TCPP = TCIPP = Tris (1-chloro-2-propyl) phosphate
CAS : 13674-87-8
Tris (1-chloro-2-propyl) phosphate is an PU foam’s additive used as flame retardant in consumer products, home insulation and electronics.
Tris (1-chloro-2-propyl) phosphate is a colorless liquid stable at ambient temperature and not volatile.
Tris (1-chloro-2-propyl) phosphate’s obtained by a reaction of 1-chloro-2-propanol with phosphoryl chloride in the presence of a catalyst.
IDENTITY
Tris (1-chloro-2-propyl) phosphate CAS NO. 13674-84-5.
Tris (1-chloro-2-propyl) phosphate (TCPP) is a clear colorless liquid which is stable at ambient temperature and is not volatile.
Tris (1-chloro-2-propyl) phosphate 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%).
Both Fyrol PCF and Antiblaze 80 (trade names) have a similar composition/purity.
TCC’s Tris (chloroisopropyl) phosphate (TCPP) is a colorless or light yellow transparent liquid.
Tris (1-chloro-2-propyl) phosphates 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 of Tris (1-chloro-2-propyl) phosphate 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 Tris (1-chloro-2-propyl) phosphate can dissolve in organic solvents such as ethyl alcohol, acetone and others.
TCPPhas 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.
Applications of Tris (1-chloro-2-propyl) phosphate:
TCC’s Tris(1-chloro-2-propyl) phosphate (TCPP) is primarily used as a flame retardant in rigid and flexible polyurethane foam.
Specifically, Tris (1-chloro-2-propyl) phosphate is used as a flame inhibitor in the production of bar-shaped or lump-shaped foam.
Tris (1-chloro-2-propyl) phosphate is a low-cost flammable inhibitor and a good stabilizer.
Other applications of Tris (1-chloro-2-propyl) phosphate include use as raw material for the manufacture of polyester foam plastic, binders and other resins.
Molecular Weight: 327.6
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 4
Rotatable Bond Count: 9
Exact Mass: 326.000829
Monoisotopic Mass: 326.000829
Topological Polar Surface Area: 44.8 Ų
Heavy Atom Count: 17
Formal Charge: 0
Complexity: 216
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 3
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Tris (1-chloro-2-propyl) phosphate (TCPP) is a clear colorless liquid which is stable at ambient temperature and is not volatile.
KEYWORDS:
13674-87-8, TCPP, TCIPP, Amgard TMCP, Hostaflam OP 820, 2-Propanol 1-chloro- phosphate (3:1), CCRIS 6111, UNII-CRT22GFY70, EINECS 237-158-7, BRN 1842347
Tris(1-chloro-2-propyl) phosphate (TCIPP) is an emerging contaminant which is ubiquitous in the indoor and outdoor environment.
Moreover, Tris (1-chloro-2-propyl) phosphates presence in human body fluids and biota has been evidenced.
Since no quantitative data exist on the biotransformation or stability of TCIPP in the human body, we performed an in vitro incubation of TCIPP with human liver microsomes (HLM) and human serum (HS).
Two metabolites, namely bis(2-chloro-isopropyl) phosphate (BCIPP) and bis(1-chloro-2-propyl) 1-hydroxy-2-propyl phosphate (BCIPHIPP), were quantified in a kinetic study using HLM or HS (only BCIPP, the hydrolysis product) and LC-MS.
The Michaelis–Menten model fitted best the NADPH-dependent formation of BCIPHIPP and BCIPP in HLM, with respective VMAX of 154 ± 4 and 1470 ± 110 pmol/min/mg protein and respective apparent Km of 80.2 ± 4.4 and 96.1 ± 14.5 μM.
Hydrolases, which are naturally present in HLM, were also involved in the production of BCIPP.
A HS paraoxonase assay could not detect any BCIPP formation above 38.6 ± 10.8 pmol/min/μL serum.
Our data indicate that BCIPP is the major metabolite of TCIPP formed in the liver.
To our knowledge, this is the first quantitative assessment of the stability of TCIPP in tissues of humans or any other species.
