Of Unsaturated Hydrocarbon Patents (Class 203/9)
  • Patent number: 11083796
    Abstract: The present invention is related to methods for lowering peroxide levels in sucrose acetate isobutyrate formulations and to composition used in and formed by such methods.
    Type: Grant
    Filed: August 15, 2019
    Date of Patent: August 10, 2021
    Assignee: Durect Corporation
    Inventors: Gunjan Junnarkar, Michael A. Desjardin, John P. Carr
  • Patent number: 9656930
    Abstract: Disclosed herein are systems and methods for monitoring and controlling a nitroxide-based polymerization inhibitor in vinyl-based monomers. A dosage of the nitroxide-based polymerization inhibitor is provided in the vinyl-based monomers. A residual concentration of the nitroxide-based polymerization inhibitor is measured substantially in real time, and an optimized dosage of the nitroxide-based polymerization inhibitor is provided in response to the measured residual concentration.
    Type: Grant
    Filed: January 12, 2016
    Date of Patent: May 23, 2017
    Assignee: ECOLAB USA INC.
    Inventors: Ramon Colorado, Jr., Vincent E. Lewis, Robert A. Geiger, Jessica M. Hancock, Andrew R. Neilson
  • Patent number: 9447002
    Abstract: A method for retarding polymerization of vinyl monomers comprising adding a quinone methide to a liquid comprising the vinyl monomers is described.
    Type: Grant
    Filed: October 29, 2014
    Date of Patent: September 20, 2016
    Assignee: NALCO Company
    Inventor: Jonathan Masere
  • Patent number: 9399622
    Abstract: Polymerization inhibitor compositions are provided. The polymerization inhibitor compositions may include at least one hydroxylamine of a nitroxide and at least one phenylenediamine. Methods of inhibiting the unwanted polymerization of monomers are also provided. The methods include adding the presently disclosed polymerization inhibitor compositions to a fluid containing the monomers. The monomers may be ethylenically unsaturated monomers, such as acrylic acid, methacrylic acid, acrylonitrile, methacrylonitrile, acrolein, methacrolein, acrylate, methacrylate, acrylamide, methacrylamide, vinyl acetate, butadiene, ethylene, propylene, and styrene.
    Type: Grant
    Filed: December 3, 2013
    Date of Patent: July 26, 2016
    Assignee: ECOLAB USA INC.
    Inventor: David Youdong Tong
  • Patent number: 9217107
    Abstract: The present invention relates to an improved amine based additive composition for control and inhibition of polymerization of aromatic vinyl monomers including styrene comprising one or more of the quinone methide or derivatives thereof, one or more of nitroxide compounds and further comprising one or more of aliphatic tertiary amines. In one embodiment, the present invention also relates to method of use of presently provided composition. In another embodiment, the present invention also relates to method of controlling and inhibiting polymerization of aromatic vinyl monomers, particularly of styrene by employing presently provided composition. In still another embodiment, the present invention also relates to method of preparation of presently provided composition.
    Type: Grant
    Filed: December 21, 2012
    Date of Patent: December 22, 2015
    Assignee: Dorf Ketal Chemicals (India) Private Limited
    Inventor: Mahesh Subramaniyam
  • Patent number: 9090526
    Abstract: The present invention provides a method for inhibiting unwanted polymerization of reactive monomers within a liquid. The method comprises the combined usage of a quinone methide with a quinone diimide to the liquid monomer. This combination has an unexpected synergistic effect. Thus, in some ratios, the combination results in practically 100% inhibition.
    Type: Grant
    Filed: June 13, 2011
    Date of Patent: July 28, 2015
    Assignee: NALCO COMPANY
    Inventor: Jonathan Masere
  • Patent number: 8771476
    Abstract: High temperatures and oxygen exposure during extractive distillation can result in polymerization of vinyl aromatic compounds. In various embodiments, the present disclosure relates to methods for inhibiting polymerization of vinyl aromatic compounds during extractive distillation. In various embodiments, the methods include a) providing a mixture containing at least one vinyl aromatic compound, b) adding at least one dinitrophenol inhibitor to the mixture, and c) after step b), performing an extractive distillation on the mixture to isolate the at least one vinyl aromatic compound. Purified styrene can be isolated by the methods described herein. In some embodiments, the dinitrophenol inhibitor is 2-sec-butyl-4,6-dinitrophenol (DNBP).
