Preparing By Hydration Of Olefin Patents (Class 568/895)
  • Patent number: 4849550
    Abstract: A industrially excellent method for producing a cycloalkanol by the hydration of a cycloalkene having from 4 to 8 carbon atoms with an aromatic sulfonic acid as a catalyst which comprises carrying out said hydration in the presence of a phenol.
    Type: Grant
    Filed: March 24, 1988
    Date of Patent: July 18, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tamio Shirafuji, Itaru Kawata
  • Patent number: 4716253
    Abstract: A method for producing a cycloalkanol important as a material for caprolactam, adipic acid and the like by the hydration of a cycloalkene with a solid acid as a catalyst, which comprises carrying out said hydration in the presence of a phenol.
    Type: Grant
    Filed: November 12, 1986
    Date of Patent: December 29, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tamio Shirafuji, Kiyomi Sakai, Ken-ichi Hirose
  • Patent number: 4661639
    Abstract: A process for producing cyclic olefins by catalytic hydration of cyclic olefins is disclosed, wherein the hydration is conducted in the presence of a crystalline aluminosilicate containing at least one member selected from the group consisting of titanium, zirconium, hafnium, chromium, molybdenum, tungsten, and thorium. The hydration reaction achieves high conversions and selectivities, and the catalytic activity is retained for a long time.
    Type: Grant
    Filed: May 28, 1985
    Date of Patent: April 28, 1987
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Masahiro Tojo, Yohei Fukuoka
  • Patent number: 4645863
    Abstract: Process for the preparation of unsaturated alcohols and/or esters thereof by reacting conjugated dienes with water and/or aqueous carboxylic acid solutions in the presence of a macroporous acid ion exchanger and suitable solvents. The diene has the general formula I ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 are hydrogen or a methyl group and R.sup.2 also can represent an aliphatic hydrocarbon radical having 2 to 6 carbon atoms which may contain a double bond which is not in a conjugated position relative to the double bonds of the diene, and preferably R.sup.1 and R.sup.3 each represent groups CH.sub.3 or CH.sub.2 --CH.sub.3. Said diene is reacted in a homogeneous or quasi-homogeneous phase in the presence of said macroporous acid ion exchanger.
    Type: Grant
    Filed: January 12, 1983
    Date of Patent: February 24, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Rebafka, Helmut Nickels
  • Patent number: 4595786
    Abstract: A catalytic process for the hydration of cyclohexene to cyclohexanol in the presence of perfluorosulfonic acid polymer.
    Type: Grant
    Filed: November 27, 1984
    Date of Patent: June 17, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Francis J. Waller
  • Patent number: 4588846
    Abstract: A process is provided for producing a cyclic alcohol by catalytic hydration of a cyclic olefin in a liquid phase, which comprises using as a catalyst a zeolite having a population ratio of acid sites on the external surface to total acid sites of 0.07/1 or more, conducting the hydration reaction in a reaction zone in the copresence of an oil phase mainly containing cyclic olefin and an aqueous phase mainly containing water and the catalyst while controlling the cyclic alcohol produced so that the concentration thereof in the oil phase is more than that in the aqueous phase, and separating and recovering the cyclic alcohol produced from the oil phase.
    Type: Grant
    Filed: November 9, 1984
    Date of Patent: May 13, 1986
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Osamu Mitsui, Yohei Fukuoka
  • Patent number: 4579984
    Abstract: A method is provided for the continuous production of isopropanol and secondary butyl alcohol by catalytically hydrating the corresponding aliphatic olefin in an elongated reaction vessel in which co-product by-product dialkyl ether is separated from the reaction product and recycled to the reaction mixture being introduced therein at a point between the olefin feed inlet and the product outlet about 5 to 30 percent of the distance before the product outlet.
    Type: Grant
    Filed: April 11, 1985
    Date of Patent: April 1, 1986
    Assignee: Deutsche Texaco Aktiengesellschaft
    Inventors: Wilhelm Neier, Werner Webers, Michael Dettmer, Gunther Osterburg
  • Patent number: 4484013
    Abstract: A process is disclosed for the production of isopropanol and tertiary butyl alcohol from C.sub.3 and C.sub.4 hydrocarbons. The preferred embodiment of the invention comprises dehydrogenation of paraffins and direct hydration of the resulting olefins. Fractional distillation steps are employed between the dehydrogenation and dehydration zones and in the recycle stream to recover unconverted hydrocarbons leaving the hydration zone. This accommodates different hydration rates and prevents the passage of propylene into the dehydrogenation zone. In an alternative embodiment, the feed stream comprises olefins and is fed to the fractionation system. The dehydrogenation zone may be deleted from this embodiment.
