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Isopropylated triphenyl phosphate is a chemical compound that belongs to the family of organophosphate esters, specifically a phosphate ester flame retardant and plasticizer.
Isopropylated triphenyl phosphate is not a single, pure compound but rather a mixture of isopropylated isomers of triphenyl phosphate, where one or more of the phenyl groups in triphenyl phosphate have isopropyl substituents (–CH(CH₃)₂) at various positions on the aromatic rings.
Isopropylated triphenyl phosphate is widely used in industrial applications due to its dual function: it serves as a flame retardant, reducing the flammability of materials, and also as a plasticizer, improving flexibility and durability in plastics.
CAS Number: 68937-41-7
Molecular Formula: C27H33O4P
Molecular Weight: 452.52
EINECS Number: 273-066-3
Synonyms: Tris(isopropylphenyl) phosphate, Tris(4-isopropylphenyl)Phosphate, DTXSID50858795, 248-147-1, Tris(4-isopropylphenyl) phosphate, 26967-76-0, 2502-15-0, Tris(p-isopropylphenyl)phosphate, tris(4-propan-2-ylphenyl) phosphate, Tri(4-isopropylphenyl) phosphate, Phenol,(1-methylethyl)-, phosphate (3:1), Y3H2FDX0NW, Phenol, 4-(1-methylethyl)-, phosphate (3:1), DTXSID80858783, Tris[4-(2-methylethyl)phenyl] phosphate, DSSTox_CID_8880, DSSTox_RID_78659, DSSTox_GSID_28880, CAS-68937-41-7, Tris(p-cumenyl)phosphate, UNII-Y3H2FDX0NW, Tri(4-isopropylphenyl)phosphate, IPPP - technical, EINECS 219-703-0, Isopropylphenylphosphat, SCHEMBL36617, CHEMBL458602, Isopropylate Triphenyl Phosphate, ANVREEJNGJMLOV-UHFFFAOYSA-N, Tox21_202764, Tox21_202765, Tox21_202766, FI40310, NCGC00260311-01, NCGC00260312-01, NCGC00260313-01, TRIS(P-ISOPROPYLPHENYL) PHOSPHATE, NS00003997, P-CUMENYL PHOSPHATE ((C9H11O)3PO), PHENOL, P-ISOPROPYL-, PHOSPHATE (3:1), Tris(4-isopropylphenyl)phosphate, technical grade, Q27294219, Phenol,isopropylated,phosphate(3:1);TRIS(ISOPROPYLPHENYL)PHOSPHATE-1M ALKYL;isopropylated phenol phosphate;ISOPROPYLATED TRIPHENYL PHOSPHATE;Isopropylphenyl phosphate;triisopropylated phenyl phosphate;Phenolphosphateisopropylated;Triarylphosphatisopropylated
Isopropylated triphenyl phosphate is commonly added to products like polyvinyl chloride (PVC), polyurethane foams, rubber, and electronic components to enhance fire resistance while maintaining mechanical properties.
Chemically, Isopropylated triphenyl phosphate is produced by reacting phosphorus oxychloride with isopropylated phenols.
The result is a mixture of compounds where the phosphate group is bonded to three phenyl rings, some of which may be substituted at the para (4) position with isopropyl groups.
These substitutions alter the physical and chemical properties of the final product, including viscosity, volatility, and compatibility with different polymers.
Isopropylated triphenyl phosphate synonymous with Isopropylated phenol phosphate and triisopropylated phenyl phosphate, is a white to yellow transparent liquid used as a flame retardant additive for paints and plastics.
Isopropylated triphenyl phosphate is recommended for use in PVC, fiber resin, synthetic rubber, pressure oil fields.
Isopropylated triphenyl phosphate is the chemical compound with the formula OP(OC6H5)3.
It is the simplest aromatic organophosphate.
This colourless solid is the ester (triester) of phosphoric acid and phenol.