Further research is needed to confirm whether these biotransformation reactions are associated with a decrease or increase in toxicity.
Chemical Name: Tris(1-chloro-2-propyl) Phosphate
Synonyms: Tris(2-chloroisopropyl) Phosphate; Antiblaze 80; Antiblaze TMCP; Daltoguard F; Fyrol PCF; Hostaflam OP 820; Levagard PP; Levagard PP-Z; PUMA 4010; TCPP; Tolgard TMCP; Tris(1-methyl-2-chloroethyl) Phosphate; Tris(2-chloro-1-methylethyl) Phosphate;Tris(chloroisopropyl) Phosphate; Tris(β-chloroisopropyl) Phosphate
CAS Number: 13674-84-5
Molecular Formula: C₉H₁₈Cl₃O₄P
Appearance: Clear Colourless Oil
Melting Point: N/A
Molecular Weight: 327.57
Storage: Refrigerator, Under Inert Atmosphere
Solubility: DMSO (Slightly), Methanol (Slightly)
Stability: Moisture Sensitive
Category: Building Blocks; Miscellaneous;
Applications: 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.
TCC’s Tris(1-chloro-2-propyl) phosphate (TCPP) is a clear colorless liquid that is stable at ambient temperature and is not volatile.
Tris (1-chloro-2-propyl) phosphates molecular formula is C9H18Cl3O4P.
Tris (1-chloro-2-propyl) phosphate 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.
Tris (1-chloro-2-propyl) phosphate can be manufactured by either a batch or continuous process.
Tris (1-chloro-2-propyl) phosphate 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.
Tris (1-chloro-2-propyl) phosphate is used as a flame retardant in rigid and flexible polyurethane foam.
Tris (1-chloro-2-propyl) phosphates known use is industrial.
Environment of Tris (1-chloro-2-propyl) phosphate:
Tris (1-chloro-2-propyl phosphate (TCPP) has low volatility at ambient temperature and pressure and is produced in a closed system, therefore, exposure to the environment is expected to be minimal.
In addition, exposure to the environment during the processing of the chemical as a flame retardant in rigid and flexible foam is also expected to be minimal.
TCPP is harmful to aquatic organisms.
Human Health:
TCPP has low volatility at ambient temperature and pressure and is produced in a closed system, therefore, exposure to workers is expected to be minimal.
In addition, exposure to the workers during the processing of the chemical as a flame retardant in rigid and flexible foam is also expected to be minimal.
TCPP shows low acute toxicity following oral, dermal or inhalation exposures.
Tris (1-chloro-2-propyl) phosphate is a slight skin and eye irritant and is not genetically active.
Repeated dose studies showed no adverse effects, Tris (1-chloro-2-propyl) phosphate is neither neurotoxic nor teratogenic.
Tris (1-chloro-2-propyl) phosphate (TCPP) is a chlorinated organic phosphate used in various applications as a flame retardant and plasticizer.
TCPP is a known suspected carcinogen and is not effectively removed by traditional water treatments such as biological, chlorination, and UV irradiation.
In this study, the UV/H2O2 reaction was employed to degrade TCPP in water.
TCPP was effectively degraded in the UV/H2O2 reaction by pseudofirst-order kinetics.
The second-order rate constant of the reaction between the TCPP and OH radical was determined to be 4.35 (±0.13) × 108 M−1 s−1 using the competition kinetics with nitrobenzene as a reference compound.
The degradation of TCPP was affected by the amount of H2O2, pH, and coexisting water components such as HCO3−, NO3−, and humic acid.
Approximately 64.2% of total organic carbon (TOC) in TCPP was mineralized in 12 h during the UV/H2O2 reaction, whereas chloride (Cl−) and phosphate (PO43−) ions were identified as ionic byproducts with the recoveries of 96% chlorine (Cl) and 50% phosphorus (P).
Five organic transformation products (TPs) of TCPP were also identified using LC-qTOF/MS.
Considering the identified TPs, the main degradation pathway of TCPP during the UV/H2O2 reaction was found to be OH-radical-induced hydroxylation.
