Selective formation of 2-hydroxy-3,3-bis(hydroxymethyl)-γ-butyrolactone from formaldehyde on hydrotalcite-type catalysts

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 2, 1996, Pages 425-429

  Mizutani, Tadashi ^a   Miki, Yasushi ^b   Nakashima, Ruka ^b   Fujita, Haruo ^a   Ogoshi, Hisanobu ^a  

^a KYOTO UNIVERSITY   (Japan)

^b TOTTORI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA HYDROXY BETA,BETA BIS(HYDROXYMETHYL) GAMMA BUTYROLACTONE; GAMMA BUTYROLACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; GAS LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029883774     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.425     Document Type: Article

References (33)

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12. Examples for hydrotalcite-type catalysts, see: a) T. Nakatsuka, H. Kawasaki, S. Yamashita, and S. Kohjiya, Bull. Chem. Soc. Jpn., 52, 2449 (1979); b) P. Gherardi, O. Ruggeri, F. Trifiro, A. Vaccari, G. Del Piero, G. Manara, and B. Notari, Stud. Surf. Sci. Catal., 16 (Prep. Catal. 3), 723 (1983); c) E. Suzuki and Y. Ono, Bull. Chem. Soc. Jpn., 61, 1008 (1988); d) V. Corma, V. Fornes, R. M. Martin-Aranda, and F. Rey, J. Catal., 134, 58 (1992); e) D. E. Laycock and R. A. Newman, Stud. Surf. Sci. Catal., 73 (Prog. Catal.), 269 (1992); f) A. L. McKenzie, C. T. Fishel, and R. J. Davis, J. Catal., 138, 547 (1992); g) T. Tatsumi, H. Tajima, K. Yamamoto, and H. Tominaga, Stud. Surf. Sci. Catal., 75 (New Frontiers in Catalysis, Pt. B), 1703 (1993); h) K. Kaneda, S. Ueno, and T. Imanaka, J. Chem. Soc., Chem. Commun., 1994, 797; i) A. Corma, S. Iborra, J. Primo, and F. Rey, Appl. Catal., A, 114, 215 (1994); j) H. Tsuji, F. Yagi, H. Hattori, and H. Kita, J. Catal., 148, 759 (1994).
13. Examples for hydrotalcite-type catalysts, see: a) T. Nakatsuka, H. Kawasaki, S. Yamashita, and S. Kohjiya, Bull. Chem. Soc. Jpn., 52, 2449 (1979); b) P. Gherardi, O. Ruggeri, F. Trifiro, A. Vaccari, G. Del Piero, G. Manara, and B. Notari, Stud. Surf. Sci. Catal., 16 (Prep. Catal. 3), 723 (1983); c) E. Suzuki and Y. Ono, Bull. Chem. Soc. Jpn., 61, 1008 (1988); d) V. Corma, V. Fornes, R. M. Martin-Aranda, and F. Rey, J. Catal., 134, 58 (1992); e) D. E. Laycock and R. A. Newman, Stud. Surf. Sci. Catal., 73 (Prog. Catal.), 269 (1992); f) A. L. McKenzie, C. T. Fishel, and R. J. Davis, J. Catal., 138, 547 (1992); g) T. Tatsumi, H. Tajima, K. Yamamoto, and H. Tominaga, Stud. Surf. Sci. Catal., 75 (New Frontiers in Catalysis, Pt. B), 1703 (1993); h) K. Kaneda, S. Ueno, and T. Imanaka, J. Chem. Soc., Chem. Commun., 1994, 797; i) A. Corma, S. Iborra, J. Primo, and F. Rey, Appl. Catal., A, 114, 215 (1994); j) H. Tsuji, F. Yagi, H. Hattori, and H. Kita, J. Catal., 148, 759 (1994).
14. Examples for hydrotalcite-type catalysts, see: a) T. Nakatsuka, H. Kawasaki, S. Yamashita, and S. Kohjiya, Bull. Chem. Soc. Jpn., 52, 2449 (1979); b) P. Gherardi, O. Ruggeri, F. Trifiro, A. Vaccari, G. Del Piero, G. Manara, and B. Notari, Stud. Surf. Sci. Catal., 16 (Prep. Catal. 3), 723 (1983); c) E. Suzuki and Y. Ono, Bull. Chem. Soc. Jpn., 61, 1008 (1988); d) V. Corma, V. Fornes, R. M. Martin-Aranda, and F. Rey, J. Catal., 134, 58 (1992); e) D. E. Laycock and R. A. Newman, Stud. Surf. Sci. Catal., 73 (Prog. Catal.), 269 (1992); f) A. L. McKenzie, C. T. Fishel, and R. J. Davis, J. Catal., 138, 547 (1992); g) T. Tatsumi, H. Tajima, K. Yamamoto, and H. Tominaga, Stud. Surf. Sci. Catal., 75 (New Frontiers in Catalysis, Pt. B), 1703 (1993); h) K. Kaneda, S. Ueno, and T. Imanaka, J. Chem. Soc., Chem. Commun., 1994, 797; i) A. Corma, S. Iborra, J. Primo, and F. Rey, Appl. Catal., A, 114, 215 (1994); j) H. Tsuji, F. Yagi, H. Hattori, and H. Kita, J. Catal., 148, 759 (1994).
