Preparing By Reduction (e.g., By Hydrogenation, Etc.) Patents (Class 568/861)
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Patent number: 6969779Abstract: The present invention is an improvement upon the process for the production of 1,3-propanediol (PDO) wherein an aqueous solution of 3-hydroxypropanal (HPA) is formed, and the HPA is subjected to hydrogenation to produce a crude PDO mixture comprising PDO, water, MW176 acetal, and high and low volatility materials, wherein the crude PDO mixture is dried to produce a first overhead stream comprising water and some high volatility materials and a dried crude PDO mixture as a first distillate bottoms stream comprising PDO, MW176 acetal, and low volatility materials, and wherein the dried crude PDO mixture is distilled to produce a second overhead stream comprising some high volatility materials, a middle stream comprising PDO and MW176 acetal, and a second distillate bottoms stream comprising PDO and low volatility materials.Type: GrantFiled: October 1, 2003Date of Patent: November 29, 2005Assignee: Shell Oil CompanyInventors: Stephen Edward Brewer, Zaida Diaz, Joseph Broun Powell, Paul Richard Weider, Glenn Charles Komplin, Robert Lawrence Blackbourn
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Patent number: 6956141Abstract: A process for preparing at least one unsaturated alcohol (B) comprises the steps (I) to (III) below: (I) reaction of at least one alkali metal hydroxide or alkaline earth metal hydroxide with at least one alcohol (A) in at least one organic solvent (L) to give a mixture (G-I) comprising at least the alcohol (A), the solvent (L) and an alkoxide (AL); (II) reaction of at least one carbonyl compound of the formula R—CO—R? with at least one alkyne of the formula R?—C?C—H and the mixture (G-I) obtained in step (I) to give a mixture (G-II) comprising at least the alcohol (A), the solvent (L) and an unsaturated alcohol (B); (III) distillation of the mixture (G-II) obtained in step (II) to give the alcohol or alcohols (B) and a mixture (G-III) comprising the solvent (L) and the alcohol (A), wherein the solvent (L) obtained in step (III) and the alcohol (A) obtained in step (III) are recycled as a mixture to step (I).Type: GrantFiled: February 22, 2000Date of Patent: October 18, 2005Assignee: BASF AktiengesellschaftInventors: Melanie Maas-Brunner, Jochem Henkelmann, Gerd Kaibel, Alois Kindler, Christian Knoll, Harald Rust, Christian Tragut, Manfred Stroezel, Udo Rheude, Rudolf Erich Lorenz, Juan Aiscar
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Patent number: 6919489Abstract: Disclosed is a process for a cyclohexanedimethanol by hydrogenation of a cyclohexane-dicarboxylate ester in the presence of a Raney metal catalyst doped with rhenium. The process is useful for the reparation of 1,4-cyclohexanedimethanol from dialkyl esters of 1,4-cyclohexanedicarboxylate or dialkyl terephthalates. When Raney nickel is used as the catalyst, the process produces CHDM having a high trans content.Type: GrantFiled: March 3, 2004Date of Patent: July 19, 2005Assignee: Eastman Chemical CompanyInventor: Jennifer Ellen McCusker-Orth
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Patent number: 6911565Abstract: The present invention relates to a process for the production of xylitol. The process utilises ribulose for the preparation of xylitol and involves several different conversion reactions, such as reduction, epimerisation and/or isomerisation. The present invention also relates to the use of ribulose for the preparation of xylitol.Type: GrantFiled: September 26, 2002Date of Patent: June 28, 2005Assignee: Danico Sweetners OyInventors: Heikki Heikkilä, Heikki Ojamo, Andrei Miasnikov, Vili Ravanko, Matti Tylli
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Patent number: 6911566Abstract: A process for producing 1,3-propanediol, comprising: hydrating acrolein in a liquid phase in the presence of a hydration catalyst to form 3-hydroxypropanal; separating any unreacted acrolein, if any is present; and carrying out catalytic hydrogenation of the 3-hydroxypropanal in a liquid or gas phase with a hydrogenation catalyst, wherein the hydration catalyst is a catalyst comprising at least one member selected from the group consisting of the following materials (a) to (c) and has a pH of 6 or less at 20° C., when made into a slurry by dispersing the catalyst in a quantity of water 5 times as much as the quantity of catalyst by weight: (a) a metalloaluminophosphate molecular sieve, (b) an FER type zeolite, and (c) an oxide or compound oxide, excluding crystalline aluminosilicate zeolites, which comprises one or more element(s) selected from the elements belonging to group 4, group 13 and group 14 of the periodic table.Type: GrantFiled: March 1, 2002Date of Patent: June 28, 2005Assignee: Asahi Kasei Kabushiki KaishaInventors: Takashi Tsunoda, Kouji Nomura
