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Triethyl phosphate

Triethyl phosphate structure

Triethyl phosphate 

structure
  • CAS No:

    78-40-0

  • Formula:

    C6H15O4P

  • Chemical Name:

    Triethyl phosphate

  • Synonyms:

    Phosphoric acid,triethyl ester;Ethyl phosphate;Triethyl phosphate;TEP;Triethoxyphosphine oxide;Levagard TEP;NSC 2677;Fyrol TEP;Levagard TEP-Z;SP 0724;Tri-n-ethyl phosphate;Disflamoll TEP

  • Categories:

    Cosmetic Ingredient  >  Dissolving Agent

Description

Triethyl phosphate is a colorless, high-boiling liquid and containing 17 wt % phosphorus; mild odor. Very stable at ordinary temperatures, compatible with many gums and resins, soluble in most organic solvents, miscible with water. When mixed with water is quite stable at room temperature, but at elevated temperatures it hydrolyzes slowly. Combustible.It is manufactured from diethyl ether and phosphorus pentoxide via a metaphosphate intermediate.

Triethyl phosphate has been used co


Triethyl phosphate appears as a colorless, corrosive liquid. Combustible. Slowly dissolves in water and sinks in water. Severely irritates skin, eyes and mucous membranes.|Liquid|COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.


Triethyl phosphate appears as a colorless, corrosive liquid. Combustible. Slowly dissolves in water and sinks in water. Severely irritates skin, eyes and mucous membranes.|Triethyl phosphate is a trialkyl phosphate that is the triethy ester derivative of phosphoric acid. It derives from an ethanol.

Triethyl phosphate Basic Attributes

182.15500

182.15

201-114-5

QIH4K96K7J

1730

2677

3265|3278

DTXSID8026228

Liquid|Colorless, high-boiling liquid

29190090

Characteristics

54.57000

0.8 (LogP)

Triethyl phosphate appears as a colorless, corrosive liquid. Combustible. Slowly dissolves in water and sinks in water. Severely irritates skin, eyes and mucous membranes.

1.0725 g/cm3 @ Temp: 19 °C

-56.4 °C

215-216 °C

130ºC

1.405-1.407

H2O: soluble

Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

1 mm Hg ( 40 °C)

6.28 (vs air)

LD50 orally in Rabbit: 1165 mg/kg

Mild

5.53e-11 cm3/molecule*sec

3.60e-08 atm-m3/mole|Henry's Law constant = 3.60X10-8 atm-cu m/mol at 20 °C

132.63 Ų [M+H]+

Liquid molar volume = 0.1708 cu-m/kmol; Enthalpy Heat of Formation = -1.245X10+9 J/kmol|Dielectric constant = 13.20|Hydroxyl radical reaction rate constant = 5.53X10-11 cu cm/molec-sec at 25 °C

Slowly dissolves in water with slight decomposition (NTP, 1992).

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

Organophosphates, such as TRIETHYL PHOSPHATE, are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.

845 °F (USCG, 1999)|850 °F (454 °C)|452 °C

Lower flammable limit: 1.2% by volume; Upper flammable limit: 10% by volume

Safety Information

3278

1

R22

S25

TC7900000

Xn

Stable. Combustible. Incompatible with strong oxidizing agents, water.

P305 + P351 + P338

H302-H319

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.

Can react vigorously with oxidizing materials.

Special Hazards of Combustion Products: May produce hazardous decomposition products such as carbon dioxide, carbon monoxide and oxides of phosphorus. (USCG, 1999)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P280, P301+P312, P305+P351+P338, P330, P337+P313, and P501|Aggregated GHS information provided by 1357 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P260, P261, P264, P270, P271, P280, P281, P301+P312, P304+P340, P305+P351+P338, P308+P313, P309+P311, P312, P330, P337+P313, P403+P233, P405, and P501

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, 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 alcohol followed by washing with a strong 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. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

Protective gloves, safety glasses, rubber gloves & rubber boots. (USCG, 1999)

Slight when exposed to heat or flame.

To fight fire, use carbon dioxide, dry chemical, alcohol foam.

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Wash away remainder with plenty of water.

Separated from strong oxidants and strong bases. Well closed. Ventilation along the floor.

A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.

The substance is mildly irritating to the eyes. The substance may cause effects on the central nervous system.

NO open flames.

Use ventilation, local exhaust or breathing protection.

Protective gloves.

Wear safety goggles.

| 1 - Materials that, under emergency conditions, can cause significant irritation.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 1 - Materials that in themselves are normally stable but that can become unstable at elevated temperatures and pressures.

