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Home > Encyclopedia > Tri-p-cresyl phosphate

Tri-p-cresyl phosphate

Tri-p-cresyl phosphate structure

Tri-p-cresyl phosphate 

structure
  • CAS No:

    78-32-0

  • Formula:

    C21H21O4P

  • Chemical Name:

    Tri-p-cresyl phosphate

  • Synonyms:

    Phosphoric acid,tris(4-methylphenyl) ester;Phosphoric acid,tri-p-tolyl ester;p-Tolyl phosphate (C7H7O)3PO;Tri-p-cresyl phosphate;Tri-p-tolyl phosphate;Tris(p-methylphenyl) phosphate;Tris(p-cresyl) phosphate;Tris(4-methylphenyl) phosphate;NSC 2181

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

WHITE TO LIGHT BROWN POWDER


Tri-p-tolyl phosphate is a crystalline solid. (NTP, 1992)


Tri-p-tolyl phosphate is a crystalline solid. (NTP, 1992)|A mixture of isomeric tritolyl phosphates. Used in the sterilization of certain surgical instruments and in many industrial processes.

Tri-p-cresyl phosphate Basic Attributes

368.36

368.36

201-105-6

5149JKD098

2181

3082|2574

DTXSID5052676

Needles from alcohol; tablets from ethanol

29199000

Characteristics

54.57000

6.25670

Tri-p-tolyl phosphate is a crystalline solid. (NTP, 1992)

1.247 g/cm3 @ Temp: 25 °C

77-78 °C

244 °C @ Press: 3.5 Torr

410 °C

Soluble in ethanol, ethyl ether, benzene, chloroform.

Tricresyl phosphates should be stored in a cool, well ventilated area, protected from direct sunlight and away from open flames. Containers should be made of galvanized steel; these should be effectively sealed and their contents clearly marked. Tricresyl phosphates should not be used in plastic articles which are likely to come into contact with foodstuffs or clothing. /Tricresyl phosphates/

4.9X10-7 mm Hg at 25 deg C (est)

Henry's Law constant = 5.4X10-8 atm-cu m/mol at 25 °C (est)

190.02 Ų [M+H]+

Flame resistant liquid; pour point: -28 °C; specific heat 0.38; index of refraction: 1.55 at 25 °C/D; oily liquid; solubility: less than 0.002% in water at 85 °C; miscible with organic solvents and thinners, linseed oil, castor oil, china wood oil /Isomeric mixture/|Hydroxyl radical reaction rate constant = 1.4X10-11 cu cm/molecule-sec at 25 °C (est)

Insoluble in water.

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

Organophosphates, such as TRI-P-TOLYL 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.

Safety Information

III

9

3082

51/53-21/22

61-28A-28

TC9330000

N-Xn,N,Xn

Stable, non-volatile /Tricresyl phosphate/

P264, P270, P273, P280, P301+P312, P302+P352, P312, P322, P330, P363, P391, P501

H302

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.|Absorb with paper towels. Place in a plastic bag. Burn in an open pan with help of flammable solvent or in a furnace. /Tricresyl phosphate/

Flash point data for this compound are not available, however, it is probably combustible. (NTP, 1992)

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P280, P301+P312, P302+P352, P312, P322, P330, P363, P391, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 1150 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H361f: Suspected of damaging fertility [Warning Reproductive toxicity]|P201, P202, P260, P273, P281, P308+P313, P314, P391, P405, and P501|Not Classified|Danger|H360: May damage fertility or the unborn child [Danger Reproductive toxicity]|P201, P202, P260, P264, P270, P281, P307+P311, P308+P313, P314, P321, P405, and P501|H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: 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, you should dampen the solid spill material with methanol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with methanol to pick up any remaining material. Your contaminated clothing and the absorbent paper should be sealed in a vapor tight plastic bag for eventual disposal. Solvent-wash contaminated surfaces with methanol 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)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)|Wear safety glasses, gas mask, long-sleeve coveralls with tight collars and cuffs, gloves, and boots. /Tricresyl phosphate/|Respiratory protection (supplied-air respirator with full facepiece or self-contained breathing apparatus) should be available where these compounds are manufactured or used and should be worn in case of emergency and overexposure. /Phosphorus compounds/

