13674-87-8

Basic information

• Product Name: Fyrol FR 2
• Synonyms: 1,3-Dichloro-2-propanol phosphate, Phosphoric acid tris(1,3-dichloro-2-propyl ester);1,3-Dichloro-2-propanol phosphate, Phosphoric acid tris(1,3-dichloro-2-propyl ester), Tris(1,3-dichloro-2-propyl) phosphate;Tris(1,3-Dichloro-2-Propyl)Phosphate(TDPP);Phosphoric acid tris(1,3-dichloropropan-2-yl;Phosphoric acid tris(1,3-dichloropropan-2-yl) ester;Tris(1,3-dichloropropane-2-yl) phosphate;1,3-Dichloro-2-propanol phosphate;tris(1,3-dichloropropan-2-yl) phosphate
• CAS NO: 13674-87-8
• Molecular Formula: C₉H₁₅Cl₆O₄P
• Molecular Weight: 430.9
• EINECS: 237-159-2
• Product Categories: Functional Materials;Phosphates (Plasticizer);Plasticizer;Organics
• Mol File: 13674-87-8.mol

Chemical Properties

• Melting Point: -64°C
• Boiling Point: 315°C
• Flash Point: 249°C
• Appearance: /solid
• Density: 1.512
• Vapor Pressure: 4.07E-08mmHg at 25°C
• Refractive Index: n20/D 1.503
• Water Solubility: <0.1 g/100 mL at 24℃
• Stability: Stable. Reacts slowly with aqueous acids and alkalies. May soften plastics.
• Merck: 14,9087
• CAS DataBase Reference: Fyrol FR 2(CAS DataBase Reference)
• NIST Chemistry Reference: Fyrol FR 2(13674-87-8)
• EPA Substance Registry System: Fyrol FR 2(13674-87-8)

Safety Data

• Hazard Codes: Xn,N
• Statements: 20/21/22-36/37/38-51/53-38-20-40
• Safety Statements: 26-36/37/39-61-36/37
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 2
• RTECS: UB1473000
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 13674-87-8(Hazardous Substances Data)

Usage

Uses

Used in Polyurethane Foams:
Fyrol FR 2 is used as a flame retardant for flexible polyurethane foams (PUFs) to improve their fire resistance and safety. This application is particularly important in industries such as furniture manufacturing, automotive seating, and bedding products.
Used in Automotive Industry:
Fyrol FR 2 is used as a component in molded automotive seating foam, including seat cushions and headrests, to enhance fire safety and meet regulatory standards.
Used in Furniture and Related Products:
Fyrol FR 2 is used as a flame retardant in slabstock foam used in furniture manufacturing, providing an additional layer of safety and protection against fire hazards.
Used in Building and Construction Materials:
Fyrol FR 2 is used in the production of building and construction materials to improve their fire resistance and meet safety regulations.
Used in Fabrics, Textiles, and Leather Products:
Fyrol FR 2 is used as a flame retardant in the manufacturing of fabrics, textiles, and leather products to enhance their fire safety and protect users from potential fire hazards.
Used in Paints and Coatings:
Fyrol FR 2 is used as an additive in the production of paints and coatings to improve their fire resistance and provide additional safety benefits.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Fyrol FR 2 hydrolyzes slowly when refluxed with an aqueous acid. Under alkaline conditions, Fyrol FR 2 exhibits a slow cleavage. Fyrol FR 2 has plasticizing properties and, as such, may soften or deteriorate certain plastics and elastomers (particularly vinyl-based resin, neoprene and natural rubbers).

Fire Hazard

Fyrol FR 2 is combustible.

Safety Profile

Moderately toxic by ingestion. An experimental teratogen. Experimental reproductive effects. Questionable carcinogen with experimental carcinogenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of Cland POx.

Environmental Fate

A series of studies have been performed to evaluate the environmental fate and bioaccumulation potential of Tris(1,3-dichloro-2-propyl)phosphate (TDCPP).EU concluded that TDCPP is expected to be persistent in water, sediment, sewage sludge, and soil. When emitted to the environment, the EU concluded that TDCPP will likely adsorb to particulate matter, based on its low volatility and relatively high adsorption coefficient. The Henry’s law constant suggests that TDCPP will preferentially partition to water, rather than air. When assessing TDCPP's potential for persistence or bioaccumulation, the EU determined that TDCPP can potentially be persistent or very persistent and that it does not meet the criteria for bioaccumulative or very bioaccumulative compounds.

