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Home > Encyclopedia > Diethyl P-[[bis(2-hydroxyethyl)amino]methyl]phosphonate

Diethyl P-[[bis(2-hydroxyethyl)amino]methyl]phosphonate

Diethyl P-[[bis(2-hydroxyethyl)amino]methyl]phosphonate structure

Diethyl P-[[bis(2-hydroxyethyl)amino]methyl]phosphonate 

structure
  • CAS No:

    2781-11-5

  • Formula:

    C9H22NO5P

  • Chemical Name:

    Diethyl P-[[bis(2-hydroxyethyl)amino]methyl]phosphonate

  • Synonyms:

    Phosphonic acid,P-[[bis(2-hydroxyethyl)amino]methyl]-,diethyl ester;Phosphonic acid,[[bis(2-hydroxyethyl)amino]methyl]-,diethyl ester;Diethyl P-[[bis(2-hydroxyethyl)amino]methyl]phosphonate;Fyrol 6;Diethyl [[N,N-bis(2-hydroxyethyl)amino]methyl]phosphonate;Diethyl [(diethanolamino)methyl]phosphonate;Diethyl [[bis(2-hydroxyethyl)amino]methyl]phosphonate;Diethyl [N,N-bis(2-hydroxyethyl)amino]methanephosphonate;Adeka FC 450;FC 450;Levagard 4090;NSC 82342;Levagard 4090N;FRC 6;N,N-Bis(2-hydroxyethyl)aminomethylphosphonic acid diethyl ester;Diethyl N,N′-bis(2-hydroxyethyl)aminomethylphosphonate;WSFR 6;2-[Diethoxyphosphorylmethyl(2-hydroxyethyl)amino]ethanol;109223-83-8;163447-57-2

  • Categories:

    Organic Chemistry  >  Phosphines

Description

Liquid


Liquid

Diethyl P-[[bis(2-hydroxyethyl)amino]methyl]phosphonate Basic Attributes

255.248

255.25

220-482-8

920Z48KJ0P

82342

DTXSID2029242

Dark amber liquid

Characteristics

89.04000

0.10

Liquid

1.2±0.1 g/cm3

150 °C @ Press: 0.1 Torr

195.0±23.7 °C

1.475

In water, 900 g/L at 25 deg C[US EPA; High Production Volume (HPV) Challenge Program. The HPV Voluntary Challenge Chemical List. Robust Summaries and Test Plans. Phosphonic Acid, [

0.43 mm Hg at 20 deg C[US EPA; High Production Volume (HPV) Challenge Program. The HPV Voluntary Challenge Chemical List. Robust Summaries and Test Plans.

Henry's Law constant = 1.6X10-7 atm-cu m/mole at 25 °C /Estimated/

pKa= 5.6 /Estimated/

Hydroxyl radical reaction rate constant = 1.4X10-10 cu cm/molec-sec at 25 °C /Estimated/

Safety Information

P261, P264, P270, P272, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, P501

H302

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.|Disposal of Fyrol 6 at the manufacturing site is done in a closed wastewater treatment system.

The U.S. high production volume (HPV) chemicals are those which are manufactured in or imported into the United States in amounts equal to or greater than one million pounds per year. Robust Summaries include health effects, ecotoxicity data, and environmental fate information for selected chemicals. EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program's Robust Summaries and Test Plans. Available from: http://www.epa.gov/chemrtk/viewsrch.htm on Fyrol 6 as of November 4, 2004.

|Warning|H302 (75.47%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P281, P301+P312, P308+P313, P330, P405, and P501|Aggregated GHS information provided by 86 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Shipments are typically done in 55 gallon drums and occasionally in bulk tank trucks.

