{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,5]],"date-time":"2026-05-05T16:26:09Z","timestamp":1777998369344,"version":"3.51.4"},"reference-count":44,"publisher":"MDPI AG","issue":"17","license":[{"start":{"date-parts":[[2022,8,26]],"date-time":"2022-08-26T00:00:00Z","timestamp":1661472000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Fondo Francisco Jos\u00e9 de Caldas","award":["RC-FP44842-212-2018"],"award-info":[{"award-number":["RC-FP44842-212-2018"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Verbenone and carvone are allylic monoterpenoid ketones with many applications in the fine chemicals industry that can be obtained, respectively, from the allylic oxidation of \u03b1-pinene and limonene over a silica-supported iron hexadecachlorinated phthalocyanine (FePcCl16-NH2-SiO2) catalyst and with t-butyl hydroperoxide (TBHP) as oxidant. As there are no reported analyses of the environmental impacts associated with catalytic transformation of terpenes into value-added products that include the steps associated with synthesis of the catalyst and several options of raw materials in the process, this contribution reports the evaluation of the environmental impacts in the conceptual process to produce verbenone and carvone considering two scenarios (SI-raw-oils and SII-purified-oils). The impact categories were evaluated using ReCiPe and IPCC methods implemented in SimaPro 9.3 software. The environmental impacts in the synthesis of the heterogeneous catalyst FePcCl16-NH2-SiO2 showed that the highest burdens in terms of environmental impact come from the use of fossil fuel energy sources and solvents, which primarily affect human health. The most significant environmental impacts associated with carvone and verbenone production are global warming and fine particulate matter formation, with fewer environmental impacts associated with the process that starts directly from turpentine and orange oils (SI-raw-oils) instead of the previously extracted \u03b1-pinene and limonene (SII-purified-oils). As TBHP was identified as a hotspot in the production process of verbenone and carvone, it is necessary to choose a more environmentally friendly and energy-efficient oxidizing agent for the oxidation of turpentine and orange oils.<\/jats:p>","DOI":"10.3390\/molecules27175479","type":"journal-article","created":{"date-parts":[[2022,8,29]],"date-time":"2022-08-29T03:34:56Z","timestamp":1661744096000},"page":"5479","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Comparison by Life-Cycle Assessment of Alternative Processes for Carvone and Verbenone Production"],"prefix":"10.3390","volume":"27","author":[{"given":"Jaime-Andr\u00e9s","family":"Becerra","sequence":"first","affiliation":[{"name":"Environmental Catalysis Research Group, Chemical Engineering Department, Engineering Faculty, Universidad de Antioquia UdeA, Calle 70 No. 52-21, Medell\u00edn 050010, Colombia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5461-6041","authenticated-orcid":false,"given":"Juan-Miguel","family":"Gonz\u00e1lez","sequence":"additional","affiliation":[{"name":"Environmental Catalysis Research Group, Chemical Engineering Department, Engineering Faculty, Universidad de Antioquia UdeA, Calle 70 No. 52-21, Medell\u00edn 050010, Colombia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3770-3223","authenticated-orcid":false,"given":"A\u00edda-Luz","family":"Villa","sequence":"additional","affiliation":[{"name":"Environmental Catalysis Research Group, Chemical Engineering Department, Engineering Faculty, Universidad de Antioquia UdeA, Calle 70 No. 52-21, Medell\u00edn 050010, Colombia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,8,26]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"110801","DOI":"10.1016\/j.foodres.2021.110801","article-title":"Headspace Volatolome of Peel Flours from Citrus Fruits Grown in Brazil","volume":"150","author":"Cunha","year":"2021","journal-title":"Food Res. Int."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"110231","DOI":"10.1016\/j.foodres.2021.110231","article-title":"Insights into the Chemical Composition and Bioactivities of Citrus Peel Essential Oils","volume":"143","author":"Singh","year":"2021","journal-title":"Food Res. Int."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"112857","DOI":"10.1016\/j.phytochem.2021.112857","article-title":"\u03b1-Pinene: A Never-Ending Story","volume":"190","author":"Allenspach","year":"2021","journal-title":"Phytochemistry"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"184","DOI":"10.1016\/S1360-1385(99)01401-6","article-title":"Resin-Based Defenses in Conifers","volume":"4","author":"Phillips","year":"1999","journal-title":"Trends Plant Sci."