Synthesis of Picramide Using Nitration and Ammonolysis in Continuous Flow

Mittal, Ankit; Prakash, Gaurav; Pathak, Pramod

doi:10.1002/asia.202201028

Chemistry An Asian Journal

2022

DOI: 10.1002/asia.202201028

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Synthesis of Picramide Using Nitration and Ammonolysis in Continuous Flow

Ankit Mittal

Gaurav Prakash

Pramod Pathak

Abstract: This paper describes a safer, scalable and continuous process for synthesis of picramide. The process consists of two steps: step-1. nitration of p-nitroanisole (PNAN) to 2,4,6-trinitrianisole (TNAN); step-2. ammonolysis of TNAN to picramide. Both the steps were optimized in flow, with yield of 90% and 98% in step-1 and step-2 respectively. Picramide with HPLC purity greater than 99% was obtained. When compared with batch, in step-1, flow process provided significant advantage in selectivity and yield. The opt… Show more

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2023

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Cited by 2 publications

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“…This is important to allow effective air and liquid contact to provide required oxygen in the reaction of alkene with TBN. Overall, continuous flow synthesis (CFS) provides benefit in three areas mainly, reducing the plant footprint, increasing the selectivity and improving the process safety. − …”

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confidence: 99%

Continuous Flow Synthesis of tert-Butyl Nitrite and Its Applications as Nitrating Agent

Mittal,

Prakash,

Pathak

et al. 2023

Org. Process Res. Dev.

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Herein we report a flow chemistry method for the synthesis of tert-butyl nitrite. The flow process provided 95% yield in a very short residence time of 1 min corresponding to a space time yield of 13 g/h/mL. In addition, we used tert-butyl nitrite for metal-free stereoselective nitration of alkenes. The reported process had a higher batch cycle time of 12 to 24 h, limiting its application for commercial production. We developed a continuous-flow nitration process using a fixed bed column reactor. In the process, we provided the continuous air purging to ensure adequate supply of oxygen in the reaction. This has helped us to reduce the reaction time from 12 h in batch to 3 min in flow. The optimized nitration process conditions were applied on a series of styrene and acrylate derivatives. The methodology has potential for industrial-scale production of tert-butyl nitrite and its use as a nitrating agent.

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confidence: 99%

Continuous Flow Synthesis of tert-Butyl Nitrite and Its Applications as Nitrating Agent

Mittal,

Prakash,

Pathak

et al. 2023

Org. Process Res. Dev.

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Highly Scalable and Inherently Safer Preparation of Di, Tri and Tetra Nitrate Esters Using Continuous Flow Chemistry

Mittal,

Pathak,

Prakash

et al. 2023

Chemistry A European J

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Nitrate esters are important organic compounds having wide application in energetic materials, medicines and fuel additives. They are synthesized through nitration of aliphatic polyols. But the process safety challenges associated with nitration reaction makes the production process complicated and economically unviable. Herein, we have developed a continuous flow process wherein polyol and nitric acid are reacted in a microreactor to produce nitrate ester continuously. Our developed process is inherently safe and efficient. The process was optimized for industrially important nitrate esters containing two, three and four nitro groups. Molecules include glycol dinitrates: 1,2‐propylene glycol dinitrate (PGDN), ethylene glycol dinitrate (EGDN), diethylene glycol dinitrate (DEGDN), triethylene glycol dinitrate (TEGDN); trinitrates: trimethylolethane trinitrate (TMETN), 1,2,4‐butanetriol trinitrate (BTTN); tetranitrates: erythritol tetranitrate (ETN). The optimized process for each molecule provided yield > 90% in a short residence time of 1 min corresponding to a space time yield of > 18 g/h/mL of reactor volume.

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Synthesis of Picramide Using Nitration and Ammonolysis in Continuous Flow

Cited by 2 publications

References 20 publications

Continuous Flow Synthesis of tert-Butyl Nitrite and Its Applications as Nitrating Agent

Continuous Flow Synthesis of tert-Butyl Nitrite and Its Applications as Nitrating Agent

Highly Scalable and Inherently Safer Preparation of Di, Tri and Tetra Nitrate Esters Using Continuous Flow Chemistry

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