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Acetone peroxide

Acetone peroxide structure

Acetone peroxide 

structure
  • CAS No:

    17088-37-8

  • Formula:

    C9H18O6

  • Chemical Name:

    Acetone peroxide

  • Synonyms:

    3,3,6,6,9,9-hexamethyl-1,2,4,5,7,8-hexaoxocyclononane;TATP cpd;triacetone triperoxide;triacetonetriperoxide;Acetone peroxide trimer;Acetone cyclic triperoxide;UNII-62T938ZGDD;1,2,4,5,7,8-Hexoxonane, 3,3,6,6,9,9-hexamethyl-

  • Categories:

    Organic Chemistry  >  Free Radicals

Acetone peroxide Basic Attributes

222.237

222.11000

62T938ZGDD

DTXSID4074803

Crystalline solid|White crystals|Crystals from methyl alcohol

2914190090

Characteristics

55.4

2.05290

1.22 g/cu cm

98°

184.9±30.0 °C(Predicted)

51.467ºC

1.382

Insoluble in water

Terpen-like to odorless, depending on purity of ingredients

Highly volatile; decomposes via an entropically favorable mechanism to form 4 gas phase molecules /SRP: decomposition products include acetone and hydrogen peroxide/|Shock, temperature and friction sensitive when air-dry; should be kept under water when not in use; sublimes at room temperature

Safety Information

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

This paper discusses methods to degrade peroxide explosives chemically, at room temperature. A number of mixtures containing metals (e.g., zinc, copper) and metal salts (e.g., zinc sulfate, copper chloride) were found effective, some capable of destroying triacetone triperoxide (TATP) solutions in a few hours. Strong acids proved useful against solid peroxide materials; however, on a 1 g scale, addition of concentrated sulfuric acid caused TATP to detonate. Thus, this technique should only be used to destroy small-laboratory quantities.

The number one way to protect yourself and others from an IED attack is to be alert to your surroundings. Advanced technologies help police and other authorities detect possible dangers, but an even more effective tool is to encourage individuals to be alert for, and to report, anything that is out of the ordinary in their daily routine. /Improvised explosive devices/|Every person can take these steps to prepare for an IED attack: Learn the emergency procedures at your place of work, any other sites you visit regularly, and any public transportation systems you use. Communication systems may be inoperable in an emergency, and you should be familiar with what steps to take. Know how to get out of the area. If you work far from home, plan backups to get home if the usual modes of transit are not operating. n Know the routes to hospitals in your community. Take a first aid course. Make a family emergency plan. Remember that family members may be in separate locations at the time of an attack. Use planning tools at ready.gov to prepare yourself and your family, Designate an "out-of-area" contact, and make sure that everyone in your family has that person's phone number. Have an emergency supply kit at work and at home that includes water and non-perishable food to last at least three days, battery-powered radio, first aid kit, flashlights, and batteries. /Improvised explosive devices/|If you are at the immediate site of an IED attack, your top priority is to get out of the area. This increases your safety in case a secondary device is present in the area and minimizes your exposure to dust, smoke, and any hazardous substances that may have been released as a result of the blast. This also allows emergency responders to find and assist the most critically injured victims. ... If you become trapped: Cover your nose and mouth with anything you have on hand to limit inhalation of dust or other hazardous materials. Dense-weave cotton material can act as a good filter. Avoid unnecessary movement so you don't kick up dust. Signal your location to rescuers by using a flashlight or whistle, or by tapping on a pipe or wall. Shout only as a last resort. Shouting can cause you to inhale dangerous amounts of dust and drain your energy. /Improvised explosive devices/|If you are in a train, on the subway, or on a bus: In general, it is best to remain inside the train car unless you are in immediate danger. Use the communication system on the train car to receive instructions. If you are in danger and must leave the car, be aware of hazards on the tracks or in the tunnel and move with caution to the nearest station or point where you can contact emergency personnel. Open windows or doors if possible and if it is safe to do so, because it can reduce the severity and number of injuries from a secondary explosion. /Improvised explosive devices/|Caring for the injured: First aid you provide may save lives. The most likely help you may need to provide is to control bleeding. Apply direct pressure to the bleeding site. Nearby hospitals may be overwhelmed with victims. If you need to transport victims who are not severely injured, go to a hospital that is further from the bombing site. /Improvised explosive devices/

Drug Information

Substances that are energetically unstable and can produce a sudden expansion of the material, called an explosion, which is accompanied by heat, pressure and noise. Other things which have been described as explosive that are not included here are explosive action of laser heating, human performance, sudden epidemiological outbreaks, or fast cell growth. (See all compounds classified as Explosive Agents.)

