- Research article
- Open Access
Synthesis of hydroxylated fatty amide from underutilized seed oil of Khaya senegalensis: a potential green inhibitor of corrosion in aluminum
© The Author(s). 2018
- Received: 28 August 2018
- Accepted: 6 November 2018
- Published: 16 November 2018
Corrosion is a serious problem all over the world. Most currently used approach to control corrosion have short comings which necessitates the search for novel materials that are green, cheap, from renewable source, and eco-friendly that can be used to combat this problem of corrosion control.
Khaya senegalensis fatty hydroxylamide (KSFA) was synthesized from K. senegalensis seed oil via simple reaction route involving esterification, transesterification, hydroxylation, and amidation reaction. KSFA was characterized using Fourier-transform infrared (FTIR), nuclear magnetic resonance (1HNMR), CHN elemental analyzer, particle size distribution (PSD), X-ray diffractometer, zeta potential, thermogravimetric analysis (TG), thermogravimetric-mass spectrometer (TG-MS), and scanning electron micrograph (SEM) coupled with energy dispersion spectroscopy (EDS). Inhibitory effect of KSFA on corrosion of aluminum (Al) in 0.5 M HCl was studied at different concentrations of KSFA and temperatures using weight loss method.
Result from gas chromatography (GC) revealed oil of K. senegalensis to predominantly contain C18:1 (68.46%) fatty acid. Hydroxyl and amide functional groups present in KSFA were confirmed by FTIR and 1HNMR. TG analysis revealed loss in mass around 80–190, 200–450, and above 450 °C while TG-MS revealed five different masses with m/z values 16, 17, 18, 28, and 44. Corrosion inhibition capacity of KSFA was by surface adsorption, which is spontaneous, and physisorption and described by Langmuir isotherm. The corrosion inhibition efficiency of KSFA increased with increase in its concentration while its corrosion rate reduced with increase in concentration.
The inhibition efficiency of 90.43% exhibited by KSFA and the fact that KSFA was synthesized via non-hazardous process from a renewable sourced biomass is an indication that KSFA is a potential green and efficient inhibitor of corrosion in aluminum. KSFA is simple to use as an inhibitor and easy to prepare.
- Corrosion inhibitors
- Khaya senegalensis
- Seed oil
Corrosion of metal can be described as an electrochemical process involving the oxidation of anode coupled with a reduction reaction. During this process, metal is in contact with water or moisture in the atmosphere, and at such, the metal is the anode while the water is the electrolyte (Aylward and TJV 2002). This simply describes what happens during the corrosion of metals. This has had several negative impacts on equipment, structures, and several appliances made of metals or containing metals. The deterioration of materials caused by corrosion is a serious concern, which has enormous economic implications. Al is an important metal that has found several domestic and industrial applications. Al is known to resist corrosion due to its low electrode potential and ability to form a protective oxide (Al2O3) film. Despite of its ability to form a protective oxide film, Al is still susceptible to pitting corrosion; a process which is initiated in the presence of anion such as chloride which is capable of penetrating its protective oxide film (Gustafsson 2011; Li et al. 2013). The stability of the protective oxide is pH dependent and it is only stable within the pH range of about 4 to 8; the stability gets altered at pH less than 4 or at pH higher than 8. As a result, this exposes the Al to damage via corrosion. The cost of replacing Al because of corrosion is expensive (Eddy et al. 2015). Although some methods have been used in time past to control corrosion of metals, some of them still surfer from certain draw backs such has toxicity, high cost, and efficiency (Lecante et al. 2011; Deshpande et al. 2014; Wei et al. 2015; Taghavikish et al. 2017). However, the use of biomass, which is biodegradable, non-toxic, readily available, and green as corrosion inhibitors, has the potential of circumventing this draw backs.
Presently, efforts are made to develop novel materials that are green, cheap, renewable, and recyclable to meet the unprecedented demands for eco-friendly chemicals. Some of these eco-friendly chemicals may have the ability of being corrosion inhibitors and as such contributing significantly to sustainable development. The use of inhibitors is a well acceptable method for the protection of metal against corrosion, mostly in acidic media (Tawfik 2015). Most corrosion inhibitors are organic compounds containing heteroatoms (nitrogen, oxygen, and sulfur) and or π-electrons in their structures; the presence of which determines the efficiency and mechanism of operation of these inhibitors (Kokalj et al. 2010; Yadav et al. 2015). These heteroatoms and π-electrons are considered to achieve the inhibition by interacting with the metal surface which results in the formation of an inhibitive surface film (Sastri 2011), although this inhibition mechanism has not been clearly understood (Kokalj et al. 2010, Yadav et al. 2015).
