Preparing By Alcoholysis, Hydrolysis Or Saponification Of An Ester Patents (Class 568/858)
  • Patent number: 11807594
    Abstract: The invention relates to a process for the preparation of ethylene glycol from ethylene, which comprises contacting the carbon dioxide stream resulting from hydrolysing ethylene carbonate, or the condensate stream resulting from condensing said carbon dioxide stream, or the waste water stream resulting from removing water from the ethylene glycol stream, such stream comprising water, 2-chloroethanol and ethylene glycol and additionally comprising 2-iodoethanol or 2-bromoethanol, with an alkali metal containing basic compound to form a mixture comprising water, 2-chloroethanol and ethylene glycol and additionally comprising alkali metal iodide or alkali metal bromide which mixture is dehydrated.
    Type: Grant
    Filed: December 6, 2019
    Date of Patent: November 7, 2023
    Assignee: SHELL USA, INC.
    Inventors: Eugene Marie Godfried Andre Van Kruchten, Petrus Johannes Gerardus Boons
  • Patent number: 11524927
    Abstract: Monoethylene glycol (MEG) may be reclaimed by a process that includes contacting a MEG-water-salt stream with a heat transfer fluid and then flash separating the MEG and water in the flash separator vessel where the pressure is higher than 0.3 barA (0.03 MPa), the temperature is in the range of above 120° C. to about 250° C., and the residence time of the MEG and water ranges from about 1 second to about 10 minutes, and then removing the MEG and water in an overhead of the flash separator vessel and removing the salt from the flash separator vessel. In some embodiments it is expected that the temperature of the process may range from above 165° C. to about 250° C. and/or that the pressure may be atmospheric.
    Type: Grant
    Filed: July 16, 2015
    Date of Patent: December 13, 2022
    Assignee: CAMERON INTERNATIONAL CORPORATION
    Inventors: Christopher Stephen King, Brian Edward Messenger, Harihara V. Nemmara, Z. Frank Zheng, Shihui Zhou
  • Patent number: 11141676
    Abstract: The present disclosure provides a system for energy recycling using mechanical vapor recompression in combined chemical process, the system including a heat exchange reactor for generating an intermediate material by means of an exothermic reaction and discharging the generated intermediate material, and heat-exchanging heat generated in the exothermic reaction with water supplied from outside so as to generate water vapor; an absorption tank for receiving the intermediate material, and mixing the intermediate material with water, so as to generate an intermediate material aqueous solution; a stripper for receiving the intermediate material aqueous solution, and separating the intermediate material into an intermediate material gas and an intermediate material water-rich aqueous solution; an endothermic reactor for receiving the intermediate material water-rich aqueous solution, and reacting the intermediate material with water, so as to generate a final product aqueous solution; an evaporation concentrator f
    Type: Grant
    Filed: July 12, 2018
    Date of Patent: October 12, 2021
    Assignee: SUNTECO LIMITED
    Inventor: Joo Sun Lee
  • Patent number: 10882803
    Abstract: A process is incorporated herein for the synthesis of bio-1,2-alkanediols, comprising: providing a bio-alkene having a carbon chain of about 5 to about 20 carbon atoms and a bio-1-alkene regioselectivity of at least about 80%, at least about 92% and/or at least about 95%; and converting the bio-alkene to a bio-1,2-alkanediol having a carbon chain length of about 5 to about 20 carbon atoms. Methods for treating catalysts which may be incorporated in the process for the synthesis of bio-1,2-alkanediols are also included herein. Such bio-1,2-alkanediols are used in compositions and products alone as antimicrobial materials, or with existing bio-compounds and/or antimicrobials, preservatives, alternative preservation systems and/or hurdle technology components. The bio-1,2-alkanediols incorporate a natural and bio-based pathway for antimicrobial effects in various compositions such as cosmetic, pharmaceutical, industrial and household products.
    Type: Grant
    Filed: January 30, 2019
    Date of Patent: January 5, 2021
    Assignee: INOLEX INVESTMENT CORPORATION
    Inventors: Rocco V. Burgo, Michael E. Wright, Gary B. Mosser, Michael J. Fevola
  • Patent number: 10822293
    Abstract: A process is described for producing biobased 1,2-propanediol, comprising reacting a glycerol-containing feed containing less than 5 weight percent of water with hydrogen in the presence of a catalyst, to partially convert glycerol in the glycerol containing feed to a crude reaction product mixture including 1,2-propanediol, removing 10 water from the crude reaction product mixture, recovering a portion but not all of the 1,2-propanediol from the crude reaction product mixture, and recycling the remainder of the 1,2-propanediol with unconverted glycerol and combining these with makeup glycerol to provide additional of the essentially anhydrous, glycerol-containing feed.
