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2,4-Dinitrotoluene-Wikipedia

2,4-Dinitrotoluene

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Organic chemical compound
2,4-Dinitrotoluene

2,4-Dinitrotoluol.svg

2,4-Dinitrotoluene-3D-balls.png

Names

Preferred IUPAC name

1-Methyl-2,4-dinitrobenzene
Other names

Dinitrotoluol, Methyldinitrobenzene
Identifiers

CAS Number

  • 121-14-2

     checkY

3D model (

JSmol

)

  • Interactive image

ChEBI

  • CHEBI:920

     checkY

ChEMBL

  • ChEMBL259865

     checkY

ChemSpider

  • 8150

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ECHA InfoCard

100.004.046

Edit this at Wikidata

KEGG

  • C11006

     checkY

PubChem

CID

  • 8461

UNII

  • 6741D310ED

     checkY

UN number

Molten:

1600

Solid or liquid:

2038

CompTox Dashboard

(EPA)

  • DTXSID0020529

    Edit this at Wikidata

InChI

  • InChI=1S/C7H6N2O4/c1-5-2-3-6(8(10)11)4-7(5)9(12)13/h2-4H,1H3 checkY
    Key: RMBFBMJGBANMMK-UHFFFAOYSA-N checkY
  • 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
Appearance Pale yellow to orange

crystalline

solid

Density

1.52 g/cm3

[1]

Melting point

70 °C (158 °F; 343 K)

[1]

Boiling point

Decomposes at 250–300 °C

[1]

Vapor pressure

1.47X10-4 mm Hg @ 22 C

[2]

Hazards
Main

hazards

carcinogen, combustible (though difficult to ignite)

[3]

Flash point

207 °C; 404 °F; 480 K
Lethal dose or concentration (LD, LC):
LD50 (

median dose

)

216 mg/kg (oral, rat, 3,5-isomer)
1,954 mg/kg (oral, mouse, 2,4-isomer)

[4]

LDLo (

lowest published

)

27 mg/kg (2,4 isomer, cat, oral)

[4]

NIOSH

(US health exposure limits):

PEL

(Permissible)

TWA 1.5 mg/m3 [skin]

[3]

REL

(Recommended)

Ca TWA 1.5 mg/m3 [skin]

[3]

IDLH

(Immediate danger)

Ca [50 mg/m3]

[3]

Explosive data

Shock sensitivity

Insensitive

Friction sensitivity

Very low
Except where otherwise noted, data are given for materials in their

standard state

(at 25 °C [77 °F], 100 kPa).

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Infobox references

Chemical compound

2,4-Dinitrotoluene (DNT) or dinitro is an

organic compound

with the formula C7H6N2O4. This pale yellow

crystalline

solid is well known as a precursor to

trinitrotoluene

(TNT) but is mainly produced as a precursor to

toluene diisocyanate

.

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Isomers of dinitrotoluene[

edit

]

Six

positional 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% 1,3-DN2-T. The nitration of

4-nitrotoluene

gives 2,4-DNT.

[5]

Applications[

edit

]

Most DNT is used in the production of

toluene diisocyanate

, which is used to produce flexible

polyurethane

foams. DNT is

hydrogenated

to produce

2,4-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.

[6]

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

[3]

and toxic, modern formulations tend to avoid its use. In this application it is often used together with

dibutyl phthalate

.[

citation needed

]

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Toxicity[

edit

]

Dinitrotoluenes are highly toxic with a

threshold limit value

(TLV) of 1.5 mg/m3.

[7]

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.

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References[

edit

]

  1. ^

    a

    b

    c

    Record of 2,4-Dinitrotoluene

    in the GESTIS Substance Database of the

    Institute for Occupational Safety and Health

    , accessed on 9. October 2007.

  2. ^

    Pella, PA. J. Chem. Thermodyn. 9: 301-305, 1977

  3. ^

    a

    b

    c

    d

    e

    NIOSH Pocket Guide to Chemical Hazards.

    “#0235”

    .

    National Institute for Occupational Safety and Health

    (NIOSH).

  4. ^

    a

    b

    “Dinitrotoluene (mixed isomers)”

    . Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH). 4 December 2014. Retrieved 17 March 2015.

  5. ^

    Gerald Booth (2007). “Nitro Compounds, Aromatic”. Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH.

    doi

    :

    10.1002/14356007.a17_411

    .

  6. ^

    Six, C.; Richter, F. “Isocyanates, Organic”.

    Ullmann’s Encyclopedia of Industrial Chemistry

    . Weinheim: Wiley-VCH.

    doi

    :

    10.1002/14356007.a14_611

    .

  7. ^

    NIOSH Pocket Guide to Chemical Hazards – Dinitroluene

External links[

edit

]

  • Media related to

    Dinitrotoluenes

    at Wikimedia Commons

Retrieved from “

https://en.wikipedia.org/w/index.php?title=2,4-Dinitrotoluene&oldid=1014341103

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