Abstract: A process for the catalytic hydrogenation of butterfat where non-deacidified butterfat is continuously reacted with hydrogen under pressures of from 20 to 300 bar and at temperatures of from 180.degree. to 250.degree. C. with molar ratios of hydrogen to fatty acid residue in the butterfat of from 10:1 to 500:1. The reaction is carried out over catalysts which contain from 30 to 40% by weight copper, from 23 to 30% by weight chromium, from 1 to 10% by weight manganese, from 1 to 10% by weight silicon, and from 1 to 7% by weight barium. The percentages by weight in each case are based on the total oxidic mass of the catalyst. Other transition metals, especially zirconium and cerium, are additionally incorporated into the catalyst. The metals in the catalyst are converted to their oxides by calcination. The catalyst is converted into shaped particulate or granulated elements with from 1 to 10% by weight of at least one binder in addition to 1 to 10% by weight graphite.

Abstract: The invention relates to a process for preparing enantiomerically pure S(+)-propan-1,2-diol and R(-)-propan-1,2-diol from L(-)-lactide or D(+)-lactide, respectively.

Abstract: A process is described for the production of substantially pure gamma-butyrolactone from a feed mixture containing a major amount of gamma-butyrolactone and a minor amount of diethyl succinate which comprises fractionally distilling the mixture in a fractionation zone in the presence of diethyl ethoxysuccinate and recovering from the fractionation zone an overhead vaporous product comprising gamma-butyrolactone which is substantially free from diethyl succinate and is liquid bottom product comprising diethyl ethoxysuccinate and diethyl succinate in admixture one with another. This procedure can be used to separate a gamma-butyrolactone rich fraction obtained by distillation in one or more stages of a crude reaction product obtained by hydrogenation of a C.sub.

Abstract: A process for the catalytic hydrogenation of liquid fatty acid triglycerides and the simultaneous recovery of fatty alcohols and C.sub.3 diols in the presence of gaseous hydrogen and hydrogenation catalysts under pressures of from 50 to 300 bar and at temperatures in the range from 160.degree. to 250.degree. C., to produce fatty alcohols in at least 99% of the theoretical yield and of 1,2-propanediol in at least 80% of the theoretical yield and a maximum paraffin content of 0.5% of the theoretical yield is disclosed. The hydrogenation reaction is carried out in a tube bundle reactor operated under isothermal conditions through a cooling or heating fluid, the liquid phase being passed as co-current trickle phase with the gaseous phase over catalyst packings in the individual reactor tubes without back-mixing, and in that the load per unit volume of the reactor is selected between 0.2 and 2.5 l starting material per 1 reactor volume per hour and the load per unit area of each individual reactor tube between 1.

Abstract: Process for the preparation of 1,4-butanediol or tetrahydrofuran or both by the catalytic hydrogenation of maleic anhydride, succinic anhydride, maleic acid, succinic acid, fumaric acid, or the alkyl esters of these acids at temperatures of from 100.degree. C. to 350.degree. C. and pressures of from 50 bar to 350 bar over a catalyst containing cobalt as the active metal and one or both of the elements copper and phosphorus, if necessary in the presence of an aliphatic alcohol.

Abstract: A process for hydrogenation of esters of the formula: ##STR1## wherein R.sub.1 represents hydrogen or a hydrocarbyl group, wherein R.sub.2 and R.sub.4 represent a hydrocarbyl group, and wherein R.sub.3 represents a hydrocarbylene group, which process comprises contacting said ester with hydrogen and carbon monoxide in the presence of a catalyst system which comprises:(a) a compound containing a cation of an element selected from Group VIII of the Periodic Table of the Elements,(b) an alcoholate of an alkali metal and/or alkaline earth metal, and(c) an alcohol.

Abstract: Disclosed are catalyst compositions comprised of chemically-mixed, copper-titanium oxides and the use of such catalyst compositions in the hydrogenation of certain esters to obtain the alcohol corresponding to the acid residue of the ester.

