Synthesis of ethyl nitrite

Preparation of ethyl nitrite

Preparation of ethyl nitrite from ethyl alcohol and sodium nitrite

Preparation of ethyl nitrite from ethyl alcohol and sodium nitrite

Preparation of ethyl nitrite from ethyl alcohol and sodium nitrite

40 ml of sulfuric acid (d=1.84) are added to 120 ml of water, followed, after cooling, by a mixture of 85 ml of alcohol (90 %) and 85 ml of water. The mixture is cooled to 0° C, when a filtered solution of 100 g of sodium nitrite in 280 ml of water is added drop by drop, the temperature being kept below +5° C. When all has been added, the liquid portion is decanted from crystals of sodium sulfate, and transferred to a cooled separator, in which the ethyl nitrite layer is separated. It is washed, first with 20 ml of ice-cold water, then with 15 ml of water containing 0.6 % of sodium carbonate (monohydrate), and dried, after careful separation, by agitation with 3 parts of anhydrous potassium carbonate and filtered.

For the preparation of ethyl nitrite solution in ethanol following procedure is used:

Preparation of ethyl nitrite from ethyl alcohol and nitric acid

Preparation of ethyl nitrite from ethyl alcohol and nitric acid

100 of sulfuric acid (d=1.84) are added to 1000 ml of 90 % ethyl alcohol, followed by 125 ml of nitric acid (d=1.4), with cooling and stirring. 100 g of copper turnings are then added and the mixture gently distilled, the commencing temperature being 77° C. The receiver contains 1000 ml of 90 % alcohol, which is cooled to 0° C. Distillation is continued until the volume in the receiver has increased to 1600 g; the contents of the still are then allowed to cool, when 25 ml more of nitric acid are added, after which distillation is resumed, and continued until a further 100 g of distillate have been collected.

Organic medical chemicals, by M. Barrowliff, 223, 1921

Preparation of ethyl nitrite

Preparation of ethyl nitrite

42 g (a slight excess) of dry silver nitrite are placed in a round-bottomed flask fitted with a reflux condenser. To recover the by-product (nitroethane), ice-water must be used in the condenser, which should be a long one. 34 g of ethyl iodide are added, gradually, through the condenser tube, so that the liquid boils vigorously but not too violently. The flask must not be disturbed during the process, for it is important that the silver nitrite should be gradually penetrated by the iodide. The flask is then warmed for 2 hours on a water bath, well cooled, fitted to a distillation apparatus, and the contents fractionally distilled. Ethyl nitrite distils over at 68° C, and is collected in a flask cooled in a good freezing mixture. The temperature then rises and the second fraction, nitroethane, is collected at 110-114° C and redistilled. The yield of nitroethane is 50% theoretical (8-9 g). Colourless liquid insoluble in water ; b.p. 113-114° C; d=1.058 g/ml. The yield of ethyl nitrite 50% theoretical b.p. 17° C;

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

IUPAC Name

ethyl nitrite

InChI

InChI=1S/C2H5NO2/c1-2-5-3-4/h2H2,1H3

InChI Key

QQZWEECEMNQSTG-UHFFFAOYSA-N

Canonical SMILES

CCON=O

MeSH Synonyms

ethyl nitrite

Depositor-Supplied Synonyms

ETHYL NITRITE, Nitrous acid, ethyl ester, 109-95-5, Spirit of nitrous ether, Nitrous ether, Ethyl-nitrite-, Hyponitrous ether, Nitrosyl ethoxide, Nitrous ethyl ether, Ethyl nitrite spirit, Ethyl nitrite solution, Sweet spirit of niter, Sweet spirit of nitre, Spirit of ethyl nitrite, nitrous acid ethyl ester, UNII-8C7CJ279RV, FEMA No. 2446, HSDB 416, QQZWEECEMNQSTG-UHFFFAOYSA-N, Ethylester kyseliny dusite [Czech], EINECS 203-722-6, UN1194, BRN 1699562, NCGC00166242-01, AI3-25307, Ethylnitrite, Nitrethyl, Ethyl alcohol nitrite, Ethyl nitrite solutions, Ethyl nitrite [Spirit], Nitrous acid, ethylester, Ethylester kyseliny dusite, AC1L1Q3F, DSSTox_CID_26574, DSSTox_RID_81733, DSSTox_GSID_46574, NITRE, SWEET SPIRIT OF, 309923_ALDRICH, 8C7CJ279RV, Jsp000778, CHEMBL1551365, CTK4A6716, Tox21_112368, AN-42973, CAS-109-95-5, LS-96768, S683, KB-201090, E0152, FT-0626215, A802116, 3B4-2683, S14-1478, Ethyl nitrite solutions [UN1194] [Flammable liquid], Ethyl nitrite solutions [UN1194] [Flammable liquid], 8013-58-9

Removed Synonyms

Ethyl nitrile, CID8026, 4-01-00-01327 (Beilstein Handbook Reference)

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