Polyoxy Containing Reactant Patents (Class 568/486)
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Patent number: 10569259Abstract: The present disclosure relates to a catalyst for dehydration of glycerin, a preparation method thereof, and a production method of acrolein using the catalyst. Particularly, the catalyst according to an embodiment of the present disclosure is used in a dehydration reaction of glycerin to exhibit high catalytic activity, a high yield, and high selectivity to acrolein and acrylic acid, and has a longer lifetime compared to the conventional catalysts due to a characteristic that coke carbon cannot be easily deposited on the surface of the catalyst.Type: GrantFiled: December 15, 2016Date of Patent: February 25, 2020Assignee: LG CHEM, LTD.Inventors: Jun Seon Choi, Ji Yeon Kim, Joo Young Cheon, Wang Rae Joe, Hye Jeong Ok, Kyung Soo Kim
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Patent number: 10046307Abstract: The present invention relates to: a catalyst for glycerin dehydration; a preparation method therefor; and an acrolein preparation method using the catalyst. According to one embodiment of the present invention, the catalyst is used in glycerin dehydration so as to exhibit high catalytic activity, a high yield and high acrolein selectivity, and has a characteristic in which carbon is not readily deposited, thereby having a long lifetime compared with that of a conventional catalyst.Type: GrantFiled: December 8, 2015Date of Patent: August 14, 2018Assignee: LG CHEM, LTD.Inventors: Ji Yeon Kim, Jun Seon Choi, Joo Young Cheon, Wang Rae Joe, Hye Jeong Ok, Kyung Soo Kim
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Patent number: 9861957Abstract: The present invention relates to: a catalyst for glycerin dehydration; a preparation method therefor; and an acrolein preparation method using the catalyst. According to one embodiment of the present invention, the catalyst is used in glycerin dehydration so as to exhibit high catalytic activity, a high yield and high acrolein selectivity, and has a characteristic in which carbon is not readily deposited, thereby having a long lifetime compared with that of a conventional catalyst.Type: GrantFiled: December 8, 2015Date of Patent: January 9, 2018Assignee: LG CHEM, LTD.Inventors: Ji Yeon Kim, Jun Seon Choi, Joo Young Cheon, Wang Rae Joe, Hye Jeong Ok, Kyung Soo Kim
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Patent number: 9393554Abstract: Provided is a method that produces a saturated aldehyde from a 1,2-alkanediol in high yield. Disclosed is a method for producing a saturated aldehyde from a 1,2-alkanediol in the presence of a regular mesoporous material.Type: GrantFiled: February 4, 2014Date of Patent: July 19, 2016Assignees: TOKUSHIMA UNIVERSITY, MITSUBISHI RAYON CO., LTD.Inventors: Shigeru Sugiyama, Yuuki Katou, Toshiya Yasukawa, Shuji Akihara, Wataru Ninomiya
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Patent number: 9365477Abstract: Provided is a method of producing lavandulal at a high yield by controlling formation of its isomer of lavandulal as a by-product. In a method of producing lavandulal by making an acetal compound represented by the following formula (I) react with 3-methyl-1-butene-3-ol in the presence of an acid catalyst, the method includes: adding, to a liquid mixture comprising an acid catalyst, an acetal compound represented by the following formula (I), and 3-methyl-1-butene-3-ol in at least a portion of an amount to be used (3-methyl-1-butene-3-ol (a)), 3-methyl-1-butene-3-ol in the other portion of the amount to be used (3-methyl-1-butene-3-ol (b)); and maintaining the liquid mixture at a temperature of 110° C. or higher: in which Each R in the formula (I) represents an alkyl group.Type: GrantFiled: March 6, 2014Date of Patent: June 14, 2016Assignee: KURARAY CO., LTD.Inventor: Junko Sato
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Patent number: 9327276Abstract: The present invention relates to a catalyst for glycerin dehydration, a preparation method thereof, and a preparation method of acrolein, and more particularly, to a catalyst for glycerin dehydration which minimizes by-product formation during glycerin dehydration to improve acrolein selectivity and maintains high catalytic activity during reaction.Type: GrantFiled: July 15, 2014Date of Patent: May 3, 2016Assignee: LG CHEM, LTD.Inventors: Jun Seon Choi, Ji Yeon Kim, Joo Young Cheon, Wang Rae Joe
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Patent number: 9255056Abstract: Provided is a method for industrially producing a conjugated Z-alken-yn-yl acetate such as Z-13-hexadecen-11-yn-yl acetate which is a sex pheromone component of a pine processionary moth, and an intermediate for the conjugated Z-alken-yn-yl acetate under mild conditions at a high yield. More specifically, provided is a method for producing a conjugated Z-alken-yn-yl acetate (5) comprising the steps of: reacting an ?-halo-2-alkynal (1) with an alkylidene triphenylphosphorane (3) through a Wittig reaction to obtain a conjugated Z-alken-yn-yl halide (4), and acetoxylating the conjugated Z-alken-yn-yl halide (4) into a conjugated Z-alken-yn-yl acetate (5).Type: GrantFiled: April 9, 2014Date of Patent: February 9, 2016Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Miyoshi Yamashita, Takehiko Fukumoto, Takeshi Kinsho
