Abstract
Considering that vegetable oils derived from oleoproteaginous plants are mainly destined for the food industry, other types of oils derived from micro-algae, micro-organisms and fruit seeds (co-products of food industry) require adapted processes of extraction. These new resources continue to boost the oleochemistry sector for the production of bioproducts. The characteristics of each of these lipid sources in terms of fatty acid profile are opportunities for generating platform molecules and elaborating functional compounds. Each lipid resource is associated with secondary metabolites sought after in the cosmetics, pharmaceutical and nutraceutical sectors. This chapter describes innovative technologies (twin-screw extrusion, ultrasound, thermal induction) thin-film reactor-separator) for isolating, processing and purifying lipids and other seed constituents. To illustrate the contributions of oleochemistry, several strategies for designing bioproducts from vegetable oils are presented. To target specific applications, the properties of several categories of oleochemical biosolvents and biosurfactants are described, in particular those of glycerol carbonate esters. The platform of polyols, the obtention of polyhydroxyurethanes and other biobased polymers show innovative routes for the obtention of novel materials. Finally, an eco-design methodology based on the choice of relevant indicators makes it possible to highlight the interest of these new value chains using some lipids.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Beaudoin, F., Sayanova, O., Haslam, R. P., et al. (2014). Oleaginous crops as integrated production platforms for food, feed, fuel and renewable industrial feedstock. OCL, 21, D606. https://doi.org/10.1051/ocl/2014042
Bergez-Lacoste, M., Thiebaud-Roux, S., De Caro, P., et al. (2014). From chemical platform molecules to new biosolvents: Design engineering as a substitution methodology. Biofuels Bioproductivity Bioreference, 8, 438–451. https://doi.org/10.1002/bbb.1480
Carre, C., Ecochard, Y., Caillol, S., & Averous, A. (2019). From the synthesis of biobased cyclic carbonate to polyhydroxyurethanes: A promising route towards renewable non-isocyanate polyurethanes. Chemsuschem, 12, 3410–3430. https://doi.org/10.1002/cssc.201900737
Clark, J. H., Hunt, A. J., & Topi, C. et al. (2017). Sustainable solvents: perspectives from research, Business and International Policy. (Green chemistry series). The Royal Society of Chemistry. https://doi.org/10.1039/9781782624035
Cornille, A., Auvergne, R., Figovsky, O., Boutevin, B., & Caillol, S. (2017). A perspective approach to sustainable routes for non-isocyanate polyurethanes. European Polymer Journal, 87, 535–552. https://doi.org/10.1016/j.eurpolymj.2016.11.027
De Caro, P., & Thiebaud-Roux, S. (2015). Biosolvants—conception, propriétés et aspects environnementaux. Les Techniques de l’Ingénieur, CHV 4020:14, updated in 2023.
Fabre, J. F., Lacroux, E., Valentin, R., & Mouloungui, Z. (2015). Ultrasonication as a highly efficient method of flaxseed mucilage extraction. Industrial Crops and Products, 65, 354–360. https://doi.org/10.1016/j.indcrop.2014.11.015
Faure, J. D., & Tepfer, M. (2015). Camelina, a swiss kniff for plant lipid biotechnology. Oilseeds and fats, Crops and Lipids (OCL), 23, D503. https://doi.org/10.1051/ocl/2016023
Fernandez-Moya, V., Martinez-Force, E., & Garces, R. (2000). Identification of triacylglycerol species from high-saturated sunflower (Helianthus annuus) mutants. Journal of Agriculture and Food Chemistry, 48, 764–769. https://doi.org/10.1021/jf9903861
Godard, A., de Caro, P., Vedrenne, E., Mouloungui, Z., & Thiebaud-Roux, S. (2016). From crops to crops: Preserving the ecosystem through the use of biobased molecules. OCL, 23, D510. https://doi.org/10.1051/ocl/2016037
Goodby, J. W., Görtz, V., Cowling, S. J., et al. (2007). Thermotropic liquid crystalline glycolipids. Chemical Society Reviews, 36, 1971. https://doi.org/10.1039/B708458G
