Abstract: A process for the preparation of 2,2-bis-hydroxymethyl-butanediol-(1,4) of formula I ##STR1## wherein 4-hydroxybutyraldehyde of formula II ##STR2## and/or 2-hydroxytetrahydrofuran of formula III ##STR3## is/are condensed with formaldehyde in the presence of a basic catalyst and the resulting reaction mixture is then catalytically hydrogenated, and 2,2-bis-hydroxymethyl-butanediol-(1,4) is isolated from the hydrogenation product.

Abstract: In a hydrogenation process, an organic feedstock, such as an unsaturated organic compound containing at least one unsaturated linkage selected from >C.dbd.C<, >C.dbd.O, --C.tbd.C--, and --C.tbd.

Abstract: In one embodiment, the invention relates to a catalyst in powdered form comprising the oxides of copper, iron, aluminum and manganese wherein the atomic ratio of copper to iron is at least 1:1. In another embodiment, the invention relates to a process for preparing such hydrogenation catalysts which comprises the steps of(A) preparing a first aqueous solution containing at least one water-soluble copper salt, at least one water-soluble iron salt, and at least one water-soluble manganese salt;(B) preparing a second solution containing at least one water-soluble basic aluminum salt and at least one alkaline precipitating agent;(C) mixing the first and second solutions wherein an insoluble solid is formed;(D) recovering the soluble solid; and(E) calcining the recovered solid to form the desired catalyst.The invention also relates to a process for hydrogenating aldehydes, ketones, carboxylic acids and carboxylic acid esters.

Abstract: Disclosed is a continuous process for the manufacture of 2-ethyl-2-(hydroxymethyl)hexanal wherein 2-ethylhexanal, formaldehyde and a tertiary amine are continuously fed to a reaction zone and crude product comprising an aqueous phase and an organic phase containing 2-ethyl-2-(hydroxymethyl)hexanal and 2-ethylhexanal is continuously removed from the reaction zone Also disclosed are processes for (1) the azeotropic distillation of the organic phase of the crude product whereby unreacted 2-ethylhexanal is recovered and (2) the catalytic hydrogenation of the refined, organic phase of the crude product to produce 2-butyl-2-ethyl-1,3-propanediol.

Abstract: Lower polyhydric alcohols are prepared by catalytic hydrogenolysis of sucrose in an aqueous solution by using a catalyst whose active material essentially consists offrom 0 to 100% by weight of cobalt,from 0 to 85% by weight of copper andfrom 0 to 80% by weight of manganese,the percentages being based on the content of the metals.

Abstract: The sugar alcohols given in the title can be prepared in epimer-free form from the corresponding sugars by catalytic hydrogenation in aqueous solution using hydrogen, the hydrogenation being carried out continuously at 100-500 bar of H.sub.2 and 60.degree.-125.degree. C. on a fixed bed of carrier-free mouldings composed of pressed powders of the elements of the iron group of the periodic table. The mouldings have a compressive strength of above 50 N and an internal surface of 10-90 m.sup.2 /g.

Abstract: A process for the preparation of lower polyhydric alcohols by catalytic hydrogenation of aqueous saccharose solutions at elevated temperature and pressure using a catalyst of which the catalytically active material essentially contains the metals cobalt, copper and manganese in the following concentrations, the total weight of said metals being standardized as 100%:from 0 to 100% w/w of cobalt,from 0 to 85% w/w of copper andfrom 0 to 80% w/w of manganese,this said metal content of said catalytically active material comprising either cobalt alone or at least two of said metals, which active material may also contain added inorganic poly acids and/or heteropoly acids, wherein from 0.01 to 5% w/w of one or more base-acting metal compounds of metals from the first and second main groups and from group IIIA of the Periodic Table are added to the saccharose solution to be hydrogenated.

Abstract: This invention relates to a process for synthesis of glycerol from formaldehyde, wherein formaldehyde under substantially anhydrous condition is self-condensed in a catalytic step is dihydroxyacetone which is separated from the self-condensation catalyst and hydrogenated catalytically to glycerol.The feature of the invention is to have less than 0.4% w/w of water in the self-condensation reaction mixture thereby improving the process to produce glycerol in commercially viable rates and yields.

