Benzene phosphorus oxydichloride

Catalog NumberACM824726

CAS Number824-72-6

CategoryOther Phosphorus Flame Retardants

Synonyms	Benzenephosphonic dichloride; Benzenephosphonyl chloride; Dichlorophenylphosphine oxide; Phenyldichlorophosphine oxide; Phenylphosphonic acid dichloride; Phenylphosphonic dichloride; Phenylphosphonodichloridic acid; Phenylphosphonyl dichloride; Benzenephosphorus oxydichloride; Phosphonyldichloride, phenyl-; NSC 66477; Phosphonic dichloride, P-phenyl-;Benzene phosphorus oxydichloride;BPOD; Dichlorophenylphosphine oxide; Phenyldichlorophosphine oxide; Phenylphosphonic dichloride
Molecular Weight	194.98
Molecular Formula	C6H5Cl2OP
InChI	1S/C6H5Cl2OP/c7-10(8,9)6-4-2-1-3-5-6/h1-5H
InChI Key	IBDMRHDXAQZJAP-UHFFFAOYSA-N
Boiling Point	258 ° C
Melting Point	1 ° C
Application	Plasticizers, Antioxidants, Flame Retardant, Acid, Additive, Lubricant
Atmospheric OH Rate Constant	1.95E-12 cm³/molecule-sec
Hazards	8 corrosive
Notes	Benzene phosphorus oxydichloride uses and applications include: Intermediate in organic synthesis for end-products such as flame retardants, plasticizers, antifoaming agents, antioxidants, oil additives, EP lubricants; acid inhibitor for urethane binders for foundry molds Suggested storage of Benzene phosphorus oxydichloride: Store under nitrogen in a cool, dry place, protected from moisture

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Case Study

Phenylphosphonic Dichloride as a Key Intermediate for High-Performance, Flame-Retardant Epoxy Curing Agents

Jirasutsakul, Isara, et al. Progress in Organic Coatings 76.12 (2013): 1738-1746.

Phenylphosphonic dichloride (PPDC) was used as the key phosphorus-containing electrophile to prepare two aromatic phosphorodiamidate curing agents - phenyl phosphonic ethylenediamine diamide (PPEDD) and phenyl phosphonic p-phenylenediamine diamide (PPPDD). These diamide products serve as dual-function additives for epoxy systems: they act as crosslinkers during cure and deliver marked flame-retardant performance in the cured coatings. Epoxy networks cured with PPEDD or PPPDD showed higher thermal stability, substantially increased char formation and much improved limiting oxygen index (LOI) values (LOI ≈ 27 for PPEDD-cured epoxy and LOI ≈ 31 for PPPDD-cured epoxy) at only ~2-3 wt% phosphorus in the cured material.
Synthetic Routes
· PPEDD: Ethylenediamine (EDA) dissolved in dry THF (0 °C, N2). PPDC in THF added dropwise at 0 °C, mixture stirred 2 h and then refluxed at 60 °C for 2 h. NaOCH3 in methanol was added, the inorganic salts filtered off, solvents removed and crude product purified by flash silica chromatography. Isolated as a white solid (yield 24%).
· PPPDD: p-Phenylenediamine (PDA) in dry THF with triethylamine (TEA) at 0 °C. PPDC in THF added dropwise under N2, stirred, then heated to 60 °C for 4 h. Workup (aqueous wash to remove TEA·HCl), solvent removal and column purification furnished PPPDD as a solid (yield 35%).

Phenylphosphonic Dichloride as a Platform Reagent for Producing Phosphorus-Containing Flame-Retardant Additives for PA66

Lyu, Wenyan, et al. Designed Monomers and Polymers 19.5 (2016): 420-428.

Phenylphosphonic dichloride (PPDC) was used as the key electrophilic building block to prepare a series of phosphorus-bearing phosphamide derivatives that were subsequently incorporated into polyamide-66 (PA66). Four PPDC-derived flame retardants - BNPO, NENP, DPPD and MCPO - were synthesized in good yields and used to replace 5 wt% of the PA66 prepolymer during polymerization. PA66 treated with these PPDC-based additives (designated FR-1 to FR-4) exhibited improved thermal stability and pronounced flame retardancy (LOI > 27% and UL-94 V-0 classification), while SEM showed that polymerization grafting mitigated dispersion/compatibility issues normally associated with additive loading.
Syntheses Enabled by PPDC: Using PPDC as the common electrophile, four flame-retardant derivatives were prepared: (1) BNPO (bis-(4-carboxyanilino) phenyl phosphamide) - made by acylation of 4-aminobenzoic acid with PPDC; yield 91%. (2) NENP (N-benzoic acid-(ethyl-N-benzoic acid formamide) phosphamide) - prepared via a two-step route involving acrylic acid and aminobenzoic acid with PPDC; yield 84%. (3) DPPD (poly-N-aniline-phenyl phosphamide) - formed from PPDC and 1,4-benzenediamine with triethylamine as base; yield 87%. (4) MCPO (bis-N-benzoguanamine-phenyl phosphamide) - synthesized by reaction of PPDC and benzoguanamine; yield 89%.
Incorporation into PA6: Flame-retardant PA66 grades (FR-1 to FR-4) were produced by replacing 5 wt% of the PA66 prepolymer with each PPDC-derived additive during polymerization. Polymerization conditions reported were 1.7 MPa at 210 °C and 0.1 MPa at 280 °C.

Phenylphosphonic Dichloride Used for Bio-based Phosphorus Polymers in Layer-by-Layer Flame-Retardant Coatings

Yan, Hongqiang, et al. Journal of Applied Polymer Science 134.20 (2017).

This study reported the use of phenylphosphonic dichloride (PDCP) as the phosphorus electrophile in the synthesis of a biomass-derived phosphorus polymer - poly(diphenolic acid-phenyl phosphate), abbreviated poly(DPA-PDCP) - and the subsequent application of that polymer in a layer-by-layer (LbL) nanocoating for flame protection of ramie fabric.
Synthesis & Layer-by-Layer Coating: Poly(DPA-PDCP) was prepared by interfacial polycondensation of diphenolic acid (DPA) with phenylphosphonic dichloride (PDCP). The presence of phosphate groups in the polymer backbone imparts acidity and char-promoting capability. Then, poly(DPA-PDCP) was dissolved in an ethanol/water mixture and adjusted to alkaline pH for use as the polyanion; PEI solution (pH adjusted) served as the polycation. Fabric pretreatment with the silane coupling agent KH550 was optionally used to enhance adsorption and layer uniformity. Ramie fabric (raw or KH550-pretreated) was alternately immersed in poly(DPA-PDCP) and PEI baths, rinsed after each immersion, and dried. Immersion times and wash steps were controlled to build 10, 20 or 30 bilayers (BL) of poly(DPA-PDCP)/PEI.
Key Performance: TGA showed enhanced char yield and delayed thermal degradation for coated fabrics. Increasing poly(DPA-PDCP) concentration and bilayer count consistently improved thermal stability. Coated fabrics exhibited progressively lower TPHRR, PHRR, THC and THR values as coating mass and bilayer number increased, indicating the nanocoating effectively limited heat release during combustion.

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