Toxicity

LD50 Rat (Sprague-Dawley) oral >5000 mg/kg|LD50 Rabbit (Stauffland albino) dermal >2000 mg/kg/24 hr

Diethyl ((diethanolamino)methyl) phosphonate's production and use as a flame retardant in rigid polyurethane foams(1,2) may result in its release to the environment through various waste streams(SRC).[(1) US EPA; High Production Volume (HPV) Challenge Program. The HPV Voluntary Challenge Chemical List. Robust Summaries and Test Plans. Phosphonic Acid, [

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 9.7(SRC), determined from a log Kow of -0.72(2) and a regression-derived equation(3), indicates that diethyl ((diethanolamino)methyl) phosphonate is expected to have very high mobility in soil(SRC). The estimated pKa of diethyl ((diethanolamino)methyl) phosphonate is 5.6(4), indicating that this compound is expected to partially exist in the protonated form in the environment, and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts(5). Volatilization of diethyl ((diethanolamino)methyl) phosphonate from moist soil surfaces is not expected(SRC) given an estimated Henry's Law constant of 1.6X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 0.43 mm Hg(2), and water solubility, 900 g/L(2). Diethyl ((diethanolamino)methyl) phosphonate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). Diethyl ((diethanolamino)methyl) phosphaonte was found to biodegrade 15-19% after 28 days in a modified Sturm test(2). Based on this screening test, diethyl ((diethanolamino)methyl) phosphonate would be expected to biodegrade slowly in soil(SRC).[(1) Swann RL et al; Res Rev 85: 17-28 (1983) (2) US EPA; High Production Volume (HPV) Challenge Program. The HPV Voluntary Challenge Chemical List. Robust Summaries and Test Plans. Phosphonic Acid, [|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 9.7(SRC), determined from a log Kow of -0.72(2) and a regression-derived equation(3), indicates that diethyl ((diethanolamino)methyl) phosphonate is not 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 1.6X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 0.43 mm Hg(2), and water solubility, 900 g/L(2). The estimated pKa of diethyl ((diethanolamino)methyl) phosphonate is 5.6(4), indicating that this compound is expected to partially exist in the protonated form in the environment, and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts(5). In general, hydrolysis may be an important fate for phosphonic acid esters at basic pH's(3). According to a classification scheme(6), an estimated BCF of 3.2(SRC), determined from its log Kow of -0.72(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Diethyl ((diethanolamino)methyl) phosphonate was found to biodegrade 15-19% after 28 days in a modified Sturm test(2). Based on this screening test, diethyl ((diethanolamino)methyl) phosphonate would be expected to biodegrade slowly in water(SRC).[(1) Swann RL et al; Res Rev 85: 17-28 (1983) (2) US EPA; High Production Volume (HPV) Challenge Program. The HPV Voluntary Challenge Chemical List. Robust Summaries and Test Plans. Phosphonic Acid, [|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diethyl ((diethanolamino)methyl) phosphonate, which has a vapor pressure of 0.43 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase diethyl ((diethanolamino)methyl) phosphonate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2.7 hours(SRC), calculated from its rate constant of 1.4X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Diethyl ((diethanolamino)methyl) phosphonate is not expected to be susceptible to direct photolysis by sunlight, since it does not contain functional groups that are expected to absorb light with wavelengths >290 nm(SRC).[(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988) (2) US EPA; High Production Volume (HPV) Challenge Program. The HPV Voluntary Challenge Chemical List. Robust Summaries and Test Plans. Phosphonic Acid, [

The rate constant for the vapor-phase reaction of diethyl ((diethanolamino)methyl) phosphonate with photochemically-produced hydroxyl radicals has been estimated to be 1.4X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Diethyl ((diethanolamino)methyl) phosphonate is not expected to be susceptible to direct photolysis by sunlight, since it does not contain functional groups that are expected to absorb light with wavelengths >290 nm (SRC). In general, hydrolysis may be an important fate for phosphonic acid esters at basic pH's(2).

