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Tricresyl Phosphate

CAS No.
1330-78-5
Chemical Name:
Tricresyl Phosphate
Synonyms
tris(methylphenyl) phosphate;TRITOLYL PHOSPHATE;tricresyl;cresylphosphate;durad;lindol;imols140;kronitex;fyrquel150;nci-c61041
CBNumber:
CB8306429
Molecular Formula:
C21H21O4P
Molecular Weight:
368.36
MDL Number:
MFCD02102116
MOL File:
1330-78-5.mol
MSDS File:
SDS
Last updated:2024-12-18 14:15:32

Tricresyl Phosphate Properties

Melting point <-40°C
Boiling point 265 °C10 mm Hg(lit.)
Density 1.143 g/mL at 25 °C(lit.)
Pour Point -28
vapor pressure 0.03 mm Hg ( 25 °C)
refractive index n20/D 1.555(lit.)
Flash point >230 °F
storage temp. Store below +30°C.
solubility organic solvents: miscible(lit.)
form Powder
color White to off-white
Viscosity 80cp (20C)
Water Solubility INSOLUBLE
Merck 14,9763
Dielectric constant 4.0(80℃)
Stability Stable. Incompatible with strong oxidizing agents. May soften some plastics. Hydrolyzes slowly under alkaline conditions.
InChIKey ISNNXHQBIBWQHG-UHFFFAOYSA-N
LogP 5.93
CAS DataBase Reference 1330-78-5(CAS DataBase Reference)
EWG's Food Scores 2-5
FDA UNII 512641US16
EPA Substance Registry System Tricresyl phosphate (1330-78-5)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS08,GHS09
Signal word  Warning
Hazard statements  H361f-H410
Precautionary statements  P201-P202-P273-P280-P308+P313-P391
Hazard Codes  Xn,N,T
Risk Statements  21/22-51/53-39/23/24/25-62-50/53
Safety Statements  28-61-45-28A-20/21-60-36/37
RIDADR  UN 2574 6.1/PG 2
WGK Germany  2
RTECS  TD0175000
Autoignition Temperature 770 °F
TSCA  Yes
HS Code  2919 90 00
HazardClass  6.1
PackingGroup  II
Hazardous Substances Data 1330-78-5(Hazardous Substances Data)
Toxicity cat,LD50,skin,1500mg/kg (1500mg/kg),BEHAVIORAL: ATAXIAPERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE),Toxicology Letters. Vol. 1000(Sp,
NFPA 704
1
1 0

Tricresyl Phosphate price More Price(15)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.14811 Tritolyl phosphate for synthesis 1330-78-5 250ML $72.4 2024-03-01 Buy
Sigma-Aldrich 8.14811 Tritolyl phosphate for synthesis 1330-78-5 1L $145 2024-03-01 Buy
Sigma-Aldrich 268917 Tritolyl phosphate technical grade, mixture of isomers, 90% 1330-78-5 500ml $84.1 2024-03-01 Buy
TCI Chemical P0273 Tricresyl Phosphate (mixture of isomers) >99.0%(GC) 1330-78-5 25g $22 2024-03-01 Buy
TCI Chemical P0273 Tricresyl Phosphate (mixture of isomers) >99.0%(GC) 1330-78-5 500g $44 2024-03-01 Buy
Product number Packaging Price Buy
8.14811 250ML $72.4 Buy
8.14811 1L $145 Buy
268917 500ml $84.1 Buy
P0273 25g $22 Buy
P0273 500g $44 Buy

Tricresyl Phosphate Chemical Properties,Uses,Production

Description

Tricresyl Phosphate (TCP) is a mixture with a slightly pungent odor: of the three isomers, the normal and meta isomers are liquids, while the para isomer is a crystalline solid. TCP can be obtained by treating cresol with phosphorus oxychloride in the presence of an aluminum catalyst. It is used to recover phenol residues in gas plant wastewater and is also used as a plasticizer in the plastics industry. Plasticizers are substances used to increase the flexibility of plastic materials. By changing the amount of plasticizer added, the flexibility, hardness, water resistance and flammability of plastic materials can be changed over a wide range. Sometimes up to 50% TCP is added to polyvinyl chloride[1]. In addition, TCP is toxic to humans and can cause neuropathy, paralysis of the hands and feet, and/or death of humans and animals through ingestion, inhalation, and even absorption through the skin.

Chemical Properties

Tricresyl phosphate is an isomeric mixture of phosphoric acid esters of cresols. It is an odourless and colourless oily liquid (molar mass 368.4 g/mol, melting point –33°C).
Tricresyl phosphate
Tricresyl phosphates were used as flame retardants and plasticisers in PVC, nitrocellulose and acrylates.

Uses

Tricresyl phosphate is used as plasticizer in vinyl plastics manufacturing; in spectacle frames; flame-retardant; solvent for nitrocellulose; in cellulose-molding compositions; additive to extreme-pressure lubricants; nonflammable fluid in hydraulic systems; lead scavenger in gasoline; used to sterilize certain surgical instruments; in polystyrene; in waterproofing; in common organic solvents and thinners; in linseed oil; emulsifying agent in cosmetics; in china wood oil; in castor oil.

