Volume 9 Issue 4
Nov.  2024
Turn off MathJax
Article Contents
Phannipha Daisuk, Seiichi Takami, Masaki Honda, Motonobu Goto, Chonlatep Usaku, Artiwan Shotipruk. Liquefied dimethyl ether as alternative extraction solvent for high γ-oryzanol rice bran oil: Systematic HSP theory and experimental evaluation[J]. Journal of Bioresources and Bioproducts, 2024, 9(4): 577-591. doi: 10.1016/j.jobab.2024.06.002
Citation: Phannipha Daisuk, Seiichi Takami, Masaki Honda, Motonobu Goto, Chonlatep Usaku, Artiwan Shotipruk. Liquefied dimethyl ether as alternative extraction solvent for high γ-oryzanol rice bran oil: Systematic HSP theory and experimental evaluation[J]. Journal of Bioresources and Bioproducts, 2024, 9(4): 577-591. doi: 10.1016/j.jobab.2024.06.002

Liquefied dimethyl ether as alternative extraction solvent for high γ-oryzanol rice bran oil: Systematic HSP theory and experimental evaluation

doi: 10.1016/j.jobab.2024.06.002
Funds:

This research project is supported by theSecond Century Fund (C2F) and Chulalongkorn University and Thailand Science Research and Innovation Fund Chulalongkorn University(No.BCG66210015).

  • Publish Date: 2024-06-28
  • This study aimed to systematically find an alternative solvent to replace hexane for the extraction of bio-oil with high γ-oryzanol content from rice bran (RB). The selection involved predicting solubility through Hansen solubility theory, experimental validation, determination of suitable extraction conditions, and comparison of oil quality with that of conventional hexane. A wide variety of solvents: subcritical water (SCW), supercritical carbon dioxide (SCCO2), bio-based solvents (alcohols and terpenes), and liquefied dimethyl ether (LDME), were initially assessed for rice bran oil (RBO) and γ-oryzanol solubility using Hansen solubility spheres. Solvents demonstrating high solubility for both RBO and γ-oryzanol, including LDME, ethyl acetate, acetone, and others (alcohols and SCCO2) known for effective vegetable oil extraction, were selected/identified for experimental extraction comparison. Among these, LDME performed better overall, affording greater solubility and requiring less solvent, shorter duration, lower pressure, and no additional co-solvents for equivalent extractions. Optimal conditions for LDME extraction were identified as 30 ℃ with a solvent-to-sample ratio of 10 mL/g and an extraction time of 10 min. Oils extracted with LDME and hexane displayed similar fatty acid compositions and no adverse effects on RB protein and carbohydrate structures after LDME extraction were observed. This study demonstrates LDME as a promising alternative to replace hexane for RBO extraction to further valorize this abundant low-cost RB residue into bio-oil and its γ-oryzanol and de-oil RB co-products.

     

