Triphenyl phosphate
Names
Preferred IUPAC name
Triphenyl phosphate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.739
UNII
  • InChI=1S/C18H15O4P/c19-23(20-16-10-4-1-5-11-16,21-17-12-6-2-7-13-17)22-18-14-8-3-9-15-18/h1-15H checkY
    Key: XZZNDPSIHUTMOC-UHFFFAOYSA-N checkY
  • InChI=1/C18H15O4P/c19-23(20-16-10-4-1-5-11-16,21-17-12-6-2-7-13-17)22-18-14-8-3-9-15-18/h1-15H
    Key: XZZNDPSIHUTMOC-UHFFFAOYAB
  • O=P(Oc1ccccc1)(Oc2ccccc2)Oc3ccccc3
Properties
C18H15O4P
Molar mass 326.288 g·mol−1
Appearance Colorless solid
Density 1.184 g/mL
Melting point 48 to 50 °C (118 to 122 °F; 321 to 323 K)
Boiling point 244 °C (471 °F; 517 K) at 10 mmHg
Vapor pressure 1 mmHg (193 °C)[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Harmful
Flash point 220 °C (428 °F; 493 K)[1]
Lethal dose or concentration (LD, LC):
1320 mg/kg (mouse, oral)
3500 mg/kg (rat, oral)[2]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 3 mg/m3[1]
REL (Recommended)
 TWA 3 mg/m3[1]
IDLH (Immediate danger)
 1000 mg/m3[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Triphenyl phosphate (TPhP) is the chemical compound with the formula OP(OC6H5)3. It is the simplest aromatic organophosphate. This colourless solid is the ester (triester) of phosphoric acid and phenol. It is used as a plasticizer and a fire retardant in a wide variety of settings and products.[3]

Preparation

Triphenyl phosphate is prepared by the SN2 reaction of phosphorus oxychloride and phenol.

Uses

Triphenyl phosphate has been used widely as a flame retardant and plasticizer.[4] It has been used as a flame retardant for a variety of materials, including electronic equipment, PVC, hydraulic fluids, glues, in nail polishes, and casting resins. Its mechanism of action as a flame retardant is as follows: first, during thermal decomposition, phosphoric acid is formed. This reacts to form pyrophosphoric acid, which, when in its condensed phase, acts to block heat transfer. One of the most effective flame retardants for certain polymers, TPhP is only active as an additive flame retardant in its gas phase.[5] Phase out of PBDEs may have increased the use of TPhP in recent years.[4]

TPhP is also used as a plasticizer in lacquers, varnishes, and hydraulic fluids. Nail polish has received particular interest as a source of exposure to TPhP.[6][7]

Toxicology

Limited information is available indicating significant toxicological effects of TPhP. Although it was initially expected to have an overall low impact, a growing body of evidence suggests that the effects may not be so harmless. Triphenyl phosphate exhibits low acute toxicity by dermal or oral contact.[3] However, an increasing number of studies have linked exposure to TPhP with reproductive and developmental toxicity, neurotoxicity, metabolic disruption, endocrine effects, and genotoxicity.[6][8][9] TPhP has also been found to induce significant estrogenic activity.[10][11] One study found that concentrations above the lowest observable effect level have been observed in a variety of other studies in coral grouper, yellow striped goat fish, and freshwater perch. This indicates that TPhP may be present in the environment at high enough concentrations to have harmful ecological effects.[11] The European Chemicals agency considers TPhP to be "very toxic" to aquatic life, with potentially long-lasting effects.[12]

In contrast to many persistent organic pollutants, TPHP has limited affinity for lipids. Still, bioaccumulation of the compound has been found to occur at varying levels in fish, with the strongest patterns showing up based on gender, feeding patterns, and metabolic efficiency. However, the mechanisms explaining why and how TPhP accumulates in this manner are not yet known.[13]

Environmental transport and transformations

Triphenyl phosphate has been detected in the environment.[9] Other triaryl phosphates have been known to enter aquatic environments through volatilization and leaching from plastics, through hydraulic fluid leakages, and, to a lesser degree, through manufacturing processes.[5] TPhP, in particular, has been found to enter the environment through industrial use, as in the manufacturing process, and through indoor use, for example through paints and electronic equipment.[12] As with many other phosphorus-containing flame retardants, TPhP has been found widely in sediment, soil, indoor dust, and air.[5][11][14][15][16]

Once in water, TPhP has been found to biodegrade relatively quickly under both aerobic and anaerobic conditions, and does not meet criteria for being categorized as persistent.[5] However, although the compound biodegrades easily and does not bioaccumulate, it is readily detected because of the sheer volume that is utilized.[9] In 2014, the United States Environmental Protection Agency added TPhP to its list of Toxic Substance Control Act Work Plan for Chemicals on the basis that the compound has exhibited "acute and chronic aquatic toxicity," "moderate bioaccumulation potential," and "moderate environmental persistence."[17] Still, there is not yet enough information to fully assess the environmental impact of TPhP.

