Preparing By Reduction Or Dehydrogenation (e.g., By Hydrogenation, Etc.) Patents (Class 568/799)
-
Patent number: 7462747Abstract: The invention relates to a process for preparing polymethylol compounds of the formula (I) where the radicals R are each, independently of one another, 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 22 carbon atoms, by condensation of aldehydes having from 2 to 24 carbon atoms with formaldehyde in an aldol reaction using tertiary amines as catalyst to form alkanals of the formula (II) where the radicals R each independently have one of the abovementioned meanings, and subsequent hydrogenation of the latter. The particular inventive feature of this process is that the aldol reaction is carried out using an aqueous formaldehyde solution having a formic acid content of <150 ppm and preferably <100 ppm. In this way of carrying out the process, the formation of by-products can advantageously be prevented in a targeted manner and the yield of the desired polymethylol compound can thereby be increased.Type: GrantFiled: April 30, 2007Date of Patent: December 9, 2008Assignee: BASF AktiengesellschaftInventors: Timan Sirch, Michael Steiniger, Steffen Maas, Stefan Rittinger, Stephan Schlitter, Maria Guixa, Todd C. Spengeman, Jeffrey T. Andress
-
Patent number: 7425657Abstract: The invention provides palladium-catalyzed hydrogenations of bio-oils and certain organic compounds. Experimental results have shown unexpected and superior results for palladium-catalyzed hydrogenations of organic compounds typically found in bio-oils.Type: GrantFiled: June 6, 2007Date of Patent: September 16, 2008Assignee: Battelle Memorial InstituteInventors: Douglas C. Elliott, Jianli Hu, Todd R. Hart, Gary G. Neuenschwander
-
Patent number: 7388116Abstract: Process for the catalytic hydrogenation of methylolalkanals of the general formula where R1 and R2 are each, independently of one another, 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 by means of hydrogen over a hydrogenation catalyst, wherein hydrogen is used in a molar ratio to methylolalkanal of greater than 1.Type: GrantFiled: June 6, 2006Date of Patent: June 17, 2008Assignee: BASF AktiengesellschaftInventors: Steffen Maas, Thorsten Johann, Michael Koch, Tilman Sirch, Stephan Schlitter, Stefan Rittinger, Michael Steiniger, Todd C Spengeman
-
Patent number: 7358399Abstract: A process is described for the preparation of N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propaneamine comprising substitution of the sulfonyloxy group of the compound of the formula in which the substituents R and R? have the meanings stated in the description, in a solvent comprising an ionic liquid, to yield the tertiary amine of the formula and the subsequent deprotection thereof.Type: GrantFiled: October 6, 2005Date of Patent: April 15, 2008Assignee: Chemi SPAInventors: Stefano Turchetta, Umberto Ciambecchini, Pietro Massardo
-
Patent number: 7230141Abstract: A process for preparing toluene derivatives of the formula I, where R1, R2 and R3 independently of one another are hydrogen, halogen, C1–C6-alkyl, hydroxyl or C1–C6-alkoxy, by hydrogenating benzaldehydes and/or benzyl alcohols of the formula II, with hydrogen in the presence of a catalyst, which is described in more detail in the description.Type: GrantFiled: January 20, 2003Date of Patent: June 12, 2007Assignee: BASF AktiengesellschaftInventors: Nils Bottke, Rolf-Hartmuth Fischer, Thomas Nöbel, Markus Rösch
-
Patent number: 6984744Abstract: The invention is concerned with new phosphine ligands of formula I wherein R1 and R2 are independently of each other unsubstituted alkyl, aryl, cycloalkyl or heteroaryl, or alkyl, aryl, cycloalkyl or heteroaryl each of which independently is substituted by alkyl, alkoxy, halogen, hydroxy, amino, mono- or dialkylamino, aryl, —SO2—R7, —SO3?, —CO—NR8R8?, carboxy, alkoxycarbonyl, trialkylsilyl, diarylalkylsilyl, dialkylarylsilyl or triarylsilyl; R3 is alkyl, cycloalkyl, aryl or heteroaryl; R4? and R4 are independently of each other hydrogen, alkyl or optionally substituted aryl; or R4? and R4 together with the C-atom they are attached, form a 3-8-membered carbocyclic ring; dotted line is optionally a double bond; R5 and R6 are independently of each other hydrogen, alkyl or aryl, R7 is alkyl or aryl; and R8 and R8? are independently of each other hydrogen, alkyl or aryl; the substituents attached by the bold bonds are in cis relation to each other; metal complexes with such ligands in asymmetric reactions.Type: GrantFiled: November 21, 2003Date of Patent: January 10, 2006Assignee: Hoffman-La Roche Inc.Inventors: Piotr Osinski, Kazimierz Michal Pietrusiewicz, Rudolf Schmid
