78-11-5 Usage
Uses
Used in Military and Defense Industry:
Pentaerythritol tetranitrate is used as a high explosive for [its high energy density and rapid decomposition rate] in the manufacture of artillery ammunition, boosters, and detonation fuses. It is commonly used as a primacord, which is a waterproof textile filled with powdered PETN.
Used in Pharmaceutical Industry:
Pentaerythritol tetranitrate is used as a medication for [its ability to prevent angina pectoris attacks and ease their course] in the treatment of chronic cardiac insufficiency.
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.
Therapeutic Function
Coronary vasodilator
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.
Health Hazard
Skin contact can cause dermatitis. There is no report of any major adverse effects in humans. However, drawing a parallelism with other nitroorganics of similar structures, PETN is expected to cause poisoning with symptoms of headache, nausea, abdominal pain, and dyspnea.
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.
Safety Profile
Human systemic effects by ingestion: dermatitis. Effects are sirmlar to those of nitroglycerin, i.e., headache, weakness, and fall in blood pressure. Very low oral toxicity. Severe explosion hazard when shocked or exposed to heat. It explodes at 215’C. On decomposition it emits hghly toxic fumes of NO,; can react vigorously with oxidizing materials. Used in detonators and explosive specialities. See also NITRATES and EXPLOSIVES, HIGH.
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.
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.
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.
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.]
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.
Check Digit Verification of cas no
The CAS Registry Mumber 78-11-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 8 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 78-11:
(4*7)+(3*8)+(2*1)+(1*1)=55
55 % 10 = 5
So 78-11-5 is a valid CAS Registry Number.
InChI:InChI=1/C5H8N4O12/c10-6(11)18-1-5(2-19-7(12)13,3-20-8(14)15)4-21-9(16)17/h1-4H2
78-11-5Relevant academic research and scientific papers
Application of [PVI-SO3H]NO3as a novel polymeric nitrating agent with ionic tags in preparation of high-energetic materials
Sepehrmansourie, Hassan,Zarei, Mahmoud,Zolfigol, Mohammad Ali,Mehrzad, Amin,Hafizi-Atabak, Hamid Reza
, p. 8367 - 8374 (2021/03/03)
In this paper, poly(vinyl imidazole) sulfonic acid nitrate [PVI-SO3H]NO3was synthesized and fully characterized. Then, [PVI-SO3H]NO3was applied for the preparation of energetic materials such as 1,1-diamino-2,2-dinitroethene (FOX-7), pentaerythritol tetranitrate (PETN), 1,3,5-trinitro-1,3,5-triazinane (RDX) and trinitrotoluene (TNT). The major advantages of the presented methodology are mild, facile workup, high yields and short reaction times. [PVI-SO3H]NO3is a suitable nitrating agent forin situgeneration of NO2and without using any co-catalysts of the described nitrating reagent.
VASODILATOR-ENHANCED CARDIOPULMONARY RESUSCITATION
-
, (2012/08/27)
A method for increasing blood flow to vital organs during cardiopulmonary resuscitation of a person experiencing a cardiac arrest may include performing standard or active compression decompression cardiopulmonary resuscitation on a person to create artificial circulation by repetitively compressing the person's chest such that the person's chest is subject to a compression phase and a relaxation or decompression phase. The method may also include administering one or more vasodilator drugs to the person to improve the artificial circulation created by the cardiopulmonary resuscitation. The method may also include binding at least a portion of the person's abdomen, either manually or with an abdominal compression device. Performing cardiopulmonary resuscitation on a person may include ventilating the person with either an impedance threshold device or a intrathoracic pressure regulator.
Synthesis of nitric acid esters from alcohols in a dinitrogen pentoxide/carbon dioxide liquid system
Kuchurov, Ilya V.,Fomenkov, Igor V.,Zlotin, Sergei G.,Tartakovsky, Vladimir A.
experimental part, p. 67 - 69 (2012/07/02)
Organic nitric acid esters have been prepared in 89-98% yield by the nitration of the corresponding alcohols and polyols with N2O5 in liquid CO2.