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Patent number: 6906228Abstract: In a process for preparing alcohols by catalytic hydrogenation of carbonyl compounds over a catalyst comprising rhenium on activated carbon, the catalyst used comprises rhenium (calculated as metal) in a weight ratio to the activated carbon of from 0.0001 to 0.5, platinum (calculated as metal) in a weight ratio to the activated carbon of from 0.0001 to 0.5 and, if appropriate, at least one further metal selected from among Zn, Cu, Ag, Au, Ni, Fe, Ru, Mn, Cr, Mo, W and V in a weight ratio to the activated carbon of from 0 to 0.25, and the activated carbon has been nonoxidatively pretreated It is also possible to prepare ethers and lactones if the hydrogen pressure is not more than 25 bar. In this case, the activated carbon in the catalyst may also have been nonoxidatively pretreated.Type: GrantFiled: March 1, 2001Date of Patent: June 14, 2005Assignee: BASF AGInventors: Rolf Hartmuth Fischer, Rolf Pinkos, Stephan Andreas Schunk, Joachim Wulff-Döring, Frank Stein, Thomas Nöbel, Sylvia Huber
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Patent number: 6894199Abstract: The present invention relates to the production of xylitol. In particular, processes utilising L-xylose as an intermediate for xylitol production are described. The present invention also relates to process for the preparation or L-xylose, as an intermediate, by-product or end-product to be used per se.Type: GrantFiled: April 29, 2002Date of Patent: May 17, 2005Assignee: Danisco Sweeteners OyInventors: Heikki Heikkilä , Heikki Ojamo, Matti Tylli, Vili Ravanko, Juha Nurmi, Piia Haimi, Raimo Alen, Hannu Koivikko
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Patent number: 6878852Abstract: A process for the hydrogenation, using molecular hydrogen (H2) of a catalytic system, wherein the catalytic system includes a base and a complex of formula (II): Ru(P2N2)Y2??(II) wherein Y represent simultaneously or independently a hydrogen or halogen atom, a hydroxy group, or an alkoxy, carboxyl or other anionic radical, and P2N2 is a tetradentate diimino-diphosphine ligand.Type: GrantFiled: November 11, 2001Date of Patent: April 12, 2005Assignee: Firmenich SAInventors: Valentin Rautenstrauch, Raphaël Churlaud, Robert Harold Morris, Kamaluddin Abdur-Rashid
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Patent number: 6841085Abstract: Methods for hydrogenolysis are described which use a Re-containing multimetallic catalyst for hydrogenolysis of both C—O and C—C bonds. Methods and compositions for reactions of hydrogen over a Re-containing catalyst with compositions containing a 6-carbon sugar, sugar alcohol, or glycerol are described. It has been surprisingly discovered that reaction with hydrogen over a Re-containing multimetallic catalyst resulted in superior conversion and selectivity to desired products such as propylene glycol.Type: GrantFiled: October 23, 2001Date of Patent: January 11, 2005Assignee: Battelle Memorial InstituteInventors: Todd A. Werpy, John G. Frye, Jr., Alan H. Zacher, Dennis J. Miller
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Patent number: 6811604Abstract: The subject matter of the invention is a new additive for mineral binders comprising a composition containing at least one product of internal dehydration of a hydrogenated sugar which can especially be a dehydrated hexitol such as isosorbide, isomannide, sorbitan or mannitan and which can be introduced at a rate of between roughly 0.001 and 5% (dry/dry) within any mineral binder, said additive being advantageously used as an accelerator for setting and/or hardening and/or as an agent for improving the mechanical properties of the mineral binder. It has a remarkable efficiency, including at low temperatures.Type: GrantFiled: July 26, 2002Date of Patent: November 2, 2004Assignee: Roquette FreresInventors: Léon Mentink, Jean-Pierre Graux
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Patent number: 6787677Abstract: In a process for the catalytic hydrogenation of a carbonyl compound or a mixture of two or more carbonyl compounds in the presence of catalyst tablets which comprise an inorganic, TiO2-containing support and, as active component, copper or a mixture of copper with at least one metal selected from the group consisting of zinc, aluminum, cerium, nobel metals and metals of transition group VIII and whose copper surface area is not more than 10 m2/g, the diameter d and/or the height h of the tablets is less than 3 mm.Type: GrantFiled: September 29, 2003Date of Patent: September 7, 2004Assignee: BASF AktiengesellschaftInventors: Michael Koch, Steffen Maas, Wolfgang Jürgen Pöpel, Matthias Dernbach
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Publication number: 20040122242Abstract: An improved catalyst of ruthenium, molybdenum and, optionally, tin with an inert support used for hydrogenation of an hydrogenatable precursor in an aqueous solution and a method for using the catalyst in the production of tetrahydrofuran and 1,4-butanediol from such a hydrogenatable precursor in an aqueous solution.Type: ApplicationFiled: December 23, 2002Publication date: June 24, 2004Inventor: Daniel Campos
