Mild steel corrosion inhibition in 200 ppm NaCl by new surfactant derivatives of bis-glucobenzimidazolones

Loubna Lakhrissi; Brahim Lakhrissi; Rachid Touir; Mohamed Ebn Touhami; Mohamed Massoui; El Mokhtar Essassi

doi:10.1016/j.arabjc.2013.12.005

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Original article

10 (

2_suppl

); S3142-S3149

doi:

10.1016/j.arabjc.2013.12.005

Mild steel corrosion inhibition in 200 ppm NaCl by new surfactant derivatives of bis-glucobenzimidazolones

Loubna Lakhrissi^{^a,^c}, Brahim Lakhrissi^{^a}, Rachid Touir^{^b,⁎}, Mohamed Ebn Touhami^{^b}, Mohamed Massoui^{^c}, El Mokhtar Essassi^{^c}

a Laboratoire d’Agroressources et Génie des Procédés, Faculté des Sciences, Université Ibn Tofail, BP 133, Kénitra 14000, Morocco

b Laboratoire de Matériaux, Electrochimie et Environnement, Faculté des Sciences, Université Ibn Tofail, BP 133, Kénitra 14000, Morocco

c Laboratoire de Chimie Organique Hétérocyclique, Université Mohammed V – Agdal, Faculté des Sciences, Rabat, Morocco

⁎Corresponding author. Tel.: +212 670 52 69 59; fax: +212 535 733 171. touir8@gmail.com (Rachid Touir) touir8@yahoo.fr (Rachid Touir)

Received: 2013-8-13, Accepted: 2013-12-5, Published: 2013-05-01

Disclaimer:
This article was originally published by Elsevier and was migrated to Scientific Scholar after the change of Publisher.

Peer review under responsibility of King Saud University.

Abstract

The new bis-glucobenzimidazolone derivatives (24a–d) have been synthesized and characterized by NMR spectroscopy. They have been tested as corrosion inhibitor for mild steel in 200 ppm NaCl solution using potentiodynamic polarization curves and electrochemical impedance spectroscopy. Potentiodynamic polarization curve measurements showed that the investigated compounds were a mixed-type inhibitor. Their inhibition efficiencies improve with concentration and reached a maximum at 10⁻⁵ M of each compound and the 24b is better. Electrochemical impedance spectroscopy measurements showed that the diagrams composed of two depressed capacitive loops. This loop can be split into two capacities’ contributions, although badly separated. The first loop is attributed to the formation of a protective layer and the second is attributed to the charge transfer resistance.

Keywords

Bis-glucobenzimidazolone derivatives

Syntheses and characterization

Corrosion inhibition

200 ppm NaCl

Mild steel

Electrochemical measurements

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1 Introduction

Corrosion process plays an important role in the field of economics and safety. Various types of steel including iron and its alloys are used in different industries (Chemical and Electrochemical industries, Medical, Nuclear, Petroleum, Power, and Food Production), and also in daily life. However, it suffers from a certain type of corrosion within some environments. Due to the aggressiveness of some medium, corrosion can be reduced by the addition of corrosion inhibitors in small concentrations. Most commercial inhibitors are organic compounds containing in their structure heteroatoms such as nitrogen, oxygen and sulfur (Cenoui et al., 2010; Deng et al., 2011; Labriti et al., 2012; Ramesh et al., 2003; Zarrouk et al., 2012 ). These compounds can form either a strong coordination bond with metal atom or a passive film on the surface (Gogoi and Barhai, 2010). There is still a continuous investigation for better inhibitors or blend of inhibitors to meet the demand of the industry. The selection criteria for various inhibitors include low concentration, stability in recirculation, cost effectiveness and low operational hazard.

However, benzimidazolone derivatives constitute an important class of benzoheterocycles, which constitute the building blocks of wide range of therapeutic, biological and industrial properties (Baragatti et al., 2000; Olesen et al., 1994; Zhang et al., 2001; Biagi et al., 2001; Singh et al., 2001; Torres et al., 2003 ). Also, some derivatives have been reported to show complexant properties (Cignitti et al., 1995; Htay and Meth-Cohen, 1976a,b; Meth-Cohen et al., 1982 ). In our previous work, we have shown that some series of glycobenzimidazolone is present an important amphiphilic property (Lakhrissi et al., 2008, 2010, 2011 ).

