New procedure for recycling homogeneous catalyst: Propylene carbonate synthesis under supercritical CO2 conditions

Green Chemistry

Volumn 5, Issue 1, 2003, Pages 92-94

  He, Liang Nian ^a   Yasuda, Hiroyuki ^a   Sakakura, Toshiyasu ^a  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON DIOXIDE; PHOSPHONIUM DERIVATIVE; PROPYLENE CARBONATE; PROPYLENE OXIDE;

ARTICLE; CARBON DIOXIDE TENSION; CATALYSIS; CATALYST; SEPARATION TECHNIQUE; SUPERCRITICAL FLUID; SYNTHESIS; TEMPERATURE SENSITIVITY;

EID: 0345257184     PISSN: 14639262     EISSN: None     Source Type: Journal    
DOI: 10.1039/b210007j     Document Type: Article

References (27)

1. (a) Chemical Synthesis Using Supercritical Fluids, ed. P. G. Jessop and W. Leitner, Wiley-VCH, Weinheim, 1999;
2. (b) P. G. Jessop, T. Ikariya and R. Noyori, Chem. Rev., 1999, 99, 475-493;
3. (c) R. T. Baker and W. Tumas, Science, 1999, 284, 1477-1479;
4. (d) M. Poliakoff and P. King, Nature, 2001, 412, 125;
5. (e) S. L. Wells and J. DeSimone, Angew. Chem., Int. Ed., 2001, 40, 518-527.
6. (a) W. Leitner, Angew. Chem., Int. Ed. Engl., 1995, 34, 2207-2221;
7. (b) P. G. Jessop, T. Ikariya and R. Noyori, Chem. Rev., 1995, 95, 259-272.
8. (a) D. J. Darensbourg and M. W. Holtcamp, Coord. Chem. Rev., 1996, 153, 155-174, and references therein.
9. For recent reports on cyclic carbonate synthesis, see (b) T. Yano, H. Matsui, T. Koike, H. Ishiguro, H. Fujihara, M. Yoshihara and T. Maeshima, Chem. Commun., 1997, 1129-1130; (c) K. Yamaguchi, K. Ebitani, T. Yoshida, H. Yoshida and K. Kaneda, J. Am. Chem. Soc., 1999, 121, 4526-4527; (d) T. Zhao, Y. Han and Y. Sun, Phys. Chem. Chem. Phys., 1999, 1, 3047-3051; (e) H. S. Kim, J. J. Kim, B. G. Lee, O. S. Jung, H. G. Jang and S. O. Kang, Angew. Chem., Int. Ed., 2000, 39, 4096-4098; (f) T. Iwasaki, N. Kihara and T. Endo, Bull. Chem. Soc. Jpn., 2000, 73, 713-719; (g) D. Ji, X. Lu and R. He, Appl. Catal. A, 2000, 203, 329-333; (h) H. Kawanami and Y. Ikushima, Chem. Commun., 2000, 2089-2090; (i) M. Tu and R. J. Davis, J. Catal., 2001, 199, 85-91; (j) B. M. Bhanage, S. Fujita, Y. Ikushima and M. Arai, Appl. Catal. A, 2001, 219, 259-266; (k) R. L. Paddock and S. T. Nguyen, J. Am. Chem. Soc., 2001, 123, 11498-11499; (l) J. Peng and Y. Deng, New J. Chem., 2001, 25, 639-641; (m) M. Aresta and A. Dibenedetto, J. Mol. Catal. A, 2002, 182-183, 399-409.
10. For recent reports on cyclic carbonate synthesis, see (b) T. Yano, H. Matsui, T. Koike, H. Ishiguro, H. Fujihara, M. Yoshihara and T. Maeshima, Chem. Commun., 1997, 1129-1130; (c) K. Yamaguchi, K. Ebitani, T. Yoshida, H. Yoshida and K. Kaneda, J. Am. Chem. Soc., 1999, 121, 4526-4527; (d) T. Zhao, Y. Han and Y. Sun, Phys. Chem. Chem. Phys., 1999, 1, 3047-3051; (e) H. S. Kim, J. J. Kim, B. G. Lee, O. S. Jung, H. G. Jang and S. O. Kang, Angew. Chem., Int. Ed., 2000, 39, 4096-4098; (f) T. Iwasaki, N. Kihara and T. Endo, Bull. Chem. Soc. Jpn., 2000, 73, 713-719; (g) D. Ji, X. Lu and R. He, Appl. Catal. A, 2000, 203, 329-333; (h) H. Kawanami and Y. Ikushima, Chem. Commun., 2000, 2089-2090; (i) M. Tu and R. J. Davis, J. Catal., 2001, 199, 85-91; (j) B. M. Bhanage, S. Fujita, Y. Ikushima and M. Arai, Appl. Catal. A, 2001, 219, 259-266; (k) R. L. Paddock and S. T. Nguyen, J. Am. Chem. Soc., 2001, 123, 11498-11499; (l) J. Peng and Y. Deng, New J. Chem., 2001, 25, 639-641; (m) M. Aresta and A. Dibenedetto, J. Mol. Catal. A, 2002, 182-183, 399-409.