  • loading
  • [1]
    Arab, F., Alemzadeh, I., Maghsoudi, V., 2011. Determination of antioxidant component and activity of rice bran extract. Sci. Iran. 18, 1402-1406.
    [2]
    Azizi, Z., Rezaeimanesh, M., Tohidian, T., Rahimpour, M.R., 2014. Dimethyl ether: a review of technologies and production challenges. Chem. Eng. Process. Process. Intensif. 82, 150-172.
    [3]
    Bauer, M.C., Kruse, A., 2019. The use of dimethyl ether as an organic extraction solvent for biomass applications in future biorefineries: a user-oriented review. Fuel 254, 115703.
    [4]
    Benito-Román, O., Varona, S., Sanz, M.T., Beltrán, S., 2019. Valorization of rice bran: Modified supercritical CO2 extraction of bioactive compounds. J. Ind. Eng. Chem. 80, 273-282.
    [5]
    Bessa, L.C.B.A., Ferreira, M.C., Rodrigues, C.E.C., Batista, E.A.C., Meirelles, A.J.A., 2017. Simulation and process design of continuous countercurrent ethanolic extraction of rice bran oil. J. Food Eng. 202, 99-113.
    [6]
    Bitencourt, R.G., Filho, W.A.R., Paula, J.T., Garmus, T.T., Cabral, F.A., 2016. Solubility of γ-oryzanol in supercritical carbon dioxide and extraction from rice bran. J. Supercrit. Fluid. 107, 196-200.
    [7]
    Boonnoun, P., Tunyasitikun, P., Clowutimon, W., Shotipruk, A., 2017. Production of free lutein by simultaneous extraction and de-esterification of marigold flowers in liquefied dimethyl ether (DME)-KOH-EtOH mixture. Food Bioprod. Process. 106, 193-200.
    [8]
    Capellini, M.C., Giacomini, V., Cuevas, M.S., Rodrigues, C.E.C., 2017. Rice bran oil extraction using alcoholic solvents: Physicochemical characterization of oil and protein fraction functionality. Ind. Crops Prod. 104, 133-143.
    [9]
    Chandi, G.K., Sogi, D.S., 2007. Functional properties of rice bran protein concentrates. J. Food Eng. 79, 592-597.
    [10]
    Chang, J., Fu, Y., Luo, Z.Y., 2012. Experimental study for dimethyl ether production from biomass gasification and simulation on dimethyl ether production. Biomass Bioenergy 39, 67-72.
    [11]
    Daisuk, P., Shotipruk, A., 2020. Recovery of γ-oryzanol from rice bran oil soapstock derived calcium soap: Consideration of Hansen solubility parameters and preferential extractability in various solvents. LWT 134, 110238.
    [12]
    Daud, N.S.M., Zaidel, D.N.A., Lai, K.S., Khairuddin, N., Jusoh, Y.M.M., Muhamad, I.I., 2018. Crude oil yield and properties of rice bran oil from different varieties as affected by extraction conditions using soxhterm method. Arab. J. Sci. Eng. 43, 6237-6244.
    [13]
    de la Peña-Gil, A., Toro-Vazquez, J.F., Rogers, M.A., 2016. Simplifying Hansen solubility parameters for complex edible fats and oils. Food Biophys. 11, 283-291.
    [14]
    Djordjević, M., Djordjević, M., Maravić, N., Teofilović, V., Šoronja-Simović, D., Šereš, Z., 2023. Processing of alfalfa seeds by convective hot air drying, vacuum drying and germination: Proximate composition, techno-functional, thermal and structural properties evaluation. Food Chem. 402, 134300.
    [15]
    Ebnesajjad, S., 2015. Chemical Properties of Fluoropolymers: Polytetrafluoroethylene and Polychlorotrifluoroethylene. Fluoroplastics. Amsterdam: Elsevier, 382-395.
    [16]
    Eghbali Babadi, F., Boonnoun, P., Nootong, K., Powtongsook, S., Goto, M., Shotipruk, A., 2020. Identification of carotenoids and chlorophylls from green algae Chlorococcum humicola and extraction by liquefied dimethyl ether. Food Bioprod. Process. 123, 296-303.
