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{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 395266835 | verifiedrevid = 428734596
| ImageFile = Trimethylolethane trinitrate.png | ImageFile = Trimethylolethane trinitrate.png
| ImageSize = 150px | ImageSize = 150px
| IUPACName = nitrate | IUPACName = nitrate
| OtherNames = TMETN; Metriol trinitrate; METN; Nitropentaglycerin; 1,1,1-trimethylolethane trinitrate | OtherNames = TMETN; Metriol trinitrate; METN; Nitropentaglycerin; 1,1,1-trimethylolethane trinitrate
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 3032-55-1 | CASNo = 3032-55-1
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem =
| UNII = HMJ3NEC9W7
⚫ | PubChem = 76423
| ChemSpiderID = 68895
| StdInChI = 1S/C5H9N3O9/c1-5(2-15-6(9)10,3-16-7(11)12)4-17-8(13)14/h2-4H2,1H3
| StdInChIKey = IPPYBNCEPZCLNI-UHFFFAOYSA-N
| SMILES = CC(CO()=O)(CO()=O)CO()=O | SMILES = CC(CO()=O)(CO()=O)CO()=O
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C = 5 | H = 9 | N = 3 | O = 9 | C=5 | H=9 | N=3 | O=9
| MolarMass = 255.14 | MolarMass = 255.14
| Appearance = | Appearance =
| Density = 1.47 g/cm<sup>3</sup> | Density = 1.47 g/cm<sup>3</sup>
| MeltingPt = -3 °C | MeltingPtC = -3
| BoilingPt = decomposes at 182 °C | BoilingPt= decomposes at
| Solubility = }} | BoilingPtC = 182
| Solubility =
⚫ | Section3 = {{Chembox Hazards
}}
⚫ |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = 26.7 °C | FlashPtC = 26.7
| AutoignitionPtC =
| Autoignition = }}
}}
| Section6 = {{Chembox Explosive |Section6={{Chembox Explosive
| ShockSens = | ShockSens =
| FrictionSens = | FrictionSens =
| ExplosiveV = | DetonationV =
| REFactor = }} | REFactor =
}}
}} }}


'''Trimethylolethane trinitrate''' ('''TMETN'''), also known as '''metriol trinitrate''' ('''METN''', '''MTN''', '''METRTN''') or '''nitropentaglycerin''', is a nitro ]. It is a ] similar to ]. It is a transparent oily liquid, colorless to light brown. It is odorless. It is used in some ]s and ]s as a ]. Its chemical formula is CH<sub>3</sub>-C(CH<sub>2</sub>-O-NO<sub>2</sub>)<sub>3</sub>. '''Trimethylolethane trinitrate''' ('''TMETN'''), also known as '''metriol trinitrate''' ('''METN''', '''MTN''', '''METRTN''') or '''nitropentaglycerin''', is a ]. It is a ] similar to ]. It is a transparent oily liquid, colorless to light brown. It is odorless. It is used in some ]s and ]s as a ]. Its chemical formula is {{chem2|CH3\sC(CH2\sO\sNO2)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 ] of ] (metriol). It does not induce headaches. TMETN was first prepared and patented in Italy under name '''Metriolo'''. Germans began producing it before World War II, 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 ] of ] (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 ], 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. TMETN can be initiated by friction, impact, and electrostatic discharge. It can be used as a high-viscosity plasticizer-binder together with ], but its poor colloidal properties has 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/colloidal agent.<ref></ref>


TMETN is miscible with ether and acetone. It is insoluble in 95% sulfuric acid.<ref>{{Cite web |url=http://www.osha.gov/dts/chemicalsampling/data/CH_273950.html |title=Trimethylolethane Trinitrate<!-- Bot generated title --> |access-date=2009-01-04 |archive-date=2009-01-06 |archive-url=https://web.archive.org/web/20090106062033/http://www.osha.gov/dts/chemicalsampling/data/CH_273950.html |url-status=dead }}</ref> It can be used as a plasticizer together with, or as an alternative to, ] (TEGDN). It can also be used as a ];<ref></ref> in fact ], ], and trimethyloleate trinitrate are being considered as replacements for nitroglycerin in propellants.<ref>{{Cite web |url=http://www.stormingmedia.us/cat/sub/subcat20-57.html |title=Guns and Ordnance: Ammunition and Explosives – Storming Media<!-- Bot generated title --> |access-date=2009-01-04 |archive-date=2012-09-03 |archive-url=https://web.archive.org/web/20120903212929/http://www.stormingmedia.us/cat/sub/subcat20-57.html |url-status=dead }}</ref>
TMETN is miscible with ether and acetone. It is insoluble in 95% sulfuric acid.

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

TMETN can also be used as a ].

], ], and trimethyloleate trinitrate are being considered as replacements for nitroglycerin in propellants.


==References== ==References==
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==External links== ==External links==
* * {{Webarchive|url=https://web.archive.org/web/20160303191727/http://www.rocketmotorparts.com/pdfs/tmetn_msds.pdf |date=2016-03-03 }}


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