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. 2026 Mar 23;11(13):20963–20970. doi: 10.1021/acsomega.5c13593

Sustainable Imidazolines Derived from Waste Cooking Oil for Corrosion and Paraffin Wax Inhibition in Petroleum Industry

Vaibhav A Edlabadkar 1,*, Hamid Rashidi Nodeh 1,*, Prasant Khadka 1, Hamed Sadatfaraji 1, Ifeanyi Nwobodo 1, Samantha Reyes 1, Crystal Rivera 1, Jaquelin Lopez 1, Erin Dugat 1, VN Ramachander Turaga 1, Justin Disney 1
PMCID: PMC13063012  PMID: 41970841

Abstract

Corrosion and paraffin deposition are the two major problems in the oil and gas industry. While corrosion impacts the integrity, safety, and longevity of structures, the formation of paraffin crystals can cause unwanted production challenges that often lead to reduced production volumes or production downtime. However, most common corrosion and paraffin inhibitors have high environmental footprints in oilfields. This study addresses this challenge by introducing waste cooking oil (WCO)-based imidazolines as corrosion and paraffin inhibitor. Imidazoline was synthesized using WCO and aminoethylethanolamine (AEEA) under atmospheric conditions. The formed imidazoline was characterized by FTIR and GC-FID with a >95% conversion rate. Their corrosion and paraffin inhibition performance was analyzed at different concentrations by rotating cylinder electrode (RCE) and coldfinger apparatus, respectively. WCO-imidazoline showed corrosion inhibition of up to 98% and paraffin inhibition of up to 51% in the oilfield samples. The results showed that the use of WCO is a good alternative for the synthesis of environmentally friendly corrosion and paraffin inhibitors with high inhibition efficiencies.

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1. Introduction

Corrosion is one of the most persistent, pervasive, and costly challenges in the oil and gas industry, exceeding USD 50 billion annually worldwide and >3.7 billion in the U.S. refinery sector, imposing substantial direct and indirect economic burdens while threatening asset integrity and operational reliability. Carbon steel pipelines, downhole tubing, and surface facilities are continuously exposed to aggressive production environments. In oil pipelines, the bottom of the line is persistently exposed to flowing liquid phases, such as condensate, water, and brine. Under wet gas transportation conditions, the presence of chloride ions, hydrogen sulfide, moisture, and carbon dioxide promotes corrosion. The dissolution of CO2 in water leads to the formation of carbonic acid (H2CO3), which subsequently dissociates into H+, HCO3 –, and CO3 2– species, thereby lowering the pH of the condensed aqueous phase. This acidic environment significantly accelerates corrosion, resulting in pipeline wall thinning, production losses, increased maintenance costs, and a higher risk of catastrophic failure. Beyond economic consequences, corrosion-related failures may also lead to environmental contamination and serious safety hazards, making corrosion control a critical priority in oilfield operations.

The application of corrosion inhibitors remains one of the most practical and cost-effective strategies for mitigating corrosion in such environments. Organic inhibitors based on tall oil fatty acids (TOFAs), coco-amines, oleic-based compounds, polymers, imidazolines, and quaternized imidazolines are widely used in the oil and gas sector, − due to their strong adsorption onto steel surfaces, where they form protective hydrophobic films that suppress both anodic and cathodic reactions. , Among these, imidazolines are multipurpose compounds extensively applied in the oil and gas industry to enhance water injection efficiency, inhibit corrosion and scale formation, improve oil recovery, and control acid gases. To further improve their corrosion inhibition performance and partitioning behavior in oil–water systems, long-chain derivatization is often employed. Long-chain imidazolines are synthesized by reacting various fatty acid sources (e.g., oleic acid, lauric acid, coconut oil, and TOFA) with polyamines such as diethylenetriamine (DETA), aminoethylethanolamine (AEEA), or triethylenetetramine (TETA). − Imidazoline–fatty acid derivatives are therefore considered key components of corrosion inhibitor formulations in the petroleum industry. Because the hydrophobic alkyl chains derived from fatty acids orient outward from the metal surface, they form a compact, water-repellent barrier that restricts the transport of corrosive species such as H+, CO2, and Cl– to the metal interface. , Concurrently, the corrosion inhibition mechanism of the imidazoline head is governed by its amphiphilic molecular structure and strong interfacial activity at the steel–electrolyte interface. The heterocyclic imidazoline ring, enriched with nitrogen atoms and lone-pair electrons, promotes chemisorption onto steel surfaces through coordination with vacant d-orbitals of iron, while electrostatic interactions facilitate physisorption under acidic and CO2-containing environments. This dual adsorption mechanism effectively suppresses both anodic iron dissolution and cathodic hydrogen evolution reactions, resulting in mixed-type inhibition behavior. Extension of the alkyl chain length enhances surface coverage, film cohesion, and stability under dynamic flow conditions while also improving oil-phase affinity and inhibitor partitioning at the oil–water interface. Therefore, long-chain imidazolines exhibit superior inhibition efficiency and persistence in multiphase oilfield environments, directly linking the molecular structure to corrosion protection performance.

