Abstract: Excess alcohol, e.g. methanol contained in a C.sub.4 -C.sub.6 hydrocarbon stream is removed in process using less water and energy than a conventional water wash by subjecting the stream to a first single stage water wash with 2 to 10 wt % water based on the hydrocarbon where most of the alcohol is removed and then washing the raffinate having reduced methanol therefrom subjected to multistage water wash to remove the remainder of the alcohol.

Abstract: 3-Methyl-2-butanol is difficult to separate from 2-pentanol by conventional distillation or rectification because of the proximity of their boiling points. 3-Methyl-2-butanol can be readily separated from 2-pentanol by extractive distillation. Effective agents are acetamide or 2,2,2-trichloroethanol.

Abstract: Dialkyl ethers having 5 to 7 carbon atoms; e.g. MTBE, and alcohols having 1 to 4 carbon atoms are extracted from wastewater with contaminant-free gasoline. Wastewater saturated with contaminants is reduced to 200 ppm contaminants in the absence of stripping. An octane enhanced gasoline is recovered. Additional ether may be added to the recovered gasoline to increase octane. The method is particularly effective in wastewater/gasoline system containing emulsifiers such as surfactants, gasoline detergents and colloidal particles.

Abstract: 1-Butanol is difficult to separate from 2-pentanol by conventional distillation or rectification because of the proximity of their boiling points. 1-Butanol can be readily separated from 2-pentanol by extractive distillation. Effective agents are ethyl benzene, d-limonene and terpinolene.

Abstract: 2-Butanol is difficult to separate from t-amyl alcohol by conventional distillation or rectification because of the proximity of their boiling points. 2-Butanol can be readily separated from t-amyl alcohol by extractive distillation. Effective agents are methyl caproate, adiponitrile and cyclopentanone.

Abstract: 1-Propanol is difficult to separate from 2-butanol by conventional distillation or rectification because of the proximity of their boiling points. 1-Propanol can be readily separated from 2-butanol by extractive distillation. Effective agents are isobutyl acetate, isobornyl methyl acetate and ethyl butyrate.

Abstract: Ethanol is difficult to separate from isopropanol by conventional distillation or rectification because of the proximity of their boiling points. Ethanol can be readily separated from isopropanol by extractive distillation. Effective agents are methyl caproate, cyclopentane and isobutyl acetate.

Abstract: For separating ETBE and ethanol the following principal stages are employed:(1) Extraction of ethanol by water, the raffinate being ETBE saturated in water and the extract an ethanol/water mixture containing a small proportion of ETBE;(2) Concentration of the above mixture, the distillate being a mixture close to the ethanol/water azeotrope in composition and containing a very small proportion of ETBE;(3) Heteroazeotropic distillation of this distillate in two coupled columns with an overhead decanter, this distillation using ETBE as azeotroping agent; the residue of the first column being ethanol which is ca. 99% by mole and the residue of the second column being practically pure water, this water and the water recovered during the concentration stage being used as extraction solvent in stage (1).Stage (3) may be an ethanol dehydration unit using ETBE as dehydrating agent.

Abstract: 1-Pentanol is difficult to separate from cyclopentanol by conventional distillation or rectification because of the closeness of their boiling points. 1-Pentanol can be readily separated from cyclopentanol by extractive distillation. Effective agents are ethylene glycol and sulfolane.

Abstract: This invention relates to a process for the production of absolute alcohol from aqueous alcohol, whereby saving of energy to a greater extent is rendered possible in a more simple process, as compared with the prior art azeotropic distillation method using benzene or cyclohexane. That is, aqueous alcohol is subjected to extractive distillation in a first distillation column under such a condition that a liquid and gas of a solvent simultaneously coexist using low pressure propane, propylene and butane as the solvent, absolute alcohol substantially free from water is recovered from the bottom of the distillation column and subjected to stripping of hydrocarbons in a second distillation column, during which the gaseous phases of the first and second distillation columns are mixed and compressed, utilized through recompression as a heat source of a reboiler of the first distillation column, subjected to separation of water content and recycled to the upper parts of the first and second distillation columns.