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Publication number: 20150141703Abstract: The invention concerns a chemical reaction process performed in a reaction chamber (1) which contains a catalyst bed, the reaction chamber (1) comprising a first end (2) and a second end (3), opposite the first end (2), the process involving alternately: a reaction phase, in which a reaction flow passes through the reaction chamber (1) from its first end (2) towards its second end (3); and a catalyst-regeneration phase, in which a regeneration flow passes through the reaction chamber (1) from its second end (3) towards its first end (2). The reaction chamber (1) preferably consists of a plurality of separate reaction compartments containing a catalyst bed and a heat-exchange system for exchanging heat therebetween.Type: ApplicationFiled: June 6, 2013Publication date: May 21, 2015Inventor: Jean-Luc Dubois
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Patent number: 8993810Abstract: Disclosed is a preparation method of the lycopene intermediate 3-methyl-4,4-dialkoxy-1-butaldehyde. The preparation method comprises the following steps: (1) reacting 2-methyl-3,3-dialkoxy-1-halopropane with magnesium powder in the solvent of anhydrous tetrahydrofuran at a temperature of 45˜65° C. to generate a mixture of Grignard reagents under the protection of an inert gas; and (2) adding N,N-disubstituted carboxamide to the mixture of Grignard reagents and reacting at a temperature of 10° C.˜35° C. to obtain 3-methyl-4,4-dialkoxy-1-butaldehyde. The process route of the present invention is simple and direct, the operation is easy, the conditions are mild and the yield is good, and thus the invention has commercial value.Type: GrantFiled: December 10, 2012Date of Patent: March 31, 2015Assignees: Nanjing University of Technology, Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical FactoryInventors: Chunlei LV, Shiqing Pi, Jianhui Chen, Dingqiang Lu, Pingkai Ouyang
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Publication number: 20150087861Abstract: The invention relates to the production of acrolein and/or acrylic acid from glycerol, and more particularly to a method for continuous production of a stream comprising acrolein by dehydration of glycerol, comprising cycles of reaction and regeneration of a dehydration catalyst.Type: ApplicationFiled: April 3, 2013Publication date: March 26, 2015Inventors: Jean-Francois Devaux, Michel Fauconet, Nabil Tlili
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Publication number: 20150031887Abstract: An organocatalyst for oxidizing alcohols in which a primary alcohol is selectively oxidized in a polyol substrate having a plurality of alcohols under environmentally-friendly conditions. The organic oxidation catalyst has an oxygen atom bonded to a nitrogen atom of an azanoradamantane skeleton and at least one alkyl group at positions 1 and 5. The oxidation catalyst has higher activity than TEMPO, which is an existing oxidation catalyst, in the selective oxidation reaction of primary alcohols, and better selectivity than AZADO and 1-Me-AZADO. This DMN-AZADO can be applied to the selective oxidation reaction of primary alcohols that contributes to shortening the synthesizing process for pharmaceuticals, pharmaceutical raw materials, agricultural chemicals, cosmetics, organic materials, and other such high value-added organic compounds.Type: ApplicationFiled: February 22, 2013Publication date: January 29, 2015Inventors: Yoshiharu Iwabuchi, Masatoshi Shibuya, Ryusuke Doi
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Patent number: 8940942Abstract: One or more embodiments of the invention are directed to the synthetic methods for making lepidopteran pheromones including navel orangeworm pheromones. The synthetic methods involve novel, efficient, and environmentally benign steps and procedures.Type: GrantFiled: December 26, 2013Date of Patent: January 27, 2015Assignee: Suterra LLCInventors: Andrew Thompson, Xiongzhi Zhang, Lonnie Robarge
