화학공학소재연구정보센터
홈 로그인 로그아웃 연락처 사이트맵
Journal of Industrial and Engineering Chemistry, Vol.90, 95-104, October, 2020
DOI10.1016/j.jiec.2020.07.001  Export Citation
Novel mono-and bi-functional phosphonium salts deriving from toxic phosphine off-gas as efficient catalysts for chemical fixation of CO2
Ju-Ping Dong, Chen Zhao1, Jin-Jun Qiu, and Cheng-Mei Liu†
  • Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education: Hubei Key Laboratory of Material Chemistry and Service Failure, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan 430074, PR China
  • 1School of Materials and Energy, Guangdong University of Technology, Guangzhou 510006, China
E-mail:
Utilizing phosphine (PH3) tail gas as starting feedstock, a series of novel mono-and bifucntional phosphonium compounds (P+(CH2CH2CN)3RX , X= Br, I) was prepaed by a sustainable preparation route. The newly prepared phosphonium halides show high thermal stability and their degradation temperature are far higher than that of CO2 chemical fixation. The mono-fucntional phosphonium salts combinate with ZnBr2 to form an efficient Lewis acid/base type catalytic system for CO2 chemical fixation and the bifucntional phosphonium salts alone shows same catalytic effects. The effects of temperature, CO2 pressure, composition of the catalytic system on coupling reaction of CO2 with epoxides are investigated to evaluate the catalytic performance. The results illustrate that 96.7% cyclic Carbonate yield can be obtained in presence of ZnBr2/P+(CH2CH2CN)3C4H9Br (molar ratio = 1:10) under 120 C, 1.5MPa of CO2 pressure in solvent-free condition, menawhile bifuntional phiospohonium salt Br- P+(CH2CH2CN)3C2H4COOH alone shows better catalytic perofromance.
Keywords:Phosphine off-gas;Mono-/bi-functional phosphonium salt;Chemical fixation of CO2;Cyclic carbonate;Tetrakis(hydroxymethyl)phosphonium;sulfate
  1. Otto A, Grube T, Schiebahn S, Stolten D, Energy Environ. Sci., 8, 3283 (2015)
  2. Buttner H, Longwitz L, Steinbauer J, Wulf C, Werner T, Topics Current Chem., 375 (2017)
  3. Appel AM, Bercaw JE, Bocarsly AB, Dobbek H, DuBois DL, Dupuis M, et al., Chem. Reviews, 113, 6621 (2013)
  4. Alves M, Grignard B, Mereau R, Jerome C, Tassaing T, Detrembleur C, Catal. Sci. Technol., 7, 2651 (2017)
  5. Lan D, Fan N, Wang Y, Gao X, Zhang P, Chen L, Au C, Yin S, Chinese J. Catal., 37, 826 (2016)
  6. Buttner H, Grimmer C, Steinbauer J, Werner T, ACS Sustainable Chem. Eng., 4, 4805 (2016)
  7. Tenhumberg N, Buettner H, Schaeffner B, Kruse D, Blumenstein M, Werner T, Green Chem., 18, 3775 (2016)
  8. Sakai T, Tsutsumi Y, Ema T, Green Chem., 10, 337 (2008)
  9. Kilic A, Durgun M, Aytar E, Yavuz R, J. Organomet. Chem., 858, 78 (2018)
  10. Yan XM, Fu R, Liu F, Pan Y, Ding X, Heo GH, Ind. Eng. Chem. Res., 57(9), 3195 (2018)