Abstract: An improvement is proposed for the removal of the precipitates of a phosphine oxide compound as a by-product from a mixture thereof with an olefin compound obtained by the Wittig reaction for the preparation of the olefin compound from a phosphorane compound and a carbonyl compound. Instead of the conventional procedure of filtration to remove the precipitates, the mixture in a hydrocarbon solvent, after replacement of a non-hydrocarbon solvent with a hydrocarbon solvent, if necessary, is admixed with a lower carboxylic acid such as acetic acid so that the precipitates of the phosphine oxide are dissolved forming a viscous fluid which is immiscible with the mixture of the olefin compound and the hydrocarbon solvent. The fluid containing the dissolved phosphine oxide compound can be easily removed by phase separation so that a great increase is obtained in the yield of the desired olefin compound.

Abstract: Disclosed is a purification process for removing lipophilic impurities coined in an aqueous crude ethanol solution, in particular, for efficiently removing impurities consisting of C.sub.3 -C.sub.4 alcohols. The process involves (a) a first extraction step wherein the aqueous crude ethanol solution is extracted with an extractant for removing the lipophilic impurities, except for the C.sub.3 -C.sub.4 alcohols, contained in the aqueous crude ethanol solution by subjecting the aqueous crude ethanol solution to extraction with the extractant in a pressurized state containing carbon dioxide in a liquidized state or carbon dioxide gas in a supercritical state; (b) a concentration-distillation step wherein a raffinate obtained in the first extraction step is fed to a distilling column to thereby obtain a highly concentrated aqueous ethanol solution from a top of the distilling column and withdraw fraction containing C.sub.3 -C.sub.

Abstract: A method of continuously distilling off the components of a mixture containing phenols, water and methanol using a single distillation column, wherein methanol is recovered from the top of the column, water containing phenols is dragged as a side stream from a recovery section of the column, and phenols are recovered as a bottom product. The method permits efficient separation by the single distillation column of the three components with high purity and low utility energy.

Abstract: A coolant recycling apparatus has a boiler and condenser for distilling a glycol and water from a used coolant. The glycol and water are recombined in a mixing tank to form a mixture having a desired ratio of water to glycol, and an inhibitor is added to the mixture to obtain a fresh coolant mixture ready for use in an engine cooling system. Contaminants in the used coolant are concentrated to form a sludge.

Abstract: The present invention is a method for the separation of impurities from a crude ethanol aqueous solution, comprising of; (i) extracting lipophilic impurities within the crude ethanol aqueous solution into an extracting solvent phase by treating the crude ethanol aqueous solution with an extracting solvent comprising carbon dioxide in a liquid state or carbon dioxide in a super-critical state under conditions wherein a ratio of the weight of the extracting solvent to the weight of the crude ethanol aqueous solution is 2 or higher; and (ii) recovering ethanol entrained with the extracting solvent or ethanol and methanol entrained with the extracting solvent into an aqueous phase by contacting the extracting solvent phase resulting after extracting the impurities to with water in a countercurrent manner under pressures in a ratio of the weight of water to the weight of the extracting solvent of 0.3 or lower.

Abstract: Methylene chloride cannot be completely separated from methanol or ethanol by conventional distillation or rectification because of the mimimum boiling azeotrope. Methyelne chloride can be readily separated from methanol or ethanol by azeotropic or extractive distillation. Typical effective agents are: for methanol by azeotropic distillation, isopropanol or t-butanol; by extractive distillation, 1-nitropropane or n-butanol; for ethanol by extractive distillation, isobutanol or n-propyl acetate.

Abstract: High purity isopropyl acetate and ethanol are recovered from a process stream containing isopropyl acetate, ethanol and water by a multiple step process including extracting substantially all of the ethanol from the stream using water as a solvent, stripping the extract stream to remove substantially all of the remaining isopropyl acetate as an overhead recycle stream, which is combined with the fresh feed stream prior to the extraction step, fractionating the ethanol-rich stripping column bottoms stream to produce a ethanol-water azeotropic overhead stream and using a portion of the fractionating column bottoms stream as the solvent for the extraction step.