Isopropylated triphenyl phosphate is used as a plasticizer and a fire retardant in a wide variety of settings and products.
Isopropylated triphenyl phosphate is prepared by the SN2 reaction of phosphorus oxychloride and phenol.
Isopropylated triphenyl phosphate that is used as a plasticizer and flame retardant in industrial, commercial, and consumer products, including some children's products.
Both high and low alkylated products are also used in polyurethanes, textile coatings, adhesives, paints and pigment dispersions.
Lower alkylated products are used in thermoplastics.
Isopropylated triphenyl phosphate is a chemical substance with the molecular formula of C27H33O4P.
Isopropylated triphenyl phosphate is a halogen-free phosphate flame retardant plasticizer and will not pollute the environment twice.
The offered Isopropylated Triphenyl Phosphate is very effective and made for use in the industries. The chemical is very safe for use.
Environmental and health concerns have been raised due to its persistence in the environment and potential for bioaccumulation.
Isopropylated triphenyl phosphate is known to be moderately toxic and has been detected in indoor dust, electronic waste, and even human tissues, indicating widespread exposure.
Regulatory agencies are monitoring it more closely, especially under chemical safety programs such as REACH and TSCA.
Isopropylated triphenyl phosphate is not a single molecule but a complex mixture of organophosphate esters.
The core structure is based on Isopropylated triphenyl phosphate, where a central phosphorus atom is bonded to three aromatic phenyl rings via oxygen atoms.
In Isopropylated triphenyl phosphate, some of these phenyl rings are substituted with isopropyl groups—most commonly at the para position, but also potentially at meta or ortho positions.
Boiling point: 400℃[at 101 325 Pa]
Density: 1.168[at 20℃]
vapor pressure: 0Pa at 25℃
storage temp.: Hygroscopic, Refrigerator, under inert atmosphere
solubility: Benzene (Slightly), Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
form: Oil
color: Colourless
Water Solubility: 330μg/L at 20℃
Stability: Hygroscopic, Moisture Sensitive
LogP: 4.92 at 25℃
Isopropylated triphenyl phosphate contains a phosphorus atom bonded to three aryl (phenyl) groups, each connected via an oxygen atom, forming aryl phosphate esters.
In this case, the phenyl groups have isopropyl groups (–CH(CH₃)₂) added mainly at the para position (4-position) on the ring.
Isopropylated triphenyl phosphate has been detected in the environment.
Other triaryl phosphates have been known to enter aquatic environments through volatilization and leaching from plastics, through hydraulic fluid leakages, and, to a lesser degree, through manufacturing processes.
Isopropylated triphenyl phosphate, in particular, has been found to enter the environment through industrial use, as in the manufacturing process, and through indoor use, for example through paints and electronic equipment.
As with many other phosphorus-containing flame retardants, TPhP has been found widely in sediment, soil, indoor dust, and air.
Once in water, Isopropylated triphenyl phosphate has been found to biodegrade relatively quickly under both aerobic and anaerobic conditions, and does not meet criteria for being categorized as persistent.
However, although the compound biodegrades easily and does not bioaccumulate, it is readily detected because of the sheer volume that is utilized.
In 2014, the United States Environmental Protection Agency added Isopropylated triphenyl phosphate to its list of Toxic Substance Control Act Work Plan for Chemicals on the basis that the compound has exhibited "acute and chronic aquatic toxicity," "moderate bioaccumulation potential," and "moderate environmental persistence." Still, there is not yet enough information to fully assess the environmental impact of TPhP.
Isopropylated triphenyl phosphate releases phosphorus-containing radicals during combustion, which interfere with flame-propagating free radicals (e.g., H•, OH•).
Isopropylated triphenyl phosphate promotes the formation of a char layer, which insulates the material and slows heat release and oxygen access.
Limited information is available indicating significant toxicological effects of Isopropylated triphenyl phosphate.
Although it was initially expected to have an overall low impact, a growing body of evidence suggests that the effects may not be so harmless.