Extinguish with dry chemical, foam, or carbon dioxide. Water may be ineffective on fire. Cool exposed containers with water. /Tricresyl phosphate/

Prolonged skin or mucous membrane contact should be avoided by use of mechanized processes, protective clothing (including gloves and goggles) and barrier creams; in addition, scrupulous personal hygiene should be encouraged ... . /Tricresyl phosphates/|Where a process entails the heating of tricresyl phosphate, exhaust ventilation should be installed to collect vapors at source or, under special circumstances, workers may be required to wear respiratory protective equipment; a high standard of general ventilation for the workplace is also necessary, and atmospheric determinations should be carried out at regular intervals to ensure that the concentration of tri-o-cresyl phosphate in air is maintained below recommended permissible levels. /Tricresyl phosphates/|Workers should not be allowed to eat, drink or smoke at the workplace. /Tricresyl phosphates/|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|... Ingestion must be prevented & breathing of vapors must not be continuous ... . Isomeric mixt/

/GUIDE 151: SUBSTANCES - TOXIC (NON-COMBUSTIBLE)/ Health: Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Tricresyl phosphate/|/GUIDE 151: SUBSTANCES - TOXIC (NON-COMBUSTIBLE)/ Fire or Explosion: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Containers may explode when heated. Runoff may pollute waterways. /Tricresyl phosphate/|/GUIDE 151: SUBSTANCES - TOXIC (NON-COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at lease 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. /Tricresyl phosphate/|/GUIDE 151: SUBSTANCES - TOXIC (NON-COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Tricresyl phosphate/|For more DOT Emergency Guidelines (Complete) data for TRI-P-CRESYL PHOSPHATE (8 total), please visit the HSDB record page.

Vapors may irritate eyes, but only at high temperatures. /Tricresyl phosphate/

The average concentration of tri-p-cresyl phosphate in wastewater discharged from industrial machinery complex into the Kurose River, Hiroshima, Japan was 0.01 ug/L(1). The average concentration of tri-p-cresyl phosphate in domestic wastewater from Hiroshima, Japan was 0.01 ug/L(1).

Tricresyl phosphate, unspecified isomer, was detected in Detroit river sediments at concentrations ranging from 0.23 to 1.30 ug/L(1). Tri-p-cresyl phosphate was detected in bottom sediment from the Kurose River, Japan at concentrations ranging from 0.003 ug/g in April 1992 to 0.03 ug/g in July 1992(1).

... TRITOLYL PHOSPHATE CONCN IN AIR OF FACTORY WHERE 3 CASES OF POLYNEURITIS OCCURRED ... & VARIOUS SAMPLES TAKEN IN THIS ATMOSPHERE SHOWED CONCN BETWEEN 0.55 MG/CU M & 1.66 MG/CU M. /ISOMERIC MIXT/|URBAN/SUBURBAN: Tri-p-cresyl phosphate concentrations of 0.003 to 0.029 ng/cu m were detected in atmospheric samples collected from the Kurose river basin, Higoshi-Hiroshima city, Japan during 1995 monitoring(1).

A tri-p-cresyl phosphate concentration of 65 ng/cu m was detected in exhaust gases from a gasoline automotive engine(1).

