Of Unsaturated Hydrocarbon Patents (Class 203/9)
  • Patent number: 4268361
    Abstract: Formation of butadiene-1,3 polymer during the extractive distillation of a C-4 hydrocarbon mixture to separate and purify butadiene-1,3 using a solvent composition in which an alkoxynitrile is present in a proportion of 50-99 percent by weight, is decreased through inclusion in the solvent of a synergistic combination of 2,4-dinitrophenol and phosphoric acid, each in a proportion of 0.05 to 0.5 percent by weight.
    Type: Grant
    Filed: May 19, 1980
    Date of Patent: May 19, 1981
    Assignee: The B. F. Goodrich Company
    Inventor: Pradeep V. Patel
  • Patent number: 4265711
    Abstract: A method for destructive distillation of hydrocarbonaceous distilland is disclosed wherein a dienophile is introduced into the vaporous phase to reduce the production of non-distillable polymeric product. Specifically dienophiles available economically in large amounts such as maleic anhydride are disclosed. The introduction of additional sulfide to further reduce production of asphaltenic polymeric product is also described.
    Type: Grant
    Filed: October 23, 1979
    Date of Patent: May 5, 1981
    Inventor: William K. T. Gleim
  • Patent number: 4261798
    Abstract: The present invention relates to a method of purifying readily polymerizable high boiling vinyl monomers, in particular the acrylates and methacrylates of alkylene oxides and their ether and ester derivatives to obtain pure water white esters. The process involves flash evaporation of the preheated esters followed by condensation in the presence of polymerization inhibitors under specific conditions. The purified esters thus produced find use either as such or in the form of their copolymers in coatings, enamel paints, weather resistant finishes, adhesive compositions, as plasticizers, as lubricants for cellulose films and fibers, in magnetic tape recording media and as oil additives.
    Type: Grant
    Filed: December 17, 1979
    Date of Patent: April 14, 1981
    Assignee: BP Chemicals Limited
    Inventor: Richard G. Palmer
  • Patent number: 4252615
    Abstract: Disclosed is a process for the distillation of readily polymerizable vinyl aromatic compounds and a new polymerization inhibitor therefor. The process comprises subjecting a vinyl aromatic compound to elevated temperatures in a distillation system in the presence of a new polymerization inhibitor comprising 2,6-dinitro-p-cresol. Also disclosed is a distillation method and apparatus for use with this inhibitor.
    Type: Grant
    Filed: July 18, 1978
    Date of Patent: February 24, 1981
    Assignee: Cosden Technology, Inc.
    Inventor: James M. Watson
  • Patent number: 4237326
    Abstract: A method of inhibiting the polymerization of styrene which comprises mixing with the styrene a minor but effective quantity of an inhibitor compound selected from the group consisting of 2-methylbenzoquinone-4-oxime, 2,3,5-trimethylbenzoquinone-4-oxime and mixtures thereof.
    Type: Grant
    Filed: May 30, 1979
    Date of Patent: December 2, 1980
    Assignee: Mitsubishi Petrochemical Company Limited
    Inventors: Nobuhiko Fuga, Kunio Uchimura, Hideyuki Takahashi
  • Patent number: 4227891
    Abstract: The recovery of a hydrocarbon capable of autopolymerization from an air stream by absorbing the hydrocarbon with a plasticizer and separating the hydrocarbon from the plasticizer by vacuum and atmospheric distillation.
    Type: Grant
    Filed: January 29, 1979
    Date of Patent: October 14, 1980
    Assignee: Youngstown Sheet and Tube Company
    Inventors: Keith D. Maguire, Royce A. Currieo
  • Patent number: 4191614
    Abstract: Apparatus for the distillation of styrene from hydrocarbon feedstock incorporating a system for injection of gaseous polymerization inhibitor.