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Publication number: 20150005526Abstract: A catalyst composition comprising at least an heteropolyacid deposited on a porous titania carrier. A catalyst composition comprising at least an heteropolyacid in which protons in the heteropolyacid may be partially exchanged by at least one cation selected from elements belonging to Group 1 to Group 16 of the Periodic Table of Elements that have been deposited on a porous titania carrier. A method for preparing the catalyst composition, comprising impregnating a titania carrier with a solution of at least one metal selected from elements belonging to the Group 1 to Group 16 of the Periodic Table of Elements or onium, drying and firing the resulting solid mixture, secondly impregnating the resulting solid mixture with a solution of heteropolyacid, drying, and firing the resulting solid mixture. A process for preparing acrolein and acrylic acid by dehydration of glycerin, carried out in the presence of the catalyst.Type: ApplicationFiled: September 19, 2014Publication date: January 1, 2015Applicants: ARKEMA FRANCE, NIPPON KAYAKU KABUSHIKI KAISHAInventors: Yasuhiro MAGATANI, Kimito OKUMURA, Jean-Luc DUBOIS, Jean-Francois DEVAUX
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Patent number: 8907135Abstract: The present disclosure relates to facilities, systems, methods and/or catalysts for use in chemical production. In particular, the disclosure provides innovations relating to dehydration of multihydric compounds such as glycerol to form acrolein. Some of these innovations include continuous reaction systems as well as system parameters that allow for long term production.Type: GrantFiled: May 10, 2013Date of Patent: December 9, 2014Assignee: Battelle Memorial InstituteInventors: James J. Strohm, Alan H. Zacher, James F. White, Michel J. Gray, Vanessa Lebarbier
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Publication number: 20140309452Abstract: Provided is a method for industrially producing a conjugated Z-alken-yn-yl acetate such as Z-13-hexadecen-11-yn-yl acetate which is a sex pheromone component of a pine processionary moth, and an intermediate for the conjugated Z-alken-yn-yl acetate under mild conditions at a high yield. More specifically, provided is a method for producing a conjugated Z-alken-yn-yl acetate (5) comprising the steps of: reacting an ?-halo-2-alkynal (1) with an alkylidene triphenylphosphorane (3) through a Wittig reaction to obtain a conjugated Z-alken-yn-yl halide (4), and acetoxylating the conjugated Z-alken-yn-yl halide (4) into a conjugated Z-alken-yn-yl acetate (5).Type: ApplicationFiled: April 9, 2014Publication date: October 16, 2014Applicant: Shin-Etsu Chemical Co., Ltd.Inventors: Miyoshi Yamashita, Takehiko Fukumoto, Takeshi Kinsho
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Patent number: 8829246Abstract: The subject of the present invention is a process for preparing acrolein by dehydration of glycerol in the presence of a catalyst system based on iron phosphorous oxide containing, in addition, one or more elements chosen from alkali metals, alkaline-earth metals, AI, Si, B, Co, Cr, Ni, V, Zn, Zr, Sn, Sb, Ag, Cu, Nb, Mo, Y, Mn, Pt, Rh and the rare earths La, Ce, Sm. The process is preferably carried out in the gas phase in the presence of oxygen starting from aqueous solutions of glycerol. The process according to the invention makes it possible of obtain high acrolein selectivities.Type: GrantFiled: September 11, 2008Date of Patent: September 9, 2014Assignee: Arkema FranceInventor: Jean-Luc Dubois
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Publication number: 20140213811Abstract: The present invention relates to the production of acrolein, acrylic acid or methacrylic acid by dehydration reaction of renewable raw material such as glycerin or hydroxycarboxylic acids, in the presence of a novel catalyst system supported on a carrier having a bimodal structure and a high pore volume and distribution. The dehydration reactions can be carried out for longer operation duration, so that acrolein, acrylic acid or methacrylic acid can be produced at higher productivity and for longer running time.Type: ApplicationFiled: July 27, 2012Publication date: July 31, 2014Inventors: Jean-Luc Dubois, Kimito Okumura, Yasushi Kobayashi, Ryota Hiraoka
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Publication number: 20140206906Abstract: One or more embodiments of the invention are directed to the synthetic methods for making lepidopteran pheromones including navel orangeworm pheromones. The synthetic methods involve novel, efficient, and environmentally benign steps and procedures.Type: ApplicationFiled: December 26, 2013Publication date: July 24, 2014Applicant: Suterra LLCInventors: Andrew Thompson, Xiongzhi Zhang, Lonnie Robarge
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Patent number: 8742178Abstract: An object of the present invention is to provide a technology which can suppress the blockage and abrasion of pipes and devices caused by the production of by-products and stably synthesize acrolein at a high yield, under a condition in which energy efficiency is improved by an elevated concentration of glycerol in a reaction liquid, in a process for synthesis of acrolein by reacting supercritical water and an acid with glycerol. An embodiment of the present invention includes: setting a concentration of glycerol in the reaction liquid at 30% by weight or lower; also cooling the reaction liquid to a temperature between a temperature (300° C. or lower) at which the reaction stops and a temperature (100° C.Type: GrantFiled: February 9, 2010Date of Patent: June 3, 2014Assignee: Hitachi, Ltd.Inventors: Takeyuki Kondo, Hiroyuki Ito, Yasunari Sase, Toshiaki Matsuo, Kenichiro Oka, Masayuki Kamikawa, Masashi Tanto
