Of Compound Containing A -coo- Group Patents (Class 568/864)
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Patent number: 12180600Abstract: A process for electrochemical conversion of carbon dioxide using a three-compartment cell provides low voltage requirements, high faradaic efficiencies, and high concentration of formic acid in product solutions. The applied voltage between anode and cathode should be less than 3.5V. Carbon dioxide may be converted to an organic acid.Type: GrantFiled: January 4, 2022Date of Patent: December 31, 2024Assignee: UOP LLCInventors: Richa Baronia, Jyoti Goel, Sachin Daulatgir Giri, Sagar Sopan Ghadage, Kuldeep Balram Mamtani
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Patent number: 11565983Abstract: Embodiments of a system and method are disclosed for obtaining high-energy fuels. In some embodiments, the system and method produces one or more fused cyclic compounds that can include one or more bridging points. The fused cyclic compounds are suitable for use as a high-energy fuels, and may be derived from biomass.Type: GrantFiled: August 27, 2021Date of Patent: January 31, 2023Assignee: Triad National Security, LLCInventors: Andrew D. Sutton, Cameron M. Moore, Orion Staples, Troy A. Semelsberger, William L. Kubic, Jr.
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Patent number: 11512035Abstract: The present disclosure provides a method for forming oxygenates from olefins which includes hydroformylation of aldehydes as a formyl source alternative to syngas. In at least one embodiment, a hydroformylation process is performed at low-temperature and at or near ambient pressure for the conversion of olefins into aldehydes, thus reducing the formation of by-products such as via double bond or skeletal isomerization of the feedstock; or via further conversion of the formed aldehydes and alcohols. In at least one embodiment, the use of gaseous olefinic products (e.g., ethylene) instead of strained olefins (e.g., norbornene) improves the control equilibria in transfer hydroformylation reactions.Type: GrantFiled: August 20, 2019Date of Patent: November 29, 2022Assignee: ExxonMobil Chemical Patents Inc.Inventors: Alex Carpenter, Andrew Wiersum, Luc Martens
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Patent number: 11492316Abstract: The present disclosure relates to the technical field of hexanediol production, and provides a production method and a production device of high-purity 1,6-hexanediol. A dipic acid and a C6 mixed alcohol are mixed to conduct esterification to obtain a product feed liquid including an adipic acid diester, and the high-purity 1,6-hexanediol is obtained through hydrogenation reduction and distillation. In addition to being used as a reaction raw material, the C6 mixed alcohol further acts as a water-carrying agent; water produced by the esterification is removed by azeotropy, thereby promoting a smooth reaction process to realize the esterification without a catalyst. The method does not need the catalyst during esterification, and the subsequent hydrogenation reduction can be directly conducted with no complicated post-treatment procedure required after the esterification.Type: GrantFiled: June 6, 2022Date of Patent: November 8, 2022Inventors: Minghe Zhou, Bihong Xu, Jieyang Xu, Jun Zhou, Zhaochang Zhou
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Patent number: 11352309Abstract: Provided is a catalyst including a metal component including a first component that is rhenium and one or more second components selected from the group consisting of silicon, gallium, germanium, and indium and a carrier on which the metal component is supported, the carrier including an oxide of a metal belonging to Group 4 of the periodic table. Also provided is an alcohol production method in which a carbonyl compound is treated using the above catalyst. It is possible to produce an alcohol by a hydrogenation reaction of a carbonyl compound with high selectivity and high efficiency while reducing side reactions.Type: GrantFiled: April 22, 2021Date of Patent: June 7, 2022Assignee: Mitsubishi Chemical CorporationInventors: Takeshi Matsuo, Yumiko Yoshikawa, Takayuki Aoshima
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Patent number: 11014863Abstract: A process for preparing C4 to C13 monohydroxy compounds from a bottom fraction arising in the distillation of a crude mixture of C4 to C13 oxo-process aldehydes from cobalt-catalyzed or rhodium-catalyzed hydroformylation, or in the distillation of a crude mixture of C4 to C13 oxo-process alcohols, which comprises contacting the bottom fraction in the presence of hydrogen with a catalyst comprising copper oxide and aluminum oxide, at a temperature of 150° C. to 300° C. and a pressure of 20 bar to 300 bar and subjecting the resulting crude hydrogenation product to distillation, and the amount of C4 to C13 monohydroxy compounds present in the crude hydrogenation product after the hydrogenation being greater than the amount of C4 to C13 monohydroxy compounds given stoichiometrically from the hydrogenation of the ester and aldehyde compounds present in the bottom fraction, including the C4 to C13 monohydroxy compounds still present in the bottom fraction before the hydrogenation.Type: GrantFiled: May 14, 2018Date of Patent: May 25, 2021Assignee: BASF SEInventors: Stephan Zuend, Rainer Papp, Boris Breitscheidel, Armin Lange De Oliveira
