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Triallyl phosphate

Triallyl phosphate structure

Triallyl phosphate 

structure
  • CAS No:

    1623-19-4

  • Formula:

    C9H15O4P

  • Chemical Name:

    Triallyl phosphate

  • Synonyms:

    Phosphoric acid,tri-2-propen-1-yl ester;Phosphoric acid,triallyl ester;Phosphoric acid,tri-2-propenyl ester;Triallyl phosphate;Triallyl orthophosphate;NSC 30703;Trially phosphate

  • Categories:

    Pharmaceutical Intermediates  >  Heterocyclic Compound

Triallyl phosphate Basic Attributes

218.18700

218.19

216-606-5

5INO747KFF

30703

DTXSID5061827

WATER-WHITE LIQ

2919900090

Characteristics

54.57000

2.70230

1.064 g/cm3 @ Temp: 25 °C

FP: BELOW -50 °C

80 °C @ Press: 0.5 Torr

120.1ºC

1.447

Water solubility = >1 g/L

0.032mmHg at 25°C

WT/VOL CONVERSION 8.91 MG/CU M IS EQUIV TO 1 PPM|Triallylphosphate polymerizes rapidly on exposure to air

Safety Information

R36/37/38

S26; S36/37/39

TC8575000

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

|Danger|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

URBAN/SUBURBAN: Triallyl phosphate was not found in ambient air samples taken from Kitakyushu, Japan. Monitoring was conducted using GC with a nitrogen-phosphorus or mass spectroscopy detector; triallyl phosphate had a detection limit of 0.04 ng(1).

Toxicity

Triallyl phosphate's production and use as a plasticizer for polymers and as a flame retardant may result in its release to the environment in various waste streams(1,SRC).

TERRESTRIAL FATE: An estimated Koc of 220(1,SRC), based on a measured log Kow(2), indicates that triallyl phosphate will have moderate mobility in soil(3); some leaching of this compound may be possible as it is relatively soluble in water(2,SRC). Under alkaline soil conditions, hydrolysis of triallyl phosphate may be rapid and will be expected to be a major fate process for this compound; the rate of hydrolysis in neutral or slightly acid soil environments should be slower(4,SRC). Some biodegradation may be possible; 0-41% biodegradation of triallyl phosphate was measured over a 4 week time period using an activated sludge inoculum(2). Exposure to air may cause triallyl phosphate to polymerize rapidly(5). Triallyl phosphate is not expected to volatilize from soil surfaces(6,SRC).|AQUATIC FATE: Hydrolysis of triallyl phosphate, particularly in alkaline waters, will be a major fate process for triallyl phosphate; in neutral or slightly acidic water, triallyl phosphate will hydrolyze less rapidly(1,SRC). Limited biodegradation may be possible; in natural water samples triallyl phosphate was degraded from 0-10% over 29 days at 7 °C(3). Greater biodegradation (0-41%) was observed in samples inoculated with activated sludge and incubated for a period of 4 weeks(2). Triallyl phosphate is not expected to volatilize from water surfaces based on an estimated Henry's Law constant of 5.6X10-7 atm-cu m/mole(4,SRC). If released to an aquatic environment, triallyl phosphate is not expected to bioconcentrate with experimental BCF values ranging from <0.1 to <1.2(2).|ATMOSPHERIC FATE: Based on an estimated vapor pressure of 0.0054 mm Hg at 25 °C(1,SRC), triallyl phosphate will exist primarily in the vapor phase in the ambient atmosphere(2,SRC). Both hydroxyl radical and ozone reactions, are expected to be major fate processes for this compound in the atmosphere. Triallyl phosphate will degrade by reaction with photochemically produced hydroxyl radicals with an estimated half-life of about 3 hours(3,SRC). A half-life of 8 hours is predicted for the reaction of triallyl phosphate with ozone molecules(4).

The rate constant for the vapor phase reaction of triallyl phosphate with photochemically produced hydroxyl radicals has been estimated as 1.3X10-10 cu cm/molecule-sec at 25 °C which corresponds to an atmospheric half-life of about 3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). The rate constant for the vapor phase reaction of triallylphosphate with ozone molecules has been estimated as 3.6X10-17 cu cm/molecule-sec at 25 °C which corresponds to an atmospheric half-life of about 8 hours at an atmospheric concentration of 7X10+11 ozone molecules/cu cm(2). Phosphate esters are generally resistant to hydrolysis in neutral or acid waters (pH 5.0-7.0) but have been found to degrade rapidly in sterile distilled water at pH 9.0-9.5(3). Hydrolysis of phosphate esters is generally promoted by alkaline conditions as the phosphate ester undergoes second order nucleophilic reactions due to the hydroxide ion involving cleavage of the O-P bond; C-O cleavage is dominant for those compounds which undergo acid and water promoted hydrolyses of esters(3). Rate constants for C-O and P-O were measured for methyl phosphate at 75 °C; 8.23 1/M-sec (P-O bond) for the anion, 0.5 1/M-sec (C-O) for the neutral form, and 2.0 and 1.08 1/M-sec for the C-O and P-O conjugate acid forms, respectively(3). Thus under alkaline conditions triallyl phosphate should hydrolyze(3,SRC). Exposure to air causes triallyl phosphate to polymerize rapidly(4).

1.20|Bioconcentration of triallyl phosphate was measured in carp over a 6 week time period. At concentrations of 0.1 mg/ml and 0.01 mg/ml triallyl phosphate, BCF values of <0.1-0.9 and <1.2 respectively, were reported(1). A BCF value of 13 was estimated for triallyl phosphate from a recommended regression-derived equation(2,SRC) and an experimental log Kow of 1.76(1). These values indicate that bioconcentration of triallyl phosphate in aquatic organisms is not an important fate process for this compound(SRC).

Using a structure estimation method(1,SRC) and an experimental Kow of 1.76(2), the Koc for triallyl phosphate was estimated as 216(2). According to a suggested classification scheme(3), this estimated Koc value indicates that triallyl phosphate is moderately mobile in soil(SRC). Based on a water solubility of >1 g/L(2), leaching of this compound may be possible(1,SRC).

The Henry's Law constant for triallyl phosphate was estimated as 5.6X10-7 atm-cu m/mole at 25 °C using a structure estimation method(1,SRC). This value indicates that triallyl phosphate is essentially not volatile from water surfaces(2,SRC).

Triallyl phosphate Use and Manufacturing

Methods of Manufacturing

Preparation of triallyl phosphate is through the condensation of phosphorus trichloride with allyl alcohol to give triallyl phosphite followed by oxidation with air.

Uses

CHEM INT FOR FLAME RETARDANTS FOR TEXTILES|FLAME-RETARDANT & PLASTICIZER FOR POLYMERS|A possible commercial application of triallylphosphate is the crosslinking with polyolefins in the presence of peroxides and, if necessary, in the presence of foaming agents.|As a flame-retardant finish for fabric.

Production

(1979) NOT COMMERCIALLY PRODUCED IN U.S.|(1981) NOT COMMERCIALLY PRODUCED IN U.S.

Phosphoric acid, tri-2-propen-1-yl ester: INACTIVE

Triallylphosphate has been measured in ambient air based on a procedure using Soxhlet extraction followed by GC with a Nitrogen-Phosphorus detector. 90-100% recovery was obtained during the extraction step; the detection limit of triallylphosphate was 0.04 ng.

Computed Properties

Molecular Weight:218.19
XLogP3:1.5
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:9
Exact Mass:218.07079595
Monoisotopic Mass:218.07079595
Topological Polar Surface Area:44.8
Heavy Atom Count:14
Complexity:199
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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