Triethyl phosphate was one of a group of six phosphate triesters detected in the leachate from the Osaka North Port Sea-Based Solid Waste Disposal Site in Japan with concentrations ranging from 0.1 to 17.0 ug/L(1). Triethyl phosphate was detected in one of five landfill leachate samples at a concentration of 1-10 ppm collected from five Danish sanitary landfills in February 1983(2). Leachate plumes from two sanitary landfills (Waterloo and North Bay, Ontario) were monitored in 1982 and triethyl phosphate was detected at 10-15 ug/L at the Waterloo site(3). Primary effluent from a wastewater treatment plant was applied to a series of basins on a kame where it was subjected to rapid infiltration treatment(4). Triethyl phosphate was not detected in the initial basin floodwater but was detected at 0.71 ug/L in a down-gradient monitoring well(4). Triethyl phosphate was detected at 0.3 ug/L in a well located in an Oklahoma landfill(5). At unreported concentrations, triethyl phosphate was detected in groundwater from Rocky Mountain Arsenal(6). Triethyl phosphate was detected in 3 samples taken from the leachate in a Swedish municipal landfill(7). Triethyl phosphate was detected in advanced waste treatment concentrates from Lake Tahoe, CA in 1974 and from Blue Plains, Washington DC in 1974(8).

SEDIMENT: Sediment samples from 23 sampling stations in a shallow marine inlet near an organophosphorus pesticide and intermediate chemicals production plant in Jutland, Denmark were collected during 1982-1983(1); total samples taken were 39, triethyl phosphate was detected in samples from 11 of 23 positions at levels ranging from a few hundred ng/kg to 1.7 ug/kg except for two sites close to the plant where the levels were 2.7 and 8.5 ug/kg dry weight(1).

URBAN/SUBURBAN: Triethyl phosphate was detected in both Soxhlet extraction and volatile organic analyses as a major component in one of seven carpet samples(1).|INDOOR: Indoor air samples taken from new or recently renovated buildings in Switzerland contained a mean triethyl phosphate concentration of 60 ug/cu m(1). Triethyl phosphate was detected in almost all indoor air samples collected from 22 houses (44 rooms) and 11 office buildings (22 offices) in Tokyo, Japan(2).|SOURCE DOMINATED: In a laboratory study of vapors (24 liters) emitted from a liquid waste lagoon (uncharacterized), triethyl phosphate was detected(1).

Toxicity

LD50 Rat oral 1.6 g/kg|LC50 Rat inhalation >8817 mg/cu m/4 hours|LD50 Rat ip 0.8 g/kg|LD50 Guinea pig dermal >21.4 g/kg|For more Non-Human Toxicity Values (Complete) data for TRIETHYL PHOSPHATE (9 total), please visit the HSDB record page.

/OTHER TERRESTRIAL SPECIES/ ... Studies were conducted to determine the phytotoxicity of TEP using sorghum-sudangrass (Sorghum bicolor (L.) Moench), tomato (Lycopersicon lycopersicum Mill.), and glossy privet (Ligustrum lucidum Ait.) as test plants grown on Mimbres-Glendale (MG) and Nickel-Tencee (NT) sod associations obtained from White Sands Missile Range. Triethyl phosphate was applied to sod and foliar tissue at rates of 0, 4, 400, and 40 000 mg m-2 sod surface. Triethyl phosphate also was applied in a thickened formulation, as used in missile testing, at an application rate of 40 000 mg m-2 on both soil and foliar tissue. Toxicity was only observed at the highest application rate with pure and thickened TEP. The method of TEP application to soil or foliar tissue did not affect the dry matter weight of tomato or glossy privet growth. There were inconsistent effects of TEP application method on sorghum-sudangrass dry matter weight, depending on soil type. Triethyl phosphate affected the test plants differently with resistance to TEP toxicity increasing in the order: tomato congruent sorghum-sudangrass on NT soil < sorghum-sudangrass on MG soil < glossy privet. A seedling emergence study using sorghum-sudangrass, tomato, and cucumber (Cucumis sativus L.) resulted in similar conclusions from the whole plant studies showing TEP toxicity only at the highest application rate of 40 000 mg m-2. There were indications from sorghum-sudangrass growth and cucumber seedling emergence that TEP toxicity may be less on soil having a higher clay and organic matter content, which may have been due to TEP sorption in soil and decreased TEP bioavailability to plant roots. The absence of phytotoxicity symptoms indicated plants would not be harmed if application rates were at or below 400 mg TEP m-2.