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Patent number: 6750373Abstract: Disclosed is a new catalyst composition comprising a bimetallic Co—Fe catalyst, optionally complexed with a ligand selected from a N-heterocycle, phosphine, or porphorine ligand, that provides a lower cost alternative for the one step synthesis of 1,3-propanediol (1,3-PDO) from ethylene oxide and synthesis gas. For example, a catalyst containing cobalt carbonyl: iron carbonyl with no ligand, or a catalyst containing a cobalt carbonyl: octaethylporphine iron acetate provide moderate yields of 1,3-PDO in a one step synthesis under mild conditions.Type: GrantFiled: May 15, 2002Date of Patent: June 15, 2004Assignee: Shell Oil CompanyInventors: John Frederick Knifton, Talmadge Gail James, Lynn Henry Slaugh, Kevin Dale Allen, Paul Richard Weider, Joseph Broun Powell
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Publication number: 20040077885Abstract: A process for production of tetrahydrofuran, gamma butyrolactone, 1,4 butanediol and the like from a hydrogenatable precursor such as maleic acid, succinic acid, corresponding esters and their mixtures and the like in an aqueous solution in the presence of hydrogen using a noble metal catalyst, wherein a deactivated noble metal catalyst is regenerated by contacting the catalyst with a solvent, separating the solvent from the catalyst, and then reusing the regenerated catalyst in the process.Type: ApplicationFiled: October 21, 2002Publication date: April 22, 2004Inventors: Daniel Campos, Richard Edward Ernst
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Patent number: 6720457Abstract: Olefins having from 5 to 24, in particular from 5 to 12, carbon atoms are hydroformylated by reacting an olefin or a mixture of olefins in the presence of an unmodified cobalt catalyst in a single-stage process in a reactor at a temperature of from 100° C. to 220° C. and a pressure of from 100 bar to 400 bar, to obtain an aldehyde, an alcohol or a mixture thereof. An aqueous bottom phase and an organic phase are present in the reactor, the aqueous bottom phase is mixed with the organic phase, and a concentration of the cobalt catalyst, calculated as metallic cobalt, in the aqueous bottom phase is in the range from 0.4 to 1.7% by mass based on the total weight of the aqueous bottom phase. A level of the aqueous bottom phase in the reactor is kept constant during steady-state operation.Type: GrantFiled: July 24, 2002Date of Patent: April 13, 2004Assignee: Oxeno Olefinchemie GmbHInventors: Stefan Drees, Bernhard Scholz, Alfred Kaizik, Walter Toetsch, Wilfried Bueschken, Martin Trocha
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Patent number: 6706932Abstract: Disclosed is a method for producing a diol mixture comprising 1,4-butanediol, 1,5-pentanediol and 1,6-hexanediol, which comprises: (A) providing a dicarboxylic acid mixture comprising succinic acid, glutaric acid and adipic acid and having a nitric acid content of 3% by weight or less, based on the total weight of the succinic, glutaric and adipic acids, wherein the dicarboxylic acid mixture is prepared by denitrating an aqueous by-product solution obtained in an adipic acid production process, and (B) subjecting the dicarboxylic acid mixture to hydrogenation in the presence of water, hydrogen gas and a hydrogenation catalyst containing an active metal species comprising ruthenium and tin, to thereby obtain a hydrogenation reaction mixture comprising a diol mixture comprising 1,4-butanediol, 1,5-pentanediol and 1,6-hexanediol.Type: GrantFiled: May 2, 2002Date of Patent: March 16, 2004Assignee: Asahi Kasei Kabushiki KaishaInventors: Mitsuo Konishi, Koshiro Yokota, Eizaburou Ueno
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Patent number: 6703528Abstract: There are disclosed are a method for producing at least one compound selected from a carbonyl compound and a hydroxy adduct compound by an oxidative cleavage or addition reaction of an olefinic double bond of an olefin compound, which contains reacting an olefin compound with hydrogen peroxide, utilizing as a catalyst, at least one member selected from (a) tungsten, (b) molybdenum, or (c) a tungsten or molybdenum metal compound containing (ia) tungsten or (ib) molybdenum and (ii) an element of Group IIIb, IVb, Vb or VIb excluding oxygen, and a catalyst composition.Type: GrantFiled: August 10, 2001Date of Patent: March 9, 2004Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Hagiya, Naoyuki Takano, Akio Kurihara
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Publication number: 20040039236Abstract: A process for the preparation of an alcohol from an olefin, wherein the olefin is reacted with syngas in the presence of a catalyst system comprising a homogeneous hydroformylation catalyst and a heterogeneous catalyst comprising copper on a support.Type: ApplicationFiled: November 22, 2002Publication date: February 26, 2004Inventor: Jean-Paul Lange
