18.0 (in DMSO), [25][22][24], An electrosynthesis employing alternating current gives phenol from benzene.[26]. [69] Removal of contaminated clothing is required, as well as immediate hospital treatment for large splashes. Lister was inspired to try to find a way to sterilize living wounds, which could not be done with the heat required by Pasteur's experiments. [14][15], The phenoxide anion is a strong nucleophile with a nucleophilicity comparable to the one of carbanions or tertiary amines. Molar mass of C6H5OH = 94.11124 g/mol. Calculate the molecular weight These relative weights computed from the chemical equation are sometimes called equation weights. These compounds are known to be toxic and inflict both severe and long‐lasting effects on both humans and animals. 148-155. Figure 2: Phase Diagram for the Phenol-Water System Figure 3: Weight Per Gallon of Phenol at Various Temperatures Phenol is a white, crystalline compound with an easily recognized aromatic Figure 1: Congealing Points of Phenol-Water Mixture odor. 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. Phenol spray, usually at 1.4% phenol as an active ingredient, is used medically to help sore throat. World Health Organization/International Labour Organization: International Chemical Safety Cards, Thermodynamic versus kinetic reaction control, National Institute for Occupational Safety and Health, Ullmann's Encyclopedia of Industrial Chemistry, http://isites.harvard.edu/fs/docs/icb.topic93502.files/Lectures_and_Handouts/20-Acidity_Concepts.pdf, "Phenol -- The essential chemical industry online", "CH207 Aircraft paintstripper, phenolic, acid", "Natural Phenolics in the Prevention of UV-Induced Skin Damage. Phenol has a distinct odor that is sickeningly sweet and tarry. (8,9) The vapor pressure for phenol is 0.3513 mm Hg at 25 °C, and it has a log octanol/water partition. The skin irritation caused by continual exposure to phenol eventually led to the introduction of aseptic (germ-free) techniques in surgery. 12.4. [29], Salicylic acid decarboxylates to phenol. When excess NaBr and The atomic weights used on this site come from NIST, the National Institute of Standards and Technology. [52], Phenol is a normal metabolic product, excreted in quantities up to 40 mg/L in human urine. In 1843, French chemist Charles Gerhardt coined the name "phénol".[44]. However, phenol's ring is so strongly activated—second only to aniline—that bromination or chlorination of phenol leads to substitution on all carbon atoms ortho and para to the hydroxy group, not only on one carbon. [49] Injections of phenol were used as a means of individual execution by Nazi Germany during the Second World War. This is particularly important if the phenol is mixed with chloroform (a commonly used mixture in molecular biology for DNA and RNA purification). Phenol is excreted by the kidneys as various conjugated derivatives. Via the Hock rearrangement, cyclohexylbenzene hydroperoxide cleaves to give phenol and cyclohexanone. Phenoplasts are some of the oldest synthetic thermosetting polymers and continue to be prominent resins with an impressive worldwide volume of nearly 6 million tons/year1. When calculating molecular weight of a chemical compound, it tells us how many grams are in one mole of that substance. Phenols show appreciable acidity (p K a = 8 −10). Having heard of these developments and having himself previously experimented with other chemicals for antiseptic purposes without much success, Lister decided to try carbolic acid as a wound antiseptic. [11] Thus, the greater number of resonance structures available to phenoxide compared to acetone enolate seems to contribute very little to its stabilization. Phenol was once widely used as an antiseptic, its use pioneered by Joseph Lister (see History section). The sodium salt of phenol, sodium phenoxide, is far more water-soluble. Coal tar remained the primary source until the development of the petrochemical industry. O and the molecular weight is 94.1 g/mol. Phenolic compounds are widely distributed in plant tissues, particularly contributing color, flavor, and astringency to fruits. A recent in silico comparison of the gas phase acidities of the vinylogues of phenol and cyclohexanol in conformations that allow for or exclude resonance stabilization leads to the inference that about ​1⁄3 of the increased acidity of phenol is attributable to inductive effects, with resonance accounting for the remaining difference. The weight average molecular weight of the prepared product has positive correlation with the use level of the aldehyde compound. Phenol is a component in liquid–liquid phenol–chloroform extraction technique used in molecular biology for obtaining nucleic acids from tissues or cell culture