Removal of Phenol from Organic System by Using Ionic Liquids

Page: [126 - 133] Pages: 8

  • * (Excluding Mailing and Handling)

Abstract

Objective: Selective removal of phenol from organic solvent mixture (benzene + toluene + hexane) or other petroleum by-products have a major concern. Hence, the experiments were conducted on the removal of phenol from synthetically prepared phenolic organic waste by using a green process, ionic liquids.

Methods: The ionic liquids, 1-ethyl-3-methyl imidazolium cyanoborohydride, and 1- butyl-3-methyl imidazolium hexafluorophosphate were used for the extraction study. The effect of various operating parameters such as the type of ionic liquids, effluent temperature, extraction time, and the phase volume ratio of ionic liquid and phenol has been studied in details. The ionic liquid, 1-ethyl-3-methyl imidazolium cyanoborohydride selectively extracted 95 % of the phenol from the synthetically prepared organic oil mixture of benzene and toluene, with an initial phenol concentration was 100 ppm. Further, ionic liquids were recycled and reused for six consecutive studies with removal efficiency of about 74%. Additionally, a batch reactor study was conducted to find the process viability for industrial use and 92% phenol removal efficiency was achieved.

Results: The study demonstrates the selective removal of phenol from petroleum oil using ionic liquids is a simple and environmentally friendly process for industrial use.

Conclusion: This method cannot only extract phenol but also phenol-derived compounds may be extracted from hydrocarbon oil.

Keywords: Solvent extraction, phenolic compounds, crude hydrocarbon oil, ionic liquids, batch reactor, organic system.

