Of Ether Patents (Class 568/865)
  • Patent number: 11746071
    Abstract: 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: Grant
    Filed: October 3, 2022
    Date of Patent: September 5, 2023
    Assignee: Chevron Phillips Chemical Company LP
    Inventors: Wei Qi, Enrique Mancillas, Jeffery C. Gee, Sean K. McLaughlin, Jared Fern, Steven Bischof, Paul Hobson
  • Patent number: 10882804
    Abstract: 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: Grant
    Filed: August 22, 2019
    Date of Patent: January 5, 2021
    Assignee: University of South Carolina
    Inventors: Blake H. MacQueen, Elizabeth Barrow, Jochen Lauterbach
  • Patent number: 10029965
    Abstract: 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: Grant
    Filed: June 3, 2014
    Date of Patent: July 24, 2018
    Assignee: KURARAY CO., LTD.
    Inventors: Shigeru Okano, Kazuyuki Yada, Yutaka Suzuki
  • Patent number: 9199961
    Abstract: 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: Grant
    Filed: March 23, 2011
    Date of Patent: December 1, 2015
    Assignee: NEDERLANDSE ORGANISATIE VOOR WETENSCHAPPELIJK ONDERZOEK (NWO)
    Inventors: Johannes Gerardus De Vries, Teddy, Pim Huat Phua, Ignacio Vladimiro Melián Cabrera, Hero Jan Heeres
  • Patent number: 9051234
    Abstract: 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: Grant
    Filed: November 19, 2012
    Date of Patent: June 9, 2015
    Assignee: UBE INDUSTRIES, LTD.
    Inventors: Yasutaka Yoshida, Kenji Hirotsu, Takashi Doi, Kouichi Kashiwagi, Ryo Fujimoto, Ryousuke Katsura, Satoru Fujitsu
  • Patent number: 9040443
    Abstract: 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: Grant
    Filed: June 12, 2013
    Date of Patent: May 26, 2015
    Assignee: Celanese International Corporation
    Inventors: Victor J. Johnston, Barbara F. Kimmich, John L. Potts, Heiko Weiner, Radmila Wollrab, James H. Zink, Josefina T. Chapman, Laiyuan Chen
  • Publication number: 20150126784
    Abstract: 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: Application
    Filed: April 17, 2013
    Publication date: May 7, 2015
    Inventor: Chi-Cheng Ma
  • Patent number: 8940946
    Abstract: 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: Grant
    Filed: November 19, 2012
    Date of Patent: January 27, 2015
    Assignee: Ube Industries, Ltd.
    Inventors: Yasutaka Yoshida, Kenji Hirotsu, Ryo Fujimoto, Ryousuke Katsura, Satoru Fujitsu, Takashi Doi, Kouichi Kashiwagi
  • Patent number: 8921617
    Abstract: 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: Grant
    Filed: May 9, 2012
    Date of Patent: December 30, 2014
    Assignee: Symrise AG
    Inventors: Oskar Koch, Angela Köckritz, Michael Kant, Andreas Martin, Axel Schöning, Udo Armbruster, Michael Bartoszek, Sigrid Evert, Brigitte Lange, Regina Bienert
  • Publication number: 20140360493
    Abstract: 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: Application
    Filed: August 22, 2014
    Publication date: December 11, 2014
    Inventors: Paul O'CONNOR, Jacob Adriaan MOULIJN, Michiel MAKKEE, Sjoerd DAAMEN, Rafael MENEGASSI DE ALMEIDA
  • Patent number: 8884036
    Abstract: 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: Grant
    Filed: December 28, 2012
    Date of Patent: November 11, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Wathudura Indika Namal De Silva, Joachim C Ritter, Christina S Stauffer
  • Publication number: 20140330049
    Abstract: 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: Application
    Filed: April 29, 2014
    Publication date: November 6, 2014
    Applicant: SHELL OIL COMPANY
    Inventors: Joseph Broun POWELL, Alouisius Nicolaas Renee BOS, Peter Anton August KLUSENER, Ingmar Hubertus Josephina PLOEMEN
  • Patent number: 8846985
    Abstract: 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: Grant
    Filed: April 25, 2013
    Date of Patent: September 30, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Alan Martin Allgeier, Wathudura Indika Namal De Silva, Carl Andrew Menning, Joachim C Ritter, Sourav Kumar Sengupta
  • Publication number: 20140275638
    Abstract: 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: Application
    Filed: March 15, 2013
    Publication date: September 18, 2014
    Applicant: Wisconsin Alumni Research Foundation
    Inventors: George W. Huber, Yong Tae Kim
  • Publication number: 20140243562
    Abstract: 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: Application
    Filed: November 25, 2013
    Publication date: August 28, 2014
    Applicant: Evonik Industries AG
    Inventors: Marianne OMEIS, Manfred NEUMANN, Volker BREHME, Christoph THEIS, Dorit WOLF, Peter CLAUS, Martin LUCAS, Rene ECKERT
  • Patent number: 8759594
    Abstract: 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: Grant
    Filed: March 29, 2010
    Date of Patent: June 24, 2014
