Tri-O-cresyl phosphate

Base Information

• Chemical Name: Tri-O-cresyl phosphate
• CAS No.: 78-30-8
• Deprecated CAS: 1336-40-9
• Molecular Formula: C21H21 O4 P
• Molecular Weight: 368.369
• Hs Code.: 29199000
• European Community (EC) Number: 201-103-5,941-548-9
• ICSC Number: 0961
• NSC Number: 438
• UN Number: 2574
• UNII: X8II18JD0A
• DSSTox Substance ID: DTXSID6032192
• Nikkaji Number: J134.726H
• Wikidata: Q20964363
• ChEMBL ID: CHEMBL3181798
• Mol file: 78-30-8.mol

Synonyms:phosphoric acid, tris(2-methylphenyl) ester;TOCP;tri-2-cresyl phosphate;tri-o-cresyl phosphate;tri-o-tolyl phosphate;triorthocresyl phosphate;triorthotolyl phosphate

Chemical Property of Tri-O-cresyl phosphate

Chemical Property:

• Appearance/Colour: colorless viscous liquid.
• Vapor Pressure: 1.44E-06mmHg at 25°C
• Melting Point: -25 °C
• Refractive Index: 1.558-1.561
• Boiling Point: 410 °C
• Flash Point: 225 °C
• PSA: 54.57000
• Density: 1.2
• LogP: 6.25670
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: sparingly soluble in water; soluble in acetic acid; freely soluble in alcohol, benzene, ether; very soluble in carbon tetrachloride, toluene. maximum allowable concentration: 0.1 mg/m3 (TLV-TWA) (ACGIH 1986)
• Water Solubility.: 0.1 mg l-1 (e)
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 368.11774614
• Heavy Atom Count: 26
• Complexity: 416

Purity/Quality:

98%,99%, ^*data from raw suppliers

PhosphoricAcidTris(2-?methylphenyl)Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Toxic by ingestion and skin absorption. The o- isomer is highly toxic. TLV: 0.1 mg/m³ (skin); Not Classifiable as a Human Carcinogen.
• Hazard Codes: N-T,N,T
• Statements: 51/53-39/23/24/25
• Safety Statements: 61-45-28A-20/21-28

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organophosphates, Other
• Canonical SMILES: CC1=CC=CC=C1OP(=O)(OC2=CC=CC=C2C)OC3=CC=CC=C3C
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance may cause effects on the central nervous system and peripheral nervous system. Exposure above the OEL could cause degeneration of the nervous system. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: The substance may have effects on the nervous system.
• Physical properties: Tri-o-cresyl phosphate is a colorless to pale yellow, odorless to faint aromatic-like liquid, and it is a solid below the 25.6 °C melting point. It is sparingly soluble in water, but is slightly soluble in ethanol and very soluble in ethyl ether (Budavari, 1996). The vapor pressure of TOCP is 0.00002mm Hg at room temperature, but is 10mm Hg at 265 °C (Bisesi, 1994). It decomposes slightly upon boiling (bp 410 °C) (Budavari, 1996).
• Uses: Tri-o-cresyl phosphate is used widely as a gasoline additive, plasticizer, fire retardant, solvent, extreme pressure additive, intermediate in pharmaceutical manufacturing, water-proofing agent, heat exchange medium, and as a lead scavenger in gasoline. TOCP finds wide applications in several areas. It is used as a flame retardant; as a plasticizer; as a waterproofing agent; as a synthetic lubricant; as an additive in gasoline to control preignition; and in hot extrusion molding, hydraulic fluid, and solvent mixture for resins.. As plasticizer in lacquers and varnishes.

Technology Process of Tri-O-cresyl phosphate

There total 8 articles about Tri-O-cresyl phosphate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

tri(O-methylphenyl)phosphite (2622-08-4) → tri-ortho-cresyl phosphate (78-30-8)

Guidance literature:

With 1-methyl-3-(4-((2,4,6-triisopropylphenyl)tellanyl)benzyl)-1H-imidazol-3-ium hexafluorophosphate; Rose Bengal lactone; at 15 ℃; for 1h; Irradiation; Ionic liquid;

DOI:10.1055/s-0040-1706068

Reference yield: 90.0%

sodium o-cresolate (4549-72-8) → tri-ortho-cresyl phosphate (78-30-8)

Guidance literature:

With Amberlyst A-26 chloride; trichlorophosphate; In benzene; for 1.16667h; Ambient temperature;

DOI:10.1080/00397919408010211

Reference yield: 89.0%

ortho-cresol (95-48-7,77504-84-8) → tri-ortho-cresyl phosphate (78-30-8)

Guidance literature:

ortho-cresol; With potassium phosphate; diphenyl diselenide; phosphorus; In dimethyl sulfoxide; toluene; at 60 ℃; for 4h; Inert atmosphere;

With dihydrogen peroxide; In dimethyl sulfoxide; toluene; at 20 ℃; for 0.5h; Inert atmosphere;

upstream raw materials:

sodium o-cresolate

ortho-cresol

tri(O-methylphenyl)phosphite

trichlorophosphate

Downstream raw materials:

2-Methylbenzonitrile

ortho-cresol

2-methyl-6-nitrophenol

bis(2-methylphenyl)phosphoric acid

Refernces

• 1、 Zhang, Yue,Cai, Ziman,Chi, Yangyang,Zeng, Xiangzhe,Chen, Shuanghui,Liu, Yan,Tang, Guo,Zhao, Yufen. "Diphenyl Diselenide-Catalyzed Synthesis of Triaryl Phosphites and Triaryl Phosphates from White Phosphorus". . p. 5158 - 5163. Retrieved 2021/07/20.
• 2、 Armstrong, Kenneth M.,Kilian, Petr. "Catalytic synthesis of triaryl phosphates from white phosphorus". experimental part. p. 2138 - 2147. Retrieved 2011/06/28.