    Type: Grant
    Filed: November 6, 2017
    Date of Patent: November 3, 2020
    Assignee: ARCHER DANIELS MIDLAND COMPANY
    Inventor: Chi Cheng Ma
  • Patent number: 10532967
    Abstract: A process for the production of propylene glycol from a lactate ester is disclosed. The process comprises supplying a feed comprising a C3-6 alkyl lactate ester. The feed is contacted with a stream of hydrogen containing gas and subjected to hydrogenation in the vapour phase in the presence of a catalyst at a temperature of from about 130° C. to about 185° C., a pressure of from about 20 bar to about 60 bar, and a weight hourly space velocity greater than about 0.3 h?1. The catalyst is a reduced copper catalyst selected from copper alumina, optionally comprising manganese, copper chromite, copper zinc oxide and Raney copper.
    Type: Grant
    Filed: October 17, 2017
    Date of Patent: January 14, 2020
    Assignee: Johnson Matthey Davy Technologies Limited
    Inventors: Roger Bence, Robert Gallen, Robert Wild
  • Patent number: 9365535
    Abstract: The invention provides a process for the preparation of an alkylene glycol from an alkene. A gas composition from an alkylene oxide reactor is supplied to an alkylene oxide absorber comprising a column of vertically stacked trays or comprising a packed column. Lean absorbent comprising at least 20 wt % water is supplied to the alkylene oxide absorber and is contacted with the gas composition in the presence of one or more catalysts that promote carboxylation and hydrolysis. At least 50% of the alkylene oxide entering the alkylene oxide absorber is converted in the alkylene oxide absorber. Fat absorbent is withdrawn from the absorber, is optionally supplied to finishing reactors and/or a flash vessel or light ends stripper, and is subsequently subjected to dehydration and purification to provide a purified alkylene glycol product stream.
    Type: Grant
    Filed: January 13, 2014
    Date of Patent: June 14, 2016
    Assignee: Shell Oil Company
    Inventors: Eugene Marie Godfried Andre Van Kruchten, Dominicus Maria Rekers, Mathias Jozef Paul Slapak
  • Patent number: 9145347
    Abstract: The present invention relates to a process for preparing deodorized 1,2-propanediol, to the use of the purified propanediol and to an apparatus for performing the process.
    Type: Grant
    Filed: July 11, 2014
    Date of Patent: September 29, 2015
    Assignee: BASF SE
    Inventors: Stephan Maurer, Roman Prochazka, Oliver Bey, Jochen Steiner, Jochem Henkelmann, Gerhard Theis, Peter Wahl, Frank Heimann
  • Publication number: 20150148560
    Abstract: Provided herein are methods that utilize polyhydroxyalkanoates (PHAs) as a substrate for further conversion to C4 and C5 compounds. Polyhydroxyalkanoates can undergo esterification to yield alkyl hydroxyalkanoates and alkyl alkenoates, which may serve as useful precursors in the production of alkadienes and alkenedioic acids, including for example butadiene and butenedioic acid.
    Type: Application
    Filed: May 31, 2013
    Publication date: May 28, 2015
    Applicant: MICROMIDAS, INC.
    Inventors: Ryan L. Smith, John Bissell, Makoto N. Masuno, Douglas Cannon, Alex B. Wood, Marc Foster
  • Patent number: 9000041
    Abstract: The present invention relates to novel hydroxyl compounds, compositions comprising hydroxyl compounds, and methods useful for treating and preventing a variety of diseases and conditions such as, but not limited to aging, Alzheimer's Disease, cancer, cardiovascular disease, diabetic nephropathy, diabetic retinopathy, a disorder of glucose metabolism, dyslipidemia, dyslipoproteinemia, hypertension, impotence, inflammation, insulin resistance, lipid elimination in bile, obesity, oxysterol elimination in bile, pancreatitis, pancreatitius, Parkinson's disease, a peroxisome proliferator activated receptor-associated disorder, phospholipid elimination in bile, renal disease, septicemia, metabolic syndrome disorders (e.g., Syndrome X), thrombotic disorder. Compounds and methods of the invention can also be used to modulate C reactive protein or enhance bile production in a patient.
    Type: Grant
    Filed: June 24, 2013
    Date of Patent: April 7, 2015
    Assignee: Esperion Therapeutics, Inc.
    Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu
  • Patent number: 8809596
    Abstract: The present invention relates to a process for preparing deodorized 1,2-propanediol, to the use of the purified propanediol and to an apparatus for performing the process.
    Type: Grant
    Filed: January 19, 2010
    Date of Patent: August 19, 2014
    Assignee: BASF SE
    Inventors: Stephan Maurer, Roman Prochazka, Oliver Bey, Jochen Steiner, Jochem Henkelmann, Gerhard Theis, Peter Wahl, Frank Heimann
  • Patent number: 8802900
    Abstract: The invention provides a process for the production of ethylene glycol from ethylene. An ethylene glycol stream comprises inorganic chloride contaminants and the process comprises steps of converting the inorganic chloride contaminants to 2-chloroethanol by reaction with ethylene oxide in one or more dehydration columns, and removing 2-chloroethanol in a waste water stream.
    Type: Grant
    Filed: November 22, 2011
    Date of Patent: August 12, 2014
    Assignee: Shell Oil Company
    Inventors: Hendrik Stichter, Jacqueline Hessing
  • Patent number: 8609905
    Abstract: The present invention provides a method for producing glycerol, including transesterifying an oil-and-fat with an alcohol in the presence of a solid catalyst to obtain a glycerol product liquid and subjecting the glycerol product liquid to adsorption treatment with an ion-exchange resin.