    Type: Grant
    Filed: February 15, 2010
    Date of Patent: July 8, 2014
    Assignee: GTC Technology LP
    Inventors: Amy Sealey, George A. Ball, B. Bryant Slimp, Jr.
  • Patent number: 8491758
    Abstract: A process for inhibiting polymerization of (meth)acrylic acid and/or (meth)acrylic esters by introducing an oxygenous gas into the (meth)acrylic acid and/or the (meth)acrylic ester, in which the (meth)acrylic acid and/or the (meth)acrylic ester has a degree of purity of at least 95% and is in the liquid state.
    Type: Grant
    Filed: December 9, 2010
    Date of Patent: July 23, 2013
    Assignee: BASF SE
    Inventors: Gunter Lipowsky, Steffen Rissel, Volker Schliephake, Ulrich Jäger, Sylke Haremza
  • Publication number: 20130165707
    Abstract: A method for suppressing isomerization of an olefin metathesis product produced in a metathesis reaction includes adding an isomerization suppression agent to a mixture that includes the olefin metathesis product and residual metathesis catalyst from the metathesis reaction under conditions that are sufficient to passivate at least a portion of the residual metathesis catalyst. The isomerization suppression agent includes (i) a salt and/or an ester of a phosphorous oxo acid, and/or (ii) a derivative of the phosphorous oxo acid in which at least one P—H bond has been replaced by a P—C bond, and/or (iii) a salt and/or an ester of the derivative. Methods of refining natural oils are described.
    Type: Application
    Filed: December 22, 2011
    Publication date: June 27, 2013
    Inventors: Bruce E. Firth, Sharon E. Kirk
  • Patent number: 8361280
    Abstract: A process is proposed for distillatively obtaining pure 1,3-butadiene from crude 1,3-butadiene in a plant comprising one or more distillation columns, comprising supply of a feed stream of crude 1,3-butadiene to the one distillation column or the first of the plurality of distillation columns, the one distillation column or the plurality of distillation columns having a flange with an internal diameter of ?80 mm, comprising two mutually opposite plane-parallel surfaces (1) with an intermediate seal (2) which seals the interior of the one distillation column or of the first of the plurality of distillation columns from an intermediate space (3) on the atmosphere side between the two mutually opposite plane-parallel surfaces (1), and the intermediate space (3) on the atmosphere side between the two mutually opposite plane-parallel surfaces (1) being closed off from the atmosphere to form a chamber, wherein the chamber is purged continuously during the operation of the plant with a low-oxygen gas or a low-oxygen
    Type: Grant
    Filed: November 3, 2009
    Date of Patent: January 29, 2013
    Assignee: BASF SE
    Inventors: Uwe Stabel, Harry Zachmann, Eberhardt Gaffron, Bernd Heida, Michael Jäger
  • Patent number: 8337671
    Abstract: Process for distillatively purifying polymerizable compounds using a high-boiling, inert, thermally long-term-stable substance as a boiling oil, characterized in that the boiling oil is disposed in the bottom of a rectification column.
    Type: Grant
    Filed: March 14, 2007
    Date of Patent: December 25, 2012
    Assignee: Evonik Röhm GmbH
    Inventors: Dirk Broell, Hermann Siegert
  • Patent number: 8207291
    Abstract: Process for devolatilization of a polymer of an aromatic alkylene, such as styrene and, in particular, an improved process using water as a stripping agent (i) in which the total amount of water to be disposed of can be reduced, (ii) which allows at least a portion of the water to be recycled as stripping agent, reducing make-up requirements for the stripping agent, and (iii) which allows at least a portion of the aromatic alkylene monomer in the water to be recycled to the polymerization process (via the devolatilization steps) rather than being disposed.
