| Revision as of 14:20, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 455783333 of page Triphenyl_phosphate for the Chem/Drugbox validation project (updated: ''). |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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|Watchedfields = changed |
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| verifiedrevid = 419120330 |
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|verifiedrevid = 470616510 |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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|ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile = OP(OPh)3.png |
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|ImageFile = OP(OPh)3.png |
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| ImageSize = 200px |
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|ImageSize = |
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| ImageFile1 = Triphenyl-phosphate-3D-vdW.png |
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|ImageFile1 = Triphenyl-phosphate-3D-vdW.png |
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| IUPACName = Triphenyl phosphate |
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|PIN = Triphenyl phosphate |
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|Section1={{Chembox Identifiers |
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| OtherNames = |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| Section1 = {{Chembox Identifiers |
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|ChemSpiderID = 7988 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|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 |
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| ChemSpiderID = 7988 |
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|InChIKey = XZZNDPSIHUTMOC-UHFFFAOYAB |
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| 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 |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| InChIKey = XZZNDPSIHUTMOC-UHFFFAOYAB |
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|ChEMBL = 454511 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ChEMBL = 454511 |
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|StdInChI =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 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI =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 |
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|StdInChIKey = XZZNDPSIHUTMOC-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| StdInChIKey = XZZNDPSIHUTMOC-UHFFFAOYSA-N |
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|CASNo = 115-86-6 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| CASNo = 115-86-6 |
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|UNII = YZE19Z66EA |
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| PubChem = 8289 |
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|PubChem = 8289 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 35033 |
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|ChEBI = 35033 |
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| SMILES = O=P(Oc1ccccc1)(Oc2ccccc2)Oc3ccccc3 |
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|SMILES = O=P(Oc1ccccc1)(Oc2ccccc2)Oc3ccccc3 |
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}} |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>18</sub>H<sub>15</sub>O<sub>4</sub>P |
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| MolarMass = 326.28 g/mol |
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| Appearance = colourless liquid |
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| Density = 1.184 g/mL |
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| MeltingPt = 48-50 °C |
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| BoilingPt = 244 °C 10 mm Hg |
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| Solubility = organic solvents |
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}} |
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| Section3 = {{Chembox Hazards |
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| MainHazards = harmful |
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| FlashPt = |
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| Autoignition = |
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|Section2={{Chembox Properties |
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|C=18 |
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|H=15 |
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|O=4 |
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|P=1 |
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|Appearance = Colorless solid |
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|Density = 1.184 g/mL |
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|MeltingPtC = 48 to 50 |
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|BoilingPtC = 244 |
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|BoilingPt_notes = at 10 mmHg |
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|VaporPressure = 1 mmHg (193 °C)<ref name=PGCH/> |
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}} |
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|Section3={{Chembox Hazards |
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|MainHazards = Harmful{{citation needed|date=November 2015}} |