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Patent number: 10961173Abstract: A process for producing methanol includes combining a hydrogenation catalyst, hydrogen, and CO2 with a condensed phase solution comprising an amine under conditions effective to form methanol and water. A process for coproduction of methanol and a glycol includes combining an epoxide, a hydrogenation catalyst, hydrogen, and CO2 with a condensed phase solution comprising an amine under conditions effective to form methanol and a glycol.Type: GrantFiled: July 14, 2020Date of Patent: March 30, 2021Assignee: Battelle Memorial InstituteInventors: Jotheeswari Kothandaraman, David J. Heldebrant, Yuan Jiang, Robert A. Dagle
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Patent number: 10894756Abstract: The invention discloses a method for catalytically hydrogenating oxalates. In the method, an oxalate and hydrogen gas are contacted with a nanotube assembled hollow sphere catalyst, to produce a product comprising glycolate or glycol. The predominant chemical components of the catalyst include copper and silica, in which the copper is in an amount of 5 to 60% by weight of the catalyst, and the silica is in an amount of 40-95% by weight of the catalyst. The catalyst has a specific surface area of 450-500 m2/g, an average pore volume of 0.5-1 cm3/g, and an average pore diameter of 5-6 nm. The catalyst is in a structure of assembling nanotubes on hollow spheres, wherein the hollow spheres have a diameter of 50-450 nm, and a wall thickness of 10-20 nm, and the nanotubes, vertically arranged on the surfaces of the hollow spheres, have a diameter of 3-5 nm, and a length of 40-300 nm.Type: GrantFiled: March 26, 2018Date of Patent: January 19, 2021Assignee: Tianjin UniversityInventors: Xinbin Ma, Yue Wang, Dawei Yao, Jing Lv, Yujun Zhao, Shengping Wang
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Patent number: 10710949Abstract: Copper-containing, multimetallic catalysts with either a zirconia or carbon support are described which have improved utility for the hydrogenolysis of a glycerol or glycerol-containing feedstock to provide a biobased 1,2-propanediol product. specially, improved carbon-supported examples of such catalysts are described for this reaction as well as for other processes wherein hydrogen is used, with methods for maintaining the activity of these catalysts. Related treatment methods in the preparation of these improved catalysts enable the use of carbons with a desired mechanical strength but which previously lacked activity, for example, for the conversion of a glycerol or glycerol-containing feed to produce 1,2-propanediol, so that copper-containing, multi-metallic catalysts may be employed for making a biobased propylene glycol using carbon supports that previously would have not been suitable.Type: GrantFiled: July 14, 2016Date of Patent: July 14, 2020Assignee: ARCHER DANIELS MIDLAND COMPANYInventors: Kevin Martin, Josh Terrian, Bethanie Platt
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Patent number: 10450252Abstract: Process for the continuous hydrogenation of a carboxylic acid (I) to an alcohol (II) by means of hydrogen at a temperature of from 100 to 300° C. and a pressure of 10 to 33 MPa abs in a reactor tube through which axial flow occurs and which has a fixed-bed catalyst which is fixed therein and comprises at least one element from the group consisting of Re, Co and Cu, and in which the carboxylic acid (I) to be hydrogenated is present in a liquid mixture (III) comprising the carboxylic acid (I), water and alcohol (II), where the mixture (III) has an acid number of from 0.2 to 25 mg KOH/g and comprises at least 15% by weight of water and at least 20% by weight of alcohol (II) and the flow velocity of the flowing liquid calculated on the basis of the geometric cross-sectional area of the empty, catalyst-free reactor tube is from 10 to 50 m/h.Type: GrantFiled: March 29, 2017Date of Patent: October 22, 2019Assignee: BASF SEInventors: Rolf Pinkos, Stefan Rittinger, Christoph Nuebling, Olivier Abillard
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Patent number: 9944579Abstract: A phosphorus ligand-free, mild, efficient and complete catalytic hydrogenation process is for the sustainable production of terminal diols from renewable terminal dialkyl esters with improved yield. Soluble, phosphorus ligand free Ru (II)-pincer type complexes can be used as catalysts in the hydrogenation process.Type: GrantFiled: January 15, 2016Date of Patent: April 17, 2018Assignee: Council of Scientific & Industrial ResearchInventors: Ekambaram Balaraman, Manoj Kumar Sahoo
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Patent number: 9260366Abstract: 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: GrantFiled: May 20, 2015Date of Patent: February 16, 2016Assignee: Shell Oil CompanyInventors: Michael Johannes Franciscus Maria Verhaak, Jeroen Van Westrenen
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Patent number: 9227896Abstract: Disclosed is a process for the purification of a mixed diol stream. The mixed diol stream comprising two-, three-, and four-carbon diols is separated into component diols by extraction with a hydrophobic solvent mixture. The diols recovered in the extractant may be removed from the extractant stream by back extraction with water or by distillation with an azeotrope-forming agent present, preferably an azeotroping agent already present in the extractant mixture.Type: GrantFiled: March 27, 2012Date of Patent: January 5, 2016Assignee: Eastman Chemical CompanyInventor: Scott Donald Barnicki