    Type: Grant
    Filed: March 1, 1976
    Date of Patent: March 4, 1980
    Assignee: Cosden Technology, Inc.,
    Inventors: James M. Watson, Michael E. Johnson
  • Patent number: 4182658
    Abstract: Disclosed is a method for preventing the polymerization of a readily polymerizable vinyl aromatic compound during distillation at elevated temperatures within a distillation apparatus which is subject to an emergency condition, such as a power outage. This method comprises force feeding a supplemental polymerization inhibitor having a high solubility in the vinyl aromatic compound, and a long duration of efficiency, into each of the distillation vessels of a conventional distillation apparatus in an amount sufficient to prevent polymerization therein. In the preferred embodiment the supplemental polymerization inhibitor comprises 2,6-dinitro-p-cresol and meta-nitro-para-cresol.
    Type: Grant
    Filed: November 23, 1977
    Date of Patent: January 8, 1980
    Assignee: Cosden Technology, Inc.
    Inventor: James M. Watson
  • Patent number: 4177110
    Abstract: A method and apparatus is disclosed for the distillation of readily polymerizable vinyl aromatic compounds with polymerization inhibitors of low volatility, particularly a phenothiazine (PZ)-tertiarybutylcatechol (TBC) polymerization inhibitor combination. The method comprises introducing a feed of impure vinyl aromatic compound into a typical distillation train comprising a first fractionation column, a recycle column, and a finishing column; introducing as a separate stream into the upper portion of said recycle column and into said first fractionation column an effective amount of the PZ-TBC inhibitor in a volatile aromatic hydrocarbon diluent; and then distilling the vinyl aromatic compound in the presence of oxygen to recover an overhead product of high purity vinyl aromatic compound and a bottoms fraction.
    Type: Grant
    Filed: July 18, 1978
    Date of Patent: December 4, 1979
    Assignee: Cosden Technology, Inc.
    Inventor: James M. Watson
  • Patent number: 4163755
    Abstract: Use of copper ion in acrylamide solution during concentration to inhibit polymerization.
    Type: Grant
    Filed: January 13, 1977
    Date of Patent: August 7, 1979
    Assignee: American Cyanamid Company
    Inventors: Ken Matsuda, Martin S. Butensky, Kin H. Tsu, Robert J. Munch
  • Patent number: 4161495
    Abstract: A method for stabilizing acetylene against explosive decomposition comprising mixing together with the acetylene a chemical free radical scavenging agent chosen from the group consisting of nitric oxide, hydrogen chloride, hydrogen bromine, hydrogen iodide and vinyl bromine as well as mixtures thereof.
    Type: Grant
    Filed: September 25, 1978
    Date of Patent: July 17, 1979
    Assignee: Union Carbide Corporation
    Inventor: Clifford M. Detz
  • Patent number: 4132603
    Abstract: Disclosed is a process for the distillation of readily polymerizable vinyl aromatic compounds which comprises subjecting such compounds to distillation conditions in the presence of an effective amount of a 4-halo-3,5-dinitrotoluene as a polymerization inhibitor.
    Type: Grant
    Filed: November 23, 1977
    Date of Patent: January 2, 1979
    Assignee: Cosden Technology, Inc.
    Inventor: James M. Watson
  • Patent number: 4132601
    Abstract: Disclosed is a process for the distillation of readily polymerizable vinyl aromatic compounds which comprises subjecting such compounds to distillation conditions in the presence of an effective amount of a polymerization inhibitor selected from the group consisting of 3-nitro-2, 5-cresotic acid and 3-nitro-2, 5-cresotaldehyde.
    Type: Grant
    Filed: November 23, 1977
    Date of Patent: January 2, 1979
    Assignee: Cosden Technology, Inc.
    Inventor: James M. Watson
  • Patent number: 4132602
    Abstract: Disclosed is a process for the distillation of readily polymerizable vinyl aromatic compounds which comprises subjecting such compounds to distillation conditions in the presence of an effective amount of a halo-6-nitro-p-cresol as a polymerization inhibitor.
