Journal of Industrial and Engineering Chemistry

  • Volume 67
  • /
  • Pages.99-108
  • /
  • 2018
  • /
  • 1226-086X(pISSN)
  • /
  • 1876-794X(eISSN)
The Korean Society of Industrial and Engineering Chemistry (한국공업화학회)
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Thiadiazole-thione surfactants: Preparation, flotation performance and adsorption mechanism to malachite

  • Huang, Yaoguo (College of Chemistry and Chemical Engineering, Central South University) ;
  • Liu, Guangyi (College of Chemistry and Chemical Engineering, Central South University) ;
  • Liu, Jun (College of Chemistry and Chemical Engineering, Central South University) ;
  • Yang, Xianglin (College of Chemistry and Chemical Engineering, Central South University) ;
  • Zhang, Zhiyong (College of Chemistry and Chemical Engineering, Central South University)
  • Received : 2018.05.14
  • Accepted : 2018.06.22
  • Published : 2018.11.25
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Abstract

In this paper, novel thiadiazole-thione surfactants including 5-heptyl-1,3,4-thiadiazole-2-thione (HpSDT), 5-phenyl-1,3,4-thiadiazole-2-thione (PSDT) and 5-(2-hydroxyphenyl)-1,3,4-thiadiazole-2-thione (HPhSDT) were synthesized and originally introduced as collectors in froth flotation. Microflotation tests showed that HpSDT exhibited better flotation response to malachite than PSDT and HPhSDT, as well as excellent flotation selectivity against quartz. The contact angle results inferred that the hydrophobization intensity of these collectors toward malachite was in the order as HpSDT> PSDT> HPhSDT. ${\zeta}$-potential recommended a chemisorption of HpSDT on malachite surfaces. FTIR deduced that cupric or cuprous atoms might bond with the S and N atoms of HpSDT to form a conjugated ring. XPS further gave an additional evidence that HpSDT-Cu(I) complexes were produced on malachite surfaces via combining surface Cu atoms with HpSDT's N and S atoms, with reducing surface Cu(II) to Cu (I). The tighter orientation arrangement on malachite and stronger hydrophobicity rendered HpSDT to possess better flotation affinity toward malachite than PSDT and HPhSDT.

