{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,13]],"date-time":"2026-10-13T10:47:11Z","timestamp":1791888431719,"version":"4.3.4"},"reference-count":58,"publisher":"Wiley","issue":"24","license":[{"start":{"date-parts":[[2016,11,17]],"date-time":"2016-11-17T00:00:00Z","timestamp":1479340800000},"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":["ChemSusChem"],"published-print":{"date-parts":[[2016,12,20]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>With the increasing restriction and control of hazardous solvents, safer alternatives need to be identified. Here a contemporary approach to solvent selection and substitution is presented that offers a more scientific alternative to the simple \u201clike\u2010for\u2010like\u201d exchange. A new family of levoglucosenonederived compounds is proposed, modeled to determine their solvent properties, synthesized, and tested. These new molecules show promise as replacements for polar aprotic solvents that have chronic toxicity issues, such as dichloromethane, nitrobenzene, and <jats:italic>N<\/jats:italic>\u2010methylpyrrolidinone. The success of this approach makes it possible for academia and industry to make calculated, intelligent choices for solvent substitution in the future.<\/jats:p>","DOI":"10.1002\/cssc.201600795","type":"journal-article","created":{"date-parts":[[2016,11,17]],"date-time":"2016-11-17T09:57:17Z","timestamp":1479376637000},"page":"3503-3512","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":51,"title":["Intelligent Approach to Solvent Substitution: The Identification of a New Class of Levoglucosenone Derivatives"],"prefix":"10.1002","volume":"9","author":[{"given":"Ana","family":"Alves\u2005Costa\u2005Pacheco","sequence":"first","affiliation":[{"name":"Department of Chemistry University of York  Heslington York YO10 5DD UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"James","family":"Sherwood","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of York  Heslington York YO10 5DD UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anna","family":"Zhenova","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of York  Heslington York YO10 5DD UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Con R.","family":"McElroy","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of York  Heslington York YO10 5DD UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andrew J.","family":"Hunt","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of York  Heslington York YO10 5DD UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Helen L.","family":"Parker","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of York  Heslington York YO10 5DD UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thomas J.","family":"Farmer","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of York  Heslington York YO10 5DD UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andri","family":"Constantinou","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of York  Heslington York YO10 5DD UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mario","family":"De\u2005bruyn","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of York  Heslington York YO10 5DD UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Adrian C.","family":"Whitwood","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of York  Heslington York YO10 5DD UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Warwick","family":"Raverty","sequence":"additional","affiliation":[{"name":"Circa Group Pty Ltd  551 Burwood Highway Knoxfield Victoria 3180 Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"James H.","family":"Clark","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of York  Heslington York YO10 5DD UK"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2016,11,17]]},"reference":[{"key":"e_1_2_5_1_1","unstructured":"Candidate List of Substances of Very High Concern for Authorisation http:\/\/echa.europa.eu\/candidate-list-table(accessed 8th June 2016)."},{"key":"e_1_2_5_2_1","unstructured":"Roche SHE goals and performance http:\/\/www.roche.com\/sustainability\/for_communities_and_environment\/environment\/our_she_goals_and_performance.htm(accessed 8th June 2016); Roche to phase out SVHCs within ten years of listing https:\/\/chemicalwatch.com\/43487\/roche-to-phase-out-svhcs-within-ten-years-of-listing(accessed 25th January 2016)."},{"key":"e_1_2_5_3_1","unstructured":"Regulation (EC) 1907\/2006 of the European Parliament and of the Council of 18 December 2006 Concerning the Registration Evaluation Authorisation and Restriction of Chemicals (REACH) http:\/\/eur-lex.europa.eu\/legal-content\/EN\/TXT\/?uri=CELEX:02006R1907-20140410(accessed 11th May 2016)."},{"key":"e_1_2_5_4_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5GC01008J"},{"key":"e_1_2_5_5_1","volume-title":"Chlorinated solvents: a forensic evaluation","author":"Morrison R. D.","year":"2013"},{"key":"e_1_2_5_5_2","unstructured":"R.\u2005B. Thomas inEvaluation of alternatives to chlorinated solvents for metal cleaning U.\u2005S. Environmental Protection Agency National Risk Management Research Laboratory Cincinnati 1997."