Bonding A Hydrocarbyl Group To The -c(=o)o- Containing Reactant Patents (Class 554/162)
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Patent number: 11725156Abstract: A hydrotreating and isomerization pre-treatment process in a biofuel production plant, which is characterized in that it occurs from a raw supply consisting of an organic feed comprising secondary materials such as frying oils, category 1 animal fats, residual oils or by-products consisting of monoglycerides, diglycerides, triglycerides and free fatty acids, which is added to a recycling stream consisting of a mixture of mono-, di- and triglycerides free of impurities and exiting an esterification unit, said process occurring by means of hydrolysis with excess water, under controlled pressure and temperature conditions, thus obtaining the partial or total conversion of the supply into glycerol and fatty acids, the excess water introduced into the hydrolysis process acting as a solvent for impurities of various nature present in ionic form, thus removing most of the heavy metals, as well as of the chlorides present in said supply.Type: GrantFiled: August 13, 2020Date of Patent: August 15, 2023Assignee: NEXTCHEM S.P.A.Inventor: Antonio Zarli
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Patent number: 11457655Abstract: Disclosed are techniques and systems for producing microbials having anaplerotic oils that are rich in odd-chain fatty acids, and other beneficial components, at higher concentrations than those present in other natural dietary sources of OCFA, at lower cost, and higher production yield. Further, disclosed are examples of incorporation of these higher concentration OCFA products into food for human and non-human animal consumption.Type: GrantFiled: April 26, 2021Date of Patent: October 4, 2022Assignee: HELIAE DEVELOPMENT, LLCInventors: Micheal LaMont, Magdalena Amezquita Emult, Eneko Ganuza Taberna
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Patent number: 10986856Abstract: Disclosed are techniques and systems for producing microbials having anaplerotic oils that are rich in odd-chain fatty acids, and other beneficial components, at higher concentrations than those present in other natural dietary sources of OCFA, at lower cost, and higher production yield. Further, disclosed are examples of incorporation of these higher concentration OCFA products into food for human and non-human animal consumption.Type: GrantFiled: November 5, 2020Date of Patent: April 27, 2021Assignee: Heliae Development, LLCInventors: Micheal LaMont, Magdalena Amezquita Ernult, Eneko Ganuza Taberna
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Patent number: 9260372Abstract: The present invention provides a pretreatment method to reduce saturated fatty acids of fatty acids used as feedstock when preparing ester polyols. The range of feedstock includes non-fractionated to fully fractionated feedstock. Performing some fractionation by distillation of the fatty acids derived from feedstock eliminates the need to fractionate the various ozone esters from each other before esterification. Further, the approach of the present invention is more economical and efficient than the conventional method of fractionation by crystallization.Type: GrantFiled: February 28, 2013Date of Patent: February 16, 2016Assignee: Petroliam Nasional BerhadInventors: Herman Paul Benecke, Daniel B. Garbark
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Publication number: 20150018572Abstract: The purpose of the present invention is to solve various problems with fatty acid alkyl ester methods using conventional homogenous-phase catalysts, and to provide a solid acid catalyst for fatty acid alkyl ester manufacturing that can be used to manufacture high-quality fatty acid alkyl esters and high-purity glycerin from various oils at low cost and with high yield.Type: ApplicationFiled: March 13, 2013Publication date: January 15, 2015Inventor: Shosei Oh
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Publication number: 20140357881Abstract: Process for coproduction of a vinyl ester of the formula R—C(O)O—CH?CH by transvinylation reaction of a carboxylic acid of the formula R—C(O)OH with a transvinylating reagent of the formula R1—C(O)O CH?CH2, characterized in that (a) the transvinylation reaction is conducted continuously at a temperature of 90 to 160° C. and at a pressure of 0.Type: ApplicationFiled: January 18, 2013Publication date: December 4, 2014Inventors: Leif Johnen, Heinz Strutz
