Diallylphthalat

DAP · Diallyl phthalate(DAP) · DAP MonoMer · Dially Phthalate · DAP(Diallyl Phthalate) · Dappu · daponr · Dapon R

Identifikatoren & physikalische Daten

CAS No.	131-17-9
Summenformel	C14H14O4
Durchschnittliche Molmasse	246,26 g/mol
Monoisotopische Masse	246,08920893 g/mol
SMILES	C=CCOC(=O)c1ccccc1C(=O)OCC=C
InChIKey	QUDWYFHPNIMBFC-UHFFFAOYSA-N
PubChem CID	8560
ChEMBL	CHEMBL1329372
EC No.	205-016-3
DTXSID	DTXSID7020392
Lokaler Name	Diallylphthalat

Chemische & physikalische Eigenschaften

XLogP	3,2
Polarare Oberfläche (TPSA)	52,6
H-Brücken-Donoren	0
H-Brücken-Akzeptoren	4
Frei drehbare Bindungen	8
Schwere Atome	18
Formalladung	0
Komplexität	290
Polymers	Plastics & Rubber -> Phthalate EstersPlastics -> PURPVC (soft)Plastics -> Plasticisers
LogP (Verteilungskoeffizient)	log Kow = 3.23
Geruch	mild lachrymatory
Plasticizers	Plasticizer
Dichte	1.12 at 68 °F (NTP, 1992) - Denser than waterwill sink1.120 at 20 °C/20 °CRelative density (water = 1): 1.11.120 @ 20°C1.121 g/mL at 25 °C (lit.)
Viscosity	13 cP at 20 °C
Color/Form	Nearly colorless, oily liquid
Löslichkeit	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 °CSolubility in water, g/100ml at 20 °C: 0.015 (very poor)0.18g/l6 g/L (20 ºC)
Flammpunkt	230 °F (NTP, 1992)166 °C330 °F (166 °C) (Closed cup)166 °C c.c.>230 °F
Endocrine Disruptors	Potential endocrine disrupting compound
Siedepunkt	554 °F at 760 mmHg (NTP, 1992)158-165 °C at 4 mm Hg290 °C157 °C @760 [mm Hg]165-167 °C/5 mmHg (lit.)
Decomposition	When heated to decomp it emits acrid smoke and irritating fumes.
Schmelzpunkt	-70 °C
Dampfdichte	8.3 (vs air)
Dampfdruck	2.3 mm Hg ( 150 °C)
Brechungsindex	n20/D 1.519(lit.)
Lagerbedingungen	Inert atmosphere,2-8°C
Aggregatzustand	Liquid
Farbe	Clear colorless to light yellow
Geruch	mild odor
BRN	1880877
Henry-Konstante	3.5×101 mol/(m3Pa) at 25℃, Sa\cc (2005)
Hauptanwendungen	cleaning productscosmeticsenvironmentalfood and beveragespersonal care
InChI	1S/C14H14O4/c1-3-9-17-13(15)11-7-5-6-8-12(11)14(16)18-10-4-2/h3-8H,1-2,9-10H2
InChIKey	QUDWYFHPNIMBFC-UHFFFAOYSA-N
SMILES	C=CCOC(=O)c1ccccc1C(=O)OCC=C
LogP (Verteilungskoeffizient)	3.23 at 20℃
CAS Datenbank	131-17-9(CAS DataBase Reference)
NIST chemische Informationen	1,2-Benzenedicarboxylic acid, di-2-propenyl ester(131-17-9)
EPA chemische Informationen	Diallyl phthalate (131-17-9)

