# US 12,006,279 B2 · Process for hydrogenation of C13 aldehydes in at least two hydrogenation stages > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,006,279 B2 - Document ID: US12006279B2 - Status: Granted - Kind: B2 - Application number: 18/113,319 - Filed: 2023-02-23 - Published: 2023-08-31 - Granted: 2024-06-11 - Earliest claimed: 2022-02-25 - Assignees: Evonik Operations GmbH - Applicants: Evonik Operations GmbH - Inventors: Robert Franke; Meike Roos; Horst-Werner Zanthoff; Julia Bauer; Christoph Weber; Andrea Heinroth; Jan Benedikt Metternich - Web page: https://patentgrep.com/patent/US12006279B2 ## CPC - C07C 29/141: with hydrogen or hydrogen-containing gases - C07C 31/125: containing five to twenty-two carbon atoms - B01J 21/02: Boron or aluminium; Oxides or hydroxides thereof - B01J 23/6525: {Molybdenum} - C07C 2523/76: combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36 - C07C 2523/88: Molybdenum - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS ## Abstract The present invention relates to a process for producing alcohols by hydrogenation of C13 aldehydes. The process according to the invention is performed in two consecutive hydrogenation stages, wherein the first hydrogenation stage employs an activated metal catalyst based on a nickel metal foam and the second stage employs a supported catalyst containing a catalytically active component from the group consisting of nickel, copper, chromium and mixtures thereof. ## Claims ### Claim 1 Process for producing alcohols by continuous hydrogenation of C13 aldehydes in at least two hydrogenation stages, wherein a stream containing the C13 aldehydes to be hydrogenated is hydrogenated with a hydrogen-containing gas over an activated metal catalyst based on a nickel metal foam in the liquid phase in the first hydrogenation stage comprising at least one recirculating reactor, wherein a crude product stream containing at least alcohols and unconverted aldehydes, of which a first portion is recycled and a second portion is passed to the second hydrogenation stage, is withdrawn from the at least one recirculating reactor, the second portion of the crude product stream is hydrogenated with a hydrogen-containing gas over a supported catalyst comprising a catalytically active component and a support material in the liquid phase in the second hydrogenation stage comprising at least one reactor operated in straight pass, wherein the catalytically active component is selected from the group consisting of nickel, copper, chromium and mixtures thereof and wherein the support material consists to an extent of more than 90% by weight of an oxidic material selected from the group consisting of aluminum oxide, aluminum silicate, silicon dioxide, titanium dioxide, zirconium oxide and mixtures of two or more thereof. ### Claim 2 (depends on 1) Process according to claim 1, wherein the stream employed in the process is an isotridecanal stream. ### Claim 3 (depends on 1) Process according to claim 1, wherein the activated metal catalyst based on a nickel metal foam is free from organic constituents, wherein free from organic constituents is defined as the sum of the weight fractions of carbon and carbon-containing compounds is less than 0.2% by weight of the total weight of the catalyst. ### Claim 4 (depends on 1) Process according to claim 1, wherein the activated metal catalyst based on a nickel metal foam contains 80% to 95% by weight of nickel and 5% to 15% by weight of aluminum in each case based on the total weight of the catalyst. ### Claim 5 (depends on 4) Process according to claim 4, wherein the activated metal catalyst based on a nickel metal foam additionally contains 0.01% to 3% by weight of molybdenum, based on the total weight of the catalyst. ### Claim 6 (depends on 1) Process according to claim 1, wherein the hydrogenation in the first hydrogenation stage is performed at a pressure of 5 to 150 bar. ### Claim 7 (depends on 1) Process according to claim 1, wherein the hydrogenation in the first hydrogenation stage is performed at a temperature of 50° C. to 250° C. ### Claim 8 (depends on 1) Process according to claim 1, wherein the conversion of the hydrogenation in the first hydrogenation stage is at least 85%. ### Claim 9 (depends on 1) Process according to claim 1, wherein the support material of the supported catalyst is aluminum oxide, aluminum silicate or silicon dioxide. ### Claim 10 (depends on 9) Process according to claim 9, wherein the support material has a BET surface area of 70 to 350 m2/g. ### Claim 11 (depends on 1) Process according to claim 1, wherein the hydrogenation in the second hydrogenation stage is performed at a pressure of 5 to 250 bar. ### Claim 12 (depends on 1) Process according to claim 1, wherein the hydrogenation in the second hydrogenation stage is performed at a temperature of 100° C. to 220° C. ### Claim 13 (depends on 1) Process according to claim 1, wherein the hydrogenation is carried out with a stoichiometric excess of hydrogen based on the aldehydes to be hydrogenated in both hydrogenation stages. ### Claim 14 (depends on 1) Process according to claim 1, wherein no aqueous phase is added in the first hydrogenation stage but an aqueous phase is added in the second hydrogenation stage. ### Claim 15 (depends on 11) The process according to claim 11, wherein the support material has a BET surface area of 150 to 280 m2/g. ### Claim 16 Process for producing alcohols by continuous hydrogenation of C13 aldehydes in at least two hydrogenation stages, wherein a stream containing the C13 aldehydes to be hydrogenated is hydrogenated with a hydrogen-containing gas over an activated metal catalyst based on a nickel metal foam in the liquid phase in the first hydrogenation stage comprising at least one recirculating reactor, wherein a crude product stream containing at least alcohols and unconverted aldehydes, of which a first portion is recycled and a second portion is passed to the second hydrogenation stage, is withdrawn from the at least one recirculating reactor, the second portion of the crude product stream is hydrogenated with a hydrogen-containing gas over a supported catalyst comprising a catalytically active component and a support material in the liquid phase in the second hydrogenation stage comprising at least one reactor operated in straight pass, wherein the catalytically active component is selected from the group consisting of nickel, copper, chromium and mixtures thereof and wherein the support material consists to an extent of more than 90% by weight of an oxidic material selected from the group consisting of aluminum oxide, aluminum silicate, silicon dioxide, titanium dioxide, zirconium oxide and mixtures of two or more thereof, wherein the volume fraction of the activated metal catalyst based on a nickel metal foam in the total catalyst volume of all hydrogenation stages is from 30% to 80%.