2-Phenylphenol

2-Phenylphenol Basic information
Product Name:2-Phenylphenol
Synonyms:BIPHENYLOL-2;HYDROXY-(2-PHENYL)BENZENE;FEMA 3959;DOWICIDE 1(R);[1,1'-BIPHENYL]-2-OL;AKOS BAR-1742;2-PHENYLPHENOL;2-DIPHENYLOL
CAS:90-43-7
MF:C12H10O
MW:170.21
EINECS:201-993-5
Product Categories:Biphenyl & Diphenyl ether;Aromatic Compounds;Industrial/Fine Chemicals;90-43-7
Mol File:90-43-7.mol
2-Phenylphenol Structure
2-Phenylphenol Chemical Properties
Melting point 57-59 °C(lit.)
Boiling point 282 °C(lit.)
density 1.21
vapor pressure 7 mm Hg ( 140 °C)
FEMA 3959 | 2-PHENYLPHENOL
refractive index 1.6188 (estimate)
Fp 255 °F
storage temp. Store below +30°C.
solubility Soluble in ethanol, acetone, benzene,sodium hydroxide, chloroform, acetonitrile, toluene, hexane, ligroin, ethyl ether, pyridine, ethylene glycol, isopropanol, glycol ethers and polyglycols.
form Crystalline Flakes
pka10.01(at 25℃)
color White
PH7 (0.1g/l, H2O, 20℃)
Odornearly wh. or lt. buff crystals, mild char. sweetish odor
explosive limit1.4-9.5%(V)
Water Solubility 0.7 g/L (20 ºC)
Sensitive Hygroscopic
Merck 14,7304
JECFA Number735
BRN 606907
Stability:Stable. Combustible. Incompatible with strong oxidizing agents, halogens.
InChIKeyLLEMOWNGBBNAJR-UHFFFAOYSA-N
LogP3.18 at 22.5℃
CAS DataBase Reference90-43-7(CAS DataBase Reference)
IARC3 (Vol. 73) 1999
NIST Chemistry Referenceo-Hydroxybiphenyl(90-43-7)
EPA Substance Registry System2-Phenylphenol (90-43-7)
Safety Information
Hazard Codes Xi,N
Risk Statements 36/37/38-50-37/38/50-36
Safety Statements 22-61
RIDADR UN 3077 9/PG 3
WGK Germany 2
RTECS DV5775000
Autoignition Temperature>520 °C
TSCA Yes
HazardClass 9
PackingGroup III
HS Code 29071900
Hazardous Substances Data90-43-7(Hazardous Substances Data)
ToxicityLD50 orally in rats: 2.48 g/kg (Hodge)
MSDS Information
ProviderLanguage
1,1'-Biphenyl-2-ol English
SigmaAldrich English
ACROS English
ALFA English
2-Phenylphenol Usage And Synthesis
Description2-phenylphenol(OPP) is a broad spectrum fungicide used to protect crops in storage. It is highly soluble in water, moderately voatile but is not expected to be persistent in the environment. OPP is more selective than other free phenols but does produce phytotoxic effects.
Chemical Propertieso-Phenylphenol is a white to buff-colored crystalline solid with a distinct odor. When heated to decomposition, it emits acrid smoke and irritating fumes.
Uses2-Phenylphenol is a agriculture fungicide and is no longer used as a food additive.
DefinitionChEBI: 2-Phenylphenol is a member of the class of hydroxybiphenyls that is biphenyl substituted by a hydroxy group at position 2. It is generally used as a post-harvest fungicide for citrus fruits. It has a role as an environmental food contaminant and an antifungal agrochemical. It derives from a hydride of a biphenyl.
Preparation2-Phenylphenol can be recovered from the distillation residue of the process of phenol production via sulfonation. The phenol distillation residue contains about 40% of phenyl phenol with the other components including phenol, inorganic salts, water and so on. After vacuum distillation, the mixed phenyl phenol fraction is separated out with the vacuum being 53.3-66.7kPa. The temperature, started to be cut at 65-75 ℃ to until 100 ℃ above, but should not higher than 1345 ℃. Then take advantage of the solubility difference of ortho, p-hydroxy biphenyl in the trichlorethylene, the two are separated into pure product. The mixed material (mainly 2-hydroxy biphenyl and 4-hydroxy biphenyl) is heated to be dissolved in the trichlorethylene, after cooling, first precipitate out 4-hydroxy biphenyl crystal. After centrifuge filtration, dry to obtain 4-hydroxy biphenyl. The mother liquor was washed with a sodium carbonate solution, followed by dilute alkaline to make the 2-hydroxybiphenyl salt. After standing stratification, take the upper 2-hydroxybiphenyl sodium salt for dehydration under reduced pressure, namely, sodium salt products. The 2-hydroxybiphenylsodium salt is white to light red powder, being easily soluble in water with the solubility in 100g of water being 122g. The pH value of the 2% aqueous solution is 11.1-12.2. It is also easily soluble in acetone, methanol, soluble in glycerol, but insoluble in oil. The sodium salt of 2-hydroxy biphenyl, after acidification, can lead to the formation of 2-hydroxy biphenyl with both of them being food additives.
