Hubbry Logo
Pentaerythritol tetranitratePentaerythritol tetranitrateMain
Open search
Pentaerythritol tetranitrate
Community hub
Pentaerythritol tetranitrate
logo
8 pages, 0 posts
0 subscribers
Be the first to start a discussion here.
Be the first to start a discussion here.
Pentaerythritol tetranitrate
Pentaerythritol tetranitrate
Pentaerythritol tetranitrate
View on Wikipedia
from Wikipedia

Pentaerythritol tetranitrate
Skeletal formula
Ball-and-stick model
Pentaerythritol tetranitrate after crystalization from acetone
Names
Preferred IUPAC name
2,2-Bis[(nitrooxy)methyl]propane-1,3-diyl dinitrate
Other names
[3-Nitrooxy-2,2-bis(nitrooxymethyl)propyl] nitrate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.987 Edit this at Wikidata
UNII
  • InChI=1S/C5H8N4O12/c10-6(11)18-1-5(2-19-7(12)13,3-20-8(14)15)4-21-9(16)17/h1-4H2 checkY
    Key: TZRXHJWUDPFEEY-UHFFFAOYSA-N checkY
  • InChI=1S/C5H8N4O12/c10-6(11)18-1-5(2-19-7(12)13,3-20-8(14)15)4-21-9(16)17/h1-4H2
  • C(C(CO[N+](=O)[O-])(CO[N+](=O)[O-])CO[N+](=O)[O-])O[N+](=O)[O-]
Properties
C5H8N4O12
Molar mass 316.137 g/mol
Appearance White crystalline solid[1]
Density 1.77 g/cm3 at 20 °C
Melting point 141.3 °C (286.3 °F; 414.4 K)
Boiling point 180 °C (356 °F; 453 K) (decomposes above 150 °C (302 °F))
Explosive data
Shock sensitivity Medium
Friction sensitivity Medium
Detonation velocity 8400 m/s (density 1.7 g/cm3)
RE factor 1.66
Hazards
GHS labelling:
GHS06: Toxic GHS01: Explosive GHS08: Health hazard
Danger
H201, H241, H302, H316, H370, H373
P210, P250, P261, P264, P301+P312, P370+P380, P372, P401, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxideSpecial hazards (white): no code
2
1
3
190 °C (374 °F; 463 K)
Pharmacology
C01DA05 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Pentaerythritol tetranitrate (PETN), also known as PENT, pentyl, PENTA (ПЕНТА, primarily in Russian), TEN (tetraeritrit nitrate), corpent, or penthrite (or, rarely and primarily in German, as nitropenta), is an explosive material. It is the nitrate ester of pentaerythritol, and is structurally very similar to nitroglycerin. Penta refers to the five carbon atoms of the neopentane skeleton. PETN is a very powerful explosive material with a relative effectiveness factor of 1.66.[2] When mixed with a plasticizer, PETN forms a plastic explosive.[3] Along with RDX it is the main ingredient of Semtex.

PETN is also used as a vasodilator drug to treat certain heart conditions, such as for management of angina.[4][5]

History

[edit]

Pentaerythritol tetranitrate was first prepared and patented in 1894 by the explosives manufacturer Rheinisch-Westfälische Sprengstoff A.G. [de] of Cologne, Germany.[6][7][8][9] The production of PETN started in 1912, when the improved method of production was patented by the German government. PETN was used by the German Military in World War I.[10][11] It was also used in the MG FF/M autocannons and many other weapon systems of the Luftwaffe in World War II.[citation needed]

Properties

[edit]

PETN is practically insoluble in water (0.01 g/100 mL at 50 °C), weakly soluble in common nonpolar solvents such as aliphatic hydrocarbons (like gasoline) or tetrachloromethane, but soluble in some other organic solvents, particularly in acetone (about 15 g/100 g of the solution at 20 °C, 55 g/100 g at 60 °C) and dimethylformamide (40 g/100 g of the solution at 40 °C, 70 g/100 g at 70 °C). It is a non-planar molecule that crystallizes in the space group P421c.[12] PETN forms eutectic mixtures with some liquid or molten aromatic nitro compounds, e.g. trinitrotoluene (TNT) or tetryl. Due to the steric hindrance of the adjacent neopentyl-like moiety, PETN is resistant to attack by many chemical reagents; it does not hydrolyze in water at room temperature or in weaker alkaline aqueous solutions. Water at 100 °C or above causes hydrolysis to dinitrate; the presence of 0.1% nitric acid accelerates the reaction.

The chemical stability of PETN is of interest, because of the presence of PETN in aging weapons.[13] Neutron radiation degrades PETN, producing carbon dioxide and some pentaerythritol dinitrate and trinitrate. Gamma radiation increases the thermal decomposition sensitivity of PETN, lowers melting point by few degrees Celsius, and causes swelling of the samples. Like other nitrate esters, the primary degradation mechanism is the loss of nitrogen dioxide; this reaction is autocatalytic.[citation needed] Studies were performed on thermal decomposition of PETN.[14]

In the environment, PETN undergoes biodegradation. Some bacteria denitrate PETN to trinitrate and then dinitrate, which is then further degraded.[15] PETN has low volatility and low solubility in water, and therefore has low bioavailability for most organisms. Its toxicity is relatively low, and its transdermal absorption also seems to be low. It poses a threat for aquatic organisms. It can be degraded to pentaerythritol by iron.[16]

Production

[edit]

Production is by the reaction of pentaerythritol with concentrated nitric acid to form a precipitate which can be recrystallized from acetone to give processable crystals.[17]

Variations of a method first published in US Patent 2,370,437 by Acken and Vyverberg (1945 to Du Pont) form the basis of all current commercial production.[citation needed]

PETN is manufactured by numerous manufacturers as a powder, or together with nitrocellulose and plasticizer as thin plasticized sheets (e.g. Primasheet 1000, Detasheet and Durasheet 1). PETN residues are easily detectable in hair of people handling it.[18] The highest residue retention is on black hair; some residues remain even after washing.[19][20]

Explosive use

[edit]
Pentaerythritol tetranitrate before crystallization from acetone

The most common use of PETN is as an explosive with high brisance. It is a secondary explosive, meaning it is more difficult to detonate than primary explosives, so dropping or igniting it will typically not cause an explosion (at standard atmospheric pressure it is difficult to ignite and burns vigorously), but is more sensitive to shock and friction than other secondary explosives such as TNT or tetryl.[17][21] Under certain conditions a deflagration to detonation transition can occur, just like that of ammonium nitrate.

It is rarely used alone in military operations due to its lower stability, but is primarily used in the main charges of plastic explosives (such as C4) along with other explosives (especially RDX), booster and bursting charges of small caliber ammunition, in upper charges of detonators in some land mines and shells, as the explosive core of detonation cord.[22][23] PETN is the least stable of the common military explosives, but can be stored without significant deterioration for longer than nitroglycerin or nitrocellulose.[24]

During World War II, PETN was most importantly used in exploding-bridgewire detonators for the atomic bombs. These exploding-bridgewire detonators gave more precise detonation compared to primacord. PETN was used for these detonators because it was safer than primary explosives like lead azide: while it was sensitive, it would not detonate below a threshold amount of energy.[25] Exploding bridgewires containing PETN remain in use in current nuclear weapons. In spark detonators, PETN is used to avoid the need for primary explosives; the energy needed for a successful direct initiation of PETN by an electric spark ranges between 10–60 mJ.

