Synthesis of Bio-based Polyol Via Epoxidation and Hydroxylation of Shea Butter Fats

Eucharia Agborma Emeka-Chioke

Department of Industrial Chemistry, Enugu State University of Science and Technology, Enugu State, Nigeria.

Prisca Ifeoma Udeozo

Department of Industrial Chemistry, Enugu State University of Science and Technology, Enugu State, Nigeria.

Okechukwu Paul Nsude

Department of Industrial Chemistry, Enugu State University of Science and Technology, Enugu State, Nigeria.

Theresa Orieiji Uchechukwu

Department of Chemistry, Faculty of Physical Sciences, Alex Ekwueme Federal University, Ndufu Alike, Nigeria.

Kingsley John Orie *

Department of Pure and Industrial Chemistry, University of Port Harcourt, Rivers State, Nigeria.

Okoro Ogbobe

Department of Industrial Chemistry, Enugu State University of Science and Technology, Enugu State, Nigeria.

*Author to whom correspondence should be addressed.


Abstract

Polyols are mostly made from petroleum and other non-biodegradable fossil fuels, and as such, they are not environmentally benign. This study presents the process of making bio-based polyols from shea butter fats (SBF) by epoxidation and hydroxylation. Wet analysis, gas chromatography with flame-ionization detection (GC-FID), and Fourier transform infrared spectroscopy (FTIR) were all used to characterize the bio-based polyols. The acid number (13.92 mg KOH/g), iodine value (19.54 mg I2/100 g), saponification value (218.03 mg KOH/g), and viscosity (107.98 poise) suggest a good quality of synthesized SBF-polyol. The FTIR analysis of SBF-polyol indicates the existence of specific vibrational frequencies: 3473 cm-1 for hydroxyl (OH) groups, 2921–2854 cm-1, and 2929–2858 cm-1 for carbon-hydrogen (C-H) and methylene (CH2) groups, respectively, and 1748 cm-1 for carbonyl (-C=O) groups. The major unsaturated fatty acids detected in SBF were oleic acid, with an estimation of 10.41%; linoleic acid and linolenic acid were reported at 0.34% and 1.67%, respectively; however, they were absent in SBF-polyol. According to this data, bio-based polyols can be synthesized using SBF and are suggested for the production of top-notch polyols.

Keywords: Epoxidation, hydroxylation, polyol, shea butter fat


How to Cite

Emeka-Chioke, E. A., Udeozo , P. I., Nsude, O. P., Uchechukwu , T. O., Orie , K. J., & Ogbobe , O. (2024). Synthesis of Bio-based Polyol Via Epoxidation and Hydroxylation of Shea Butter Fats. Journal of Applied Chemical Science International, 15(1), 1–9. https://doi.org/10.56557/jacsi/2023/v14i28487

Downloads

Download data is not yet available.

References

Fang Z, Qiu C, Ji D, Yang Z, Zhu N, Meng J, Guo K. Development of high-performance biodegradable rigid polyurethane foams using full modified soy-based polyols. Journal of agricultural and food chemistry. 2019;67(8):2220-2226.

Available:https://doi.org/10.1021/acs.jafc.8b05342

Zareanshahraki F, Lu J, Yu S, Kiamanesh A, Shabani B, Mannari V. Development of sustainable polyols with high bio-renewable content and their applications in thermoset coatings. Progress in Organic Coatings. 2020;147:105725.

Kirpluks M, Cabulis U, Kurańska M, Prociak A. Three different approaches for polyol synthesis from rapeseed oil. Key Engineering Materials. 2013;559:69-74.

Yeoh FH, Lee CS, Kang YB, Wong SF, Cheng SF, Ng WS. Production of biodegradable palm oil-based polyurethane as potential biomaterial for biomedical applications. Polymers, 2020; 12(8):1842.

Nsude OP, Agboeze E, Ezeh EC, Ike OC, Omuluche OC, Orie KJ, Ogbobe O. Isolation and characterization of cellulose from Pentaclethra macrophylla Benth pod biomass wastes for polymer reinforcement composite. Journal of Chemical Society of Nigeria. 2022;47(3). Available:https://doi.org/10.46602/jcsn.v47i3.765

Chibor SB, Barine KKD, Joy EE. Physicochemical properties and fatty acid profile of shea butter and fluted pumpkin seed oil, a suitable blend in bakery fat production. International Journal of Nutrition and Food Sciences. 2017; 6(3): 122-128.

Dhaliwal GS, Anandan S, Chandrashekhara K, Lees J, Nam P. Development and characterization of polyurethane foams with substitution of polyether polyol with soy-based polyol. European Polymer Journal. 2018;107:105-117.

Suhendra D, Gunawan ER, Handayani SS. Synthesis of Polyol Through Epoxidation and Hydroxylation Reactions of Ricinus Communis L. Oil. In 2nd International Conference on Science Education and Sciences. 2022;(ICSES 2022):300-307.

Okullo JBL, Omujal F, Agea JG, Vuzi PC, Namutebi A, Okello JBA, Nyanzi SA. Physico-chemical characteristics of Shea butter (Vitellaria paradoxa CF Gaertn.) oil from the Shea district of Uganda. African Journal of Food, Agriculture, Nutrition and Development. 2010;10(1).

Yamin AF, Jalil MJ, Adnan I, Vsiduru VG. Numerical modeling of epoxidation palm kernel oil based oleic acid. Int. J. Eng. Technol. 2018;7(4):123-6.

