{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,1]],"date-time":"2026-04-01T15:49:32Z","timestamp":1775058572340,"version":"3.50.1"},"reference-count":28,"publisher":"Wiley","issue":"13","license":[{"start":{"date-parts":[[2018,5,14]],"date-time":"2018-05-14T00:00:00Z","timestamp":1526256000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemCatChem"],"published-print":{"date-parts":[[2018,7,9]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>It is well established that the transformation of abundant and cheap natural products, such as terpenoids, can produce other more valuable compounds. Thymoquinone, which has a commercial value significantly higher than that of its precursors, can be obtained by oxidation of carvacrol and thymol. In this work, a new water\u2010soluble Mn<jats:sup>III<\/jats:sup> PEG\u2010porphyrin is reported as catalyst in a water\/hexane (1:1) biphasic medium for the oxidation of carvacrol and thymol into thymoquinone. The reactions were performed using <jats:italic>tert<\/jats:italic>\u2010butyl hydroperoxide as oxidant in the presence of ammonium acetate as co\u2010catalyst, reaching 94 and 78\u2009% of conversion after 5\u2005h of reaction for thymol and carvacrol, respectively. Experiments with oregano essential oil as substrate revealed selective transformation of thymol and carvacrol into thymoquinone. The main advantage of this biphasic system based on a water\u2010soluble catalyst and on substrates and products soluble in hexane, is the straightforward isolation, recovery and recycling of the catalyst by simple phase separation. Recycling studies of the Mn<jats:sup>III<\/jats:sup> PEG\u2010porphyrin using thymol as substrate showed high conversion values throughout four catalytic cycles.<\/jats:p>","DOI":"10.1002\/cctc.201800239","type":"journal-article","created":{"date-parts":[[2018,4,12]],"date-time":"2018-04-12T09:47:18Z","timestamp":1523526438000},"page":"2804-2809","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Oxidation of Monoterpenes Catalysed by a Water\u2010Soluble Mn<sup>III<\/sup> PEG\u2010Porphyrin in a Biphasic Medium"],"prefix":"10.1002","volume":"10","author":[{"given":"Cl\u00e1udia M. B.","family":"Neves","sequence":"first","affiliation":[{"name":"Department of Chemistry &amp; QOPNA University of Aveiro  3810-193 Aveiro Portugal"}]},{"given":"Jo\u00e3o P. C.","family":"Tom\u00e9","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural (CQE) Departmento de Engenharia Qu\u00edmica, Instituto Superior T\u00e9cnico Universidade de Lisboa  1049-001 Lisboa Portugal"}]},{"given":"Zhanyao","family":"Hou","sequence":"additional","affiliation":[{"name":"Supramolecular Chemistry Group Center of Macromolecular Chemistry (CMaC) Department of Organic and Macromolecular Chemistry Ghent University  Krijgslaan 281 S4 B-9000 Ghent Belgium"}]},{"given":"Wim","family":"Dehaen","sequence":"additional","affiliation":[{"name":"Department of Chemistry KU Leuven  Celestijnenlaan 200f-bus 02404 3001 Leuven Belgium"}]},{"given":"Richard","family":"Hoogenboom","sequence":"additional","affiliation":[{"name":"Supramolecular Chemistry Group Center of Macromolecular Chemistry (CMaC) Department of Organic and Macromolecular Chemistry Ghent University  Krijgslaan 281 S4 B-9000 Ghent Belgium"}]},{"given":"M. Gra\u00e7a P. M. S.","family":"Neves","sequence":"additional","affiliation":[{"name":"Department of Chemistry &amp; QOPNA University of Aveiro  3810-193 Aveiro Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9071-2252","authenticated-orcid":false,"given":"M\u00e1rio M. Q.","family":"Sim\u00f5es","sequence":"additional","affiliation":[{"name":"Department of Chemistry &amp; QOPNA University of Aveiro  3810-193 Aveiro Portugal"}]}],"member":"311","published-online":{"date-parts":[[2018,5,14]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"publisher","DOI":"10.1080\/10575639808044955"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/1099-1573(200008)14:5<323::AID-PTR621>3.0.CO;2-Q"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/ptr.1309"},{"key":"e_1_2_7_4_1","first-page":"8","volume":"82","author":"Amin B.","year":"2016","journal-title":"Planta Med."},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biocel.2005.10.009"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bcp.2011.09.029"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.18632\/oncotarget.17206"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2004.12.034"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf070094x"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.2174\/138161208786404227"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2016.04.111"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0308-8146(00)00144-8"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/jsfa.6089"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1080\/00397918508076837"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1381-1169(98)00083-1"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1381-1169(03)00181-X"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/ie050185o"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1381-1169(02)00582-4"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10562-016-1850-2"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0926-860X(01)00560-9"},{"key":"e_1_2_7_21_1","doi-asserted-by":"crossref","first-page":"1","DOI":"10.3390\/molecules22060980","volume":"22","author":"Luciano M.","year":"2017","journal-title":"Molecules"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr00014a008"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.crci.2006.11.001"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)00639-1"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2013.05.010"},{"key":"e_1_2_7_26_1","first-page":"119","volume-title":"The Porphyrin Handbook, Vol.\u20054","author":"Meunier B.","year":"2000"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC03128A"},{"key":"e_1_2_7_28_1","first-page":"389","volume-title":"Porphyrins Vol.\u2005I Struct. 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