Gunstone, F. D. (2011). Supplies of vegetable oils for non-food purpose. European Journal of Lipid Science and Technology, 113, 3–7. https://doi.org/10.1002/ejlt.201000104
Hashemi, B., Shiri, F., Svec, F., & Navakova, L. (2022). Green Solvents and Approaches Recently Applied for Extraction of Natural Bioactive Compounds. https://doi.org/10.1016/j.trac.2022.116732
Holmiere, S., Valentin, R., Maréchal, P., & Mouloungui, Z. (2017). Esters of oligo-(glycerol carbonate-glycerol): New biobased oligomeric surfactants. Journal of Collidal Interface Science, 487, 418–425. https://doi.org/10.1016/j.jcis.2016.10.072
Javni, I., Hong, D. P., & Petrovic, Z. S. (2008). Soy-Based Polyurethanes by nonisocyanate route. Journal of Applied Polymer Science, 108, 3867–3875. https://doi.org/10.1002/app.27995
Klasson, K. T., Qi, Y., Bruni, G. O., Watson, T. T., Pancio, B. T., & Terrell, E. (2023). Recovery of aconitic acid from sweet sorghum plant extract using a solvent mixture, and its potential use as a nematicide. Life, 13(3), 724. https://doi.org/10.3390/life13030724
Leser, M. E., Sagalowicz, L., Michel, M., & Watzke, H. J. (2006). Self-assembly of polar food lipids. Advances in Colloid and Interface Science, 123–126, 125–136. https://doi.org/10.1016/j.cis.2006.07.003
Liu, C., Wang, G., Sui, W., et al. (2017). Preparation and characterization of chitosan by a novel deacetylation approach using glycerol as green reaction solvent. ACS Sustainaible Chemical Engineering, 5, 4690–4698. https://doi.org/10.1021/acssuschemeng.7b00050
Lligadas, G., Ronda, J. C., Galaià, M., & Cadiz, V. (2010). Plant oils as platform chemicals for urethane synthesis: Current state of the art. Biomacromolecules, 11, 2825–2835. https://doi.org/10.1021/bm100839x
Maisonneuve, L., Chollet, G., Grau, E., & Cramail, H. (2016). Vegetable oils: a source of polyols for polyurethane material. Oilseeds and fats, Crops and Lipids (OCL) 23, D508. https://doi.org/10.1051/ocl/2016031
Moity, L., Benazzouz, A., Molinier, V., et al. (2015). Glycerol acetals and ketals as bio-based solvents: Positioning in Hansen and COSMO-RS spaces, volatility and stability towards hydrolysis and autoxidation. Green Chemistry, 17, 1779–1792. https://doi.org/10.1039/C4GC02377C
Mouloungui, Z., Pelet, S., Eychenne, V., & Matéo, S. (2006). La lipochimie. Colonna P (pp. 305–356). Chimie Verte. Lavoisier Tec et Doc.
Nagtode, V. S., & Cardoza, C., et al. (2023) Green surfactants (biosurfactants): a petroleum-free substitute for sustainability-Comparison, applications, market, and future prospects. ACS Omega, 8, 11674–11699. https://pubs.acs.org/doi/10.1021
Nohra, B., Candy, L., Blanco, J. F., et al. (2016). Synthesis of high-molecular weight multifunctional glycerol polyhydroxyurethanes PHUs. Molecules, 21, 1220–1233. https://doi.org/10.3390/molecules21091220
Nyame Mendendy Boussambe, G., Valentin, R., Fabre, J. F., et al. (2017). Self-assembling behavior of glycerol monoundecenoate in water. Langmuir, 33, 3223–3233. https://doi.org/10.1021/acs.langmuir.6b03584
Ochsenreither, K., Glück, C., Stressler, T., Fischer, L., & Syldatk, C. (2016). Production strategies and applications of microbial single cell oils. Frontier Microbiology, 7. https://doi.org/10.3389/fmicb.2016.01539
Oil-World Energy Outlook 2019 (IEA, 2019). https://iea.blob.core.windows.net/assets/98909c1b-aabc-4797-9926-35307b418cdb/WEO2019-free.pdf
Palaskar, D. V., Boyer, A., Clouet, E., et al. (2010). Synthesis of biobased polyurethane from oleic and ricinoleic acids as the renewable resources via the AB-type self-condensation approach. Biomacromolecules, 11, 1202–1211. https://doi.org/10.1021/bm100233v
Pilogé, E. (2020). Sunflower in the global vegetable oil system: situation, specificities and perspectives. Oilseeds and fats, Crops and Lipids (OCL), 27, 34. https://doi.org/10.1051/ocl/2020028
Plastics insight: Polyurethane Production, Pricing and Market Demand. Retrieved from https://www.plasticsinsight.com/resin-intelligence/resin-prices/polyurethane/
