Group Viii Metal Containing Catalyst Utilized Patents (Class 564/422)
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Patent number: 6479704Abstract: The present invention relates to an improved for the hydrogenation of an immiscible mixture of an organic reactant in water. The immiscible mixture can result from the generation of water by the hydrogenation reaction itself or, by the addition of, water to the reactant prior to contact with the catalyst. The improvement resides in effecting the hydrogenation reaction in a monolith catalytic reactor from 100 to 800 cpi, at a superficial velocity of from 0.1 to 2 m/second in the absence of a cosolvent for the immiscible mixture. In a preferred embodiment, the hydrogenation is carried out using a monolith support which has a polymer network/carbon coating onto which a transition metal is deposited.Type: GrantFiled: April 20, 2001Date of Patent: November 12, 2002Assignee: Air Products and Chemicals, Inc.Inventors: Andrew Francis Nordquist, Frederick Carl Wilhelm, Francis Joseph Waller, Reinaldo Mario Machado
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Patent number: 6472564Abstract: Toluylene diisocyanate is produced by nitration of toluene toy yield dinitrotoluene, hydrogenation of the dinitrotoluene, optionally in the presence of a solvent or diluent, to yield a crude solution of toluylene diamine and reaction water, processing the crude solution of toluylene diamine and water to yield an intermediate mixture of toluylene diamine and water wherein the processing is interrupted to result in a water content of about 1-40% by weight, preferably about 2-10% by weight of the intermediate mixture, transporting this intermediate mixture from a first production facility to a second production facility, whereat the intermediate mixture of TDA and water is completed to yield dry toluylene diamine of commercial quality, and followed by phosgenation of the toluylene diamine to give toluylene diisocyanate. It is optional to additionally process the dry toluylene diamine prior to phosgenation.Type: GrantFiled: September 8, 1998Date of Patent: October 29, 2002Assignee: Bayer AktiengesellschaftInventors: Klaus Biskup, Berthold Keggenhoff
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Publication number: 20020151751Abstract: A process for the preparation of substituted amines by catalytic hydrogenation of substituted organic nitro compounds with hydrogen or hydrogen-containing gas mixtures in the presence of a shaped Raney catalyst as the hydrogenation catalyst, wherein the Raney catalyst is in the form of hollow bodies or shell-activated tablets. Nickel, cobalt, copper, iron, platinum, palladium or ruthenium are preferably used as catalytically active constituents.Type: ApplicationFiled: January 16, 2002Publication date: October 17, 2002Inventors: Daniel Ostgard, Monika Berweiler, Stefan Roeder
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Patent number: 6423872Abstract: Nitrated aromatic compounds are continuously catalytically hydrogenated into their corresponding aromatic amines in the presence of an effective amount of a nickel or nickel/aluminum catalyst, the nickel catalyst being essentially devoid of aluminum values and the nickel/aluminum catalyst containing up to 5.5% by weight of aluminum values; the subject hydrogenation is thus conducted under conditions such as to limit the formation of nickel aluminates and the nickel or nickel/aluminum catalyst is continuously catalytically active for at least three days.Type: GrantFiled: March 28, 2001Date of Patent: July 23, 2002Assignee: Rhodia ChimieInventor: Philippe Marion
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Patent number: 6414192Abstract: The invention provides a process for preparing 4-aminodiphenylamine, an important starting product for synthesizing antioxidants and stabilizers in the rubber and polymer industry, by hydrogenating nitrosobenzene with hydrogen in the presence of a proton acid as catalyst and in the presence of a hydrogenating catalyst, optionally in the presence of an inert organic solvent and thermally decomposing the 4-ADPA ammonium salt produced in this way, wherein 4-ADPA is obtained. 4-aminodiphenylamine is produced in good yields and high purity by the process according to the present invention. Furthermore, no effluent is produced, which makes the process particularly economic and ecological.Type: GrantFiled: November 6, 2001Date of Patent: July 2, 2002Assignee: Bayer AktiengesellschaftInventors: Michael Schelhaas, Carl Casser, Dietmar Bielefeldt, Pieter Ooms, Joachim Haider, Manfred Jautelat, Christian Laue, Henry Giera
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Patent number: 6403833Abstract: The present invention provides a single step process for the preparation of p-aminophenol by hydrogenation of nitrobenzene in presence of an aqueous acid over a mono or bimetallic nickel catalyst at a temperature in the range of 80-120° C. for a period of 1 to 4 hrs. The resulting reaction mixture is extracted with an organic solvent like ethyl acetate, cyclohexane or toluene to separate the aqueous layer containing PAP and neutralizing it with ammonia solution to recover the solid p-aminophenol.Type: GrantFiled: January 30, 2001Date of Patent: June 11, 2002Assignee: Council of Scientific and Industrial ResearchInventors: Chandrashekhar Vasant Rode, Manisha Jagdeeshrao Vaidya, Raghunath Vitthal Chaudhari
