Oxy Or -coo- Containing Reactant Patents (Class 568/465)
  • Publication number: 20140357900
    Abstract: Disclosed is a preparation method of the lycopene intermediate 3-methyl-4,4-dialkoxy-1-butaldehyde. The preparation method comprises the following steps: (1) reacting 2-methyl-3,3-dialkoxy-1-halopropane with magnesium powder in the solvent of anhydrous tetrahydrofuran at a temperature of 45˜65° C. to generate a mixture of Grignard reagents under the protection of an inert gas; and (2) adding N,N-disubstituted carboxamide to the mixture of Grignard reagents and reacting at a temperature of 10° C.˜35° C. to obtain 3-methyl-4,4-dialkoxy-1-butaldehyde. The process route of the present invention is simple and direct, the operation is easy, the conditions are mild and the yield is good, and thus the invention has commercial value.
    Type: Application
    Filed: December 10, 2012
    Publication date: December 4, 2014
    Inventors: Chunlei Lv, Shiqing Pl, Jianhui Chen, Dingqiang Lu, Pingkai Ouyang
  • Patent number: 8809594
    Abstract: Disclosed is a process for the production of higher aldehydes from lower alcohols using a two-stage vapor phase heterogeneous catalyst system. Ethanol feeds afford aldehydes such as butyraldehyde and crotonaldehyde while butanol feeds yield 2-ethylhexanal and 2-ethylhexenal. Higher product selectivities are obtained when the alcohol is first dehydrogenated in the upper catalyst stage followed by aldol condensation of the resulting lower aldehyde to a higher aldehyde.
    Type: Grant
    Filed: September 21, 2012
    Date of Patent: August 19, 2014
    Assignee: Eastman Chemical Company
    Inventors: David William Norman, Damon Ray Billodeaux, Melissa Dawn Page
  • Patent number: 8143454
    Abstract: The invention provides a technology for producing acrolein from glycerol while maintaining high reagent partial pressures, which leads to higher yield. The invention more particularly relates to a method for producing acrolein from glycerol that comprises the intermediate step of forming glycerol and acrolein cyclic acetals.
    Type: Grant
    Filed: December 16, 2008
    Date of Patent: March 27, 2012
    Assignee: Arkema France
    Inventor: Jean-Luc Dubois
  • Patent number: 8044246
    Abstract: The present invention relates to a process for the selective preparation of acetaldehyde, characterized in that acrolein and one or more ammonium salts dissolved in water are reacted continuously under high pressures and at temperatures of 300-400° C.
    Type: Grant
    Filed: July 27, 2010
    Date of Patent: October 25, 2011
    Assignee: Lonza Ltd.
    Inventors: Wolfgang Wenger, Andreas Heyl, Lothar Ott, Herbert Vogel, Paul Hanselmann, Gökhan Aras
  • Patent number: 7956203
    Abstract: Alcohols are catalytically oxidized to aldehydes, in particular to benzaldehyde and diformylfuran, which are useful as intermediates for a multiplicity of purposes. The invention also relates to the polymerization of the dialdehyde and to the decarbonylation of the dialdehyde to furan.
    Type: Grant
    Filed: March 27, 2001
    Date of Patent: June 7, 2011
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Vladimir Grushin, Walter Partenheimer, Leo E. Manzer
  • Publication number: 20110034737
    Abstract: The present invention is directed to alkanal derivatives of water-soluble polymers such as poly(ethylene glycol), their corresponding hydrates and acetals, and to methods for preparing and using such polymer alkanals. The polymer alkanals of the invention are prepared in high purity and exhibit storage stability.
    Type: Application
    Filed: October 20, 2010
    Publication date: February 10, 2011
    Applicant: Nektar Therapeutics
    Inventor: Antoni Kozlowski
  • Publication number: 20110028764
    Abstract: The present invention relates to a process for the selective preparation of acetaldehyde, characterized in that acrolein and one or more ammonium salts dissolved in water are reacted continuously under high pressures and at temperatures of 300-400° C.
    Type: Application
    Filed: July 27, 2010
    Publication date: February 3, 2011
    Inventors: Wolfgang WENGER, Andreas HEYL, Lothar OTT, Herbert VOGEL, Paul HANSELMANN, Gökhan ARAS
  • Publication number: 20090105506
    Abstract: There is provided a process for producing 3,3,3-trifluoropropionaldehyde, including the step of hydrolyzing a benzyl vinyl ether of the formula [1] in the presence of a catalyst selected from the group consisting of Arrhenius acids and Lewis acids, where R represents phenyl or phenyl having a substituent R1 selected from the group consisting of alkyl groups, alkoxy groups, halogen atoms, nitro groups and amino groups.