},{"key":"ref_5","first-page":"234","article-title":"Clean Limonene Transformations into Added-Value Compounds of Fine Chemistry Using Heterogeneous Catalysis","volume":"Volume 47","author":"Taylor","year":"2019","journal-title":"Advances in Chemistry Research"},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Bajpai, P. (2018). Chapter 17\u2014Kraft Spent Liquor Recovery. Biermann\u2019s Handbook of Pulp and Paper: Raw Material and Pulp Making, Elsevier. [3rd ed.].","DOI":"10.1016\/B978-0-12-814240-0.00017-3"},{"key":"ref_7","unstructured":"Pandey, A., H\u00f6fer, R., Taherzadeh, M., Nampoothiri, K.M., and Larroche, C. (2015). Chapter 3B\u2014The Pine Biorefinery Platform Chemicals Value Chain. Industrial Biorefineries & White Biotechnology, Elsevier."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"413","DOI":"10.1016\/j.foodchem.2005.01.003","article-title":"Carvone: Why and How Should One Bother to Produce This Terpene","volume":"95","year":"2006","journal-title":"Food Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"128375","DOI":"10.1016\/j.chemosphere.2020.128375","article-title":"Ecotoxicity of Pesticides and Semiochemicals Used for Control and Prevention of Conifer Bark Beetle (Dendroctonus Spp.) Outbreaks","volume":"263","year":"2021","journal-title":"Chemosphere"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"107628","DOI":"10.1016\/j.biotechadv.2020.107628","article-title":"Microbial Production of Limonene and Its Derivatives: Achievements and Perspectives","volume":"44","author":"Ren","year":"2020","journal-title":"Biotechnol. Adv."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"125","DOI":"10.1016\/S1572-5995(01)80007-7","article-title":"Biotransformation of Terpenoids by Microorganisms","volume":"Volume 25","year":"2001","journal-title":"Bioactive Natural Products (Part F)"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"77","DOI":"10.1016\/j.cofs.2018.03.005","article-title":"Biogeneration of Aroma Compounds","volume":"19","author":"Sales","year":"2018","journal-title":"Curr. Opin. Food Sci."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"241","DOI":"10.1016\/j.molcata.2004.12.008","article-title":"Oxyfunctionalization of Limonene Using Vanadium Complex Anchored on Functionalized SBA-15","volume":"229","author":"Joseph","year":"2005","journal-title":"J. Mol. Catal. A Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"266","DOI":"10.1016\/j.apcata.2017.11.016","article-title":"Novel Access to Verbenone via Ruthenium Nanoparticles-Catalyzed Oxidation of \u03b1-Pinene in Neat Water","volume":"550","author":"Rauchdi","year":"2018","journal-title":"Appl. Catal. A Gen."},{"key":"ref_15","first-page":"8","article-title":"Oxidation of Olefins Employing Mesoporous Molecular Sieves Modified with Copper","volume":"462\u2013463","author":"Eimer","year":"2013","journal-title":"Appl. Catal. A Gen."},{"key":"ref_16","unstructured":"Davey, P.N., Newman, C.P., Thiam, W.A., and Tse, C.-L. (2000). Preparation of Carvone. (WO2000058253A1)."},{"key":"ref_17","unstructured":"Derfer, J.M., Kane, B.J., and Young, D.G. (1966). Preparation of Carvone. (U.S. Patent US3293301)."},{"key":"ref_18","unstructured":"Bain, J.P., and Gary, W.Y. (1956). Preparation of Verbenone. (U.S. Patent US2767215A)."},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Yang, M., Long, Q., Li, W., Wang, Z., He, X., Wang, J., Wang, X., Xiong, H., Guo, C., and Zhang, G. (2020). Mapping the Environmental Cost of a Typical Citrus-Producing County in China: Hotspot and Optimization. Sustainability, 12.","DOI":"10.3390\/su12051827"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"291","DOI":"10.1016\/j.egyr.2022.01.063","article-title":"Life Cycle Energy and Carbon Emissions of Essential Oil Extraction from Rosemary","volume":"8","author":"Moura","year":"2022","journal-title":"Energy Rep."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"152574","DOI":"10.1016\/j.scitotenv.2021.152574","article-title":"Circular Bioeconomy: Life Cycle Assessment of Scaled-up Cascading Production from Orange Peel Waste under Current and Future Electricity Mixes","volume":"812","author":"Teigiserova","year":"2022","journal-title":"Sci. Total Environ."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"105844","DOI":"10.1016\/j.biombioe.2020.105844","article-title":"Identification of Environmental Aspects of Citrus Waste Valorization into D-Limonene from a Biorefinery Approach","volume":"143","author":"Santiago","year":"2020","journal-title":"Biomass Bioenergy"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.algal.2017.01.001","article-title":"Life Cycle Analysis of a Large-Scale Limonene Production Facility Utilizing Filamentous N2-Fixing Cyanobacteria","volume":"23","author":"Jahandideh","year":"2017","journal-title":"Algal Res."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"152","DOI":"10.1016\/j.spc.2018.03.001","article-title":"Life Cycle Assessments of Bio-Based Sustainable Polylimonene Carbonate Production Processes","volume":"14","author":"Zhang","year":"2018","journal-title":"Sustain. Prod. Consum."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1016\/j.spc.2020.10.017","article-title":"Identification by Life Cycle Assessment of the Critical Stage in the Catalytic Synthesis of Nopol Using Heterogeneous Catalysis","volume":"27","author":"Hasenstab","year":"2021","journal-title":"Sustain. Prod. Consum."