Among all fatty acid-based imidazolines, the TOFA-imidazolines, made from tall-oil fatty acids, are widely used as corrosion inhibitors in commercial oilfield formulations. However, their reliance on specific feedstocks presents limitations, and the bulk crude nature increases the process cost. TOFA is not uniformly available worldwide; its cost can fluctuate with supply, and its production still depends on industrial processing that carries environmental burdens. These factors motivate the search for alternative, more sustainable raw materials for imidazoline synthesis.

Waste cooking oil (WCO) is an abundant and inexpensive residue generated from domestic and industrial food processing and is already recognized as a sustainable feedstock for biodiesel production. , Owing to its high triglyceride content composed of diverse fatty acid chains, WCO offers a chemically viable precursor for the synthesis of various long-chain imidazolines. Through amidation and subsequent cyclization reactions with polyamines, such as aminoethylethanolamine (AEEA), WCO can be efficiently converted into imidazoline structures suitable for corrosion inhibition applications in the petroleum industry. Using WCO not only adds value to an otherwise problematic waste stream but also reduces dependence on conventional feedstock, lowering both the cost and environmental impact.

Along with corrosion, crystallization of paraffin wax in crude oil, with subsequent deposition on the walls of pipelines and process equipment, is another major problem in the petroleum industry. Due to paraffin wax deposition, there is a reduction in the actual diameter of the pipeline, resulting in higher pressure drops and the formation of gelled interlocking structures in the pipeline and process equipment, which leads to the interruption of crude oil production. Paraffin deposition is generally managed with pour point depressants or crystal modifiers, which include maleic acid esters, polymeric acrylate and methacrylate esters, ethylene vinyl acetate polymers and copolymers, and alkyl phenol resins. , While effective, they have long-term negative environmental impacts due to their slow biodegradation rate.

In this work, we synthesized an imidazoline from waste cooking oil (WCO) and AEEA and investigated its performance as both a corrosion inhibitor and a paraffin inhibitor under oilfield-representative conditions. Electrochemical tests (RCE), weight-loss studies, and coldfinger tests were combined to evaluate the compound’s dual performance as a corrosion and paraffin inhibitor. By comparing conventional TOFA-derived imidazoline and commercial wax inhibitors, we demonstrated the technical viability of WCO-imidazolines as efficient and sustainable corrosion inhibitors acting as a dual-function flow assurance solution. This work highlights a pathway to reduce the overall chemical usage and improve environmental sustainability in oil and gas operations.

2. Experimental Section

2.1. Chemicals and Reagents

Waste cooking oil (WCO) was sourced directly from local fast-food markets (Midland, TX, USA) and filtered before use. Aminoethylethanolamine (AEEA) used for synthesis was purchased from Sigma-Aldrich (St. Louis, MO, USA) with the highest available purity. Commercial TOFA-imidazoline was obtained from Jacam Chemicals (Sterling, KS, USA). All salts including sodium chloride (NaCl), sodium bicarbonate (NaHCO3), sodium sulfate (Na2SO4 10H2O), calcium chloride (CaCl2 2H2O), magnesium chloride (MgCl2 6H2O), strontium chloride (SrCl2 6H2O), and potassium chloride (KCl) for making brines and solvents (xylene, isopropanol, and acetone) were obtained from Fisher Scientific (Waltham, MA, USA) and Sigma-Aldrich (St. Louis, MO, USA) and used as received without further purification. The crude oil used in all experiments was supplied by regional producers (Midland, TX, USA) and characterized prior to testing to determine relevant physical and chemical properties.

