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Diallyl phthalate

Diallyl phthalate structure

Diallyl phthalate 

structure
  • CAS No:

    131-17-9

  • Formula:

    C14H14O4

  • Chemical Name:

    Diallyl phthalate

  • Synonyms:

    1,2-Benzenedicarboxylic acid,1,2-di-2-propen-1-yl ester;Phthalic acid,diallyl ester;1,2-Benzenedicarboxylic acid,di-2-propenyl ester;Dapon R;Diallyl phthalate;Allyl phthalate;Dappu;DAP-M;DT 170;DAP Monomer;Dap Tohto DT 170;NSC 7667;Daiso DAP monomer;KY 5200;DAP;Monoplex DAP;DCP-A;124743-27-7;143318-73-4

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

clear colourless to light yellow liquidClear pale-yellow liquid. Odorless.


Diallyl phthalate is a clear pale-yellow liquid. Odorless. (NTP, 1992)|Liquid; PelletsLargeCrystals|COLOURLESS LIQUID.


Diallyl phthalate is a clear pale-yellow liquid. Odorless. (NTP, 1992)

Diallyl phthalate Basic Attributes

246.26

246.26

1880877

205-016-3

F79L0UL6ST

0430

7667

3082

DTXSID7020392

Nearly colorless, oily liquid

29173400

Characteristics

52.6

3.2

Clear colorless to light yellow Liquid

1.120 g/cm3 @ Temp: 20 °C

-70 °C

158-165 °C @ Press: 4 Torr

>230 °F

n 20/D 1.519(lit.)

H2O: 6 g/L (20 ºC)

Refrigerator

2.3 mm Hg ( 150 °C)

8.3 (vs air)

Oral-Rat LD50: 656 mg/kg

Combustible in case of open flame, high temperature and strong oxidant; burning emits irritating smoke

mild lachrymatory

Henry's Law constant = 3.86X10-7 atm- cu m/mol at 25 °C (est)

Conversion factor: 10.08 mg/cu m= 1 ppm|Phthalate esters would be expected to have UV maxima in the 230 nm and 270 nm regions. /Phthalate esters/|... Resistance to migration from polymers, low temperature flexibility ... compatibility with polar polymers and additives over a wide range of compositions. /Phthalate esters/|Hydroxyl radical reaction rate constant = 5.57X10-11 cu cm/molec-sec at 25 °C (est)

Incompatible with water and oxygen. Should be stored air tight, with inhibitor, to prevent polymerization reaction (NTP, 1992).

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

Polymerizable

DIALLYL PHTHALATE can react with oxidizers. It can also react with acids and alkalis. It is incompatible with water and oxygen. (NTP, 1992)

385 °C

Safety Information

III

9

UN 3082 9/PG 3

2

22-50/53

24/25-60-61

CZ4200000

Xn,N

Completely packed, lightly placed; storeroom ventilated, away from open flames, high temperature, and stored separately from oxidants

No risk of explosion

Stable under normal temperatures and pressures.

P273-P501

H302-H410

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.

...Can react with oxidizing materials.

Diallyl phthalate is an indirect food additive for use only as a component of adhesives.

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)

This chemical is combustible. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P301+P312, P330, P391, and P501|H302 (96.45%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, P391, and P501|Aggregated GHS information provided by 564 companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P260, P261, P264, P270, P271, P272, P280, P301+P312, P302+P352, P304+P312, P304+P340, P309+P311, P312, P314, P321, P330, P333+P313, P363, P405, and P501|Danger|P201, P202, P260, P261, P264, P270, P271, P272, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P308+P313, P309+P311, P312, P314, P321, P330, P333+P313, P363, P405, and P501

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

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. STORAGE PRECAUTIONS: You should store this chemical under refrigerated temperatures, and keep it away from oxidizing materials. (NTP, 1992)

RECOMMENDED RESPIRATOR: When working with this chemical, wear a NIOSH-approved full face chemical cartridge respirator equipped with the appropriate organic vapor cartridges. If that is not available, a half face respirator similarly equipped plus airtight goggles can be substituted. However, please note that half face respirators provide a substantially lower level of protection than do full face respirators. (NTP, 1992)

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.

Water or foam may cause frothing.

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.

Ventilation. Do NOT let this chemical enter the environment. Collect leaking liquid in covered containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Separated from strong oxidants, strong bases and acids. Store only if stabilized. Store in an area without drain or sewer access.

A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.