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Publication number: 20140343310Abstract: The present invention relates to a continuous, catalytic process for preparing a vinyl ester of the formula R—C(O)O—CH?CH2 by reaction of a carboxylic acid of the formula R—C(O)OH with a transvinylating reagent of the formula R1—C(O)O—CH?CH2, wherein the reaction is effected at a temperature of 90 to 160° C. and at a pressure of 0.5 to 15 MPa without withdrawal of a reactant in the presence of a transition metal catalyst containing at least one transition metal from the group of ruthenium, osmium, rhodium, iridium, palladium and platinum, and then the resulting reaction mixture is separated into its constituents.Type: ApplicationFiled: January 18, 2013Publication date: November 20, 2014Inventors: Leif Johnen, Heinz Strutz, Kurt Schalapski, Norman Nowotny, Wolfgang Höfs, Sebastian Geisel
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Patent number: 8497389Abstract: Embodiments of the present application provide methods for processing biodiesel from feedstock using a single-step process. The methods can include, for example, use of a gaseous catalyst as part of the esterification/transesterification process. Embodiments of the present application also provide systems for the methods thereof.Type: GrantFiled: December 8, 2009Date of Patent: July 30, 2013Assignee: Initio Fuels LLCInventor: Raveendran Pottathil
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Publication number: 20130172589Abstract: A surface active agent comprising an arylated methyl ester of a fatty acid, or mixture of fatty acids, derived from biodiesel or a triglyceride source is disclosed. The fatty acid mixture is condensed to methyl esters and alkylated with aromatic substituents under Friedel-Crafts conditions. The alkylated methyl esters may be alkoxylated using a catalyst derived from fatty acids, alkaline earth salts, and strong acids. The resulting nonionic surfactant may also be sulfonated to produce one class of anionic surfactants. The alkylated methyl esters may also be directly sulfonated to produce another class of anionic surfactants.Type: ApplicationFiled: September 19, 2011Publication date: July 4, 2013Applicant: Huntsman Petrochemical LLCInventors: George A. Smith, Daniel R. Weaver, Zheng Chai
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Patent number: 8420840Abstract: A method comprising providing a starting composition comprising a polyunsaturated fatty acid, a polyunsaturated fatty ester, a carboxylate salt of a polyunsaturated fatty acid, a polyunsaturated triglyceride, or a mixture thereof; self-metathesizing the starting composition or cross-metathesizing the starting composition with at least one short-chain olefin in the presence of a metathesis catalyst to form self-/cross-metathesis products comprising: cyclohexadiene; at least one olefin; and one or more acid-, ester-, or salt-functionalized alkene; and reacting cyclohexadiene to produce at least one cycloalkane or cycloalkane derivatives.Type: GrantFiled: December 2, 2011Date of Patent: April 16, 2013Inventor: Edwin S. Olson
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Patent number: 8420842Abstract: This invention proposes a lanolin substitute, capable of absorbing up to at least twice its weight of water or aqueous solution or aqueous suspension. It forms true emulsions, stable over time with a capacity for water absorption superior to that of lanolin. It also possesses the known emollient, moisturizing and occlusive properties of lanolin. This substitute is usable in all the present and future areas of application of lanolin: in the cosmetics industry, dermatology, and in industrial applications (polishes, lubricants . . . ). It is obtained by hemi-synthesis from a mixture of unsaturated fatty acids, esters of unsaturated fatty acids, unsaturated hydrocarbons or unsaturated derivatives of the latter and compounds comprising or generating hydroxyl functions, such as glycerol, preferably without a catalyst and in an atmosphere devoid of oxygen. Classical thermal treatment or preferably treatment by dielectric heating.Type: GrantFiled: June 28, 2002Date of Patent: April 16, 2013Assignee: Aldivia SAInventors: Pierre Charlier De Chily, Mikaele Raynard
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Patent number: 8362288Abstract: A process for preparing a composition of alcoholic esters of straight chain monocarboxylic acids containing 6 to 26 carbon atoms and glycerin, starting from a vegetable or animal oil, neutral or acidic, virgin or recycled with mono-alcohols containing 1 to 18 atoms, in the presence of a zinc aluminate catalyst and in the presence of a controlled quantity of water, can directly produce, in one or more steps, an ester which can be used as a propellant or fuel along with glycerin having improved purity containing a reduced quantity of ethers by using a partially dried catalyst.Type: GrantFiled: September 10, 2010Date of Patent: January 29, 2013Assignee: IFP Energies NouvellesInventors: Vincent Coupard, Sylvie Maury, Veronique Pugnet