    [17]
    Fang, Y.Z., Gu, S.Q., Liu, S.L., Zhang, J.Y., Ding, Y.T., Liu, J.H., 2018. Extraction of oil from high-moisture tuna liver by subcritical dimethyl ether: feasibility and optimization by the response surface method. RSC Adv. 8, 2723-2732.
    [18]
    Food and Agriculture Organization Statistics, 2019. Food and Agriculture Organization of the United Nations. Italy: Rome.
    [19]
    Fraterrigo Garofalo, S., Demichelis, F., Mancini, G., Tommasi, T., Fino, D., 2022. Conventional and ultrasound-assisted extraction of rice bran oil with isopropanol as solvent. Sustain. Chem. Pharm. 29, 100741.
    [20]
    Fraterrigo Garofalo, S., Tommasi, T., Fino, D., 2021. A short review of green extraction technologies for rice bran oil. Biomass Convers. Biorefin. 11, 569-587.
    [21]
    Gasparetto, H., de Castilhos, F., Salau, N.P.G., 2023. Screening, experimental data, and robust kinetic modeling of vegetable oil extraction using p-cymene as a neoteric solvent for n-hexane replacement. J. Clean. Prod. 392, 136336.
    [22]
    Hansen, C.M., 2007. Hansen Solubility Parameters: A User's Handbook, Second Edition. Boca Raton: CRC Press.
    [23]
    Hara, Y., Kikuchi, A., Noriyasu, A., Furukawa, H., Takaichi, H., Inokuchi, R., Bouteau, F., Chin, S., Li, X.H., Nishihama, S., Yoshizuka, K., Kawano, T., 2016. Batch extraction of oil from rice bran with liquefied low temperature dimethyl ether. Solvent Extr. Res. Dev. Jpn. 23, 87-99.
    [24]
    Hoang, A.T., Tabatabaei, M., Aghbashlo, M., Carlucci, A.P., Ölçer, A.I., Le, A.T., Ghassemi, A., 2021. Rice bran oil-based biodiesel as a promising renewable fuel alternative to petrodiesel: a review. Renew. Sustain. Energy Rev. 135, 110204.
    [25]
    Hu, W.C., Wells, J.H., Shin, T.S., Godber, J.S., 1996. Comparison of isopropanol and hexane for extraction of vitamin E and oryzanols from stabilized rice bran. J. Am. Oil Chem. Soc. 73, 1653-1656.
    [26]
    Imsanguan, P., Roaysubtawee, A., Borirak, R., Pongamphai, S., Douglas, S., Douglas, P.L., 2008. Extraction of α-tocopherol and γ-oryzanol from rice bran. LWT Food Sci. Technol. 41, 1417-1424.
    [27]
    Irnawati, Riyanto, S., Martono, S., Rohman, A., 2019. Determination of sesame oil, rice bran oil and pumpkin seed oil in ternary mixtures using FTIR spectroscopy and multivariate calibrations. Food Res. 4, 135-142.
    [28]
    Ji, Y., Yang, X.L., Ji, Z., Zhu, L.H., Ma, N.N., Chen, D.J., Jia, X.B., Tang, J.M., Cao, Y.L., 2020. DFT-calculated IR spectrum amide I, Ⅱ, and Ⅲ band contributions of N-methylacetamide fine components. ACS Omega 5, 8572-8578.
    [29]
    Juliano, C., Cossu, M., Alamanni, M.C., Piu, L., 2005. Antioxidant activity of gamma-oryzanol: mechanism of action and its effect on oxidative stability of pharmaceutical oils. Int. J. Pharm. 299, 146-154.
    [30]
    Kalpanadevi, C., Singh, V., Subramanian, R., 2018. Influence of milling on the nutritional composition of bran from different rice varieties. J. Food Sci. Technol. 55, 2259-2269.
    [31]
    Kayathi, A., Chakrabarti, P.P., Bonfim-Rocha, L., Cardozo-Filho, L., Bollampalli, A., Jegatheesan, V., 2021. Extraction of γ-Oryzanol from defatted rice bran using supercritical carbon dioxide (SC-CO2): Process optimisation of extract yield, scale-up and economic analysis. Process. Saf. Environ. Prot. 148, 179-188.
    [32]
