Pentaerythritol trinitrate esters

Pentaerythritol trinitrate esters of nitrobenzoic acid have been also obtained by Marans, Elrick and Preckel [52] who have esterified pentaerythritol trinitrate by means of the corresponding nitrobenzoyl chloride. 

Marans and co-workers used pentaerythritol trinitrate (81) to synthesize a number of aryl and alkyl esters, including the formate, propionate (84), oxalate, succinate, benzoate (85), 3,5-dinitrobenzoate (86), and ortho-, meta-, and para- (87) nitrobenzoate esters. The para-nitrobenzoate ester (87) has also been prepared from the nitration of pentaerythritol monobenzoate with mixed acid. ... 

Marans and Preckel " synthesized both the mononitrate (95) and the dinitrate (92) esters of metriol by using a similar strategy to that used for pentaerythritol trinitrate. Thus, nitration of both the mono- (90) and the di- (93) acetate esters of metriol, followed by selective hydrolysis of the acetate groups, yields (92) and (95) respectively the latter could be useful as a monomer for the synthesis of energetic polyurethane polymers. 

Wyler [54] suggested to producing mixed esters of nitric acid and of an organic acid also containing a hydroxylic group which would also be esterified by the nitric acid (a similar ester (V) was described above). This method has been applied by Wyler to obtain (nitrate-lactoyl)-pentaerythritol trinitrate, i.e. (a-nitroxypropionyl-pentaerythritol trinitrate) ... 

Pentaerythritol trinitrate can be used for preparing a range of mixed pentaery-thritol esters. 

Succinic Acid-Bis- [3-Nitryloxy-2,2-Bis-Nitryloxy-methyl-Propyl Ester]. Ci4H2oN6022 mw 624.40 N 37.46% OB to CO2 —4i.0% mp 88— 90°. Prepn is by wanning succinyl chloride with 0,0, 0 -Pentaerythritol Trinitrate in py. Its expl properties were not investigated (Ref 1, <1920>)... 

Pentaerythritol trinitrate with the code of ITMETN, also called 1,1,1-trimethylol ethane trinitrate, trimethylol methane trinitrate, dimethylol-2-propanol-l-trinitrate, methyl isobutanetriol trinitrate, methyl isobutyl glycerine trinitrate, or methyl tert-butanetriol trinitrate, is a very important nitrate ester. 

Pentaerythritol diglycollic ester tetranitrate (m.p. below room, temperature) Pentaerythritol monomethyl ether trinitrate (m.p. 79-80 C)... 

A variety of solvents, monomers, medicines, perfumes, and explosives are made from esters of nitric acid. Ethyl acetate, //-butyl acetate, iso-butyl acetate, glycerol trinitrate, pentaerythritol tetranitrate (PETN), glycol dinitrate, and cellulose nitrate are examples of such reactions. 

An interesting method of hydrolysis of nitrate esters to alcohols was given by Pews 1158). It consists in refluxing nitrate esters with formic acid followed by refluxing with methanol. Pemaerythritol trinitrate yielded pentaerythritol. 

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