    Type: Grant
    Filed: December 21, 2009
    Date of Patent: December 17, 2013
    Assignee: Kao Corporation
    Inventors: Hiroshi Ohnishi, Hiroshi Danjo
  • Patent number: 8575402
    Abstract: The invention provides a process for the production of an alkylene glycol comprising converting an alkene to the corresponding alkylene oxide; absorbing the alkylene oxide in an aqueous absorbent and then stripping; supplying the aqueous alkyene oxide stream to a carboxylation reactor; converting the alkylene oxide to a corresponding alkylene carbonate; converting the alkylene carbonate to the alkylene glycol; removing water to form a dehydrated alkylene glycol stream; and purifying the dehydrated alkylene glycol stream, wherein the start-up procedure comprises supplying water, carboxylation-hydrolysis catalyst and carbon dioxide streams to the carboxylation reactor and providing a start-up stream comprising the alkylene glycol at an injection point at or downstream of the inlet used in supplying the stream to the carboxylation reactor and recovering an alkylene glycol stream from the glycol distillation column.
    Type: Grant
    Filed: October 17, 2011
    Date of Patent: November 5, 2013
    Assignee: Shell Oil Company
    Inventors: Roel Guillaume Hubertus Leonardus Bastings, Arthur Willibrordus Titus Rots
  • Patent number: 8545703
    Abstract: Process and steps for the production of biodiesel and/or glycerin from feedstock are provided.
    Type: Grant
    Filed: November 27, 2012
    Date of Patent: October 1, 2013
    Assignee: Menlo Energy Management, LLC
    Inventors: Gaurav Shah, Sunil Suri
  • Patent number: 8540881
    Abstract: Process and steps for the production of biodiesel and/or glycerin from feedstock are provided.
    Type: Grant
    Filed: November 27, 2012
    Date of Patent: September 24, 2013
    Assignee: Menlo Energy Management, LLC
    Inventors: Gaurav Shah, Sunil Suri
  • Patent number: 8530706
    Abstract: Processes and reactors for the preparation of an alkylene glycol from an alkylene oxide are provided. In one embodiment, a reactor is provided comprising a carboxylation zone, a hydrolysis zone, and a channel whereby carbon dioxide can be supplied from the hydrolysis zone to the carboxylation zone, wherein the carboxylation zone and the hydrolysis zone are contained within one reactor vessel and wherein the carboxylation zone is separated from the hydrolysis zone by an internal baffle.
    Type: Grant
    Filed: October 25, 2012
    Date of Patent: September 10, 2013
    Assignee: Shell Oil Company
    Inventors: Hendrik Johannes Van Milligen, Peter Veenstra
  • Patent number: 8497301
    Abstract: The present invention relates to novel hydroxyl compounds, compositions comprising hydroxyl compounds, and methods useful for treating and preventing a variety of diseases and conditions such as, but not limited to aging, Alzheimer's Disease, cancer, cardiovascular disease, diabetic nephropathy, diabetic retinopathy, a disorder of glucose metabolism, dyslipidemia, dyslipoproteinemia, hypertension, impotence, inflammation, insulin resistance, lipid elimination in bile, obesity, oxysterol elimination in bile, pancreatitis, pancreatitius, Parkinson's disease, a peroxisome proliferator activated receptor-associated disorder, phospholipid elimination in bile, renal disease, septicemia, metabolic syndrome disorders (e.g., Syndrome X), thrombotic disorder. Compounds and methods of the invention can also be used to modulate C reactive protein or enhance bile production in a patient.
    Type: Grant
    Filed: May 14, 2012
    Date of Patent: July 30, 2013
    Assignee: Esperion Therapeutics, Inc.
    Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu
  • Publication number: 20130126779
    Abstract: Deicing compositions comprised of glycerol-containing by-products of triglyceride processing processes are disclosed.
    Type: Application
    Filed: January 10, 2013
    Publication date: May 23, 2013
    Applicant: MLI Associates, LLC
    Inventor: MLI Associates, LLC
  • Publication number: 20130072727
    Abstract: Disclosed is a process for producing ethylene glycol catalyzed by an ionic liquid, characterized in that the process includes the following three steps: (a) a carbonylation step of ethylene oxide and CO2 catalyzed by an ionic liquid composite catalyst comprising a hydroxyl functionalized ionic liquid and an alkali metal salt under an aqueous condition to produce ethylene carbonate and ethylene glycol; (b) a hydrolysis step of reacting the reaction solution containing ethylene carbonate and the ionic liquid composite catalyst obtained in step (a) with water to produce ethylene glycol; (c) a purification step of dehydrating and refining ethylene glycol from the aqueous solution containing ethylene glycol and the catalyst produced in step (b). The present process has the following advantages: the catalyst has high activity, high suitability, and good stability, the reaction condition is wild, the conversion of ethylene oxide is high, the selectivity of ethylene glycol is high, and the process is simple.