Toxicity

LD50 RAT ORAL GREATER THAN 12.8 G/KG /FROM TABLE/|LD50 Cat sc greater than 1.0 g/kg /FROM TABLE/|LD50 Chicken oral greater than 2.0 g/kg /From table/

/AQUATIC SPECIES/ Rainbow trout (Salmo gairdneri) were exposed to IMOL S-140, a synthetic high-temperature lubricating oil composed of tri-aryl phosphates and, although no sign of acute toxicity was evident, the fish slowly developed symptoms of chronic posioning. Thus, floating food pellets were refused, the activities of glutamic oxalacetic transaminase and lactate dehydrogenase in serum were greatly elevated, and internal fatty tissues became discoloured. Neither serum nor brain cholinesterase activities were inhibited. /Triaryl Phosphates/

Tri-p-cresyl phosphate's production and use as a plasticizer in vinyl plastic manufacture, as a flame retardant, gasoline additive, heat exchange medium, solvent for nitrocellulose, and in hydraulic fluids(1,2) may result in its release to the environment through various waste streams(SRC). Rainfall and runoff from agricultural plastic films has been identified as a source of environmental release of tricresyl phoshates(3,4). Tri-p-cresyl phosphate has been detected in gasoline automobile exhaust(5).

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 4.4X10+4(SRC), determined from a structure estimation method(2), indicates that tri-p-cresyl phosphate is expected to be immobile in soil(SRC). Volatilization of tri-p-cresyl phosphate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.4X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Tri-p-cresyl phosphate is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 4.9X10-7 mm Hg(SRC), determined from a fragment constant method(2). Biodegradation of tri-p-cresyl phosphate in soil is expected to be an important fate process(SRC), based on its ready biodegradability in water and sediments(3-6).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 4.4X10+4(SRC), determined from a structure estimation method(2), indicates that tri-p-cresyl phosphate is expected to adsorb to suspended solids and sediment in water(SRC). Tri-p-cresyl phosphate has been observed to adsorb to sediment in the water column and precipitate to the bottom in sorption studies(3). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 5.4X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(5), a BCF range of 928 to 1589 measured in fathead minnows, rainbow trout, and bluegills(6) suggests bioconcentration in aquatic organisms is high to very high(SRC). A base-catalyzed second-order hydrolysis rate constant of 0.068 L/mole-sec(SRC) and a neutral hydrolysis rate constant 1.18X10-7/day(SRC) were estimated using a structure estimation method(2); this corresponds to half-lives of 3.2 years, 118 days, 11.8 and 1.18 days at pH values of 7, 8, 9 and 10, respectively(2). The half-life of tri-p-cresyl phosphate in lake water, river water and sediment bottoms has been observed to range from 2 to 5.3 days(7,8). Tri-p-cresyl phosphate was readily biodegradable in sewage treatment and activated sludge studies(9,10).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tri-p-cresyl phosphate, which has an estimated vapor pressure of 4.9X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase tri-p-cresyl 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 1.2 days(SRC), calculated from its rate constant of 1.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Monitoring studies have observed that tri-p-cresyl phosphate is removed from the atmosphere by both wet and dry deposition(3). Tri-p-cresyl phosphate does not absorb UV wavelengths >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 tri-p-cresyl phosphate with photochemically-produced hydroxyl radicals has been estimated as 1.4X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.2 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Phosphoric acid esters are susceptible to hydrolysis(2). The hydrolysis half-life of tri-p-cresyl phosphate in pH 13 0.1 N sodium hydroxide:acetone (1:1) at 22 °C was 1.66 hours(3). A base-catalyzed second-order hydrolysis rate constant of 0.068 L/mole-sec(SRC) and a neutral hydrolysis rate constant 1.18X10-7/day were estimated using a structure estimation method(1); this corresponds to half-lives of 3.2 years, 118 days, 11.8 and 1.18 days at pH values of 7, 8, 9 and 10, respectively(1). The UV spectra of triaryl phosphates do not show absorbance above 290 nm(4); therefore, tri-p-cresyl phosphate is not expected to be susceptible to direct photolysis by sunlight(SRC).

