By Alcoholysis, Hydrolysis, Or Saponification Of An Ester Patents (Class 568/877)
  • Patent number: 9353036
    Abstract: Subject-matter of the invention is a process for producing fatty alcohols by catalytic hydrogenation of fatty acid methyl ester (FAME), in which the FAME initially is hydrogenated to fatty alcohol (FA). The fractions of non-converted FAME remaining in the hydrogenation product are converted to wax ester and methanol in a succeeding transesterification step with FA. According to the invention, catalysts on the basis of magnesium oxide or hydrotalcite are used. After separating the methanol and the FA as target product, a stream enriched in wax ester is recirculated to the hydrogenation reactor.
    Type: Grant
    Filed: June 17, 2014
    Date of Patent: May 31, 2016
    Assignee: L'Air Liquide Société Anonyme Pour L'Étude Et L'Exploitation Des Procedes Georges Claude
    Inventors: Rudolf Bönsch, Ingo Bauer
  • Patent number: 9212114
    Abstract: In a process for producing fatty alcohol, fatty acid is subjected to esterification with a lower alkanol to form a stream of lower alkyl fatty acid ester(s). The stream is vaporized and then subjected to hydrogenation. The stream is then subjected to transesterification in a wax ester reactor to convert at least a portion of the lower alkyl fatty acid ester(s) to lower alkanol and wax ester(s). The resulting stream is then separated to yield a fatty alcohol(s) steam, a wax ester(s) stream, and an overhead stream comprising fatty alkanol(s) and alkane. The overhead stream is reacted in a wax ester reactor to convert at least a portion of the lower alkyl fatty acid ester to lower alkanol and wax ester(s). The wax ester(s) formed from the alkane is separated, along with any water and/or lower alkanol present.
    Type: Grant
    Filed: October 3, 2013
    Date of Patent: December 15, 2015
    Assignee: JOHNSON MATTHEY DAVY TECHNOLOGIES LIMITED
    Inventors: Paul John Cassidy, Robert Wild, Rikard Umberto Andersson, Simon Nicholas Tilley, Adrian Backes
  • Patent number: 9150473
    Abstract: A method for producing allyl alcohol is disclosed. The method includes steps of feeding allyl acetate and water into a reactive distillation column; performing a reaction in a reaction zone and separating a product containing allyl alcohol, acetic acid and water from the reactive distillation column. Accordingly, the method effectively enhances a conversion rate of hydrolysis for allyl acetate, simplifies the process and reduces energy consumption.
    Type: Grant
    Filed: March 21, 2014
    Date of Patent: October 6, 2015
    Assignee: Dairen Chemical Corporation
    Inventors: Shien-Chang Chen, Tian-Yuan Lin, Shih-Bo Hung
  • Publication number: 20150105592
    Abstract: A method of making alcohols involves forming of alcohol esters from liquid alkane halides and a solution of metallic salts of organic acids to produce gaseous alcohol esters for reaction with magnesium or metal hydroxides to form the alcohol and the metal salt of the organic acids. In an improvement method liquid phase alcohol esters instead of gaseous alcohol esters are produced from liquid alkane halides and a solution of metal salts of organic acids whose alkane esters are less soluble in water than that of the alkane halide and treating of the alcohol ester formed with magnesium or metal hydroxides to form the alcohol and the metal salt of the organic acids.
    Type: Application
    Filed: December 19, 2014
    Publication date: April 16, 2015
    Applicant: Sajet Development LLC
    Inventors: Jorge Miller, Luisa Kling Miller
  • Publication number: 20150080615
    Abstract: A process for recovering alcohol from a fatty acid and/or diacid alcohol ester using water in an equal or lesser amount than oil on a mass basis. The process uses multiple reactors with separation of the alcohol product of hydrolysis between successive reactors. The use of low amounts of water allows recovery of the alcohol with a lower evaporation requirement, thus making a more energy efficient process.
    Type: Application
    Filed: September 12, 2014
    Publication date: March 19, 2015
    Inventors: STUART B. FERGUSSON, LARIN GODFROY, MICHAEL CHARLES GRADY, DAVID F. KRAYNIE, WILLIAM D. PARTEN, STEPHEN M. TIERI
  • Publication number: 20140364656
    Abstract: A method of making alcohols involves forming of alcohol esters from liquid alkane halides and a solution of metallic salts of organic acids to produce gaseous alcohol esters for reaction with magnesium or metal hydroxides to form the alcohol and the metal salt of the organic acids. In an improvement method liquid phase alcohol esters instead of gaseous alcohol esters are produced from liquid alkane halides and a solution of metal salts of organic acids whose alkane esters are less soluble in water than that of the alkane halide and treating of the alcohol ester formed with magnesium or metal hydroxides to form the alcohol and the metal salt of the organic acids.
    Type: Application
    Filed: August 25, 2014
    Publication date: December 11, 2014
    Applicant: Sajet Development LLC
    Inventors: Jorge Miller, Luisa Kling Miller
  • Publication number: 20140364655
    Abstract: A method for producing allyl alcohol is disclosed. The method includes steps of feeding allyl acetate and water into a reactive distillation column; performing a reaction in a reaction zone and separating a product containing allyl alcohol, acetic acid and water from the reactive distillation column. Accordingly, the method effectively enhances a conversion rate of hydrolysis for allyl acetate, simplifies the process and reduces energy consumption.