An estimated BCF of 3.2 was calculated for diethyl ((diethanolamino)methyl) phosphonate(SRC), using a log Kow of -0.72(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).[(1) US EPA; High Production Volume (HPV) Challenge Program. The HPV Voluntary Challenge Chemical List. Robust Summaries and Test Plans. Phosphonic Acid, [

The Koc of diethyl ((diethanolamino)methyl) phosphonate is estimated as 9.7(SRC), using a log Kow of -0.72(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that diethyl ((diethanolamino)methyl) phosphonate is expected to have very high mobility in soil. However, the estimated pKa of diethyl ((diethanolamino)methyl) phosphonate is 5.6(4), indicating that this compound is expected to partially exist in the protonated form in the environment, and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts(5).[(1) US EPA; High Production Volume (HPV) Challenge Program. The HPV Voluntary Challenge Chemical List. Robust Summaries and Test Plans. Phosphonic Acid, [

The Henry's Law constant for diethyl ((diethanolamino)methyl) phosphonate is estimated as 1.6X10-7 atm-cu m/mole(SRC) derived from its vapor pressure, 0.43 mm Hg(1), and water solubility, 900 g/L(1). This Henry's Law constant indicates that diethyl ((diethanolamino)methyl) phosphonate is not expected to volatilize from water surfaces(2). Diethyl ((diethanolamino)methyl) phosphonate's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected(SRC). Diethyl ((diethanolamino)methyl) phosphonate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).[(1) US EPA; High Production Volume (HPV) Challenge Program. The HPV Voluntary Challenge Chemical List. Robust Summaries and Test Plans. Phosphonic Acid, [

NIOSH (NOES Survey 1974) has statistically estimated that 441 workers are potentially exposed to diethyl ((diethanolamino)methyl) phosphonate in the US(1). Occupational exposure to diethyl ((diethanolamino)methyl) phosphonate may occur through inhalation and dermal contact with this compound at workplaces where diethyl ((diethanolamino)methyl) phosphonate is produced or used(SRC). Exposure to the general population would not be expected(SRC), since diethyl ((diethanolamino)methyl) phosphonate reacts and becomes an integral part of the foam structure when it is added to polyurethane foams as flame retardants(2,3).[(1) NIOSH; National Occupational Exposure Survey (NOES) (1974) (2) US EPA; High Production Volume (HPV) Challenge Program. The HPV Voluntary Challenge Chemical List. Robust Summaries and Test Plans. Phosphonic Acid, [

Drug Information

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/

diethyl N,N-bis(2-hydroxyethyl)aminomethylphosphonate

Diethyl P-[[bis(2-hydroxyethyl)amino]methyl]phosphonate Use and Manufacturing

Methods of Manufacturing

REACTION OF DIETHANOLAMINE WITH FORMALDEHYDE & DIETHYL PHOSPHITE

Uses

Flame retardants


Foam seating and bedding products

Production

Phosphonic acid, [[bis(2-hydroxyethyl)amino]methyl]-, diethyl 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).[EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program. Phosphonic acid, [|(1977) AT LEAST 4.54X10+8 GRAMS|(1981) No Data

"FYROL" TRADEMARK FOR A SERIES OF PHOSPHATE FLAME RETARDANT PLASTICIZERS. USED IN POLYESTERS, RIGID URETHANE FOAM, POLYURETHANE, PHENOLIC, EPOXY, PVC, PVA, NITROCELLULOSE, CELLULOSE ACETATE, & ETHYL CELLULOSE RESINS. /FYROL/

Asphalt paving, roofing, and coating materials manufacturing|Phosphonic acid, P-[[bis(2-hydroxyethyl)amino]methyl]-, diethyl ester: ACTIVE|Fyrol 6 is a flame retardant that is reacted into rigid polyurethane foam. ...Fyrol 6 reacts with and becomes an integral part of the resin system during production.

Computed Properties

Molecular Weight:255.25
XLogP3:-1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:10
Exact Mass:255.12355980
Monoisotopic Mass:255.12355980
Topological Polar Surface Area:79.2
Heavy Atom Count:16
Complexity:198
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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