Abstract: A homogeneous process for hydrocracking of carbohydrates in the presence of soluble transition metal hydrogenation catalyst with the production of lower polyhydric alcohols. A carbohydrate is contacted with hydrogen in the presence of a soluble transition metal catalyst and a strong base at a temperature of from about 25.degree. C. to about 200.degree. C. and a pressure of from about 15 to about 3000 psi.

Abstract: Mannitol having the crystalline form of gamma sorbitol is made by co-crystallizing relatively high mannitol containing sorbitol melt in a twin screw mixer. Tablets, chocolate and chewing gum made with the co-crystallized product offer improvements similar to those realized with pure crystalline components.

Abstract: Unsaturated alcohols are prepared by hydrogenation of the corresponding carbonyl compounds in the presence of a platinum-cobalt bi-metallic catalyst having an alloy structure.

Abstract: Hydrogen is supplied first to a last hydrogenation zone, and gases recovered from the last hydrogenation zone are passed to the first hydrogenation zone of a continuous multi-zone liquid phase process for hydrogenating an organic compound to a corresponding hydrogenation product. The organic compound, with a suitable diluent or recycle hydrogenation product, flows successively through the zones beginning with the first and ending with the last hydrogenation zone to undergo hydrogenation with the hydrogenation product being recovered from the last hydrogenation zone.

Abstract: A single-step process for the conversion of polysaccharides to polyhydric alcohols by hydrogenation at high pressure and temperature in the presence of a catalyst comprising (i) a supported metal selected from ruthenium, copper, nickel, cobalt and their mixtures, the metal being highly dispersed on the support so as to be capable of adsorbing more than 0.58 molecules of CO per atom of metal, and (ii) a solid having acidic functions, which may or may not be identical to the support, the solid having sufficient acid functions so that the rate constant of hydrolysis of sucrose on the catalyst is greater than 70% of the rate constant of hydrogenation of glucose on the catalyst. The process gives substantially pure polyhydric alcohols in a single step.

Abstract: A process for production of neopentyl glycol by hydrogenation of hydroxypivaldehyde in the presence of a Pt-Ru-W catalyst. This catalyst exhibits high activity and selectivity, and further has a long life. Neopentyl glycol is an important intermediate for use in production of a wide variety of chemicals.

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: Process for the preparation of a product with a high content of maltitol, characterized by the following steps:catalytic hydrogenation of a maltose syrup,chromatographic fractionation of the maltitol syrup formed during the hydrogenation step,adjustment to the desired dry matter of at least the fraction enriched in maltitol.

Abstract: Process for the preparation of crystalline maltitol comprising successively:catalytic hydrogenation of a saccharified starch milk in a vessel 203,a step of chromatographic fractionation of the hydrogenated syrup in a vessel 204,crystallation and separation of the maltitol crystals in vessels 206 and 207 andrecycling through a pipe 309 emerging from the vessel 207 of the crystallization mother-liquors to the head of the chromatographic fractionation step.

Abstract: A process for the production of 3,4-dideoxyhexitol and for its cyclodehydration to 2,5-bis(hydroxymethyl)tetrahydrofuran. The 3,4-dideoxyhexitol is obtained by hydrogenolysis in the presence of a copper chromite catalyst, of hexitols, or of compound which undergo reaction with hydrogen to give hexitols.

Abstract: A method for hydrogenating an aldehyde and/or a ketone in the presence of a ruthenium catalyst, wherein said ruthenium catalyst is obtained by reducing an alkali metal ruthenate with a reducing agent selected from the group consisting of methanol, formaldehyde and formic acid.

Abstract: A synthetic resin product contains various substances such as perfumes, insectifuges/insecticides, mold/mildew-proofing agents and anti-fungi agents which are inactivated by forming an inclusion compound thereof in cyclodextrin and coating them with glycitol(s) to thereby prolong the duration period of the substance. A process for the production of the same is further disclosed wherein the glycitol is provided in the form of reduced millet jelly or reduced cyclodextrin millet jelly.