    Type: Application
    Filed: September 12, 2006
    Publication date: April 23, 2009
    Applicant: Central Glass Company, Limited
    Inventors: Takeo Komata, Kenji Hosoi, Shinya Akiba
  • Publication number: 20090069604
    Abstract: A process for catalytically hydrogenating methylolalkanals of the general formula in which R1 and R2 are each independently a further methylol group or an alkyl group having from 1 to 22 carbon atoms or an aryl or aralkyl group having from 6 to 33 carbon atoms, in the liquid phase over a hydrogenation catalyst, which comprises setting a pH of from 7.0 to 9.0 in the hydrogenation effluent by adding at least one tertiary amine, an inorganic base or an inorganic or organic acid to the hydrogenation feed.
    Type: Application
    Filed: February 23, 2007
    Publication date: March 12, 2009
    Applicant: BASF SE
    Inventors: Steffen Maas, Thorsten Johann, Michael Koch, Tilman Sirch, Stephan Schlitter, Stefan Rittinger, Michael Steiniger
  • Patent number: 7498451
    Abstract: The invention relates to a process for obtaining a pure aliphatic dialdehyde monoacetal by reaction of the corresponding aliphatic dialdehyde or a precursor of the corresponding aliphatic dialdehyde with one or more aliphatic mono- or polyhydric alcohols while distillatively removing water to obtain a reaction mixture which is separated distillatively, which comprises carrying out the distillative separation continuously in a dividing wall column to obtain pure aliphatic dialdehyde monoacetal as a sidestream from the dividing wall column, or in two distillation columns to obtain crude aliphatic dialdehyde monoacetal as a sidestream in the first distillation column, feed the crude aliphatic dialdehyde monoacetal to the second distillation column and obtain pure aliphatic dialdehyde monoacetal as the sidestream from the second distillation column.
    Type: Grant
    Filed: November 27, 2003
    Date of Patent: March 3, 2009
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Haderlein, Hans-Georg Göbbel, Wolfgang Siegel
  • Patent number: 7094932
    Abstract: The present invention provides a method for the production of glycolaldehyde with high specificity. The hydrous thermolysis consists of the spraying of aqueous sugar solutions containing from 25 to 80% of water but preferably 30 to 60% water, as a fine mist into a reactor held at the between 500 and 600° C., but preferably between 520 and 560° C. and the condensation of the resulting vaporous product in a surface condenser with optional heat recovery. The residence time of the vaporous product in the reactor should be in the range 0.1–5 seconds, but preferably in the range 0.5 to 2 seconds. Aldose monomeric sugars, preferably glucose (also known as dextrose), are preferred for use in the aqueous solution. The yield of glycolaldehyde in the condensed liquid is minimum 50% by weight of the sugar fed for glucose solutions.
    Type: Grant
    Filed: November 8, 2001
    Date of Patent: August 22, 2006
    Assignee: Resource Transforms International Ltd.
    Inventors: Piotr A. Majerski, Jan K. Piskorz, Desmond St. A. G. Radlein
  • Publication number: 20040220429
    Abstract: Dimethyl ether is converted to formaldehyde using a supported catalyst comprising molybdenum and/or vanadium oxides. The surface density of the oxide(s) ranges from greater than that for the isolated monomeric oxides upwards, so long as there is a substantial absence of bulk crystalline molybdenum and/or vanadium oxide(s). Conversion and selectivity to formaldehyde are improved as compared to data reported for known catalysts. Also disclosed is a supported catalyst comprising molybdenum and/or vanadium oxides wherein the support comprises one or more reducible metal oxides, preferably a layer or layers of one or more reducible metal oxides disposed on the surface of a particulate alumina or zirconia support.
    Type: Application
    Filed: June 3, 2004
    Publication date: November 4, 2004
    Applicant: Regents of the University of California
    Inventors: Haichao Liu, Enrique Iglesia
  • Publication number: 20040210094
    Abstract: A process for the production of 3,3-dimethylbutyraldehyde is disclosed. The 3,3-dimethylbutyraldehyde is obtained by the reduction of 3,3-dimethylbutyric acid using trimethylacetic anhydride and a phosphine. The 3,3-dimethylbutyric acid is preferably obtained by a process in which tert-butanol and vinylidene chloride are reacted in the presence of sulfuric acid. The disclosed process has improved cost and yield.
    Type: Application
    Filed: March 18, 2003
    Publication date: October 21, 2004
    Inventors: Indra Prakash, Robert L. Augustine, Setrak K. Tanielyan
  • Patent number: 6639112
    Abstract: The invention concerns a method for preparing ketones of formula (I) wherein A and B are as defined in claim 1, consisting of reacting at a temperature ranging between 250 and 500° C. a compound of formula (II): A—X with a compound of formula (III): B—Y, wherein A, B, X and Y are as defined in claim 1, in a coolant solvent having a boiling point higher than 250 ° C.
