2-Phenylphenol, or o-phenylphenol, is an organic compound. In terms of structure, it is one of the monohydroxylated isomers of biphenyl. It is a white solid. It is a biocide used as a preservative with E number E231 and under the trade names Dowicide, Torsite, Fungal, Preventol, Nipacide and many others.
|Preferred IUPAC name
3D model (JSmol)
|E number||E231 (preservatives)|
CompTox Dashboard (EPA)
|Molar mass||170.211 g·mol−1|
|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)|
|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 their standard state (at 25 °C [77 °F], 100 kPa).
The primary use of 2-phenylphenol is as an agricultural fungicide. It is generally applied post-harvest. It is a fungicide used for waxing citrus fruits. It is no longer a permitted food additive in the European Union, but is still allowed as a post-harvest treatment in 4 EU countries.
It is also used for disinfection of seed boxes. It is a general surface disinfectant, 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 to disinfect hospital 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 a preservative, used to treat the surface of citrus fruits.
Orthophenyl phenol is also used as a fungicide in food packaging and may migrate into the contents.
It is prepared by condensation of cyclohexanone to give cyclohexenylcyclohexanone. The latter undergoes dehydrogenation to give 2-phenylphenol.
- ^ "2-Phenylphenol". pubchem.ncbi.nlm.nih.gov. Retrieved 11 September 2022.
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- ^ 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.
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- ^ 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. PMID 16881670.
- ^ a b Helmut Fiege; Heinz-Werner Voges; Toshikazu Hamamoto; Sumio Umemura; Tadao Iwata; Hisaya Miki; Yasuhiro Fujita; Hans-Josef Buysch; Dorothea Garbe (2007). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313.