Its basic explosion characteristics are:

  • Explosion energy: 5810 kJ/kg (1390 kcal/kg), so 1 kg of PETN has the energy of 1.24 kg TNT.
  • Detonation velocity: 8350 m/s (1.73 g/cm3), 7910 m/s (1.62 g/cm3), 7420 m/s (1.5 g/cm3), 8500 m/s (pressed in a steel tube)
  • Volume of gases produced: 790 dm3/kg (other value: 768 dm3/kg)
  • Explosion temperature: 4230 °C
  • Oxygen balance: −6.31 atom -g/kg
  • Melting point: 141.3 °C (pure), 140–141 °C (technical)
  • Trauzl lead block test: 523 cm3 (other values: 500 cm3 when sealed with sand, or 560 cm3 when sealed with water)
  • Critical diameter (minimal diameter of a rod that can sustain detonation propagation): 0.9 mm for PETN at 1 g/cm3, smaller for higher densities (other value: 1.5 mm)

In mixtures

[edit]

PETN is used in a number of compositions. It is a major ingredient of the Semtex plastic explosive. It is also used as a component of pentolite, a castable mixture with TNT (usually 50/50 but may contain more TNT), which is, along with pure PETN, a common explosive for boosters for the blasting work (as in mining).[26][27] The XTX8003 extrudable explosive, used in the W68 and W76 nuclear warheads, is a mixture of 80% PETN and 20% of Sylgard 182, a silicone rubber.[28] It is often phlegmatized by addition of 5–40% of wax, or by polymers (producing polymer-bonded explosives); in this form it is used in some cannon shells up to 30 mm caliber, though it is unsuitable for higher calibers. It is also used as a component of some gun propellants and solid rocket propellants. Nonphlegmatized PETN is stored and handled with approximately 10% water content. PETN alone cannot be cast as it explosively decomposes slightly above its melting point,[citation needed][clarification needed] but it can be mixed with other explosives to form castable mixtures.

PETN can be initiated by a laser.[29] A pulse with duration of 25 nanoseconds and 0.5–4.2 joules of energy from a Q-switched ruby laser can initiate detonation of a PETN surface coated with a 100 nm thick aluminium layer in less than half of a microsecond.[citation needed]

PETN has been replaced in many applications by RDX, which is thermally more stable and has a longer shelf life.[30] PETN can be used in some ram accelerator types.[31] Replacement of the central carbon atom with silicon produces Si-PETN, which is extremely sensitive.[32][33]

Terrorist and military use

[edit]
Main articles: Shoe Bomber, 2009 Christmas Day bomb plot, and 2010 cargo plane bomb plot

Ten kilograms of PETN was used in the 1980 Paris synagogue bombing.

In 1983, 307 people were killed after a truck bomb filled with PETN was detonated at the Beirut barracks.

In 1983, the "Maison de France" house in Berlin was brought to a near-total collapse by the detonation of 24 kilograms (53 lb) of PETN by terrorist Johannes Weinrich.[34]

In 1999, Alfred Heinz Reumayr used PETN as the main charge for his fourteen improvised explosive devices that he constructed in a thwarted attempt to damage the Trans-Alaska Pipeline System.

In 2001, al-Qaeda member Richard Reid, the "Shoe Bomber", used PETN in the sole of his shoe in his unsuccessful attempt to blow up American Airlines Flight 63 from Paris to Miami.[20][35] He had intended to use the solid triacetone triperoxide (TATP) as a detonator.[21]

In 2009, PETN was used in an attempt by al-Qaeda in the Arabian Peninsula to assassinate the Saudi Arabian Deputy Minister of Interior Prince Muhammad bin Nayef, by Saudi suicide bomber Abdullah al-Asiri. The target survived and the bomber died in the blast. The PETN was hidden in the bomber's rectum, which security experts described as a novel technique.[36][37][38]

On 25 December 2009, PETN was found in the underwear of Umar Farouk Abdulmutallab, the "Underwear bomber", a Nigerian with links to al-Qaeda in the Arabian Peninsula.[39] According to US law enforcement officials,[40] he had attempted to blow up Northwest Airlines Flight 253 while approaching Detroit from Amsterdam.[41] Abdulmutallab had tried, unsuccessfully, to detonate approximately 80 grams (2.8 oz) of PETN sewn into his underwear by adding liquid from a syringe;[42] however, only a small fire resulted.[21]

In the al-Qaeda in the Arabian Peninsula October 2010 cargo plane bomb plot, two PETN-filled printer cartridges were found at East Midlands Airport and in Dubai on flights bound for the US on an intelligence tip. Both packages contained sophisticated bombs concealed in computer printer cartridges filled with PETN.[43][44] The bomb found in England contained 400 grams (14 oz) of PETN, and the one found in Dubai contained 300 grams (11 oz) of PETN.[44] Hans Michels, professor of safety engineering at University College London, told a newspaper that 6 grams (0.21 oz) of PETN—"around 50 times less than was used—would be enough to blast a hole in a metal plate twice the thickness of an aircraft's skin".[45] In contrast, according to an experiment conducted by a BBC documentary team designed to simulate Abdulmutallab's Christmas Day bombing, using a Boeing 747 plane, even 80 grams of PETN was not sufficient to materially damage the fuselage.[46]

On 12 July 2017, 150 grams of PETN was found in the Assembly of Uttar Pradesh,[47][48] India's most populous state.[49][50]

PETN was used by Israel in the manufacturing of pagers provided to Hezbollah. On September 17, 2024, the pagers detonated, killing 12 people and injuring thousands.[51]

Detection

[edit]

In the wake of terrorist PETN bomb plots, an article in Scientific American noted PETN is difficult to detect because it does not readily vaporize into the surrounding air.[43] The Los Angeles Times noted in November 2010 that PETN's low vapor pressure makes it difficult for bomb-sniffing dogs to detect.[20]

Many technologies can be used to detect PETN, including chemical sensors, X-rays, infrared, microwaves[52] and terahertz,[53] some of which have been implemented in public screening applications, primarily for air travel. PETN is one of the explosive chemicals typically of interest in that area, and it belongs to a family of common nitrate-based explosive chemicals which can often be detected by the same tests.