    Type: Grant
    Filed: June 3, 2008
    Date of Patent: June 26, 2012
    Assignee: Ineos Europe Limited
    Inventor: Jean-Marc Galewski
  • Patent number: 8157969
    Abstract: Accumulation of polymer on equipment, which is in contact with polymerizable material during normal process operation, is minimized by the method and apparatus of the present invention. The method involves positioning and affixing the equipment, such as a pressure relief device, to process apparatus, such as a distillation column, proximate to a wetted region comprising liquid phase fluid in the process apparatus, such that the moving liquid phase fluid is at least intermittently in contact with the equipment and one or more of accumulated polymerizable material, condensate comprising same, and polymer, is washed off of the equipment.
    Type: Grant
    Filed: April 26, 2007
    Date of Patent: April 17, 2012
    Assignee: Rohm and Haas Company
    Inventors: Barnett John O., Michael Stanley DeCourcy, Michael W. Hurley
  • Patent number: 8118995
    Abstract: A method for inhibiting the formation of fouling materials including contacting hydrocarbon media containing aldehyde compounds with an antifoulant while treating the hydrocarbon media with a basic wash. The antifoulant includes a reducing sugar.
    Type: Grant
    Filed: March 31, 2009
    Date of Patent: February 21, 2012
    Assignee: General Electric Company
    Inventors: Mary King, Cato Russell McDaniel
  • Patent number: 7981255
    Abstract: There is provided a method for rectifying a vinyl compound liquor. The method includes the steps of a) providing a rectification column operated at a temperature and pressure and b) feeding the vinyl compound liquor to be rectified into the rectification column, wherein the pressure of the rectification column and the temperature of the fed vinyl compound liquor are controlled, such that the temperature of the fed vinyl compound liquor ranges from its bubble point at the pressure of the rectification column to 10° C. lower than the bubble point.
    Type: Grant
    Filed: September 26, 2007
    Date of Patent: July 19, 2011
    Assignee: Shanghai HuaYi Acrylic Acid Co., Ltd.
    Inventors: Jingming Shao, Jun Yin, Shuju Liu, Xiaodong Chu, Shengxian Xu
  • Patent number: 7892403
    Abstract: A condenser includes: a top face of a tube plate on which acrylic acid may be condensed inside the condenser; a spray for spreading a polymerization inhibitor on the tube plate; a first polymerization inhibitor supply tube for supplying the polymerization inhibitor to the spray; and a supporter for supporting the spray at a predetermined position. The supporter supports the first polymerization inhibitor supply tube outside the condenser. The condenser allows a stable continuous operation for a long period of time by preventing polymerization of an easily polymerizable compound in the condenser into which a vapor of an easily polymerizable compound is supplied with a simple structure thereof.
    Type: Grant
    Filed: September 7, 2004
    Date of Patent: February 22, 2011
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Shuhei Yada, Yasushi Ogawa, Yoshiro Suzuki, Kimikatsu Jinno
  • Publication number: 20100126843
    Abstract: A process is proposed for distillatively obtaining pure 1,3-butadiene from crude 1,3-butadiene in a plant comprising one or more distillation columns, comprising supply of a feed stream of crude 1,3-butadiene to the one distillation column or the first of the plurality of distillation columns, the one distillation column or the plurality of distillation columns having a flange with an internal diameter of ?80 mm, comprising two mutually opposite plane-parallel surfaces (1) with an intermediate seal (2) which seals the interior of the one distillation column or of the first of the plurality of distillation columns from an intermediate space (3) on the atmosphere side between the two mutually opposite plane-parallel surfaces (1), and the intermediate space (3) on the atmosphere side between the two mutually opposite plane-parallel surfaces (1) being closed off from the atmosphere to form a chamber, wherein the chamber is purged continuously during the operation of the plant with a low-oxygen gas or a low-oxygen
    Type: Application
    Filed: November 3, 2009
    Publication date: May 27, 2010
    Applicant: BASF SE
    Inventors: Uwe Stabel, Harry Zachmann, Eberhardt Gaffron, Bernd Heida, Michael Jäger
  • Patent number: 7560590
    Abstract: A process for rectificatively separating an acrylic acid-containing liquid, by withdrawing an acrylic acid-rich stream from the rectification column above the feed point and polymerization-inhibiting the upper section of the rectification column by means of diacrylic acid.
