Journal of Heterocyclics (ISSN 2639-6734)

Research Article :

Cefuroxime Axetil: A Commercially Available Pro-Drug as Corrosion Inhibitor for Aluminum in Hydrochloric Acid Solution


Paul O Ameh and Umar M. Sani

Abstract

Cefuroxime axetil (CA) a pro-drug was tested as corrosion inhibitor for aluminum in hydrochloric acid solution using thermometric, gasometric weight loss and scanning electron microscope (SEM) techniques. Results obtained showed that this compound has good inhibiting properties for aluminum corrosion in acidic medium, with inhibition efficiencies values reaching 89.87 % at 0.5 g / L. It was also found out that the results from weight loss method are highly consistent with those obtained by hydrogen evolution method and gasometric method; and all indicate that inhibitor efficiency increases with increasing inhibitor concentration. Cefuroxime axetil inhibited the corrosion of aluminum in solutions of HCl through the mechanism of physiosorption as confirmed by values of activation energy and free energy of adsorption. The adsorption of the inhibitor was also found to be spontaneous, exothermic and best fitted the Langmuir adsorption model. SEM analysis confirmed the existence of an absorbed protective film on the aluminum surface.

 

Full-Text

Introduction

In developed and developing countries, billions of dollars every year are spent on capital replacement and control methods for corrosion infrastructure [1,2]. In recent years, owing to the growing interest and attention of the world towards the protection of the environment and the hazardous effects of using chemicals on the ecological balance, the use of eco-friendly inhibitors to replace the older, which is more toxic and harmful to the environment are been intensified [3-5].

Research has shown that for an inhibitor to be an effective protector against metal corrosion, it should be readily adsorbed on the metal surface through either physisorption or chemisorption processes [6-11]. Either of these adsorption processes depends primarily on the physicochemical properties of the inhibitor group such as functional groups, electronic density at the donor atom, molecular structure, etc. For instance, organic molecules, which have had a wide applicability and that have been extensively studied and used as corrosion inhibitors, often contain the hetroatoms nitrogen, oxygen, and sulfur atoms, as well as multiple bonds in their molecules. Several researches have been carried out on the use of drugs as corrosion inhibitors for several metals in various media. For example, Fouda et al., studied the corrosion inhibition characteristics of floxacillin, cloxacillin, dicloxacillin, cefadroxil and cephalexin on aluminum in 0.5 M H3PO4 using weight loss and galvanostatic polarization techniques

Results obtained revealed that the inhibition occurs through adsorption of the inhibitor molecules on the metal surface.

Other drugs that have been found to be good corrosion inhibitors include norfloxacin, Streptomycin, Cefatrexyl, and Cefazolin [13-15]. The choice of some of the drugs used as corrosion inhibitors may be due to the fact that they have a large number of functional adsorption centers, are biodegradable, can be easily produced and purified. 

In the present investigation, the corrosion inhibiting behavior of Cefuroxime axetil [Chemical name: 1-Acetoxyethyl (6R,7R)-3-{(aminocarbonyl)oxy]methyl}-7-{[(2Z)-2-(2-furyl)-2-(methoxyimino) acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate] was investigated on aluminum in hydrochloric acid at 303 and 333 K using weight loss, thermometric gasometric and scanning electron microscope techniques.

Cefuroxime is a broad-spectrum, β-lactamase-stable second generation cephalosporin antibiotic drug with well-defined pharmacokinetics after injection [16]. It is commercially available for parenteral (intramuscular and intravenous) administration as a sodium salt and for oral administration as cefuroxime axetil, the 1-(acetoxy)ethyl ester of the drug [17]. In humans, gastrointestinal absorption of cefuroxime is negligible, whereas cefuroxime axetil shows a bioavailability of 30 to 40% when taken on fasting and 50 to 60% when taken after food [18-23]. In fact like the other cephalosporins, the parenteral cefuroxime, is not orally absorbed due to the presence of a highly polar carboxyl group that is ionized at intestinal pH, making transport across intestinal mucosa unlikely [24,25]. Cefuroxime axetil is a prodrug of cefuroxime and has little, if any, antibacterial activity until hydrolyzed in vivo to cefuroxime. The cefuroxime axetil esterase can hydrolyze cefuroxime axetil to the non-absorbable cefuroxime in the gut lumen [26]. Esterase hydrolysis leads to ethanoic acid and an unstable hydroxyethyl ester, which dissociates rapidly to ethanol and the parent cefuroxime [27]. Figure 1 shows the chemical structures of both cefuroxime and cefuroxime axetil.

