European Journal of Chemistry

Metathesis of 9-octadecenoic acid methyl ester: diversity and mechanism of product formation at various Grubbs’ catalyst concentrations



Main Article Content

Yelchuri Vyshnavi
Rachapudi Badari Narayana Prasad
Mallampalli Sri Lakshmi Karuna

Abstract

Self-metathesis of 9-octadecenoic acid methyl ester was carried out with varying the concentration of Grubbs’ second generation catalyst from 0.03 mmol to 0.18 mmol at 40-45 °C for 36 h. Only two products (9-octadecene 30%, and dimethyl-9-octadecene-dienoate 23%) resulted when 0.06 mmol of catalyst was employed, while at other concentrations four metathesized products were observed. 9-Octadecene generated at 0.03, 0.06 and 0.12 mmol completely disappeared and dimethyl-9-octadecene-dienoate (64%) was observed in major amounts at 0.18 mmol concentration.


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Vyshnavi, Y.; Prasad, R. B. N.; Karuna, M. S. L. Metathesis of 9-Octadecenoic Acid Methyl Ester: Diversity and Mechanism of Product Formation at Various Grubbs’ Catalyst Concentrations. Eur. J. Chem. 2015, 6, 275-278.

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References

[1]. Christensen, C. H.; Raas-Hansen, J.; Marsden, C. C.; Taarning, E.; Gallezot, K. Chem. Sus. Chem. 2008, 1, 734-737.
http://dx.doi.org/10.1002/cssc.200700168

[2]. Corma, A.; Iborra, S.; Velty, A. Chem. Rev. 2007, 107, 2411-2502
http://dx.doi.org/10.1021/cr050989d

[3]. Dodds, P. R.; Gross, R. A. Science 2007, 318, 1250-1251.
http://dx.doi.org/10.1126/science.1146356

[4]. Erhan, S. Z.; Bagby, M. O.; Nelsen, T. C. J. Am. Oil Chem. Soc. 1997, 74, 703-706.
http://dx.doi.org/10.1007/s11746-997-0204-z

[5]. Ohlmann, D. M.; Gooben, L. J.; Dieter, M. Chem. Eur. J. 2011, 17, 9508-9519.
http://dx.doi.org/10.1002/chem.201100654

[6]. Vennestrom, P. N. R.; Osmundsen, C. M.; Christensen, C. H.; Taarning, E. Angew. Chem. Int. Ed. 2011, 50, 10502-10509.
http://dx.doi.org/10.1002/anie.201102117

[7]. Vyshnavi, Y.; Prasad, R. B. N.; Karuna, M. S. L. Ind. Crops. Prod. 2013, 50, 701‐706.
http://dx.doi.org/10.1016/j.indcrop.2013.08.020

[8]. Marshall, A. L.; Alaimo, P. J. Chem. Eur. J. 2010, 16, 4970-4980.
http://dx.doi.org/10.1002/chem.200903028

[9]. Bosma, R. H. A.; Vanden Aardweg, G. C. N.; Mol, J. C. J. Organomet. Chem. 1983, 255, 159-171.
http://dx.doi.org/10.1016/0022-328X(83)87019-3

[10]. Lynn, D. M.; Kanaoka, S.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 784-790.
http://dx.doi.org/10.1021/ja950327d

[11]. Priya, A. T.; Marvey, B. B. Int. J. Mol. Sci. 2009, 10, 5020-5030.
http://dx.doi.org/10.3390/ijms10115020

[12]. Verkuijlen, E.; Boelhouwer, C. J. Chem. Soc. Chem. Commun. 1974, 793-794.
http://dx.doi.org/10.1039/c39740000793

[13]. Marvey, B. B. Int. J. Mol. Sci. 2008, 9, 1393-1406.
http://dx.doi.org/10.3390/ijms9081393

[14]. Philippe, M.; Didillon, B.; Gilbert, L. Green Chem. 2012, 14, 952-956.
http://dx.doi.org/10.1039/c2gc16341a

[15]. Ngo, H. L.; Foglia, T. A. J. Am. Oil Chem. Soc. 2007, 84, 777-784.
http://dx.doi.org/10.1007/s11746-007-1089-6

[16]. Ngo, H. L.; Jones, K.; Foglia, T. A. J. Am. Oil Chem. Soc. 2006, 83, 629-634.
http://dx.doi.org/10.1007/s11746-006-1249-0

[17]. Gooben, L. J.; Ohlmann, D. M.; Dierker, M. Green Chem. 2010, 12, 197-200.
http://dx.doi.org/10.1039/B916853B

[18]. Behr, A.; Westfechtel, A.; Perez Gomes. J. Chem. Eng. Technol. 2008, 31, 700-714.
http://dx.doi.org/10.1002/ceat.200800035

[19]. Refvik, M. D.; Larock, R. C.; Tian, Q. J. Am. Oil Chem. Soc. 1999, 75, 93-98.
http://dx.doi.org/10.1007/s11746-999-0053-z

[20]. Ronda, J. C.; Ligadas, G.; Galia, M.; Cadiz, V. Eur. J. Lipid Sci. Technol. 2011, 113, 46-58.
http://dx.doi.org/10.1002/ejlt.201000103

[21]. Marvey, B. B.; DuPlessis, J. A. K.; Vosloo, H. C. M.; Mol, J. C. J. Mol. Catal. A Chem. 2003, 201, 297-308.
http://dx.doi.org/10.1016/S1381-1169(03)00155-9

[22]. Behr, A.; Perez Gomes, J. Eur. J. Lipid Sci. Technol. 2010, 112, 31-50.
http://dx.doi.org/10.1002/ejlt.200900091

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Academy of Scientific & Innovative Research - Indian Institute of Chemical Technology, India
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