Abstract: An alcohol is effective produced by catalytically reducing an organic carboxylic acid ester with hydrogen in the presence of a catalyst obtained by reducing a catalyst precursor comprising (A) copper oxide and (B) titanium oxide and/or titanium hydroxide at a weight ratio of (A) to (B) in the range between 15/85 and 65/35. The component (A) may be alternatively a composite metal oxide comprises copper oxide and up to 20 wt. % of zinc oxide.

Abstract: A process for the reduction of carbonyl compounds by an alkali or alkaline-earth metal borohydride in the presence of a phase transfer catalyst which is an N-benzyl-N,N-bis (2-hydroxyethyl)cocoammonium halide.

Abstract: The invention relates to a novel supported catalyst comprising (a) copper, (b) a metal having an atomic weight greater than 100 and selected from Groups VIIB and VIII of the Periodic Table and (c) an alkali metal in a weight ratio of about 8-40:0.05-5:1.5-10 and to the use of the catalyst in the hydrogenation of butyrolactone to 1,4-butanediol.

Abstract: A process for the hydrogenation of esters into alcohols which comprises converting esters of the formula ##STR1## wherein R.sub.1 is hydrogen or a hydrocarbyl group and preferably an alkyl group containing 1-20 carbon atoms or an aryl alkyl group containing 1-6 carbon atoms in the alkyl residue, the aryl being preferably phenyl, and R.sub.2 is a hydrocarbyl group as specified hereinbefore for R.sub.1, in the presence of hydrogen and carbon monoxide and a catalyst system, obtainable by combining the following components(a) a hydride of an alkali metal and/or a hydride of an alkaline earth metal,(b) an alcohol or an alkali metal and/or alkaline earth metal alcoholate thereof, and(c) a compound containing a cation of an element of Group VIII of the Periodic Table of the Elements,and allowing these components to react.

Abstract: Dihydroxy and polyhydroxy compounds are obtained from polymerized fatty acids by a liquid phase reaction at a temperature at about 500.degree. F. to about 650.degree. F., pressures up to about 1000 psi in the presence of a catalytic amount of a hydrogenation catalyst, along with removal of water by-product during the reaction.

Abstract: Process for the hydrogenation of carbonyl-containing compounds at mild conditions of temperature and pressure to produce alcohols or amines is disclosed, employing palladium on zinc oxide catalysts. A method for the preparation of the palladium on zinc oxide catalysts useful for the desired reductive conversion is also disclosed.

Abstract: Disclosed is the hydrogenation of maleic acid in the presence of a solid iron-containing ruthenium catalyst containing the elements and the ratios indicated by the empirical formula,RuFe.sub.a M.sub.b O.sub.xwhereM is one or more of Pd and Rh,a is 0.1-5,b is zero-3, andx is a number sufficient to satisfy the valency requirements of the cations present in the catalyst,said process being effected by contacting in a reaction zone an excess of hydrogen with an aqueous solution of maleic acid in admixture with said catalyst.

Abstract: A process for the production of alkane polyols and especially alkane triols where mono- and/or poly-epoxidized fatty acids and/or fatty acid esters and mixtures thereof, especially derivates of natural fatty acids, are reacted with short-chain alkane-carboxylic acids such as formic or acetic acids; and the ester alcohols produced are hydrogenated on a hydrogenation catalyst such as those containing copper chromite at elevated temperature and pressure. The maximum possible number of alcohols groups per molecule can be formed in this way thus producing alkane triols, for example, which are useful in cosmetic formulations as well as in polyurethanes.

Abstract: Glycerides are reacted with ammonia in an amount of at least 200 liters per kilogram of glyceride per hour, at a temperature of 220.degree. to 300.degree. C., and in the presence of special catalysts. Of the product mixture which is formed and removed from the reaction with the excess ammonia, and which is composed essentially of the components water, the desired glycerol and fatty acid nitrile containing fatty acid and fatty acid amide, the latter component is returned to the reaction during the glyceride reaction. After completion of the glyceride reaction, which is indicated when the product mixture contains virtually no more glycerol, all the fatty acid nitrile containing fatty acid and fatty acid amide is further treated, in an after-reaction with a reduced amount of ammonia and at higher temperature, in order to convert the fatty acid and fatty acid amide impurities into fatty acid nitrile.