    Assignee: BASF SE
    Inventors: Olivier Abillard, Rolf Pinkos, Gerd-Dieter Tebben, Tilman Sirch, Daniel Urbanczyk, Heiko Urtel, Rolf Tompers
  • Publication number: 20140121420
    Abstract: 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: Application
    Filed: October 30, 2013
    Publication date: May 1, 2014
    Applicant: SHELL OIL COMPANY
    Inventors: Joseph Broun POWELL, Kimberly Ann JOHNSON
  • Publication number: 20140066666
    Abstract: 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: Application
    Filed: May 9, 2012
    Publication date: March 6, 2014
    Applicant: Symrise AG
    Inventors: Oskar Koch, Angela Köckritz, Michael Kant, Andreas Martin, Axel Schöning, Udo Armbruster, Michael Bartoszek, Sigrid Evert, Brigitte Lange, Regina Bienert
  • Publication number: 20140018557
    Abstract: 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: Application
    Filed: January 23, 2012
    Publication date: January 16, 2014
    Inventor: Michiel Johannes Franciscus Maria Verhaak
  • Publication number: 20140018556
    Abstract: 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: Application
    Filed: January 23, 2012
    Publication date: January 16, 2014
    Inventors: Michiel Johannes Franciscus Maria Verhaak, Jeroen Van Westrenen
  • Patent number: 8501652
    Abstract: 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: Grant
    Filed: February 2, 2010
    Date of Patent: August 6, 2013
    Assignee: Celanese International Corporation
    Inventors: Victor J. Johnston, Laiyuan Chen, Barbara F. Kimmich, Josefina T. Chapman, James H. Zink, Heiko Weiner, John L. Potts, Radmila Jevtic
  • Publication number: 20130172586
    Abstract: 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: Application
    Filed: December 28, 2012
    Publication date: July 4, 2013
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventor: E I DU PONT DE NEMOURS AND COMPANY
  • Publication number: 20130137863
    Abstract: 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: Application
    Filed: March 23, 2011
    Publication date: May 30, 2013
    Applicant: NEDERLANDSE ORGANISATIE VOOR WETENSCHAPPELIJK ONDERZOEK (NWO)
    Inventors: Johannes Gerardus De Vries, Teddy, Pim Huat Phua, Ignacio Vladimiro Melián Cabrera, Hero Jan Heeres
  • Patent number: 8309771
    Abstract: 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: Grant
    Filed: July 31, 2009
    Date of Patent: November 13, 2012
    Assignee: Dow Technology Investments LLC
    Inventors: Joseph C. Noronha, Elbert J. Campbell, Brian T. Keen, Dick A. Nagaki, Hwaili Soo, David A. Spears, John F. Szul
  • Publication number: 20120283487
    Abstract: 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: Application
    Filed: June 29, 2012
    Publication date: November 8, 2012
    Applicant: Dalian Institute of Chemical Physics, Chinese Academy of Sciences
    Inventors: Tao Zhang, Na JI, Mingyuan Zheng, Aiqin WANG, Yuying SHU, Xiaodong WANG, Jingguang CHEN
  • Patent number: 8138381
    Abstract: 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: Grant
    Filed: January 5, 2010
    Date of Patent: March 20, 2012
    Assignee: Shell Oil Company
    Inventors: Mahendra Ladharam Joshi, Jingyu Cui, Frederik Arnold Buhrman, Scott Lee Wellington, Stanley Nemec Milam, Rogier Maarten Kamerbeek
  • Publication number: 20100267973
    Abstract: 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: Application
    Filed: April 5, 2010
    Publication date: October 21, 2010
    Applicant: DOW TECHNOLOGY INVESTMENTS LLC
    Inventors: Albert C. Liu, Liping Zhang
  • Publication number: 20100234586
    Abstract: 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: Application
    Filed: June 24, 2008
    Publication date: September 16, 2010
    Applicant: BIOeCON International Holding N.V.
    Inventors: Paul O'Connor, Jacob Adriaan Moulijn, Michiel Makkee, Sjoerd Daamen
  • Patent number: 7754926
    Abstract: 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: Grant
    Filed: February 4, 2005
    Date of Patent: July 13, 2010
    Assignee: Showa Denko K.K.
    Inventors: Nobuyuki Kibino, Yasushi Kadowaki, Masaaki Sakai, Yukiharu Hetsugi
  • Publication number: 20100036177
    Abstract: 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: Application
    Filed: November 16, 2007
    Publication date: February 11, 2010
    Inventor: Derik J. Ward
  • Patent number: 7560601
    Abstract: 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: Grant
    Filed: April 24, 2007
    Date of Patent: July 14, 2009
    Assignee: Kuraray Co., Ltd.
    Inventors: Kenichi Hino, Kazuyuki Yada, Keisuke Saeki
  • Patent number: 7230145
    Abstract: 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: Grant
    Filed: June 28, 2004
    Date of Patent: June 12, 2007
    Assignee: Showa Denko K.K.
