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

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

. 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 sli ...

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 ...

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 pesticides used to kill parasitic fungi or their spores. Fungi can cause serious damage in agriculture, resulting in losses of yield and quality. Fungicides are used both in agriculture and to fight fungal infections in animals, ...

used for waxing

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

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, such as vinegar ( pickling), salt ( salting), smoke ( smoking) and sugar ( crystallization), have been used f ...

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 ...

, 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 endospore, bacterial spores; it is less effect ...

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 a precursor to

9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide 9,10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) is an organophosphorus compound that is used to produce fire retardants. From the chemistry perspective, it is a derivative of hypophosphorous acid as well as a derivative of phenanthrene. ...

, a commercial

fire retardant A fire retardant is a substance that is used to slow down or stop the spread of fire or reduce its intensity. This is commonly accomplished by chemical reactions that reduce the flammability of fuels or delay their combustion. Fire retardants ...

. 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 ...

, used to treat the surface of

citrus ''Citrus'' is a genus of flowering trees and shrubs in the family Rutaceae. Plants in the genus produce citrus fruits, including important crops such as oranges, mandarins, lemons, grapefruits, pomelos, and limes. ''Citrus'' is nativ ...

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

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 a sweet odor reminiscent of benzaldehyde. Over time, samples of ...

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 given substance. The value of LD50 for a substance is the dose requ ...

(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- 2-Hydroxyphenyl compounds Household chemicals Fungicides Antiseptics Fumigants Preservatives Biphenyls