2-Phenylphenol, or ''o''-phenylphenol, is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

. In terms of structure, it is one of the monohydroxylated isomers of

biphenyl Biphenyl (also known as diphenyl, phenylbenzene, 1,1′-biphenyl, lemonene or BP) is an organic compound that forms colorless crystals. Particularly in older literature, compounds containing the functional group consisting of biphenyl less one ...

. It is a white solid. It is a

biocide A biocide is defined in the European legislation as a chemical substance or microorganism intended to destroy, deter, render harmless, or exert a controlling effect on any harmful organism. The US Environmental Protection Agency (EPA) uses a slig ...

used as a

preservative A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or by ...

with E number E231 and under the trade names Dowicide, Torsite, Fungal, Preventol, Nipacide and many others.

Uses

The primary use of 2-phenylphenol is as an agricultural fungicide. It is generally applied post-harvest. It is a

fungicide Fungicides are biocidal chemical compounds or biological organisms used to kill parasitic fungi or their spores. A fungistatic inhibits their growth. Fungi can cause serious damage in agriculture, resulting in critical losses of yield, quality, ...

used for waxing

citrus fruit ''Citrus'' is a genus of flowering trees and shrubs in the rue family, Rutaceae. Plants in the genus produce citrus fruits, including important crops such as oranges, lemons, grapefruits, pomelos, and limes. The genus ''Citrus'' is native to So ...

s. It is no longer a permitted

food additive Food additives are substances added to food to preserve flavor or enhance taste, appearance, or other sensory qualities. Some additives have been used for centuries as part of an effort to preserve food, for example vinegar (pickling), salt (salt ...

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 A disinfectant is a chemical substance or compound used to inactivate or destroy microorganisms on inert surfaces. Disinfection does not necessarily kill all microorganisms, especially resistant bacterial spores; it is less effective than st ...

, 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 A disinfectant is a chemical substance or compound used to inactivate or destroy microorganisms on inert surfaces. Disinfection does not necessarily kill all microorganisms, especially resistant bacterial spores; it is less effective than ste ...

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 Sodium orthophenyl phenol is a compound used as a disinfectant. It is the sodium salt of 2-phenylphenol. As a food additive, it has E number E232.preservative A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or by ...

, used to treat the surface of

citrus ''Citrus'' is a genus of flowering plant, flowering trees and shrubs in the rue family, Rutaceae. Plants in the genus produce citrus fruits, including important crops such as Orange (fruit), oranges, Lemon, lemons, grapefruits, pomelos, and lim ...

fruit In botany, a fruit is the seed-bearing structure in flowering plants that is formed from the ovary after flowering. Fruits are the means by which flowering plants (also known as angiosperms) disseminate their seeds. Edible fruits in particu ...

s. Orthophenyl phenol is also used as a fungicide in food packaging and may migrate into the contents.

Preparation

It is prepared by condensation of

cyclohexanone Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oily liquid has an odor reminiscent of acetone. Over time, samples of cyclohexan ...

to give cyclohexenylcyclohexanone. The latter undergoes dehydrogenation to give 2-phenylphenol.

Safety

LD50 In toxicology, the median lethal dose, LD50 (abbreviation for "lethal dose, 50%"), LC50 (lethal concentration, 50%) or LCt50 is a toxic unit that measures the lethal dose of a toxin, radiation, or pathogen. The value of LD50 for a substance is the ...

(rats) is 2700 to 3000 mg/kg.

References

External links

List of brand name products which contain 2-phenylphenol

National Center for Biotechnology Information 2-Phenylphenol - Substance Summary
{{DEFAULTSORT:Phenylphenol, 2- Phenols Household chemicals Fungicides Antiseptics Fumigants Preservatives Biphenyls