Microwave-ultrasonic assisted extraction of lignin to synthesize new nano micellar organometallic surfactants for refining oily wastewater

Abstract

In this work, a beneficial approach for efficient depolymerization of lignin and controllable product distribution is provided. Lignin, an abundant aromatic biopolymer, has the potential to produce various biofuels and chemical adsorption agents and is expected to benefit the future circular economy. Microwave-ultrasonic (MW/US) assisted efficient depolymerization of lignin affords some aromatic materials used in manufacturing the starting material to be investigated. Some nano organometallic surfactants (NOMS) based on Ni²⁺, Cu²⁺, Co²⁺, Fe³⁺, and Mn²⁺ besides 2-hydroxynaphth-sulphanilamide are synthesized to enhance oil recovery (EOR). In this work, the assessment of the NOMS’s efficiency was improving the heavy oil recovery via the study of the dynamic interfacial tension (IFT), contact angle, and chemical flooding scenarios. The NOMS-Ni²⁺ exhibited the maximum reduction of viscosity and yield values. Dropping the viscosity to 819.9, 659.89, and 499.9 Pa s from blank crude oil viscosity of 9978.8, 8005.6, and 5008.6 Pa s respectively at temperatures of 40, 60, and 80 °C was investigated. The reduction of τ_B values was obtained also by OMS-Ni²⁺. The minimum IFT was recorded against the Ni²⁺ derivatives (0.1 × 10^–1 mN m⁻¹). The complete wettability alteration was achieved with the NOMS-Ni²⁺ surfactant (ɵ $\cong 6.01).$ The flooding test has been steered in 3 sets using the sand-packed model as a porous media at surfactant concentrations (1, 1.5, 2 and 2.5%) at 50 °C and 499 psi as injection pressure. The best value (ORs) formed for NOMS-Ni²⁺ were 62, 81, 85.2, and 89% respectively as compared with other NOMS-M²⁺ at the same concentrations. The mechanism of alternating wettability was described in the text. The rheology of the used heavy crude oil was investigated under temperatures of 40, 60, and 80 °C.

Keywords

Nano-micellar surfactants / Improving heavy oil recovery / Organometallic surfactants / Salen metal complexes / Wettability alteration

References

[1] Abdelhamid MM, Rizk SA, Betiha MA, Desouky SM, Alsabagh AM. Improving heavy oil recovery, part (I): synthesis and surface activity evaluation of some novel organometallic surfactants based on salen–M complexes. RSC Adv, 2021, 11(3): 1750-1761.

[2] Afolabi OR. Enhanced oil recovery for emergent energy demand: challenges and prospects for a nanotechnology paradigm shift”. Int Nano Lett, 2018, 9(1): 1-15.

[3] Al-Kindi S, Al-Bahry S, Al-Wahaibi Y, Taura U, Joshi S. Partially hydrolyzed polyacrylamide enhanced oil recovery applications oil-field produced water pollution and possible solutions. Environ Monit Assess, 2022, 194: 875-881.

[4] Alsabagh AM, Hassan ME, Desouky SEM, Nasser NM, Elsharaky EA, Abdelhamid MM. Demulsification of W/O emulsion at petroleum field and reservoir conditions using some demulsifiers based on polyethylene and propylene oxides. Egypt J Pet, 2016, 25(4): 585-595.

[5] Ayirala, S C. 2002. Surfactant-induced relative permeability modifications for oil recovery enhancement. MSc Thesis Graduate Faculty of the Louisiana State University and Agricultural and Mechanical College Department of Petroleum Engineering, Baton Rouge, Louisiana.

[6] Badamali SK, Clark JH, Breeden SW. Microwave assisted selective oxidation of lignin model phenolic monomer over SBA-15. Catal Commun, 2008, 9: 2168-2170.

[7] Chaturvedi KR, Sharma T. Rheological analysis and EOR potential of surfactant treated single-step silica nanofluid at high temperature and salinity. J Petrol Sci Eng, 2021, 196.

[8] ClearTech. 2006. Industrial chemicals, north corman industrial park, saskatoon S7L 5Z3, Canada. http://www.cleartech.ca/products.html.

[9] Curbelo FDS, Santanna VC, Barros Neto EL, Dutra TV Jr, Castro Dantas TN, Dantas Neto AA, Garnica AIC. Adsorption of nonionic surfactants in sandstones. colloids and surfaces a: physicochem. Eng Asp, 2007, 29: 1-4.

[10] Da Cruz AFT, Sanches RD, Miranda CR, Brochsztain S. Evaluation of cyclodextrins as environmentally friendly wettability modifiers for enhanced oil recovery. Colloid Interfac, 2018, 2: 10-18.

[11] Davoodi S, Al-Shargabi M, Wood DA, RukavishnikovK.M. VSM. Experimental and field applications of nanotechnology for enhanced oil recovery purposes: a review. Fuel, 2022, 324: 124669-124676.