    Type: Application
    Filed: March 21, 2014
    Publication date: December 11, 2014
    Applicant: Dairen Chemical Corporation
    Inventors: Shien-Chang Chen, Tian-Yuan Lin, Shih-Bo Hung
  • Patent number: 8884078
    Abstract: In a process for the production of fatty alcohol(s) a fatty acid or fatty acid mixture is subjected to esterification with a lower alkanol to form a stream comprising the corresponding lower alkyl ester or esters. The stream is vaporized and subjected to hydrogenation to form a stream comprising fatty alcohol(s) and an amount of unconverted lower alkyl ester(s). This stream is subjected to transesterification in a wax ester reactor in the presence of a solid transesterification catalyst. Fatty alcohol(s) and wax ester(s) are then separated by distillation to yield a fatty alcohol(s) product and a stream comprising wax ester(s). The stream of wax ester(s) is passed to a second hydrogenation zone to effect hydrogenation in the liquid phase to revert the wax ester(s) to fatty alcohol(s), which are returned to the distillation separation step.
    Type: Grant
    Filed: November 1, 2012
    Date of Patent: November 11, 2014
    Assignee: Davy Process Technology Limited
    Inventors: Paul Appleton, Michael Anthony Wood, Robert Wild
  • Publication number: 20140323773
    Abstract: In a process for the production of fatty alcohol(s) a fatty acid or fatty acid mixture is subjected to esterification with a lower alkanol to form a stream comprising the corresponding lower alkyl ester or esters. The stream is vaporised and subjected to hydrogenation to form a stream comprising fatty alcohol(s) and an amount of unconverted lower alkyl ester(s). This stream is subjected to transesterification in a wax ester reactor in the presence of a solid transesterification catalyst. Fatty alcohol(s) and wax ester(s) are then separated by distillation to yield a fatty alcohol(s) product and a stream comprising wax ester(s). The stream of wax ester(s) is passed to a second hydrogenation zone to effect hydrogenation in the liquid phase to revert the wax ester(s) to fatty alcohol(s), which are returned to the distillation separation step.
    Type: Application
    Filed: November 1, 2012
    Publication date: October 30, 2014
    Applicant: Davy Process Technology Limited
    Inventors: Paul Appleton, Michael Anthony Wood, Robert Wild
  • Publication number: 20140020283
    Abstract: This invention relates to the use of a tunicate or an extract obtained from a tunicate for the production of one or more biofuel selected from an alcohol and biodiesel. The invention also relates to a method for producing a biofuel from a tunicate wherein the biofuel is selected from an alcohol and biodiesel and wherein said method comprises the steps of: (a)(i) subjecting said tunicate or one or more polysaccharides extracted from said tunicate to enzymatic or acid hydrolysis to form a hydrolysate containing one or more monosaccharides and (ii) fermenting said one or more monosaccharides to form an alcohol; or (b)(i) extracting lipids/fatty acids from said tunicate and (ii) converting said lipids/fatty acids into biodiesel by transesterification or alcoholysis or (iii) subjecting said tunicate to transesterification or alcoholysis thereby converting lipids/fatty acids present in said tunicate into biodiesel.
    Type: Application
    Filed: June 17, 2011
    Publication date: January 23, 2014
    Applicant: Bergen Teknologioverforing AS
    Inventor: Willy Dalheim
  • Patent number: 8575403
    Abstract: Recovery of ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid by hydrolyzing a portion of the crude ethanol product or one or more derivative streams obtained therefrom. The one or more derivative streams comprise ethyl acetate and the hydrolyzed stream is directly or indirectly fed to the distillation zone or the hydrogenation reactor.
    Type: Grant
    Filed: July 9, 2010
    Date of Patent: November 5, 2013
    Assignee: Celanese International Corporation
    Inventors: Victor J. Johnston, Lincoln Sarager, R. Jay Warner, Trinity Horton, Radmila Jevtic
  • Publication number: 20130172602
    Abstract: A process for production of allyl acetate includes steps of reacting acetic acid 3, oxygen 1 and propylene 2 in the presence of a catalyst in an oxidation reactor 5 to form allyl acetate and water; separating the unreacted acetic acid by a distillation column 9; and recovering an acetic acid-containing liquid which contains acetic acid and returning the acetic acid-containing liquid to the oxidation reactor 5 via an acetic acid-water evaporator 4, the process further including a heating step of heating a process liquid which contains the acetic acid-containing liquid to a temperature of 80 to 250° C. by a heater.
    Type: Application
    Filed: September 20, 2011
    Publication date: July 4, 2013
    Applicant: SHOWA DENKO K.K.
