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Improved Synthesis of Soluble Metal-Free/Metal Phthalocyanine Tetracarboxylic Acids and Their Application in the Catalytic Epoxidation of Cyclohexene

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Abstract

Soluble metal-free and metal (copper (II), iron (III), and cobalt (II)) phthalocyanine tetracarboxylic acids (5–8) were synthesized using a novel method consisting of improved hydrolysis based on the diazo reaction. The obtained compounds (5–8) were characterized by X-ray diffraction, UV–Vis spectrometry, and FT-IR spectrometry and then utilized as catalysts for the epoxidation of cyclohexene with molecular oxygen as oxidant. Reaction conditions including reaction time, temperature, catalyst amount, and isobutyraldehyde/cyclohexene ratio were optimized to achieve the highest selectivity of cyclohexene oxide. Metal-free phthalocyanine tetracarboxylic acid (5) and metal (copper (II), iron (III), and cobalt (II)) phthalocyanine tetracarboxylic acids (6–8, respectively) were compared. Complexes 6–8 exhibited higher catalytic activity than compound 5 under the optimal conditions.

Graphical Abstract

Four soluble metal-free and metal PTCs were synthesized using a novel method, and were utilized as catalysts for the epoxidation of cyclohexene with molecular oxygen as the oxidant. A total of 58.1% selectivity and yield of cyclohexene oxide were achieved under the optimal condition.

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References

  1. Liu AZ, Lei SB (2007) Surf Interface Anal 39:33

    Article  Google Scholar 

  2. Moons H, Łapok Ł, Loas A, Van Doorslaer S, Gorun SM (2010) Inorg Chem 49:8779

    Article  CAS  Google Scholar 

  3. Sakamoto K, Ohno-Okumura E (2009) Materials 2:1127

    Article  CAS  Google Scholar 

  4. Lu WY, Li N, Chen WX, Yao YY (2009) Carbon 47:3337

    Article  CAS  Google Scholar 

  5. Chen WX, Lu WY, Yao YY, Xu MH (2007) Environ Sci Technol 41:6240

    Article  CAS  Google Scholar 

  6. Shu JH, Wikle HC, Chin BA (2010) Sens Actuator B Chem 148:498

    Article  CAS  Google Scholar 

  7. Wu WT, Wu WH, Ji SM, Guo HM, Wang X, Zhao JZ (2011) Dyes Pigm 89:199

    Article  CAS  Google Scholar 

  8. Kimura M, Nomoto H, Suzuki H, Ikeuchi T, Matsuzaki H, Murakami TN, Furube A, Masaki N, Griffith MJ, Mori S (2013) Chem A Eur J 19:7496