2.2. Material Synthesis

Synthesis of WCO-imidazoline was carried out using a modified literature procedure. It involved a two-stage reaction including (i) amidation and then (ii) cyclization to form an imidazoline ring, as illustrated in Scheme . WCO (1 mmol) and AEEA (3 mmol) were added to a three-neck round-bottom flask connected with an overhead stirrer, a condenser, and a thermocouple. The WCO and AEEA mixture was heated to 185 °C and stirred for 5 h. After this, the condenser was converted to the distillation apparatus, and the mixture was heated to 230 °C for 3 h to complete cyclization. Finally, the product (WCO-imidazoline) was obtained as a yellow wax in a 95% yield. FTIR (neat): νmax 3302, 3002, 2922, 2854, 1640, 1552, 1365, 1058, 723 cm–1.

1. Synthesis of WCO-Imidazoline from WCO and AEEA.

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2.3. Characterization

Fourier transform infrared (FTIR) spectra were obtained by using a PerkinElmer Spectrum Two spectrometer equipped with an attenuated total reflectance (ATR) accessory. The triglyceride content of WCO and synthesized product was obtained using an Agilent Technologies gas chromatography with flame ionization detection (GC-FID) equipped with a cool-on column apparatus. The coldfinger experiments were performed using a PSL Cold Finger apparatus (Osterode am Harz, Germany), designed for controlled wax deposition studies. Electrochemical corrosion testing employed a rotating-cyclone electrode (RCE) system manufactured by Gamry Instruments Company (Warminster, PA).

2.4. RCE Procedure (Corrosion Test)

Corrosion testing was conducted using an RCE system in accordance with established electrochemical protocols. Prior to each experiment, all RCE components including the cells, electrodes, and drive shafts were rigorously cleaned using sequential rinses of 15% HCl, deionized water with lab-grade detergent, xylene, and acetone, followed by final rinses with deionized and RO water. Brines were prepared based on field-representative water analyses using a custom simulation template, with cation salts added first and bicarbonate introduced last to avoid precipitation (brine composition: NaCl, NaHCO3, Na2SO4 10H2O, CaCl2 2H2O, MgCl2 6H2O, SrCl2 6H2O, and KCl). Brines were spiked with synthesized imidazoline at different concentrations (10, 15, 25, and 50 mg/L) and commercial TOFA–imidazoline (50 mg/L) for performance comparison, and unspiked brine was used as control. Each cell was filled with 1000 mL of brine and sparged with CO2 for a minimum of 30 min to remove dissolved oxygen. Preweighed carbon steel coupons were cleaned of protective coating via xylene–acetone sonication and mounted on the drive shafts using a washer–coupon–washer configuration. After insertion, the system was operated at 2000 rpm and 75 °C under continuous CO2 sparging to remove dissolved oxygen and establish CO2-saturated conditions, thereby maintaining carbonic acid equilibrium and solution pH representative of oilfield corrosion environments. The electrochemical measurements were collected by using a Gamry Instruments system operating the RPec Trend script. Open circuit potential (OCP) stabilization was confirmed prior to dosing, and corrosion rates were monitored continuously over a 12 h period. Data were analyzed using Gamry Echem Analyst and processed through a standardized template for corrosion rate and inhibition efficiency calculations.

2.5. Coldfinger Procedure (Wax Deposition Test)

Wax deposition performance was evaluated using a PSL Cold Finger apparatus designed to simulate paraffin precipitation under controlled thermal condition. A total of 80 mL of preheated crude oil at 70 °C was placed in the test cell (round beaker), and the coldfinger rod was maintained at a fixed temperature of 0 °C, while the bulk fluid temperature was held at 30 °C. These temperature conditions were selected based on the oil’s measured cloud point of 16 °C, ensuring a consistent driving force for wax crystallization. The system was stirred continuously to maintain a uniform heat transfer. Tests were conducted with and without the presence of synthesized imidazoline-based additives, dosed (spiked) at concentrations of 500 and 1000 mg/L. Each test was run for a duration of 4 h, after which the coldfingers were removed, and the adhered wax was carefully weighed and compared to blank measurements to evaluate the additive’s inhibition performance.

