American Journal of Heterocyclic Chemistry

| Peer-Reviewed |

Frugal Utilization of Flue-Cured Virginia Nicotiana tabacum Leaf Wastes as a Vicissitudinous Substrate for Optimized Synthesis of Pyridine-3-Carboxylic Acid

Received: Nov. 19, 2018    Accepted: Dec. 08, 2018    Published: Jan. 25, 2019
Views:       Downloads:

Share This Article

Abstract

Agrotransformation of tobacco leaves into cigarettes and cigars spawns upto 75% wastes which is an environmental and public nuisance owing to its noxious 0.6-3% (w/w) 3-(1-methyl-2-pyrrolindyl) pyridine (MPP) content. Considerately, this volumetric agrowaste is a prodigal loss during tobacco processing. Consequently, the utilization of these frugal wastes as a substrate for pyridine-3-carboxylic acid (PCA) synthesis is a green strategy to obliterate the ecological backlashes of tobacco waste. This concerted study reported the feasibility of utilizing Flue-Cured Virginia (FCV) tobacco waste as a starting substrate for synthesis of pyridine-3-carboxylic acid through MPP as a synthetic intermediate. The intermediate was extracted from powdered FCV wastes using petroleum ether and subsequently oxidized to PCA using 69% concentrated Nitric acid of volumes: 120, 115, 110,105, 100, 95, 90 and 85ml at 87±2°C. The results of the bench scale experiments indicated that the yield of PCA increases with increase in the volume of hot nitric acid; a maximum yield of 25ml was obtained with 100ml of hot nitric acid. The lowest yield of 17ml was from 85ml of hot nitric acid. MPP had a statistical mean boiling point of 249.3±2.082°C, mean density of 1.024±0.006g/cm3 whereas PCA had a mean boiling point of 262±3°C, mean density of 1.505843±0.05503g/cm3, mean pH of 3.3±0.19 and a computed mean solubility of 1.5±0.017g/L. The study has shown that FCV tobacco leaf wastes is a green environmental substrate for organic synthesis of pyridine-3-carboxylic acid.

DOI 10.11648/j.ajhc.20180404.11
Published in American Journal of Heterocyclic Chemistry ( Volume 4, Issue 4, December 2018 )
Page(s) 49-54
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