Triethyl phosphate's production and use as an insecticide production intermediate, a fire retardant, a plasticizer, an ethylating agent, a catalyst, a desensitizing agent for peroxides, and a laquer remover(1-3) 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 65(SRC), determined from a log Kow of 0.80(2) and a regression-derived equation(3), indicates that triethyl phosphate is expected to have high mobility in soil(SRC). Volatilization of triethyl phosphate from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 3.60X10-8 atm-cu m/mole(4). Triethyl phosphate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.393 mm Hg(5). Triethyl phosphate, present at 100 mg/L, reached 0% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(6) and is therefore not expected to readily biodegrade in the environment.|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 65(SRC), determined from a log Kow of 0.80(2) and a regression-derived equation(3), indicates that triethyl phosphate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 3.60X10-8 atm-cu m/mole(4). According to a classification scheme(5), measured BCF values ranging from 2.4-22(6) suggests the bioconcentration in aquatic organisms is low(SRC). Triethyl phosphate, present at 100 mg/L, reached 0% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(6) and is therefore not expected to readily biodegrade in aquatic environments.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), triethyl phosphate, which has a vapor pressure of 0.393 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase triethyl phosphate 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 7.0 hours(SRC), calculated from its rate constant of 5.53X10-11 cu cm/molecule-sec at 25 °C(3). Triethyl phosphate does not absorb light at wavlenghts >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of triethyl phosphate with photochemically-produced hydroxyl radicals is 5.53X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 7.0 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2). Triethyl phosphate is expected to undergo hydrolysis in the environment due to the presence of functional groups (esters) that hydrolyze under environmental conditions(3). A neutral rate of hydrolysis at 25 °C was measured as 2.4X10-10/sec(4). Second-order alkaline hydrolysis rate constants of 1.75X10-5/M-sec(5) (half-life of 1.3X10+3 years at pH 8) and 7.9X10-4 L/mol-min(6) (half-life of 1.7X10+3 years at pH 8) were measured for triethyl phosphate at 27 and 25 °C, respectively; neutral and alkaline hydrolysis products will be the same(5). Hydrolysis rate constants for triethyl phosphate over a range of pH values was measured as follows: pH 4.9, k = 0.95X10-5/sec; pH 7.1, k = 1.3X10-5/sec; pH 8.9, k = 0.95X10-5/sec; pH 10.1, k = 1.65X10-5/sec at 101 °C(7). The corresponding half-lives for these rate constants were calculated as 2.3X10+6 years, 1.7X10+4 years, 230 years, and 13 years, respectively(SRC). Hydrolysis of triethyl phosphate does not proceed rapidly until the pH reaches 10-11(7). Triethyl phosphate has low susceptibility to acid-catalyzed hydrolysis(4). There was no systemic increase in the rate of hydrolysis (0.835X10-5 at 101 °C) of triethyl phosphate in water with increasing amounts of acid (0.25 and 0.50 M H2SO4)(4). Triethyl phosphate does not absorb light at wavelengths >290 nm(8) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

1.29|Bioconcentration of triethyl phosphate was measured in carp (5.1% average lipid content) over a 6 week time period. At triethyl phosphate concentrations of 2.0 and 0.2 mg/ml, BCF values of 2.4-6.5 and 9.2-22, respectively, were reported(1). According to a classification scheme(2), these BCF values suggest the bioconcentration in aquatic organisms is low(SRC).

The Koc of triethyl phosphate is estimated as 65(SRC), using a log Kow of 0.80(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that triethyl phosphate is expected to have high mobility in soil. Leaching through soil may be possible(SRC) as this compound has a very high water solubility of 5.0X10+5 mg/L(4). Triethyl phosphate has been detected in leachates from several landfills(5,6). During rapid infiltration studies, surface water was passed through infiltration terrain consisting of fine-ground dune sand mixed with clay and lens-shaped peat layers. A 70% reduction in the amount of triethyl phosphate initially found in the surface water was found in water which had passed through the dune(7); the loss of triethyl phosphate could be due to biotic and/or abiotic transformations(SRC). In a second rapid infiltration study, triethyl phosphate was detected in a down-gradient monitoring well after primary effluent was placed in basins situated on a kame consisting of poorly graded sands or gravelly sands with interspersed lenses of silty and sandy gravels(8).

The Henry's Law constant for triethyl phosphate is 3.60X10-8 atm-cu m/mole(1). This Henry's Law constant indicates that triethyl phosphate is expected to be essentially nonvolatile from water surfaces(2). Triethyl phosphate's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Triethyl phosphate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.393 mm Hg(3).

