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Home > Encyclopedia > Phenol, 2,5-dimethyl-, 1,1′,1′′-phosphate

Phenol, 2,5-dimethyl-, 1,1′,1′′-phosphate

Phenol, 2,5-dimethyl-, 1,1′,1′′-phosphate structure

Phenol, 2,5-dimethyl-, 1,1′,1′′-phosphate 

structure
  • CAS No:

    19074-59-0

  • Formula:

    C24H27O4P

  • Chemical Name:

    Phenol, 2,5-dimethyl-, 1,1′,1′′-phosphate

  • Synonyms:

    Phenol,2,5-dimethyl-,1,1′,1′′-phosphate;2,5-Xylenol,phosphate (3:1);Phenol,2,5-dimethyl-,phosphate (3:1);2,5-Xylyl phosphate ((C8H9O)3PO);Tris(2,5-dimethylphenyl) phosphate;SP 10 (ester);SP 10;NSC 66475

Phenol, 2,5-dimethyl-, 1,1′,1′′-phosphate Basic Attributes

410.44300

410.44

242-799-0

PP52A5JDYU

66475

Crystals (from crystallization with dilute alcohol)

2919900090

Characteristics

54.57000

7.18190

1.197 g/cm3 @ Temp: 25 °C

79.8 °C

260-265 °C @ Press: 8 Torr

245.3ºC

1.569

Sol in ether, benzene; slightly soluble in ethanol

3.28E-08mmHg at 25°C

log Kow= 5.63 /Kronitex TXP/|Vapor presure: 5.15X10-8 mm Hg @ 30 °C /Kronitex TXP/

Safety Information

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.

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+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.

Toxicity

Specific use information for tris(2,5-xylenyl)phosphate was not located. However, trixylenyl phosphates are produced and used as flame retardants and plasticizers(1) and hydraulic fluids(2) and tris(2,5-xylenyl)phosphate may be released to the environment through various waste streams during such production and/or use(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.0X10+5(SRC), determined from a structure estimation method(2), indicates that tris(2,5-xylenyl)phosphate is expected to be immobile in soil(SRC). Volatilization of tris(2,5-xylenyl)phosphate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.2X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Tris(2,5-xylenyl)phosphate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.6X10-8 mm Hg(SRC), determined from a fragment constant method(4). Tris(2,5-xylenyl)phosphate may be susceptible to hydrolysis in alkaline soils based on aquatic data for other triaryl phosphates(6). Biodegradation of aryl phosphates may occur slowly in the environment based on activated sludge tests showing 13 to 65% biodegradation of trixylenyl phosphate over 14 and 25 weeks, respectively(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.0X10+5(SRC), determined from a structure estimation method(2), indicates that tris(2,5-xylenyl)phosphate 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 7.2X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Tris(2,5-xylenyl)phosphate may be stable to degradation in waters having slightly acidic and neutral pH values; however, decomposition of tris(2,5-xylenyl)phosphate may occur in alkaline waters(8). According to a classification scheme(5), an estimated BCF of 720(SRC), from a log Kow of 5.63(6), measured for Kronitex TXP, a commercial product containing tris(2,5-xylenyl)phosphate and other trixylenyl and triethylphenyl phosphate isomers, and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Biodegradation of aryl phosphates may occur slowly in the environment based on activatd sludge tests showing 13 to 65% biodegradation of trixylenyl phosphate over 14 and 25 weeks, respectively(6).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tris(2,5-xylenyl)phosphate, which has an estimated vapor pressure of 2.6X10-8 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 tris(2,5-xylenyl)phosphate may be removed from the air by wet and dry deposition(SRC).

Triaryl phosphates are generally stable to hydrolysis at neutral pH values and undergo moderate hydrolysis in acidic solutions(1). Triaryl phosphates will degrade at appreciable rates in natural waters under alkaline conditions to apparently stable, water soluble, anionic diesters such as diaryl phosphates(1). No persistence data specific to tris(2,5-xylenyl)phosphate was available; however, based on data pertaining to triphenyl and tricresyl phosphates(1), tris(2,5-xylenyl)phosphate is expected to hydrolyze in natural alkaline waters. Tris(2,5-xylenyl)phosphate is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm)(SRC).

An estimated BCF value of 720 was calculated for tris(2,5-xylenyl)phosphate(SRC) using a log Kow of 5.63(2) measured for Kronitex TXP, a commercial product primarily consisting of the 2,5-, 3,4-, 3,5- and/or the 2,4-isomers of trixylylphosphates along with mixes of xylenyl phosphates or xylenyl/ethylphenyl phosphates(1), and a regression-derived equation(3). The actual BCF of tris(2,5-xylenyl)phosphate would be expected to be slightly higher, for a greater Kow value would be anticipated for tris(2,5-xylenyl)phosphate due to the presence of lower molecular weight constituents among the TXP mixture. This is in keeping with this class of chemicals as analogous tri-p-cresyl phosphate has measured BCFs of 1,420 and 928 in rainbow trout and fathead minnows, respectively(4). According to a classification scheme(5), this BCF value suggests the potential for bioconcentration of tris(2,5-xylenyl)phosphate in aquatic organisms is high(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for tris(2,5-xylenyl)phosphate can be estimated to be 1.0X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that tris(2,5-xylenyl)phosphate is expected to be immobile in soil.

The Henry's Law constant for tris(2,5-xylenyl)phosphate is estimated as 7.2X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that tris(2,5-xylenyl)phosphate is expected to be essentially nonvolatile from water surfaces(2). Tris(2,5-xylenyl)phosphate's Henry's Law constant(1) indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Tris(2,5-xylenyl)phosphate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.6X10-8 mm Hg(SRC), determined from a fragment constant method(3).

Specific use information pertaining to tris(2,5-xylenyl)phosphate was not available, although triaryl phosphates are generally employed as flame-retardants and plasticizers(1) and in hydraulic fluids(2). Occupational exposure to tris(2,5-xylenyl)phosphate may occur through inhalation of dust particles and dermal contact with this compound at workplaces where tris(2,5-xylenyl)phosphate is produced or used(SRC).

Drug Information

Tri-o-cresyl phosphate and other o-cresyl-components /TXP formulations/

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

Phenol, 2,5-dimethyl-, 1,1′,1′′-phosphate Use and Manufacturing

Methods of Manufacturing

Xylenol, mixed + phosphorus oxychloride (dehydrochlorination) /Trixylyl phosphate/

Uses

Used in flame retardants' formulations|Non-flammable hydraulic fluid (steel works, furnaces, mines); polyvinyl chloride plasticizer /Trixylyl phosphate/

Production

In million pounds: (1980) 5.0; (1981) 4.1; (1982) 3.4; (1983) 3.4; (1984) 3.7 /Trixylyl phosphate/

TRIS(2,5-XYLENYL)PHOSPHATE IS PRESENT IN BOTH KRONITEX TXP AND FYRQUELL 220, WHICH ARE COMMERCIALLY USED FLAME RETARDANTS.

Determination of phosphate esters in environmental samples or technical products is best accomplished using gas chromatography (GLC) with phosphorus-specific detectors. However, the related isomers in such products as TCP and TXP are difficult to separate even with capillary columns. Thus, for determination of specific components such as TOCP, analysis of phenolic moieties by GLC following alkaline hydrolysis of the phosphate esters is a useful technique. /Phosphate esters/

Computed Properties

Molecular Weight:410.4
XLogP3:7.2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:410.16469634
Monoisotopic Mass:410.16469634
Topological Polar Surface Area:44.8
Heavy Atom Count:29
Complexity:491
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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