Sicherheit & Vorschriften

GHS-Einstufung	WarningH302: Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)H302+H332 (17.7%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oralacute 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)
Regulatorische Informationen	Chemical: 1,2-Benzenedicarboxylic acid, di-2-propenyl esterHazard Traits - CarcinogenicityDevelopmental ToxicityEndocrine ToxicityImmunotoxicityReproductive ToxicityRespiratory Toxicity1,2-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/12746Diallyl phthalate: Does not have an individual approval but may be used under an appropriate group standard
DOT-Kennzeichnung	Class 9
Brandgefahren	This chemical is combustible. (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire.
Brandpotenzial	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.
Gesundheitsgefahren	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.
Gefahrenübersicht	May cause skin sensitization[ICSC] A skin, eye, and mucous membrane irritantA lachrymatorMay cause liver damage[CAMEO] LachrymatorHarmful if skin contact, ingested, or inhaled[MSDSonline] See PHTHALATE ESTERS.
FDA-Anforderungen	Diallyl phthalate is an indirect food additive for use only as a component of adhesives.
Reaktive Gruppe	Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
EG-Einstufung	Symbol: Xn, NR: 22-50/53S: (2)-24/25-60-61
UN-Einstufung	UN Hazard Class: 9UN Pack Group: III
Special Reports	Nat'l Research Council CanadaPhthalate Esters in the Aquatic Environment (1980) NRCC No. 17583USEPAAmbient Water Quality Criteria Doc: Phthalate Esters (1980) EPA 440/5-80-067USEPA/ECAOAtlas Document for: Phthalate Esters (1980)
TSCA-Anforderungen	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 04/13/89Sunset date 12/19/95.
Brandbekämpfung	Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)Use powder, carbon dioxide, foam.
Erste-Hilfe-Maßnahmen	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.
Erste Hilfe	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.
Sichere Lagerung	Separated from strong oxidants, strong bases and acids. Store only if stabilized. Store in an area without drain or sewer access.
Brandbekämpfungsverfahren	Water or foam may cause frothing.
Freisetung ohne Brand	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.
Entsorgungsverfahren	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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.
Verschüttetes entsorgen	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.
Preventive Measures	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.
Isolation and Evacuation	Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Eye Prevention	Wear safety spectacles.
Fire Prevention	NO open flames.
Gesundheitliche Auswirkungen	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)
Ökotoxizitätswerte	EC50Species: Scenedesmus subspicatus (Green algae, log growth phase)Conditions: freshwater, static, 24 °C, pH 8.0-9.3Concentration: 5300 ug/L for 48 hrEffect: decreased population biomass /formulated product/Concentration: 3800 ug/L for 72 hrConcentration: 4500 ug/L for 96 hrConcentration: 11000 ug/L for 48 hrEffect: decreased population changes, general /formulated product/For more Ecotoxicity Values (Complete) data for DIALLYL PHTHALATE (9 total), please visit the HSDB record page.
Umweltverhalten	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).
Unerwünschte Wirkungen	Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Expositionspfade	The substance can be absorbed into the body by inhalation of its aerosol and by ingestion.Oral (L1903)inhalation (L1903)dermal (L1903)
Toxizitätsübersicht	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)
Ökotoxizitätsauszüge	/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...
Signs and Symptoms	Redness.Phthalate esters are endocrine disruptors and can cause a number of developmental malformations termed 'phthalate syndrome'. (A2883)
Ongoing Test Status	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]
ICSC Environmental Data	The substance is very toxic to aquatic organisms. It is strongly advised not to let the chemical enter into the environment.
Soil Adsorption/Mobility	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.
Human Toxicity Excerpts	/SIGNS AND SYMPTOMS/ Diallyl phthalate appears to be a low human dermal irritant.
F	19
Wassergefährdungsklasse (WGK)	2
TSCA-Inventar-Status	TSCA listed
UN-Transportnummer	UN 3082 9/PG 3
Zollcode	29173400
RTECS-Nr.	CZ4200000
R-Sätze (R)	22-50/53
Gefahrensymbole	Xn,N
Sicherheitshinweise (S)	24/25-60-61
Gefahrenklasse	9Acute Tox. 4 InhalationAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Skin Sens. 1B
Verpackungsgruppe	III
Lagerklasse	10 - Combustible liquids
Gefahrstoffdaten	131-17-9(Hazardous Substances Data)
Selbstentzündungstemperatur	725 °F

Anwendungen & Verwendung

Beschreibung

Diallyl phthalate is a widely used crosslinking agent for unsaturated polyesters. Diallyl phthalate or diallyl phthalate polyester blends are used primarily as plasticizers and carriers for adding catalysts and pigments to polyesters and in molding, electrical parts, laminating compounds, and impregnation of metal castings. Rubber compounds, epoxy formulations, and polyurethane foams may also contain diallyl phthalate[1].

Verwenden

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

Herstellung & Synthese

synthetische

Diallyl phthalate (DAP) is prepared by reaction of phthalic anhydride and allyl alcohol: