A method of making of 1,2,5,6-hexanetetrol (“tetrol”). The method includes the steps of contacting a reaction solution containing water as well as levoglucosenone, dihydrolevoglucosenone, and/or levoglucosanol, with a catalyst containing metal and acid functionalities, at temperature of from about 100° C. to about 175° C., and a hydrogen partial pressure of from about 1 bar to about 50 bar (about 0.1 MPa to about 5 MPa), and for a time wherein at least a portion of the reactant is converted into 1,2,5,6-hexanetetrol.

A method and catalyst for producing an alcohol, which method includes supplying water and a C2-C5 olefin to a reactor and performing hydration in a gas phase using a solid acid catalyst. The solid acid catalyst is one in which a heteropolyacid or a salt thereof is supported on a silica carrier. The silica carrier is obtained by kneading a fumed silica obtained by a combustion method, a silica gel obtained by a gel method, and a colloidal silica obtained by a sol-gel method or a water glass method; molding the resulting kneaded product; and calcining the resulting molded body.

A reactor for performing a gas/liquid biphasic high-pressure reaction with a foaming medium, comprising an interior formed by a cylindrical, vertically oriented elongate shell, a bottom and a cap, wherein the interior is divided by internals into a backmixed zone and a zone of limited backmixing, wherein the backmixed zone and the zone of limited backmixing are consecutively traversable by the reaction mixture, wherein the backmixed zone comprises means for introducing gas and liquid and a gas outlet and also comprises at least one mixing apparatus selected from a stirrer, a jet nozzle and means for injecting the gas, and the zone of limited backmixing comprises a reaction product outlet, a first cylindrical internal element which in the interior extends in the longitudinal direction of the reactor and which delimits the zone of limited backmixing from the backmixed zone, backmixing-preventing second internal elements in the form of random packings, structured packings or liquid-permeable trays arranged in the zone of limited backmixing and a riser tube whose lower end is arranged within the backmixed zone and whose upper end opens into the zone of limited backmixing so that liquid from the backmixed zone can ascend into the zone of limited backmixing via the riser tube, wherein flow into the zone of limited backmixing enters from below. The reactor is configured such that the high-pressure reaction space is optimally utilized and contamination of workup steps or subsequent reactions arranged downstream of the high-pressure reaction with foam is substantially avoided. The invention further relates to a process for performing a continuous gas/liquid biphasic high-pressure reaction in the reactor.

A reactor for performing a gas/liquid biphasic high-pressure reaction with a foaming medium, comprising an interior formed by a cylindrical, vertically oriented elongate shell, a bottom and a cap, wherein the interior is divided by internals into a backmixed zone and a zone of limited backmixing, wherein the backmixed zone and the zone of limited backmixing are consecutively traversable by the reaction mixture, wherein the backmixed zone comprises means for introducing gas and liquid and a gas outlet and also comprises at least one mixing apparatus selected from a stirrer, a jet nozzle and means for injecting the gas, and the zone of limited backmixing comprises a reaction product outlet, a first cylindrical internal element which in the interior extends in the longitudinal direction of the reactor and which delimits the zone of limited backmixing from the backmixed zone, backmixing-preventing second internal elements in the form of random packings, structured packings or liquid-permeable trays arranged in the zone of limited backmixing and a riser tube whose lower end is arranged within the backmixed zone and whose upper end opens into the zone of limited backmixing so that liquid from the backmixed zone can ascend into the zone of limited backmixing via the riser tube, wherein flow into the zone of limited backmixing enters from below. The reactor is configured such that the high-pressure reaction space is optimally utilized and contamination of workup steps or subsequent reactions arranged downstream of the high-pressure reaction with foam is substantially avoided. The invention further relates to a process for performing a continuous gas/liquid biphasic high-pressure reaction in the reactor.

By this invention processes are provided for the conversion of carbohydrate to ethylene glycol by retro-aldol catalysis and sequential hydrogenation using control methods having at least one of acetol (hydroxyacetone) and a tracer as inputs.