15. Examples for hydrotalcite-type catalysts, see: a) T. Nakatsuka, H. Kawasaki, S. Yamashita, and S. Kohjiya, Bull. Chem. Soc. Jpn., 52, 2449 (1979); b) P. Gherardi, O. Ruggeri, F. Trifiro, A. Vaccari, G. Del Piero, G. Manara, and B. Notari, Stud. Surf. Sci. Catal., 16 (Prep. Catal. 3), 723 (1983); c) E. Suzuki and Y. Ono, Bull. Chem. Soc. Jpn., 61, 1008 (1988); d) V. Corma, V. Fornes, R. M. Martin-Aranda, and F. Rey, J. Catal., 134, 58 (1992); e) D. E. Laycock and R. A. Newman, Stud. Surf. Sci. Catal., 73 (Prog. Catal.), 269 (1992); f) A. L. McKenzie, C. T. Fishel, and R. J. Davis, J. Catal., 138, 547 (1992); g) T. Tatsumi, H. Tajima, K. Yamamoto, and H. Tominaga, Stud. Surf. Sci. Catal., 75 (New Frontiers in Catalysis, Pt. B), 1703 (1993); h) K. Kaneda, S. Ueno, and T. Imanaka, J. Chem. Soc., Chem. Commun., 1994, 797; i) A. Corma, S. Iborra, J. Primo, and F. Rey, Appl. Catal., A, 114, 215 (1994); j) H. Tsuji, F. Yagi, H. Hattori, and H. Kita, J. Catal., 148, 759 (1994).
16. Examples for hydrotalcite-type catalysts, see: a) T. Nakatsuka, H. Kawasaki, S. Yamashita, and S. Kohjiya, Bull. Chem. Soc. Jpn., 52, 2449 (1979); b) P. Gherardi, O. Ruggeri, F. Trifiro, A. Vaccari, G. Del Piero, G. Manara, and B. Notari, Stud. Surf. Sci. Catal., 16 (Prep. Catal. 3), 723 (1983); c) E. Suzuki and Y. Ono, Bull. Chem. Soc. Jpn., 61, 1008 (1988); d) V. Corma, V. Fornes, R. M. Martin-Aranda, and F. Rey, J. Catal., 134, 58 (1992); e) D. E. Laycock and R. A. Newman, Stud. Surf. Sci. Catal., 73 (Prog. Catal.), 269 (1992); f) A. L. McKenzie, C. T. Fishel, and R. J. Davis, J. Catal., 138, 547 (1992); g) T. Tatsumi, H. Tajima, K. Yamamoto, and H. Tominaga, Stud. Surf. Sci. Catal., 75 (New Frontiers in Catalysis, Pt. B), 1703 (1993); h) K. Kaneda, S. Ueno, and T. Imanaka, J. Chem. Soc., Chem. Commun., 1994, 797; i) A. Corma, S. Iborra, J. Primo, and F. Rey, Appl. Catal., A, 114, 215 (1994); j) H. Tsuji, F. Yagi, H. Hattori, and H. Kita, J. Catal., 148, 759 (1994).
17. Examples for hydrotalcite-type catalysts, see: a) T. Nakatsuka, H. Kawasaki, S. Yamashita, and S. Kohjiya, Bull. Chem. Soc. Jpn., 52, 2449 (1979); b) P. Gherardi, O. Ruggeri, F. Trifiro, A. Vaccari, G. Del Piero, G. Manara, and B. Notari, Stud. Surf. Sci. Catal., 16 (Prep. Catal. 3), 723 (1983); c) E. Suzuki and Y. Ono, Bull. Chem. Soc. Jpn., 61, 1008 (1988); d) V. Corma, V. Fornes, R. M. Martin-Aranda, and F. Rey, J. Catal., 134, 58 (1992); e) D. E. Laycock and R. A. Newman, Stud. Surf. Sci. Catal., 73 (Prog. Catal.), 269 (1992); f) A. L. McKenzie, C. T. Fishel, and R. J. Davis, J. Catal., 138, 547 (1992); g) T. Tatsumi, H. Tajima, K. Yamamoto, and H. Tominaga, Stud. Surf. Sci. Catal., 75 (New Frontiers in Catalysis, Pt. B), 1703 (1993); h) K. Kaneda, S. Ueno, and T. Imanaka, J. Chem. Soc., Chem. Commun., 1994, 797; i) A. Corma, S. Iborra, J. Primo, and F. Rey, Appl. Catal., A, 114, 215 (1994); j) H. Tsuji, F. Yagi, H. Hattori, and H. Kita, J. Catal., 148, 759 (1994).
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25. Yields for the product mixture are listed in Table 1.
26. Starting from 0.9 g of the sample formed on HT-Mg-Al catalyst, and reprecipitated from acetonitrile-water, 0.155 g of 2, 0.034 g of 1, and 0.028 g of 3 were obtained after partition chromatography on celite. However, purity of 3 was low, < 50% based on gas-liquid chromatography.
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33. 2O) δ/ppm 79.48 (s), 74.47 (d), 66.41 (t), 64.85 (t).