11. For recent reports on cyclic carbonate synthesis, see (b) T. Yano, H. Matsui, T. Koike, H. Ishiguro, H. Fujihara, M. Yoshihara and T. Maeshima, Chem. Commun., 1997, 1129-1130; (c) K. Yamaguchi, K. Ebitani, T. Yoshida, H. Yoshida and K. Kaneda, J. Am. Chem. Soc., 1999, 121, 4526-4527; (d) T. Zhao, Y. Han and Y. Sun, Phys. Chem. Chem. Phys., 1999, 1, 3047-3051; (e) H. S. Kim, J. J. Kim, B. G. Lee, O. S. Jung, H. G. Jang and S. O. Kang, Angew. Chem., Int. Ed., 2000, 39, 4096-4098; (f) T. Iwasaki, N. Kihara and T. Endo, Bull. Chem. Soc. Jpn., 2000, 73, 713-719; (g) D. Ji, X. Lu and R. He, Appl. Catal. A, 2000, 203, 329-333; (h) H. Kawanami and Y. Ikushima, Chem. Commun., 2000, 2089-2090; (i) M. Tu and R. J. Davis, J. Catal., 2001, 199, 85-91; (j) B. M. Bhanage, S. Fujita, Y. Ikushima and M. Arai, Appl. Catal. A, 2001, 219, 259-266; (k) R. L. Paddock and S. T. Nguyen, J. Am. Chem. Soc., 2001, 123, 11498-11499; (l) J. Peng and Y. Deng, New J. Chem., 2001, 25, 639-641; (m) M. Aresta and A. Dibenedetto, J. Mol. Catal. A, 2002, 182-183, 399-409.
12. For recent reports on cyclic carbonate synthesis, see (b) T. Yano, H. Matsui, T. Koike, H. Ishiguro, H. Fujihara, M. Yoshihara and T. Maeshima, Chem. Commun., 1997, 1129-1130; (c) K. Yamaguchi, K. Ebitani, T. Yoshida, H. Yoshida and K. Kaneda, J. Am. Chem. Soc., 1999, 121, 4526-4527; (d) T. Zhao, Y. Han and Y. Sun, Phys. Chem. Chem. Phys., 1999, 1, 3047-3051; (e) H. S. Kim, J. J. Kim, B. G. Lee, O. S. Jung, H. G. Jang and S. O. Kang, Angew. Chem., Int. Ed., 2000, 39, 4096-4098; (f) T. Iwasaki, N. Kihara and T. Endo, Bull. Chem. Soc. Jpn., 2000, 73, 713-719; (g) D. Ji, X. Lu and R. He, Appl. Catal. A, 2000, 203, 329-333; (h) H. Kawanami and Y. Ikushima, Chem. Commun., 2000, 2089-2090; (i) M. Tu and R. J. Davis, J. Catal., 2001, 199, 85-91; (j) B. M. Bhanage, S. Fujita, Y. Ikushima and M. Arai, Appl. Catal. A, 2001, 219, 259-266; (k) R. L. Paddock and S. T. Nguyen, J. Am. Chem. Soc., 2001, 123, 11498-11499; (l) J. Peng and Y. Deng, New J. Chem., 2001, 25, 639-641; (m) M. Aresta and A. Dibenedetto, J. Mol. Catal. A, 2002, 182-183, 399-409.
