The environmental fate of 3-Aminophenol

3-Aminophenol is  a kind of white crystals with formula C6H4(NH2)(OH). It is an aromatic amine and aromatic alcohol. It is an isomer of 2-aminophenol and 4-aminophenol. It can be prepared by caustic fusion of metanilic acid.One of the most relevant applications of the substance is the synthesis of 3-(diethylamino)phenol, key intermediate for the preparation of several fluorescent dyes.

A method of dehydrogenating 3-amino-2-cyclohexene-1-one with a supported palladium or palladium-platinum catalyst in a solvent in the presence of base to produce 3-Aminophenol(CAS NO:591-27-5) and its use directly without purification to produce 3,4'-oxydianiline.

3-Aminophenol is purified by vacuum distillation. Alternatively, resorcinol reacts with ammonia, for example, in the presence of diammonium phosphate and arsenic pentoxide or ammonium sulfite to form 3-aminophenol. The compound also may be made by hydrolysis of 3-aminoaniline.

3-Aminophenol's production and use as a hair dye and chemical intermediate may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 1.86X10-3 mm Hg at 25 deg C indicates 3-aminophenol will exist solely as a vapor in the atmosphere. 

3-Aminophenol absorbs light at wavelengths of 270 nm (0.1 M HCl) and therefore is not expected to be susceptible to direct photolysis by sunlight. If released to soil, it is expected to have high mobility based upon an estimated Koc of 90. However, anilines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group, suggesting that mobility may be much lower in some soils. 

3-Aminophenol is amphoteric and behaves either as a weak acid or weak base; the basic character usually predominates. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 2.7X10-10 atm-cu m/mole. Utilizing the Japanese MITI test, 0% of the theoretical BOD was reached in 4 weeks, indicating that biodegradation may not be an important environmental fate process. 

If released into water, 3-aminophenol may adsorb to suspended solids and sediment based upon the estimated Koc. Based on two grab studies, 3-aminophenol(CAS NO:591-27-5) appears to be slowly mineralized, from 0.4 to 0.7% per day, in aquifer solids and degraded by 37% in 16 days in soil. 

Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to it may occur through dermal contact with this compound at workplaces where it is produced or used. Use data indicate that the general population may be exposed to 3-aminophenol via dermal contact with consumer products, particularly hair dye products, containing 3-aminophenol. 

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