Oleochemicals are chemicals obtained from plants and animals. They have found a wide range of domestic and industrial applications, which includes use as cosmetics, fuels, cleaners, lubricants, bioplastics, surfactants, and surface coatings. Oleochemicals synthesized from plant seed oil have the possibility of containing heteroatoms and or π-electrons in their structures, which presents them as potential inhibitors for corrosion control. They are possible replacements for petroleum-based chemicals, are eco-friendly, are biodegradable, and are from a renewable source. Therefore, the search for lesser-known or underutilized plant oil for oleochemical production has been of interest. Khaya senegalensis seed oil is an example of underutilized oil that can serve as feedstock for the production of oleochemicals.
K. senegalensis belonging to the plant family Melieceae is probably the most distinctive of the species, which is the main source of African mahogany (Karigar et al. 2010), often planted as shade tree and sometimes for beautification. The oil from the plant has been reportedly used as a fumigant in pest control in Asia and Africa (Bamaiyi et al. 2007). Okieimen and Eromosele (1999) reported the fatty acid content from the seed oil obtained from Eastern part of Nigeria as stearic acid (10.41%), palmitic acid (21.39%), oleic acid (64.62%), and unidentifiable acid (3.58%) while Karigar et al. (2010) reported the fatty acid from Indian sourced K. senegalensis seed oil as myristic acid (0.1%), palmitic acid (10.93%), stearic acid (7.77%), oleic acid (72.95%), and linoleic acid (7.92%). The high unsaturation of the fatty acid content of the seed oil was a pointer of π-electron system and that this oil can be modified for better production of oleochemicals, which could act as corrosion inhibitors.
In this light, the aim of this present work is to develop an Al corrosion inhibitor that is green, from a renewable source, and eco-friendly. To achieve this, we synthesized fatty hydroxylamide (an oleochemical) from the seed oil of K. senegalensis and also evaluated it for its corrosion inhibition capacity against Al in acidic medium.
The seeds of K. senegalensis were obtained from a garden in Ibadan, Oyo state, Nigeria. The seeds were air dried and ground into powder. Hydrogen peroxide, n-hexane, ethylenediamine, formic acid, sodium methoxide, and all other chemicals used were purchased from Sigma-Aldrich (Brazil). Oil was later extracted from the powdered seeds of K. senegalensis using n-hexane for 10 h in a soxhlet extractor.
Fatty acid composition
The oil of K. senegalensis was analyzed for its fatty acid composition as previously described by Adewuyi et al. (2014) with little modification. The fatty acids were determined as fatty methyl esters of the oil of K. senegalensis. Oil of K. senegalensis was refluxed at 70 °C for 3 h in 2% sulfuric acid in methanol to produce the methyl esters. Identification of the fatty acids, and their composition was carried out on a HP7820A gas chromatograph (Agilent) equipped with flame ionization detector. A SP2560 column (30 m × 0.25 mm × 0.20 μm) was used for the analysis while keeping the injector and detector temperature at 250 °C and 260 °C, respectively. Oven temperature was also programmed at 120 °C with steady increase at 7 °C/min until this was finally increased to 240 °C. The carrier gas was hydrogen at a flow rate of 1.5 mL/min, and the volume of injection was 1 μL. Data acquisition program EZChrom Elite Compact (Agilent) was used while identification of peaks was made by comparison with standards of fatty acid methyl esters C14-C22 FAME (Supelco cat no 18917).
Hydroxylated methyl esters from the seed oil of K. senegalensis
The seed oil of K. senegalensis was converted to methyl esters as previously described (Adewuyi et al. 2012) and later hydroxylated. Briefly, this was achieved by firstly esterifying the seed oil using 2% sulfuric acid in methanol at 70 °C for 2 h to convert the free fatty acid content of the oil to methyl esters. This was later transesterified using 1% KOH in methanol at 70 °C for 4 h. The product obtained was extracted with ethyl acetate, washed with distilled water until free of KOH, and passed over sodium sulfate, and ethyl acetate was removed using a rotary evaporator.
The methyl esters formed were finally hydroxylated using performic acid produced in situ (Adewuyi et al. 2013). Methyl esters of K. senegalensis (0.0482 mol) and formic acid (0.106 mol) were poured into a three-necked round-bottom flask; the mixture was gently cooled to a temperature of 15 °C. Hydrogen peroxide (0.407 mol) was further added dropwise to the mixture while the temperature of the mixture was later raised to 70 °C and the reaction was allowed to continue for 15 h. The mixture was cooled to room temperature, and the hydroxylated methyl esters were extracted from the product using ethyl acetate; this was washed severally with distilled water until acid free and passed over sodium sulfate. The hydroxylated methyl esters were separated from the ethyl acetate using a rotary evaporator.
