Nitroethane

Common industrial solvent more recently a commercial artificial nail remover 

Toxicology. In animals, nitroethane is a respiratory irritant and, at high concentrations, it causes narcosis and liver damage methemo-globin has been reported after ingestion by humans. 

Rabbits died from exposure to 5000 ppm for 3 hours but survived 3 hours at 2500ppm. Exposure to the higher concentrations caused irritation of mucous membranes, lacrima-tion, dyspnea, pulmonary rales, and, in a few animals, pulmonary edema convulsions were rare and of brief duration. Autopsy of animals exposed to lethal concentrations showed mild to severe liver damage and nonspecific changes in the kidneys. Nitroethane was not hepato-toxic after administration of 9mmol/kg to mice.  

Nitromethane was not genotoxic in Salmonella typhimurium tester strains.  

The liquid is a mild skin irritant due to solvent action. 

---

Figure 5 shows the isothermal data of Edwards (1962) for n-hexane and nitroethane. This system also exhibits positive deviations from Raoult s law however, these deviations are much larger than those shown in Figure 4. At 45°C the mixture shown in Figure 5 is only 15° above its critical solution temperature. Again, representation with the UNIQUAC equation is excellent.

Table 5.4 gives the specific energies of selected organic liquid compounds. Compared with the isooctane chosen as the base reference, the variations from one compound to another are relatively small, on the order of 1 to 5%, with the exception of some particular chemical structures such as those of the short chain nitroparaffins (nitromethane, nitroethane, nitropropane) that are found to be energetic . That is why nitromethane, for example, is recommended for very small motors such as model airplanes it was also used in the past for competitive auto racing, for example in the Formula 1 at Le Mans before being forbidden for safety reasons. 

Sengers and coworkers (1999) have made calculations for the coexistence curve and the heat capacity of the real fluid SF and the real mixture 3-methylpentane + nitroethane and the agreement with experiment is excellent their comparison for the mixture [28] is shown in figure A2.5.28. 

Figure A2.5.28. The coexistence curve and the heat capacity of the binary mixture 3-methylpentane + nitroethane. The circles are the experimental points, and the lines are calculated from the two-tenn crossover model. Reproduced from [28], 2000 Supercritical Fluids—Fundamentals and Applications ed E Kiran, P G Debenedetti and C J Peters (Dordrecht Kluwer) Anisimov M A and Sengers J V Critical and crossover phenomena in fluids and fluid mixtures, p 16, figure 3, by kind pemiission from Kluwer Academic Publishers.

Since aliphatic hydrocarbons (unlike aromatic hydrocarbons, p. 155) can be directly nitrated only under very special conditions, indirect methods are usually employed for the preparation of compounds such as nitroethane, CjHsNO. When ethyl iodide is heated with silver nitrite, two isomeric compounds are formed, and can be easily separated by fractional distillation. The first is the true ester, ethyl nitrite, C,HiONO, of b.p. 17° its identity is shown by the action of hot sodium hydroxide solution, which hydrolyses it, giving ethanol and... 

C2H5ONO + NaOH C2H5OH + NaNOa sodium nitrite. The second compound is nitroethane, C,H NO, of b.p. 114° its identity is clearly shown by the action of reducing agents, which convert it into ethylamiiie, CjHjNHj, thus proving the presence of a nitrogen carbon... 

Nitroethane may be similarly obtained from sodium a chloropropionate. This is a general reaction for a chloro carboxylic acids, but in practice only monochloroacetic acid and a chloropropionic acid are readily available. 

The simpler nitrop>arafIins (nitromethane, nitroethane, 1- and 2-nitroproj)ane) are now cheap commercial products. They are obtained by the vapour phase nitration of the hydrocarbons a gaseous mixture of two mols of hydrocarbon and 1 mol of nitric acid vapour is passed through a narrow reaction tube at 420-476°. Thus with methane at 476° a 13 per cent, conversion into nitro methane is obtained ethane at 420° gives a 9 1 mixture of nitroethane (b.p. 114°) and nitromethane (b.p. 102°) propane at 420° afifords a 21 per cent, yield of a complex mixture of 1- (b.p. 130-6°) and 2-nitropropane (b.p. 120°), nitroethane and nitromethane, which are separated by fractional distillation. 

