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Synthesis, characterization and electrochemical performance of a new imidazoline derivative as an environmentally friendly corrosion and scale inhibitor

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Abstract

A new imidazoline derivative, {[(benzimidazol-2-ylmethyl)imino]bis(methylene)} bis(phosphonicacid), named as BMIBMBPA, was synthesized as an environmentally friendly corrosion and scale inhibitor. The performance of BMIBMBPA for carbon steel in cooling tower water was evaluated using weight loss, electrochemical measurements and a scale test and compared to that of sodium tungstate. The optimum concentration of BMIBMBPA was measured to be 40 mg/L and a much higher value, even at lower inhibition efficiencies, was determined for sodium tungstate. The electrochemical measurements demonstrated that BMIBMBPA acts as a mixed-type corrosion inhibitor. Surface analyses revealed adsorption of BMIBMBPA and scale inhibition through disruption in growth of precipitates.

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Authors and Affiliations

  1. School of Metallurgy and Materials Engineering, College of Engineering, University of Tehran, Tehran, Iran

    Sina Borghei, Changiz Dehghanian & Saeed Yari

  2. Department of Chemistry, Tarbiat Modares University, Tehran, Iran

    Rouhollah Yaghoubi

Authors
  1. Sina Borghei
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  2. Changiz Dehghanian
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  3. Rouhollah Yaghoubi
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  4. Saeed Yari
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Corresponding author

Correspondence to Sina Borghei.

Appendix: NMR, FTIR spectroscopy and elemental analysis of the synthesized corrosion inhibitor

Appendix: NMR, FTIR spectroscopy and elemental analysis of the synthesized corrosion inhibitor

P-NMR

31PNMR (202.46 MHz, DMSO): δ = 20.17 ppm.

Interpretation

The resultant peak at δ = 20.17 ppm indicates the presence of phosphorous atoms only in one functional group (phosphonate functional group) in the synthesized product.

H-NMR

1HNMR (500.13 MHz, DMSO): δ = [5.043 (s, 1H, NH), 7.34–7.53 (m, 4H, Ar–H), 10.83 (s, 4H, OH), 3.45 (d, 2JP,H = 12.7 Hz, 4H, CH2).]

Interpretation

5043 (s, 1H, NH) represents magnetic resonance of hydrogen atom in an NH couple. Therefore, the presence of one NH couple is verified. Magnetic resonances of hydrogen atoms in the benzene group are located in the δ = 7–8 ppm domain, so 7.34–7.53 (m, 4H, Ar–H) relates to four hydrogen atoms to four carbon atoms in the benzene functional group in the chemical structure of the synthesized product. Four hydrogen atoms in the hydroxyl functional group (OH) were identified with displacement of their nucleus within 10.83 ppm. The interference of magnetic resonance of the phosphorous atom (in the phosphonate functional group) in the hydrogen atom (in the CH2 couple) leads to nuclear fission of the hydrogen atom, indicated by 3.45 (d, 2JP,H = 12.7 Hz, 4H, CH2). This incidence took place two times (2JP,H) for four hydrogen atoms (4H) in two CH2 couples. This can be one proof for the chemical bond of phosphorous and carbon atoms (P–C bond).

C-NMR

13CNMR (125.77 MHz, DMSO): δ = [56.10 (d, 2JP,C = 146.7 Hz, CH2), 81.92 (s), 111.6 (s), 127.89 (s), 139.38 (s).]

Interpretation

81.92 (s), 111.6 (s) and 127.89 (s) relate to carbon atoms located in three different functional groups (four carbon atoms in the benzene ring, two residual carbon atoms of the benzene functional group which are located at the interface of the benzene ring and the adjacent amin group, and the carbon atom surrounded by three nitrogen atoms). 56.10 (d, 2JP,C = 146.7 Hz, CH2) means interference of the magnetic resonance of phosphorous atom nucleus with that of the carbon atom nucleus in the P–C bond, and is another demonstration for the chemical bond of phosphorous and carbon atoms in the synthesized compounds.

FTIR spectroscopy

The adsorption reflection of FTIR spectra for the synthesized compound are shown in Fig. 12. The indication of P–C, P–OH, P=O, C–N, C=C, C=N, C–H and N–H stretching are located in 750–900, 900–1200, 1100–1275, 1020–1250, 1400–1600, 1600–1800, 2400–2550 and 3200–3500 cm−1 regions, respectively. As a result, the peaks at 790.59, 937.85, 1161.66, 1072.14, 1481.72, 1610.59, 2311.16 and 3400.90 cm−1 are related to them, respectively. Therefore, the presence of P–C, P–OH, P=O, C–N, C=C, C=N, C–H and N–H bonds are verified.

Fig. 12
figure 12

The adsorption reflection of FTIR spectra for the synthesized compound

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Elemental analysis

Elemental analysis of the synthesized compound indicated C at 35.58, H at 4.01 and N at 13.03 which has an acceptable conformity to the one calculated through theoretical elemental analysis of C10H15N3O6P2 which is C at 33.64, H at 4.05 and N at 13.08.

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Borghei, S., Dehghanian, C., Yaghoubi, R. et al. Synthesis, characterization and electrochemical performance of a new imidazoline derivative as an environmentally friendly corrosion and scale inhibitor. Res Chem Intermed 42, 4551–4568 (2016). https://doi.org/10.1007/s11164-015-2296-7

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