    Type: Grant
    Filed: December 30, 1983
    Date of Patent: November 20, 1984
    Assignee: UOP Inc.
    Inventor: Robert J. Schmidt
  • Patent number: 4482767
    Abstract: A hydrocarbon conversion process is disclosed for the production of lower alcohols and LPG from a mixture of C.sub.3 -minus paraffins and olefins. The feed stream is passed into a hydration zone wherein portions of the ethylene and propylene are converted to ethanol and propanol. The hydrocarbons which are not hydrated are passed into a hydrogenation zone wherein the remaining olefins are converted to paraffins. The feed stream is preferably a hydrogen-containing C.sub.1 to C.sub.3 cut separated from the effluent of a fluidized catalytic cracking unit.
    Type: Grant
    Filed: December 20, 1983
    Date of Patent: November 13, 1984
    Assignee: UOP Inc.
    Inventor: Tamotsu Imai
  • Patent number: 4424388
    Abstract: A low temperature, low pressure process for the production of alcohol by the hydration of olefins. The olefin is contacted with a sulfonated ion-exchange resin in the presence of water and glycol diethyl solvent to hydrate said olefin, preferably propylene, and form from the olefin the corresponding aliphatic, monohydric alcohol. The solvent, a key and novel feature of the invention, at reaction conditions forms two liquid phases, a glycol diether phase and a water phase. The alcohol forms predominanty in the glycol diether phase and to a lesser extent in the water phase, with the products, inclusive of by product either, being distributed between the two phases. The glycol diethyl phase effectively displaces the equilibrium toward higher alcohol production, and the ether by product suppresses the equilibrium and minimizes formation of the ether product.
    Type: Grant
    Filed: June 25, 1982
    Date of Patent: January 3, 1984
    Assignee: Improtec
    Inventors: David G. Braithwaite, deceased, Joe D. Pickle
  • Patent number: 4423251
    Abstract: A hydrocarbon conversion process is disclosed which may be used to produce high purity isobutylene and/or tertiary butyl alcohol and methyl tertiary butyl ether. A mixed C.sub.4 feed stream is divided into two portions with a first portion being passed through a hydration zone to produce the tertiary butyl alcohol. The remaining hydrocarbons withdrawn from the hydration zone and the second portion of the feed stream are changed to an etherification zone. The unconverted hydrocarbons exiting the etherification zone may be subjected to isomerization and/or dehydrogenation to produce additional isobutylene. The high purity isobutylene is obtained by dehydrating the tertiary butyl alcohol.
    Type: Grant
    Filed: September 9, 1982
    Date of Patent: December 27, 1983
    Assignee: UOP Inc.
    Inventors: Peter R. Pujado, Bipin V. Vora
  • Patent number: 4406760
    Abstract: An improved process is provided for treating spent sulfuric acid streams formed in the catalytic hydration of olefins to prepare alcohols, wherein the spent acid stream containing organo-sulfonic acid impurities is treated in an electrolysis zone under conditions sufficient to electrolytically oxidize at least a portion of said organo-sulfonic acid impurities to form partially oxidized organic compounds therefrom and thereby provide a treated sulfuric acid stream of increased thermal stability. The improved process permits continuous operation at levels of total organic carbon in the treated acid which would otherwise be unacceptable and minimizes the substantial operating problems associated with formation of heavy carbon deposits in the process equipment.
    Type: Grant
    Filed: November 25, 1981
    Date of Patent: September 27, 1983
    Assignee: Exxon Research & Engineering Co.
    Inventors: George A. Knudsen, Charles Savini
  • Patent number: 4395576
    Abstract: A process for the preparation of ethanol by catalytic hydration of ethylene in which the crude ethanol is separated by distillation in a first column into a bottom stream consisting of aqueous ethanol and a top stream containing diethyl ether and acetaldehyde, the bottom stream is processed further in a second column, the top stream is hydrogenated and then fractionated in a third column together with an impurities containing stream originating from the second column, and optionally the diethyl ether containing top stream of the third column is recycled to the hydration reactor.
