Preparing By Reacting An Olefin And An Organic Hydroxy Containing Compound (h Of -oh May Be Replaced By A Group Ia Or Iia Light Metal) Patents (Class 568/697)
  • Patent number: 4256465
    Abstract: A method for producing methyl tert-butyl ether which comprises the steps of: allowing isobutylene-containing hydrocarbon and methyl alcohol in a given molar ratio to react at a given temperature, pressure and liquid space velocity in the presence of strongly acidic cation-exchange resin catalyst; then passing the reaction product through a fixed bed filled with a water-insoluble, solid particulate acid-neutralizing agent; and subjecting the effluent to flashing operation, preferably also to rectification, to obtain methyl tert-butyl ether. Further included in the invention is the preparation of a fuel composition by mixing the thus obtained methyl tert-butyl ether into an internal combustion fuel.
    Type: Grant
    Filed: July 20, 1979
    Date of Patent: March 17, 1981
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Tetsuya Takezono, Yasuo Fujiwara
  • Patent number: 4242526
    Abstract: Methyl tertiary butyl ether is produced from a mixture of C.sub.4 hydrocarbons containing isobutylene and butadiene. The isobutylene is selectively reacted with a greater than stoichiometric amount of methanol at a temperature of 50 to 120 degrees C., in a homogeneous liquid phase and in the presence of a catalytic amount of sulfuric acid. The sulfuric acid is present in an amount less than 20% by weight based on the weight of the reaction mixture. The homogeneous liquid phase is maintained throughout the reaction whereby a reaction mixture containing methyl tertiary butyl ether is produced and undesired polymerization of the badadiene is avoided. The reaction mixture is cooled then reaction mixture which has been washed free of methanol, or separated unreacted C.sub.4 fraction which is isobutylene-free, is added. An upper phase containing hydrocarbons and methyl tertiary butyl ether and a part of the methanol and a lower phase containing methanol and 10 to 50% sulfuric acid is formed.
    Type: Grant
    Filed: March 8, 1978
    Date of Patent: December 30, 1980
    Assignee: Magyar Asvanyolaj es Foldgaz Kiserleti Intezet
    Inventors: Janos Laky, Rezso Csikos, Lajos Peterfy, Lajos Szvetelszky, Istvan Pallay
  • Patent number: 4219678
    Abstract: Process for the preparation of pure methyl tert.-butyl ether. Isobutene or isobutene-containing hydrocarbon mixtures are reacted with methanol in a molar ratio of 1:1 to 1:2 in the liquid phase at temperatures of between 30.degree. and 100.degree. C. on sulfonated, strongly acidic, macroporous organic ion exchange resins. After separation of the unreacted hydrocarbons, the reaction mixture is distilled under pressure; the methanol-containing distillate formed during the distillation is recycled into the zone of the reaction between methanol and isobutene; and pure methyl tert.-butyl ether is withdrawn from the sump of the distillation column.
    Type: Grant
    Filed: December 29, 1978
    Date of Patent: August 26, 1980
    Assignee: Chemische Werke Huls AG
    Inventors: Fritz Obenaus, Wilhelm Droste, Wolf Streubel, Michael Zolffel, Wolfgang Muller
  • Patent number: 4218569
    Abstract: Mixed hydrocarbons of predominantly four carbon atoms each are subjected to etherification with methanol, to make ether from the tertiary olefin in the mixture; the unreacted hydrocarbons, after separation from the ether by distillation, are contaminated with methanol which is removed by absorption or extraction with a glycol before the hydrocarbons are subjected to further processing in which the methanol is detrimental.
    Type: Grant
    Filed: March 14, 1978
    Date of Patent: August 19, 1980
    Assignee: Gulf Canada Limited
    Inventors: John D. Chase, Buenaventura B. Galvez, Bruce W. Kennedy
  • Patent number: 4204077
    Abstract: In the processing of olefinic hydrocarbon mixtures containing isobutylene and isoamylene which are etherified with methanol to obtain higher octane components, unreacted methanol is removed from the etherified mixture by contact with a separate liquid glycol phase before unreacted hydrocarbons, substantially free of methanol, are distilled from the etherified mixture for further catalytic processing in which methanol is deleterious to the catalyst.
    Type: Grant
    Filed: October 2, 1978
    Date of Patent: May 20, 1980
    Assignee: Gulf Canada Limited
    Inventors: Hanbury J. Woods, John D. Chase, Buenaventura B. Galvez
  • Patent number: 4198530
    Abstract: A mixed C.sub.4 hydrocarbon stream containing from 5 to 60% isobutene is mixed with methanol providing from about 2% to about 20% excess methanol (stoichiometry based on isobutene content) to provide fresh feed for preparing tertiary butyl methyl ether in a reaction zone containing acidic ion exchange catalyst. Formation of trouble-some amounts of diisobutylene is repressed by the presence of the excess methanol. The effluent comprising TBME, excess methanol, and unreacted C.sub.4 hydrocarbons is directed to a unique purification zone. The butenes are distilled from the effluent at a pressure from about 7 to 25 atmospheres, preferably at about 12 to 20 atmospheres. Surprisingly all of the excess methanol is azeotropically removed with the C.sub.4 hydrocarbons by the pressurized azeotropic distillation, leaving a bottoms consisting of a technical grade of TBME free from troublesome amounts of methanol.
