リン酸トリクレシル 化学特性,用途語,生産方法
外観
無色～わずかにうすい黄色, 澄明の液体
溶解性
水に不溶, 有機溶剤に可溶。エタノール及びアセトンに溶け、水にほとんど溶けない。
解説
リン酸トリクレシル，無臭またはかすかなフェノール臭をもつ液体。ビニル系、セルロース系合成樹脂とはとくに良好な適合性をもち、可塑剤として用いられる。とくにポリ塩化ビニル（PCV）可塑剤として知られる。［垣内 弘］[補完資料] | リン酸トリクレシル（データノート）
小学館 日本大百科全書(ニッポニカ) ）
用途
抽出溶媒、プラスチック可塑剤、難燃性添加剤。
用途
合成ゴム、キレート剤
用途
可塑剤,難燃剤,安定剤
製造
リン酸トリクレシル，リン酸エステルの一種。略号TCP。クレゾールとオキシ塩化リンとを塩化アルミニウムなどの触媒で脱塩素縮合させて得る。
主な用途／役割
リン酸系可塑剤。主にPVCに使用。
化学的特性
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.
使用
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.
製造方法
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.
健康ハザード
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.
安全性プロファイル
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.
職業ばく露
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.
純化方法
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.]
リン酸トリクレシル 上流と下流の製品情報
原材料
準備製品