Benzyl alcohol is composed of the molecular formula C6H5CH2OH. It is known by several chemical names, including, Phenylmethanol, Benzenemethanol, Phenylcarbinol and Hydroxytoluene. Benzyl alcohol is a liquid that has a slight odor, intense burning taste and no color. It is naturally produced by plants and found in many teas and fruits. Benzyl alcohol is prepared using sodium hydroxide for the hydrolysis of benzyl chloride, with a molecular formula of C6H5CH2Cl + NaOH → C6H5CH2OH + NaCl. Benzyl alcohol can additionally be prepared by reacting phenylmagnesium bromide with formaldehyde, then by acidification, known as a Grignard reaction.
Benzyl alcohol has a molecular weight of 108.14 g/mol, a melting point of -15.2°C and a boiling point of 205.3°C. It is similar to most alcohols in that it forms esters in reaction to carbolic acids. In a Ritter reaction, benzyl alcohol reacts with acrylonitrile to give
N-benzylacrylamide. Benzyl alcohol can be found in castoreum, which occurs naturally in the castor sacs of beavers.
Benzyl alcohol metabolizes to benzoic acid, which is excreted as hippuric acid when it reacts with glycine. The PubChem CID of Benzyl alcohol is 244 and its InChl Key is WVDDGKGOMKODPV-UHFFFAOYSA-N. The solubility of benzyl alcohol in water is 3.50 g/100 mL (20 ° C), 4.29 g/100 mL (25 ° C). It is soluble in methanol, benzene, ethanol, acetone, chloroform and ether.
Benzyl alcohol is found in various essential oils including ylang-ylang, jasmine and hyacinth. It is utilized commonly as a general solvent for paints, shellacs, waxes, inks, epoxy resin coatings and lacquers. When working in combination with viscosity enhancers, benzyl alcohol works in paint strippers as it aids the mixture in clinging to painted surfaces. Benzyl alcohol is used in flavor enhancers in flavored e-cigarettes as well as fragrances in perfumes and soaps. It is also used occasionally as a degreaser in products manufactured for cleaning rugs and can enhance the process of dying nylon, leather and wool as a dye solvent.
Benzyl alcohol is used in the medical field in a variety of ways. It has been used in low concentration in reducing pain as a topical agent when Lidocaine is injected. It is used as a Pediculicide and for treating head lice in adults and children over 6 months old by stopping the louse’s spiracles from closing. The insects eventually die from asphyxiation because their spiracles become clogged with mineral oil, water or other substances. In nanotechnical uses, benzyl alcohol has been used to reconfigure nanowires as a dielectric solvent.
When it comes to safety, benzyl alcohol can be toxic in very high concentrations and should be used safely at concentrations of 5% and below. It is not a sensitizer at 10%. Too much may lead to hypotension, respiratory failure, vasodilation, paralysis and convulsions. Benzyl alcohol is associated with neonate gasping syndrome and can cause skin allergies. It is very toxic to eyes and in its pure form, benzyl alcohol creates corneal necrosis. In hair dyes, benzyl alcohol is considered safe up to 10%.