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Patent number: 6395933Abstract: The invention is directed to a method of producing one or more 4-aminodiphenylamine intermediates comprising the steps of bringing an aniline or aniline derivative and nitrobenzene into reactive contact; and reacting the aniline and nitrobenzene in a confined zone at a suitable time and temperature, in the presence of a mixture comprising a strong base and a suitable phase transfer catalyst. Certain phase transfer catalysts may also function as the strong base.Type: GrantFiled: July 23, 2001Date of Patent: May 28, 2002Assignee: Flexsys America, L.P.Inventors: Ralph Dale Triplett, II, Roger Keranen Rains
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Patent number: 6395934Abstract: Raney nickel catalysts obtainable by a process in which the melt of an alloy comprising 50 to 94 wt. % aluminum, 10 to 50 wt. % nickel, 0 to 20 wt. % iron, 0 to 15 wt. % cerium, cerium mixed metal, vanadium, niobium, tantalum, chromium, molybdenum or manganese and, optionally, further glass-forming elements is allowed to solidify rapidly with a cooling rate of >104 K/s and the rapidly solidified alloy is then subjected to a treatment with organic or inorganic bases are described. A process for the preparation of the Raney nickel catalysts mentioned and their use in the hydrogenation of organic compounds, in particular aromatic nitro compounds, are furthermore described.Type: GrantFiled: July 19, 2000Date of Patent: May 28, 2002Assignee: Bayer AktiengesellschaftInventors: Gerhard Wegener, Eckart Waldau, Bernd Pennemann, Bodo Temme, Hans Warlimont, Uta Kühn
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Patent number: 6350911Abstract: The invention relates to a process for the preparation of amines by hydrogenation of nitro compounds, which comprises carrying out the hydrogenation in a vertical reactor whose length is greater than its diameter, having a downward-facing jet nozzle arranged in the upper region of the reactor through which the starting materials and the reaction mixture are fed in, and having an outlet at any desired point of the reactor, through which the reaction mixture is fed back to the jet nozzle in an external circuit by means of a conveying means, and having flow reversal in the lower region of the reactor.Type: GrantFiled: June 11, 2001Date of Patent: February 26, 2002Assignee: BASF AktiengesellschaftInventors: Michael Sander, Ulrich Penzel, Hans Volkmar Schwarz, Eckhard Ströfer, Dieter Stützer, Jörn Müller, Markus Maurer, Peter Zehner, Ekkehard Schwab, Ralf Böhling, Dominic Vanoppen
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Publication number: 20020006862Abstract: A novel precious metal doped porous metal catalyst is disclosed. The precious metal is present in from 0.01 to 1.5 weight percent and distributed throughout the particles of porous metal to provide a surface to bulk ratio distribution of not greater than 60. The present invention is further directed to a process of forming said doped catalyst and to improved processes of catalytic hydrogenation of organic compounds.Type: ApplicationFiled: July 6, 2001Publication date: January 17, 2002Inventor: Stephen Raymond Schmidt
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Publication number: 20010027257Abstract: Nitrated aromatic compounds are continuously catalytically hydrogenated into their corresponding aromatic amines in the presence of an effective amount of a nickel or nickel/aluminum catalyst, the nickel catalyst being essentially devoid of aluminum values and the nickel/aluminum catalyst containing up to 5.5% by weight of aluminum values; the subject hydrogenation is thus conducted under conditions such as to limit the formation of nickel aluminates and the nickel or nickel/aluminum catalyst is continuously catalytically active for at least three days.Type: ApplicationFiled: March 28, 2001Publication date: October 4, 2001Inventor: Philippe Marion
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Patent number: 6294696Abstract: A process for hydrogenating organic compounds containing at least one function selected from aldehyde, ketone, ester, acid and nitro functions and/or containing an aromatic group is carried out in the presence of a catalyst comprising at least one support, at least one metal from group VIII of the periodic table and at least one additional element M selected from the group formed by germanium, tin, lead, rhenium, gallium, indium, gold, silver and thallium. The process is characterized in that the catalyst is prepared using a process in which said metal M is introduced in an aqueous solvent, in the form of at least one organometallic compound comprising at least one carbon-M bond.Type: GrantFiled: October 30, 1998Date of Patent: September 25, 2001Assignee: Institut Francais du PetroleInventors: Blaise Didillon, Fabienne Le Peltier