    Type: Grant
    Filed: November 23, 1977
    Date of Patent: January 2, 1979
    Assignee: Cosden Technology, Inc.
    Inventor: James M. Watson
  • Patent number: 4105506
    Abstract: Disclosed is a process for the distillation of readily polymerizable vinyl aromatic compounds and a new polymerization inhibitor therefor. The process comprises subjecting a vinyl aromatic compound to elevated temperatures in a distillation system in the presence of a new polymerization inhibitor comprising 2,6-dinitro-p-cresol.
    Type: Grant
    Filed: February 24, 1977
    Date of Patent: August 8, 1978
    Assignee: Cosden Technology, Inc.
    Inventor: James M. Watson
  • Patent number: 4087335
    Abstract: A method is disclosed for stabilizing vinylbenzyl chloride and vinyltoluene against violent decomposition in the presence of iron and chlorine at ambient and above ambient temperatures which comprises contacting the vinylbenzyl chloride or vinyltoluene with an amount of a Lewis base sufficient to inhibit the decomposition during the preparation, purification or storage of said vinylbenzyl chloride or vinyltoluene.
    Type: Grant
    Filed: May 5, 1977
    Date of Patent: May 2, 1978
    Assignee: Rohm and Haas Company
    Inventor: Allen P. Marks
  • Patent number: 4086147
    Abstract: Disclosed is a process for the distillation of readily polymerizable vinyl aromatic compounds and a new polymerization inhibitor therefor. The process comprises subjecting a vinyl aromatic compound to elevated temperatures in a distillation system in the presence of a new polymerization inhibitor comprising m-nitro-p-cresol.
    Type: Grant
    Filed: December 10, 1976
    Date of Patent: April 25, 1978
    Assignee: Cosden Technology, Inc.
    Inventor: James M. Watson
  • Patent number: 4061545
    Abstract: Disclosed is a process for the distillation of readily polymerizable vinyl aromatic compounds which comprises subjecting such compounds to distillation conditions in the presence of an effective amount of a combination of phenothiazine and a phenolic compound, preferably tert-butylcatechol (TBC), as a polymerization inhibitor system in the presence of oxygen.
    Type: Grant
    Filed: February 19, 1976
    Date of Patent: December 6, 1977
    Assignee: Cosden Technology, Inc.
    Inventor: James M. Watson
  • Patent number: 4050993
    Abstract: The present invention relates to a process for the distillation of readily polymerizable ethylenically unsaturated compounds comprising subjecting such compounds to distillation conditions in the presence of nitroso methylaniline as a polymerization inhibitor and in the absence of oxygen (air) and sulfur.
    Type: Grant
    Filed: September 11, 1972
    Date of Patent: September 27, 1977
    Assignee: Cosden Oil & Chemical Company
    Inventor: Calvin L. Daniels
  • Patent number: 4040912
    Abstract: Disclosed is a process for the distillation of readily polymerizable vinyl aromatic compounds and a new polymerization inhibitor therefor. The process comprises subjecting a vinyl aromatic compound to distillation conditions in a distillation system and adding to the system the new polymerization inhibitor comprising an adduct of nitric oxide and styrene.
    Type: Grant
    Filed: December 9, 1974
    Date of Patent: August 9, 1977
    Assignee: Cosden Technology, Inc.
    Inventor: James M. Watson
  • Patent number: 4040911
    Abstract: The present invention relates to a process for inhibiting the polymerization of styrene monomers during the purification of crude styrene.