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Patent number: 9127160Abstract: The present invention relates to a process for the work-up of polymer solutions comprising N-methyl-2-pyrrolidone and a polymer where the polymer solution is hydrogenated with hydrogen in the presence of a hydrogenation catalyst. The present invention also relates to the product obtainable from said process, and to its use for producing, in particular, polyarylene ether products.Type: GrantFiled: May 24, 2013Date of Patent: September 8, 2015Assignee: BASF SEInventors: Martin Weber, Rolf Pinkos, Thomas Vogler
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Patent number: 9114328Abstract: Disclosed is a process for producing glycolate ester oligomers. The process comprises reacting ethylene glycol and glycolic acid to produce a stream of glycolate ester oligomers and glycolic acid oligomers while simultaneously removing water. The stream of glycolate ester oligomers and glycolic acid oligomers has a low concentration of water and glycolic acid-ends, and thus is useful in a subsequent hydrogenation reaction to produce ethylene glycol.Type: GrantFiled: May 16, 2012Date of Patent: August 25, 2015Assignee: Eastman Chemical CompanyInventors: Daniel Latham Terrill, Kelley Margaret Moran, Stephen Neal Falling
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Patent number: 9102583Abstract: A process for producing ethylene glycol includes contacting an oxalate with a fluidized bed catalyst under the following conditions: a reaction temperature of from about 170 to about 270° C., a weight space velocity of oxalate of from about 0.2 to about 7 hours?1, a hydrogen/ester molar ratio of about 20˜200:1, a reaction pressure of from about 1.5 to about 10 MPa, and a reaction temperature difference T of from about 1 to about 15° C. The fluidized bed catalyst includes: a) from about 5 to about 80 parts by weight of copper and the oxide thereof, b) from about 10 to about 90 parts by weight of at least one carrier selected from silica, molecular sieve or alumina, c) from about 0.01 to about 30 parts by weight of bismuth and tungsten metallic elements or the oxides thereof, or cerium and niobium metallic elements or the oxides thereof.Type: GrantFiled: February 24, 2012Date of Patent: August 11, 2015Assignees: CHINA PETROLEUM & CHEMICAL CORPORATION, SHANGHAI RESEARCH INSTITUTE OF PETROCHEMICAL TECHNOLOGY, SINOPECInventors: Weimin Yang, Juntao Liu, Wanmin Wang, Jun Kuai
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Patent number: 9029613Abstract: Provided is an alicyclic alcohol compound which can be used as a raw material for a compound perfume, and which has excellent floral-green-like aromas which are crisp and fresh; also provided are a manufacturing method for the same, and a perfume composition which contains the alicyclic alcohol compound. An alicyclic alcohol compound having a specified structure represented by chemical formula (1) has excellent floral-green-like aromas which are crisp and fresh; and a method for manufacturing the alicyclic alcohol compound represented by chemical formula (1) by reacting, in the presence of hydrogen fluoride, 4-isopropyl-1-methylcyclohexene and carbon monoxide, isomerizing the resulting 4-isopropyl-1-methylcyclohexane carboxylic acid fluoride, thus making 2-methyl-2-(4-methylcyclohexyl)-propionyl fluoride, reacting with alcohol and acquiring a cyclohexane carbonyl compound, and then reducing the cyclohexane carbonyl compound.Type: GrantFiled: December 27, 2011Date of Patent: May 12, 2015Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Mitsuharu Kitamura, Yoshiharu Ataka, Kazuyuki Fukuda
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Patent number: 8987528Abstract: The method for hydrogenolysis of sugar or sugar alcohols comprises the steps of: mixing in the absence of any phosphine a suspension of a supported osmium catalyst, water, a sugar or sugar alcohol, and a base; pressurizing the suspension with hydrogen to a range of 30 to 90 bar at room temperature; heating the suspension to a temperature in the range of 180° C. to 250° C.; and mixing the suspension for an amount of time ranging from 1 to 6 hours.Type: GrantFiled: January 27, 2010Date of Patent: March 24, 2015Assignee: Mossi & Ghisolfi International S.a.r.l.Inventor: Milan Hronec
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Patent number: 8969632Abstract: A process for making ethylene glycol by feeding reactants including 1,2-dioxygenated organic compounds, an organometallic homogeneous catalyst, and hydrogen to a hydrogenation reactor, reacting at least a portion of the reactants with hydrogen in the presence of the organometallic homogeneous catalyst to produce a reaction product mixture containing ethylene glycol, and passivating the catalyst by contacting the catalyst with a carbon monoxide to thereby suppress the formation of by-product diols other that the ethylene glycol primary product, and suppress the formation of by-product tetrols and by-product glycolaldehyde acetals; and separating at least a portion of the ethylene glycol from the reaction product mixture.Type: GrantFiled: March 23, 2012Date of Patent: March 3, 2015Assignee: Eastman Chemical CompanyInventors: David William Norman, Jonathan Michael Penney, Peter Borden Mackenzie