Abstract: A process for production of sorbitol from 50-98.5 DE hydrolyzed starch solution by hydrogenation over a nickel catalyst at a pH of from 3.0 to 7.0, 120.degree. to 160.degree. C. and 500 to 2000 psig (35 to 140 Bars) until the reducing sugar value is below 5 percent; removal of nickel catalyst, acidification to pH 1.0 to 2.5 and hydrogenation of the acidified solution over a ruthenium catalyst, 100.degree. to 180.degree. C. and 500 to 2000 psig, until hydrogen uptake is substantially complete, and removal of the ruthenium catalyst.

Abstract: In the preparation of a mixture of .alpha.-D-glucopyranosido-1,6-mannitol and .alpha.-D-glucopyranoside-1,6-sorbitol by catalytically hydrogenating .alpha.-D-glucopyranosido-1,6-fructose in aqueous solution with hydrogen under increased pressure and at elevated temperature, the improvement which comprises effecting the hydrogenation continuously over a fixed bed of support-free shaped pieces of elements of sub-group 8 of the periodic table, which serve as the hydrogenation catalyst. The product can be directly used as a sweetener, without purification. The catalyst life is extremely long.

Abstract: The instant invention relates to an improved process for the preparation of low molecular weight polyalcohols by the catalytic hydrogenation of a mixture of different low molecular weight hydroxy aldehydes, hydroxy ketones and optionally also polyhydric alcohols such as is formed from the autocondensation of formaldehyde (such a mixture will hereinafter be referred to as "formose"). The invention also relates to the use of these polyalcohols for the production of polyurethane resins.

Abstract: A modified sorbitol with improved tableting properties, viz, has a melting point of about 96.degree. C., a bulk density of 0.3-0.6 g/ml, a .gamma.-sorbitol content of at least 90%, a purity of at least 98%, a specific surface area of 0.7-1.5 m.sup.2 /g, a bending strength of at least 7 N/mm.sup.2 at a compressive force of at least 10,000 N, and a friability of less than 1% at a compressive force of at least 10,000 N, can be prepared by obtaining a sorbitol solution by hydrogenation of crystallized glucose at a temperature below 170.degree. C., and spray-drying this solution at a temperature of 140.degree. to 170.degree. C. The sorbitol thus obtained has a water content of less than 1%.The sorbitol is useful for the production of compressed formulations.

Abstract: This invention provides a process for the production of C.sub.4 -C.sub.5 hydroxyketones by reaction of formaldehyde and synthesis gas in a basic organic solvent in the presence of a tungsten and Group VIII metal-containing catalyst composition.

Abstract: This invention is directed to the preparation of polyhydric alcohols. More specifically, this invention is directed to a continuous process for preparing polyhydric alcohols by the hydrogenation of carbohydrates in the presence of ruthenium-containing catalysts at elevated temperatures and elevated pressure, the improvement wherein the catalyst comprises a catalyst solid bed of ruthenium carrier catalyst in lumps.

Abstract: Improved lifetimes of group VIII metals used as hydrogenation catalysts for carbohydrates in aqueous solution may be obtained by utilizing carbohydrate feedstocks containing less than about 0.5 ppm dissolved oxygen prior to contact with catalyst under hydrogenation conditions. Using ruthenium as a catalyst, effective lifetime may be doubled with dissolved oxygen levels less than about 0.2 ppm.

Abstract: A modified sorbitol with improved tableting properties, viz, has a melting point of about 96.degree. C., a bulk density of 0.3-0.6 g/ml, a .gamma.-sorbitol content of at least 90%, a purity of at least 98%, a specific surface area of 0.7-1.5 m.sup.2 /g, a bending strength of at least 7 N/mm.sup.2 at a compressive force of at least 10,000 N, and a friability of less than 1% at a compressive force of at least 10,000 N, can be prepared by obtaining a sorbitol solution by hydrogenation of crystallized glucose at a temperature below 170.degree. C., and spray-drying this solution at a temperature of 140.degree. to 170.degree. C. The sorbitol thus obtained has a water content of less than 1%.The sorbitol is useful for the production of compressed formulations.