One detection system in use at airports involves analysis of swab samples obtained from passengers and their baggage. Whole-body imaging scanners that use radio-frequency electromagnetic waves, low-intensity X-rays, or T-rays of terahertz frequency that can detect objects hidden under clothing are not widely used because of cost, concerns about the resulting traveler delays, and privacy concerns.[54]

Both parcels in the 2010 cargo plane bomb plot were x-rayed without the bombs being spotted.[55] Qatar Airways said the PETN bomb "could not be detected by x-ray screening or trained sniffer dogs".[56] The Bundeskriminalamt received copies of the Dubai x-rays, and an investigator said German staff would not have identified the bomb either.[55][57] New airport security procedures followed in the U.S., largely to protect against PETN.[20]

Medical use

[edit]

Like nitroglycerin (glyceryl trinitrate) and other nitrates, PETN is also used medically as a vasodilator in the treatment of heart conditions.[4][5] These drugs work by releasing the signaling gas nitric oxide in the body. The heart medicine Lentonitrat is nearly pure PETN.[58]

Monitoring of oral usage of the drug by patients has been performed by determination of plasma levels of several of its hydrolysis products, pentaerythritol dinitrate, pentaerythritol mononitrate and pentaerythritol, in plasma using gas chromatography-mass spectrometry.[59]

See also

[edit]

References

[edit]

Further reading

[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

Pentaerythritol tetranitrate

View on Grokipedia
from Grokipedia

Pentaerythritol tetranitrate (PETN) is a powerful organic with the molecular formula C₅H₈N₄O₁₂, formed by the esterification of with . It appears as a , crystalline solid with a of 141.3 °C and exhibits high sensitivity to shock and friction, classifying it as a secondary high suitable for initiation by primary explosives. First synthesized in 1891 through the nitration of by Bernhard Tollens, PETN demonstrates exceptional due to its of approximately 8,300–8,400 m/s at a of 1.77 g/cm³. These properties enable its use as a booster charge in detonators and blasting caps, where it reliably propagates in less sensitive high explosives. PETN's relative stability at ambient conditions, combined with its energy output, has made it a staple in ordnance, commercial , and applications. While prized for its performance in controlled settings, PETN's concealability and potency have rendered it a material of choice in improvised explosive devices, underscoring the dual-edged of such energetic materials in both legitimate and illicit contexts. Its decomposition primarily yields , , and , consistent with the rapid oxidation characteristic of explosives.

History

Discovery and synthesis

Pentaerythritol tetranitrate (PETN), with the chemical formula C(CH₂ONO₂)₄, was first synthesized in by German chemist Bernhard Tollens and his student P. Wigand through the of , a neopentane-based tetraol (C(CH₂OH)₄) they had prepared from and in an aldol-type condensation followed by reduction. This marked the initial laboratory-scale production of PETN as a , with Tollens' work published in Liebig's Annalen der Chemie (volume 265, page 318). The synthesis relied on the fundamental principle of nitrate ester formation, wherein the primary hydroxyl groups of react with under strongly acidic conditions to yield the tetranitrated product via esterification: C(CH₂OH)₄ + 4 HNO₃ → C(CH₂ONO₂)₄ + 4 H₂O. This process involves of the , enhancing its electrophilicity, followed by by the alcohol oxygens, with elimination; complete tetranitration requires excess nitrating agent and controlled temperature to avoid partial substitution or . Early verification of PETN's structure and purity involved reduction back to , confirming the quantitative addition of four nitrooxy groups, while its explosive nature was empirically demonstrated through ignition and tests in Tollens' laboratory, revealing rapid energy release characteristic of high-order explosives.

Commercial and military adoption

Following its initial military application by German forces during , pentaerythritol tetranitrate (PETN) transitioned to broader commercial use in the , driven by postwar industrial expansion in and that demanded explosives with higher than trinitrotoluene (TNT). PETN's of approximately 8,300 m/s enabled more efficient fragmentation in blasting operations compared to TNT's 6,900 m/s, facilitating adoption in boosters and initiating charges where precise propagation was critical. A pivotal advancement occurred in 1936 when the Ensign-Bickford Company introduced Primacord, a featuring a PETN core encased in textiles and waterproofing layers, based on earlier French patents; this product revolutionized synchronized blasting in quarries and tunnels by allowing rapid, reliable detonation over distances up to thousands of meters at velocities around 6,400 m/s. Interwar booms, particularly in and metal extraction, amplified demand for such systems, as PETN's sensitivity to —lower than primary explosives but sufficient for secondary roles—reduced misfires in complex underground arrays. In military contexts, PETN's adoption expanded during for use in autocannons like the MG FF/M and as a booster in various munitions, leveraging its stability under compression and high performance in confined charges. Postwar, its integration into plastic explosives such as —developed by the Czech firm Synthesia in 1964, combining PETN with for moldable demolition applications—further entrenched its role in both commercial blasting and tasks. By the mid-20th century, PETN constituted a standard component in detonators and primers across ordnance, prized for enabling compact, high-velocity initiation without excessive sensitivity risks during handling.

Chemical and physical properties

Molecular structure and composition

Pentaerythritol tetranitrate (PETN), with the molecular formula C₅H₈N₄O₁₂, features a neopentane-derived core where a central carbon atom is bonded to four methylene (-CH₂-) groups, each esterified with a group (-ONO₂). This symmetric tetrahedral arrangement, represented as C(CH₂ONO₂)₄, positions the nitrate esters at equivalent distances from the core, influencing its packing in the crystalline lattice. The compound has a of 316.14 g/mol. As a white crystalline solid at , PETN exhibits a of 1.77 g/cm³ and a of 141 °C. It shows low in (approximately 0.0043 mg/100 mL at 20 °C) but dissolves readily in organic solvents such as acetone.

Explosive and thermal properties

Pentaerythritol tetranitrate (PETN) exhibits a relative effectiveness factor of approximately 1.66 relative to trinitrotoluene (TNT) in standard tests, reflecting its superior energy release and blast performance. Its reaches about 8,300 m/s at a of 1.76 g/cm³, enabling a high-pressure that propagates supersonically through the material. This velocity underpins PETN's , or shattering power, quantified at 131% of TNT in sand-crush tests, making it effective for initiating secondary via rapid compression and localized heating that triggers rapid decomposition. The detonation process follows Chapman-Jouguet theory, where a leading shock front compresses and heats the explosive, igniting exothermic reactions that produce high-temperature gases (primarily CO₂, H₂O, N₂, and NOₓ), sustaining the wave's equilibrium pressure and velocity without external support. PETN's heat of is approximately 6,230 kJ/kg, corresponding to the liberated during complete to gaseous products under conditions. Despite this potency, it demonstrates relative stability under ambient conditions, with no spontaneous , though it is sensitive to mechanical : impact sensitivity yields at drop heights of 15 cm (using a 2 kg weight) and sensitivity requires forces around 36 N for reaction. These sensitivities arise from localized hot spots formed by adiabatic shear or void collapse under shock, lowering the for bond rupture. Thermally, PETN melts at 141 °C before decomposition onset at roughly 160 °C, where it releases (NO₂) and other oxides alongside carbon oxides and . Full thermal stability holds to 210–225 °C for short exposures (5–10 seconds), beyond which rapid gas evolution risks runaway reaction, though it withstands standard storage without ignition.