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Patent number: 6680414Abstract: The present invention provides a process, which includes: in a homogeneous liquid phase including water, and over a fixed-bed catalyst, continuously hydrogenating at least one hydroformylation product obtained from a hydroformylation of one or more C4-16 olefins to produce at least one output mixture; wherein the fixed-bed catalyst includes at least one element of transition group eight of the Periodic Table of the Elements; wherein the output mixture includes at least one corresponding alcohol and from 0.05 to 10% by weight of water; and wherein in a steady-state operation of the process, from 3 to 50% more hydrogen is fed to the hydrogenation than is consumed by the hydrogenation.Type: GrantFiled: December 14, 2001Date of Patent: January 20, 2004Assignee: Oxeno Olefinchemie GmbHInventors: Cord Knoop, Bernhard Scholz, Alfred Kaizik, Dietmar Gubisch, Joachim Schuler, Walter Tötsch, Wilfried Büschken
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Patent number: 6670300Abstract: A textured catalyst having a hydrothermally-stable support, a metal oxide and a catalyst component is described. Methods of conducting aqueous phase reactions that are catalyzed by a textured catalyst are also described. The invention also provides methods of making textured catalysts and methods of making chemical products using a textured catalyst.Type: GrantFiled: June 18, 2001Date of Patent: December 30, 2003Assignee: Battelle Memorial InstituteInventors: Todd Werpy, John G. Frye, Jr., Yong Wang, Alan H. Zacher
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Patent number: 6660892Abstract: This invention is a process for synthesizing aliphatic 1,3-diols in one step by hydroformylation and hydrogenation of oxirane, carbon monoxide, and hydrogen employing a catalyst comprising a cobalt carbonyl compound and a cocatalyst metal compound ligated with a ligand in a ligand to cocatalyst metal atom molar ratio in the range of 0.2:1.0 to 0.6:1.0, optionally in the presence of a promoter, where recovery of product is preferably accomplished via water extraction of a diol rich phase from the bulk reaction mixture. The process modifications can, particularly in combination, be beneficial with respect to product recovery, catalyst recycle, and overall economics of a one-step process for producing aliphatic 1,3-diols.Type: GrantFiled: February 7, 2003Date of Patent: December 9, 2003Assignee: Shell Oil CompanyInventors: Joseph Broun Powell, Paul Richard Weider, John Frederick Knifton, Kevin Dale Allen, Lynn Henry Slaugh, Juan Pedro Arhancet
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Publication number: 20030195369Abstract: A (R) or (S) chiral diphosphine of formula (I): 1Type: ApplicationFiled: January 31, 2003Publication date: October 16, 2003Applicant: PPG-SIPSYInventors: Michel Bulliard, Blandine Laboue, Sonia Roussiasse
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Patent number: 6617478Abstract: A process for preparing a 1,3-alkandiol from a 3-hydroxyester, comprises preparing a catalyst by adding an alkaline precipitator to an aqueous copper salt solution to form copper hydroxide particles, and aging the particles following the addition of a colloidal silica thereto; activating the catalyst by reduction with a H2 gas or a H2-containing gas and applying a pressure of about 5 psig to about 2000 psig at a temperature of about 100° C. to about 250° C. in the presence of an activation solvent; and hydrogenating a 3-hydroxyester in a liquid phase slurry with a H2 gas or a H2-containing gas and applying a pressure of about 50 psig to about 3000 psig at a temperature of about 100° C. to about 250° C. in the presence of the activated catalyst and a reaction solvent, whereby a 1,3-alkanediol can be selectively prepared from a 3-hydroxyester with a high yield.Type: GrantFiled: August 6, 2002Date of Patent: September 9, 2003Assignees: Samsung Electronics Co., Ltd., Korea Research Institute of Chemical TechnologyInventors: Byeong No Lee, In Sun Jung, Eun Joo Jang, Jung Ho Lee, Hyung Rok Kim, Yo Han Han
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Patent number: 6617477Abstract: A process for preparing an 1,3-alkanediol from a 3-hydroxyester includes hydrogenating a 3-hydroxyester in an alcohol-containing solvent in the presence of a hydrogenation catalyst prepared by adding an alkaline precipitator to an aqueous solution containing a copper salt to form particles, and then aging the particles following addition of colloidal silica thereto. Novel hydrogenation catalysts so prepared are also disclosed.Type: GrantFiled: November 29, 2001Date of Patent: September 9, 2003Assignees: Samsung Electronics Co., Ltd., Korea Research Institute of Chemical TechnologyInventors: Byeong No Lee, Eun Joo Jang, Jung Ho Lee, Hyung Rok Kim, Yo Han Han, Hyun Kwan Shin, Ho Sun Lee