-
Patent number: 6936738Abstract: A process is described for the preparation of phenol characterized in that the phenol is obtained by means of the hydrodeoxygenation of benzene-diols with hydrogen, operating in continuous, in an aqueous solution, at temperatures ranging from 250 to 500° C., at pressures of 1-100 bar and in the presence of a catalyst based on elements of group VIB or group VIII of the periodic table.Type: GrantFiled: October 14, 2003Date of Patent: August 30, 2005Assignees: ENI S.p.A., Polimeri Europa S.p.A.Inventors: Leonardo Dalloro, Alberto Cesana, Roberto Buzzoni, Franco Rivetti
-
Patent number: 6806395Abstract: A process for producing a 3,5-bisalkylphenol (2) according to the following reaction scheme: (wherein R1 represents a hydrogen atom, an alkali metal atom, an alkaline earth metal atom, or a hydroxyl-protecting group (other than methyl group); R2 represents a C1 to C5 lower alkyl group or an optionally substituted phenyl group; and each of R3 and R4, which may be identical to or different from each other, represents a lower alkyl group, an aralkyl group, or an aryl group); a carbinol compound (1); and a process for producing the carbinol compound. The production process of the present invention enables efficient and safe production of a variety of 3,5-bisalkylphenols including 3,5-diisopropylphenol, which are important as synthesis intermediates for drugs and agricultural chemicals, in shorter steps at high purity in high yield, thus contributing to consistent supply of drugs and agricultural chemicals.Type: GrantFiled: March 18, 2003Date of Patent: October 19, 2004Assignee: Kowa Co., Ltd.Inventors: Kimiyuki Shibuya, Tadaaki Ohgiya, Toru Miura, Kazuhiro Onogi
-
Patent number: 6765118Abstract: In a process for the preparation of alcohols by catalytic hydrogenation of carbonyl compounds, the catalyst used is 0.01 to 50% by weight of rhenium and 0 to 20% by weight, in each case based on the total weight of the catalyst, of at least one further metal chosen from Zn, Cu, Ag, Au, Ni, Fe, Cr, V on oxidatively pretreated activated carbon as support.Type: GrantFiled: September 23, 2002Date of Patent: July 20, 2004Assignee: BASF AktiengesellschaftInventors: Rolf-Hartmuth Fischer, Rolf Pinkos, Stephan Andreas Schunk, Joachim Wulff-Döring
-
Publication number: 20040077906Abstract: A process is described for the preparation of phenol characterized in that the phenol is obtained by means of the hydrodeoxygenation of benzene-diols with hydrogen, operating in continuous, in an aqueous solution, at temperatures ranging from 250 to 500° C., at pressures of 1-100 bar and in the presence of a catalyst based on elements of group VIB or group VIII of the periodic table.Type: ApplicationFiled: October 14, 2003Publication date: April 22, 2004Applicants: ENI S.p.A., POLIMERI EUROPA S.p.A.Inventors: Leonardo Dalloro, Alberto Cesana, Roberto Buzzoni, Franco Rivetti
-
Publication number: 20040044256Abstract: The invention relates to a method for catalytically hydrating a poly- or monomethylol alkanal of the general formula (I), wherein R is the same or different and may represent a substituted or unsubstituted aliphatic hydrocarbon with 6 to 22 carbon atoms, an aryl or arylalkyl group with 6 to 22 carbon atoms or a methylol group, in the presence of a copper-containing catalyst. The inventive method is characterized in that the poly- or monomethylol alkanal containing batch to be hydrated has a total content of up to 5 ppm of metal ions of the groups 3 to 14 of the periodic system.Type: ApplicationFiled: April 17, 2003Publication date: March 4, 2004Inventors: Matthias Dernbach, Michael Koch, Gerhard Schulz, Hagen Weigl, Steffen Maas
-
Patent number: 6676919Abstract: The invention relates to a method for producing catalysts by immersion coating a metallic support with at least one platinum metal. An aqueous medium which comprises at least one platinum metal complex, at least one reduction agent and at least one complexer and which has a pH value of more than 4 is brought into contact with the metallic support in order to deposit the platinum metal, the platinum metal being deposited in the form of discreet, immobilised particles. The invention also relates to the catalysts obtained using this method and to their use for producing hydrogen peroxide and for hydrogenating organic compounds.Type: GrantFiled: October 4, 2001Date of Patent: January 13, 2004Assignee: BASF AktiengesellschaftInventors: Martin Fischer, Markus Hölzle, Stefan Quaiser, Achim Stammer