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Publication number: 20120102827Abstract: A method comprising the steps of providing a fatty acyl mixture comprising: (i) a C10-C16 acyl carbon atom chain content of at least 30 wt. % wherein at least 80% of the C10-C16 acyl carbon atom chains are saturated; and (ii) a C18-C22 acyl carbon atom chain content of at least 20 wt. % wherein at least 50% of the acyl C16-C22 carbon atom chains contain at least one double bond; hydrolyzing at least some of the mixture to yield a quantity of C10-C16 saturated fatty acids and C18-C22 unsaturated fatty acids; oligomerizing at least some of the C18-C22 unsaturated fatty acids to yield a quantity of C36+ fatty acid oligomers; separating at least some of the C10-C16 saturated fatty acids from the C36+ fatty acid oligomers.Type: ApplicationFiled: October 28, 2010Publication date: May 3, 2012Inventor: Stephen J. Miller
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Publication number: 20120088885Abstract: The invention relates to a device for continuously carrying out chemical reactions. The device comprises a microwave generator, a microwave applicator accommodating a microwave-transparent tube, and an isothermal reaction section which is arranged such that the material to be reacted is guided inside the microwave-transparent tube through a microwave applicator which is used as the heating zone and in which it is heated to reaction temperature by means of microwaves that are emitted from the microwave generator into the microwave applicator. The material to be reacted, which is heated and optionally under pressure, is transferred from the microwave applicator to an isothermal reaction zone once it has left the heating zone, said reaction zone being arranged downstream of the heating zone, and is cooled once it has left the isothermal reaction zone.Type: ApplicationFiled: June 9, 2010Publication date: April 12, 2012Applicant: CLARIANT FINANCE (BVI) LIMITEDInventors: Matthias Krull, Roman Morschhaeuser
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Publication number: 20120065260Abstract: Compounds of formula (I); wherein R1 and R2 are the same or different and may be selected from the group consisting of a hydrogen atom, a hydroxy group, an alkyl group, a halogen atom, an alkoxy group, an acyloxy group, an acyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylthio group, an alkoxycarbonyl group, an alkylsulfinyl group, an alkylsulfonyl group, an amino group, and an alkylamino group; and X represents a carboxylic acid group, a carboxylate group, or a carboxamide group; or any pharmaceutically acceptable salt, solvate, complex or pro-drug thereof, with the provisos that the compound of formula (I) is not (all-Z)-4,7,10,13,16,19-docosahexaenoic acid (DHA), alpha-methyl DHA, alpha-methyl DHA methyl ester, alpha-methyl DHA ethyl ester or alpha-hydroxy DHA ethyl ester, are disclosed. A fatty acid composition and a pharmaceutical composition comprising such compounds are also disclosed.Type: ApplicationFiled: September 6, 2011Publication date: March 15, 2012Inventors: Morten Bryhn, Jan Kopecky, Anne Kristin Holmeide
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Patent number: 8071799Abstract: A method comprising providing a starting composition comprising a polyunsaturated fatty acid, a polyunsaturated fatty ester, a carboxylate salt of a polyunsaturated fatty acid, a polyunsaturated triglyceride, or a mixture thereof; self-metathesizing the starting composition or cross-metathesizing the starting composition with at least one short-chain olefin in the presence of a metathesis catalyst to form self-/cross-metathesis products comprising: cyclohexadiene; at least one olefin; and one or more acid-, ester-, or salt-functionalized alkene; and reacting cyclohexadiene to produce at least one cycloalkane or cycloalkane derivatives.Type: GrantFiled: January 29, 2009Date of Patent: December 6, 2011Assignee: Energy & Environmental Research Center FoundationInventor: Edwin S. Olson
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Publication number: 20110245523Abstract: Embodiments of the present application provide methods for processing biodiesel from feedstock using a single-step process. The methods can include, for example, use of a gaseous catalyst as part of the esterification/transesterification process. Embodiments of the present application also provide systems for the methods thereof.Type: ApplicationFiled: December 8, 2009Publication date: October 6, 2011Applicant: XL ONESTEP, LLCInventor: Raveendran Pottathil
