European Journal of Chemistry 2014, 5(3), 532-535 | doi: https://doi.org/10.5155/eurjchem.5.3.532-535.1088 | Get rights and content






  OPEN ACCESS | PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

Synthesis of industrially important platform chemicals via olefin metathesis of palash fatty acid methyl esters


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: 03 May 2014 | Revised: 06 Jun 2014 | Accepted: 06 Jun 2014 | Published: 30 Sep 2014 | Issue Date: September 2014

Abstract


The study signifies the importance of olefin metathesis in developing industrially important platform chemicals from a non-edible renewable resource, palash oil using Grubb’s second generation catalyst. The reaction conditions were optimized by varying the concentration of the catalyst, 0.03-0.05 mM and the temperature, 45-100 °C of the reaction. Maximum yield of the metathesized products, as analysed using GC/GC-MS were obtained employing lower concentration of the catalyst, 0.03 Mm and temperature, 45 °C for 36 h. The metathesized products showed the formation of hydrocarbons namely 9-octadecene (10.9%) and cyclodecacyclotetradecene (27%) as major. The formation of cyclodecacyclotetradecene was observed for the first time. The study also describes the possible routes and the molecules involved in the formation of the metathesized products.


Keywords


9-Octadecene; Non-edible oils; Self-metathesis; Synthetic intermediates; Palash fatty acid methyl esters; Grubb’s second generation catalyst

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.5.3.532-535.1088

Links for Article


| | | | | | |

| | | | | | |

| |

Related Articles




Article Metrics

This Abstract was viewed 503 times | PDF Article downloaded 277 times

Funding information


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

Citations

/


[1]. Godwin Ameh Abel, Sridhar Viamajala, Sasidhar Varanasi, Kana Yamamoto
Toward Sustainable Synthesis of PA12 (Nylon-12) Precursor from Oleic Acid Using Ring-Closing Metathesis
ACS Sustainable Chemistry & Engineering  4(10), 5703, 2016
DOI: 10.1021/acssuschemeng.6b01648
/


[2]. James W. Herndon
The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2014
Coordination Chemistry Reviews  317, 1, 2016
DOI: 10.1016/j.ccr.2015.09.012
/


[3]. 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]. Meier, M. A. R.; Metzger, J. O.; Schubert, U. S. Chem. Soc. Rev. 2007, 36, 1788-1802.
http://dx.doi.org/10.1039/b703294c

[2]. Mol, J. C. J. Mol. Catal. 1994, 90, 185-199.
http://dx.doi.org/10.1016/0304-5102(94)00009-3

[3]. Kamalakar, K.; Amit, K. R.; Prasad, R. B. N.; Karuna, M. S. L. Ind. Crops Prod. 2013, 51, 249-257.
http://dx.doi.org/10.1016/j.indcrop.2013.08.058

[4]. 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

[5]. 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

[6]. Marvey, B. B.; Segakweng, C. K.; Vosloo, H. C. M. Int. J. Mol. Sci. 2008, 9, 615-625.
http://dx.doi.org/10.3390/ijms9040615

[7]. Holser, R. A.; Doll, K. M.; Erhan, S. Z. Fuel 2006, 85, 393-395.
http://dx.doi.org/10.1016/j.fuel.2005.07.018

[8]. Refvik, M. D.; Larock, R. C.; Tian, Q. J. Am. Oil Chem. Soc. 1999, 76, 93-98.
http://dx.doi.org/10.1007/s11746-999-0053-z

[9]. 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

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

[11]. Marvey, B. B.; Du-Plessis, 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

[12]. Biermann, U.; Friedt, W.; Lang, S.; Luhs, W.; Machmuller, G.; Metzger, J. O.; Klaas, M.; Schafer, J. H.; Scheider, M. P. Angew. Chem. Int. Ed. 2000, 39, 2206-2224.
http://dx.doi.org/10.1002/1521-3773(20000703)39:13<2206::AID-ANIE2206>3.0.CO;2-P

[13]. Mol, J. C. Green Chem. 2002, 4, 5-13.
http://dx.doi.org/10.1039/b109896a

[14]. Joachim, R.; Johannes, L. M. S. J. Chem. Ecol. 2000, 26, 1205-1217.
http://dx.doi.org/10.1023/A:1005484027559

[15]. Choo, Y. M.; Ooi, K. E.; Ooi, I. H.; Tan, D. D. H. J. Am. Oil Chem. Soc. 1996, 73, 333-336.
http://dx.doi.org/10.1007/BF02523427

[16]. 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

How to cite


Vyshnavi, Y.; Prasad, R.; Karuna, M. Eur. J. Chem. 2014, 5(3), 532-535. doi:10.5155/eurjchem.5.3.532-535.1088
Vyshnavi, Y.; Prasad, R.; Karuna, M. Synthesis of industrially important platform chemicals via olefin metathesis of palash fatty acid methyl esters. Eur. J. Chem. 2014, 5(3), 532-535. doi:10.5155/eurjchem.5.3.532-535.1088
Vyshnavi, Y., Prasad, R., & Karuna, M. (2014). Synthesis of industrially important platform chemicals via olefin metathesis of palash fatty acid methyl esters. European Journal of Chemistry, 5(3), 532-535. doi:10.5155/eurjchem.5.3.532-535.1088
Vyshnavi, Yelchuri, Rachapudi Badari Narayana Prasad, & Mallampalli Sri Lakshmi Karuna. "Synthesis of industrially important platform chemicals via olefin metathesis of palash fatty acid methyl esters." European Journal of Chemistry [Online], 5.3 (2014): 532-535. Web. 28 Nov. 2020
Vyshnavi, Yelchuri, Prasad, Rachapudi, AND Karuna, Mallampalli. "Synthesis of industrially important platform chemicals via olefin metathesis of palash fatty acid methyl esters" European Journal of Chemistry [Online], Volume 5 Number 3 (30 September 2014)

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.5.3.532-535.1088

| | | | | | | |

| | | | | |

Save to Zotero Save to Mendeley



European Journal of Chemistry 2014, 5(3), 532-535 | doi: https://doi.org/10.5155/eurjchem.5.3.532-535.1088 | 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.