Bioconcentration factors for C-14 tri-p-cresyl phosphate, determined by total radioactivity, in rainbow trout and fathead minnows using short-term static exposure were 1420 and 928, respectively(1). An equilibrium BCF of 1589 for C14 tri-p-cresyl phosphate was determined in bluegills(1). Depuration half-lives of tricresyl phosphate isomers range from 4 to 6 days; tri-m-cresyl phosphate is more rapidly eliminated by fathead minnows and rainbow trout fry than tri-p-cresyl phosphate(2). A BCF of 722 for C14 tri-p-cresyl phosphate was determined in daphnids using flow-through conditions(2). According to a classification scheme(3), the fish BCF range of 928 to 1589 suggests bioconcentration in aquatic organisms is high to very high(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for tri-p-cresyl phosphate can be estimated to be 4.4X10+4(SRC). According to a recommended classification scheme(2), this estimated Koc value suggests that tri-p-cresyl phosphate is expected to be immobile in soil(SRC). Tri-p-cresyl phosphate was found to adsorb strongly to clay minerals in sorption tests(3). Using bottom sediment from a river, tri-p-cresyl phosphate was found to adsorb strongly to the sediment with a Freundlich isotherm constant of 138(4); it was further observed that tri-p-cresyl phosphate in the water column adsorbed to sediment and precipitated to the bottom(4).

The Henry's Law constant for tri-p-cresyl phosphate is estimated as 5.4X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that tri-p-cresyl phosphate will be essentially nonvolatile from water surfaces(2). Tri-p-cresyl phosphate's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Tri-p-cresyl phosphate is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 4.9X10-7 mm Hg(SRC), determined from a fragment constant method(1).

DRINKING WATER: Tricresyl phosphate, unspecified isomer, was detected in drinking water from the Smith Falls, Ontario, Canada water treatment plant in September 1978 at a concentration of 0.3 ng/L(1).|SURFACE WATER: Tri-p-cresyl phosphate was detected in river water from the Kurose River, Japan at concentrations of 0.46 and 0.01 ug/L in July and April 1992, respectively(1).|RAIN/SNOW: Tri-p-cresyl phosphate was detected in rain near Hiroshima, Japan at a concentration of 0.026 ug/L(1). Tri-p-cresyl phosphate was detected in rain near the Kurose basin Japan at a concentrations of 0.004-0.010 ug/L(2).

Occupational exposure to tri-p-cresyl phosphate may occur through inhalation of dust particles and dermal contact with this compound at workplaces where tri-p-cresyl phosphate is produced or used. Monitoring and use data indicate that the general population may be exposed to tri-p-cresyl phosphate via inhalation of ambient air, ingestion of drinking water, and dermal contact with water or consumer products containing tri-p-cresyl phosphat. (SRC)|Intoxication during production of tricresyl phosphate is a rare occurrence since the process is totally enclosed, and most cases of occupational poisoning occur during the industrial use of the product. /Isomeric mixt/

