Pentaerythritol, tetranitrate

Pentaerythritol tetranitrate [C(CH2N03)4 pentaerythritol (PE) with nitric acid (d = 

Chemical Name 2,2-bis[(nitroxy)methyl]-1,3-propanediol dinitrate 

Trade Name Manufacturer Country Year Intrc 

After reaching 110°F the charge was maintained at about said temperature from 12 to 14 minutes during which time approximately 30 parts pentaerythritol was added to the nitrator. During the following 14 minutes, approximately, the remainder of the 92 parts pentaerythritol was added in like manner to the charge and the temperature gradually reduced. 

The pentaerythritol was introduced into the acid in finely divided and well-dispersed particles and not in large unitary quantities. The entire 92 parts of pentaerythritol tetranitrate was introduced in 35 to 40 minutes. The pentaerythritol thus obtained was separated from the spent acid by filtering or drowning in water. To recover the spent acid the charge was passed onto a nutsch and filtered. The crude product was washed with water, then with a weak water-soluble alkali solution, such as sodium carbonate for example, and subsequently with water in order to remove the acid. 

After the removal of acid, the nitrate was dried by suction on the nutsch for about 15 minutes. The dried material was refined by means of acetone treatment or other suitable refining means. About 210 parts refined pentaerythritol tetranitrate per charge was obtained. 

Chemical Abstracts Registry No. 78-11 -5 Trade Name Manufacturer 

Molecular formula C5H8N4O12 Molecular weight 316.14 CAS Registry No 78-11 -5 Merck Index 13, 7186 

Sample preparation Vigorously shake 5 mL plasma with 8 mL ethyl acetate for 1 min, sonicate for 5 min, centrifuge at 3000 rpm for 3 min, repeat extraction with 8 mL ethyl acetate, repeat extraction with 6 mL ethyl acetate. Pass the extracts through a C18 SPE cartridge, filter (0.5 M-m) the eluate. Evaporate the eluate to 200 xL under a stream of nitrogen at 35°, inject a 25 m-L aliquot. 

Detector TEA (Thermal Energy Analyzer nitrosyl specific). Thermo Electron Corporation Model 502, pyrolyzer 500°, carrier gas nitrogen at 5 mL/min, reaction chamber 0.6 torr, cryogenic trap -78° 

Measurement of plasma concentrations of vasodilators and metabolites by the TEA Analyzer, Biopharm.Drug Dispos., 1983, 4, 311-319. 

---

The commercially important explosive pentaerythritol tetranitrate [78-11-5] (PETN), C HgN40 2>... 

Exothermic oxidation—reduction reactions provide the energy released in both propellant burning and explosive detonation. The reactions are either internal oxidation—reductions, as in the decomposition of nitroglycerin and pentaerythritol tetranitrate, or reactions between discrete oxidizers and fuels in heterogeneous mixtures. 

Pentaeiythritol Tetranitrate. Specification-grade pentaerythritol tetranitrate (PETN) can be stored up to 18 months at 65°C without significant deterioration. However, many materials have been found to be incompatible with PETN and the presence of as Htfle as 0.01% occluded acid or alkah greatly accelerates decomposition. The decomposition of PETN is autocatalytic with reported kinetic constants oi E = 196.6 kJ/mol (47 kcal/mol) and Z = 6.31 x 10 . The decomposition products of PETN at 210°C in wt % are 47.7 NO, 21.0 CO, 11.8 NO2, 9.5 N2O, 6.3 CO2, 2.0 H2, and 1.6... 

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. 

Pentaerythritol tetranitrate is a high energy explosive that is used as a pressed base charge in blasting caps and detonators, as the core explosive in commercial detonating cord, and as the main explosive ingredient in sheet explosives. It is also mixed in various proportions with TNT to form the less sensitive pentoHtes, eg, PETN 50/TNT 50. PETN is easily initiated, its responses are reproducible, and it is readily available (144—146). 

D. M. Coleman and R. N. Rogers, "Pentaerythritol Tetranitrate (PETN) StabiHty and CompatibiHty," in Proceedings of Conference on Compatibility of... 

Polyols. Several important polyhydric alcohols or polyols are made from formaldehyde. The principal ones include pentaerythritol, made from acetaldehyde and formaldehyde trimethylolpropane, made from -butyraldehyde and formaldehyde and neopentyl glycol, made from isobutyraldehyde and formaldehyde. These polyols find use in the alkyd resin (qv) and synthetic lubricants markets. Pentaerythritol [115-77-5] is also used to produce rosin/tall oil esters and explosives (pentaerythritol tetranitrate). Trimethylolpropane [77-99-6] is also used in urethane coatings, polyurethane foams, and multiftmctional monomers. Neopentyl glycol [126-30-7] finds use in plastics produced from unsaturated polyester resins and in coatings based on saturated polyesters. 

Pentaerythritol. Pentaerythritol tetranitrate, the tetranitrate derivative of 2,2-bis(hydroxymeth5l)-l-3-propanediol [115-77-5] is... 

Pentaerythritol Tetranitrate (PETN listed as 1,3-Propanediol, 2,2-[bis-(nitroxy)methyl] -dinitrate in CA since 1972, Penta Penthrite in Fr Pentrit, Niperyth, Nitropenta (NP) in Ger TEN in Russ). C(CH20N02)4, mw 316.15,... 

---