    Inventor: Wataru Oguchi
  • Patent number: 8426654
    Abstract: Method for producing fatty alcohols includes splitting vegetable oils and animal fats under pressure into fatty acids and glycerol in counterflow to steam. The reaction product is physically separated into fatty acids and sweet water containing glycerol. The fatty acids are subjected to a distillation, and the separated fatty acid fraction is mixed together with fatty alcohol at 230 to 270° C. and atmospheric pressure. The wax esters obtained by esterification are hydrogenated to fatty alcohols by adding hydrogen on a fixed-bed catalyst, and the reaction product is separated into fatty alcohols and hydrogen. The wax esters are hydrogenated on a fixed bed of uniformly shaped catalyst bodies produced by extrusion, which consist of the main components copper and copper-chromium oxide and the secondary components zinc, aluminum, iron, silicon and alkaline earth elements, at 180 to 220° C. and 70 to 100 bar(a).
    Type: Grant
    Filed: February 12, 2009
    Date of Patent: April 23, 2013
    Assignee: Lurgi GmbH
    Inventors: Rudolf Boensch, Klaus Noweck
  • Patent number: 8378156
    Abstract: Process for homologation of alcohol(s), by 1 introducing alcohol(s) into an etherification unit to produce alkyl ether(s), 2, introducing at least a part of the alkyl ether(s) from step 1, together with CO and optionally H2, into a carbonylation unit, in the presence of an acidic homogeneous or heterogeneous carbonylation catalyst, to produce alkyl ester(s), and 3, introducing at least a part of the alkyl ester(s) from step 2, together with H2, into a hydrogenation unit, to produce homologated alcohol(s). Optionally, at least a part of the homologated alcohol(s) from step 3 is recycled into the etherification unit of step 1. Alcohol(s) from the hydrogenation unit of step 3 are recovered.
    Type: Grant
    Filed: December 12, 2008
    Date of Patent: February 19, 2013
    Assignee: BP P.L.C.
    Inventors: Berian John Daniel, Benjamin Patrick Gracey, John Glenn Sunley
  • Publication number: 20130035516
    Abstract: In one embodiment, the invention is to a process for purifying a crude ethanol product. The process comprises the step of hydrogenating acetic acid in a first reaction zone in the presence of a first catalyst to form the crude ethanol product comprising ethanol, acetaldehyde, acetic acid, water, and acetal. The process further comprises the step of separating at least a portion of the crude ethanol product into a refined ethanol stream and a by-product stream. The refined ethanol stream comprises ethanol and acetaldehyde; and the by-product stream comprises acetic acid and a substantial portion of the water from the crude ethanol product. The process further comprises the step of hydrolyzing in a second reaction zone at least a portion of the acetal.
    Type: Application
    Filed: August 3, 2011
    Publication date: February 7, 2013
    Applicant: CELANESE INTERNATIONAL CORPORATION
    Inventors: Adam Orosco, Lincoln Sarager, R. Jay Warner, Radmila Jevtic
  • Publication number: 20120289636
    Abstract: A method for preparation of secondary alcohols with a high proportion of hydroxyl group at the C2 position is disclosed. Alkyl carboxylates, high in alpha-methylcarboxylate content, are produced via reaction of an alpha-olefin and a carboxylic acid in the presence of a cerium catalyst. The resultant alkyl carboxylate is hydrolyzed to yield a secondary alcohol with a high 2-hydroxyl content. The secondary alcohol may be used to prepare esters, especially phthalate esters or cyclohexanoate diesters, which are useful as plasticizers. These esters are more effective as plasticizers than esters derived from other secondary alcohols due to their high C2 point of attachment.
    Type: Application
    Filed: November 16, 2010
    Publication date: November 15, 2012
    Inventors: Karla S. Colle, Allen D. Godwin
  • Patent number: 8309758
    Abstract: A process for purifying allyl acetate is disclosed. An acetoxylation mixture is distilled at elevated pressure to remove propylene and generate a first bottoms mixture comprising allyl acetate, acetic acid, acrolein, allyl diacetate, and 3-acetoxypropionaldehyde. The first bottoms mixture is flash vaporized, and the resulting vapor is contacted with a solid acidic catalyst under conditions effective to decompose allyl diacetate and 3-acetoxypropionaldehyde. The flashed product, which comprises allyl acetate, acetic acid, and acrolein, is then distilled to remove acrolein and generate a second bottoms mixture comprising allyl acetate and acetic acid. The second bottoms mixture can be used to manufacture allyl alcohol.
    Type: Grant
    Filed: December 17, 2009
    Date of Patent: November 13, 2012
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Stephen H. Harris, Shaw-Chan Lin
  • Publication number: 20120273339
    Abstract: Recovery of alcohol, in particular ethanol, from a crude product obtained from the hydrogenation of acetic acid using various combinations of membranes and/or distillation columns.
    Type: Application
    Filed: April 26, 2011
    Publication date: November 1, 2012
    Applicant: CELANESE INTERNATIONAL CORPORATION
    Inventors: David Lee, Adam Orosco, Lincoln Sarager, R. Jay Warner, Trinity Horton, Radmila Jevtic, Victor J. Johnston
  • Patent number: 8242295
    Abstract: Disclosed is a process for producing a fatty alkyl ester and glycerin, including step 1 of reacting fats and oils with C1 to C5 lower alcohols, step 2 of removing the lower alcohols discharged from the outlet of a rector in step 1 until the lower alcohol content is reduced to 8 wt % or less, step 3 of separating the product obtained in step 2 into oil and aqueous phases, step 4 of reacting the oil phase obtained in step 3 with lower alcohols in the presence of an acid catalyst, and step 5 of separating the product discharged from the outlet of a reactor in step 4 into oil and aqueous phases thereby giving fatty acid alkyl esters and glycerin, as well as a process for producing fatty alcohols from hydrogen and the fatty acid alkyl esters obtained in the above process.