Abstract: A process is disclosed for preparing butyrolactones, butanediols, and mixtures thereof comprising hydrogenating a hydrogenatable precursor in the presence of an aqueous reaction medium and a catalyst comprising palladium or combinations thereof with rhenium and at least one support selected from the oxides of titanium, zirconium, and hafnium.

Abstract: The inventive method is particularly advantageous for the preparation of an unsaturated alcohol or aldehyde by the reduction of a corresponding unsaturated carboxylic acid since the unsaturated double bond in the starting acid is not hydrogenated by the reaction of reduction. The method comprises first reacting the starting acid with an alkyl chloroformate to form an intermediate compound by the dehydrochlorination and the intermediate compound is then reduced by using sodium borohydride as the reducing agent. The proportion of the aldehyde to alcohol in the product mixture can be controlled by modifying the amount of the reducing agent and/or the reaction time.

Abstract: Butane-1,4-diol is produced by vapor phase hydrogenolysis of an alkyl ester of a C.sub.4 dicarboxylic acid, e.g. diethyl maleate, over a reduced Cu-Cr or Cu-Zn mixed oxide catalyst. Two adiabatic hydrogenolysis zones are used. The mixture exiting the first of these zones is cooled (by, for example, 5.degree. C.) and the resulting cooled mixture is fed to the second zone in which is reequilibriates at a lower temperature to increase the butane-1,4-diol yield at the expense of gamma-butyrolactone. Typical reaction conditions include use of temperatures of 150.degree. C. to 200.degree. C., pressures of 25 to 70 bar, and a H.sub.2 :ester molar ratio of 100:1 to 800:1. When using a maleate ester it is often advantageous to hydrogenate this to the corresponding succinate ester in an upstream hydrogenation zone prior to entry to the first hyrogenolysis zone.

Abstract: A method of producing substantially pure dialkyl maleate by separating monoalkyl maleate from dialkyl maleate in a short residence time distillation zone while minimizing reversion of the monoalkyl maleate to alkanol and maleic anhydride and without having to neutralize the monoalkyl maleate.

Abstract: The present invention relates to a process for producing alcohols comprising hydrogenating compounds selected from the group consisting of acids, esters and aldehydes under sufficient hydrogen pressure and temperature in the presence of a catalyst comprising a copper chromite first component and a second component consisting essentially of copper deposited on a support.

Abstract: A process for the preparation of ethylene glycol by the vapor phase catalytic hydrogenation of at least one of di(lower alkyl) oxalate and lower alkyl glycolate in the presence of a hydrogenation catalyst comprising a carrier, which catalyst is suitable for the hydrogenation of alkyl oxalate and alkyl glycolate to ethylene glycol, wherein the improvement lies in preparing the catalyst by contacting the carrier with a cooper ammonium carbonate complex medium and reducing the catalytically-active copper moiety to its active copper form.

Abstract: Mixtures of tetrahydrofuran and 1,4-butanediol at a predetermined mole ratio are produced by the hydrogenation of dimethylsuccinate in the presence of a copper chromite catalyst wherein said ratio is controlled by conducting the hydrogenation within a particular temperature range. Methanol is added to the ester feed to increase conversion and reduce transesterification. Tetrahydrofuran and 1,4-butanediol are separated from a mixture which also contains water and methanol by a series of distillations including a superatmospheric distillation.

Abstract: Lactones, particularly gamma-butyrolactone, are hydrogenated in the vapor phase to glycols over a copper chromite catalyst.