Poulenat, G., Sentenac, S., & Mouloungui, Z. (2004). Double decomposition reactions for the production of alkaline and alkaline-earth oleic soaps under salting-out conditions. Industrial and Engineering Chemistry Research, 43, 1574–1579. https://doi.org/10.1021/ie030508l
Reznik, G. O., Vishwanath, P., & Pynn, M. A., et al. (2010). Use of sustainable chemistry to produce an acyl amino acid surfactant. Application Microbiology Biotechnology, 86, 1387–97. https://doi.org/10.1007/s00253-009-2431-8
Roche, J., Bouniols, A., Cerny, M., et al. (2016). Fatty acid and phytosterol accumulation during seed ripening in three oilseed species. International Journal of Food Science Technology, 51, 1820–1826. https://doi.org/10.1111/ijfs.13153
Ronda, J. C., Lligadas, G., Galià, M., & Cadiz, V. (2011). Vegetable oils as platform chemicals for polymer synthesis. European Journal of Lipid Science and Technology, 113, 45–58. https://doi.org/10.1002/ejlt.201000103
Salim, D., de Caro, P., Chasseray, X., & Shum, A. (2022). Development of biobased emulsions for postharvest citrus fruit preservation. Sustainable Chemistry and Pharmacy, 25, 100583. https://doi.org/10.1016/j.scp.2021.100583
Savoire, R., Lanoiselle, J. L., & Vorobiev, E. (2013). Mechanical continuous oil expression from oilseeds: A review. Food and Bioprocess Technology, 6, 1–16. https://doi.org/10.1007/s11947-012-0947-x
Sheldon, R. A. (2007). The E factor : Fifteen years on. Green Chemistry, 9, 1273–1283. https://doi.org/10.1039/B713736M
Sutter, M., Da Silva, E., Duguet, N., et al. (2015). Glycerol ether synthesis: A bench test for green chemistry concepts and technologies. Chemical Reviews, 115, 8609–8651. https://doi.org/10.1021/cr5004002
Trost, B. M. (1991). The atom economy–a search for synthetic efficiency. Science, 254, 1471–1477. https://doi.org/10.1126/science.1962206
Uitterhaegen, E., & Evon, P. (2017). Twin-screw extrusion technology for vegetable oil extraction: a review. Journal of Food Engineering, 212, 190–200. https://doi.org/10.1016/j.jfoodeng.2017.06.006
Urata, K., & Taraishi, N. (1996). Ether lipids based on the glycidyl ether skeleton: Present state, future potential. Journal of the American Oil Chemists Society, 73, 819–830. https://doi.org/10.1007/BF02517982
Valentin, R., Alignan, M., Giacinti, G., et al. (2012). Pure short-chain glycerol fatty acid esters and glycerylic cyclocarbonic fatty acid esters as surface-active and antimicrobial coagels protecting surfaces. Journal of Collidal Interface Science, 365, 280–288. https://doi.org/10.1016/j.jcis.2011.09.010
Wu-Tiu-Yen, J., Lameloise, M. L., Petit, A., Lewandowski, R., Broyart, B., & Fargues, C. (2021). Aconitic acid recovery from sugar-cane stillage: From the modeling of the anion-exchange step to the conception of a novel combined process. Separation Science and Technology, 56(10), 1752–1768. https://doi.org/10.1080/01496395.2020.1795677
Yoo, J. W., & Mouloungui, Z. (2003). Catalytic carbonylation of glycerin by urea in the presence of zinc mesoporous system for the synthesis of glycerol carbonate. Studies in Surface Science and Catalysis, 146, 757–760. https://doi.org/10.1016/S0167-2991(03)80494-9
Yuan L, Li R (2020) Metabolic engineering a model oilseed camelina sativa for the sustainable production of high-value designed oils. Frontier Plant Science, 11.https://doi.org/10.3389/fpls.2020.00011
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2024 The Author(s), under exclusive license to Springer Nature Switzerland AG
About this chapter
Cite this chapter
Mouloungui, Z. et al. (2024). Edible Oils and Oleochemistry. In: Baumberger, S. (eds) Green Chemistry and Agro-food Industry: Towards a Sustainable Bioeconomy. Springer, Cham. https://doi.org/10.1007/978-3-031-54188-9_3
Download citation
DOI: https://doi.org/10.1007/978-3-031-54188-9_3
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-031-54187-2
Online ISBN: 978-3-031-54188-9
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)