Abstract: The reduction of an aqueous solution of a carbohydrate to its polyols using as a catalyst zerovalent ruthenium on a hydrothermally stable support can be further improved using the catalyst resulting from production of zerovalent ruthenium by reduction in hydrogen at a temperature in the range 100.degree.-300.degree. C. Reduction of a ruthenium compound to afford zerovalent ruthenium at these lower temperatures affords a more active catalyst.

Abstract: Polyols such as carbohydrates including glucose, fructose, sorbitol, etc. may be subjected to a hydrocracking process to obtain lower polyols such as glycerol, ethylene glycol, 1,2-propanediol. The catalyst system which is used to effect this reaction will comprise a noble metal of Group VIII of the Periodic Table composited on a solid support plus an alkaline earth metal oxide, an example of this catalyst system being ruthenium composited on a titanited alumina support plus barium oxide.

Abstract: Zerovalent Group VIII metals dispersed on titanium dioxide reduced and calcined at a temperature less than about 300.degree. C. are hydrothermally stable hydrogenation catalysts which may be used advantageously in the reduction of aqueous solutions of carbohydrates. The use of ruthenium on titanium dioxide in the hydrogenation of glucose affords sorbitol in excellent yields with quite high selectivity.

Abstract: A method for hydrolyzing coffee extraction residue materials to produce manno-saccharides having a degree of polymerization from 1 to 10 and subsequently neutralizing and reducing said mixture of manno-saccharides to their corresponding alcohols. The coffee material, preferably spent coffee grounds from a commercial percolation system, is hydrolyzed in a Plug Flow tubular reactor in the presence of an acid catalyst, such as sulfuric acid. Depending on the time, temperature, pressure and catalyst concentration selected, manno-saccharides or mannose is produced. The manno-saccharides or mannose produced are separated from coffee residue material in the form of a syrup and neutralized with calcium hydroxide. The neutralized mixture of manno-saccharides or mannose is reduced to their corresponding alcohols or mannitol.

Abstract: A process for the production of a lower polyhydric alcohol or a mixture thereof by the hydrogenation and hydrolysis of a carbohydrate. The first stage hydrogenation produces higher polyhydric alcohols, such as sorbitol. In the second stage these higher polyhydric alcohols are selectively converted under the appropriate reaction conditions to lower polyhydric alcohols, such as ethylene glycol and 1,2-propylene glycol, using a sulfide-modified ruthenium catalyst.

Abstract: Theta-alumina is a hydrothermally stable support which can be used advantageously as an inert carrier for metals effective as a hydrogenation catalyst, thereby affording means to conduct hydrogenation in aqueous media. Ruthenium on theta-alumina is especially effective in reducing aqueous solution of carbohydrates to their polyols with high conversion and, in the case of glucose, high selectivity to sorbitol.

Abstract: This invention relates to a starch hydrolysate which can be optionally hydrogenated as well as the process for preparing said hydrolysate and uses thereof.Its glucidic spectrum corresponds to:a content of monosaccharides (DP=1) less than 14%,a content of disaccharides (DP=2) less than 35%, preferably less than 20%,a content of oligosaccharides of DP 4 to DP 10 ranging from 42% to 70%, preferably from 42 to 60%, the oligosaccharides of DP 5 to DP 7 representing by themselves a proportion preferably higher than 25% and more preferably higher than 30%,a content of polysaccharides of DP higher than 10, less than 32%, and preferably less than 25%.The hydrolysate is useful in the preparation notably of human foodstuff.

Abstract: Monosaccharides, such as glucose-water solution, are catalytically hydrogenated by being passed through multiple reaction zones connected in series and each containing a high-activity supported nickel catalyst to produce 99.8 W % overall conversion to an alditol solution such as sorbitol. The pH of liquid in each reaction zone is controlled to between 4.5 and 7 by adding an alkali solution such as sodium hydroxide to the feed to prevent acid leaching of catalyst metal and to help maintain catalyst activity therein. Reaction zone conditions used are 130.degree.-180.degree. C. temperature, 500-2000 psig hydrogen partial pressure, and a ratio of hydrogen gas/feed liquid within the range of about 500-5000. Feedstream liquid space velocity is maintained within range of 0.5-16 V.sub.f /Hr/V.sub.c, with higher space velocities being used for achieving lower incremental conversion desired in the subsequent reaction zones to help maintain pH of the effluent liquid within the desired range.

