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.
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.
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.
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.
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.
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
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.
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.
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
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.
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.
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
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.
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
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.
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.
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.
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.
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
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.
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
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
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