    Type: Grant
    Filed: December 19, 2006
    Date of Patent: August 14, 2012
    Assignee: Kao Corporation
    Inventors: Yuichiro Seki, Nobuhiro Tatsumi, Takanobu Katayama
  • Publication number: 20120157707
    Abstract: Provided is a method for producing an alcohol compound, which enables the alcohol compound to be obtained at a high yield from an amide compound or amine compound. The method for producing an alcohol compound, which is characterized by comprising allowing an alcohol in a supercritical state to act on the amide compound or amine compound in the presence of a carboxylic acid derivative to obtain the alcohol compound.
    Type: Application
    Filed: August 2, 2010
    Publication date: June 21, 2012
    Applicants: UBE INDUSTRIES, LTD., YAMAGUCHI UNIVERSITY
    Inventors: Akio Kamimura, Kouji Kaiso, Tsunemi Sugimoto
  • Publication number: 20120142977
    Abstract: A method of making alcohols involves forming of alcohol esters from liquid alkane halides and a solution of metallic salts of organic acids to produce gaseous alcohol esters for reaction with magnesium or metal hydroxides to form the alcohol and the metal salt of the organic acids. In an improvement method liquid phase alcohol esters instead of gaseous alcohol esters are produced from liquid alkane halides and a solution of metal salts of organic acids whose alkane esters are less soluble in water than that of the alkane halide and treating of the alcohol ester formed with magnesium or metal hydroxides to form the alcohol and the metal salt of the organic acids.
    Type: Application
    Filed: February 8, 2012
    Publication date: June 7, 2012
    Inventors: Jorge Miller, Louisa Kling Miller
  • Patent number: 8193396
    Abstract: A process for producing allyl alcohol is disclosed. The process comprises reacting propylene, acetic acid, and oxygen to produce a reaction mixture. The reaction mixture is distilled to produce a vapor stream comprising propylene and a liquid stream comprising allyl acetate, acetic acid, acrolein, and allyl diacetate. The liquid stream is distilled to produce a lights stream comprising acrolein; a side draw comprising allyl acetate, acetic acid, and water; and a bottoms stream comprising acetic acid and allyl diacetate. The bottoms stream is distilled to remove a heavies stream comprising allyl diacetate. The side draw is hydrolyzed to produce allyl alcohol.
    Type: Grant
    Filed: February 25, 2010
    Date of Patent: June 5, 2012
    Assignee: Lyondell Chemical Technology, L.P.
    Inventors: Shaw-Chan Lin, Lawrence M. Candela, Andrew P. Kahn, Elizabeth I. Ross-Medgaarden, Gary A. Sawyer
  • Publication number: 20110312044
    Abstract: In an alcohol fermentation process, oil derived from biomass is chemically converted into an extractant available for in situ removal of a product alcohol such as butanol from a fermentation broth. The glycerides in the oil can be chemically converted into a reaction product, such as fatty acids, fatty alcohols, fatty amides, fatty acid methyl esters, fatty acid glycol esters, and hydroxylated triglycerides, and mixtures thereof, which forms a fermentation product extractant having a partition coefficient for a product alcohol greater than a partition coefficient of the oil of the biomass for the product alcohol. Oil derived from a feedstock of an alcohol fermentation process can be chemically converting into the fermentation product extractant.
    Type: Application
    Filed: June 17, 2011
    Publication date: December 22, 2011
    Applicant: BUTAMAX(TM) ADVANCED BIOFUELS LLC
    Inventors: DOUGLAS ROBERT ANTON, JELENA CIRAKOVIC, BRUCE A. DINER, MICHAEL CHARLES GRADY, FRANCIS J. WOERNER
  • Publication number: 20110275861
    Abstract: Recovery of ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid by hydrolyzing a portion of the crude ethanol product or one or more derivative streams obtained therefrom. The one or more derivative streams comprise ethyl acetate and the hydrolyzed stream is directly or indirectly fed to the distillation zone or the hydrogenation reactor.
    Type: Application
    Filed: July 9, 2010
    Publication date: November 10, 2011
    Applicant: CELANESE INTERNATIONAL CORPORATION
    Inventors: Victor J. Johnston, Lincoln Sarager, R. Jay Warner, Trinity Horton, Radmila Jevtic
  • Publication number: 20110275862
    Abstract: Recovery of ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid. Separation and purification processes of the crude ethanol products are employed to allow recovery of ethanol and remove acetal impurities.
