# US 8,772,550 B2 · Catalysed phenol hydrogenation > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,772,550 B2 - Document ID: US8772550B2 - Status: Granted - Kind: B2 - Application number: 13/516,897 - Filed: 2010-12-15 - Published: 2012-12-20 - Granted: 2014-07-08 - Earliest claimed: 2009-12-18 - Assignees: Dsm IP Assets B.V. - Applicants: Rudy Francois Maria Jozef Parton; Johan Thomas Tinge; Bert Hoeksema - Inventors: Rudy Francois Maria Jozef Parton; Johan Thomas Tinge; Bert Hoeksema - Web page: https://patentgrep.com/patent/US8772550B2 ## CPC - C07C 29/20: in a non-condensed rings substituted with hydroxy groups - C07C 45/006: {by hydrogenation of aromatic hydroxy compounds} - C07C 2601/14: The ring being saturated - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract The invention relates to a method for hydrogenating an aromatic compound. The invention in particular relates to a method for preparing cyclohexanone, cyclohexanol or a mixture thereof in a continuous way by catalytically hydrogenating phenol fed into a reactor comprising a supported hydrogenation catalyst, comprising a dopant selected from the group of alkali metal hydroxides, alkaline earth metal hydroxides, alkaline earth metal oxides, carbonates of alkali metals and carbonates of alkaline earth metals, and in which process during the hydrogenation of phenol continuously or intermittently water is fed into the reactor, the weight to weight ratio of water fed into the reactor to phenol fed into the reactor on average being 0.1 or less. ## Claims ### Claim 1 A method for preparing cyclohexanone, cyclohexanol or a mixture thereof in a continuous process, the process comprising: (a) feeding phenol to a reactor comprising a hydrogenation catalyst; (b) catalytically hydrogenating the phenol fed into the reactor in the presence of the hydrogenation catalyst, wherein the hydrogenation catalyst is a supported catalyst comprising a dopant selected from the group consisting of alkali metal hydroxides, alkaline earth metal hydroxides, alkaline earth metal oxides, carbonates of alkali metals and carbonates of alkaline earth metals; and (c) continuously or intermittently feeding water into the reactor during hydrogenation of the phenol according to step (a) at an average weight to weight ratio of water fed into the reactor to phenol fed into the reactor of 0.10 or less. ### Claim 2 (depends on 1) The method according to claim 1, wherein step (c) is practiced such that the water is fed into the reactor in a weight to weight ratio of water fed into the reactor to phenol fed into the reactor in the range of from 0.0010 to 0.10. ### Claim 3 (depends on 2) The method according to claim 2, wherein step (c) is practiced such that the water is fed into the reactor in a weight to weight ratio of water fed into the reactor to phenol fed into the reactor in the range of from 0.0010 to 0.05. ### Claim 4 (depends on 3) The method according to claim 3, wherein step (c) is practiced such that the water is fed into the reactor in a weight to weight ratio of water fed into the reactor to phenol fed into the reactor in the range of from 0.0015 to 0.02. ### Claim 5 (depends on 1) The method according to claim 1, which comprises feeding each of the phenol and water into the reactor as a vapour. ### Claim 6 (depends on 1) The method according to claim 1, which comprises feeding each of the phenol and water into the reactor as a liquid. ### Claim 7 (depends on 1) The method according to claim 1, which comprises feeding the phenol into the reactor as a liquid and feeding the water into the reactor as vapour. ### Claim 8 (depends on 1) The method according to claim 1, wherein the catalyst is a supported catalyst comprising a support selected from the group consisting of alumina, activated carbon, titanium oxide, calcium carbonate and carbon black. ### Claim 9 (depends on 1) The method according to claim 1, wherein the hydrogenation catalyst comprises at least one catalytic metal selected from the group consisting of palladium, platinum, ruthenium, rhodium, iridium, rubidium and osmium. ### Claim 10 (depends on 9) The method according to claim 9, wherein the hydrogenation catalyst comprises at least one catalytic metal selected from the group consisting of palladium and platinum. ### Claim 11 (depends on 10) The method according to claim 10, wherein the catalyst comprises palladium and a support selected from the group consisting of alumina and activated carbon. ### Claim 12 (depends on 9) The method according to claim 9, wherein the catalytic metal is present in a concentration of 0.1-20 wt. %, based on the weight of the support. ### Claim 13 (depends on 1) The method according to claim 1, wherein step (a) comprises hydrogenating the phenol in a shell and tubes heat exchange reactor. ### Claim 14 (depends on 8) The method according to claim 8, which comprises feeding each of the phenol and water into a slurry in the reactor in which the catalyst is present in a liquid phase comprising phenol and water. ### Claim 15 (depends on 12) The method according to claim 12, wherein the catalytic metal is present in a concentration of 0.2-10 wt. % based on the weight of the support ### Claim 16 (depends on 12) The method according to claim 12, wherein the catalytic metal is present in a concentration of 0.5-2 wt. % based on the weight of the support.