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Patent number: 8962895Abstract: The present invention relates to a method for the production of ethylene glycol using a feedstock comprising an oxalate and a catalyst containing copper and/or a copper oxide, comprising contacting the feedstock with the catalyst in a reactor under the conditions of a temperature in the range from about 170 to about 270° C., a weight hourly space velocity of the oxalate in the range from about 0.2 to about 5 h?1, a molar ratio of hydrogen to the oxalate in the range from about 40:1 to about 200:1 and a reaction pressure in the range from about 1.5 to about 10 MPa, to produce an effluent containing ethylene glycol, in which the reactor is a tube-array reactor using partitioned heat exchange and adopting outer and inner tubes configured in a double-tube structure to facilitate the heat exchange of the catalyst.Type: GrantFiled: February 24, 2012Date of Patent: February 24, 2015Assignees: China Petroleum & Chemical Corporation, Shanghai Research Institute of Petrochemical Technology, SinopecInventors: Juntao Liu, Weimin Yang, Lei Li, Wanmin Wang, Linna Zhang, Haifeng Song
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Publication number: 20150025279Abstract: A process for synthesizing dodecane-1,12-diol, and by-products thereof, by the reduction of lauryl lactone produced from the oxidation of cyclododecanone.Type: ApplicationFiled: January 21, 2013Publication date: January 22, 2015Applicant: INVISTA North America S.a.r.l.Inventors: James D. Hastings, Frank E. Herkes, Gurusamy Rajendran, Qun Sun
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Publication number: 20140336418Abstract: Hydrocarbons may be formed from six carbon sugars. This process involves obtaining a quantity of a hexose sugar. The hexose sugar may be derived from biomass. The hexose sugar is reacted to form an alkali metal levulinate, an alkali metal valerate, an alkali metal 5-hydroxy pentanoate, or an alkali metal 5-alkoxy pentanoate. An anolyte is then prepared for use in a electrolytic cell. The anolyte contains the alkali metal levulinate, the alkali metal valerate, the alkali metal 5-hydroxy pentanoate, or the alkali metal 5-alkoxy pentanoate. The anolyte is then decarboxylated. This decarboxylating operates to decarboxylate the alkali metal levulinate, the alkali metal valerate, the alkali metal 5-hydroxy pentanoate, or the alkali metal 5-alkoxy pentanoate to form radicals, wherein the radicals react to form a hydrocarbon fuel compound.Type: ApplicationFiled: July 2, 2014Publication date: November 13, 2014Inventors: Sai Bhavaraju, Mukund Karanjikar
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Patent number: 8884076Abstract: The present invention relates to a process for distilling an aqueous polymethylol mixture which comprises a polymethylol of the formula (I) (HOCH2)2—C—R2??(I) in which each R is independently a further methylol group or an alkyl group having 1 to 22 carbon atoms or an aryl or aralkyl group having 6 to 22 carbon atoms, a tertiary amine, water and the adduct of tertiary amine and formic acid (amine formate), which comprises performing the distillation in a distillation column which is connected at the bottom to an evaporator, the bottom temperature being above the evaporation temperature of the monoester of formic acid and polymethylol (polymethylol formate) which forms during distillation. The present invention further relates to a composition comprising polymethylol and 1 to 10 000 ppm by weight of polymethylol formate, and to the use thereof.Type: GrantFiled: December 7, 2009Date of Patent: November 11, 2014Assignee: BASF SEInventors: Tilman Sirch, Michael Steiniger, Steffen Maas, Stefan Rittinger, Stephan Schlitter
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Publication number: 20140328748Abstract: The present application discloses complexes useful as catalysts for organic chemical synthesis including hydrogenation and dehydrogenation of unsaturated compounds or dehydrogenation of substrates. The range of hydrogenation substrate compounds includes esters, lactones, oils and fats, resulting in alcohols, diols, and triols as reaction products. The catalysts of current application can be used to catalyze a hydrogenation reaction under solvent free conditions. The present catalysts also allow the hydrogenation to proceed without added base, and it can be used in place of the conventional reduction methods employing hydrides of the main-group elements. Furthermore, the catalysts of the present application can catalyze a dehydrogenation reaction under homogenous and/or acceptorless conditions. As such, the catalysts provided herein can be useful in substantially reducing cost and improving the environmental profile of manufacturing processes for variety of chemicals.Type: ApplicationFiled: August 20, 2012Publication date: November 6, 2014Inventors: Dmitri Goussev, Denis Spasyuk
