Trikresylphosphat (m-m-m,m-m-p,m-p-p,p-p-p)

Bezeichnung:Trikresylphosphat (m-m-m,m-m-p,m-p-p,p-p-p)

CAS-Nr1330-78-5

Englisch Name:Tricresyl Phosphate

CBNumberCB8306429

SummenformelC21H21O4P

Molgewicht368.36

MOL-Datei1330-78-5.mol

Synonyma

Tris(methylphenyl)phosphat

Trikresylphosphat (m-m-m,m-m-p,m-p-p,p-p-p)

Trikresylphosphat (o-o-o,o-o-m,o-o-p,o-m-m,o-m-p,o-p-p)

Trikresylphosphat (m-m-m,m-m-p,m-p-p,p-p-p) physikalisch-chemischer Eigenschaften

Schmelzpunkt	<-40°C
Siedepunkt	265 °C10 mm Hg(lit.)
Dichte	1.143 g/mL at 25 °C(lit.)
Pour Point	-28
Dampfdruck	0.03 mm Hg ( 25 °C)
Brechungsindex	n20/D 1.555(lit.)
Flammpunkt	>230 °F
storage temp.	Store below +30°C.
Löslichkeit	organic solvents: miscible(lit.)
Aggregatzustand	Powder
Farbe	White to off-white
Wasserlöslichkeit	INSOLUBLE
Merck	14,9763
Henry's Law Constant	1.2×10¹ mol/(m³Pa) at 25℃, HSDB (2015)
Expositionsgrenzwerte	PC-TWA: 0.3 mg/m3
Dielectric constant	4.0(80℃)
Stabilität	Stable. Incompatible with strong oxidizing agents. May soften some plastics. Hydrolyzes slowly under alkaline conditions.
Kosmetik-Inhaltsstoffe Funktionen	PLASTICISER
InChI	1S/C21H21O4P/c1-16-4-10-19(11-5-16)23-26(22,24-20-12-6-17(2)7-13-20)25-21-14-8-18(3)9-15-21/h4-15H,1-3H3
InChIKey	ISNNXHQBIBWQHG-UHFFFAOYSA-N
SMILES	Cc1ccc(OP(=O)(Oc2ccc(C)cc2)Oc3ccc(C)cc3)cc1.Cc4ccc(OP(=O)(Oc5cccc(C)c5)Oc6ccccc6C)cc4.Cc7ccccc7OP(=O)(Oc8ccccc8C)Oc9ccccc9C
LogP	5.93
Oberflächenspannung	40.9mN/m at 20°C
CAS Datenbank	1330-78-5(CAS DataBase Reference)
EPA chemische Informationen	Tricresyl phosphate (1330-78-5)

Sicherheit

Kennzeichnung gefährlicher	Xn,N,T
R-Sätze:	21/22-51/53-39/23/24/25-62-50/53
S-Sätze:	28-61-45-28A-20/21-60-36/37
RIDADR	UN 2574 (TRICRESYL PHOSPHATE with more than 3 % ortho isomer)
WGK Germany	2
RTECS-Nr.	TD0175000
Selbstentzündungstemperatur	770 °F
TSCA	TSCA listed
HS Code	2919 90 00
HazardClass	6.1
PackingGroup	II
Speicherklasse	6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials
Hazard Classifications	Aquatic Acute 1 Aquatic Chronic 1 Repr. 2
Giftige Stoffe Daten	1330-78-5(Hazardous Substances Data)
Toxizität	cat,LD50,skin,1500mg/kg (1500mg/kg),BEHAVIORAL: ATAXIAPERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE),Toxicology Letters. Vol. 1000(Sp,

Gefahreninformationscode (GHS)

Tricresyl Phosphate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R21/22:Gesundheitsschädlich bei Berührung mit der Haut und beim Verschlucken.
R51/53:Giftig für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
R39/23/24/25:Giftig: ernste Gefahr irreversiblen Schadens durch Einatmen, Berührung mit der Haut und durch Verschlucken.
S-Sätze Betriebsanweisung:
S28:Bei Berührung mit der Haut sofort abwaschen mit viel . . . (vom Hersteller anzugeben).
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S20/21:Bei der Arbeit nicht essen, trinken,rauchen.
Beschreibung
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.
Chemische Eigenschaften
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 phosphates were used as flame retardants and plasticisers in PVC, nitrocellulose and acrylates.
Verwenden
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.
Verwenden
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.
Verwenden
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.
synthetische
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.
Sicherheitsprofil
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.
mögliche Exposition
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.
läuterung methode
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.
Einzelnachweise
[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 Upstream-Materialien And Downstream Produkte

Trikresylphosphat (m-m-m,m-m-p,m-p-p,p-p-p) Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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