-
Patent number: 6555717Abstract: Secondary alcohols, specifically diols and polyols, are dehydroxylated to the corresponding primary alcohols using a homogeneous organometallic ruthenium complex catalyst.Type: GrantFiled: June 20, 2001Date of Patent: April 29, 2003Assignees: E. I. du Pont de Nemours and Company, Brookhaven Science AssociatesInventors: R. Morris Bullock, Marcel Schlaf, Paul Joseph Fagan, Elisabeth M. Hauptman
-
Patent number: 6508753Abstract: A novel phosphine ligand is an enantiomerically enriched compound of formula 5 or the opposite enantiomer thereof, wherein Ar1 and Ar2 represent the same or different aromatic groups of up to 20 C atoms. A transition metal complex of this ligand is useful as a catalyst in stereoselective hydrogenation.Type: GrantFiled: June 4, 2001Date of Patent: January 21, 2003Assignee: Chirotech Technology LimitedInventors: Mark Joseph Burk, Christophe Guillaume Malan
-
Patent number: 6486337Abstract: The present invention concerns novel complexes, suitable in particular for use as catalysts in the asymmetric hydrogenation of ketones, of formula 1 or a diastereoisomer thereof, wherein each Ar is an aromatic or heteroaromatic group of up to 20 atoms; X is halide or carboxylate; and R1, R2, R3, and R4 are independently hydrogen, aryl or alkyl, optionally linked or part of a ring.Type: GrantFiled: March 29, 2001Date of Patent: November 26, 2002Assignee: Chirotech Technology LimitedInventors: Mark Joseph Burk, William Hems, Antonio Zanotti-Gerosa
-
Patent number: 6201160Abstract: Alcohols are prepared by the catalytic hydrogenation of the corresponding carbonyl compounds at elevated temperatures and at superatmospheric pressure in the liquid phase by a process in which the catalyst used contains copper on an SiO2-containing carrier in the presence or absence of one or more of the elements magnesium, barium, zinc and chromium.Type: GrantFiled: November 19, 1996Date of Patent: March 13, 2001Assignee: BASF AktiengesellschaftInventors: Martin Brudermüller, Matthias Irgang, Martin Schmidt-Radde, Franz Merger, Tom Witzel, Detlef Kratz, Eckehard Danz, Arnold Wittwer, Michael Hesse, Manfred Sauerwald, Cristina Freire Erdbrügger
-
Patent number: 6156933Abstract: Process for the selective hydrogenation of alphatic or aromatic substrates under supercritical or near critical conditions. Hydrogenation is effected using a heterogeneous catalyst in a continuous flow reactor containing a supercritical or near critical reaction medium and selectively of product formation is achieved by varying one or more of the temperature, pressure, catalyst and flow rate.Type: GrantFiled: February 18, 1999Date of Patent: December 5, 2000Assignees: Degussa-Huls AG, Thomas Swan & Co. Ltd.Inventors: Martyn Poliakoff, Thomas M. Swan, Thomas Tacke, Martin G. Hitzler, Stephen K. Ross, Stefan Wieland
-
Patent number: 6140545Abstract: In a process for preparing alcohols by gas phase hydrogenation of carboxylic acids or esters thereof at elevated temperature and elevated pressure in the presence of catalysts consisting of or comprising, as hydrogenating components, oxides of main group VI and/or subgroup IV, the hydrogenation is carried outa) at from 250.degree. C. to 400.degree. C. and from 5 bar to 100 bar in the presence ofb) primary or secondary alcohols, the molar hydrogen/alcohol ratio being at most 800.Type: GrantFiled: February 17, 1999Date of Patent: October 31, 2000Assignee: BASF AktiengesellschaftInventors: Martin Merger, Shelue Liang, Rolf Fischer, Joachim Wulff-Doring
-
Patent number: 6054627Abstract: Disclosed are catalysts in powdered form comprising a major amount of the oxides of a first metal selected from copper or zinc, a second metal selected from chromium, molybdenum, tungsten and vanadium, and optionally, a minor amount of the oxide of a promoter metal selected from the group consisting of manganese, barium, zinc, nickel, cobalt, cadmium, iron and any combination thereof provided that the promoter metal is not zinc if the first metal is zinc, wherein the average particle diameter of the powder is from about 6 to about 20 microns; and the particle surface area is from about 20 to about 70 m.sup.2 /g. Also disclosed is a process for preparing such catalysts and a process for hydrogenating aldehydes, ketones, carboxylic acids and carboxylic acid esters with catalysts of the type described.Type: GrantFiled: May 27, 1992Date of Patent: April 25, 2000Assignee: Engelhard CorporationInventors: Deepak S. Thakur, Eugene Palka, Thomas I. Sullivan, Eugene Nebesh, Brian D. Roberts