Finally, a 70% decrease in bioluminescence inhibition in Vibrio fischeri was observed during the UV/H2O2 reaction, and the time-toxicity profile was similar to the time-peak area profile of TPs.
The result of this study implies that TCPP can be efficiently removed with significant mineralization and toxicity reduction by the UV/H2O2 process.
General Discussion of Tris (1-chloro-2-propyl) phosphate:
Production levels are greater than 15,000 metric tons per year.
Tris (1-chloro-2-propyl) phosphate can be manufactured by either a batch or continuous process.
Tris (1-chloro-2-propyl) phosphate 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.
Tris (1-chloro-2-propyl) phosphate 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 use is as a flame retardant in rigid and flexible polyurethane foam.
The known use is industrial.
Tris (1-chloro-2-propyl) phosphate has a log Pow of 2.59 which would indicate a low potential for bioaccumulation in aquatic organisms.
Toxic liquid tris (1-chloro-2-propyl) phosphate) (TCPP) was microencapsulated with the melamine-formaldehyde resin in water and added as the fire-retardant into the polyurethane foam to slow down its diffusion out.
The effect of sodium dodecyl benzenesulfonate and polyvinyl alcohol contents on the particle size was studied and the average size of about 50–250 μm was produced.
Increasing the stirring rate and PVA content decreased the diameter of the microcapsule.
The cell size of polyurethane foams containing TCPP microcapsules was in the range of 100–600 μm.
The polyurethane foam containing 9 wt% of the TCPP microcapsules was HB grade flame-rated.
Environmental Exposure:
No specific information on environmental levels of TCPP is included in the SIDS.
Production Releases:
No specific information on releases from production is included in the SIDS.
However, all emissions which may occur during the manufacturing process are controlled via a tail gas scrubber system.
Organophosphorus flame retardants (OPFRs) are a group of chemicals widely used in various everyday use products.
Tris(2-chloroethyl)phosphate (TCEP) and tris(1-chloro-2-propyl)phosphate (TCPP) are one of the commonly used chemicals belonging to this group.
Due to the need of limitation of the use of polybrominated diphenyl ethers (PBDEs) as retardants, the share of the compounds tested in our experiments in chemicals production systematically increases.
There is limited information about the influence of halogenated OPFRs on living cells, especially on the immune system cells.
That is why the aim of this study was to assess the impact of TCEP and TCPP on viability and morphological alterations of human peripheral blood mononuclear cells (PBMCs).
The cells were incubated with selected flame retardants in the concentrations ranging from 0.001 to 1 mM for 24 h.
Tris (1-chloro-2-propyl) phosphate was found that TCEP at 1 mM and TCPP at 0.5 mM decreased viability of PBMCs, while only TCPP induced morphological alterations in the incubated cells.
The results of our experiments suggest that TCPP is more cytotoxic than TCEP, which can be explained by the presence of methyl groups in the molecule of this compound.
Similar to other studies, our data also suggest that OPFRs are suitable replacements for PBDEs.
Tris(1-chloro-2-propyl) phosphate (TCPP) and tris(1,3-dichloro-2-propyl) phosphate (TDCPP) are added to polyurethane foams in a variety of industrial and consumer products to prevent flame ignition.
The gradual release of these flame retardants (FRs) from such products leads to contamination of various abiotic and biotic media, including wild birds.
Recent studies demonstrated endocrine-disrupting effects of TCPP and TDCPP, including alteration of circulating thyroid hormone (TH) levels.
The TH-pathway is essential for normal growth and development in birds.
There are limited data on the toxicological effects of TCPP and TDCPP in avian species and, prior to this work, no study has examined their effects in avian embryos.
This M.Sc. thesis investigates the developmental, molecular and biochemical effects of TCPP and TDCPP in chicken (Gallus gallus domesticus) embryos via egg injection studies.
TCPP delayed pipping at doses ≥9.24 μg/g, both TCPP and TDCPP reduced embryo growth at the highest dose (51.6 μg TCPP/g and 45 μg TDCPP/g), and TDCPP decreased free plasma thyroxine and gallbladder size at 7.64 μg/g and 45 μg/g, respectively.