The selection of cefuroxime axetil as a corrosion inhibitor is based on the following facts: 

1.     It contains three kinds of heteroatoms (four nitrogen, ten oxygen and one sulphur atom) as reactive center through which they can adsorb readily on the metal surface.

2.     The compound is readily soluble in medium.

3.     It does not cause any health hazards, but also find its diverse applications in various biological and pharmacological activities; hence the use of Cefuroxime axetil as corrosion inhibitors is safe.

Materials and Methods

Weight loss method

A previously weighed metal (aluminum sheet) was completely immersed in 250 ml of the test solution in an open beaker. The beaker was inserted into a water bath maintained at a temperature of 30 °C. Similar experiments were repeated at 60°C. In each case, the weight of the sample before immersion was measured using Scaltec high precision balance (Model SPB31) After every 24

hours, each sample was removed from the test solution, washed in a solution of NaOH containing zinc dust and dried in acetone before re-weighing. The difference in weight for a period of 168 hours was taken as total weight loss. The inhibition efficiency (% I) for each inhibitor was calculated using equation (1) [28]

Where, W1 and W2 are the weight losses (g/dm3) for mild steel in the presence and absence of inhibitor in HCl solution respectively. The degree of surface coverage θ is given by the equation (2) [29]:

The corrosion rates for mild steel corrosion in different concentrations of the acid was determined for 168 h immersion period from weight loss using equation (3) [6]

 Where, W = weight loss (mg); D = density of specimen (g/ cm3), A = area of specimen (square inches) and T = period of immersion (hour).

 Gasometry method

The method used for hydrogen evolution measurement is as described elsewhere [30]. The test solution (different concentrations of acid, inhibitor or their mixtures) was poured into the reaction vessel (gasometer). Upon the introduction of mild steel, the flask was quickly corked and the rise in volume of the paraffin due to hydrogen evolution was noted after every minute until a steady volume was observed. From the results obtained, the corrosion inhibition efficiency was calculated using the following equation,

Where, Vb is the volume of hydrogen gas evolved by the blank and Vt is the volume of hydrogen gas evolved in the presence of the inhibitor, after time, t.

Thermometric method

This was also carried out as reported elsewhere [31]. The reaction number (RN) of each system was calculated by dividing the difference between the highest and lowest temperature attained by the time interval. From the reaction number, the inhibition efficiency (% I) of the inhibitor was calculated using equation (5)Where, RNaq is the reaction number in the absence of inhibitors (blank solution) and RNwi is the reaction number of 2 M HCl containing the studied inhibitor.

 Scanning electron microscopy

The scanning electron microscope (SEM) Model No JSM-5600 LV was used to study the morphology of corroded in the presence and absence of inhibitor. The photographs were taken from that portion of the specimen where better information was expected.

Results and Discussions

Effect of cefuroxime axetil

 The corrosion rate (CR) and reaction number (RN) of aluminum in HCl containing various concentrations of Cefuroxime axetil determined for 168h immersion period from gravimetric, gasometric and thermometric are presented in Table 1. The results obtained indicates that the aluminum corrosion is reduced by the presence of Cefuroxime axetil in HCL at all concentrations used in this study, since there is a general decrease in the rate of corrosion of the aluminum with increase in concentration of the inhibitor. This may be ascribed to the adsorption of this compound on the aluminum, producing a barrier, which isolates the surface from the corrosion environment.

