Of Ether Patents (Class 568/865)
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Patent number: 11746071Abstract: Metathesis of olefins in a loop reactor having liquid reaction medium circulated therein that contains reactant olefins and homogeneous metathesis catalyst system in liquid phase. Recovery of product olefin(s) occurs after removing a liquid reactor effluent from the loop reactor, and unreacted reactant olefin(s) recovered from the liquid reactor effluent can be recycled to the loop reactor.Type: GrantFiled: October 3, 2022Date of Patent: September 5, 2023Assignee: Chevron Phillips Chemical Company LPInventors: Wei Qi, Enrique Mancillas, Jeffery C. Gee, Sean K. McLaughlin, Jared Fern, Steven Bischof, Paul Hobson
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Patent number: 10882804Abstract: This disclosure provides embodiments directed to compositions, methods, and processes to produce compounds having the structure: each of R1-R5 is selected from a hydroxyl group and hydrogen; and R1-R5 include at least one hydroxyl group and at least one hydrogen; and n=0-2. In particular, methods of the disclosure can include reacting a precursor, the precursor containing more oxygen (O) atoms than the compound, with a gas containing hydrogen (H2) in the presence of a catalyst.Type: GrantFiled: August 22, 2019Date of Patent: January 5, 2021Assignee: University of South CarolinaInventors: Blake H. MacQueen, Elizabeth Barrow, Jochen Lauterbach
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Patent number: 10029965Abstract: A process for producing a polyhydric alcohol includes a step (I) of hydrogenating hemiacetal having a specific structure to obtain a reaction solution (I), and a step (II) of adding water to the reaction solution (I) obtained in the step (I) and further conducting hydrogenation.Type: GrantFiled: June 3, 2014Date of Patent: July 24, 2018Assignee: KURARAY CO., LTD.Inventors: Shigeru Okano, Kazuyuki Yada, Yutaka Suzuki
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Patent number: 9199961Abstract: The present invention relates to a method for preparing caprolactone, comprising converting 5-hydroxymethyl-2-furfuraldehyde by hydrogenation into at least one intermediate compound selected from the group of 2,5-tetrahydrofuran-dimethanol, 1,6-hexanediol and 1,2,6-hexanetriol, and preparing caprolactone from said intermediate compound. Further, the invention relates to a method for preparing 1,2,6-hexanetriol comprising preparing 5-hydroxymethyl-2-furfaldehyde from a renewable source, converting 5-hydroxymethyl-2-furfaldehyde into 2,5-tetrahydrofuran-dimethanol and converting 2,5-tetrahydrofuran-dimethanol into 1,2,6-hexanetriol. Further, the invention relates to a method for preparing 1,6-hexanediol from 1,2,6-hexanetriol, wherein 1,2,6-hexanetriol is subjected to a ring closure reaction, thereby forming (tetrahydro-2H-pyran-2-yl)methanol, and the (tetrahydro-2H-pyran-2-yl)methanol is hydrogenated, thereby forming 1,6-hexane diol.Type: GrantFiled: March 23, 2011Date of Patent: December 1, 2015Assignee: NEDERLANDSE ORGANISATIE VOOR WETENSCHAPPELIJK ONDERZOEK (NWO)Inventors: Johannes Gerardus De Vries, Teddy, Pim Huat Phua, Ignacio Vladimiro Melián Cabrera, Hero Jan Heeres
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Patent number: 9051234Abstract: Provided by the present invention is a method for producing an alkanediol, such as 1,5-pentanediol, with a high reaction selectivity thereto by reacting a cyclic ether group-containing methanol such as tetrahydrofurfuryl alcohol by using a non-chromium catalyst not containing chromium atom. More specifically, the method is to produce an alkanediol having hydroxy groups at both molecular terminals shown by the formula (2), includes reacting a cyclic ether group-containing methanol shown by the formula (1) with hydrogen in the presence of a metal catalyst which contains copper atom, at least one co-existing atom selected from the group consisting of elements of the third to the sixth periods of the II to XIV groups (excluding chromium) in the periodical table and lanthanide elements.Type: GrantFiled: November 19, 2012Date of Patent: June 9, 2015Assignee: UBE INDUSTRIES, LTD.Inventors: Yasutaka Yoshida, Kenji Hirotsu, Takashi Doi, Kouichi Kashiwagi, Ryo Fujimoto, Ryousuke Katsura, Satoru Fujitsu
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Patent number: 9040443Abstract: Catalysts and processes for forming catalysts for use in hydrogenating acetic acid to form ethanol. In one embodiment, the catalyst comprises a first metal, a silicaceous support, and at least one metasilicate support modifier. Preferably, the first metal is selected from the group consisting of copper, iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, titanium, zinc, chromium, rhenium, molybdenum, and tungsten. In addition the catalyst may comprise a second metal preferably selected from the group consisting of copper, molybdenum, tin, chromium, iron, cobalt, vanadium, tungsten, palladium, platinum, lanthanum, cerium, manganese, ruthenium, rhenium, gold, and nickel.Type: GrantFiled: June 12, 2013Date of Patent: May 26, 2015Assignee: Celanese International CorporationInventors: Victor J. Johnston, Barbara F. Kimmich, John L. Potts, Heiko Weiner, Radmila Wollrab, James H. Zink, Josefina T. Chapman, Laiyuan Chen