A process for the production of normal-butanol, iso-butanol and 2-alkyl alkanol is disclosed. The process comprises: hydrogenating a feed comprising normal butyraldehyde, iso-butyraldehyde and 2-alkyl alkenal to form a crude product stream comprising normal-butanol, iso-butanol, 2-alkyl alkanol, unreacted normal butyraldehyde, unreacted iso-butyraldehyde and one or more of unreacted 2-alkyl alkenal, 2-alkyl alkanal or 2-alkyl alkenol; separating the crude product stream to produce: a mixed butanol stream having higher concentrations of normal butanol, iso-butanol, unreacted normal butyraldehyde and unreacted iso-butyraldehyde than the crude product stream; and a crude 2-alkyl alkanol stream having higher concentrations of 2-alkyl alkanol and the one or more of unreacted 2-alkyl alkenal, 2-alkyl alkanal or 2-alkyl alkenol than the crude product stream; separating the mixed butanol stream to produce: a refined normal butanol stream having a higher concentration of normal butanol than the mixed butanol stream; and a crude iso-butanol stream having a higher concentration of iso-butanol than the mixed butanol stream; feeding the crude iso-butanol stream to a first polishing hydrogenation reactor wherein at least some of the unreacted iso-butyraldehyde is converted to iso-butanol to produce a polished iso-butanol stream; separating the polished iso-butanol stream to produce: a refined iso-butanol stream having a higher concentration of iso-butanol than the polished iso-butanol stream; and a light waste stream; separating the crude 2-alkyl alkanol stream to produce: an intermediate 2-alkyl alkanol stream having higher concentrations of 2-alkyl alkanol and the one or more of unreacted 2-alkyl alkenal, 2-alkyl alkanal or 2-alkyl alkenol than the crude 2-alkyl alkanol stream; and a heavy waste stream; feeding the intermediate 2-alkyl alkanol stream to a second polishing hydrogenation reactor wherein at least some of the one or more of unreacted 2-alkyl alkenal, 2-alkyl alkanal or 2-alkyl alkenol is converted to 2-alkyl alkanol to produce a polished 2-alkyl alkanol stream having a higher concentration of 2-alkyl alkanol than the intermediate 2-alkyl alkanol stream; separating the polished 2-alkyl alkanol stream to produce: a refined 2-alkyl alkanol stream having a higher concentration of 2-alkyl alkanol than the polished 2-alkyl alkanol stream; and an intermediate waste stream.

A process for the production of normal-butanol, iso-butanol and 2-alkyl alkanol is disclosed. The process comprises: hydrogenating a feed comprising normal butyraldehyde, iso-butyraldehyde and 2-alkyl alkenal to form a crude product stream comprising normal-butanol, iso-butanol, 2-alkyl alkanol, unreacted normal butyraldehyde, unreacted iso-butyraldehyde and one or more of unreacted 2-alkyl alkenal, 2-alkyl alkanal or 2-alkyl alkenol; separating the crude product stream to produce: a mixed butanol stream having higher concentrations of normal butanol, iso-butanol, unreacted normal butyraldehyde and unreacted iso-butyraldehyde than the crude product stream; and a crude 2-alkyl alkanol stream having higher concentrations of 2-alkyl alkanol and the one or more of unreacted 2-alkyl alkenal, 2-alkyl alkanal or 2-alkyl alkenol than the crude product stream; separating the mixed butanol stream to produce: a refined normal butanol stream having a higher concentration of normal butanol than the mixed butanol stream; and a crude iso-butanol stream having a higher concentration of iso-butanol than the mixed butanol stream; feeding the crude iso-butanol stream to a first polishing hydrogenation reactor wherein at least some of the unreacted iso-butyraldehyde is converted to iso-butanol to produce a polished iso-butanol stream; separating the polished iso-butanol stream to produce: a refined iso-butanol stream having a higher concentration of iso-butanol than the polished iso-butanol stream; and a light waste stream; separating the crude 2-alkyl alkanol stream to produce: an intermediate 2-alkyl alkanol stream having higher concentrations of 2-alkyl alkanol and the one or more of unreacted 2-alkyl alkenal, 2-alkyl alkanal or 2-alkyl alkenol than the crude 2-alkyl alkanol stream; and a heavy waste stream; feeding the intermediate 2-alkyl alkanol stream to a second polishing hydrogenation reactor wherein at least some of the one or more of unreacted 2-alkyl alkenal, 2-alkyl alkanal or 2-alkyl alkenol is converted to 2-alkyl alkanol to produce a polished 2-alkyl alkanol stream having a higher concentration of 2-alkyl alkanol than the intermediate 2-alkyl alkanol stream; separating the polished 2-alkyl alkanol stream to produce: a refined 2-alkyl alkanol stream having a higher concentration of 2-alkyl alkanol than the polished 2-alkyl alkanol stream; and an intermediate waste stream.

