Oxy Or -coo- Containing Reactant Patents (Class 568/465)
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Publication number: 20140357900Abstract: 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: ApplicationFiled: December 10, 2012Publication date: December 4, 2014Inventors: Chunlei Lv, Shiqing Pl, Jianhui Chen, Dingqiang Lu, Pingkai Ouyang
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Patent number: 8809594Abstract: 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: GrantFiled: September 21, 2012Date of Patent: August 19, 2014Assignee: Eastman Chemical CompanyInventors: David William Norman, Damon Ray Billodeaux, Melissa Dawn Page
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Patent number: 8143454Abstract: 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: GrantFiled: December 16, 2008Date of Patent: March 27, 2012Assignee: Arkema FranceInventor: Jean-Luc Dubois
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Patent number: 8044246Abstract: 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: GrantFiled: July 27, 2010Date of Patent: October 25, 2011Assignee: Lonza Ltd.Inventors: Wolfgang Wenger, Andreas Heyl, Lothar Ott, Herbert Vogel, Paul Hanselmann, Gökhan Aras
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Patent number: 7956203Abstract: 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: GrantFiled: March 27, 2001Date of Patent: June 7, 2011Assignee: E. I. du Pont de Nemours and CompanyInventors: Vladimir Grushin, Walter Partenheimer, Leo E. Manzer
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Publication number: 20110034737Abstract: 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: ApplicationFiled: October 20, 2010Publication date: February 10, 2011Applicant: Nektar TherapeuticsInventor: Antoni Kozlowski
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Publication number: 20110028764Abstract: 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: ApplicationFiled: July 27, 2010Publication date: February 3, 2011Inventors: Wolfgang WENGER, Andreas HEYL, Lothar OTT, Herbert VOGEL, Paul HANSELMANN, Gökhan ARAS
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Publication number: 20090105506Abstract: 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: ApplicationFiled: September 12, 2006Publication date: April 23, 2009Applicant: Central Glass Company, LimitedInventors: Takeo Komata, Kenji Hosoi, Shinya Akiba
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Publication number: 20090069604Abstract: 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: ApplicationFiled: February 23, 2007Publication date: March 12, 2009Applicant: BASF SEInventors: Steffen Maas, Thorsten Johann, Michael Koch, Tilman Sirch, Stephan Schlitter, Stefan Rittinger, Michael Steiniger
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Patent number: 7498451Abstract: 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: GrantFiled: November 27, 2003Date of Patent: March 3, 2009Assignee: BASF AktiengesellschaftInventors: Gerd Haderlein, Hans-Georg Göbbel, Wolfgang Siegel
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Patent number: 7094932Abstract: 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: GrantFiled: November 8, 2001Date of Patent: August 22, 2006Assignee: Resource Transforms International Ltd.Inventors: Piotr A. Majerski, Jan K. Piskorz, Desmond St. A. G. Radlein
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Publication number: 20040220429Abstract: 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: ApplicationFiled: June 3, 2004Publication date: November 4, 2004Applicant: Regents of the University of CaliforniaInventors: Haichao Liu, Enrique Iglesia
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Publication number: 20040210094Abstract: 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: ApplicationFiled: March 18, 2003Publication date: October 21, 2004Inventors: Indra Prakash, Robert L. Augustine, Setrak K. Tanielyan
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Patent number: 6639112Abstract: 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: GrantFiled: April 12, 2002Date of Patent: October 28, 2003Assignee: Rhodia ChimieInventor: Michel Alas
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Patent number: 6610638Abstract: 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: GrantFiled: November 30, 2000Date of Patent: August 26, 2003Assignee: Daicel Chemical Industries, Ltd.Inventors: Hiroto Tanigawa, Hiroto Miyake, Hiroshi Koyama, Akihiko Fujita, Katsuya Maruo
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Publication number: 20030144558Abstract: 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: ApplicationFiled: December 13, 2002Publication date: July 31, 2003Inventors: Wolfram Hendel, Ferdinand Heu, Peter Poechlauer, Berthold WInkler
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Patent number: 6548713Abstract: 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: GrantFiled: November 9, 2001Date of Patent: April 15, 2003Assignee: Daicel Chemical Industries, Ltd.Inventors: Yasutaka Ishii, Takahiro Iwahama, Satoshi Sakaguchi, Tatsuya Nakano
