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)

Flash point:

-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(1-chloro-2-propyl) phosphate (13674-84-5)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-37

WGK Germany 

1

RTECS 

TC9000000

Hazardous Substances Data

13674-84-5(Hazardous Substances Data)

MSDS

• Language:English Provider:Phosphoric acid tris(2-chloro-1-methylethyl) ester

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

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