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2,4-Dinitrotoluene
	File:2,4-Dinitrotoluol.svg
	File:Dinitrotoluene-3D-balls.png
Names
	IUPAC name 1-methyl-2,4-dinitro benzene
Identifiers
CAS Number	121-14-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:920 ;
ChEMBL	ChEMBL259865 ;
ChemSpider	8150 ;
ECHA InfoCard	Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value).
KEGG	C11006 ;
PubChem CID	8461;
	InChI InChI=1S/C7H6N2O4/c1-5-2-3-6(8(10)11)4-7(5)9(12)13/h2-4H,1H3 Key: RMBFBMJGBANMMK-UHFFFAOYSA-N ; InChI=1/C7H6N2O4/c1-5-2-3-6(8(10)11)4-7(5)9(12)13/h2-4H,1H3 Key: RMBFBMJGBANMMK-UHFFFAOYAC;
	SMILES Cc1ccc(cc1[N+](=O)[O-])[N+](=O)[O-];
Properties
Chemical formula	C7H6N2O4
Molar mass	182.134 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

VisualWikitext

Latest revision as of 02:38, 13 August 2012

Template:Chembox E number Template:Chembox UNNumber Template:Chembox Appearance Template:Chembox Density Template:Chembox MeltingPt Template:Chembox BoilingPt Template:Chembox Explosive

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

2,4-Dinitrotoluene (DNT) or Dinitro is an organic compound with the formula CH₃C₆H₃)(NO₂)₂. This pale yellow crystalline solid is well known as a precursor to trinitrotoluene (TNT) but is mainly produced as a precursor to toluene diisocyanate.

Isomers of dinitrotoluene

Six isomers are possible for dinitrotoluene. The most common one is 2,4-dinitrotoluene.

The nitration of toluene gives sequentially mononitrotoluene, DNT, and finally TNT. 2,4-DNT is the principal product from dinitration, the other main product being about 30% 2,6-DNT. The nitration of 4-nitrotoluene gives 2,4-DNT.^[2]

Applications

Most DNT is used in the production of toluene diisocyanate, which is used to produce flexible polyurethane foams. DNT is hydrogenated to produce toluenediamine, which in turn is phosgenated to give toluene diisocyanate. In this way, about 1.4 billion kilograms are produced annually, as of the years 1999-2000.^[3] Other uses include the explosives industry. It is not used by itself as an explosive, but some of the production is converted to TNT.

Dinitrotoluene is frequently used as a plasticizer, deterrent coating, and burn rate modifier in propellants (e.g., smokeless gunpowders). As it is carcinogenic and toxic, modern formulations tend to avoid its use. In this application it is often used together with dibutyl phthalate.^{[citation needed]}

Toxicity

Dinitrotoluenes are highly toxic with a TLV of 1.5 mg/m³. It converts hemoglobin into methemoglobin.

2,4 Dinitrotoluene is also a listed hazardous waste under 40 CFR 261.30. Its United States Environmental Protection Agency (EPA) hazardous waste Number is D030. The maximum concentration that may be contained to not have toxic characteristics is 0.13 mg/L.

References

↑ ^1.0 ^1.1 ^1.2 Template:GESTIS
↑ Gerald Booth (2007). "Nitro Compounds, Aromatic". In: Ullmann's Encyclopedia of Industrial Chemistry. John Wiley & Sons: New York. doi:10.1002/14356007.a17_411
↑ Christian Six, Frank Richter "Isocyanates, Organic" in Ulmann's Encyclopedia of Industrial Chemistry, 2005 Wiley-VCH, Weinheim doi:10.1002/14356007.a14_611

de:2,4-Dinitrotoluol nl:2,4-dinitrotolueen Template:WH Template:WS

[GESTIS-1] 1.0 ^1.1 ^1.2 Template:GESTIS

[Booth-2] Gerald Booth (2007). "Nitro Compounds, Aromatic". In: Ullmann's Encyclopedia of Industrial Chemistry. John Wiley & Sons: New York. doi:10.1002/14356007.a17_411

[Ullmann-3] Christian Six, Frank Richter "Isocyanates, Organic" in Ulmann's Encyclopedia of Industrial Chemistry, 2005 Wiley-VCH, Weinheim doi:10.1002/14356007.a14_611

[2]

[3]

