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para-Menthane as a Stable Terpene Derived from Orange By-Products as a Novel Solvent for Green Extraction and Solubilization of Natural Substances

This study aims at investigating p-menthane, a novel bio-based solvent resulting from the hydrogenation of d-limonene, as a green alternative to n-hexane or toluene for the extraction and solubilization of natural substances. First, conductor-like combination of quantum chemistry (COSMO) coupled wit...

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Autores principales: Madji, Sara, Hilali, Soukaina, Fabiano-Tixier, Anne-Sylvie, Tenon, Mathieu, Bily, Antoine, Laguerre, Mickaël, Chemat, Farid
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6600425/
https://www.ncbi.nlm.nih.gov/pubmed/31181870
http://dx.doi.org/10.3390/molecules24112170
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author Madji, Sara
Hilali, Soukaina
Fabiano-Tixier, Anne-Sylvie
Tenon, Mathieu
Bily, Antoine
Laguerre, Mickaël
Chemat, Farid
author_facet Madji, Sara
Hilali, Soukaina
Fabiano-Tixier, Anne-Sylvie
Tenon, Mathieu
Bily, Antoine
Laguerre, Mickaël
Chemat, Farid
author_sort Madji, Sara
collection PubMed
description This study aims at investigating p-menthane, a novel bio-based solvent resulting from the hydrogenation of d-limonene, as a green alternative to n-hexane or toluene for the extraction and solubilization of natural substances. First, conductor-like combination of quantum chemistry (COSMO) coupled with statistical thermodynamics (RS) calculations show a comparable solubilization profile of p-menthane and n-hexane for carotene, volatile monoterpenes such as carvone and limonene, and model triglycerides. Other data obtained experimentally in solid/liquid extraction conditions further indicate that p-menthane showed similar performances to n-hexane for extracting carotenes from carrots, aromas from caraway seeds, and oils from rapeseeds, as these products showed a comparable composition. p-Menthane was also tested using common analytical extraction procedures such as Soxhlet for determination of oil content via multiple extraction stages, and Dean–Stark for determination of water content via azeotropic distillation. For both systems, yields were comparable, but for Dean–Stark, the distillation curve slope was higher when using p-menthane, and the time needed to attain 100% water recovery was 55% shorter than for toluene. Taken together, these results reveal the potential of p-menthane as a green replacer for petroleum-based solvents such as n-hexane or toluene.
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spelling pubmed-66004252019-07-16 para-Menthane as a Stable Terpene Derived from Orange By-Products as a Novel Solvent for Green Extraction and Solubilization of Natural Substances Madji, Sara Hilali, Soukaina Fabiano-Tixier, Anne-Sylvie Tenon, Mathieu Bily, Antoine Laguerre, Mickaël Chemat, Farid Molecules Article This study aims at investigating p-menthane, a novel bio-based solvent resulting from the hydrogenation of d-limonene, as a green alternative to n-hexane or toluene for the extraction and solubilization of natural substances. First, conductor-like combination of quantum chemistry (COSMO) coupled with statistical thermodynamics (RS) calculations show a comparable solubilization profile of p-menthane and n-hexane for carotene, volatile monoterpenes such as carvone and limonene, and model triglycerides. Other data obtained experimentally in solid/liquid extraction conditions further indicate that p-menthane showed similar performances to n-hexane for extracting carotenes from carrots, aromas from caraway seeds, and oils from rapeseeds, as these products showed a comparable composition. p-Menthane was also tested using common analytical extraction procedures such as Soxhlet for determination of oil content via multiple extraction stages, and Dean–Stark for determination of water content via azeotropic distillation. For both systems, yields were comparable, but for Dean–Stark, the distillation curve slope was higher when using p-menthane, and the time needed to attain 100% water recovery was 55% shorter than for toluene. Taken together, these results reveal the potential of p-menthane as a green replacer for petroleum-based solvents such as n-hexane or toluene. MDPI 2019-06-09 /pmc/articles/PMC6600425/ /pubmed/31181870 http://dx.doi.org/10.3390/molecules24112170 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Madji, Sara
Hilali, Soukaina
Fabiano-Tixier, Anne-Sylvie
Tenon, Mathieu
Bily, Antoine
Laguerre, Mickaël
Chemat, Farid
para-Menthane as a Stable Terpene Derived from Orange By-Products as a Novel Solvent for Green Extraction and Solubilization of Natural Substances
title para-Menthane as a Stable Terpene Derived from Orange By-Products as a Novel Solvent for Green Extraction and Solubilization of Natural Substances
title_full para-Menthane as a Stable Terpene Derived from Orange By-Products as a Novel Solvent for Green Extraction and Solubilization of Natural Substances
title_fullStr para-Menthane as a Stable Terpene Derived from Orange By-Products as a Novel Solvent for Green Extraction and Solubilization of Natural Substances
title_full_unstemmed para-Menthane as a Stable Terpene Derived from Orange By-Products as a Novel Solvent for Green Extraction and Solubilization of Natural Substances
title_short para-Menthane as a Stable Terpene Derived from Orange By-Products as a Novel Solvent for Green Extraction and Solubilization of Natural Substances
title_sort para-menthane as a stable terpene derived from orange by-products as a novel solvent for green extraction and solubilization of natural substances
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6600425/
https://www.ncbi.nlm.nih.gov/pubmed/31181870
http://dx.doi.org/10.3390/molecules24112170
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