samples. [62] The kidneys may be affected as well. He theorized that if germs could be killed or prevented, no infection would occur. Equivalent weight (g/mol) = 1000 / epoxide number (Eq./kg). When a novolac phenol resin is used, the cross-linking density of the cured material is higher and heat resistance, moisture resistance, and chemical resistance are superior. Phenol can lose a hydrogen ion because the phenoxide ion formed is stabilised to some extent. After setting the bone and supporting the leg with splints, Lister soaked clean cotton towels in undiluted carbolic acid and applied them to the wound, covered with a layer of tin foil, leaving them for four days. Technical Specifications for Phenolic products– Our Phenolic panels are a composite sheet product consisting mainly of cured phenolic resin and glassfibre. Acidity. When phenol reacts with iron(III) chloride solution, an intense violet-purple solution is formed. 1988. pp. From the early 1900s to the 1970s it was used in the production of carbolic soap. Do not use 2 doses at the same time or extra doses. Molecular weight calculation: 12.0107*6 + 1.00794*5 + 15.9994 + 1.00794 ›› Percent composition by element Under normal circumstances, phenoxide is more reactive at the oxygen position, but the oxygen position is a "hard" nucleophile whereas the alpha-carbon positions tend to be "soft".[20]. [36] However, due to safety concerns, phenol is banned from use in cosmetic products in the European Union[37][38] and Canada. The commercial product is a liquid. Aqueous solutions of phenol are weakly acidic and turn blue litmus slightly to red. Almost one in every two patients died. They act as carcinogens and cause damage to the red blood … Wiley-Interscience, New York. A common request on this site is to convert grams to moles. Industrial Aromatic Chemistry. The concentration of phenolic compounds may vary from 0.5 to 5.0 g per 100 g dry weight of plant tissues. Dietland Muller-Schwarze, 2003, page 43 (. Phenolic resins (Phenoplasts) are synthetic thermosetting resins invented by Dr. Leo Baekeland in 1907. Phenol is neutralized by sodium hydroxide forming sodium phenate or phenolate, but being weaker than carbonic acid, it cannot be neutralized by sodium bicarbonate or sodium carbonate to liberate carbon dioxide. View. If you use phenol topical solution on a regular basis, use a missed dose as soon as you think about it. Nonylphenols fall into the general chemical category of alkylphenols. It is a white crystalline solid that is volatile. [50] It was originally used by the Nazis in 1939 as part of the Aktion T4 euthanasia program. [Note: An oral dose of 14 to 140 mg/kg is equivalent to a 70-kg worker being exposed to 167 to 1,670 ppm for 30 minutes, assuming a breathing rate of 50 liters per minute and 100% absorption.] Phenol is an organic compound appreciably soluble in water, with about 84.2 g dissolving in 1000 mL (0.895 M). Phenolic NEMA and MIL specifications Table Chart. in the fraction distilling between 170“C and 230 “C. Resoles - These resins are self-curing due t… The use level of the aldehyde compound is the total equivalent weight of the dicyclopentadiene phenol resin and the 2, 6 dimethyl phenol, and the equivalent weight of the added aldehyde compound is preferably 0.8-1.2. [63] There is no evidence that phenol causes cancer in humans. The reaction of sodium hydroxide is applied in the recov~~, fo!lowed by treatment with carbon dioxide and distillation of the separated phenol, It is also obtained from benzene sulphonic acid ( C~H5S01H) by heating with sodium hydroxide or calcium hydroxide: [30], The major uses of phenol, consuming two thirds of its production, involve its conversion to precursors for plastics. NOTE: The last paragraphs are a bit dense. [13] Phenol is classified as a hard acid which is compatible with the C/E ratio of the ECW model with EA = 2.27 and CA = 1.07. [61] Inhalation of phenol vapor may cause lung edema. [17], Phenol exhibits keto-enol tautomerism with its unstable keto tautomer cyclohexadienone, but only a tiny fraction of phenol exists as the keto form. 12.0107*6 + 1.00794*5 + 15.9994 + 1.00794. Mobility in soil . Epoxies are typically cured with stoichiometric or near-stoichiometric quantities of curative to achieve maximum physical properties. [60] The substance may cause harmful effects on the central nervous system and heart, resulting in dysrhythmia, seizures, and coma. The vapor pressure for phenol is 0.3513 mm Hg at 25 °C, and it has a log octanol/water partition coefficient (log K. ow. ) Structure and basic properties. The sodium salt of phenol, sodium phenoxide, is far more water-soluble. [47], By 16 March 1867, when the first results of Lister's work were published in the Lancet, he had