    Type: Grant
    Filed: April 12, 2002
    Date of Patent: October 28, 2003
    Assignee: Rhodia Chimie
    Inventor: Michel Alas
  • Patent number: 6610638
    Abstract: The present invention No. I is to obtain a high purity 3-alkoxy-1-propanol having the content of alcoholic impurities of not more than 0.3% by weight by allowing to react acrolein with a linear or branched alcohol having a carbon number of 1-4 using acrolein having the content of propionaldehyde of not more than 1% by weight as a raw material, a 3-alkoxy-1-propanol is produced by a hydrogenation reaction using hydrogen of a reaction mass under the presence of a catalyst, followed by recovering through a distillation of the 3-alkoxy-1-propanol having the content of alcoholic impurities of not more than 0.3% by weight from a crude solution in the hydrogenation reaction.
    Type: Grant
    Filed: November 30, 2000
    Date of Patent: August 26, 2003
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Hiroto Tanigawa, Hiroto Miyake, Hiroshi Koyama, Akihiko Fujita, Katsuya Maruo
  • Publication number: 20030144558
    Abstract: The invention relates to a method for producing optionally substituted aliphatic, aromatic or heteraromatic aldehydes of formula (I), whereby the R represents a C1-C20 Alkyl radical, an aromatic or heteraromatic radical Ar which can optionally be substituted once or on a number of occasions by OH, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 carboxylic acids or ester containing 1-6 C atoms in the ester part, phenyl, halogen, SO3H, NO2, NR1R2 or SR1 whereby R1 and R2 can be independently H, phenyl or C1-C6 alkyl. The invention is characterised by a compound of formula (II) wherein R has the above meaning, a) is diazotized in an acidic medium, at a temperature of between −10 −+100 ° C. by a diazoation reagent and is transformed into the corresponding hydroxy carboxy acid whereby b) is transformed, by means of oxygen, into the appropriate aldehyde of formula (I) in the presence of a metal, the salt thereof, oxide or hydroxide as a catalyst.
    Type: Application
    Filed: December 13, 2002
    Publication date: July 31, 2003
    Inventors: Wolfram Hendel, Ferdinand Heu, Peter Poechlauer, Berthold WInkler
  • Patent number: 6548713
    Abstract: The process of this invention efficiently produces a compound having an alkyl group or alkenyl group bonded at the alpha position of an electron attractive group, or a derivative thereof, by catalytic radical addition reaction. The process reacts a compound containing an electron attractive group of Formula (1) as defined in the specification with a compound containing an unsaturated carbon-carbon bond of Formula (2) or (7) as defined in the specification to produce a compound of Formula (3) or (8) as defined in the specification. The invention is characterized by carrying out the reaction in the presence of oxygen and a catalytic compound of a Group 7, 8, or 9 element of the Periodic Table of Elements.
    Type: Grant
    Filed: November 9, 2001
    Date of Patent: April 15, 2003
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yasutaka Ishii, Takahiro Iwahama, Satoshi Sakaguchi, Tatsuya Nakano
  • Patent number: 6531635
    Abstract: Processes for the preparation of 3-alkoxyalkanols useful as solvents for coating materials, photoresists, or the like.
    Type: Grant
    Filed: November 19, 2001
    Date of Patent: March 11, 2003
    Assignee: Idemitsu Petrochemicals Co., Ltd.
    Inventors: Toshihide Yoshitome, Hiroshi Kawasaki, Naoya Kawano
  • Patent number: 6531634
    Abstract: Methods, compositions, and devices for alleviating the problems of toxic discharge of aldehydes present in waste streams are disclosed. The methods relate to forming neutralized aldehydes by treating aldehydes with oxidizing agents. The oxidizing agents offer a simple, effective, fast and inexpensive solution for treatment of toxic aldehydes prior to disposal into the environment.
    Type: Grant
    Filed: June 29, 2001
    Date of Patent: March 11, 2003
    Inventor: Peter Zhu
  • Patent number: 6229053
    Abstract: Abstract A process for purifying formaldehyde in which the formaldehyde is scrubbed with alcohol in an absorption unit and in the course of this reacted virtually completely to form the hemiformal and is simultaneously separated off from gaseous impurities in a first purification step. In a desorption unit, the residual impurities are then converted into a gaseous state and separated off from the liquid hemiformal, whereupon the purified hemiformal is thermally cleaved into alcohol and formaldehyde in a pyrolysis unit. The formaldehyde thus prepared is suitable, for example, for preparing oligomers, polymers, dyestuffs and fertilizers, as well as for the treatment of seeds.