    Type: Grant
    Filed: September 14, 2004
    Date of Patent: July 14, 2009
    Assignee: BASF Aktiengesellschaft
    Inventors: Frank Hoefer, Volker Schliephake, Klaus Joachim Mueller-Engel
  • Patent number: 7476299
    Abstract: A decomposition reaction apparatus or distillation apparatus for acrylic acid in which a column bottom liquid heated in a reboiler (5) is supplied from a supply port (1a) provided on a side wall of a column body (1) having: a top plate (12a) above the supply port (1a); and an impingement plate (12b) provided vertically to the top plate (12a), for preventing scattering of the column bottom liquid to a supply direction. The top plate (12a) is provided such that the top face of the top plate (12a) is inclined downward from a base end to a tip end. The present invention allows: suppression of formation of a polymerized product due to flowing of a liquid or gas heated in a reboiler into a column with a simple structure; and a stable continuous operation of column equipment over a long period of time.
    Type: Grant
    Filed: April 7, 2006
    Date of Patent: January 13, 2009
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Shuhei Yada, Yasushi Ogawa, Yoshiro Suzuki, Kenji Takasaki
  • Patent number: 7393986
    Abstract: Process for the production of vinyl aromatic monomers which comprises: a) feeding an aromatic stream and an olefinic stream to an alkylation unit; b) feeding the reaction product coming from the alkylation section to a first separation section; c) recovering the mono-alkylated aromatic hydrocarbon and the heavy bottom product from the first separation section; d) feeding the mono-alkylated aromatic to a dehydrogenation section; e) feeding the reaction product coming from the dehydrogenation section to a second purification/separation section; f) also feeding the heavy bottom product of step (c) to the second purification/separation section; g) recovering a stream consisting of the vinyl aromatic monomer with a purity higher than 99.7 by weight.
    Type: Grant
    Filed: December 13, 2004
    Date of Patent: July 1, 2008
    Assignee: Polimeri Europa S.p.A.
    Inventors: Armando Galeotti, Elena Bencini, Leonardo Trentini
  • Patent number: 7351310
    Abstract: A process for rectificatively separating fluids including (meth)acrylic monomers in a rectification column by directly cooling the vapor including (meth)acrylic monomers rising to the top of the rectification column to form top condensate including (meth)acrylic monomers, the condensation space at the top of the column being separated from the region of the rectification column containing the separating internals only by at least one chimney tray from which the top condensate formed is removed from the rectification column, which includes effecting the direct cooling of the vapor in the condensation space in at least two spray zones which are spatially successive and are flowed through by vapor by spraying supercooled top condensate including added polymerization inhibitor, and the temperature of the sprayed supercooled top condensate becoming lower from spray zone to spray zone in the flown direction of the vapor.
    Type: Grant
    Filed: September 10, 2003
    Date of Patent: April 1, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Joachim Thiel, Albrecht Dams, Juergen Schroeder
  • Patent number: 7304196
    Abstract: A method for dimerizing isobutene, wherein, in dimerizing conditions, the isobutene is brought into contact with a porous cation exchange resin comprising a styrene polymer, which is cross-linked with divinyl benzene, and any sulphonic acid groups adhering to the polymer. The harmful deactivation of this catalyst, which is caused by the accumulation of the oligomers and polymers of isobutene and other C4-olefins in the cation exchange resin catalyst, is essentially decreased by selecting the cation exchange resin from a group including cation exchange resins, the acid,capacity of which is 4.7 equivalents/kg at a minimum, and the portion of divinyl benzene units of which is 5% by weight at a minimum and smaller than 20% by weight.
    Type: Grant
    Filed: October 29, 2004
    Date of Patent: December 4, 2007
    Assignee: Neste Oil OYJ
    Inventors: Veli-Matti Purola, Sami Toppinen, Antti Pyhalahti, Marina Lindblad, Johan Gronqvist, Pirjo Siira
  • Patent number: 7128826
    Abstract: Quinone methide derivatives such as 4-benzylidene-2,6-di-tert-butyl-cyclohexa-2,5 dienone are used to inhibit styrene monomer polymerization in the dehydrogenator portion of a styrene monomer production system. The inhibitor contacts the dehydrogenation effluent and does not partition in substantial amounts to the aqueous phase that is separated in the phase separator.