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Publication number: 20110172450Abstract: The present invention relates to methods and apparatus for producing alkyl esters from lipid feed stocks, such as plant oils and/or animal fats, and systems including the same. In an embodiment, the invention includes a process for producing alkyl esters including mixing a lipid feed stock with an alcohol to form a reaction mixture; and contacting the reaction mixture with a catalyst under supercritical conditions for the alcohol, the catalyst comprising an unmodified metal oxide selected from the group consisting of alumina, titania, zirconia, and hafnia, and removing residual free fatty acids from the reaction mixture. Other embodiments are included herein.Type: ApplicationFiled: January 10, 2011Publication date: July 14, 2011Inventors: Clayton V. McNeff, Larry C. McNeff, Arlin E. Gyberg, Bingwen Yan, Daniel Thomas Nowlan, Brian Krohn
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Patent number: 7951967Abstract: A method and an apparatus for preparing fatty acid alkyl ester for bio-diesels are disclosed, wherein fatty acid, specifically fatty acid distillate reacts with alcohol, without a catalyst. The method does not require the purification process of the catalyst and glycerin, and has the superior conversion ratio of fatty acid. The method for preparing fatty acid alkyl ester for bio-diesel fuels comprises the step of esterifying fatty acid raw material with alcohol, under a temperature of 200 to 350° C. and a pressure of atmospheric pressure to 10 bar. The apparatus for preparing fatty acid alkyl ester for bio-diesel fuels, comprises: the first reactor for esterifying fatty acid raw material with alcohol under a temperature of 200° C. to 350° C. and a pressure of atmospheric pressure to 10 bar and for converting 80 to 90% of total fatty acid into fatty acid alkyl ester; and the second reactor for converting remaining fatty acid unconverted at the first reactor into fatty acid alkyl ester.Type: GrantFiled: April 28, 2006Date of Patent: May 31, 2011Assignee: SK Chemicals Co., Ltd.Inventors: Shin-ho Chun, Hyun-Jun Cho, Hang-Duk Roh, Jae-Bong Lim, Jong-In Lee, Chan-Woo Moon, Byung-Hui Kim
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Publication number: 20110065942Abstract: A process for preparing a composition of alcoholic esters of straight chain monocarboxylic acids containing 6 to 26 carbon atoms and glycerin, starting from a vegetable or animal oil, neutral or acidic, virgin or recycled with mono-alcohols containing 1 to 18 atoms, in the presence of a zinc aluminate catalyst and in the presence of a controlled quantity of water, can directly produce, in one or more steps, an ester which can be used as a propellant or fuel along with glycerin having improved purity containing a reduced quantity of ethers by using a partially dried catalyst.Type: ApplicationFiled: September 10, 2010Publication date: March 17, 2011Applicant: IFP ENERGIES NOUVELLESInventors: Vincent COUPARD, Sylvie Maury, Veronique Pugnet
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Publication number: 20100228042Abstract: A method and an apparatus for preparing fatty acid alkyl ester for bio-diesels are disclosed, wherein fatty acid, specifically fatty acid distillate reacts with alcohol, without a catalyst. The method does not require the purification process of the catalyst and glycerin, and has the superior conversion ratio of fatty acid. The method for preparing fatty acid alkyl ester for bio-diesel fuels comprises the step of esterifying fatty acid raw material with alcohol, under a temperature of 200 to 35O0 C and a pressure of atmospheric pressure to 10 bar.Type: ApplicationFiled: April 28, 2006Publication date: September 9, 2010Inventors: Shin-ho Chun, Hyun-Jun Cho, Hang-Duk Roh, Jae-Bong Lim, Jong-In Lee, Chan-Woo Moon, Byung-Hui Kim
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Patent number: 7119216Abstract: An olefin metathesis process involving contacting an unsaturated fatty acid ester or unsaturated fatty acid, such as methyloleate or oleic acid, with a lower olefin, preferably ethylene, in the presence of a metathesis catalyst so as to prepare a first product olefin, preferably, a reduced chain ?-olefin, such as methyl-9-decenoate or 9-decenoic acid, respectively. The metathesis catalyst contains ruthenium or osmium and a chelating ligand, preferably, a chelating ligand containing a carbene moiety and a second donor moiety of a Group 15 or 16 element Optionally, the catalyst can be supported on a catalyst support, such as, a cross-linked polymeric resin.Type: GrantFiled: February 27, 2002Date of Patent: October 10, 2006Assignee: Dow Global Technologies Inc.Inventors: Thomas H. Newman, Cynthia L. Rand, Kenneth A. Burdett, Bob R. Maughon, Donald L. Morrison, Eric P. Wasserman