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Publication number: 20030153795Abstract: A process is described for the production of propane-1,3-diol. The process comprises subjecting a vaporous feed mixture comprising a hydrogen-containing gas and a feedstock selected from 3-hydroxypropanal, &bgr;-propiolactone, oligomers of &bgr;-propiolactone, esters of 3-hydroxypropanoic acid, and mixtures of two or more thereof to hydrogenation conditions in a hydrogenation zone in the presence of a heterogeneous hydrogenation catalyst, and recovering a reaction product comprising propane-1,3-diol.Type: ApplicationFiled: January 30, 2003Publication date: August 14, 2003Inventors: Simon Peter Crabtree, Richard Kevin Henderson
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Patent number: 6586643Abstract: Disclosed is a new catalyst composition comprising a bimetallic Co—Ru catalyst complexed with a N-heterocylcic ligand that is effective, economical, and provides improvements in oxidative stability in the one step synthesis of 1,3-propanediol (1,3-PDO) from ethylene oxide and synthesis gas. For example, cobalt-ruthenium-2,2′-bipyrimidine, 2,2′-dipyridyl, or 2,4,6-tripridyl-s-triazine catalyst precursors in cyclic ether solvents, such as 1,3-dioxolane, 1,4-dioxolane, 1,4-dioxane, and 2-ethyl-2-methyl-1,3-dioxolane, provide good yields of 1,3-PDO in a one step synthesis.Type: GrantFiled: May 15, 2002Date of Patent: July 1, 2003Assignee: Shell Oil CompanyInventors: John Frederick Knifton, Talmadge Gail James, Kevin Dale Allen, Paul Richard Weider, Joseph Broun Powell, Lynn Henry Slaugh, Timothy Williams
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Publication number: 20030119952Abstract: Methods for hydrogenolysis are described which use a Re-containing multimetallic catalyst for hydrogenolysis of both C—O and C—C bonds. Methods and compositions for reactions of hydrogen over a Re-containing catalyst with compositions containing a 6-carbon sugar, sugar alcohol, or glycerol are described. It has been surprisingly discovered that reaction with hydrogen over a Re-containing multimetallic catalyst resulted in superior conversion and selectivity to desired products such as propylene glycol.Type: ApplicationFiled: October 23, 2001Publication date: June 26, 2003Inventors: Todd A. Werpy, John G. Frye, Alan H. Zacher, Dennis J. Miller
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Publication number: 20030100777Abstract: A process for the co-production of a diol product (e.g. butane-1,4-diol) and a cyclic ether (e.g. tetrahydrofuran) by hydrogenation of an aliphatic diester or lactone feedstock (e.g. dimethyl or diethyl maleate), which contains a minor amount of acidic material, such as the corresponding monoester. The process utilizes a plurality of hydrogenation zones connected in series, each containing a charge of a granular ester hydrogenation catalyst. The catalyst in the first hydrogenation zone is tolerant of a minor amount of acidic material, while the catalyst in the second hydrogenation zone provides enhanced yields of cyclic ethers compared to the catalyst of the first hydrogenation zone. The catalyst in a third hydrogenation zone exhibits low selectivity towards conversion of the diester to at least one by product (e.g. 2-4′-hydroxybutoxy-tetrahydrofuran).Type: ApplicationFiled: June 10, 2002Publication date: May 29, 2003Inventors: Michael Anthony Wood, Paul Willett, Robert Wild, Stephen William Colley
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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
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Patent number: 6548716Abstract: A process for preparing a 1,3-diol by hydrogenating a feed having a 3-hydroxyaldehyde in the presence of a catalyst and a hydrogen source, wherein syngas is used as hydrogen source, and the catalyst is a heterogeneous catalyst having copper on a support.Type: GrantFiled: September 18, 2002Date of Patent: April 15, 2003Assignee: Shell Oil CompanyInventor: Jean-Paul Lange
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Publication number: 20030069456Abstract: A process for preparing a 1,3-alkandiol from a 3-hydroxyester, comprises preparing a catalyst by adding an alkaline precipitator to an aqueous copper salt solution to form copper hydroxide particles, and aging the particles following the addition of a colloidal silica thereto; activating the catalyst by reduction with a H2 gas or a H2-containing gas and applying a pressure of about 5 psig to about 2000 psig at a temperature of about 100° C. to about 250° C. in the presence of an activation solvent; and hydrogenating a 3-hydroxyester in a liquid phase slurry with a H2 gas or a H2-containing gas and applying a pressure of about 50 psig to about 3000 psig at a temperature of about 100° C. to about 250° C. in the presence of the activated catalyst and a reaction solvent, whereby a 1,3-alkanediol can be selectively prepared from a 3-hydroxyester with a high yield.Type: ApplicationFiled: August 6, 2002Publication date: April 10, 2003Applicant: Samsung Electronics Co., Ltd. andInventors: Byeong No Lee, In Sun Jung, Eun Joo Jang, Jung Ho Lee, Hyung Rok Kim, Yo Han Han