2.6. GC-FID Analysis

The analysis method was set based on the direct triglyceride analysis protocol with GC-FID. , The cool-on-column system with oven tracking mode was used under a capillary column of Restek MXT-1HT Sim Dist (L. Five m, i.d. 0.53 mm, and 0.1 μm), and the oven program was set with a gradient from 80 °C (1 min), ramp 5 °C/min to 150 °C (1 min), ramp 15 °C/min to 350 °C (10 min); helium 18 mL/min; FID temperature 400 °C.

For the experiment, 0.1 g of plain WCO, synthesized WCO-imidazoline, and TOFA-imidazoline were each dissolved in different vials and diluted with isopropyl alcohol to 10 mL. Then, 0.3 μL of each sample was injected into the GC-FID, and chromatograms were recorded properly.

3. Results and Discussion

3.1. Synthesis of WCO-Imidazoline

Scheme summarizes the route for the synthesis of WCO-imidazoline. The synthesis was performed using modified literature procedures. , The first step involves the formation of the fatty acid hydroxyethylaminoethylamide and glycerol by the reaction of AEEA and WCO at 185 °C. In the second step, the fatty amide was distilled at 230 °C to complete cyclization to form WCO-imidazoline.

3.2. FTIR

Figure compares the FTIR spectra of WCO and the final imidazoline product. The peak at 1745 cm–1 in WCO corresponds to the CO stretch of the triglycerides in the oil. After the reaction, this peak vanished completely, and a new band appeared at 1640 cm–1 of CN stretch indicating the formation of cyclic imidazoline molecule. The WCO-imidazoline shows a peak at 3302 cm–1, which corresponds to the O–H stretch. This stretch originally from AEEA was retained throughout the transformation into the final product. The imidazoline spectrum also presented new absorption bands at 1552 and 1365 cm–1, which were ascribed to N–H bending and C–N stretching bonds, respectively. This agreed well with characteristic absorption peaks for imidazoline reported in the literature. −

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FTIR of WCO and WCO–imidazoline.

3.3. WCO-Imidazoline Analysis with GCFID

The gas chromatograms in Figure clearly demonstrate the compositional differences among plain WCO, the synthesized WCO-imidazoline, and the commercial reference TOFA-imidazoline product. The WCO chromatogram (blue trace) exhibits a dominant peak near 38 min corresponding to the major triglyceride. After imidazoline synthesis, the chromatographic profile (green trace) changes significantly. The disappearance or reduction of the main triglyceride peak, together with the appearance of several new peaks at shorter retention times (12–18 min), indicates the successful conversion of triglyceride to monofatty acid with nitrogen-containing heterocycles (imidazoline). These new components likely represent imidazoline derivatives and intermediate amides formed through the cyclization and dehydration of fatty acid–amine intermediates. This claim has been confirmed by the analysis of commercial TOFA-imidazoline. Hence, the TOFA chromatogram (red trace) displays a similar distribution of peaks, confirming structural similarity but suggesting compositional differences due to the mixed long fatty acid chain lengths in WCO. Moreover, it can be claimed that the conversion rate for WCO-imidazoline is higher than that for TOFA-imidazoline, because the intense peak of the unreacted fatty acid present in TOFA-imidazoline still appears (retention 28 min). Overall, the shift in retention pattern and the emergence of multiple nitrogen-bearing species confirm that waste cooking oil was effectively transformed into imidazoline.

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GC-FID chromatograms for WCO, WCO-imidazoline, and TOFA-imidazoline.