Keywords

Acknowledgement

Supported by : National Natural Science Foundation of China

References

  1. K.C. Corin, M. Kalichini, C.T. O'Connor, S. Simukanga, Miner. Eng. 102 (2017) 15. https://doi.org/10.1016/j.mineng.2016.11.011
  2. K. Lee, D. Archibald, J. McLean, M.A. Reuter, Miner. Eng. 22 (2009) 395. https://doi.org/10.1016/j.mineng.2008.11.005
  3. C. Marion, A. Jordens, R.H. Li, M. Rudolph, K.E. Waters, Sep. Purif. Technol. 183 (2017) 258. https://doi.org/10.1016/j.seppur.2017.02.056
  4. G. Liu, J. Liu, Y. Huang, X. Yang, H. Zhong, Miner. Eng. 118 (2018) 78. https://doi.org/10.1016/j.mineng.2018.01.009
  5. M.C. Fuerstenau, G.J. Jameson, R.H. Yoon, Froth Flotation: A Century of Innovation, Society for Mining, Metallurgy, and Exploration, Littleton, CO, 2007.
  6. D.R. Nagaraj, R.S. Farinato, Miner. Eng. 96 (2016) 2.
  7. G. Liu, X. Yang, H. Zhong, Adv. Colloid Interface Sci. 246 (2017) 181. https://doi.org/10.1016/j.cis.2017.05.008
  8. M. Kalichini, K.C. Corin, C.T. O'Connor, S. Simukanga, J. S. Afr. Inst. Min. Metall. 117 (2017) 803. https://doi.org/10.17159/2411-9717/2017/v117n8a11
  9. J.S. Lee, D.R. Nagaraj, J.E. Coe, Miner. Eng. 11 (1998) 929. https://doi.org/10.1016/S0892-6875(98)00080-6
  10. K. Park, S. Park, J. Choi, G. Kim, M. Tong, H. Kim, Sep. Purif. Technol. 168 (2016) 1. https://doi.org/10.1016/j.seppur.2016.04.053
  11. L.M. Shengo, S. Gaydardzhiev, N.M. Kalenga, Miner. Eng. 65 (2014) 145. https://doi.org/10.1016/j.mineng.2014.06.005
  12. Q. Feng, W. Zhao, S. Wen, Q. Cao, J. Ind. Eng. Chem. 48 (2017) 125. https://doi.org/10.1016/j.jiec.2016.12.029
  13. Q. Feng, W. Zhao, S. Wen, Appl. Surf. Sci. 436 (2018) 823. https://doi.org/10.1016/j.apsusc.2017.12.113
  14. Q. Feng, W. Zhao, S. Wen, J. Alloys Compd. 744 (2018) 301. https://doi.org/10.1016/j.jallcom.2018.02.056
  15. G. Liu, Y. Huang, X. Qu, J. Xiao, X. Yang, Z. Xu, Colloids Surf A: Physicochem. Eng. Asp. 503 (2016) 34. https://doi.org/10.1016/j.colsurfa.2016.05.028
  16. F. Li, H. Zhong, H. Xu, H. Jia, G. Liu, Miner. Eng. 71 (2015) 188. https://doi.org/10.1016/j.mineng.2014.11.013
  17. X. Yang, S. Liu, G. Liu, H. Zhong, J. Ind. Eng. Chem. 46 (2017) 404. https://doi.org/10.1016/j.jiec.2016.11.010
  18. S. Liu, H. Zhong, G. Liu, Z. Xu, J. Colloid Interface Sci. 512 (2018) 701. https://doi.org/10.1016/j.jcis.2017.10.063
  19. S. Liu, G. Liu, H. Zhong, X. Yang, J. Ind. Eng. Chem. 52 (2017) 359. https://doi.org/10.1016/j.jiec.2017.04.015
  20. C.C.D. Witt, F.V. Batchelder, J. Am. Chem. Soc. 61 (1939) 1250. https://doi.org/10.1021/ja01874a071
  21. H. Xu, H. Zhong, S. Wang, Y. Niu, G. Liu, Miner. Eng. 66 (2014) 173.
  22. J. Xiao, G. Liu, H. Zhong, Int. J. Miner. Process. 166 (2017) 53. https://doi.org/10.1016/j.minpro.2017.07.003
  23. G.A. Hope, A.N. Buckley, G.K. Parker, A. Numprasanthai, R. Woods, J. McLean, Miner. Eng. 36 (2012) 2.
  24. J. Deng, S. Wen, Q. Yin, D. Wu, Q. Sun, J. Taiwan Inst. Chem. Eng. 71 (2017) 20. https://doi.org/10.1016/j.jtice.2016.11.013
  25. A.M. Marabini, M. Ciriachi, P. Plescia, M. Barbaro, Miner. Eng. 20 (2007) 1014. https://doi.org/10.1016/j.mineng.2007.03.012
  26. G. Liu, H. Zeng, Q. Lu, H. Zhong, P. Choi, Z. Xu, Colloids Surf A: Physicochem. Eng. Asp. 409 (2012) 1. https://doi.org/10.1016/j.colsurfa.2012.04.036
  27. P. Nowak, M. Barbaro, A.M. Marabini, Int. J. Miner. Process. 32 (1991) 23. https://doi.org/10.1016/0301-7516(91)90017-D
  28. A.M. Marabini, G. Bornengo, V. Alesse, F. Bergamini, 2-Mercapto-benzoxazole derivatives as collectors for the selective flotation of metal ores, U.S. Patent 5505310 (1996).
  29. G.S. Maier, B. Dobias, Miner. Eng. 10 (1997) 1375. https://doi.org/10.1016/S0892-6875(97)00128-3
  30. M. Barbaro, R. Herrera-Urbina, C. Cozza, D. Fuerstenau, A. Marabini, Int. J. Miner. Process. 50 (1997) 275. https://doi.org/10.1016/S0301-7516(97)00045-8