-
Patent number: 6015927Abstract: Substituted or unsubstituted cyclohexanones are advantageously prepared by hydrogenation of the corresponding phenols in the presence of a palladium-on-carbon catalyst at from 100 to 250.degree. C. and from 1 to 20 bar of hydrogen pressure if the reaction is carried out in the presence of straight-chain, branched or cyclic alkanes having a boiling point at atmospheric pressure of over 70.degree. C. as solvents. This makes it possible to obtain substituted or unsubstituted cyclohexanones in short hydrogenation times and in high yields using low-toxicity, physically problem-free solvents which are easy to handle from a safety point of view.Type: GrantFiled: June 29, 1998Date of Patent: January 18, 2000Assignee: Bayer AktiengesellschaftInventor: Wolfgang Kiel
-
Patent number: 5969196Abstract: For the preparation of 3,5-dimethylphenol by catalytic demethylation of isophorone in the gas phase in the presence of a metal or a metal alloy as catalyst, an isophorone-containing process stream is guided through reaction zones that contain said catalyst, whereby the reactivity of the catalyst varies in the reaction zones and the process stream between these reaction zones is thermostated in zones that do nor contain any catalyst, whereby the residual isophorone is greatly reduced, and the yield of 3,5-dimethylphenol is increased.Type: GrantFiled: April 27, 1998Date of Patent: October 19, 1999Assignee: Rutgers VFT AGInventors: Wolfgang Bergins, Jorg Talbiersky
-
Patent number: 5874649Abstract: The object of the present invention resides in efficiently providing unsaturated alcohol from an .alpha.,.beta.-unsaturated aldehyde.The present invention provides a process for preparing unsaturated alcohol by selectively reducing the aldehyde group of an .alpha.,.beta.-unsaturated aldehyde in the presence of a primary or a secondary alcohol having 2 to 8 carbon atoms using an aluminum alcoholate to produce an unsaturated alcohol such as compounds represented by the formula (III). ##STR1## (wherein R represents an alkyl group having 1 to 3 carbon atoms) wherein the reaction is carried out with addition of a protonic acid.Type: GrantFiled: November 5, 1997Date of Patent: February 23, 1999Assignee: Kao CorporationInventors: Shigeyoshi Tanaka, Shinji Kotachi, Junji Koshino, Junko Yamamoto
-
Patent number: 5817891Abstract: A process for the preparation of alkylphenols of the formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 stand for hydrogen or C.sub.1 -C.sub.8 alkyl, by reaction of an alkylcyclohex-2-en-1-one of the formula II ##STR2## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 have the aforementioned meanings, at temperatures of from 200.degree. to 400.degree. C. and pressures ranging from 0.01 to 50 bar in the presence of palladium-on-.alpha.-Al.sub.2 O.sub.3 catalysts, wherein the catalyst used has a specific surface area (BET) of from 1 to 10 m.sup.2 /g, a pore diameter of from 5 nm to 300 .mu.m and a pore volume of from 0.1 to 0.5 cm.sup.3 /g, from 80 to 100% of the pores having a diameter of from 40 to 400 nm, and also novel palladium-on-.alpha.-Al.sub.2 O.sub.3 catalysts as obtained from a fine-grained alumina powder by steps of molding, pyrolysis and calcination.Type: GrantFiled: September 19, 1996Date of Patent: October 6, 1998Assignee: BASF AktiengesellschaftInventors: Franz Josef Brocker, Peter Trubenbach, Manfred Baumann, Jurgen Schubert
-
Patent number: 5763353Abstract: The present invention provides a hydrogenation catalyst precursor which does not bring about a problem of environmental pollution involved in copper-chromium catalysts and has a high activity, a high durability and a high selectivity as compared with those of conventional copper-iron-aluminum catalysts, a hydrogenation catalyst obtained by reducing the same, and a production process for alcohols using the above hydrogenation catalyst. The hydrogenation catalyst precursor described above comprises copper, iron and aluminum and containing as a principal component a compound oxide of copper, iron and aluminum in which an atomic ratio Cu:Fe:Al is 1:(0.02 to 0.4):(1.0 to 4.0) and which has a copper-aluminum spinel structure.Type: GrantFiled: January 27, 1997Date of Patent: June 9, 1998Assignee: Kao CorporationInventors: Yasuo Kadono, Yasuyuki Hattori, Masamitsu Horio, Fumihiko Nakamura
-