    Type: Grant
    Filed: May 25, 2000
    Date of Patent: May 8, 2001
    Assignee: Ticona GmbH
    Inventors: Werner Sievers, Elke Schweers, Christine Meister
  • Patent number: 6013842
    Abstract: A process for preparing glyoxal monoacetals of the formula I, ##STR1## where R.sup.1 and R.sup.2, which can be identical or different, are C.sub.1 -C.sub.4 alkyl or C.sub.2 -C.sub.4 alkenyl involves reacting a mixture of glyoxal and glyoxal bisacetals of the formula II, ##STR2## where R.sup.1 and R.sup.2 have the meaning given above, with an excess of an alcohol of the formula R.sup.1 OH or R.sup.2 OH or mixtures of these in the presence of an acid catalyst until reaction equilibrium is achieved.
    Type: Grant
    Filed: November 25, 1997
    Date of Patent: January 11, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Carsten Groning, Jorg Therre, Gerd Kaibel, Klaus Ebel
  • Patent number: 5892129
    Abstract: A process for the preparation of 1,1,3-trialkoxypropane by acid-catalyzed reaction of acrolein with a C.sub.1 to C.sub.6 alcohol, which can be carried out well on a large scale and leads to a higher selectivity. The process involves (a) the reaction, in the presence of a solid acid catalyst which is insoluble in the reaction mixture, (b) a partial neutralization of the reaction mixture, using an amine or basic ion exchanger, and (c) specific recovery by distillation of the reaction mixture and recirculation of fractions containing useful materials; aqueous fractions containing recyclable useful materials are largely dehydrated by pervaporation prior to being recirculated.
    Type: Grant
    Filed: May 21, 1997
    Date of Patent: April 6, 1999
    Assignee: Degussa Aktiengesellschaft
    Inventors: Mathias Hoepp, Dietrich Arntz, Hans-Peter Ohlinger, Willi Hofen
  • Patent number: 5811591
    Abstract: An unsaturated aldehyde expressed by Formula (I) below is hydrated with a solution in the presence of a carboxylic-acid-based resin having of a structure expressed by Formula (II) below: ##STR1## where R represents one of a hydrogen atom and a hydrocarbon group having up to five carbons; ##STR2## where R.sub.1 and R.sub.2 respectively represent a hydrogen atom, hydrocarbon group having up to five carbons, or --(--CH.sub.2 --).sub.p1 --X group, p.sub.1, k.sub.1, and m.sub.1 respectively represent an integer from zero to six, n.sub.1 represents an integer from one to six, Y.sub.1 represents --O--, --S--, or --NR.sub.3 --, R.sub.3 represents a hydrogen atom or hydrocarbon group having up to five carbons, and X represents a carboxylic-acid-based resin main body. Using a heat-resistant catalyst as above makest it possible to increase the reaction rate by heating, and produce hydroxyalkanal at high selectivity and yield out of an industrially advantageous high-concentration unsaturated aldehyde solution.
    Type: Grant
    Filed: November 20, 1995
    Date of Patent: September 22, 1998
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Hiroshi Yamamoto, Hisakazu Shindou, Hirokazu Itoh, Tadahiro Yoneda, Masatoshi Yoshida
  • Patent number: 5723498
    Abstract: A composition which is capable of releasing acrolein and is easy to handle contains (i) an acetal of acrolein with a C.sub.1-6 alcohol with 1 to 4 hydroxyl groups and (ii) an acid soluble therein and chemically compatible with a pK.sub.s value of less than 4 and (iii) is anhydrous. A preferred composition contains 2-vinyl-1,3-dioxolane as acetal, anhydrous oxalic acid, fumaric acid or maleic acid or a mixture of mono- and di(C.sub.1 - to C.sub.3 -)alkyl phosphate as acid and, in addition, a non-ionic surfactant. The acrolein is released at the site of use upon contact with for example water for the purpose of combatting microbial, vegetable and animal pests.
    Type: Grant
    Filed: September 13, 1995
    Date of Patent: March 3, 1998
    Assignee: Degussa Aktiengellschaft
    Inventors: Peter Werle, Martin Trageser, Oswald Helmling, Harold Jakob
  • Patent number: 5639920
    Abstract: In a process of producing hydroxyalkanal, a raw material, namely, an unsaturated aldehyde, is hydrated with a solution in the presence of a catalyst, and alcohol is added to the solution. A adding amount of the alcohol with respect to the unsaturated aldehyde is preferably in a range between 0.001 percent by weight and 10 percent by weight. According to this process, a consecutive reaction (side reaction) of a reaction product, namely, hydroxyalkanal, is curbed by the alcohol added to the solution, thereby making it possible to produce hydroxyalkanal at high selectivity out of a high-density unsaturated aldehyde solution. Therefore, the above process can trigger a reaction of an industrially advantageous unsaturated aldehyde solution, and thus improves the yield of hydroxyalkanal.