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Patent number: 6268536Abstract: A process for the conversion of a picrate salt, preferably ammonium pricrate, to picric acid by acidifying the picrate salt in a two phase liquid system. One phase is an aqueous phase which contains an acid which is effective for acidifying ammonium picrate to picric acid and the other phase is an organic solvent phase in which the picric acid is soluble.Type: GrantFiled: December 6, 1999Date of Patent: July 31, 2001Inventors: Duane A. Goetsch, Kym B. Arcuri
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Patent number: 6245943Abstract: A disclosed method of preparing p-phenylenediamine includes the steps of: reacting urea and nitrobenzene with a base in the presence of a polar solvent to yield 4-nitrosoaniline and 4-nitroaniline; and subsequently, diluting the resulting mixed solution in an alcohol and performing hydrogenation using a catalyst, thereby providing highly pure p-phenylenediamine destitute of an ortho- or meta-isomer as a byproduct. The method has some advantages in that: the process is simplified in such a manner that the hydrogenation is performed in the presence of the hydrogenation catalyst in a single reactor (i.e., one pot) without a need of isolating 4-nitrosoaniline or purifying the product; inexpensive urea and an alkali base are used to reduce the production cost; and 4-nitrosoaniline is formed as an intermediate to yield p-phenylenediamine with a high selectivity, thereby requiring no purification process after isolation of the product.Type: GrantFiled: August 16, 2000Date of Patent: June 12, 2001Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Young J. Joo, Jin Eok Kim, Jeong Im Won
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Patent number: 6242649Abstract: A continuous process for the preparation of aromatic di- and/or polyamines by catalytic hydrogenation of the corresponding aromatic di- and/or polynitro compounds with hydrogen, characterized in that, in a reactor with a catalytic fixed bed or trickle bed at a pressure between 5 and 100 bar and a reaction temperature of from 100 to 220° C. a) the aromatic di- and/or polynitro compounds, optionally in the presence of a solvent, are introduced into a product stream comprising essentially recycled hydrogenated product, water and hydrogen, and b) a part of the product stream is removed continuously from the reactor system.Type: GrantFiled: April 7, 2000Date of Patent: June 5, 2001Assignee: Bayer AktiengesellschaftInventors: Heiko Beckhaus, Reinhard Langer
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Patent number: 6204413Abstract: The invention relates to a process for the preparation of specific salts of 1-substituted 2,4-diaminobenzenes by catalytic hydrogenation of 1-substituted 2,4-dinitrobenzenes and addition of the reaction product obtained after the hydrogenation and separated from the catalyst to an aqueous solution of an acid.Type: GrantFiled: April 11, 2000Date of Patent: March 20, 2001Assignee: Bayer AktiengesellschaftInventors: Lars Rodefeld, Alexander Klausener, Horst Behre
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Patent number: 6140539Abstract: In a process for preparing amines, in which at least one compound containing at least one nitro group is reacted with hydrogen in the presence of a supported catalyst comprising, as catalytically active metal, nickel, if desired together with at least one metal of transition group I, V, VI and/or VIII, the reduced and stabilized supported catalyst comprises nickel crystallites having a bimodal nickel crystallite size distribution having maxima at 30-80 Angstrom and 81-150 Angstrom on a support comprising ZrO.sub.2, ZrO.sub.2 --HfO.sub.2 and/or SiO.sub.2 --ZrO.sub.2 and/or SiO.sub.2 --ZrO.sub.2 --HfO.sub.2 and in the reduced and passivated state has a nickel content of 60-80 percent by mass, an SiO.sub.2 content of 0-20 percent by mass, a ZrO.sub.2 content of 0-40 percent by mass, an HfO.sub.2 content of 0-4 percent by mass and after further reduction for one hour at 100.degree. C. has a degree of reduction of at least 70%.Type: GrantFiled: March 3, 2000Date of Patent: October 31, 2000Assignee: BASF AktiengesellschaftInventors: Michael Sander, Dietmar Peisker, Klaus Werner, Holger Braunsberg, Gunter Georgi, Ulrich Penzel
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Patent number: 6096924Abstract: One object of the invention is a process for the catalytic hydrogenation of aromatic nitro compounds in solution or in melt in the presence of hydrogen and at least one noble metal catalyst, nickel catalyst or cobalt catalyst, in which process a catalytic amount of at least one vanadium compound is present, wherein the vanadium has the oxidation state 0, II, IV or V. It has been found that in the catalytic hydrogenation of aromatic nitro compounds the accumulation of hydroxylamines can be almost completely prevented by the addition of catalytic amounts of vanadium compounds, which usually results in concentrations of <1% hydroxylamine. The resulting hydrogenated products are whiter (purer) than those obtained without the addition of the vanadium compound because almost no azo or azoxy compounds are obtained. The hydrogenation, in particular the final phase, proceeds faster than without said addition. Accordingly, substantial advantages with respect to quality constancy and economy are obtained.Type: GrantFiled: November 13, 1997Date of Patent: August 1, 2000Assignee: Novartis AGInventors: Martin Studer, Peter Baumeister