Table 2. presents inhibition efficiencies of various concentrations of Cefuroxime axetil in HCL. The inhibition efficiency was estimated to be 73.40 % even at extremely low inhibition concentration (0.1 M) and reaches 89.87 % at a concentration of 0.5 M. Such remarkable performances may be due to, the high molecular weight of CA, the presence of C=N, O-H, C=O, etc. which are electron donation groups and the presence of aryl groups. The inhibition efficiency was found to increases with increase in the concentration of the inhibitor but decreases with increase in temperature indicating that the mechanism of physical adsorption favours the adsorption of Cefuroxime axetil on aluminum surface. For a physical adsorption mechanism, the inhibition efficiency is expected to decrease with increase in temperature but for a chemical adsorption mechanism, the reverse is expected [31].

Also, the inhibition efficiency of CA obtained from the two methods were found correlate strongly (R2 = 0.8798 and 0.9644 for gasometric and thermometric respectively) with those obtained from gravimetric method. However, values of inhibition efficiency obtained from the weight loss were higher than the values obtained from thermometric and gasometric methods indicating that the average inhibition efficiency of CA is better than its instantaneous inhibition efficiency.

The stability of the inhibitive properties of the studied inhibitor over 168 hours of immersion was studied by plotting values of inhibition efficiencies gotten from weight loss studies against time as shown in Figure 2. From the plots, it is also evident that the inhibition efficiency first decreased with time until a critical value was attained after which it started increasing. This trend suggests that at first, there was competition between the forces of adsorption and desorption and that after the critical zone, adsorption facilitated the formation of a protective layer and thus protected the metal against further corrosion attack.

 Effect of temperature

According to Eddy [32], temperature affects the rate of any chemical reaction such that an increase in temperature leads to a corresponding increase in the rate of the reaction. Hence the effect of temperature on the corrosion of aluminum in HCl (in the absence and presence of CA) was studied using the Arrhenius Equation (equation 6) where the apparent activation energies (Ea) for the corrosion process in absence and presence of inhibitor were evaluated [6,33].

Where, CR1 and CR2 are the corrosion rates of aluminum in solution of HCl at the temperatures, T1(303 K) and T2 (333 K) respectively, Ea is the activation energy for the adsorption of CA on Al surface and R is the gas constant. Calculated values of the Ea are shown in Table 3. It can be seen from the table that the activation energies are lower than the value of 80 kJmol-1 required for a chemical adsorption mechanism supporting the earlier claims the adsorption of CA on aluminum proceeds by physical adsorption mechanism.

Conclusions

From the study, the following conclusions can be drawn. CA efficiently inhibits the corrosion of mild steel in 0.1M HCl medium. Adsorption of CA on the surface of aluminum from 1M HCl obeys Langumur adsorption isotherm. The inhibition efficiency of CA increases with increasing the inhibitor concentration and on increasing the temperature, the corrosion rate increases. The calculated values of Ea, Qads, ∆Gads indicates that the adsorption of inhibitor on the metal surface

Acknowledgment

The authors are grateful to TEFUND for sponsoring the research and Mrs Janet Onoja Ameh for typesetting the manuscript.

References

1. Thompson NG, Yunovich M, Dunmire D. Cost of corrosion and corrosion maintenance strategies (2007) Corros Rev 25:247–262.

2. Cherry BW, Skerry BS, Clayton Vic. Corrosion in Australia: the report of the Australian National Centre for Corrosion Prevention and Control feasibility Study (1983) Department of Materials Engineering, Monash University:Australia.

3. Patni N, Agarwal S, Shah Pallav. Greener approach towards corrosion inhibition (2013) Chin J Eng 2013:1–10.

4. Dalo Abu AM, Othman AA, Rawashdeh Al FAN. Exudate gum from Acacia trees as green corrosion inhibitor for mild steel in acidic media (2012) Int J Electrochem Sci 7:9303–9324.