If this liquid is swallowed, aspiration into the lungs may result in chemical pneumonitis.

Repeated or prolonged contact may cause skin sensitization.

NO open flames.

PREVENT GENERATION OF MISTS!

Use ventilation.

Protective gloves. Protective clothing.

Wear safety spectacles.

| 1 - Materials that, under emergency conditions, can cause significant irritation.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 1 - Materials that in themselves are normally stable but that can become unstable at elevated temperatures and pressures.

SEDIMENT: Diallyl phthalate was detected at 2 of 7 sites on the Chester River, MD which flows into Chesapeake Bay. The sites were located below a plasticizer manufacturing plant. Samples were collected in June, 1978(1).

Toxicity

moderately toxic

LD50 Rat oral 656 mg/kg|LD50 Rabbit oral 1.7 g/kg /From table/|LD50 Rabbit dermal 3400 mg/kg /From table/|LD50 Mouse ip 700 mg/kg|For more Non-Human Toxicity Values (Complete) data for DIALLYL PHTHALATE (7 total), please visit the HSDB record page.

/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...

Toxicology and carcinogenesis studies of diallyl phthalate (approximately 99% pure) were conducted by administering the test chemical in corn oil by gavage to groups of 50 male and 50 female F344/N rats at doses of 0 (vehicle control), 50, or 100 mg/kg 5 days per week for 103 weeks. The diallyl phthalate doses used in the 2 year studies were chosen on the basis of 13 week studies, wherein doses of 200 or 400 mg/kg caused death, reductions in body weight gains, or periportal hepatocellular necrosis and fibrosis in both sexes. Mean body weights and survival of male and female rats administered diallyl phthalate were essentially the same as those of the vehicle controls throughout the 2 year studies, although hepatotoxicity was produced in both sexes by the 100 mg/kg dose. Based on the results of the prechronic studies and the effects on the liver in the 2 year studies, the doses used in the 2 year studies were considered to be adequate for carcinogenicity testing. Male and female rats receiving the 100 mg/kg dose of diallyl phthalate in the 2 year studies developed chronic liver disease characterized by periportal fibrosis, periportal accumulation of pigment, and severe bile duct hyperplasia. Pigment accumulation also occurred at the 50 mg/kg dose in both sexes. Diallylphthalate administration increased the occurrence of mononuclear cell leukemia in female rats (p <0.05 by trend tests), and the incidence in the 100 mg/kg dose female rats was greater (p <0.05) than in the vehicle controls by pairwise comparisons (vehicle control, 15/50, 30%; low dose, 15/43, 35%; high dose, 25/49, 51%). An increased occurrence of mononuclear cell leukemia was not observed in male rats receiving diallylphthalate. ... Under the conditions of this study, the administration of diallyl phthalate by gavage in corn oil to male and female F344/N rats for 2 years caused chronic liver disease characterized by periportal fibrosis and pigment accumulation and an increased severity of bile duct hyperplasia. The incidence of mononuclear cell leukemia was significantly increased in female rats receiving 100 mg/kg. Because of the variability in the incidence of this neoplasm in aged Fischer 344 rats and the difficulty in definitively diagnosing this lesion in Fischer 344 rats, this increase was considered to be equivocal evidence of carcinogenicity of diallyl phthalate in female rats. There was no evidence of carcinogenicity in male rats.|A carcinogenesis bioassay of diallyl phthalate (99% pure) was conducted by administering 0 (vehicle control), 150, or 300 mg/kg diallyl phthalate in corn oil by gavage, 5 days per week for 103 weeks, to groups of 50 male and 50 female B6C3F1 mice. Survival rates and mean body weights of dosed mice were not different from those of vehicle controls, and pathological lesions unrelated to proliferative changes were not observed. Therefore, a maximally tolerated dose for the purposes of carcinogenicity testing may not have been achieved. The incidences of lymphoma or either lymphoma & leukemia in dosed male mice were not significantly greater than those in the controls according to pairwise comparisons (p= 0.051 to p=0.096), but the trend tests were statistically significant by either life table or incidental tumor analyses (p= 0.031 to p= 0.045). The incidence of lymphomas in the high dose male mice was 12/50 (24%) in comparison with 6/50 (12%) in the controls. Recent historical incidences at the performing laboratory and in the NTP Bioassay Program were 18/120 (15%) and 71/661 (11%), respectively. Since the incidence of high dose male mice with leukemia was not significantly greater than that of concurrent or historical controls at the performing laboratory by pairwise comparisons, this marginal increase was considered only to be equivocally related to diallyl phthalate administration. Increased incidences of squamous cell papillomas, hyperplasia, and inflammatory lesions of the forestomach were observed in diallyl phthalate dosed mice of both sexes in a dose related manner. Because of the numerical elevation of forestomach papillomas in high dose mice of both sexes, the concomitant observation of dose related forestomach hyperplasia, and the rarity of this tumor in corn oil (gavage) control B6C3F1 mice, the development of squamous cell papillomas of the forestomach may have been related to diallyl phthalate administration. Under the conditions of this bioasssay, the development of chronic inflammation and hyperplasia of the forestomach in both male and female B6C3F1 mice was considered to be related to the administration of diallyl phthalate. The development of squamous cell papillomas of the forestomach may also have been related to chemical administration, but the available data are insufficient to indicate a clear cause and effect relationship. An increase in the incidence of male mice with lymphomas was observed, but this increase was considered only to be equivocally related to diallyl phthalate administration. The results of this bioassay, therefore, do not indicate that diallyl phthalate is carcinogenic in B6C3F1 mice, although a maximally tolerated dose may not have been achieved.