    Type: Application
    Filed: September 24, 2010
    Publication date: November 10, 2011
    Applicant: Celanese International Corporation
    Inventors: Victor J. Johnston, Josefina T. Chapman, Radmila Jevtic, Heiko Weiner, Tianshu Pan, R. Jay Warner, Gerald Grusendorf, Nathan Bower, Lincoln M. Sarager
  • Publication number: 20110207973
    Abstract: A process for producing allyl alcohol is disclosed. The process comprises reacting propylene, acetic acid, and oxygen to produce a reaction mixture. The reaction mixture is distilled to produce a vapor stream comprising propylene and a liquid stream comprising allyl acetate, acetic acid, acrolein, and allyl diacetate. The liquid stream is distilled to produce a lights stream comprising acrolein; a side draw comprising allyl acetate, acetic acid, and water; and a bottoms stream comprising acetic acid and allyl diacetate. The bottoms stream is distilled to remove a heavies stream comprising allyl diacetate. The side draw is hydrolyzed to produce allyl alcohol.
    Type: Application
    Filed: February 25, 2010
    Publication date: August 25, 2011
    Inventors: Shaw-Chan Lin, Lawrence M. Candela, Andrew P. Kahn, Elizabeth I. Ross-Medgaarden, Gary A. Sawyer
  • Publication number: 20110130597
    Abstract: A method comprising reacting an alkane gas with a halogen gas in a halogenations reactor to form a halogenation reaction product mixture comprising alkane halide and hydrogen halide mixture; mixing the halogenations reaction product mixture with a countercurrent flow of a metal organic salt thereby forming an extractor product mixture of a metal halide, organic salt, and organic acid separating the organic ester and organic acid mixture from the metal halide; oxygenating the metal halide to form a metal oxide and halide containing gasses; separating the metal oxide from the halide containing gasses; mixing the metal oxide with water to form a metal oxide slurry; mixing the metal oxide slurry with a countercurrent flow of the organic ester and organic acid mixture to form a raw product comprising alkanol, a metal organic salt is provided.
    Type: Application
    Filed: November 30, 2010
    Publication date: June 2, 2011
    Inventors: Jorge Miller, Marie-Francine Moens
  • Patent number: 7816568
    Abstract: Catalytic reactions conducted during acid digestion of cellulose materials, including paper, a wide range of grasses including prairie grass, switch grass, pine wood sawdust, bagasse dried after sugar cane processing, cotton, waste cellulose products and starch materials, are taught for direct conversion to ethanol. The cellulose material is thoroughly wet in concentrated sulfuric acid in the presence of transition metal complexes possessing a degree of symmetry. Ethanol formed during the reaction can be removed by distillation affording a continuous process.
    Type: Grant
    Filed: December 17, 2007
    Date of Patent: October 19, 2010
    Inventor: Melvin Keith Carter
  • Publication number: 20100197977
    Abstract: A process for purifying an acetoxylation mixture is disclosed. Allyl acetate, water, acetic acid, and from 0.1 to 10 wt. % allyl diacetate are contacted in the vapor phase with a solid acidic catalyst under conditions effective to decompose the allyl diacetate and generate an intermediate stream comprising allyl acetate, water, acetic acid, and acrolein. Acrolein is then removed from the intermediate stream, preferably by distillation, to give an allyl acetate-containing product stream. Usually, this product stream is then hydrolyzed to produce allyl alcohol. The invention includes processes in which propylene first reacts with oxygen and acetic acid in the presence of a noble metal catalyst to generate the acetoxylation mixture.
    Type: Application
    Filed: February 5, 2009
    Publication date: August 5, 2010
    Inventor: Stephen H. Harris
  • Publication number: 20080293977
    Abstract: The invention relates to a method for preparing linear long chain fatty alcohols having 20 to 40 carbon atoms by a growth reaction of ethylene on aluminum compounds.
    Type: Application
    Filed: June 22, 2005
    Publication date: November 27, 2008
    Inventor: Holger Ziehe
  • Patent number: 7176336
    Abstract: A process of preparing an unsaturated alcohol (olefin alcohol), such as, a homo-allylic mono-alcohol or homo-allylic polyol, involving protecting a hydroxy-substituted unsaturated fatty acid or fatty acid ester, such as methyl ricinoleate, derived from a seed oil, to form a hydroxy-protected unsaturated fatty acid or fatty acid ester; homo-metathesizing or cross-metathesizing the hydroxy-protected unsaturated fatty acid or fatty acid ester to produce a product mixture containing a hydroxy-protected unsaturated metathesis product; and deprotecting the hydroxy-protected unsaturated metathesis product under conditions sufficient to prepare the unsaturated alcohol. Preferably, methyl ricinoleate is converted by cross-metathesis or homo-metathesis into the homo-allylic mono-alcohol 1-decene-4-ol or the homo-allylic polyol 9-octadecene-7,12-diol, respectively.
    Type: Grant
    Filed: September 14, 2004
    Date of Patent: February 13, 2007
    Assignee: Dow Global Technologies Inc.
