Synthesis of dinitroglycerin

Preparation of dinitroglycerin

Glycerin dinitrate is formed from glycerin and nitric acid according to the equation:

Preparation of dinitroglycerin

Preparation of dinitroglycerin

100 parts of glycerin require 137 parts of nitric acid monohydrate, giving theoretically 197.8 parts of the dinitrate. Since this esterification proceeds by stages, embracing three possible steps, dinitroglycerin is never formed alone, but is always accompanied by the two other possible stages, namely the mononi­trate and the trinitrate to a greater or lesser extent. If glycerin is added to 3 to 5 times its quantity of highly concentrated nitric acid, a mixture of di and trinitrate is formed after standing for some time, which remains dissolved in the nitric acid. The less the nitric acid used the poorer the mixture in trinitrate. The more the nitric acid present the further is the esterification in the sense of trinitrate formation. The velocity of reaction is considerably less than in the esterification by mixed acid, and equilibrium is attained only after long standing, in some cases for several hours. If a quantity of nitric acid equal to 3 to 4 times the weight of the glycerin is poured into the glycerin, so that at first the latter is in excess and never comes into contact with highly concentrated acid, mostly the dinitrate is formed, with a little mononitrate, while in the opposite case the glycerin first dissolves in the still highly concen­trated acid, forming at first the trinitrate. If glycerin is poured into a mixture of nitric and sulfuric acids high in water and low in nitric acid, there is formed nitrogly­cerine containing proportions of dinitroglycerin dependent upon the quantity and concentration conditions. The same thing occurs if the quantity of sulfuric acid present is insufficient to combine with the water up to the point of complete formation of the trinitrate. In order to obtain pure dinitroglycerin, free from nitroglycerin, the crude product is dissolved in a larger quantity (13 to 15 times) of water, separated from the undissolved nitroglycerin, and the aqueous solution extracted by ether. The dinitroglycerin can also be obtained from the aqueous solution by distilling off the water under a vacuum. By repeated solution in water and extraction it can be freed from the last traces of nitroglycerin. In thin layers over sulfuric acid, or by gentle heating at 40 to 50° C the aqueous dinitroglycerin can be readily and completely dried.

Nitroglycerine and Nitroglycerine Explosives, by P Naoum, 162-163, 1928

IUPAC Name

(2-hydroxy-3-nitrooxypropyl) nitrate

InChI

InChI=1S/C3H6N2O7/c6-3(1-11-4(7)8)2-12-5(9)10/h3,6H,1-2H2

InChI Key

ASIGVDLTBLZXNC-UHFFFAOYSA-N

Canonical SMILES

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

MeSH Synonyms

1,2-dinitroglycerol, 1,2-glyceryl dinitrate, 1,3-dinitroglycerol, dinitroglycerol, glyceryl 1,2-dinitrate, glyceryl 1,3-dinitrate, glyceryl dinitrate, glyceryl-1,2-dinitrate, glyceryl-1,3-dinitrate, propanetriol 1,2-dinitrate, propanetriol 1,3-dinitrate

Depositor-Supplied Synonyms

1,3-Dinitroglycerin, 1,3-Glyceryl dinitrate, 1,3-Dinitroglycerol, 1,3-Dng, 1,2,3-Propanetriol, 1,3-dinitrate, Glyceryl-1,3-dinitrate, GLYCEROL, 1,3-DINITRATE, Glycerol-1,3-dinitrate, 623-87-0, CHEBI:18921, ASIGVDLTBLZXNC-UHFFFAOYSA-N, 1,2,3-propanetriol 1,3-dinitrate, Glycerol-1,3-dinitrate [Forbidden], BRN 1784163, 2-hydroxy-3-(nitrooxy)propyl nitrate, c0063, propanetriol 1,3-dinitrate, AC1L1Z2I, CHEMBL1634, UNII-3P3G498O9T, SCHEMBL2728056, CTK5B5003, 1,3-GDN, 3P3G498O9T, 1,2,3-Propanetriol,1,3-dinitrate, 2-hydroxypropane-1,3-diyl dinitrate, ZINC31483506, (2-hydroxy-3-nitrooxypropyl) nitrate, AKOS006272811, LS-72128, OR184946, DB-008023, 1,2,3-Propanetriol, 1,3-dinitrate (9CI), 3B1-006772, 3B3-067242

Removed Synonyms

Glycerol-1,2-dinitrate, C3H6N2O7, CID12200, 1,2,3-propanetriol 1,2-dinitrate, 2-01-00-00591 (Beilstein Handbook Reference)

IUPAC Name

(1-hydroxy-3-nitrooxypropan-2-yl) nitrate

InChI

InChI=1S/C3H6N2O7/c6-1-3(12-5(9)10)2-11-4(7)8/h3,6H,1-2H2

InChI Key

GFVHBTOOPNJKLV-UHFFFAOYSA-N

Canonical SMILES

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

MeSH Synonyms

1,2-dinitroglycerol, 1,2-glyceryl dinitrate, 1,3-dinitroglycerol, dinitroglycerol, glyceryl 1,2-dinitrate, glyceryl 1,3-dinitrate, glyceryl dinitrate, glyceryl-1,2-dinitrate, glyceryl-1,3-dinitrate, propanetriol 1,2-dinitrate, propanetriol 1,3-dinitrate

Depositor-Supplied Synonyms

1,2-Dinitroglycerin, Dinitroglycerol, Glyceryl-1,2-dinitrate, Glycerol, 1,2-dinitrate, Glycerol dinitrate, 1,2-Dinitroglycerol, Glyceryl 1,2-dinitrate, 621-65-8, CHEBI:18898, 3-hydroxypropane-1,2-diyl dinitrate, 1,2,3-Propanetriol, 1,2-dinitrate, BRN 1788957, 27321-62-6, 2,3-bis(nitrooxy)propan-1-ol, Dinitroglycerine, glyceroldinitrate, 1,2-Glyceryl Dinitrate, AC1L2WLS, propanetriol 1,2-dinitrate, AC1Q28KH, CHEMBL1635, Ex088, SCHEMBL462502, CTK5B4440, GFVHBTOOPNJKLV-UHFFFAOYSA-N, EINECS 248-402-7, 1,2,3-Propanetriol,1,2-dinitrate, AR-1I5901, c0062, AKOS006272810, LS-72127, OR017149, OR189029, OR251398, OR303554, 1,2-DINITROGLYCERIN, 100 UG/ML, (1-hydroxy-3-nitrooxypropan-2-yl) nitrate, DB-008015, 1,2,3-Propanetriol, 1,2-dinitrate (9CI), 1-01-00-00272 (Beilstein Handbook Reference), 3B1-006744, 3B3-067241

Removed Synonyms

Glycerol-1,3-dinitrate, C3H6N2O7, 1,2,3-Propanetriol, dinitrate, UNII-8542I4GE54, CID79076, 1,2,3-propanetriol 1,3-dinitrate, 6324-58-9

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