[12] Duana D, Wanga Y, Ruana R, Tayiera M, Daia L, Zhao Y, Zhoua Y, Liu Y. Comparative study on various alcohols solvolysis of organosolv lignin using microwave energy: physicochemical and morphological properties. Chem Eng Process Process Int, 2018, 126: 38-44.

[13] Elkamel A, Al-Sahhaf T, Ahmed AS. Studying the interactions between an Arabian heavy crude oil and alkaline solutions. J Pet Sci Tech, 2002, 20: 789-807.

[14] Huaping ZHU, Zongbin WU, Yuan Xiong CHEN, Ping ZHANG, Shijie DUAN, Xiaohua LIU, Zongqiang MAO. reparation of biodiesel catalyzed by solid super base of calcium oxide and its refining process. Chin J Catal, 2006, 27(5): 391-396.

[15] Kazemzadeh Y, Shojaei S, Riazi M, Sharifi M. Review on application of nanoparticles for EOR purposes: a critical review of the opportunities and challenges. Chin J Chem Eng, 2019, 27(2): 237-246.

[16] Khan MI, Islam MR. Handbook of sustainable oil and gas operations management, 2008, Houston: Gulf Publishing Company.

[17] Leng L, Chen J, Leng S, Li W, Huang H, Li H, Yuan X, Li J, Zhou W. Surfactant assisted upgrading fuel properties of waste cooking oil biodiesel. J Clean Prod, 2019, 210: 1376-1384.

[18] Liu Q, Dong M, Yue X, Hou J. Synergy of alkali and surfactant in emulsification of heavy oil in brine. colloids and surfaces a: physicochem. Eng Asp, 2006, 273: 219-228.

[19] Liu Q, Dong M, Ma S, Tu Y. Surfactant enhanced alkaline flooding for western Canadian heavy oil recovery. colloids and surfaces a: physicochem. Eng Asp, 2007, 293: 63-71.

[20] Luo KH, Zhao SJ, Fan GZ, Cheng QP, Chai B, Song GS. Oxidative conversion of lignin isolated from wheat straw into aromatic compound catalyzed by NaOH/NaAlO₂. Food Sci Nutr, 2020, 8(7): 3504-3514.

[21] Nanayakkara S, Patti AF, Saito K. Chemical depolymerization of lignin involving the redistribution mechanism with phenols and repolymerization of depolymerized products. Green Chem, 2014, 16: 1897-1903.

[22] Novriansyah A, Bae W, Park C, Permadi AK, Riswati SS. Optimal design of alkaline–surfactant–polymer flooding under low salinity environment. Polymers, 2020, 12(3): 626-631.

[23] Pashapouryeganeh F, Zargar G, Kadkhodaie A, Rabiee A, Misaghi A, Zakariaei SJS. Experimental evaluation of designed and synthesized alkaline-surfactant-polymer (ASP) for chemical flooding in carbonate reservoirs. Fuel, 2022, 321: 124090-124102.

[24] Rahman MS. Natural materials for EOR and environmental applications, 2007, Halifax Nova Scotia: MA.Sc Thesis, Faculty of Engineering, Dalhousie University.

[25] Rizk SA, Atta-Allah SR. Microwave-assisted regioselective reaction of furanone derivative supported by DFT stimulation and molecular docking to afford controlling insecticidal agents. J Iran Chem Soc, 2021, 18: 2407-2423.

[26] Rizk SA, Abdelwahab SS, Abdo AM. Ultrasonic-assisted synthesis and quantum chemical analysis of spiro[indoline-3,3′-pyrazol]-2-one derivatives as effective bactericidal and viricidal agents. Polycycl Aromat Compd, 2022, 43(3): 2052118.

[27] Ruiquan Z, Chenghao L, Di W, Shubo D. Colloids and surfaces a: physicochemical and engineering aspects characterization and demulsification of produced liquid from weak base ASP flooding. Colloid Surf A, 2006, 290(13): 164-171.

[28] Satyarthi JK, Srinivas D, Ratnasamy P. Hydrolysis of vegetable oils and fats to fatty acids over solid acid catalysts. Appl Catal A, 2011, 391(12): 427-435.

[29] Song XW, Zhao R, Cao XL, Zhang JC, Zhang L, Zhang L, Zhao S. Dynamic interfacial tensions between offshore crude oil and enhanced oil recovery surfactants. J Dispers Sci Technol, 2013, 34(2): 234-239.

[30] Taylor KC, Schramm LL. Measurement of short-term low dynamic interfacial tensions: application to surfactant enhanced alkaline flooding in enhanced oil recovery. Colloid Surf, 1990, 47: 245-253.

[31] Toledano A, Serrano L, Pineda A, Romero AA, Luque R, Labidi J. Microwaveassisteddepolymerisation of organosolv lignin via mild hydrogen-free hydrogenolysis:catalyst screening. Appl Catal B: Environ, 2014, 145: 43-55.

[32] Zehua C, Xiutai Z. Enhancing heavy-oil recovery by using middle carbon alcohol-enhanced waterflooding, surfactant flooding, and foam flooding. Energ Fuel, 2015, 29: 150407060547007.

Funding

Ministry of Education, Saudi Arabia (R-2023-899)