Alkyl nitrate

Many alkyl alcohols will dehydrate to an ester on addition of nitric acid with loss of water. This process, called nitration, causes the formation of a nitroxy group on the carbon atom.

MeOH + HNO₃ → MeONO₂ + H₂O

Single Alcohol Nitrate Esters

• Methanol / Methyl nitrate
• Ethanol / Ethyl nitrate
• Isopropanol / Isopropyl nitrate

Non-Cyclic Alkyl Polyol Nitrate Esters

• Ethylene glycol / Ethylene glycol dinitrate
• Propylene glycol / Propylene glycol dinitrate
• Glycerol / Glycerol trinitrate (nitroglycerin)
• Erythritol / Erythritol tetranitrate
• Xylitol / Xylitol pentanitrate
• Sorbitol / Sorbitol hexanitrate
• Isosorbitol / Isosorbitol dinitrate
• Mannitol / Mannitol hexanitrate
• Pentaerythritol / Pentaerythritol tetranitrate

Cyclic Polyol Nitrate Esters

• Inositol / Inositol hexanitrate

• Cellulose / Nitrocellulose

• Sucrose / Sucrose octanitrate

Properties

Alkyl nitrates are oily liquids or colorless solids, insoluble in water, but more soluble in organic solvents. Due to vasodilatory effects, nitrate esters can cause strong headaches, because blood vessels in the brain widen. The more volatile the ester is, the simpler it is to get a "nitrate headache".

Handling

Safety

Most alkyl nitrates tend to be explosive, which means proper protection must be worn when working with said compounds.