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Patent number: 8692029Abstract: An object of the present invention is to provide an industrially applicable method for producing acrolein via treatment with supercritical water from glycerin obtained as a by-product during the process of biodiesel fuel production from waste animal/plant fat or oil with the use of an alkali catalyst. The present invention provides a method for producing acrolein, which comprises: a determination step of determining the hydrogen ion concentration in glycerin obtained as a by-product; an acid addition step of adding to the glycerin an acid at an amount calculated based on the results of the determination step so as to make the glycerin acidic; and a supercritical water treatment step of allowing supercritical water to act on the glycerin after the acid addition so as to produce acrolein from the glycerin.Type: GrantFiled: June 30, 2010Date of Patent: April 8, 2014Assignee: Hitachi, Ltd.Inventors: Masashi Tanto, Yasunari Sase, Hiroyuki Ito, Toshiaki Matsuo, Takeyuki Kondo
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Publication number: 20140094617Abstract: A chemical reactor including: a plurality of heat exchange plates which between them define reaction compartments, in which reactor each heat exchange plate includes two walls between them defining at least one heat exchange space, the respective walls being fixed together by joining regions, and the reactor also comprises at least one injection device for injecting substance into the reaction compartments, said substance-injection device passing through the heat-exchange plates in respective joining regions thereof. Also, a chemical reaction process that can be carried out in this reactor.Type: ApplicationFiled: June 1, 2012Publication date: April 3, 2014Applicant: ARKEMA FRANCEInventor: Jean-Luc Dubois
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Patent number: 8648216Abstract: One or more embodiments of the invention are directed to the synthetic methods for making lepidopteran pheromones including navel orangeworm pheromones. The synthetic methods involve novel, efficient, and environmentally benign steps and procedures.Type: GrantFiled: November 19, 2012Date of Patent: February 11, 2014Inventors: Andrew S. Thompson, Xiongzhi Shawn Zhang, Lonnie Robarge
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Publication number: 20140005442Abstract: The present invention relates to 2,6,10-trimethyl-3,5,9-undecatrienyl-1-aldehyde represented by formula (3), and a method for preparing this intermediate. The process route of the present invention is simple, the starting materials are available easily, and the cost is low.Type: ApplicationFiled: December 3, 2012Publication date: January 2, 2014Applicants: SHAOXING UNIVERSITY, ZHEJIANG MEDICINE CO., LTD. XINCHANGInventors: Runpu Shen, Chunlei LV, Xiaoyue Jiang, Xuejun Lao, Weidong Ye, Luo Liu, Xiaohua Song, Chunlei Wu
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Patent number: 8609904Abstract: The present invention relates to the manufacture of bioresourced acrolein and bioresourced acrylic acid from glycerol as starting material and more particularly comes within the scope of a process for the manufacture of acrolein and acrylic acid according to which the reaction for the dehydration of glycerol to give acrolein is carried out and a stage of oxidizing a water-rich phase separated from the reaction mixture coming from this dehydration reaction is carried out, before it is recycled to the glycerol dehydration stage. This oxidation treatment prevents organic impurities from accumulating during the process, while minimizing the consumption of water and the discharge of polluted aqueous streams.Type: GrantFiled: December 13, 2010Date of Patent: December 17, 2013Assignee: Arkema FranceInventors: Jean-Francois Devaux, Michel Fauconet, Nabil Tlili, Philippe Haller, Jean-Paul Combet
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Patent number: 8604234Abstract: The invention relates to a method for preparing acrolein from glycerol or glycerin, according to which dehydration of glycerol or glycerin is carried out in the presence of a catalyst which consists in at least one silica modified with zirconium dioxide, titanium dioxide or tungsten trioxide or any combination of these oxides, and a heteropolyacid. This method may be used for making 3-(methylthio)propionic aldehyde (MMP), 2-hydroxy-4-methylthiobutyronitrile (HMBTN), methionine or its analogs, from acrolein.Type: GrantFiled: December 21, 2010Date of Patent: December 10, 2013Assignees: Adisseo France S.A.S., Centre National de la Recherche Scientifique, Universite Lille 1-Sciences et TechnologiesInventors: Sebastien Paul, Benjamin Katryniok, Franck Dumeignil, Mickael Capron
