Cyclopentadiene From Its Polymer Patents (Class 585/354)
  • Patent number: 9849440
    Abstract: Disclosed is a process for the conversion of acyclic C5 feedstock to a product comprising cyclic C5 compounds, such as for example, cyclopentadiene, and catalyst compositions for use in such process. The process comprising the steps of contacting said feedstock and, optionally, hydrogen under acyclic C5 conversion conditions in the presence of a catalyst composition to form said product. The catalyst composition comprises a Group 10 metal, and, optionally, a Group 11 metal, on a catalyst support with a Group 1 alkali metal silicate and/or a Group 2 alkaline earth metal silicate.
    Type: Grant
    Filed: October 7, 2016
    Date of Patent: December 26, 2017
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Larry L. Iaccino, Jeremy W. Bedard, Tilman W. Beutel, Jocelyn A. Kowalski
  • Patent number: 9845433
    Abstract: A method for producing an olefin and a monocyclic aromatic hydrocarbon of the present invention includes a dicyclopentadiene removal treatment step of removing dicyclopentadienes having a dicyclopentadiene skeleton from a feedstock oil which is a thermally-cracked heavy oil obtained from an apparatus for producing ethylene and which has a 90 volume % distillate temperature, as a distillation characteristic, of 390° C. or lower; and a cracking and reforming reaction step of obtaining a product containing an olefin and a monocyclic aromatic hydrocarbon by bringing the feedstock oil having a content of dicyclopentadienes adjusted to 10% by weight or less by treating a part or all of the feedstock oil through the dicyclopentadiene removal step into contact with a catalyst and reacting the feedstock oil.
    Type: Grant
    Filed: October 25, 2013
    Date of Patent: December 19, 2017
    Assignee: JX Nippon Oil & Energy Corporation
    Inventors: Shinichiro Yanagawa, Masahide Kobayashi, Yukihiro Yoshiwara, Ryoji Ida
  • Patent number: 8704022
    Abstract: Embodiments of the present invention are directed generally to methods for producing high purity exo-alkenylnorbornenes from a mixture of conformational isomers thereof.
    Type: Grant
    Filed: August 6, 2008
    Date of Patent: April 22, 2014
    Assignee: Promerus, LLC
    Inventors: Andrew Bell, Dane Jablonski, Elaine Koronich, Brian Knapp, Dino Amoroso
  • Patent number: 8057714
    Abstract: The present invention relates to a synthesis method of metal cyclopentadienide by direct reaction of dicyclopentadiene with a group 1 metal in the presence of an aprotic solvent. Unlike the conventional method depending on retro Diels-Alder reaction of dicyclopentadiene to generate indirectly cyclopentadiene, the method of the present invention favors generation of cyclopentadiene and metal cyclopentadienide as well by adding dicyclopentadiene directly when the reaction temperature reaches to the boiling point of a reaction solvent.
    Type: Grant
    Filed: November 2, 2007
    Date of Patent: November 15, 2011
    Assignee: LG Chem, Ltd.
    Inventors: Yong gyu Han, Ki-soo Lee, Heon-yong Kwon, Jong-sang Park, Nicola Maggiarosa
  • Publication number: 20080097132
    Abstract: This invention provides a process for forming monomers from a dimer, wherein the dimer is dicyclopentadiene, di(methylcyclopentadiene), di(ethyleyclopentadiene), or a mixture of any two or more of these. The process comprises i) heating a liquid mixture comprising at least one dimer and at least one liquefying agent in a vaporization zone to at least the vaporization temperature of said mixture to form a vaporized mixture, wherein the vaporization zone consists essentially of a substantially straight conduit in which said liquid mixture occupies less than the entire cross sectional area of said conduit; and ii) introducing at least a portion of the vaporized mixture from i) into a cracking zone such that monomers are formed. This process is conducted at about atmospheric pressure.
    Type: Application
    Filed: June 30, 2004
    Publication date: April 24, 2008
    Applicant: ALBEMARLE CORPORATION
    Inventors: John C. Prindle Jr, Dru J. Manuel
  • Patent number: 7145050
    Abstract: The invention relates to modified supported catalysts based on Re2O7/?-Al2O3 for use in the preparation of cycloalkadienes in a metathesis reaction, a process for preparing cycloalkadienes in the presence of these supported catalysts and the use of the resulting cycloalkadienes for the preparation of fragrances.
    Type: Grant
    Filed: August 23, 2002
    Date of Patent: December 5, 2006
    Assignee: Symrise GmbH & Co. KG
    Inventors: Ingo Wöhrle, Aurélia Reckziegel, Peter Esser, Martin Stürmann
  • Patent number: 7041862
    Abstract: A method for thermally cracking Diels-Alder adducts and for altering organic streams containing Diels-Alder adducts using controlled cavitation conditions.
