Trimethylolethane trinitrate

Trimethylolethane trinitrate
IUPAC name [2-methyl-3-nitrooxy-2-(nitrooxymethyl)propyl] nitrate
Other names TMETN; Metriol trinitrate; METN; Nitropentaglycerin; 1,1,1-trimethylolethane trinitrate
Identifiers
CAS number	3032-55-1 Y
Jmol-3D images	Image 1
SMILES CC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O
Properties
Molecular formula	C5H9N3O9
Molar mass	255.14 g mol−1
Density	1.47 g/cm3
Melting point	-3 °C
Boiling point	decomposes at 182 °C
Hazards
Flash point	26.7 °C
Y trinitrate (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Trimethylolethane trinitrate (TMETN), also known as metriol trinitrate (METN, MTN, METRTN) or nitropentaglycerin, is a nitro ester. It is a high explosive similar to nitroglycerin. It is a transparent oily liquid, colorless to light brown. It is odorless. It is used in some solid propellants and smokeless powders as a plasticizer. Its chemical formula is CH₃-C(CH₂-O-NO₂)₃.

TMETN was first prepared and patented in Italy under name Metriolo. Germans began producing it before WWII when it was demonstrated to be an erosion and flash reducing agent in smokeless powders. It is a liquid explosive with properties similar to nitroglycerin but more stable to heat. It is prepared by nitration of trimethylolethane (metriol). It does not induce headaches.

TMETN can be initiated by friction, impact, and electrostatic discharge. It can be used as a high viscosity plasticizer-binder together with nitrocellulose, but its poor coloiding properties made such use rare; long-term milling can however assist here; success can also be achieved by adding an inert plasticizer and a volatile solvent/colloiding agent. ^[1]

TMETN is miscible with ether and acetone. It is insoluble in 95% sulfuric acid. ^[2]

TMETN can be used as a plasticizer together, or as an alternative to, triethyleneglycol dinitrate (TEGDN).

TMETN can also be used as a monopropellant. ^[3]

Triethylene glycol dinitrate, diethylene glycol dinitrate, and trimethyloleate trinitrate are being considered as replacements for nitroglycerin in propellants. ^[4]

References

1. ^ Explosive composition comprising HMX, RDX, or PETN and a high viscosity nitrocellulose binder plasticized with TMETN - The United States of America as represented by the Secre...
2. ^ Trimethylolethane Trinitrate
3. ^ Liquid Nitrate Ester Monopropellant Composition - Camp, Albert T
4. ^ Guns and Ordnance: Ammunition and Explosives - Storming Media

External links

• MSDS