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Patent number: 6077974Abstract: Amino-halogenophenyl alkyl thioethers prepared in an advantageous manner by catalytic reduction of the corresponding nitro compound by the nitro compound being continuously hydrogenated with hydrogen in the presence of a supported noble-metal catalyst.Type: GrantFiled: July 21, 1999Date of Patent: June 20, 2000Assignee: Bayer AktiengesellschaftInventor: Wolfgang Kiel
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Patent number: 6057479Abstract: This invention relates to a process for preparing indan derivatives and comprises a process for preparing cis-1-amino-2-indanol by treating (.+-.)indan-1,2-diol and/or its 2-formate derivative with specific microbes to give optically active 2-hydroxy-1-indanone, converting the optically active 2-hydroxy-1-indanone to its oxime, and treating the oxime with hydrogen or a hydrogen donor in the presence of a heterogeneous hydrogenation catalyst, a process for preparing optically active 2-hydroxy-1-indanone and/or optically active indan-1,2-diol by treating (.+-.)indan-1,2-diol and/or its 2-formate derivative with specific microbes, and a process for preparing cis-1-amino-2-indanol by treating the oxime of 2-hydroxy-1-indanone with hydrogen or a hydrogen donor in the presence of a heterogeneous hydrogenation catalyst.Type: GrantFiled: July 9, 1998Date of Patent: May 2, 2000Assignee: Nippon Steel Chemical Co., Ltd.Inventors: Shuichi Mitamura, Yasuhisa Asano, Tamejiro Hiyama, Hiroshi Kajiro
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Patent number: 6049008Abstract: Shaped catalyst compositions are disclosed comprising (i) at least one metal selected from the group consisting of copper, manganese, zinc, nickel, cobalt and iron, (ii) calcium silicate and (iii) at least one clay material. Also disclosed are a process for preparing the foregoing shaped compositions and a process for hydrogenating aldehydes, ketone, carboxylic acids, carboxylic acid esters and nitro aroniate compounds using these shaped catalysts.Type: GrantFiled: July 6, 1999Date of Patent: April 11, 2000Assignee: Engelhard CorporationInventors: Brian D. Roberts, William J. Carrick, Deepak S. Thakur
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Patent number: 6043394Abstract: A process for the production of aromatic amines by catalylic hydrogenation.Type: GrantFiled: June 4, 1999Date of Patent: March 28, 2000Assignee: Bayer AktiengesellschaftInventors: Reinhard Langer, Hans-Josef Buysch, Manfred Gallus, Burkhard Lachmann, Franz-Ulrich von Gehlen
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Patent number: 6040481Abstract: A method for hydrogenating aromatic nitro compounds by reacting at least one aromatic nitro compound with hydrogen in two adiabatically operated fixed-bed catalytic reactors arranged in series, wherein one part of the reaction mixture from the first reactor is recirculated therein while the other part is fed into the second reactor.Type: GrantFiled: November 12, 1998Date of Patent: March 21, 2000Assignee: Rhodia ChimieInventors: Bernard Chambost, Philippe Marion, Corinne Mathieu
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Patent number: 6034276Abstract: Disclosed is an improved process for preparing 1-chloro-2,4-diaminobenzene by the selective hydrogenation of 1-chloro-2,4-dinitro-benzene wherein the hydrogenation is carried out in the presence of a modified Raney nickel catalyst containing about 70 to 95 weight percent nickel, about 4 to 10 weight percent aluminum, about 0.1 to 4 weight percent molybdenum, and from 0 to about 20 weight percent cobalt. The 1-chloro-2,4-diaminobenzene is useful as an intermediate for disperse dyes and for color photography.Type: GrantFiled: March 22, 1999Date of Patent: March 7, 2000Assignee: Eastman Chemical CompanyInventors: Robert Joseph Maleski, Edward Tipton Mullins
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Patent number: 5990354Abstract: Ammonium picrate, Explosive "D", is converted to picric acid, which is then converted to triaminophenol by the conversion of the aromatic nitro groups to amino groups. The triaminophenols are then converted to triaminobenzenes by the removal of the hydroxyl groups and the triaminobenzenes are converted to m-phenylenediamine, aniline, and primary aliphatic amines by the removal of amino groups.Type: GrantFiled: November 17, 1998Date of Patent: November 23, 1999Assignee: Gradient TechnologyInventors: Duane A. Goetsch, Kym B. Arcuri