    Type: Grant
    Filed: July 31, 2003
    Date of Patent: October 31, 2006
    Assignee: General Electric Company
    Inventors: Sherif Eldin, Ronnie L. Deason, John Link, Tiffany N. Morris
  • Patent number: 7125475
    Abstract: Inhibitor blends that include both nitrosophenols and nitrosoanilines, optionally in combination with air or oxygen, reduce the premature polymerization of ethylenically unsaturated monomers. unsaturated monomers.
    Type: Grant
    Filed: January 29, 2003
    Date of Patent: October 24, 2006
    Assignee: Crompton Corporation
    Inventor: Brigitte Benage
  • Patent number: 6835288
    Abstract: A process for preventing undesired polymerization is conducted by maintaining an effective concentration of a stabilizer which comprises N-oxyl radicals in a mixture containing ethylenically unsaturated compounds, wherein (i) an electronic signal which correlates with the concentration of the N-oxyl radicals in the mixture is obtained periodically or continuously, (ii) the electronic signal is compared with a reference value, and (iii) addition of a stabilizer to the mixture is controlled according to the comparison (ii). The signal is preferably obtained by ESR measurement. The process permits efficient use of the stabilizer.
    Type: Grant
    Filed: December 11, 2001
    Date of Patent: December 28, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz Friedrich Sutoris, Konrad Mitulla
  • Publication number: 20040089586
    Abstract: Disclosed herein is a method for inhibiting the premature polymerization of ethylenically unsaturated monomers comprising adding to said monomers an effective amount of at least one inhibitor selected from the group consisting of C-nitrosoaniline and quinone imine oxime compounds.
    Type: Application
    Filed: November 10, 2003
    Publication date: May 13, 2004
    Applicant: Uniroyal Chemical Company, Inc.
    Inventors: Brigitte Benage, Gerald J. Abruscato, Andrew J. Eisenstein
  • Publication number: 20030205503
    Abstract: A method for inhibiting and dissolving the deposits formed on caustic or alkaline scrubbers used in scrubbing acidic gases such as carbon dioxide, hydrogen sulfide, which are formed during the pyrolytic cracking of naphtha, ethane, and propane. The cracking operations produce certain oxygenated compounds such as vinyl acetate or acetaldehyde, which undergo polymerization under alkaline condition. The vinyl acetate on hydrolysis releases acetaldehyde under alkaline conditions. Amino acids such as 6 amino caproic acid and lactams such as epsilon caprolactam not only prevent but also dissolve the polymers formed by aldol condensation.
    Type: Application
    Filed: April 29, 2002
    Publication date: November 6, 2003
    Inventors: Mahesh Subramaniyam, Bankar Prashant
  • Publication number: 20030155227
    Abstract: Inhibitor blends comprising nitrosophenols and nitrosoanilines, optionally in combination with air or oxygen, reduce the premature polymerization of ethylenically unsaturated monomers.
    Type: Application
    Filed: January 29, 2003
    Publication date: August 21, 2003
    Applicant: CROMPTON CORPORATION
    Inventor: Brigitte Benage
  • Patent number: 6592722
    Abstract: This invention relates to a process of inhibiting the polymerization of vinyl-containing materials through the use of an effective amount of a polymerization inhibitor comprising quinone diimide and a nitroxyl stable free radical under various conditions. This invention also relates to the polymerization inhibitor composition.
    Type: Grant
    Filed: September 4, 2002
    Date of Patent: July 15, 2003
    Assignee: GE Betz, Inc.
    Inventor: Grace B. Arhancet
  • Patent number: 6579442
    Abstract: Methods and compositions for inhibiting the polymerization of vinyl monomers are disclosed. Combinations of nitroxyl compounds and aliphatic amines are effective at inhibiting the polymerization of vinyl monomers under both processing and storage conditions.
    Type: Grant
    Filed: May 22, 2001
    Date of Patent: June 17, 2003
    Assignee: GE Betz, Inc.