Abstract: The present invention relates to a method and an apparatus to condense and rectify alcohol, and more particularly to a method and an apparatus suitable for the energy-saving condensation and rectification of high-purity alcohol from the synthesized alcohol, the used alcohol aqueous solution in food industry and the fermented alcohol.The invention provides a method, which makes it possible to extract and recover alcohol of 99 wt % or higher with small quantity of propane solvent, using the propane in supercritical or pseudocritical conditions in the process of condensation and recovery of alcohol from aqueous solution of alcohol. Further, the method makes it possible to condense alcohol to the concentration of 95 wt % or higher by increasing the selectivity of alcohol through the cooling of the propane to liquid state.

Abstract: A process for separation of components of a mixture of more than one organic substance or of a mixture of at least one organic substance and water by extraction using a supercritical fluid as an extractant. During the extraction an extraction aid having a higher affinity with an unextractable component of the mixture than with an extractable component of the mixture is present. Also disclosed is an apparatus for carrying out this process.

Abstract: According to the process of the present invention, carboxylic acids are recovered from aqueous strong acid mixtures thereof which mixtures are formed as an alcohol-depleted phase by the extraction of alcohols from aqueous strong acid solution with carboxylic acids, by contacting the mixtures with a liquid organic solvent, to form a purified aqueous strong acid stream depleted in such carboxylic acid by contacting such aqueous strong acid mixtures with a liquid organic solvent, such as an alkane, alkene or di-alkyl ether to form a purified aqueous strong acid depleted in such carboxylic acid.

Abstract: According to the process of the present invention, alcohols are recovered from aqueous mixtures thereof with a concentrated strong acid by contacting such alcohol-containing aqueous concentrated acid mixtures with a carboxylic acid selected from the group consisting of acids of the formula RCO.sub.2 H wherein R is a straight or branched-chain or cyclic alkyl of from 5 to 19 carbon atoms per molecule to form an extract phase containing the carboxylic acid in addition to said alcohol, and an aqueous raffinate phase depleted in the alcohol.

Abstract: This invention relates to a method for separating organic compounds, particularly lower aliphatic alcohols from fermentation fluids. This is accomplished by the use of a two-step extraction process whereby said lower aliphatic alcohols are selectively extracted from said fermentation fluids by a first solvent. The fermentation fluids from which the lower aliphatic alcohols have been extracted contain some of this first solvent. Therefore, a second solvent, which substantially differs from the first solvent in polarity is employed to extract the residual amounts of first solvent from said fermentation fluids. Then, the fermentation fluids, thus purified, can be returned to the fermentation process without the danger of toxic influences on the fermentation by the presence of said first solvent.

Abstract: A process for forming a purified solute from an aqueous solution is provided whereby a mixture of an extractant, a hydrate former and the aqueous solution is first formed. The hydrate former forms a hydrate with water while the solute does not form a hydrate. The extractant takes up the solute from the aqueous solution. The mixture is subjected to a temperature and pressure sufficient to form the solid hydrate of the hydrate former, an aqueous solution of the solute and a portion comprising the extractant containing the solute. The solute is recovered from the portion comprising the extractant and the solute.

Abstract: Formamide is prepared continuously from methyl formate and ammonia, pure methanol being recovered, by a process wherein(a) the reaction of methyl formate and ammonia is carried out predominantly in the liquid phase in the upper region of a reaction column R having a total of from 15 to 30 theoretical plates,(b) the methanol formed in this reaction is removed, together with small amounts of formamide, from the column or the evaporator in vaporus form at the level of plates 1-5 (counted from the bottom),(c) the formamide is removed from this methanol/formamide mixture, together with small amounts of methanol, in a distillation column D1 and recycled to R, and(d) the small amounts of methanol contained in the bottom product from R, which substantially consists of formamide and in this column should be at from 110.degree. to 130.degree. C., are separated off in a distillation column D2.

