Properties and Preparation of 2,2-Dinitropropanol

2-dinitropropanol (DNPOH), also known as gem-nitropropanol, is an important 

2-Nitro-l-propanol is a highly explosive colorless liquid with an aromatic odor, melting point of -21.4 °C, boiling point of 103 °C, refractive index of 1.465420. It is soluble in ether, but insoluble in water. It has five hydrogen bond acceptors, topological molecular polar surface area of 112, heavy atom number of 10, rotatable bond number of one, the number of hydrogen bond donor of 1, and the number of covalent bond units of one. 

Early DNPOH synthesis methods include nitrification oxidization method, chlorination nitration method and electrochemical method. In 1961, Kaplan et al. [37] proposed a reaction with a redox process to synthesize gem-dinitro compounds, in which nitro ethane, as the raw materials, reacts with formaldehyde in the presence of sodium hydroxide, followed by the synthesis of DNPOH through the nitration reaction of silver nitrate and sodium nitrate. The reaction mechanism is  

In the company Aerojet, based on the TerMeer method [37], DNPOH was synthesized from as the starting material nitroethane in dichloroethane (EDC), through the chlorification with sodium chloride, substitution of chlorine atom with nitro, and finally reaction with formaldehyde under the action of sulfuric acid. The reaction mechanism is  

Wright et al. used silver as a medium to electrolyze and oxidize salts of polynitro compounds to prepare gem-polynitroaUcanes [64]. The reaction mechanism is  

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