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; Chémat, Farid

doi:10.3390/molecules24112170

Cited by 12 publications

(5 citation statements)

References 38 publications

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“…168 °C) and p-cymene (b.p. 177 °C) can be separated through azeotropic or extractive distillation processes, [33] with pure p-menthane useful as a green solvent for cleaning applications [34] and natural product extraction, [35] as well as for the production of p-menthane hydroperoxide as an initiator for polymerization reactions. [36] Importantly, combining the low soot combustion properties of p-menthane with the greater engine seal compatibility of aromatic p-cymene (minimum of 8% aromatic content required for good seal compatibility for military jet fuel specifications) means that use of unfractionated mixtures of p-menthane and p-cymene as biofuel blends is also potentially attractive.…”

Section: Hydrogenation Of Desulfurized P-menthadienes Mixtures To Afford a Mixture Of P-menthane And P-cymene As A Potential Biofuelmentioning

confidence: 99%

p‐Menthadienes as Biorenewable Feedstocks for a Monoterpene‐Based Biorefinery

Tibbetts

Bull

2021

Advanced Sustainable Systems

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the upgrading of biomass into biofuels and platform chemicals will need to be developed and integrated into new/existing chemical processes. [2] The large volumes and wide geographical distribution of lignocellulosic biomass means that it will undoubtedly play a key role as a biorenewable feedstock for bulk chemical production. [3] In this approach, fermentative processes are used to depolymerize lignocellulose biomass into sugars (e.g., glucose and fructose), with these monomers then transformed into low-value feedstocks such as bioethanol, succinic acid, glutamic acid, and 5-hydroxymethylfurfural. [4] Although highly promising, technological difficulties associated with large-scale catalytic upgrading of these highly oxygenated biopolymers cause significant problems that still need to be overcome before lignocellulose-based biorefineries become more widely established. [5] Monoterpenes (and monoterpenoids) represent an alternative biomass source for the production of biofuels, polymers, and chemicals that are available in significant volumes at low cost. Significant amounts of commercially available monoterpenes are currently produced as products and waste from the forestry and agricultural industries, all of which can be considered as potentially useful biorenewable feedstocks for fuel and chemical production. These include turpentine (≈360 000 tonnes pa), limonene-containing citrus oil (≈30 000 tonnes pa), mentholcontaining mint oil (≈20 000 tonnes pa), and 1,8-cineole from eucalyptus oil (≈7000 tonnes pa with an estimated multimillion tonne production potential per annum). [6] The structures of these energy-dense, lightly oxygenated, alkene-containing C 10 building blocks more closely resemble those of petroleum-based hydrocarbons, which means they can potentially be catalytically upgraded using existing refining technologies to produce a wide range of chemical products (including aromatics).Crude sulfate turpentine (CST) is the cheapest and most widely available source of monoterpene biomass, with around 260 000 tonnes of CST produced as a waste by-product of the paper industry annually. High pressure cooking of wood chips to produce paper pulp in the Kraft process generates around 15 kg of CST per tonne of pulp, [7] which is comprised of a mixture of monoterpenes and around 5% volatile sulfur compounds (e.g., Me 2 S). [6a] A further annual 100 000 tonnes of pinene-rich gum turpentine (GT) is also produced through sustainable tapping of the trunks of living trees. The major monoterpene components of turpentine are α-pinene, β-pinene, 3-carene, and limonene, along with small amounts of camphene and C 15 A terpene-based biorefinery is described that uses crude sulfate turpentine (CST) and gum turpentine (GT) to produce mixtures of p-menthadienes (p-MeDs) as biorenewable terpene feedstocks. An acid catalyzed ring opening reaction (6 m aq. H 2 SO 4 , 90 °C) is first used to convert the major bicyclic monoterpenes (α-pinene, β-pinene, and 3-carene) in untreated CST (or GT with 5 mol% Me 2 S) into mixtures of ...