Arua, Tobacco, Flue-Cured Virginia, Leaf Wastes, Strategy

References
[1] The observer: Tobacco farmers smile to the bank. June 29, 2011. Retrieved January 21st, 2017. https: //www. observer. ug/business/38-business/14052-tobacco-farmers-smile-to-the-bank.
[2] The New Vision. Uganda: Arua tobacco's cash itch, 14 February 2002, Joseph Olanyo, accessed 16th January 2017. https: //allafrica. com/stories/200202140438. html.
[3] Uganda National Tobacco Control Association (UNTCA) Shadow Report on The Status of Implementation of the World Health Organization Framework Convention on Tobacco Control (WHO-FCTC), Articles 8 & 13 in Uganda, pp. 1-20, 2012.
[4] R. Jacob, M. Swenseid. Niacin. In: Ziegler, E. E., Filer, L. J., (Eds.). Present Knowledge in Nutrition. 7th ed. ILSI Press, Washington D. C., pp. 185-190, 1996.
[5] M. F. Murray. “Niacin as a potential AIDs preventive facator”. Medical Hypotheses, vol. 53, no. 5, pp. 375-79, 1999.
[6] M. F. Murray, M. Langan, R. R. MacGregor. “Increased Plasma Tryptophan in HIV-patients treated with pharmacologic doses of Nicotinamide”. Nutrition, vol. 17, no. (7-8), pp. 654-56, 2001.
[7] P. L. Canner, K. G. Berge, N. K. Wenger, J. Stamler, L. Friedman, R. J. Prineas, W. Friedewald. “Fifteen-year mortality in Coronary Drug Project patients: long-term benefit with niacin”. Journal of the American College of Cardiology, vol. 8, no. 6, pp. 1245-55, Dec 1986.
[8] A. C. Boyonoski, J. C. Spronck, L. M. Gallacher, R. M. Jacobs, G. M. Shah, G. G. Poirier, J. B. Kirkland. “Niacin deficiency decreases bone marrow poly (ADP-ribose) and the latency of ethylnitrosourea-induced carcinogenesis in rats”. Journal of Nutrition, vol. 132, no. 1, pp. 108-14, Jan 2002.
[9] E. Negri, S. Franceschi, C. Bosetti. “Selected micronutrients and oral and pharyngeal cancer”. International Journal of Cancer, vol. 86, no. 1, pp. 122-27, Apri 2002. ”
[10] S. Franceschi, E. Bidoli, E. Negri, P. Zambon, R. Talamini, A. Roul, M. Parpinel, F. Levi, L. Simonato, C. La Vecchia. “Role of macronutrients, vitamins and minerals in the aetiology of squamous-cell carcinoma of the oesophagus”. International Journal of Cancer, vol. 86, no. pp. 626, Jun 2000.
[11] E. A. Gale, P. J. Bingley, C. L. Emmett, T. Collier. “European Nicotinamide Diabetes Intervention Trial (ENDIT) Group”. Lancet., vol. 363, no. 9413, pp. 925-31, Mar 2004.
[12] E. F. Lampeter, A. Klinghammer, W. A. Scherbaum, E. Heinze, B. Haastert, G. Giani and H. Kolb. “The Deutsche Nicotinamide Intervention Study: an attempt to prevent type 1 diabetes”. Diabetes, vol. 47, no. 6, pp. 980-84, 1998.
[13] C. J. Greenbaum, S. E. Kahn, J. P. Palmer. “Nicotinamide’s effects on glucose metabolism in subjects at risk for IDDM”. Diabetes, vol. 45, no. 11, pp. 1631-4, Nov. 1996.
[14] Knopp, R. H. Drug treatment of lipid disorders. The New England Journal of Medicine, vol. 341, no. 7, pp. 498-511, 1999.
[15] J. G. Speight. “Chemical and Process Design Handbook”. McGraw-Hill. pp. 2. 352-353, 2002. ISBN 0-07-137433-7.
[16] S. Kumar and B. V. Babu. “Process Intensification of Nicotinic Acid Production via Enzymatic Conversion using Reactive Extraction”. Chemical and Biochemical Engineering Quarterly, vol. 23, no. 3, pp. 367–76, 2009.
[17] N. J. Rasul, J. Shah, A. Shah, F. Gul. “Seperation identification and determination of Nicotinic acid and Nicotinamide from cigarette tobacco and smoke part I”. Journal of the Chemical Society of Pakistan, vol. 19, no. 4, pp. 306-09, 1997.
[18] A. F. Mulyadia, S. Wijanab, A. S. Wahyudi. Optimization of Nicotine Extraction in Tobacco Leaf (Nicotiana tabacum L.): (Study: Comparison of Ether and Petroleum Ether). The International Conference on Chemical Engineering, UNPAR, 2013.
[19] S. Purwono, B. Murachman, J. Wintoko, B. A. Simanjuntak, P. P. Sejati, N. E. Permatasari and D. Lidyawati. “The Effect of Solvent for Extraction for Removing Nicotine on the Development of Charcoal Briquette from Waste of Tobacco Stem”. Journal of Sustainable Energy & Environment, vol. 2, pp. 11-13, 2011.
[20] K. Mahendra, C. V. Narasimha Rao, Y. L. N. Murthy, K. K. Bala Murali. Development of High Value Phytochemicals From Green Tobacco. Int. J. Chem. Res., vol. 01, pp. 23-28, 2011.
[21] C. D. Mathew, T. T. Nagasawa, H. Yamada, M. Kobayashi. “Nitrilase-catalyzed production of nicotinic acid from 3-Cyanopyridine in Rhodococcus rhodochrous J1”. Applied and Environmental Microbiology, vol. 54, no. 4, pp. 1030-32, 1988.
[22] A. V. Peter, J. K. Christopher, S. J. C. Peter. Conversion of 3-cyanopyridine to nicotinic acid by Nocardia rhodochrous LL100-21. Enzyme Microbial Technology, vol. 11, no. 12, pp. 815-23, 1989.
[23] Q.A. Almatawah, D.A. Cowan. ‘‘Thermostable nitrilase catalysed production of nicotinic acid from 3-cyanopyridine’’. Enzyme and Microbial Technology, vol. 25, pp. 718-24, 1999.
[24] O. Kaplan, V. Vejvoda, O. Plíhal, P. Pompach, D. Kavan, P. Fialová, K. Bezouška, M. Macková, M. Cantarella, V. Jirku, V. Kren, L. Martínková. “Purification and characterization of a nitrilase from Aspergillus niger K10”. Applied Microbiology and Biotechnology, vol. 73, pp. 567-75, 2006.
[25] K. Maria, C. Laura, G. Alberto, I. Roberta, E. M. T. Ondîej, S. Agata, M. Ludmila and F. Ahmad, A. G. Moat. “Nicotinic acid biosynthesis in prototrophs and tryptophan auxotrophs of Saccharomyces cerevisiae”. Journal of Biological Chemistry, vol. 241, no. 4, pp. 775-80, 1966.
Cite This Article
  • APA Style