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Patent number: 6982155Abstract: The present invention provides a method for producing a fatty acid ester inexpensively and efficiently by reacting a lipase or an intact mircroorganism containing a lipase, an oil and fat, and a linear lower alcohol in a system containing little or no solvent in the presence of water. The intact microorganism has not been treated with a solvent or the like, and is used as such, so that a fatty acid ester can be prepared in a simple manner. An oil and fat, a natural oil and fat such as a vegetable oil and fat, an animal oil and fat, as well as a waste oil thereof can be used. According to the method of the present invention, a reaction proceeds even in the presence of water, so that waste oils containing a large amount of water can be used as a raw material. Therefore, the waste oil to be dumped into the environment can be recycled, and a biodiesel fuel, which hardly pollutes the environment, can be provided at the same time.Type: GrantFiled: November 20, 2000Date of Patent: January 3, 2006Assignee: Kansai Chemical Engineering Co., Ltd.Inventors: Hideki Fukuda, Hideo Noda
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Patent number: 6958407Abstract: A phenyl ester is produced by allowing benzene, a carboxylic acid and molecular oxygen to react with each other in the presence of a catalyst comprising (A) palladium, (B) at least one element selected from elements of groups 13, 14, 15, and 16 and the fourth to sixth periods of the periodic table, and (C) at least one element selected from elements of groups 3, 4 and lanthanoid elements of the periodic table. Preferably, element (B) is selected from elements of group 16 and the fourth to sixth periods of the periodic table, and element (C) is contained in a metal oxide form in the catalyst. The catalytic activity can be maintained at a high level, and a phenyl ester is stably produced. The phenyl ester can be converted to phenol by a conventional procedure.Type: GrantFiled: November 4, 2004Date of Patent: October 25, 2005Assignee: Tosoh CorporationInventors: Yoshihiko Mori, Takao Doi, Tetsuo Asakawa, Takanori Miyake
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Patent number: 6841691Abstract: Method for the preparation of an enantiomerically enriched ester, in which a mixture of the enantiomers of the corresponding secondary alcohol is subjected, in the presence of an acyl donor, to an enantioselective conversion in the presence of a racemisation catalyst upon which the ester is formed and an acyl donor residue is obtained, and in which the acyl donor residue is irreversibly removed from the phase in which the enantioselective conversion takes place. Preferably the enantioselective conversion is carried out enzymatically and a transfer hydrogenation catalyst is used as racemisation catalyst. The secondary alcohol can be formed in situ from the corresponding ketone, in the presence of a hydrogen donor. It is also possible to use a mixture of the secondary alcohol and the corresponding ketone as substrate. Preferably the acyl donor is chosen so that the acyl donor residue is converted in situ into another compound and/or the acyl donor residue is removed via distillation under reduced pressure.Type: GrantFiled: May 21, 2001Date of Patent: January 11, 2005Assignee: DSM N.V.Inventors: Gerardus Karel Maria Verzijl, Johannes Gerardus Vries De, Quirinus Bernardus Broxterman
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Publication number: 20040054205Abstract: Branched fatty compounds are made by a process which comprises reacting an unsaturated fatty compound and an a-olefin in the presence of a transition metal catalyst and a solvent mixture wherein the solvent mixture is a single liquid phase above 20° C. and is two liquid phases below 20° C.Type: ApplicationFiled: July 2, 2003Publication date: March 18, 2004Inventors: Christian Faengewisch, Arno Behr
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Patent number: 6541655Abstract: Complexes of a selected class of chiral ligands with molybdenum, tungsten or chromium, preferably molybdenum, are effective as catalysts in highly enantioselective and regioselective alkylation of allylic substrates.Type: GrantFiled: September 7, 2001Date of Patent: April 1, 2003Assignee: The Board of Trustees of the Leland Stanford Junior UniversityInventors: Barry M. Trost, Iwao Hachiya