Isopropylated triphenyl phosphate exhibits low acute toxicity by dermal or oral contact.
However, an increasing number of studies have linked exposure to Isopropylated triphenyl phosphate with reproductive and developmental toxicity, neurotoxicity, metabolic disruption, endocrine effects, and genotoxicity.
Isopropylated triphenyl phosphate has also been found to induce significant estrogenic activity.
One study found that concentrations above the lowest observable effect level have been observed in a variety of other studies in coral grouper, yellow striped goat fish, and freshwater perch.
This indicates that Isopropylated triphenyl phosphate may be present in the environment at high enough concentrations to have harmful ecological effects.
The European Chemicals agency considers Isopropylated triphenyl phosphate to be "very toxic" to aquatic life, with potentially long-lasting effects.
In contrast to many persistent organic pollutants, Isopropylated triphenyl phosphate has limited affinity for lipids.
Still, bioaccumulation of the compound has been found to occur at varying levels in fish, with the strongest patterns showing up based on gender, feeding patterns, and metabolic efficiency.
However, the mechanisms explaining why and how TPhP accumulates in this manner are not yet known.
Isopropylated triphenyl phosphate is typically synthesized by reacting phosphorus oxychloride (POCl₃) with isopropylated phenols, using a catalyst.
The process yields a technical-grade product, which is a mixture of different isomers and homologs.
Manufacturers may tailor the level of isopropylation based on the intended application.
Some isomers within the Isopropylated triphenyl phosphate mixture are toxic to aquatic life and may disrupt endocrine function in mammals.
Studies have detected IPPP in indoor air, house dust, soil, water, and even human blood and breast milk, suggesting its persistence and potential for bioaccumulation.
People can be exposed through inhalation of dust, skin contact, or ingestion of contaminated materials.
Isopropylated triphenyl phosphate is under scrutiny, with some forms possibly requiring restriction or authorization.
The U.S. Environmental Protection Agency has assessed IPPP under the Toxic Substances Control Act as part of its flame retardant cluster.
Some organophosphate esters, including Isopropylated triphenyl phosphate components, are listed due to concerns about developmental and reproductive toxicity.
Isopropylated triphenyl phosphate is a technically valuable chemical in flame retardancy and plasticization, but its complex isomeric mixture, environmental persistence, and potential health risks have led to increased scientific and regulatory scrutiny.
Isopropylated triphenyl phosphate highlights the challenge of balancing performance with safety in industrial chemical applications.
Some isomers, especially mono-isopropyl derivatives, have shown developmental neurotoxicity in animal studies.
Isopropylated triphenyl phosphate exposure has been linked to altered behavior, learning deficits, and endocrine disruption in lab models.
Certain components have weak estrogenic or anti-androgenic activity.
Animal studies have noted decreased fertility, disrupted hormone levels, and developmental toxicity.
No strong human data exist yet, but long-term rodent studies have raised concerns about liver and kidney effects.
The mixture is not classified as a known human carcinogen, but is under study.
Uses:
Isopropylated triphenyl phosphate has been used widely as a flame retardant and plasticizer.
Isopropylated triphenyl phosphate has been used as a flame retardant for a variety of materials, including electronic equipment, PVC, hydraulic fluids, glues, in nail polishes, and casting resins.
Its mechanism of action as a flame retardant is as follows: first, during thermal decomposition, phosphoric acid is formed.
This reacts to form pyrophosphoric acid, which, when in its condensed phase, acts to block heat transfer.
One of the most effective flame retardants for certain polymers, Isopropylated triphenyl phosphate is only active as an additive flame retardant in its gas phase.
Phase out of PBDEs may have increased the use of TPhP in recent years.
Isopropylated triphenyl phosphate is also used as a plasticizer in lacquers, varnishes, and hydraulic fluids. Nail polish has received particular interest as a source of exposure to TPhP.