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Publication number: 20130253227Abstract: The present disclosure relates to facilities, systems, methods and/or catalysts for use in chemical production. In particular, the disclosure provides innovations relating to dehydration of multihydric compounds such as glycerol to form acrolein. Some of these innovations include continuous reaction systems as well as system parameters that allow for long term production.Type: ApplicationFiled: May 10, 2013Publication date: September 26, 2013Applicant: Battelle Momerial InstituteInventors: James J. Strohm, Alan H. Zacher, James F. White, Michel J. Gray, Vanessa Lebarbier
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Patent number: 8530703Abstract: The present disclosure relates to facilities, systems, methods and/or catalysts for use in chemical production. In particular, the disclosure provides innovations relating to dehydration of multihydric compounds such as glycerol to form acrolein. Some of these innovations include continuous reaction systems as well as system parameters that allow for long term production.Type: GrantFiled: December 20, 2010Date of Patent: September 10, 2013Assignee: Battelle Memorial InstituteInventors: James J. Strohm, Alan H. Zacher, James F. White, Michel J. Gray, Vanessa Lebarbier
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Publication number: 20130217909Abstract: A continuous process for obtaining acrolein by catalytic dehydration of glycerol or glycerin, in the presence of an acid catalyst, wherein said process comprises the concomitant regeneration of said catalyst and is carried out in a fluidized bed reactor, said reactor comprising two zones, a first zone, or lower zone, termed catalyst regeneration zone, in which a fluidization gas comprising oxygen is introduced, and a second zone, or upper zone, termed reaction zone, in which the glycerol or glycerin is introduced and converted into acrolein.Type: ApplicationFiled: October 26, 2011Publication date: August 22, 2013Applicants: ECOLE CENTRALE DE LILLE, ADISSEO FRANCE S.A.S.Inventors: Stephane Pariente, Virginie Belliere-Baca, Sebastien Paul, Nouria Fatah
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Publication number: 20130197258Abstract: The invention concerns a method for preparing acrolein from glycerol or glycerine, wherein dehydration of the glycerol or glycerine is achieved in the presence of a catalyst based on zirconium oxide and which active phase consists in at least a) a silicon oxide, a zirconium oxide and at least one metal M oxide, said metal being selected from tungsten, cerium, manganese, niobium, tantalum, vanadium and titanium, b) a titanium oxide, a zirconium oxide and at least one metal M oxide, said metal being selected from tungsten, cerium, manganese, niobium, tantalum, vanadium and silicon. This method can be used for making 3-(methylthio)propionic aldehyde MMP, 2-hydroxy-4-,methylthiobutyronitrile HMTBN, methionine and its analogs.Type: ApplicationFiled: June 16, 2011Publication date: August 1, 2013Applicants: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, ADISSEO FRANCE S.A.S.Inventors: Pascaline Lauriol-Garbey, Virginie Belliere-Baca, Stéphane Loridant, Jean-Marc Millet
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Publication number: 20130190523Abstract: Novel synthetic routes, which are highly applicable for industrial preparation of therapeutically beneficial oxidized phospholipids are disclosed. Particularly, novel methods for efficiently preparing compounds having a glycerolic backbone and one or more oxidized moieties attached to the glycerolic backbone, which are devoid of column chromatography are disclosed. Further disclosed are novel methods of introducing phosphorous-containing moieties such as phosphate moieties to compounds having glycerolic backbone and intermediates firmed thereby.Type: ApplicationFiled: March 12, 2013Publication date: July 25, 2013Applicant: Vascular Biogenics Ltd.Inventor: Vascular Biogenics Ltd.
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Publication number: 20130158283Abstract: Novel synthetic routes, which are highly applicable for industrial preparation of therapeutically beneficial oxidized phospholipids are disclosed. Particularly, novel methods for efficiently preparing compounds having a glycerolic backbone and one or more oxidized moieties attached to the glycerolic backbone, which are devoid of column chromatography are disclosed. Further disclosed are novel methods of introducing phosphorous-containing moieties such as phosphate moieties to compounds having glycerolic backbone and intermediates formed thereby.Type: ApplicationFiled: December 10, 2012Publication date: June 20, 2013Applicant: Vascular Biogenics Ltd.Inventor: Vascular Biogenics Ltd.