Synthesis and production

Raw materials and precursors

Pentaerythritol (C(CH₂OH)₄, or C₅H₁₂O₄) constitutes the key organic precursor for pentaerythritol tetranitrate (PETN) production, serving as the polyol backbone that undergoes esterification with nitrate groups. It is manufactured industrially via a base-catalyzed process involving acetaldehyde (CH₃CHO) and excess formaldehyde (HCHO), where acetaldehyde undergoes aldol condensation with formaldehyde to form an intermediate aldol, followed by a Cannizzaro disproportionation to yield the tetrol structure. This reaction typically employs aqueous sodium hydroxide as the catalyst, with molar ratios favoring three equivalents of formaldehyde per acetaldehyde to maximize pentaerythritol yield over neopentyl glycol byproducts. Formaldehyde, the primary reactant, is sourced from the of (CH₃OH) over silver or iron-molybdenum catalysts at elevated temperatures, yielding aqueous formalin solutions that are concentrated for use. production historically relied on oxidation or hydration, but modern routes favor the using (C₂H₄) and oxygen with palladium-copper catalysts, enhancing scalability and cost-efficiency for large-scale synthesis. For the nitration step enabling PETN formation, concentrated (HNO₃, typically 90-100% purity) acts as the nitrating agent, often mixed with (H₂SO₄) to facilitate and generate the nitronium ion (NO₂⁺) catalyst. concentrations around 90-98% are common in mixed-acid processes, with ratios adjusted to control reaction temperature and minimize side products like trinitrates. Post-World War II advancements emphasized high-purity fuming routes without to simplify recovery and reduce in industrial setups, reflecting shifts toward efficient synthetic acid production from oxidation for . Sourcing these acids involves established and industries, though precursor controls on and derivatives have emerged due to dual-use potential in explosives.

Nitration process

The nitration of to form pentaerythritol tetranitrate (PETN) involves the esterification of its four hydroxyl groups with , typically using concentrated (97-100% HNO₃) as the nitrating agent. is added gradually to the acid while maintaining a low initial temperature of 0-5°C to control the highly , which generates significant heat and requires continuous cooling, often via baths or jacketed reactors, to prevent or decomposition. The process favors pure over mixed acid (HNO₃/H₂SO₄) to minimize side reactions such as sulfonation, which can reduce yield and purity. The reaction proceeds under stirring for 1-2 hours, with the temperature controlled below 20°C to optimize tetra-nitration while limiting of nitrate esters back to the . Nitric oxides (NOₓ) are evolved as byproducts and must be captured or scrubbed to mitigate environmental and safety hazards. Theoretical yields approach 100% based on complete esterification, but practical yields range from 90-95% due to incomplete conversion, minor degradation, and losses from occluded acid.

Purification and scaling challenges

Following , the crude pentaerythritol tetranitrate (PETN) is separated from the spent mixed acid via or and subjected to with water to remove adhering acids, often followed by treatment with dilute alkaline solutions such as to neutralize residual acidity. This initial step eliminates free nitric and sulfuric acids, preventing degradation and ensuring stability, but leaves behind organic impurities including under-nitrated species like pentaerythritol trinitrate. For higher purity, recrystallization from acetone is employed: the washed product is dissolved in hot acetone, hot-filtered to exclude insoluble contaminants, and then cooled to induce , routinely achieving purities greater than 99%. This solvent-based purification exploits differences in , selectively precipitating PETN while solubilizing or excluding partially nitrated impurities and homologs, though it incurs yield losses typically of 5-10% due to co-precipitation or dissolution of product. (HPLC) analysis confirms the removal of these impurities, with methods detecting homologs at trace levels to meet quality standards. Scaling PETN production from laboratory to industrial levels introduces significant challenges, primarily in managing the intensely exothermic reaction within larger batch reactors, where inefficient can create hotspots leading to premature or runaway reactions. Early 20th-century processes relied on batch with vigorous stirring and cooling jackets, but transitions to semi-continuous or continuous flow systems—incorporating for acid separation—emerged to enhance , consistency, and throughput while mitigating control issues. Yield optimization at scale demands precise control of acid composition and , as deviations favor formation of trinitrate impurities, reducing overall efficiency and necessitating additional purification cycles. Quality assurance in scaled operations includes testing alongside HPLC to verify explosive performance, with velocities below 8,000 m/s indicating impurities or inconsistent that compromise reliability. These empirical metrics ensure purity correlates with detonation consistency, as even minor trinitrate depresses velocity and increases sensitivity variability.

Legitimate applications

Industrial and blasting uses

Pentaerythritol tetranitrate (PETN) serves as the primary in detonating cords for industrial blasting applications, including , quarrying, and controlled . These cords consist of a PETN core encased in a protective or sheath, with typical loadings ranging from 5 to 100 grams per meter to facilitate reliable initiation of secondary explosives such as emulsions, , or dynamites. The high of PETN, exceeding 6,900 meters per second, enables precise timing and sequential firing of charges, minimizing uneven fragmentation and overbreak in rock faces. In cast boosters, PETN is commonly formulated into pentolite—a 50/50 mixture with trinitrotoluene (TNT)—to amplify initiation energy for less-sensitive bulk explosives used in quarrying and . This composition offers superior and thermal stability over , which has a lower (around 6,000 meters per second) and greater sensitivity to handling impacts, thereby reducing misfire rates and enhancing operational safety in large-scale blasts. PETN-based boosters transmit shock waves more effectively, allowing for deeper penetration into boreholes and improved fragmentation efficiency, which optimizes material handling and reduces energy consumption in downstream crushing processes. The reliability of PETN in these systems has supported advancements in civilian blasting since the post-World War II era, enabling consistent performance in open-pit operations where precise control over blast patterns is critical for . By lowering initiation failures to below 1% in optimized setups, PETN contributes to cost savings through reduced downtime and explosive waste, though its use requires stringent storage protocols due to sensitivity to friction and impact.

Military and detonator applications

Pentaerythritol tetranitrate (PETN) serves as a key component in detonators, blasting caps, and fuzes, functioning as a booster to reliably propagate from primary initiators to secondary charges in ordnance assemblies. Its use in detonating cords, such as those containing PETN as the core , enables synchronized initiation across multiple charges in and munitions systems. This application leverages PETN's high and velocity of , typically exceeding 8,000 m/s under confinement, to ensure efficient transmission. In castable formulations like Pentolite—a 50:50 mixture of PETN and TNT—PETN enhances explosive performance as a bursting or booster charge, offering superior shattering power and readiness for initiation compared to TNT alone. Adopted by multiple nations during , including as a bursting charge in Japanese 7.7 mm projectiles, Pentolite provided strategic advantages in munitions requiring high-density, melt-cast fills for reliable performance in variable conditions. Superfine grades of PETN demonstrate advantages over primary explosives like lead azide in detonator applications, exhibiting lower impact sensitivity (Bureau of Mines drop height >15 cm versus 8 cm for lead azide) and reduced risk (0.27–9.76 J versus 0.004–0.006 J), which improves safety during handling and assembly while maintaining propagative efficiency when primed with minimal lead azide (less than 0.005 g). These properties sustain PETN's role in contemporary military fuzes and initiators, where aging studies confirm its long-term reliability in booster functions despite gradual changes affecting thresholds.

