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Tris(2-chloropropyl) phosphate (TCPP) is a trialkyl phosphate.
Clear colorless viscous liquid.
Tris(2-chloropropyl) phosphate (TCPP), mixture of isomers is suitable for use in environmental and food residue analysis.
CAS: 13674-84-5
MF: C9H18Cl3O4P
MW: 327.57
EINECS: 237-158-7
Synonyms
Phosphoric acid tris(2-chloro-1-methylethyl) ester;TRIS(1-CHLORO-2-PROPYL) PHOSPHATE;TRIS(1-CHLOROPROPYL)PHOSPHATE;TRIS(2-CHLORO-1-METHYLETHYL) PHOSPHATE;TRIS(CHLOROISOPROPYL)PHOSPHATE;TRIS(MONOCHLOROPROPYL) PHOSPHATE;tris(2-chloroisopropyl)phosphate;TcppTris(1-Chloro-2-Propyl)Phosphate]
Tris(2-chloropropyl) phosphate (TCPP) is a mixture of isomers, composition may vary, typical composition: main isomer tris(1-chloro-2-propyl) phosphate 66%, minor components: bis(1-chloro-2-propyl) (2-chloropropyl) phosphate and (1-chloro-2-propyl) bis(2-chloropropyl) phosphate.
Tris(2-chloropropyl) phosphate (TCPP) is a chlorinated organophosphate flame retardant commonly added to polyurethane foams.
Comparatively minor amounts are used in PVC and EVA.
Tris(2-chloropropyl) phosphate (TCPP) acts as a flame retardant.
Except the flame retarding, it can also promote the moisture resisting, low temperature resisting, the capability of antistatic and the softness of the materials.
Tris(2-chloropropyl) phosphate (TCPP) has the best hydrolysis stability among currently available halogenated organic phosphates.
Tris(2-chloropropyl) phosphate (TCPP) does not dissolve in water but in most organic solvent, and have good compatibility with resins.
Tris(2-chloropropyl) phosphate (TCPP) is compatible with acetate fiber, polyvinyl-chloride, PU foams, EVA, phenolics materials.
Tris(2-chloropropyl) phosphate (TCPP) is an additive low molecular weight halogen phosphorus flame retardant with good flame retardant effect.
Tris(2-chloropropyl) phosphate (TCPP) is mainly used in polyvinyl chloride, polystyrene, phenolic resin, acrylic resin, and rubber.
Tris(2-chloropropyl) phosphate (TCPP) is also widely used in polyurethane soft foam, hard foam and plastic products for flame retardancy and coating.
Tris(2-chloropropyl) phosphate (TCPP) is also a good plasticizer.
Tris(2-chloropropyl) phosphate (TCPP) has good flame retardant effect, low volatility, good oil resistance and hydrolysis resistance.
Tris(2-chloropropyl) phosphate (TCPP) is a low-cost flame retardant suitable for soft and rigid polyurethane and foam plastics, polyvinyl chloride, epoxy resin, unsaturated polyester, phenolic resin and other plastics.
Tris(2-chloropropyl) phosphate (TCPP) is an additive low molecular weight halogenated phosphorus flame retardant with good flame retardant effect, which is mainly used in the flame retardancy of polyvinyl chloride, polystyrene, phenolic resins, acrylic resins, rubbers and coatings, and is also widely used in polyurethane soft foam, hard foam and plastic products.
Tris(2-chloropropyl) phosphate (TCPP) is also a good plasticizer.
Tris(2-chloropropyl) phosphate (TCPP) is an organophosphorus flame retardant with the chemical formula C₁₂H₁₉ClO₄P.
Tris(2-chloropropyl) phosphate (TCPP) is a colorless to pale yellow liquid with a mild, aromatic odor.
Tris(2-chloropropyl) phosphate (TCPP) is a halogenated compound, featuring a phosphate group bonded to three isopropyl-chloro groups (1-chloro-2-isopropyl), which contribute to its flame-retardant properties.
Tris(2-chloropropyl) phosphate (TCPP) is highly soluble in organic solvents, such as ethanol, acetone, and chloroform, but insoluble in water.
Tris(2-chloropropyl) phosphate (TCPP) is mainly used to improve the fire resistance of materials, making it suitable for a range of applications in various industries.
