Synthesis of mononitroglycerin

Preparation of mononitroglycerin

Alternative Names: 1-Mononitroglycerin; Glycerol, 1-nitrate; Glyceryl 1-mononitrate; Mononitroglycerol; 1-Mng; Glycerol-1-nitrat; 2-Mononitroglycerol; Glycerin 2-nitrate; Glycerol-2-nitrate; 2-Glyceryl mononitrate; Glycerol, 2-nitrate; Glycerol 2-mononitrate;

Preparation of mononitroglycerin

Preparation of mononitroglycerin

A mixture of 250 g of concentrated nitric acid and 50 g of concentrated sulfuric acid, very well cooled, was put into 100 g of glycerin. Toward the end of the operation, a temperature of 5 to 10° C being maintained, there was a great tendency toward oxidation, so that 300 parts of crushed ice was added at once, whereupon a small quantity of dinitroglycerin and trinitroglycerin mixture separated, which was drawn off. It was then extracted several times with ether, and the ether solution neutralized. The first extract yielded 26 g of a mixture of 40% dinitroglycerin and 60% mononitroglycerin. The second to eighth extracts inclusive gave 23 g of pure mononitroglycerin. The neutralized and evaporated solution gave 8 g more of the mononitrate on extraction of the salt residue. Since 100 parts of glycer­in theoretically give 149 parts of mononitrate the 47 g obtained corre­spond to about 30% of the theoretical yield. The separation of mononitroglycerin and dinitroglycerin is done by the different solubilities in water and ether. From a dilute solution of both nitrates in water ether easily removes the dinitroglycerin. The mononitroglycerin is then obtained by removal of the water in a vacuum, or by an intensive ether treatment of the concentrated solution.

Nitroglycerine and Nitroglycerine Explosives, by P Naoum, 171-172, 1928

IUPAC Name

2,3-dihydroxypropyl nitrate

InChI

InChI=1S/C3H7NO5/c5-1-3(6)2-9-4(7)8/h3,5-6H,1-2H2

InChI Key

HXWLJBVVXXBZCM-UHFFFAOYSA-N

Canonical SMILES

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

MeSH Synonyms

G-1-N, glycerin-1-nitrate, glycerol-1-nitrate, glycerol-1-nitrate, (+-)-isomer, glyceryl-1-nitrate

Depositor-Supplied Synonyms

1-Mononitroglycerin, Glycerol, 1-nitrate, Glyceryl 1-mononitrate, Mononitroglycerol, 1-Mng, Glycerol-1-nitrat, GLYCEROL 1-MONONITRATE, 1,2,3-Propanetriol, 1-nitrate, Glycerol-1-nitrate, Glycerol-1-nitrat [German], HXWLJBVVXXBZCM-UHFFFAOYSA-N, 624-43-1, BRN 1761580, 3-(nitrooxy)propane-1,2-diol, 1-Mononitroglycerol, 1-nitrate-1,2,3-propanetriol, Glycerin 1-nitrate, Glyceryl mononitrate, 1-Glyceryl mononitrate, AC1L1Z3F, 2,3-Dihydroxypropyl nitrate, CHEMBL1636, SCHEMBL62389, 1,2,3-Propanetriol, nitrate, 3-Nitrooxy-propane-1,2-diol, 2,3-Dihydroxypropyl nitrate #, 1,2,3-Propanetriol,1-nitrate, CTK5B5094, c0065, AKOS006272812, 1,2,3-Propanetriol, 1-nitrate (9CI), LS-72129, OR017137, OR189235, OR189236, OR251397, OR350039, 4-01-00-02761 (Beilstein Handbook Reference), 3B1-006778, 3B3-067243

Removed Synonyms

nitroglycerin, Nitroglycerine, GLYCEROL-?-NITRATE, 1,2,3-Propanetriol, mononitrate, CID12211, 27321-61-5

IUPAC Name

1,3-dihydroxypropan-2-yl nitrate

InChI

InChI=1S/C3H7NO5/c5-1-3(2-6)9-4(7)8/h3,5-6H,1-2H2

InChI Key

QYZBMMOLPVKAPU-UHFFFAOYSA-N

Canonical SMILES

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

MeSH Synonyms

glycerol-2-nitrate

Depositor-Supplied Synonyms

2-Mononitroglycerol, Glycerin 2-nitrate, Glycerol-2-nitrate, 2-Glyceryl mononitrate, Glycerol, 2-nitrate, Glycerol 2-mononitrate, 2-nitrooxy-propane-1,3-diol, 1,2,3-Propanetriol, 2-nitrate, 620-12-2, BRN 1765006, c0064, 2-NITROGLYCERIN, AC1L2BIH, 2-MONONITROGLYCERIN, AC1Q21WV, UNII-K3K9AJ5J41, SCHEMBL711996, CHEMBL462931, K3K9AJ5J41, 2-(nitrooxy)propane-1,3-diol, 1,2,3-Propanetriol,2-nitrate, CTK5B4156, 1,3-dihydroxypropan-2-yl nitrate, ZINC1845947, AR-1E4227, AKOS006275562, 1,2,3-Propanetriol, 2-nitrate (9CI), LS-72130, OR038399, OR189022, OR302408, 3B1-006732

Removed Synonyms

Cellulose PAB, 4-Aminobenzyl-cellulose, GLYCEROL-?-NITRATE, CID69280, 2-01-00-00591 (Beilstein Handbook Reference), 6315-32-8, 9032-51-3

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