Toluol-3,5-diamin

TERRESTRIAL FATE: By analogy to similar aromatic amines, when toluene-3,5-diamine is released to soil it may undergo a covalent chemical bonding with humic materials which can result in its chemical alteration to a latent form and tight adsorption(1); when covalently bound in this latent form, leaching in soil systems is not generally expected to occur(1). This covalent bonding proceeds in two steps(1); a rapid and reversible bonding followed by a slower and much less reversible reaction(1). Leaching in soil may be possible prior to the occurrence of the slower bonding reaction. In the absence of covalent bonding, leaching may be possible based upon an estimated Koc of 1.34(2,SRC). A single biological screening study has indicated that toluene-3,5-diamine is resistant to biodegradation(3); however, insufficient data are available to assess the relative importance of biodegradation in soil(SRC).

AQUATIC FATE: By analogy to similar aromatic amines(1), toluene-3,5-diamine may undergo covalent bonding with humic materials in the water column and in sediment(1); partitioning from the water column to sediment and suspended material may therefore be an important transport mechanism. By analogy to the aromatic amine chemical class(2), toluene-3,5-diamine in the water column may be susceptible to photooxidation via hydroxyl and peroxy radicals. A single biological screening study has indicated that toluene-3,5-diamine is resistant to biodegradation(3); however, insufficient data are available to assess the relative importance of biodegradation in water. Aquatic hydrolysis, volatilization, and bioconcentration do not appear to be environmentally important(SRC).

ATMOSPHERIC FATE: Based upon an estimated vapor pressure of 0.00159 mm Hg at 25 °C(1), toluene-3,5-diamine is expected to exist primarily in the vapor-phase in the ambient atmosphere(2,SRC). It is degraded relatively rapidly in an average ambient atmosphere by reaction with photochemically produced hydroxyl radicals at an estimated half-life rate of about 1.6 hr(3,SRC).

Aromatic amines (such as the toluidine isomers) have been observed to undergo rapid and reversible covalent bonding with humic materials in aqueous solution; the initial bonding reaction is followed by a slower and much less reversible reaction believed to represent the addition of the amine to quinoidal structures followed by oxidation of the product to give an amino-substituted quinone; these processes represent pathways by which aromatic amines may be converted to latent forms in the biosphere(1). In the absence of covalent bonding, a Koc value of approximately 1.34 can be estimated from toluene-3,5-diamine estimated log Kow of 0.337(2) using an appropriate regression-derived equation(3,SRC); this Koc values indicates very high soil mobility(4).

Environmental and medical surveys were conducted ... to evaluate dinitrotoluene and toluenediamine exposures /of/ workers. ... Dinitrotoluene and toluenediamine concentrations ranged from 0.013-0.42 mg/cu m during the initial survey and from undetectable to 0.10 mg/cu m during the follow-up survey. ... Medical findings included a significant reduction in sperm count among exposed workers. A slight excess of miscarriages among the wives of exposed workers was found, but could not be conclusively related to the exposures. ...

... Toluenediamine used as a dye on the eyelashes is reported in one instance to have caused keratoconjunctivitis and blepharitis with opacities of the cornea which gradually cleared in the course of several weeks. /Toluenediamine/

Toluene-3,5-diamine is formed as a minor by-product during the industrial manufacture of other toluenediamine isomers, such as the 2,4- and 2,6-isomers(1); wastewater streams generated at sites of 2,4- and 2,6-toluenediamine manufacture contain toluenediamine isomers(2).

Based on an estimated log Kow of 0.337(1), the bioconcentration factor (BCF) for toluene-3,5-diamine can be estimated to be 1.06 from a recommended regression-derived equation(2,SRC). This BCF value is not indicative of significant bioconcentration in aquatic organisms(SRC).

The Henry's Law constant for toluene-3,5-diamine can be estimated to be 7.43X10-10 atm-cu m/mole using a structure estimation method(1,SRC); this value of Henry's Law constant indicates that a compound is essentially non-volatile from environmental waters(2).

Certain diamines (eg, toluenediamine and diaminodiphenylmethane) have potent hepatotoxic effect in experimental animals ... . /Toluenediamines/

The toluenediamines appear not to be primary irritants, according to tests on rabbit eyes in which 0.02 M solutions of each of the isomers all at pH 6.5 were tested by dropping on rabbit eyes for ten minutes after mechanical removal of the corneal epithelium to permit penetration. The eyes healed and returned to normal within two to four days without evidence of chemical injury. /Toluenediamines/

The rate constant for the vapor-phase reaction of toluene-3,5-diamine with photochemically produced hydroxyl radicals has been estimated to be 2.4X10-10 cu cm/molecule-sec at 25 °C which corresponds to an atmospheric half-life of about 1.6 hr at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Aromatic amines are generally resistant to aqueous environmental hydrolysis(2); therefore, toluene-3,5-diamine is not expected to hydrolyze in water(SRC). As a class, aromatic amines react relatively rapidly in sunlit natural water via reaction with photochemically produced hydroxyl radicals and peroxy radicals(3); typical half-lives for hydroxyl radical and peroxy radical reaction are on the order of 19-30 sunlight hours(3); however, rate data specific to toluene-3,5-diamine were not located(SRC).

Toluene-3,5-diamine is formed as a minor by-product during the industrial manufacture of other toluenediamine isomers(1); occupational exposure to toluenediamines occurs through dermal contact and inhalation, with skin contact being the most likely route of exposure(2).

Toluene-3,5-diamine may be released to the environment in wastewater streams generated at sites of industrial 2,4- and 2,6-toluenediamine manufacture. If released to the atmosphere, toluene-3,5-diamine is expected to degrade relatively rapidly (estimated half-life of 1.6 hr) by reaction with photochemically produced hydroxyl radicals. If released to soil, toluene-3,5-diamine may undergo a covalent chemical bonding with humic materials which can result in its chemical alteration to a latent form and prevent leaching. In the absence of covalent bonding, leaching may be possible. If released to water, covalent bounding with humic materials in the water column and sediments may result in partitioning from the water column to sediments. By analogy to the aromatic amine chemical class, toluene-3,5-diamine in the water column may be susceptible to photooxidation via hydroxyl and peroxy radicals. A single biological screening study has indicated that toluene-3,5-diamine is resistant to biodegradation; however, insufficient data are available to assess the relative importance of biodegradation in soil or water. Occupational exposure to toluene-3,5-diamine may occur through dermal contact and inhalation, with skin contact being the most likely route of exposure. (SRC)

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,3-Benzenediamine, 5-methyl is included on this list.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble of the 51 FR 41329.