Medical and pharmaceutical uses

Pentaerythritol tetranitrate (PETN) functions as an organic in medical contexts, undergoing to release (NO), which activates in vascular cells, leading to increased (cGMP) levels and subsequent relaxation of vascular . This primarily affects venous capacitance vessels, reducing preload on the heart and myocardial oxygen demand, while also modestly decreasing to improve coronary blood flow in ischemic regions, thereby providing relief from pectoris symptoms. Unlike its potent explosive properties at gram-scale quantities, therapeutic applications exploit PETN's pharmacological effects at milligram doses, which are orders of magnitude below any detonation threshold and akin to other nitrates like , though PETN exhibits a longer plasma due to slower hepatic denitration. Historically, PETN was marketed under names like Peritrate for prophylaxis and treatment of angina pectoris, with oral formulations introduced in the mid-20th century and recognized by the U.S. (FDA) under pre-1962 safety standards as potentially effective for angina prevention, though not for acute treatment. Typical dosing in clinical studies involved –100 mg orally, often in sustained-release forms administered two to three times daily, with regimens titrated to balance efficacy and tolerance development. However, in , the FDA withdrew approval for relevant new drug applications, citing insufficient substantial evidence from adequate and well-controlled modern trials to demonstrate efficacy, despite earlier observational data. PETN remains unavailable in the U.S. but has been studied or used elsewhere for stable . Clinical evidence from mid-20th-century trials indicated reductions in attack frequency, with one study of 14 patients reporting fewer episodes after PETN administration compared to baseline. Later investigations, including a comparison of 30 mg versus 100 mg doses, demonstrated improved exercise tolerance and decreased anginal pain in stable patients, with higher doses showing superior outcomes without proportional increases in adverse events. PETN's hemodynamic effects, such as lowered preload and , were confirmed to enhance cardiac performance in select cohorts, potentially with reduced relative to , as evidenced by lower markers in treated patients. Nonetheless, these benefits must be weighed against common side effects including , , facial flushing, and , which arise from systemic and may diminish with continued use due to partial tolerance, though full with other nitrates is not universal.

Terrorist incidents and misuse

In 2001, British national attempted to detonate approximately 200 grams of PETN-based concealed in the soles of his shoes aboard Flight 63 from to on December 22; the device failed to fully initiate when Reid struggled to ignite the fuse with matches, leading to his subduing by passengers and crew with no explosion or casualties beyond minor injuries from the struggle. On December 25, 2009, , a Nigerian national trained by (AQAP), concealed about 80 grams of PETN sewn into his underwear on approaching ; he attempted chemical initiation using a , but the PETN only partially deflagrated into flames rather than detonating, injuring himself and causing for a few passengers but no fatalities. In October 2010, AQAP shipped two packages from containing 300-400 grams each of PETN hidden inside printer toner cartridges destined for via cargo flights; Saudi intelligence tipped off authorities, leading to interceptions in the UK and before detonation, with no casualties or blasts occurring. – wait, no wiki, but from [web:30] wiki but avoid, use NYT. PETN's appeal in these non-state attacks stems from its low , which hinders vapor-based detection methods, and its ability to be plasticized into flexible sheets resembling innocuous materials like or tape for easy concealment in , devices, or shipments. These incidents empirically demonstrated PETN's stability requiring precise high-velocity initiation—such as a booster charge—which failed in the 2001 and 2009 cases due to inadequate fuses or chemical triggers, limiting outcomes to non-detonative fires or prevention; while direct casualties remained low (zero deaths, isolated injuries), the plots imposed substantial security expenditures, including policy shifts toward enhanced passenger screening.

Factors enabling concealment

PETN's odorless nature and negligible vapor pressure—approximately 1.1 × 10⁻⁹ —render it undetectable by conventional canine or trace vapor sampling methods, as it produces no appreciable headspace vapors under ambient conditions. Its white, crystalline powder form lacks distinctive visual or olfactory signatures, allowing facile integration into bulk materials without alerting handlers. The compound's of 138–141°C enables at moderate temperatures without , permitting admixture with plasticizers, waxes, or oils to yield a flexible, moldable composite akin to , which can be shaped to conform to concealed voids in luggage, apparel, or . This plasticity, combined with a of 1.75–1.77 g/cm³, supports dense packing into compact volumes while maintaining structural integrity during transit. As a secondary high explosive, PETN exhibits relative insensitivity to , impact, and shock—lacking reliable without a primary booster or —thereby minimizing inadvertent detonation risks during handling or concealment efforts. Its high (around 8,300 m/s) and (relative effectiveness factor of 1.66 versus TNT) allow potent payloads in minimal quantities, ideal for embedding within everyday objects without excessive bulk. Pre-2010 and protocols, which emphasized volatile detection over comprehensive screening, exacerbated these properties' concealability; layered measures like advanced imaging and swab protocols proliferated only post-incident, addressing prior emphases on liquids and vapors.

Detection and countermeasures

Technological detection methods

Ion mobility spectrometry (IMS) is a primary trace detection method for PETN, capable of identifying vapor or particulate residues at parts-per-billion (ppb) levels through the separation of ionized molecules based on their drift time in an . Studies demonstrate detection limits as low as 9.8 × 10^{-15} g/cm³ for PETN using dopant-assisted , with dopant-enhanced negative improving peak separation and reducing false positives from interferents like common environmental ions. IMS devices, often integrated into airport swab-based systems, underwent enhancements post-2010 following PETN-related incidents, incorporating automated swabbing for non-metallic threats to achieve sub-nanogram sensitivity while minimizing operator variability. Raman spectroscopy and its surface-enhanced variant (SERS) enable non-contact identification of PETN traces by analyzing molecular vibrational signatures, with SERS substrates achieving detection of tens of picograms through signal amplification via plasmonic nanostructures. SERS platforms using metal nanogaps or sputtered substrates have shown specificity for PETN's nitrate ester bands, even in mixtures, though substrate reproducibility affects false positive rates in field conditions. These methods complement IMS by providing standoff capabilities, avoiding sample collection. Proton transfer reaction mass spectrometry (PTR-MS) facilitates real-time vapor detection of PETN by soft ionization and high-resolution mass analysis, targeting low-vapor-pressure explosives with sensitivities in the sub-ppb range for trace emissions. Developed for online monitoring, PTR-MS systems have been validated for PETN in controlled tests, though humidity and interferent VOCs can elevate false alarms without calibration. For bulk detection, dual-energy imaging distinguishes PETN based on effective (Z_eff) and , matching simulants to real material profiles around 1.77 g/cm³, though pose differentiation challenges. Explosives detection canines, trained via pseudoscents or inert simulants, reliably alert to PETN odors at nanogram thresholds, with programs like TSA's achieving high specificity across environmental variables. In forensic contexts, the Terrorist Explosive Device Analytical Center (TEDAC) integrates residue analysis for PETN post-detonation, employing gas chromatography-mass spectrometry to profile degradation products and trace handling residues, aiding attribution with chain-of-custody protocols.