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/OTHER TOXICITY INFORMATION/ Immediate Health Effects. Explosions create a high-pressure blast that sends debris flying and lifts people off the ground. The type of injuries and the number of people hurt will vary depending on: the physical environment and the size of the blast; the amount of shielding between victims and the blast; fires, or structural damage that result from the explosion; and whether the explosion occurs in a closed space or an open area. Injuries common to explosions include: Overpressure damage to the lungs, ears, abdomen, and other pressure-sensitive organs. Blast lung injury, a condition caused by the extreme pressure of an explosion, is the leading cause of illness and death for initial survivors of an explosion. Fragmentation injuries caused by projectiles thrown by the blast - material from the bomb, shrapnel, or flying debris that penetrates the body and causes damage. n Impact injuries caused when the blast throws a victim into another object, i.e. fractures, amputation, and trauma to the head and neck. Thermal injuries caused by burns to the skin, mouth, sinus, and lungs. Other injuries including exposure to toxic substances, crush injuries, and aggravation of pre-existing conditions (asthma, congestive heart failure, etc.). Delayed Health Effects. Some health effects caused by IEDs, including eye injuries and abdominal injuries, may not be apparent initially, but can cause symptoms and even fatalities hours to months after the event. Psychological effects in attack survivors, first responders, and others are not unusual in the aftermath of a high-casualty event. While most symptoms diminish with time, in some cases assistance and guidance from mental health professionals may be required. /improvised explosive devices/

3,3,6,6,9,9-hexamethyl-1,2,4,5,7,8-hexaoxocyclononane

Acetone peroxide Use and Manufacturing

Uses

In explosives.

Chemicals containing multiple peroxide functionalities, such as triacetone triperoxide (TATP), diacetone diperoxide (DADP), or hexamethylene triperoxide diamine (HMTD) ... are impractical and are not used by legitimate military groups because they are shock and heat sensitive compared to military explosives.|Discovered by Wolffenstein in 1895, but due to instability it was rarely applied until the 1980's ... Slightly less powerful explosive than TNT.

Method: EPA-OSW 8330B; Procedure: high performance liquid chromatography using a dual wavelength ultraviolet detector; Analyte: triacetone triperoxide; Matrix: water, soils and sediment; Detection Limit: not provided.|The explosive triacetone triperoxide (TATP) has been analyzed by gas chromatography/mass spectrometry (GC/MS) and sub-nanogram detection limits are reported by ammonia positive ion chemical ionization (PICI), electron ionization (EI) and methane negative ion chemical ionization (NICI). Analysis by methane PICI and ammonia NICI gave detection limits in the low nanogram range. ... These results provide a method for pico-gram detection levels of TATP using commercial instrumentation commonly available in forensic laboratories. As a point of comparison, a detection limit of 15 ng was obtained by flame ionization detection.|Triacetone triperoxide (TATP) ... was measured by means of gas chromatography/multiphoton ionization/time-of-flight mass spectrometry using a deep-ultraviolet (deep-UV) femtosecond laser as an ionization source. ... The detection limits obtained using the molecular ion and two dominant fragment ions, C(2)H(3)O(+) and CH(3) (+), were determined to be 670, 83 and 150 pg, respectively.|An HPLC-APCI-MS(/MS) method for the (trace) analysis of the most commonly encountered peroxide explosives, hexamethylenetriperoxidediamine (HMTD) and triacetonetriperoxide (TATP), has been developed. With this method, HMTD and TATP have been analyzed in the same run. ... The method presented has been applied successfully for the identification of peroxides in the bulk solid state (powder sample), as well as in post-blast extracts originating from a forensic case. For the post-blast extracts, the use of tandem MS has been shown clearly to be of crucial importance for the identification and detection of the peroxide explosives.|For more Analytic Laboratory Methods (Complete) data for Triacetone triperoxide (10 total), please visit the HSDB record page.

Conventional explosives 2,4,6-trinitrotoluene (TNT), nitroglycerin (NG), and ethylene glycol dinitrate (EGDN) sorbed to hair can be directly detected by an ion mobility spectrometer (IMS) in E-mode (for explosives). Terrorist explosive, triacetone triperoxide (TATP), difficult to detect by IMS in E-mode, was detected in N-mode (for narcotics). ... Three modes of sample introduction to IMS vapor desorption unit were used: (i) placement of hair directly into the unit, (ii) swabbing of hair and placement of swabs (i.e., paper GE-IMS sample traps) into the unit, and (iii) acetonitrile extracts of hair positioned on sample traps and placed into the unit. ... IMS in N-mode detected TATP from hair by all three modes of sample introduction.

Computed Properties

Molecular Weight:222.24
XLogP3:1.8
Hydrogen Bond Acceptor Count:6
Exact Mass:222.11033829
Monoisotopic Mass:222.11033829
Topological Polar Surface Area:55.4
Heavy Atom Count:15
Complexity:167
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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