Abstract: An improved calcined hydrogenation catalyst shape which is useful for the catalysis of hydrogenation reactions in a tubular reactor is provided. The catalyst shape has an annular configuration with an open center core, and wherein the shape contains, as a reinforcing matrix distributed therein, up to about 50 percent by weight of milled glass fibers having specific dimensions and wherein the crush strength of the shape is vastly improved with little change in catalytic activity over the non-reinforced shape of comparable size. Additionally, when the shapes of the present invention are employed pressure-drop and diffusion problems are reduced. The catalyst shapes are particularly useful for the hydrogenation of alkyl oxalates to ethylene glycol whereby the reaction can be conducted at lower temperatures and hence by-product formation is minimized.

Abstract: A process for the preparation of ethylene glycol by the catalytic hydrogenation of at least one of di(lower alkyl) oxalate and lower alkyl glycolate in the presence of a hydrogenation catalyst comprising a carrier, which catalyst is suitable for the hydrogenation of alkyl oxalate and alkyl glycolate to ethylene glycol, wherein the carrier has a leachable iron content not greater than about 0.03%, by weight of the carrier.

Abstract: A process for the preparation of ethylene glycol by the vapor phase catalytic hydrogenation of at least one of di(lower alkyl) oxalate and lower alkyl glycolate in the presence of a hydrogenation catalyst comprising a carrier, which catalyst is suitable for the hydrogenation of alkyl oxalate and alkyl glycolate to ethylene glycol, the improvement lies within the preparation of the catalyst by employment of catalysts comprising carriers having specific ranges of physical parameters, including average pore diameter and pore volume, which parameters are interrelated by a relative activity index.

Abstract: The invention has as an object the production of alcohols by hydrogenolysis of carboxylic acid esters, under hydrogen pressure, in the presence of a catalyst resulting from the incorporation of at least one compound of at least one metal from the group consisting of germanium, tin and lead to Raney nickel or to a nickel-containing carrier. The reaction is preferably conducted at a temperature from 180.degree. to 330.degree. C. and under a pressure from 1 to 10 MPa.

Abstract: A hydrogenation catalyst composition composed of a reduction product of a copper-containing material formed by contacting an aqueous solution of an amine/copper complex with a carrier, characterized in that the carrier is a hydrolyzed product obtained by hydrolyzing a silicate ester in the presence of ammonia; a process for producing the aforesaid hydrogenation catalyst composition; and a process for producing ethylene glycol or a glycolate ester in the presence of the aforesaid hydrogenation catalyst.

Abstract: The reduction of organic compounds to the corresponding hydroxy compounds which comprises contacting a suitable organic compound selected from the group consisting of organic carboxylic acid compounds, aldehydes and ketones with a reducing agent in the presence of a catalyst comprising at least one member selected from the group consisting of copper aluminum borate and zero valent copper on an aluminum borate support.

Abstract: The present invention relates to the vapour phase hydrogenation of carboxylic acid esters to give alcohols. More particularly, this invention pertains to a process for the production of an alcohol by hydrogenation of an ester with a hydrogenation catalyst comprising a Group VIII element, a promoter, and a carbon support. This process is characterized in that (1) the Group VIII element is ruthenium, nickel, or rhodium, (2) the promoter is introduced on to the carbon as a water stable compound of Group IA, IIA metal, a lanthanide or actinide, and (3) the carbon has a BET surface area of at least 100 m.sup.2 /g, and a ratio of BET to basal plane surface area not greater than 4:1, and (4) the hydrogenation is carried out in the vapor phase at a temperature in the range 100.degree. C. to 400.degree. C. at a total space velocity of 100 to 120,000.

Abstract: Palladium/rhenium-on-carbon catalyst; a method employing said catalyst to produce tetrahydrofuran, 1,4-butanediol or mixtures thereof in selectable ratios from a number of starting reactants; and a method for making the Pd/Re/C catalyst.

Abstract: C.sub.4 olefins comprising cis- and trans-butane-2 and butene-1 may be oxidized to their corresponding mono- and diacetates in the presence of acetic acid and an olefin-activated palladium catalyst under mild conditions. With this catalyst, and depending in part upon the solvent employed, as well as other operating conditions, the formation of linear allylic 1-acetates over the corresponding branched compounds can be favored in order to increase the yield of the corresponding linear 1,4-diacetates. The latter, in turn, may then be converted, for example, to butanediol by known hydrogenation methods.In a similar manner, isobutylene may be converted to a dialcohol.

