A Twitchell Reagent Revival: Biodiesel Generation from Low Cost Oils
compound (7.0 g, 7.0 mmol) was carried out in THF
(40 mL) under 4 bar of hydrogen pressure at 408C with Pd/
C (5%) (500 mg) in 12 h. The catalyst was removed by filtra-
tion, the solvent evaporated and the residue purified by per-
colation through silica gel (hexane as eluent) to yield the sa-
turated hydrocarbon, 1,3-di(tritriacontan-17-yl)benzene;
yield: 6.1 g (86%). The sulphonation of this compound
(6.1 g, 6 mmol) was carried out under the same conditions
previously described for catalyst 4, to afford the expected
compound as a white solid; yield: 6.2 g (96%); mp 79–808C.
1H NMR (200 MHz, CDCl3): d=7.85 (d, J=8.4 Hz, 2H),
7.14 (s, 1H), 7.00 (d, J=8.4 Hz, 2H), 2.51 (m, 2H), 1.60 (m,
8H), 1.25 (br s, 112H), 0.88 (t, J=6.4 Hz, 12H); 13C NMR
(50 MHz, CDCl3): d=151.8, 146.5, 135.7, 128.2, 127.7, 124.9,
50.9, 46.2, 40.6, 37.1, 36.9, 32.2, 30.4, 30.0, 29.9, 29.6, 27.8,
27.6, 22.9, 14.3; IR (film): n=3403, 2916, 2365, 1599, 1456,
1378, 1314, 1164, 1074, 1002, 892, 710 cmÀ1; HR-MS: m/z=
1128.0108, calcd. for C72H138O3S [MÀH+Na]+Na+:
1128.0078.
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Acknowledgements
The authors thank the Spanish Direcciꢀn General de Investi-
gaciꢀn, Ciencia y Tecnologꢁa (DGI-CYT) (CTQ2010-19906/
BQU) and the EU (European Re-integration Grant
PERG04-GA-2008-239244) for their support in this work.
The Spanish Ministerio de Educaciꢀn y Ciencia (MEC) is ac-
knowledged for the fellowship (A. L. F. A.). The authors are
also grateful to Miguel Cobo for jatropha oil supply and for
his fruitful advice. Thanks to Repsol, Biotel, Bio-Oils, Bio-
carburantes de Castilla SA and Andalusi Corporation for
supporting this project and Diego Garcꢁa-Gꢀmez for provid-
ing the pH indicators.
Melero, L. F. Bautista, G. Morales, J. Iglesias,
R
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Lien, L.-S. Hsieh, J. C. S. Wu, Ind. Eng. Chem. Res.
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