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Patent number: 5877350Abstract: Aromatic amines are produced by hydrogenation of the appropriate aromatic nitro compounds in the vapour phase on fixed catalysts. The catalysts contain supported metals active in hydrogenation, the reaction is carried out under adiabatic conditions at a pressure of from 1 to 30 bar, an inlet temperature of from 200.degree. to 400.degree. C. and a maximum catalyst temperature of 500.degree. C.Type: GrantFiled: August 4, 1995Date of Patent: March 2, 1999Assignee: Bayer AktiengesellschaftInventors: Reinhard Langer, Hans-Josef Buysch, Ursula Pentling, Paul Wagner
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Patent number: 5872300Abstract: 2-Amino-6-chlorophenyl-alkylsulfanes are prepared in a particularly advantageous manner by hydrogenating 2-chloro-6-nitrophenyl-alkylsulfanes catalytically in the presence of a solvent without the addition of a further sulfur compound, and the novel compound 2-amino-6-chlorophenyl-isopropylsulfane is provided.Type: GrantFiled: November 14, 1996Date of Patent: February 16, 1999Assignee: Bayer AktiengesellschaftInventors: Ferdinand Hagedorn, Wolfgang Kiel, Helmut Fiege
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Patent number: 5849947Abstract: Toluylene diisocyanate is produced by nitration of toluene toy yield dinitrotoluene, hydrogenation of the dinitrotoluene, optionally in the presence of a solvent or diluent, to yield a crude solution of toluylene diamine and reaction water, processing the crude solution of toluylene diamine and water to yield an intermediate mixture of toluylene diamine and water wherein the processing is interrupted to result in a water content of about 1-40% by weight, preferably about 2-10% by weight of the intermediate mixture, transporting this intermediate mixture from a first production facility to a second production facility, whereat the intermediate mixture of TDA and water is completed to yield dry toluylene diamine of commercial quality, and followed by phosgenation of the toluylene diamine to give toluylene diisocyanate. It is optional to additionally process the dry toluylene diamine prior to phosgenation.Type: GrantFiled: August 1, 1996Date of Patent: December 15, 1998Assignee: Bayer AktiengesellschaftInventors: Klaus Biskup, Berthold Keggenhoff
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Patent number: 5808157Abstract: Aromatic amines are produced by hydrogenation of the associated aromatic nitro compounds in the gas phase over fixed catalysts. The catalysts contain active hydrogenation metals on supports. The reaction is conducted at a pressure of 2-50 bar and at a temperature in the range 250.degree.-500.degree. C. under adiabatic conditions. A circulating gas is passed over the catalyst, which circulating gas contains 3-150 moles of hydrogen, 2-100 moles of the amino groups to be formed per mole of nitro groups, and 2 to 6 moles of water per amino group equivalent. The amine and water formed, as well as a purification stream, are separated from the circulating gas. Thereafter the circulating gas is enriched with volatilised aromatic nitro compound and fresh hydrogen and recycled.Type: GrantFiled: August 4, 1995Date of Patent: September 15, 1998Assignee: Bayer AktiengesellschaftInventors: Reinhard Langer, Hans-Josef Buysch, Paul Wagner, Ursula Pentling
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Patent number: 5728880Abstract: Amine mixtures generated during the production of diaminotoluene by hydrogenating dinitrated aromatic compounds are treated to separate high boiling materials from the desired amine products. In this process, any water of reaction and any solvent are first removed from the diaminotoluene isomer mixture (TDA mixture). The low-boiling TDA isomers are then separated using a TDA isomer distillation column. In the process of the present invention, the bottom phase remaining after the initial distillation contains a mixture of m-TDA and high-boiling materials. This bottom phase is separated and concentrated until the high-boiling material content is from approximately 25 to 60 wt. %. This concentrated bottom phase is then mixed with o-TDA in a ratio of 1:1 to 1:5 and a m-/o-TDA mixture is removed by distillation. The m-/o-TDA mixture thus recovered is then returned to the TDA isomer distillation column.Type: GrantFiled: February 25, 1997Date of Patent: March 17, 1998Assignee: Bayer AktiengesellschaftInventors: Heiko Beckhaus, Harro Witt, Uwe-Jens Zarnack, Gerd Greger
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Patent number: 5714634Abstract: This invention relates to an improved process for storing and transporting toluenediamine, particularly for long term storage or storage in large containers, e.g., shipboard containers. The improvement in the process resides in substantially reducing the melting or freezing point of anhydrous toluenediamine obtained by the fractional distillation of a reaction product generated by the hydrogenation of dinitrotoluene. Such melting point reduction is accomplished by maintaining a water concentration in the toluenediamine in an amount of from 5 to 15% by weight under molten conditions for storage and transport. Preferably the level of water maintained in the toluenediamine is from about 7 to 10% by weight.Type: GrantFiled: June 25, 1996Date of Patent: February 3, 1998Assignee: Air Products and Chemicals, Inc.Inventors: Andrew James Casale, Richard Van Court Carr