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Patent number: 8877984Abstract: Disclosed is a process for the preparation of 1,3-cyclohexanedimethanol from isophthalic acid. Isophthalic acid is esterified with (3-methylcyclohexyl)methanol and the isophthalate ester hydrogenated to 1,3-cyclohexanedimethanol in a 2-stage process. The (3-methylcyclohexyl)methanol that is formed during the hydrogenation step is recycled to the esterification reaction. Also disclosed is a method for purifying and recovering the 1,3-cyclohexanedimethanol product.Type: GrantFiled: May 21, 2012Date of Patent: November 4, 2014Assignee: Eastman Chemical CompanyInventors: Benjamin Fredrick Barton, Steven Leroy Cook, Jeff Scott Howell, Noah Glenn McMillan, Damon Bryan Shackelford, Brent Alan Tennant, Phillip Wayne Turner
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Patent number: 8865949Abstract: A hydrocarbon conversion process comprises contacting a renewable feedstock under hydroprocessing conditions with supported catalyst comprising at least one metal selected from the group consisting of Group VIII metals, Group VIB metals to form oleochemicals such as fatty alcohols, esters, and normal paraffins. Advantageously, the reaction conditions can be selected to directly convert the renewable feedstock to the desired product(s).Type: GrantFiled: December 9, 2011Date of Patent: October 21, 2014Assignee: Chevron U.S.A. Inc.Inventor: Cong-Yan Chen
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Publication number: 20140296466Abstract: The present invention relates to a method of producing bio-based homoserine lactone and bio-based organic acid through hydrolysis of O-acyl homoserine produced by a microorganism in the presence of an acid catalyst. According to the present invention, O-acyl homoserine produced by a microorganism is used as a raw material for producing 1,4-butanediol, gamma-butyrolactone, tetrahydrofuran and the like, which are industrially highly useful. The O-acyl homoserine produced by a microorganism can substitute conventional petrochemical products, can solve environmental concerns, including the emission of pollutants and the exhaustion of natural resources, and can be continuously renewable so as not to exhaust natural resources.Type: ApplicationFiled: March 19, 2014Publication date: October 2, 2014Inventors: Han Won Lee, Young Lyeol Yang, So Young Kim, Yong Uk Shin, Jin Sook Chang, Hye Won Um, Young Hyoung Goh, Sung Hoo Jhon
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Patent number: 8829248Abstract: Disclosed is a process for the extractive recovery of a homogeneous ruthenium catalyst from the reaction product of the hydrogenation of glycolic acid, glycolate esters, and/or glycolic acid oligomers with an extractant comprising a hydrophobic solvent and an optional hydrophilic solvent. The ruthenium catalyst, which can include 1,1,1-tris(diaryl- or dialkylphosphinomethyl)alkane ligands, can be recovered from the hydrophobic extract phase by back extraction with a hydrophilic solvent and recycled to a process for the preparation of ethylene glycol by the hydrogenation of glycolic acid and glycolic acid derivatives.Type: GrantFiled: August 12, 2011Date of Patent: September 9, 2014Assignee: Eastman Chemical CompanyInventors: Scott Donald Barnicki, Jeffrey Scott Kanel, Kenneth Wayne Hampton, Jr., Eduardo Gallas Cervo
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Patent number: 8791166Abstract: The invention provides a method for producing methanol and its products exclusively from a geothermal source as the sole source material also using the needed energy from the geothermal energy source. The method includes separating or isolating carbon dioxide accompanying hot water or steam of the source, generating hydrogen from the water and subsequently preparing methanol from the carbon dioxide and hydrogen. The methanol can be further converted into dimethyl ether or other products.Type: GrantFiled: July 10, 2009Date of Patent: July 29, 2014Assignee: University of Southern CaliforniaInventors: George A. Olah, G. K. Surya Prakash
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Publication number: 20140206895Abstract: The present disclosure is a method and system for production of oxalic acid and oxalic acid reduction products. The production of oxalic acid and oxalic acid reduction products may include the electrochemical conversion of CO2 to oxalate and oxalic acid. The method and system for production of oxalic acid and oxalic acid reduction products may further include the acidification of oxalate to oxalic acid, the purification of oxalic acid and the hydrogenation of oxalic acid to produce oxalic acid reduction products.Type: ApplicationFiled: March 20, 2014Publication date: July 24, 2014Applicant: Liquid Light, Inc.Inventors: Zbigniew Twardowski, Emily Barton Cole, Jerry J. Kaczur, Kyle Teamey, Kate A. Keets, Rishi Parajuli, Alexander Bauer, Narayanappa Sivasankar, George Leonard, Theodore J. Kramer, Paul Majsztrik, Yizu Zhu
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Publication number: 20140206896Abstract: The present disclosure is a method and system for production of oxalic acid and oxalic acid reduction products. The production of oxalic acid and oxalic acid reduction products may include the electrochemical conversion of CO2 to oxalate and oxalic acid. The method and system for production of oxalic acid and oxalic acid reduction products may further include the acidification of oxalate to oxalic acid, the purification of oxalic acid and the hydrogenation of oxalic acid to produce oxalic acid reduction products.Type: ApplicationFiled: March 20, 2014Publication date: July 24, 2014Applicant: Liquid Light, Inc.Inventors: Narayanappa Sivasankar, Robert Farrauto, Robert Augustine, Setrak Tanielyan, Mohanreddy Kasireddy, Emily Barton Cole, Kate A. Keets, Rishi Parajuli, Jerry J. Kaczur, Yizu Zhu, Farah Dhun, Kyle Teamey, Alexander Bauer, Theodore J. Kramer, Paul Majsztrik, George Leonard