    Type: Application
    Filed: June 7, 2010
    Publication date: March 21, 2013
    Applicant: Institute of Process Engineering, Chinese Academy of Sciences
    Inventors: Suojiang Zhang, Jian Sun, Weiguo Cheng, Jinquan Wang, Jianxin Zhang, Zengzeng Fu, Ziangping Zhang
  • Patent number: 8329959
    Abstract: The invention provides a process and a reactor for the preparation of an alkylene glycol from an alkylene oxide. Alkylene oxide, water, a homogeneous carboxylation catalyst and a homogenous hydrolysis catalyst are supplied to a reactor comprising a carboxylation zone and a hydrolysis zone. One or more ejectors are used to mix carbon dioxide and the liquid reagents in the carboxylation zone so that alkylene oxide reacts with carbon dioxide in the presence of water in the carboxylation zone to form a reaction solution comprising alkylene carbonate, water, the homogeneous carboxylation catalyst and the homogeneous hydrolysis catalyst. The reaction solution is supplied from the carboxylation zone to a hydrolysis zone, wherein alkylene carbonate and water react to form a product solution comprising alkylene glycol, the homogeneous carboxylation catalyst and the homogeneous hydrolysis catalyst.
    Type: Grant
    Filed: December 5, 2008
    Date of Patent: December 11, 2012
    Assignee: Shell Oil Company
    Inventors: Hendrik Johannes Van Milligen, Peter Veenstra
  • Publication number: 20120197048
    Abstract: A process for the production of ethylene glycol comprising: (i) supplying ethylene and oxygen and an organic chloride moderator to an EO reactor, thereby producing a reactor product stream; (ii) supplying the reactor product stream to an EO absorber, thereby producing a fat absorbent stream; (iii) supplying the fat absorbent stream to an EO stripper, thereby producing a concentrated ethylene oxide stream and a lean absorbent stream; (iv) recirculating the lean absorbent stream to the EO absorber; and (v) supplying the ethylene oxide stream and/or the ethylene carbonate stream to hydrolysis reactors with an alkali metal salt hydrolysis catalyst to form an ethylene glycol stream; wherein the process additionally comprises: (vi) removing a glycol bleed stream from the ethylene oxide stripper; and (vii) adding a base to the ethylene oxide stripper such that the pH in the bottom section of the stripper is maintained from 9.5 to 12.0.
    Type: Application
    Filed: January 31, 2012
    Publication date: August 2, 2012
    Applicant: SHELL OIL COMPANY
    Inventors: Jan VAN OGTROP, Abraham Adriaan SMAARDIJK, Jacqueline Hessing, Hendrik STICHTER
  • Publication number: 20120190891
    Abstract: Embodiments of the invention include processing lipid feedstocks into various products. In an embodiment, the invention includes a method of processing a lipid feedstock including combining the lipid feedstock with water to form a reaction mixture; and contacting the reaction mixture with a catalyst, the catalyst including a metal oxide. Methods can be used to form polyols, diols, and carboxylic acids, amongst others. Other embodiments are also included herein.
    Type: Application
    Filed: November 21, 2011
    Publication date: July 26, 2012
    Inventors: Clayton V. McNeff, Bingwen Yan, Daniel Thomas Nowlan
  • Publication number: 20120095271
    Abstract: The invention provides a process for the production of an alkylene glycol comprising converting an alkene to the corresponding alkylene oxide; absorbing the alkylene oxide in an aqueous absorbent and then stripping; supplying the aqueous alkyene oxide stream to a carboxylation reactor; converting the alkylene oxide to a corresponding alkylene carbonate; converting the alkylene carbonate to the alkylene glycol; removing water to form a dehydrated alkylene glycol stream; and purifying the dehydrated alkylene glycol stream, wherein the start-up procedure comprises supplying water, carboxylation-hydrolysis catalyst and carbon dioxide streams to the carboxylation reactor and providing a start-up stream comprising the alkylene glycol at an injection point at or downstream of the inlet used in supplying the stream to the carboxylation reactor and recovering an alkylene glycol stream from the glycol distillation column.
    Type: Application
    Filed: October 17, 2011
    Publication date: April 19, 2012
    Applicant: SHELL OIL COMPANY
    Inventors: Roel Guillaume Hubertus Leonardus BASTINGS, Arthur Willibrordus Titus ROTS
  • Patent number: 8110712
    Abstract: The invention provides a process for the preparation of an alkylene glycol from an alkylene oxide. Alkylene oxide reacts with carbon dioxide in the presence of a carboxylation catalyst to provide alkylene carbonate; alkylene carbonate reacts with water in the presence of a hydrolysis catalyst to provide alkylene glycol. An initial charge of the carboxylation catalyst and an initial charge of the hydrolysis catalyst are added, the degradation and activity of the hydrolysis catalyst are monitored, and when the activity of the hydrolysis catalyst has fallen below a minimum level, an additional charge of the hydrolysis catalyst is added.