Drug Information

The distribution and excretion of (14)C-labeled isomerically pure tri-o-, tri-m- and tri-p-cresyl phosphates has been examined in F344/N rats... Groups of male rats were administered /0.5, tri-m and tri-p only/, 2, 20, or 200 mg/kg of the respective (14)C-labeled isomerically pure tricresyl phosphate in corn oil by gavage, or 20 mg/kg was administered intravenously. All three compounds were well absorbed after oral administration; however, the pattern of excretion of each of the three triesters was different. Tri-o-cresyl phosphate was excreted primarily in the urine with approximately 70% of the label appearing in urine and 20% in feces within 24 hours for all three dose levels administered. Tri-m-cresyl phosphate was excreted primarily in the feces at all four dose levels administered (0.5, 2, 20, or 200 mg/kg); however, as the dose increased the percentage excreted in the feces also increased and that excreted in urine decreased. Tri-p-cresyl phosphate exhibited yet a different excretion pattern; at low doses (0.5 or 2 mg/kg) the primary route of excretion was the urine, whereas at higher doses (20 or 200 mg/kg) the primary route of excretion was the feces. Evaluation of biliary excretion following intravenous administration indicated that after administration of 2 or 20 mg/kg tri-o-cresyl phosphate or tri-m-cresyl phosphate approximately 40% to 60% of the label was excreted in the bile within the first 6 hours. However, tri-p-cresyl phosphate exhibited a dose dependent increase which represented an approximate doubling of biliary excretion between the 2 mg/kg and 20 mg/kg doses. The percentage of administered label appearing in feces was less than that excreted in bile for all three triesters, suggesting that substantial enterohepatic recycling occurs. Within 3 days after administration essentially 100% of the label of all three isomers had been excreted. All three isomers were rapidly distributed to muscle and liver and then redistributed to adipose tissue and skin; however, the parent compounds were rapidly cleared with no tendency to bioaccumulate in specific organs or tissues. Within 12 hours of dermal administration of a 50 mg/kg dose of (14)C-tri-o-cresyl phosphate to the intrascapular region of cats, 73% of the radioactivity had disappeared from the site of application, and within 24 hours it reached its maximum concentration in all organs and tissues examined... Within 10 days after administration, 28% of the applied radio activity had been excreted in the urine and 20% in the feces. Although studies of skin absorption have not been conducted with other isomeric tricresyl phosphate esters, the similarity of structure and physical properties (solubility, etc.) make it likely that these compounds are also absorbed through the skin.|... TRI-PARATOLYL PHOSPHATE ... ABSORBED WITH DIFFICULTY BY HUMAN BODY (DIGESTION ROUTE & VIA SKIN).|... /TRITOLYL PHOSPHATE/ CAN NORMALLY PENETRATE INTO BODY BY INGESTION OF LIQ OR SPRAY IN ATMOSPHERE & BY CUTANEOUS ABSORPTION. ... IT SEEMS THAT ONLY PHOSPHATES CONTAINING ORTHO-SUBSTITUTED PHENOL ARE ABSORBED THROUGH SKIN. /ISOMERIC MIXT/|The metabolism and disposition of tri-p-cresyl phosphate (TPCP) were studied in the rat after a single oral administration of [methyl-(14)C] TPCP. At a dosage of 7.8 mg/kg, most of the administered radioactivity was excreted in the urine (41%) and feces (44%) in 7 days. For 3 days, the expiratory excretion as (14)CO2 amounted to 18% of the radioactivity, but was reduced to 3% by treatment of the animal with neomycin. In separate rats, the biliary excretion amounted to 28% of the dose in 24 hr. At a dose of 89.6 mg/kg, the radioactivity was excreted in urine (12%) and feces (77%) in 7 days, and the expired air (6%) in 3 days. At 24, 72, and 168 hr after oral administration, the concentration of radioactivity was relatively high in adipose tissue, liver, and kidney...Following oral administration, TPCP was absorbed from the intestine, distributed to the fatty tissues, and moderately metabolized to a variety of products of oxidation and dearylation of TPCP, which were then excreted in the urine, feces, bile, and expired air. The intestinal microflora appeared to play an important role in degrading biliary metabolites to (14)CO2 through the enterohepatic circulation in rats.|For more Absorption, Distribution and Excretion (Complete) data for TRI-P-CRESYL PHOSPHATE (6 total), please visit the HSDB record page.

The metabolism and disposition of tri-p-cresyl phosphate (TPCP) were studied in the rat after a single oral administration of [methyl-(14)C] TPCP.... The major urinary metabolites were p-hydroxybenzoic acid, di-p-cresyl phosphate (DCP), and p-cresyl p-carboxyphenyl phosphate (1coDCP). The biliary metabolites were DCP, 1coDCP, and the oxidized triesters, di-p-cresyl p-carboxyphenyl phosphate (1coTPCP), and p-cresyl di-p-carboxyphenyl phosphate (2coTPCP). The main fecal metabolite was TPCP, and the others were similar to those of bile. Following oral administration, TPCP was absorbed from the intestine, distributed to the fatty tissues, and moderately metabolized to a variety of products of oxidation and dearylation of TPCP, which were then excreted in the urine, feces, bile, and expired air. The intestinal microflora appeared to play an important role in degrading biliary metabolites to (14)CO2 through the enterohepatic circulation in rats.