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|FlashPtC = 220 |
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|FlashPt_ref = <ref name=PGCH>{{PGCH|0644}}</ref> |
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|AutoignitionPt = |
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|IDLH = 1000 mg/m<sup>3</sup><ref name=PGCH/> |
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|REL = TWA 3 mg/m<sup>3</sup><ref name=PGCH/> |
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|PEL = TWA 3 mg/m<sup>3</sup><ref name=PGCH/> |
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|LD50 = 1320 mg/kg (mouse, oral)<br/>3500 mg/kg (rat, oral)<ref>{{IDLH|115866|Triphenyl phosphate}}</ref> |
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'''Triphenyl phosphate''' ('''TPhP''') is the ] with the ] OP(OC<sub>6</sub>H<sub>5</sub>)<sub>3</sub>. It is the simplest aromatic ]. This colourless solid is the ] (triester) of ] and ]. It is used as a ] and a ] in a wide variety of settings and products.<ref name=":0">{{Cite book|title=Phosphorus Compounds, Organic|last1=Svara|first1=Jürgen|last2=Weferling|first2=Norbert|last3=Hofmann|first3=Thomas|date=2000-01-01|publisher=Wiley-VCH Verlag GmbH & Co. KGaA|isbn=978-3-527-30673-2|language=en|doi=10.1002/14356007.a19_545.pub2}}</ref> |
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==Preparation == |
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Triphenyl phosphate is prepared by the ] of ] and ].{{Citation needed|date=January 2021|reason=Other mechanisms may be involved}} |
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== Uses == |
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Triphenyl phosphate has been used widely as a flame retardant and plasticizer.<ref name=":1">{{Cite journal|last1=Stapleton|first1=Heather M.|last2=Klosterhaus|first2=Susan|last3=Eagle|first3=Sarah|last4=Fuh|first4=Jennifer|last5=Meeker|first5=John D.|last6=Blum|first6=Arlene|last7=Webster|first7=Thomas F.|date=2009-08-13|title=Detection of Organophosphate Flame Retardants in Furniture Foam and U.S. House Dust|journal=Environmental Science & Technology|language=EN|volume=43|issue=19|pages=7490–7495|doi=10.1021/es9014019|pmid=19848166|pmc=2782704|bibcode=2009EnST...43.7490S}}</ref> It has been used as a flame retardant for a variety of materials, including electronic equipment, ], hydraulic fluids, glues, in nail polishes, and casting resins. Its mechanism of action as a flame retardant is as follows: first, during ], ] is formed. This reacts to form ], 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.<ref name=":4">{{Cite journal|last1=van der Veen|first1=Ike|last2=de Boer|first2=Jacob|date=2012-08-01|title=Phosphorus flame retardants: Properties, production, environmental occurrence, toxicity and analysis|journal=Chemosphere|volume=88|issue=10|pages=1119–1153|doi=10.1016/j.chemosphere.2012.03.067|pmid=22537891|bibcode=2012Chmsp..88.1119V}}</ref> Phase out of PBDEs may have increased the use of TPhP in recent years.<ref name=":1" /> |
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TPhP is also used as a ] in lacquers, varnishes, and hydraulic fluids. Nail polish has received particular interest as a source of exposure to TPhP.<ref name=":2">{{Cite journal|last1=Mendelsohn|first1=Emma|last2=Hagopian|first2=Audrey|last3=Hoffman|first3=Kate|last4=Butt|first4=Craig M.|last5=Lorenzo|first5=Amelia|last6=Congleton|first6=Johanna|last7=Webster|first7=Thomas F.|last8=Stapleton|first8=Heather M.|date=2016-01-01|title=Nail polish as a source of exposure to triphenyl phosphate|journal=Environment International|volume=86|pages=45–51|doi=10.1016/j.envint.2015.10.005|pmc=4662901|pmid=26485058|bibcode=2016EnInt..86...45M }}</ref><ref>{{Cite web|url=http://www.chicagotribune.com/news/watchdog/ct-nail-polish-toxic-chemical-20151023-story.html|title=Triphenyl phosphate, found in 'eco-friendly' nail polish, spurs worries|last=Tribune|first=Chicago|website=chicagotribune.com|access-date=2016-04-09}}</ref> |
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== Toxicology == |
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Limited information is available indicating significant ] 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 ] by dermal or oral contact.<ref name=":0"/> However, an increasing number of studies have linked exposure to TPhP with reproductive and ], neurotoxicity, metabolic disruption, ] effects, and ].<ref name=":2" /><ref>{{Cite journal|last1=Zhang|first1=Quan|last2=Ji|first2=Chenyang|last3=Yin|first3=Xiaohui|last4=Yan|first4=Lu|last5=Lu|first5=Meiya|last6=Zhao|first6=Meirong|date=2016-03-01|title=Thyroid hormone-disrupting activity and ecological risk assessment of phosphorus-containing flame retardants by in vitro, in vivo and in silico approaches|journal=Environmental Pollution|volume=210|pages=27–33|doi=10.1016/j.envpol.2015.11.051|pmid=26701863}}</ref><ref name=":5">{{Cite journal|last1=Du|first1=Zhongkun|last2=Zhang|first2=Yan|last3=Wang|first3=Guowei|last4=Peng|first4=Jianbiao|last5=Wang|first5=Zunyao|last6=Gao|first6=Shixiang|date=2016-02-22|title=TPhP exposure disturbs carbohydrate metabolism, lipid metabolism, and the DNA damage repair system in zebrafish liver|journal=Scientific Reports|language=en|volume=6|doi=10.1038/srep21827|pmc=4761896|pmid=26898711|pages=21827|bibcode=2016NatSR...621827D}}</ref> TPhP has also been found to induce significant estrogenic activity.