European Journal of Chemistry 2015, 6(3), 275-278. doi:10.5155/eurjchem.6.3.275-278.1250

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


Yelchuri Vyshnavi (1) , Rachapudi Badari Narayana Prasad (2) , Mallampalli Sri Lakshmi Karuna (3,*)

(1) Centre for Lipid Research, Council of Scientific and Industrial Research, Indian Institute of Chemical Technology, Hyderabad 500007, India
(2) Centre for Lipid Research, Council of Scientific and Industrial Research, Indian Institute of Chemical Technology, Hyderabad 500007, India
(3) Centre for Lipid Research, Council of Scientific and Industrial Research, Indian Institute of Chemical Technology, Hyderabad 500007, India
(*) Corresponding Author

Received: 02 Feb 2015, Accepted: 25 Apr 2015, Published: 30 Sep 2015

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.


Keywords


9-Octadecene; Olefin metathesis; Fatty acid methyl esters; Synthetic organic intermediates; Dimethyl 9-octadecene-dienoate; Grubbs’ second generation catalyst

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DOI: 10.5155/eurjchem.6.3.275-278.1250

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Citations

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[1]. James W. Herndon
The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2015
Coordination Chemistry Reviews  329, 53, 2016
DOI: 10.1016/j.ccr.2016.08.007
/


[2]. Vyshnavi Yelchuri, K Srikanth, R B N Prasad, M S L Karuna
Olefin metathesis of fatty acids and vegetable oils
Journal of Chemical Sciences  131(5), , 2019
DOI: 10.1007/s12039-019-1615-8
/


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


How to cite


Vyshnavi, Y.; Prasad, R.; Karuna, M. Eur. J. Chem. 2015, 6(3), 275-278. doi:10.5155/eurjchem.6.3.275-278.1250
Vyshnavi, Y.; Prasad, R.; Karuna, M. Metathesis of 9-octadecenoic acid methyl ester: diversity and mechanism of product formation at various Grubbs’ catalyst concentrations. Eur. J. Chem. 2015, 6(3), 275-278. doi:10.5155/eurjchem.6.3.275-278.1250
Vyshnavi, Y., Prasad, R., & Karuna, M. (2015). Metathesis of 9-octadecenoic acid methyl ester: diversity and mechanism of product formation at various Grubbs’ catalyst concentrations. European Journal of Chemistry, 6(3), 275-278. doi:10.5155/eurjchem.6.3.275-278.1250
Vyshnavi, Yelchuri, Rachapudi Badari Narayana Prasad, & Mallampalli Sri Lakshmi Karuna. "Metathesis of 9-octadecenoic acid methyl ester: diversity and mechanism of product formation at various Grubbs’ catalyst concentrations." European Journal of Chemistry [Online], 6.3 (2015): 275-278. Web. 22 Sep. 2019
Vyshnavi, Yelchuri, Prasad, Rachapudi, AND Karuna, Mallampalli. "Metathesis of 9-octadecenoic acid methyl ester: diversity and mechanism of product formation at various Grubbs’ catalyst concentrations" European Journal of Chemistry [Online], Volume 6 Number 3 (30 September 2015)

DOI Link: https://doi.org/10.5155/eurjchem.6.3.275-278.1250

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