@@ Line 1: / Line 1: @@
-#redirect:[[2,4-dinitrotoluene]]
+__NOTOC__
+{{chembox
+| Watchedfields = changed
+| verifiedrevid = 443312449
+| ImageFile = 2,4-Dinitrotoluol.svg
+| ImageSize = 130px
+| ImageFile1 = Dinitrotoluene-3D-balls.png
+| ImageSize1 = 150px
+| IUPACName = 1-methyl-2,4-dinitro benzene
+| OtherNames =
+| Section1 = {{Chembox Identifiers
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID = 8150
+| KEGG_Ref = {{keggcite|correct|kegg}}
+| KEGG = C11006
+| InChI = 1/C7H6N2O4/c1-5-2-3-6(8(10)11)4-7(5)9(12)13/h2-4H,1H3
+| InChIKey = RMBFBMJGBANMMK-UHFFFAOYAC
+| ChEMBL_Ref = {{ebicite|correct|EBI}}
+| ChEMBL = 259865
+| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChI = 1S/C7H6N2O4/c1-5-2-3-6(8(10)11)4-7(5)9(12)13/h2-4H,1H3
+| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChIKey = RMBFBMJGBANMMK-UHFFFAOYSA-N
+| CASNo_Ref = {{cascite|correct|CAS}}
+| CASNo = 121-14-2
+| PubChem = 8461
+| UNNumber = ''raztopljen:'' [[List of UN Numbers 1501 to 1600|1600]]<br/>''tekoč ali trden:'' [[List of UN Numbers 2001 to 2100|2038]]
+| ChEBI_Ref = {{ebicite|correct|EBI}}
+| ChEBI = 920
+| SMILES = Cc1ccc(cc1[N+](=O)[O-])[N+](=O)[O-]
+}}
+| Section2 = {{Chembox Properties
+| C = 7 | H = 6 | N = 2 | O = 4
+| MolarMass = 182.134 g/mol
+| Appearance = Pale yellow to orange [[crystal]]line solid
+| Density = 1.52 g/cm<sup>3</sup><ref name="GESTIS">{{GESTIS|Name=2,4-Dinitrotoluene|ZVG=17900|CAS=121-14-2 |Date=9. October 2007}}</ref>
+| MeltingPt = 70 °C<ref name="GESTIS"/>
+| BoilingPt = Decomposes at 250–300 °C<ref name="GESTIS"/>
+| Solubility = }}
+| Section3 = {{Chembox Hazards
+| MainHazards =
+| FlashPt =
+| Autoignition = }}
+| Section6 = {{Chembox Explosive
+| ShockSens = Insensitive
+| FrictionSens = Very low
+| ExplosiveV =
+| REFactor = }}
+}}
+{{SI}}
+{{CMG}}
+==Overview==
+'''2,4-Dinitrotoluene''' ('''DNT''') or '''Dinitro''' is an [[organic compound]] with the formula CH<sub>3</sub>C<sub>6</sub>H<sub>3</sub>)(NO<sub>2</sub>)<sub>2</sub>. This pale yellow [[crystalline]] solid is well known as a precursor to [[Trinitrotoluene|trinitrotoluene (TNT)]] but is mainly produced as a precursor to [[toluene diisocyanate]].
+==Isomers of dinitrotoluene==
+Six [[isomers]] are possible for dinitrotoluene. The most common one is 2,4-dinitrotoluene.
+The nitration of toluene gives sequentially [[mononitrotoluene]], DNT, and finally TNT.  2,4-DNT is the principal product from dinitration, the other main product being about 30% 2,6-DNT.  The nitration of 4-nitrotoluene gives 2,4-DNT.<ref name=Booth>Gerald Booth (2007). "Nitro Compounds, Aromatic". In: ''Ullmann's Encyclopedia of Industrial Chemistry''. John Wiley & Sons: New York. {{DOI|10.1002/14356007.a17_411}}</ref>
+==Applications==
+Most DNT is used in the production of [[toluene diisocyanate]], which is used to produce flexible [[polyurethane]] foams.  DNT is [[hydrogenation|hydrogenated]] to produce toluenediamine, which in turn is [[phosgene|phosgenated]] to give [[toluene diisocyanate]].  In this way, about 1.4 billion kilograms are produced annually, as of the years 1999-2000.<ref name=Ullmann>Christian Six, Frank Richter "Isocyanates, Organic" in Ulmann's Encyclopedia of Industrial Chemistry, 2005 Wiley-VCH, Weinheim {{DOI|10.1002/14356007.a14_611}}</ref>  Other uses include the explosives industry. It is not used by itself as an explosive, but some of the production is converted to TNT.
+Dinitrotoluene is frequently used as a [[plasticizer]], deterrent coating, and burn rate modifier in [[propellant]]s (e.g., [[smokeless gunpowder]]s). As it is [[carcinogen]]ic and toxic, modern formulations tend to avoid its use. In this application it is often used together with [[dibutyl phthalate]].{{Citation needed|date=November 2009}}
+==Toxicity==
+Dinitrotoluenes are highly toxic with a [[Threshold limit value|TLV]] of 1.5&nbsp;mg/m<sup>3</sup>.  It converts [[hemoglobin]] into [[methemoglobin]].
+,4 Dinitrotoluene is also a listed hazardous waste under 40 CFR 261.30. Its [[United States Environmental Protection Agency]] (EPA) hazardous waste Number is D030. The maximum concentration that may be contained to not have toxic characteristics is 0.13 mg/L.
+==References==
+{{reflist|2}}
+{{Commons category|Dinitrotoluene}}
+[[de:2,4-Dinitrotoluol]]
+[[fr:2,4-dinitrotoluène]]
+[[nl:2,4-dinitrotolueen]]
+{{WH}}
+{{WS}}