Abstract: Zerovalent Group VIII metals dispersed on titanated alumina are hydrothermally stable hydrogenation catalysts which may be used advantageously in the reduction of aqueous solutions of carbohydrates. The use of ruthenium on titanated alumina in the hydrogenation of glucose affords sorbitol in excellent yields with quite high selectivity, and with minimal leaching of either ruthenium, titanium, or alumina.

Abstract: Polyhydroxylated compounds such as glucose, sucrose, sorbitol, etc. are subjected to a hydrogenolysis reaction at hydrogenolysis conditions which include a temperature in the range of from about 175.degree. to about 250.degree. C. and a pressure in the range of from about 10 to about 2000 pounds per square inch in the presence of a catalytic composition of matter. The catalyst comprises a carbonaceous pyropolymer possessing recurring units containing at least carbon and hydrogen atoms which is impregnated with a transition metal. The products which are obtained will include alcohols, acids, ketones, ethers, and hydrocarbons.

Abstract: A process is provided for producing adipic acid from a renewable resource, i.e., biomass. The process comprises: hydrolyzing the renewable resource to provide 5-hydroxymethylfurfural, hydrogenating the 5-hydroxymethylfurfural in the presence of a catalyst to provide 2, 5-tetrahydrofurandiomethanol, treating the 2, 5-tetrahydrofurandiomethanol with hydrogen in the presence of a catalyst to provide 1, 6 hexanediol, and oxidizing the 1, 6 hexanediol in the presence of a microorganism to provide adipic acid. The formation of the adipic acid is provided with the microorganism of Gluconobacter oxydans subsp. oxydans. The renewable resources are wastes selected from the group consisting of paper, wood, corn stalks, and logging residues.

Abstract: A process for preparing a mixture of polyhydroxyl compounds having low molecular weight by catalytically hydrogenating a formose mixture with hydrogen on a metal catalyst. The hydrogenation is carried out at a pH of 7.5 to 12.5 and at elevated temperature and pressure. The formose mixture comprises (i) up to 70 wt. % formose, (ii) up to 1.6 wt. % lead ions and (iii) up to 5 wt. % calcium ions with at least one of (ii) or (iii) being present. The catalyst which is present in an amount of 4-240 wt. % (based on formose solution) is a compound taken from the group consisting of nickel, cobalt and compounds thereof. The mixture of polyhydroxyl compounds made in accordance with the present invention is useful as a starting material in the production of polyether polyols, polyester polyols and polyurethane plastics.

Abstract: Zerovalent Group VIII metals dispersed on titanium dioxide reduced and calcined at a temperature less than about 300.degree. C. are hydrothermally stable hydrogenation catalysts which may be used advantageously in the reduction of aqueous solutions of carbohydrates. The use of nickel on titanium dioxide in the hydrogenation of glucose affords sorbitol in excellent yields with quite high selectivity.

Abstract: Aldoses such as glucose solution are catalytically hydrogenated in a multiple-stage fixed-bed reaction process to produce glycerol and other polyol products. The feedstream pH to each reactor is controlled to between about 7 and 14 by adding an alkaline promotor material such as calcium hydroxide. First-stage reaction zone conditions are 130.degree.-180.degree. C. temperature, 500-2000 psig hydrogen partial pressure, and feedstream liquid space velocity is within range of 0.5-3.5 V.sub.f /Hr/V.sub.c. The first reactor uses a high activity nickel catalyst to produce at least about 98 W % conversion to alditol such as sorbitol solution.The resulting alditols such as 15-40 W % sorbitol solution in water is catalytically hydrocracked in a second-stage fixed-bed reaction zone preferably using a high-activity nickel catalyst to produce at least about 30 W % conversion to glycerol and glycols products. Second-stage reaction zone conditions are 420.degree.-520.degree. F.

