Chemical Properties
white crystalline powder
Definition
ChEBI: A pentaerythritol nitrate in which all four hydroxy groups of pentaerythritol have been converted to the corresponding nitrate ester. It is a vasodilator with properties similar to those of glyceryl trinitrate, but with a more prolonged duration of action,
and is used for treatment of angina pectoris. It is also one of the most powerful high explosives known and is a component of the plastic explosive known as Semtex.
Uses
Mainly in the manufacture of detonating fuse (Primacord), a waterproof textile filled with powdered PETN.
Reactivity Profile
Pure PENTAERYTHRITE TETRANITRATE is an explosive. Severe explosion hazard when shocked or exposed to heat. Explodes when heated to 205-215°C. Highly dangerous when mixed with oxidizing agents. On decomposition Pentaerythritol tetranitrate emits highly toxic fumes of NOx (Sax and Lewis, 1987 pp. 699-700).
Health Hazard
Some are toxic and may be fatal if inhaled, swallowed or absorbed through skin. Contact may cause burns to skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may cause pollution.
Potential Exposure
First introduced following WWII,
PETN shares the same chemical family as nitroglycerine.
It is 70% more powerful than TNT. Used in the manufacture
of fuses for detonation and explosive specialties, including
the plastic explosive, Semtex, and in blasting caps. PETN
is also used as a medical vasodilator to lower blood pressure
by widening blood vessels to improve blood flow. PRTN
has been used in terrorism attempts in 2001 by the so-called
“shoe bomber,” in 2009 by the “underwear bomber,” and
most recently in October 2010, hidden in printer cartridges
being shipped internationally by passenger jet.
First aid
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, including
resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medical
attention. Give large quantities of water and induce
vomiting. Do not make an unconscious person vomit.
Shipping
UN3344 Pentaerythrite tetranitrate mixture,
desensitized, solid, n.o.s. with ＞10% but not ＞20%
PETN, by mass, Hazard Class: 4.1; Labels: 4.1-Flammable
solid. UN0150 Pentaerythrite tetranitrate, wetted or
Pentaerythritol tetranitrate, wetted, or PETN, wetted or
Pentaerythrite tetranitrate, or Pentaerythritol tetranitrate
or PETN, desensitized, Hazard Class: 1D; Labels:1DExplosive
(with a mass explosion hazard); D-Substances
or articles which may mass detonate (with blast and/or
fragment hazard) when exposed to fire.
Incompatibilities
Treat PETN as an unstable explosive.
Rapid heating can cause detonation when heated to 210C.
PETN is a dangerous high explosive and a strong oxidizer.
PETN normally requires a blasting cap or other kind of
detonator but may decompose explosively from concussion,
shock, friction, static charges. Keep away from combustible
materials; other oxidizers, for example, nitrates and
permanganates. Contact with sulfur trioxide may cause
detonation. Contact with reducing agents, e.g., zinc and
alkaline metals may cause explosion. May explode in
the presence of strong bases (i.e., sodium or potassium
hydroxide). May react with heavy metals.
Waste Disposal
Seek expert help with this
explosive material. Consult with environmental regulatory
agencies for guidance on acceptable disposal practices.
governing storage, transportation, treatment, and waste
disposal.
Originator
Pentanitrine, Promedica ,France,1948
Manufacturing Process
Cooling water was turned on and 420 parts nitric acid of 94% strength was introduced into the nitrator. The amount of acid was such that the ratio of nitric acid to pentaerythritol was 4.29. The agitator was started and the agitator speed adjusted to 120 rpm. 92 parts pentaerythritol, which had been screened previously through a 14-mesh screen was used in each charge. About 45 parts pentaerythritol was added to the nitrator at such a rate that the temperature in the nitrator gradually rose to 110°F. This required about 12 minutes. Time was allowed for the temperature rise to cease before each succeeding increment of material was added.
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 welldispersed 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.
Brand name
Pentritol Tempules
(Rhone-Poulenc Rorer); Peritrate (Parke-Davis).
Therapeutic Function
Coronary vasodilator
Fire Hazard
PETN is a high explosive, as powerful as cyclonite. It is more sensitive than TNT to shock. It explodes on percussion or heating. The detonating temperature is 210°C (410°F). The detonation velocity is 7.9 km/s.
Synthesis
Pentaerythritol tetranitrate, 2,2-bis(hydroxymethyl)-1,3-
propandioltetranitrate (19.1.2), is also synthesized by a nitration reaction of pentaerythritol with nitric acid, but using 2,2-bis(hydroxymethyl)-1,3-propandiol instead of glycerol as the starting material.
Purification Methods
Crystallise pentaerythritol tetranitrate from acetone or acetone/EtOH. When crystallised from H2O at 0o, it may have m 26-28o (hydrate). It detonates more easily than TNT on percussion. The O-acetate, when crystallised from EtOH, has m 87-88o. Although it has been distilled at 60o/2mm, distillation should NOT be attempted as it is VERY EXPLOSIVE. Itis a vasodilator. [Marans et al. J Am Chem Soc 76 1304 1954, Camp et al. J Am Chem Soc 77 751 1955, Beilstein 1 IV 2816, 2 IV 264.]
