{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,27]],"date-time":"2026-05-27T21:30:33Z","timestamp":1779917433840,"version":"3.53.1"},"reference-count":37,"publisher":"MDPI AG","issue":"11","license":[{"start":{"date-parts":[[2020,11,23]],"date-time":"2020-11-23T00:00:00Z","timestamp":1606089600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"The Russian Foundation for Basic Research","award":["18-08-00435"],"award-info":[{"award-number":["18-08-00435"]}]},{"name":"The Russian Science Foundation","award":["20-19-00386)"],"award-info":[{"award-number":["20-19-00386)"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Catalysts"],"abstract":"<jats:p>Supercritical (SC) fluid technologies are well-established methods in modern green chemical synthesis. Using SC fluids as solvents instead of traditional liquids gives benefits of higher diffusivity and lower viscosity, which allows mass transfer intensification and, thus, an increased production rate of chemical transformations. Therefore, a conjugation of heterogeneous catalysis with SC media is a large step toward a green chemistry. Tetralin (TL) is an important hydrogen donor solvent used for biomass liquefaction. In industry, TL is obtained via catalytic hydrogenation of naphthalene (NL). Herein, for the first time we have demonstrated the NL hydrogenation with close to 100% selectivity to TL at almost full conversion in the SC hexane. The observed transformation rates in SC hexane were much higher allowing process intensification. The downstream processes can be also facilitated since hexane after depressurisation can be easily separated from the reaction products via simple rectification. The TL synthesis was studied in a batch reactor at variation of reaction temperature and overall pressure. For the first time for this process, low Pt-loaded (1 wt.%) nanoparticles stabilized within hyper-cross-linked aromatic polymer (HAP) were applied. The Pt\/HAP catalyst was stable under reaction conditions (250 \u00b0C, 6 MPa) allowing its recovery and reuse.<\/jats:p>","DOI":"10.3390\/catal10111362","type":"journal-article","created":{"date-parts":[[2020,11,23]],"date-time":"2020-11-23T11:50:34Z","timestamp":1606132234000},"page":"1362","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":21,"title":["New Approach to Synthesis of Tetralin via Naphthalene Hydrogenation in Supercritical Conditions Using Polymer-Stabilized Pt Nanoparticles"],"prefix":"10.3390","volume":"10","author":[{"given":"Alexey V.","family":"Bykov","sequence":"first","affiliation":[{"name":"Department of Biotechnology, Chemistry and Standardization, Tver State Technical University, A.Nikitina Street, 22, 170026 Tver, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daria V.","family":"Alekseeva","sequence":"additional","affiliation":[{"name":"Department of Biotechnology, Chemistry and Standardization, Tver State Technical University, A.Nikitina Street, 22, 170026 Tver, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Galina N.","family":"Demidenko","sequence":"additional","affiliation":[{"name":"Department of Biotechnology, Chemistry and Standardization, Tver State Technical University, A.Nikitina Street, 22, 170026 Tver, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexandre L.","family":"Vasiliev","sequence":"additional","affiliation":[{"name":"National Research Centre, Kurchatov Institute, 123182 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6348-3623","authenticated-orcid":false,"given":"Linda","family":"Nikoshvili","sequence":"additional","affiliation":[{"name":"Department of Biotechnology, Chemistry and Standardization, Tver State Technical University, A.Nikitina Street, 22, 170026 Tver, Russia"},{"name":"Regional Technological Centre, Tver State University, Zhelyabova Street, 33, 170100 Tver, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lioubov","family":"Kiwi-Minsker","sequence":"additional","affiliation":[{"name":"Regional Technological Centre, Tver State University, Zhelyabova Street, 33, 170100 Tver, Russia"},{"name":"Ecole Polytechnique F\u00e9d\u00e9rale de Lausanne, GGRC-ISIC-EPFL, CH-1015 Lausanne, Switzlerand"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,11,23]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"109296","DOI":"10.1016\/j.rser.2019.109296","article-title":"Advances in production of bio-based ester fuels with heterogeneous bifunctional catalysts","volume":"114","author":"Zhang","year":"2019","journal-title":"Renew. Sustain. Energy Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"6589","DOI":"10.1021\/ja9061954","article-title":"Advancing the frontiers in nanocatalysis, biointerfaces, and renewable energy conversion by innovations of surface techniques","volume":"131","author":"Somorjai","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"453","DOI":"10.1021\/cr970090z","article-title":"Supercritical Fluids in Heterogeneous Catalysis","volume":"99","author":"Baiker","year":"1999","journal-title":"Chem. Rev."