},{"key":"e_1_2_5_6_1","doi-asserted-by":"publisher","DOI":"10.1038\/ngeo2363"},{"key":"e_1_2_5_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC04133J"},{"key":"e_1_2_5_8_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4GC01677G"},{"key":"e_1_2_5_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/sc5002287"},{"key":"e_1_2_5_10_1","doi-asserted-by":"publisher","DOI":"10.2174\/157017941206150828102108"},{"key":"e_1_2_5_10_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cs60241a"},{"key":"e_1_2_5_11_1","doi-asserted-by":"publisher","DOI":"10.3390\/ijms160817101"},{"key":"e_1_2_5_12_1","volume-title":"Green chemistry: an introductory text","author":"Lancaster M.","year":"2002"},{"key":"e_1_2_5_13_1","unstructured":"New multi-million-dollar industry in non-petroleum based solvent could come to Tasmania http:\/\/www.abc.net.au\/news\/2015-11-13\/tasmanias-new-multi-billion-dollar-green-chemical-industry\/6939522(accessed 8th June 2016)."},{"key":"e_1_2_5_14_1","doi-asserted-by":"publisher","DOI":"10.1039\/c0gc00918k"},{"key":"e_1_2_5_15_1","first-page":"42","volume":"76","author":"Taylor P.","year":"1989","journal-title":"Plat. Surf. Finish."},{"key":"e_1_2_5_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/cen-v086n029.p032"},{"key":"e_1_2_5_16_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4GC02377C"},{"key":"e_1_2_5_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/3527600701.ch3"},{"key":"e_1_2_5_18_1","doi-asserted-by":"publisher","DOI":"10.1134\/S1070428015040181"},{"key":"e_1_2_5_19_1","doi-asserted-by":"publisher","DOI":"10.1134\/S1070428014010205"},{"key":"e_1_2_5_19_2","doi-asserted-by":"publisher","DOI":"10.1134\/S1070428014100169"},{"key":"e_1_2_5_19_3","doi-asserted-by":"publisher","DOI":"10.1134\/S1070428010020144"},{"key":"e_1_2_5_20_1","doi-asserted-by":"crossref","DOI":"10.1201\/9781420006834","volume-title":"Hansen Solubility Parameters: A User's Handbook, 2nd\u2005ed.","author":"Hansen C. M.","year":"2007"},{"key":"e_1_2_5_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/ie402410w"},{"key":"e_1_2_5_22_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5GC01534K"},{"key":"e_1_2_5_22_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1111166"},{"key":"e_1_2_5_23_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4RA10662H"},{"key":"e_1_2_5_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.200900169"},{"key":"e_1_2_5_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/macp.201400137"},{"key":"e_1_2_5_24_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.memsci.2012.05.006"},{"key":"e_1_2_5_24_3","doi-asserted-by":"publisher","DOI":"10.1002\/app.36711"},{"key":"e_1_2_5_25_1","doi-asserted-by":"publisher","DOI":"10.1039\/b923631g"},{"key":"e_1_2_5_26_1","unstructured":"ACD\/I-lab version\u20052.0 http:\/\/ilab.cds.rsc.org(accessed through the National Chemical Database Service (RSC) 8th June 2016)."},{"key":"e_1_2_5_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ijpharm.2012.01.001"},{"key":"e_1_2_5_28_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4GC01231C"},{"key":"e_1_2_5_29_1","doi-asserted-by":"publisher","DOI":"10.1134\/S107042801409140"},{"key":"e_1_2_5_29_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.carres.2014.03.017"},{"key":"e_1_2_5_29_3","doi-asserted-by":"publisher","DOI":"10.1081\/CAR-120003745"},{"key":"e_1_2_5_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.56"},{"key":"e_1_2_5_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201001743"},{"key":"e_1_2_5_31_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2gc16515e"},{"key":"e_1_2_5_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr00032a005"},{"key":"e_1_2_5_33_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF00647061"},{"key":"e_1_2_5_33_2","volume-title":"Solvents and Solvent Effects in Organic Chemistry, 3rd\u2005ed.","author":"Reichardt C.","year":"2003"},{"key":"e_1_2_5_34_1","doi-asserted-by":"publisher","DOI":"10.1039\/B303095D"},{"key":"e_1_2_5_35_1","doi-asserted-by":"publisher","DOI":"10.1039\/cs9932200409"},{"key":"e_1_2_5_36_1","doi-asserted-by":"publisher","DOI":"10.1039\/p29860001071"},{"key":"e_1_2_5_37_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0378-3812(01)00754-3"},{"key":"e_1_2_5_38_1","doi-asserted-by":"publisher","DOI":"10.1039\/c0gc00797h"},{"key":"e_1_2_5_39_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2gc16670d"},{"key":"e_1_2_5_40_1","unstructured":"J. W.Kim S. H.Hwang Y. K.Kim H. J.Jung J. H.Park E. Y.Lee J. O.Lim S. H.Han K. H.Kim E. J.Jeong S. Y.Kim US pat. 20150069344 2015."},{"key":"e_1_2_5_41_1","first-page":"2186","volume":"25","author":"Biajoli A. F. P.","year":"2014","journal-title":"J. Braz. Chem. Soc."},{"key":"e_1_2_5_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200900587"},{"key":"e_1_2_5_41_3","doi-asserted-by":"publisher","DOI":"10.1021\/cr0505268"},{"key":"e_1_2_5_42_1","doi-asserted-by":"publisher","DOI":"10.1039\/B703488C"},{"key":"e_1_2_5_43_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-1139(00)81957-0"}],"container-title":["ChemSusChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fcssc.201600795","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fcssc.201600795","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cssc.201600795","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T19:14:17Z","timestamp":1760382857000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cssc.201600795"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2016,11,17]]},"references-count":58,"journal-issue":{"issue":"24","published-print":{"date-parts":[[2016,12,20]]}},"alternative-id":["10.1002\/cssc.201600795"],"URL":"https:\/\/doi.org\/10.1002\/cssc.201600795","archive":["Portico"],"relation":{},"ISSN":["1864-5631","1864-564X"],"issn-type":[{"value":"1864-5631","type":"print"},{"value":"1864-564X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2016,11,17]]},"assertion":[{"value":"2016-06-14","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2016-11-17","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}