Abstract: The process of extracting butyric acid and normal butanol from microbial fermentation broth, comprising contacting an aqueous solution of a microbial fermentation broth with vinyl bromide to extract any butyric acid and normal butanol which is present from the fermentation broth into the vinyl bromide. The vinyl bromide is thereafter separated from the aqueous fermentation broth and then evaporated, leaving the butyric acid and/or normal butanol in substantially pure, isolated form.

Abstract: A process for producing a lower aliphatic alcohol by splitting ethers whereby ethers are reacted at an elevated temperature and pressure with an excess of water in the presence of acidic hydration catalysts is disclosed.

Abstract: A process is presented for extracting polar organic compounds, in particular lower aliphatic alcohols, out of their aqueous solutions, which is based on the use of fluids which contain a significant amount of polyoxaalkanols, polyoxaalkanediols and/or polyoxaalkanepolyols. These compounds, by virtue of their high molar masses, their low solubility in water and their good affinity for polar organic compounds, are particularly suitable for use as extractants.

Abstract: An improved process for the acid-catalyzed hydrolysis tertiary butyl hydroperoxide to form hydrogen peroxide wherein an organic solvent is added to the hydrolysis zone, which solvent promotes the partitioning of hydrogen peroxide and oxidizable organic material into separate aqueous and organic phases, respectively.

Abstract: A method for the extraction of lower alcohols from aqueous solutions by contacting said solutions with various phosphine oxides, in the presence or absence of alkali or alkaline earth metal salts, is disclosed.

Abstract: According to the process of this invention, saturated mono-alcohols are recovered from solutions containing such mono-alcohols together with a carboxylic acid extraction solvent therefor by passing the mono-alcohol solution to an alcohol vaporization zone, introducing a substantially anhydrous stripping gas to the alcohol vaporization zone in an amount and under conditions sufficient to form vapors comprising the mono-alcohol and to form an alcohol-depleted liquid phase comprising the carboxylic acid extraction solvent.

Abstract: A process for the separation of ethanol from water using solvent extraction at elevated pressures is disclosed. Separation is effected by contacting aqueous ethanol with either propylene (propene), allene (propadiene), methyl acetylene (propyne), or methyl allene (1,2-butadiene). This produces two liquid layers which separate because of the difference in their densities, and are easily drawn off as separate streams. The solvent is recovered by reverse osmosis means in a liquid state. The ethanol and water remain in a liquid state and are substantially recovered.

Abstract: Alcohol substantially free of water is prepared by fermenting a fermentable biomass feedstock in a fermentation unit, thereby forming an aqueous fermentation liquor containing alcohol; extracting said aqueous fermentation liquor with an organic solvent containing an extractant for said alcohol, thereby forming an alcohol-organic solvent extract phase and an aqueous raffinate; contacting said alcohol-organic solvent phase with a carrier gas thereby separating said alcohol from said alcohol-organic solvent phase and forming an alcohol laden solvent vapor; and separating alcohol substantially free of water from said carrier gas.

Abstract: Ethanol is recovered from fermentation products by a countercurrent extraction process which employs diethyl ether as the extraction solvent to form a diethyl ether-ethanol mixture. The ethanol is salted out by adding calcium chloride to the mixture, and the diethyl ether layer is separated and recycled. The calcium chloride in ethanol solution is removed by adding sodium carbonate to form the solids calcium carbonate and sodium chloride which are removed by filtration. The ethanol is recovered as the filtrate.

Abstract: A process for the separation of ethanol from water using solvent extraction at elevated pressures is disclosed. Separation is effected by contacting aqueous ethanol with either propylene (propene), allene (propadiene), methyl acetylene (propyne), or methyl allene (1,2-butadiene). This produces two liquid phases which separate because of the difference in their densities, and are easily drawn off as separate streams. The solvent is recovered by distillation and condensation using a heat pump to transfer heat. The ethanol and water remain in a liquid state and are substantially recovered.