    Type: Grant
    Filed: April 8, 2009
    Date of Patent: February 7, 2012
    Assignee: Shell Oil Company
    Inventors: Eugene Marie Godfried Andre Van Kruchten, Abraham Adriaan Smaardijk, Hendrik Stichter
  • Publication number: 20120029250
    Abstract: Embodiments of methods for making renewable diesel by deoxygenating (decarboxylating/decarbonylating/dehydrating) fatty acids to produce hydrocarbons are disclosed. Fatty acids are exposed to a catalyst selected from a) Pt and MO3 on ZrO2 (M is W, Mo, or a combination thereof), or b) Pt/Ge or Pt/Sn on carbon, and the catalyst decarboxylates at least 10% of the fatty acids. In particular embodiments, the catalyst consists essentially of 0.7 wt % Pt and 12 wt % WO3, relative to a mass of catalyst, or the catalyst consists essentially of a) 5 wt % Pt and b) 0.5 wt % Ge or 0.5 wt % Sn, relative to a mass of catalyst. Deoxygenation is performed without added hydrogen and at less than 100 psi. Disclosed embodiments of the catalysts deoxygenate at least 10% of fatty acids in a fatty acid feed, and remain capable of deoxygenating fatty acids for at least 200 minutes to more than 350 hours.
    Type: Application
    Filed: August 2, 2010
    Publication date: February 2, 2012
    Inventors: Richard T. Hallen, Karl O. Albrecht, Heather M. Brown, James F. White
  • Publication number: 20120015411
    Abstract: The present application relates to a process for manufacturing maleic anhydride that comprising the following steps: a) fermentation of renewable raw materials and optionally purification to produce a mixture comprising at least butanol; b) oxidation of the butanol to maleic anhydride at a temperature generally between 300° C. to 600° C., using a catalyst based on oxides of vanadium and/or molybdenum; c) isolation of the maleic anhydride obtained at the end of step b). It also relates to the maleic anhydride obtained from renewable raw materials, to the copolymers and compositions comprising said maleic anhydride and also uses of use of this maleic anhydride.
    Type: Application
    Filed: July 17, 2009
    Publication date: January 19, 2012
    Applicant: Arkema France
    Inventor: Jean-Luc Dubois
  • Patent number: 8093416
    Abstract: The present invention has an object to provide the following method for producing fatty acid alkyl esters and/or glycerin and the following catalyst used in the production method. According to the production method, a fat or oil is reacted with an alcohol to give a fatty acid alkyl ester and/or glycerin suitably used in a food or fuel application, etc., with high efficiency, and complicated steps such as a step of recovering a catalyst can be simplified or omitted. According to the catalyst, an active metal component is not eluted even if the catalyst is used repeatedly or for a long period of time, and further, such a catalyst can maintain an excellent catalyst activity for a long time even in the presence of water and exhibit a high activity to both of transesterification of a glyceride contained in the fat or oil and esterification of free fatty acid.
    Type: Grant
    Filed: October 17, 2008
    Date of Patent: January 10, 2012
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Takeo Akatsuka, Masanori Nonoguchi, Tomoharu Oku
  • Patent number: 8049044
    Abstract: The invention relates to a process for remediation of a fluid contaminated with alkylene oxide, involving contacting the contaminated fluid with an aqueous absorbent to yield a fat absorbent having absorbed fluid, conferring intimate contact of fat absorbent and alkylene oxide and conversion of alkylene oxide; and, an apparatus for remediation of the fluid which has a converter having inlet means connected to the outlet of a fluid absorber for contacting fluid and aqueous absorbent, a holding unit having a volume V for the fat absorbent, and outlet means connected to the inlet of a fluid desorber.
    Type: Grant
    Filed: December 18, 2003
    Date of Patent: November 1, 2011
    Assignee: Shell Oil Company
    Inventors: Alouisius Nicolaas Rene Bos, Dominicus Maria Rekers, Arthur Willibrordus Titus Rots
  • Publication number: 20110263908
    Abstract: The present invention provides a method for producing glycerol, including transesterifying an oil-and-fat with an alcohol in the presence of a solid catalyst to obtain a glycerol product liquid and subjecting the glycerol product liquid to adsorption treatment with an ion-exchange resin.
    Type: Application
    Filed: December 21, 2009
    Publication date: October 27, 2011
    Applicant: KAO CORPORATION
    Inventors: Hiroshi Ohnishi, Hiroshi Danjo
  • Patent number: 8039651
    Abstract: In the method of the present invention for producing fatty acid alkyl ester and/or glycerin, as a heat source for an alcohol refining step of refining alcohol from unreacted alcohol that remains without reacting in a first reaction step, at least a part of heat of the unreacted alcohol is used. This allows reducing costs in production of fatty acid alkyl ester and/or glycerin over a solid catalyst.
    Type: Grant
    Filed: October 31, 2007
    Date of Patent: October 18, 2011
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Masanori Nonoguchi, Hiroko Izumi, Atsushi Tachibana, Tomoharu Oku, Toshimitsu Moriguchi, Takeo Akatsuka, Izuho Okada, Hideaki Tsuneki, Hironori Horie
  • Patent number: 8022257
    Abstract: Methods for producing a polyols and polyurethanes are described. The polyols described herein can be produced directly from crude glycerin or through liquefaction of lignocellulosic biomass using a solvent comprising crude glycerin. The polyols produced in accordance with certain aspects may be derived from a significant proportion of renewable resources.