13. For recent reports on cyclic carbonate synthesis, see (b) T. Yano, H. Matsui, T. Koike, H. Ishiguro, H. Fujihara, M. Yoshihara and T. Maeshima, Chem. Commun., 1997, 1129-1130; (c) K. Yamaguchi, K. Ebitani, T. Yoshida, H. Yoshida and K. Kaneda, J. Am. Chem. Soc., 1999, 121, 4526-4527; (d) T. Zhao, Y. Han and Y. Sun, Phys. Chem. Chem. Phys., 1999, 1, 3047-3051; (e) H. S. Kim, J. J. Kim, B. G. Lee, O. S. Jung, H. G. Jang and S. O. Kang, Angew. Chem., Int. Ed., 2000, 39, 4096-4098; (f) T. Iwasaki, N. Kihara and T. Endo, Bull. Chem. Soc. Jpn., 2000, 73, 713-719; (g) D. Ji, X. Lu and R. He, Appl. Catal. A, 2000, 203, 329-333; (h) H. Kawanami and Y. Ikushima, Chem. Commun., 2000, 2089-2090; (i) M. Tu and R. J. Davis, J. Catal., 2001, 199, 85-91; (j) B. M. Bhanage, S. Fujita, Y. Ikushima and M. Arai, Appl. Catal. A, 2001, 219, 259-266; (k) R. L. Paddock and S. T. Nguyen, J. Am. Chem. Soc., 2001, 123, 11498-11499; (l) J. Peng and Y. Deng, New J. Chem., 2001, 25, 639-641; (m) M. Aresta and A. Dibenedetto, J. Mol. Catal. A, 2002, 182-183, 399-409.
14. For recent reports on cyclic carbonate synthesis, see (b) T. Yano, H. Matsui, T. Koike, H. Ishiguro, H. Fujihara, M. Yoshihara and T. Maeshima, Chem. Commun., 1997, 1129-1130; (c) K. Yamaguchi, K. Ebitani, T. Yoshida, H. Yoshida and K. Kaneda, J. Am. Chem. Soc., 1999, 121, 4526-4527; (d) T. Zhao, Y. Han and Y. Sun, Phys. Chem. Chem. Phys., 1999, 1, 3047-3051; (e) H. S. Kim, J. J. Kim, B. G. Lee, O. S. Jung, H. G. Jang and S. O. Kang, Angew. Chem., Int. Ed., 2000, 39, 4096-4098; (f) T. Iwasaki, N. Kihara and T. Endo, Bull. Chem. Soc. Jpn., 2000, 73, 713-719; (g) D. Ji, X. Lu and R. He, Appl. Catal. A, 2000, 203, 329-333; (h) H. Kawanami and Y. Ikushima, Chem. Commun., 2000, 2089-2090; (i) M. Tu and R. J. Davis, J. Catal., 2001, 199, 85-91; (j) B. M. Bhanage, S. Fujita, Y. Ikushima and M. Arai, Appl. Catal. A, 2001, 219, 259-266; (k) R. L. Paddock and S. T. Nguyen, J. Am. Chem. Soc., 2001, 123, 11498-11499; (l) J. Peng and Y. Deng, New J. Chem., 2001, 25, 639-641; (m) M. Aresta and A. Dibenedetto, J. Mol. Catal. A, 2002, 182-183, 399-409.
15. For recent reports on cyclic carbonate synthesis, see (b) T. Yano, H. Matsui, T. Koike, H. Ishiguro, H. Fujihara, M. Yoshihara and T. Maeshima, Chem. Commun., 1997, 1129-1130; (c) K. Yamaguchi, K. Ebitani, T. Yoshida, H. Yoshida and K. Kaneda, J. Am. Chem. Soc., 1999, 121, 4526-4527; (d) T. Zhao, Y. Han and Y. Sun, Phys. Chem. Chem. Phys., 1999, 1, 3047-3051; (e) H. S. Kim, J. J. Kim, B. G. Lee, O. S. Jung, H. G. Jang and S. O. Kang, Angew. Chem., Int. Ed., 2000, 39, 4096-4098; (f) T. Iwasaki, N. Kihara and T. Endo, Bull. Chem. Soc. Jpn., 2000, 73, 713-719; (g) D. Ji, X. Lu and R. He, Appl. Catal. A, 2000, 203, 329-333; (h) H. Kawanami and Y. Ikushima, Chem. Commun., 2000, 2089-2090; (i) M. Tu and R. J. Davis, J. Catal., 2001, 199, 85-91; (j) B. M. Bhanage, S. Fujita, Y. Ikushima and M. Arai, Appl. Catal. A, 2001, 219, 259-266; (k) R. L. Paddock and S. T. Nguyen, J. Am. Chem. Soc., 2001, 123, 11498-11499; (l) J. Peng and Y. Deng, New J. Chem., 2001, 25, 639-641; (m) M. Aresta and A. Dibenedetto, J. Mol. Catal. A, 2002, 182-183, 399-409.