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Patent number: 5712414Abstract: The present invention relates to a process for the preparation of hydroxycarboxylic acid amides of the general formula (1): ##STR1## in which R.sup.1 and R.sup.2 are identical or different and are hydrogen, halogen, cyano, a linear or branched alkyl, alkenyl, alkynyl or alkoxy group having 1 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a cycloalkyl group having 6 to 12 carbon atoms or an aryl group having 6 to 12 carbon atoms, R.sup.3 is hydrogen or a linear or branched alkyl group having 1 to 4 carbon atoms, R.sup.4 is hydrogen or a linear or branched alkyl group having 1 to 6 carbon atoms, or R.sup.3 and R.sup.4, together with the carbon atom to which they are attached, form a five- or six-membered cycloalkane ring, and n is an integer from 1 to 12, wherein an aniline of the general formula (2) ##STR2## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.Type: GrantFiled: July 10, 1996Date of Patent: January 27, 1998Assignee: Hoechst AktiengesellschaftInventors: Andreas Dierdorf, Theodor Papenfuhs
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Patent number: 5693862Abstract: The present invention is directed to a process for transporting toluenediamine (TDA) from a first site to a second site. The process of the invention comprises the steps of (a) providing a molten mass of TDA isomers at the first site; (b) cooling the molten mass to a temperature below the melting point, the molten mass thereby forming flowable particles of solid TDA in an inert gas; (c) providing an airtight storage vessel lined with a chemically inert liner; (d) storing the flowable particles of solid TDA in the lined storage vessel; (e) charging the storage vessel with inert gas; (f) transporting the storage vessel from the first site to the second site; and (g) remelting the TDA flowable particles in inert gas with TDA liquid that is superheated above the melting point to produce a molten TDA isomer mixture in inert gas having substantially the same isomer ratio as that of the molten mass.Type: GrantFiled: December 18, 1996Date of Patent: December 2, 1997Assignee: Arco Chemical Technology, L.P.Inventors: Majid Keyvani, Rekha Menon, James L. Meyer, Thomas W. Offill
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Patent number: 5665756Abstract: Novel aminoalkyloximes of the formula ##STR1## wherein: a. X is hydrogen, loweralkyl, loweralkoxy, halogen, trifluoromethyl, or a group of the formula ##STR2## wherein Y is hydrogen or loweralkyl, and p is 1 or 2; b. A is a group of the formula ##STR3## c. R.sup.1 and R.sup.2 are independently hydrogen or lowerakyl; and d. m is 2 to 6 and n is 0, or 2 to 6, inclusive, serotonin reuptake inhibitors, useful for treating depression and obsessive compulsive disorders are described. Also described are precursors of and processes for the preparation of such aminoakyloximes.Type: GrantFiled: August 3, 1994Date of Patent: September 9, 1997Assignee: Hoechst Marion Roussel, Inc.Inventors: Gregory M. Shutske, Brian S. Freed, John D. Tomer, IV, R. Richard L. Hamer
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Patent number: 5633407Abstract: A process for preparing substituted aromatic azo compounds is provided which comprises contacting a nucleophilic compound and an azo containing compound in the presence of a suitable solvent system, and reacting the nucleophilic compound and the azo containing compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 10.degree. C. to about 150.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1. In another embodiment, the substituted aromatic azo compounds are further reacted with a nucleophilic compound in the presence of a suitable solvent system, a suitable base and a controlled amount of protic material at a temperature of about 70.degree. C. to about 200.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1 to produce a substituted aromatic amine.Type: GrantFiled: May 18, 1995Date of Patent: May 27, 1997Assignee: Flexsys America L. P.Inventors: Michael K. Stern, Brian K-M Cheng
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Patent number: 5629449Abstract: Disclosed is a method of making 3,5-diaminobenzotrifluoride from 4-chloro-3,5-dinitrobenzotrifluoride. A solution of 4-chloro-3,5-dinitrobenzotrifluoride in an alcohol is prepared. Separately, a slurry is prepared of a palladium catalyst on a suitable substrate, at least one equivalent of magnesium oxide per equivalent of 4-chloro-3,5-dinitrobenzotrifluoride, sufficient hydrogen-donating reducing agent to reduce the 4-chloro-3,5-dinitrobenzotrifluoride to 3,5-diaminobenzotrifluoride, and an amount of alcohol sufficient to make the slurry stirrable. The solution is added to the slurry with stirring at a rate that does not exceed the reaction rate of the 4-chloro-3,5-dinitrobenzotrifluoride so that no unreacted 4-chloro-3,5-dinitrobenzotrifluoride accumulates in the slurry. The reaction mixture is heated at about 75.degree. to about 100.degree. C.Type: GrantFiled: August 17, 1992Date of Patent: May 13, 1997Assignee: Occidental Chemical CorporationInventor: David E. Albright, Jr.