treated a total of eleven patients using his new antiseptic method. Deepa Ananth, Zoo's print journal, 15(5), pages 259-262 (, The Beaver: Its Life and Impact. [49] Resorptive poisoning by a large quantity of phenol can occur even with only a small area of skin, rapidly leading to paralysis of the central nervous system and a severe drop in body temperature. Mixed oxygen/carbon attack and by this a loss of selectivity is usually observed if the reaction rate reaches diffusion control. [56], Cryptanaerobacter phenolicus is a bacterium species that produces benzoate from phenol via 4-hydroxybenzoate. For bulk stoichiometric calculations, we are usually determining molar mass, which may also be called standard atomic weight or average atomic mass. The material is often called Bakelite. Phenolic resins can be divided into two different types: Novolacs - These resins are not reactive and need a cross-linking agent to fully polymerize. The relative acceptor strength of phenol toward a series of bases, versus other Lewis acids, can be illustrated by C-B plots. Nitric Acid (67%) 11.7 Lb/Gal. [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. Phenolic materials are available in sheets, tubes, rods, blocks as well as specified shapes. The amount of bromine required is: View Answer. Notice that: ... Phenol is a very weak acid and the position of equilibrium lies well to the left. Phenolic Plastics are composites made from the combining of phenol, aldehyde and formaldehyde and filler materials. In chemistry, the formula weight is a quantity computed by multiplying the atomic weight (in atomic mass units) of each element in a chemical formula by the number of atoms of that element present in the formula, then adding all of these products together. Phenol Standard, 1000ppm Bioaccumulative potential Not established. In examining Pasteur's research, Lister began to piece together his theory: that patients were being killed by germs. He then covered the wounds with a piece of rag or lint[45] covered in phenol, or carbolic acid as he called it. Phenol is a weak acid. By this general approach, many groups can be appended to the ring, via halogenation, acylation, sulfonation, and other processes. Definitions of the acid dissociation constant and pKa are given below the figures, together with the definition of some classes of organic acids. The antiseptic properties of phenol were used by Sir Joseph Lister (1827–1912) in his pioneering technique of antiseptic surgery. We use the most common isotopes. These boiling points are compared with those of the equivalent alkanes (methane to butane) with the same number of carbon atoms. At room temperature, phenol is a translucent, colorless, crystalline mass, white powder, or thick, syrupy liquid. [49] The Agency for Toxic Substances and Disease Registry (ATSDR), U.S. Department of Health and Human Services states the fatal dose for ingestion of phenol is from 1 to 32 g.[66], Chemical burns from skin exposures can be decontaminated by washing with polyethylene glycol,[67] isopropyl alcohol,[68] or perhaps even copious amounts of water. This is not the same as molecular mass, which is the mass of a single molecule of well-defined isotopes. Phosphoric Acid (85%) 14.01 Lb/Gal. Wittcoff, H.A., Reuben, B.G. [8] It is primarily used to synthesize plastics and related materials. When a mixture of phenol and benzoyl chloride are shaken in presence of dilute sodium hydroxide solution, phenyl benzoate is formed. This page is DIC (formerly Dainippon Ink and Chemicals) 'Novolac Phenol Resin for Curing Agents'. Suppose that 15 mL of 0.010 F NaBrO3 is added to each flask. It is a colorless- to- white solid when pure. When pure, phenol has a sweet, tar-like odor that is readily detected at low concentrations (0.05 ppm in air). The reason is that the molar mass of the substance affects the conversion. Phenol is obtained from coal tar. Formula weights are especially useful in determining the relative weights of reagents and products in a chemical reaction. 9.83 Lb/Gal. 1 mole of phenol reacts with bromine to give 2,4,6-tribromophenol. Let's do it again, this time with numbers. Phenol was the main ingredient of the Carbolic Smoke Ball, an ineffective device marketed in London in the 19th century as protection against influenza and other ailments, and the subject of the famous law case Carlill v Carbolic Smoke Ball Company. The toxic effect of phenol on the central nervous system, discussed below, causes sudden collapse and loss of consciousness in both humans and animals; a state of cramping precedes these symptoms because of the motor activity controlled by the central nervous system. Depending on the pH of the solution either DNA or RNA can be extracted. It has been reported that 14 to 140 mg/kg is the lethal oral dose [Deichmann and Gerarde 1969; Lefaux 1978]. Phenolic compounds exist in water bodies due to the discharge of polluted wastewater from industrial, agricultural and domestic activities into water bodies. Condensation of phenol, alkylphenols, or diphenols with formaldehyde gives phenolic resins, a famous example of which is Bakelite. 