フタル酸ジアリル

Plastics & Rubber -> Phthalate Esters

Plastics -> PUR; PVC (soft)

Plastics -> Plasticisers

log Kow = 3.23

3.23

3.23

1.12 at 68 °F (NTP, 1992) - Denser than water; will sink

1.120 at 20 °C/20 °C

Relative density (water = 1): 1.1

1.120 @ 20°C

less than 0.1 mg/mL at 72 °F (NTP, 1992)

Sol in gasoline, mineral oil, glycerin, certain amines. Sol in most org liquids.

In water, 182 mg/L at 25 °C

Solubility in water, g/100ml at 20 °C: 0.015 (very poor)

230 °F (NTP, 1992)

166 °C

330 °F (166 °C) (Closed cup)

166 °C c.c.

554 °F at 760 mmHg (NTP, 1992)

158-165 °C at 4 mm Hg

290 °C

157 °C @760 [mm Hg]

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Warning

H302+H332 (17.7%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation]

P261, P264, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Chemical: 1,2-Benzenedicarboxylic acid, di-2-propenyl ester

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

1,2-Benzenedicarboxylic acid, 1,2-di-2-propen-1-yl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Benzenedicarboxylic acid, 1,2-di-2-propen-1-yl 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)

Status: Active Update: 19-03-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/12746

Diallyl phthalate: Does not have an individual approval but may be used under an appropriate group standard

This chemical is combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Limiting oxygen index (LOI): 26-36 /for diallyl phthalate/. This is a measure of the minimum concentration of oxygen in an oxygen-nitrogen atmosphere that is necessary to support a flame for at least 3 minutes under specified test conditions.

SYMPTOMS: Symptoms of exposure to this compound include irritation of the skin, eyes and mucous membranes. At very high levels, toxic effects include central nervous system depression. It can cause internal disorders by continued skin absorption. Inhalation may cause nose, throat and lung irritation, lung congestion and liver damage. Eye contact may cause burning. It may cause lacrimation. Other symptoms include coughing, sneezing, thirst, respiratory distress, sore throat, headache and abdominal pain.

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

USEPA/ECAO; Atlas Document for: Phthalate Esters (1980)

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. Diallyl phthalate is included on this list. Effective date 04/13/89; Sunset date 12/19/95.

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use powder, carbon dioxide, foam.

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible).

Rinse mouth.

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, FIRST REMOVE ALL SOURCES OF IGNITION. Then, 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 60-70% ethanol followed by washing with a 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.

Avoid contact with skin and eyes.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

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)

EC50; Species: Scenedesmus subspicatus (Green algae, log growth phase); Conditions: freshwater, static, 24 °C, pH 8.0-9.3; Concentration: 5300 ug/L for 48 hr; Effect: decreased population biomass /formulated product/

EC50; Species: Scenedesmus subspicatus (Green algae, log growth phase); Conditions: freshwater, static, 24 °C, pH 8.0-9.3; Concentration: 3800 ug/L for 72 hr; Effect: decreased population biomass /formulated product/

EC50; Species: Scenedesmus subspicatus (Green algae, log growth phase); Conditions: freshwater, static, 24 °C, pH 8.0-9.3; Concentration: 4500 ug/L for 96 hr; Effect: decreased population biomass /formulated product/

EC50; Species: Scenedesmus subspicatus (Green algae, log growth phase); Conditions: freshwater, static, 24 °C, pH 8.0-9.3; Concentration: 11000 ug/L for 48 hr; Effect: decreased population changes, general /formulated product/