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Publication number: 20150126784Abstract: A process for regenerating catalysts that have been deactivated or poisoned during hydrogenation of biomass, sugars and polysaccharides is described, in which polymerized species that have agglomerated to catalyst surfaces can be removed by means of washing the catalyst with hot water at subcritical temperatures. A feature of the process regenerates the catalysts in situ which allows the process to be adapted for used in continuous throughput reactor systems. Also described is a continuous hydrogenation process that incorporated the present regeneration process.Type: ApplicationFiled: April 17, 2013Publication date: May 7, 2015Inventor: Chi-Cheng Ma
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Patent number: 8940946Abstract: The present invention has an object to provide a method for efficiently producing high-purity 1,5-pentanediol by reacting tetrahydrofurfuryl alcohol with hydrogen. This manufacturing method for producing high-purity 1,5-pentanediol comprises: step (I): a step of obtaining a crude reaction product by a hydrogenolysis reaction of tetrahydrofurfuryl alcohol with hydrogen carried out in the presence of a copper-containing catalyst with reaction temperature of 200 to 350° C. and reaction pressure of 1 to 40 MPa until conversion rate of tetrahydrofurfuryl alcohol reaches 80% or less; step (II): a step of separating tetrahydrofurfuryl alcohol and crude 1,5-pentanediol (A) from the crude reaction product obtained in the step (I), and then, supplying recovered tetrahydrofurfuryl alcohol as a raw material for the step (I); and step (III): a step of obtaining the high-purity 1,5-pentanediol by distillation of the crude 1,5-pentanediol (A) obtained in the step (II).Type: GrantFiled: November 19, 2012Date of Patent: January 27, 2015Assignee: Ube Industries, Ltd.Inventors: Yasutaka Yoshida, Kenji Hirotsu, Ryo Fujimoto, Ryousuke Katsura, Satoru Fujitsu, Takashi Doi, Kouichi Kashiwagi
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Patent number: 8921617Abstract: A process for the preparation of 1,2-pentanediol by reaction of a starting material comprising one or both compounds from the group consisting of furfuryl alcohol and furfural with hydrogen in the presence of a first heterogeneous catalyst is described.Type: GrantFiled: May 9, 2012Date of Patent: December 30, 2014Assignee: Symrise AGInventors: Oskar Koch, Angela Köckritz, Michael Kant, Andreas Martin, Axel Schöning, Udo Armbruster, Michael Bartoszek, Sigrid Evert, Brigitte Lange, Regina Bienert
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Publication number: 20140360493Abstract: A process for converting cellulose to glucose, said process comprising the steps of: providing a hydrated molten salt; contacting the hydrated molten salt with a cellulose-containing material to form dissolved glucose; removing the dissolved glucose from the hydrated molten salt.Type: ApplicationFiled: August 22, 2014Publication date: December 11, 2014Inventors: Paul O'CONNOR, Jacob Adriaan MOULIJN, Michiel MAKKEE, Sjoerd DAAMEN, Rafael MENEGASSI DE ALMEIDA
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Patent number: 8884036Abstract: Disclosed are processes comprising contacting an aqueous reaction mixture having an initial pH between about 3 and about 6 and comprising levoglucosenone with a catalyst, and heating the reaction mixture to form a product mixture comprising 5-hydroxymethyl-2-furfural. The processes may further comprise heating the product mixture comprising 5-hydroxymethyl-2-furfural in the presence of hydrogen and a hydrogenation catalyst to form a second product mixture comprising one or more of 2,5-furandimethanol, tetrahydrofuran 2,5-dimethanol, 1,2,6-hexanetriol, 2-hydroxymethyltetrahydropyran, and 1,6-hexanediol.Type: GrantFiled: December 28, 2012Date of Patent: November 11, 2014Assignee: E I du Pont de Nemours and CompanyInventors: Wathudura Indika Namal De Silva, Joachim C Ritter, Christina S Stauffer
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Publication number: 20140330049Abstract: Biomass compaction during hydrothermal digestion of cellulosic biomass solids may become problematic, particularly as the vertical height of a cellulosic biomass charge increases. Compaction may be decreased in a horizontally configured hydrothermal digestion unit.Type: ApplicationFiled: April 29, 2014Publication date: November 6, 2014Applicant: SHELL OIL COMPANYInventors: Joseph Broun POWELL, Alouisius Nicolaas Renee BOS, Peter Anton August KLUSENER, Ingmar Hubertus Josephina PLOEMEN
