Synthesis and Evaluation of Zwitterionic Surfactants Bearing Benzene Ring in the Hydrophobic Tail
Abstract
:1. Introduction
2. Materials and Synthesis
2.1. Materials
2.2. Determination of Structure
2.3. Solubility and Salt Tolerance Tests
2.4. Thermal Gravimetric Analysis (TGA)
2.5. Surface Tension
2.6. Synthesis
2.6.1. Synthesis of Intermediate 5
2.6.2. Synthesis of 4-Tert-Butylphenyl Ethoxylate Amidopropyl Carboxybetaine (TEAC)
2.6.3. Synthesis of 4-Tert-Butylphenyl Ethoxylate Amidopropyl Sulfobetaine (TEAS)
2.6.4. Synthesis of 4-Tert-Butylphenyl Ethoxylate Amidopropyl Hydroxy Sulfobetaine (TEAH)
3. Results and Discussion
3.1. Structure Interpretation
3.2. Solubility and Salt Tolerance
3.3. Thermal Gravimetric Analysis (TGA)
3.4. Surface Tension
4. Conclusions
Supplementary Materials
Author Contributions
Acknowledgments
Conflicts of Interest
References
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ZwitterIonic Surfactants | 1H NMR Values (500 MHz, δ in ppm, CDCl3) | |||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Lipophilic Tail | Ethoxy Units | Acetic | Amide | Amido-Amine | Benzene Ring | |||||||||||
3 × CH3 | CH3CH2 | CH2 | CH2 | 2 × CH2 | CH2 | NH | 2 × CH3 | CH2 | CH2 | CH2 | CH2 | CH2 | CH2 | 2 × CH | 2 × CH | |
TEAC | 1.27 | - | - | - | 3.64 | 4.07 | 8.02 | 3.22 | 1.96 | - | 3.30 | 3.32 | 3.61 | - | 6.82 | 7.26 |
TEAS | 1.27 | - | - | - | 3.63 | 4.07 | 8.01 | 3.11 | 1.95 | 2.18 | 2.91 | 3.34 | 3.51 | 3.80 | 6.82 | 7.27 |
TEAH | 1.26 | - | - | - | 3.64 | 4.06 | 7.98 | 3.20 | 2.04 | 4.67 CH | 3.15 | 3.33 | 3.52 | 3.79 | 6.81 | 7.25 |
NEAC | - | 0.80 | 1.25 | 1.50 | 3.63 | 4.10 | 8.01 | 3.23 | 1.98 | - | 3.32 | 3.34 | 3.60 | - | 6.83 | 7.19 |
NEAS | - | 0.77 | 1.23 | 1.53 | 3.64 | 4.09 | 8.00 | 3.10 | 1.99 | 2.17 | 2.89 | 3.34 | 3.49 | 3.82 | 6.82 | 7.20 |
NEAH | - | 0.79 | 1.25 | 1.52 | 3.63 | 4.03 | 8.00 | 3.23 | 2.06 | 4.68 CH | 3.15 | 3.34 | 3.53 | 3.80 | 6.82 | 7.18 |
Zwitterionic Surfactants | 13C NMR (CDCl3, δ in ppm, 125 MHz) |
---|---|
TEAC | 22.9, 31.5, 34.0, 35.9, 51.0, 62.2, 64.5, 67.3, 69.0–71.0, 114.0, 126.1, 143.5, 156.3, 168.1, 172.5 |
TEAS | 18.5, 22.6, 31.4, 33.9, 35.8, 50.6, 60.5, 62.6, 67.2, 69.0–71.0, 113.9, 126.0, 143.4, 156.2, 171.3 |
TEAH | 22.9, 31.5, 34.0, 35.9, 51.9, 55.3 63.0, 67.3, 67.5, 69.0–71.0, 114.0, 126.1, 143.4, 156.4, 171.3 |
NEAC | 14.4, 22.9, 29.1, 35.9, 51.0, 62.2, 64.5, 67.2, 69.0–71.0, 113.8, 126.8, 156.1, 167.8, 172.3 |