    Inventors: Bob R. Maughon, Kenneth A. Burdett, Zenon Lysenko
  • Patent number: 7164049
    Abstract: 3,3-Dimethylbutanal is prepared from 3,3-dimethylbutanol. Intermediate 3,3-dimethylbutanol is obtained by reacting ethylene, isopropylene and a mineral acid to produce a 3,3-dimethylbutyl ester which is hydrolyzed to the alcohol. The hydrolysis step is effectively carried out by reactive distillation. Alternatively, 3,3-dimethylbutanal is prepared from 3,3-dimethylbutanol obtained by reduction of the corresponding carboxylic acid or 1,2-epoxy-3,3-dimethylbutane, or by hydrolysis of 1-halo-3,3-dimethylbutane. Fixed bed gas phase and stirred tank liquid phase processes are provided for converting 3,3-dimethylbutanol to 3,3-dimethylbutanal by catalytic dehydrogenation.
    Type: Grant
    Filed: March 27, 2003
    Date of Patent: January 16, 2007
    Assignee: The Nutrasweet Company
    Inventors: Jerry R. Ebner, Zhi Guo, Arnold Hershman, Loraine M. Klein, William D. McGhee, Mark Paster, Indra Prakash
  • Patent number: 7041199
    Abstract: A process and a device for the catalytic hydrolysis of a carboxylate, e.g., methyl acetate, ethyl acetate, i- or n-propyl acetate, i- or n-butyl acetate, allyl acetate and methyl formate, into the corresponding carboxylic acid and alcohol, by a combination of a pre-reactor and a reactive distillation column are disclosed. By the combination of a pre-reactor and a reactor distillation column, the conversion ratio can be substantially improved. The device can compensate for fluctuations in the supply quantity or in the composition of the feed flow. The product composition can also be controlled in a wide range.
    Type: Grant
    Filed: October 11, 2000
    Date of Patent: May 9, 2006
    Assignees: Sulzer Chemtech AG, Wacker Chemie GmbH
    Inventors: Peter Moritz, Franz Ramgraber, Claudia von Scala, Harald Michl
  • Patent number: 7034060
    Abstract: The present invention provides a novel method for the preparation of a unique profile of primary aliphatic alcohols, having 24 to 30 carbon atoms, from the wax secreted by the insect Ericerus pela. Included in the present invention is the composition of matter, referred to herein as “polycosanol” produced by the method of this invention. The polycosanol composition is comprised primarily of the four primary aliphatic alcohols, tetracosanol, hexacosanol, octacosanol and triacontanol. Further included in this invention is the use of said composition of matter for the prevention and treatment of obesity, syndrome X, diabetes, hypercholesterolemia, atherosclerotic complications, ischemia and thrombosis.
    Type: Grant
    Filed: November 16, 2004
    Date of Patent: April 25, 2006
    Assignee: Unigen Pharmaceuticals, Inc.
    Inventors: Qi Jia, Ji-Fu Zhao
  • Patent number: 6984666
    Abstract: The present invention provides a novel method for the preparation of a unique profile of primary aliphatic alcohols, having 24 to 30 carbon atoms, from the wax secreted by the insect Ericerus pela. Included in the present invention is the composition of matter, referred to herein as “polycosanol” produced by the method of this invention. The polycosanol composition is comprised primarily of the four primary aliphatic alcohols, tetracosanol, hexacosanol, octacosanol and triacontanol. Further included in this invention is the use of said composition of matter for the prevention and treatment of obesity, syndrome X, diabetes, hypercholesterolemia, atherosclerotic complications, ischemia and thrombosis.
    Type: Grant
    Filed: November 16, 2004
    Date of Patent: January 10, 2006
    Assignee: Unigen Pharmaceuticals, Inc.
    Inventors: Qi Jia, Ji-Fu Zhao
  • Patent number: 6683116
    Abstract: The present invention provides a novel method for the preparation of a unique profile of primary aliphatic alcohols, having 24 to 30 carbon atoms, from the wax secreted by the insect Ericerus pela. Included in the present invention is the composition of matter, referred to herein as “polycosanol” produced by the method of this invention. The polycosanol composition is comprised primarily of the four primary aliphatic alcohols, tetracosanol, hexacosanol, octacosanol and triacontanol. Further included in this invention is the use of said composition of matter for the prevention and treatment of obesity, syndrome X, diabetes, hypercholesterolemia, atherosclerotic complications, ischemia and thrombosis.
    Type: Grant
    Filed: January 31, 2003
    Date of Patent: January 27, 2004
    Assignee: Unigen Pharmaceuticals, Inc.
    Inventors: Qi Jia, Ji-Fu Zhao
  • Publication number: 20030069455
    Abstract: Disclosed is a method for preparing a substantially pure mixture of cyclododecanediol isomers. The isomers include 1,4-cyclododecanediol, 1,5-cyclododecanediol, and 1,6-cyclododecanediol. Also disclosed is a method for using a substantially pure mixture of cyclododecanediol isomers, which include the preparation of diamines; esters; diesters, such as diacetates and diacrylates; bis-phenol cyclododecane; and cyclododecanediol-based polyester polymers and polyester polyols.
    Type: Application
    Filed: September 16, 2002
    Publication date: April 10, 2003
    Inventors: Samuel Livingston Lane, Edward Francis Moran, John Joseph Ostermaier
  • Patent number: 6538162
    Abstract: The invention discloses a method for converting alkane to oxygenate which comprises the following steps: (i) contacting an alkane-containing gas with non-metal, regenerable, electrophile ions in a concentrated sulfuric acid medium under conditions sufficient to provide electrophilicly activated alkane and reduced electrophile ions; (ii) contacting said electrophilicly activated alkane with sulfate to form a sulfate ester; (iii) exposing the sulfate ester to hydrolyzing conditions sufficient to convert it to oxygenate; and (iv) collecting the oxygenate.
