2-Phenylphenol,oro-phenylphenol, is anorganic compound.In terms of structure, it is one of the monohydroxylated isomers ofbiphenyl.[2][3]It is a white solid. It is abiocideused as apreservativewith E number E231 and under the trade names Dowicide, Torsite, Fungal, Preventol, Nipacide and many others.
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| Names | |
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| Preferred IUPAC name
[1,1′-Biphenyl]-2-ol | |
Other names
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.001.812 |
| EC Number |
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| E number | E231(preservatives) |
| KEGG | |
PubChemCID
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| RTECS number |
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| UNII | |
| UN number | 3077 |
CompTox Dashboard(EPA)
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| Properties | |
| C12H10O | |
| Molar mass | 170.211g·mol−1 |
| Density | 1.293 g/cm3 |
| Melting point | 55.5 to 57.5 °C (131.9 to 135.5 °F; 328.6 to 330.6 K) |
| Boiling point | 280 to 284 °C (536 to 543 °F; 553 to 557 K) |
| Pharmacology | |
| D08AE06(WHO) | |
| Hazards | |
| GHSlabelling:[1] | |
 
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| Warning | |
| H315,H319,H335,H400 | |
| P261,P264,P264+P265,P271,P273,P280,P302+P352,P304+P340,P305+P351+P338,P319,P321,P332+P317,P337+P317,P362+P364,P391,P403+P233,P405,P501 | |
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).
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Uses
editThe primary use of 2-phenylphenol is as an agricultural fungicide. It is generally applied post-harvest. It is afungicideused for waxingcitrus fruits.It is no longer a permittedfood additivein the European Union, but is still allowed as a post-harvest treatment in 4 EU countries.[4]
It is also used for disinfection of seed boxes. It is a general surfacedisinfectant,used in households, hospitals, nursing homes, farms, laundries, barber shops, and food processing plants. It can be used on fibers and other materials. It is used todisinfecthospital and veterinary equipment. Other uses are in rubber industry and as a laboratory reagent. It is also used in the manufacture of other fungicides, dye stuffs, resins and rubber chemicals.
2-Phenylphenol is found in low concentrations in some household products such as spray disinfectants and aerosol or spray underarm deodorants.
The sodium salt of orthophenyl phenol,sodium orthophenyl phenol,is apreservative,used to treat the surface ofcitrusfruits.[5]
Orthophenyl phenol is also used as a fungicide in food packaging and may migrate into the contents.[6]
Preparation
editIt is prepared by condensation ofcyclohexanoneto give cyclohexenylcyclohexanone. The latter undergoes dehydrogenation to give 2-phenylphenol.[7]
Safety
editReferences
edit- ^"2-Phenylphenol".pubchem.ncbi.nlm.nih.gov.Retrieved11 September2022.
- ^O'Neil, M.J., ed. (2001).Merck Index: an encyclopedia of chemicals, drugs, & biologicals(13th ed.). United States: MERCK & CO INC. pp.7388.ISBN0911910131.
- ^Budavari, Susan (1997).The Merck index an encyclopedia of chemicals, drugs, and biologicals(12th, 2nd printing ed.). Whitehouse Station, NJ: Merck. p. 7458.ISBN0911910123.
- ^Uhr, Hermann; Mielke, Burkhard; Exner, Otto; Payne, Ken R.; Hill, Edward (2013). "Biocides".Ullmann's Encyclopedia of Industrial Chemistry.Weinheim: Wiley-VCH. pp. 1–26.doi:10.1002/14356007.a16_563.pub2.ISBN9783527306732.
- ^"Environmental Fate and Exposure Potential".2-Phenylphenol - Substance Summary.National Center for Biotechnology Information, U.S. National Library of Medicine.Retrieved2 June2012.
- ^Mehmet Coelhan; Karl-Heinz Bromig; Karl Glas; A. Lynn Roberts (2006). "Determination and Levels of the Biocide ortho-Phenylphenol in Canned Beers from Different Countries".J. Agric. Food Chem.54(16): 5731–5735.doi:10.1021/jf060743p.PMID16881670.
- ^abHelmut Fiege; Heinz-Werner Voges; Toshikazu Hamamoto; Sumio Umemura; Tadao Iwata; Hisaya Miki; Yasuhiro Fujita; Hans-Josef Buysch; Dorothea Garbe; Wilfried Paulus (2007). "Phenol Derivatives".Ullmann's Encyclopedia of Industrial Chemistry.Weinheim: Wiley-VCH.doi:10.1002/14356007.a19_313.ISBN978-3527306732.