Abstract: Molded catalyst materials contain metallic cobalt and/or nickel particles and a lubricant, the said particles being obtained by reduction of cobalt oxide and/or nickel oxide particles containing less than 0.1% by weight of alkali metal oxides and/or alkaline earth metal oxides at .ltoreq.500.degree. C., and the molded catalyst material having an indentation hardness greater than 300 kp/cm.sup.2.

Abstract: Butane-1,4-diol is prepared by catalytic hydrogenation of dibutyl succinate by a process in which hydrogenation is terminated before complete conversion is reached, butanol is distilled off from the reaction mixture, the liquid distillation residue is cooled to below 108.degree. C., the upper phase, which is formed as a result of phase separation and essentially consists of dibutyl succinate, is recycled to the hydrogenation, and the butane-1,4-diol is obtained from the lower phase, which essentially consists of this compound, by fractional distillation under reduced pressure.

Abstract: A hydrogenation catalyst composition useful for the hydrogenation of an oxalate diester, said composition being composed of a reduction product of copper-containing silica gel formed by contacting an ammine complex of copper with colloidal silica sol; and a process for producing the aforesaid composition. Using a catalyst composed of the aforesaid composition, ethylene glycol and/or a glycolic acid ester can be produced from an oxalate diester efficiently with high conversions and selectivities and without causing pollution attributed to the use of a chromium-containing catalyst composition.

Abstract: A process for the production of butane-1,4-diol comprises hydrogenating a di(C.sub.1 to C.sub.3 alkyl) ester of a C.sub.4 dicarboxylic acid, e.g. an ester of a but-2-en-1,4-dioic acid, such as diethyl maleate, in the vapor phase at a temperature of from about 150.degree. C. to about 240.degree. C. and at a pressure in the range of from about 25 bar to about 75 bar in the presence of a reduced copper chromite catalyst, and recovering resulting butane-1,4-diol containing reaction product. The catalyst contains, before reduction, from about 25 to about 45% by weight of copper and from about 20 to about 35% by weight of chromium and preferably has an internal surface area of at least about 30 sq. m. per gram. The process is preferably conducted in two or more reaction zones, which are preferably operated adiabatically, the feed temperature to the first zone being higher than that to at least one subsequent reaction zone.

Abstract: Maleic anhydride is separated off from gaseous reaction mixtures by a continuous process in which the gaseous reaction mixture containing the maleic anhydride is brought into contact with butanol, the gaseous substances obtained in this procedure are brought into contact with butyl maleate by a countercurrent method, and the liquid product is removed from the bottom.

Abstract: In a process for producing ethylene glycol and/or a glycollic acid ester by the vapor phase catalytic hydrogenation of an oxalic acid diester in the presence of a catalyst and hydrogen gas, the improvement wherein the catalyst has the following composition formulaCuMo.sub.k Ba.sub.p O.sub.qwherein k, p and q represent gram-atoms of Mo, Ba and O, respectively, per gram-atom of Cu, k is a number of from 0 to 3, p is a number of from 0 to 6, and q is a number determined depending upon the atomic valence and gram-atoms of Cu, Mo and Ba, provided that k and p are not zero at the same time; and the aforesaid catalyst.

Abstract: Palladium/rhenium-on-carbon catalyst; a method employing said catalyst to produce tetrahydrofuran, 1,4-butanediol or mixtures thereof in selectable ratios from a number of starting reactants; and a method for making the Pd/Re/C catalyst.

Abstract: Spent copper "chromite" catalyst from the hydrogenation of carboxylic acids or esters of such acids is regenerated by vacuum treatment at high temperature to reduce the level of organic residue on the catalyst to less than about 25%, followed by oxidation.