Tris(2-chloropropyl) phosphate (TCPP), chemically known as tri (2-chloropropyl) phosphate, is an organophosphorus halide flame retardant.
Good hydrolysis stability, insoluble in water, soluble in ethanol, acetone, lipids, aromatics and chloroform and other organic solvents.
Tris(2-chloropropyl) phosphate (TCPP) has good anti-ultraviolet ability.
Widely used in soft and hard polyurethane foam, polyvinyl chloride, polyvinyl acetate, phenolic resin and epoxy resin and other materials.
Tris(2-chloropropyl) phosphate (TCPP) can be used directly or made into emulsion, used in carpet, raincoat, fabric finishing, rubber products, etc., and can also be used as an additive for fireproof coatings.
Tris(2-chloropropyl) phosphate (TCPP) is a chemical compound used as a flame retardant, plasticizer, and viscosity regulator in various types of polymers including polyurethanes, polyester resins, and polyacrylates.
Tris(2-chloropropyl) phosphate (TCPP) Chemical Properties
Melting point: -39.9°C
Boiling point: 270°C
Density: 1.28
Refractive index: 1.460～1.466 (20℃/D)
Fp: -218 °C
Storage temp.: Sealed in dry,Room Temperature
Solubility: DMSO (Slightly), Methanol (Slightly)
Form: liquid
Color: Clear Colourless
Odor: mild odor
Water Solubility: <0.1 g/100 mL at 19.5 ºC
BRN: 1842347
Stability: Moisture Sensitive
InChIKey: KVMPUXDNESXNOH-UHFFFAOYSA-N
CAS DataBase Reference: 13674-84-5(CAS DataBase Reference)
NIST Chemistry Reference: 2-Propanol, 1-chloro-, phosphate (3:1)(13674-84-5)
EPA Substance Registry System: Tris(2-chloropropyl) phosphate (TCPP) (13674-84-5)
Tris(2-chloropropyl) phosphate (TCPP) is clear colorless oily liquid with high water solubility and low lipophilicity (as indicated by logKOW).
Tris(2-chloropropyl) phosphate (TCPP) is manufactured as a reactionmixture, which contains four isomers.
Tris(2-chloropropyl) phosphate (TCPP) is the primary isomer in the mixture at 50–85% weight/weight (w/w), followed by bis(1- chloro-2-propyl)-2-chloropropyl phosphate [15–40% (w/w); CASRN: 76025-08-6], bis(2-chloropropyl)-1-chloro-2-propyl phosphate [<15% (w/w); CASRN: 76649-15-5], and tris(2- chloropropyl) phosphate [<1% (w/w); CASRN: 6145-73-9] (EURAR, 2008).
Uses
Tris(2-chloropropyl) phosphate (TCPP) is a flame retardant of low hydrolytic stability, used in polyurethane (PU) rigid and flexible foam, PVC, EVA, phenolics and epoxy resin.
Tris(2-chloropropyl) phosphate (TCPP) Flame Retardant is used in the production of acetate fiber, polyvinyl-chloride, PU foams, EVA, and phenolics materials.
Except flame retarding, Tris(2-chloropropyl) phosphate (TCPP) can also promote moisture resisting, low-temperature resisting, the capability of antistatic, and the softness of the materials.
Tris(2-chloropropyl) phosphate (TCPP) is clear colorless oily liquid with high water solubility and low lipophilicity (as indicated by logKOW).
Tris(2-chloropropyl) phosphate (TCPP) is a flame retardant of low hydrolytic stability, used in polyurethane (PU) rigid and flexible foam, PVC, EVA, phenolics and epoxy resin.
Flame Retardant in Polymers: Tris(2-chloropropyl) phosphate (TCPP) is widely used as a flame retardant in plastics, especially in the production of flexible foams, including polyurethane foams used in furniture, mattresses, and automotive seating.
Tris(2-chloropropyl) phosphate (TCPP)'s ability to inhibit combustion and reduce the spread of fire makes it crucial for meeting safety standards in these materials.
Building Materials: Tris(2-chloropropyl) phosphate (TCPP) is incorporated into building materials such as insulation, flooring, and coatings, where it significantly enhances the fire resistance of these products.
Tris(2-chloropropyl) phosphate (TCPP) is used in both residential and commercial applications to help meet fire safety regulations.