GROUNDWATER: Triethyl phosphate was qualitatively detected in groundwater samples collected over a period of 16 months from an EPA National Priority (Superfund) site during groundwater investigations(1).|DRINKING WATER: Triethyl phosphate was detected in Canadian drinking water from the Great Lakes area (12 municipalities, positive detection for Toronto, 13.0 and 11.8 ng/L, and Kingston, 11.3 and 10.3 ng/L)(1). Triethyl phosphate was detected in drinking water from two of six eastern Ontario water treatment plants in 1978 (Prescott, 24.0 and 19.9 ng/L; Brockville, 17.2 and 27.1 ng/L)(2). Triethyl phosphate was detected in drinking water in 4 of 29 large municipalities in Canada(3). Concentrations reported ranged from 1.1-23 ng/L but are probably higher due to poor recovery for triethyl phosphate(3). Drinking water from bank-filtered Rhine water in the Netherlands had a maximum concentration of triethyl phosphate of 1000 ng/L(4). Triethyl phosphate was detected in drinking water from the following locations: Cincinnati, OH in 1978, 1980; Miami, FL in 1976; Philadelphia, PA in 1976; Ottumwa, IA in 1976(5).|SURFACE WATER: Triethyl phosphate was detected in the rivers in Osaka City, Japan during a long-term monitoring project started in 1976 with a mean concentration of 1.5 ug/L found in river water samples taken in 1989-1990(1). Detected, not quantified, in River Waal at Brakel, Netherlands during 1974(2).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 5,855 workers (1,898 of these are female) are potentially exposed to triethyl phosphate in the US(1). Occupational exposure to triethyl phosphate may occur through dermal contact with this compound at workplaces where triethyl phosphate is produced or used(SRC). Monitoring data indicate that the general population may be exposed to triethyl phosphate via inhalation of ambient air, ingestion of drinking water, and dermal contact with this compound and other products containing triethyl phosphate(SRC). Rough estimates of consumer exposure to triethyl phosphate during its use as a flame retardant in plastic materials were calculated for inhalation with C (inhalation) = 0.001 mg/cu m. When exposed to triethyl phosphate as a plasticizer in plastic materials more evaporation is likely to take place with C (inhalation) = 0.01 mg/cu m, C (dermal) = 300 mg/cu cm, and C (oral) = 0.6 mg(2).

Drug Information

3(?). 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OZ & 1 PINT (OR 1 LB) FOR 70 KG PERSON (150 LB).

0.08 Days

May be harmful by inhalation, ingestion or absorption. May cause irritation. (USCG, 1999)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, administer a slurry of activated charcoal in water and simultaneously call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)


Fresh air, rest.


Rinse skin with plenty of water or shower.


Rinse with plenty of water (remove contact lenses if easily possible).

/OTHER TOXICITY INFORMATION/ Some ethyl phosphate derivatives (e.g. parathion) are highly toxic cholinesterase inhibitors. Triethyl phosphate is thought to be weak enzyme inhibitor.

triethyl phosphate

The substance can be absorbed into the body by ingestion.

See Ingestion.


Redness.

Triethyl phosphate Use and Manufacturing

Methods of Manufacturing

Prepared from tetraethyl hypophosphate with ethanol in the presence of aluminum ethoxide; Manufactured by treating triethylphosphite with diethyl hydrogen phosphate.|... Manufactured from diethyl ether and phosphorus pentoxide via a metaphosphate intermediate.

Uses

Flame retardant enhancer for rubber and plastics; raw materials for pesticides and insecticides; ancient agents and stabilizers for resins; high boiling point solvents, catalysts, etc.


Flame retardants


Building/construction materials not covered elsewhere

Production

1,000,000 - 10,000,000 lb|This chemical is listed as a High Production Volume (HPV) (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).|(1972) 3.63X10+9 GRAMS|(1974) 3.18X10+9 GRAMS (EST)|(1986) >1 million-10 million pounds|For more U.S. Production (Complete) data for TRIETHYL PHOSPHATE (8 total), please visit the HSDB record page.

Grade: Technical 97%

Agriculture, forestry, fishing and hunting|Phosphoric acid, triethyl ester: ACTIVE|Compatible with many gums and resins. ...When mixed with water is quite stable at room temperature, but at elevated temperature it hydrolyzes slowly.

Computed Properties

Molecular Weight:182.15
XLogP3:0.8
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:182.07079595
Monoisotopic Mass:182.07079595
Topological Polar Surface Area:44.8
Heavy Atom Count:11
Complexity:113
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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