Abstract: A process is disclosed for the separation of ethanol from an ethanol containing water solution, wherein the ethanol containing solution is extracted by means of a solvent which is in the liquid or supercritical state, the ethanol containing solvent phase is separated into its components by being conducted over an adsorption medium without changing the pressure or temperature, and the ethanol is recovered by treating the ethanol containing adsorption medium with the solvent used for the extraction at a pressure from 1 to 30 bar and at a temperature from 150.degree. to 300.degree. C.

Abstract: Purified isopropanol is obtained from a crude reaction mixture by removing high boiling oils with activated carbon, extraction with a high boiling solvent and distillation with energy saving use of distillation vapors to heat successive distillation steps. Recyle of components also improves the overall economics of the process.

Abstract: A process is disclosed for the production of aliphatic alcohol by the direct hydration of an olefinic hydrocarbon. The process is directed to the production of isopropyl alcohol. The process includes the recovery of the alcohol from a water-rich hydration zone effluent stream by countercurrent liquid-liquid extraction against a paraffinic solvent. The solvent is derived from paraffins originally admixed with the olefin-containing feed stream, and the raffinate stream comprises water which is recycled in the process. Expensive product fractionation is eliminated in the production of a fuel grade isopropyl alcohol.

Abstract: A process for producing and recovering a C.sub.2 to C.sub.6 alcohol, which comprises contacting water and a C.sub.2 to C.sub.6 olefin with a hydration catalyst comprising an acidic ion exchange resin in a reaction zone under reaction conditions, said reaction zone containing multiple water quench points and multiple olefin injection points, and counter-currently contacting the reaction product with a solvent to extract the C.sub.2 to C.sub.6 alcohols therefrom.

Abstract: A process for the recovery of a water soluble alcohol from an aqueous mixture of the alcohol comprises incorporating in the mixture at least about 0.5% of a base selected from the group consisting of ammonium or alkali or alkaline metal hydroxide, ammonium or an alkali or alkaline metal carbonate or mixtures thereof; and at least about 0.2% of an electrolyte. The aqueous-alcohol mixture separates into two immiscible layers, and the layers are separated.

Abstract: A process is disclosed for separating low molecular weight alcohols, especially ethanol, from aqueous mixtures. The process involves subjecting alcohol-water mixtures to extraction and/or extractive distillation procedures. Extractive solvents useful for the process of this invention include phenols having at least six carbon atoms and a boiling point between about 180.degree. C. and about 350.degree. C.

Abstract: Alcohol/water mixtures, such as those produced by fermentation of biomass material, are separated by extraction of alcohol with a solvent, comprising a higher aliphatic alcohol in major amount and an aliphatic hydrocarbon in minor amount, especially suited to such extraction and to subsequent removal. The solvent alcohol desirably has a branched chain, or the hydrocarbon an unsaturated bond, or both. Conventional distillation steps to concentrate alcohol and eliminate water are rendered unnecessary at a considerable reduction in heat energy requirement (usually met with fossil fuel). Optional addition of gasoline between the solvent extraction and solvent recovery steps not only aids the latter separation but produces alcohol already denatured for fuel use.

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.

Abstract: A thermally efficient process for recovering ethanol present in dilute aqueous solution is disclosed which comprises contacting said dilute aqueous ethanol solution with at least one inert extractant which is liquid at ambient temperature and pressure, said extractant being selected from the group consisting of unsubstituted and substituted cyclic secondary amines and unsubstituted and substituted aromatic cyclic amines having a distribution coefficient of at least about 0.70 or a separation factor of at least about 1.0.