Synthesis of KSFA
The FTIR spectra of the starting material (oil) and final product (KSFA) were recorded using FTIR (Perkin Elmer, spectrum RXI 83303). The samples were blended with KBr, pressed into pellets, and analyzed in the range of 400–4500 cm− 1.
1HNMR spectra of starting material (oil) and final product (KSFA) were obtained using a 400 MHz Bruker Advance DRX 400 NMR spectrophotometer in CDCl3 containing some amount of TMS as internal standard.
CHN elemental analysis and particle size distribution
Elemental analysis was achieved using Perkin Elmer series II CHNS/O analyzer (Perkin Elmer, 2400, USA). Zeta potential analyzer (DT1200, Dispersion technology) was used to obtain the surface potential and particle size distribution, KSFA was made into powder form and the zeta potential analyzer was operated at 25 °C.
X-ray diffraction, TG and TG-MS analysis
The structural information was obtained using X-ray diffractometer (XRD-7000X-Ray diffractometer, Shimadzu) with filtered Cu Kα radiation operated at 40 kV and 40 mA. The XRD pattern was recorded from 10 to 80 °C of 2θ/s with a scanning speed of 2.00° of 2θ/min while TG analysis was carried out on DTG-60 (Shimadzu, C30574600245) under nitrogen atmosphere. The TG-MS (NETZSCH thermobalance model STA 449 F3 coupled with mass spectrometer NETZSCH Aëolos model QMS 403C with EI and quadrupole analyzer) was carried out in an argon flux of 20 mL min− 1 at a temperature range of 40–1000 °C and heating rate of 5 °C min− 1.
Surface morphology of samples was carried out using SEM (JEOL JSM-6360LV, Japan) coupled with EDS (Thermo Noran, 6714A-ISUS-SN, USA).
The Al sheets used in this study were 0.6 mm in thickness and were mechanically pressed cut into 3 × 3 cm coupons. Al sheets were degreased using ethanol; they were dried in acetone, and later stored before their use in corrosion studies. The corrosion process was initiated using HCl (0.5 M) while KSFA was used as the corrosion inhibitor. Concentrations of KSFA ranging from 5 × 10− 5 to 1 × 10− 3 mg/L were prepared using 0.5 M HCl as solvent to study the inhibitory capacity of KSFA during corrosion initiated by the 0.5 M HCl. The 0.5 M HCl solution was used as control while the other solutions prepared containing KSFA were used as test solution.
The corrosion taking place at the surface of the Al metal was studied using the procedure for weight loss determination of corrosion rates. Weight loss was determined by total immersion at room temperature using 100-mL capacity beakers containing 50 mL test solution. The Al sheets were pre-weighed, after which they were separately suspended in different beakers filled with the solution. The coupons were retrieved at 30-min intervals progressively for 72 h, washed thoroughly in deionized water, cleaned, dried in acetone, and re-weighed. The weight loss was considered as the difference in weight of the Al coupons before and after immersion in test solutions. The tests were repeated at different temperatures (298–333 K) in order to determine the effect of temperature on rate of corrosion.
Synthesis of KSFA
Fatty acid composition of Khaya senegalensis
where n is the amount of water molecules displaced by one inhibitor molecule. The charge on inhibitors depends on the presence of loosely bound electrons, lone pairs of electrons, π-electron clouds, aromatic ring systems, and functional groups containing elements of group V or VI of the periodic table (Sastri 1998). The strength of adsorption or displacement of the water molecules depends on the charge on the heteroatoms present in the inhibitor. In the case of KSFA, oxygen and nitrogen are present in its molecule, which may have played active role in this regard.
Corrosion rates and inhibition
Values of corrosion rate, inhibition efficiency, and surface covering at 298 K
Corrosion rate (mg cm−2 h− 1)
Inhibition efficiency (%IEw)
Degree of surface covering (θ)
Interpretation of KR parameter
Values of KR
Type of isotherm
KR > 1
KR = 1
0 < KR < 1
KR = 0
where Kads is the equilibrium constant of adsorption, R the gas constant, T is the absolute temperature, and the value 55·5 is the molar concentration of water solution in mol L− 1. The calculated ∆Goads was − 31.06 kJ mol− 1 at 298 K, − 30.04 kJ mol− 1 at 313 K, − 30.86 kJ mol− 1 at 323 K, and − 31.64 kJ mol− 1 at 333 K. The negative value of ∆Goads is an indication that the adsorption of KSFA on Al was spontaneous. Previously, the absolute magnitude of change in free energy for physisorption has been reported to range between − 20 and 0 kJ/mol while chemisorption has a range of value more negative than − 40 kJ/mol (Behpour et al. 2008). In this study, the value lies in a range between − 20 kJ/mol and − 40 kJ/mol; hence, there may be the possibility of both physisorption and chemisorption taking place at the same time. Ansari et al. (2015) have reported similar observation in their study on Isatin derivatives as corrosion inhibitors. Yadav et al. (2015) also gave similar accounting indicating the possibility of both physisorption and chemisorption taking place at the same time from their research on acetohydrazide derivatives in acidic medium. However, sorption type may not be solely established based on the value of ∆Goads other parameters needed to be considered (Tourabi et al. 2013); this includes the fact that physisorption has been established to precede chemisorption (Wang et al. 2008).
