Email this article 
Hide
Show all
OPEN ACCESS | 
PEER-REVIEWED |
RESEARCH ARTICLE
|
DOWNLOAD PDF
|
VIEW FULL-TEXT PDF
| TOTAL VIEWS
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 | Revised: 15 Apr 2015 | Accepted: 25 Apr 2015 | Published: 30 Sep 2015 | Issue Date: September 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
DOI: 10.5155/eurjchem.6.3.275-278.1250
Links for Article
| | | | | | |
| | | | | | |
Related Articles
Article Metrics
This Abstract was viewed 508 times |
PDF Article downloaded 243 times
Funding information
Academy of Scientific & Innovative Research - Indian Institute of Chemical Technology, India
Citations
[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
The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item
DOI Link: https://doi.org/10.5155/eurjchem.6.3.275-278.1250
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
Save to Zotero
Save to Mendeley
European Journal of Chemistry 2015, 6(3), 275-278 | doi: https://doi.org/10.5155/eurjchem.6.3.275-278.1250 | Get rights and content
Refbacks
- There are currently no refbacks.
Copyright (c)
© Copyright 2010 - 2020 • Atlanta Publishing House LLC • All Right Reserved.
The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.
Copyright 2010-2020 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.