Patent number: 5723694Abstract: Phenols monomethylated or dimethylated in the ortho or para position to the OH group and having the formula ##STR1## can be prepared by reaction of tert-alkyl-substituted phenols of the formula ##STR2## in which at least one free ortho or para position to the OH group is present, in three reaction steps a), b) and c). In a), (II) is reacted with formaldehyde or its polymers and a carboxylic acid of the formulaR.sup.3 --COOH, (III)which gives a mixture of substituted phenols of the formulae ##STR3## In b) the mixture of (IV)/(V) is hydrogenated using catalytically activated hydrogen to give the substituted phenols of the formula ##STR4## which, if m=0, are reacted in c) in the presence of an acid cleavage catalyst with elimination of tert-alkenes to give the methylated phenols of the formula (I).Before or during the hydrogenation, the phenols of the formulae (IV) and (V) can be reacted with the aid of an alcohol of the formulaR.sup.Type: GrantFiled: November 22, 1996Date of Patent: March 3, 1998Assignee: Bayer AktiengesellschaftInventors: Artur Botta, Hans-Josef Buysch
-
Patent number: 5663458Abstract: According to a process for producing .alpha.-phenylethyl alcohol by hydrogenation of acetophenone, which uses a copper-based catalyst containing at least one alkaline earth metal carbonate and/or at least one alkali metal compound, the hydrogenolysis of starting acetophenone is inhibited, and hence the production of ethylbenzene as a by-product is reduced, so that it becomes possible to produce .alpha.-phenylethyl alcohol useful as a starting material for styrene with high selectivity.Type: GrantFiled: November 29, 1995Date of Patent: September 2, 1997Assignee: Sumitomo Chemical Company, Limited.Inventors: Shinya Ito, Takuo Hibi
-
Patent number: 5639922Abstract: A process is described for the selective decomposition of aromatic primary hydroperoxides by contacting a hydroperoxide mixture containing aromatic primary hydroperoxides and aromatic tertiary hydroperoxides obtained by oxidation of alkylaromatic compounds under non-aqueous conditions with an alkali and an organic aromatic carboxylic acid salt.Type: GrantFiled: July 14, 1995Date of Patent: June 17, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Yoichi Ikeda, Motoo Hazama, Nobuhiro Kawara, Maki Okumura, Takanori Ito
-
Patent number: 5614641Abstract: The present invention concerns a process for enantioselective catalytic hydrogenation of the ketone C.dbd.O double bond to a secondary alcohol function, said process using a neutral ruthenium complex as the catalyst and a compound containing a C.dbd.O group as the substrate to be hydrogenated, characterised in that it comprises hydrogenation of the substrate using a diallyl (diphosphino) ruthenium compound with formula ##STR1## where al preferably represents CH.sub.2 CH.dbd.CH.sub.2 or CH.sub.2 C(CH.sub.3).dbd.CH.sub.2,Q represents a hydrocarbon bridge containing at least two catenary carbon atoms and which can contain one to four catenary heteroatoms selected from O, S, N and Si,R.sup.1 to R.sup.4 may be identical or different and each represents a C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.7 cycloalkyl or C.sub.6 -C.sub.12 aryl group.Type: GrantFiled: March 9, 1995Date of Patent: March 25, 1997Assignee: Elf AquitaineInventors: Jean-Pierre Genet, Sylvain Juge, Jean-Alex Laffitte, Catherine Pinel, Serge Mallart
-
Patent number: 5600026Abstract: There is disclosed a process for the production of cresols, including the steps of: (a) conducting oxygenation of cymene with oxygen gas or an oxygen-containing gas, thereby obtaining a solution of oxygenation products containing tertiary and primary hydroperoxides of cymene; (b) reacting the solution of oxygenation products obtained in the step (a) with an organic quaternary ammonium salt and an alkali, or with an organic quaternary ammonium hydroxide, thereby decreasing the content of primary hydroperoxide; (c) subjecting the reaction mixture in the step (b) to decomposition in the presence of a catalyst; and (d) subjecting the decomposition mixture in the step (c) to hydrogenation, thereby obtaining the desired cresols.Type: GrantFiled: February 23, 1995Date of Patent: February 4, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Kiyoshi Ikimi, Yoichi Ikeda, Akira Murakami, Kazushige Okamoto, Tooru Tokumaru, Motoo Hazama
-