Limitations and ongoing research

PETN's exceptionally low vapor pressure, on the order of 10^{-9} to 10^{-10} mmHg at ambient temperatures, severely limits the efficacy of vapor-phase detection methods such as (IMS) and canine olfaction, often resulting in detection thresholds that fail to identify trace quantities below 1 ng. This inherent property enables evasion in concealed configurations, where PETN is embedded within non-porous plastics or composite materials that minimize particle shedding and vapor emission, as evidenced in aviation security breaches involving printer cartridge concealment. Encapsulation strategies exacerbate false negatives in swab-based trace explosive detectors (ETDs), with environmental interferences and substrate effects contributing to inconsistent sensitivity for esters like PETN. U.S. Government Accountability Office assessments highlight systemic gaps in current technologies, noting that while layered screening reduces risks, adaptive threats—such as chemically masked or aged PETN—persist without a singular, reliable across bulk and trace modalities. Post-2020 research emphasizes AI-augmented to address these deficits, including near-infrared integrated with convolutional neural networks for standoff detection of low-volatility explosives, achieving classification accuracies exceeding 90% in controlled trials. Complementary efforts explore desorption coupled with IMS for enhanced trace recovery from varied substrates, aiming to bypass volatility constraints. Aging investigations reveal rapid evolution in PETN's volatile emission profiles and microstructure—such as increased surface area from particle fragmentation under accelerated conditions—prompting development of dynamic signature libraries and models to track degradation-induced detectability shifts. These multi-modal advancements, driven by persistent imperatives, underscore the absence of comprehensive solutions amid iterative evasion tactics.

Safety, hazards, and regulations

Handling and explosion risks

Pentaerythritol tetranitrate (PETN) is classified by the U.S. as an 1.1D material, indicating a high risk of mass upon , with potential for to nearby explosives. As a secondary high explosive, it requires a strong shock or for reliable but remains sensitive to mechanical impact, with a typical 50% probability of reaction (h50) in drop-weight tests occurring at energies of approximately 3-5 J, depending on size and purity. This sensitivity arises from adiabatic compression and hotspot formation under rapid loading, leading to localized and potential transition to if confinement or momentum is sufficient. (ESD) poses additional risks during manufacturing and handling of dry PETN, with thresholds around 0.1-1 J for powdered forms, though less severe than for primary explosives. During production, particularly in the stage, intermediate acidic PETN exhibits heightened and impact sensitivity compared to purified material, increasing the potential for unintended from equipment or impurities. Historical incidents underscore these hazards; for instance, in , a 1:1 mixture of powder and PETN ignited spontaneously during routine mixing operations at a U.S. facility, attributed to frictional heating and reactive metal interaction, resulting in a confined . processes carry inherent runaway reaction risks due to exothermic and potential accumulation of unstable intermediates, though specific PETN detonations are rare in documented records, often mitigated by controlled cooling and dilution. Safe storage requires dedicated high-explosive magazines maintaining cool, dry conditions (below 65°C for extended periods, with noted after at that temperature), segregation from oxidizers, fuels, and ignition sources, and often with at least 25% to desensitize during . strategies include grounding equipment and personnel to prevent ESD accumulation, enclosing operations with local exhaust ventilation, using antistatic and gloves, and employing remote or automated handling to minimize direct contact. Compared to primary explosives like , which detonate at ESD energies below 10 mJ and minimal impact, PETN's higher thresholds allow safer bulk handling when proper protocols are followed, though it demands rigorous adherence to avoid propagation in quantity.

Toxicological effects

Pentaerythritol tetranitrate (PETN) primarily exerts toxicological effects through mediated by release, leading to acute symptoms upon , dermal contact, or , including , , flushing, and . Severe exposure may induce dyspnea, , and convulsions, with rare instances of reported in humans at high doses due to reduction impairing oxygen transport. Animal studies confirm low , with no mortality observed in rats or mice at oral doses up to 1,310 mg/kg-day or 2,530 mg/kg-day, respectively, and an oral LD50 of 1.66 g/kg in rats. National Toxicology Program (NTP) gavage and feed studies in F344/N rats and B6C3F1 mice at doses up to 50,000 ppm showed no significant nonneoplastic effects attributable to PETN beyond minor body weight reductions in female rats, and no elevation in levels exceeding 1% in blood. Carcinogenicity was equivocal in rats, with marginal increases in Zymbal's gland neoplasms (e.g., 0/49 controls vs. 2/41 high-dose males), but absent in mice, supporting non-carcinogenic classification at therapeutic doses of 2-3 mg/kg-day used for prevention. Occupational handling of PETN, akin to other organic nitrates, initially provokes headaches and , but rapid tolerance develops within days of repeated low-level exposure, mitigating these effects; withdrawal after can trigger rebound headaches. In contexts, rapid systemic absorption from residues may heighten risks of convulsions or beyond chronic exposure patterns observed in pharmaceutical or industrial settings. Provisional EPA toxicity values derive subchronic and chronic oral reference doses at 2 × 10−3 mg/kg-day based on human headache LOAELs of 0.86 mg/kg-day, underscoring sensitivity to vasodilatory endpoints over oncogenic or hemolytic ones.

Environmental and regulatory aspects

Pentaerythritol tetranitrate (PETN) primarily degrades in environmental settings via in aqueous media, producing and ions, alongside by such as , which sequentially removes nitro groups to yield without initial release. Abiotic reduction by zero-valent iron in soils further accelerates breakdown under anaerobic conditions, bypassing pathways. Its low (16 mg/L at 20°C) and strong sorption to restrict leaching, though hydrolysis-derived nitrates pose a potential risk for contamination and if residues accumulate from or waste sites. Bioaccumulation of PETN in organisms remains low due to its limited and rapid transformation, with assessments indicating minimal in like earthworms. Controlled applications in and yield negligible ecological releases, but improper disposal of production waste or residues can elevate local levels, exacerbating issues in vulnerable aquifers. In the United States, PETN qualifies as a high explosive under Bureau of Alcohol, Tobacco, Firearms and Explosives (ATF) jurisdiction, mandating federal explosives licenses, storage magazines compliant with 27 CFR Part 555, and tracking to prevent diversion. The (ECHA) registers PETN under REACH (EC 204-488-7) as a hazardous substance with production/import volumes of 10–100 tonnes annually, requiring registration dossiers, safety data sheets, and exposure scenario assessments for handlers. Global export controls intensified after PETN's role in terrorist plots, including the 2009 underwear bomb attempt and 2010 Yemen cargo bombings, incorporating it into Chemical Facility Anti-Terrorism Standards appendices and munitions lists for end-user verification and licensing.

