Sodium hydrazide
| Names | |
|---|---|
| IUPAC name
Sodium hydrazide
| |
| Other names
Sodium aminoazanide
| |
| Properties | |
| NaN2H3 NaNH-NH2 | |
| Molar mass | 54.027 g/mol |
| Appearance | White to yellow crystalline solid |
| Odor | Odorless |
| Melting point | 100 °C (212 °F; 373 K) (Decomposes) |
| Boiling point | Decomposes |
| Reacts | |
| Solubility | Reacts with alcohols, acids[1] Soluble in anh. ammonia, hydrazine Insoluble in ethers, hydrocarbons |
| Vapor pressure | ~0 mmHg |
| Hazards | |
| Safety data sheet | None |
| Related compounds | |
| Related compounds
|
Hydrazine |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Sodium hydrazide is an organic chemical compound, a colorless or yellow crystalline compound that is known to explode violently in contact with air. It has the chemical formula NaN2H3.
Contents
Properties
Chemical
Sodium hydrazide explodes on contact with air or when heated at high temperatures.[2] It also reacts with water violently, yielding sodium hydroxide and hydrazine.[3]
- NaNH-NH2 + H2O → NaOH + NH2-NH2
Moisture and alcohol are also reported to result in explosion.[2]
Sodium hydrazide does not attack compounds containing isolated double bonds, apart from those in which the bond angle is strained. On the other hand, it adds onto C=C double bonds that are conjugated with a phenyl residue or another C=C double bond. Styrene, for example, adds on sodium hydrazide in ether very rapidly, even at 0 °C.[4]
Sodium hydrazide reacts with nitriles, followed by water, at low temperatures to yield amidrazones.[5]
Pyridine can be converted directly into 2-hydrazinopyridine by treatment with sodium hydrazide/hydrazine and subsequent hydrolysis with water.[6] If no free hydrazine is present, the reaction of sodium hydrazide with aromatic nitrogenous heterocycles like pyridine produces hydrazo compounds.[7]
Aliphatic ethers are unaffected by sodium hydrazide at 60 °C. Ethers with one or two aromatic residues are also fairly resistant: when heated at 50 °C for five hours with sodium hydrazide in benzene containing free hydrazine, anisole and diphenyl ether are split to the extent of only 9 and 21 %, respectively.
Physical
Sodium hydrazide is a white to yellowish crystalline compound, very soluble in anh. hydrazine[8] insoluble in organic solvents, but reacts (potentially explosively) with water and acids. It is known to react explosively in open air, or when heated at high temperatures.
Explosive
Sodium hydrazide is known to explode violently on contact with oxygen, such as atmospheric air, and also when heated above 100 °C. While most sources indicate that it is stable in an oxygen-free atmosphere, some sources claim it can be explosive even under nitrogen or hydrogen atmosphere, but no indications why.[9][10]
Availability
Sodium hydrazide is not sold by suppliers and has to be made in situ.
Preparation
Sodium hydrazide can be prepared by reacting finely divided sodium amide or sodium hydride with anhydrous hydrazine, under inert atmosphere. If the sodium amide is not finely divided, the reaction is very slow.[9]
- NaR + H2N-NH2 → NaNH-NH2 + R-H (R = NH2 or H)
Another way is the reaction of sodium metal with absolutely anhydrous hydrazine with benzene layered on top of it:[11]
- 2 Na + 3 N2H4 → 2 NaNHNH2 + 2 NH3
On very careful distillation (removing benzene and excess hydrazine) using a water bath at no more than 70 °C, very pure sodium hydrazide is left behind.[11]
Projects
- Pyrotechnic demonstration
- Prepare amidrazones
Handling
Safety
Sodium hydrazide is explosive in contact with air and poses a serious fire hazard.
Storage
Should not be stored and used immediately.
Disposal
There are several way to safely dispose of this compound: One involves slow addition of organic esters or long-chain alcohols, which are diluted in an inert solvent (like ether), under inert gas and diluted in another solvent, until the compound is neutralized completely. Another involves the addition of a nitrile compound, like acetonitrile, followed by the careful addition of water, which converts it to non-explosive amidrazones. A third method involves very slow decomposition under benzene using a dilute solution of alcohol in benzene has been used to decompose the substance without explosion. Afterwards (!) the solution can be neutralized with dilute aq. acids.[11]
References
- ↑ Comey A. M., Hahn D. A. A dictionary of Chemical Solubilities Inorganic. - 2 ed. - New York, The MacMillan Company, 1921 pp. 851
- ↑ 2.0 2.1 Gmelins Handbuch der anorganischen Chemie, Natrium, Berlin, Verlag Chemie GmbH, 8th edition 1928, p. 260-261
- ↑ Kauffmann, T.; Kosel, C.; Wolf, D.; Chemische Berichte; vol. 95; (1962); p. 1540 - 1551
- ↑ Angew. Chem. internat. Edit, Vol. 3 (1964) I No. 5, p. 342-353
- ↑ Th. Kauffmann, S. Spaude, and D. Wulf, Angew. Chem. 75, 344 (1963); Angew. Chem. internat. Edit. 2, 217 (1963)
- ↑ Th. Kauffmann, J. Hansen, Ch. Kosel, and W. Schoeneck, Liebigs, Ann. Chem. 656, 103 (1962)
- ↑ Th. Kauffmann, If. Hacker, and Ch. Kosel, Z. Naturforsch. 14h, 602 (1959)
- ↑ Некрасов Б.В. Основы общей химии. - Т.1. - М.: Химия, 1973 (Nekrasov B.V. Fundamentals of General Chemistry. - T.1. - M.: Chemistry, 1973)
- ↑ 9.0 9.1 T. W. B. Welsh, J. Amer. chem. Soc. 37, 497 (1915)
- ↑ https://onlinelibrary.wiley.com/doi/abs/10.1002/047084289X.rs072
- ↑ 11.0 11.1 11.2 W. Schlenk, T. Weichselfelder, Ber. Dtsch. Chem. Ges. 1915, 48, 669-676. https://doi.org/10.1002/cber.19150480190
Relevant Sciencemadness threads
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- Chemical compounds
- Inorganic compounds
- Sodium compounds
- Nitrogen compounds
- Hydrazines
- Energetic materials
- Primary explosives
- Hair-trigger explosives
- Things that should NOT be messed with except by professionals
- Things that can kill you very quickly
