If phenol is inhaled or swallowed, local cauterization occurs with headaches, dizziness, vomiting, irregular breathing, respiratory arrest and heart failure. The peaks are very intense in phenol, methylphenol, and dimethylphenol, as would be predicted for aromatic compounds. Later in this chapter, SCWO of phenol will be discussed. Excellent reviews summarizing environmental and health risks of phenol are recommended.222, 223, Robert J. Ouellette, J. David Rawn, in Organic Chemistry, 2014. Concentrated phenol liquids are commonly used for permanent treatment of ingrown toe and finger nails, a procedure known as a chemical matrixectomy. Phenol is a highly toxic compound causing protein degradation and tissue erosion. The environmental pollution proceeds from industrial sources by the manufacture of dyes, papers, plastics, drugs, and antioxidants or from the use of phenols as pesticides and insecticides. [39][40], Phenol was discovered in 1834 by Friedlieb Ferdinand Runge, who extracted it (in impure form) from coal tar. “Pomegranate Fruit as a Rich Source of Biologically Active Compounds.” BioMed [22][23] In 2010, worldwide demand for acetone was approximately 6.7 million tonnes, 83 percent of which was satisfied with acetone produced by the cumene process. Interestingly, right after their emergence as adults, females show a preference of feeding on nectar, … It is oxidized to a hydroperoxide, akin to the production of cumene hydroperoxide. A Review", "Anti-Tyrosinase and DPPH Radical Scavenging Activities of Selected Thai Herbal Extracts Traditionally Used as Skin Toner", "Prohibited substances in cosmetic product (Annex II, #1175, Phenol) - European Commission", "CosIng - Cosmetics - GROWTH - European Commission", "Cosmetic Ingredient Hotlist - Canada.ca", "Cosmetic Ingredient Hotlist: Prohibited and Restricted Ingredients - Canada.ca", "Ueber einige Produkte der Steinkohlendestillation", "Ueber einige Produkte der Steinkohlendestillation,", "Antiseptic Principle Of The Practice Of Surgery", "Peat, Phenol and PPM, by Dr P. Brossard", http://www.inchem.org/documents/icsc/icsc/eics0070.htm, "Medical Management Guidelines for Phenol (C6H6O)", National Pollutant Inventory: Phenol Fact Sheet, CDC - Phenol - NIOSH Workplace Safety and Health Topic, Arcane Radio Trivia outlines competing uses for Phenol circa 1915, https://en.wikipedia.org/w/index.php?title=Phenol&oldid=997847649, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Creative Commons Attribution-ShareAlike License, This page was last edited on 2 January 2021, at 14:49. The LD50 for oral toxicity is less than 500 mg/kg for dogs, rabbits, or mice; the minimum lethal human dose was cited as 140 mg/kg. Upon skin contact, skin becomes white with a subsequent red blister-like appearance and an accompanying burning sensation. Horticulturae (ISSN 2311-7524) is an international peer-reviewed open access journal published monthly online by MDPI. INTRODUCTION. Although the pKa values increase for electron-donating groups such as p-methyl or p-methoxy, the decrease in acidity is less than a factor of 2 in pKa. Gerd Brunner, in Supercritical Fluid Science and Technology, 2014. [30], The major uses of phenol, consuming two thirds of its production, involve its conversion to precursors for plastics. [33], Phenol derivatives have been used in the preparation of cosmetics including sunscreens,[34] hair colorings, skin lightening preparations,[35] as well as in skin toners/exfoliators. The Journal of Organic Chemistry, Articles ASAP (Featured Article) Publication Date (Web): January 19, 2021. It is not to be confused with, Except where otherwise noted, data are given for materials in their, Drago, R S. Physical Methods For Chemists, (Saunders College Publishing 1992), IBSN 0-03-075176-4, Laurence, C. and Gal, J-F. Lewis Basicity and Affinity Scales, Data and Measurement, (Wiley 2010) pp 50-51 IBSN 978-0-470-74957-9. After antiseptic surgery was introduced in the summer of 1865, there were only six deaths in forty cases. Phenol was once widely used as an antiseptic, its use pioneered by Joseph Lister (see History section). In 1841, the French chemist Auguste Laurent obtained phenol in pure form. Left: Influence of temperature, PO2≈0.5MPa. The decomposition products consist of small molecules such as carbon, H2, CH4, C2H6, and C2H4 as well as some benzene, phenol, and lower levels of condensation products such as biphenyl, diphenyl ether, hydroxy-diphenyl, and dihydroxydiphenyl. From the early 1900s to the 1970s it was used in the production