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Patent number: 6515154Abstract: The present invention relates to acetoacetic acid derivatives of the formula Ia or Ib, to processes for their preparation and to their use for the preparation of 2,15-hexadecanedione. The invention further relates to the use of the compounds of the formula Ia or Ib where R is an optionally substituted straight-chain or branched C1-C6-alkyl, C1-C6-alkoxyalkyl or phenyl radical, alkoxy groups are a combination of an alkyl group according to the above definition with an oxygen atom, e.g. methoxy, ethoxy, propoxy, butoxy or pentoxy groups, which comprises adding an acetoacetic ester of the formula II to 1,9-decadiene by a free-radical means, as intermediate for the preparation of muscone (3-methylcyclopentadecanone).Type: GrantFiled: May 3, 2001Date of Patent: February 4, 2003Assignee: BASF AktiengesellschaftInventor: Klaus Ebel
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Patent number: 6509487Abstract: The present invention provides a process for producing lower alkyl fatty esters from fatty acids and lower alcohols, wherein lower alkyl fatty esters are produced in higher yield with a reduction in the amount of the remaining fatty acids. The process of the present invention comprises bringing fatty acids into contact with gaseous lower alcohols in fixed bed(s) charged with a weakly acidic solid catalyst by countercurrent operation, by co-current operation and subsequent countercurrent operation or by pseudo-countercurrent operation, thus feeding and reacting the fatty acids and lower alcohols in fixed-bed reactor(s) charged with a weakly acidic solid catalyst to produce lower alkyl fatty esters.Type: GrantFiled: November 21, 2001Date of Patent: January 21, 2003Assignee: Kao CorporationInventors: Nobuhiro Tatsumi, Takanobu Katayama, Osamu Tabata, Taku Mimura, Noriaki Fukuoka, Katsutoshi Yamamoto
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Patent number: 6383970Abstract: The present invention provides a solid acid catalyst developing high activity and exhibiting high durability in various organic reactions. That is, the present invention provides a solid acid catalyst having the structure (A) in which a hydrogen atom is eliminated from at least one of OH groups contained in an inorganic phosphorus acid, the structure (B) in which a hydrogen atom is eliminated from at least one of OH groups contained in an organic phosphorus acid represented by the formula (1) or (2) and at least one metal atom (C) selected from aluminum, gallium and iron and a method for producing an ester, a ketal or an acetal by using the solid acid catalyst; wherein each of —R1 and —R2 is selected from —R, —OR, —OH and —H in which at least one of —R1 and —R2 is —R or —OR, given that —R is an organic group having 1-22 carbon atoms.Type: GrantFiled: June 19, 2000Date of Patent: May 7, 2002Assignee: Kao CorporationInventors: Taku Mimura, Jun Kaita, Noriaki Fukuoka, Yasuyuki Hattori
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Patent number: 6342620Abstract: A phenyl carboxylate is produced by allowing benzene, a carboxylic acid and molecular oxygen to react with each other in the coexistence of a palladium catalyst with at least one additive selected from alcohols, aldehydes, cyclic hydrocarbons and formic acid. By using the additive, the reduction of catalytic activity of the palladium catalyst with time is minimized.Type: GrantFiled: March 29, 2000Date of Patent: January 29, 2002Assignee: Tosoh CorporationInventor: Yoshihiko Mori
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Patent number: 6153772Abstract: A cobalt catalytic system that makes it possible to obtain branched compounds from fatty substances by reacting simple olefins on polyunsaturated esters, which may or may not be conjugated, is described.The compounds that are obtained may be hydrogenated and used as lubricant bases.Type: GrantFiled: July 24, 1998Date of Patent: November 28, 2000Assignee: Institut Francais du PetroleInventors: Gerard Hillion, Helene Olivier, Katja Siepen, Robert Stern
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Patent number: 5883272Abstract: Rhenium oxide catalysts carried on aluminium silicates, if required with added boric oxide, tungsten oxide, molybdenum oxide or vanadium oxide for the metathesis of olefins and functionalised olefins, in particular of carboxylic acid esters, are provided, whereby the carrier material was hydrothermally treated.Type: GrantFiled: June 20, 1997Date of Patent: March 16, 1999Assignee: RWE-DEA Aktiengesellschaft fur Mineraloel und ChemieInventors: Klaus Noweck, Andreas Hoffmann