    Type: Grant
    Filed: June 29, 1978
    Date of Patent: April 15, 1980
    Assignee: Atlantic Richfield Company
    Inventors: W. Wayne Wentzheimer, Frank W. Melpolder
  • Patent number: 4193770
    Abstract: A process for preparing, from tertiary olefin containing hydrocarbon fractions, a hydrocarbon fraction containing tertiaryamyl methyl ether, the process achieving high conversion of 2-methyl butenes to the ether by etherification with methanol after adequate separation of the 2-methyl butenes from other tertiary olefins, the improved conversion being achieved by separating unreacted 2-methyl butenes from etherified material and recycling them for further reaction.
    Type: Grant
    Filed: May 15, 1978
    Date of Patent: March 18, 1980
    Assignee: Gulf Canada Limited
    Inventors: John D. Chase, Hanbury J. Woods, Bruce W. Kennedy
  • Patent number: 4187384
    Abstract: Mono- and poly-ethylene glycol dialkyl ethers IR.sup.1 --O--(--CH.sub.2 --CH.sub.2 --O--).sub.n --R.sup.2where R.sup.1 is C.sub.1 -C.sub.4 -alkyl, R.sup.2 is C.sub.3 -C.sub.5 -alkyl and n is from 1 to 100, are prepared by reacting monoalkyl ethers IIR.sup.1 --O--(--CH.sub.2 --CH.sub.2 --O--).sub.n --Hwith a C.sub.3 -C.sub.5 -olefin III in the presence of an acid ion exchanger at from 1 to 200 bar and from 40.degree. to 150.degree. C., the reaction being started at from 100.degree. to 150.degree. C. and the temperature then being lowered, in at least two approximately equal steps, to from 40.degree. to 80.degree. C., the temperature being dropped in each case to the next-lower level when the conversion per unit time no longer changes significantly.
    Type: Grant
    Filed: January 10, 1979
    Date of Patent: February 5, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Platz, Werner Fuchs, Wolfgang Vodrazka
  • Patent number: 4182914
    Abstract: There is disclosed a process for continuously producing diisopropyl ether of high purity from isopropyl alcohol and propylene at a high yield, which comprises the steps of: continuously passing isopropyl alcohol and propylene at a given molar ratio through a first fixed bed filled with particles of strongly acidic cation-exchange resin at a temperature in the range from 100.degree. C. to 130.degree. C.; then passing the reaction mixture through a second fixed bed filled with a water-insoluble, solid, particulate acid-neutralizing agent; and flash-removing unreacted propylene from the mixture, followed by solvent refining and distillation, whereby diisopropyl ether of high purity is continuously obtained at a high yield.
    Type: Grant
    Filed: December 29, 1977
    Date of Patent: January 8, 1980
    Assignee: Nippon Oil Company Limited
    Inventor: Masao Imaizumi
  • Patent number: 4182913
    Abstract: A method for producing methyl tert-butyl ether which comprises the steps of: allowing isobutylene-containing hydrocarbon and methyl alcohol in a given molar ratio to react at a given temperature, pressure and liquid space velocity in the presence of strongly acidic cation-exchange resin catalyst; then passing the reaction product through a fixed bed filled with a water-insoluble, solid particulate acid-neutralizing agent; and subjecting the effluent to flashing operation, preferably also to rectification, to obtain methyl tert-butyl ether. Further included in the invention is the preparation of a fuel composition by mixing the thus obtained methyl tert-butyl ether into an internal combustion fuel.
    Type: Grant
    Filed: November 21, 1977
    Date of Patent: January 8, 1980
    Assignee: Nippon Oil Company Ltd.
    Inventors: Tetsuya Takezono, Yasuo Fujiwara
  • Patent number: 4175210
    Abstract: A process for converting an olefin, or a mixture of olefins, to an ether, or a mixture of ethers, which comprises reacting said olefin, or said mixture of olefins, with an alcohol in contact with silicatungstic acid.
    Type: Grant
    Filed: June 19, 1978
    Date of Patent: November 20, 1979
    Assignee: Gulf Research and Development Company
    Inventors: Charles M. Selwitz, John G. McNulty
  • Patent number: 4148695
    Abstract: Methyl t-butyl ether may be recovered from etherification reaction effluent by extractive distillation in the presence of n-butanol.
    Type: Grant
    Filed: July 27, 1978
    Date of Patent: April 10, 1979
    Assignee: Texaco Inc.
    Inventors: Kung-You Lee, Richard V. Kessler, Uygur Kokturk