Diundecyl phthalate

Insoluble (<1 mg/ml at 70 °F) (NTP, 1992)

In water, 1.11 mg/L at 20 °C

Diundecyl phthalate is an oily colorless odorless liquid. Less dense than water. (USCG, 1999)

Liquid; Large Crystals; Liquid

Solid; mp = 35.5 deg C; [HSDB] Colorless odorless liquid; [CAMEO] mp = -9 deg C; [eChemPortal: HPVIS] Liquid; [MSDSonline]

This chemical does not meet GHS hazard criteria for 86.7% (65 of 75) of all reports.

H412 (12%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P273, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 75 reports by companies from 3 notifications to the ECHA C&L Inventory.

Not Classified

H413: May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]

Chemical: 1,2-Benzenedicarboxylic acid, diundecyl ester

Hazard Traits - Carcinogenicity; Developmental Toxicity; Endocrine Toxicity; Immunotoxicity; Reproductive Toxicity; Respiratory Toxicity

1,2-Benzenedicarboxylic acid, 1,2-diundecyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Benzenedicarboxylic acid, 1,2-diundecyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

REACH registered substance: Diundecyl phthalate (EC: 222-884-9)

1,2-Benzenedicarboxylic acid, diundecyl ester: Does not have an individual approval but may be used under an appropriate group standard

Santicizer 711: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

PIERCE ET AL; NATL RES COUNC CAN ASSOC COMM SCI CRITER ENVIRON QUAL PUBL 0(17583) 1-100 (1980) THE PHYSICAL-CHEMICAL PROPERTIES, ANALYTICAL DETN AND ENVIRONMENTAL DYNAMICS OF PHTHALATE ESTERS (INDUSTRIAL PLASTICIZERS) ARE REVIEWED.

Nat'l Research Council Canada; Phthalate Esters In The Aquatic Environment (1980) NRCC No. 17583

USEPA; Ambient Water Quality Criteria Doc: Phthalate Esters (1980) EPA 440/5-80-067

Health & Welfare Canada; Phthalic Acid Esters (1980) Report # 80-EDH-62

For more Special Reports (Complete) data for DIUNDECYL PHTHALATE (6 total), please visit the HSDB record page.

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. 1,2-Benzenedicarboxylic acid, diundecyl ester is included on this list. Effective date 10/04/82; Sunset date 10/04/92.

A testing consent order is in effect for diundecyl phthalate for environmental effects and chemical fate testing. FR citation: 1/9/89.

DIUNDECYL PHTHALATE reacts with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by interaction with caustic solutions. Flammable hydrogen is generated by mixing with alkali metals and hydrides. Can generate electrostatic charges [Handling Chemicals Safely, 1980. p. 250].

Aquatic Chronic 3 (12%)

Hazardous to the aquatic environment (Long-term) - Category 4

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

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.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Phthalate esters are endocrine disruptors. Animal studies have shown that they disrupt reproductive development and can cause a number of malformations in affected young, such as reduced anogenital distance (AGD), cryptorchidism, hypospadias, and reduced fertility. The combination of effects associated with phthalates is called 'phthalate syndrome’. (A2883)

LC50; Species: Cyprinodon variegatus (Sheepshead minnow, juvenile, length 6-17 mm); Conditions: freshwater, static, 22 °C, pH 7.6-7.9, hardness 25-50 mg/L CaCO3, alkalinity 25-50 mg/L CaCO3; Concentration: >220 ug/L for 96 hr /> or = 95% purity/

LC50; Species: Lepomis macrochirus (Bluegill, juvenile, length 29-40 mm); Conditions: freshwater, static, 22 °C, pH 7.6-7.9, hardness 25-50 mg/L CaCO3, alkalinity 25-50 mg/L CaCO3; Concentration: >730 ug/L for 96 hr /> or = 95% purity/

LC50 Lepomis macrochirus (bluegill) >1 mg/L (limit of solubility)/96 hr; Conditions: static, hardness 42 to 48 mg/L, alkalinity 30 to 34 mg/L, pH 7.7 to 7.9, specific conductance 150 to 160 umhos/cm, dissolved oxygen levels 89 to 100%, 22 + or - 1 °C.

LC50 Oncorhynchus mykiss (rainbow trout, mean length = 39 mm and mean wet weight = 0.6 g) > 1.4 mg/L/96 hr; Conditions: flow through, 11 + or - 1 °C, pH 7.1 to 7.5, dissolved oxygen 9.8 to 10.0 mg/L, total hardness and alkalinity as CaCO3 20 to 26 mg/L and 14 to 22 mg/L.

