Synthesis of nitromethane

Preparation of nitromethane (methane, nitro-;nitrocarbol; nitrometan; nitro-methane)

Preparation of nitromethane (methane, nitro-;nitrocarbol; nitrometan; nitro-methane)

Preparation of nitromethane (methane, nitro-;nitrocarbol; nitrometan; nitro-methane)

In a 1-liter distilling flask, containing, a mixture of 125 g of chloroacetic acid and 125 g of crushed ice, with stirring sufficient 40% sodium hydroxide solution (about 90 ml) is added to render the solution faintly alkaline to phenolphthalein (alternatively, the neutralization is achieved with about 75 g of finely powdered, anhydrous sodium carbonate added in small portions with frequent stirring or shaking). During the addition, the temperature is kept bellow 20° C in order to prevent the formation of sodium glycolate. Then a solution of 73 g of pure sodium nitrite dissolved in 100 ml of water is added into the flask, the distilling flask is connected to an efficient condenser set for downward distillation and the receiver is cooled in ice water. The reaction mixture is slowly warmed and when the temperature reaches 80-85° C evaluation of bubbles of carbon dioxide occurs. In order to avoid frothing and serious loss of nitromethane the heating source is removed and the reaction (decomposition of the sodium nitroacetate) sets in with the liberation of heat and the temperature rises to almost 100° C without external heating. During this exothermic process ~30 ml of nitromethane and ~40 ml of water, distil over. When the exothermic reaction apparently ceases (temperature below 90° C), the mixture is gently heated until the temperature rises to 110° C. The obtained distillate is transferred to a separatory funnel, and after 30 minutes the separation of the two layers is complete. The lower layer of nitromethane is removed, dried with· anhydrous calcium chloride or anhydrous calcium sulfate. Nitromethane is purified by distillation. The fraction boiling at 100-102° C is collected yielding 30 grams of pure nitromethane. A further small quantity (3-4 g) may be isolated by mixing the aqueous layer with one-quarter of its weight of sodium chloride, distilling, and separating the nitromethane from the distillate.

A text book of practical organic chemistry, by A. I. Vogel, 307-308, 1974

Preparation of nitromethane

Preparation of nitromethane

44 g of dry silver nitrite are mixed with an equal bulk of dry sand and placed in a reflux apparatus; 41 g of methyl iodide are gradually added, and the whole heated on a water bath for 2 hours. The mixture is then distilled from a water bath, the fraction 95-101° C being separately collected. It is redistilled over silver nitrite to remove the last traces of iodide. Nitromethane is heavy, inert, insoluble, colourless liquid; b.p. 101° C;

Systematic organic chemistry, by W. M. Cumming, 280, 1937.

Nitromethane can be obtained from the reaction of dimethyl sulfate with sodium nitrite (M. J. Decombe, Bull. Soc. Chini. France 1953, 1038)

IUPAC Name

nitromethane

InChI

InChI=1S/CH3NO2/c1-2(3)4/h1H3

InChI Key

LYGJENNIWJXYER-UHFFFAOYSA-N

Canonical SMILES

C[N+](=O)[O-]

MeSH Synonyms

nitromethane

Depositor-Supplied Synonyms

NITROMETHANE, Methane, nitro-, 75-52-5, Nitrocarbol, Nitrometan, nitro-methane, Nitrometan [Polish], NSC 428, CH3NO2, CCRIS 1205, HSDB 106, CHEBI:77701, LYGJENNIWJXYER-UHFFFAOYSA-N, EINECS 200-876-6, UN1261, AI3-00111, 104306-48-1, nitro methane, MeNO2, N,N-dihydroxymethanamine, Nitro fuel (Salt/Mix), DSSTox_CID_977, Nitromethane [UN1261] [Flammable liquid], ACMC-1BL9U, CH2NO2, UNII-RU5WG8C3F4, AC1L1ME0, AC1L42IX, AC1Q29QR, AC1Q29QS, WLN: WN1, DSSTox_RID_75900, RU5WG8C3F4, DSSTox_GSID_20977, KSC378C4T, Ex172, 108170_ALDRICH, 154946_ALDRICH, 230731_ALDRICH, 270423_ALDRICH, CHEMBL276924, NSC428, 02484_FLUKA, 73478_FLUKA, CTK2H8149, NSC-428, MolPort-000-871-968, 73478_SIAL, LTBB001387, 108170_SIAL, 154946_SIAL, 230731_SIAL, 270423_SIAL, 360554_SIAL, Tox21_200822, AKOS009031372, LS-1668, MCULE-8704524604, RP18259, RTR-037681, TRA0002607, UN 1261, CAS-75-52-5, NCGC00091494-01, NCGC00091494-02, NCGC00258376-01, AN-41994, InChI=1/CH3NO2/c1-2(3)4/h1H, Nitromethane [UN1261] [Flammable liquid], TR-037681, FT-0659976, N0019, N0209, N0239, C19275, A838443, 3B4-0605, S14-0988, NITROMETHANE (SEE ALSO FISH PROJECT (NITROMETHANE)), FISH PROJECT 1 (NITROMETHANE)(SEE ALSO NITROMETHANE)

Removed Synonyms

CID6375, C008640, NM

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