Bonding A Hydrocarbyl Group To The -c(=o)o- Containing Reactant Patents (Class 554/162)
  • Patent number: 11725156
    Abstract: 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: Grant
    Filed: August 13, 2020
    Date of Patent: August 15, 2023
    Assignee: NEXTCHEM S.P.A.
    Inventor: Antonio Zarli
  • Patent number: 11457655
    Abstract: 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: Grant
    Filed: April 26, 2021
    Date of Patent: October 4, 2022
    Assignee: HELIAE DEVELOPMENT, LLC
    Inventors: Micheal LaMont, Magdalena Amezquita Emult, Eneko Ganuza Taberna
  • Patent number: 10986856
    Abstract: 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: Grant
    Filed: November 5, 2020
    Date of Patent: April 27, 2021
    Assignee: Heliae Development, LLC
    Inventors: Micheal LaMont, Magdalena Amezquita Ernult, Eneko Ganuza Taberna
  • Patent number: 9260372
    Abstract: 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: Grant
    Filed: February 28, 2013
    Date of Patent: February 16, 2016
    Assignee: Petroliam Nasional Berhad
    Inventors: Herman Paul Benecke, Daniel B. Garbark
  • Publication number: 20150018572
    Abstract: 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: Application
    Filed: March 13, 2013
    Publication date: January 15, 2015
    Inventor: Shosei Oh
  • Publication number: 20140357881
    Abstract: 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: Application
    Filed: January 18, 2013
    Publication date: December 4, 2014
    Inventors: Leif Johnen, Heinz Strutz
  • Publication number: 20140343310
    Abstract: 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: Application
    Filed: January 18, 2013
    Publication date: November 20, 2014
    Inventors: Leif Johnen, Heinz Strutz, Kurt Schalapski, Norman Nowotny, Wolfgang Höfs, Sebastian Geisel
  • Patent number: 8497389
    Abstract: 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: Grant
    Filed: December 8, 2009
    Date of Patent: July 30, 2013
    Assignee: Initio Fuels LLC
    Inventor: Raveendran Pottathil
  • Publication number: 20130172589
    Abstract: 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: Application
    Filed: September 19, 2011
    Publication date: July 4, 2013
    Applicant: Huntsman Petrochemical LLC
    Inventors: George A. Smith, Daniel R. Weaver, Zheng Chai
  • Patent number: 8420842
    Abstract: 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: Grant
    Filed: June 28, 2002
    Date of Patent: April 16, 2013
    Assignee: Aldivia SA
    Inventors: Pierre Charlier De Chily, Mikaele Raynard
  • Patent number: 8420840
    Abstract: 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: Grant
    Filed: December 2, 2011
    Date of Patent: April 16, 2013
    Inventor: Edwin S. Olson
  • Patent number: 8362288
    Abstract: 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: Grant
    Filed: September 10, 2010
    Date of Patent: January 29, 2013
    Assignee: IFP Energies Nouvelles
    Inventors: Vincent Coupard, Sylvie Maury, Veronique Pugnet
  • Publication number: 20120102827
    Abstract: 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: Application
    Filed: October 28, 2010
    Publication date: May 3, 2012
    Inventor: Stephen J. Miller
  • Publication number: 20120088885
    Abstract: 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: Application
    Filed: June 9, 2010
    Publication date: April 12, 2012
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Matthias Krull, Roman Morschhaeuser
  • Publication number: 20120065260
    Abstract: 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: Application
    Filed: September 6, 2011
    Publication date: March 15, 2012
    Inventors: Morten Bryhn, Jan Kopecky, Anne Kristin Holmeide
  • Patent number: 8071799
    Abstract: 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: Grant
    Filed: January 29, 2009
    Date of Patent: December 6, 2011
    Assignee: Energy & Environmental Research Center Foundation
    Inventor: Edwin S. Olson
  • Publication number: 20110245523
    Abstract: 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: Application
    Filed: December 8, 2009
    Publication date: October 6, 2011
    Applicant: XL ONESTEP, LLC
    Inventor: Raveendran Pottathil
  • Publication number: 20110172450
    Abstract: 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: Application
    Filed: January 10, 2011
    Publication date: July 14, 2011
    Inventors: Clayton V. McNeff, Larry C. McNeff, Arlin E. Gyberg, Bingwen Yan, Daniel Thomas Nowlan, Brian Krohn
  • Patent number: 7951967
    Abstract: 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: Grant
    Filed: April 28, 2006
    Date of Patent: May 31, 2011
    Assignee: 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
  • Publication number: 20110065942
    Abstract: 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: Application
    Filed: September 10, 2010
    Publication date: March 17, 2011
    Applicant: IFP ENERGIES NOUVELLES
    Inventors: Vincent COUPARD, Sylvie Maury, Veronique Pugnet
  • Publication number: 20100228042
    Abstract: 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: Application
    Filed: April 28, 2006
    Publication date: September 9, 2010
    Inventors: Shin-ho Chun, Hyun-Jun Cho, Hang-Duk Roh, Jae-Bong Lim, Jong-In Lee, Chan-Woo Moon, Byung-Hui Kim
  • Patent number: 7119216
    Abstract: 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: Grant
    Filed: February 27, 2002
    Date of Patent: October 10, 2006
    Assignee: Dow Global Technologies Inc.
    Inventors: Thomas H. Newman, Cynthia L. Rand, Kenneth A. Burdett, Bob R. Maughon, Donald L. Morrison, Eric P. Wasserman
  • Patent number: 6982155
    Abstract: 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: Grant
    Filed: November 20, 2000
    Date of Patent: January 3, 2006
    Assignee: Kansai Chemical Engineering Co., Ltd.