Textiles and Fabrics: Tris(2-chloropropyl) phosphate (TCPP) is used to treat textiles and fabrics, including upholstery, drapes, and clothing, to improve their flame resistance.
Tris(2-chloropropyl) phosphate (TCPP) is especially useful in applications where materials are exposed to heat or fire risks, such as in public spaces or industrial settings.
Electrical and Electronic Components: Tris(2-chloropropyl) phosphate (TCPP) is added to electrical insulation materials and wires to prevent ignition and reduce the risk of electrical fires.
Tris(2-chloropropyl) phosphate (TCPP) is used in the production of cables, circuit boards, and other components that require enhanced fire resistance.
Rubber and Elastomers: TCPP is used as a flame retardant in the rubber industry, especially in the production of automotive parts, seals, and gaskets that are exposed to high temperatures.
The chemical properties of Tris(2-chloropropyl) phosphate (TCPP) improve the heat stability and fire resistance of rubber materials.
Polyurethane and Foam Products: As a flame retardant, Tris(2-chloropropyl) phosphate (TCPP) is commonly used in polyurethane foams, particularly in flexible foams found in mattresses, seating, and insulation.
Tris(2-chloropropyl) phosphate (TCPP)'s presence in foam products significantly reduces the likelihood of ignition, contributing to improved fire safety.
Consumer Goods and Furniture: Tris(2-chloropropyl) phosphate (TCPP) is used in the treatment of consumer goods, including furniture, carpets, and toys, to meet fire safety regulations and standards.
Tris(2-chloropropyl) phosphate (TCPP) is often employed in products that require prolonged exposure to heat or fire, ensuring that they remain safe for use in homes, offices, and other environments.
Industrial Applications: Tris(2-chloropropyl) phosphate (TCPP) is also used in various industrial applications that require flame-retardant properties, such as in the coating of metal parts, plastics in construction, and machinery exposed to high temperatures.
Tris(2-chloropropyl) phosphate (TCPP)'s chemical stability and performance under heat make it ideal for these demanding environments.
Synthesis
In a 5000 L stirred reactor equipped with a solid feeder, 4600 kg of phosphorous trichloride was first added, followed by 15 kg of anhydrous aluminum trichloride as a catalyst through the solid feeder and stirred at room temperature until complete dissolution.
The propylene oxide was continuously dewatered by passing Tris(2-chloropropyl) phosphate (TCPP) through a dewatering tower equipped with a dewatering agent, calcium oxide, and then collected in a 10,000 L metering tank, and the water content was measured to be 28 PPM. 5,300 kg of the dewatered propylene oxide was added to the reactor and mixed with the trichlorophosphorus solution.
The reaction temperature was controlled to be 65°C and the feed rate was adjusted to maintain the weight ratio of phosphorous trichloride to propylene oxide at 1:1.152.
After the materials were added proportionally, the reaction was held at 65°C until the reaction was completed.
At the end of the reaction, the crude product Tris(2-chloropropyl) phosphate (TCPP) 16000L was transferred to a washing tank, 5000kg of 1% sodium hydroxide solution was added, stirred at 70℃ for 1 hour, and the lower layer was removed after standing and stratifying.
Then add 5000kg of deionized water, stir for 1 hour at 70°C, and remove the water layer after static stratification.
The washed Tris(2-chloropropyl) phosphate (TCPP) crude product was transferred to a dehydration kettle for heating vacuum dehydration.
Finally, 9715 kg of product was obtained by filtration with a yield of 98.1%.
After GC analysis, the ether content in TCPP was 226PPM.
Toxicology
Tris(2-chloropropyl) phosphate (TCPP) is considered a suspected carcinogenic, suspected reprotoxic, and suspected PBT (persistent, bioaccumulative and toxic) and is a potential endocrine disruptor (ECHA, 2019).
Thus, the presence of Tris(2-chloropropyl) phosphate (TCPP) in the receiving water can affect aquatic organisms and potentially affect human health.
Synthesis
Tris(2-chloropropyl) phosphate (TCPP) is prepared industrially by the reaction of propylene oxide with phosphoryl chloride.
In practise this produces a range of products, of which the tris(2-chloro-1-methylethyl) isomer tends to dominate (50-85% w/w).
