# US 10,766,025 B2 · Preparation and use of copper containing hydrogenation catalyst > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,766,025 B2 - Document ID: US10766025B2 - Status: Granted - Kind: B2 - Application number: 15/580,482 - Filed: 2016-06-07 - Published: 2018-05-24 - Granted: 2020-09-08 - Earliest claimed: 2015-06-09 - Assignees: Shell Oil Company - Applicants: Shell Oil Company - Inventors: Frank Peter Friedel; Wolfgang Dirk Lose; Andreas Klemt - Web page: https://patentgrep.com/patent/US10766025B2 ## CPC - B01J 37/031: {Precipitation} - B01J 21/06: Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof - B01J 23/72: Copper - B01J 35/40: characterised by dimensions, e.g. grain size (in a colloidal state B01J35/23; crystallite size B01J35/77) - B01J 37/0009: {Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst} - B01J 37/0036: {Grinding} - B01J 37/04: Mixing {(B01J37/0009, B01J37/0018 take precedence)} - B01J 37/06: Washing {(B01J37/0009, B01J37/0018 take precedence)} - B01J 37/08: Heat treatment {(B01J37/0009, B01J37/0018 take precedence)} - B01J 37/18: with gases containing free hydrogen - C07C 29/145: with hydrogen or hydrogen-containing gases - C07C 33/22: Benzylalcohol; phenethyl alcohol - B01J 2231/643: of R2C=O or R2C=NR (R= C, H) - C07C 2523/72: Copper - B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract The invention relates to a process for preparing a catalyst, which comprises: mixing a copper salt containing solution with a silicate salt containing composition resulting in a precipitated solid; and subjecting the precipitated solid to a temperature in the range of from 150 to 500° C. Further, the invention relates to a copper containing catalyst obtainable by said process. Still further, the invention relates to a hydrogenation process wherein such copper containing catalyst is used, more in particular a process wherein methyl phenyl ketone is hydrogenated into methyl phenyl carbinol. ## Claims ### Claim 1 A process for preparing a catalyst useful in the hydrogenation of methyl phenyl ketone (MPK) to methyl phenyl carbinol, which process comprises: mixing a copper salt containing solution with a composition containing a silicate salt selected from the group consisting of sodium silicate and calcium silicate resulting in a mixture containing a precipitated solid; recovering the precipitate solid from the mixture; subjecting the recovered precipitated solid to a temperature in the range of from 150 to 500° C. to provide a thermally treated precipitated solid; mixing the thermally treated precipitated solid with a silica sol containing silica particles having an average size in the range of from 1 to 100 nm to provide a second mixture; forming the second mixture into a shaped body; and drying the shaped body at a temperature in the range of from 80 to 160° C. followed by subjecting the shaped body to a temperature in the range of from 150 to 500° C. to yield the catalyst. ### Claim 2 (depends on 1) The process according to claim 1, wherein the silicate salt is sodium silicate. ### Claim 3 (depends on 2) The process according to claim 2, wherein the catalyst comprises an amount of copper in the range of from 40 to 95 wt %, calculated as copper (II) oxide (CuO) based on the total weight of the catalyst. ### Claim 4 (depends on 3) The process according to claim 3, further comprising: adding a base to the mixture of copper salt containing solution and silicate salt to provide for a pH of 7 or greater; and heating the mixture to a temperature in the range of from 50 to 95° C. ### Claim 5 A process for preparing a catalyst, wherein the process comprises: mixing a copper salt-containing solution with an alkali metal silicate salt resulting in a precipitated solid; mixing the mixture with an alkaline earth metal silicate salt to provide a mixture; and subjecting the mixture to a temperature in the range of from 150 to 500° C. ### Claim 6 (depends on 5) The process according to claim 5, wherein the catalyst comprises an amount of copper in the range of from 40 to 95 wt %, calculated as copper (II) oxide (CuO) based on the total weight of the catalyst. ### Claim 7 (depends on 6) The process according to claim 6, further comprising: mixing a base with the copper salt-containing solution and alkali metal silicate salt that results in the precipitate solid; and heating the resulting mixture of copper salt-containing solution, alkali metal silicate salt, and base at a temperature in the range of from 50 to 95° C. ### Claim 8 (depends on 7) The process according to claim 