  11. Wu Y, Zhao Y, Li R, Yu B, Chen Y, Liu X, Wu C, Luo X, Liu Z, ACS Catal., 7, 6251 (2017)
  12. Wei-Li D, Bi J, Sheng-Lian L, Xu-Biao L, Xin-Man T, Chak-Tong A, Appl. Catal. A: Gen., 470, 183 (2014)
  13. Wu SS, Zhang XW, Dai WL, Yin SF, Li WS, Ren YQ, Au CT, Appl. Catal. A: Gen., 341(1-2), 106 (2008)
  14. Sun J, Wang L, Zhang SJ, Li ZX, Zhang XP, Dai WB, Mori RH, J. Mol. Catal. A-Chem., 256(1-2), 295 (2006)
  15. Liu S, Suematsu N, Maruoka K, Shirakawa S, Green Chem., 18, 4611 (2016)
  16. Buttner H, Steinbauer J, Werner T, Chem. Sus. Chem., 8, 2655 (2015)
  17. Steinbauer J, Longwitz L, Frank M, Epping J, Kragl U, Werner T, Green Chem., 19, 4435 (2017)
  18. Lu XB, He R, Bai CX, J. Mol. Catal. A-Chem., 186(1-2), 1 (2002)
  19. Peng J, Yang H, Wang S, Ban B, Wei Z, Lei B, Guo C, J. CO2 Util., 24, 1 (2018)
  20. Buettner H, Steinbauer J, Wulf C, Dindaroglu M, Schmalz H, Werner T, Chem. Sus. Chem., 10, 1076 (2017)
  21. Liu Y, Cheng W, Zhang Y, Sun J, Zhang S, Green Chem., 19, 2184 (2017)
  22. Wang W, Wang Y, Li C, Yan L, Jiang M, Ding Y, ACS Sustainable Chem. Eng., 5, 4523 (2017)
  23. Sun YJBAQ, Xiao F, Chem. Sus. Chem., 10, 1160 (2017)
  24. Yang XY, Wen YM, Chumanov G, Smith RC, J. Polym. Sci. A: Polym. Chem., 55(9), 1620 (2017)
  25. Wang J, Yang JGW, Yi G, Zhang Y, Chem. Commun., 51, 15708 (2015)
  26. Chen JX, Jin B, Dai WL, Deng SL, Cao LR, Cao ZJ, Luo SL, Luo XB, Tu XM, Au CT, Appl. Catal. A: Gen., 484, 26 (2014)
  27. Wei-Li D, Bi J, Sheng-Lian L, Xu-Biao L, Xin-Man T, Chak-Tong A, Catal. Today, 233, 92 (2014)
  28. Ende DJA, Clifford PJ, DeAntonis DM, SantaMaria C, Brenek SJ, Org. Process Res. Dev., 3, 319 (1999)
  29. Kapias T, Griffiths RF, J. Hazard. Mater., 81(3), 223 (2001)
  30. Segall Y, Quistad GB, Sparks SE, Casida JE, Chem. Res. Toxicol., 16, 350 (2003)
  31. Tan ZW, Sun J, Wu CY, Qiu JJ, Liu CM, J. Hazard. Mater., 322, 540 (2017)
  32. Zhu R, Kong D, Sun L, Geng J, Wang X, Chinese Sci. Bull., 52, 131 (2007)
  33. Chen W, Niu X, AnS, Sheng H, Tang Z, Yang Z, Gu X, Sci. Total Environ., 952, 599 (2017)
  34. VULLO WJ, Ind. Eng. Chem. Prod. Res. Dev., 5, 346 (1966)
  35. Weston MH, Morris W, Siu PW, Hoover WJ, Cho D, Richardson RK, Farha OK, Inorg. Chem., 54(17), 8162 (2015)
  36. Aoyagi N, Furusho Y, Endo T, Tetrahedron Lett., 54, 7031 (2013)
  37. Song Q, He L, Wang J, Yasuda H, Sakakura T, Green Chem., 15, 110 (2013)
  38. Li C, Wang W, Yan L, Wang Y, Jiang M, Ding Y, J. Mater. Chem. A, 4, 16017 (2016)
  39. Kim YJ, Varma RS, J. Org. Chem., 70, 7882 (2005)
  40. Tian J, Cai F, Wang J, Du Y, He L, Phosphorus Sulfur Silicon Relat. Elem., 183, 494 (2008)
  41. Ingle GK, Watkins RW, Arif AM, Berreau LM, J. Coord. Chem., 61, 61 (2008)
  42. Jeong J, Suzuki K, Yamaguchi K, Mizuno N, New J. Chem., 41, 13226 (2017)
  43. Toda Y, Komiyama Y, Kikuchi A, Suga H, ACS Catal., 6, 6906 (2016)