    Article  CAS  Google Scholar 

  9. Zhang MJ, Lv JY, Pan QJ, Guo YR (2014) Theor Chem Acc 133:1582

    Article  Google Scholar 

  10. Matsuzaki H, Murakami TN, Masaki N, Furube A, Kimura M, Mori S (2014) J Phys Chem C 118:17205

    Article  CAS  Google Scholar 

  11. Demirbaş Ü, Bayrak R, Pişkin M, Akçay HT, Durmuş M, Kantekin H (2013) J Organomet Chem 724:225

    Article  Google Scholar 

  12. Zheng BY, Zhang HP, Ke MR, Huang JD (2013) Dyes Pigm 99:185

    Article  CAS  Google Scholar 

  13. Bayrak R, Akçay HT, Beriş FŞ, Şahin E, Bayrak H, Demirbaş Ü (2014) Spectrochim Acta A 133:272

    Article  CAS  Google Scholar 

  14. Çakır V, Çakır D, Pişkin M, Durmuş M, Bıyıklıoğlu Z (2014) J Lumin 154:274

    Article  Google Scholar 

  15. Nabid MR, Asadi S, Shamsianpour M, Sedghi R, Osati S, Safari N (2010) React Funct Polym 70:75

    Article  CAS  Google Scholar 

  16. Nabid MR, Sedghi R, Jamaat PR, Safari N, Entezami AA (2007) Appl Catal A Gen 328:52

    Article  CAS  Google Scholar 

  17. Bayιr ZA (2005) Dyes Pigm 65:235

    Article  Google Scholar 

  18. Sevim AM, Ilgün C, Gül A (2011) Dyes Pigm 89:162

    Article  CAS  Google Scholar 

  19. Minnes R, Weitman H, Lee HJ, Gorun SM, Ehrenberg B (2006) Photochem Photobiol 82:593

    Article  CAS  Google Scholar 

  20. Jung KS, Kwon JH, Son SM, Shin JS, Lee GD, Park SS (2004) Synth Met 141:259

    Article  CAS  Google Scholar 

  21. Kharisov BI, Blanco LM, Torres-Martinez LM, García-Luna A (1999) Ind Eng Chem Res 38:2880

    Article  CAS  Google Scholar 

  22. Negri RM, Zalts A, San Román EA, Aramendía PF, Braslavsky SE (1991) Photochem Photobiol 53:317

    Article  Google Scholar 

  23. Chen JM, Zhang JC, Shen Y, Liu XH (2000) Proc SPIE 4086:749

    Article  CAS  Google Scholar 

  24. Ghorbanloo M, Rahmani S, Yahiro H (2013) Transit Met Chem 38:725

    Article  CAS  Google Scholar 

  25. Peng Y, Li ZY, Tang RR (2013) RSC Adv 3:19965

    Article  Google Scholar 

  26. Sreethawong T, Yamada Y, Kobayashi T, Yoshikawa S (2006) J Mol Catal A Chem 248:226

    Article  CAS  Google Scholar 

  27. Jiang YQ, Li XW, Zhang SC, He YD, Li GH, Li DF, Xu XZ, Lin KF (2014) Mater Lett 132:270

    Article  CAS  Google Scholar 

  28. He S, Liu X, Zhao HY, Zhu Y, Zhang FZ (2015) J Colloid Interface Sci 437:58

    Article  CAS  Google Scholar 

  29. Li ZY, Tang RR, Liu GY (2013) Catal Lett 143:592

    Article  CAS  Google Scholar 

  30. Yamada T, Takai T, Rhode O, Mukaiyama T (1991) Chem Lett 20:5

  31. Punniyamurthy T, Bhatia B, Iqbal J (1993) Tetrahedron Lett 34:4657

    Article  CAS  Google Scholar 

  32. Punniyamurthy T, Velusamy S, Iqbal J (2005) Chem Rev 105:2329

    Article  CAS  Google Scholar 

  33. Sharman WM, Van Lier JE (2005) J Porphyr Phthalocyanines 9:651

    Article  CAS  Google Scholar 

  34. Achar BN, Lokesh KS (2004) J Solid State Chem 177:1987

    Article  CAS  Google Scholar 

  35. Nas A, Kantekin H, Durmuş M, Gümrükçüoğlu N (2014) J Lumin 154:15

    Article  CAS  Google Scholar 

  36. Zhang XF, Lin Y, Guo WF, Zhu JZ (2014) Spectrochim Acta A 133:752

    Article  CAS  Google Scholar 

  37. Özil M, Ağar E, Şaşmaz S, Kahveci B, Akdemir N, Gümrükçüoğlu İE (2007) Dyes Pigm 75:732

    Article  Google Scholar 

  38. Ghani F, Kristen J, Riegler H (2012) J Chem Eng Data 57:439

    Article  CAS  Google Scholar 

  39. Li DP, Ge SX, Sun GF, He Q, Huang BJ, Tian GZ, Lu WY, Li GB, Chen YL, An SN, Zheng Z (2015) Dyes Pigm 113:200

    Article  CAS  Google Scholar 

  40. Mani V, Devasenathipathy R, Chen SM, Gu JA, Huang ST (2015) Renew Energy 74:867

    Article  CAS  Google Scholar 

  41. Nam W, Kim JH, Kim SH, Ho RYN, Valentine JS (1996) Inorg Chem 35:1045

    Article  CAS  Google Scholar 

  42. Li ZY, Liu CH, Tang RR, Liu G (2013) RSC Adv 3:9745

    Article  CAS  Google Scholar 

  43. Angelescu E, Ionescu R, Pavel OD, Zăvoianu R, Bîrjega R, Luculescu CR, Florea M, Olar R (2010) J Mol Catal A Chem 315:178

    Article  CAS  Google Scholar 

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Acknowledgments

The work was supported by the Shanghai Natural Science Foundation (No. 4ZR1440900) and Shanghai Alliance Program (No. LM201336). The authors thank the Analysis and Testing Center of Shanghai Institute of Technology for support.

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Authors and Affiliations

  1. School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai, 201418, China

    Xiaoling Sun, Li Wang & Zhi Tan

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  1. Xiaoling Sun
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  2. Li Wang
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  3. Zhi Tan
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Correspondence to Xiaoling Sun.

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Sun, X., Wang, L. & Tan, Z. Improved Synthesis of Soluble Metal-Free/Metal Phthalocyanine Tetracarboxylic Acids and Their Application in the Catalytic Epoxidation of Cyclohexene. Catal Lett 145, 1094–1102 (2015). https://doi.org/10.1007/s10562-015-1500-0

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  • DOI: https://doi.org/10.1007/s10562-015-1500-0

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