    Type: Grant
    Filed: December 7, 2009
    Date of Patent: September 20, 2011
    Assignee: The Ohio State University Research Foundation
    Inventors: Yebo Li, Yuguang Zhou
  • Publication number: 20110172461
    Abstract: Methods of recycling a post-consumer polymer material comprise depolymerizing the polymer material by heating the polymer material in the presence of a hydrogen donor material and a strong base compound, and optionally a catalyst, to effect catalytic transfer hydrogenation and base cleavage and produce intermediate and/or monomer products of molecular weights lower than that of the polymeric material. In a specific embodiment, the methods comprise recycling post-consumer polyethylene terephthalate. The methods comprise depolymerizing the polyethylene terephthalate by heating in the presence of a hydrogen donor material and a strong base compound, and optionally a catalyst, to effect catalytic transfer hydrogenation and base cleavage and produce terephthalic and/or naphthalic acid, or a salt thereof, and ethylene glycol.
    Type: Application
    Filed: September 8, 2008
    Publication date: July 14, 2011
    Inventor: Charles J. Rogers
  • Publication number: 20110137053
    Abstract: The present invention provides a process for producing ethylene oxide, comprising: a. cracking an ethane-comprising feed in a cracking zone under cracking conditions to obtain olefins including at least ethylene and hydrogen; b. converting an oxygenate feedstock in an oxygenate-to-olefin zone to obtain olefins, including at least ethylene; c. providing at least part of the ethylene obtained in step (a) and/or (b) to an ethylene oxidation zone together with a feed containing oxygen and oxidising ethylene to obtain at least ethylene oxide and carbon dioxide; and wherein at least part of the oxygenate feedstock is obtained by providing carbon dioxide obtained in step (c) and a feed containing hydrogen to an oxygenate synthesis zone and synthesising oxygenates, which feed containing hydrogen comprises hydrogen obtained in step (a). In another aspect the invention provides an integrated system for producing ethylene oxide.
    Type: Application
    Filed: November 9, 2010
    Publication date: June 9, 2011
    Inventors: Leslie Andrew CHEWTER, Herve Henry, Jeroen Van Westrenen
  • Publication number: 20100312023
    Abstract: The present invention relates to a process for preparing 1,2-propanediol, in which a glycerol-containing stream, especially a stream obtained on the industrial scale in the production of biodiesel, is subjected to a hydrogenation in an at least three-stage reactor cascade.
    Type: Application
    Filed: August 29, 2008
    Publication date: December 9, 2010
    Applicant: BASF SE
    Inventors: Jochem Henkelmann, Roman Prochazka, Oliver Bey, Stephan Maurer, Jochen Steiner, Heiko Urtel, Gerhard Theis, Peter Wahl
  • Publication number: 20100286453
    Abstract: When producing hydrocarbons from fatty acid esters contained in fats or fat oils, the fatty acid esters initially are split up by hydrolytic decomposition into a first stream containing crude alcohol and water and a second stream containing free fatty acids, and subsequently the free fatty acids of the second stream are hydrogenated with hydrogen to obtain saturated hydrocarbons.
    Type: Application
    Filed: November 25, 2008
    Publication date: November 11, 2010
    Applicant: Lurgi GmbH
    Inventors: Norbert Palauschek, Peter Trabold, Helmut Heurich, Manfred Hoffmann
  • Publication number: 20100286420
    Abstract: The present invention has an object to provide the following method for producing fatty acid alkyl esters and/or glycerin and the following catalyst used in the production method. According to the production method, a fat or oil is reacted with an alcohol to give a fatty acid alkyl ester and/or glycerin suitably used in a food or fuel application, etc., with high efficiency, and complicated steps such as a step of recovering a catalyst can be simplified or omitted. According to the catalyst, an active metal component is not eluted even if the catalyst is used repeatedly or for a long period of time, and further, such a catalyst can maintain an excellent catalyst activity for a long time even in the presence of water and exhibit a high activity to both of transesterification of a glyceride contained in the fat or oil and esterification of free fatty acid.
    Type: Application
    Filed: October 17, 2008
    Publication date: November 11, 2010
    Applicant: Nippon Shokubai Co., Ltd.
    Inventors: Takeo Akatsuka, Masanori Nonoguchi, Tomoharu Oku
  • Patent number: 7825285
    Abstract: A process and an apparatus for the separation of a homogeneous catalyst solution from crude monoethylene glycol (MEG) and for purifying MEG is disclosed. The process comprises separating catalyst solution by evaporating crude MEG and feeding crude MEG to a rectification section, a stripping section, and thence to a pasteurisation section, each section operated at subatmospheric pressure of 0.5×105 Nm?2 or less, the rectification and pasteurisation sections being at pressure less than that of the catalyst separation section, wherein the process provides a pressure differential across the catalyst separation and rectification sections and wherein vapour phase crude MEG from the catalyst separation section is fed as substantially vapour phase feed to the rectification section.