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Patent number: 8846985Abstract: Disclosed herein are processes for preparing an ?,?-Cn-diol, wherein n is 5 or greater, from a feedstock comprising a Cn oxygenate. In one embodiment, the process comprises contacting the feedstock with hydrogen gas in the presence of a catalyst comprising a first metal component comprising Ni, Ir, Pt, Rh, Ru, Pd, Fe, Ag, or Au; a heteropoly acid component comprising H3[P(W3O10)4], H4[Si(W3O10)4], H4[P(Mo3O10)4], H4[Si(Mo3O10)4], Cs2.5H0.5[P(W3O10)4]Cs2.5H0.5[Si(W3O10)4], or mixtures thereof; optionally a second metal component comprising Cr, a Cr oxide, Ni, a Ni oxide, Fe, a Fe oxide, Co, a Co oxide, Mn, a Mn oxide, Mo, a Mo oxide, W, a W oxide, Re, a Re oxide, Zn, a Zn oxide, SiO2, or Al2O3; optionally at least one promoter comprising Na, K, Mg, Rb, Cs, Ca, Sr, Ba, Ce, or mixtures thereof; and optionally a support.Type: GrantFiled: April 25, 2013Date of Patent: September 30, 2014Assignee: E I du Pont de Nemours and CompanyInventors: Alan Martin Allgeier, Wathudura Indika Namal De Silva, Carl Andrew Menning, Joachim C Ritter, Sourav Kumar Sengupta
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Publication number: 20140275638Abstract: A method to make triols and diols is described. The method includes the steps of performing an aqueous-phase hydrodeoxygenation reaction on a feedstock containing a biomass-derived reactant in aqueous solution. The feedstock is contacted with a heterogeneous metal-containing bifunctional catalyst or a combination of two or more heterogeneous metal-containing catalysts that catalyze cleavage of C—C and C—O bonds, for a time, temperature, pressure, and weight hourly space velocity to yield a product mix comprising triols, diols, or combinations thereof.Type: ApplicationFiled: March 15, 2013Publication date: September 18, 2014Applicant: Wisconsin Alumni Research FoundationInventors: George W. Huber, Yong Tae Kim
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Publication number: 20140243562Abstract: The present invention provides a process for preparing 1,2-pentanediol by reacting furfuryl alcohol with hydrogen in the presence of a catalyst system. The catalyst system contains platinum oxide or contains ruthenium supported on aluminum oxide or activated carbon. The invention also relates to the respective catalysts and processes for producing the catalyst system.Type: ApplicationFiled: November 25, 2013Publication date: August 28, 2014Applicant: Evonik Industries AGInventors: Marianne OMEIS, Manfred NEUMANN, Volker BREHME, Christoph THEIS, Dorit WOLF, Peter CLAUS, Martin LUCAS, Rene ECKERT
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Patent number: 8759594Abstract: The present invention relates to a process for hydrogenating oligo- and/or polyesters obtainable by esterifying a DCS with a diol or diol mixture, said hydrogenation being performed in the presence of a catalyst whose catalyst precursor comprises copper oxide, aluminum oxide and at least one oxide of lanthanum, of iron, of tungsten, of molybdenum, of titanium or of zirconium, and to a process for preparing 1,6-hexanediol by catalytically hydrogenating ester mixtures which comprise, as main components, oligo- and polyesters of adipic acid and 6-hydroxycaproic acid, and are obtained by esterifying DCS with diols, especially 1,6-hexanediol or diol mixtures.Type: GrantFiled: March 29, 2010Date of Patent: June 24, 2014Assignee: BASF SEInventors: Olivier Abillard, Rolf Pinkos, Gerd-Dieter Tebben, Tilman Sirch, Daniel Urbanczyk, Heiko Urtel, Rolf Tompers
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Publication number: 20140121420Abstract: Hydrothermal digestion of cellulosic biomass solids may be conducted such that a glycol reaction product is formed for subsequent processing. Processing of a glycol reaction product may include a drying operation conducted prior to condensation of the glycol reaction product into higher molecular weight compounds. Methods for digesting cellulosic biomass solids to form a glycol reaction product can comprise: providing cellulosic biomass solids and a slurry catalyst in a hydrothermal digestion unit, the slurry catalyst being capable of activating molecular hydrogen; heating the cellulosic biomass solids in the hydrothermal digestion unit in the presence of the slurry catalyst, a digestion solvent, and molecular hydrogen, thereby forming a liquor phase comprising soluble carbohydrates; and performing a first catalytic reduction reaction on the soluble carbohydrates within the hydrothermal digestion unit, thereby at least partially converting the soluble carbohydrates into a reaction product comprising a glycol.Type: ApplicationFiled: October 30, 2013Publication date: May 1, 2014Applicant: SHELL OIL COMPANYInventors: Joseph Broun POWELL, Kimberly Ann JOHNSON