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Publication number: 20130144086Abstract: One or more embodiments of the invention are directed to the synthetic methods for making lepidopteran pheromones including navel orangeworm pheromones. The synthetic methods involve novel, efficient, and environmentally benign steps and procedures.Type: ApplicationFiled: November 19, 2012Publication date: June 6, 2013Applicant: SUTERRA LLCInventor: SUTERRA LLC
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Publication number: 20130096322Abstract: A method of production of value-added, biobased chemicals, derivative products, and/or purified glycerin from bioglycerin of recycled oil, grease, and/or fat origin is described herein. A method of purification of bioglycerin of recycled oil, grease, and/or fat origin is also described herein. The method of purification of bioglycerin of recycled oil, grease, and/or fat origin described provides methods for desalinating, decolorizing, and/or concentrating bioglycerin of recycled oil, grease, and/or fat origin for the production of biobased chemicals, derivative products, and/or purified glycerin.Type: ApplicationFiled: January 12, 2012Publication date: April 18, 2013Applicant: THESIS CHEMISTRY, LLCInventors: John R. Peterson, Christopher M. Yost
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Publication number: 20130066100Abstract: A process for preparing a catalyst used in a production of acrolein and acrylic acid by dehydration reaction of glycerin, characterized by the steps of mixing a solution of heteropolyacid or constituents of heteropolyacid, a solution of at least one metal selected from elements belonging to Group 1 to Group 16 of the Periodic Table of Elements or its onium and a carrier to obtain a solid substance, and then of effecting at least one time of calcination before said solid substance is used in the dehydration reaction of glycerin. A catalyst obtained by the process for use in a production of acrolein and acrylic acid by dehydration reaction of glycerin. A process for preparing acrolein by catalytic dehydration of glycerin carried out in the presence of the catalyst and under a pressurized condition. A process for preparing acrylic acid obtained by oxydation of acrolein obtained. A process for preparing acrylonitrile obtained by ammoxidation of acrolein obtained.Type: ApplicationFiled: October 15, 2010Publication date: March 14, 2013Applicant: NIPPON KAYAKU KABUSHIKI KAISHAInventors: Yasuhiro Magatani, Kimito Okumura, Jean-Luc Dubois
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Publication number: 20130053595Abstract: A catalyst composition comprising at least an heteropolyacid deposited on a porous titania carrier. A catalyst composition comprising at least an heteropolyacid in which protons in the heteropolyacid may be partially exchanged by at least one cation selected from elements belonging to Group 1 to Group 16 of the Periodic Table of Elements that have been deposited on a porous titania carrier. A method for preparing the catalyst composition, comprising impregnating a titania carrier with a solution of at least one metal selected from elements belonging to the Group 1 to Group 16 of the Periodic Table of Elements or onium, drying and firing the resulting solid mixture, secondly impregnating the resulting solid mixture with a solution of heteropolyacid, drying, and firing the resulting solid mixture. A process for preparing acrolein and acrylic acid by dehydration of glycerin, carried out in the presence of the catalyst.Type: ApplicationFiled: September 18, 2009Publication date: February 28, 2013Applicants: ARKEMA FRANCE, NIPPON KAYAKU KABUSHIKI KAISHAInventors: Yasuhiro Magatani, Kimito Okumura, Jean-Luc Dubois, Jean-Francois Devaux
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Patent number: 8378136Abstract: The subject of the present invention is a process for preparing acrolein by dehydration of glycerol in the presence of a catalyst system comprising oxygen, phosphorus and at least one metal chosen from vanadium, boron or aluminium. The process is preferably carried out in the gas phase in the presence of oxygen starting from aqueous solutions of glycerol.Type: GrantFiled: October 5, 2009Date of Patent: February 19, 2013Assignee: Arkema FranceInventor: Jean-Luc Dubois
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Publication number: 20130018161Abstract: A catalyst for glycerin dehydration of the present invention comprises boron phosphate or a rare-earth metal phosphate, wherein a molar ratio P/B of phosphorus (P) to boron (B) or a molar ratio P/R of phosphorus (P) to a rare-earth metal (R) is more than 1.0 and 2.0 or less. An another catalyst for glycerin dehydration of the present invention comprises a combination of boron phosphate and a metal element or a combination of a rare-earth metal phosphate and a metal element other than a rare-earth metal, wherein a molar ratio M/(P+B) of a metal element (M) to phosphorus (P) and boron (B) or a molar ratio M/(P+R) of a metal element (M) to phosphorus (P) and a rare-earth metal (R) is more than 0.00005 and 0.5 or less.Type: ApplicationFiled: March 28, 2011Publication date: January 17, 2013Inventors: Takayuki Ezawa, Masaki Okada, Yoshitaka Arita