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Publication number: 20030050516Abstract: 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: ApplicationFiled: September 23, 2002Publication date: March 13, 2003Inventors: Rolf-Hartmuth Fischer, Rolf Pinkos, Stephan Andreas Schunk, Joachim Wulff-Doring
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Patent number: 6528689Abstract: A hydrogenation catalyst of the general formula AB(y)C(z) wherein A is a support comprising of a salt of a Group II A metal or zeolite, B is a noble metal selected from Pt or Pd, y=0.2 to 10%, C is nickel and z=0 to 15.0%, with the proviso that when B is Pt, z=0.Type: GrantFiled: August 28, 2001Date of Patent: March 4, 2003Assignee: Council of Scientific and Industrial ResearchInventors: Raghunath Vitthal Chaudhari, Chandrashekhar Vasant Rode, Rengaswamy Jaganathan, Manisha Madhukar Telkar, Vilas Hari Rane
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Patent number: 6518466Abstract: The invention provides a process for an improved oxirane hydroformylation catalyst, the improved oxirane hydroformylation catalyst, and a one step process for preparing a 1,3-diol in the presence of such a catalyst. One process for preparing the hydroformylation catalyst involves: a) forming a complex (A) by contacting a ruthenium(0) compound with a ditertiary phosphine ligand; and b) forming a complex (B) by subjecting complex (A) to a redox reaction with a cobalt(0) carbonyl compound. This catalyst is used in a one step hydroformylation process for preparing a 1,3-diol, comprising the reaction of an oxirane with syngas at hydroformylation conditions in an inert solvent in the presence of the above hydroformylation catalyst where recovery of product is preferably accomplished via phase separation of a diol rich phase from the bulk reaction liquor.Type: GrantFiled: September 20, 2001Date of Patent: February 11, 2003Assignee: Shell Oil CompanyInventors: John Frederick Knifton, Lynn Henry Slaugh, Paul Richard Weider, Talmadge Gail James, Joseph Broun Powell, Kevin Dale Allen, Timothy Scott Williams
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Patent number: 6489373Abstract: The present invention provides a method of recovering a polyamine compound and/or a polyol compound useful for starting materials of polyurethane resin in an industrially advantageous manner by first dissolving the polyurethane resin such as polyurethane foams discharged in a large amount as industrial wastes in a solubilizing agent containing a polyamine compound, a low molecular glycol or an amino alcohol, hydrolyzing the resulting solution with liquid water at 200 to 320° C., then recovering the polyamino compound and/or polyol compound thus formed.Type: GrantFiled: October 1, 1999Date of Patent: December 3, 2002Assignee: Mitsui Takeda Chemicals Inc.Inventors: Katsuhisa Kodama, Kouichi Murayama, Takashi Kumaki
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Patent number: 6479713Abstract: Methods and compositions for reactions of hydrogen over a Re-containing catalyst with compositions containing a 5-carbon sugar, sugar alcohol, or lactic acid are described. It has been surprisingly discovered that reaction with hydrogen over a Re-containing multimetallic catalyst resulted in superior conversion and selectivity to desired products such as propylene glycol. A process for the synthesis of PG from lactate or lactic acid is also described.Type: GrantFiled: October 23, 2001Date of Patent: November 12, 2002Assignee: Battelle Memorial InstituteInventors: Todd A. Werpy, John G. Frye, Jr., Alan H. Zacher, Dennis J. Miller
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Patent number: 6469221Abstract: The present invention relates to a process for the conversion of 1,4 butynediol to 1,4 butanediol or a mixture of 1,4 butanediol and 1,4 butenediol comprising hydrogenating an aqueous solution of 1,4 butynediol using platinum supported CaCO3 catalyst at a temperature in the range of 20-190° C. under a hydrogen pressure in the range between 5-100 bar and collecting the product by any known method.Type: GrantFiled: November 20, 2000Date of Patent: October 22, 2002Assignee: Council of Scientific and Industrial ResearchInventors: Raghunath Vitthal Chaudhari, Chandrashekhar Vasant Rode, Rengaswamy Jaganathan, Manisha Madhukar Telkar, Vilas Hari Rane
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Publication number: 20020133048Abstract: The present invention provides a method of converting sugars to their corresponding sugar alcohols by catalytic hydrogenation in the aqueous phase. It has been found that surprisingly superior results can be obtained by utilizing a relatively low temperature (less than 120° C.), selected hydrogenation conditions, and a hydrothermally stable catalyst. These results include excellent sugar conversion to the desired sugar alcohol, in combination with long life under hydrothermal conditions.Type: ApplicationFiled: April 27, 2001Publication date: September 19, 2002Inventors: Douglas C. Elliott, Todd A. Werpy, Yong Wang, John G. Frye