Abril-Milán D, Valdés O, Mirabal-Gallardo YF, de la Torre A, Bustamante C, Contreras J. Preparation of renewable bio-polyols from two species of Colliguaja for rigid polyurethane foams. Materials. 2018; 11(11):2244.

Available:https://doi.org/10.3390/ma11112244

Li W, Gao Y, Chen W, Tang P, Li W, Shi Z, Ma D. Catalytic epoxidation reaction over N-containing sp2 carbon catalysts. Acs Catalysis. 2014;4(5):1261-1266.

Orie KJ, Duru RU, Ngochindo RI. Synthesis and Complexation of Monotosylated 4-Aminopyridine with Nickel (II) and Iron (II) Ions. Makara Journal of Science. 2021;25(3):6.

Available:https://doi.org/10.7454/mss.v25i3.1242

Hazmi B, Rashid U, Ibrahim ML, Nehdi IA, Azam M, Al-Resayes SI. Synthesis and characterization of bifunctional magnetic nano-catalyst from rice husk for production of biodiesel. Environmental Technology & Innovation. 2021; 21:101296. Available:https://doi.org/10.1016/j.eti.2020.101296

Nilawar S, Chatterjee K. Olive oil-derived degradable polyurethanes for bone tissue regeneration. Industrial Crops and Products. 2022;185:115136.

Musik M, Bartkowiak M, Milchert E. Advanced methods for hydroxylation of vegetable oils, unsaturated fatty acids and their alkyl esters. Coatings. 2021;12(1):13-21.

Senan, AM, Yin B, Zhang Y, Nasiru MM, Lyu YM, Umair M, Liu L. Efficient and selective catalytic hydroxylation of unsaturated plant oils: a novel method for producing anti-pathogens. BMC chemistry. 2021;15:1-11.

Konuskan DB, Arslan M, Oksuz A. Physicochemical properties of cold pressed sunflower, peanut, rapeseed, mustard and olive oils grown in the Eastern Mediterranean region. Saudi Journal of Biological Sciences. 2019;26(2): 340-344.

AOAC. Association of Official Analytical Chemist, official methods of Analysis, 19th edition, Washington, D. C; 2012.

Lee JH, Kim SH, Oh KW. Bio-based polyurethane foams with castor oil based multifunctional polyols for improved compressive properties. Polymers. 2021; 13(4):576.

Okocha BI, Orie KJ, Duru RU, Ngochindo RL. Analysis of the active metabolites of ethanol and ethyl acetate extract of Justicia carnea. African Journal of Biomedical Research. 2023;26(1): 109-117.

DOI:10.4314/ajbr.v26i1.15

Adetuyi BO, Oluwole EO, Dairo JO. Biochemical effects of shea butter and groundnut oils on white albino rats. International Journal of Chemistry and Chemical Processes. 2015;1(8):1-17.

Nna PJ, Orie KJ. Comparative Studies on Chemical Compositions and Bioactivity of Fresh Fruit and Seed of Aratocarpusheterophyllus. Direct Research Journal Chemical Material Science. 2023; 11(6):40-48.

Available:https://doi.org/10.26765/DRJCMS281006153

Enaberue LO, Obisesan IO, Okolo EC, Akinwale RO, Aisueni NO, Ataga CD. Genetic diversity of shea butter tree (Vitellaria paradoxa CF Gaernt) in the Guinea savanna of Nigeria based on morphological markers. American-Eurasian Journal of Agricultural & Environmental Sciences. 2014;14(7):615-623.

Folayan AJ, Anawe PAL, Aladejare AE, Ayeni AO. Experimental investigation of the effect of fatty acids configuration, chain length, branching and degree of unsaturation on biodiesel fuel properties obtained from lauric oils, high-oleic and high-linoleic vegetable oil biomass. Energy Reports. 2019;5:793-806.

Stavila E, Yuliati F, Adharis A, Laksmono JA, Iqbal M. Recent advances in synthesis of polymers based on palm oil and its fatty acids. RSC advances. 2023;13(22):14747-14775.

Gurgel D, Bresolin D, Sayer C, Cardozo-Filho L, de-Araújo PHH. Flexible polyurethane foams produced from industrial residues and castor oil. Industrial Crops and Products. 2021;164:113377.

Paciorek-Sadowska J, Borowicz M, Czupryński B, Tomaszewska E, Liszkowska J. Oenothera biennis seed oil as an alternative raw material for production of bio-polyol for rigid polyurethane-polyisocyanurate foams. Industrial Crops and Products. 2018;126: 208-217.

Emeka-Chioke EA, Orie KJ, Nsude OP, Udeozo PI, Onyia S. Comparative studies on the physico-mechanical properties of polyurethane foams derived from bio-based polyols. Asian Journal of Research Current Science. 2024;6(1):13–22.

Tenorio-Alfonso A, Sánchez MC, Franco JM. A review of the sustainable approaches in the production of bio-based polyurethanes and their applications in the adhesive field. Journal of Polymers and the Environment. 2020; 28: 749-774 Available:https://doi.org/10.1007/s10924-020-01659-1

Bresolin D, Valério A, de-Oliveira D, Lenzi MK, Sayer C, de Araújo PHH. Polyurethane foams based on biopolyols from castor oil and glycerol. Journal of Polymers and the Environment. 2018;26: 2467-2475.

Nsude OP, Orie KJ. Microcrystalline cellulose of oil bean pod: Extraction, physico-chemical, brunauer–emmett–teller (BET), and flow-ability analysis. Asian Journal of Applied Chemistry Research. 2022;2(4)1-12.