Pentaerythritol trinitrate

Initially, attempts to introduce fewer nitro groups into a molecule of pentaerythritol by means of direct nitration were unsuccessful. When less concentrated nitric acid was used the only result was a decreased yield of PETN contaminated by small quantity of pentaerythritol trinitrate. 

For a long time the only practicable method was the nitration of an organic acid pentaerythritol ester followed by removal of the acyl. 

In this way Marans, Elrick and Preckel [52] have obtained pentaerythritol monoacetate together with certain amounts of di- and triacetate by heating pentaerythritol tetra-acetate with pentaerythritol at 180-185°C. The monoacetate was nitrated to yield pentaerythritol acetate trinitrate (XII). Careful hydrolysis of the latter produced pentaerythritol trinitrate (XIII)  

POLYHYDRO XYLIC BRANCHED-CHAIN ALCOHOL BSTBRS 195 

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

Eiowever, it has been discovered that pentaerythritol trinitrate can also be produced by direct nitration of pentaerythritol with a mixed acid composed of 80% nitric acid and 80% sulphuric acid (Camp, Marans, Elrick and Preckel [56]). The nitration is performed at a temperature close to 0°C. The product, representing a mixture of PETN with trinitrate, is precipitated by adding water. To separate the components the acetone solution neutralized by means of ammonium carbonate is treated with aqueous alcohol so as to form a mixture of 7 parts of acetone. 3 parts 

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Pentaerythritol may be nitrated by a batch process at 15.25°C using concentrated nitric acid in a stainless steel vessel equipped with an agitator and cooling coils to keep the reaction temperature at 15—25°C. The PETN is precipitated in a jacketed diluter by adding sufficient water to the solution to reduce the acid concentration to about 30%. The crystals are vacuum filtered and washed with water followed by washes with water containing a small amount of sodium carbonate and then cold water. The water-wet PETN is dissolved in acetone containing a small amount of sodium carbonate at 50°C and reprecipitated with water the yield is about 95%. Impurities include pentaerythritol trinitrate, dipentaerythritol hexanitrate, and tripentaerythritol acetonitrate. Pentaerythritol tetranitrate is shipped wet in water—alcohol in packing similar to that used for primary explosives. 

Infrared Spectrophotometric Method for Determination of Acetone Content of Pentaerythritol trinitrate , NOTS 1877, NAVORD 5649 (1958) 5a) A.R. Lawrence AJ. Matuszko, JPhysChem 65,1903 (1961) CA 56, 5483 (1962)... 

Determination of Acetone In Pentaerythritol-trinitrate By Gas Chromatography , NAVORD 7014, AD 231855 (I960) 110) J. Carol,... 

Petrin. See as Pentaerythritol Trinitrate under Pentaerythritol and its Derivatives in this Vol... 

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. 

Italian Detonators of WWII contd as a primary charge a mixt of LSt (Lead Styphnate), LA (Lead Azide) and, as a secondary (base) charge, PETN (Pentaerythritol Trinitrate)... 

Crude PE cannot be used for manuf of expls suitable for military purposes, such as PETN (Pentaerythritol Tetranitrate), C(CH2ON02)41or PETrN (Pentaerythritol Trinitrate), called Petrin,... 

Note In our opinion, abbr PETN should be used for Pentaerythritol Trinitrate, while for Pentaerythritol Tetranitrate it is more correct to use PETeN... 

Petrin pentaerythritol trinitrate PIC Parr Instrument Company, Moline... 

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. 

Wagner [53] prepared pentaerythritol dinitrate diacetate and pentaerythritol trinitrate monoaoetate and examined their explosive properties. 

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) ... 

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