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Didodecyl phosphate

Didodecyl phosphate structure

Didodecyl phosphate 

structure
  • CAS No:

    7057-92-3

  • Formula:

    C24H51O4P

  • Chemical Name:

    Didodecyl phosphate

  • Synonyms:

    Phosphoric acid,didodecyl ester;Dodecyl phosphate ((C12H25O)2(HO)PO);Didodecyl phosphate;Dilauryl phosphate;Ortholeum 162;Dilauryl acid phosphate;Di-n-dodecyl phosphate;ELA;Di(dodecyl) monohydrogen phosphate;Dilauryl hydrogen phosphate;Didodecyl hydrogen phosphate;NSC 12427

  • Categories:

    Organic Chemistry  >  Phosphines

Didodecyl phosphate Basic Attributes

434.633101

434.63

230-341-2

9P58XP0JBR

12427

Crystals (methanol)

Characteristics

55.8

10.2

0.946g/cm3

48-49 °C

507.9°C at 760 mmHg

261ºC

1.457

In water, 4.0X10-6 mg/L at 25 deg C (est)

1.8X10-10 mm Hg at 25 deg C (est)

Henry's Law constant = 3.97X10-7 atm-cu m/mol at 25 °C (est)

pKa = 0.88 (est)

Hydroxyl radical reaction rate constant = 7.5X10-11 cu cm/molec-sec at 25 °C (est)

Safety Information

P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P337+P313, P363, P405, P501

H314

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.

|Danger|H314 (51.85%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P337+P313, P363, P405, and P501|Aggregated GHS information provided by 81 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Di-n-dodecyl phosphate's production and use as a lubricant additive(1) 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 2.7X10+6(SRC), determined from a structure estimation method(2), indicates that di-n-dodecyl phosphate is expected to be immobile in soil(SRC). The estimated pKa of di-n-dodecyl phosphate is 0.88(3), indicating that this compound will primarily exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of di-n-dodecyl phosphate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.0X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(5). Di-n-dodecyl phosphate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.8X10-10 mm Hg(SRC), determined from a fragment constant method(6). Biodegradation data were not available(SRC, 2006).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2.7X10+6(SRC), determined from a structure estimation method(2), indicates that di-n-dodecyl 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 4.0X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). The estimated pKa of di-n-dodecyl phosphate is 0.88(5), indicating that this compound will primarily exist as an anion in the environment and anions generally do not adsorb more strongly to organic carbon than their neutral counterparts(6). The sorption of organophosphorus compounds in soil depends on both organic matter and clay content of soil and the sorption increases as the pH of soil decreases(7), therefore, adsorption to suspended solids and sediments is expected to be pH dependent. According to a classification scheme(8), an estimated BCF of 3.2(SRC), from an estimated log Kow of 10.2(9) and a regression-derived equation(10), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2006).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), di-n-dodecyl phosphate, which has an estimated vapor pressure of 1.8X10-10 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 di-n-dodecyl phosphate may be removed from the air by wet or dry deposition(SRC). Di-n-dodecyl phosphate does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Di-n-dodecyl phosphate is expected to undergo hydrolysis in the environment due to the presence of functional groups (esters) that hydrolyze under environmental conditions(1). The hydrolysis half-life of the analog dimethyl phosphoric acid in neutral solution at 100 °C was found to be 2.4 days(2). Increasing the carbon chain substituent on phosphoric acid (as in the case of di-n-dodecyl phosphate) may not increase the rate of hydrolysis(2). Di-n-dodecyl phosphate does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3.2 was calculated for di-n-dodecyl phosphate(SRC), using an estimated log Kow of 10.2(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of di-n-dodecyl phosphate can be estimated to be 2.7X10+6(SRC). According to a classification scheme(2), this estimated Koc value suggests that di-n-dodecyl phosphate is expected to be immobile in soil. The estimated pKa of di-n-dodecyl phosphate is 0.88(3), indicating that this compound will primarily exist in anion form in the environment and anions generally do not adsorb more strongly to organic carbon and clay than their neutral counterparts(4). The sorption of organophosphorus compounds in soil depends on both organic matter and clay content of soil and the sorption increases as the pH of soil decreases(5).

The Henry's Law constant for di-n-dodecyl phosphate is estimated as 4.0X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that di-n-dodecyl is not expected to volatilize from water surfaces(2). Di-n-dodecyl phosphate's Henry's Law constant indicates that volatilization from moist soil surfaces will not occur(SRC). Di-n-dodecyl phosphate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.8X10-10 mm Hg(SRC), determined from a fragment constant method(3).

Occupational exposure to di-n-dodecyl phosphate may occur through dermal contact with this compound at workplaces where di-n-dodecyl phosphate is produced or used. (SRC)

Drug Information

/SRP:/ 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/|/SRP:/ 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/

didodecyl phosphate

Didodecyl phosphate Use and Manufacturing

Methods of Manufacturing

Production Synthesis of Dilaurylphosphate To a mixture of lauryl alcohol (15.227 g, 81.7 mmol) and benzene (50 ml), phosphorus oxychloride (2.5 ml, 26.8 mmol) was added dropwise at 80° C. (solvent reflux temperature) and further stirred for 21 hours. The solvent of the reaction solution was evaporated under a reduced pressure. To the obtained residue, hexane (10 ml) was added and cooled overnight. The precipitate generated was filtrated to obtain the titled compound (white powder, 4.12 g, 9.5 mmol, yield: 35percent).

Uses

Antistatic agent in textile processing|/SRP66: Former use:/ Lubricant additive /Ortholeum/

Production

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS|(1975) GREATER THAN 4.54X10+5 GRAMS (EST)|(1986) 10 thousand-500 thousand pounds

Ortholeum: trademark for series of lubricant additives /Ortholeum/

Phosphoric acid, didodecyl ester: ACTIVE|Not known to be domestically produced or imported in substantial quantities

Computed Properties

Molecular Weight:434.6
XLogP3:10.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:24
Exact Mass:434.35249710
Monoisotopic Mass:434.35249710
Topological Polar Surface Area:55.8
Heavy Atom Count:29
Complexity:333
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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