Patent number: 5576467Abstract: The present invention relates to a method of preparing an alcohol by reducing a carboxylic acid or a derivative thereof, more particularly, a method of preparing an alcohol by a reduction reaction in the presence of a zirconium-titanium oxide catalyst. A carboxylic acid or a carboxylic acid derivative is converted into a corresponding alcohol by a reduction reaction in the presence of a zirconium-titanium oxide catalyst using an alcohol as a hydrogen source. An alcohol can be prepared in a high yield in the present invention. To be more specific, the method of the present invention can convert a higher fatty acid or a carboxylic acid derivative, which has given a corresponding alcohol in a low yield in the presence of a zirconium catalyst alone, into the corresponding alcohol in a high yield. Further, the reaction can be performed easily, and the product can be easily separated from the catalyst.Type: GrantFiled: June 7, 1995Date of Patent: November 19, 1996Assignee: Japan Tobacco Inc.Inventors: Kyoko Takahashi, Makoto Shibagaki, Hajime Matsushita
-
Patent number: 5495054Abstract: A method for the enantioselective reduction of prochiral ketones using catalytic amounts of tetrahydroindeno[1,2-d][1,3,2] oxazaboroles of formula II is disclosed. ##STR1## The oxazaboroles can be generated in situ from the corresponding cis-1-amino-2-indanols or imino indanols (III) ##STR2## Novel compounds of formulas II and III are also disclosed.Type: GrantFiled: May 31, 1994Date of Patent: February 27, 1996Assignee: Sepracor, Inc.Inventors: Yun Gao, Yaping Hong, Charles M. Zepp
-
Patent number: 5488173Abstract: A cyclohexanone having at least one ortho-hydrogen is selectively methylated in the ortho-position in the vapor phase. High conversion of the selected cyclohexanone and high selectivity in the ortho-position are obtained. The reaction products include 2-methylcyclohexanone, 2,6-dimethylcyclohexanone and 2,6-xylenol.Type: GrantFiled: August 3, 1994Date of Patent: January 30, 1996Inventor: Fey-Long Wang
-
Patent number: 5399791Abstract: There is disclosed a process for the production of cresols, including the steps of: (a) conducting oxygenation of cymene with oxygen gas or an oxygen-containing gas without any addition of an alkali, thereby obtaining a solution of oxygenation products containing tertiary and primary hydroperoxides of cymene; (b) washing the solution of oxygenation products obtained in step (a) with an aqueous alkali solution at a temperature in the range of from 10.degree. to 95.degree. C.; (c) subjecting the solution of oxygenation products obtained in step (b) to hydrogenation at a temperature in the range of from 60.degree. to 100.degree. C. to decrease the content of primary hydroperoxide in such a manner that the weight ratio of primary hydroperoxide to tertiary hydroperoxide is not greater than 1/25 (w/w); (d) subjecting the solution treated in step (c) to decomposition in the presence of a catalyst; and (e) subjecting the solution treated in step (d) to hydrogenation to obtain cresols.Type: GrantFiled: February 25, 1994Date of Patent: March 21, 1995Assignee: Suitomo Chemical Company, LimitedInventors: Kiyoshi Ikimi, Yoichi Ikeda, Akira Murakami, Kazushige Okamoto, Tooru Tokumaru, Motoo Hazama
-
Patent number: 5227538Abstract: A process is provided for the catalytic asymmetric reduction of ketones to provide alcohol reaction products which are enriched in one enantiomer. The asymmetric reduction is accomplished utilizing an achiral metal precatalyst in combination with an optically active additive.Type: GrantFiled: November 14, 1991Date of Patent: July 13, 1993Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Alberto Gutierrez, Robert B. Grossman
-
Patent number: 5220020Abstract: A process is provided whereby organic carbonyl substrates, including esters, lactones, ketones, amides and imides are reduced in a reaction with a silane reducing reagent and a catalyst. Exemplary catalysts include metal alkoxides and metal aryloxides.Type: GrantFiled: November 14, 1991Date of Patent: June 15, 1993Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Alberto Gutierrez, Scott C. Berk, Kristina A. Kreutzer
-
Patent number: 5180871Abstract: A process for producing a phenol from the steps of:(a) partially hydrogenating a benzene, followed by separating the reaction mixture into respective components of a cyclohexene, a cyclohexane and a benzene;(b) oxidizing or hydrating the separated a cyclohexene into oxygen-containing compounds of a cyclohexane;(c) dehydrogenating the oxygen-containing compounds of a cyclohexane into a phenol;(d) dehydrogenating the cyclohexane separated in step (a) to convert the cyclohexane into a benzene; and(e) returning a part or all of hydrogen formed in steps (c) and (d) back to step (a).Type: GrantFiled: February 24, 1992Date of Patent: January 19, 1993Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Fujihisa Matsunaga, Hiroshi Fukuhara, Mitsuki Yasuhara