    Type: Grant
    Filed: June 12, 2007
    Date of Patent: November 2, 2010
    Assignee: Shell Oil Company
    Inventors: Roel Guillaume Hubertus Leonardus Bastings, Anton Pieter Westerink
  • Patent number: 7812199
    Abstract: The present invention relates to novel hydroxyl compounds, compositions comprising hydroxyl compounds, and methods useful for treating and preventing a variety of diseases and conditions such as, but not limited to aging, Alzheimer's Disease, cancer, cardiovascular disease, diabetic nephropathy, diabetic retinopathy, a disorder of glucose metabolism, dyslipidemia, dyslipoproteinemia, hypertension, impotence, inflammation, insulin resistance, lipid elimination in bile, obesity, oxysterol elimination in bile, pancreatitis, pancreatitius, Parkinson's disease, a peroxisome proliferator activated receptor-associated disorder, phospholipid elimination in bile, renal disease, septicemia, metabolic syndrome disorders (e.g., Syndrome X), thrombotic disorder. Compounds and methods of the invention can also be used to modulate C reactive protein or enhance bile production in a patient.
    Type: Grant
    Filed: February 28, 2007
    Date of Patent: October 12, 2010
    Assignee: Esperion Therapeutics, Inc.
    Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu
  • Publication number: 20100249441
    Abstract: In the method of the present invention for producing fatty acid alkyl ester and/or glycerin, as a heat source for an alcohol refining step of refining alcohol from unreacted alcohol that remains without reacting in a first reaction step, at least a part of heat of the unreacted alcohol is used. This allows reducing costs in production of fatty acid alkyl ester and/or glycerin over a solid catalyst.
    Type: Application
    Filed: October 31, 2007
    Publication date: September 30, 2010
    Inventors: Masanori Nonoguchi, Hiroko Izumi, Atsushi Tachibana, Tomoharu Oku, Toshimitsu Moriguchi, Takeo Akatsuka, Izuho Okada, Hideaki Tsuneki, Hironori Horie
  • Patent number: 7718820
    Abstract: An alkanediol and a dialkyl carbonate are prepared in a process comprising: (a) reacting an alkylene carbonate and an alkanol feedstock in a first reaction zone under transesterification conditions to obtain a product mixture of dialkyl carbonate, unconverted alkanol, the alkanediol, unconverted alkylene carbonate and dimers of the alkanediol; (b) separating dialkyl carbonate and alkanol from the product mixture to obtain a bottom product stream containing alkanediol, unconverted alkylene carbonate and dimers of the alkanediol; (c) recovering the dialkyl carbonate; and (d) separating alkanediol from the bottom product stream to leave a recycle stream comprising unconverted alkylene carbonate and dimers of the alkanediol, which process further comprises (e) passing at least part of the recycle stream to a second reaction zone in which the dimers of the alkanediol are converted to higher-boiling oligomers of alkanediol, yielding an oligomers-containing effluent; (f) separating the higher-boiling oligomers from
    Type: Grant
    Filed: January 21, 2008
    Date of Patent: May 18, 2010
    Assignee: Shell Oil Company
    Inventors: Timothy Michael Nisbet, Garo Garbis Vaporciyan, Cornelis Leonardus Maria Vrouwenvelder, Paul Wood
  • Patent number: 7674919
    Abstract: A process for the preparation of an alkylene carbonate, said process comprising contacting the corresponding alkylene oxide with carbon dioxide in the presence of water and in the presence of a catalytic composition comprising an organic base neutralized with a hydrogen halide, wherein the organic base comprises a carbon-based compound comprising one or more nitrogen atoms with at least one free electron pair and/or one or more phosphorous atoms with at least one free electron pair and wherein the organic base has a pKa greater than 8.
    Type: Grant
    Filed: September 14, 2007
    Date of Patent: March 9, 2010
    Assignee: Shell Oil Company
    Inventors: Dirk Michiel Boele, Henricus Petrus Bernardus Duijghuisen, Eugene Marie Godfried Andre Van Kruchten, Jan Herman Hendrik Meurs
  • Patent number: 7501531
    Abstract: A process for the preparation of an alkylene carbonate, said process comprising contacting the corresponding alkylene oxide with carbon dioxide in the presence of a metal salt immobilised on a solid support, wherein the metal salt comprises a cation of a metal selected from those in the third period and group 2, the fourth period and groups 2 and 4 to 12, the fifth period and groups 2, 4 to 7, 12 and 14, and the sixth period and groups 2 and 4 to 6 of the periodic table according to IUPAC nomenclature, and an anion selected from anions of inorganic acids and organic acids, and wherein the solid support contains a quaternary ammonium, a quaternary phosphonium, a quaternary arsenonium, a quaternary stibonium, or a ternary sulfonium cation.
    Type: Grant
    Filed: August 2, 2007
    Date of Patent: March 10, 2009
    Assignee: Shell Oil Company
    Inventors: Eugene Marie Godfried Andre Van Kruchten, Hendrik Stichter
  • Patent number: 7465840
    Abstract: A process for the preparation of an alkylene glycol, said process comprising reacting the corresponding alkylene carbonate with water and/or an alcohol in the presence of a metalate immobilised on a solid support, wherein the solid support is a strongly basic ion exchange resin having cations attached to a polymeric backbone.