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Patent number: 6531634Abstract: 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: GrantFiled: June 29, 2001Date of Patent: March 11, 2003Inventor: Peter Zhu
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Patent number: 6531635Abstract: Processes for the preparation of 3-alkoxyalkanols useful as solvents for coating materials, photoresists, or the like.Type: GrantFiled: November 19, 2001Date of Patent: March 11, 2003Assignee: Idemitsu Petrochemicals Co., Ltd.Inventors: Toshihide Yoshitome, Hiroshi Kawasaki, Naoya Kawano
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Patent number: 6229053Abstract: 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: GrantFiled: May 25, 2000Date of Patent: May 8, 2001Assignee: Ticona GmbHInventors: Werner Sievers, Elke Schweers, Christine Meister
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Patent number: 6013842Abstract: 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: GrantFiled: November 25, 1997Date of Patent: January 11, 2000Assignee: BASF AktiengesellschaftInventors: Carsten Groning, Jorg Therre, Gerd Kaibel, Klaus Ebel
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Patent number: 5892129Abstract: 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: GrantFiled: May 21, 1997Date of Patent: April 6, 1999Assignee: Degussa AktiengesellschaftInventors: Mathias Hoepp, Dietrich Arntz, Hans-Peter Ohlinger, Willi Hofen
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Patent number: 5811591Abstract: 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: GrantFiled: November 20, 1995Date of Patent: September 22, 1998Assignee: Nippon Shokubai Co., Ltd.Inventors: Hiroshi Yamamoto, Hisakazu Shindou, Hirokazu Itoh, Tadahiro Yoneda, Masatoshi Yoshida
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Patent number: 5723498Abstract: 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: GrantFiled: September 13, 1995Date of Patent: March 3, 1998Assignee: Degussa AktiengellschaftInventors: Peter Werle, Martin Trageser, Oswald Helmling, Harold Jakob
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Patent number: 5639920Abstract: 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: GrantFiled: November 20, 1995Date of Patent: June 17, 1997Assignee: Nippon Shokubai Co., Ltd.Inventors: Hiroshi Yamamoto, Hisakazu Shindou, Tadahiro Yoneda
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Patent number: 5434313Abstract: 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: GrantFiled: October 6, 1994Date of Patent: July 18, 1995Assignee: Davy McKee (London) LimitedInventors: George E. Harrison, Arthur J. Reason, Alan J. Dennis, Mohammad Sharif
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Patent number: 5430062Abstract: 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: GrantFiled: June 23, 1993Date of Patent: July 4, 1995Assignee: Research Corporation Technologies, Inc.Inventors: Mark S. Cushman, Ernest Hamel
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Patent number: 5426239Abstract: 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: GrantFiled: January 13, 1994Date of Patent: June 20, 1995Assignee: Societe Francaise HoechstInventors: Gilles Dressaire, Alain Schouteeten
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Patent number: 5371297Abstract: 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: GrantFiled: September 16, 1993Date of Patent: December 6, 1994Assignee: BASF AktiengesellschaftInventor: Rolf Fischer
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Patent number: 5354915Abstract: 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: GrantFiled: December 21, 1992Date of Patent: October 11, 1994Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Walter T. Reichle
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Patent number: 5243082Abstract: Acrolein is prepared by the heating of 3,4-dihydro-2H-pyran-2-carboxaldehyde. The process provides acrolein in very high yields and with few impurities. The process is advantageously employed to produce acrolein at the point of use.Type: GrantFiled: September 22, 1992Date of Patent: September 7, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: William G. Etzkorn, William D. Neilsen
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Patent number: 5196608Abstract: 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: GrantFiled: December 2, 1991Date of Patent: March 23, 1993Assignee: Duphar International Research B.V.Inventors: Gerrit J. Lagerweij, Cornelis Bakker, Monique E. A. De Bruin-Van Der Flier
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Patent number: 5183944Abstract: 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: GrantFiled: November 26, 1991Date of Patent: February 2, 1993Assignee: Degussa AGInventors: Peter Werle, Martin Trageser, Hermann Piana