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Publication number: 20140066666Abstract: A process for the preparation of 1,2-pentanediol by reaction of a starting material comprising one or both compounds from the group consisting of furfuryl alcohol and furfural with hydrogen in the presence of a first heterogeneous catalyst is described.Type: ApplicationFiled: May 9, 2012Publication date: March 6, 2014Applicant: Symrise AGInventors: Oskar Koch, Angela Köckritz, Michael Kant, Andreas Martin, Axel Schöning, Udo Armbruster, Michael Bartoszek, Sigrid Evert, Brigitte Lange, Regina Bienert
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Publication number: 20140018557Abstract: The invention relates to a process for the production of ethylene oxide, comprising the steps of producing ethylene resulting in a stream comprising ethylene and ethane; producing ethylene oxide by subjecting ethylene and ethane from the stream comprising ethylene and ethane to oxidation conditions resulting in a stream comprising ethylene oxide, unconverted ethylene and ethane; and recovering ethylene oxide from the stream comprising ethylene oxide, unconverted ethylene and ethane.Type: ApplicationFiled: January 23, 2012Publication date: January 16, 2014Inventor: Michiel Johannes Franciscus Maria Verhaak
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Publication number: 20140018556Abstract: The invention relates to a process for the production of ethylene oxide, comprising the steps of: producing ethylene by converting a stream comprising an oxygenate into a stream comprising ethylene and ethane; producing ethylene oxide by subjecting ethylene and ethane from the stream comprising ethylene and ethane to oxidation conditions resulting in a stream comprising ethylene oxide, unconverted ethylene and ethane; and recovering ethylene oxide from the stream comprising ethylene oxide, unconverted ethylene and ethane.Type: ApplicationFiled: January 23, 2012Publication date: January 16, 2014Inventors: Michiel Johannes Franciscus Maria Verhaak, Jeroen Van Westrenen
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Patent number: 8501652Abstract: Catalysts and processes for forming catalysts for use in hydrogenating acetic acid to form ethanol. In one embodiment, the catalyst comprises a first metal, a silicaceous support, and at least one metasilicate support modifier. Preferably, the first metal is selected from the group consisting of copper, iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, titanium, zinc, chromium, rhenium, molybdenum, and tungsten. In addition the catalyst may comprise a second metal preferably selected from the group consisting of copper, molybdenum, tin, chromium, iron, cobalt, vanadium, tungsten, palladium, platinum, lanthanum, cerium, manganese, ruthenium, rhenium, gold, and nickel.Type: GrantFiled: February 2, 2010Date of Patent: August 6, 2013Assignee: Celanese International CorporationInventors: Victor J. Johnston, Laiyuan Chen, Barbara F. Kimmich, Josefina T. Chapman, James H. Zink, Heiko Weiner, John L. Potts, Radmila Jevtic
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Publication number: 20130172586Abstract: Disclosed herein are processes comprising contacting isosorbide with hydrogen in the presence of a first hydrogenation catalyst to form a first product mixture comprising tetrahydrofuran-2,5-dimethanol. The processes can further comprise heating the first product mixture in the presence of hydrogen and a second hydrogenation catalyst to form a second product mixture comprising 1,6-hexanediol. The first and second hydrogenation catalysts can be the same or different.Type: ApplicationFiled: December 28, 2012Publication date: July 4, 2013Applicant: E I DU PONT DE NEMOURS AND COMPANYInventor: E I DU PONT DE NEMOURS AND COMPANY
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Publication number: 20130137863Abstract: The present invention relates to a method for preparing caprolactone, comprising converting 5-hydroxymethyl-2-furfuraldehyde by hydrogenation into at least one intermediate compound selected from the group of 2,5-tetrahydrofuran-dimethanol, 1,6-hexanediol and 1,2,6-hexanetriol,and preparing caprolactone from said intermediate compound. Further, the invention relates to a method for preparing 1,2,6-hexanetriol comprising preparing 5-hydroxymethyl-2-furfaldehyde from a renewable source, converting 5-hydroxymethyl-2-furfaldehyde into 2,5-tetrahydrofuran-dimethanol and converting 2,5-tetrahydrofuran-dimethanol into 1,2,6-hexanetriol. Further, the invention relates to a method for preparing 1,6-hexanediol from 1,2,6-hexanetriol, wherein 1,2,6-hexanetriol is subjected to a ring closure reaction, thereby forming (tetrahydro-2H-pyran-2-yl)methanol, and the (tetrahydro-2H-pyran-2-yl)methanol is hydrogenated, thereby forming 1,6-hexane diol.Type: ApplicationFiled: March 23, 2011Publication date: May 30, 2013Applicant: NEDERLANDSE ORGANISATIE VOOR WETENSCHAPPELIJK ONDERZOEK (NWO)Inventors: Johannes Gerardus De Vries, Teddy, Pim Huat Phua, Ignacio Vladimiro Melián Cabrera, Hero Jan Heeres