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Patent number: 5627293Abstract: The invention relates to ferrocenyldiphosphine ligands containing a silylene group, ferrocenyldiphosphines bound to inorganic or polymeric organic supports by this silylene group, their preparation and also their metal complexes with transition metals such as rhodium or iridium. The invention also relates to the use of these complexes for hydrogenating organic double or triple bonds, in particular olefinic double bonds and carbon-heteroatom double bonds. The complexes are particularly suitable for enantioselective hydrogenation using chiral diphosphines and prochiral unsaturated compounds.The preparation of these immobilized ferrocenyldiphosphines has only been made possible by the provision of correspondingly functionalized ferrocenyldiphosphines. These compounds and their preparation are likewise novel.Accordingly, the invention also provides compounds of the formula I ##STR1## in which R.sub.1 is C.sub.1 -C.sub.8 alkyl, phenyl or phenyl substituted by from 1 to 3 C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.Type: GrantFiled: February 23, 1996Date of Patent: May 6, 1997Assignee: Ciba-Geigy CorporationInventor: Benoit Pugin
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Patent number: 5618979Abstract: A process for preparing substituted aromatic amines which comprises contacting a nucleophilic compound and a substituted aromatic azo compound in the presence of a suitable solvent system, and reacting the nucleophilic compound and the substituted aromatic azo compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 70.degree. C. to about 200.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1. In another embodiment, the substituted aromatic amines of the invention are reductively alkylated to produce alkylated diamines or substituted derivatives thereof.Type: GrantFiled: May 18, 1995Date of Patent: April 8, 1997Assignee: Flexsys America L. P.Inventors: Michael K. Stern, Brian K-M Cheng
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Patent number: 5608111Abstract: A method of producing 4-ADPA is disclosed wherein aniline or substituted aniline derivatives and nitrobenzene are reacted under suitable conditions to produce 4-nitrodiphenylamine or substituted derivatives thereof and/or 4-nitrosodiphenylamine or substituted derivatives thereof and/or their salts, either or both of which are subsequently reduced to produce 4-ADPA or substituted derivatives thereof. The 4-ADPA or substituted derivatives thereof can be reductively alkylated to produce p-phenylenediamine products or substituted derivatives thereof which are useful as antiozonants.Type: GrantFiled: May 5, 1995Date of Patent: March 4, 1997Assignee: Flexsys America L. P.Inventors: Michael K. Stern, James M. Allman, James K. Bashkin, Roger K. Rains
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Patent number: 5563296Abstract: Aromatic diamines and polyamines are produced by a continuous process for the catalytic hydrogenation of the corresponding dinitro and polynitro compounds at elevated temperature. Heat removed from the reaction mixture may be used to produce steam with an overpressure of .gtoreq.2 bar.Type: GrantFiled: June 30, 1994Date of Patent: October 8, 1996Assignee: Bayer AktiengesellschaftInventors: Uwe J. Zarnack, Fritz Pohl, Dieter Grenner, Hartmut Hetzel, Helmut Judat
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Patent number: 5451702Abstract: A process for preparing substituted aromatic amines is provided which comprises contacting a nucleophilic compound and an azo containing compound in the presence of a suitable solvent system, reacting the nucleophilic compound and the azo containing compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 10.degree. C. to about 150.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1 and reducing the product of the reaction of the nucleophilic compound and the azo containing compound under conditions which produce the substituted aromatic amine. In another embodiment, the substituted aromatic amines of the invention are reductively alkylated to produce alkylated diamines or substituted derivatives thereof.Type: GrantFiled: April 26, 1993Date of Patent: September 19, 1995Assignee: Monsanto CompanyInventors: Michael K. Stern, Brian K-M Cheng
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Patent number: 5449832Abstract: This invention relates to an improved process for storing and transporting toluenediamine, particularly for long term storage or storage in large containers, e.g., shipboard containers. The improvement in the process resides in substantially reducing the melting or freezing point of anhydrous toluenediamine obtained by the fractional distillation of a reaction product generated by the hydrogenation of dinitrotoluene. Such melting point reduction is accomplished by adding water in an amount of from 5 to 15% by weight of the toluenediamine and mixing therein for storage and transport. Preferably the level of water introduced to the anhydrous toluenediamine is from about 7 to 10% by weight.Type: GrantFiled: October 5, 1994Date of Patent: September 12, 1995Assignee: Air Products and Chemicals, Inc.Inventors: Richard Van Court Carr, Andrew J. Casale
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Patent number: 5442114Abstract: There is disclosed a process for producing an aromatic amide compound of the general formula (4), including the steps of subjecting an o-nitrophenol compound of the general formula (1) to catalytic reduction in acetone or an aromatic hydrocarbon solvent under the presence of a nickel catalyst to give an o-aminophenol compound of the general formula (2); and (b) subjecting the o-aminophenol compound of the general formula (2) to condensation with an acid chloride compound having a sulfur content of 0.5% or less, based on the weight of the acid chloride compound, of the general formula (3) in acetone or an aromatic hydrocarbon solvent under an atmosphere of an inert gas having an oxygen concentration of 1% or less. The acid chloride compound having a sulfur content of 0.5% or less, based on the weight of the acid chloride compound, of the general formula (3) may be obtained by allowing a carboxylic acid compound of the general formula (5) to react with thionyl chloride and by concentrating the reaction mixture.Type: GrantFiled: January 18, 1994Date of Patent: August 15, 1995Assignee: Sumitomo Chemical Company, LimitedInventors: Kan Takamine, Michio Yamato, Akira Murakami, Tooru Tokumaru, Yoshinori Nakayama, Motoo Hazama