For more Ecotoxicity Values (Complete) data for DIUNDECYL PHTHALATE (18 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 7.7X10+6(SRC), determined from a structure estimation method(2), indicates that diundecyl phthalate is expected to be immobile in soil(SRC). Volatilization of diundecyl phthalate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.6X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil is expected to attenuate volatilization(SRC). Diundecyl phthalate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.2X10-9 mm Hg(SRC), determined from a fragment constant method(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 7.7X10+6(SRC), determined from a structure estimation method(2), indicates that diundecyl 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 5.6X10-5 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 1.7 and 19 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The volatilization half-life from a model pond is about 1320 years when adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from an estimated log Kow of 11.49(7) and a regression-derived equation(8), suggests 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 7.7 years and 280 days at pHs 7 and 8, respectively(9). Di(heptyl,nonyl,undecyl)phthalate subjected to river die-away tests exhibited half-lives ranging from 6 to 8 days(10) to 2.5 weeks (11), suggesting that biodegadation may occur in the aquatic environment(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diundecyl phthalate, which has an estimated vapor pressure of 1.2X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase diundecyl phthalate may be removed from the air by wet or dry deposition(SRC). Diundecyl phthalate does contain chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Phthalate esters are endocrine disruptors. They decrease foetal testis testosterone production and reduce the expression of steroidogenic genes by decreasing mRNA expression. Some phthalates have also been shown to reduce the expression of insulin-like peptide 3 (insl3), an important hormone secreted by the Leydig cell necessary for development of the gubernacular ligament. Animal studies have shown that these effects disrupt reproductive development and can cause a number of malformations in affected young. (A2883)

/AQUATIC SPECIES/ Chronic toxicity studies were performed with commercial phthalate esters and Daphnia magna (14 phthalates) and rainbow trout (Oncorhynchus mykiss) (six phthalates). For the lower-molecular-weight phthalate esters - dimethyl phthalate (DMP), diethyl phthalate (DEP), di-n-butyl phthalate (DBP), and butylbenzyl phthalate (BBP) - the results of the studies indicated a general trend in which toxicity for both species increased as water solubility decreased. The geometric mean maximum acceptable toxicant concentration (GM-MATC) for D. magna ranged from 0.63 to 34.7 mg/L. For the higher-molecular-weight phthalate esters - dihexyl phthalate (DHP), butyl 2-ethylhexyl phthalate (BOP), di-(n-hexyl, n-octyl, n-decyl) phthalate (610P), di-(2-ethylhexyl) phthalate (DEHP), diisooctyl phthalate (DIOP), diisononyl phthalate (DINP), di-(heptyl, nonyl, undecyl) phthalate (711P), diisodecyl phthalate (DIOP), diundecyl phthalate (DUP), and ditridecyl phthalate (DTDP) - the GM-MATC values ranged from 0.042 to 0.15 mg/L. Survival was equally sensitive and sometimes more sensitive than reproduction. The observed toxicity to daphnids with most of the higher-molecular-weight phthalate esters appeared to be due to surface entrapment or a mode of toxicity that is not due to exposure to dissolved aqueous-phase chemical. Early life-stage toxicity studies with rainbow trout indicated that survival (DMP) and growth (DBP) were affected at 24 and 0.19 mg/g, respectively. This pattern of observed toxicity with the lower-molecular-weight phthalate esters and not the higher-molecular-weight phthalate esters is consistent with previously reported acute toxicity studies for several aquatic species.

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=3648-20-2][Available at http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=3648-20-2]

Using a structure estimation method based on molecular connectivity indices(1), the Koc of diundecyl phthalate can be estimated to be 7.7X10+6(SRC). According to a classification scheme(2), this estimated Koc value suggests that diundecyl phthalate is expected to be immobile in soil.

Effects on the liver and liver lipids were evaluated in groups of male and female Fischer 344 rats (5/sex/dose level) fed nominal concentrations of 0, 0.3, 1.2 or 2.5% diundecyl phthalate in the diet for 21 days. Toxicity was evident by statistical differences between dosed groups and controls for: mean body weights (1.2 and 2.5% group females & 2.5% group males), absolute and relative liver weights (1.2 and 2.5% group, males and females), absolute kidney weights (1.2 and 2.5% group males), relative kidney weights (1.2 and 2.5% group females) and relative testis weights (1.2 and 2.5% group males). There was a statistically significant decrease in serum triglycerides and cholesterol for 1.2 and 2.5% dietary males, while female treatment groups remained comparable to controls. There was a moderate increase in peroxisome proliferation for the high dose animals. Liver biochemistry revealed statistically significant differences between treated and controls as indicated by cyanide-insensitive palmitoyl-CoA oxidation levels (1.2 and 2.5% group, males and females), lauric acid 11- and 12- hydroxylase activities (all treated males & 2.5% group females) and hepatic protein levels (1.2 and 2.5% group females). There was a dose related increase in fat deposition in the centrilobular and midzonal regions of the liver in male rats; also males in the lower treatment groups showed a reduction in the normal distribution of periportal fat. In females the only effect on hepatic lipids was a reduction of the normal distribution of periportal neutral lipid.

