Tetraphenyl resorcinol bis(diphenylphosphate)

• CAS: 57583-54-7
• Catalog Number: ACM57583547
• Category: Main Products
• Molecular Weight: 574.45
• Molecular Formula: C₃₀H₂₄O₈P₂
• Synonyms: Fyrolflex RDP, Mark PFK, Oligomeric phosphate ester, CRR-733S, Tetraphenylresorcinol diphosphate, 1,3-Phenylene tetraphenyl phosphate, m-Phenylenebis(diphenyl phosphate), Resorcinol bis(diphenyl phosphate), EINECS 260-830-6, PMN 89-234, Tetraphenyl m-phenylene bis(phosphate), CID93311, LS-107873, Phosphoric acid, 1,3-phenylene tetraphenyl ester, Phosphoric acid, P,P-1,3-phenylene P,P,P,P-tetraphenyl ester, 156929-96-3, 168255-49-0, 210475-88-0, 57583-54-7
• IUPAC Name: (3-diphenoxyphosphoryloxyphenyl) diphenyl phosphate
• InChI Key: OWICEWMBIBPFAH-UHFFFAOYSA-N
• Boiling Point: 587.1ºC at 760 mmHg
• Flash Point: 321.7ºC
• Density: 1.347 g/cm³
• Appearance: Colorless to yellow clear liquid
• Exact Mass: 574.09500
• H-Bond Acceptor: 8
• H-Bond Donor: 0

Case Study

In vitro metabolism of tetraphenyl resorcinol bis(diphenylphosphate)

Ballesteros-Gómez, Ana, Nele Van den Eede, and Adrian Covaci. Environmental Science & Technology 49.6 (2015): 3897-3904.

Tetraphenyl resorcinol bis(diphenylphosphate) (RDP) is widely used as a flame retardant in electrical/electronic products and is a suitable alternative to decabromodiphenyl ether. There is growing concern about human exposure to this emerging contaminant due to its toxicity and recently reported prevalence in electronic products and house dust. In vitro metabolism of RDP and its oligomers was investigated using human liver microsomes and human liver cytoplasm in order to identify human-specific biomarkers. Mono- and dihydroxy metabolites, as well as glucuronidated and sulfated metabolites were detected. Regarding RDP oligomers, only the hydroxy metabolite of the dimer could be detected. RDP and its oligomers are also susceptible to hydrolysis to produce various compounds such as diphenyl phosphate, p-hydroxy triphenyl phosphate, and p-hydroxy RDP, which are further metabolized.
Preparation of tetraphenyl resorcinol bis(diphenylphosphate) (RDP) in TRIS buffer (pH 7.4 at 37°C). The incubation was stopped on ice and methanol (50% v/v in the final extract) was added to minimize further chemical hydrolysis Metabolism of HLM by CYP enzymes: A reaction mixture was prepared in a 2 mL Eppendorf tube containing 100 mM TRIS buffer (with 5 mM MgCl2; pH 7.4 at 37°C), HLM (0.5 mg/mL, final protein concentration), and RDP (20 μM, final concentration, 1% methanol v/v) in a total volume of 1 mL. The mixture was preincubated in a shaking water bath at 37°C for 5 min. The reaction was started by adding NADPH (1 mM, final concentration) dissolved in buffer. A new aliquot of NADPH was added after 1 h of incubation to ensure sufficient cofactor amounts throughout the experiment.

Flame retardant effect of tetraphenyl resorcinol bis(diphenylphosphate) in blends

Murashko, E. A., et al. Journal of fire sciences 16.4 (1998): 233-249.

The combustion performance of flame retardant polyphenylene ether (PPO), high impact polystyrene (HIPS) or PPO/HIPS blends with tetraphenyl resorcinol bis(diphenylphosphate) (RDP) was investigated experimentally. RDP is an efficient flame retardant additive in PPO/HIPS because of its high flame retardant effect on PPO. In HIPS, RDP showed moderate flame retardant activity. Thermogravimetric analysis in an inert atmosphere or air showed that RDP increased the char yield of plastics. Chemical analysis and infrared spectroscopy showed that PPO/HIPS blends volatilized very little phosphorus during thermal decomposition or combustion. The flame retardant effect of RDP was discussed from the perspective of chemical interaction between PPO and RDP and the catalytic effect of RDP.
The pure polymer and Norylg resin were mixed with RDP in a homemade Brabender type mixer at a speed of 30-60rev/min in a closed chamber for 5 minutes. The following processing temperatures were used: 230°C for HIPS, 250°C for Norylg, and 300°C for PPO. PPO appears to undergo some thermal transitions during formulation as the polymer turns brown. Plaques of 3 mm or 1.6 mm (1/16 inch) thickness for oxygen index or UL94 testing, respectively, were hot pressed from the prepared mixes at the same temperatures used in formulation. The plaques were cut into bars of appropriate size for the burn tests. The samples used in the thermal analysis experiments were cut from the bars.

Tetraphenyl resorcinol bis(diphenylphosphate) impurities in plastics and dust collected on electrical/electronic materials

Ballesteros-Gómez, Ana, et al. Environmental Science & Technology 50.4 (2016): 1934-1940.