Graphical Abstract

[1]
Klapötke TM, Sabaté CM. 1,2,4-Triazolium and tetrazolium picrate salts: “On the way” from nitroaromatic to azole-based energetic materials. Eur J Inorg Chem 2008; 2008(34): 5350-66.
[2]
O’Connell JE, Fox PF. Significance and applications of phenolic compounds in the production and quality of milk and dairy products: A review. Int Dairy J 2001; 11: 103-20.
[3]
Martillanes S, Rocha-Pimienta J, Vertedor DM, Delgado-Adámez J. Application of phenolic compounds for food preservation: Food additive and active packaging. Intech Open 2017; 2: 64.
[4]
Field E, Dempster FH, Tilson GE. Phenolic compounds from petroleum sources. Ind Eng Chem 1940; 32: 489-96.
[5]
Schlosberg RH, Scouten CG. Removal of phenols from phenol-containing streams United States patent US 4256568 1981.
[6]
Gleim WKT. Removal of phenolic compounds from petroleum fractions United States patent US 2683108 1954.
[7]
Kodera Y, Ukegawa K, Matsumura A, Xiaoliang M. Methanol-mediated extraction process for the separation of phenolic compounds from coal liquids. Fuel 1993; 72: 57-8.
[8]
Aval AE, Hasani AH, Omrani GA, Karbassi A. Removal of landfill leachate’s organic load by modified electro-fenton process. Int J Electrochem Sci 2017; 12: 9348-63.
[9]
Olawepo GK, Ogunkunle CO, Adebisi OO, Fatoba PO. Enhanced bioremediation of brass crude-oil (hydrocarbon), using cow dung and implication on microbial population. pollution 2018; 4: 273-80.
[10]
Usharani K, Sreejina K, Sruthi T, Vineeth T. Diesel oil utilization efficiency of selective bacterial isolates from automobile workshop and Thesjaswini river of Kerala. Pollution 2016; 2: 221-32.
[11]
Shahriari T, Karbassi AR, Reyhani M. Treatment of oil refinery wastewater by electrocoagulation-flocculation (Case Study: Shazand Oil Refinery of Arak). Int J Environ Sci Technol 2018; 1-8.
[http://dx.doi.org/10.1007/s13762-018-1810-z]
[12]
Sato S, Matsumura A, Saito I, Ukegawa K. Methanol-mediated extraction of coal liquid (5). Conceptual design and mass balance of a continuous methanol-mediated extraction process. Energy Fuels 2002; 16: 1337-42.
[13]
Fardhyanti D, Sediawan W, Mulyono P. Complex extraction of phenol, o-Cresol and p-Cresol from model coal tar using methanol and acetone solutions. Br J Appl Sci Technol 2015; 8: 427-36.
[14]
Gao J, Dai Y, Ma W, Xu H, Li C. Efficient separation of phenol from oil by acid-base complexing adsorption. Chem Eng J 2015; 281: 749-58.
[15]
Bhadra BN, Ahmed I, Jhung SH. Remarkable adsorbent for phenol removal from fuel: Functionalized metal-organic framework. Fuel 2016; 174: 43-8.
[16]
Fan J, Fan Y, Pei Y, Wu K, Wang J, Fan M. Solvent extraction of selected endocrine-disrupting phenols using ionic liquids. Separ Purif Tech 2008; 61: 324-31.
[17]
Sidek N, Ninie NS, Mohamad S. Efficient removal of phenolic compounds from model oil using benzyl Imidazolium-based ionic liquids. J Mol Liq 2017; 240: 794-802.
[18]
Lakshmi AB, Balasubramanian A, Venkatesan S, Tiruchirappalli T, Nadu T. Extraction of phenol and chlorophenols using ionic liquid [ Bmim ] þ [ BF 4 ] À dissolved in tributyl phosphate 2013; 41: 349-55.
[19]
Fan Y, Li Y, Dong X, et al. Extraction of phenols from water with functionalized ionic liquids. Ind Eng Chem Res 2014; 53: 20024-31.
[20]
Deng N, Li M, Zhao L, Lu C, De Rooy SL, Warner IM. Highly efficient extraction of phenolic compounds by use of magnetic room temperature ionic liquids for environmental remediation. J Hazard Mater 2011; 192: 1350-7.
[21]
Yao C, Hou Y, Ren S, Ji Y, Wu W. Ternary phase behavior of phenol + toluene + zwitterionic alkaloids for separating phenols from oil mixtures via forming deep eutectic solvents. Fluid Phase Equilib 2017; 448: 116-22.
[22]
Ji Y, Hou Y, Ren S, Yao C, Wu W. Tetraethylammonium amino acid ionic liquids and CO2 for separation of phenols from oil mixtures. Energy Fuels 2018; 32: 11046-54.
[23]
Jiao T, Li C, Zhuang X, Cao S, Chen H, Zhang S. The new liquid-liquid extraction method for separation of phenolic compounds from coal tar. Chem Eng J 2015; 266: 148-55.
[24]
Bhosale VK, Kulkarni PS. Ultrafast igniting, imidazolium based hypergolic ionic liquids with enhanced hydrophobicity. New J Chem 2017; 41: 1250-8.
[25]
Amde M, Liu JF, Pang L. Environmental application, fate, effects, and concerns of ionic liquids: A review. Environ Sci Technol 2015; 49: 12611-27.
[26]
Bhosale VK, Patil NV, Kulkarni PS. Treatment of energetic material contaminated wastewater using ionic liquids. RSC Adv 2015; 5: 20503-10.
[27]
Ji Y, Hou Y, Ren S, Yao C, Wu W. Highly efficient separation of phenolic compounds from oil mixtures by imidazolium-based dicationic ionic liquids via forming deep eutectic solvents. Energy Fuels 2017; 31: 10274-82.
[28]
Wasserscheid P, Welton T. Ionic liquids in synthesis Weinheim, Germany: Wiley-VCH Verlag GmbH & Co KGaA; 2008.
[29]
Nosrati S, Jayakumar NS, Hashim MA. Performance evaluation of supported ionic liquid membrane for removal of phenol. J Hazard Mater 2011; 192: 1283-90.
[30]
Wei GT, Yang Z, Chen CJ. Room temperature ionic liquid as a novel medium for liquid/liquid extraction of metal ions. Anal Chim Acta 2003; 488: 183-92.
[31]
Sakal SA, Lu YZ, Jiang XC, Shen C, Li CX. A promising ionic liquid [BMIM][FeCl4] for the extractive separation of aromatic and aliphatic hydrocarbons. J Chem Eng Data 2014; 59: 533-9.
[32]
Girish CR, Ramachandra Murty V. Adsorption of phenol from aqueous solution using Lantana camara, forest waste: Kinetics, isotherm, and thermodynamic studies. Int Sch Res Notices 2014; 2014: 1-16.
[33]
Yao C, Hou Y, Ren S, Ji Y, Wu W, Liu H. Efficient separation of phenolic compounds from model oils by dual-functionalized ionic liquids. Chem Eng Process-Process Intensif 2018; 128: 216-22.
[34]
Pang K, Hou Y, Wu W, Guo W, Peng W, Marsh KN. Efficient separation of phenols from oils via forming deep eutectic solvents. Green Chem 2012; 14: 2398-401.
[35]
Hou Y, Ren Y, Peng W, Ren S, Wu W. Separation of phenols from oil using imidazolium-based ionic liquids. Ind Eng Chem Res 2013; 52: 18071-5.
[36]
Meng H, Ge CT, Ren NN, Ma WY, Lu YZ, Li CX. Complex extraction of phenol and cresol from model coal tar with polyols, ethanolamines, and ionic liquids thereof. Ind Eng Chem Res 2014; 53: 355-62.
[37]
Guo W, Hou Y, Wu W, Ren S, Tian S, Marsh KN. Separation of phenol from model oils with quaternary ammonium salts via forming deep eutectic solvents. Green Chem 2013; 15: 226-9.
[38]
Yao C, Hou Y, Ren S, Wu W, Ji Y, Liu H. Sulfonate based zwitterions: A new class of extractants for separating phenols from oils with high efficiency via forming deep eutectic solvents. Fuel Process Technol 2018; 178: 206-12.
[39]
Bhosale VK, Kulkarni SG, Kulkarni PS. Ionic liquid and biofuel blend : A low-cost and high-performance hypergolic fuel for propulsion application. Chem Sel 2016; 1: 1921-5.
[40]
Yao C, Hou Y, Ren S, et al. Efficient separation of phenol from model oils using environmentally benign quaternary ammonium-based zwitterions via forming deep eutectic solvents. Chem Eng J 2017; 326: 620-6.
[41]
Mokrani A, Madani K. Effect of solvent, time and temperature on the extraction of phenolic compounds and antioxidant capacity of peach (Prunus persica L.) fruit. Separ Purif Tech 2016; 162: 68-76.