Firstly, the present work is aimed to synthesize and characterize the bis-glucobenzimidazolone derivatives by NMR spectroscopy and secondly to evaluate their inhibition effect for mild steel in 200 ppm NaCl using electrochemical techniques.

2 Experimental details

2.1

2.1 General method

All chemicals were purchased from Aldrich or Acros (France). All solvents were distilled before use. Thin-layer chromatography (TLC) was performed on Silica Gel 60 F254 (E. Merck) plates with visualization by UV light (254 nm) and/or charring with the vanillin-H₂SO₄ reagent. Column chromatography was performed using 230–400 mesh E. Merck silica gel. Melting points were determined on an automatic electrothermal IA 9200 digital melting point apparatus in capillary and are uncorrected. Optical rotations, for solutions in chloroform or methanol, were measured with a digital polarimeter JASCO model DIP-370, using a sodium lamp at 25 °C. ¹H NMR spectra were recorded on a Bruker 300 WB spectrometer at 300 MHz, and ¹³C NMR spectra were recorded at 75 MHz for solutions in CDCl₃ or Me₂SO-d₆. Chemical shifts are given as δ values with reference to tetramethylsilane (TMS) as internal standard. Analytical TLC was performed on a Merck aluminum backed silica gel (Silica Gel F254), spots were visualized in UV light. Column chromatography was performed on silica gel (60 meshes, Matrix) by elution with hexane–acetone mixture.

2.2

2.2 Compounds synthesis: synthesis of N,N′-1,3-bis-[N-3-(6-deoxy-3-O-methyl-d-glucopyranose-6-yl)-2-oxo-benz-imidazol-1-yl)]-2-alkyloxypropanes (24a–d)

Bis-benzimidazolone derivatives of glucose were synthesized by grafting the 6-deoxy-3-O-methyl-d-glucopyranos-6-yl group on the N-3 nitrogen atom of two benzimidazolone units that are linked by an alkyloxypropylene group, as described earlier (Lakhrissi et al., 2010). N,N′-1,3-bis-[N-3-(6-deoxy-3-O-methyl-d-glucopyranose-6-yl)-2-oxobenzimidazol-1-yl)]-2-alkyloxypropanes 24a–d were synthesized following Scheme 1. The junction of the two N-isopropenylbenzimidazolone units (Meth-Cohen et al., 1982) (step a) was performed by condensing the 1-N-isopropenylbenzimidazolone 1 with epichlorohydrin in DMF in the presence of K₂CO₃ (Lakhrissi et al., 2010). Subsequent alkylation of the free OH group by n-bromoalkanes (Lakhrissi et al., 2010) (step b), N-3 deprotection (step c), glucose derivative 6 (Gouéth et al., 1994; Lakhrissi et al., 2004, 2010 ) condensation (Lakhrissi et al., 2010) (step d), and final deacetylation (step e), gave the compounds 24a–d.

Synthesis of N,N’-1,3-bis-[N-3-(6-deoxy-3-O-methyl-d-glucopyranos-6-yl)-2-oxobenzimidazol-1-yl)]-2-alkyloxypropanes 24a–d.

2.3

2.3 Corrosion and its inhibition studies

The molecular formulas of the examined inhibitors are shown in Fig. 1. Their concentration ranges were from 10⁻⁷ to 10⁻⁵ M. Corrosive solutions were prepared using NaCl powder with distilled water. Before each experiment, mild steel which its chemical composition is summarized in Table 1, was mechanically polished with emery paper until 1200 grade, degreased with acetone, rinsed with distilled water and dried at hot air.

Structure of N,N′-1,3-bis-[N-3-(6-deoxy-3-O-methyl-d-glucopyranos-6-yl)-2-oxobenzimidazol-1-yl)]-2-alkyloxypropanes (n = 10, 12, 14, 16).

