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Tris(chloropropyl) phosphate (commonly abbreviated TCPP) is a chlorinated organophosphate flame retardant commonly added to polyurethane foams.
Comparatively minor amounts are used in PVC and EVA.
CAS : 13674-87-8
IUPAC name
Tris(2-chloro-1-methylethyl) phosphate
Synonyms:
Tris(1-chloro-2-propyl)phosphate,Tris(2-chloroisopropyl)phosphate,Tris(monochloroisopropyl) phosphate (TMCP), Tris(2-chloroisopropyl) phosphate (TCIP) Fyrol PCF,tri(2-chloropropyl)phosphate,tri(chloropropyl) phosphate,tris(2-chloropropyl)phosphate,tris(chloropropyl)phosphate, Tris(2-chloropropyl) phosphate,6145-73-9,Fyrol pcf,1-Propanol, 2-chloro-, phosphate (3:1),Tris(2-chloropropyl)phosphate,Tris(beta-chloropropyl) phosphate,AP 33,EINECS 228-150-4,NSC 524664,2-Chloro-1-propanol phosphate (3:1),N90B627VHY,DTXSID3027615,NSC-524664,tri(2-chloropropyl) phosphate,DTXCID207615,1-Propanol, 2-chloro-, 1,1',1''-phosphate,TRI(.BETA.-CHLOROPROPYL) PHOSPHATE,TRIS(.BETA.-CHLOROPROPYL) PHOSPHATE,tri(beta-chloropropyl) phosphate,228-150-4,UNII-N90B627VHY,SCHEMBL25060,Tri(2-chloropropyl)phosphate,Tris(b-Chloropropyl)phosphate,1-Propanol, phosphate (3:1),CHEMBL3182409,GTRSAMFYSUBAGN-UHFFFAOYSA-,Tris(.beta.-chloropropyl)phosphate,Tox21_302421,NSC524664,NCGC00255270-01,CAS-6145-73-9,NS00073946,Q27284721,1-[bis(2-chloropropoxy)phosphoryloxy]-2-chloro-propane,InChI=1/C9H18Cl3O4P/c1-7(10)4-14-17(13,15-5-8(2)11)16-6-9(3)12/h7-9H,4-6H2,1-3H3
SYNTHESIS
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).[3]
TCPP – (Tris (1-chloro-2-propyl) phosphate)is an PU foam’s additive used as flame retardant in consumer products, home insulation and electronics.
The product is a colorless liquid stable at ambient temperature and not volatile.
It’s obtained by a reaction of 1-chloro-2-propanol with phosphoryl chloride in the presence of a catalyst.
TCC’s Tris (chloroisopropyl) phosphate (TCPP) is a colorless or light yellow transparent liquid. Its molecular formula is C9H18Cl3O4P.
The chemical is used as a low-cost flame inhibitor in the production of bar-shaped and lump-shaped foam.
Other applications include use as raw material for the manufacture of polyester foam plastic, binder and other resins.
TCCP is harmful if swallowed and is irritating to the respiratory system.
The liquid chemical does not dissolve in water, but it can dissolve in organic solvents such as ethyl alcohol, acetone and others.
TCPP has good heat conductivity and is a hydrolysis stabilizer with good retarding ability for containing phosphor and chlorine. TCPP is normally used at 10~15 phr depending on applications.
TCC’s Tris(1-chloro-2-propyl) phosphate (TCPP) is a clear colorless liquid that is stable at ambient temperature and is not volatile.
Its molecular formula is C9H18Cl3O4P.
It is manufactured to a purity of 75 ± 10%. Major impurities are bis(1-chloro-2-propyl)-2-chloropropyl phosphate (20-30%) and bis(2-chloropropyl)-1-chloro-2-propyl phosphate (3-5%).
TCPP is harmful if swallowed, and is irritating to the respiratory system.
If ingested, the targeted organs are the liver and bladder.
TCPP can be manufactured by either a batch or continuous process.
TCPP is the reaction of phosphorous oxytrichloride with propylene oxide in the presence of a catalyst.
The reaction is carried out in a closed reactor.