-
Patent number: 5017729Abstract: Phenol is produced in a recycle manner by (a) reacting benzene with propylene to synthesize cumene, (b) oxidizing the cumene of step (a) into cumene hydroperoxide, (c) acid cleaving cumene hydroperoxide into phenol and acetone, (d) hydrogenating the acetone of step (c) into isopropanol, (e) dehydrating the isopropanol of step (d) into propylene, and (f) recycling the propylene of step (e) to step (a). It is also possible to take propylene from step (e). The acetone by-product produced upon preparation of phenol is converted into propylene which is useful by itself for any other uses or recycled to the phenol producing process.Type: GrantFiled: September 5, 1989Date of Patent: May 21, 1991Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Hiroshi Fukuhara, Fujihisa Matsunaga
-
Patent number: 4933507Abstract: Phenol is produced by dehydrogenating cyclohexenone through a vapor-phase reaction in the presence hydrogen using a solid-phase catalyst having platinum and alkali metal carried on a support.Type: GrantFiled: November 29, 1988Date of Patent: June 12, 1990Assignee: Mitsui Petrochemical Industries, Inc.Inventors: Satoshi Inoki, Yasushi Nakashima, Fujihisa Matsunaga
-
Patent number: 4929762Abstract: A phenol and/or a cyclohexanone is prepared by dehydrogenation of cyclohexenone and/or a cyclohexenol in liquid phase under the presence of a solid catalyst comprising a platinum-group metal loaded on a carrier. The solid catalyst comprises a carrier selected from activated carbon and hydrotalcites.Type: GrantFiled: March 2, 1989Date of Patent: May 29, 1990Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Fujihisa Matsunaga, Hiroshi Fukuhara
-
Patent number: 4769501Abstract: There is disclosed a process for producing an alkylphenol comprising reacting a phenol with an aldehyde and hydrogen in the presence of (a) an alkaline or alkaline earth metal catalyst selected from a hydroxide of an alkaline metal, hydroxide of an alkaline earth metal, a carbonate of an alkaline metal, and a hydrogencarbonate of an alkaline metal and (b) a hydrogenation catalyst. By the use of the process, the alkylphenols can be produced in good yield in one stage method.Type: GrantFiled: July 21, 1987Date of Patent: September 6, 1988Assignee: Idemitsu Petrochemical Co., Ltd.Inventor: Masahiro Iwahara
-
Patent number: 4731491Abstract: Liquefaction of lignin by hydrogenolysis in the presence of a catalytic composition of metal sulfides which are prepared in situ and in the presence of a lower aliphatic alcohol affords substantially increased yields of monophenols. When methanol is used in the presence of a catalyst which is a mixture of the sulfides of divalent iron, copper, and tin the total monophenols can be as high as 65% with the total cresols being about 45%. Phenol, which is used as a liquefying solvent, can itself be formed in good yield when lignin tar is used as the liquefying solvent. This affords the opportunity of conducting the liquefaction in a continuous fashion using two stages of reaction.Type: GrantFiled: January 22, 1986Date of Patent: March 15, 1988Assignee: UOP Inc.Inventors: Peter Urban, Dusan J. Engel
-
Patent number: 4728671Abstract: The present invention relates to a process for producing alcohols comprising hydrogenating compounds selected from the group consisting of acids, esters and aldehydes under sufficient hydrogen pressure and temperature in the presence of a catalyst comprising a copper chromite first component and a second component consisting essentially of copper deposited on a support.Type: GrantFiled: April 25, 1985Date of Patent: March 1, 1988Assignee: Oleofina, S.A.Inventor: Herve Hinnekens
-
Patent number: 4716252Abstract: Bis-hydroxyphenyl-n-alkanes are prepared by contacting dicarboxylic acids or dicarboxylic acid derivatives with fluorine-containing organic sulphonic acids, where appropriate with the addition of a phenolic compound, and converting the alkanediones, which are thus obtainable, into bis-hydroxyphenyl-n-alkanes by hydrogenation and, where appropriate, an additional ether cleavage. The invention also relates to new bis-hydroxyphenyl-n-alkanes and to new alkanediones.Type: GrantFiled: July 28, 1986Date of Patent: December 29, 1987Assignee: Bayer AktiengesellschaftInventors: Rudolf Wagner, Kurt Halcour, Hans-Rudolf Dicke, Volker Eckhardt
-