Diallyl phthalate's production and use as a plasticizer(1) in industry and as a monomer in the processing of thermosetting plastics, polyester resins, and varnishes(2), may result in its release to the environment through various waste streams(SRC).

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 rate constant for the vapor-phase reaction of diallyl phthalate with photochemically-produced hydroxyl radicals has been estimated as 5.6X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 6.9 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of diallyl phthalate with ozone has been estimated as 2.4X10-7 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 11 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). A base-catalyzed second-order hydrolysis rate constant of 0.22 L/mole-sec(SRC) was estimated using a structure estimation method(3); this corresponds to half-lives of 1.0 years and 37 days at pH values of 7 and 8, 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).

An estimated BCF of 61 was calculated in fish for diallyl phthalate(SRC), using a log Kow of 3.23(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

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.

The Henry's Law constant for diallyl phthalate is estimated as 3.9X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that diallyl phthalate is expected to be essentially nonvolatile from water surfaces(2). 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(3).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 8,784 workers (2,027 of these were female) were potentially exposed to diallyl phthalate in the US(1). Occupational exposure to diallyl phthalate may occur through inhalation of aerosols and dermal contact with this compound at workplaces where diallyl phthalate is produced or used. Use data indicate that the general population may be exposed to diallyl phthalate via dermal contact with products containing diallyl phthalate(SRC).

Drug Information

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.

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.

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. ACUTE/CHRONIC HAZARDS: This compound is toxic by ingestion. It may cause irritation of the eyes, skin and mucous membranes. It is also a lacrimator. It can be absorbed through the skin. When heated to decomposition this compound emits acrid smoke, irritating fumes and toxic fumes of carbon monoxide and carbon dioxide. (NTP, 1992)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)


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).

/SIGNS AND SYMPTOMS/ Diallyl phthalate appears to be a low human dermal irritant.

diallyl phthalate

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

Redness.

Diallyl phthalate Use and Manufacturing

Methods of Manufacturing

Phthalic anhydride reacts with liquid alkali to form phthalic acid sodium salt, and then it is esterified with chloropropene at 40-60℃ under normal pressure to obtain crude product. After filtration, neutralization, washing with water, and vacuum distillation, it is the finished product. Raw material consumption quota: phthalic anhydride (≥90%) 780kg/t, chloropropene (≥95) 1060kg/t, liquid alkali (40%) 1080kg/t.

Uses

Diallyl Phthalate is used as a reagent in ring-closing ruthenium based reactions.


Adhesives and sealant chemicals


Plastic and rubber products not covered elsewhere

Production

1,000,000 - 10,000,000 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#4850]

Adhesive manufacturing|1,2-Benzenedicarboxylic acid, 1,2-di-2-propen-1-yl ester: ACTIVE|1,2-Benzenedicarboxylic acid, 1,2-di-2-propen-1-yl ester, homopolymer: ACTIVE|XU - indicates a substance exempt from reporting under the Chemical Data Reporting Rule, (40 CFR 711).|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.

Computed Properties

Molecular Weight:246.26
XLogP3:3.2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:8
Exact Mass:246.08920892
Monoisotopic Mass:246.08920892
Topological Polar Surface Area:52.6
Heavy Atom Count:18
Complexity:290
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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