Trimethyl phosphate

Catalog NumberACM512561-5

CAS Number512-56-1

CategoryPhosphate Standard

Description	Trimethyl phosphate appears as a pale straw colored liquid. Inhalation may irritate respiratory tract. Vapor or liquid may irritate skin or eyes. Ingestion may irritate the mucous membranes of the gastrointestinal tract.;Liquid;COLOURLESS LIQUID.
Synonyms	Phosphoric acid, trimethyl ester
IUPAC Name	Trimethyl phosphate
Molecular Weight	140.07
Molecular Formula	C3H9O4P
SMILES	COP(=O)(OC)OC
InChI	WVLBCYQITXONBZ-UHFFFAOYSA-N
InChI Key	InChI=1S/C3H9O4P/c1-5-8(4,6-2)7-3/h1-3H3
Boiling Point	197 °C(lit.)
Melting Point	-46 °C(lit.)
Flash Point	107 °C
Purity	>98.0%(GC)
Density	1.197g/ml
Solubility	soluble in Ether,Alcohol
Appearance	Colorless to Almost colorless clear liquid
Application	Trimethyl phosphate, a colorless and nonvolatile liquid, serves a variety of purposes due to its chemical stability and solubility in most organic solvents. Predominantly used within industries, it plays a crucial role as an electrolyte additive in lithium-ion battery production, enhancing performance. Additionally, trimethyl phosphate is utilized in gasoline engines to control issues like spark plug fouling, surface ignition, and rumble. Its applications extend further as a reagent for zirconium determination, a solvent, extractant, and a gas chromatography stationary phase. Trimethyl phosphate also acts as a methylating agent and a chemical intermediate in the synthesis of polymethyl polyphosphates. Furthermore, it functions as a flame retardant solvent in paints and polymers and as a catalyst in manufacturing polymers and resins.
Storage	Ambient (>5 °C)
Analyte Name	Trimethyl phosphate (TMP)
Components Number	1
Matrix	100 µg/mL in Toluene
MDL Number	MFCD00008348
Refractive Index	1.4
Specific Gravity	1.22
Stability	Stable under recommended storage conditions.
Vapor Pressure	1 mm Hg at 78.8 °F ; 5 mm Hg at 128.7° F; 10 mm Hg at 154.0° F (NTP, 1992);0.85 mmHg;0.85 mm Hg at 25 °C;Vapor pressure, kPa at 20 °C: 0.11

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Case Study

Enabling High-Voltage and Nonflammable Supercapacitors with Trimethyl Phosphate Electrolyte

Nguyen, Hoai Van T., et al. Journal of Materials Chemistry A 9.36 (2021): 20725-20736.

This study examined the application of trimethyl phosphate (TMP) as a nonflammable electrolyte solvent to enhance the safety and performance of supercapacitors. Conventional nitrile or carbonate-based electrolytes pose flammability risks, limiting their use in large-scale energy storage. TMP offers a promising alternative by combining intrinsic safety with electrochemical stability.
Methods: A TMP-based electrolyte was formulated using 1.0 M DMPBF4 as the salt. Its physical and electrochemical properties were evaluated through self-extinguishing time tests, ionic conductivity measurements, viscosity analysis, cyclic voltammetry, and galvanostatic charge-discharge (GCD) cycling. Electrochemical stability window (ESW) was determined, and long-term stability was assessed via floating tests at 3.0 V and extended GCD cycles at 3.3 V.
Key Results:
· The TMP-based electrolyte demonstrated exceptional safety characteristics, exhibiting nonflammable behavior in combustion tests. Its ionic conductivity (10.0 mS/cm) was slightly lower than that of conventional propylene carbonate (PC)-based electrolytes (12.1 mS/cm) but remained highly functional. The inherent ESW of TMP reached 5.9 V, enabling stable operation at high voltages.
· Supercapacitors using the TMP electrolyte maintained stable performance over 10,000 cycles at 3.3 V, with minimal capacitance degradation. A key mechanism was identified: TMP decomposes to form a passivation layer composed of P-O and C-O bonds on the electrode surface, which inhibits further electrolyte decomposition and enhances interfacial stability.

Improving Room-Temperature Sodium-Sulfur Batteries Safety by Addition of Trimethyl Phosphate

Zhao, Xiao-Min, et al. ChemElectroChem 6.4 (2019): 1229-1234.

Trimethyl phosphate (TMP) was studied as a flame retardant additive in carbonate-based electrolytes for room temperature sodium-sulfur (RT Na-S) batteries to address the safety issues of the electrolyte's flammability without degrading electrochemical performance.
Methods: A sulfur-carbon composite (YP50F/S) was prepared by infiltrating sulfur into mesoporous carbon at 155°C under argon atmosphere. The base electrolyte consisted of 1.0 M NaClO4 in a 1:1 volume mixture of ethylene carbonate (EC) and propylene carbonate (PC). TMP was dehydrated using 3Å molecular sieves to achieve water content ≤30 ppm before being incorporated into the base electrolyte at concentrations ranging from 5 to 25 wt%. Electrolytes with varying TMP content (5-25 wt%) were systematically evaluated for flammability, thermal stability, and electrochemical performance.
Key Results:
· The electrolyte containing 15 wt% TMP demonstrated optimal performance, exhibiting complete nonflammability, enhanced thermal stability, excellent electrochemical compatibility, stable capacity of 788 mAh/g at 0.1 C rate, and outstanding rate capability with 441 mAh/g at 1 C and 177 mAh/g at 5 C over 200 cycles.
· Higher TMP concentrations (25 wt%) led to significant capacity decay due to unstable solid-electrolyte interphase (SEI) formation. The 15 wt% formulation achieved an ideal balance between flame retardancy and battery performance.

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