InChI:InChI=1/C9H15Cl6O4P/c10-1-7(2-11)17-20(16,18-8(3-12)4-13)19-9(5-14)6-15/h7-9H,1-6H2

Synthetic route

1,3-Dichloro-2-propanol (96-23-1) → CRP (13674-87-8)

Conditions	Yield
With sulphate-doped anatase; trichlorophosphate at 150℃; for 4h; Reagent/catalyst; Temperature;	96.8%
With hydrogenchloride; trichlorophosphate at 110 - 180℃; for 3h; Temperature; Autoclave;	89.72%
With phosphorus pentoxide at 160℃; for 7h; Catalytic behavior; Temperature; Reagent/catalyst;	87.8%
With pyridine; trichlorophosphate; benzene

epichlorohydrin (106-89-8) → CRP (13674-87-8)

Conditions	Yield
With hydrogenchloride; trichlorophosphate

chloral hydrate (302-17-0) + CRP (13674-87-8) → (2,2,2-trichloro-1-hydroxy-ethyl)-phosphonic acid bis-(2-chloro-1-chloromethyl-ethyl) ester (14634-03-8)

Conditions	Yield
In hexane Heating;	80%

Upstream product

• 96-23-1 1,3-Dichloro-2-propanol 
• 106-89-8 epichlorohydrin 

Relevant articles and documents

Method for preparing tris(1,3-dichloropropyl) phosphate

The invention discloses a method for preparing tris(1,3-dichloropropyl) phosphate. The method specifically comprises the following steps: adding phosphorus oxychloride and 1,3-dichloropropanol into areaction kettle at a time, stirring the phosphorus oxychloride and the 1,3-dichloropropanol, raising the temperature to 110 DEG, performing a reaction on the phosphorus oxychloride and the 1,3-dichloropropanol for 1-3h, raising the temperature to 180 DEG according to the 15-30-DEG C gradient, removing generated hydrogen chloride gas under a negative pressure condition and reducing the temperature,so as to obtain a crude product; washing the crude product with alkali and water in sequence and distilling, so as to obtain the tris(1,3-dichloropropyl) phosphate. Under a catalyst-free condition, the method has the advantages of being high in product purity, high in conversion rate, mild in process conditions, and simple in operation, avoiding a problem of aftertreatment of a catalyst and lowering the production cost.

Preparation method of tris(1,3-dichloropropyl) phosphonate

The invention discloses a preparation method of tris(1,3-dichloropropyl) phosphonate. The preparation method comprises the following specific steps: (1) preparation of catalyst: preparing a solid acidcatalyst from soluble salt of metals such as Ti, Zr and Fe; and (2) preparation of tris(1,3-dichloropropyl) phosphonate: adding the solid acid catalyst and reaction materials to a reactor at one time, raising the temperature to 120-160 DEG C for reacting for 6-10 hours, simultaneously distilling off the water generated by reaction in a pressure range of -0.2 to 0 MPa, and performing alkali washing, water washing and distillation on a crude product to obtain the tris(1,3-dichloropropyl) phosphonate. The preparation method disclosed by the invention adopts a home-made catalyst and takes dichloropropanol and phosphorus pentoxide as reaction raw materials to synthesize the tris(1,3-dichloropropyl) phosphonate, the catalyst is easy to recover and has good catalytic performance, the synthetic process of the tris(1,3-dichloropropyl) phosphonate is simple in route and easy to operate, water is generated by reaction, the process is safe and environment-friendly, and industrial production is easy to realize.

Method for preparing tri(1,3-dichloro-2-propyl) phosphonate

The invention provides a method for preparing tri(1,3-dichloro-2-propyl) phosphonate, which relates to the technical field of a preparation method of a fire retardant. The method adopts a self-made catalyst, and uses phosphorus oxychloride and 1,3-dichloro-2-propanol as a raw material, and adopts the following steps: phosphorus oxychloride, 1,3-1,3-dichloro-2- propanol and the self-made solid acidcatalyst are added to a reaction kettle, the materials are heated to the temperature of 100-160 DEG C for 4-6 hours, the generated hydrogen chloride gas is distilled under vacuum of -0.2-0 MPa, a crude product is washed with alkali, washed with water, and is subjected to underpressure distillation to remove water. A reaction equation is shown as the specification. The raw materials of the invention are easy to obtain, the catalyst has good catalytic performance, the product has high purity, the yield is high, the reaction is mild, the operation is simple, and the product is more suitable forindustrial production.