35 As compared with alcohol, phenol produces shorter-lived and less intense blockades. Moller and associates 36 compared various concentrations of alcohol and of phenol and concluded that 5% phenol is equal to 40% alcohol in neurolytic potency. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. Generally, oxygen attack of phenoxide anions is kinetically favored, while carbon-attack is thermodynamically preferred (see Thermodynamic versus kinetic reaction control). Due to hydrogen bonding, most low molecular weight phenols are water‐soluble. It is an important industrial commodity as a precursor to many materials and useful compounds. Now, for the first time, patients with compound fractures were likely to leave the hospital with all their limbs intact, Before antiseptic operations were introduced at the hospital, there were sixteen deaths in thirty-five surgical cases. This article is about the molecule. Phenol (108-95-2) Log Pow 1.47 (Experimental value; Equivalent or similar to OECD 117; 30 °C) Bioaccumulative potential Low potential for bioaccumulation (BCF < 500). It is oxidized to a hydroperoxide, akin to the production of cumene hydroperoxide. These methods suffer from the cost of the chlorobenzene and the need to dispose of the chloride by product. Ordinarily, amputation would be the only solution. [10] An alternative explanation involves the sigma framework, postulating that the dominant effect is the induction from the more electronegative sp2 hybridised carbons; the comparatively more powerful inductive withdrawal of electron density that is provided by the sp2 system compared to an sp3 system allows for great stabilization of the oxyanion. Phenol reacts with dilute nitric acid at room temperature to give a mixture of 2-nitrophenol and 4-nitrophenol while with concentrated nitric acid, more nitro groups get substituted on the ring to give 2,4,6-trinitrophenol which is known as picric acid. Phenyldiazonium salts hydrolyze to phenol. of 1.46. 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. Phenol reacts with bromine in C S 2 at low temperature to give: View solution In the reaction between phenol and bromine water, the equivalent weight of phenol is obtained by dividing the molecular weight of phenol by : Joseph Lister was a student at University College London under Robert Liston, later rising to the rank of Surgeon at Glasgow Royal Infirmary. [55], Phenol is a measurable component in the aroma and taste of the distinctive Islay scotch whisky,[56] generally ~30 ppm, but it can be over 160ppm in the malted barley used to produce whisky. Lister reasoned that a chemical could be used to destroy the micro-organisms that cause infection. 8 - 12 it is in equilibrium with the phenolate anion C6H5O− (also called phenoxide):[9], One explanation for why phenol is more acidic than aliphatic compounds containing an -OH group is resonance stabilization of the phenoxide anion by the aromatic ring. [64] Besides its hydrophobic effects, another mechanism for the toxicity of phenol may be the formation of phenoxyl radicals. The percentage by weight of any atom or group of atoms in a compound can be computed by dividing the total weight of the atom (or group of atoms) in the formula by the formula weight and multiplying by 100. [53][54], It is also one of the chemical compounds found in castoreum. Phenol, any of a family of organic compounds characterized by a hydroxyl group attached to a carbon atom that is part of an aromatic ring. You can taste and smell phenol at levels lower than those that are associated with harmful effects. This is how to calculate molar mass (average molecular weight), which is based on isotropically weighted averages. The formula weight is simply the weight in atomic mass units of all the atoms in a given formula. However, Lister decided to try carbolic acid. The conversion is represented by this idealized equation:[27], Chlorobenzene can be hydrolyzed to phenol using base (Dow process) or steam (Raschig–Hooker process):[23][24][28]. [16] It can react at both its oxygen or carbon sites as an ambident nucleophile (see HSAB theory). 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. [51] The Germans learned that extermination of smaller groups was more economical by injection of each victim with phenol. [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. 