Tetraphenyl resorcinol bis(diphenylphosphate) (RDP) is an organophosphorus flame retardant widely used in electrical and electronic equipment. Similar to other flame retardants, RDP formulations and products treated with RDP (e.g., plastics) may contain RDP impurities, byproducts, and decomposition products. We used a screening approach based on broad-spectrum solvent extraction and high-resolution time-of-flight mass spectrometry to identify RDP-related compounds in products and dust. Plastics from electrical/electronic equipment containing RDP and indoor dust collected on and around these devices were analyzed. Various compounds were detected in plastics containing high concentrations of RDP. For dust samples collected from electronic equipment, TPHP, meta-HO-TPHP, meta-HO-RDP, RDP-[Phe], and RDP oligomers were detected.
For screening purposes, sample extracts were analyzed in APCI and ESI, and in positive and negative modes. The ESI source had additional soft voltages and vaporizer temperature to enhance ionization and in this way cover a wider range of compound polarities than the standard ESI source. For the quantification of TPHP, m-HO-TPHP, and RDP, samples were run in APCI(+) by monitoring [M+H]+ as the major ion. Calibration standards were prepared in methanol in the concentration range of 1-5,000 ng/mL. For the analysis of dust, TPHP-d15 was used as the IS for TPHP, while TnBP-d27 was used for m-HO TPHP and RDP in dust.

Preparation and flame retardant properties of cotton fabric treated with tetraphenyl resorcinol bis(diphenylphosphate)

Jang, Yong-Man, et al. Cellulose 28 (2021): 4455-4467.

The bridging agent of tetraphenyl resorcinol bis(diphenylphosphate) (RDP) and urea-formalin resin (UFR) was applied to cotton fabric to make it flame retardant. Vertical flammability tests were conducted, which showed that cotton fabric treated with 25% RDP and 15% UFR could show the most reasonable flame retardancy. Here, other properties of cotton fabric, such as mass gain, color change, resistance to washing and hand feel, were found to be almost intact. The suitable heat treatment conditions of temperature and duration were determined to be 160 °C and 2 min. Scanning electron microscopy, energy dispersive X-ray and Fourier transform infrared spectroscopy results showed that RDP was tightly bound to cotton fibers and the UFR bridging effect was successful. Thermogravimetric analysis confirmed that the coated cotton fabric had flame retardant properties.
The flame retardant synthesized from Tetraphenyl resorcinol bis(diphenylphosphate) (RDP) (mass concentration of 15%, 20%, 25%, 30% and 35%) was dissolved in alcohol to prepare the impregnation solution. Urea and formalin were mixed in a molar ratio of 1:2 to prepare the crosslinking solution to obtain urea-formalin resin (UFR mass concentration of 5%, 10%, 15%, 20% and 25%). The treatment procedure of cotton fabric was impregnation pressing, crosslinking treatment, heat treatment, alkali washing (sodium carbonate), water washing and drying. First, the cotton fabric was immersed in the RDP impregnation solution in an airtight state and then compressed. After that, the RDP coated cotton fabric was immersed in the UFR solution and then heated at different temperatures of 140 °C, 160 °C and 180 °C for different durations of 2 min and 4 min. The heat-treated cotton fabric was washed with sodium carbonate alkali solution and then washed with distilled water. The treated fabric was dried in the open air.

Custom Q&A

What is the molecular formula of Tetraphenyl resorcinol bis(diphenylphosphate)?

The molecular formula is C30H24O8P2.

What are the synonyms for Tetraphenyl resorcinol bis(diphenylphosphate)?

The synonyms are Resorcinol bis(diphenyl phosphate), Fyrolflex RDP, and (3-diphenoxyphosphoryloxyphenyl) diphenyl phosphate.

What is the molecular weight of Tetraphenyl resorcinol bis(diphenylphosphate)?

The molecular weight is 574.5 g/mol.

When was Tetraphenyl resorcinol bis(diphenylphosphate) created and modified?

It was created on 2005-08-08 and last modified on 2023-10-21.

What is the IUPAC name of Tetraphenyl resorcinol bis(diphenylphosphate)?

The IUPAC name is (3-diphenoxyphosphoryloxyphenyl) diphenyl phosphate.

What is the InChI of Tetraphenyl resorcinol bis(diphenylphosphate)?

The InChI is InChI=1S/C30H24O8P2/c31-39(33-25-14-5-1-6-15-25,34-26-16-7-2-8-17-26)37-29-22-13-23-30(24-29)38-40(32,35-27-18-9-3-10-19-27)36-28-20-11-4-12-21-28/h1-24H.

What is the InChIKey of Tetraphenyl resorcinol bis(diphenylphosphate)?

The InChIKey is OWICEWMBIBPFAH-UHFFFAOYSA-N.

What is the canonical SMILES of Tetraphenyl resorcinol bis(diphenylphosphate)?

The canonical SMILES is C1=CC=C(C=C1)OP(=O)(OC2=CC=CC=C2)OC3=CC(=CC=C3)OP(=O)(OC4=CC=CC=C4)OC5=CC=CC=C5.

What is the CAS number of Tetraphenyl resorcinol bis(diphenylphosphate)?

The CAS number is 57583-54-7.

What is the physical description of Tetraphenyl resorcinol bis(diphenylphosphate)?

It is a liquid.