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Patent number: 6426437Abstract: A process for the production of 1,4-butanediol is described. The process comprises hydroformylating allyl alcohol in the presence of a solvent and a catalyst system comprising a rhodium complex, a ruthenium complex and a diphosphine ligand and hydrogenating the resulting 4-hydroxybutyraldehyde using the same catalyst system. The process gives high yield of 1,4-butanediol compared to 2-methyl-1,3-propanediol.Type: GrantFiled: December 13, 2000Date of Patent: July 30, 2002Assignee: Arco Chemical Technology, L.P.Inventor: Wilfred P. Shum
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Patent number: 6426438Abstract: A process for the preparation of 1,6-hexanediol and 6-hydroxycaproic acid or esters thereof by catalytic hydrogenation of adipic acid, adipic acid monoesters or adipic acid diesters or streams of starting material which contain adipic acid or esters thereof as essential constituents, in which the bottom product obtained in the distillation of the hydrogenation product, following removal of the hexanediol and hydroxycaproic acid or esters thereof, and essentially comprises oligomeric esters of 6-hydroxycaproic acid, is recycled to the hydrogenation, and the resulting mixture of starting material and recycle stream is reacted at from 100 to 300°C., at from 10 to 300 bar in the liquid phase and at a molar ratio of carboxyl groups to be hydrogenated to hydrogen in the reactor of from 1:5 to 1:100 on hydrogenation catalysts is described.Type: GrantFiled: April 20, 2000Date of Patent: July 30, 2002Assignee: BASF AktiengesellschaftInventors: Rolf Hartmuth Fischer, Rolf Pinkos, Frank Stein
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Patent number: 6420615Abstract: A process for the preparation of 1,4 butenediol comprising hydrogenating an aqueous solution of 1,4 butynediol under stirring conditions over a supported platinum or palladium and nickel catalyst in basic medium at a temperature in the range of 20-110° C. and pressure in the range between 200-700 psig till the reaction is completed, cooling the reaction mixture to room temperature and separating the catalyst by known methods to obtain 1,4 butenediol.Type: GrantFiled: November 20, 2000Date of Patent: July 16, 2002Assignee: Council of Scientific and Industrial ResearchInventors: Raghunath Vitthal Chaudhari, Chandrashekhar Vasant Rode, Rengaswamy Jaganathan, Manisha Madhukar Telkar, Vilas Hari Rane
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Patent number: 6414201Abstract: To obtain a Raney catalyst for fixed bed permitting a continuous use with a high initial activity and to produce a high purity sugar-alcohol at a low cost using the same. For this object, sugar-alcohol is produced by: using the powder type Raney catalyst made by using for the hydrogenation under the hydrogen pressure a lump form Raney catalyst made by (i) the first step for melting nickel and aluminum, (ii) the second step for obtaining quenched lump alloy by quenching droplets of said melted mixture and (iii) the third step for classifying and activating said quenched lump alloy as it is or once it is broken, collecting said lump form Raney catalyst, crushing into powder and reactivating, and hydrogenating sugars under the hydrogen pressure.Type: GrantFiled: November 4, 1996Date of Patent: July 2, 2002Assignees: Towa Chemical Industry Co., Ltd., Nikko Rica CorporationInventors: Koshiro Shimazu, Yoshiaki Tateno, Mitsuo Magara, Naoki Okamoto, Takao Ohshima, Minoru Nagasawa, Hideki Sakamura
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Patent number: 6403845Abstract: are prepared by single-stage reaction of alkoxydihydropyrans of the formula (II) with water and hydrogen in the presence of a catalyst comprising oxides of nickel, zirconium and copper. In the formulae (I) and (II), R, R′, R″, R′″ can be identical or different and are each hydrogen or a linear or branched saturated hydrocarbon radical having from 1 to 20 carbon atoms in which the hydrocarbon chain may contain O, S and N as heteroatoms and which may be monosubstituted or polysubstituted by hydroxy, thiol or amino groups or halogens.Type: GrantFiled: July 25, 2000Date of Patent: June 11, 2002Inventors: Joachim Pfeffinger, Peter Wahl, Jan Nouwen, Karsten Eller, Arthur Höhn, Jürgen Hunger
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Patent number: 6380438Abstract: A process for producing 3-hydroxypropanal includes reacting formaldehyde and acetaldehyde to form an aqueous solution of acrolein; and hydrating the aqueous solution of acrolein to form 3-hydroxypropanal, wherein the aqueous solution of acrolein is capable of being hydrated to 3-hydroxypropanal without having to remove excess formaldehyde or acetaldehyde.Type: GrantFiled: July 13, 2000Date of Patent: April 30, 2002Assignee: TTC Labs, Inc.Inventor: George Robert Winter