    Type: Grant
    Filed: January 30, 2001
    Date of Patent: March 25, 2003
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Clarence D. Chang, Jose G. Santiesteban
  • Patent number: 6278016
    Abstract: Methods for preparing ester derivatives of 3-methyl-2-buten-1-ol (prenyl alcohol) from 2-methyl-1,3-butadiene (isoprene) and alkanoic acids in the presence of an inorganic acid catalyst are disclosed. The resultant prenyl ester (e.g., prenyl acetate) can be converted to prenyl alcohol by reaction with water in the presence of either a suitable enzyme or a base.
    Type: Grant
    Filed: December 9, 1999
    Date of Patent: August 21, 2001
    Assignee: Loyola University of Chicago
    Inventor: James H. Babler
  • Patent number: 6166270
    Abstract: High purity tertiary butyl alcohol is obtained from mixtures comprised of tertiary butyl alcohol and tertiary butyl acetate by extractive distillation using a hydrocarbon extractive solvent such as decane.
    Type: Grant
    Filed: July 6, 1999
    Date of Patent: December 26, 2000
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Vijai P. Gupta, Michael J. Szady
  • Patent number: 6133484
    Abstract: A tertiary butyl alcohol charge stock typically contaminated with from about 0.5 to about 2 wt. % of formates and peroxides, is passed through an oxygenates decomposition reactor containing a bed of a decomposition catalyst comprising rhodium, platinum, palladium or mixture thereof at a temperature of from about 100 to about 280C to decompose the peroxides and formates, and to dehydrate a portion of the tertiary butyl alcohol to form isobutylene and water to thereby form a non-corrosive tertiary butyl alcohol feedstock that is substantially free from formates that is suitable for reaction with methanol in a methyl tertiary butyl ether etherification reactor to form a non-corrosive methyl tertiary butyl ether etherification reaction product from which methyl tertiary butyl ether can be recovered.
    Type: Grant
    Filed: February 18, 1999
    Date of Patent: October 17, 2000
    Assignee: Huntsman ICI Chemical LLC
    Inventors: John Frederick Knifton, John Ronald Sanderson, William Alan Smith, James Douglas Goshinska, Mark Allen Mueller
  • Patent number: 5939592
    Abstract: A tertiary butyl alcohol charge stock typically contaminated with from about 0.5 to about 2 wt. % of formates and peroxides, is passed through an oxygenates decomposition reactor containing a bed of a decomposition catalyst comprising rhodium, platinum, palladium or mixture thereof at a temperature of from about 100 to about 280.degree. C. to decompose the peroxides and formates, and to dehydrate a portion of the tertiary butyl alcohol to form isobutylene and water to thereby form a non-corrosive tertiary butyl alcohol feedstock that is substantially free from formates that is suitable for reaction with methanol in a methyl tertiary butyl ether etherification reactor to form a non-corrosive methyl tertiary butyl ether etherification reaction product from which methyl tertiary butyl ether can be recovered.
    Type: Grant
    Filed: November 10, 1997
    Date of Patent: August 17, 1999
    Assignee: Huntsman Specialty Chemicals Corp.
    Inventors: John Frederick Knifton, John Ronald Sanderson, William Alan Smith
  • Patent number: 5888923
    Abstract: The present invention relates to a modified Raney nickel catalyst which can serves as hydrogenation catalyst for hydroxy aldehydes, such as 4-hydroxy-butanal, and 2-methyl-3-hydroxypropanal and hydroxy cyclic ethers such as 2-hydroxy-tetrahydrofuran. Further, a process for preparing diols by using the modified Raney nickel catalyst is provided.
    Type: Grant
    Filed: April 15, 1996
    Date of Patent: March 30, 1999
    Assignee: Dairen Chemical Corporation
    Inventors: Shien Chang Chen, C. C. Chu, F. S. Lin, J. Y. Chou, C. C. Huang
  • Patent number: 5872277
    Abstract: Methods for preparing 3-methyl-2-buten-1-ol (prenyl alcohol) from 2-methyl-1,3-butadiene (isoprene) and carboxylic acids are disclosed. Carboxylic acids which can be used in the process have a K.sub.a (relative to water) greater than 10.sup.-4 ; dichloroacetic acid is especially preferred. The process involves the slow (e.g., dropwise) addition of isoprene to the carboxylic acid to form a prenyl ester. The ester-formation reaction proceeds at room temperature in most cases; use of an organic base catalyst, preferably a sodium or potassium salt of the reactant carboxylic acid, improves the yield. The resultant prenyl ester can be converted to prenyl alcohol by reaction with a base. Prenyl alcohol can be readily converted to citral, a chemical intermediate in the synthesis of vitamins A and E, and several widely-used carotenoids.
