Nitration and flow chemistry

Research Article
Open access

Nitration and flow chemistry

Jingyi Lu 1* , Chennan He 2
  • 1 Beijing International Bilingual Academy    
  • 2 Baylor university    
  • *corresponding author jingy.lu@outlook.com
Published on 21 July 2023 | https://doi.org/10.54254/2755-2721/7/20230333
ACE Vol.7
ISSN (Print): 2755-273X
ISSN (Online): 2755-2721
ISBN (Print): 978-1-915371-61-4
ISBN (Online): 978-1-915371-62-1

Abstract

The paper introduced the principle of nitration reaction and flow chemistry, beginning with background information and the reaction mechanism of nitration. Then the correlation between nitration and flow chemistry is further explored by comparing the nitration reaction in conventional batch mode and under continuous flow. As the dangerous corrosive acids and strong exotherms make the reaction especially difficult to increase production scale, flow chemistry is utilized and proved to be a better alternative to the conventional production method to perform nitration. Using flow chemistry to scale up the exothermic and hazardous nitration reactions offer advantages including better yield, higher production rate, enhanced safety, etc.

Keywords:

nitration, flow chemistry, organic chemistry

Lu,J.;He,C. (2023). Nitration and flow chemistry. Applied and Computational Engineering,7,390-399.
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References

[1]. Clayden, Jonathan, et al. Organic Chemistry. Oxford; New York, Oxford University Press, 2012.

[2]. Smith, Keith, et al. “A Novel Method for the Nitration of Deactivated Aromatic Compounds.” Journal of the Chemical Society, no. 16, 19 July 2000, pp. 2753–2758, 10.1039/B002158J.

[3]. Hoggett, J. G., et al. Nitration and Aromatic Reactivity. Cambridge University Press, 1971.

[4]. Marsh, Neville, and Alexander Marsh. “A Short History of Nitroglycerine and Nitric Oxide in Pharmacology and Physiology.” Clinical and Experimental Pharmacology and Physiology, vol. 27, no. 4, 2000, pp. 313–319, 10.1046/j.1440-1681.2000.03240.x.

[5]. Thompson, Mike, and Charlie Thompson. “Glycerol - Molecule of the Month - January 2018 (HTML Version).” Figshare, 2017, doi.org/10.6084/m9.figshare.5567872.v1.

[6]. Kyprianou, Dimitris, et al. “Synthesis of 2,4,6-Trinitrotoluene (TNT) Using Flow Chemistry.” Molecules, vol. 25, no. 16, 6 Aug. 2020, 10.3390/molecules25163586. Accessed 8 Feb. 2021.

[7]. Jensen, Klavs. “Flow Chemistry-Microreaction Technology Comes of Age.” AIChE Journal, vol. 63, no. 3, 2017, pp. 858–869, 10.1002/aic.15642.

[8]. Brocklehurst, Cara E., et al. “Nitration Chemistry in Continuous Flow Using Fuming Nitric Acid in a Commercially Available Flow Reactor.” Organic Process Research & Development, vol. 15, no. 6, 2011, pp. 1447–1453, 10.1021/op200055r.

[9]. Zolfigol, Mohammad Ali, et al. “Nitration of Aromatic Compounds on Silica Sulfuric Acid.” Bulletin of the Korean Chemical Society, vol. 25, no. 9, 2004, pp. 1414–1416.

[10]. Brown, Catrin, and Mike Ford. Higher Level Chemistry. 2nd ed., Harlow, Essex, Pearson Education, 2014.

[11]. Loudon, Marc, and Jim Parise. Organic Chemistry. Ben Roberts, 2016.

[12]. “Research status and technological progress of nitration process.” n.p. 01 Apr 2022 https://www.sohu.com/a/534518295_121117454

[13]. Amol A. Kulkarni. ”Continuous flow nitration in miniaturized devices.” Beilstein J. Org. Chem. 2014, 10, 405–424. https://doi.org/10.3762/bjoc.10.38

[14]. “What Is a Micro Channel Reactor & Details || KOBE STEEL, LTD.” Kobelco, www.kobelco.co.jp/english/products/ecmachinery/smcr/overview.html.‌

[15]. Wen, Zhenghui, et al. “Process Development and Scale-up of the Continuous Flow Nitration of Trifluoromethoxybenzene.” Organic Process Research & Development, vol. 21, no. 11, Nov. 2017, pp. 1843–50, https://doi.org/10.1021/acs.oprd.7b00291.

[16]. Zhao, Junhong & Wang, Yan & Ding, Guifu & Sun, Cecilia & Wang, Guilian. (2014). Design, fabrication and measurement of a microchannel heat sink with a pin-fin array and optimal inlet position for alleviating the hot spot effect. Journal of Micromechanics and Microengineering. 24. 10.1088/0960-1317/24/11/115013.