    Type: Grant
    Filed: January 2, 1976
    Date of Patent: August 9, 1977
    Assignee: Gulf Research & Development Company
    Inventors: John D. Bacha, Charles M. Selwitz
  • Patent number: 4036905
    Abstract: In the epoxidation of propylene with tertiary butyl hydroperoxide to form propylene oxide, a by-product, tertiary butyl alcohol is formed. This alcohol can be dehydrated to form isobutylene which can be sold as a product or hydrogenated, followed by oxidation, and the resulting hydroperoxide reacted with propylene to produce propylene oxide and tertiary butyl alcohol for recycle. In this process, the operation of the tertiary butyl alcohol vaporizer is substantially improved by increasing the quantity of liquid purge to at least 15 weight percent of the input. Under such operating conditions, the organic content of the waste water effluent from the entire plant is reduced, fouling of the vaporizer heat transfer surfaces is minimized thereby increasing the on-stream time between cleanings by as much as 2-3 times the normal, and deposits are more easily removed from the vaporizer when it is shut down for cleaning.
    Type: Grant
    Filed: April 12, 1976
    Date of Patent: July 19, 1977
    Assignee: Oxirane Corporation
    Inventor: Alan D. Kornfeld
  • Patent number: 4033829
    Abstract: Styrene is inhibited against polymerization during the distillation thereof by incorporating therein, in an amount sufficient to inhibit polymerization thereof, the dinitrophenol solution recovered from styrene still residues or tars resulting from the distillation of styrene in the presence of dinitrophenol. The recovered dinitrophenol solution is a more effective polymerization inhibitor than dinitrophenol per se.
    Type: Grant
    Filed: December 15, 1975
    Date of Patent: July 5, 1977
    Assignee: Monsanto Company
    Inventors: Thomas D. Higgins, Jr., Raymond A. Newsom
  • Patent number: 4032572
    Abstract: A method for economically concentrating an acrylamide aqueous solution by catalytic hydration without substantial deterioration in the product. According to the method, an acrylamide aqueous solution obtained from catalytic hydration, is concentrated by distillation while maintaining the solution in good contact with at least 0.1 mole. or more of air per mole of water distilled from the acrylamide aqueous solution.
    Type: Grant
    Filed: December 3, 1975
    Date of Patent: June 28, 1977
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Shiro Asano, Kiyotaka Yoshimura, Ryoji Tsuchiya, Tadatoshi Honda
  • Patent number: 4003800
    Abstract: The present invention relates to the use of quinone alkides as polymerization inhibitors in a styrene purification process. The inhibitors are prepared by oxidizing hindered phenols to the corresponding quinone alkide.
    Type: Grant
    Filed: January 2, 1976
    Date of Patent: January 18, 1977
    Assignee: Gulf Research & Development Company
    Inventors: John D. Bacha, Charles M. Selwitz
  • Patent number: 3993547
    Abstract: Disclosed is a process for the distillation of readily polymerizable vinyl aromatic compounds and a new polymerization inhibitor therefor. The process comprises subjecting a vinyl aromatic compound to distillation conditions in a distillation system and adding to the system the new polymerization inhibitor comprising alpha, gamma-bis-diphenylene-beta-phenyl allyl.
    Type: Grant
    Filed: January 24, 1975
    Date of Patent: November 23, 1976
    Assignee: Cosden Technology, Inc.
    Inventor: James M. Watson
  • Patent number: 3988212
    Abstract: Disclosed is a process for the distillation of readily polymerizable vinyl aromatic compounds and a new polymerization inhibitor therefor. The process comprises subjecting a vinyl aromatic compound to distillation conditions in a distillation system and adding to the system the new polymerization inhibitor comprising a mixture of N-nitroso diphenyl amine and a dinitro-O-cresol.
    Type: Grant
    Filed: March 21, 1975
    Date of Patent: October 26, 1976
    Assignee: Cosden Technology, Inc.
    Inventor: James M. Watson
  • Patent number: 3988213
    Abstract: A method of distilling a polymerizable vinyl compound selected from the group consisting of acrolein, methacrolein, acrylic acid, methacrylec acid, hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, glycidyl acrylate and glycidyl methacrylate, the method comprising distilling the polymerizable vinyl compound in the presence of a polymerization inhibitor using a distillation tower having perforated trays without downcomers and wherein the temperature of the inner wall of the tower is maintained at a temperature sufficient to prevent the condensation of the vapor being distilled, whereby the polymerizable vinyl compound is distilled without the formation of polymer.