Uses

Tricresyl phosphate (TCP) is used as a solvent for nitrocellulose esters and numerous natural resins. It is a plasticizer for chlorinated rubber, vinyl plastics, polystyrene and polyacrylic and polymethacrylic esters. Tricresyl phosphate also acts as a binder for resins and nitrocellulose to improve toughness, elasticity and polishing properties of coatings. Alone or associated with hydrocarbons, it is used as an antiwear and antifriction additive in numerous synthetic lubricants, incorrectly termed “oils” by reason of their appearance. It is also employed as a hydraulic fluid. When incorporated in gasoline, tricresyl phosphate counteracts the harmful effects of lead deposits. In addition, it is an excellent fire retardant in many industries.
Usually used as a mediator in the preparation of uranium-sensitive electrode based on membrane containing uranium di-(4-octylphenyl)phosphate as sensor.

Uses

Tricresyl Phosphate is used as plasticizer in vinyl plastics manufacture, as flame-retardant, solvent for nitrocellulose, in cellulosic molding compositions, as additive to extreme pressure lubricants, as a nonflammable fluid in hydraulic systems, as lead scavenger in gasoline: Yust, Bame, US 2889212 (1959 to Shell); to sterilize certain surgical instruments.

Preparation

Tricresyl phosphate is prepared by reaction of cresols with phosphorus oxychloride, phosphoric acid, or phosphorus pentachloride:
OPCl3 + 3 HOC6H4CH3 → OP(OC6H4CH3)3 + 3 HCl
The grades of cresol commonly is a mixture of three isomers (o-, m-, p-). The fact that tricresyl phosphate is derived from a mixture and itself is a mixture ensures that it remains liquid over a wide span of temperatures.
A "refined grade" of tricresyl phosphate is prepared by vacuum distillation, or alternatively by washing with 2% sodium hydroxide and water.

Health Hazard

The tricresyl phosphates (TCPs) are part of a series of organophosphorus compounds which have been shown to cause delayed neurotoxicity. The 1930 outbreak of “ginger jake” paralysis was caused by the contamination of ginger extract by cresyl phosphates, used in the processing of the spice. Since that time, there have been several incidents reported of accidental poisoning of food by tri-o-cresyl phosphate (TOCP). There are few case series reports of occupational exposure in the literature. Acute occupational exposures have been described as causing gastrointestinal symptoms followed by a latent period of days to 4 weeks, after which extremity pain and tingling progress to motor paralysis of the lower extremities up to the thighs, and of the upper extremities to the elbow. There is rarely sensory loss. Partial to total recovery may take years. Fatalities have occurred in high-dose ingestion.

Safety Profile

Moderately toxic by ingestion and skin contact. Human systemic effects by ingestion: flaccid paralysis without anesthesia, motor activity changes, and muscle weakness. An experimental teratogen. Experimental reproductive effects. An eye and skin irritant. Combustible. When heated to decomposition it emits toxic fumes of POx.

Potential Exposure

According to the World Health Organization there is no safe level of exposure to Tricresyl Phosphate(TCP).
TCP has been used as a flame retardant in fabric, plastics and rubbers and as a plasticizer in PVC, lacquers, varnishes and nitrocellulose. It is also used as a heat exchange medium and hydraulic fluid. TCP was detected in all house dust samples gathered in two different North American studies.Biomonitoring studies detected TCP in the breast milk of women in Asia and Sweden. EPA has characterized TCP to exhibit moderate persistence in the environment based on biodegradation studies.

Purification Methods

Dry the ester with CaCl2, percolate it through a column of alumina, then distil it under a vacuum. Alernatively pass it through a packed column of alumina at 150o, with a counter-current stream of nitrogen, under reduced pressure, to remove residual traces of volatile impurities. It also crystallises from pet ether (b 60-80o). [Cherbuliez in Organic Phosphorus Compounds (Kosolapoff & Maier eds) Wiley-Interscience Vol 6 pp 454-457 1973.]

Toxicity evaluation

Tricresyl Phosphate is classified by the EPA as a high hazard for reproductive toxicity based on studies of rodents fed TCP. Adverse health effects included reduced fertility, sperm motility, number of live pups per litter, testicular and epidydimal weights, and increased incidence of interstitial cell hypertrophy and ovarian interstitial cell vacuolization.
Ovarian and adrenal gland lesions were observed in rats and liver and adrenal gland lesions in mice fed an isomer mixture of TCP for 2 years in an NTP study. Rodents fed TCP for 13 weeks developed neuropathy.
TCP has been shown to influence neurological damage in humans.
There are three tricresyl phosphate isomers, of which, the ortho isomer demonstrates the highest toxicity.

References

[1] D. HUNTER  B. E  K Perry. Toxic Polyneuritis arising during Manufacture of Tricresyl Phosphate[J]. British Journal of Industrial Medicine, 1944, 2 1: 227-231. DOI:10.1136/oem.1.4.227.

Tricresyl Phosphate Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Tricresyl Phosphate manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Tricresyl phosphate pictures 2024-10-29 Tricresyl phosphate
1330-78-5
US $0.00 / kg 20kg 99% 20 tons Qingdao RENAS Polymer Material Co., Ltd.
Tricresyl Phosphate pictures 2024-10-28 Tricresyl Phosphate
1330-78-5
US $100.00 / KG 1KG 99%min 200TON Hebei Weibang Biotechnology Co., Ltd
Tricresyl Phosphate pictures 2024-10-11 Tricresyl Phosphate
1330-78-5
US $5.00-2.00 / KG 1KG 99% 10000kg Hebei Chuanghai Biotechnology Co,.LTD
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