    Lai, O.M., Jacoby, J.J., Leong, W.F., Lai, W.T., 2019. Nutritional studies of rice bran oil. In: Cheong, L.Z., Xu, X.B. (Eds.). Rice Bran and Rice Bran Oil. Champaign: AOCS Press, 19-54.
    [33]
    Liu, S.X., Mamidipally, P.K., 2005. Quality comparison of rice bran oil extracted with D-limonene and hexane. Cereal Chem. 82, 209-215.
    [34]
    Meedam, A., Usaku, C., Daisuk, P., Shotipruk, A., 2020. Comparative study on physicochemical hydrolysis methods for glycerides removal from rice bran acid oil for subsequent γ-oryzanol recovery. Biomass Convers. Biorefin. 12, 245-252.
    [35]
    Mitrea, L., Teleky, B.E., Leopold, L.F., Nemes, S.A., Plamada, D., Dulf, F.V., Pop, I.D., Vodnar, D.C., 2022. The physicochemical properties of five vegetable oils exposed at high temperature for a short-time-interval. J. Food Compos. Anal. 106, 104305.
    [36]
    Nakamura, A., Hara, Y., Kawano, T., 2017. Dewatering and extraction of hydrophilic solutes and essential oils from cryo-preserved lemon peels using liquefied dimethyl ether. Solvent Extr. Res. Dev. Japan 24, 37-45.
    [37]
    Pestana-Bauer, V.R., Zambiazi, R.C., Mendonça, C.R.B., Beneito-Cambra, M., Ramis-Ramos, G., 2012. γ-Oryzanol and tocopherol contents in residues of rice bran oil refining. Food Chem. 134, 1479-1483.
    [38]
    Pourali, O., Salak Asghari, F., Yoshida, H., 2009. Simultaneous rice bran oil stabilization and extraction using sub-critical water medium. J. Food Eng. 95, 510-516.
    [39]
    Prat, D., Wells, A., Hayler, J., Sneddon, H., McElroy, C.R., Abou-Shehada, S., Dunn, P.J., 2016. CHEM21 selection guide of classical- and less classical-solvents. Green Chem. 18, 288-296.
    [40]
    Punia, S., Kumar, M., Siroha, A.K., Purewal, S.S., 2021. Rice bran oil: emerging trends in extraction, health benefit, and its industrial application. Rice Sci. 28, 217-232.
    [41]
    Ribas, F.B.T., Gasparetto, H., Salau, N.P.G., 2023. Sustainable extraction of rice bran Oil: Assessing renewable solvents, kinetics, and thermodynamics. Chem. Eng. Res. Des. 197, 342-354.
    [42]
    Rigo, L.A., Pohlmann, A.R., Guterres, S.S., Ruver Beck, R.C., 2014. Rice bran oil: benefits to health and applications in pharmaceutical formulations. In: Watson, R.R., Preedy, V.R., Zibadi, S. (Eds.). Wheat and Rice in Disease Prevention and Health. San Diego: Academic Press, 311-322.
    [43]
    Sánchez-Camargo, A.P., Montero, L., Cifuentes, A., Herrero, M., Ibáñez, E., 2016. Application of Hansen solubility approach for the subcritical and supercritical selective extraction of phlorotannins from Cystoseira abies-marina. RSC Adv. 6, 94884-94895.
    [44]
    Sayasoonthorn, S., Kaewrueng, S., Patharasathapornkul, P., 2012. Rice bran oil extraction by screw press method: optimum operating settings, oil extraction level and press cake appearance. Rice Sci. 19, 75-78.
    [45]
    Seddon, D., 2011. Methanol and dimethyl ether (DME) production from synthesis gas. In: Khan, M. (Ed.), Advances in Clean Hydrocarbon Fuel Processing. Cambridge: Woodhead Publishing, 363-386.
    [46]
    Sharif, M.K., Butt, M.S., Anjum, F.M., Khan, S.H., 2014. Rice bran: a novel functional ingredient. Crit. Rev. Food Sci. Nutr. 54, 807-816.
    [47]
    Sharma, N., Sahil, Madhumita, M., Kumar, Y., Prabhakar, P.K., 2023. Ultrasonic modulated rice bran protein concentrate: Induced effects on morphological, functional, rheological, and thermal characteristics. Innov. Food Sci. Emerg. Technol. 85, 103332.
    [48]