Real-time reverse transcription polymerase chain reaction was used to measure changes in mRNA levels of hepatic genes that were responsive to these FRs in a previous in vitro study.
TCPP dysregulated the expression of TH-responsive genes and xenobiotic metabolizing enzymes (cytochrome P450s; CYPs), whereas TDCPP only affected CYPs.
Less than 1% of the administered TCPP or TDCPP was detected in egg contents following 19 days of incubation, indicating extensive metabolism of the parent compounds.
DNA microarrays were used to perform a global transcriptional analysis on liver samples from embryos that exhibited adverse effects following TDCPP injection.
47 differentially expressed genes were identified at the 45 μg/g dose.
Functional analysis revealed that immune function and lipid and steroid metabolism were major targets of TDCPP toxicity and indicated a state of cholestatic liver/biliary fibrosis.
Since the TH-pathway is a key regulator of metabolic homeostasis, its disruption early in development is a potential cause of the observed adverse effects.
This thesis demonstrates, for the first time, developmental and endocrine-disrupting effects of TCPP and TDCPP in an avian species and attempts to link phenotypic changes to molecular-level disruptions in hopes to improve the understanding of their modes of action.
Trade name: TCPP
Chemical name of the compound: Tris(1-chloro-2-propyl) phosphate
Chemical and physical properties: Colorless or slightly yellow liquid, immiscible with water. Undergoes rapid reaction with strong bases and oxidants.
Application: Flame redartant used in polyurethanes, PVC, EVA and phenol/epoxide resins.
Health safety: Toxic, swallowing may cause harm. Irritating for eyes and skin. Not genetically active.
TCPP, Tris(1-chloro-2-propyl)phosphate, CAS 13674-84-5, is a clear colorless liquid, stable and not volatile at ambient temperature.
Tris (1-chloro-2-propyl) phosphate is produced starting from phosphorous oxytrichloride and propylene oxide in the presence of a catalyst agent.
13674-84-5
Tris(1-chloro-2-propyl) phosphate
tris(1-chloropropan-2-yl) phosphate
TRIS(2-CHLOROISOPROPYL)PHOSPHATE
Amgard TMCP
Tris(1-chloro-2-propyl)phosphate
Tris(2-chloro-1-methylethyl) phosphate
Hostaflam OP 820
2-Propanol, 1-chloro-, phosphate (3:1)
TRIS(2-CHLOROISOPROPYL) PHOSPHATE
CCRIS 6111
UNII-CRT22GFY70
EINECS 237-158-7
BRN 1842347
Tris(1-chloro-2-propyl) phosphate, tech grade
TCPP, mixture of isomers
CRT22GFY70
Phosphoric acid, tris(2-chloro-1-methylethyl) ester
TCPP, Tris(1-chloro-2-propyl)phosphate
2-Propanol, 1-chloro-, 2,2',2''-phosphate
DSSTox_CID_6259
DSSTox_RID_78077
DSSTox_GSID_26259
Tri-(2-chloroisopropyl)phosphate
TCPP phosphate cpd
CAS-13674-84-5
Phosphoric acid tris(2-chloro-1-methylethyl) ester
C9H18Cl3O4P
HSDB 8112
Tris(1-chloro-2-propanyl) phosphate
tris(2-chloro-1-methylethyl)phosphate
Flame retardant TCPP
AK109623
EC 237-158-7
SCHEMBL35713
CHEMBL3188873
DTXSID5026259
CHEBI:143728
Tris(1-chloropropan-2-yl)phosphate
Tox21_202982
Tox21_303533
tris(2-chloro-1-methylethyl) ester
MFCD0004040
AKOS015899872
NCGC00257407-01
NCGC00260528-01
Tris(2-chloroisopropyl)phosphate (TCPP)
I990
FT-0689156
Flame retardant Tris(2-chloroisopropyl)phosphate
A886642
Q-201899
Q2454095
Tris(1-chloropropan-2-yl) phosphate, mixture of isomers
Tri(chloropropyl) phosphate & Tetrabromophthalic acid diester
98112-32-4