Stability and degradation

Aging mechanisms

The primary aging mechanism of pentaerythritol tetranitrate (PETN) involves homolytic scission of the O–NO₂ bonds within its nitrate ester groups, initiating by generating alkoxy radicals and (NO₂). This NO₂ release is autocatalytic, as the liberated gas accelerates further bond cleavage and radical propagation, leading to progressive molecular breakdown even at ambient temperatures. In the presence of residual acids from synthesis or moisture-induced , these reactions intensify, with water facilitating nitrate group loss and forming alcohols alongside , which catalyzes additional ester . Environmental factors such as elevated and markedly accelerate PETN degradation by enhancing reaction kinetics and ingress, respectively; for instance, exposure to 70–75 °C induces rapid changes in particle morphology within weeks. Under controlled conditions (e.g., dry, sealed storage at 25 °C), PETN exhibits a projected of approximately 40–50 years before significant , though prolonged exposure beyond 18 months at 65 °C reveals instability markers like gas evolution. Empirical studies, including those from 2020–2024, document aging-induced physical alterations such as increased , particle coarsening via , and density reductions of up to 5–10% in vapor-deposited films or powders over accelerated timelines equivalent to decades. These changes correlate with drops (e.g., 5–15% in aged fills) due to microstructural evolution, as observed in large-scale analyses of commercial PETN batches. Incorporation of stabilizers, such as derivatives or additives, mitigates these effects by scavenging NO₂ and inhibiting , preserving density and performance metrics in tests spanning 1.5 years of artificial aging.

Implications for long-term storage

Long-term storage of PETN requires consideration of its physical aging processes, primarily particle coarsening via mechanisms such as and sublimation-recrystallization, which reduce and can degrade initiation performance in s. Accelerated aging studies at elevated temperatures (e.g., 75°C) demonstrate that unstabilized PETN experiences substantial surface area loss, dropping from approximately 13,000 cm²/g to 5,800 cm²/g over 12 months, resulting in increased detonator function times (from 1.23 µs to 1.38 µs) and altered threshold initiation voltages. Stabilized formulations, such as those coated with TriPEON, exhibit minimal coarsening (surface area reduction to ~9,800 cm²/g under similar conditions) and maintain consistent performance metrics, underscoring the value of stabilizers in preserving reliability over decades. These changes necessitate periodic surveillance in and industrial s, where small-scale function tests serve as causal indicators for requalification, detecting shifts in sensitivity before bulk impacts become evident—though such velocity reductions are typically modest (e.g., <2% in PETN-based formulations after extended high-temperature exposure). Large-scale aging analyses, including batch-to-batch variability assessments over 1.5 years, inform management protocols by validating that stabilized PETN sustains prompt initiation without significant degradation, supporting its use in critical applications like nuclear s. remains negligible at ambient conditions, with extrapolated half-lives exceeding millions of years, but moisture control is essential to prevent accelerated physical alterations. Compared to less stable nitrate esters like , PETN's inherent robustness justifies its continued deployment despite the need for stabilization and monitoring, as evidenced by shelf-life projections of approximately 48 years at 25°C derived from vacuum stability testing—far surpassing alternatives prone to rapid chemical breakdown. Ongoing emphasizes empirical validation through function time measurements over extrapolated models, ensuring integrity without over-reliance on unverified assumptions.