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Publication number: 20120330049Abstract: The invention relates to a method for preparing acrolein from glycerol or glycerin, according to which dehydration of glycerol or glycerin is carried out in the presence of a catalyst which consists in at least one silica modified with zirconium dioxide, titanium dioxide or tungsten trioxide or any combination of these oxides, and a heteropolyacid. This method may be used for making 3-(methylthio)propionic aldehyde (MMP), 2-hydroxy-4-methylthiobutyronitrile (HMBTN), methionine or its analogs, from acrolein.Type: ApplicationFiled: December 21, 2010Publication date: December 27, 2012Applicants: ADISSEO FRANCE S.A.S., UNIVERSITE LILLE 1 - SCIENCES ET TECHNOLOGIES, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUEInventors: Sebastien Paul, Benjamin Katryniok, Franck Dumeignil, Mickael Capron
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Publication number: 20120330058Abstract: The present invention relates to the manufacture of bioresourced acrolein and bioresourced acrylic acid from glycerol as starting material and more particularly comes within the scope of a process for the manufacture of acrolein and acrylic acid according to which the reaction for the dehydration of glycerol to give acrolein is carried out and the organic compounds which are heavier than water liable to be present in the various streams of the process arc removed, so as to obtain a stream which can be recycled to the dehydration stage without accumulation of heavy impurities, while minimizing the consumption of water and the discharge of polluted aqueous streams.Type: ApplicationFiled: December 10, 2010Publication date: December 27, 2012Inventors: Jean-Francois Devaux, Andre Lozowski, Nabil Tlili
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Patent number: 8329957Abstract: One or more embodiments of the invention are directed to the synthetic methods for making lepidopteran pheromones including navel orangeworm pheromones. The synthetic methods involve novel, efficient, and environmentally benign steps and procedures.Type: GrantFiled: February 13, 2012Date of Patent: December 11, 2012Assignee: Suterra LLCInventors: Andrew Thompson, Xiongzhi Zhang, Lonnie Robarge
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Publication number: 20120302797Abstract: The present invention relates to the manufacture of bioresourced acrolein and bioresourced acrylic acid from glycerol as starting material and more particularly comes within the scope of a process for the manufacture of acrolein and acrylic acid according to which the reaction for the dehydration of glycerol to give acrolein is carried out and a stage of oxidizing a water-rich phase separated from the reaction mixture coming from this dehydration reaction is carried out, before it is recycled to the glycerol dehydration stage. This oxidation treatment prevents organic impurities from accumulating during the process, while minimizing the consumption of water and the discharge of polluted aqueous streams.Type: ApplicationFiled: December 13, 2010Publication date: November 29, 2012Applicant: Arkema FranceInventors: Jean-Francois Devaux, Michel Fauconet, Nabil Tlili, Philippe Haller, Jean-Paul Combet
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Patent number: 8318978Abstract: The invention offers an improvement in a process for start-up in the occasion of producing acrylic acid by catalytically oxidizing acrolein at vapor phase under high load conditions, the start-up meaning the step of increasing the acrolein supply rate (loading) from the non-reacting condition to the prescribed reaction conditions. This process is characterized in that the acrolein supply rate is increased in the start-up stage of the reaction until the prescribed composition of starting reactant gas and the flow rate of the starting reactant gas are obtained, while adjusting at least one of the reaction temperature, the composition of the starting reactant gas and the flow rate of the starting reactant gas, so as to maintain the acrolein conversion at not lower than 90 mol %, the maximum peak temperature of the catalyst layer in each reaction zone at no higher than 400° C.Type: GrantFiled: March 26, 2010Date of Patent: November 27, 2012Assignee: Nippon Shokubai Co., Ltd.Inventors: Michio Tanimoto, Hideo Onodera
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Patent number: 8252960Abstract: The subject of the present invention is a process for preparing acrolein by dehydration of glycerin, characterized in that the dehydration is carried out in the presence of a catalyst comprising mainly a compound in which protons in a heteropolyacid are exchanged at least partially with at least one cation selected from elements belonging to Group 1 to Group 16 of the Periodic Table of Elements. The process according to the invention permits to obtain acrolein at higher yield.Type: GrantFiled: April 14, 2009Date of Patent: August 28, 2012Assignee: Arkema FranceInventors: Jean-Luc Dubois, Yasuhiro Magatani, Kimito Okumura
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Patent number: 8198477Abstract: The present invention relates to a process for producing acrolein by liquid phase dehydration of glycerol by preparing a mixture of a catalyst suspended in an organic solvent comprising one or more vinyl polymers and glycerol; and then mixing and heating the mixture to between 150° C. and 350° C. to dehydrate the glycerol and form acrolein. The vinyl polymers are selected from the group consisting of polyolefins, polystyrene, and mixtures thereof. The polyolefins may be polyethylene, polypropylene, polybutylene, polyisobutylene, polyisoprene, polypentene, or mixtures thereof. The acrolein may be subjected to vapor phase oxidation in the presence of a catalyst, such as a mixed metal oxide, to produce acrylic acid.Type: GrantFiled: November 20, 2009Date of Patent: June 12, 2012Inventors: Leonard Edward Bogan, Jr., Mark Anthony Silvano