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Patent number: 5430189Abstract: An arylisonitrosoalkanone is hydrogenated in the presence of a noble metal catalyst and a weak carboxylic acid to form an arylalkanolamine which is then hydrogenated in the presence of a strong mineral acid and the transition metal catalyst to form an arylalkylamine. When the arylisonitrosoalkanone is an isonitrosoacetophenone, the isonitrosoacetophenone is prepared by one of two methods.In the first method, a substituted or an unsubstituted isonitrosoacetophenone is prepared from a corresponding substituted or unsubstituted acetophenone by oxidizing the acetophenone to form a substituted or an unsubstituted phenylglyoxalacetal in a reactor, hydrolyzing the phenylglyoxal acetal in the same reactor to form a corresponding substituted or unsubstituted phenylglyoxal, and condensing the phenylglyoxal with hydroxylamine or a salt thereof in the same reactor to form the substituted or unsubstituted isonitrosoacetophenone.Type: GrantFiled: January 19, 1994Date of Patent: July 4, 1995Assignee: Hoechst Celanese CorporationInventors: Joseph A. McDonough, Ahmed M. Tafesh, Olan S. Fruchey
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Patent number: 5420354Abstract: A process of preparing para phenylenediamines, such as, p-aminodiphenylamine. The process involves contacting nitrobenzene or a substituted derivative thereof with hydrogen and an amine, such as aniline, in the presence of a hydrogenation catalyst, a hydrogenation inhibitor, and an acid cocatalyst under reaction conditions.Type: GrantFiled: October 6, 1994Date of Patent: May 30, 1995Assignee: Uniroyal Chemical Company, Inc.Inventors: Russell E. Malz, Gerard V. Smith, Mark P. Ferrandino, Ruozhi Song
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Patent number: 5410085Abstract: Chlorine-substituted aromatic amines are prepared by the hydrogenation of chlorine-substituted aromatic nitro compounds in the presence of a catalyst containing platinum and nickel and/or cobalt on an activated charcoal support, the platinum having been simultaneously deposited and reduced on the activated charcoal support in the preparation of the catalyst. Such catalysts are furthermore prepared, as are catalysts containing noble metals on an activated charcoal support, it also being possible for the latter to be used for the reduction of nitronaphthalenes or nitrotoluenes.Type: GrantFiled: October 20, 1993Date of Patent: April 25, 1995Assignee: Bayer AktiengesellschaftInventors: Udo Birkenstock, Walter Kipshagen, Herbert Schmidt, Thomas-Jorn Schulz, Eberhard Zirngiebl
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Patent number: 5399768Abstract: The present invention relates to a method of preparing 4,6-diaminoresorcinol from 1,2-dichloro-3,5-dinitrobenzene comprising the steps of:(a) contacting 1,2-dichloro-3,5-dinitrobenzene with a hydroperoxide in the presence of anhydrous base to form 2,3-dichloro-4,6-dinitrophenol;(b) contacting 2,3-dichloro-4,6-dinitrophenol with a hydroxy-containing compound to form 2-chloro-4,6-dinitroresorcinol; and(c) converting 2-chloro-4,6-dinitroresorcinol to 4,6-diaminoresorcinol, which is isolated as a salt or other stabilized form thereof,Type: GrantFiled: December 23, 1993Date of Patent: March 21, 1995Assignee: The Dow Chemical CompanyInventors: Zenon Lysenko, Richard G. Pews
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Patent number: 5347052Abstract: 3,5-Diaminobenzotrifluoride can be produced, in a single step, by reacting 4-chloro-3,5-dinitrobenzotrifluoride, in methanol, with hydrogen gas, in the presence of magnesium oxide, and in the presence of a catalyst comprising palladium on a carbon support.Type: GrantFiled: April 15, 1991Date of Patent: September 13, 1994Assignee: Occidental Chemical CorporationInventor: David E. Albright, Jr.
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Patent number: 5315040Abstract: Aminoanthraquinones which are materials for dyes are prepared by allowing nitroanthraquinones to react with carbon monoxide and water in a liquid phase in the presence of a homogeneous catalyst comprising rhodium compounds or ruthenium compounds and solvents therefor.Type: GrantFiled: February 3, 1992Date of Patent: May 24, 1994Assignee: Sumitomo Chemical Company, LimitedInventors: Kotohiro Nomura, Masaru Ishino
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Patent number: 5252737Abstract: A process for preparing N-aliphatic substituted p-phenylenediamine intermediates is provided which comprises contacting an aliphatic amine or substituted aliphatic amine derivative and nitrobenzene in the presence of a suitable solvent system, and reacting the aliphatic amine or substituted aliphatic amine derivative and nitrobenzene in the presence of a suitable base and a controlled amount of protic material at a suitable temperature in a confined reaction zone. In one embodiment, the N-aliphatic substituted p-phenylenediamine intermediates are reduced to N-aliphatic substituted p-phenylenediamines and the N-aliphatic substituted p-phenylenediamines can be reductively alkylated to N'-alkylated, N-aliphatic substituted p-phenylenediamines. In another embodiment of the invention, N-aliphatic substituted p-phenylenediamine intermediates are reductively alkylated to N'-alkylated, N-aliphatic substituted p-phenylenediamines.Type: GrantFiled: May 22, 1992Date of Patent: October 12, 1993Assignee: Monsanto CompanyInventors: Michael K. Stern, Brian K. Cheng