Fatty Amides in Minutes: Direct Formation from Fatty Esters in a Green Synthetic Process
Science Journal of Analytical Chemistry
Volume 8, Issue 1, March 2020, Pages: 18-28
Received: Jul. 25, 2019; Accepted: Aug. 20, 2019; Published: Feb. 13, 2020
Views 214      Downloads 101
Authors
Onyanobi Abel-Anyebe, Science Laboratory Technology Department, Benue State Polytechnic, Ugbokolo, Nigeria; Department of Environmental and Interdisciplinary Sciences, Texas Southern University, Houston, The United States
Nabil Idris, Chemistry Department, Howard University, Washington DC, The United States
Djene Keita, Department of Environmental and Interdisciplinary Sciences, Texas Southern University, Houston, The United States
Kieran Ita Ekpenyong, Chemistry Department, University of Jos, Jos, Nigeria
Momoh Audu Yakubu, Department of Environmental and Interdisciplinary Sciences, Texas Southern University, Houston, The United States
Article Tools
Follow on us
Abstract
Fatty amides are used in the manufacture of drugs, cosmetics, plastics, insecticides, etc. but the synthetic process involves fatty ester-derived fatty acid steps with economic and environmental consequences. Fatty esters (vegetable oils) are available in abundance and renewable but have not been used directly or cost effectively in the production of fatty amides. The fatty ester is usually first stripped to fatty acids resulting in a two-step instead of a single step synthesis which requires high temperatures (100 – 240°C), long reaction time (3 – 72 hours) and the use of catalyst. We had previously reported on a novel green method for the direct formation of fatty amides from a fatty ester. In the present study, the functionality and applicability of this green method is evaluated using a culinary and non-culinary oil namely peanut and castor oils. Each oil sample was hydrolyzed with NaOH in a non-aqueous medium and reacted in-situ with NH4Cl at 50°C in a reaction time of 60 minutes with no catalyst added. Conversions of 83 and 79% were recorded for the reactions of peanut and castor oils, respectively. The products of synthesis were characterized by Fourier-transform infrared spectroscopy (FT-IR) and various concentrations of product samples and two reference samples - erucamide and oleamide obtained from Sigma Aldrich - were subjected to Gas chromatography – Mass spectrometry (GC/MS) analysis. The qualitative GC-MS reports revealed the presence of 9-octadecenamide (oleamide) and hexadecanamide (palmitamide) at retention times of 27.76 and 23.90 minutes, respectively for all samples, including the reference. The predominant component of the second reference sample, erucamide, was found to be 13-docosenamide (erucamide) appearing at GC retention time of 32.58 minutes. The IR spectra of the products are strongly indicative of the presence of amides. The GC-MS analysis of the product samples confirms the formation of fatty amides. The detection of oleamide and erucamide in the reference samples and the detection of methyl ricinoleate at GC retention time of 26.573 minutes in the castor oil product sample validates the GC-MS analysis and confirms the functionality and applicability of this novel method of synthesis.
Keywords
Fatty Acids, Fatty Amides, Fatty Esters, Green Process, Synthetic Method, Gas Chromatogram, Mass Spectra
To cite this article
Onyanobi Abel-Anyebe, Nabil Idris, Djene Keita, Kieran Ita Ekpenyong, Momoh Audu Yakubu, Fatty Amides in Minutes: Direct Formation from Fatty Esters in a Green Synthetic Process, Science Journal of Analytical Chemistry. Vol. 8, No. 1, 2020, pp. 18-28. doi: 10.11648/j.sjac.20200801.14
Copyright
Copyright © 2020 Authors retain the copyright of this article.
This article is an open access article distributed under the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
References
[1]
Harwood, H. J. Nitrogen-containing derivatives of the fatty acids. Journal of the American Oil Chemists Society 1954, Volume 31, Issue 11, pp 559–564.
[2]
Abel-Anyebe, O. Fatty Amide Formation by Direct Vegetable Oil Stripping. Doctoral Dissertation, University of Jos 2011.
[3]
Getachew, P.; Getachew, M.; Joo, J.; Choi, Y. S.; Hwang, D. S.; Hong, Y. The Slip Agents Oleamide and Erucamide Reduce Biofouling by Marine Benthic Organisms (Diatoms, Biofilms and Abalones). Tox. and Env Health Sciences 2016 8 (5) 341–348.
[4]
Mathew’s Chemistry Blog Extraction of the slip-additives erucamide, behenamide and oleamide https://www.mjlphd.net/blog/extraction-of-the-slip-additives-erucamide-behenamide-and-oleamide.
[5]
Jaeger, C. W.; Titterington, D. R.; Bui, L. V. US Patent 5,902,841, Google Patents, 1/jo400509n.
[6]
Abel-Anyebe, O.; Ekpenyong, K. I.; Eseyin, A. Int. J. Chem, 2013, 5, 1, 80-86.
[7]
Milne, J. C.; Jirousek, R.; Bemis, J. E.; Vu, C. B.; Ting, A. Patents no US20130059801, 2013.
[8]
M. Vishe, M.; J. N. Johnston, J. N.; The Inverted Ketene Synthon: A Double Umpolung Approach to Enantioselective B2,3-Amino Amide Synthesis Chem. Sci., 2019, Advance Article DOI: 10.1039/c8sc04330b.