Application2-phenylphenol is remarkably versatile organic chemical products, widely used antiseptic, auxiliaries and surfactant synthesis of new plastics, resins and polymer materials in areas such as stabilizers and flame retardants. It is used for the post-harvest control of storage diseases of apples, citrus fruit, stone fruit, tomatoes, cucumbers and other vegetables. It is also used for the protection of textiles and timber and as a fungistat in water-soluble paints.
Production MethodsOPP is produced as a by-product in the manufacture of diphenyl oxide or by aldol condensation of hexazinone.
Synthesis Reference(s)Journal of the American Chemical Society, 75, p. 2947, 1953 DOI: 10.1021/ja01108a047
Tetrahedron, 40, p. 4981, 1984 DOI: 10.1016/S0040-4020(01)91336-5
The Journal of Organic Chemistry, 26, p. 283, 1961 DOI: 10.1021/jo01060a632
General DescriptionLight lavender crystals or solid.
Air & Water ReactionsInsoluble in water.
Reactivity Profile2-Phenylphenol react as a weak organic acid. Exothermically neutralizes bases. May react with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides to generate flammable gas (H2) and the heat of the reaction may ignite the gas. Is sulfonated very readily (for example, by concentrated sulfuric acid at room temperature) in exothermic reactions. May be nitrated very rapidly. Nitrated phenols often explode when heated and also form metal salts that tend toward detonation by rather mild shock. Can react with oxidizing agents .
Fire Hazard2-Phenylphenol is combustible.
Flammability and ExplosibilityNonflammable
Agricultural UsesFungicide, Disinfectant, Microbiocide: Used to make fungicides. Also used to make dye stuffs and rubber chemicals, but used primarily as a disinfectant cleaner. Registered for use in the U.S. and U.K.
Trade nameANTHRAPOLE 73®; DOWCIDE-1®; Invalon OP®; KIWI LUSTR-277®; NECTRYL®; PREVENTOL-O Extra®; REMOL TRF®; TETROSIN OE®; TETROSIN OE-N®; TORSITE®; TUMESCAL OPE®
Safety ProfileA poison by intraperitoneal route.Moderately toxic by ingestion and possibly other routes.An experimental teratogen. Other experimentalreproductive effects. Human mutation data reported.Severe eye and moderate skin irritant. Questionablecarcinogen wi
Potential Exposureo-Phenylphenol is used in the manufacture of plastics, resins, rubber, as Agricultural chemical, in making fungicides; as an intermediate in making dye stuffs and rubber chemicals; a germicide; used in food packaging.
CarcinogenicityIARC classified SOPP as a B2 carcinogen in 1983, based on reports from Japan that high dietary levels of this sodium salt caused bladder tumors in male rats. Both sodium saccharin and sodium cyclamate also cause bladder tumors at high doses in male rats, but classification of these food additives as B2 carcinogens was recently rescinded by IARC at a meeting in 1998.
The U.S. National Toxicology Program conducted a skin painting study with OPP in groups of 50 mice per sex. The OPP was applied as an acetone solution on 3 days per week for 2 years, both alone and as a promoter with DMBA. No skin neoplasms were observed in either sex treated with OPP alone, and there were no tumor enhancing or inhibiting effects when OPP and DMBA were given in combination.
Metabolic pathway2-Phenylphenol is not used on growing plants because it is too phytotoxic and there appears to be no information published on its metabolism in plants. Its widespread use as a preservative, disinfectant and fungistat on stored food (either by direct application or impregnated in packaging) requires studies on its environmental fate and metabolism in mammals. Several studies in mammals are available and the compound has been the subject of an evaluation by the UK MAFF Pesticide Safety Directorate (PSD); the results have been published (PSD, 1993). This evaluation was prompted by the discovery of bladder tumours in rats treated with high doses of the compound.
2-Phenylphenol is also used as the sodium and potassium salts where water solublity is important. No information is available specifically on the latter. The metabolism of the free phenol and the sodium salt have been studied separately. Once absorbed into a cell, provided that internal pH control is maintained, the two forms should be indistinguishable.
ShippingUN3143 Dyes, solid, toxic, n.o.s. or Dye intermediates, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required
Purification MethodsCrystallise it from pet ether. [Beilstein 6 IV 4579.]
Toxicity evaluation2-phenylphenol has a moderate to low toxicity to biodiversity. This substance has a low oral mammalian toxicity, is carcinogenic, a neurotoxin and recognised irritant. 2-Phenylphenol and its sodium salt have a low acute toxicity in mammals when administered orally, with LD50 values ranging from 600 to 3500 mg/kg of body weight.
http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/1340.htm
Degradation2-Phenylphenol is readily degraded in surface waters and municipal waste mixtures, and the degradation is biologically mediated. In river water, radiolabelled 2- phenylphenol at concentrations ranging from 1.2 to 120 μg/litre was degraded to about 50% of the initial concentration in 1 week. The addition of mercuric chloride to inhibit biological activity reduced the decrease to only 10% after 30 days. In activated sludge, radiolabelled 2-phenylphenol at 9.6 mg/litre was degraded to 50% of the initial concentration in 24 h. 2-Phenylphenol therefore meets the criteria to be classified as readily biodegradable (FAO/WHO, 1999).
IncompatibilitiesStrong bases, strong oxidizers
Waste DisposalIn accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.
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