Nitroethane

From Infogalactic: the planetary knowledge core
Jump to: navigation, search
Nitroethane
100px
100px
150px
Names
IUPAC name
nitroethane
Identifiers
79-24-3 YesY
ChEBI CHEBI:16268 N
ChEMBL ChEMBL15625 YesY
ChemSpider 6338 YesY
Jmol 3D model Interactive image
KEGG C01837 YesY
PubChem 6587
RTECS number KI5600000
UN number UN 2842
  • InChI=1S/C2H5NO2/c1-2-3(4)5/h2H2,1H3 YesY
    Key: MCSAJNNLRCFZED-UHFFFAOYSA-N YesY
  • InChI=1/C2H5NO2/c1-2-3(4)5/h2H2,1H3
    Key: MCSAJNNLRCFZED-UHFFFAOYAB
  • CC[N+](=O)[O-]
Properties
C2H5NO2
Molar mass 75.07 g/mol
Density 1.054 g/cm3, liquid
Melting point −90 °C (−130 °F; 183 K)
Boiling point 112.0 to 116.0 °C (233.6 to 240.8 °F; 385.1 to 389.1 K)
slightly soluble (4.6 g/100 ml at 20 °C)
Vapor pressure 21 mmHg (25°C)[1]
Viscosity 0.677 Pa·s at 20 °C
Vapor pressure {{{value}}}
Related compounds
2-Nitropropane
nitromethane
1,1-dichloro-1-nitroethane
Related compounds
 ethyl nitrite
ethyl nitrate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Nitroethane is an organic compound having the chemical formula C2H5NO2. Similar in many regards to nitromethane, nitroethane is an oily liquid at standard temperature and pressure. Pure nitroethane is colourless and has a fruity odor.

Preparation

Nitroethane is produced industrially by treating propane with nitric acid at 350–450 °C. This exothermic reaction produces four industrially significant nitroalkanes: nitromethane, nitroethane, 1-nitropropane, and 2-nitropropane. The reaction involves free radicals, such as CH3CH2CH2O., which arise via homolysis of the corresponding nitrite ester. These alkoxy radicals are susceptible to C—C fragmentation reactions, which explains the formation of a mixture of products.[2]

Alternatively, nitroethane can be produced by the Victor Meyer reaction with either bromoethane or iodoethane with silver nitrite in a diethyl ether solvent or with the Kornblum Modification which uses the prior mentioned alkyl halides with the less soluble sodium nitrite salt in either a dimethyl sulfoxide or dimethylformamide solvent.[3]

Uses

Via condensations like the Henry reaction, nitroethane converts to several compounds of commercial interest. Condensation with 3,4-dimethoxybenzaldehyde affords the precursor to the antihypertensive drug methyldopa; condensation with unsubstituted benzaldehyde yields phenyl-2-nitropropene. Nitroethane condenses with two equivalents of formaldehyde to give, after hydrogenation, 2-amino-2-methyl-1,3-propanediol, which in turn condenses with oleic acid to give an oxazoline, which protonates to give a cationic surfactant.[2]

Like some other nitrated organic compounds, nitroethane is also used as a fuel additive and a precursor to explosives.

Nitroethane is a useful solvent for polymers such as polystyrene and is particularly useful for dissolving cyanoacrylate adhesives.[citation needed] In niche applications, it has been used as a component in artificial nail remover and in overhead ceiling sealant sprays.

Toxicity

Nitroethane is suspected to cause genetic damage and be harmful to the nervous system. Typical TLV/TWA is 100 ppm. Typical STEL is 150 ppm. Skin contact causes dermatitis in humans. In animal studies, nitroethane exposure was observed to cause lacrimation, dyspnea, pulmonary rales, edema, liver and kidney injury, and narcosis.[4] Children have been poisoned by accidental ingestion of artificial nail remover.[5]

The LD50 for rats is reported as 1100 mg/kg.[6]

References

<templatestyles src="Reflist/styles.css" />

Cite error: Invalid <references> tag; parameter "group" is allowed only.

Use <references />, or <references group="..." />

External links

Lua error in package.lua at line 80: module 'strict' not found.

  1. ↑ Cite error: Invalid <ref> tag; no text was provided for refs named PGCH
  2. ↑ 2.0 2.1 Sheldon B. Markofsky “Nitro Compounds, Aliphatic” Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a17_401.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ "Chemical Sampling Information Nitroethane." Retrieved February 9, 2007, from the website of the US Occupational Safety & Health Administration.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ MSDS for nitroethane (revised October 3, 2005), as reported by Fisher Scientific.
Retrieved from "https://infogalactic.com/w/index.php?title=Nitroethane&oldid=1052373"