    Type: Grant
    Filed: June 11, 1981
    Date of Patent: July 26, 1983
    Assignee: Shell Oil Company
    Inventors: Arien Kwantes, Cornelis W. J. De Goederen
  • Patent number: 4358626
    Abstract: Secondary alcohols are produced by the hydration of a n-olefin substantially free from an isoolefin in the presence as catalyst of an acidic cation exchange resin such as a sulfonated styrene-divinylbenzene copolymer and in the presence of an oxy acid or lactone thereof such as .gamma.-valerolactone. The process is especially useful for hydrating a n-butene feed or a feed consisting essentially of n-butenes and butane to produce secondary butyl alcohol.
    Type: Grant
    Filed: August 6, 1981
    Date of Patent: November 9, 1982
    Assignee: Toa Nenryo Kogyo Kabushiki Kaisha
    Inventors: Yoshiharu Okumura, Tadamori Sakakibara, Katsumi Kaneko
  • Patent number: 4351970
    Abstract: A method is disclosed of preparing alcohols having 2 to 4 carbon atoms by catalytic hydration of the corresponding olefins on acid catalysts at elevated temperature and elevated pressure, characterized in that byproducts of the hydration, namely corresponding ethers and/or low-polymerized hydrocarbons and/or undesired alcohols, which form upon the passage of the input product through catalyst bed, are fed to the input product before entry into the reactor, said method being characterized in that:A. When ethylene is the olefin, the reaction is conducted at a temperature of 200.degree.-300.degree. C.; andB: When propylene is the olefin the reaction is conducted at a temperature of 150.degree. to 220.degree. C.
    Type: Grant
    Filed: May 21, 1980
    Date of Patent: September 28, 1982
    Assignee: Veba-Chemie Aktiengesellschaft
    Inventors: August Sommer, Wilhelm Heitmann, Rainer Brucker
  • Patent number: 4339617
    Abstract: Olefinic hydrocarbons may be hydrated to form corresponding alcohols by treating said olefins with water in the presence of an acidic compound which acts as a catalyst, said hydration reaction being effected at a temperature in the range of from about 100.degree. to about 300.degree. C. and a pressure in the range of from about 1 to about 100 atmospheres. In addition, the reaction medium also contains a salt of a metal selected from the group consisting of magnesium, barium, beryllium and radium, said metal salts suppressing the corrosive nature of the acid catalyst and thus permitting the reaction to be effected in normal metal reactors.
    Type: Grant
    Filed: March 9, 1981
    Date of Patent: July 13, 1982
    Assignee: UOP Inc.
    Inventors: Tamotsu Imai, Robert J. Schmidt
  • Patent number: 4334890
    Abstract: A gasoline blending stock is produced by the simultaneous reaction of a hydrocarbon feed containing at least one tertiary olefin, at least one aliphatic alcohol, and water over a suitable catalyst. In a typical embodiment, a mixed C.sub.4 stream containing isobutylene is reacted with aqueous ethanol to form a mixture of ethyl tertiary butyl ether and tertiary butanol, with minimal formation of secondary alcohols from any normal butenes present in the hydrocarbon feed.
    Type: Grant
    Filed: February 3, 1981
    Date of Patent: June 15, 1982
    Assignee: The Halcon SD Group, Inc.
    Inventors: Nand K. Kochar, Richard L. Marcell
  • Patent number: 4327231
    Abstract: Tertiary alcohols are produced by the hydration of an isoolefin in the presence as catalyst of an acidic cation exchange resin such as a sulfonated styrene-divinylbenzene copolymer, and a polyhydric neo-type alcohol such as neopentyl glycol. The process is useful for separating isobutylene from a hydrocarbon mixture containing its isomers via preparation of the alcohol, separation from the unreacted hydrocarbons and dehydration of the tertiary butyl alcohol to isobutylene.