    Timothy Omara, Bashir Musau, Sarah Kagoya. (2019). Frugal Utilization of Flue-Cured Virginia Nicotiana tabacum Leaf Wastes as a Vicissitudinous Substrate for Optimized Synthesis of Pyridine-3-Carboxylic Acid. American Journal of Heterocyclic Chemistry, 4(4), 49-54. https://doi.org/10.11648/j.ajhc.20180404.11

    Copy | Download

    ACS Style

    Timothy Omara; Bashir Musau; Sarah Kagoya. Frugal Utilization of Flue-Cured Virginia Nicotiana tabacum Leaf Wastes as a Vicissitudinous Substrate for Optimized Synthesis of Pyridine-3-Carboxylic Acid. Am. J. Heterocycl. Chem. 2019, 4(4), 49-54. doi: 10.11648/j.ajhc.20180404.11

    Copy | Download

    AMA Style

    Timothy Omara, Bashir Musau, Sarah Kagoya. Frugal Utilization of Flue-Cured Virginia Nicotiana tabacum Leaf Wastes as a Vicissitudinous Substrate for Optimized Synthesis of Pyridine-3-Carboxylic Acid. Am J Heterocycl Chem. 2019;4(4):49-54. doi: 10.11648/j.ajhc.20180404.11

    Copy | Download

  • @article{10.11648/j.ajhc.20180404.11,
      author = {Timothy Omara and Bashir Musau and Sarah Kagoya},
      title = {Frugal Utilization of Flue-Cured Virginia Nicotiana tabacum Leaf Wastes as a Vicissitudinous Substrate for Optimized Synthesis of Pyridine-3-Carboxylic Acid},
      journal = {American Journal of Heterocyclic Chemistry},
      volume = {4},
      number = {4},
      pages = {49-54},
      doi = {10.11648/j.ajhc.20180404.11},
      url = {https://doi.org/10.11648/j.ajhc.20180404.11},
      eprint = {https://download.sciencepg.com/pdf/10.11648.j.ajhc.20180404.11},
      abstract = {Agrotransformation of tobacco leaves into cigarettes and cigars spawns upto 75% wastes which is an environmental and public nuisance owing to its noxious 0.6-3% (w/w) 3-(1-methyl-2-pyrrolindyl) pyridine (MPP) content. Considerately, this volumetric agrowaste is a prodigal loss during tobacco processing. Consequently, the utilization of these frugal wastes as a substrate for pyridine-3-carboxylic acid (PCA) synthesis is a green strategy to obliterate the ecological backlashes of tobacco waste. This concerted study reported the feasibility of utilizing Flue-Cured Virginia (FCV) tobacco waste as a starting substrate for synthesis of pyridine-3-carboxylic acid through MPP as a synthetic intermediate. The intermediate was extracted from powdered FCV wastes using petroleum ether and subsequently oxidized to PCA using 69% concentrated Nitric acid of volumes: 120, 115, 110,105, 100, 95, 90 and 85ml at 87±2°C. The results of the bench scale experiments indicated that the yield of PCA increases with increase in the volume of hot nitric acid; a maximum yield of 25ml was obtained with 100ml of hot nitric acid. The lowest yield of 17ml was from 85ml of hot nitric acid. MPP had a statistical mean boiling point of 249.3±2.082°C, mean density of 1.024±0.006g/cm3 whereas PCA had a mean boiling point of 262±3°C, mean density of 1.505843±0.05503g/cm3, mean pH of 3.3±0.19 and a computed mean solubility of 1.5±0.017g/L. The study has shown that FCV tobacco leaf wastes is a green environmental substrate for organic synthesis of pyridine-3-carboxylic acid.},
     year = {2019}
    }
    