    Type: Grant
    Filed: March 26, 2003
    Date of Patent: May 9, 2006
    Assignee: Equistar Chemicals, LP
    Inventor: Donald H. Powers
  • Patent number: 6916966
    Abstract: The present invention relates to a process for preparing cycloalkadienes using supported catalysts based on Re2O7/?-Al2O3 and also to the use of the resulting cycloalkadienes for the preparation of fragrances.
    Type: Grant
    Filed: August 23, 2002
    Date of Patent: July 12, 2005
    Assignee: Symrise GmbH & Co. KG
    Inventors: Ingo Wöhrle, Peter Esser, Aurélia Reckziegel, Matthias Brandt, Stephan Klein, Thomas Turek
  • Patent number: 6903241
    Abstract: The present invention relates to supported catalysts based on Re2O7/(—Al2O3 for use in the preparation of cycloalkadienes in a metathesis reaction, a process for preparing cycloalkadienes in the presence of these supported catalysts and also the use of the resulting cycloalkadienes for preparing fragrances.
    Type: Grant
    Filed: August 23, 2002
    Date of Patent: June 7, 2005
    Assignee: Symrise GmbH & Co. KG
    Inventors: Ingo Wöhrle, Peter Esser, Aurélia Reckziegel, Matthias Brandt, Stephan Klein, Thomas Turek
  • Patent number: 6586648
    Abstract: The present invention provides a process for producing cyclopentadiene or a derivative thereof by heating a mixture containing at least one of dicyclopentadiene or a derivative thereof, the process comprising: a first step comprising heating the mixture into vapor; a second step comprising maintaining while heating the vapor at a temperature higher than the boiling point of the desired cyclopentadiene or derivative thereof to condense and remove high-boiling components and simultaneously collect residual vapor; and a third step comprising maintaining while heating the collected vapor at a temperature lower than the boiling point of the desired cyclopentadiene or derivative thereof to condense and collect the cyclopentadiene or derivative thereof. In the third step, the vapor may be contact with nitrogen gas to improve the yield of the cyclopentadiene or derivative thereof.
    Type: Grant
    Filed: April 2, 2001
    Date of Patent: July 1, 2003
    Assignee: Tanaka Kikinzoku Kogyo K.K.
    Inventors: Katsutsugu Kitada, Hiroaki Suzuki
  • Patent number: 6479719
    Abstract: This process for the manufacture of norbornene from dicyclopentadiene (DCPD) and ethylene is characterized in that the DCPD is subjected to partial monomerization to CPD by preheating: at a temperature of 140° C. to 240° C.; and under a pressure of 20 to 300 bar abs., before reacting it with the ethylene; with an ethylene/DCPD molar ratio of 1 to 20; at a temperature of 200° C. to 320° C.; under a pressure of 20 to 300 bar abs.; and with a residence time of 1 to 10 minutes, under stable reaction conditions between the DCPD, the CPD and the ethylene.
    Type: Grant
    Filed: August 2, 2000
    Date of Patent: November 12, 2002
    Assignee: Atofina
    Inventors: Roland Kotwica, André Marbach
  • Publication number: 20010047120
    Abstract: The present invention provides a process for producing cyclopentadiene or a derivative thereof by heating a mixture containing at least one of dicyclopentadiene or a derivative thereof, the process comprising: a first step comprising heating the mixture into vapor; a second step comprising maintaining while heating the vapor at a temperature higher than the boiling point of the desired cyclopentadiene or derivative thereof to condense and remove high-boiling components and simultaneously collect residual vapor; and a third step comprising maintaining while heating the collected vapor at a temperature lower than the boiling point of the desired cyclopentadiene or derivative thereof to condense and collect the cyclopentadiene or derivative thereof. In the third step, the vapor may be contact with nitrogen gas to improve the yield of the cyclopentadiene or derivative thereof.
    Type: Application
    Filed: April 2, 2001
    Publication date: November 29, 2001
    Applicant: Tanaka Kikinzoku Kogyo K.K.
    Inventors: Katsutsugu Kitada, Hiroaki Suzuki
  • Patent number: 6294706
    Abstract: Disclosed is a method for the preparation of norbornene and substituted norbornene compounds via a Diels-Alder reaction, in which a cyclic diene is reacted with an olefinic compound in order to prepare a norbornene compound. According to the invention a cyclic diene is gradually added to react with an olefinic compound, in order to keep the concentration of the cyclic diene in the reaction mixture as low as possible during the reaction. It is possible to obtain a very pure product, high yield, short reaction time and high concentrations of the exo diastereomer with the method of the invention.
    Type: Grant
    Filed: October 29, 1998
    Date of Patent: September 25, 2001
    Assignee: Opatatech Corporation
    Inventors: Christer Bergström, Jukka Koskinen, Erkki Halme, Matti Lindström, Mika Perälä
  • Patent number: 6239300
    Abstract: A number of process steps are provided that can be combined to produce bridged cyclopentadienyl-fluorenyl metallocenes. The process steps include production of a cyclopentadiene compound from dicyclopentadiene; production and recovery of a fulvene compound using the cyclopentadiene compound; production of a raw metallocene product using the fulvene compound; and recovery of the pure metallocene from the raw product.
