Isopropylphenyl phosphate
[CAS# 68937-41-7]

Identification

• Classification: Catalysts and additives >> Flame retardant
• Name: Isopropylphenyl phosphate
• Synonyms: Isopropylated phenol phosphate; Triisopropylated phenyl phosphate
• Molecular Formula: C₂₇H₃₃O₄P
• Molecular Weight: 452.52
• CAS Registry Number: 68937-41-7
• EC Number: 273-066-3
• SMILES: CC(C)C1=CC=C(C=C1)OP(=O)(OC2=CC=C(C=C2)C(C)C)OC3=CC=C(C=C3)C(C)C

Properties

• Solubility: 2.586e-005 mg/L (25 °C water)
• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.551, Calc.^*
• Melting point: 90.27 °C
• Boiling Point: 489.7±44.0 °C (760 mmHg), Calc.^*, 480.00 °C
• Flash Point: 263.1±48.8 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS08 Warning
• Risk Statements: H361f-H373
• Safety Statements: P203-P260-P280-P318-P319-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Reproductive toxicity	Repr.	2	H361
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Reproductive toxicity	Repr.	2	H361fd
Reproductive toxicity	Repr.	2	H361f
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin sensitization	Skin Sens.	1B	H317

Discovery and Applications

Isopropylphenyl phosphate (IPP) is an organophosphate compound that has been the subject of interest due to its unique chemical properties and various applications. The discovery of isopropylphenyl phosphate dates back to the mid-20th century when researchers began exploring organophosphate compounds for their potential utility in diverse fields, including agriculture, chemical synthesis, and materials science. This compound is synthesized through the reaction of isopropyl alcohol with phenyl phosphate, resulting in a stable ester with significant functional versatility.

Isopropylphenyl phosphate is primarily utilized as a plasticizer and flame retardant in various polymer formulations. Its ability to improve flexibility and durability makes it an essential additive in the production of plastics, especially polyvinyl chloride (PVC) and other thermoplastic materials. In addition to enhancing mechanical properties, IPP also contributes to the thermal stability of polymers, reducing the risk of degradation during processing and use.

The applications of isopropylphenyl phosphate extend to the formulation of lubricants and hydraulic fluids. Its properties as a surfactant enable it to reduce friction and wear in mechanical systems, enhancing performance and extending the lifespan of components. Furthermore, IPP is often employed in formulations for cutting fluids in metalworking processes, where it acts to cool and lubricate cutting tools, thus improving efficiency and surface finish.

In the agricultural sector, isopropylphenyl phosphate is used as a surfactant in pesticide formulations, improving the wetting and spreading properties of active ingredients on plant surfaces. This enhanced efficacy leads to better absorption and overall effectiveness of the pesticides, contributing to improved crop protection.

Despite its widespread applications, there are concerns regarding the environmental impact and toxicity of organophosphate compounds, including isopropylphenyl phosphate. Research has focused on assessing its safety profile and potential effects on human health and ecosystems. Regulatory agencies have established guidelines to ensure that the use of isopropylphenyl phosphate in various applications complies with safety standards, minimizing risks to health and the environment.

In conclusion, isopropylphenyl phosphate is a significant organophosphate compound with diverse applications in plastics, lubricants, and agriculture. Its unique chemical properties allow it to function effectively as a plasticizer, flame retardant, and surfactant, demonstrating its importance in modern industrial practices while emphasizing the need for responsible usage and environmental stewardship.

References

2023. Unbalanced Pollution and Ecological Risk of Organophosphate Esters in Chinese Surface Water and Land Use Under Multiple Driving Factors. Reviews of Environmental Contamination and Toxicology, 262(1).
DOI: 10.1007/s44169-023-00041-1