Difference between revisions of "Hexamethylene triperoxide diamine"

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{{Chembox
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| Name = Hexamethylene triperoxide diamine
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| Reference =
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| IUPACName = 3,4,8,9,12,13-Hexaoxa-1,6-diazabicyclo[4.4.4]tetradecane
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| PIN =
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| SystematicName =
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| OtherNames = 1,6-diaza-3,4,8,9,12,13-hexaoxabicyclo[4.4.4]tetradecane<br>HMTD
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| ImageFile = Hexamethylene triperoxide diamine HMTD by Explosiopedia.jpg
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| ImageSize = 300
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| ImageCaption = HMTD as powder
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| Section1 = {{Chembox Identifiers
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| 3DMet =
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| Abbreviations =
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| SMILES =
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| Section2 = {{Chembox Properties
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| AtmosphericOHRateConstant =
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| Appearance = White crystalline solid
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| BoilingPt =
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| BoilingPtC =
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| BoilingPt_ref =
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| BoilingPt_notes = Detonates
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| Density = 0.88 g/cm<sup>3</sup><br>1.57 g/cm<sup>3</sup><br>1.597 g/cm<sup>3</sup> (at -123.15 °C)<ref>Wierzbicki, Andrzej; Salter, E. Alan; Cioffi, Eugene A.; Stevens, Edwin D.; Journal of Physical Chemistry A; vol. 105; nb. 38; (2001); p. 8763 - 8768</ref>
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| Formula = C<sub>6</sub>H<sub>12</sub>N<sub>2</sub>O<sub>6</sub>
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| HenryConstant =
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| LogP =
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| MolarMass = 208.17 g/mol
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| MeltingPt =
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| MeltingPt_notes = Decomposes at 75 °C<br>Ignites spontaneously at 133 °C
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| pKa =
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| pKb =
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| Solubility = 0.01 g/100 ml
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| SolubleOther = Soluble in [[ethanol]], [[Tetrahydrofuran|THF]]
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| Solubility1 = 0.41 g/100 ml
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| Solvent1 = acetone
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| Solubility2 = 0.024 g/100 ml
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| Solvent2 = diethyl ether
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| Solubility3 = 0.36 g/100 ml
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| Solvent3 = chloroform
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| VaporPressure =
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| Section5 = {{Chembox Explosive
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| ShockSens = High
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| FrictionSens = High
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| DetonationV = ~4511 m/s
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| REFactor = 0.8
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| Section6 = {{Chembox Hazards
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| AutoignitionPt = 133 °C
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| ExploLimits =
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| ExternalMSDS = None
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| FlashPt =
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| MainHazards = Sensitive explosive
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| Section7 = {{Chembox Related
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| OtherAnions =
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| OtherCations =
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| OtherFunction =
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| OtherFunction_label =
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| OtherCompounds = [[Acetone peroxide]]<br>[[Methyl ethyl ketone peroxide]]
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  }}
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}}
 
'''Hexamethylene triperoxide diamine''' or '''HMTD''' is a dangerous high explosive organic compound. It has very little use outside of amateur explosives, and because it was used in many terrorist bombings, it gets a bad reputation.
 
'''Hexamethylene triperoxide diamine''' or '''HMTD''' is a dangerous high explosive organic compound. It has very little use outside of amateur explosives, and because it was used in many terrorist bombings, it gets a bad reputation.
  
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===Physical===
 
===Physical===
−
HMTD is a white solid, which decomposes if heated to 75 °C. It has a density of 0.88 g/cm<sup>3</sup>. HMTD is soluble in [[Tetrahydrofuran|THF]], and somewhat soluble in [[ethanol]].<ref>http://actachemscand.org/pdf/acta_vol_42a_p0165-0170.pdf</ref>
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HMTD is a white solid, which decomposes if heated to 75 °C. It has a density of 0.88 g/cm<sup>3</sup>. HMTD is soluble in [[Tetrahydrofuran|THF]], and somewhat soluble in [[ethanol]].<ref>http://actachemscand.org/pdf/acta_vol_42a_p0165-0170.pdf</ref> It is almost insoluble in [[acetone]], [[chloroform]], [[diethyl ether]] and [[water]].<ref>Haid; Globig; Z. Schiess-Sprengstoffw.; vol. 21; p. 164; Chem. Zentralbl.; vol. 98; nb. I; (1927); p. 967</ref>
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===Explosive===
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HMTD is can detonate when subjected to moderate shock, friction, and heat, but it is less sensitive than most peroxide-based explosives. It has a detonation velocity of 4511 m/s (though some sources give the value of 5100 m/s) and a R.E. factor of 0.8, identical to that of TATP (acetone peroxide).
  
 
==Availability==
 
==Availability==
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==Projects==
 
==Projects==
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Due to its instability, HMTD doesn't have many uses outside amateur explosives. As it is a stronger initiating explosive than [[mercury(II) fulminate]], it can be used to make blasting caps, albeit they should be used quickly. Unfortunately, due to its use in terrorist bombings it's best to stay away from using this compound as mush as possible.
  
 
==Handling==
 
==Handling==
 
===Safety===
 
===Safety===
 
Although it is more stable than most explosive peroxides, it is still sensitive to friction, shock and heat, especially when dry. Contact with metals should be avoided. If wet or underwater, it is more stable.
 
Although it is more stable than most explosive peroxides, it is still sensitive to friction, shock and heat, especially when dry. Contact with metals should be avoided. If wet or underwater, it is more stable.
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===Legal===
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The manufacture, possession or use of HMTD without a permit/license is a crime in most countries.
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Like acetone peroxide, it is a federal offense to make, possess, or use HMTD in the United States.
  