5. Sharma SK, Mudhoo A, Khamis E. Adsorption studies, modeling and use of green inhibitors in corrosion inhibition: an overview of recent research, green corrosion inhibitors: status in developing countries (2011) Green corrosion chemistry and engineering. Wiley–VCH Publications:319.

6. Ameh PO, Oyeniyi S, Qand Sani UM. Quantum Chemical Studies on the Corrosion Inhibitions of Mild Steel in Acidic Medium by 5-amino-1-cyclopropyl-7-[(3R,5S)-3,5-dimethylpiperazin-1-yl]-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (2015) International Journal of Chemical, Material and Environmental Research 2:1-16.

7. Abdel Hameed RS. Expired drugs as corrosion inhibitors for metals and alloys (2013) Journal of physical chemistry PCAIJ 8:146-149.

8. Deepa Rani P, Selvaraj S. Inhibitive action of Vitis vinifera (grape) on copper and brass in natural sea water environment (2010) Rasayan J Chem 3:473-482.

9. Saratha R, Kasthuri N, Thilagavathy P. Environment friendly acid corrosion inhibition of mild steel by Ricinus communis Leaves (2009) Der Pharma Chemica1 2:249-257.

10.  Satapathy AK, Gunasekaran G, Sahoo SC, Kumar Amit Rodrigues PV. Corrosion inhibition by Justicia gendarussa plant extract in hydrochloric acid solution (2009) Corros Sci 51:2848–2856.

11.  Morad MS. Inhibition of iron corrosion in acid solutions by Cefatrexyl, Behaviour near and at the corrosion potential (2008) Corros Sci 50:436-441.

12.  Fouda AS, Al-Sarawy AA, Ahmed FS, El-Abbasy HM. Corrosion inhibition of aluminum 6063 using some pharmaceutical compounds (2009) Corrosion Science 51:485–492.

13.  Eddy NO, Odoemelam SA. Adsorption and inhibitive properties of norfloxacin for the corrosion of mild steel in H2SO4 (2008) Internat J of Pure and Applied Chem 3:1-10.

14.   Shukla SK, Singh AK, Ahamad I, Quraishi MA. Streptomycin: A commercially available drug as corrosion inhibitor for mild steel in hydrochloric acid solution (2009) Materials Letters 63:819.

15.  Singh AK, Quraishi MA. Effect of Cefazolin on the corrosion of mild steel in HCl solution (2010) Corros Sci 52:152-161.

16.  [McEvoy GK. Cephalosporins: cefuroxime sodium and cefuroxime axetil (2003) AHFS Drug Information, American Society of Hospital Pharmacists, Wisconsin Avenue:223-231.

17. Nieves Ruiz-Balaguer, Amparo Nacher, Vicente G. Casabo, and Matilde Merino (1997). Nonlinear Intestinal Absorption Kinetics of Cefuroxime Axetil in Rats. ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, Vol. 41, No. 2: 445–448.

18. Ridgway E, Stewart K, Rai G, Kelsey MC, Bielawska C. The pharmacokinetics of cefuroxime axetil in the sick elderly patient (1991) J Antimicrob Chemother 27:663-668.

19.  Wozniak T, J Hicks. Cefuroxime sodium (1991) Anal Profiles Drug Subst 20:209–237.

20.  Sommers DK, van Wyk M, Moncrieff J, Schoeman HS. Influence of food and reduced gastric acidity on the bioavailability of bacampicillin and cefuroxime axetil (1984) Br J Clin Pharmacol 18:535-539.

21.  Finn A, Straughn A, Meyer M, Chubb J. Effect of dose and food on the bioavailability of cefuroxime axetil (1987) Biopharm Drug Dispos 8:519-526.

22.  McEvoy GK. Cephalosporins: cefuroxime sodium. Cefuroxime axetil (1994) American Society of Hospital Pharmacists Inc:152–159.

23.  Williams PE, Harding SM. The absolute bioavailability of oral cefuroxime axetil in male and female volunteers after fasting and after food (1984) J Antimicrob Chemother 13:191-196.