    Type: Grant
    Filed: March 3, 1980
    Date of Patent: April 27, 1982
    Assignee: Toa Nenryo Kogyo Kabushiki Kaisha
    Inventors: Yoshiharu Okumura, Hiroshi Furukawa, Katsumi Kaneko
  • Patent number: 4284831
    Abstract: Tertiary alcohols are produced by the hydration of an isoolefin in the presence as catalyst of an acidic cation exchange resin such as a sulfonated styrene-divinylbenzene copolymer and in the presence of an oxy acid or lactone thereof such as .gamma.-valerolactone. The process is useful for separating isobutylene from a hydrocarbon mixture containing its isomers via preparation of the alcohol, separation from the unreacted hydrocarbons and dehydration of the tertiary butyl alcohol to isobutylene.
    Type: Grant
    Filed: May 5, 1980
    Date of Patent: August 18, 1981
    Assignee: Toa Nenryo Kogyo Kabushiki Kaisha
    Inventors: Yoshiharu Okumura, Katsumi Kaneko
  • Patent number: 4281206
    Abstract: Trickle-type fixed-bed catalytic reactions are improved, prior to starting or resuming an on-stream period, by purging air from the catalyst bed and reaction zone by downward flow of an inert gas therethrough, flooding the purged reaction zone by flowing a liquid upwardly through the catalyst bed to cover same, then removing the liquid and instituting the on-stream period by introducing gaseous and liquid reactants at the upper end of the catalyst bed to flow downwardly therethrough.
    Type: Grant
    Filed: January 30, 1975
    Date of Patent: July 28, 1981
    Assignee: Deutsche Texaco Aktiengesellschaft
    Inventors: Gunter Brandes, Johannes Wollner, Wilhelm Neier, Werner Webers
  • Patent number: 4236034
    Abstract: A process for producing tert-butanol by selective hydration of isobutylene in a hydrocarbon mixture comprising isobutylene and n-butene where an aqueous solution is used which contains a heteropolyacid, characterized in that the hydration reaction of isobutylene is carried out at a temperature of less than 100.degree. C.
    Type: Grant
    Filed: June 7, 1979
    Date of Patent: November 25, 1980
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Atsushi Aoshima, Toshiaki Murobushi, Ryoichi Mitsui, Nobuhiro Tamura
  • Patent number: 4234748
    Abstract: Olefins such as ethylene and propylene are hydrated in the liquid phase at elevated temperature and superatmospheric pressure to the corresponding alkanols in an aqueous reaction medium containing a catalytically effective amount of at least one substantially water-insoluble olefin hydration catalyst in the form of solid particles substantially uniformly distributed therein.
    Type: Grant
    Filed: June 28, 1979
    Date of Patent: November 18, 1980
    Assignee: National Distillers and Chemical Corp.
    Inventors: Orville D. Frampton, William R. Birchall
  • Patent number: 4182920
    Abstract: An improved process for making an alcohol by hydration of an olefin in the presence of a cation exchange resin in the acid form as catalyst and in the presence of a solvent for the reactants and product alcohol, wherein the solvent and reactants are introduced to the reactor as a single homogeneous phase to a first-stage reactor. Part of the olefin is added to a second-stage reactor. The effluent from the second stage is passed to a third-stage reactor and the unreacted olefin and solvent from the third-stage effluent are recycled to the first-stage reactor after removal of substantially all of the product alcohol. The process provides improved conversions and yields and enables the use of smaller amounts of solvent.
    Type: Grant
    Filed: July 11, 1977
    Date of Patent: January 8, 1980
    Assignee: The Dow Chemical Company
    Inventors: James H. Giles, Jeffery H. Stultz, Sandra W. Jones
  • Patent number: 4180688
    Abstract: A continuous method for producing tert-butyl alcohol from water and isobutylene in the presence of a strongly acidic cation exchange resin as a catalyst is characterized by: said catalyst particles being filled in a reactor, a liquid isobutylene being continuously brought into contact with water such that said liquid isobutylene is filled in a continuous phase in the gaps between said catalyst particles, and that water streams downwardly along the surface of said catalyst particle and subsequently the reaction mixture being continuously taken out from the reactor. According to the method of this invention, tert-butyl alcohol is obtained in a high yield with little formation of by-products.
    Type: Grant
    Filed: July 26, 1978
    Date of Patent: December 25, 1979
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Masao Imaizumi, Mitsuo Yasuda, Ko Sakata, Noboru Hirano