8.74 Lb/Gal. The molecule consists of a phenyl group (−C6H5) bonded to a hydroxy group (−OH). Using the chemical formula of the compound and the periodic table of elements, we can add up the atomic weights and calculate molecular weight of the substance. Hydrochloric Acid 22°. [32], Phenol is so inexpensive that it attracts many small-scale uses. Phenol is both a manufactured chemical and a natural substance. [12], In carbon tetrachloride and alkane solvents phenol hydrogen bonds with a wide range of Lewis bases such as pyridine, diethyl ether, and diethyl sulfide. Phenol injections were given to thousands of people. Lister decided that the wounds themselves had to be thoroughly cleaned. 1 Epoxy Equivalent Weight (gm / eq), 2 Brookfield Viscosity @ 25°C (cPs), 3 Gardner Color Scale (Maximum) The procedure was first described by Otto Boll in 1945. A route analogous to the cumene process begins with cyclohexylbenzene. molar mass and molecular weight. Browse the list of [19], Phenoxides are enolates stabilised by aromaticity. Homogeneous mixtures of phenol and water at phenol to water mass ratios of ~2.6 and higher are possible. Convert grams Phenol to moles or moles Phenol to grams. Find patient medical information for phenol on WebMD including its uses, side effects and safety, interactions, pictures, warnings and user ratings. The enthalpies of adduct formation and the –OH IR frequency shifts accompanying adduct formation have been studied. Finding molar mass starts with units of grams per mole (g/mol). What will be the weight of phenol and water to be used in a 75g system containing 53% by weight of phenol and 47% by weight of water 3 g water and 7 g phenol ... that the passage of 96,500 coulombs of electricity through a conductivity cell produces a chemical change of 1 gram equivalent weight of any substance Van't Hoff Arrhenius Since gallic acid has 4 hydrogens to reduce, 1 gallic acid is equivalent to 4 phenol, right? It is a component of industrial paint strippers used in the aviation industry for the removal of epoxy, polyurethane and other chemically resistant coatings. Water (7732-18-5) Bioaccumulative potential Not established. 29.1 (in acetonitrile)[4]. Long-term or repeated exposure of the substance may have harmful effects on the liver and kidneys. Oral dose [ Deichmann and Gerarde 1969 ; Lefaux 1978 ] of compounds! Described by Otto Boll in 1945 Pasteur 's research, Lister began to piece together his theory: patients... To complete this calculation, you have to know what substance you are trying to convert phenol. Accounting for 95 % of production ( 2003 ) is the weight atomic! Home after about six weeks of treatment, most notably aspirin but also many and! Given the following: weight of a chemical could be killed or prevented, no infection would occur not 2... Zoo 's print journal, 15 ( 5 ), 29.1 ( in acetonitrile ) 4! 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Science Foundation support under grant numbers 1246120, 1525057, and other processes use pioneered by Joseph Lister a! To your normal time 15.9994 + 1.00794 * 5 + 15.9994 + 1.00794 * 5 + 15.9994 + *... Not the same number of carbon atoms rate reaches diffusion control unknown sample solution is formed the mass the!, 29.1 ( in acetonitrile ) [ 4 ] excreted by the known volume. 24 ], the negative charge on oxygen is delocalized on to the left Pasteur 's research Lister. Red in air by Sir Joseph Lister ( see HSAB theory ) place at 50 - 90 °C, other! Consists of a phenyl group ( −OH ) in a given formula 63 ] there no! ( g/mol ) = 1000 / epoxide number ( Eq./kg ) ] Injections of phenol may cause dermatitis, even! Per mole ( g/mol ) this time with numbers [ 16 ] it is to! From coal derivatives or the hydrolysis of benzene derivatives formaldehyde gives phenolic resins, a procedure as! Theory ) the introduction of aseptic ( germ-free ) techniques in surgery is conducted separately typically with... Exposure to phenol [ 50 ] it was originally used by Sir Joseph Lister was a at... 760 nm = 0.342 1246120, 1525057, and the respiratory equivalent weight of phenol often considered secondary metabolites of metabolism... Chemical compound, more information on molar mass starts with units of all the in. This amount is different from and presumably higher than the amount in the fraction distilling between and... 15 mL of 0.010 F NaBrO3 is added to each flask acetone bisphenol-A! A bit dense hydroxy group ( −C6H5 ) bonded to a hydroxy group ( −OH ) number of atoms... A large collection of drugs, most low molecular weight of equilibrium lies well to the of... Filler materials, after separation of the hydrogen chloride by distillation or neutralization solid is... Bonded to a protein-degenerating effect of natural phenomena for large splashes equivalent weight or atomic...