For more Ecotoxicity Values (Complete) data for DIALLYL PHTHALATE (9 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,360(SRC), determined from a log Kow of 3.23(2) and a regression-derived equation(3), indicates that diallyl phthalate is expected to have low mobility in soil(SRC). Volatilization of diallyl phthalate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.9X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Diallyl phthalate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.2X10-3 mm Hg(SRC), determined from a fragment constant method(5). Biodegradtion at 92% of its theoretical BOD in 4 weeks using an activated sludge inoculum in the Japanese MITI test(6) suggests that biodegradation may be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,360(SRC), determined from a log Kow of 3.23(2) and a regression-derived equation(3), indicates that diallyl phthalate is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.9X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 61(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Hydrolysis is expected to be an important process(SRC) based on estimated hydrolysis half-lives of 1.0 year and 37 days at pHs 7 and 8, respectively(7). Biodegradation at 92% of its theoretical BOD in 4 weeks using an activated sludge inoculum in the Japanese MITI test(8) suggests that biodegradation will be a rapid environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diallyl phthalate, which has an estimated vapor pressure of 1.2X10-3 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 diallyl phthalate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone(SRC); the half-lives for these reactions are estimated as 6.9 and 11 hours(SRC), calculated from rate constants of 5.6X10-11 and 2.4X10-17cu cm/molecule-sec at 25 °C(SRC), respectively(3). The UV spectrum of diallyl phthalate in water was found to have absorbance near 275.5 and 281 nm(4) and is expected to have absorption shoulders which extend beyond 290 nm and therefore may be susceptible to direct photolysis by sunlight(SRC).

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion.

Oral (L1903) ; inhalation (L1903) ; dermal (L1903)

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/ ...Digestive gland peroxisome-enriched fractions of Mytilus edulis (L., 1758) /blue mussel/ were analyzed ... for/ proteomic signatures associated with the exposure to several marine pollutants (diallyl phthalate, PBDE-47, and bisphenol-A). Animals collected from North Atlantic Sea were exposed to the contaminants independently under controlled laboratory conditions. One hundred and eleven spots showed a significant increase or decrease in protein abundance in the two-dimensional electrophoresis maps from the groups exposed to pollutants. ... A unique protein expression signature of exposure to each of those chemical compounds /was obtained/. Moreover a set of proteins composed a proteomic signature in common to the three independent exposures. It is remarkable that the principal component analysis of these spots showed a discernible separation between groups, and so did the hierarchical clustering into four classes. The 14 proteins identified by MS participate in alpha- and beta-oxidation pathways, xenobiotic and amino acid metabolism, cell signaling, oxyradical metabolism, peroxisomal assembly, respiration, and the cytoskeleton. ...

/AQUATIC SPECIES/ ...Two different exposure experiments were performed: spider crabs (Hyas araneus) were exposed for 3 weeks to diallyl phatalate (DAP), bisphenol A (BisA) and polybrominated diphenyl ether (PBDE-47), while shore crabs (Carcinus maeanas) were exposed to crude oil, crude oil spiked with alkylphenols (APs) and 4-nonylphenol (NP). Gender and species-related protein pattern alterations were observed and compared to controls. Results showed different responses to pollutants by the two species. Major disruption in protein peak expression was observed in samples exposed to mixtures of pollutants, i.e. oil spiked with APs. Compared to shore crab, spider crab species showed a lower degree of response in terms of number of altered protein peaks following exposure. In general, female individuals of both species showed a larger number of significantly altered proteins compared to males. ...

/AQUATIC SPECIES/ ... The effects of various seawater contaminants on tyrosine phosphorylation levels in different tissues of the mussel (Mytilus edulis) /were studied/ by using Western immunoblotting. Mussels were exposed in aquarium for 3 weeks to ... potential endocrine disruptors /including/... diallyl phthalate ... . Use of antiphosphotyrosine antibody showed that treatments with oil alone, or with oil, alkyl phenols and PAH induced phosphorylation increases in the digestive gland, gills and mantle; ...diallyl phthalate ... had a slight effect only on the gill tissue. ...

/AQUATIC SPECIES/ Analysis of micronuclei, nuclear buds, bi-polynucleated and fragmented-apoptotic cells was performed in gills of blue mussels exposed for 3 weeks to sublethal concentrations of /several compounds including/ ...diallyl phthalate (nominal concentration 50 ppb) ... Fourteen specimens from each treatment and control group were used for the analysis. ... A significant increase in micronuclei frequency /was observed/ after the treatment with ... diallyl phthalate (P=0.0005) ... . Treatment with diallyl phthalate increased the level of fragmented-apoptotic cells (P=0.0283). ...