From the above equation, ∆Goads is the standard free energy of adsorption, T is the temperature for the adsorption process, ∆Hoads is the enthalpy of the process, and ∆Soads is the entropy of adsorption process. The values of ∆Hoads and ∆Soads were calculated from the slope (∆Hoads/R) and intercept (∆Soads/R-In 55.5) of van’t Hoff plots by plotting the values of In K against 1/T. The ∆Hoads was calculated to be 25.853 kJ mol− 1, which is an indication that the adsorption process was endothermic. Previous studies have shown that ∆Hoads lower than 41.86 kJ mol− 1 indicates physisorption while ∆Hoads approaching 100 kJ mol− 1 indicates chemisorption (Popova et al. 2003; Tareq et al. 2013). The present value of ∆Hoads suggests the adsorption of KSFA on Al to be through physisorption. ∆So was found to be 969.135 J mol− 1 K− 1; this positive value of ∆So is an indication of the degree of randomness at the Al/KSFA interface during the adsorption process.
where θ1 and θ2 represents degree of surface coverage at 298 K (T1) and 333 K (T2) respectively.
Ea and Qads for corrosion of Al in 0.5 M HCl in the presence and absence of KSFA
Ea (kJ mol− 1)
Qads (kJ mol− 1)
Mechanism of KSFA as a corrosion inhibitor
The ability of KSFA to act as a corrosion inhibitor may be attributed to the presence of hydroxyl and amide functional groups in its molecule. This inhibition process can be considered as being physisorption. This process requires an electrically charged Al surface and charged species of KSFA in solution. In this system, Al may be present with vacant low-energy electron orbital while KSFA may exist in solution with relatively loosely bound electrons which can be described as hydroxyl group (oxygen as heteroatom)/amide group (nitrogen and oxygen as heteroatoms) lone pair electrons. These functional groups may adsorb at the surface of Al with three different possibilities: (a) Both the hydroxyl and amide group may be adsorbed on the Al surface site, (b) either the hydroxyl or amide group may be adsorbed on the Al surface site, while the other group is free in solution phase, and (c) both (a) and (b) may co-exist.
In Eq. 6 above, the X− may be considered the chloride ions (Cl− 1) from the corrosion initiator (HCl); this was also found on the surface of Al being corroded as shown in Fig. 4b, c. In this medium, KSFA cations ([KSFA]2+) are driven towards the Cl− 1 ions by electrostatic interactions and as a result reducing the attack of Cl− 1 ions on Al which further reduces the dissolution of Al and hence corrosion is inhibited. Since the Al is capable of existing in the + 3 state in the medium, there is the possibility of electron transfer from the heteroatoms in KSFA molecules. As a result, there can be an electronic interaction between the surface of Al and the highest occupied molecular orbital of KSFA leading to the adsorption of KSFA on Al; similar observation has been reported in previous works (Quraishi and Sardar 2004; Obot and Obi-Egbedi 2010). In addition to this, the hydroxyl group in KSFA can readily form complex with trivalent aluminum in order for KSFA to adsorb at the surface of Al. In all, KSFA restricted the diffusion of ions to and/or from the surface of Al and thus inhibited the overall corrosion process.
KSFA has been synthesized from underutilized seed oil of K. senegalensis using simple reaction route. KSFA inhibited corrosion process on Al in 0.5 M HCl with an inhibition efficiency of 90.43% at 0.001 mg/L concentration. The corrosion inhibition of KSFA was by surface adsorption, which is spontaneous, and physisorption and described by Langmuir isotherm. The presence of heteroatoms in the molecules of KSFA was considered as the important features that determine the adsorption capacity exhibited by KSFA on Al.
The research work was supported by TWAS/CNPq. The authors are most grateful to TWAS/CNPq for awarding a postdoctoral fellowship at Universidade Federal de Minas Gerais, Minas Gerais, Brazil. Authors are grateful to the Department of Chemistry, Universidade Federal de Minas Gerais, Minas Gerais, Brazil, for research space and chemicals.
The present work was funded by TWAS-CNPq.
Availability of data and materials
Data sharing is not applicable to this article as no datasets were generated or analyzed during the current study.
Authors have done a team work to carry out this study. AA and RAO carried out experimental studies. AA and RAO wrote the manuscript. All authors read and approved the final manuscript.
The authors declare that they have no competing interests.
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