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Patent number: 5840942Abstract: A novel method for preparing an aryl-substituted fatty acid or fatty ester is disclosed. According to the method, an olefinic composition selected from among mono-unsaturated fatty acids, mono-unsaturated fatty esters and mixtures thereof is introduced to a reaction zone comprising a liquid aromatic hydrocarbon and a catalytic amount of a clay catalyst to produce a reaction that is allowed to proceed for a time and at a temperature sufficient to produce a reaction product comprising a desired yield of aryl-substituted fatty acid or fatty ester. Preferably, the introduction of the olefinic composition is conducted slowly, such as over a period of one to four, more preferably, two to four, hours. Related methods and compositions, including xylylstearic acid, are also disclosed.Type: GrantFiled: January 19, 1995Date of Patent: November 24, 1998Assignee: Baker Hughes IncorporatedInventor: Bernardus A. Oude Alink
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Patent number: 5498733Abstract: Nylon-11 monomer, 11-aminoundecanoic acid, is synthesized from 12-oxododecanoic acid oxime in a three-step reaction sequence which involves a Beckmann rearrangement, Hofmann degradation and hydrolysis. The aldoxime acid is hydrolyzed in the presence of nickel acetate tetrahydrate to give 11-carbamoylundecanoic acid. This amide is then treated with a solution of sodium methoxide and bromine at 70.degree.-80.degree. C. to give 11-(methoxycarbonylamino)undecanoic acid, which upon basic hydrolysis and subsequent neutralization, yields the 11-aminoundecanoic acid.Type: GrantFiled: July 19, 1993Date of Patent: March 12, 1996Assignee: Howard UniversityInventors: Folahan O. Ayorinde, Chukwuma P. Nwaonicha
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Patent number: 5476956Abstract: Co dimerization is conducted of at least one monoolefin, for example a monoolefinic hydrocarbon such as ethylene, propylene or 1-butene, a halogenated monoolefin such as vinyl chloride, or an olefinic functional compound such as methyl acrylate, acrylonitrile, allyl acetate or vinyl acetate, with at least one polyolefin containing at least two conjugated or unconjugated ethylene bonds, for example a diene hydrocarbon such as 1,3-butadiene, piperylene, or isoprene or a polyolefin containing a carboxylic function, such as a fatty acid or a fatty acid ester having 14 to 24 carbon atoms in the fatty chain derived, for example, from a natural oil. The reaction is carried out in the presence of a catalytic system having general formula [RhX.sub.4 ][YR.sub.4 ] where X represents a halogen ion or a SO.sub.4.sup.--, SO.sub.3.sup.-, OH.sup.-, OR.sup.- or R.sup.Type: GrantFiled: April 25, 1994Date of Patent: December 19, 1995Assignee: Institut Francais Du PetroleInventors: Gerard Hillion, Robert Stern, Abakar Kotoko, Yves Chauvin
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Patent number: 5420317Abstract: Olefinically unsaturated adducts of propylene on polyunsaturated fatty acids with 18 to 22 carbon atoms or on esters of these fatty acids with C.sub.1 -C.sub.36 alkanols in molar ratios of propylene to fatty acids or fatty acid esters in the range from 1:1 to 2:1, obtainable by reacting the fatty acids or fatty acid esters with propylene at elevated temperature and pressure in the presence of compounds of the transition metals Ru, Rh, Pd, Ir and Pt as catalysts to form an olefinically unsaturated adduct.Type: GrantFiled: July 24, 1992Date of Patent: May 30, 1995Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Alfred Laufenberg, Arno Behr
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Patent number: 5405980Abstract: Condensates (K) of(A) oligohydroxy-C.sub.3-8 -alkanes containing at least 3 hydroxy groups and (B) KOH,that contain at least 5% by weight of K.sup.+ and at least one alcoholic hydroxy groupare eminently suitable as oxyalkylation catalysts, in particular for the oxyalkylation of ester group-containing substrates, before all of natural, vegetable or animal fats or oils or their modification products.Type: GrantFiled: February 24, 1993Date of Patent: April 11, 1995Assignee: Sandoz Ltd.Inventor: Hans-Peter Baumann
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Patent number: 5364949Abstract: Process for the production of branched fatty acids and their esters comprising reacting unsaturated fatty acids or esters thereof with aliphatic nonactivated olefins in the presence of layer silicates and active carbon.Type: GrantFiled: November 19, 1992Date of Patent: November 15, 1994Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Michael Neuss, Horst Eierdanz