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Publication number: 20140206894Abstract: The present disclosure is a method and system for production of oxalic acid and oxalic acid reduction products. The production of oxalic acid and oxalic acid reduction products may include the electrochemical conversion of CO2 to oxalate and oxalic acid. The method and system for production of oxalic acid and oxalic acid reduction products may further include the acidification of oxalate to oxalic acid, the purification of oxalic acid and the hydrogenation of oxalic acid to produce oxalic acid reduction products.Type: ApplicationFiled: March 20, 2014Publication date: July 24, 2014Applicant: Liquid Light, Inc.Inventors: Emily Barton Cole, Jerry J. Kaczur, Kyle Teamey, Kate A. Keets, Rishi Parajuli, Alexander Bauer, Narayanappa Sivasankar, George Leonard, Theodore J. Kramer, Paul Majsztrik, Yizu Zhu, Robert Farrauto, Robert Augustine, Setrak Tanielyan, Mohanreddy Kasireddy
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Patent number: 8779214Abstract: Disclosed is a process for the extractive recovery of a homogeneous ruthenium catalyst from the reaction product of the hydrogenation of glycolic acid, glycolate esters, and/or glycolic acid oligomers with an extractant comprising a hydrophobic solvent and an optional hydrophilic solvent. The ruthenium catalyst, which can include 1,1,1-tris(diaryl- or dialkylphosphinomethyl)alkane ligands, can be recovered from the hydrophobic extract phase by back extraction with a hydrophilic solvent and recycled to a process for the preparation of ethylene glycol by the hydrogenation of glycolic acid and glycolic acid derivatives.Type: GrantFiled: May 17, 2013Date of Patent: July 15, 2014Assignee: Eastman Chemical CompanyInventors: Scott Donald Barnicki, Jeffrey Scott Kanel, Kenneth Wayne Hampton, Jr.
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Publication number: 20140162326Abstract: Methods for forming ammonium salts of C4 diacids in a fermentation process with removal of divalent metal carbonate salts are disclosed. The pH of fermentation broths for production of C4 diacids is controlled by adding alkaline oxygen containing calcium or magnesium compounds, which forms divalent metal salts of the diacids. The divalent metal salts of the diacids are substituted with ammonium by introduction of ammonium salts at elevated temperature and pressure forming soluble ammonium salts thereof. C02 or bicarbonate is simultaneously added to the fennentation media at the elevated temperature and pressure. Reducing the temperature and pressure forms insoluble divalent metal carbonate salts that are separated from the solubilized ammonium diacid salts.Type: ApplicationFiled: July 9, 2012Publication date: June 12, 2014Inventors: ChiCheng Ma, Todd Werpy
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Patent number: 8704007Abstract: A hydrocarbon conversion process comprises contacting a renewable feedstock under hydroprocessing conditions with a bulk catalyst to form oleochemicals such as fatty alcohols, esters, and normal paraffins. Advantageously, the reaction conditions can be selected to directly convert the renewable feedstock to the desired product(s).Type: GrantFiled: December 9, 2011Date of Patent: April 22, 2014Assignee: Chevron U.S.A. Inc.Inventors: Cong-Yan Chen, Alexander E. Kuperman, William J. Cannella
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Patent number: 8692033Abstract: The present invention refers to a process for hydrogenation of caprolactone and/or its oligomers or polymers to 1,6-hexanediol. The process is performed in liquid phase at a pressure between 100 and 350 bar and is performed in the presence of a catalytically effective amount of at least one catalyst comprising Cu, Mn, Al, Cr, Zn, Ba and/or Zr.Type: GrantFiled: July 11, 2011Date of Patent: April 8, 2014Assignee: Perstorp ABInventors: Christoffer Paulsson, Katri Nikkila, Hakan Bjornberg
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Patent number: 8686198Abstract: An integrated process for producing paraffins and polyols from renewable feedstocks has been developed in which a hydrolysis process is integrated with the hydroprocessing step, producing products suitable for use as transportation fuels. Integration allows the use of common equipment which minimizes cost, raw material consumption, and energy requirements.Type: GrantFiled: May 18, 2012Date of Patent: April 1, 2014Assignee: UOP LLCInventor: Tom N. Kalnes
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Patent number: 8629306Abstract: The invention relates to a process for preparing 1,6-hexanediol, preferably with at least 99.5% purity, which are especially virtually free of 1,4-cyclohexanediols, from a carboxylic acid mixture which is obtained as a by-product of the catalytic oxidation of cyclohexane to cyclohexanone/cyclohexanol with oxygen or oxygen-comprising gases and by water extraction of the reaction mixture, by hydrogenating the carboxylic acid mixture, esterifying and hydrogenating a substream to hexanediol.Type: GrantFiled: March 29, 2010Date of Patent: January 14, 2014Assignee: BASF SEInventors: Rolf Pinkos, Daniel Breuninger, Gerd-Dieter Tebben