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Patent number: 5053552Abstract: The present invention provides a novel process for producing .alpha.,.beta.-unsaturated aldehydes including industrial important fragrances such as citral and sinensal, starting materials for preparing pharmaceutical drugs such as senecioaldehyde, farnesal, 8-acetoxy-2,6-dimethyl-2,6-octadienal and the like, directly and in high yield, from formic acid esters of allylic alcohols in the presence of a catalytic amount of aluminum alkoxide by the oxidation of the corresponding alehyde.Type: GrantFiled: June 14, 1990Date of Patent: October 1, 1991Assignee: Kuraray Company, Ltd.Inventors: Toshiki Mori, Shigeaki Suzuki, Takashi Onishi, Kazuo Yamamoto
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Patent number: 4933500Abstract: 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: GrantFiled: May 15, 1989Date of Patent: June 12, 1990Assignee: Rhone-Poulenc SanteInventors: Pierre Chabardes, Jacques Chazal
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Patent number: 4892976Abstract: 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: GrantFiled: July 15, 1988Date of Patent: January 9, 1990Assignee: SollacInventors: Jean Cordier, Bernard Dussart, Francis Petit, Yves Castanet, Serge Melloul, Andre Mortreux
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Patent number: 4851583Abstract: 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: GrantFiled: January 4, 1988Date of Patent: July 25, 1989Assignee: Betz Laboratories, Inc.Inventors: Edmund Bockowski, Cato R. McDaniel
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Patent number: 4835320Abstract: 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: GrantFiled: June 1, 1987Date of Patent: May 30, 1989Assignee: Societe Francaise HoechstInventors: Alain Blanc, Farid Hamedi-Sangsari, Francine J. Chastrette
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Patent number: 4812593Abstract: 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: GrantFiled: August 6, 1987Date of Patent: March 14, 1989Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer
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Patent number: 4748279Abstract: A liquid sterlizing composition comprising the reaction product of a non-ionic surfactant, a gluteraldehyde and triethylene glycol.Type: GrantFiled: June 23, 1987Date of Patent: May 31, 1988Inventor: Reginald K. Whiteley
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Patent number: 4710316Abstract: 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: GrantFiled: August 13, 1986Date of Patent: December 1, 1987Assignee: Consortium fur Elektrochemische Industrie GmbHInventors: Walter Hafner, Peter Ritter, Helmut Gebauer, Marlies Regiert
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Patent number: 4701562Abstract: 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: GrantFiled: June 25, 1986Date of Patent: October 20, 1987Assignee: Union Carbide CorporationInventor: Kurt D. Olson
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Patent number: 4691062Abstract: 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: GrantFiled: October 22, 1986Date of Patent: September 1, 1987Assignee: Degussa AktiengesellschaftInventors: Juan Andrade, Gunter Prescher, Klaus Kohler
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Patent number: 4638091Abstract: 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: GrantFiled: February 11, 1985Date of Patent: January 20, 1987Assignee: Imperial Chemical Industries PLCInventor: Roy D. Bowden
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Patent number: 4608443Abstract: 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: GrantFiled: January 24, 1985Date of Patent: August 26, 1986Assignee: Degussa AktiengesellschaftInventors: Juan Andrade, Gunter Prescher, Marc Samson
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Patent number: 4607126Abstract: 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: GrantFiled: December 17, 1984Date of Patent: August 19, 1986Assignee: Chemie Linz AktiengesellschaftInventor: Alexander Sajtos
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Patent number: 4562296Abstract: 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: GrantFiled: November 13, 1984Date of Patent: December 31, 1985Assignee: Ethyl CorporationInventor: Duane C. Hargis
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Patent number: 4551560Abstract: 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: GrantFiled: November 9, 1984Date of Patent: November 5, 1985Assignee: The Halcon SD Group, Inc.Inventor: Nabil M. Rizkalla
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Patent number: 4504671Abstract: 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: GrantFiled: October 15, 1982Date of Patent: March 12, 1985Assignee: PPG Industries, Inc.Inventors: Dennis K. Krass, John C. Crano, Melvin S. Newman
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Patent number: 4499308Abstract: 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: GrantFiled: December 5, 1983Date of Patent: February 12, 1985Assignee: The Standard Oil CompanyInventors: Christos Paparizos, Robert S. Shout, Wilfrid G. Shaw