    Stefanis, E., Panayiotou, C., 2008. Prediction of Hansen solubility parameters with a new group-contribution method. Int. J. Thermophys. 29, 568-585.
    [49]
    Tirado, D.F., Calvo, L., 2019. The Hansen theory to choose the best cosolvent for supercritical CO2 extraction of β-carotene from Dunaliella salina. J. Supercrit. Fluid. 145, 211-218.
    [50]
    Tomita, K., Machmudah, S., Wahyudiono, Fukuzato, R., Kanda, H., Quitain, A.T., Sasaki, M., Goto, M., 2014. Extraction of rice bran oil by supercritical carbon dioxide and solubility consideration. Sep. Purif. Technol. 125, 319-325.
    [51]
    Trevisani Juchen, P., Nolasco Araujo, M., Hamerski, F., Corazza, M.L., Pedersen Voll, F.A., 2019. Extraction of parboiled rice bran oil with supercritical CO2 and ethanol as co-solvent: Kinetics and characterization. Ind. Crops Prod. 139, 111506.
    [52]
    Wang, C.H., Chen, C.R., Wu, J.J., Wang, L.Y., Chang, C.M J., Ho, W.J., 2008. Designing supercritical carbon dioxide extraction of rice bran oil that contain oryzanols using response surface methodology. J. Sep. Sci. 31, 1399-1407.
    [53]
    Wang, Q., Oshita, K., Takaoka, M., 2021. Effective lipid extraction from undewatered microalgae liquid using subcritical dimethyl ether. Biotechnol. Biofuel. 14, 17.
    [54]
    Wang, S.R., Wang, T.Y., Sun, Y., Cui, Y.J., Yu, G.P., Jiang, L.Z., 2022. Effects of high hydrostatic pressure pretreatment on the functional and structural properties of rice bran protein hydrolysates. Foods 11, 29.
    [55]
    Wang, Y., 2019. Applications of rice bran oil. In: Cheong, L.Z., Xu, X.B. (Eds.). Rice Bran and Rice Bran Oil. Champaign: AOCS Press, 159-168.
    [56]
    Williams, L.L., Rubin, J.B., Edwards, H.W., 2004. Calculation of Hansen solubility parameter values for a range of pressure and temperature conditions, including the supercritical fluid region. Ind. Eng. Chem. Res. 43, 4967-4972.
    [57]
    Wongwaiwech, D., Kamchonemenukool, S., Ho, C.T., Li, S.M., Majai, N., Rungrat, T., Sujipuli, K., Pan, M.H., Weerawatanakorn, M., 2023. Bioactives from crude rice bran oils extracted using green technology. Molecules 28, 2457.
    [58]
    Xu, Z.M., Godber, J.S., 2000. Comparison of supercritical fluid and solvent extraction methods in extracting γ-oryzanol from rice bran. J. Am. Oil Chem. Soc. 77, 547-551.
    [59]
    Xu, Z.M., Godber, J.S., 1999. Purification and identification of components of γ-oryzanol in rice bran oil. J. Agric. Food Chem. 47, 2724-2728.
    [60]
    Yara-Varón, E., Fabiano-Tixier, A.S., Balcells, M., Canela-Garayoa, R., Bily, A., Chemat, F., 2016. Is it possible to substitute hexane with green solvents for extraction of carotenoids? A theoretical versus experimental solubility study. RSC Adv. 6, 27750-27759.
    [61]
    Yoon, S.W., Pyo, Y.G., Lee, J., Lee, J.S., Kim, B.H., Kim, I.H., 2014. Concentrations of tocols and γ-oryzanol compounds in rice bran oil obtained by fractional extraction with supercritical carbon dioxide. J. Oleo Sci. 63, 47-53.
    [62]
    Zheng, Q.X., Watanabe, M., 2022. Advances in low-temperature extraction of natural resources using liquefied dimethyl ether. Resour. Chem. Mater. 1, 16-26.
  • 加载中

Catalog

    通讯作者: 陈斌, bchen63@163.com
    • 1. 

      沈阳化工大学材料科学与工程学院 沈阳 110142

    1. 本站搜索
    2. 百度学术搜索
    3. 万方数据库搜索
    4. CNKI搜索

    Article Metrics

    Article views (193) PDF downloads(56) Cited by()
    Proportional views
    Related

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return