    Type: Grant
    Filed: September 5, 2007
    Date of Patent: December 16, 2008
    Assignee: Shell Oil Company
    Inventor: Eugene Marie Godfried Andre Van Kruchten
  • Patent number: 7462748
    Abstract: A process for the preparation of an alkylene glycol, said process comprising reacting the corresponding alkylene carbonate with water in the presence of a catalyst, wherein the catalyst comprises bicarbonate as active phase, immobilized on a solid support, having one or more electropositive sites.
    Type: Grant
    Filed: September 5, 2007
    Date of Patent: December 9, 2008
    Assignee: Shell Oil Company
    Inventor: Eugene Marie Godfried Andre Van Kruchten
  • Patent number: 7459588
    Abstract: A method for producing an unsaturated vicinal diol compound represented by the formula (2): wherein R1, R2, R3, R4, R5 and R are the same or different and each independently represent a hydrogen atom; a C1-C20 alkyl group which may be substituted with a halogen atom or atoms, a C1-C6 alkoxy group or groups, a C2-C7 alkoxycabonyl group or groups, a C6-C10 aryl group or groups, or a carboxyl group or groups; or a C6-C10 aryl group which may be substituted with a halogen atom or atoms, a C1-C6 alkoxy group or groups, a C6-C10 aryl group or groups, or a carboxyl group or groups; which comprises reacting an unsaturated epoxy compound represented by the formula (1): wherein R1, R2, R3, R4, R5 and R6 are the same as defined above, with water in the presence of a silicate containing at least one element selected from a group 5 element and a group 6 element of the long periodic table as a constituent.
    Type: Grant
    Filed: September 9, 2005
    Date of Patent: December 2, 2008
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Koji Hagiya
  • Patent number: 7453014
    Abstract: The invention provides a process for the preparation of an alkaline glycol from an alkaline carbonate, wherein alkaline carbonate is hydrolyzed in the presence of catalyst in a baffled reactor. The baffled reactor has at least four compartments, the compartments are formed by internal baffles and the internal baffles provide a sinuous route for reaction fluid through the reactor.
    Type: Grant
    Filed: December 3, 2007
    Date of Patent: November 18, 2008
    Assignee: Shell Oil Company
    Inventors: Gerrit Jan Harmsen, Arthur Willibrordus Titus Rots, Anton Pieter Westerink
  • Publication number: 20080154070
    Abstract: The invention provides a process for the preparation of an alkylene glycol from an alkylene carbonate, wherein alkylene carbonate is hydrolysed in the presence of catalyst in a baffled reactor. The baffled reactor has at least four compartments, the compartments are formed by internal baffles and the internal baffles provide a sinuous route for reaction fluid through the reactor.
    Type: Application
    Filed: December 3, 2007
    Publication date: June 26, 2008
    Inventors: Gerrit Jan Harmsen, Authur Willibrordus Titus Rots, Anton Pieter Westerink
  • Patent number: 7385092
    Abstract: A process for preparing diols or triols made up of a1) reacting at least one monoolefin having 4 to 20 carbon atoms with hydrogen peroxide and formic acid in the presence of water to form a mixture or a2) reacting at least one monoolefin alcohol having 4 to 20 carbon atoms first with formic acid, and then reacting the product formed thereby with hydrogen peroxide in the presence of water to form a mixture, b) removing, by distillation, the water and formic acid from the mixture obtained in a1) or a2), c) reacting the mixture obtained from b) with an aliphatic alcohol in the presence of a sulfonic acid to form the diol or triol and at least one formic ester by-product, and d) optionally removing, by distillation, the at least one formic ester by-product formed together with any residual at least one aliphatic C1-C4-alcohol to isolate the diol or triol.
    Type: Grant
    Filed: December 15, 2005
    Date of Patent: June 10, 2008
    Assignee: Degussa AG
    Inventors: Clemens Osterholt, Volker Brehme, Thomas Kübelbäck, Günther Köhler
  • Patent number: 7335799
    Abstract: The present invention relates to novel hydroxyl compounds, compositions comprising hydroxyl compounds, and methods useful for treating and preventing a variety of diseases and conditions such as, but not limited to aging, Alzheimer's Disease, cancer, cardiovascular disease, diabetic nephropathy, diabetic retinopathy, a disorder of glucose metabolism, dyslipidemia, dyslipoproteinemia, hypertension, impotence, inflammation, insulin resistance, lipid elimination in bile, obesity, oxysterol elimination in bile, pancreatitis, pancreatitius, Parkinson's disease, a peroxisome proliferator activated receptor-associated disorder, phospholipid elimination in bile, renal disease, septicemia, metabolic syndrome disorders (e.g., Syndrome X), thrombotic disorder. Compounds and methods of the invention can also be used to modulate C reactive protein or enhance bile production in a patient.
    Type: Grant
    Filed: December 23, 2003
    Date of Patent: February 26, 2008
    Assignee: Esperion Therapeutics, Inc.
    Inventors: Jean-Louis Henri Dasseux, Carmen Daniela Oniciu