  31. T.G. Deligeorgiev, S.S. Kaloyanova, N.Y. Lesev, J.J. Vaquero, Monatsh. Chem. 142 (2011) 895. https://doi.org/10.1007/s00706-011-0551-1
  32. S. Mor, S. Nagoria, Synth. Commun. 46 (2016) 169. https://doi.org/10.1080/00397911.2015.1127383
  33. X. Qu, J. Xiao, G. Liu, S. Liu, Z. Zhang, Miner. Eng. 89 (2016) 10. https://doi.org/10.1016/j.mineng.2015.12.015
  34. G. Liu, J. Xiao, J. Liu, X. Qu, Q. Liu, H. Zeng, X. Yang, L. Xie, H. Zhong, Q. Liu, Z. Xu, Colloids Surf A: Physicochem. Eng. Asp. 511 (2016) 285. https://doi.org/10.1016/j.colsurfa.2016.10.017
  35. M.H. Mashhadizadeh, K. Eskandari, A. Foroumadi, A. Shafiee, Talanta 76 (2008) 497. https://doi.org/10.1016/j.talanta.2008.02.019
  36. P. Bharati, A. Bharti, M.K. Bharty, S. Kashyap, U.P. Singh, N.K. Singh, Polyhedron 63 (2013) 222. https://doi.org/10.1016/j.poly.2013.07.027
  37. P. Bharati, A. Bharti, P. Nath, S. Kumari, N.K. Singh, M.K. Bharty, Inorg. Chim. Acta 443 (2016) 160. https://doi.org/10.1016/j.ica.2016.01.003
  38. B. Geboes, K. Baert, A. Hubin, T. Breugelmans, Electrochim. Acta 156 (2015) 308. https://doi.org/10.1016/j.electacta.2015.01.036
  39. O.L. Blajiev, T. Breugelmans, R. Pintelon, H. Terryn, A. Hubin, Electrochim. Acta 53 (2008) 7451. https://doi.org/10.1016/j.electacta.2008.01.048
  40. F. Matsumoto, M. Ozaki, Y. Inatomi, S.C. Paulson, N. Oyama, Langmuir 15 (1999) 857. https://doi.org/10.1021/la980919k
  41. S. Varvara, R. Bostan, L. Gaina,  L.M. Muresan, Mater. Corros. 65 (2014) 1202. https://doi.org/10.1002/maco.201307072
  42. A. Saha, R. Kumar, R. Kumar, C. Devakumar, J. Heterocycl. Chem. 47 (2010) 838. https://doi.org/10.1002/jhet.345
  43. P. Li, L. Shi, M. Gao, X. Yang, W. Xue, L. Jin, D. Hu, B. Song, Bioorg. Med. Chem. Lett. 25 (2015) 481. https://doi.org/10.1016/j.bmcl.2014.12.038
  44. J. Tian, L. Xu, W. Deng, H. Jiang, Z. Gao, Y. Hu, Chem. Eng. Sci. 164 (2017) 99. https://doi.org/10.1016/j.ces.2017.02.013
  45. F. Hipler, R.A. Fischer, J. Muller, J. Chem. Soc. Perkin Trans. 2 9 (2002) 1620.
  46. N.U. Guzeldemirci, O. Kucukbasmaci, Eur. J. Med. Chem. 45 (2010) 63. https://doi.org/10.1016/j.ejmech.2009.09.024
  47. W. Chen, S. Hong, H. Li, H. Luo, M. Li, N. Li, Corros. Sci. 61 (2012) 53. https://doi.org/10.1016/j.corsci.2012.04.023
  48. E.E. Chufan, J.C. Pedregosa, J. Borras, Vib. Spectrosc. 15 (1997) 191. https://doi.org/10.1016/S0924-2031(97)00033-7
  49. L. Huang, J. Shen, J. Ren, Q.J. Meng, T. Yu, Chin. Sci. Bull. 46 (2001) 387. https://doi.org/10.1007/BF03183270
  50. Q. Feng, W. Zhao, S. Wen, Q. Cao, Sep. Purif. Technol. 178 (2017) 193. https://doi.org/10.1016/j.seppur.2017.01.053
  51. Q. Feng, S. Wen, J. Deng, W. Zhao, Appl. Surf. Sci. 425 (2017) 8. https://doi.org/10.1016/j.apsusc.2017.07.017
  52. G. Liu, Z. Qiu, J. Wang, Q. Liu, J. Xiao, H. Zeng, H. Zhong, Z. Xu, J. Colloid Interface Sci. 437 (2015) 42. https://doi.org/10.1016/j.jcis.2014.08.069
  53. J. Zhou, S. Chen, L. Zhang, Y. Feng, H. Zhai, J. Electroanal. Chem. 612 (2008) 257. https://doi.org/10.1016/j.jelechem.2007.10.011
  54. P. Kalimuthu, S.A. John, Electrochem. Commun. 11 (2009) 367. https://doi.org/10.1016/j.elecom.2008.12.006
  55. Z. He, G. Liu, X. Yang, W. Liu, J. Ind. Eng. Chem. 37 (2016) 107. https://doi.org/10.1016/j.jiec.2016.03.013
  56. C.D. Taylor, A. Chandra, J. Vera, N. Sridhar, J. Electrochem. Soc. 162 (2015) C347. https://doi.org/10.1149/2.0691507jes
  57. L. Xu, H. Wu, F. Dong, L. Wang, Z. Wang, J. Xiao, Miner. Eng. 41 (2013) 41. https://doi.org/10.1016/j.mineng.2012.10.015
  58. L. Deng, H. Zhong, S. Wang, G. Liu, Sep. Purif. Technol. 145 (2015) 8. https://doi.org/10.1016/j.seppur.2015.02.029

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