    Inventors: Yasushi Kadowaki, Masato Kaneda, Hiroshi Uchida
  • Patent number: 6750373
    Abstract: 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: Grant
    Filed: May 15, 2002
    Date of Patent: June 15, 2004
    Assignee: Shell Oil Company
    Inventors: John Frederick Knifton, Talmadge Gail James, Lynn Henry Slaugh, Kevin Dale Allen, Paul Richard Weider, Joseph Broun Powell
  • Patent number: 6586643
    Abstract: 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: Grant
    Filed: May 15, 2002
    Date of Patent: July 1, 2003
    Assignee: Shell Oil Company
    Inventors: John Frederick Knifton, Talmadge Gail James, Kevin Dale Allen, Paul Richard Weider, Joseph Broun Powell, Lynn Henry Slaugh, Timothy Williams
  • Patent number: 6555720
    Abstract: 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: Grant
    Filed: April 28, 2000
    Date of Patent: April 29, 2003
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Lionel O'Young, Kazuyuki Ookubo, Nobuo Toratani, Hiroshi Iwasaka
  • Patent number: 6403845
    Abstract: 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: Grant
    Filed: July 25, 2000
    Date of Patent: June 11, 2002
    Inventors: Joachim Pfeffinger, Peter Wahl, Jan Nouwen, Karsten Eller, Arthur Höhn, Jürgen Hunger
  • Patent number: 6350714
    Abstract: 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: Grant
    Filed: May 31, 2000
    Date of Patent: February 26, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Arnd Böttcher, Jochem Henkelmann, Thomas Preiss, Melanie Brunner
  • Patent number: 5981811
    Abstract: 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: Grant
    Filed: April 27, 1998
    Date of Patent: November 9, 1999
    Assignee: Kuraray Co., Ltd.
    Inventors: Katuji Ujita, Koichi Kanehira, Yoshin Tamai
  • Patent number: 5952533
    Abstract: 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: Grant
    Filed: June 2, 1998
    Date of Patent: September 14, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Detlef Kratz, Rolf Pinkos, Martin Schafer, Arthur Hohn
  • Patent number: 5945571
    Abstract: 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: Grant
    Filed: December 27, 1996
    Date of Patent: August 31, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Pinkos, Rolf Fischer, Boris Breitscheidel, Peter Polanek
  • Patent number: 5905159
    Abstract: 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: Grant
    Filed: September 16, 1997
    Date of Patent: May 18, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Rolf Pinkos
  • Patent number: 5583270
    Abstract: 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: Grant
    Filed: June 23, 1994
    Date of Patent: December 10, 1996
    Assignee: Daicel Chemical Industries, Ltd.
    Inventor: Kazuhisa Nishiguchi
  • Patent number: 5508394
    Abstract: 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: Grant
    Filed: September 16, 1993
    Date of Patent: April 16, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Elisabeth Kappes, Alfred Oftring, Richard Baur, Alexander Kud, Dieter Boeckh, Heinrich Hartmann, Volker Schwendemann
  • Patent number: 5481048
    Abstract: 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: Grant
    Filed: December 13, 1994
    Date of Patent: January 2, 1996
    Assignee: Kao Corporation
    Inventors: Kiyoshi Tsukada, Yasuyuki Hattori, Taku Mimura
  • Patent number: 5414138
    Abstract: 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: Grant
    Filed: June 2, 1994
    Date of Patent: May 9, 1995
    Assignee: Kuraray Company Ltd.
    Inventors: Toshihiro Omatsu, Yasuo Tokitoh
  • Patent number: 5395992
    Abstract: 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: Grant
    Filed: February 8, 1993
    Date of Patent: March 7, 1995
    Assignee: Enichem S.p.A.
    Inventors: Marco Ricci, Francesco Gementi, Francesco Panella, Cecilia Querci, Raffaele Ungarelli
  • Patent number: 5364987
    Abstract: 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: Grant
    Filed: July 6, 1993
    Date of Patent: November 15, 1994
    Assignee: Degussa Aktiengesellschaft
    Inventors: Thomas Haas, Dietrich Arntz
  • Patent number: 5345004
    Abstract: 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: Grant
    Filed: December 8, 1993
    Date of Patent: September 6, 1994
    Assignee: Daicel Chemical Industries, Ltd.
    Inventor: Kazuhisa Nishiguchi
  • Patent number: 5243095
    Abstract: 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: Grant
    Filed: April 24, 1992
    Date of Patent: September 7, 1993
    Assignee: Engelhard Corporation
    Inventors: Brian D. Roberts, Deepak S. Thakur, Thomas J. Sullivan, Robert A. Plundo
  • Patent number: 5210337
    Abstract: 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: Grant
    Filed: March 28, 1990
    Date of Patent: May 11, 1993
    Assignee: Hoechst Celanese Corporation
    Inventor: Jerry A. Broussard