<ref>{{Cite journal|last1=Krivoshiev|first1=Boris V.|last2=Dardenne|first2=Freddy|last3=Covaci|first3=Adrian|last4=Blust|first4=Ronny|last5=Husson|first5=Steven J.|date=2016-06-01|title=Assessing in-vitro estrogenic effects of currently-used flame retardants|journal=Toxicology in Vitro|volume=33|pages=153–162|doi=10.1016/j.tiv.2016.03.006|pmid=26979758|hdl=10067/1358930151162165141|hdl-access=free}}</ref><ref name=":3">{{Cite journal|last1=Zhang|first1=Quan|last2=Lu|first2=Meiya|last3=Dong|first3=Xiaowu|last4=Wang|first4=Cui|last5=Zhang|first5=Chunlong|last6=Liu|first6=Weiping|last7=Zhao|first7=Meirong|date=2014-06-02|title=Potential Estrogenic Effects of Phosphorus-Containing Flame Retardants|journal=Environmental Science & Technology|language=EN|volume=48|issue=12|pages=6995–7001|doi=10.1021/es5007862|pmid=24844797|bibcode=2014EnST...48.6995Z}}</ref> 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.<ref name=":3" /> The European Chemicals agency considers TPhP to be "very toxic" to aquatic life, with potentially long-lasting effects.<ref name=":6">{{Cite web|url=http://echa.europa.eu/ja/substance-information/-/substanceinfo/100.003.739|title=Triphenyl phosphate - Substance Information - ECHA|website=echa.europa.eu|access-date=2016-04-09|archive-date=2016-04-20|archive-url=https://web.archive.org/web/20160420073634/http://echa.europa.eu/ja/substance-information/-/substanceinfo/100.003.739|url-status=dead}}</ref> |
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In contrast to many ], TPHP has limited affinity for ]s. Still, ] 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.<ref>{{Cite journal|last1=Hou|first1=Rui|last2=Xu|first2=Yiping|last3=Wang|first3=Zijian|date=2016-06-01|title=Review of OPFRs in animals and humans: Absorption, bioaccumulation, metabolism, and internal exposure research|journal=Chemosphere|volume=153|pages=78–90|doi=10.1016/j.chemosphere.2016.03.003|pmid=27010170|bibcode=2016Chmsp.153...78H|url=http://ir.rcees.ac.cn/handle/311016/36209}}</ref> |
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== Environmental transport and transformations == |
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Triphenyl phosphate has been detected in the environment.<ref name=":5" /> Other triaryl phosphates have been known to enter aquatic environments through ] and leaching from plastics, through ] leakages, and, to a lesser degree, through manufacturing processes.<ref name=":4" /> 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.<ref name=":6" /> As with many other phosphorus-containing flame retardants, TPhP has been found widely in sediment, soil, indoor dust, and air.<ref name=":4" /><ref name=":3" /><ref>{{Cite journal|last1=He|first1=Ruiwen|last2=Li|first2=Yunzi|last3=Xiang|first3=Ping|last4=Li|first4=Chao|last5=Zhou|first5=Chunyang|last6=Zhang|first6=Shujun|last7=Cui|first7=Xinyi|last8=Ma|first8=Lena Q.|date=2016-05-01|title=Organophosphorus flame retardants and phthalate esters in indoor dust from different microenvironments: Bioaccessibility and risk assessment|journal=Chemosphere|volume=150|pages=528–535|doi=10.1016/j.chemosphere.2015.10.087|pmid=26585356|bibcode=2016Chmsp.150..528H}}</ref><ref>{{Cite journal|last1=Abdallah|first1=Mohamed Abou-Elwafa|last2=Covaci|first2=Adrian|date=2014-04-23|title=Organophosphate Flame Retardants in Indoor Dust from Egypt: Implications for Human Exposure|journal=Environmental Science & Technology|language=EN|volume=48|issue=9|pages=4782–4789|doi=10.1021/es501078s|pmid=24738854|bibcode=2014EnST...48.4782A}}</ref><ref>{{Cite journal|last1=Salamova|first1=Amina|last2=Hermanson|first2=Mark H.|last3=Hites|first3=Ronald A.|date=2014-05-21|title=Organophosphate and Halogenated Flame Retardants in Atmospheric Particles from a European Arctic Site|journal=Environmental Science & Technology|language=EN|volume=48|issue=11|pages=6133–6140|doi=10.1021/es500911d|pmid=24848787|bibcode=2014EnST...48.6133S}}</ref> |
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Once in water, TPhP has been found to ] relatively quickly under both aerobic and anaerobic conditions, and does not meet criteria for being categorized as persistent.<ref name=":4" /> However, although the compound biodegrades easily and does not bioaccumulate, it is readily detected because of the sheer volume that is utilized.<ref name=":5" /> In 2014, the ] added TPhP to its list of ] Work Plan for Chemicals on the basis that the compound has exhibited "acute and chronic aquatic toxicity," "moderate bioaccumulation potential," and "moderate environmental persistence."<ref>{{Cite web|url=https://www.epa.gov/assessing-and-managing-chemicals-under-tsca/tsca-work-plan-chemical-assessments-2014-update|title=TSCA Work Plan for Chemical Assessments : 2014 Update|last=EPA,OCSPP,OPPT,CCD|first=US|website=www.epa.gov|language=en|access-date=2016-04-09|date=2015-01-08}}</ref> Still, there is not yet enough information to fully assess the environmental impact of TPhP. |
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==References== |
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{{Reflist}} |
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