Pentaerythrityltetramine

Abstract

Treating pentaerythrityl tetrachloride with excess hot, highly compressed ammonia yields the tetramine C(CH2NH2)4 in 57% yield at 52% conversion; unconverted starting material is easily recovered for recycling. The ammonolysis may be conducted either in supercritical ammonia alone or in methanol as the solvent. The product amine is isolated by precipitating it as the water-insoluble disulfate; simply washing the precipitate with water yields disulfate of high purity.

Pentaerythrityltetramine Scaffolds for Solid-Phase Combinatorial Chemistry1

“…The first large-scale synthesis of pentaerythrityltetramine [tetrakis(aminomethyl)methane, TAM] was based on displacement of the bromo substituents from pentaerythrityl tetrabromide with p -toluenesulfonamide ion and subsequent hydrolysis of the sulfonamide groups with sulfuric acid . The more recent syntheses include treatment of pentaerythrityl tetrachloride with excess of supercritical ammonia and reduction of the explosive tetra azide analogue. − The conversion of commercially available 2,2-bis(bromomethyl)propane-1,3-diol ( 14 ) to 2,2-bis(azidomethyl)propane-1,3-diol and further to 2,2-bis(hydroxymethyl)propane-1,3-diamine ( 15 ), described by Bitha et al, , appeared, however, a more appropriate method to obtain the desired branching units 1 and 2 . The amino groups of 15 were Boc-protected ( 16 ) and the hydroxy groups mesylated ( 17 ).…”

ReaxFF reactive molecular dynamics on silicon pentaerythritol tetranitrate crystal validates the mechanism for the colossal sensitivity

“…The explosive properties of pentaerythritol tetranitrate (PETN, C-(CH 2 -O-NO 2 ) 4 ) have been studied thoroughly both experimentally [1][2][3][4][5][6][7][8][9] and theoretically. [10][11][12][13][14][15][16] It has good detonation velocity and pressure, slightly below those of RDX (cyclotrimethylene trinitramine) but well above TNT (trinitrotoluene), 17 making it extensively used in blasting cap fillings, detonation cords, demolition devices, industrial explosives, etc.…”

The Sila-Explosives Si(CH2N3)4 and Si(CH2ONO2)4: Silicon Analogues of the Common Explosives Pentaerythrityl Tetraazide, C(CH2N3)4, and Pentaerythritol Tetranitrate, C(CH2ONO2)4

“…The neopentane derivatives pentaerythrityl tetraazide, C(CH 2 N 3 ) 4 ( 1a ), , and pentaerythritol tetranitrate (Nitropenta, PETN), C(CH 2 ONO 2 ) 4 ( 2a ), are well-known compounds for many years, compound 2a in particular, and have been studied for their explosive properties. − Great interest in studying the properties of 2a is demonstrated by the very recent literature. − Furthermore, the crystal structure of 1a has also been reinvestigated very recently . The precursors for these energetic materials, pentaerythrityl tetrachloride/bromide, C(CH 2 X) 4 (X = Cl, Br), and pentaerythritol, C(CH 2 OH) 4 , are easily available and produced in bulk.…”