SYMPTOMS: Nausea, vomiting, abdominal pain, diarrhea. After 3-28 days incubation period: non-tender enlargement of parotid gland; coldness and sweating of hands and legs; muscular pain and cramping of hands and legs; parethesias of extremities; muscular tremor; symmetrical polyneuritis. (NTP, 1992)

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. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. 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)

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Tri-Ortho-Cresyl Phosphate (TOCP) and Related Compounds/|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) 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. Administer activated charcoal ... . /Tri-Ortho-Cresyl Phosphate (TOCP) and Related Compounds/|Advanced treatment: Use proparacaine hydrochloride to assist eye irrigation ... . /Tri-Ortho-Cresyl Phosphate (TOCP) and Related Compounds/

/SIGNS AND SYMPTOMS/... CHRONIC TOXICITY OF TRITOLYL PHOSPHATE, WHEN THERE WAS SIMULTANEOUS INHALATION & CUTANEOUS ABSORPTION. MAIN SYMPTOMS WERE HYPERHYDROSIS, HYPOTENSION, GENERAL FATIGUE, AFFECTIVE IRRITABILITY, & PARESTHESIA IN LIMBS. /ISOMERIC MIXT/|/SIGNS AND SYMPTOMS/ NONE OF USUAL TOXIC EFFECTS OF CRESOLS OR PHENOLS IS DESCRIBED IN CLINICAL POISONINGS. DOES NOT PRODUCE TYPICAL SYNDROME ASSOC WITH CHOLINESTERASE INHIBITION AS DO PHOSPHATE ESTERS LIKE PARATHION. META & PARA ISOMERS ARE RELATIVELY INACTIVE. /O-TRICRESYL PHOSPHATE/|/SIGNS AND SYMPTOMS/... ABSORPTION OF TRITOLYL PHOSPHATE THROUGH SKIN GIVES RISE ONLY TO ATTACK ON PERIPHERAL NERVES, WHILE BREATHING VAPORS IS FOLLOWED, IN PARTICULAR, BY ATTACK ON PYRAMIDAL TRACT. /ISOMERIC MIXT/|/CASE REPORTS/ CASE OF PERMANENT PARALYSIS IN MAN ENGAGED IN MANUFACTURING META & PARA ISOMERS OF TRICRESYL PHOSPHATE ... FINAL PRODUCT CONTAINED ONLY 1% TOCP, AS MUCH AS 6 TO 10% WAS PRESENT AS CONTAMINANT DURING MANUFACTURING. ... PATIENT HAD WORKED ... 5 MO ... BEFORE SYMPTOMS OF ANOREXIA, NAUSEA, & ACHING OF LEGS HAD DEVELOPED.|For more Human Toxicity Excerpts (Complete) data for TRI-P-CRESYL PHOSPHATE (6 total), please visit the HSDB record page.

Phosphate, Tricresyl

Tri-p-cresyl phosphate Use and Manufacturing

Methods of Manufacturing

Prepared from cresol and phosphorus oxychloride, phosphoric acid, or phosphorus pentachloride. The grades of cresol commonly used are the isomeric (o-, m-, p-), and meta-para mixtures from coal tar and cresylic acid from petroleum. Purification of the product is based on the intended use; the commercial product is generally obtained as a mixture. A "refined grade" of tricresyl phosphate is prepared by vacuum distillation, or alternatively by washing with 2% sodium hydroxide and water ... . /Tricresyl phosphate/

Uses

Like phthalic acid esters, they are all plasticizers. The testing items in EU EN719 are not mandatory testing items.