Abstract: A hydrogenation catalyst composition for use in the hydrogenation of a lower alkyl ester of a lower hydroxycarboxylic acid. The composition is composed of a reduction product of copper-containing silica gel formed by contacting an ammine complex of copper with silica gel having an average particle diameter of not more than 200 microns or colloidal silica sol. A process for producing the catalyst composition is also provided. By using the aforesaid catalyst composition, a lower alkylene glycol can be produced efficiently in high conversions and selectivities without causing pollution attributed to the use of a chromium-containing catalyst composition.

Abstract: The hydrogenation of carboxylic acids having 6 or less C atoms, as obtained as by-products of cyclohexane oxidation, to give corresponding diols is improved by the addition of a small amount of phosphoric acid or a phosphoric ester before hydrogenation.

Abstract: There is disclosed a process for continuously preparing ethylene glycol, which comprises (1) a first step of contacting a gas containing carbon monoxide and an ester of nitrous acid with a solid catalyst of platinum group metal series in the gaseous phase thereby to obtain a product containing a diester of oxalic acid, (2) a second step of condensing the product of the first step thereby to separate a non-condensed gas containing nitrogen monoxide formed by the catalytic reaction of the first step from a condensed liquid containing the diester of oxalic acid, (3) a third step of contacting the non-condensed gas of the second step with a gas containing molecular oxygen and an alcohol, and recycling the resulting gas containing an ester of nitrous acid to the first step, (4) a fourth step of contacting the condensed liquid of the second step containing the diester of oxalic acid and hydrogen with a catalyst for hydrogenation in the gaseous phase thereby to obtain a product containing ethylene glycol, (5) a fift

Abstract: 1,2,4-Butanetriol is produced by hydroformylation of a solution of glycidol and reduction of the hydroformylation reaction products.

Abstract: An improved process is provided for the production of alcohols from carboxylic acids using the reaction of carboxylic acids with alcohols in the presence of hydrogen and carbon monoxide to form esters which are subsequently hydrogenated over a suitable hydrogenation catalyst. The invention is useful because the temperature and pressure conditions are reduced from current commercial processes while hydrogenation catalyst activity and lifetime are promoted by the removal of catalyst poisons such as water.

Abstract: The life of the hydrogenation catalyst in reducing a mixture of glycolate ester to ethylene glycol can be extended by lowering the polyglycolide ester content of the mixture by transesterification, that is, heating in the presence of alcohol, after which the resulting mixture is hydrogenated.

Abstract: A process for the preparation of butane-1,4-diol by catalytic hydrogenation of a mixture obtained by treating maleic anhydride with an aliphatic alcohol at elevated temperatures, wherein a monohydric or dihydric aliphatic alcohol of boiling point above 180.degree. C. is used and the mixture of maleic acid and the alcohol is obtained by washing a gaseous reaction mixture, which contains maleic anhydride and is obtained in the catalytic oxidation of hydrocarbons by air, with the alcohol.

Abstract: A novel class of heterogeneous catalysts, containing Group VIII transition metals in combination with alkali organic compounds is prepared, such as potassium naphthalene on ruthenium on carbon. The catalysts are useful as heterogeneous catalysts in the hydrogenation of carboxylic acid esters. A process for producing the materials is described. The catalysts permit the process of the hydrogenation of carboxylic acid esters to primary alcohols to be conducted with the ester in the liquid phase at a temperature not exceeding about 150.degree. C. with high selectivity. Catalysts of Group VIII transition metals and alkali metal on carbon are also useful in such processes.

Abstract: A novel class of heterogeneous catalysts, containing Group VIII transition metals in combination with alkali organic compounds is prepared, such as potassium naphthalene on ruthenium on carbon. The catalysts are useful as heterogeneous catalysts in the hydrogenation of carboxylic acid esters. A process for producing the materials is described. The catalysts permit the process of the hydrogenation of carboxylic acid esters to primary alcohols to be conducted with the ester in the liquid phase at a temperature not exceeding about 150.degree. C. with high selectivity. Catalysts of Group VIII transition metals and alkali metal on carbon are also useful in such processes.