Table 1 Chemical composition of low carbon steel used in wt.%.

C	Si	Mn	Cr	Mo	Ni	Al	Cu	Co	V	W	Fe
0.11	0.24	0.47	0.12	0.02	0.1	0.03	0.14	<0.0012	<0.003	0.06	Balance

For electrochemical measurements, the working electrode was coated in a pressure into a polytetrafluoroethylene holder (PTFE) exposing only a 1 cm² of area to the solution. Platinum and saturated calomel were used as counter and reference electrode (SCE), respectively. All potentials were measured against this last electrode. The working electrode was immersed in test solution during 1 h until the steady state corrosion potential (E_corr) was reached. The cathodic polarization curve was recorded by polarization from E_corr toward more negative direction with a sweep rate of 1 mV/s. After this scan, the same electrode remained in solution until obtaining the steady state corrosion potential (E_corr ± 0.002 V), and then the anodic polarization curve was recorded from E_corr to positive direction with the same sweep rate. The obtained polarization curves were corrected for the ohmic drop with the electrolyte resistance determined by electrochemical impedance spectroscopy. These measurements were carried out using a Potentiostat/Galvanostat/Voltalab PGZ 100 monitored by a personal computer. Three experiments were performed in each case and the average corrosion rate was reported. All the obtained standard deviation (SD) values are lower.

However, the overall current density, i, is considered as the sum of two contributions, anodic and cathodic current i_a and i_c, respectively. For the potential domain not too far from the open circuit, we can consider that both processes obey the Tafel law (Stern and Geary, 1957), so we can draw:

(1)

i = i_{a} + i_{c} = i_{corr} \times {\exp [b_{a} \times (E - E_{corr})] - \exp [b_{c} \times (E - E_{corr})]}

where i_corr is the corrosion current density (A cm⁻²), and b_a and b_c are respectively the Tafel constant of anodic and cathodic reactions (V⁻¹). These constants are related to the Tafel slope β (V dec⁻¹) in the usual logarithmic scale by:

(2)

b = \frac{\ln (10)}{β} \approx \frac{2.303}{β}

Corrosion parameters were then evaluated by the method of nonlinear least square using Eq. (1). However, for this calculation, the applied potential range was limited to ±0.100 V/SCE with respect to E_corr still significant divergence has sometimes been systematically observed for both anodic and cathodic branches.

The inhibition efficiency of the studied compounds was calculated using the following equation:

(3)

η = \frac{i_{corr}^{0} - i_{corr}}{i_{corr}^{0}} \times 100

where

i_{corr}^{0}

and i_corr are the corrosion rates in the absence and presence of inhibitors, respectively. The electrochemical impedance spectroscopy measurements were carried out using a transfer function analyzer (PGZ 100, Radiometer Analytical), with a small amplitude ac: signal (10 mV rms), over a frequency range of 100 kHz to 10 mHz with ten points per decade. The impedance diagrams were given in the Nyquist presentation. To ensure reproducibility, all experiments were repeated three times and the evaluated inaccuracy does not exceed 10%. The results were then analyzed using Bouckamp program (Bouckamp, 1993). The inhibition efficiency was calculated using the following equation:

(4)

η = \frac{R_{p} - R_{p}^{0}}{R_{p}} \times 100

where

R_{p}^{0}

and R_p are the polarization resistance values without and with inhibitors, respectively.

3 Results and discussion

3.1

3.1 Compounds characterization

The synthesized compounds were characterized by their melting points and spectral ¹H and ¹³C NMR data. Physico-chemical constants are given in Tables 2 and 3.

Table 2 Physico-chemical constants of compounds 24a–d and their precursors 23a–d.

Compound	Yield (%)	Mp (°C)	${[α]}_{D}^{26} (c = 1.0)$	α/β
23a (n = 10)	95	78–80	−53.0^⁎	–
23b (n = 12)	93	70–72	−49.5^⁎	–
23c (n = 14)	93	66–68	−51.6^⁎	–
23d (n = 16)	92	62–64	−47.7^⁎	–
24b (n = 10)	83	119–121	31.8–38.1^⁎⁎	6/5
24b (n = 12)	80	116–118	32,6–35,1^⁎⁎	4/3
24b (n = 14)	79	112–114	34,1–35,9^⁎⁎	6/5
24b (n = 16)	78	100–102	35,5–31,1^⁎⁎	4/3

⁎ In CHCl₃.