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"12","DOI":"10.1016\/j.molcata.2016.05.029","article-title":"Kinetic Study of \u03b1-Pinene Allylic Oxidation over FePcCl16-NH2-SiO2 Catalyst","volume":"423","author":"Becerra","year":"2016","journal-title":"J. Mol. Catal. A"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"250","DOI":"10.1016\/j.cattod.2017.07.012","article-title":"A Bio-Inspired Heterogeneous Catalyst for the Transformation of Limonene from Orange Peel Waste Biomass into Value-Added Products","volume":"302","author":"Becerra","year":"2018","journal-title":"Catal. Today"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"707","DOI":"10.1021\/acs.oprd.8b00083","article-title":"Continuous Production of Anhydrous Tert-Butyl Hydroperoxide in Nonane Using Membrane Pervaporation and Its Application in Flow Oxidation of a \u03b3-Butyrolactam","volume":"22","author":"Li","year":"2018","journal-title":"Org. Process Res. Dev."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1065","DOI":"10.1021\/ic00176a014","article-title":"Synthesis and Properties of Substituted (phthalocyaninato)-Iron and -Cobalt Compounds and Their Pyridine Adducts","volume":"23","author":"Metz","year":"1984","journal-title":"Inorg. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"473","DOI":"10.1039\/a901689i","article-title":"Heterogeneous Oxidation of Aromatic Compounds Catalyzed by Metallophthalocyanine Functionalized Silicas","volume":"23","author":"Sorokin","year":"1999","journal-title":"New J. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"2295","DOI":"10.1002\/ceat.201900691","article-title":"Techno-Economic Evaluation of D-Limonene and \u03b1-Pinene Separation from Citrus and Turpentine Oils","volume":"43","author":"Becerra","year":"2020","journal-title":"Chem. Eng. Technol."},{"key":"ref_32","unstructured":"International Organization for Standardization (2006). Environmental Management\u2014Life Cycle Assessment\u2014Principles and Framework, ISO. [2nd ed.]. ISO 14040:2006."},{"key":"ref_33","unstructured":"International Organization for Standardization (2006). Environmental Management\u2014Life Cycle Assessment\u2014Requirements and Guidelines, ISO. [1st ed.]. ISO 14044:2006."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"707","DOI":"10.1007\/s00267-008-9251-y","article-title":"Resource Consumption and Environmental Impacts of the Agrofood Sector: Life Cycle Assessment of Italian Citrus-Based Products","volume":"43","author":"Beccali","year":"2009","journal-title":"Environ. Manag."},{"key":"ref_35","unstructured":"Winkler, D.L.E., and Hearne, G.W. (1958). Shell Development Co. Non-Catalytic Liquid Phase Isobutane Oxidation. No. (U.S. Patent US2845461A)."},{"key":"ref_36","unstructured":"Jubin, J.C. (1978). Manufacture of Tertiary Butyl Hydroperoxide. Lyondell Chemical Technology LP. No. (U.S. Patent US4128587A)."},{"key":"ref_37","unstructured":"Takatsuna, K., Shiozawa, K., and Okumura, Y. (1990). Process for Preparing Amino-Propyl Silanes. (Eur. Pat. EP0403706A2)."},{"key":"ref_38","unstructured":"Converse, W. (1940). Process for Production of Unsaturated Amines. (U.S. Patent US2216548A)."},{"key":"ref_39","unstructured":"Ronzio, R.A., Davis, P.K., and Ziegler, R.C. (1978). Process for Producing Ammonium Heptamolybdate and\/or Ammonium Dimolybdate. (U.S. Patent US4079116)."},{"key":"ref_40","unstructured":"Blume, P.W., Thomas, G.A., and Gervais, B. (1947). Chlorination of Phthalic Anhydride. (U.S. Patent US2429985A)."},{"key":"ref_41","unstructured":"Yongsheng, Z., Renjie, Y., Chen, J., and Jiangyin Jingcheng Glass Co., Ltd. (2006). Production Process of Triethoxy Silane. (China Pat. CN1810811A)."},{"key":"ref_42","unstructured":"PR\u00e9 Sustainability, B.V. (2022, March 15). SimaPro. Available online: https:\/\/simapro.com\/."},{"key":"ref_43","doi-asserted-by":"crossref","unstructured":"Huijbregts, M.A.J., Steinmann, Z.J.N., Elshout, P.M.F., Stam, G., Verones, F., Vieira, M.D.M., Hollander, A., Zijp, M., and van Zelm, R. (2016). ReCiPe 2016 v1.1. A Harmonized Life Cycle Impact Assessment Method at Midpoint and Endpoint Level Report I: Characterization, National Institute for Public Health and the Environment.","DOI":"10.1007\/s11367-016-1246-y"},{"key":"ref_44","unstructured":"IPCC (2022, March 15). The Intergovernmental Panel on Climate Change. Available online: https:\/\/www.ipcc.ch\/."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/17\/5479\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T00:15:46Z","timestamp":1760141746000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/17\/5479"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,8,26]]},"references-count":44,"journal-issue":{"issue":"17","published-online":{"date-parts":[[2022,9]]}},"alternative-id":["molecules27175479"],"URL":"https:\/\/doi.org\/10.3390\/molecules27175479","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,8,26]]}}}