a hydroxide or carbonate of an alkali metal or alkaline earth metal or an unbranched tertiary aliphatic amine.
    Type: Grant
    Filed: March 19, 1979
    Date of Patent: January 27, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Immel, Hans-Helmut Schwarz, Hein Quast
  • Patent number: 4233247
    Abstract: An improvement in a process for the preparation of 2,2-dimethylolalkanal of the formula ##STR1## where R denotes an optionally substituted aliphatic radical by reacting 2-alkylacrylaldehyde with formaldehyde in presence of water and a base, the improvement residing in employing an aldehyde of the formula ##STR2## wherein R has the meaning indicated above and a mol ratio of the same to formaldehyde of 1:8-30 at a temperature in the range from -10 to 100.degree. C.
    Type: Grant
    Filed: March 13, 1978
    Date of Patent: November 11, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Immel, Hans-Helmut Schwarz
  • 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