},{"key":"ref_4","first-page":"79","article-title":"Process intensification in green synthesis","volume":"1","author":"Kumar","year":"2012","journal-title":"Green Process. Synth."},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Hart, A., Adam, M., Robinson, J.P., Rigby, S.P., and Wood, J. (2020). Hydrogenation and dehydrogenation of tetralin and naphthalene to explore heavy oil upgrading using NiMo\/Al2O3 and CoMo\/Al2O3 catalysts heated with steel balls via induction. Catalysts, 10.","DOI":"10.3390\/catal10050497"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"34955","DOI":"10.1039\/C4RA03487B","article-title":"Chemical loop systems for biochar liquefaction: Hydrogenation of naphthalene","volume":"4","author":"Feiner","year":"2014","journal-title":"RSC Adv."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"17898","DOI":"10.1039\/c3ra43516d","article-title":"Liquefaction of pyrolysis derived biochar: A new step towards biofuel from renewable resources","volume":"3","author":"Feiner","year":"2013","journal-title":"RSC Adv."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1343","DOI":"10.1007\/s12155-014-9469-x","article-title":"Kinetics of biochar liquefaction","volume":"7","author":"Feiner","year":"2014","journal-title":"BioEnergy Res."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"266","DOI":"10.1080\/10916466.2019.1697288","article-title":"Kinetics of naphthalene catalytic hydrogenation under high temperature and high pressure","volume":"38","author":"Bie","year":"2020","journal-title":"Petrol. Sci. Technol."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"365","DOI":"10.1016\/j.fuel.2012.12.025","article-title":"Hydrogenation of naphthalene over noble metal supported on mesoporous zeolite in the absence and presence of sulfur","volume":"106","author":"He","year":"2013","journal-title":"Fuel"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"197","DOI":"10.1007\/s10562-006-0042-x","article-title":"NanosizedPd\/Pt and Pd\/Rh catalysts for naphthalene hydrogenation and hydrogenolysis\/ring-opening","volume":"108","author":"Albonetti","year":"2006","journal-title":"Catal. Lett."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"405703","DOI":"10.1155\/2014\/405703","article-title":"The reactants\u2019 phase state: A nonnegligible factor in tetralin hydrogenation catalysts evaluation","volume":"2014","author":"Luo","year":"2014","journal-title":"Int. J. Chem. Eng."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1061","DOI":"10.1039\/b904305e","article-title":"Enhancing the selectivity of the hydrogenation of naphthalene to tetralin by high temperature water","volume":"11","author":"Cheng","year":"2009","journal-title":"Green Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"2566","DOI":"10.1016\/j.cjche.2020.05.010","article-title":"Selective catalytic hydrogenation of naphthalene to tetralin over a Ni-Mo\/Al2O3 catalyst","volume":"28","author":"Su","year":"2020","journal-title":"Chin. J. Chem. Eng."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"244","DOI":"10.1134\/S0965544120030135","article-title":"Application of Supercritical Fluid Technologies in Chemical and Petrochemical Industries (Review)","volume":"60","author":"Makaryan","year":"2020","journal-title":"Pet. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"573","DOI":"10.1016\/j.chemosphere.2010.09.078","article-title":"Catalytic hydrogenation rate of polycyclic aromatic hydrocarbons in supercritical carbon dioxide containing polymer-stabilized palladium nanoparticles","volume":"82","author":"Liao","year":"2011","journal-title":"Chemosphere"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/S0360-0564(08)60428-9","article-title":"Stereochemistry and mechanism of hydrogenation of naphthalene on transition metal catalysts and conformational analysis of the products","volume":"18","author":"Weitkamp","year":"1968","journal-title":"Adv. Catal."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1140","DOI":"10.1021\/ie00043a016","article-title":"Kinetic study of naphthalene hydrogenation over Pt\/Al2O3 catalyst","volume":"34","author":"Huang","year":"1995","journal-title":"Ind. Eng. Chem. Res."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"865","DOI":"10.1002\/cjce.23064","article-title":"Competitive reactive adsorption desulphurization of dibenzothiophene and hydrogenation of naphthalene over Ni\/ZnO","volume":"96","author":"Huang","year":"2018","journal-title":"Can. J. Chem. Eng."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"319","DOI":"10.1016\/j.jcat.2006.06.014","article-title":"Hydrogenation of naphthalene over NiO\/SiO2-Al2O3 catalysts: Structure-activity correlation","volume":"242","author":"Kirumakki","year":"2006","journal-title":"J. Catal."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"5966","DOI":"10.1021\/ie020395q","article-title":"Liquid-phase hydrogenation of naphthalene and tetralin on Ni\/Al2O3: Kinetic modeling","volume":"41","author":"Rautanen","year":"2002","journal-title":"Ind. Eng. Chem. Res."