NEAS | 14.1, 22.7, 24.8, 29.2, 35.9, 50.8, 60.6, 62.7, 67.3, 69.0–71.0, 113.7, 126.9, 156.3, 171.5 |
NEAH | 14.1, 22.6, 29.1, 35.6, 51.8, 55.3, 62.9, 67.2, 67.5, 69.0–71.0, 113.8, 126.9, 156.1, 171.3 |
Zwitterionic Surfactants | FTIR Data (in cm−1) | |||||||
---|---|---|---|---|---|---|---|---|
(υN-H) | υC-H Asym. | υC-H Sym. | Amide (I) | CH2 (bend) | CH3 (bend) | Ethoxy Stretch | Asym. Stretch | |
TEAC | 3398 | 2959 | 2872 | 1625 | 1393 | 1248 | 1106 | 941 |
TEAS | 3406 | 2954 | 2871 | 1654 | 1393 | 1245 | 1114 | 925 |
TEAH | 3405 | 2953 | 2871 | 1656 | 1393 | 1246 | 1104 | 926 |
NEAC | 3405 | 2957 | 2872 | 1628 | 1393 | 1248 | 1101 | 944 |
NEAS | 3404 | 2956 | 2872 | 1651 | 1349 | 1290 | 1104 | 947 |
NEAH | 3405 | 2944 | 2891 | 1621 | 1371 | 1275 | 1164 | 973 |
Zwitterionic Surfactants | Base Peak | Proposed Structure |
---|---|---|
TEAC | 527.3 | |
TEAS | 591.3 | |
TEAH | 607.3 | |
NEAC | 641.4 | |
NEAS | 675.4 | |
NEAH | 765.5 | |
Ions | FW (g L−1) | SW (g L−1) |
---|---|---|
Na+ | 59.5 | 18.3 |
Ca2+ | 19.1 | 0.7 |
Mg2+ | 2.5 | 2.1 |
SO42− | 0.4 | 4.3 |
Cl− | 132.1 | 32.2 |
HCO3− | 0.4 | 0.1 |
Total | 214 | 57.7 |
Surfactant | Solvent | CMC (mmol L−1) | γcmc (mN m−1) | гmax × 106 (mol m−2) | Amin (nm2) |
---|---|---|---|---|---|
NEAC | DW | 0.1043 | 32.18 | 2.53 | 0.65 |
NEAS | DW | 0.1045 | 30.53 | 2.35 | 0.70 |
NEAH | DW | 0.1308 | 31.55 | 2.27 | 0.73 |
NEAC | NaCl | 0.0507 | 32.34 | 1.95 | 0.89 |
NEAS | NaCl | 0.0522 | 31.39 | 1.92 | 0.86 |
NEAH | NaCl | 0.0568 | 31.89 | 2.22 | 0.74 |
TEAC | DW | 6.142 | 30.226 | 3.02 | 0.59 |
TEAS | DW | 6.667 | 28.98 | 2.78 | 0.59 |
TEAH | DW | 3.828 | 31.79 | 3.46 | 0.47 |
TEAC | NaCl | 5.792 | 31.43 | 2.35 | 0.70 |
TEAS | NaCl | 6.010 | 29.09 | 2.43 | 0.68 |
TEAH | NaCl | 3.163 | 32.79 | 3.63 | 0.45 |
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Hussain, S.M.S.; Mahboob, A.; Kamal, M.S. Synthesis and Evaluation of Zwitterionic Surfactants Bearing Benzene Ring in the Hydrophobic Tail. Materials 2020, 13, 1858. https://doi.org/10.3390/ma13081858
Hussain SMS, Mahboob A, Kamal MS. Synthesis and Evaluation of Zwitterionic Surfactants Bearing Benzene Ring in the Hydrophobic Tail. Materials. 2020; 13(8):1858. https://doi.org/10.3390/ma13081858
Chicago/Turabian StyleHussain, Syed Muhammad Shakil, Ahmad Mahboob, and Muhammad Shahzad Kamal. 2020. "Synthesis and Evaluation of Zwitterionic Surfactants Bearing Benzene Ring in the Hydrophobic Tail" Materials 13, no. 8: 1858. https://doi.org/10.3390/ma13081858