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Lignin is converted into novel polymer building blocks through four steps: catalytic hydroprocessing of softwood to form 4\u2010alkylguaiacols, their conversion into 4\u2010alkylcyclohexanols, followed by dehydrogenation to form cyclohexanones, and Baeyer\u2013Villiger oxidation to give caprolactones. The formation of alkylated cyclohexanols is one of the most difficult steps in the series. A liquid\u2010phase process in the presence of nickel on CeO<jats:sub>2<\/jats:sub> or ZrO<jats:sub>2<\/jats:sub> catalysts is demonstrated herein to give the highest cyclohexanol yields. The catalytic reaction with 4\u2010alkylguaiacols follows two parallel pathways with comparable rates: 1)\u2005ring hydrogenation with the formation of the corresponding alkylated 2\u2010methoxycyclohexanol, and 2)\u2005demethoxylation to form 4\u2010alkylphenol. Although subsequent phenol to cyclohexanol conversion is fast, the rate is limited for the removal of the methoxy group from 2\u2010methoxycyclohexanol. Overall, this last reaction is the rate\u2010limiting step and requires a sufficient temperature (&gt;250\u2009\u00b0C) to overcome the energy barrier. Substrate reactivity (with respect to the type of alkyl chain) and details of the catalyst properties (nickel loading and nickel particle size) on the reaction rates are reported in detail for the Ni\/CeO<jats:sub>2<\/jats:sub> catalyst. The best Ni\/CeO<jats:sub>2<\/jats:sub> catalyst reaches 4\u2010alkylcyclohexanol yields over 80\u2009%, is even able to convert real softwood\u2010derived guaiacol mixtures and can be reused in subsequent experiments. A proof of principle of the projected cascade conversion of lignocellulose feedstock entirely into caprolactone is demonstrated by using Cu\/ZrO<jats:sub>2<\/jats:sub> for the dehydrogenation step to produce the resultant cyclohexanones (\u224880\u2009%) and tin\u2010containing beta zeolite to form 4\u2010alkyl\u2010\u03b5\u2010caprolactones in high yields, according to a Baeyer\u2013Villiger\u2010type oxidation with H<jats:sub>2<\/jats:sub>O<jats:sub>2<\/jats:sub>.<\/jats:p>","DOI":"10.1002\/cssc.201403375","type":"journal-article","created":{"date-parts":[[2015,4,16]],"date-time":"2015-04-16T13:01:12Z","timestamp":1429189272000},"page":"1805-1818","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":160,"title":["Selective Nickel\u2010Catalyzed Conversion of Model and Lignin\u2010Derived Phenolic Compounds to Cyclohexanone\u2010Based Polymer Building Blocks"],"prefix":"10.1002","volume":"8","author":[{"given":"Wouter","family":"Schutyser","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sander","family":"Van\u2005den\u2005Bosch","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jan","family":"Dijkmans","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stuart","family":"Turner","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maria","family":"Meledina","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gustaaf","family":"Van\u2005Tendeloo","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Damien P.","family":"Debecker","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bert F.","family":"Sels","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2015,4,16]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr068360d"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1114736"},{"key":"e_1_2_6_4_2","first-page":"1","volume-title":"Selective Catalysis for Renewable Feedstocks and Chemicals, Vol.\u2005353","author":"Dusselier M.","year":"2014"},{"key":"e_1_2_6_5_2","first-page":"566","volume-title":"Aqueous Pretreatment of Plant Biomass for Biological and Chemical Conversion to Fuels and Chemicals","year":"2013"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr4002269"},{"key":"e_1_2_6_7_2","first-page":"496","volume-title":"The Role of Green Chemistry in Biomass Processing and Conversion","year":"2012"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201400922"},{"key":"e_1_2_6_8_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201400922"},{"key":"e_1_2_6_9_2","unstructured":"\u00a0"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.201000302"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1cy00093d"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cy00500j"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201105125"},{"key":"e_1_2_6_13_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201105125"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.200900188"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/c004654j"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201200610"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201100782"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3ee00069a"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1039\/C2EE23057G"},{"key":"e_1_2_6_20_2","doi-asserted-by":"crossref","first-page":"85","DOI":"10.1007\/128_2014_540","volume-title":"Selective Catalysis for Renewable Feedstocks and Chemicals, Vol.\u2005353","author":"Dusselier M.","year":"2014"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4EE01523A"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1gc15350a"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1cc10422e"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/sc5001463"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201300765"},{"key":"e_1_2_6_26_2","unstructured":"\u00a0"},{"key":"e_1_2_6_27_2","first-page":"79","volume-title":"Top Value\u2010Added Chemicals from Biomass, Vol.\u2005II","author":"Holladay J. 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