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Section: Hydrogenation Of Desulfurized P-menthadienes Mixtures To Afford a Mixture Of P-menthane And P-cymene As A Potential Biofuelmentioning

confidence: 99%

p‐Menthadienes as Biorenewable Feedstocks for a Monoterpene‐Based Biorefinery

Tibbetts

Bull

2021

Advanced Sustainable Systems

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“…Filly et al [241] calculated sigma potential similarities of solvents and solutes for the comparison of the solvents in lipid extraction for caraway seeds, being the values in agreement with experimental results [241]. In addition, relative solubilities have been calculated and applied in prediction of the extraction of lipids from rapeseeds [236][237][238], carotenoids from carrots [237,238], aromas from caraway seeds [237,238] and betulin from bitch bark [245] using terpenes. Lastly, as it was previously mentioned, Rodríguez-Llorente et al applied the COSMO-RS method for calculating the infinite dilution activity coefficients as solvent screening of terpenes and terpenoids in extraction of volatile fatty acids from water [26] and separation of phenols from industrial wastewater [27], obtaining very similar trends in predictions and experimental data using various terpenes and terpenoids.…”

Section: Predictive Methods In Extraction With Terpenes and Terpenoidsmentioning

confidence: 80%

A Review of the Use of Eutectic Solvents, Terpenes and Terpenoids in Liquid–liquid Extraction Processes

et al. 2020

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Diverse and abundant applications of the eutectic solvents have appeared in the last years. Their promising tunable properties, eco-friendly character and the possibility of being prepared from numerous compounds have led to the publication of numerous papers addressing their use in different areas. Terpenes and terpenoids have been employed in the formulation of eutectic solvents, though they also have been applied as solvents in extraction processes. For their hydrophobic nature, renewable character, low environmental impact, cost and being non-hazardous, they have also been proposed as possible substitutes of conventional solvents in the separation of organic compounds from aqueous streams, similarly to hydrophobic eutectic solvents. The present work reviews the application of eutectic solvents in liquid–liquid extraction and terpenes and terpenoids in extraction processes. It has been made a research in the current state-of-the-art in these fields, describing the proposed applications of the solvents. It has been highlighted the scale-up feasibility, solvent regeneration and reuse procedures and the comparison of the performance of eutectic solvents, terpenes and terpenoids in extraction with conventional organic solvents or ionic liquids. Ultimately, it has been also discussed the employ of predictive methods in extraction, the reliability of thermodynamic models in correlation of liquid–liquid equilibria and simulation of liquid–liquid extraction processes.

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“…p -menthane (stable saturated derivative of d-limonene) and cis/trans-pinane: 7:3 (stable saturated derivative of α-pinene and β-pinene) were investigated as new saturated terpene solvents for oil extraction. Both solvents showed promising results with comparable oil yields to n -hexane (40.5 vs. 39.5 g/100 g DM for p -menthane and n -hexane, respectively [ 99 ], and 42.5 vs. 43.2 g/100 g DM for pinane and n -hexane, respectively [ 98 ]). The encouraging lab-scale results still need further research for the development of a pilot-scale terpene extraction process.…”

Section: Green Solvents’ Extractionmentioning

confidence: 99%

Leading Edge Technologies and Perspectives in Industrial Oilseed Extraction

Cravotto

Claux²,

Bartier³

et al. 2023

Molecules

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With the increase in the world’s population and per capita wealth, oil producers must not only increase edible oil production but also meet the demand for a higher quality and variety of products. Recently, the focus has shifted from single processing steps to the entire vegetable oil production process, with an emphasis on introducing innovative technologies to improve quality and production efficiency. In this review, conventional methods of oilseed storage, processing and extraction are presented, as well as innovative processing and extraction techniques. Furthermore, the parameters most affecting the products’ yields and quality at the industrial level are critically described. The extensive use of hexane for the extraction of most vegetable oils is undoubtedly the main concern of the whole production process in terms of health, safety and environmental issues. Therefore, special attention is paid to environmentally friendly solvents such as ethanol, supercritical CO2, 2-methyloxolane, water enzymatic extraction, etc. The state of the art in the use of green solvents is described and an objective assessment of their potential for more sustainable industrial processes is proposed.

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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

Cited by 12 publications

References 38 publications

p‐Menthadienes as Biorenewable Feedstocks for a Monoterpene‐Based Biorefinery

p‐Menthadienes as Biorenewable Feedstocks for a Monoterpene‐Based Biorefinery

A Review of the Use of Eutectic Solvents, Terpenes and Terpenoids in Liquid–liquid Extraction Processes

Leading Edge Technologies and Perspectives in Industrial Oilseed Extraction

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