24.  Foord RD. Cefuroxime:human pharmacokinetics (1976) Antimicrob Agents Chemother 9:741-747.

25.  Tsuji A, Hirooka H, Tamai I, Terasaki T. Evidence for a Carrier-Mediated Transport System in the Small Intestine Available for FK089, a New Cephalosporin Antibiotic Without an Amino Group(1986) J Antibiot 39:1592– 1597.

26.   Harding SM. Comparative pharmacokinetics of tablets and suspension (1990) Res ClinForums12:23-29.

27.   Bundgaard H. Design of Prodrugs: Bioreversible Derivatives for Various Functional Groups and Chemical Entities (1985) Design of Prodrugs, NY Elsevier Science Publishing Co:1–92

28.   Oguzie EE. Evaluation of some inhibitive effect of some plant extracts on the acid corrosion of mild steel (2008) Corros Sci 50:2993-2998.

29.   Nnanna LA, Nwadiuko OC, Ekekwe ND, Ukpabi CF, Udensi SC, et al. Adsorption and Inhibitive Properties of Leaf Extract of Newbouldia leavis as a Green Inhibitor for Aluminium Alloy in H2SO4 ( 2011) American Journal of Materials Science 1:143-148.
30.  Umoren SA, Ebenso EE, Okafor PC, Ogbobe O. Water soluble polymers as corrosion inhibitors of mild steel in acidic medium (2006) Pigment Resin Technol 35:346-52.

31. Umoren SA, Ogbobe O, Ebenso EE, Okafor PC. Polyethylene glycol and polyvinyl alcohol as corrosion inhibitors for aluminium in acidic medium (2007) J Appl Polym Sci 105:3363-3370.

32.  Eddy NO. Inhibition of the corrosion of mild steel in H2SO4 by some antibiotics (2008) Ph. D Thesis, University of Calabar.

33. Momoh Yahaya H, Eddy NO, Iyun JF, Gimba CE, Oguzie EE. Inhibitive and Adsorptive Behaviour of Guanine on Corrosion of Mild Steel in 0.1M HCl and H2SO4 (2012) International Journal of Modern Chemistry 2:127-142.

34.  Bhajiwala HM, Vashi RT. Ethanolamine, Diethanolamine and Triethanolamine as Corrosion Inhibitors for Zinc in Binary Acid Mixture [HNO3+H3PO4] (2001) Bull Electrochem Soc 17:441-448.

35. Eddy NO, Ibok UJ, Ebenso EE. Adsorption, synergistic inhibitive effect and quantum chemical studies on ampicillin and halides for the corrosion of mild steel (2010) Journal of Applied Electrochemistry 40:445-456.

36. Ghasemi Z, Tizpar A. The inhibition effect of some amino acids towards Pb Sb–Se–As alloy corrosion in sulfuric acid solution (2006) Appl Sci 252:3667– 3672.

37. Flis J, T Zakroczymski. Impedance study of reinforcing steel in simulated pore solution with tannin (1996) Journal of the Electrochemical Society 143:2458–2464.

38. Bilgic S, Sahin M.The corrosion inhibition of austenitic chromium–nickel steel in H2SO4 by 2-butyn-1-ol (2001) Mater Chem Phys 70:290–295. 

39. Rafiquee MZA, Khan S, Saxena N, Quraishi MA. Influence of Some Thiadiazole Derivatives on Corrosion Inhibition of Mild Steel in Formic and Acetic Acid Media (2007) Portugaliae Electrochimica Acta 25:419–430.

*Corresponding author:

Paul O Ameh, Department of Chemistry, Nigeria Police Academy Wudil, Kano State, Nigeria E-mail: nocaseoche@yahoo.com

Citation:

AmehOP, Sani UM (2015) CefuroximeAxetil: A Commercially Available Pro-Drug as Corrosion Inhibitor for Aluminum in Hydrochloric Acid Solution. J O Heterocyclics 101: 1-6

Keywords

Adsorption; Aluminium; Corrosion Inhibition; Cefuroxime axetil; SEM


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