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Publication number: 20020049258Abstract: The present invention provides a method of recovering a polyamine compound and/or a polyol compound useful for starting materials of polyurethane resin in an industrially advantageous manner by first dissolving the polyurethane resin such as polyurethane foams discharged in a large amount as industrial wastes in a solubilizing agent containing a polyamine compound, a low molecular glycol or an amino alcohol, hydrolyzing the resulting solution with liquid water at 200 to 320° C., then recovering the polyamino compound and/or polyol compound thus formed.Type: ApplicationFiled: October 1, 1999Publication date: April 25, 2002Inventors: KATSUHISA KODAMA, KOUICHI MURAYAMA, TAKASHI KUMAKI
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Patent number: 6376723Abstract: A carbonylation process, wherein formaldehyde or a derivative thereof is reacted with carbon monoxide in the presence of a catalyst composition including: a) an acidic compound with pKa value below −1, and b) a sulfone.Type: GrantFiled: December 18, 2000Date of Patent: April 23, 2002Assignee: Shell Oil CompanyInventors: Eit Drent, Wilhelmus Petrus Mul, Bart Johan Ruisch
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Patent number: 6350924Abstract: A process for preparing 1,4-butanediol and, if desired, &ggr;-butyrolactone and THF by oxidizing butane or benzene to form a product stream including maleic anhydride, absorbing maleic anhydride from the product stream with a high-boiling inert solvent in an absorption stage to give a liquid absorption product, esterifying the liquid absorption product with a C1-C5 esterifying alcohol in an esterification stage to form an esterification product comprising the corresponding diester and high-boiling inert solvent, then hydrogenating the esterification product to give a hydrogenation product which comprises the products of value, 1,4-butanediol and, if desired, &ggr;-butyrolactone and tetrahydrofuran and the esterifying alcohol and which is separated by distillation into the products of value and the esterifying alcohol, and recycling the esterifying alcohol to the esterification zone, which comprises separating the esterification product into the diester and the inert solvent by distillation under reduced pressType: GrantFiled: October 11, 2000Date of Patent: February 26, 2002Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Gerd Kaibel, Rolf Pinkos, Ralf-Thomas Rahn
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Patent number: 6320084Abstract: The invention pertains to a process for the preparation of glyceraldehyde, or an acetal or a hemiacetal thereof, characterized in that 3-butene-1,2-diol is dissolved in a lower alkanol and is subjected to ozonolysis to obtain a 3-hydroperoxy-3-alkoxy-propane-1,2-diol, which is subjected to a reductive treatment to obtain a hemiacetal of glyceraldehyde, which optionally may be converted into glyceraldehyde or an acetal or hemiacetal thereof, and to a process wherein the hemiacetal of glyceraldehyde is converted to a 3-aminopropane-1,2-diol derivative, by subjecting the hemiacetal of glyceraldehyde to a reductive treatment in the presence of ammonia or a primary or secondary amine.Type: GrantFiled: February 26, 2001Date of Patent: November 20, 2001Assignee: Akzo Nobel NVInventors: Ulrich Wecker, Manfred Josef Bergfeld
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Patent number: 6316646Abstract: A process for the continuous catalytic conversion of organic compounds, that, together with unwanted attendant materials, form a starting substance: first the organic compounds of the starting material are purposely extracted by means of condensed fluids. Then the extract, containing the condensed fluids and organic compounds as the reaction mixture is contacted with a catalyst for the catalytic conversion of the organic compounds to form a product mixture, which contains the individual products of the catalytic conversion. The product mixture is separated from the reaction mixture and the fluids employed are, optionally, conducted back for extraction.Type: GrantFiled: May 7, 1998Date of Patent: November 13, 2001Assignee: Degussa AGInventors: Thomas Tacke, Stefan Röder, Inge Beul, Steffen Laporte, Peter Panster
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Patent number: 6313358Abstract: Hexanediol is prepared by hydrogenating dialkyl adipates or mixtures which contain a dialkyl adipate as the essential component and organic halogen compounds as impurities, by a process in which, before the hydrogenation, the dialkyl adipates or the mixtures containing dialkyl adipates are passed at from 50 to 250° C. and from 1 to 100 bar over copper catalysts which have a copper content, calculated as CuO, of from 0.5 to 80% by weight, a surface area of from 5 to 1500 m2/g, a porosity of from 0.05 to 1.5 cm3/g and a copper surface area of from 0.1 to 20 m2/g, in order to remove the organic halogen compounds.Type: GrantFiled: October 11, 2000Date of Patent: November 6, 2001Assignee: BASF AktiengesellschaftInventors: Boris Breitscheidel, Rolf Pinkos, Frank Stein