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Publication number: 20130338406Abstract: The present invention relates to a method for the production of ethylene glycol using a feedstock comprising an oxalate and a catalyst containing copper and/or a copper oxide, comprising contacting the feedstock with the catalyst in a reactor under the conditions of a temperature in the range from about 170 to about 270° C., a weight hourly space velocity of the oxalate in the range from about 0.2 to about 5 h?1, a molar ratio of hydrogen to the oxalate in the range from about 40:1 to about 200:1 and a reaction pressure in the range from about 1.5 to about 10 MPa, to produce an effluent containing ethylene glycol, in which the reactor is a tube-array reactor using partitioned heat exchange and adopting outer and inner tubes configured in a double-tube structure to facilitate the heat exchange of the catalyst.Type: ApplicationFiled: February 24, 2012Publication date: December 19, 2013Applicants: SHANGHAI RESEARCH INSTITUTE OF PETROCHEMICAL TECHNOLOGY, SINOPEC, CHINA PETROLEUM & CHEMICAL CORPORATIONInventors: Juntao Liu, Weimin Yang, Lei Li, Wanmin Wang, Linna Zhang, Haifeng Song
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Publication number: 20130331618Abstract: A method for improving the quality of ethylene glycol products, which mainly solves the technical problem of low UV-light transmittance of the ethylene glycol products present in the prior art. The method successfully solves the problem by use of the technical solution wherein the ethylene glycol raw material and hydrogen are passed through a rotating packed bed reactor loaded with solid oxide catalyst at a temperature of about 20 to about 280 ° C., a pressure of about 0.1 to about 4.0 MPa, a space velocity of about 0.2 to about 100.0 hr?1 and a molar ratio of hydrogen to ethylene glycol of from about 0.01 to 40:1, and ethylene glycol is obtained after the reaction. The solid oxide catalyst is at least one of copper-based, nickel-based and palladium-based catalysts, and the rotation rate of the rotating packed bed reactor is about 300 to about 5000 rpm.Type: ApplicationFiled: February 24, 2012Publication date: December 12, 2013Applicants: SHANGHAI RESEARCH INSTITUTE OF PETROCHEMICAL TECHNOLOGY, SINOPEC, CHINA PETROLEUM & CHEMICAL CORPORATIONInventors: Juntao Liu, Yuhong Zhang, Wanmin Wang
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Publication number: 20130331617Abstract: A process for producing ethylene glycol includes contacting an oxalate with a fluidized bed catalyst under the following conditions: a reaction temperature of from about 170 to about 270° C., a weight space velocity of oxalate of from about 0.2 to about 7 hours?1, a hydrogen/ester molar ratio of about 20˜200:1, a reaction pressure of from about 1.5 to about 10 MPa, and a reaction temperature difference T of from about 1 to about 15° C. The fluidized bed catalyst includes: a) from about 5 to about 80 parts by weight of copper and the oxide thereof, b) from about 10 to about 90 parts by weight of at least one carrier selected from silica, molecular sieve or alumina, c) from about 0.01 to about 30 parts by weight of bismuth and tungsten metallic elements or the oxides thereof, or cerium and niobium metallic elements or the oxides thereof.Type: ApplicationFiled: February 24, 2012Publication date: December 12, 2013Applicants: Shanghai Research Institute of Petrochemical Technology, Sinopec, China Petroleum & Chemical CorporationInventors: Weimin Yang, Juntao Liu, Wanmin Wang, Jun Kuai
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Publication number: 20130310598Abstract: Disclosed is a process for producing glycolate ester oligomers. The process comprises reacting ethylene glycol and glycolic acid to produce a stream of glycolate ester oligomers and glycolic acid oligomers while simultaneously removing water. The stream of glycolate ester oligomers and glycolic acid oligomers has a low concentration of water and glycolic acid-ends, and thus is useful in a subsequent hydrogenation reaction to produce ethylene glycol.Type: ApplicationFiled: May 16, 2012Publication date: November 21, 2013Applicant: EASTMAN CHEMICAL COMPANYInventors: Daniel Latham Terrill, Kelley Margaret Moran, Stephen Neal Falling
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Publication number: 20130281664Abstract: The present invention relates to novel Ruthenium catalysts and related borohydride complexes, and the use of such catalysts, inter alia, for (1) hydrogenation of amides (including polyamides) to alcohols and amines; (2) preparing amides from alcohols with amines (including the preparation of polyamides (e.g., polypeptides) by reacting dialcohols and diamines and/or by polymerization of amino alcohols); (3) hydrogenation of esters to alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di-lactones) or polyesters); (4) hydrogenation of organic carbonates (including polycarbonates) to alcohols and hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (5) dehydrogenative coupling of alcohols to esters; (6) hydrogenation of secondary alcohols to ketones; (7) amidation of esters (i.e.Type: ApplicationFiled: October 11, 2011Publication date: October 24, 2013Inventors: David Milstein, Ekambaram Balaraman, Chidambaram Gunanathan, Boopathy Gnanaprakasam, Jing Zhang