References

  1. https://pubchem.ncbi.nlm.nih.gov/compound/Pentaerythritol-Tetranitrate
  2. https://psemc.com/resources/pyrotechnic-white-papers/properties-of-selected-high-explosives-rev/
  3. https://www.researchgate.net/publication/331552769_Pentaerythritol_Tetranitrate
  4. https://www.science.gov/topicpages/p/pentaerythritol%2Btetranitrate%2Bpetn
  5. https://pmc.ncbi.nlm.nih.gov/articles/PMC9928408/
  6. https://www.nap.edu/read/24862/chapter/4
  7. http://www.orgsyn.org/demo.aspx?prep=CV1P0425
  8. https://edoc.ub.uni-muenchen.de/19458/1/Schmid_Philipp.pdf
  9. https://www.hadmernok.hu/kulonszamok/newchallenges/kovacsz.html
  10. https://www.britannica.com/science/PETN
  11. https://www.britannica.com/technology/Primacord
  12. https://www.britannica.com/technology/explosive/Detonating-cord
  13. https://www.theguardian.com/world/2010/oct/30/petn-explosive-choice-semtex-terrorists
  14. https://www.lanl.gov/media/publications/national-security-science/1221-petn
  15. https://webbook.nist.gov/cgi/cbook.cgi?ID=C78115&Mask=200
  16. https://www.chemicalbook.com/ChemicalProductProperty_US_CB4292971.aspx
  17. https://www.indiatoday.in/information/story/petn-explosive-the-key-component-in-mossads-deadly-operations-2601746-2024-09-18
  18. https://pubs.acs.org/doi/10.1021/acsmaterialsau.2c00022
  19. https://onlinelibrary.wiley.com/doi/10.1002/prep.202200150
  20. https://www.opastpublishers.com/open-access-articles-pdfs/synthesis-and-characterization-of-pentaeritritol-tetranitrate-petn.pdf
  21. https://cdn.intratec.us/docs/reports/previews/per-e11a-b.pdf
  22. https://research.chalmers.se/publication/544755/file/544755_Fulltext.pdf
  23. https://cdn.intratec.us/docs/icc/previews/REPORT-ICC-PREV-014-A-PREM-USA.pdf
  24. https://patents.google.com/patent/US3968176A/en
  25. https://patents.google.com/patent/US3116320A/en
  26. https://irispublishers.com/abeb/fulltext/potential-replacement-of-pentaeritritol-tetranitrate-explosive-aggregate-polymer.ID.000549.php
  27. https://publications.jrc.ec.europa.eu/repository/bitstream/JRC139448/JRC139448_01.pdf
  28. https://www.osti.gov/servlets/purl/563855
  29. https://www.primaryinfo.com/pentaerythritol-tetranitrate.htm
  30. https://patents.google.com/patent/US1933754A/en
  31. https://digital.library.unt.edu/ark:/67531/metadc1406586/m2/1/high_res_d/15005943.pdf
  32. https://www.osti.gov/servlets/purl/886931
  33. http://www.prvaiskra-namenska.com/wp-content/uploads/2019/02/PRTN-RDX.pdf
  34. https://patents.google.com/patent/US2294592A/en
  35. https://www.researchgate.net/figure/presents-the-detonation-velocity-of-ultrafine-PETN-versus-the-height-of-the-explosive_fig12_309544507
  36. https://onlinelibrary.wiley.com/doi/10.1002/prep.202200288
  37. https://www.dynonobel.com/products-services/products/initiation-systems/det-cord/
  38. https://austinpowder.com/unitedstates/products/detonating-cord-options/?language=English
  39. https://www.epc-groupe.co.uk/products/detonating-cord/
  40. https://www.oricaminingservices.com/sn/en/product/products_and_services/initiating_systems/cast_booster/1327
  41. https://www.sciencedirect.com/topics/earth-and-planetary-sciences/petn
  42. https://www.dynonobel.com/siteassets/resource-hub/product-application-guides/41160-nonelprimacord-manual.pdf
  43. https://scholars.okstate.edu/en/publications/proficiency-testing-for-the-thermal-sensitivity-of-pentaerythrito
  44. https://ui.adsabs.harvard.edu/abs/2022APS..SHKE01003C/abstract
  45. https://www.goaeis.com/portals/goaeis/files/eis/final_eis_2011/sections/GOA_FEIS_3_2_Expended_Materials.pdf
  46. https://cameochemicals.noaa.gov/chemical/12290
  47. https://bulletpicker.com/pentolite.html
  48. https://apps.dtic.mil/sti/tr/pdf/ADA022479.pdf
  49. https://www.osti.gov/pages/biblio/1846137
  50. https://pmc.ncbi.nlm.nih.gov/articles/PMC3977134/
  51. https://go.drugbank.com/drugs/DB06154
  52. https://www.sciencedirect.com/topics/neuroscience/pentaerythritol-tetranitrate
  53. https://www.federalregister.gov/documents/2020/07/13/2020-15010/pentaerythritol-tetranitrate-final-decision-on-proposal-to-withdraw-approval-from-new-drug
  54. https://www.researchgate.net/publication/286661416_Comparison_of_the_clinical_efficacy_of_two_doses_of_pentaerythritol_tetranitrate_100_mg_and_30_mg_in_patients_with_stable_angina
  55. https://www.sciencedirect.com/science/article/pii/0002870352901324
  56. https://journal.chestnet.org/article/S0012-3692%2816%2931592-6/pdf
  57. https://www.sciencedirect.com/science/article/pii/S0735109701014140
  58. https://www.fbi.gov/history/artifacts/richard-reids-shoes
  59. https://www.nytimes.com/2010/10/31/world/middleeast/31petn.html
  60. https://www.justice.gov/archives/opa/pr/umar-farouk-abdulmutallab-sentenced-life-prison-attempted-bombing-flight-253-christmas-day
  61. https://ctc.westpoint.edu/the-evolving-challenges-for-explosive-detection-in-the-aviation-sector-and-beyond/
  62. https://www.govinfo.gov/content/pkg/CHRG-111shrg63867/html/CHRG-111shrg63867.htm
  63. https://www.ojp.gov/pdffiles1/nij/grants/237837.pdf
  64. https://chemicalsafety.ilo.org/dyn/icsc/showcard.display?p_card_id=1576
  65. https://cameochemicals.noaa.gov/chemical/12283
  66. https://researchcentre.army.gov.au/library/australian-army-journal-aaj/volume-10-number-1-autumn/niche-threat-organic-peroxides-terrorist-explosives
  67. https://www.icao.int/sites/default/files/2025-02/6601_en.pdf
  68. https://www.sciencedirect.com/science/article/abs/pii/S0039914022002107
  69. https://pubmed.ncbi.nlm.nih.gov/23199155/
  70. https://www.theguardian.com/world/2010/nov/01/petn-explosive-airport-cargo-scanners
  71. https://nicoletcz.cz/app/uploads/2021/08/5f8e6c45.pdf
  72. https://www.mdpi.com/1424-8220/21/16/5567
  73. https://www.ionicon.com/blog/2010/real-time-detection-of-petn-explosive-with-ptr-ms
  74. https://pmc.ncbi.nlm.nih.gov/articles/PMC6930616/
  75. https://www.tsa.gov/videos/inside-look-explosives-detection-canine-teams
  76. https://www.fbi.gov/investigate/terrorism/tedac
  77. https://www.semanticscholar.org/paper/Pentaerythritol-tetranitrate-%28PETN%29-profiling-in-to-Brust-Asten/3613e110c033e0ef43b8c1c5ed786ab7597b7656
  78. https://www.researchgate.net/publication/235396039_Limits_of_detection_of_explosives_as_determined_with_IMS_and_field_asymmetric_IMS_vapour_detectors
  79. https://nvlpubs.nist.gov/nistpubs/Legacy/IR/nistir7240.pdf
  80. https://www.gao.gov/assets/a307835.html
  81. https://www.spectroscopyonline.com/view/ai-powered-near-infrared-imaging-remotely-identifies-explosives
  82. https://www.mdpi.com/1420-3049/29/18/4482
  83. https://www.sciencedirect.com/science/article/pii/S1355030622001150
  84. https://pmc.ncbi.nlm.nih.gov/articles/PMC11270678/
  85. https://pubs.acs.org/doi/10.1021/acs.iecr.0c06294
  86. https://www.osti.gov/biblio/5375739
  87. https://www.osti.gov/biblio/7018517
  88. https://www.sciencedirect.com/science/article/abs/pii/S0032591021009244
  89. https://www.austinpowder.com/wp-content/uploads/2021/08/AP-Primary-Explosive-PETN-TDS-ENG.pdf
  90. https://nj.gov/health/eoh/rtkweb/documents/fs/1474.pdf
  91. https://www.maxamcorp.com/-/media/files/maxam/hrus/hru-un-exp-1001-ed-6en.ashx
  92. https://synapse.patsnap.com/article/what-are-the-side-effects-of-pentaerithrityl-tetranitrate
  93. https://hhpprtv.ornl.gov/issue_papers/PentaerythritoltetranitratePETN.pdf
  94. https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4292971.htm
  95. https://ntp.niehs.nih.gov/sites/default/files/ntp/htdocs/lt_rpts/tr365.pdf
  96. https://ntp.niehs.nih.gov/publications/reports/tr/tr365
  97. https://pmc.ncbi.nlm.nih.gov/articles/PMC2860203/
  98. https://apps.dtic.mil/sti/tr/pdf/ADA068989.pdf
  99. https://journals.asm.org/doi/pdf/10.1128/aem.62.4.1214-1219.1996
  100. https://pubs.acs.org/doi/abs/10.1021/es7029703
  101. https://pubmed.ncbi.nlm.nih.gov/18605582/
  102. https://apps.dtic.mil/sti/trecms/pdf/AD1017629.pdf
  103. https://www.researchgate.net/publication/5246604_Degradation_of_Pentaerythritol_Tetranitrate_PETN_by_Granular_Iron
  104. https://austinpowder.com/wp-content/uploads/2021/08/SDS-ASD-004-Detonators-Non-Electric-finished-produst-Eng-Us-NHN.pdf
  105. https://echa.europa.eu/substance-information/-/substanceinfo/100.003.737
  106. https://www.federalregister.gov/documents/2007/11/20/07-5585/appendix-to-chemical-facility-anti-terrorism-standards
  107. https://www.sciencedirect.com/topics/chemistry/nitrate-ester
  108. https://www.sciencedirect.com/science/article/pii/S2667134425000379
  109. https://onlinelibrary.wiley.com/doi/10.1002/prep.202000181
  110. https://www.researchgate.net/figure/Estimated-shelf-life-of-the-PBXs-and-PETN-samples-The-shelf-life-at-ambient-temperature_fig1_325696860
  111. https://www.researchgate.net/publication/346375954_The_Role_of_Pentaerythritol_Tetranitrate_PETN_Aging_in_Determining_Detonator_Firing_Characteristics
  112. https://pubs.acs.org/doi/10.1021/acsomega.4c04251
  113. https://www.osti.gov/biblio/966904
  114. https://www.researchgate.net/publication/325696860_Thermal_decomposition_and_shelf-life_of_PETN_and_PBX_based_on_PETN_using_thermal_methods
Add your contribution
Related Hubs
User Avatar
No comments yet.