    Type: Grant
    Filed: November 20, 1995
    Date of Patent: June 17, 1997
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Hiroshi Yamamoto, Hisakazu Shindou, Tadahiro Yoneda
  • 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: 5430062
    Abstract: The present invention relates to stilbene derivatives which possess utility as anti-cancer agents. The compounds can be used to treat cancers which are susceptible to treatment therewith, and can be utilized in a method of treating such cancers. Pharmaceutical compositions containing the compounds are disclosed. Three preferred compounds among those disclosed are (Z)-1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene, (Z)-1-(4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)ethene, and 4-methyl-3',4',5'-trimethoxybenzylaniline hydrochloride.
    Type: Grant
    Filed: June 23, 1993
    Date of Patent: July 4, 1995
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Mark S. Cushman, Ernest Hamel
  • Patent number: 5426239
    Abstract: Process for the continuous preparation of dimethoxy ethanal (DME) in which a 70% by weight of an aqueous solution of glyoxal is continuously reacted with 8 to 12 moles of methanol/mole of glyoxal in the presence of a cation exchange resin, then the reaction solution obtained is subjected to an initial distillation, at atmospheric pressure, in order to recover more than 90% of the unreacted methanol, which is recycled, then to a second distillation under a pressure of less than 10.+-.2 kPa in order to isolate an aqueous mixture containing the greater part of DME and 1,1,2,2-tetramethoxyethane (TME) formed. This mixture, after dilution with water (molar ratio of water/TME 29.+-.4), is subjected to a distillation under a pressure of less than 19 kPa in order to remove from the top fraction an aqueous mixture containing more than 98.5% of the TME present and to also obtain an aqueous solution of DME having a purity greater than 98.
    Type: Grant
    Filed: January 13, 1994
    Date of Patent: June 20, 1995
    Assignee: Societe Francaise Hoechst
    Inventors: Gilles Dressaire, Alain Schouteeten
  • Patent number: 5371297
    Abstract: A process for the preparation of aldehydes of the general formula I ##STR1## in which R.sup.1, R.sup.2 denote hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.8 cycloalkyl, acyl, aryl, or C.sub.7 -C.sub.20 aralkyl or together stand for --(CH.sub.2).sub.n --X--(CH.sub.2).sub.m --,X denotes methylene, oxygen, sulfur, NH or NR.sub.3 andn, m stand for an integer from 0 bis 8,wherein a geminal formyl ester of the general formula II ##STR2## in which R.sup.1 and R.sup.2 have the aforementioned meanings and R.sup.3 denotes C.sub.1 -C.sub.12 alkyl, is caused to react in the presence of an acid catalyst at temperatures ranging from 150.degree. to 400.degree. C.
    Type: Grant
    Filed: September 16, 1993
    Date of Patent: December 6, 1994
    Assignee: BASF Aktiengesellschaft
    Inventor: Rolf Fischer
  • Patent number: 5354915
    Abstract: This invention provides an improved process for converting .alpha.,.beta.-olefinically unsaturated aldehydic or ketonic compounds into the corresponding allylic alcohol using an alcohol as a hydrogen donor. This process is conducted in the presence of a supported tetragonal zirconium oxide catalyst or supported HfO.sub.2, V.sub.2 O.sub.5, NbO.sub.5, TiO.sub.2 and Ta.sub.2 O.sub.5 catalysts.
    Type: Grant
    Filed: December 21, 1992
    Date of Patent: October 11, 1994
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Walter T. Reichle
  • Patent number: 5243082
    Abstract: Acrolein is prepared by the heating of 3,4-dihydro-2H-pyran-2-carboxaldehyde. The process provides acrolein in very high yields and with few impurities. The process is advantageously employed to produce acrolein at the point of use.
    Type: Grant
    Filed: September 22, 1992
    Date of Patent: September 7, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: William G. Etzkorn, William D. Neilsen
  • Patent number: 5196608
    Abstract: The present invention relates to the use of an allylchloride of the general formula ##STR1##wherein R is a C.sub.1 -C.sub.12 alkyl group or a C.sub.2 -C.sub.12 alkenyl group, which groups may be substituted with one or more substitutents selected from the group consisting of C.sub.1 -C.sub.4 alkoxy, halogen, unsubstituted phenyl and substituted phenyl; a (trihydrocarbyl)silyl group; a (dihydrocarbyl) (hydrocarbyloxy)silyl group; or a dihydropyran-2-yl group, a tetrahydropyran-2-yl group, a dihydrofur-2-yl group or a tetrahydrofur-2-yl group, which groups may be substituted with C.sub.1 -C.sub.6 alkyl;for preparing an aldehyde compound via an intermediate alcohol compound.The invention further relates to a new allylchloride.