Isopropylated triphenyl phosphate, is a flame retardant
One of the most significant and widespread uses of Isopropylated triphenyl phosphate is as a flame retardant additive in plastic materials, particularly in flexible polyvinyl chloride (PVC).
In these applications, Isopropylated triphenyl phosphate is incorporated into the polymer matrix to reduce flammability, inhibit ignition, and slow down the spread of fire by promoting the formation of a protective char layer or by interfering with flame-propagating chemical reactions in the gas phase.
Isopropylated triphenyl phosphate is especially valued in cases where halogen-free fire protection is desired, due to concerns over toxic halogenated byproducts like dioxins and furans.
Isopropylated triphenyl phosphate is used as a plasticizer and flame retardant.
It has been used in Europe in polyurethanes, polyvinyl chloride (PVC) products, textile coatings, paints, adhesives, and pigment dispersions.
An isomeric mixture of phosphate esters makes up IPTPP and may vary in composition.
Isopropylated triphenyl phosphate is also a component of the commercial flame retardant mixture Firemaster 550, which is widely used in flexible polyurethane foam as a flame retardant.
Firemaster 550 that contains Isopropylated triphenyl phosphate has been detected in children’s products.
In the furniture industry, Isopropylated triphenyl phosphate is widely used as a flame retardant in polyurethane foam found in upholstered furniture, mattresses, bedding, and automotive seating.
By blending Isopropylated triphenyl phosphate into foam formulations, manufacturers aim to meet flammability standards such as California's Technical Bulletin 117 (TB117), which tests for resistance to ignition from smoldering sources.
Its use helps extend the fire escape time in case of household fires and improves consumer safety without significantly altering the comfort or performance of the foam.
In addition to its flame-retardant function, Isopropylated triphenyl phosphate acts as a secondary plasticizer in various plastics, meaning it is used to increase flexibility, workability, and durability in materials that would otherwise be too brittle or rigid for practical use.
For instance, in flexible PVC products such as coated fabrics, vinyl flooring, cables, hoses, and synthetic leather, Isopropylated triphenyl phosphate enhances softness, reduces brittleness, and improves resistance to cracking or tearing during use or aging.
Isopropylated triphenyl phosphate is used as a performance-enhancing additive in fire-resistant hydraulic fluids, particularly in applications where both flame retardancy and lubricity are important.
These include heavy machinery, industrial presses, and mining equipment, where hydraulic systems must operate under high pressure and temperatures, often in flammable environments.
Isopropylated triphenyl phosphate's chemical stability and lubricating characteristics make it useful in phosphate ester-based fluids, which are common in aerospace and defense applications as well.
Within the construction industry, Isopropylated triphenyl phosphate is added to various building materials such as insulation panels, sealants, adhesives, coatings, and wall coverings to reduce their susceptibility to fire.
These applications help building components meet national and international fire safety building codes, while maintaining their mechanical integrity and ease of installation.
In the automotive sector, Isopropylated triphenyl phosphate is used in interior components, including dashboards, trim panels, seat cushions, headliners, and cable insulation, where both thermal resistance and flexibility are essential.
Its use contributes to vehicle fire safety standards and enhances the durability of polymer-based components exposed to mechanical stress, UV light, and varying temperatures over time.
In consumer products, it is used in automotive care products; in photographic supplies, film and photo chemicals; in unspecified plastic and rubber products, and in foam seating and bedding products.
Isopropylated triphenyl phosphate isomers are a listed ingredient of Firemaster®550 which is used as an additive flame retardant in flexible polyurethane foam. U.S. consumer product testing has identified the profile of flame retardants contained in Firemaster®550 in foam baby products and U.S. upholstered furniture.
As a plasticizer or flame retardant added in PVC, PU, PE, PP, PC/ABS, PPO/HIPS, PVAC, PS, fabric coatings, circuit boards, spinning Chemicalbook fabrics, phenolic resin, polyethylene, artificial leather, film, plate, conveyor belt, air pipe, floor material cable, synthetic resin, plastic, rubber and fiber to increase the process performance of the product.
