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| | Tris(1-Chloro-2-Propyl) Phosphate Basic information |
| Product Name: | Tris(1-Chloro-2-Propyl) Phosphate | | Synonyms: | Phosphoric acid tris(2-chloro-1-methylethyl) ester;TRIS(1-CHLORO-2-PROPYL) PHOSPHATE;TRIS(1-CHLOROPROPYL)PHOSPHATE;TRIS(MONOCHLOROPROPYL) PHOSPHATE;TcppTris(1-Chloro-2-Propyl)Phosphate];TRIS-(1-CHLORO-2-PROPYL)PHOSPHATE (TCPP);Tri(chloroisopropyl)phosphate;Tris(1-chloro-2-propyl) phosphate, Tris(2-chloroisopropyl) phosphate | | CAS: | 13674-84-5 | | MF: | C9H18Cl3O4P | | MW: | 327.57 | | EINECS: | 237-158-7 | | Product Categories: | Organics;13674-84-5;TCPP | | Mol File: | 13674-84-5.mol |  |
| | Tris(1-Chloro-2-Propyl) Phosphate 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 | | Henry's Law Constant | 1.6×102 mol/(m3Pa) at 25℃, HSDB (2015) | | Stability: | Moisture Sensitive | | Major Application | agriculture | | InChI | 1S/C9H18Cl3O4P/c1-7(4-10)14-17(13,15-8(2)5-11)16-9(3)6-12/h7-9H,4-6H2,1-3H3 | | InChIKey | KVMPUXDNESXNOH-UHFFFAOYSA-N | | SMILES | CC(CCl)OP(=O)(OC(C)CCl)OC(C)CCl | | 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(1-chloro-2-propyl) phosphate (13674-84-5) |
| | Tris(1-Chloro-2-Propyl) Phosphate Usage And Synthesis |
| Chemical Properties | Tris(2-chloro-1-methylethyl) phosphate is clear colorless oily liquid with high water solubility and low lipophilicity (as indicated by logKOW). This substance ismanufactured as a reactionmixture, which contains four isomers. It 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(1-chloro-2-propyl) Phosphate is a flame retardant of low hydrolytic stability, used in polyurethane (PU) rigid and flexible foam, PVC, EVA, phenolics and epoxy resin. | | Definition | ChEBI: Tris(1-chloropropan-2-yl) phosphate is a trialkyl phosphate. | | General Description | Clear colorless viscous liquid. Tris(2-chloroisopropyl) Phosphate(TCPP), mixture of isomers is suitable for use in environmental and food residue analysis. It 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. | | Air & Water Reactions | Insoluble in water. | | Reactivity Profile | Phosphoric acid tris(2-chloro-1-methylethyl) ester may hydrolyze under acidic or alkaline conditions. | | Health Hazard | ACUTE/CHRONIC HAZARDS: When heated to decomposition Phosphoric acid tris(2-chloro-1-methylethyl) ester emits very toxic fumes. | | Fire Hazard | Phosphoric acid tris(2-chloro-1-methylethyl) ester is probably combustible. | | Toxicology | Tris(1-Chloro-2-Propyl) 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 TCPP in the receiving water can affect aquatic organisms and potentially affect human health. | | 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 it 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 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 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. | | References | [1] Patent: CN105085568, 2017, B. Location in patent: Paragraph 0031-0038
[2] J. Gen. Chem. USSR (Engl. Transl.), 1966, vol. 36, # 8, p. 1461 - 1464
[3] Zhurnal Obshchei Khimii, 1966, vol. 36, # 8, p. 1454 - 1459 |
| | Tris(1-Chloro-2-Propyl) Phosphate Preparation Products And Raw materials |
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