Production

< 25,000 lb|(1972) 2.28X10+10 GRAMS|(1974) 2.32X10+10 GRAMS (EST)

55% AS A FLAME RETARDANT IN FUNCTIONAL FLUIDS AND LUBRICANTS; 30% AS A FLAME RETARDANT PLASTICIZER FOR POLYVINYL CHLORIDE, CELLULOSE ESTERS, AND NITRILE RUBBER COMPOUNDS; 5% AS AN AIR FILTER ADHESIVE MEDIUM; 10% IN MISC APPLICATIONS (1974)

Phosphoric acid, tris(4-methylphenyl) ester: ACTIVE|TRICRESYL PHOSPHATE SHOULD NOT BE USED IN PLASTIC ARTICLES WHICH ARE LIKELY TO COME INTO CONTACT WITH FOODSTUFFS OR CLOTHING. /ISOMERIC MIXT/|A tricresyl phosphate prepared from m- or p-cresol has the same properties as the technical product, but the cost of separating and purifying these isomers is prohibitive. /Isomeric mixt/|... A) ARYL PHOSPHATES ... NOT SUITABLE FOR PLASTICS IN CONTACT WITH FOODSTUFFS; C) ... SHOULD NOT BE USED IN ARTICLES INTENDED FOR WEAR DIRECTLY ON SKIN OR ARTICLES ... HANDLED BY CHILDREN. /ARYL PHOSPHATES/|The commercial tricresyl phosphate product is essentially a meta, para-isomer mixture.

Method: EPA-RCA 8270D; Procedure: gas chromatography/mass spectrometry; Analyte: tri-p-tolyl phosphate; Matrix: solid waste matrices, soils, air sampling media and water; Detection Limit: 10 ug/L.|Several techniques were evaluated for extracting triphenyl phosphate (TPP), (14)C-labeled TPP, cresyl diphenyl phosphate and tricresyl phosphate isomers (o-TCP, m-TCP and p-TCP) from fish and sediment samples. Extracts of fish samples were cleaned up by gel permeation chromatography/alumina column chromatography; sediment extracts received alumina treatment only. Compounds were determined by GLC with N-P detection. Methanololytron and hexane/ball mill extraction of fish samples fortified at 0.01, 0.1 and 1.0 mug/g levels gave overall recoveries of the 5 compounds of 89 and 97%, respectively. Methanol recovered more radioactivity (97%) from fish exposed to (14)C-TPP in aquaria for 24 hr than hexane from fish exposed for 16 hr (79%). Refluxing fortified sediment (0.05 and 0.5 ug/g) with methanol-water (9 + 1) gave significantly higher recoveries (88%) of the 5 triaryl phosphates than dichloromethane-methanol (1 + 1) reflux or acetone-hexane (1+1) Soxhlet extraction. Recoveries of TPP and o-, m- and p-TCP from fortified river water (0.5, 5.0 and 50 ug/L) by shaking with dichloromethane ranged from 91-118%. Some problems were encountered with interfering GLC peaks at low (ug/g) levels in fish and sediment extracts despite the use of N-P specific detectors.|The method for the determination of the isomers of tricresyl phosphate isomers is based on saponification of tricresyl phosphate and triphenyl phosphate with alkali and combining the mixture of phenol and o-, m-, and p-cresols obtained with diazotized p-nitroaniline in an alkaline medium with subsequent separation of the mixture in a thin layer in the solvent system benzene-methanol-diethylamine and spectrophotometry of the solutions. /Tricresyl phosphate isomers/|EPA Method 1618: Determination of tricresyl phosphate using wide bore capillary column gas chromatography with electron capture detector. /Tricresyl phosphate/

INDUSTRIAL

Computed Properties

Molecular Weight:368.4
XLogP3:5.1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:368.11774614
Monoisotopic Mass:368.11774614
Topological Polar Surface Area:44.8
Heavy Atom Count:26
Complexity:392
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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