[17]. Mándity, István M et al. “Strategic Application of Residence-Time Control in Continuous-Flow Reactors.” ChemistryOpen vol. 4,3 (2015): 212-23. doi:10.1002/open.201500018

[18]. Corning Reactor Technologies, Inc. “Review l Progress in the application of continuous nitration of aromatic compounds” n.d. https://www.yiqi.com/zt2721/article_24786.html


Cite this article

Lu,J.;He,C. (2023). Nitration and flow chemistry. Applied and Computational Engineering,7,390-399.

Data availability

The datasets used and/or analyzed during the current study will be available from the authors upon reasonable request.

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About volume

Volume title: Proceedings of the 3rd International Conference on Materials Chemistry and Environmental Engineering (CONF-MCEE 2023), Part II

ISBN:978-1-915371-61-4(Print) / 978-1-915371-62-1(Online)
Editor:Ioannis Spanopoulos, Niaz Ahmed, Sajjad Seifi Mofarah
Conference website: https://www.confmcee.org/
Conference date: 18 March 2023
Series: Applied and Computational Engineering
Volume number: Vol.7
ISSN:2755-2721(Print) / 2755-273X(Online)

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References

[1]. Clayden, Jonathan, et al. Organic Chemistry. Oxford; New York, Oxford University Press, 2012.

[2]. Smith, Keith, et al. “A Novel Method for the Nitration of Deactivated Aromatic Compounds.” Journal of the Chemical Society, no. 16, 19 July 2000, pp. 2753–2758, 10.1039/B002158J.

[3]. Hoggett, J. G., et al. Nitration and Aromatic Reactivity. Cambridge University Press, 1971.

[4]. Marsh, Neville, and Alexander Marsh. “A Short History of Nitroglycerine and Nitric Oxide in Pharmacology and Physiology.” Clinical and Experimental Pharmacology and Physiology, vol. 27, no. 4, 2000, pp. 313–319, 10.1046/j.1440-1681.2000.03240.x.

[5]. Thompson, Mike, and Charlie Thompson. “Glycerol - Molecule of the Month - January 2018 (HTML Version).” Figshare, 2017, doi.org/10.6084/m9.figshare.5567872.v1.

[6]. Kyprianou, Dimitris, et al. “Synthesis of 2,4,6-Trinitrotoluene (TNT) Using Flow Chemistry.” Molecules, vol. 25, no. 16, 6 Aug. 2020, 10.3390/molecules25163586. Accessed 8 Feb. 2021.

[7]. Jensen, Klavs. “Flow Chemistry-Microreaction Technology Comes of Age.” AIChE Journal, vol. 63, no. 3, 2017, pp. 858–869, 10.1002/aic.15642.

[8]. Brocklehurst, Cara E., et al. “Nitration Chemistry in Continuous Flow Using Fuming Nitric Acid in a Commercially Available Flow Reactor.” Organic Process Research & Development, vol. 15, no. 6, 2011, pp. 1447–1453, 10.1021/op200055r.

[9]. Zolfigol, Mohammad Ali, et al. “Nitration of Aromatic Compounds on Silica Sulfuric Acid.” Bulletin of the Korean Chemical Society, vol. 25, no. 9, 2004, pp. 1414–1416.

[10]. Brown, Catrin, and Mike Ford. Higher Level Chemistry. 2nd ed., Harlow, Essex, Pearson Education, 2014.

[11]. Loudon, Marc, and Jim Parise. Organic Chemistry. Ben Roberts, 2016.

[12]. “Research status and technological progress of nitration process.” n.p. 01 Apr 2022 https://www.sohu.com/a/534518295_121117454

[13]. Amol A. Kulkarni. ”Continuous flow nitration in miniaturized devices.” Beilstein J. Org. Chem. 2014, 10, 405–424. https://doi.org/10.3762/bjoc.10.38

[14]. “What Is a Micro Channel Reactor & Details || KOBE STEEL, LTD.” Kobelco, www.kobelco.co.jp/english/products/ecmachinery/smcr/overview.html.‌

[15]. Wen, Zhenghui, et al. “Process Development and Scale-up of the Continuous Flow Nitration of Trifluoromethoxybenzene.” Organic Process Research & Development, vol. 21, no. 11, Nov. 2017, pp. 1843–50, https://doi.org/10.1021/acs.oprd.7b00291.

[16]. Zhao, Junhong & Wang, Yan & Ding, Guifu & Sun, Cecilia & Wang, Guilian. (2014). Design, fabrication and measurement of a microchannel heat sink with a pin-fin array and optimal inlet position for alleviating the hot spot effect. Journal of Micromechanics and Microengineering. 24. 10.1088/0960-1317/24/11/115013.

[17]. Mándity, István M et al. “Strategic Application of Residence-Time Control in Continuous-Flow Reactors.” ChemistryOpen vol. 4,3 (2015): 212-23. doi:10.1002/open.201500018

[18]. Corning Reactor Technologies, Inc. “Review l Progress in the application of continuous nitration of aromatic compounds” n.d. https://www.yiqi.com/zt2721/article_24786.html