⁎⁎ In fresh MeOH and after 3 days.

Table 3 NMR spectroscopic data of compound 23a in CDCl₃ and its precursor 24a in DMSO-d₆.

Compound	Galactosyl moiety	Oxo-benzimidazolyl	Alkyl chain	Propyloxy moiety
		Moiety	Moiety
23a (n = 10)	H¹:5.85(d, 2H, J_1,2 = 3.3 Hz)	H_arom:7.00–7.20(m,8H)	${CH}_{3}^{ω} : 0.80 (t, 3 H)$	OCH:4.10(m,1H)
	H²:4.55(d,2H, J_2,3 = 0.0 Hz)		${CH}_{2}^{ω - 1} : 1.03 (sext, 2 H)$	NCH₂:3.95(m,4H)
	H³:3.85(d, 2H, J_3,4 = 3.0 Hz)		7CH₂:1.15–1.40 (m, 14H)
	H⁴:3.90(dd, 2H, J_4,5 = 7.1 Hz)		${OCH}_{2}^{α} : 3.30 (t, 2 H)$	J_1,2 = 5.5
	H⁵:4.15(m, 2H, J_5,6a = 14.5 Hz)		J_ω_,_ω_-1 = 7, 2
	H^6a:4.30(dd, 4H J_6,6 = 6.4 Hz)		J_α,β = 6,4
	H^6b:4.05(dd, 4H, J_5,6b = 2.7 Hz)
	OCH₃:3.40 (s, 6H)
	CH_3iso:1.25–1.28 (4s,12 Hz)
	OH:2.12 (s, 2H)

23a (n = 10)	C¹:105.1	C^2α⚌O:155.9	${CH}_{3}^{ω} : 14.0$	NCH₂:43.6
	C³: 83.5	C^2β⚌O:155.8	${CH}_{2}^{ω - 1} : 22.6$	OCH:76.4
	C²: 81.8	C-8,C-9:129.4;129.6	${CH}_{2}^{γ} : 25.7$
	C⁴:80.3	C-5,C-6:121.4;121.6	5CH₂:29.3–31.8
	C⁵:68.3	C-4,C-7:108.5;108.6	${CH}_{2}^{β} : 29.6$
	C⁶:45.5		${OCH}_{2}^{α} : 71.4$
	OCH₃:58.2
	(CH_3iso)₂:26.2;26.5
	C_iso:111.7

24a (n = 10)	C^1α:92.2	C^2α⚌O:153.7	${CH}_{3}^{ω} : 13.8$	NCH₂:42.6
	C^1β:96.7	C^2β⚌O:153.8	${CH}_{2}^{ω - 1} : 22.0$	OCH:75.4
	C^3α:82.8	C-8,C-9:129.3;129.7	${CH}_{2}^{γ} : 25.0$
	C^3β:85,9	C-5,C-6:120.6	5CH₂:28.5–31.2
	C^2α,C^4α,C^5α:71,7;71,3;69,3	C-4,C-7:108.2;108.6	${CH}_{2}^{β} : 29.1$
	C^2β,C^4β,C^5β:74,2;73,8;73,6		${OCH}_{2}^{α} : 69.9$
	C-6:43.0
	OCH₃:59.8