    Type: Grant
    Filed: December 2, 1991
    Date of Patent: March 23, 1993
    Assignee: Duphar International Research B.V.
    Inventors: Gerrit J. Lagerweij, Cornelis Bakker, Monique E. A. De Bruin-Van Der Flier
  • Patent number: 5183944
    Abstract: Aqueous solutions can be doped in a simple, safe and economic manner with acrolein in biocidally effective concentration by converting acrolein acetals in aqueous phase in the presence of a strongly acidic deacetalation catalyst into acrolein, cleaving the alcohol component, constantly removing the formed acrolein from the decetalation mixture and transferring it by means of an inert gas stream or a liquid jet pump with the aqueous solution to be doped as jet fluid into the aqueous solution to be doped.
    Type: Grant
    Filed: November 26, 1991
    Date of Patent: February 2, 1993
    Assignee: Degussa AG
    Inventors: Peter Werle, Martin Trageser, Hermann Piana
  • Patent number: 5053552
    Abstract: The present invention provides a novel process for producing .alpha.,.beta.-unsaturated aldehydes including industrial important fragrances such as citral and sinensal, starting materials for preparing pharmaceutical drugs such as senecioaldehyde, farnesal, 8-acetoxy-2,6-dimethyl-2,6-octadienal and the like, directly and in high yield, from formic acid esters of allylic alcohols in the presence of a catalytic amount of aluminum alkoxide by the oxidation of the corresponding alehyde.
    Type: Grant
    Filed: June 14, 1990
    Date of Patent: October 1, 1991
    Assignee: Kuraray Company, Ltd.
    Inventors: Toshiki Mori, Shigeaki Suzuki, Takashi Onishi, Kazuo Yamamoto
  • Patent number: 4933500
    Abstract: Citral is prepared from prenol and prenal by condensation to form an acetal followed by cracking, both operations being effected in the presence of a lithium halide (e.g. lithium chloride) as catalyst.
    Type: Grant
    Filed: May 15, 1989
    Date of Patent: June 12, 1990
    Assignee: Rhone-Poulenc Sante
    Inventors: Pierre Chabardes, Jacques Chazal
  • Patent number: 4892976
    Abstract: The process for the preparation of an aldehyde of formula R--CHO in which R is an alkyl group of C.sub.1 -C.sub.7 comprises according to the invention the reaction on an alkyl formate of formula H--COOR in which R has the meaning given above, of a gas constituted mainly by CO, in the presence of(a) a catalyst based on a metal chosen from among Rh, Ru, Ir, mixtures of them or a mixture of Rh and/or Ru and/or Ir with Co, Ni or Fe,(b) a promoter chosen from among iodides and mixtures of covalent compounds of iodine and a phosphine or a tertiary amine,(c) a solvent consisting of a cyclic N-alkyl amide.
    Type: Grant
    Filed: July 15, 1988
    Date of Patent: January 9, 1990
    Assignee: Sollac
    Inventors: Jean Cordier, Bernard Dussart, Francis Petit, Yves Castanet, Serge Melloul, Andre Mortreux
  • Patent number: 4851583
    Abstract: This invention relates to the generation of acrolein from an acetal of acrolein via exposure to a sulfonic acid reusable catalytic material. The acrolein acetals have the following general structures; ##STR1## where R may or may not be equal to R' R/R' is an alkyl group having from 1 to 6 carbons; and ##STR2## where R is a cyclic diol derived from ethylene glycol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol, glycerol hexoses or polyaccharides.
    Type: Grant
    Filed: January 4, 1988
    Date of Patent: July 25, 1989
    Assignee: Betz Laboratories, Inc.
    Inventors: Edmund Bockowski, Cato R. McDaniel
  • Patent number: 4835320
    Abstract: This process for the preparation of products of general formula (I): ##STR1## wherein either R.sub.1 and R.sub.2, which are identical, represent a --CHRR.sub.3 group, in which R and R.sub.3, which are identical or different, represent an alkyl, alkenyl or aralkyl group, or R.sub.1 and R.sub.2, which are identical, represent a --CH.sub.2 R group, in which R represents a hydrogen atom, an alkyl, alkenyl or aralkyl radical, or R.sub.1 and R.sub.2 together form a --CH.sub.2 --(CRR).sub.n --CHR-- radical, in which n represents 0 or 1 and R retains the meaning given previously, is characterized by reacting glyoxal in the presence of an acid catalyst with an excess of the corresponding alcohol of general formula (II) RR.sub.3 CHOH, (III) RCH.sub.2 OH or (IV) --(CRR).sub.n --CHROH, in which R, R.sub.3 and n retain the meaning given previously, then stopping the reaction as soon as the concentration of the desired monoacetal of general formula (I) decreases in the reaction medium in favor of bisacetal.