},{"key":"ref_22","unstructured":"US20110049016A1, McGrady, G.S., Brough, S.A., and Fredericton, W. (2011). Bitumen Upgrading using Supercritical Fluids. (8,691,084B2), U.S. Patent."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1336","DOI":"10.1021\/ja01211a074","article-title":"The vapor pressures and saturated liquid and vapor densities of the isomeric hexanes","volume":"68","author":"Kay","year":"1946","journal-title":"J. Am. Chem. Soc."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"531","DOI":"10.1021\/je00019a001","article-title":"Vapor-liquid critical properties of elements and compounds. 2. Normal Alkenes","volume":"40","author":"Ambrose","year":"1995","journal-title":"J. Chem. Eng. Data"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"177","DOI":"10.1006\/jcht.1994.1036","article-title":"BessonovaNCritical constants of n-alkanes with from 17 to 24 carbon atoms","volume":"26","author":"Nikitin","year":"1994","journal-title":"J. Chem. Thermodyn."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"869","DOI":"10.1006\/jcht.1993.1084","article-title":"SkripovPMeasurement of the critical properties of thermally unstable substances mixtures by the pulse-heating method","volume":"25","author":"Nikitin","year":"1993","journal-title":"J. Chem. Thermodyn."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1016\/S0021-9614(05)80060-6","article-title":"Measurement of the critical temperatures and critical pressures of some thermally stable or mildly unstable alkanols","volume":"23","author":"Quadri","year":"1991","journal-title":"J. Chem. Thermodyn."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"317","DOI":"10.1016\/0378-3812(90)85130-3","article-title":"The critical temperatures and densities of the n-alkanes from pentane to octadecane","volume":"57","author":"Anselme","year":"1990","journal-title":"Fluid Phase Equilib."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"6441","DOI":"10.1039\/c2jm30634d","article-title":"Pd(ii) nanoparticles in porous polystyrene: Factors influencing the nanoparticle size and catalytic properties","volume":"22","author":"Tsvetkova","year":"2012","journal-title":"J. Mater. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"6262176","DOI":"10.1155\/2019\/6262176","article-title":"Pd nanoparticles stabilized by hypercrosslinked polystyrene catalyze selective triple C-C bond hydrogenation and Suzuki cross-coupling","volume":"2019","author":"Nikoshvili","year":"2019","journal-title":"J. Nanomater."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"18234","DOI":"10.1021\/jp046459n","article-title":"Structure and Catalytic Properties of Pt-Modified Hyper-Cross-Linked Polystyrene Exhibiting Hierarchical Porosity","volume":"108","author":"Bronstein","year":"2004","journal-title":"J. Phys. Chem. B"},{"key":"ref_32","doi-asserted-by":"crossref","unstructured":"Pretsch, E., B\u00fchlmann, P., and Affolter, C. (2000). Structure Determination of Organic Compounds: Tables of Spectral Data, Springer.","DOI":"10.1007\/978-3-662-04201-4"},{"key":"ref_33","unstructured":"Silverstein, R.M., Webster, F.X., and Kiemle, D.J. (2005). Spectrometric Identification of Organic Compounds, Jonson Willey & Sons Inc.. [7th ed.]."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"973","DOI":"10.1016\/j.reactfunctpolym.2011.03.002","article-title":"On the nature of \u201cfunctional groups\u201d in non-functionalized hypercrosslinked polystyrenes","volume":"72","author":"Tsyurupa","year":"2012","journal-title":"React. Funct. Polym."},{"key":"ref_35","unstructured":"(2020, November 21). NIST X-Ray Photoelectron Spectroscopy Database, Version 4.1 (National Institute of Standards and Technology, Gaithersburg, 2012), Available online: http:\/\/srdata.nist.gov\/xps\/."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"492","DOI":"10.1007\/s11244-012-9810-6","article-title":"Palladium containing catalysts based on hypercrosslinked polystyrene for selective hydrogenation of acetylene alcohols","volume":"55","author":"Sulman","year":"2012","journal-title":"Top. Catal."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"256","DOI":"10.1016\/j.cej.2007.03.069","article-title":"Kinetics of phenol oxidation over hypercrosslinked polystyrene impregnated with Pt nanoparticles","volume":"134","author":"Doluda","year":"2007","journal-title":"Chem. Eng. J."}],"container-title":["Catalysts"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2073-4344\/10\/11\/1362\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T10:36:13Z","timestamp":1760178973000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2073-4344\/10\/11\/1362"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,11,23]]},"references-count":37,"journal-issue":{"issue":"11","published-online":{"date-parts":[[2020,11]]}},"alternative-id":["catal10111362"],"URL":"https:\/\/doi.org\/10.3390\/catal10111362","relation":{},"ISSN":["2073-4344"],"issn-type":[{"value":"2073-4344","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,11,23]]}}}