3.4. Corrosion Inhibition Performance

The corrosion inhibition efficiency of the WCO-imidazoline and commercial product (TOFA–imidazoline) was studied under the RCE system for 12 h, and the inhibition efficacy is shown in Figure . The results show that WCO-imidazoline delivered strong corrosion protection under field brine conditions. At 50 mg/L inhibitors, the corrosion rate dropped from 187.65 to 3.44 mpy (see Table S2 in Appendix IV), giving a 98.2% inhibition and indicating rapid formation of a stable protective film over the coupons. This trend is consistent with imidazoline concentration increasing from 10 to 50 mg/L, where excess polar species can interfere with the surface of carbon steel and making a film over it. Looking closely at the inhibition data, for WCO-imidazoline, the inhibition efficiency increased markedly from 89.2% at 10 mg/L to 94.5% at 15 mg/L, indicating rapid surface coverage at low concentrations. A further increase to 25 mg/L resulted in no significant improvement (94.7%), suggesting that near-complete surface coverage was achieved. Although a higher efficiency of 98.2% was observed at 50 mg/L, the improvement was incremental relative to the additional inhibitor dosage. Therefore, 15 mg/L was identified as the optimum concentration, providing effective corrosion protection with minimal inhibitor consumption under RCE conditions. The corrosion efficiency was compared with the commercial inhibitors TOFA-imidazoline (50 mg/L) and WCO-imidazoline (25 mg/L), which perform competitively with inhibition efficiency (>98%) and even showed a lower final corrosion rate. Overall, the higher efficiency of WCO-imidazoline compared to that of the TOFA-based commercial inhibitor is probably due to the broader and longer-chain fatty acid distribution present in the WCO precursor, as long-chain hydrocarbons enhanced the hydrophobic packing barrier to water and chloride ingress over steel.

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Corrosion inhibition efficiencies of WCO-imidazoline at different concentrations (blue) and TOFA-imidazoline at 50 mg/L (red).

3.5. Possible Inhibition Mechanism

The inhibition mechanism is strongly influenced by the solution pH. CO2 saturation of the brine at 75 °C typically results in acidic conditions (pH ∼3–4), as reported for similar CO2-brine systems. Continuous CO2 purging was applied to maintain a constant CO2 partial pressure and carbonic acid equilibrium, thereby preserving steady-state pH conditions during RCE testing. Under these acidic conditions, corrosion is primarily governed by anodic iron dissolution coupled with cathodic carbonic acid reduction, while the formation of protective FeCO3 films is thermodynamically unfavorable and further suppressed by high shear stress. Consequently, the observed corrosion inhibition is attributed mainly to adsorption of the WCO-imidazoline inhibitor.

The oilfield brine used in this study contains a high concentration of chloride ions (79,141 mg/L), along with significant amounts of Ca2+, Mg2+, and HCO3 –. Under RCE conditions at 75 °C and 2000 rpm, the aggressive CO2-saturated chloride brine promotes active anodic dissolution of iron, resulting in continuous generation of Fe2+ species in solution. − Although the steel surface is not uniformly charged, the specific adsorption of chloride ions occurs preferentially at anodic sites, producing locally negatively charged interfacial regions. At acidic pH typical of CO2-saturated brine, WCO-imidazoline molecules exist predominantly in protonated form. Adsorption of the inhibitor is therefore facilitated by the electrostatic interaction between protonated imidazoline molecules and adsorbed chloride ions, leading to the formation of an anion-bridged protective film on the steel surface. In addition to electrostatic attraction, donor–acceptor interactions between heteroatoms in the inhibitor molecule and vacant iron orbitals may further stabilize adsorption. This combined physical and chemical adsorption mechanism is consistent with the widely reported behavior of imidazoline-type inhibitors in chloride-containing CO2 corrosion systems. ,, This adsorption mechanism provides rapid initial surface coverage, which explains the rapid decrease in corrosion rate (3.44 mpy; see Table S2 in Appendix IV) observed in the RCE test. This dual adsorption pathway is shown in Figure . The combined effect of electrostatic adsorption, Fe–N chemisorption, and long-chain hydrophobic film formation is responsible for the strong corrosion inhibition efficiency exhibited by WCO-imidazoline under RCE conditions.

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Possible corrosion inhibition mechanisms of WCO-imidazoline under oilfield conditions.

