Diheptyl phthalate

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Removal of phthalate esters (PAEs) by alpha-cyclodextrin (CD)-linked chitosan bead in aqueous solution was studied. Results of kinetic experiments indicated that diheptyl phthalate (DHpP) was adsorbed most efficiently (3.21 mg/g) ... It was concluded that the application of low cost alpha-CD-linked chitosan bead could have the potential to effectively remove PAEs from different aquatic environments.

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The ability of phthalic acid, phthalic acid anhydride, and various phthalate esters to enhance the mutagenicity of many amino acid pyrolysates was observed with the Ames test (Salmonella typhimurium TA98), but not the SOS Chromotest. Phthalate enhancement of the mutagenicity of 4-nitroquinoline-1-oxide, 2-nitrofluorene, and benzo[a]pyrene was not observed with either test. The mutagenicity-enhancing ability may be related to the induction of enzymes such as P450IIB, that metabolize amino acid pyrolysates. By quantitative structure activity relationship (QSAR) analysis, a good correlation was observed between the mutagenicity-enhancing activity of phthalates and their octanol-water partition coefficients.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5.7X10+4(SRC), determined from a structure estimation method(2), indicates that diheptyl phthalate is expected to be immobile in soil(SRC). In sterile microcosms containing lake water and sediment, approximately 80% of a mixture of di(heptyl,nonyl,undecyl) phthalate partitioned to sediment(3). Volatilization of diheptyl phthalate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.5X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(4). However, adsorption to soil is expected to attenuate volatilization(SRC). Diheptyl phthalate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.1X10-6 mm Hg(SRC), determined from a fragment constant method(5). A 36% theoretical BOD in two weeks using an activated sludge inoculum in the Japanese MITI test suggests that biodegradation is expected to be an important process in soil(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5.7X10+4(SRC), determined from a structure estimation method(2), indicates that diheptyl phthalate is 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 3.5X10-6 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 20 and 150 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. According to a classification scheme(5), BCFs of 0.9 to 16.7(6), suggest the potential for bioconcentration in aquatic organisms is low(SRC). Hydrolysis is not expected to be an important process(SRC) based on estimated hydrolysis half-lives of 3.4 years and 130 days at pH 7 and 8, respectively(7). The mixture di(heptyl,nonyl,undecyl)phthalate had a half-life of 6 to 8 days in river die-away tests(8), suggesting that biodegradation is expected to be an important process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diheptyl phthalate, which has an estimated vapor pressure of 2.1X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase diheptyl phthalate 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 22 hours(SRC), calculated from its rate constant of 1.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase diheptyl phthalate may be removed from the air by wet or dry deposition(SRC). Diheptyl phthalate does contain chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

/AQUATIC SPECIES/ The extensive database of acute and chronic aquatic toxicity data for 18 phthalate esters was reviewed and summarized for freshwater and saltwater aquatic microorganisms, algae, invertebrates, and fish. Phthalate esters have been tested with six species of microorganisms, including bacteria and protozoans. Fifteen algal species have been tested, including green and bluegreen algae in both freshwater and saltwater. Nineteen freshwater and saltwater invertebrate species inhabiting surface waters and sediments and 21 freshwater and saltwater fish inhabiting cold and warm water bodies have been tested. The results of most studies indicate that acute and chronic toxicity to microorganisms, algae, aquatic invertebrates, and fish are limited to the lower molecular weight phthalate esters (i.e., dimethyl-, diethyl-, diallyl-, dipropyl-, dibutyl-, diisobutyl-, and butylbenzylphthalate). In contrast, higher molecular weight phthalate esters are not acutely or chronically toxic to aquatic organisms. Although conflicting data on chronic effects for high molecular weight phthalate esters have been reported for daphnids, these inconsistencies are attributed to physical effects imposed on daphnids when exposed to test concentrations in excess of true water solubilities. Altogether, nearly 400 test results covering more than 60 species of microorganisms, algae, invertebrates, and fish are reported for both freshwater and saltwater aquatic species. While most investigators used several common species and standard protocols to assay conventional endpoints, many nontraditional species and toxicological endpoints were also used. This has created a toxicological database of both sufficient depth to compare many similar tests and sufficient breadth to encompass virtually al important types of aquatic habitats and classes of aquatic species.

Using a structure estimation method based on molecular connectivity indices(1), the Koc of diheptyl phthalate can be estimated to be 5.7X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that diheptyl phthalate is expected to be immobile in soil. In sterile microcosms containing lake water and sediment, approximately 80% of di(heptyl,nonyl,undecyl) phthalate partitioned to sediment(3).

AEROBIC: Diheptyl phthalate present at 100 mg/L, reached 36% of its theoretical BOD in two weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(1,4). Diheptyl phthalate, added to an aerobic semi-continuous activated sludge apparatus at 5, 10, and 20 mg/24 hr, underwent 52, 48, and 54% degradation, respectively(2-3). Di(heptyl,nonyl,undecyl) phthalate had a half-life of 6 to 8 days in river die-away tests(5). In active microcosms containing lake water and sediment, 40 to 48% of (14)C-di(heptyl,nonyl,undecyl) phthalate radioactivity was evolved as carbon dioxide over a 41 day period; after six weeks no residual (14)C-di(heptyl,nonyl,undecyl) phthalate was found in the water column and only 2 to 6% was associated with sediments(5). In semi-continuous activated sludge tests, a primary degradation half-life of <1 day at an addition rate of 5 to 200 mg/L per 24-hour cycle was observed for di(heptyl,nonyl,undecyl) phthalate(5). In shake flask studies using an acclimated bacterial inoculum, an ultimate degradation half-life of 5 days was observed for di(heptyl,nonyl,undecyl) phthalate at an initial concentration of 20 mg/L(5). Diheptyl phthalate was biodegraded in river water from the Kako River in Japan(6). Diheptyl phthalate was biodegraded 11-16% over a 40 day incubation period with activated sludge(7).

SEDIMENT: Sediment samples taken Sept 1995 from the mouth of 3 rivers (The Hokura flows 54.7 km and includes industrial and agricultural areas; The Shinano flows 366.8 km and includes urban and agricultural areas; The Tainai includes industrial and agricultural areas, draining 151 sq km) were negative for diheptyl phthalate(1). It was detected, not quantified in 1 port in Niigata, Japan(1).

BCFs of 0.9 to 2.2 and 6.2 to 16.7 were measured for diheptyl phthalate in carp at chemical concentrations of 1 and 0.1 mg/L, respectively(1). According to a classification scheme(2), these measured BCFs suggest that bioconcentration in aquatic organisms is low(SRC).