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Patent number: 8309771Abstract: A two-stage, gas phase process for manufacturing alkylene glycol (e.g., ethylene glycol) from an alkene (e.g., ethylene), oxygen and water, the process comprising the steps of: (A) Contacting under gas phase, oxidation conditions gaseous alkene and oxygen over a heterogeneous oxidation catalyst to produce a gaseous oxidation product comprising alkylene oxide, water and unreacted alkene; (B) Contacting under gas phase, hydrolysis conditions the gaseous oxidation product of (A) with added water over a heterogeneous hydrolysis catalyst to produce a gaseous alkylene glycol and unreacted alkene; and (C) Recycling the unreacted alkene of (B) to (A). The hydrolysis catalyst is selected from the group consisting of hydrotalcites, metal-loaded zeolites, phosphates, and metal-loaded ion-exchanged molecular sieves.Type: GrantFiled: July 31, 2009Date of Patent: November 13, 2012Assignee: Dow Technology Investments LLCInventors: Joseph C. Noronha, Elbert J. Campbell, Brian T. Keen, Dick A. Nagaki, Hwaili Soo, David A. Spears, John F. Szul
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Publication number: 20120283487Abstract: Tungsten carbide catalysts are used in preparation of ethylene glycol by hydrogenating degradation of cellulose. The catalyst includes tungsten carbide as main catalytic active component, added with small amount of one or more transition metals such as nickel, cobalt, iron, ruthenium, rhodium, palladium, osmium, iridium, platinum, and copper as the second metal, supported on one or more porous complex supports such as active carbon, alumina, silica, titanium dioxide, silicon carbide, zirconium oxide, for conversion of cellulose to ethylene glycol. The catalyst realizes high efficiency, high selectivity, and high yield in the conversion of cellulose to ethylene glycol at the temperature of 120-300° C., hydrogen pressure of 1-10 MPa, and hydrothermal conditions. Compared to the existing industrial synthetic method of ethylene glycol using ethylene as feedstock, the invention has the advantages of using renewable raw material resources, environment friendly process, and excellent atom economy.Type: ApplicationFiled: June 29, 2012Publication date: November 8, 2012Applicant: Dalian Institute of Chemical Physics, Chinese Academy of SciencesInventors: Tao Zhang, Na JI, Mingyuan Zheng, Aiqin WANG, Yuying SHU, Xiaodong WANG, Jingguang CHEN
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Patent number: 8138381Abstract: The present invention provides a method for recovering a natural gas contaminated with high levels of carbon dioxide. A gas containing methane and carbon dioxide is extracted from a reservoir containing natural gas, where carbon dioxide comprises greater than 40 vol. % of the extracted gas. The extracted gas is scrubbed with a wash effective to produce a washed extracted gas containing less carbon dioxide than the extracted gas and at least 20 vol. % carbon dioxide. The washed extracted gas is oxidized with an oxygen containing gas in the presence of a partial oxidation catalyst to produce an oxidation product gas containing hydrogen, carbon monoxide, and carbon dioxide. The oxidation product gas is then utilized to produce a liquid methanol product.Type: GrantFiled: January 5, 2010Date of Patent: March 20, 2012Assignee: Shell Oil CompanyInventors: Mahendra Ladharam Joshi, Jingyu Cui, Frederik Arnold Buhrman, Scott Lee Wellington, Stanley Nemec Milam, Rogier Maarten Kamerbeek
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Publication number: 20100267973Abstract: A method for enhancing the efficiency of a rhenium-promoted epoxidation catalyst is provided. Advantageously, the method may be carried out in situ, i.e., within the epoxidation process, and in fact, may be carried out during production of the desired epoxide. As such, a method for the epoxidation of alkylenes incorporating the efficiency-enhancing method is also provided, as is a method for using the alkylene oxides so produced for the production of 1,2-diols, 1,2-carbonates, 1,2-diol ethers, or alkanolamines.Type: ApplicationFiled: April 5, 2010Publication date: October 21, 2010Applicant: DOW TECHNOLOGY INVESTMENTS LLCInventors: Albert C. Liu, Liping Zhang
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Publication number: 20100234586Abstract: A process for converting cellulose to glucose, said process comprising the steps of: providing a hydrated molten salt; contacting the hydrated molten salt with a cellulose-containing material to form dissolved glucose; removing the dissolved glucose from the hydrated molten salt.Type: ApplicationFiled: June 24, 2008Publication date: September 16, 2010Applicant: BIOeCON International Holding N.V.Inventors: Paul O'Connor, Jacob Adriaan Moulijn, Michiel Makkee, Sjoerd Daamen