Abstract: A process for producing sec-butanol and sec-butyl tert-butyl ether from butane comprises: (a) partially isomerizing n-butane to produce a mixture of n-butane and isobutane; (b) catalytically dehydrogenating said butanes to produce a mixture containing at least butene-1, isobutene and butadiene; (c) selectively hydrogenating butadiene and converting butene-1 to butene-2; (d) etherifying isobutene contained in the dehydrogenation reaction mixture with sec-butanol to form a mixture of sec-butyl tert-butyl ether and unreacted hydrocarbons; (e) converting butene-2 from the unreacted hydrocarbon mixture by hydration to produce sec-butanol; (f) recycling said sec-butanol to the etherification step; recovering said sec-butyl tert-butyl ether.

Abstract: A process for producing an oxygenated fuel composition comprising gasoline and isopropanol in which a dilute propylene feedstock is hydrated to produce isopropanol in a single pass, the unreacted olefins are oligomerized to produce gasoline blending stock and the isopropanol is added directly to the gasoline pool from a water-isopropanol azeotropic mixture without the use of energy intensive extractors.

Abstract: Alcohol substantially free of water is produced by a process comprising extracting an aqueous alcohol solution with an organic solvent system containing an extractant for said alcohol thereby forming an organic solvent-alcohol phase and an aqueous phase, and vacuum distilling said organic solvent-alcohol phase thereby obtaining the product alcohol substantially free of water.

Abstract: A process for producing isopropyl alcohol and isopropyl tert-butyl ether from a mixture of light hydrocarbons containing propane and butane, comprises:(a) separating from the mixture of light hydrocarbons a propane fraction and a butane fraction containing at least n-butane;(b) isomerizing at least a portion of the n-butane in the butane fraction from step (a) whereby a hydrocarbon mixture containing at least n-butane and isobutane is formed;(c) catalytically dehydrogenating the isobutane in the hydrocarbon mixture from step (b) whereby a hydrocarbon mixture containing at least isobutene is produced;(d) catalytically dehydrogenating the propane in the propane fraction from step (a) whereby a hydrocarbon mixture containing at least propene is produced;(e) reacting the propene in the hydrocarbon mixture from step (d) with water, whereby a mixture containing hydrocarbons and isopropyl alcohol is formed;(f) reacting the isopropyl alcohol from step (e) with at least part of the isobutene in the hydrocarbon mixture

Abstract: Alcohol/water mixtures, such as those produced by fermentation of biomass material, are separated by extraction of alcohol with a solvent especially suited to such extraction and to subsequent removal. Conventional distillation steps to concentrate alcohol and eliminate water are rendered unnecessary at a considerable reduction in heat energy requirement (usually met with fossil fuel). Addition of gasoline between the solvent extraction and solvent recovery steps not only aids the latter separation but produces alcohol already denatured for fuel use.

Abstract: A C.sub.1 -C.sub.2 alkanol is separated from aqueous calcium chloride by adding a C.sub.4 or C.sub.5 hydrocarbon feed comprising an isoolefin to an aqueous solution of a calcium chloride-alkanol complex wherein the alkanol is methanol or ethanol at a temperature of about 80.degree.-120.degree. C. and a pressure of about 20-180 psig to provide an upper phase comprising the hydrocarbon feed and alkanol and a lower phase comprising aqueous calcium chloride. The invention is particularly useful as a step in a process for preparing and purifying methyl t-butyl ether by (1) reacting an excess of methanol with isobutylene or a C.sub.4 hydrocarbon stream containing isobutylene to form a crude reaction product comprising methyl t-butyl ether and excess methanol, (2) intimately mixing the crude reaction product with aqueous calcium chloride to complex the methanol and separate it from the ether, and (3) adding the hydrocarbon stream to extract the methanol from the aqueous calcium chloride-methanol complex solution.

Abstract: Certain fluorocarbon liquid materials are particularly effective solvents for the removal of lower alcohols from aqueous solutions, an extraction process. The fluorocarbons have low heats of vaporization. The specific fluorocarbons recited have boiling points near room temperature which permits the separation of alcohols from the aqueous solutions with much lower energy requirements than required by distillation. The solvent systems are intended for use in fermentation separations such as those recited in my co-pending application Ser. No. 06/076 250 and similar anaerobic and aerobic fermentations to produce alcohols and related fermentation products.