3.2

3.2 Polarization measurements

The effect of 24a, 24b, 24c and 24d was studied using potentiodynamic polarization curves. Fig. 2 shows the obtained results of mild steel in 200 ppm NaCl in the absence and presence of each compound at different concentrations. It can be remarked that the cathodic branches do not show any linearity and considered as the sum of two curves, oxygen reduction (Eq. (5)) and hydrogen evolution (Eq. (6)). However, the anodic branches also do not show any linearity due to the metal dissolution (Eq. (7)). For this, i_corr, E_corr, b_a and b_c were evaluated from the experimental results using a user defined function of “Non-linear least squares curve fit” (using Eq. (1)) of graphic software (Origin, Origin Lab). In all cases, the correlation factor R² is greater than 0.999 indicating a reliable result. Fig. 3 shows, for example, the results of regression calculation for the cathodic and anodic scan in the presence of 24b at various concentrations. In this calculation, the potential domain is limited to E_corr ± 0.100 V/SCE as mentioned in our previous work (Ghailane et al., 2013). It can be seen in this figure a good agreement between the calculated and the experimentally polarization data. Table 4 summarizes various corrosion kinetic parameters so obtained.

(5)

O_{2} + 2 H_{2} O + 4 e^{-} \to 4 {HO}^{-}

(6)

2 H_{2} O + 2 e^{-} \to H_{2} + 2 {HO}^{-}

(7)

Fe \to {Fe}^{2 +} + 2 e^{-}

Potentiodynamic polarization curves for mild steel in 200 ppm NaCl solution in the absence and the presence of 24a, 24b, 24c and 24d at various concentrations.

Wide potential range polarization curves for mild steel in 200 ppm NaCl solution in the presence of 24b at various concentrations.

Table 4 Electrochemical parameters for mild steel in 200 ppm NaCl in the absence and the presence of 24a, 24b, 24c and 24d at various concentrations.

Compounds		E_corr mV/SCE	i_corr μA cm⁻²	b_a V⁻¹	b_c V⁻¹	η%
NaCl	200 ppm	−500	21.64	12.42	−1.21	–
24a	10⁻⁷	−617	14.99	32.74	−0.32	31
	10⁻⁶	−448	7.51	38.77	−5.72	65
	10⁻⁵	−406	2.55	25.53	−11.06	88
24b	10⁻⁷	−444	8.37	18.98	−6.01	61
	10⁻⁶	−449	5.60	39.36	−7.58	74
	10⁻⁵	−406	2.14	25.15	−13.06	90
24c	10⁻⁷	−522	38.92	21.85	−3.40	−79
	10⁻⁶	−495	15.49	8.03	−2.27	28
	10⁻⁵	−426	5.64	16.22	−10.90	74
24d	10⁻⁷	−510	8.82	36.94	−4.64	59
	10⁻⁶	−486	6.57	19.76	-6.88	70
	10⁻⁵	−493	6.10	23.80	−4.74	72

It is noted that the presence of all compounds suppressed the cathodic or anodic reactions exceptionally 24c at 10⁻⁷ M. These results indicated that these products act as mixed or anodic-type inhibitor and the inhibition efficiency follows the order 24d < 24c < 24a < 24b. The cathodic Tafel slopes, b_c, are changed with the inhibitor concentrations, indicating a change in the hydrogen evolution reaction and reduction of dissolved oxygen. But in the anodic domain, the I–E characteristics are almost the same in the absence and presence of inhibitors; this can be explained by that these compounds block the reaction sites of iron without affecting the anodic reaction mechanism.

3.3

3.3 Electrochemical impedance spectroscopy

To confirm the obtained results by potentiodynamic polarization curves and study the inhibition mechanism in more detail, EIS was used. Nyquist plots for mild steel in 200 ppm NaCl after one hour of immersion time at the corrosion potential in the absence and the presence of 24a, 24b, 24c and 24d at different concentrations are shown in Fig. 4. It may be noted that the obtained impedance responses were significantly changed by different inhibitor addition. It is also noted that these plots consisted of two badly separated capacitive loops. The one at high frequency was attributed to the adsorbed film resistance due to adsorption of the inhibitors and all other accumulated products. Conversely, the one at low frequency was usually attributed to the double layer capacitance and the charge transfer resistance. Because of this poor separation and in order to analyze the Nyquist plots impedance spectra more quantitatively, an equivalent electric circuit with two time constants was tried to reproduce these results by non linear regression calculation. This circuit for the impedance diagrams presented in Fig. 4 is shown in Fig. 5. Where R_s indicates the electrolyte resistance; R_f is the resistance associated with the corrosion product layer formed with some amount of inhibitor; C_f (CPE2) is that associated with the capacitance of the same layer; R_ct corresponds to the charge transfer resistance; C_ct (CPE1) is attributed to the double-layer capacitance.

