Phosphonium-based hydrophobic ionic liquids with fluorous anions for biodiesel production from waste cooking oil
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Abstract
In this work, ionic liquids (ILs) containing the phosphonium cation and four different types of fluorous anions were synthesized and characterized with nuclear magnetic resonance spectroscopy, Fourier-transform infrared spectroscopy, elemental analyser (CHNS) and thermogravimetric techniques. The catalytic transesterification properties of the prepared ILs were investigated through the synthesis of biodiesel from waste cooking oil (WCO). The biodiesel synthesis was performed in two-step processes. Initially, the WCO was esterified with sulphuric acid to reduce its acid value (0.7 mg KOH/g). Later the transesterification reaction was carried out with the prepared ILs, and the process was optimized with respect to IL types, catalyst loading, methanol–oil ratios, temperature, agitation speed and time. Tetrabutylphosphonium bis(trifluoromethylsulfonyl)imide ([TBP][NTf2]) was identified as a promising catalyst with the highest yield of biodiesel up to 81% at 4.5 wt% of IL loading, 18:1 ratio of methanol:WCO, 10 h of treatment time, 60 °C heating temperature and 600 rpm of agitation speed. The obtained product of biodiesel was characterized and analysed by different techniques, and its physicochemical properties were further determined using the known standard methods of American Society for Testing and Materials and European standards (ASTM and EN).
Keywords
Biodiesel Characterization Optimization Phosphonium-based ionic liquids Physiochemical propertiesNotes
Acknowledgements
The author gratefully acknowledges the financial assistance provided by the Centre of Research in Ionic Liquids (CORIL), all the research officers, Chemical Engineering Department, Universiti Teknologi PETRONAS (UTP), Malaysia.
Supplementary material
References
- Almeida HF, Lopes-da-Silva JA, Freire MG, Coutinho JA (2013) Surface tension and refractive index of pure and water-saturated tetradecyltrihexylphosphonium-based ionic liquids. J Chem Thermodyn 57:372–379Google Scholar
- Amde M, Liu J-F, Pang L (2015) Environmental application, fate, effects, and concerns of ionic liquids: a review. Environ Sci Technol 49:12611–12627Google Scholar
- Bates ED, Mayton RD, Ntai I, Davis JH (2002) CO2 capture by a task-specific ionic liquid. J Am Chem Soc 124:926–927Google Scholar
- Bösmann A, Datsevich L, Jess A, Lauter A, Schmitz C, Wasserscheid P (2001) Deep desulfurization of diesel fuel by extraction with ionic liquids. Chem Commun 23:2494–2495Google Scholar
- Bradaric CJ, Downard A, Kennedy C, Robertson AJ, Zhou Y (2003) Industrial preparation of phosphonium ionic liquids. Green Chem 5:143–152Google Scholar
- Chiappe C, Pieraccini D (2005) Ionic liquids: solvent properties and organic reactivity. J Phys Org Chem 18:275–297Google Scholar
- De los Ríos A, Fernández FH, Gómez D, Rubio M, Víllora G (2011) Biocatalytic transesterification of sunflower and waste cooking oils in ionic liquid media. Process Biochem 46:1475–1480Google Scholar
- Del Sesto RE, McCleskey TM, Macomber C, Ott KC, Koppisch AT, Baker GA et al (2009) Limited thermal stability of imidazolium and pyrrolidinium ionic liquids. Thermochim Acta 491:118–120Google Scholar
- Dupont J, de Souza RF, Suarez PA (2002) Ionic liquid (molten salt) phase organometallic catalysis. Chem Rev 102:3667–3692Google Scholar