    Inventor: Sherif Eldin
  • Patent number: 6540881
    Abstract: This invention relates to a method for preventing (meth)acrylic acid from polymerizing during the course of distillation. The method provides for refining (meth)acrylic acid by a procedure including the steps of feeding a mixed gas obtained by catalytic gas phase oxidation of propylene and/or acrolein with a molecular oxygen-containing gas or a mixed gas obtained by catalytic gas phase oxidation of at least one compound of isobutylene, t-butyl alcohol, or methacrolein with a molecular oxygen-containing gas, to a (meth)acrylic acid collection column, collecting a (meth)acrylic acid-containing solution from the mixed gas, and feeding the (meth)acrylic acid-containing solution to a distillation column while maintaining the total concentration of aldehydes of 2-4 carbon atoms and acetone in the solution at a level of not more than 2000 ppm based on the amount of (meth)acrylic acid.
    Type: Grant
    Filed: March 22, 2000
    Date of Patent: April 1, 2003
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Kazuhiko Sakamoto, Kouji Ueno, Sei Nakahara, Masatoshi Ueoka
  • Publication number: 20030010676
    Abstract: Methods and compositions for inhibiting the polymerization of vinyl monomers are disclosed. Combinations of nitroxyl compounds and aliphatic amines are effective at inhibiting the polymerization of vinyl monomers under both processing and storage conditions.
    Type: Application
    Filed: May 22, 2001
    Publication date: January 16, 2003
    Inventor: Sherif Eldin
  • Patent number: 6475348
    Abstract: A mixture contains one or more vinyl-containing compounds as component (A) and, as a further component, a stabilizer (B) which contains one or more readily volatile nitroxyl compounds as component (b1), one or more sparingly volatile nitroxyl compounds as component (b2), if required one or more aromatic nitro compounds as component (b3) and, if required, one or more iron compounds as component (b4). Stabilizers (B) contain the components (b1) and (b2), (b1) and (b2) and (b3), (b1) and (b2) and (b4), and (b1), (b2), (b3) and (b4), and the premature polymerization of vinyl-containing compounds during their purification or distillation is inhibited by a process in which a stabilizer (B) is added or the components of stabilizer (B) are added as individual substances or in at least two groups of the components.
    Type: Grant
    Filed: December 17, 1999
    Date of Patent: November 5, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz Friedrich Sutoris, Konrad Mitulla, Jacques Dupuis, Claus Kaliba
  • Patent number: 6471865
    Abstract: The present invention provides a solvent exchange column for continuously exchanging styrene monomer with the solvent used to produce polybutadiene and a method of use therefor. The solvent exchange column includes an exchange plate support structure coupled to and supporting spaced apart exchange plates, wherein each of the exchange plates has holes located therein to allow a passage of fluid therethrough. The solvent exchange column further includes a vapor ventilation system for allowing the volatized solvent to exit the solvent exchange column.
    Type: Grant
    Filed: October 25, 2000
    Date of Patent: October 29, 2002
    Assignee: Fina Technology, Inc.
    Inventors: J. Todd Reaves, Aron T. Griffith, Jose M. Sosa, Douglas Berti, Brad Klussmann
  • Patent number: 6447649
    Abstract: This invention relates to a process of inhibiting the polymerization of vinyl-containing materials through the use of an effective amount of a polymerization inhibitor comprising quinone diimide and a nitroxyl stable free radical under various conditions. This invention also relates to the polymerization inhibitor composition.
    Type: Grant
    Filed: July 24, 2000
    Date of Patent: September 10, 2002
    Assignee: GE Betz, Inc.
    Inventor: Grace B. Arhancet
  • Patent number: 6409887
    Abstract: A monomer composition, stabilized against premature polymerization, comprising: a) an ethylenically unsaturated monomer or mixture of monomers polymerizable by free radical initiation, and b) an effective amount, sufficient to inhibit premature polymerization of component (a) of a mixture of: i) 1 to 99% by weight, based on the total weight of components (i) and (ii), of a mixture of at least one aromatic amine and at least one organic acid in a molar ratio of 10:1 to 1:10, and ii) 99 to 1% by weight, based on the total weight of components (i) and (ii), of at least one stable radical compound.