    Type: Grant
    Filed: June 1, 1987
    Date of Patent: May 30, 1989
    Assignee: Societe Francaise Hoechst
    Inventors: Alain Blanc, Farid Hamedi-Sangsari, Francine J. Chastrette
  • Patent number: 4812593
    Abstract: Bifunctional compounds of the formula ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each alkyl of 1 to 6 carbon atoms, R.sup.2 and R.sup.3 may furthermore be hydrogen, R.sup.2 is furthermore alkoxy and R.sup.4 is hydrogen, alkyl of 1 to 6 carbon atoms or alkoxy, and a double bond may be present between carbon atoms 2 and 3, are prepared by converting a tetraalkoxyalkane or a dialkoxyalkanoate of the formulae ##STR2## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the above meanings, in the presence of a catalyst, such as a zeolite, in particular one of the pentasil type, and/or a phosphate and/or phosphoric acid on a carrier.
    Type: Grant
    Filed: August 6, 1987
    Date of Patent: March 14, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer
  • Patent number: 4748279
    Abstract: A liquid sterlizing composition comprising the reaction product of a non-ionic surfactant, a gluteraldehyde and triethylene glycol.
    Type: Grant
    Filed: June 23, 1987
    Date of Patent: May 31, 1988
    Inventor: Reginald K. Whiteley
  • Patent number: 4710316
    Abstract: Compounds of the general formula (I) ##STR1## and compounds of the general formula (II) ##STR2## in which R.sup.1 represents --OH, --CH.sub.2 OH, --CH.sub.2 --OCH.sub.3, --CHOH--CH.sub.3, --CHO or --CH(OCH.sub.3).sub.2,R.sup.2 represents methyl or ethyl,R.sup.3 represents hydrogen or methyl, andX represents hydrogen or methyl, are disclosed.Processes for the manufacture of certain compounds of formula (I) and for those of formula (II) are also provided. The compounds are useful as perfume materials.
    Type: Grant
    Filed: August 13, 1986
    Date of Patent: December 1, 1987
    Assignee: Consortium fur Elektrochemische Industrie GmbH
    Inventors: Walter Hafner, Peter Ritter, Helmut Gebauer, Marlies Regiert
  • Patent number: 4701562
    Abstract: Aldehydes can be condensed with ketones or aldehydes to produce higher aldehydes or ketones by contacting the materials to be condensed with a nonzeolitic molecular sieve. The condensation may be carried out in the presence of hydrogen to give as product a saturated aldehyde or ketone. The ketone and/or aldehyde may be generated in situ by dehydrogenation of an alcohol, and the hydrogen thus liberated used to effect hydrogenation of the immediate unsaturated product of the condensation, thereby producing as the final product a saturated aldehyde or ketone. The non-zeolitic molecular sieves can achieve improved conversion rates and selectivities as compared with conventional catalysts for the reaction.
    Type: Grant
    Filed: June 25, 1986
    Date of Patent: October 20, 1987
    Assignee: Union Carbide Corporation
    Inventor: Kurt D. Olson
  • Patent number: 4691062
    Abstract: 4-chloro-butanals of the formula ##STR1## where R is hydrogen or a straight or branched chain alkyl group of 1 to 4 carbon atoms are produced by reacting the corresponding 1,1-dimethoxy-4-hydroxybutane at a temperature between -20.degree. and +80.degree. C. in the presence of triphenylphosphine with carbon tetrachloride and hydrolyzing the 1,1-dimethoxy-4-chloro-butane obtained in acid medium.
    Type: Grant
    Filed: October 22, 1986
    Date of Patent: September 1, 1987
    Assignee: Degussa Aktiengesellschaft
    Inventors: Juan Andrade, Gunter Prescher, Klaus Kohler
  • Patent number: 4638091
    Abstract: A method for the preparation of a fluorinated amine of the formula: ##STR1## wherein X represents hydrogen or fluorine, R represents hydrogen, lower alkyl, difluoromethyl or trifluoromethyl and each of R.sup.1 and R.sup.2, independently, represents hydrogen or lower alkyl, which comprises reacting a carbonyl compound of the formula:XCF.sub.2 CORat an elevated temperature with a nitrogenous base of the formula: ##STR2## and hydrogen in the presence of a hydrogenation catalyst.