Abstract: Saccharides such as glucose, fructose, starch, etc. may be hydrogenated by treatment with hydrogen in the presence of a catalyst which comprises a metal of Group VIII of the Periodic Table composited on a support comprising a carbonaceous pyropolymer possessing recurring units containing at least carbon and hydrogen atoms at a temperature in the range of from about 90.degree. to about 150.degree. C. and a pressure in the range of from about 500 to about 3000 psi to obtain polyols. In such a manner, glucose may be hydrogenated to sorbitol and mannitol.

Abstract: Zerovalent Group VIII metals dispersed on alpha-alumina are hydrothermally stable hydrogenation catalysts which may be used advantageously in the reduction of aqueous solutions of carbohydrates. The use of ruthenium on alpha-alumina in the hydrogenation of glucose affords sorbitol in excellent yields with quite high selectivity, and with minimal leaching of either ruthenium or alumina.

Abstract: Alditols such as 15-40 W. % sorbitol solution in water are catalytically hydrocracked in a fixed bed reaction process using a high activity nickel catalyst to produce at least about 30 W. % conversion to glycerol and glycol products. The feedstream pH is controlled to prevent catalyst damage by adding a basic promotor material such as calcium hydroxide. Reaction zone conditions are maintained at 420.degree.-520.degree. F. temperature, 1200-2000 psig hydrogen partial pressure, and liquid hourly space velocity of 1.5 to 3.0. To maintain desired activity and glycerol yield, the catalyst is regenerated to provide catalyst age of 8-200 hours. The reaction products are separated in a recovery step, and any alditols can be recycled to the reaction zone for further hydrogenolysis to produce 40-90 W. % glycerol product. Sorbitol conversion is maintained preferably at between about 30-70 W.

Abstract: The instant invention relates to an improved process for the production of formose from formaldehyde. The improvement resides in using relatively small quanities of basic lead compounds as catalysts for the condensation reaction of the formaldehyde and, at the same time, for controlling the pH-value. By following this technique, organic or inorganic bases which, hitherto, have normally been used for this purpose are no longer needed.

Abstract: A process is disclosed for preparing mixtures of low molecular weight polyhydroxyl compounds and optionally hydroxyaldehydes and ketones by condensing formaldehyde hydrate with itself in the presence of(A) soluble or insoluble lead(II) salts or of divalent lead attached to a high molecular weight carrier; and(B) a co-catalyst, comprising a mixture of hydroxyaldehydes and hydroxyketones obtainable by condensation of formaldehyde, which mixture contains at least 75%, by weight, of C.sub.3 to C.sub.6 compounds and is characterized by the following molar ratios:Compounds having 3 carbon atoms/compounds having 4 carbon atoms from 0.5:1 to 2.0:1;Compounds having 4 carbon atoms/compounds having 5 carbon atoms from 0.2:1 to 2.0:1;Compounds having 5 carbon atoms/compounds having 6 carbon atoms from 0.5:1 to 5.0:1.The pH of the reaction mixture is held at from 6.0 to 7.0 until from 10 to 60% conversion has occurred and is then lowered to between 4.0 to 6.0 until 90-100% conversion has occurred.

Abstract: This invention relates to an improved process for the preparation of formose by the condensation of aqueous formaldehyde. In the process according to this invention, tertiary amines which contain an electrophilic hetero atom in the .beta.-position to the tertiary nitrogen atom are used for controlling the pH instead of the inorganic bases which have previously been used for this purpose.

Abstract: A method for the synthesis of L-gulonic acid by catalytically hydrogenating D-glucuronic acid utilizing a ruthenium-based catalyst.

Abstract: Carbohydrates, especially aldose or ketose sugars, including those whose carbonyl group is masked by hemi-acetal or hemi-ketal formation, are decarbonylated by heating the feed carbohydrate together with a transition metal complex in a suitable solvent. Also, primary alcohols, including sugar alditols are simultaneously dehydrogenated and decarbonylated by heating a mixture of rhodium and ruthenium complexes and the alcohol and optionally a hydrogen acceptor in an acceptable solvent. Such defarbonylation and/or dehydrogenation of sugars provides a convenient procedure for the synthesis of certain carbohydrates and may provide a means for the conversion of biomass into useful products.