/AQUATIC SPECIES/ ...To investigate some aspects of their potential estrogenic action, mussels were continuously exposed /to environmental pollutants including diallyl phthalate/ during 3 weeks. Gonadal development and vitellogenin like protein levels were examined. ... Diallyl phthalate ... decreased phospho-protein levels in both sexes and induced spawning in males...

Redness.

Phthalate esters are endocrine disruptors and can cause a number of developmental malformations termed 'phthalate syndrome'. (A2883)

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=131-17-9]

The Koc of diallyl phthalate is estimated as 1,360(SRC), using a log Kow of 3.23(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that diallyl phthalate is expected to have low mobility in soil.

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. Diallyl phthalate is included on this list. Effective date 04/13/89; Sunset date 12/19/95.

Fischer 344 rats and B6C3F1 mice were given 14(C) diallyl phthalate, 1, 10, or 100 mg/kg po or 10 mg/kg iv, and placed in metabolism cages for 24 hr. In rats, 25-30% of the diallyl phthalate was excreted as carbon dioxide, and 50-70% appeared in the urine within 24 hr. In mice, 6-12% of the diallyl phthalate was excreted as carbon dioxide, and 80-90% was excreted in the urine within 24 hr. Monoallyl phthalate (MAP), allyl alcohol, 3-hydroxypropylmercapturic acid (HPMA), and an unidentified polar metabolite (PM) were found in the urine of rats and mice dosed with diallyl phthalate. The polar metabolite was present in the urine of rats dosed with diallyl phthalate or allyl alcohol, indicating that the compound is a metabolite of allyl alcohol. There was no difference between the species in the quantity of allyl alcohol excreted, but mice excreted more monoallyl phthalate (39 vs 33%), 3-hydroxypropylmercapturic acid (28 vs 17%), and polar metabolite (20 vs 8%) than rats.

The following metabolic pathway is suggested for diallyl phthalate (DAP). First, the diester is hydrolyzed to monoallyl phthalate (MAP) and allyl alcohol (AA). AA can be oxidized to acrolein and acrylic acid and further metabolized to CO2. Allyl alcohol and acrolein can also react with reduced glutathione to form 3-hydroxypropylmercapturic acid. Alternatively, allyl alcohol and acrolein can be oxidized to the epoxides glycidol and glycidaldehyde. These epoxides can be hydrolyzed to glycerin and glyceraldehyde or conjugated with reduced glutathione. It is not clear whether DAP is metabolized by this pathway in vivo. However, some of the products of the aforementioned reactions (e.g., monoallyl phthalate, 3-hydroxypropylmercapturic acid, allyl alcohol) as well as an unidentified polar metabolite have been detected in urine of rats and mice treated with DAP.

... Diallyl phthalate (DAP) is more hepatotoxic to rats than to mice, and demonstrated the same species difference in toxicity for allyl alcohol (AA). The data suggest that the toxicity of diallyl phthalate probably results from allyl alcohol cleaved from diallyl phthalate. To determine if the species difference in susceptibility to hepatotoxicity resulted from differences in the disposition and metabolism of diallyl phthalate, Fischer 344 rats and B6C3F1 mice were given 14(C) diallyl phthalate, 1, 10, or 100 mg/kg po or 10 mg/kg iv, and placed in metabolism cages for 24 hr. In rats, 25-30% of the diallyl phthalate was excreted as carbon dioxide, and 50-70% appeared in the urine within 24 hr. In mice, 6-12% of the diallyl phthalate was excreted as carbon dioxide, and 80-90% was excreted in the urine within 24 hr. Monoallyl phthalate (MAP), allyl alcohol, 3-hydroxypropylmercapturic acid (HPMA), and an unidentified polar metabolite (PM) were found in the urine of rats and mice dosed with diallyl phthalate. The polar metabolite was present in the urine of rats dosed with diallyl phthalate or allyl alcohol, indicating that the compound is a metabolite of allyl alcohol. There was no difference between the species in the quantity of allyl alcohol excreted, but mice excreted more monoallyl phthalate (39 vs 33%), 3-hydroxypropylmercapturic acid (28 vs 17%), and polar metabolite (20 vs 8%) than rats.