Patent number: 4628130Abstract: The invention has as an object the production of alcohols by hydrogenolysis of carboxylic acid esters, under hydrogen pressure, in the presence of a catalyst resulting from the incorporation of at least one compound of at least one metal from the group consisting of germanium, tin and lead to Raney nickel or to a nickel-containing carrier. The reaction is preferably conducted at a temperature from 180.degree. to 330.degree. C. and under a pressure from 1 to 10 MPa.Type: GrantFiled: August 8, 1985Date of Patent: December 9, 1986Assignee: Institut Francais du PetroleInventors: Jean-Paul Bournonville, Jean-Pierre Candy, Gil Mabilon
-
Patent number: 4600799Abstract: 2,3,6-Trimethylhydroquinone is prepared by catalytic hydrogenation of 2,3,6-trimethylquinone with hydrogen in the presence of a solvent by a continuous process in which the reaction is carried out over a platinum/alumina catalyst.Type: GrantFiled: February 7, 1985Date of Patent: July 15, 1986Assignee: BASF AktiengesellschaftInventors: Franz J. Broecker, Peter Tavs, Harald Laas, Wolf-Karlo Aders
-
Patent number: 4584417Abstract: p-Alkylphenols such as p-cresol are prepared by the reaction of p-hydroxyalkylphenols with water and oxygen in the presence of at least one oxide of a Group II metal having an atomic weight less than 70, preferably zinc oxide. At least part of the p-hydroxyalkylphenol contains a p-hydroxymethyl group, and it is preferably entirely p-hydroxybenzyl alcohol. The reaction temperature is about 350.degree.-550.degree. C.Type: GrantFiled: February 6, 1984Date of Patent: April 22, 1986Assignee: General Electric CompanyInventor: John J. Talley
-
Patent number: 4538009Abstract: Substituted phenols of the general formula I ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each hydrogen or an aliphatic or aromatic hydrocarbon radical, are prepared by dehydrogenating a cyclic alcohol of the general formula II ##STR2## or a cyclic ketone of the general formula III ##STR3## where one of the broken lines can be an additional C-C bond, in the gas phase at from 150.degree. to 380.degree. C. over a supported noble metal catalyst, by a process in which the dehydrogenation catalyst used is palladium or platinum on an aluminum spinel carrier, in particular an aluminum spinel which has a BET specific surface area of from 5 to 150 m.sup.2 /g or, for the dehydrogenation of cyclohexenones, preferably from 10 to 50 m.sup.2 /g. Particularly suitable aluminum spinels are those which, in addition to aluminum, contain magnesium, zinc, cobalt or nickel.Type: GrantFiled: April 12, 1984Date of Patent: August 27, 1985Assignee: BASF AktiengesellschaftInventors: Norbert Goetz, Harald Laas, Peter Tavs, Leopold Hupfer, Karl Baer
-
Patent number: 4503271Abstract: A process for the production of p-vinyl phenol by the dehydrogenation of p-ethyl phenol in a gaseous phase in the presence of a catalyst and a diluent wherein the dehydrogenation of p-ethyl phenol is effected with phenol and/or p-cresol being present in the reaction system in an amount of 5 to 50 wt % of the amount of p-ethyl phenol.Type: GrantFiled: September 2, 1983Date of Patent: March 5, 1985Assignee: Maruzen Oil Co., Ltd.Inventors: Hiroshi Fujiwara, Hatsutaro Yamazaki, Kazuo Ozawa
-
Patent number: 4503249Abstract: Iron (II) hexacyanocobaltate and ruthenium (III) hexacyanocobaltate have been found to be useful in the catalytic hydrogenation of organic materials.Type: GrantFiled: September 21, 1982Date of Patent: March 5, 1985Assignee: Phillips Petroleum CompanyInventors: Gerhard P. Nowack, Marvin M. Johnson, Donald C. Tabler
-
Patent number: 4480140Abstract: Phenols alkylated in the ortho and/or para positions are produced in good yields and in the absence of isomers from phenolic compounds having at least two alkylateable ortho-ortho or ortho-para positions open. The phenolic compound is first partially chlorinated or brominated and the desired halogenated phenol having at least one open position ortho or para is reacted with an aldehyde having one to four carbon atoms and a secondary non-aromatic amine. The reaction is conducted in the liquid phase with a stoichiometric amount of the phenolic compound and stoichiometric or excess of stoichiometric amounts of the aldehyde and the amine. The reaction is performed at a temperature of from about 0.degree. C. to about 100.degree. C. to produce an aminoalkylated halogenated phenolic compound. This aminoalkylated halogenated phenolic compound is contacted with hydrogen in the presence of a metal catalyst at a temperature of about 100.degree. C. to about 175.degree. C.Type: GrantFiled: March 16, 1983Date of Patent: October 30, 1984Assignee: Koppers Company, Inc.Inventor: Gerd Leston