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Patent number: 7754926Abstract: The present invention reacts an allyl alcohol with an alcohol compound in the presence of a catalyst containing at least one element selected from the group consisting of elements of the group III, lanthanoid elements and actinoid elements of the Periodic Table, as depicted in the following reaction and provides a method for efficiently producing 3-alkoxy-1-propanol in a single step using an alcohol as a starting material.Type: GrantFiled: February 4, 2005Date of Patent: July 13, 2010Assignee: Showa Denko K.K.Inventors: Nobuyuki Kibino, Yasushi Kadowaki, Masaaki Sakai, Yukiharu Hetsugi
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Publication number: 20100036177Abstract: Methods for the removal of volatilizable components from a natural oil-based product having a high viscosity are provided. The natural oil-based product can be a high viscosity oligomeric polyol prepared from epoxidized vegetable oils. The method involves heating a natural oil-based product to relatively low temperatures (about 225° C. or below) and then exposing the natural oil-based product to an environment comprising a reduced pressure and a sparging vapor. In particular, deodorization methods are provided. In deodorization processes, odor components such as hexanal, nonanal, and decanal are substantially removed from the natural oil-based product. The lower temperature process provides effective removal of the volatilizable components, while maintaining desirable product properties, such as the clarity of the product, and chemical and physical properties similar to that of the starting material.Type: ApplicationFiled: November 16, 2007Publication date: February 11, 2010Inventor: Derik J. Ward
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Patent number: 7560601Abstract: Provided is a method for producing 3-methyl-1,5-pentanediol by hydrogenating 2-hydroxy-4-methyltetrahydropyran in the presence of a hydrogenation catalyst, characterized in that the hydrogenation is further carried out in the presence of a basic compound. By this method, in producing MPD by hydrogenation of MHP, high-purity MPD can be produced by effectively suppressing generation of by-products such as MPAE and MVL even when a known hydrogenation catalyst is used.Type: GrantFiled: April 24, 2007Date of Patent: July 14, 2009Assignee: Kuraray Co., Ltd.Inventors: Kenichi Hino, Kazuyuki Yada, Keisuke Saeki
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Patent number: 7230145Abstract: A process for producing a both end-hydroxyl group-terminated diol, wherein an epoxy alcohol represented by the general formula (1) is subjected to a hydrogenolysis reaction in the presence of a catalyst for producing both end-hydroxyl group terminated diols, which catalyst contains at least one element selected from the group consisting of Group V elements, Group VI elements, Group VII elements, Group VIII elements, Group IX elements, Group X elements, and Group XI elements in the periodic table, in the presence of at least one solvent selected from the group consisting of ethers, esters, aromatic hydrocarbon compounds, alicyclic hydrocarbon compounds and aliphatic hydrocarbon compounds, to thereby obtain a both end-hydroxyl group-terminated diol represented by general formula (2). General formula (1) and (2) are as described in the specification.Type: GrantFiled: June 28, 2004Date of Patent: June 12, 2007Assignee: Showa Denko K.K.Inventors: Yasushi Kadowaki, Masato Kaneda, Hiroshi Uchida
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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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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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Patent number: 6555720Abstract: A method and system for producing 1,4-butanediol (1,4-BG), and optionally additionally tetrahydrofuran (THF), that promotes more efficient usage of water (H2O) is provided. In one aspect, the method is comprised of supplying at least one feed stream including 1,4-diacetoxybutane (1,4-DAB), 1,4-hydroxyacetoxybutane (1,4-HAB) and H2O to at least one reactor. 1,4-DAB, 1,4-HAB and H2O are reacted in the reactor to produce at least one effluent stream that includes 1,4-BG, 1,4-HAB, H2O, unreacted 1,4-DAB and acetic acid. The effluent stream is supplied to a separation system having one or more separators where at least a portion of the 1,4-HAB is removed from the effluent stream and recycled back to the reaction. Alternatively, 1,4-HAB may be supplied directly to the reactor as a feed stream, or a combination of feed stream and recycled 1,4-HAB may be used.Type: GrantFiled: April 28, 2000Date of Patent: April 29, 2003Assignee: Mitsubishi Chemical CorporationInventors: Lionel O'Young, Kazuyuki Ookubo, Nobuo Toratani, Hiroshi Iwasaka