    Type: Grant
    Filed: February 11, 1985
    Date of Patent: January 20, 1987
    Assignee: Imperial Chemical Industries PLC
    Inventor: Roy D. Bowden
  • Patent number: 4608443
    Abstract: The preparation of 1,4-butandial (succindialdehyde) is obtained using acrolein. The acrolein is first converted with an alkanol into 3,3-dialkoxy-1-propene and this is then hydroformylated in the presence of hydridotristriphenylphosphine-rhodiumcarbonyl mixed with triphenylphosphine or triphenylphosphite as the catalyst. The thereby obtained 4,4-dialkoxy-butanal is removed from the hydroformylation product by means of distillation and is then hydrolyzed to 1,4-butandial.
    Type: Grant
    Filed: January 24, 1985
    Date of Patent: August 26, 1986
    Assignee: Degussa Aktiengesellschaft
    Inventors: Juan Andrade, Gunter Prescher, Marc Samson
  • Patent number: 4607126
    Abstract: The invention relates to a process for the preparation of glyoxal, alkylglyoxals and acetals thereof by reacting .alpha.,.beta.-unsaturated dialkylacetals with the equivalent amount of ozone and subsequently subjecting the ozonization products to catalytic hydrogenation, the peroxide-containing ozonization solution being fed continuously into a suspension of the hydrogenation catalyst, while a peroxide content of not more than 0.1 mole/liter is maintained, and cleaving the ozonization products by reduction, after which the dialkylacetals formed in the hydrogenation are, if desired, cleaved to give glyoxal or alkylglyoxals.
    Type: Grant
    Filed: December 17, 1984
    Date of Patent: August 19, 1986
    Assignee: Chemie Linz Aktiengesellschaft
    Inventor: Alexander Sajtos
  • Patent number: 4562296
    Abstract: One or more aldehydes or ketones, or both, are produced by pyrolyzing an alcohol having at least two carbon atoms or an aldehyde having at least two carbon atoms, or both, over a Group VIII metal oxide catalyst, preferably a catalyst composed predominantly of iron oxide, notably ferric oxide. Preferably, the catalyst additionally contains a minor proportion of a Group IV-A metal oxide, most preferably germanium dioxide. The process provides a good yield of lower molecular weight aldehydes, such as formaldehyde, or higher molecular weight ketones, such as acetone, 2-pentanone and the like. Selective manufacture of products enriched either in aldehyde or in ketone can be achieved by a simple adjustment in the reaction conditions employed.
    Type: Grant
    Filed: November 13, 1984
    Date of Patent: December 31, 1985
    Assignee: Ethyl Corporation
    Inventor: Duane C. Hargis
  • Patent number: 4551560
    Abstract: A process for the selective, thermally-induced hydrolysis of acetals to the corresponding aldehydes and alcohols is disclosed, involving heating and pressurizing a substantially acid-free acetal containing solution to effect the rapid hydrolysis of the acetals without significant harm to the remaining reaction system components, and removing the treated solution from the reaction zone as product.
    Type: Grant
    Filed: November 9, 1984
    Date of Patent: November 5, 1985
    Assignee: The Halcon SD Group, Inc.
    Inventor: Nabil M. Rizkalla
  • Patent number: 4504671
    Abstract: Aldoxime or ketoxime-O-alkanoic acid is prepared by transoximation of an aldehyde or ketone, the reaction being conducted in a liquid phase at a pressure below one atmosphere. Conversion of the aldoxime or ketoxime-O-alkanoic acid to the ester or salt form is also described.
    Type: Grant
    Filed: October 15, 1982
    Date of Patent: March 12, 1985
    Assignee: PPG Industries, Inc.
    Inventors: Dennis K. Krass, John C. Crano, Melvin S. Newman
  • Patent number: 4499308
    Abstract: Disclosed is the reaction acrolein or methacrolein with a mono- or dihydroxyalkane to produce a 3-alkoxypropionaldehyde or a 3-(hydroxyalkoxy)propionaldehyde in the case of acrolein; or to produce a 3-alkoxy-2-methylpropionaldehyde or a 3-(hydroxyalkoxy)-2-methylpropionaldehyde in the case of methacrolein, by contacting a mixture of the recited reactants with a particulate solid metallic catalyst comprising an alloy of palladium and cadmium.
    Type: Grant
    Filed: December 5, 1983
    Date of Patent: February 12, 1985
    Assignee: The Standard Oil Company
    Inventors: Christos Paparizos, Robert S. Shout, Wilfrid G. Shaw