recovery and confirmed the hydrolysis reaction was continuously
executable.
1 H. K. Mangold, Angew. Chem., Int. Ed., 1979, 18, 493; S. Snyder,
Prog. Chem. Fats Other Lipids, 1970, 10, 289; E. S. Lower, Manuf.
Chem., 1981, 52:46, 63; C. A. A. van Boeckel, G. A. van der Marel, P.
Westerduin and J. H. van Boom, Synthesis, 1982, 399; G. Hirth and
R. Barner, Helv. Chim. Acta, 1982, 65, 1059; G. Hirth, H. Saroka,
W. Bannwarth and R. Warner, Helv. Chim. Acta, 1983, 66, 1210; K.
Urata and N. Takaishi, J. Am. Oil Chem. Soc., 1996, 73, 819.
2 H. Tsutsumi and A. Ishida, Yukagaku, 1984, 33, 270; H. Tsutsumi
and Y. Suzuki, Yukagaku, 1984, 33, 786.
Acknowledgements
We are grateful to Dr A. Kawamata and Mr N. Katada of
Kao Corporation for permission to publish this paper. And we
also acknowledge for Mr M. Okutsu, Mr S. Tamaki and Mr
O. Tabata for useful comments and suggestions.
3 K. Urata, Oreo Science, 2002, 2, 637; K. Urata and N. Takaishi,
J. Am. Oil Chem. Soc., 1994, 71, 1027; K. Urata and N. Takaishi,
J. Am. Oil Chem. Soc., 1996, 73, 1027.
4 K. Urata, S. Yano, A. Kawamata, N. Takaishi and Y. Inamoto, J. Am.
Oil Chem. Soc., 1988, 65, 1299.
5 R. Mori and Y. Kobata, Jpn. Kokai Tokkyo Koho, 1988, 77833; H.
Morita, T. Inaki and T. Goto, Jpn. Kokai Tokkyo Koho, 1993, 32578.
6 I. Vilotijevic and T. E. Jamison, Science, 2007, 317, 1189.
7 Z. Wang, Y.-T. Cui, Z.-B. Xu and J. Qu, J. Org. Chem., 2008, 73,
2270.
8 O. Tavakoli and H. Yoshida, Green Chem., 2006, 8, 100; O. Tavakoli
and H. Yoshida, Ind. Eng. Chem. Res., 2006, 45, 5675; A. Basile,
M. M. J-Carmona and A. A. Clifford, J. Agric. Food Chem., 1998,
46, 5205.
9 Y. Yang and F. Hidebrand, Anal. Chim. Acta, 2006, 555, 364.
10 R. L. Holliday, J. W. King and G. R. List, Ind. Eng. Chem. Res., 1997,
36, 932; J. W. King, R. L. Holliday and G. R. List, Green Chem., 1999,
1, 261.
11 R. L. Holliday, B. Y. M. Jong and J. W. Kolis, J. Supercrit. Fluids,
1998, 12, 255; A. R. Katritzky and S. M. Allin, Acc. Chem. Res.,
1996, 29, 399.
12 D. G. Archerand and P. Wang, J. Phys. Chem. Ref. Data, 1990,
19, 371; Y. Yang, M. Brlghazi, S. B. Hawthorne and D. J. Mille,
J. Chromatogr., A, 1998, 810, 149.
Notes and references
† The flow reaction system (Fig. 1); deionized water was introduced
into the preheated coil from a plunger pump and heated with oil
bath. The preheated water from the coil went through a T-connector
and the glycidyl ether was introduced at this connector from another
plunger pump. The water–glycidyl ether mixture then passed through
the reaction coil (1 mm i.d., 1700 mm). At the end of the reaction tube,
the overall reaction pressure was checked with an indicator. After passing
the cooling coil, the reaction mixture was introduced into a water–oil
separator through a back pressure regulating valve. For a typical reaction
(Table 2, entry 9), the oil bath was set to a temperature at 250 ◦C, the
water pump was then set to a constant flow of 300 mL min-1, and then
water flow was commenced as the oil bath was heated. The back pressure
regulator was set for an overall system pressure of 5.0 MPa and the
cooling bath was operated at 80 ◦C. The pump for 2-ethylhexyl glycidyl
ether 1b was set to a constant flow of 43.1 mL min-1 (the molar ratio of
water/1b became 80/1) and introduced into the system. After hydrolysis,
the water/oil stream was cooled and depressurized, and collected in a
water–oil separator. 2-Ethylhexyl glyceryl ether 2b was obtained from
oil phase.
This journal is
The Royal Society of Chemistry 2009
Green Chem., 2009, 11, 753–755 | 755
©