2-Phenylphenol

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2-Phenylphenol
Ball-and-stick model of 2-Phenylphenol 2-Phenylphenol.svg
Ball-and-stick model of 2-Phenylphenol
2-Phenylphenol-from-xtal-Mercury-3D-bs.png
Names
Preferred IUPAC name
[1,1′-Biphenyl]-2-ol
Other names
  • 2-Phenylphenol
  • 2-Biphenylol
  • o-Phenylphenol
  • Biphenylol
  • 2-Hydroxybiphenyl
  • Orthophenyl phenol
  • o-Xenol
  • Orthoxenol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.812 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-993-5
E number E231 (preservatives)
KEGG
PubChem CID
RTECS number
  • DV5775000
UNII
UN number 3077
  • InChI=1S/C12H10O/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9,13H Yes check.svgY
    Key: LLEMOWNGBBNAJR-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C12H10O/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9,13H
    Key: LLEMOWNGBBNAJR-UHFFFAOYAF
  • Oc2ccccc2c1ccccc1
Properties
C12H10O
Molar mass 170.211 g·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
GHS labelling: [1]
GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
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 their standard state (at 25 °C [77 °F], 100 kPa).
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2-Phenylphenol, or o-phenylphenol, is an organic compound with the formula C6H5−C6H4OH. It is one of three isomers of monohydroxylated biphenyl. [2] It is a white solid. It is a biocide used as a preservative [3] with E number E231 and under the trade names Dowicide, Torsite, Fungal, Preventol, Nipacide and many others.

Contents

Uses

The primary use of 2-phenylphenol is as an agricultural fungicide. It is generally applied post-harvest as a fungicide used for waxing citrus fruits. [3]

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. The sodium salt of orthophenyl phenol, sodium orthophenyl phenol, is a preservative, used to treat the surface of citrus fruits. [4]

2-Phenylphenol is a precursor to 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, a commercial fire retardant.

Preparation

It can be prepared by condensation of cyclohexanone to give cyclohexenylcyclohexanone. The latter undergoes dehydrogenation to give 2-phenylphenol. Another route, it is a significant and recovered by product of the reaction of chlorobenzene with alkali which primarily gives phenol. [3]

Safety

LD50 (rats) is 2700 to 3000 mg/kg. 2-Phenylphenol is no longer a permitted food additive in the European Union but is still allowed as a post-harvest treatment in 4 EU countries. [3] As a fungicide in food packaging orthophenyl phenol may migrate into the contents. [5]

References

  1. ↑ "2-Phenylphenol". pubchem.ncbi.nlm.nih.gov. Retrieved 11 September 2022.
  2. ↑ O'Neil, M.J., ed. (2001). Merck Index : an encyclopedia of chemicals, drugs, & biologicals (13th ed.). United States: MERCK & CO INC. pp.  7388. ISBN   0911910131.
  3. 1 2 3 4 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. ISBN   9783527306732.
  4. ↑ "Environmental Fate and Exposure Potential". 2-Phenylphenol - Substance Summary. National Center for Biotechnology Information, U.S. National Library of Medicine. Retrieved 2 June 2012.
  5. ↑ 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. Bibcode:2006JAFC...54.5731C. doi:10.1021/jf060743p. PMID   16881670.
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