    Type: Grant
    Filed: February 17, 1999
    Date of Patent: May 29, 2001
    Assignee: Phillips Petroleum Company
    Inventors: Carleton E. Stouffer, Syriac J. Palackal, Gary L. Glass, M. Bruce Welch, John D. Hottovy, Michael D. Jensen
  • Patent number: 6100435
    Abstract: A process is disclosed for converting dicyclopentadiene to cyclopentane and/or cyclopentene, wherein dicyclopentadiene is fed to a catalytic distillation column, the dicyclopentadiene is cracked to cyclopentadiene in the catalytic distillation column, the cyclopentadiene is hydrogenated to cyclopentane in the catalytic distillation column, and the cyclopentane is recovered from the catalytic distillation column. The dicyclopentadiene is fed into and cracked to cyclopentadiene at the bottom of the catalytic distillation column. Hydrogen is then fed to the catalytic distillation column below the catalytic zone, where cyclopentadiene is hydrogenated as it is produced, thus suppressing polymerization of the cyclopentadiene. The resulting cyclopentane and/or cyclopentene vapor phase stream is condensed, thereby producing a liquid stream of cyclopentane and/or cyclopentene and a vapor stream of hydrogen and other off-gas by-products.
    Type: Grant
    Filed: November 13, 1998
    Date of Patent: August 8, 2000
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Steven E. Silverberg, Leonel E. Sanchez, James R. Lattner
  • Patent number: 6093865
    Abstract: The present invention relates to a method for using a single distillation column to recover the reactants and products from the reaction of a cyclic diolefin and an olefin to produce an alkenyl bridged ring compound.
    Type: Grant
    Filed: June 16, 1998
    Date of Patent: July 25, 2000
    Assignee: Exxon Chemical Patent Inc.
    Inventors: James R. Lattner, Leonel E. Sanchez, Christopher L. Becker, Bruce C. Devoy
  • Patent number: 5877366
    Abstract: A process and a system for cracking dicyclopentadiene are disclosed pursuant to the process preheated dicyclopentadiene is introduced into a heated transfer fluid sufficiently below the transfer fluid surface to accomplish substantially complete conversion of said dicyclopentadiene to monomeric cyclopentadiene vapor.
    Type: Grant
    Filed: March 25, 1992
    Date of Patent: March 2, 1999
    Assignee: Boulder Scientific Company
    Inventor: John M. Birmingham
  • Patent number: 5569804
    Abstract: The present invention relates to a method for using a single distillation column to recover the reactants and products from the reaction of a cyclic diolefin and an olefin to produce an alkenyl bridged ring compound.
    Type: Grant
    Filed: December 30, 1993
    Date of Patent: October 29, 1996
    Assignee: Exxon Chemical Patents Inc (ECPI)
    Inventors: James R. Lattner, Leonel E. Sanchez
  • Patent number: 5321177
    Abstract: Recently, as a process for manufacturing cyclopentadiene resin-shaped articles, an attention has been given to reaction injection molding (RIM). To conduct RIM, it is necessary to use high purity dicyclopentadiene (DCPD) as the raw material. Vapor-phase thermal cracking of DCPD is usually used as a step of process for manufacturing high purity DCPD. Hithertofore, when conducting thermal cracking of DCPD, coke formation within cracking tubes is the most serious and troublesome problem. A vapor-phase thermal cracking process for resolving the problem by a very simple procedure is described herein. Further, a process for manufacturing high purity DCPD suitable as a raw material for use in RIM utilizing the vapor-phase thermal cracking process just mentioned above is also described.
    Type: Grant
    Filed: April 16, 1992
    Date of Patent: June 14, 1994
    Assignee: Maruzen Petrochemical Co., Ltd.
    Inventors: Takao Nakamura, Masaru Kawakita, Katsumi Minomiya
  • Patent number: 4522688
    Abstract: The process gives highly pure cyclopentadiene and methylcyclopentadiene from a cracked gasoline fraction. The merit of the process is that cyclopentadiene and methylcyclopentadiene are recovered by adding a simple distillation system to a conventional cracked gasoline treating plant without altering the plant and operating conditions thereof. An internal reflux stream is withdrawn from the stripping section of a BTX column of a conventional cracked gasoline treating plant, and is sent to a depolymerization-distillation column operated at a bottom temperature of 160.degree.-230.degree. C. The overhead stream of the column is sent to a cyclopentadiene column operated at a bottom temperature of 160.degree.-230.degree. C. Cyclopentadiene is recovered from the overhead of the column, and the bottom stream is sent to methylcyclopentadiene column operated at a bottom temperature of 170.degree.-210.degree. C. Methylcyclopentadiene is recovered from the overhead of the column.
    Type: Grant
    Filed: October 26, 1983
    Date of Patent: June 11, 1985
    Assignee: Maruzen Petrochemical Co., Ltd.
    Inventors: Akira Yokogawa, Asao Takahashi, Isao Maruyama, Takao Hosaka