- Earle MJ, Plechkova NV, Seddon KR (2009) Green synthesis of biodiesel using ionic liquids. Pure Appl Chem 81:2045–2057Google Scholar
- Endres F (2002) Ionic liquids: solvents for the electrodeposition of metals and semiconductors. ChemPhysChem 3:144–154Google Scholar
- Fan M, Huang J, Yang J, Zhang P (2013) Biodiesel production by transesterification catalyzed by an efficient choline ionic liquid catalyst. Appl Energy 108:333–339Google Scholar
- Farooq M, Ramli A (2015) Biodiesel production from low FFA waste cooking oil using heterogeneous catalyst derived from chicken bones. Renew Energy 76:362–368Google Scholar
- Fukumoto K, Ohno H (2006) Design and synthesis of hydrophobic and chiral anions from amino acids as precursor for functional ionic liquids. Chem Commun 29:3081–3083Google Scholar
- Gamero-Casta-icirc M, Hruby V (2001) Electrospray as a source of nanoparticles for efficient colloid thrusters. J Propul Power 17:977–987Google Scholar
- Gnanaprakasam A, Sivakumar VM, Surendhar A, Thirumarimurugan M, Kannadasan T (2013) Recent strategy of biodiesel production from waste cooking oil and process influencing parameters: a review. Journal of Energy. https://doi.org/10.1155/2013/926392 CrossRefGoogle Scholar
- Gordon CM (2001) New developments in catalysis using ionic liquids. Appl Catal A 222:101–117Google Scholar
- Gordon CM, McLean AJ (2000) Photoelectron transfer from excited-state ruthenium(II) tris (bipyridyl) to methylviologen in an ionic liquid. Chem Commun 15:1395–1396Google Scholar
- Gordon CM, Holbrey JD, Kennedy AR, Seddon KR (1998) Ionic liquid crystals: hexafluorophosphate salts. J Mater Chem 8:2627–2636Google Scholar
- Hecke K, Meervelt L (2010) Hydrophobic ionic liquids with strongly coordinating anions. Chem Commun 46:234–236Google Scholar
- Kailasa SK, Rawat KA, Wu H-F (2015) Ionic liquids in bioanalysis. Bioanalysis 7:2251–2264Google Scholar
- Keskin S, Kayrak-Talay D, Akman U, Hortaçsu Ö (2007) A review of ionic liquids towards supercritical fluid applications. J Supercrit Fluids 43:150–180Google Scholar
- Khan AS, Man Z, Bustam MA, Kait CF, Nasrullah A, Ullah Z et al (2018) Dicationic ionic liquids as sustainable approach for direct conversion of cellulose to levulinic acid. J Clean Prod 170:591–600Google Scholar
- Lethesh KC, Shah SN, Mutalib MA (2014) Synthesis, characterization, and thermophysical properties of 1,8-diazobicyclo[5.4. 0]undec-7-ene based thiocyanate ionic liquids. J Chem Eng Data 59:1788–1795Google Scholar
- Lethesh KC, Shah SN, Mutalib MA (2015) Synthesis, characterization, physical and thermodynamic properties of diazobicyclo undecene based dicyanamide ionic liquids. J Mol Liq 208:253–258Google Scholar
- Leung D, Guo Y (2006) Transesterification of neat and used frying oil: optimization for biodiesel production. Fuel Process Technol 87:883–890Google Scholar
- Leung DY, Wu X, Leung M (2010) A review on biodiesel production using catalyzed transesterification. Appl Energy 87:1083–1095Google Scholar
- Liang X (2013) Novel acidic ionic liquid polymer for biodiesel synthesis from waste oils. Appl Catal A 455:206–210Google Scholar
- Liu Y, Chen D, Yan Y, Peng C, Xu L (2011) Biodiesel synthesis and conformation of lipase from Burkholderia cepacia in room temperature ionic liquids and organic solvents. Bioresour Technol 102:10414–10418Google Scholar
- Lozano P, Bernal JM, Vaultier M (2011) Towards continuous sustainable processes for enzymatic synthesis of biodiesel in hydrophobic ionic liquids/supercritical carbon dioxide biphasic systems. Fuel 90:3461–3467Google Scholar