Nyquist diagrams for mild steel in 200 ppm NaCl containing different concentrations of 24a, 24b, 24c and 24d at the corrosion potential.

Electrical equivalent circuit proposed to simulate the impedance diagrams.

The most important data obtained from the equivalent circuit are presented in Table 5. It may be remarked that R_p value increases with concentration of all compounds with 24b have the greater polarization resistance. This change can result from a decrease in local dielectric constant and/or an increase in the thickness of the electrical double layer suggests that the inhibitor molecules function by adsorption at the metal–solution interface (Touir et al., 2010).

Table 5 Characteristic parameters evaluated from impedance diagram for mild steel in 200 ppm NaCl at various concentrations of different inhibitors.

Compounds	Con. M	R_s Ω cm²	R_f Ω cm²	C_f μF cm⁻²	R_ct Ω cm²	C_ct μF cm⁻²	R_p Ω cm²	η%
200 ppm NaCl	00	583	718	553	2902	548	3090
24a	10⁻⁷	462.6	2375	0.33	3451	115	4494	31
	10⁻⁶	564.6	102	2.45	4078	390	4841	36
	10⁻⁵	878.3	6815	0.58	7339	173	8272	63
24b	10⁻⁷	951.4	4221	0.75	5025	316	5332	42
	10⁻⁶	977.8	2578	0.123	4942	322	5068	39
	10⁻⁵	892.6	5404	0.58	9989	159	11125	72
24c	10⁻⁷	602.5	543.5	0.73	2237	569	2439	−27
	10⁻⁶	912	4804	0.26	3255	983	6417	52
	10⁻⁵	641.4	47.9	0.25	6012	824	6512	53
24d	10⁻⁷	470.4	2275	0.11	3485	575	3686	16
	10⁻⁶	766.9	286.5	0.27	4801	523	4984	39
	10⁻⁵	783.6	2018	0.12	6637	191	7916	61

EIS impedance study also confirms the inhibition character of inhibitor obtained with polarization curve measurements.

4 Conclusion

The corrosion inhibition of mild steel in 200 ppm NaCl solution by new bis-glucobenzimidazolone derivatives was investigated using potentiodynamic polarization curves and electrochemical impedance spectroscopy. Potentiodynamic polarization curve measurements showed that the investigated compounds were a mixed-type inhibitor at low concentration. Their inhibition efficiencies improve with concentration and reached a maximum at 10⁻⁵ M of each compound and the 24b is better. This behavior was confirmed using electrochemical impedance spectroscopy measurements by the formation of a protective layer.

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Zarrouk A., Zarrok H., Salghi R., Bouroumane N., Hammouti B., Al-Deyab S.S., Touzani R., . The adsorption and corrosion inhibition of 2-[bis-(3,5-dimethyl-pyrazol-1-ylmethyl)-amino]-pentanedioic acid on carbon steel corrosion in 1 M HCl. Int. J. Electrochem. Sci.. 2012;7:10215-10232.
[Google Scholar]
Zhang P., Terefenko E.A., Wrobel J., Zhang Z., Zhu Y., Cohen J., Marschke et K.B., Mais D., . Synthesis and progesterone receptor antagonist activities of 6-aryl benzimidazolones and benzothiazolones. Bioorg. And Med. Chem. Lett.. 2001;11(20):2747-2750.
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Introduction

Experimental details

General method
Compounds synthesis: synthesis of N,N′-1,3-bis-[N-3-(6-deoxy-3-O-methyl-d-glucopyranose-6-yl)-2-oxo-benz-imidazol-1-yl)]-2-alkyloxypropanes (24a–d)
Corrosion and its inhibition studies

Results and discussion

Compounds characterization
Polarization measurements
Electrochemical impedance spectroscopy

Conclusion

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[Google Scholar]

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[Google Scholar]