16. For recent reports on cyclic carbonate synthesis, see (b) T. Yano, H. Matsui, T. Koike, H. Ishiguro, H. Fujihara, M. Yoshihara and T. Maeshima, Chem. Commun., 1997, 1129-1130; (c) K. Yamaguchi, K. Ebitani, T. Yoshida, H. Yoshida and K. Kaneda, J. Am. Chem. Soc., 1999, 121, 4526-4527; (d) T. Zhao, Y. Han and Y. Sun, Phys. Chem. Chem. Phys., 1999, 1, 3047-3051; (e) H. S. Kim, J. J. Kim, B. G. Lee, O. S. Jung, H. G. Jang and S. O. Kang, Angew. Chem., Int. Ed., 2000, 39, 4096-4098; (f) T. Iwasaki, N. Kihara and T. Endo, Bull. Chem. Soc. Jpn., 2000, 73, 713-719; (g) D. Ji, X. Lu and R. He, Appl. Catal. A, 2000, 203, 329-333; (h) H. Kawanami and Y. Ikushima, Chem. Commun., 2000, 2089-2090; (i) M. Tu and R. J. Davis, J. Catal., 2001, 199, 85-91; (j) B. M. Bhanage, S. Fujita, Y. Ikushima and M. Arai, Appl. Catal. A, 2001, 219, 259-266; (k) R. L. Paddock and S. T. Nguyen, J. Am. Chem. Soc., 2001, 123, 11498-11499; (l) J. Peng and Y. Deng, New J. Chem., 2001, 25, 639-641; (m) M. Aresta and A. Dibenedetto, J. Mol. Catal. A, 2002, 182-183, 399-409.
17. For recent reports on cyclic carbonate synthesis, see (b) T. Yano, H. Matsui, T. Koike, H. Ishiguro, H. Fujihara, M. Yoshihara and T. Maeshima, Chem. Commun., 1997, 1129-1130; (c) K. Yamaguchi, K. Ebitani, T. Yoshida, H. Yoshida and K. Kaneda, J. Am. Chem. Soc., 1999, 121, 4526-4527; (d) T. Zhao, Y. Han and Y. Sun, Phys. Chem. Chem. Phys., 1999, 1, 3047-3051; (e) H. S. Kim, J. J. Kim, B. G. Lee, O. S. Jung, H. G. Jang and S. O. Kang, Angew. Chem., Int. Ed., 2000, 39, 4096-4098; (f) T. Iwasaki, N. Kihara and T. Endo, Bull. Chem. Soc. Jpn., 2000, 73, 713-719; (g) D. Ji, X. Lu and R. He, Appl. Catal. A, 2000, 203, 329-333; (h) H. Kawanami and Y. Ikushima, Chem. Commun., 2000, 2089-2090; (i) M. Tu and R. J. Davis, J. Catal., 2001, 199, 85-91; (j) B. M. Bhanage, S. Fujita, Y. Ikushima and M. Arai, Appl. Catal. A, 2001, 219, 259-266; (k) R. L. Paddock and S. T. Nguyen, J. Am. Chem. Soc., 2001, 123, 11498-11499; (l) J. Peng and Y. Deng, New J. Chem., 2001, 25, 639-641; (m) M. Aresta and A. Dibenedetto, J. Mol. Catal. A, 2002, 182-183, 399-409.
18. For recent reports on cyclic carbonate synthesis, see (b) T. Yano, H. Matsui, T. Koike, H. Ishiguro, H. Fujihara, M. Yoshihara and T. Maeshima, Chem. Commun., 1997, 1129-1130; (c) K. Yamaguchi, K. Ebitani, T. Yoshida, H. Yoshida and K. Kaneda, J. Am. Chem. Soc., 1999, 121, 4526-4527; (d) T. Zhao, Y. Han and Y. Sun, Phys. Chem. Chem. Phys., 1999, 1, 3047-3051; (e) H. S. Kim, J. J. Kim, B. G. Lee, O. S. Jung, H. G. Jang and S. O. Kang, Angew. Chem., Int. Ed., 2000, 39, 4096-4098; (f) T. Iwasaki, N. Kihara and T. Endo, Bull. Chem. Soc. Jpn., 2000, 73, 713-719; (g) D. Ji, X. Lu and R. He, Appl. Catal. A, 2000, 203, 329-333; (h) H. Kawanami and Y. Ikushima, Chem. Commun., 2000, 2089-2090; (i) M. Tu and R. J. Davis, J. Catal., 2001, 199, 85-91; (j) B. M. Bhanage, S. Fujita, Y. Ikushima and M. Arai, Appl. Catal. A, 2001, 219, 259-266; (k) R. L. Paddock and S. T. Nguyen, J. Am. Chem. Soc., 2001, 123, 11498-11499; (l) J. Peng and Y. Deng, New J. Chem., 2001, 25, 639-641; (m) M. Aresta and A. Dibenedetto, J. Mol. Catal. A, 2002, 182-183, 399-409.
