DPHP

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DPHP
File:DPHP.svg
Names
Preferred IUPAC name
Bis(2-propylheptyl) benzene-1,2-dicarboxylate
Other names
Bis(2-propylheptyl) phthalate
Identifiers
3D model (JSmol)
ChemSpider
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EC Number
  • 258-469-4
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  • InChI=1S/C28H46O4/c1-5-9-11-17-23(15-7-3)21-31-27(29)25-19-13-14-20-26(25)28(30)32-22-24(16-8-4)18-12-10-6-2/h13-14,19-20,23-24H,5-12,15-18,21-22H2,1-4H3
    Key: MTYUOIVEVPTXFX-UHFFFAOYSA-N
  • CCCCCC(CCC)COC(=O)c1ccccc1C(=O)OCC(CCC)CCCCC
Properties
C28H46O4
Molar mass 446.672 g·mol−1
Appearance Clear oily liquid[1]
Density 0.957-0.965 g/cm3[1]
< 0.01 mg/L[1]
1.482-1.484
Viscosity 120-130 mPas
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Di(2-propylheptyl) phthalate (also known as bis(2-propylheptyl) benzene-1,2-dicarboxylate, di(propylheptyl) orthophthalate, or DPHP) is an organic compound with the formula C28H46O4. It is a phthalate and is the diester of phthalic acid and the 10-carbon branched-chain alcohol 2-propylheptanol.[2] This colorless, viscous liquid is used for softening PVC plastics and is a general purpose PVC plasticizer.[3] It possesses very good plasticizing properties and may be used as a direct replacement for DEHP and DINP in many applications.[4]

History of discovery

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The introduction of Di(2-propylheptyl) phthalate (DPHP) was driven by increasing regulatory scrutiny and health concerns associated with traditional plasticizers.[5]

DPHP was developed to meet the demand for plasticizers with improved safety profiles, particularly in applications involving human contact. As a result of its production through the esterification of phthalic anhydride with 2-propylheptanol, it results in a compound with low volatility and high thermal stability, making it suitable for various applications, including automotive interiors, wire and cable insulation, and flooring materials.[6]

The compound gained regulatory attention in the European Union, where it was included in the Community Rolling Action Plan (CoRAP) under the REACH regulation in 2014. This inclusion was due to concerns about its widespread use, potential endocrine-disrupting properties, and exposure risks to sensitive populations. Germany was tasked with evaluating DPHP's health and environmental impacts, with the assessment process beginning in 2020.[5]

Research into DPHP's metabolism and exposure markers has been conducted to better understand its behavior in biological systems. A 2019 study utilized ultra-performance liquid chromatography-mass spectrometry (UPLC-MS) in a rat model to identify potential biomarkers for DPHP exposure, aiding in the assessment of human exposure levels.[7][8][9]

References

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