[9]
Tremblay, H.; St-Georges, C.; Legault, M. A.; Morin, C.; Fortin, S.; Marsault, E.; One-pot Synthesis of Polyunsaturated Fatty Acid Amides with Anti-proliferative Properties, Bioorganic & Med. Chem. Letts., 2014, 24, 24, 5635-5638.
[10]
Viveros, M.; Marco, E.; Llorente, R.; L´opez-Gallardo, M.; Endocannabinoid System and Synaptic Plasticity: Implications for Emotional Responses Neural Plasticity, 2007, 52908.
[11]
Tan, B.; Bradshaw, H. B.; Rimmerman, N.; Srinivasan, H.; Yu, Y. W.; Krey, J. F.; Monn, M. F.; Chen, J. S.; Hu, S. S.; Pickens, S. R.; Walker, J. M.). Targeted Lipidomics: Discovery of New Fatty Acyl Amides. AAPSJ, 2006, 8, 3, 54.
[12]
Christie, W. W.; Anandamide, Oleamide and other Fatty Amides: Structure, Occurrence, Biology and Analysis Lipid Library, http://www.lipidlibrary.co.uk.
[13]
http://www.en.wikipedia.org/wiki/Anandamide.
[14]
Hanus, L.; Gopher, A.; Almong S.; Mechoulam, R.; Two New Unsaturated Fatty Acid Ethanolamides in Brain that Bind to the Cannabinoid Receptor J. Med. Chem., 1993, 36: 3032-3034.
[15]
Kunos, G.; Varga, K.; Wagner, J.; Ellis, E. F.; Sanyai, A. Cardiovascular Uses of Cannabinoid Compounds. US Patent 5939429.
[16]
Brown University News Services, 11th October, 1999.
[17]
Hedlund, P. B.; Carson, M. J.; Sutcliffe, J. G.; Thomas, E. A.; Allosteric Regulation by Oleamide of the Binding Properties of 5-Hydroxytryptamine7 Receptors Biochem pharmacol, 1999, 58, 11, 1807-13.
[18]
Hoong, S. S.; Ahmad, S.; Hassan, H. A. Process for the Production of Fatty Acid Amides. Grant publication number US7098351 B2Grant no US7098351 B2.
[19]
Research and Markets Fatty amides: Global market report (2018-2022) forecast, April 13 2018.
[20]
Orsavova, J.; Misurcova, L.; Ambrozova, J. V.; Vicha, R.; Mlcek, J. Fatty Acids Composition of Vegetable Oils and Its Contribution to Dietary Energy Intake and Dependence of Cardiovascular Mortality on Dietary Intake of Fatty Acids. Int. J. Mol. Sci. 2015 16 12871-12890 doi: 10.3390/ijms160612871.
[21]
Mancini, A.; Imperlini, E.; Nigro, E.; Montagnese, C.; Daniele, A.; Orrù, S.; Buono, P. Biological and Nutritional Properties of Palm Oil and Palmitic Acid: Effects on Health Molecules 2015 20 (9) 17339-17361 DOI: 10.3390/molecules200917339.
[22]
Salimon, J.; Mohd Noor, D. A; Nazrizawati, A. T.; Mohd Firdaus, M. Y.; Noraishah, A.; Fatty acid composition and physicochemical properties of Malaysian castor bean ricinus communis L. seed oil Sains Malaysiana, 2010, 39, 5, 761-764.
[23]
Özcan, M.; Seven, S.; Physical and Chemical Analysis and Fatty Acid Composition of Peanut, Peanut Oil and Peanut Butter From ÇOM and NC-7 Cultivars. Grasas y Aceites 2003 Vol. 54 (1) 12-18.
[24]
Youngs, C. G.; Mallard, T. M.; Craig, B. M.; Sallans, H. R. Component Fatty Acids of Rapeseed Oil. Canadian J. Chem. 1921 29 871-876.
[25]
https://www.quirkyscience.com/olive-oil-peanut-oil/.
[26]
https://www.thekitchn.com/whats-the-difference-between-canola-and-rapeseed-206047.
[27]
https://www.foodsafety.gov.mo/e/sense/detail.aspx?id=b70be5cf-6b48-4a6c.
[28]
www.erinnudi.com/2015/06/25/difference-between-canola-oil-and-rapeseed-oil/.
[29]
Schafer, M. G.; Ross, A. A.; Londo, J. P.; Burdick, C. A.; Lee, E. H.; Travers, S. E.; Van de Water, P. K.; Sagers, C. L. The Establishment of Genetically Engineered Canola Populations in the U.S. PLoS One 2011 6 (10) 25736. doi: 10.1371/journal.pone.0025736.
[30]
Canola Council of Canada. Canola: The Myths Debunked - https://www.canolacouncil.org.
[31]
http://www2.ups.edu/faculty/hanson/Spectroscopy/IR/IRfrequencies.html.
[32]
https://www1.udel.edu/chem/fox/Chem333/Fall2013/.../Welcome.../IR%20handout.pdf.
ADDRESS
Science Publishing Group
1 Rockefeller Plaza,
10th and 11th Floors,
New York, NY 10020
U.S.A.
Tel: (001)347-983-5186