The present invention relates to a process for the preparation of an optically active carbonyl compound by asymmetric hydrogenation of a prochiral α,β-unsaturated carbonyl compound with hydrogen in the presence of at least one optically active transition metal catalyst that is soluble in the reaction mixture and which has rhodium as catalytically active transition metal and a chiral, bidentate bisphosphine ligand, wherein the reaction mixture during the hydrogenation of the prochiral α,β-unsaturated carbonyl compound additionally comprises at least one compound of the general formula (I): ##STR00001## in which R.sup.1, R.sup.2: are identical or different and are C.sub.6- to C.sub.10-aryl which is unsubstituted or carries one or more, e.g. 1, 2, 3, 4 or 5, substituents which are selected from C.sub.1- to C.sub.6-alkyl, C.sub.3- to C.sub.6-cycloalkyl, C.sub.6- to C.sub.10-aryl, C.sub.1- to C.sub.6-alkoxy and amino; Z is a group CHR.sup.3R.sup.4 or aryl which is unsubstituted or carries one or more, e.g. 1, 2, 3, 4 or 5, substituents which are selected from C.sub.1- to C.sub.6-alkyl, C.sub.3- to C.sub.6-cycloalkyl, C.sub.6- to C.sub.10-aryl, C.sub.1- to C.sub.6-alkoxy and amino, wherein R.sup.3 and R.sup.4 are as defined in the claims and the description.

The present invention relates to a process for the preparation of an optically active carbonyl compound by asymmetric hydrogenation of a prochiral α,β-unsaturated carbonyl compound with hydrogen in the presence of at least one optically active transition metal catalyst that is soluble in the reaction mixture and which has rhodium as catalytically active transition metal and a chiral, bidentate bisphosphine ligand, wherein the reaction mixture during the hydrogenation of the prochiral α,β-unsaturated carbonyl compound additionally comprises at least one compound of the general formula (I): ##STR00001## in which R.sup.1, R.sup.2: are identical or different and are C.sub.6- to C.sub.10-aryl which is unsubstituted or carries one or more, e.g. 1, 2, 3, 4 or 5, substituents which are selected from C.sub.1- to C.sub.6-alkyl, C.sub.3- to C.sub.6-cycloalkyl, C.sub.6- to C.sub.10-aryl, C.sub.1- to C.sub.6-alkoxy and amino; Z is a group CHR.sup.3R.sup.4 or aryl which is unsubstituted or carries one or more, e.g. 1, 2, 3, 4 or 5, substituents which are selected from C.sub.1- to C.sub.6-alkyl, C.sub.3- to C.sub.6-cycloalkyl, C.sub.6- to C.sub.10-aryl, C.sub.1- to C.sub.6-alkoxy and amino, wherein R.sup.3 and R.sup.4 are as defined in the claims and the description.

A carbon-coated transition metal nanocomposite material includes carbon-coated transition metal particles having a core-shell structure. The shell layer of the core-shell structure is a graphitized carbon layer doped with oxygen and/or nitrogen, and the core of the core-shell structure is a transition metal nanoparticle. The nanocomposite material has a structure rich in mesopores, is an adsorption/catalyst material with excellent performance, can be used for catalyzing various hydrogenation reduction reactions, or used as a catalytic-oxidation catalyst useful for the treatment of volatile organic compounds in industrial exhaust gases.