Isopropylated triphenyl phosphate is commonly used in the electronics industry as a flame-retardant additive in the manufacturing of electronic casings, circuit boards, wiring insulation, and connectors, where the risk of overheating or electrical fire is present.
Its use in such products helps manufacturers comply with fire safety regulations such as UL 94 V-0, while also providing plasticizing properties that improve the mechanical flexibility of polymer components used in electronics.
Isopropylated triphenyl phosphate may also be found in specialty coatings, inks, and adhesives, where it helps to reduce flammability and improve adhesion, chemical resistance, and film flexibility.
It is particularly useful in formulations for industrial floor coatings, anti-corrosion primers, and solvent-resistant adhesives used in manufacturing and construction settings.
Historically, some phosphate-based plasticizers, including Isopropylated triphenyl phosphate derivatives, were explored for use in food packaging and conveyor belts.
However, due to migration concerns and increasing regulatory scrutiny, the use of IPPP in direct food-contact applications is now highly restricted or avoided in most regions.
Modern food safety standards typically require migration testing, and safer alternatives are generally preferred in these contexts.
In laboratory settings and toxicological research, Isopropylated triphenyl phosphate is often included in chemical screening programs like Tox21, which study its effects on human health, including endocrine activity, cytotoxicity, and gene expression changes.
These efforts aim to understand long-term health risks and help regulatory agencies determine appropriate restrictions or safer substitutions.
In summary, Isopropylated triphenyl is a multifunctional industrial chemical, valued primarily for its flame retardant and plasticizing properties, with widespread use in plastics, electronics, furniture, automotive parts, coatings, and hydraulic fluids.
While it enhances product safety and performance, its environmental persistence and toxicological profile have led to increasing regulatory attention and a push toward safer alternatives, especially in applications involving close or long-term human exposure.
Safety Profile:
Exposure to Isopropylated triphenyl phosphate has been associated with potential neurotoxic effects, particularly concerning during early developmental stages.
Animal studies suggest that certain isomers or metabolites of IPPP may interfere with normal brain development, potentially leading to cognitive impairments, behavioral changes, and learning deficits in offspring.
These concerns arise from its structural similarity to known neurotoxic organophosphate compounds, which can interfere with neurotransmitter function.
There is growing evidence that components of Isopropylated triphenyl phosphate can act as endocrine disruptors, meaning they can interfere with hormone regulation in the body.
Long-term or repeated exposure has been linked in some studies to altered estrogen and androgen activity, which may lead to disruptions in reproductive function, such as reduced fertility, menstrual irregularities, and developmental issues in offspring.
These effects are of particular concern for pregnant women, infants, and children, who may be more vulnerable to hormone-related toxicity.
Some animal studies have reported that high doses of Isopropylated triphenyl phosphate can result in damage to the liver, kidneys, and thyroid gland, suggesting that repeated or chronic exposure may lead to organ dysfunction over time.
The liver, in particular, appears to be a target organ, with signs of enzyme induction, inflammation, or fatty liver changes observed in toxicity studies.
Although Isopropylated triphenyl phosphate is not considered highly irritating under normal use, direct skin contact or inhalation of aerosolized particles or vapors may cause mild skin and eye irritation in some individuals.
Prolonged occupational exposure, particularly in poorly ventilated environments, could lead to respiratory discomfort, headaches, or allergic sensitization in sensitive individuals.
While Isopropylated triphenyl phosphate functions as a flame retardant, it is still considered a combustible liquid and can contribute to fire hazards under specific conditions, particularly at elevated temperatures or in the presence of other flammable substances.
When burned, Isopropylated triphenyl phosphate can release toxic combustion byproducts such as phosphoric acid fumes, carbon monoxide (CO), carbon dioxide (CO₂), and aromatic hydrocarbons, all of which are harmful when inhaled.