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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: 6350714Abstract: The present invention relates to a process for preparing a catalyst by activating a catalytic composition which comprises a) at least one metal of group IB or IIB or a compound thereof, b) where appropriate a carrier which comprises treating the composition with an alkyne of the general formula I R1—C≡C—R2 (I) in which R1 is alkyl, cycloalkyl, aryl, hydroxyalkyl, haloalkyl, alkoxy or alkoxyalkyl, R2 is a hydrogen atom, alkyl, cycloalkyl or aryl, and a carbonyl compound of the general formula II in which R3 and R4 are, independently of one another, a hydrogen atom, alkyl, haloalkyl, cycloalkyl or aryl, to catalysts obtainable by this process, and to alkynylations and aminoalkylations employing these catalysts.Type: GrantFiled: May 31, 2000Date of Patent: February 26, 2002Assignee: BASF AktiengesellschaftInventors: Arnd Böttcher, Jochem Henkelmann, Thomas Preiss, Melanie Brunner
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Patent number: 5981811Abstract: A process for the preparation of a polyprenol represented by formula (1): ##STR1## where Y and Z individually represent a hydrogen atom or are coupled together to form a carbon-carbon bond; R represents a hydrogen atom or a protective group for a hydroxyl group, and n is 0 or an integer not less than 1, by reacting an organic complex of an alkali metal with a compound represented by formula (2): ##STR2## where either V represents a halogen atom, while W and X are coupled together to form a carbon-carbon bond, or X represents a halogen atom, while V and W are coupled together to form a carbon-carbon bond; A represents a protective group for a hydroxyl group, and Y, Z and n are as defined above.Type: GrantFiled: April 27, 1998Date of Patent: November 9, 1999Assignee: Kuraray Co., Ltd.Inventors: Katuji Ujita, Koichi Kanehira, Yoshin Tamai
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Patent number: 5952533Abstract: 1,6-Hexanediol is prepared bya) Reacting epoxybutadiene in the presence of a metathesis catalyst with elimination of ethene to give bisepoxyhexatrienes of the formulae Ia and Ib ##STR1## and b) hydrogenating these bisepoxyhexatrienes with hydrogen to give 1,6-hexanediol.Type: GrantFiled: June 2, 1998Date of Patent: September 14, 1999Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Detlef Kratz, Rolf Pinkos, Martin Schafer, Arthur Hohn
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Patent number: 5945571Abstract: Described is a method of producing 1,4-butanediol, the method calling for 2,3-dihydrofuran to be decomposed in a single stage over a hydrogenation catalyst in the presence of water and hydrogen at a temperature of 20 to 300.degree. C. and a pressure of 1 to 300 bar and in neutral or acid conditions.Type: GrantFiled: December 27, 1996Date of Patent: August 31, 1999Assignee: BASF AktiengesellschaftInventors: Rolf Pinkos, Rolf Fischer, Boris Breitscheidel, Peter Polanek
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Patent number: 5905159Abstract: 1,4-butanediol and THF are prepared from furan by a process which comprises converting furan in the presence of water and hydrogen but in the absence of a water-soluble acid in a single stage over a hydrogenation catalyst, the hydrogenation catalyst containing at least one element of subgroup I, V, VI, VII or VIII in the form of a compound or in elemental form and the restriction that the catalyst does not contain nickel alone being applicable.Type: GrantFiled: September 16, 1997Date of Patent: May 18, 1999Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Rolf Pinkos
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Patent number: 5583270Abstract: Disclosed are the improvements of a process for the preparation of 1,3-butylene glycol, in which the generation of by-products can be decreased, resulting in being capable of productiong 1,3-butylene glycol having high quality (e.g. an odorless, so-called "cosmetic grade") at a high-yield.Type: GrantFiled: June 23, 1994Date of Patent: December 10, 1996Assignee: Daicel Chemical Industries, Ltd.Inventor: Kazuhisa Nishiguchi
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Patent number: 5508394Abstract: Esters of citric acid or acetylcitric anhydride with compounds of at least 3 OH groups selected from the group consisting of polyglycerol, sugarcarboxylic acids, alkyl glucosides, derivatives of oligosaccharides, aminosorbitol, aminodisorbitol, glucosamine, triethanolamine and trishydroxyethylmelamine, each OH group of the alcohol component of the esters being esterified on average with from 0.15 to 1 molecule of citric acid or acetylcitric anhydride, are useful as additives in low-phosphate or phosphate-free detergents.Type: GrantFiled: September 16, 1993Date of Patent: April 16, 1996Assignee: BASF AktiengesellschaftInventors: Elisabeth Kappes, Alfred Oftring, Richard Baur, Alexander Kud, Dieter Boeckh, Heinrich Hartmann, Volker Schwendemann
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Patent number: 5481048Abstract: A copper-containing hydrogenation reaction catalyst is prepared by reducing a precursor of a copper-containing catalyst usable in hydrogenation reaction with hydrogen gas or a mixture of hydrogen and an inert gas by liquid phase reduction in a stream of a solvent in the temperature range of from 50.degree. to 140.degree. C. An alcohol is produced using the catalyst thus obtained in a fixed bed continuous reaction system.Type: GrantFiled: December 13, 1994Date of Patent: January 2, 1996Assignee: Kao CorporationInventors: Kiyoshi Tsukada, Yasuyuki Hattori, Taku Mimura