7, wherein the alkali metal silicate salt is a sodium silicate salt and the alkaline earth metal silicate salt is a calcium silicate salt. ### Claim 9 A process for preparing a catalyst, wherein the process comprises: mixing either an alkaline earth metal silicate salt or a silicate salt-containing composition with a precipitated solid, wherein the precipitated solid results from mixing a copper salt containing solution with a first silicate salt-containing composition, to provide a mixture; and subjecting the mixture to a temperature in the range of from 150 to 500° C. ### Claim 10 (depends on 9) The process according to claim 9, wherein the first silicate salt of the silicate salt containing composition is an alkali metal silicate salt. ### Claim 11 (depends on 10) The process according to claim 10, wherein the precipitated solid is thermally treated at a temperature in the range of from 150 to 500° C. before mixing with the alkaline earth metal silicate salt or the first silicate salt-containing composition. ### Claim 12 (depends on 10) The process according to claim 10, further comprising: mixing a second alkaline earth metal silicate salt with the copper salt containing solution and the first silicate salt containing composition in providing the mixture. ### Claim 13 (depends on 12) The process according to claim 12, wherein the first silicate salt of the silicate salt-containing composition is an alkali metal silicate salt. ### Claim 14 (depends on 10) The process according to claim 10, further comprising: mixing a second alkaline earth metal silicate salt with the precipitated solid before the thermal treatment of the precipitated solid. ### Claim 15 (depends on 10) The process according to claim 10, further comprising: mixing a second alkaline earth metal silicate salt and a shaping aid with the thermally treated precipitated solid to provide a second mixture; forming the second mixture into a shaped body; and drying the shaped body at a temperature in the range of from 80 to 160° C. followed by subjecting the shaped body to a temperature in the range of from 150 to 500° C. to yield the catalyst. ### Claim 16 (depends on 10) The process according to claim 10, wherein the catalyst comprises an amount of copper in the range of from 40 to 95 wt %, calculated as copper (II) oxide (CuO) based on the total weight of the catalyst. ### Claim 17 (depends on 16) The process according to claim 16, further comprising: activating the catalyst by contacting it with hydrogen gas to thereby provide an exothermic reduction reaction of the catalyst to provide an activated catalyst. ### Claim 18 (depends on 17) The process according to claim 17, wherein the alkali metal silicate salt is a sodium silicate salt, the alkaline earth metal silicate salt is a calcium silicate salt, and the silicate salt of the silicate salt-containing composition is a sodium silicate salt. ### Claim 19 A process for preparing an activated catalyst, which process comprises: mixing a copper salt containing solution with a silicate salt containing composition resulting in a precipitated solid; subjecting the precipitated solid to a temperature in the range of from 150 to 500° C. resulting in a thermally treated precipitated solid; mixing the thermally treated precipitated solid with a shaping aid containing suspension; shaping the mixture thus obtained resulting in shaped bodies; and subjecting the shaped bodies to a temperature in the range of from 150 to 500° C. to provide a catalyst; and activating the catalyst by contacting it with hydrogen gas to thereby provide an exothermic reduction reaction of the catalyst to provide the activated catalyst. ### Claim 20 (depends on 19) The process according to claim 19, wherein the silicate salt is either an alkali metal silicate salt or an alkaline earth metal silicate salt. ### Claim 21 (depends on 20) The process according to claim 20, wherein the silicate salt comprises an alkali metal silicate salt. ### Claim 22 (depends on 21) The process according to claim 21, wherein the catalyst comprises an amount of copper in the range of from 40 to 95 wt %, calculated as copper (II) oxide (CuO) based on the total weight of the catalyst. ### Claim 23 (depends on 22) The process according to claim 22, further comprising: mixing a base with the copper salt-containing solution and alkali metal silicate salt that results in the precipitate solid; and heating the resulting mixture of copper salt-containing solution, alkali metal silicate salt, and base at a temperature in the range of from 50 to 95° C.