6
58
KUZNETSOV et al.
mixture was distilled in a vacuum collecting the
fraction boiling at 127–150°С (6 mm Hg). Yield 13.40 g
6. Zurita, R., Franco, L., Puiggalí, J., and Rodríguez-
Galañ, A., Polym. Degrad. Stabil., 2007, vol. 92,
p. 975.
(
70%). The compound was recrystallized from 26 mL
7. Naira, L.S. and Laurencin C.T., Prog. Polymer. Sci.,
2007, vol. 32, p. 762.
of acetone. Yield 11.90 g (62%), mp 42–43°С (mp 45°С
1
[
(
20]), purity 99.99% (GLC). Н NMR spectrum
CDCl ), δ, ppm: 2.15 m (2H, CH ), 4.46 t (4H, CH ).
8. Bowman, M.P. and Kreutzberger, C.B., US Patent no.
3
2
2
6
580001, 2003; Chem. Abstr., 2003, vol. 139,
Found, %: С 47.06; Н 5.93. М 102. C H O . Calcu-
4
6
3
p. 38261n.
lated, %: С 47.06; Н 5.92. М 102.09.
9. Bowman, M.P. and Kreutzberger, C.B., US Patent no.
Reaction with propyl and isopropyl carbonates was
performed analogously.
6506909, 2003; Chem. Abstr., 2003, vol. 138, p. 37719u.
1
1
0. Muller, K.R., Buchholz, B., and Hess, J., US Patent no.
212321, 1993; Chem. Abstr., 1993, vol. 115, p. 9590t.
1. Wei-Yang, S. and Speranza, G.P., US Patent no.
003084, 1991; Chem. Abstr., 1991, vol. 114,
p. 247258q.
5
At the use of dibutyl carbonate an azeotrope
mixture formed of butanol−dibutyl carbonate in a
molar ratio 1 : 0.4, therefore in the reaction with
dibutyl carbonate the latter was taken in an appropriate
excess. In a flask was placed 31.50 g (0.18 mol) of
dibutyl carbonate, 7.60 g (0.1 mol) of trimethylene
glycol, 0.20 g of sodium butylate, and 20 mL of the
azeotrope mixture butanol−dibutyl carbonate was
distilled off at atmospheric pressure. The residual
mixture was distilled in a vacuum collecting the
fraction boiling at 127–150°С (6 mm Hg). Yield 8.90 g
5
12. Shaikh, A.-A.G. and Sivaram, S., Chem. Rev., 1996,
vol. 96, p. 951.
13. Qibiao, L., Wenyu, Z., Ning, Z., Wei, W., and Yuhan, S.,
Catal. Today, 2006, vol. 115, p. 111.
4. Kondo, K., Sonoda, N., and Tsutsumi, S., Tetrahedron
Lett., 1971, vol. 51, p. 4885.
5. Rivetti, F. and Romano, U., EP Patent Appl. no.
1
1
1
1
1
1
2
2
0534545, 1991; Chem. Abstr., 1993, vol. 119, p. 138752.
6. Wang, H., Lu, B., Wang, X., Zhang, J., and Cai, Q.,
Fuel Proc. Tech., 2009, vol. 90, p. 1198.
7. Jong, R.D. and Abrakham, D., RF Patent no. 2367648,
2004; Ref. Zh. Khim., 2010, vol. 07, no. 19N 48P.
8. Shaikh, A.-A.G. and Sivaram, S., Chem. Rev., 1996,
vol. 96, p. 951.
9. Shim, H.-L., Udayakumar, S., Yu, J.-I., Kim, I., and
Park, D.-W., Catal. Today, 2009, vol. 148, p. 350.
0. Chu, F., Dueno, E.E., and Jung, K.W., Tetrahedron,
(
87%). The compound was recrystallized from 16 mL
of acetone. Yield 8.20 g (80%) of trimethylene
carbonate, mp 42–44°С (mp 45°С [30]), purity 99.99%
1
(
GLC). Н NMR spectrum (CDCl ), δ, ppm: 2.15 m
3
(
2H, CH ), 4.46 t (4H, CH ). Found, %: С 47.06; Н
2
2
5
.92. М 102. C H O .Calculated, %: С 47.06; Н 5.92.
4 6 3
М 102.09.
At the use as catalyst potassium alkoxides instead
of sodium alkoxides the yields coincide within ~1%.
1
999, vol. 40, p. 1847.
1. Salvatore, R.N., Chu, F., Nagle, A.S., Kapxhiu, E.A.,
Cross, R.M., and Jung, K.W., Tetrahedron, 2002,
vol. 58, p. 3329.
22. Allais, C.P., Boelens, M., and Van Der Heide, E., US
Patent no. 20100121078, 2010; Chem. Abstr., 2010,
vol. 151, p. 552989.
3. Kuznetsov, V.A., Pestov, A.V., Pervova, M.G., and
Yatluk, Yu.G., Russ. J. Org. Chem., 2013, vol. 49, p. 1078.
4. Hoebbel, D., Nacken, M., and Schmidt, H., J. Sol-Gel
Sci. Tech., 2001, vol. 21, p. 177.
The study was carried out under the financial
support of the Government of the Sverdlovsk oblast
and the Russian Foundation for Basic Research in the
framework of the project no. 13-03-96085 r_ural_а,
and also of the Ural Branch of the Russian Academy of
Sciences (project no. 14-3-IP-34).
2
2
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