19. For recent reports on cyclic carbonate synthesis, see (b) T. Yano, H. Matsui, T. Koike, H. Ishiguro, H. Fujihara, M. Yoshihara and T. Maeshima, Chem. Commun., 1997, 1129-1130; (c) K. Yamaguchi, K. Ebitani, T. Yoshida, H. Yoshida and K. Kaneda, J. Am. Chem. Soc., 1999, 121, 4526-4527; (d) T. Zhao, Y. Han and Y. Sun, Phys. Chem. Chem. Phys., 1999, 1, 3047-3051; (e) H. S. Kim, J. J. Kim, B. G. Lee, O. S. Jung, H. G. Jang and S. O. Kang, Angew. Chem., Int. Ed., 2000, 39, 4096-4098; (f) T. Iwasaki, N. Kihara and T. Endo, Bull. Chem. Soc. Jpn., 2000, 73, 713-719; (g) D. Ji, X. Lu and R. He, Appl. Catal. A, 2000, 203, 329-333; (h) H. Kawanami and Y. Ikushima, Chem. Commun., 2000, 2089-2090; (i) M. Tu and R. J. Davis, J. Catal., 2001, 199, 85-91; (j) B. M. Bhanage, S. Fujita, Y. Ikushima and M. Arai, Appl. Catal. A, 2001, 219, 259-266; (k) R. L. Paddock and S. T. Nguyen, J. Am. Chem. Soc., 2001, 123, 11498-11499; (l) J. Peng and Y. Deng, New J. Chem., 2001, 25, 639-641; (m) M. Aresta and A. Dibenedetto, J. Mol. Catal. A, 2002, 182-183, 399-409.
20. For recent reports on cyclic carbonate synthesis, see (b) T. Yano, H. Matsui, T. Koike, H. Ishiguro, H. Fujihara, M. Yoshihara and T. Maeshima, Chem. Commun., 1997, 1129-1130; (c) K. Yamaguchi, K. Ebitani, T. Yoshida, H. Yoshida and K. Kaneda, J. Am. Chem. Soc., 1999, 121, 4526-4527; (d) T. Zhao, Y. Han and Y. Sun, Phys. Chem. Chem. Phys., 1999, 1, 3047-3051; (e) H. S. Kim, J. J. Kim, B. G. Lee, O. S. Jung, H. G. Jang and S. O. Kang, Angew. Chem., Int. Ed., 2000, 39, 4096-4098; (f) T. Iwasaki, N. Kihara and T. Endo, Bull. Chem. Soc. Jpn., 2000, 73, 713-719; (g) D. Ji, X. Lu and R. He, Appl. Catal. A, 2000, 203, 329-333; (h) H. Kawanami and Y. Ikushima, Chem. Commun., 2000, 2089-2090; (i) M. Tu and R. J. Davis, J. Catal., 2001, 199, 85-91; (j) B. M. Bhanage, S. Fujita, Y. Ikushima and M. Arai, Appl. Catal. A, 2001, 219, 259-266; (k) R. L. Paddock and S. T. Nguyen, J. Am. Chem. Soc., 2001, 123, 11498-11499; (l) J. Peng and Y. Deng, New J. Chem., 2001, 25, 639-641; (m) M. Aresta and A. Dibenedetto, J. Mol. Catal. A, 2002, 182-183, 399-409.
21. (a) H. Yasuda, L.-N. He and T. Sakakura, J. Catal., 2002, 209, 547-550.
22. 2, see (b) X.-B. Lu, R. He and C.-X. Bai, J. Mol. Catal. A, 2002, 186, 1-11.
23. 2 by using fluorinated phosphine ligands have been reported, see: (a) D. Hâncu and E. J. Beckman, Green Chem., 2001, 3, 80-86; (b) M. McCarthy, H. Stemmer and W. Leitner, Green Chem., 2002, 4, 501-504.
24. 2 by using fluorinated phosphine ligands have been reported, see: (a) D. Hâncu and E. J. Beckman, Green Chem., 2001, 3, 80-86; (b) M. McCarthy, H. Stemmer and W. Leitner, Green Chem., 2002, 4, 501-504.
25. 4P1 (4) were analogously synthesized by reacting the tri(polyfluoroalkyl)phosphines with either methyl iodide or the corresponding polyfluoroalkyl iodides.
26. 2 was slowly released by bubbling into DMF at -20°C for trapping any unreacted propylene oxide. The liquid products and the DMF solution were mixed and analyzed by means of GC and GC-MS.
27. T. Nishikubo, A. Kameyama, J. Yamashita, T. Fukumitsu, C. Maejima and M. Tomoi, J. Polvm. Sci., Polym. Chem., 1995, 33, 1011-1017.