The toxicity of diundecyl phthalate was evaluated in the mouse lymphoma L5178Y cell line in the presence and absence of rat liver S9 metabolic activation. All cultures were treated in duplicate with concentrations of 9.77, 19.50, 39.10, 78.10, 156.00, 313.00, 625.00, 1250.00, 2500.00 or 5000.00nl/ml, and growth was determined at 24 and 48 hours after initiation of the treatment. Under nonactivated conditions, diundecyl phthalate appeared to be soluble up to 5000nl/ml, but a precipitate was observed in the 5000nl/ml treatment after 24 hours. For the nonactivated cultures, a dose-response relationship was noted, with the average percent suspension growth 50% of the control (acetone) cultures at 1250nl/ml, while at 5000nl/ml the average suspension growth was reduced to 30.1% of the controls. Activated assays appeared soluble up to 5000nl/ml, with a similar toxicity pattern as observed in the nonactivated cultures. The average percent suspension growth was 39.5% of the solvent control growth at 1250nl/ml and was reduced to 23.6% of the control value at 5000nl/ml.

The ability of diundecyl phthalate to induce morphological transformation was evaluated in the Balb/c-3T3 mouse cell line (Cell Transformation Assay). Preliminary toxicity assays preformed in plastic vessels did not produce a clear dose response relationship for diundecyl phthalate; thus five arbitrary doses at and above the test article's solubility (ranging from 4000 to 100000nl/ml) were chosen for the transformation assay, and resulted in cell survival approximately 64 to 86% relative to the control (culture medium). Assays conducted in glass bottle culture vessels, also did not a produce a clear dose response; thus five arbitrary doses were chosen both above and below the solubility limit (ranging from 400 to 40000nl/ml) and resulted cell survival approximately 44 to 86% relative to the control (culture medium). None of the treatments in plastic vessels produced significantly greater transformation frequencies relative to the negative control. At a concentration of 12,650nl/ml in the glass culture flasks, a statistically significant (02<p<.05) increase in the number of transformed foci was observed relative to the negative control (culture medium).

The ability of diundecyl phthalate to induce specific locus mutations at the TK locus in cultured L5178Y mouse lymphoma cells (Mouse Lymphoma Mutagenicity Test) was evaluated in the presence and absence of rat liver S9 metabolic activation. The test material was incompletely soluble in the test medium at all concentrations tested. Under nonactivation conditions, concentrations of 2000, 4000, 5000, 6000, 8000, and 10,000 nl/ml induced moderate to high toxicities (21.1 to 70.7% relative growths) but no increase in mutation frequency. Under activation conditions, concentrations of 1000, 2500, 4000, 5000, 5540, and 8000 nl/ml induced moderate to high toxicities (3.5 to 62.7% relative growths) but again no increase in mutation frequency..

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. 1,2-Benzenedicarboxylic acid, diundecyl ester is included on this list. Effective date 10/04/82; Sunset date 10/04/92.

A testing consent order is in effect for diundecyl phthalate for environmental effects and chemical fate testing. FR citation: 1/9/89.

Phthalate esters are first hydrolyzed to their monoester derivative. Once formed, the monoester derivative can be further hydrolyzed in vivo to phthalic acid or conjugated to glucuronide, both of which can then be excreted. The terminal or next-to-last carbon atom in the monoester can also be oxidized to an alcohol, which can be excreted as is or first oxidized to an aldehyde, ketone, or carboxylic acid. The monoester and oxidative metabolites are excreted in the urine and faeces. (A2884)

Used as a primary plasticizer for polyvinyl chloride in electrical wire insulation and car interiors; [HSDB]

In car interiors

Diundecyl phthalate is a primary plasticizer for polyvinyl chloride (PVC) ... /and insulator/ on electrical wiring.

... In perfumes and cosmetics, ... vinyl swimming pools, plasticized vinyl seats (on furniture and in cars), and clothing (jackets, raincoats, boots, etc.) /Phthalates/

... Recommended for use in wire insulation for use at about 100 °C.

Phthalate esters are mainly used as plasticizers, primarily used to soften polyvinyl chloride. They are found in a number of products, including glues, building materials, personal care products, detergents and surfactants, packaging, children's toys, paints, pharmaceuticals, food products, and textiles. Phthalates are used in a variety of household applications such as shower curtains, vinyl upholstery, adhesives, floor tiles, food containers and wrappers, and cleaning materials. Personal care items containing phthalates include perfume, eye shadow, moisturizer, nail polish, liquid soap, and hair spray. (L1903)

2023: 25,000,000 - <40,000,000 lb

(1977) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1979) 7X10+9 GRAMS (EST DEMAND)

1,2-Benzenedicarboxylic acid, diundecyl ester is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5179]

Plasticizer

ESSENTIALLY 100% AS A PLASTICIZER (1980)

Commercial test substance, 711P, is actually an equal composition mixture of six phthalate esters consisting of C7, C9, and C11 ester side chains. This test substance is considered by EPA under the following CAS numbers: 68515-44-6 (di C7), 68515-45-7 (di C9), 3648-20-2 (di C11), 111381-89-6 (C7, C9), 111381-90-9 (C7, C11), and 111381-91-0 (C9, C11).

Plastics Product Manufacturing

1,2-Benzenedicarboxylic acid, 1,2-diundecyl ester: ACTIVE