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Publication number: 20120130108Abstract: Novel synthetic routes, which are highly applicable for industrial preparation of therapeutically beneficial oxidized phospholipids are disclosed. Particularly, novel methods for efficiently preparing compounds having a glycerolic backbone and one or more oxidized moieties attached to the glycerolic backbone, which are devoid of column chromatography are disclosed. Further disclosed are novel methods of introducing phosphorous-containing moieties such as phosphate moieties to compounds having glycerolic backbone and intermediates formed thereby.Type: ApplicationFiled: January 26, 2012Publication date: May 24, 2012Applicant: Vascular Biogenics Ltd.Inventors: Gideon Halperin, Eti Kovalevski-Ishai
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Publication number: 20120095269Abstract: An object of the present invention is to provide an industrially applicable method for producing acrolein via treatment with supercritical water from glycerin obtained as a by-product during the process of biodiesel fuel production from waste animal/plant fat or oil with the use of an alkali catalyst. The present invention provides a method for producing acrolein, which comprises: a determination step of determining the hydrogen ion concentration in glycerin obtained as a by-product; an acid addition step of adding to the glycerin an acid at an amount calculated based on the results of the determination step so as to make the glycerin acidic; and a supercritical water treatment step of allowing supercritical water to act on the glycerin after the acid addition so as to produce acrolein from the glycerin.Type: ApplicationFiled: June 30, 2010Publication date: April 19, 2012Inventors: Masashi Tanto, yasunari Sase, Hiroyuki Ito, Toshiaki Matsuo, Takeyuki Kondo
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Patent number: 8143455Abstract: What is described is a process for preparing 2-hydroxyacetals of the general formula in which R1 is hydrogen, a branched or unbranched C1-C12-alkyl radical, an electron-deficient, halogen-, NO2—, CN—, CF3—, acyl group- or branched or unbranched alkyl group-substituted or unsubstituted C5-C6-aryl or heteroaryl, and R2 is a branched or unbranched C1-C5-alkyl radical, or both R2 radicals are bonded directly to one another or to one another via a C1-C4 unit, by reacting an enol compound of the general formula (II) in which R3 is the same and R1 is as defined for formula (Ia), with bromine to give the corresponding dibromo adduct and then reacting this dibromo adduct with an alkoxide of the general formula (III) M-O—R2 (III) in which R2 is as defined for formula (Ia) and O is oxygen and M is lithium, sodium or potassium. What is likewise described is the preparation of the corresponding 2-hydroxyalkanals from the 2-hydroxyacetals thus obtained by acidic hydrolysis.Type: GrantFiled: June 11, 2008Date of Patent: March 27, 2012Assignee: SALTIGO GmbHInventors: Thomas-Norbert Müller, Michael Dockner
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Publication number: 20120065429Abstract: The present invention is directed to alkanal derivatives of water-soluble polymers such as poly(ethylene glycol), their corresponding hydrates and acetals, and to methods for preparing and using such polymer alkanals. The polymer alkanals of the invention are prepared in high purity and exhibit storage stability.Type: ApplicationFiled: November 21, 2011Publication date: March 15, 2012Applicant: NEKTAR THERAPEUTICSInventor: Antoni Kozlowski
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Patent number: 8115035Abstract: One or more embodiments of the invention are directed to the synthetic methods for making lepidopteran pheromones including navel orangeworm pheromones. The synthetic methods involve novel, efficient, and environmentally benign steps and procedures.Type: GrantFiled: April 20, 2010Date of Patent: February 14, 2012Assignee: Suterra, LLCInventors: Andrew Thompson, Xiongzhi Zhang, Lonnie Robarge
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Publication number: 20110319667Abstract: In order to perform organic synthesis process through action with supercritical water and acid stably while suppressing a trouble caused by a by-product, a method and an apparatus are provided, including the following steps. Water is supplied to high-pressure pumps (110) and (210) from water headers (101) and (201), and a pressure-reducing valve (324) is regulated to increase the pressure to 35 MPa. Temperatures of preheaters (120) and (220) and a heater (310) are increased until the reaction solution is at a temperature of 400° C. Acid (sulfuric acid) and an organic compound raw material (glycerin) are supplied from an acid header (203) and a raw-material header (203?) for action with the supercritical water to obtain a reaction solution. The obtained reaction solution is cooled to 100 to 200° C.Type: ApplicationFiled: February 5, 2010Publication date: December 29, 2011Inventors: Takeyuki Kondo, Hiroyuki Ito, Naruyasu Okamoto, Yasunari Sase, Toshiaki Matsuo, Kenichiro Oka, Masayuki Kamikawa