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Patent number: 5414138Abstract: A process for producing 2-formyl-1,4-butanediol comprises effecting reaction of 2-butene-1,4-diol with hydrogen and carbon monoxide in the presence of:(a) a rhodium compound,(b) a tris(substituted aryl) phosphite having an electronic parameter, .nu.-value, of 2,080 to 2,090 cm.sup.-1 and a steric parameter, .theta.-value, of 135.degree. to 190.degree. and being represented by the formula P(OR).sub.3wherein each of R's, which may be the same or different, represents a substituted aryl group having at least 7 carbon atoms, and(c) a bis (diphenylphosphino) alkane represented by the formula Ph.sub.2 P-(CH.sub.2)n-PPh.sub.2 where n n is an integer of 2 to 6, andat a temperature of not more than 80.degree. C.Type: GrantFiled: June 2, 1994Date of Patent: May 9, 1995Assignee: Kuraray Company Ltd.Inventors: Toshihiro Omatsu, Yasuo Tokitoh
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Patent number: 5395992Abstract: Disclosed is the synthesis of terminal diols, which are organic intermediates used in order to produce polymeric materials, by starting from terminal diolefins, which synthesis is based on the oxidation of diolefins to yield diepoxides, in a double-phase aqueous-organic system with hydrogen peroxide and in the presence of catalysts soluble in the organic phase, followed by a reaction of reduction of the resulting diepoxides.Type: GrantFiled: February 8, 1993Date of Patent: March 7, 1995Assignee: Enichem S.p.A.Inventors: Marco Ricci, Francesco Gementi, Francesco Panella, Cecilia Querci, Raffaele Ungarelli
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Patent number: 5364987Abstract: 1,3-propanediol (PD) is obtained by hydration of acrolein to 3-hydroxypropionaldehyde (HPA) with subsequent catalytic hydrogenation; 3,3'-oxybis-1-propanol (OD) occurs as a yield-reducing by-product. Disclosed is a process which increases the 1,3-propanediol yield. The OD which is separated by distillation during treatment of the reaction mixture containing PD and OD is treated in aqueous solution at from 100 to 300.degree. C. with an acid solid catalyst, in particular an acid zeolite, and the reaction mixture from which the solid catalyst has been removed is returned into the treatment stage of the reaction mixture containing PD and OD.Type: GrantFiled: July 6, 1993Date of Patent: November 15, 1994Assignee: Degussa AktiengesellschaftInventors: Thomas Haas, Dietrich Arntz
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Patent number: 5345004Abstract: Disclosed are the improvements of a process for the preparation of 1,3-butylene glycol, in which the generation of by-products can be decreased, resulting in being capable of producing 1,3-butylene glycol having high quality (e.g. an odorless, so-called "cosmetic grade") at a high-yield.Type: GrantFiled: December 8, 1993Date of Patent: September 6, 1994Assignee: Daicel Chemical Industries, Ltd.Inventor: Kazuhisa Nishiguchi
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Patent number: 5243095Abstract: In one embodiment, the invention relates to a catalyst in powdered form comprising the oxides of copper, iron, aluminum and manganese wherein the atomic ratio of copper to iron is at least 1:1. In another embodiment, the invention relates to a process for preparing such hydrogenation catalysts which comprises the steps of(A) preparing a first aqueous solution containing at least one water-soluble copper salt, at least one water-soluble iron salt, and at least one water-soluble manganese salt;(B) preparing a second solution containing at least one water-soluble basic aluminum salt and at least one alkaline precipitating agent;(C) mixing the first and second solutions wherein an insoluble solid is formed;(D) recovering the soluble solid; and(E) calcining the recovered solid to form the desired catalyst.The invention also relates to a process for hydrogenating aldehydes, ketones, carboxylic acids and carboxylic acid esters.Type: GrantFiled: April 24, 1992Date of Patent: September 7, 1993Assignee: Engelhard CorporationInventors: Brian D. Roberts, Deepak S. Thakur, Thomas J. Sullivan, Robert A. Plundo
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Patent number: 5210337Abstract: Rhenium has been found to be formaldehyde resistant catalyst and is thus useful in the catalytic hydrogenation of carbonyls, acetals and esters to alcohols when the reaction medium contains formaldehyde as a reactant or impurity. Also, rhenium is a useful catalyst in the hydrogenolysis of acylic acetals to alcohols.Type: GrantFiled: March 28, 1990Date of Patent: May 11, 1993Assignee: Hoechst Celanese CorporationInventor: Jerry A. Broussard