3.6. Wax Inhibition Performance

The coldfinger instrument was used to study the wax inhibition performance of the WCO-imidazoline. Four different types of oils were used to evaluate the inhibition performance. The percentage inhibition was calculated based on the amount of wax deposition on the blank compared to the treated sample. The weight data for all the experiments is shown in Table S3, Appendix V. Images in Figure show fingers with wax deposition after testing WCO-imidazoline in different crude oil matrices. In all selected oils, including high sludgy, medium sludgy, high asphaltene, and light oil, the blank samples show a thick wax layer deposited on the metal surfaces, confirming a high natural wax tendency of these crude systems. Upon treatment with WCO-imidazoline at 500 and 1000 mg/L, a decrease in wax accumulation and deposit thickness was observed. As shown in Figure , the visual differences between 500 and 1000 mg/L concentrations are not equally pronounced for all crude types. In high asphaltene oil (Figure c), the inhibition improvement between 500 mg/L (16.0%) and 1000 mg/L (16.5%) is minimal, which is consistent with a similar visual appearance. In medium and high sludgy oils (Figure a,b), although gravimetric measurements indicate moderate improvement at higher dosage, the nonuniform and irregular morphology of wax deposits masks thickness variations in photographic images. In contrast, the light oil system (Figure d) shows both visually distinguishable reduction in deposition and significant numerical improvement (36.7% to 51.2%). These observations confirm that visual assessment alone is insufficient for quantitative comparison, and gravimetric measurements were, therefore, used to determine inhibition efficiency.

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Coldfinger wax deposition for WCO-imidazoline. From left to right: blank, 500 mg/L, and 1000 mg/L. (a) High sludgy oil; (b) medium sludgy oil; (c) high asphaltene oil; and (d) light oil.

The optimal WCO-imidazoline concentration for wax inhibition was evaluated based on gravimetric coldfinger measurements. The results indicate that the effectiveness of the inhibitor is crude-dependent. For light oil, inhibition efficiency increased significantly from 36.7% at 500 mg/L to 51.2% at 1000 mg/L, indicating that 1000 mg/L provides superior wax control. In medium and high sludgy oils, the improvement between 500 and 1000 mg/L was moderate (38.5%–41.8% and 20.0%–39.1%, respectively). In contrast, high asphaltene oil showed negligible improvement (16.0%–16.5%), suggesting limited sensitivity to increased dosage. Therefore, 1000 mg/L can be considered the optimal concentration for light and sludgy crude systems under the studied conditions, whereas increasing dosage in high asphaltene crude does not yield significant additional benefit. Compared to wax-inhibitors in the literature such as poly­(BA-co-SMA-co-MA), amine-modified maleic anhydride, and polyaminoamide from soybean oil, with inhibition 45.6%, 73.63%, and 66.2%, respectively, our WCO-imidazoline showed competitive inhibition (51%).

4. Conclusion

In this work, an imidazoline inhibitor based on waste cooking oil was successfully synthesized. The evaluation of corrosion inhibition efficacy by electrochemical and weight-loss measurements confirmed its suitability as a promising corrosion inhibitor for carbon steel pipelines in a CO2-containing environment. The corrosion inhibition efficiency increased with increasing inhibitor concentration, reaching >98% at 50 mg/L, which is better than the widely used commercial TOFA-imidazoline at the same concentration. Under the studied RCE conditions, 15 mg/L was determined to be the optimal WCO-imidazoline concentration, providing efficient corrosion protection with minimal dosage. The wax inhibition efficiency varied with oil type, reaching 51% inhibition for light oil, which is comparable to conventional paraffin inhibitors. For wax mitigation, 1000 mg/L provided the highest inhibition efficiency in light and sludgy crude oils, while higher dosages did not significantly improve performance in high-asphaltene systems. WCO represents a circular and sustainable raw material for the synthesis of value-added products. The use of WCO as a biodegradable feedstock for synthesis is advantageous. The excellent performance of this imidazoline clearly positions it as an environmentally friendly, low-cost, and sustainable dual-function flow assurance solution in oil and gas operations.

Supplementary Material

ao5c13593_si_001.pdf (209.5KB, pdf)

Acknowledgments

The authors thank Jacam Catalyst for allowing this work to be published.

The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsomega.5c13593.

  • Brine composition used for RCE corrosion testing (Table S1); variation of inhibition efficiency over 12 h for WCO-imidazoline and TOFA-imidazoline (Figure S1); variation of corrosion rate over 12 h (Figure S2); initial and final corrosion rate data with inhibition efficiency from RCE testing (Table S2); and paraffin wax deposition data from coldfinger experiments for different oil types (Table S3) (PDF)

The authors declare no competing financial interest.

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