3-Chloro-4-(dichloromethyl)-2(5H)-furanone

201.43 g/mol

201.44

427RD33L4C

DTXSID6021535

26.3 Ų

log Kow = 0.95 (est)

42.5-44.5 °C

In water, 6,602 mg/L at 25 °C (est)

2.34X10-3 mm Hg at 25 °C (est)

Henry's Law constant = 6.76X10-6 atm-cu m/mole at 25 °C (est)

Hydroxyl radical reaction rate constant = 7.30X10-12 cu cm/molec-sec at 25 °C (est)|Ozone rate constant = 1.06X10-17 cu cm/molec-sec at 25 °C (est)

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

During a survey of 12 U.S. water treatment plants conducted between 2000-2002, the highest level of halogenated furanones (as a sum) occurred at a plant that disinfected water containing 11.3 mg/L of TOC and 0.27 mg/L of bromide with chlorine-chloramines (2380 ng/L in plant effluent drinking water) and at a plant that disinfected water containing 3.5 mg/L of TOC and 0.21 mg/L of bromide with chlorine dioxide-chlorine-chloramines (1000 ng/L in the distribution system). The authors noted that an effort was made to selects plants that treat water with high TOC and/or bromide to enable detection of priority disinfection byproducts. The median concentration of halogenated furanones (as a sum, measured in plant effluent) was 310 ng/L, with a 75th percentile concentration of 610 ng/L and a maximum concentration of 2,380 ng/L(1). /Halogenated furnanones/|3-Chloro-4-dichloromethyl)-2(5H)-furanone concentrations in six pairs of US drinking water plants from different geographical regions as defined by the EPA(1). [Table#7334]

3-Chloro-4-(dichloromethyl)-2-(5H)-furanone's formation in water as a result of chlorine-treatment processes(1) may result in its release to the environment through various waste streams(SRC). Disinfection byproducts are formed when chlorine or other disinfectants, which are used to control contaminants in drinking water, react with naturally occurring organic and inorganic matter present in water(2).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 59(SRC), determined from a structure estimation method(2), indicates that 3-chloro-4-(dichloromethyl)-2-(5H)-furanone is expected to have high mobility in soil(SRC). Volatilization of 3-chloro-4-(dichloromethyl)-2-(5H)-furanone from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.7X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 3-Chloro-4-(dichloromethyl)-2-(5H)-furanone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.3X10-3 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2008).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 59(SRC), determined from a structure estimation method(2), indicates that 3-chloro-4-(dichloromethyl)-2-(5H)-furanone is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 6.7X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 7.9 days and 62 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3.2(SRC), from an estimated log Kow of 0.95(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2008).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3-chloro-4-(dichloromethyl)-2-(5H)-furanone, which has an estimated vapor pressure of 2.3X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 3-chloro-4-(dichloromethyl)-2-(5H)-furanone is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2.2 days(SRC), calculated from its rate constant of 7.4X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 3-Chloro-4-(dichloromethyl)-2-(5H)-furanone contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of 3-chloro-4-(dichloromethyl)-2-(5H)-furanone with photochemically-produced hydroxyl radicals has been estimated as 7.4X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.2 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of 3-chloro-4-(dichloromethyl)-2-(5H)-furanone with ozone has been estimated as 1.1X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.1 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). 3-Chloro-4-(dichloromethyl)-2-(5H)-furanone is expected to undergo hydrolysis in the environment due to the presence of functional groups that hydrolyze under environmental conditions(3). 3-Chloro-4-(dichloromethyl)-2-(5H)-furanone contains chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3.2 was calculated in fish for 3-chloro-4-(dichloromethyl)-2-(5H)-furanone(SRC), using an estimated log Kow of 0.95(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 3-chloro-4-(dichloromethyl)-2-(5H)-furanone can be estimated to be 59(SRC). According to a classification scheme(2), this estimated Koc value suggests that 3-chloro-4-(dichloromethyl)-2-(5H)-furanone is expected to have high mobility in soil.

The Henry's Law constant for 3-chloro-4-(dichloromethyl)-2-(5H)-furanone is estimated as 6.7X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 3-chloro-4-(dichloromethyl)-2-(5H)-furanone is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 7.9 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 62 days(SRC). 3-Chloro-4-(dichloromethyl)-2-(5H)-furanone's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 3-Chloro-4-(dichloromethyl)-2-(5H)-furanone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.3X10-3 mm Hg(SRC), determined from a fragment constant method(3).

The most likely pathway by which the general public is exposed to this compound is by ingestion of and dermal contact with chlorinated drinking water and effluent. (SRC)

Disinfection byproducts are formed when disinfectants used in water treatment plants react with bromide and/or natural organic matter (i.e., decaying vegetation) present in the source water. /Disinfection byproducts/