    Type: Grant
    Filed: October 1, 1974
    Date of Patent: October 26, 1976
    Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.
    Inventors: Sadao Yoshida, Kunihiro Kubota, Daizo Kobayashi, Noboru Shimizu, Takashi Ohara
  • Patent number: 3986937
    Abstract: Disclosed is a process for the distillation of readily polymerizable vinyl aromatic compounds which comprises subjecting such compounds to distillation conditions in the presence of an effective amount of N.sub.2 O.sub.3 as a polymerization inhibitor.
    Type: Grant
    Filed: December 9, 1974
    Date of Patent: October 19, 1976
    Assignee: Cosden Technology, Inc.
    Inventor: James M. Watson
  • Patent number: 3979473
    Abstract: A process for the stabilization of indene against discoloration comprising adding to the indene a minor amount of an insoluble compound selected from the group consisting of neutral, acidic and basic inorganic salts, inorganic acids and organic acids.
    Type: Grant
    Filed: December 23, 1974
    Date of Patent: September 7, 1976
    Assignee: Standard Oil Company
    Inventors: George S. Li, Gerald P. Coffey
  • Patent number: 3964979
    Abstract: Disclosed is a process for the distillation of readily polymerizable vinyl aromatic compounds which comprises subjecting such compounds to distillation conditions in the presence of an effective amount of NO as a polymerization inhibitor in the substantial absence of oxygen.
    Type: Grant
    Filed: December 9, 1974
    Date of Patent: June 22, 1976
    Assignee: Cosden Technology, Inc.
    Inventor: James M. Watson
  • Patent number: 3964978
    Abstract: Disclosed is a process for the distillation of readily polymerizable vinyl aromatic compounds which comprises subjecting such compounds to distillation conditions in the presence of an effective amount of NO.sub.2 as a polymerization inhibitor.
    Type: Grant
    Filed: December 9, 1974
    Date of Patent: June 22, 1976
    Assignee: Cosden Technology, Inc.
    Inventor: James M. Watson
  • Patent number: 3951754
    Abstract: A method of inhibiting the thermopolymerization of isoprene or butadiene in the process of isolation thereof by extractive distillation from a mixture of hydrocarbons obtained in dehydrogenation of isopentane and butane. The method of inhibiting includes, prior to the introduction of said mixture of hydrocarbons and a polar extractant into an extractive distillation metal apparatus, treating the surface of the apparatus with a 1-25% aqueous solution of passivators, viz. nitrites, sulphites or phosphates of alkali metals at a temperature of 20.degree.-100.degree.C. The mixture of hydrocarbons and the polar extractant with an inhibitor of isoprene or butadiene thermopolymerization introduced into the polar extractant are then fed into said apparatus in an amount of 0.01-1% of the extractant weight. The present method makes it possible to reduce markedly the formation of isoprene and butadiene and, hence, to prevent the plugging of the extractive distillation apparatuses with the aforementioned thermopolymers.
    Type: Grant
    Filed: February 19, 1974
    Date of Patent: April 20, 1976
    Inventors: Alexandr Grigorievich Liakumovich, Boris Izrailevich Pantukh, Aida Pavlovna Zakharova, Vitaly Ivanovich Butin, Vladimir Alexeevich Tulupov, Zoya Stephanovna Baiburina
  • Patent number: 3933599
    Abstract: Disclosed is a process for the distillation of readily polymerizable vinyl aromatic compounds which comprises subjecting such compounds to distillation conditions in the presence of an effective amount of NOCl as a polymerization inhibitor in the substantial absence of oxygen.
    Type: Grant
    Filed: December 9, 1974
    Date of Patent: January 20, 1976
    Assignee: Cosden Technology, Inc.
    Inventor: James M. Watson