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Patent number: 8563784Abstract: The invention relates to a catalytic method for the industrial production of a diol compound, such as 2-methyl-2-4-pentanediol, also called 2,4-hexylene glycol (HGL), from a ?-hydroxy carbonyl compound, Formula (I), in particular diacetone alcohol (DAA).Type: GrantFiled: December 15, 2009Date of Patent: October 22, 2013Assignee: Rhodia Poliamida e Especialidades LtdaInventors: Danilo Zim, Philippe Marion
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Publication number: 20130261328Abstract: Disclosed is a process for the production and purification of glycolic acid or glycolic acid derivatives by the carbonylation of formaldehyde in the presence of a homogeneous acid catalyst and a carboxylic acid. This invention discloses hydrocarboxylations and corresponding homogeneous acid catalyst and glycolic acid separations. The homogeneous acid catalyst is readily separated from the hydrocarboxylation reaction effluent and recycled and the carboxylic acid is readily removed from the glycolic acid and the carboxylic acid is recycled.Type: ApplicationFiled: March 27, 2012Publication date: October 3, 2013Applicant: EASTMAN CHEMICAL COMPANYInventors: Scott Donald Barnicki, Robert Thomas Hembre, Stephen Neal Falling, Andrew James Vetter
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Publication number: 20130261329Abstract: Disclosed is a process for the production and purification of glycolic acid or glycolic acid derivatives by the carbonylation of methylene dipropionate in the presence of a homogeneous acid catalyst and propionic acid. This invention discloses hydrocarboxylations and corresponding homogeneous acid catalyst and glycolic acid separations.Type: ApplicationFiled: March 27, 2012Publication date: October 3, 2013Applicant: EASTMAN CHEMICAL COMPANYInventors: Scott Donald Barnicki, Robert Thomas Hembre, Stephen Neal Falling
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Publication number: 20130253232Abstract: Disclosed is a process for the extractive recovery of a homogeneous ruthenium catalyst from the reaction product of the hydrogenation of glycolic acid, glycolate esters, and/or glycolic acid oligomers with an extractant comprising a hydrophobic solvent and an optional hydrophilic solvent. The ruthenium catalyst, which can include 1,1,1-tris(diaryl- or dialkylphosphinomethyl)alkane ligands, can be recovered from the hydrophobic extract phase by back extraction with a hydrophilic solvent and recycled to a process for the preparation of ethylene glycol by the hydrogenation of glycolic acid and glycolic acid derivatives.Type: ApplicationFiled: May 17, 2013Publication date: September 26, 2013Applicant: Eastman Chemical CompanyInventors: Scott Donald Barnicki, Jeffrey Scott Kanel, Kenneth Wayne Hampton, JR.
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Publication number: 20130225875Abstract: The present invention refers to a process for hydrogenation of caprolactone and/or its oligomers or polymers to 1,6-hexanediol. The process is performed in liquid phase at a pressure between 100 and 350 bar and is performed in the presence of a catalytically effective amount of at least one catalyst comprising Cu, Mn, Al, Cr, Zn, Ba and/or Zr.Type: ApplicationFiled: July 11, 2011Publication date: August 29, 2013Applicant: PERSTORP ABInventors: Christoffer Paulsson, Katri Nikkila, Hakan Bjornberg
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Publication number: 20130184499Abstract: A reduced metallic catalyst or pre-activated catalyst is formed by contacting a precursor catalyst or a reduced metallic catalyst with a modifier solution in the presence of a source of hydrogen and heat treating the precursor catalyst or the reduced metallic catalyst at super-atmospheric pressure to obtain the reduced metallic catalyst from the precursor catalyst or the pre-activated catalyst from the reduced metallic catalyst. A method of hydrogenating a hydrogenatable precursor includes providing a reduced metallic catalyst or the pre-activated catalyst prepared with modifier buffer and contacting the reduced metallic catalyst or pre-activated catalyst with the hydrogenatable precursor in the presence of hydrogen and, optionally, in the presence of a modifier solution.Type: ApplicationFiled: January 8, 2013Publication date: July 18, 2013Applicant: BioAmber International S.a.r.l.Inventor: BioAmber International S.a.r.l.
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Patent number: 8471048Abstract: The present invention relates to a ruthenium carbonyl complex that is represented by the following Formula (1): RuXY(CO)(L)??(1) (in the Formula (1), X and Y, which may be the same or different from each other, represent an anionic ligand and L represents a tridentate aminodiphosphine ligand which has two phosphino groups and a —NH— group), its production method, and a method for production of alcohols by hydrogenation-reduction of ketones, esters, and lactones using the complex as a catalyst. The ruthenium carbonyl complex of the invention has a high catalytic activity and it can be easily prepared and handled.Type: GrantFiled: June 30, 2010Date of Patent: June 25, 2013Assignee: Takasago International CorporationInventors: Wataru Kuriyama, Takaji Matsumoto, Yasunori Ino, Osamu Ogata