METHODS OF PRODUCING NITRATE ESTERS
-
Page/Page column 4, (2012/06/01)
Methods of forming a nitrate ester include combining at least one nitrate salt and sulfuric acid to form a nitrating solution and adding an aliphatic polyol to the nitrating solution. Nitrate esters formed by this method may be, for example, triethylene glycol dinitrate (TEGDN), pentaerythritol tetranitrate (PETN), diglycerol tetranitrate (DGTN), 1,1,1-tris(methylol)ethane trinitrate (TMETN), 1,2,4-butanetriol trinitrate (BTTN), nitroglycerin (NG), diethylene glycol dinitrate (DEGDN), ethylene glycol dinitrate (EGDN), metriol trinitrate (MTN), nitrocellulose (NC), or 1,2-propanediol dinitrate (PDDN).
NO donors. Part 18: Bioactive metabolites of GTN and PETN-Synthesis and vasorelaxant properties
Lange, Kathrin,Koenig, Andreas,Roegler, Carolin,Seeling, Andreas,Lehmann, Jochen
experimental part, p. 3141 - 3144 (2010/01/17)
The vasodilators glyceryl trinitrate (GTN) and pentaerythrityl tetranitrate (PETN) are supposed to be degraded in vivo to the lower nitrates PETriN, PEDN, PEMN, 1,2-GDN, 1,3-GDN, 1-GMN, and 2-GMN. We synthesized these bioactive metabolites as reference compounds for pharmacokinetic studies. The use of HPLC-methods for monitoring the stepwise reduction of PETN to lower nitrates and the syntheses of the glyceryl dinitrates proved advantageous. Furthermore, we measured the vasorelaxant properties of all metabolites by performing organ bath experiments with porcine pulmonary arteries. In general, the vasodilator potency increases with the number of nitrate moieties in the compound.
Synthesis of haptens and their protein conjugates for immunological determination of nitrate esters and nitramines
Blackburn, G. Michael,Beadham, Ian G.,Adams, Harry,Hutchinson, Alistair P.,Nicklin, Stephen
, p. 225 - 230 (2007/10/03)
Isosteric, isopolar analogues of the nitrate ester pentaerythritol tetranitrate (PETN) and of the cyclic nitramine sym-cyclotrimethylene trinitramine (RDX) having a spacer arm have been linked to carrier proteins to provide immunologically active peptide conjugates. X-Ray structures of RDX, RDX analogue 10, and hapten 14 are compared to establish their conformational relationships. The Royal Society of Chemistry 2000.
Nitration of alcohols by nitryl fluoride
Fedorov,Eremenko
, p. 1022 - 1023 (2007/10/03)
A general method for the preparation of nitrates by treatment of alcohols with nitryl fluoride (FNO2) in MeCN in the presence of KF has been developed.
Derivatives of Pentaerythritol, I. - Formaldehyde Bis(pentaerythrityl) Acetal and Tetrapentaerythritol
Werle, Peter,Nonnenmacher, Gerhard,Kruse, Karsten
, p. 938 - 945 (2007/10/02)
Pure formaldehyde bis(pentaerythrityl) acetal (9) and tetrapentaerythritol (4) were isolated for the first time as by-products during the synthesis of pentaerythritol from acetaldehyde and formaldehyde.The spectra show that 4 is not a branched molecule as suggested but a straight-chained one.
Pharmaceutical composition and process of treatment
-
, (2008/06/13)
A process for alleviating proliferative skin diseases such as psoriasis, atopic dermatitis, etc. comprising administering to humans, or domesticated animals, topically and/or systemically a composition comprising a pharmaceutical carrier and at least one active compound selected from the groups, substituted alkyl zanthines, tricyclic antidepressants, organic nitrates, antihypertensives, anti-asthma agents and central nervous system depressants and combinations of certain compounds from specifically named groups of compounds.