    Copy | Download

  • TY  - JOUR
    T1  - Frugal Utilization of Flue-Cured Virginia Nicotiana tabacum Leaf Wastes as a Vicissitudinous Substrate for Optimized Synthesis of Pyridine-3-Carboxylic Acid
    AU  - Timothy Omara
    AU  - Bashir Musau
    AU  - Sarah Kagoya
    Y1  - 2019/01/25
    PY  - 2019
    N1  - https://doi.org/10.11648/j.ajhc.20180404.11
    DO  - 10.11648/j.ajhc.20180404.11
    T2  - American Journal of Heterocyclic Chemistry
    JF  - American Journal of Heterocyclic Chemistry
    JO  - American Journal of Heterocyclic Chemistry
    SP  - 49
    EP  - 54
    PB  - Science Publishing Group
    SN  - 2575-5722
    UR  - https://doi.org/10.11648/j.ajhc.20180404.11
    AB  - Agrotransformation of tobacco leaves into cigarettes and cigars spawns upto 75% wastes which is an environmental and public nuisance owing to its noxious 0.6-3% (w/w) 3-(1-methyl-2-pyrrolindyl) pyridine (MPP) content. Considerately, this volumetric agrowaste is a prodigal loss during tobacco processing. Consequently, the utilization of these frugal wastes as a substrate for pyridine-3-carboxylic acid (PCA) synthesis is a green strategy to obliterate the ecological backlashes of tobacco waste. This concerted study reported the feasibility of utilizing Flue-Cured Virginia (FCV) tobacco waste as a starting substrate for synthesis of pyridine-3-carboxylic acid through MPP as a synthetic intermediate. The intermediate was extracted from powdered FCV wastes using petroleum ether and subsequently oxidized to PCA using 69% concentrated Nitric acid of volumes: 120, 115, 110,105, 100, 95, 90 and 85ml at 87±2°C. The results of the bench scale experiments indicated that the yield of PCA increases with increase in the volume of hot nitric acid; a maximum yield of 25ml was obtained with 100ml of hot nitric acid. The lowest yield of 17ml was from 85ml of hot nitric acid. MPP had a statistical mean boiling point of 249.3±2.082°C, mean density of 1.024±0.006g/cm3 whereas PCA had a mean boiling point of 262±3°C, mean density of 1.505843±0.05503g/cm3, mean pH of 3.3±0.19 and a computed mean solubility of 1.5±0.017g/L. The study has shown that FCV tobacco leaf wastes is a green environmental substrate for organic synthesis of pyridine-3-carboxylic acid.
    VL  - 4
    IS  - 4
    ER  - 

    Copy | Download

Author Information
  • Department of Health Sciences, Unicaf University, Lusaka, Zambia; Department of Quality Control, Quality Assurance and Product Development, AgroWays Uganda Limited, Jinja, Uganda; Department of Chemistry, Faculty of Science, Kyambogo University, Kampala, Uganda; Department of Quality Control and Quality Assurance, Leading Distillers Uganda Limited, Kampala, Uganda

  • Department of Chemistry, Faculty of Science, Kyambogo University, Kampala, Uganda; Department of Quality Control and Quality Assurance, Leading Distillers Uganda Limited, Kampala, Uganda

  • Department of Chemistry, Faculty of Science, Kyambogo University, Kampala, Uganda

  • Section