- Man Z, Elsheikh YA, Bustam MA, Yusup S, Mutalib MIA, Muhammad N (2013) A Brønsted ammonium ionic liquid–KOH two-stage catalyst for biodiesel synthesis from crude palm oil. Ind Crops Prod 41:144–149Google Scholar
- Meher L, Sagar DV, Naik S (2006) Technical aspects of biodiesel production by transesterification—a review. Renew Sustain Energy Rev 10:248–268Google Scholar
- Muhammad N, Elsheikh YA, Mutalib MIA, Bazmi AA, Khan RA, Khan H et al (2015) An overview of the role of ionic liquids in biodiesel reactions. J Ind Eng Chem 21:1–10Google Scholar
- Nasir Shah S, Mutalib MIA, Pilus RBM, Lethesh KC (2014) Extraction of naphthenic acid from highly acidic oil using hydroxide-based ionic liquids. Energy Fuels 29:106–111Google Scholar
- Quinn BM, Ding Z, Moulton R, Bard AJ (2002) Novel electrochemical studies of ionic liquids. Langmuir 18:1734–1742Google Scholar
- Rashid U, Rehman HA, Hussain I, Ibrahim M, Haider MS (2011) Muskmelon (Cucumis melo) seed oil: a potential non-food oil source for biodiesel production. Energy 36:5632–5639Google Scholar
- Saraiva M, Costa S, Pinto P, Azevedo A (2017) Environmental impact of ionic liquids: an overview of recent (eco)toxicological and(bio) degradability literature. Chemsuschem. https://doi.org/10.1002/cssc.201700261 CrossRefGoogle Scholar
- Shah SN, Lethesh KC, Mutalib MA, Pilus RBM (2015) Evaluation of thermophysical properties of imidazolium-based phenolate ionic liquids. Ind Eng Chem Res 54:3697–3705Google Scholar
- Sheldon R (2001) Catalytic reactions in ionic liquids. Chem Commun 23:2399–2407Google Scholar
- Sowmiah S, Srinivasadesikan V, Tseng M-C, Chu Y-H (2009) On the chemical stabilities of ionic liquids. Molecules 14:3780–3813Google Scholar
- Ullah Z, Bustam MA, Man Z (2014) Preparation of biodiesel from waste cooking oil catalyzed by basic ionic liquid. In: Ahmed I (ed) Applied mechanics and materials. Trans Tech Publications, Zurich, pp 874–876Google Scholar
- Ullah Z, Bustam MA, Muhammad N, Man Z, Khan AS (2015) Synthesis and thermophysical properties of hydrogensulfate based acidic ionic liquids. J Solution Chem 44:875–889Google Scholar
- Ullah Z, Bustam MA, Man Z, Khan AS, Muhammad N, Sarwono A (2017a) Preparation and kinetics study of biodiesel production from waste cooking oil using new functionalized ionic liquids as catalysts. Renew Energy 114:755–765Google Scholar
- Ullah Z, Bustam MA, Man Z, Khan AS, Muhammad N, Sarwono A et al (2017b) A detail description on catalytic conversion of waste palm cooking oil into biodiesel and its derivatives: new functionalized ionic liquid process. ChemistrySelect 2:8583–8595Google Scholar
- Visser AE, Swatloski RP, Griffin ST, Hartman DH, Rogers RD (2001) Liquid/liquid extraction of metal ions in room temperature ionic liquids. Sep Sci Technol 36:785–804Google Scholar
- Wasserscheid P, Keim W (2000) Ionische Flüssigkeiten–neue „Lösungen “für die Übergangsmetallkatalyse. Angew Chem 112:3926–3945Google Scholar
- Ye C, Liu W, Chen Y, Yu L (2001) Room-temperature ionic liquids: a novel versatile lubricant. Chem Commun 21:2244–2245Google Scholar
- Yue C, Fang D, Liu L, Yi T-F (2011) Synthesis and application of task-specific ionic liquids used as catalysts and/or solvents in organic unit reactions. J Mol Liq 163:99–121Google Scholar
- Ziyada AK, Bustam MA, Murugesan T, Wilfred CD (2011) Effect of sulfonate-based anions on the physicochemical properties of 1-alkyl-3-propanenitrile imidazolium ionic liquids. New J Chem 35:1111–1116Google Scholar