    Type: Grant
    Filed: April 13, 2001
    Date of Patent: June 25, 2002
    Assignee: AAH Marks and Company Limited
    Inventors: Anthony Pryce, Robert Charles Callin
  • Publication number: 20020040174
    Abstract: A monomer composition, stabilized against premature polymerization, comprising: a) an ethylenically unsaturated monomer or mixture of monomers polymerizable by free radical initiation, and b) an effective amount, sufficient to inhibit premature polymerization of component (a) of a mixture of: i) 1 to 99% by weight, based on the total weight of components (i) and (ii), of a mixture of at least one aromatic amine and at least one organic acid in a molar ratio of 10:1 to 1:10, and ii) 99 to 1% by weight, based on the total weight of components (i) and (ii), of at least one stable radical compound.
    Type: Application
    Filed: April 13, 2001
    Publication date: April 4, 2002
    Applicant: A H MARKS AND COMPANY LIMITED
    Inventors: Anthony Pryce, Robert Charles Callin
  • Patent number: 6348136
    Abstract: The present invention is directed to an apparatus and method for the distillation of a readily polymerizable vinyl aromatic compound employing a polymerization inhibitor. The vinyl aromatic compound is subjected to distillation in at least one fractionation column having at least one reboiler for maintaining the bottoms of said column at a proper temperature. The reboiler includes a heating section and a vapor phase section. The bottoms fraction from the fractionation column is cycled to the reboiler and subjected to heat to vaporize at least a portion of the bottoms fraction to form a vapor phase in the vapor section, A slip stream of the bottoms fraction is introduced to the vapor phase section of the reboiler. The slipstream contains polymerization inhibitor that had been added to the process at the fractionation column. The invention reduces fouling at the reboilers. The slipstream is optionally introduced to the reboiler using one or more spray nozzles.
    Type: Grant
    Filed: February 29, 2000
    Date of Patent: February 19, 2002
    Assignee: Fina Technology, Inc.
    Inventors: Marcus E. Ledoux, Kelli E. Prince, Adrian M. Jacobsen, Larry P. Braud, Jr.
  • Patent number: 6342648
    Abstract: The present invention provides compositions and methods inhibiting polymerization of vinyl aromatic compounds comprising a bisphenol compound and an oxidized p-phenylenediamine. In a specific, non-limiting embodiment, the polymerization of the vinyl aromatic compound styrene is inhibited by a composition comprising the bisphenol compound 4,4′-methylenebis(2,6-di-tert-butyphenol) and the oxidized p-phenylenediamine compound N-phenyl-N′-methyl-benzoquinonediimide.
    Type: Grant
    Filed: September 30, 1999
    Date of Patent: January 29, 2002
    Assignee: Baker Hughes Incorporated
    Inventor: Muslim D. Shahid
  • Publication number: 20010052481
    Abstract: Popcorn polymer growth is inhibited in unstabilized materials comprising olefinically unsaturated organic compounds by adding thereto an effective amount of an aliphatic alcohol of the formula I
    Type: Application
    Filed: March 2, 1999
    Publication date: December 20, 2001
    Inventors: MAIK ARON, MICHAEL BACHTLER, JURGEN KANAND
  • Publication number: 20010009968
    Abstract: Methods and compositions for inhibiting the polymerization of ethylenically unsaturated hydrocarbons are disclosed. Combinations of aminophenol compound and either of phenylenediamine or hydroxylamine compounds are effective at inhibiting this polymerization under both processing and storage conditions.
    Type: Application
    Filed: January 24, 2001
    Publication date: July 26, 2001
    Applicant: BETZDEARBORN INC.
    Inventor: Sherif Eldin
  • Patent number: 6210536
    Abstract: This invention is directed to certain N,N′-dinitroso phenylenediamines useful as polymerization inhibitors for acrylic acids and esters thereof. Also disclosed are compositions containing such compounds, and methods for inhibiting polymerization using such compounds and compositions.
    Type: Grant
    Filed: September 2, 1993
    Date of Patent: April 3, 2001
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: Anthony Vincent Grossi, Paul Edwin Stott
  • Patent number: 6200461
    Abstract: Methods and compositions for inhibiting the polymerization of ethylenically unsaturated hydrocarbons are disclosed. Combinations of aminophenol compound and either of phenylenediamine or hydroxylamine compounds are effective at inhibiting this polymerization under both processing and storage conditions.