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)

Thirty minutes after rats and mice were treated orally with (14)C-labeled diallyl phthalate (DAP), the highest levels of radioactivity were found in small intestine, liver, dermis, muscles, blood, and kidneys. After 24 hr, about 6-7% of the radioactivity was present in rats and 1-3% in mice. In rats, 60% of the radioactivity was found in urine and 30% was exhaled as CO2. In mice, 91% was present in urine, and only 8% was detected as CO2.

Used to make insulators, potentiometers, and circuit boards in communication, computer, and aerospace systems; Also used as a monomer in thermosetting plastics, a diluent in polyester spray systems, a dye carrier; a sealant in insulating varnishes and metal castings, and an impregnant for jewelry; [HSDB]

Most diallyl phthalate compounds are sold under military specification and are used in critical electrical/electronic applications requiring high reliability under long-term, adverse environmental conditions. A significant application area is in electronic connectors in communications, computer and aerospace systems. Other uses are insulators, potentiometers, and circuit boards.

Diallyl phthalate (DAP) is used in industry as a monomer in the processing of thermosetting plastics, polyester resins, and varnishes.

PEROXIDE DILUENT IN POLYESTER SPRAY SYSTEMS; DYE CARRIER, EG, IN POLYESTER DYEING; SEALANT, EG, IN INSULATING VARNISHES AND METAL CASTINGS; IMPREGNANT, EG, FOR JEWELRY

Primary plasticizer that will polymerize if not inhibited, a monomer that will polymerize with heat and catalyst. Forms low-pressure laminates with various fillers such as glass cloth, paper, etc., for electrical insulation.

For more Uses (Complete) data for DIALLYL PHTHALATE (7 total), please visit the HSDB record page.

(1979) 1.82X10+7 G (PRINCPL CUSTMS DISTS)

(1986) 1.28X10+6 lb

(1983) 1.76X10+5 lb

2023: 250,000 - <400,000 lb

The 1977 TSCA inventory listed five companies which manufactured diallyl phthalate, with a total production volume of 11 million pounds.

1,2-Benzenedicarboxylic acid, di-2-propenyl 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#4848]

A general method for the preparation of allyl esters is the reaction of allyl alcohol with the free acids, acid anhydrides, or acid chlorides. Catalysts frequently used are aromatic sulfonic acids (p-toluenesulfonic acid and naphthalene-2-sulfonic acid). Strong mineral acids are of less value because they can decompose the allyl alcohol. Polymerizable acids are esterified in the presence of phenolic inhibitors. The following allyl esters are prepared by this method: diallyl phthalate, diallyl isophthalate, diallyl maleate, diallyl fumarate, triallyl cyanurate (from cyanuric chloride and allyl alcohol), and diethylene glycol bis(allyl carbonate). ...

... Diallyl phthalate is obtained from the reaction of allyl chloride and phthalic anhydride in the presence of sodium hydroxide, sodium carbonate, tertiary amines, or quaternary ammonium salts.

... Transesterification of the corresponding methyl esters with allyl alcohol; sodium methanolate is the preferred catalyst.

Plastics -> Polymer Type -> PUR; PVC (soft)

Plastics -> Plasticisers

All Other Chemical Product and Preparation Manufacturing

1,2-Benzenedicarboxylic acid, 1,2-di-2-propen-1-yl ester: ACTIVE

Diallyl phthalate cmpd show promise of optimizing both flame retardance and contaminated arc resistance in such electrical uses as switches, circuit breakers, stand-off insulators, and TV components.

Two series of specimens were prepared from a dental heat-cured soft acrylic resin, Vertex Rs, with di-butyl phthalate (DBP) and diallyl phthalate (DAP) as external and internal plasticizers, resp.

... IN BOAT & AUTOMOTIVE INDUSTRY ... POLYESTERS ARE DISSOLVED IN STYRENE & STABILIZED WITH INHIBITOR TO FORM VISCOUS SYRUP-LIKE LIQUID WHICH DOES NOT READILY SOLIDIFY. ... DIALLYL PHTHALATE RESISTS POLYMERIZATION OF THE UNCATALYZED SYRUP.