    Type: Grant
    Filed: March 10, 1997
    Date of Patent: February 16, 1999
    Assignee: Loyola University of Chicago
    Inventor: James H. Babler
  • Patent number: 5872289
    Abstract: A liquid-phase process for hydrolyzing a carboxylic acid alkyl ester having 2 to 18 carbon atoms to provide a product mixture comprising a carboxylic acid and an alcohol comprising contacting a feedstock comprising the carboxylic acid alkyl ester and water with an acidic carbon catalyst under reaction conditions sufficient to form the product mixture comprising the carboxylic acid and the alcohol. Suitable acidic carbon catalysts include charcoal and carbons produced from a variety of sources including coconut shells, coal, wood and peat. Carbon catalysts may be rendered acidic by treatment with nitric acid.
    Type: Grant
    Filed: March 6, 1998
    Date of Patent: February 16, 1999
    Assignee: Air Products and Chemicals, Inc.
    Inventors: John Bruce Appleby, Francis Joseph Waller, Stephen Charles Webb
  • Patent number: 5856316
    Abstract: A mixture of higher primary aliphatic alcohols of 22 to 38 carbon atoms can be obtained by saponifying and extracting steps with organic solvents from sugar cane wax. The mixture which contains tetracosanol, hexacosanol, heptacosanol, octacosanol, nonacosanol, triacontanol, dotriacontanol and tetratriacontanol can be used for the treatment of hypercholesterolemia, and atherosclerotic complications as platelet hyperaggregabiulity, ischemia and thrombosis, and prevents drug induced gastric ulcer and improves male sexual activity.
    Type: Grant
    Filed: December 23, 1996
    Date of Patent: January 5, 1999
    Assignee: Laboratorios Dalmer SA
    Inventors: Abilio Laguna Granja, Juan Magraner Hernandez, Daisy Carbajal Quintana, Lourdes Arruzazabala Valmana, Rosa Mas Ferreiro, Milagros Garcia Mesa
  • Patent number: 5847239
    Abstract: Dihydromyrcene is reacted with a carboxylic acid, eg acetic acid, to produce an ester which is then reacted with an alcohol in a transesterification reaction to produce (dihydro)myrcenol and another ester. The preferred alcohol is 4-tertiarybutylcyclohexanol. Myrcenol can be produced in a similar way.
    Type: Grant
    Filed: January 15, 1997
    Date of Patent: December 8, 1998
    Assignee: Quest International B.V.
    Inventors: Paul Nicolas Davey, Clive Derek Richardson, Christopher Paul Newman, Barrie R. Hart
  • Patent number: 5696299
    Abstract: A process for producing an optically active alcohol comprising carrying out interesterification between a racemic alcohol and an ester selected from the group consisting of (a) a diester between a lower monohydric alcohol and a saturated dicarboxylic acid having 14 or more carbon atoms, (b) a triglyceride of a saturated fatty acid having 16 or more carbon atoms, and (c) a monoester between a lower monohydric alcohol and a saturated fatty acid having 18 or more carbon atoms in the presence of lipase, preferably heat-resistant lipase, and in the presence or absence of a solvent, preferably in the absence of a solvent, under a substantially water-free condition, separating an optically active alcohol rich in either one of R- and S-forms from the reaction mixture, and adding an optically inactive non-racemic alcohol to the residue of the previous step to carry out interesterification under the same conditions as in the previous reaction to separate the other enantiomer.
    Type: Grant
    Filed: September 15, 1995
    Date of Patent: December 9, 1997
    Assignee: The Nisshin Oil Mills, Ltd.
    Inventors: Satoshi Negishi, Seiichi Shirasawa, Junko Suzuki, Yukie Masuda
  • Patent number: 5663156
    Abstract: A mixture of higher primary aliphatic alcohols of 22 to 38 carbon atoms can be obtained by saponifying and extracting steps with organic solvents from sugar cane wax. The mixture which contains tetracosanol, hexacosanol, heptacosanol, octacosanol, nonacosanol, triacontanol, dotriacontanol and tetratriacontanol can be used for the treatment of hypercholesterolemia, and atherosclerotic complications as platelet hyperaggregabiulity, ischemia and thrombosis, and prevents drug induced gastric ulcer and improves male sexual activity.
    Type: Grant
    Filed: July 25, 1994
    Date of Patent: September 2, 1997
    Assignees: Laboratorios Dalmer SA, Adanifer, S.A.
    Inventors: Abilio Laguna Granja, Juan Magraner Hernandez, Daisy Carbajal Quintana, Lourdes Arruzazabala Valmana, Rosa Mas Ferreiro, Milagros Garcia Mesa
  • Patent number: 5635542
    Abstract: The present invention relates to a process for the production of hydroxyl-group-containing compounds suitable for the polyisocyanate polyaddition process from polyurea and/or polyurethane polyurea wastes by treating polyurea and/or polyurethane polyurea wastes with diols and/or polyols at temperatures from 160.degree. to 260.degree. C., the water present in the reaction vessel preferably being removed by distillation during the heating-up phase, characterized in that 1,3-dicarbonyl compounds are added to the reaction mixture before or during the reaction.
    Type: Grant
    Filed: June 16, 1995
    Date of Patent: June 3, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Thomas Munzmay, Werner Rasshofer, Walter Meckel