    Type: Grant
    Filed: November 5, 1998
    Date of Patent: March 13, 2001
    Assignee: BetzDearborn Inc.
    Inventor: Sherif Eldin
  • Patent number: 6175049
    Abstract: The production of 1,2-butadiene in purities of at least 85% becomes possible by means of a process in which a polymerization-inhibitor-containing C4 hydrocarbon fraction is subjected to at least one fractional distillation.
    Type: Grant
    Filed: August 17, 1999
    Date of Patent: January 16, 2001
    Assignee: EC Erdolchemie GmbH
    Inventors: Arnd St{umlaut over (u)}we, J{umlaut over (u)}rgen Linnemann, Jens Herwig, Christian Gabel, Bernd Hohmann, Joachim Grub
  • Patent number: 6117276
    Abstract: When a nitroxyl compound is heated in an oxygen-free atmosphere with a vinyl aromatic monomer at 50-140.degree. C. for up to 60 days, it forms an activated inhibitor mixture which is superior to the nitroxyl compound itself in preventing the premature polymerization of a vinyl aromatic monomer during its processing and purification.
    Type: Grant
    Filed: March 26, 1998
    Date of Patent: September 12, 2000
    Assignee: Nalco/Exxon Energy Chemicals, L.P.
    Inventors: Glen T. Cunkle, Thomas F. Thompson, Volker H. von Ahn, Roland A. E. Winter
  • Patent number: 6096941
    Abstract: Process technology is described making possible substantial improvements in the separation and recovery of highly pure vinyl aromatic monomers, notably styrene. A number of design, construction and operational features are made available for selection and use both for new plant facilities and for upgrading existing plant facilities. One major aspect of the invention is reduction in retention or residence times in the distillation towers. In another embodiment, a startup process comprises (i) introducing a feed comprising vinylaromatic monomer, polymerization inhibitor, aromatic hydrocarbon components having boiling points above that of the vinylaromatic monomer to a packed distillation column, said column having a maximum theoretical .DELTA.
    Type: Grant
    Filed: February 25, 1998
    Date of Patent: August 1, 2000
    Inventor: Billie E. Art
  • Patent number: 5954924
    Abstract: Process technology is described making possible substantial improvements in the separation and recovery of highly pure vinyl aromatic monomers, notably styrene. A number of design, construction and operational features are made available for selection and use both for new plant facilities and for upgrading existing plant facilities. One major aspect of the invention is reduction in retention or residence times in the distillation towers.
    Type: Grant
    Filed: September 29, 1995
    Date of Patent: September 21, 1999
    Assignee: Yield Improvement Engineering, Inc.
    Inventor: Billie E. Art
  • Patent number: 5910232
    Abstract: Inhibition performance is improved in styrene processing through the addition of a stable nitroxide free radical compound to the styrene feed and to the reflux of at least one column.
    Type: Grant
    Filed: June 10, 1998
    Date of Patent: June 8, 1999
    Assignee: Nalco/Exxon Energy Chemicals, L.P.
    Inventors: Zara Hyde, Vincent E. Lewis
  • Patent number: 5907071
    Abstract: The polymerization of vinyl aromatic monomers such as styrene is inhibited by the addition of a composition of a stable hindered nitroxyl radical and an oxime compound.
    Type: Grant
    Filed: April 21, 1998
    Date of Patent: May 25, 1999
    Assignee: BetzDearborn Inc.
    Inventor: Graciela B. Arhancet
  • Patent number: 5888356
    Abstract: The polymerization of a vinylaromatic or vinylaliphatic compound at elevated temperature in the absence of air is inhibited by processing the vinylaromatic or vinylaliphatic compound in the presence of 4-hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl or 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxylalone or in admixture with p-nitrosophenol or 2-methyl-4-nitrosophenol.
    Type: Grant
    Filed: October 7, 1997
    Date of Patent: March 30, 1999
    Assignee: Huels Aktiengesellschaft
    Inventors: Thomas Keil, Manfred Kaufhold, Bernd Helpap