References

  1. 1 2 3 4 5 NIOSH Pocket Guide to Chemical Hazards. "#0644". National Institute for Occupational Safety and Health (NIOSH).
  2. ↑ "Triphenyl phosphate". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. 1 2 Svara, Jürgen; Weferling, Norbert; Hofmann, Thomas (2000-01-01). Phosphorus Compounds, Organic. Wiley-VCH Verlag GmbH & Co. KGaA. doi:10.1002/14356007.a19_545.pub2. ISBN 9783527306732.
  4. 1 2 Stapleton, Heather M.; Klosterhaus, Susan; Eagle, Sarah; Fuh, Jennifer; Meeker, John D.; Blum, Arlene; Webster, Thomas F. (2009-08-13). "Detection of Organophosphate Flame Retardants in Furniture Foam and U.S. House Dust". Environmental Science & Technology. 43 (19): 7490–7495. Bibcode:2009EnST...43.7490S. doi:10.1021/es9014019. PMC 2782704. PMID 19848166.
  5. 1 2 3 4 van der Veen, Ike; de Boer, Jacob (2012-08-01). "Phosphorus flame retardants: Properties, production, environmental occurrence, toxicity and analysis". Chemosphere. 88 (10): 1119–1153. Bibcode:2012Chmsp..88.1119V. doi:10.1016/j.chemosphere.2012.03.067. PMID 22537891.
  6. 1 2 Mendelsohn, Emma; Hagopian, Audrey; Hoffman, Kate; Butt, Craig M.; Lorenzo, Amelia; Congleton, Johanna; Webster, Thomas F.; Stapleton, Heather M. (2016-01-01). "Nail polish as a source of exposure to triphenyl phosphate". Environment International. 86: 45–51. doi:10.1016/j.envint.2015.10.005. PMC 4662901. PMID 26485058.
  7. ↑ Tribune, Chicago. "Triphenyl phosphate, found in 'eco-friendly' nail polish, spurs worries". chicagotribune.com. Retrieved 2016-04-09.
  8. ↑ Zhang, Quan; Ji, Chenyang; Yin, Xiaohui; Yan, Lu; Lu, Meiya; Zhao, Meirong (2016-03-01). "Thyroid hormone-disrupting activity and ecological risk assessment of phosphorus-containing flame retardants by in vitro, in vivo and in silico approaches". Environmental Pollution. 210: 27–33. doi:10.1016/j.envpol.2015.11.051. PMID 26701863.
  9. 1 2 3 Du, Zhongkun; Zhang, Yan; Wang, Guowei; Peng, Jianbiao; Wang, Zunyao; Gao, Shixiang (2016-02-22). "TPhP exposure disturbs carbohydrate metabolism, lipid metabolism, and the DNA damage repair system in zebrafish liver". Scientific Reports. 6: 21827. Bibcode:2016NatSR...621827D. doi:10.1038/srep21827. PMC 4761896. PMID 26898711.
  10. ↑ Krivoshiev, Boris V.; Dardenne, Freddy; Covaci, Adrian; Blust, Ronny; Husson, Steven J. (2016-06-01). "Assessing in-vitro estrogenic effects of currently-used flame retardants". Toxicology in Vitro. 33: 153–162. doi:10.1016/j.tiv.2016.03.006. hdl:10067/1358930151162165141. PMID 26979758.
  11. 1 2 3 Zhang, Quan; Lu, Meiya; Dong, Xiaowu; Wang, Cui; Zhang, Chunlong; Liu, Weiping; Zhao, Meirong (2014-06-02). "Potential Estrogenic Effects of Phosphorus-Containing Flame Retardants". Environmental Science & Technology. 48 (12): 6995–7001. Bibcode:2014EnST...48.6995Z. doi:10.1021/es5007862. PMID 24844797.
  12. 1 2 "Triphenyl phosphate - Substance Information - ECHA". echa.europa.eu. Retrieved 2016-04-09.
  13. ↑ Hou, Rui; Xu, Yiping; Wang, Zijian (2016-06-01). "Review of OPFRs in animals and humans: Absorption, bioaccumulation, metabolism, and internal exposure research". Chemosphere. 153: 78–90. Bibcode:2016Chmsp.153...78H. doi:10.1016/j.chemosphere.2016.03.003. PMID 27010170.
  14. ↑ He, Ruiwen; Li, Yunzi; Xiang, Ping; Li, Chao; Zhou, Chunyang; Zhang, Shujun; Cui, Xinyi; Ma, Lena Q. (2016-05-01). "Organophosphorus flame retardants and phthalate esters in indoor dust from different microenvironments: Bioaccessibility and risk assessment". Chemosphere. 150: 528–535. Bibcode:2016Chmsp.150..528H. doi:10.1016/j.chemosphere.2015.10.087. PMID 26585356.
  15. ↑ Abdallah, Mohamed Abou-Elwafa; Covaci, Adrian (2014-04-23). "Organophosphate Flame Retardants in Indoor Dust from Egypt: Implications for Human Exposure". Environmental Science & Technology. 48 (9): 4782–4789. Bibcode:2014EnST...48.4782A. doi:10.1021/es501078s. PMID 24738854.
  16. ↑ Salamova, Amina; Hermanson, Mark H.; Hites, Ronald A. (2014-05-21). "Organophosphate and Halogenated Flame Retardants in Atmospheric Particles from a European Arctic Site". Environmental Science & Technology. 48 (11): 6133–6140. Bibcode:2014EnST...48.6133S. doi:10.1021/es500911d. PMID 24848787.
  17. ↑ EPA,OCSPP,OPPT,CCD, US (2015-01-08). "TSCA Work Plan for Chemical Assessments : 2014 Update". www.epa.gov. Retrieved 2016-04-09.{{cite web}}: CS1 maint: multiple names: authors list (link)
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