    Inventors: Hideki Fukuda, Hideo Noda
  • Patent number: 6958407
    Abstract: 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: Grant
    Filed: November 4, 2004
    Date of Patent: October 25, 2005
    Assignee: Tosoh Corporation
    Inventors: Yoshihiko Mori, Takao Doi, Tetsuo Asakawa, Takanori Miyake
  • Patent number: 6841691
    Abstract: 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: Grant
    Filed: May 21, 2001
    Date of Patent: January 11, 2005
    Assignee: DSM N.V.
    Inventors: Gerardus Karel Maria Verzijl, Johannes Gerardus Vries De, Quirinus Bernardus Broxterman
  • Publication number: 20040054205
    Abstract: 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: Application
    Filed: July 2, 2003
    Publication date: March 18, 2004
    Inventors: Christian Faengewisch, Arno Behr
  • Patent number: 6541655
    Abstract: 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: Grant
    Filed: September 7, 2001
    Date of Patent: April 1, 2003
    Assignee: The Board of Trustees of the Leland Stanford Junior University
    Inventors: Barry M. Trost, Iwao Hachiya
  • Patent number: 6515154
    Abstract: 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: Grant
    Filed: May 3, 2001
    Date of Patent: February 4, 2003
    Assignee: BASF Aktiengesellschaft
    Inventor: Klaus Ebel
  • Patent number: 6509487
    Abstract: 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: Grant
    Filed: November 21, 2001
    Date of Patent: January 21, 2003
    Assignee: Kao Corporation
    Inventors: Nobuhiro Tatsumi, Takanobu Katayama, Osamu Tabata, Taku Mimura, Noriaki Fukuoka, Katsutoshi Yamamoto
  • Patent number: 6383970
    Abstract: 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: Grant
    Filed: June 19, 2000
    Date of Patent: May 7, 2002
    Assignee: Kao Corporation
    Inventors: Taku Mimura, Jun Kaita, Noriaki Fukuoka, Yasuyuki Hattori
  • Patent number: 6342620
    Abstract: 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: Grant
    Filed: March 29, 2000
    Date of Patent: January 29, 2002
    Assignee: Tosoh Corporation
    Inventor: Yoshihiko Mori
  • Patent number: 6153772
    Abstract: 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: Grant
    Filed: July 24, 1998
    Date of Patent: November 28, 2000
    Assignee: Institut Francais du Petrole
    Inventors: Gerard Hillion, Helene Olivier, Katja Siepen, Robert Stern
  • Patent number: 5883272
    Abstract: 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: Grant
    Filed: June 20, 1997
    Date of Patent: March 16, 1999
    Assignee: RWE-DEA Aktiengesellschaft fur Mineraloel und Chemie
    Inventors: Klaus Noweck, Andreas Hoffmann
  • Patent number: 5840942
    Abstract: 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: Grant
    Filed: January 19, 1995
    Date of Patent: November 24, 1998
    Assignee: Baker Hughes Incorporated
    Inventor: Bernardus A. Oude Alink
  • Patent number: 5498733
    Abstract: 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: Grant
    Filed: July 19, 1993
    Date of Patent: March 12, 1996
    Assignee: Howard University
    Inventors: Folahan O. Ayorinde, Chukwuma P. Nwaonicha
  • Patent number: 5476956
    Abstract: 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: Grant
    Filed: April 25, 1994
    Date of Patent: December 19, 1995
    Assignee: Institut Francais Du Petrole
    Inventors: Gerard Hillion, Robert Stern, Abakar Kotoko, Yves Chauvin
  • Patent number: 5420317
    Abstract: 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: Grant
    Filed: July 24, 1992
    Date of Patent: May 30, 1995
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Alfred Laufenberg, Arno Behr
  • Patent number: 5405980
    Abstract: 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: Grant
    Filed: February 24, 1993
    Date of Patent: April 11, 1995
    Assignee: Sandoz Ltd.
    Inventor: Hans-Peter Baumann
  • Patent number: 5364949
    Abstract: 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: Grant
    Filed: November 19, 1992
    Date of Patent: November 15, 1994
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Michael Neuss, Horst Eierdanz
  • Patent number: 5324847
    Abstract: 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: Grant
    Filed: July 24, 1992
    Date of Patent: June 28, 1994
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Alfred Laufenberg, Arno Behr
  • Patent number: 5298650
    Abstract: 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: Grant
    Filed: April 15, 1992
    Date of Patent: March 29, 1994
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Francis J. Waller, William F. Burgoyne, Jr.
  • Patent number: 5218131
    Abstract: 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: Grant
    Filed: February 22, 1991
    Date of Patent: June 8, 1993
    Assignee: Huels Aktiengesellschaft
    Inventors: Siegfried Warwel, Hans-Gerd Jagers, Barbara Ercklentz
  • Patent number: 5194640
    Abstract: 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: Grant
    Filed: June 10, 1991
    Date of Patent: March 16, 1993
    Assignee: Westvaco Corporation
    Inventors: John P. Cosgrove, J. George Hayden, Philip L. Robinson
  • Patent number: 5177229
    Abstract: 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: Grant
    Filed: July 10, 1991
    Date of Patent: January 5, 1993
    Assignee: Huls Aktiengesellschaft
    Inventors: John Kahsnitz, Alfred Oberholz, Udo Knippenberg, Michael Zolffel
  • Patent number: 5143885
    Abstract: 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: Grant
    Filed: February 22, 1991
    Date of Patent: September 1, 1992
    Assignee: Huls Aktiengesellschaft
    Inventors: Siegfried Warwel, Hans-Gerd Jagers, Andreas Deckers
  • Patent number: 5114624
    Abstract: 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: Grant
    Filed: April 17, 1990
    Date of Patent: May 19, 1992
    Assignee: Shell Oil Company
    Inventor: Herbert E. Fried