 
===Storage===
 
===Storage===
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===Sciencemadness Library===
 
===Sciencemadness Library===
 
*[http://library.sciencemadness.org/library/books/the_chemistry_of_powder_and_explosives.pdf The Chemistry of Powder and Explosives]
 
*[http://library.sciencemadness.org/library/books/the_chemistry_of_powder_and_explosives.pdf The Chemistry of Powder and Explosives]
 +
 
===Relevant Sciencemadness threads===
 
===Relevant Sciencemadness threads===
 
*[http://www.sciencemadness.org/talk/viewthread.php?tid=14563 HMTD safety]
 
*[http://www.sciencemadness.org/talk/viewthread.php?tid=14563 HMTD safety]

Revision as of 15:41, 3 December 2016

Hexamethylene triperoxide diamine
Hexamethylene triperoxide diamine HMTD by Explosiopedia.jpg
HMTD as powder
Names
IUPAC name
3,4,8,9,12,13-Hexaoxa-1,6-diazabicyclo[4.4.4]tetradecane
Other names
1,6-diaza-3,4,8,9,12,13-hexaoxabicyclo[4.4.4]tetradecane
HMTD
Properties
C6H12N2O6
Molar mass 208.17 g/mol
Appearance White crystalline solid
Density 0.88 g/cm3
1.57 g/cm3
1.597 g/cm3 (at -123.15 °C)[1]
Melting point Decomposes at 75 °C
Ignites spontaneously at 133 °C
Boiling point Detonates
0.01 g/100 ml
Solubility Soluble in ethanol, THF
Solubility in acetone 0.41 g/100 ml
Solubility in diethyl ether 0.024 g/100 ml
Solubility in chloroform 0.36 g/100 ml
Hazards
Safety data sheet None
Related compounds
Related compounds
 Acetone peroxide
Methyl ethyl ketone peroxide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Hexamethylene triperoxide diamine or HMTD is a dangerous high explosive organic compound. It has very little use outside of amateur explosives, and because it was used in many terrorist bombings, it gets a bad reputation.

Properties

Chemical

Like most organic peroxides, such as acetone peroxide, HMTD is unstable and detonates when subjected to shock, friction, and heat. It is, however, less unstable than many other peroxides under normal conditions. It's sensitivity is greatly increased from exposure to ultraviolet light or in contact with most common metals. HMTD is chemically very stable when pure (free of acids, bases, and metal ions) and does not quickly sublime like its acetone counterparts.

Physical

HMTD is a white solid, which decomposes if heated to 75 °C. It has a density of 0.88 g/cm3. HMTD is soluble in THF, and somewhat soluble in ethanol.[2] It is almost insoluble in acetone, chloroform, diethyl ether and water.[3]

Explosive

HMTD is can detonate when subjected to moderate shock, friction, and heat, but it is less sensitive than most peroxide-based explosives. It has a detonation velocity of 4511 m/s (though some sources give the value of 5100 m/s) and a R.E. factor of 0.8, identical to that of TATP (acetone peroxide).

Availability

HMTD is not sold by any supplier due to its sensitivity.

Preparation

The preparation of HMTD always presents the risk of premature detonation and should not be attempted by amateurs. But if you really want to know:

14 g of hexamine is dissolved in 45 ml of hydrogen peroxide 30% concentration and stirred (mechanically) at 0 °C. An amount of 21 grams of finely powdered citric acid is then slowly added under continuous stirring for 3 h, at 0 °C. After 3 hours, the product is allowed to reach room temperature and left for 2 h. The white crystalline product is filtered off, and washed thoroughly with water, to remove any water soluble impurities and rinsed with methanol. The wet product is air dried. This part is risky as the product may explode during drying. The yield is around 50-70%.[4]

Larger amounts are not safe to handle, so it's best to try to make smaller amounts based on the process above.

Projects

Due to its instability, HMTD doesn't have many uses outside amateur explosives. As it is a stronger initiating explosive than mercury(II) fulminate, it can be used to make blasting caps, albeit they should be used quickly. Unfortunately, due to its use in terrorist bombings it's best to stay away from using this compound as mush as possible.

Handling

Safety

Although it is more stable than most explosive peroxides, it is still sensitive to friction, shock and heat, especially when dry. Contact with metals should be avoided. If wet or underwater, it is more stable.

Legal

The manufacture, possession or use of HMTD without a permit/license is a crime in most countries.

Like acetone peroxide, it is a federal offense to make, possess, or use HMTD in the United States.

Storage

NEVER STORE HMTD!

Disposal

Being a sensitive explosive, it is easy to dispose of, though this is unsafe.

Safe disposal can be done by adding a mixture of zinc sulfate, copper(II) chloride with Zn and Cu powder, in a solution containing the peroxide. The salt/metal/peroxide ratio is 5:5:1. Small amounts of sulfuric acid are also added. [5]

References

  1. ↑ Wierzbicki, Andrzej; Salter, E. Alan; Cioffi, Eugene A.; Stevens, Edwin D.; Journal of Physical Chemistry A; vol. 105; nb. 38; (2001); p. 8763 - 8768
  2. ↑ http://actachemscand.org/pdf/acta_vol_42a_p0165-0170.pdf
  3. ↑ Haid; Globig; Z. Schiess-Sprengstoffw.; vol. 21; p. 164; Chem. Zentralbl.; vol. 98; nb. I; (1927); p. 967
  4. ↑ http://pubs.acs.org/doi/abs/10.1021/ja00294a043
  5. ↑ http://energetics.chm.uri.edu/?q=/system/files/2008+Destruction+of+Peroxide+Explosives.pdf

Sciencemadness Library

Relevant Sciencemadness threads

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