In a flask the chemist mixes 50g piperonal into 200mL glacial acetic acid, then adds 45mL nitroethane and 17g ammonium acetate. The solution is then refluxed 4 hours and takes on the color of yellow to yellow-orange. After 4 hours and cooling, yellowish crystals of p-nitropropene will spontaneously form. If not, the solution can be diluted with 50ml of dHjO and chilled in an ice bath for an hour to form the crystals with some slushy glacial acetic acid and water intermixed. The mass of crystals is broken up and plopped into a Buchner funnel to be vacuum filtered. The filter cake is washed with a little extra acetic acid or water. All of the filtrate is saved. 

It has been shown that by doubling the amount of nitroethane respective to that of the aldehyde in a ratio of 2 to 1, then the amount of ammonium acetate used can be reduced considerably [28 p703J. 

Russian articles make some outrageous claims and this one is no different [43], These mothers claim that piperonal or benzaldehyde will react with nitroethane by sitting in the dark at 10°C with only a couple of drops of ethylenediamine. Almost 100% yield no less Strike has never tried this nor does Strike fall for Russian science, but if anyone is interested... 

Nitroethane and 1-(3,4 methylenedioxy) 2- nitropropane This method of producing the above mentioned nitro compounds is by far the best Ritter has come across yet The problem with standard nitroethane synthesis is that the -NO2 source most commonly used is silver nitrite (a la Merck Index citing). Needless to say, this is going to be an expensive compound to make as it is not available commercially but must be synthesized from costly silver nitrate. The other methods mentioned in Vogels 5th masterpiece... 

Strike couldn t find any decent nitroethane synths except for a couple of Chemical Abstract articles. One suggestion is to treat 1.5 moles of Na2C02 with 1 mole of sodium ethylsulfite and 0.0645 moles of K2CO3 at 125-130°C. Another route would be to use silver nitrate and ethyl iodide [8 p119]. This type of reaction has been used to nitrate other paraffins and would probably work. 

Chemoselective C-alkylation of the highly acidic and enolic triacetic acid lactone 104 (pAl, = 4.94) and tetronic acid (pA, = 3.76) is possible by use of DBU[68]. No 0-alkylation takes place. The same compound 105 is obtained by the regioslective allylation of copper-protected methyl 3,5-dioxohexano-ate[69]. It is known that base-catalyzed alkylation of nitro compounds affords 0-alkylation products, and the smooth Pd-catalyzed C-allylation of nitroalkanes[38.39], nitroacetate[70], and phenylstilfonylnitromethane[71] is possible. Chemoselective C-allylation of nitroethane (106) or the nitroacetate 107 has been applied to the synthesis of the skeleton of the ergoline alkaloid 108[70]. 

The telomer 145 of nitroethane was used for the synthesis of recifeiolide (148)[121], The nitro group was converted into a hydroxy group via the ketone and the terminal double bond was converted into iodide to give 146. The ester 147 of phenythioacetic acid was prepared and its intramolecular alkylation afforded the 12-membered lactone, which was converted into recifeiolide (148),... 

Chloro-5-methoxy Nitroethane, NH4OAC. AcjO AIH3 47,97 [9]... 

Nitro-Disc Nitrodisc Nitro-Dur Nitro-dur Nitro-Dur Nitro dyes Nitroesters Nitroethane Nitroethane [79-24-3]... 

RocketPropella.nts, Liquid propellants have long been used to obtain maximum controUabiUty of rocket performance and, where required, maximum impulse. Three classes of rocket monopropellants exist that differ ia the chemical reactions that release energy (/) those consisting of, eg, hydrogen peroxide, ethylene oxide, C2H4O and nitroethane, CH2CH2NO2 that can undergo internal oxidation—reduction reactions (2) those... 

Nitrations can be performed in homogeneous media, using tetramethylene sulfone or nitromethane (nitroethane) as solvent. A large variety of aromatic compounds have been nitrated with nitronium salts in excellent yields in nonaqueous media. Sensitive compounds, otherwise easily hydroly2ed or oxidized by nitric acid, can be nitrated without secondary effects. Nitration of aromatic compounds is considered an irreversible reaction. However, the reversibihty of the reaction has been demonstrated in some cases, eg, 9-nitroanthracene, as well as pentamethylnitrobenzene transnitrate benzene, toluene, and mesitylene in the presence of superacids (158) (see Nitration). 

Nitromethane, nitroethane, 1-nitropropane, and 2-nitropropane are produced by a vapor-phase process developed ia the 1930s (2). 

---