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Patent number: 5324847Abstract: Olefinically unsaturated adducts of ethylene on polyunsaturated fatty acids with 18 to 22 carbon atoms or on esters of these fatty acids with C.sub.1 -C.sub.36 alkanols in molar ratios of ethylene to fatty acids or fatty acid esters in the range from 1:1 to 3:1 obtainable by reacting the fatty acids or fatty acid esters with ethylene at elevated temperature and pressure in the presence of compounds of the transition metals Ru, Rh, Pd, Ir and Pt as catalysts to form an olefinically unsaturated adduct.Type: GrantFiled: July 24, 1992Date of Patent: June 28, 1994Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Alfred Laufenberg, Arno Behr
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Patent number: 5298650Abstract: The present invention is a process for producing organic esters wherein a dialkyl ether and a carboxylic acid are reacted in the presence of a solid phase acidic catalyst having an acidity factor of at least 0.30, preferably at least 1, under reaction conditions sufficient to form a reaction mixture comprising the desired organic ester and an alcohol and recovering the organic ester. For example, methyl acetate can be prepared by reacting dimethyl ether and acetic acid in the presence of montmorillonite, amorphous silica-alumina or .kappa.-alumina under conditions sufficient to form methyl acetate. While typical processes produce an azeotropic mixture of the desired organic ester and water, the claimed process utilizes a combination or reactants and catalysts wherein water is not produced in appreciable amounts. Therefore, the organic ester product can be separated conveniently thereby avoiding a cumbersome azeotropic distillation step as required in prior art processes.Type: GrantFiled: April 15, 1992Date of Patent: March 29, 1994Assignee: Air Products and Chemicals, Inc.Inventors: Francis J. Waller, William F. Burgoyne, Jr.
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Patent number: 5218131Abstract: A process for the metathesis of olefins and functionalized olefins on Re.sub.2 O.sub.7 /Al.sub.2 O.sub.3 -containing catalysts, which comprises effecting metathesis reaction in the presence of one or more halogen-free organoaluminum compounds as activators.Type: GrantFiled: February 22, 1991Date of Patent: June 8, 1993Assignee: Huels AktiengesellschaftInventors: Siegfried Warwel, Hans-Gerd Jagers, Barbara Ercklentz
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Patent number: 5194640Abstract: An oleic acid containing adduct is produced by reacting tall oil fatty acid (which contains pre-conjugated linoleic acid) with a dienophile at a temperature between 180.degree. C. and 300.degree. C. No catalyst or solvent is necessary for the reaction to occur. The adduct is subsequently distilled to yield a high-purity, light color oleic acid.Type: GrantFiled: June 10, 1991Date of Patent: March 16, 1993Assignee: Westvaco CorporationInventors: John P. Cosgrove, J. George Hayden, Philip L. Robinson
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Patent number: 5177229Abstract: Alcohols and acids are esterified by means of liquid-phase equilibrium reactions on ion exchangers in an apparatus comprising a prereactor and a rectifying column with external reactors. The process is characterized by the fact that a portion of one of the starting compounds is fed directly to the external reactors.Type: GrantFiled: July 10, 1991Date of Patent: January 5, 1993Assignee: Huls AktiengesellschaftInventors: John Kahsnitz, Alfred Oberholz, Udo Knippenberg, Michael Zolffel
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Patent number: 5143885Abstract: A catalyst for the metathesis of olefins and functionalized olefins, which contains a compound having the formula B.sub.2 O.sub.3 --Re.sub.2 O.sub.7 /Al.sub.2 O.sub.3 --SiO.sub.2.Type: GrantFiled: February 22, 1991Date of Patent: September 1, 1992Assignee: Huls AktiengesellschaftInventors: Siegfried Warwel, Hans-Gerd Jagers, Andreas Deckers
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Patent number: 5114624Abstract: In a process for the preparation of higher alkyl acrylic acid esters which comprises reacting one or more C.sub.10+ olefins with one or more alkyl acrylic acid esters in the presence of a halogen containing catalyst, the invention is the improvement which comprises contacting the reaction product mixture with an aqueous acid solution to extract catalyst residues therefrom and distilling the extracted product mixture to remove unreacted olefin.Type: GrantFiled: April 17, 1990Date of Patent: May 19, 1992Assignee: Shell Oil CompanyInventor: Herbert E. Fried