The crude product is washed and dehydrated in a closed vessel to remove acidic impurities and residual catalyst.
All transfers are done using closed lines.
The product is then filtered, transferred, and packaged using sealed pumps through closed lines.
Storage is in closed vessels under nitrogen to exclude moisture and oxygen.
TCPP is used as a flame retardant in rigid and flexible polyurethane foam.
Its known use is industrial.
APPLICATIONS
TCC’s Tris(1-chloro-2-propyl) phosphate (TCPP) is primarily used as a flame retardant in rigid and flexible polyurethane foam.
Specifically, it is used as a flame inhibitor in the production of bar-shaped or lump-shaped foam.
It is a low-cost flammable inhibitor and a good stabilizer.
Other applications include use as raw material for the manufacture of polyester foam plastic, binders and other resins.
PROPERTIES OF TRIS(2-CHLOROISOPROPYL) PHOSPHATE (TCPP)
CAS Number
13674-84-5
3D model (JSmol)
Interactive image
ChEBI
CHEBI:143728
ChEMBL
ChEMBL3188873
ChemSpider
24387
ECHA InfoCard 100.033.766 Edit this at Wikidata
EC Number
237-158-7
PubChem CID
26176
UNII
CRT22GFY70
CompTox Dashboard (EPA)
DTXSID5026259 Edit this at Wikidata
Chemical formula C9H18Cl3O4P
Molar mass 327.56 g·mol−1
Appearance Liquid
Melting point 20 °C (68 °F; 293 K)
Boiling point 290 °C (554 °F; 563 K) decomposes
Solubility in water 1,080 mg/l at 20°C
Molecular Weight
327.6 g/mol
Computed by PubChem 2.2 (PubChem release 2025.04.14)
XLogP3-AA
2.6
Computed by XLogP3 3.0 (PubChem release 2025.04.14)
Hydrogen Bond Donor Count
0
Computed by Cactvs 3.4.8.18 (PubChem release 2025.04.14)
Hydrogen Bond Acceptor Count
4
Computed by Cactvs 3.4.8.18 (PubChem release 2025.04.14)
Rotatable Bond Count
9
Computed by Cactvs 3.4.8.18 (PubChem release 2025.04.14)
Exact Mass
326.000829 Da
Computed by PubChem 2.2 (PubChem release 2025.04.14)
Monoisotopic Mass
326.000829 Da
Computed by PubChem 2.2 (PubChem release 2025.04.14)
Topological Polar Surface Area
44.8 Ų
Computed by Cactvs 3.4.8.18 (PubChem release 2025.04.14)
Heavy Atom Count
17
Computed by PubChem
Formal Charge
0
Computed by PubChem
Complexity
216
Computed by Cactvs 3.4.8.18 (PubChem release 2025.04.14)
Isotope Atom Count
0
Computed by PubChem
Defined Atom Stereocenter Count
0
Computed by PubChem
Undefined Atom Stereocenter Count
3
Computed by PubChem
Defined Bond Stereocenter Count
0
Computed by PubChem
Undefined Bond Stereocenter Count
0
Computed by PubChem
Covalently-Bonded Unit Count
1
Computed by PubChem
Compound Is Canonicalized
Yes
SAFETY INFORMATION ABOUT TRIS(2-CHLOROISOPROPYL) PHOSPHATE (TCPP)
First aid measures:
Description of first aid measures:
General advice:
Consult a physician.
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
If inhaled:
If breathed in, move person into fresh air.
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately.
Wash off with soap and plenty of water.
Consult a physician.
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
If swallowed:
Do NOT induce vomiting.
Never give anything by mouth to an unconscious person.
Rinse mouth with water.
Consult a physician.
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment.
Avoid breathing vapours, mist or gas.
Evacuate personnel to safe areas.
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste.
Keep in suitable, closed containers for disposal.
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles.
Faceshield (8-inch minimum).
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection:
Handle with gloves.
Gloves must be inspected prior to use.
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product.
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls.
If the respirator is the sole means of protection, use a full-face supplied air respirator.
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions.
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product