of carbolic soap. [41] Runge called phenol "Karbolsäure" (coal-oil-acid, carbolic acid). In an alkoxide ion, such as the one derived from cyclohexanol, the negative charge is localized at the oxygen atom. 148-155. [31] It is the active ingredient in some oral analgesics such as Chloraseptic spray, TCP and Carmex, commonly used to temporarily treat pharyngitis. Routes for the generation of nitrous oxide however remain uncompetitive. The reaction can be done using a catalytic quantity of sulfuric acid to protonate the carbonyl oxygen atom of the anhydride. The pKa value of a typical alcohol is in the neighborhood of 17. Robert J. Ouellette, J. David Rawn, in Organic Chemistry (Second Edition), 2018. Phenol is an organic compound appreciably soluble in water, with about 84.2 g dissolving in 1000 mL (0.895 M). The mortality rate had dropped from almost 50 per cent to around 15 per cent. This compound is ingested from the plants the beaver eats. Phenol was first extracted from coal tar, but today is produced on a large scale (about 7 billion kg/year) from petroleum-derived feedstocks. Phenols represent a class of compounds that are mainly composed of an aromatic ring bearing one or more hydroxyl substituents, thus creating an extended range from simple molecules to highly polymerized phenolics [55]. An important point about the mass spectra of substituted phenols is the ortho effect. By this general approach, many groups can be appended to the ring, via halogenation, acylation, sulfonation, and other processes. Accounting for 95% of production (2003) is the cumene process, also called Hock process. The induction period is inversely proportional to the dissolved oxygen concentration. The human oral LDLo (lethal dose low) value is 140 mg k g −1. Phenol red exists as a red crystal that is stable in air. [17], Phenol exhibits keto-enol tautomerism with its unstable keto tautomer cyclohexadienone, but only a tiny fraction of phenol exists as the keto form. Phenol is more acidic than cyclohexanol and acyclic alcohols because the phenoxide ion is more stable than the alkoxide ion. Cyclohexanone is an important precursor to some nylons.[24]. [36] However, due to safety concerns, phenol is banned from use in cosmetic products in the European Union[37][38] and Canada. Because of phenol's commercial importance, many methods have been developed for its production, but only the cumene process is the dominant technology. Phenol is also a versatile precursor to a large collection of drugs, most notably aspirin but also many herbicides and pharmaceutical drugs. Phenol is also a recoverable byproduct of coal pyrolysis. However, the position of the aromatic substitution cannot be determined using only mass spectrometry. Solid or liquid phenol is rapidly absorbed by the skin and results in very severe tissue damage. The carboxylate ion is more stabilized relative to the phenoxide ion because the negative charge is located on the oxygen atoms of the carboxylate ion. Condensation of phenol, alkylphenols, or diphenols with formaldehyde gives phenolic resins, a famous example of which is Bakelite. Bhim Prasad Kafle, in Chemical Analysis and Material Characterization by Spectrophotometry, 2020. We use cookies to help provide and enhance our service and tailor content and ads. In an alkoxide ion, the negative charge is localized at the oxygen atom. When he checked the wound, Lister was pleasantly surprised to find no signs of infection, just redness near the edges of the wound from mild burning by the carbolic acid. In contrast, phenol is 10 million times more acidic: its pKa is 10. Phenoxide ion is therefore resonance stabilized. Only the adult females can feed on blood, important for the production of their offspring, and therefore transmitting these pathogens for the human host. Enthalpies of adduct formation have been studied pKa value of a phenyl group ( −C6H5 ) to... Found in castoreum tar remained the primary source until the development of the phenoxide ion whereas! Acid ) effective, and p-heptyloxyphenol after intraperitoneal ( ip ) and dermal exposure was examined or Repeated exposure the. 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Of Nutritional Biochemistry 23.11 ( 2012 ): January 19, 2021 hydrolysis benzene! For chemical matrixectomies performed by podiatrists Lister ( see History section ) to nylon piece. Laurent ( 1836 ) `` Sur la chlorophénise et les acides chlorophénisique et chlorophénèsique ''... But more stable compared to the threshold limit value ( TLV ) of 5 p.p.m rapidly.