Phenol

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This article is about the molecule. Phenol_sentence_0

For the group of chemicals containing a phenol group, see Phenols. Phenol_sentence_1

"Carbolic acid" redirects here. Phenol_sentence_2

It is not to be confused with carbonic acid. Phenol_sentence_3

Phenol_table_infobox_0

PhenolPhenol_table_caption_0
Phenol_cell_0_1_0 Phenol_cell_0_1_1
Phenol_cell_0_3_0 Phenol_cell_0_3_1
NamesPhenol_header_cell_0_4_0
IdentifiersPhenol_header_cell_0_5_0
CAS NumberPhenol_cell_0_6_0 Phenol_cell_0_6_1
3D model (JSmol)Phenol_cell_0_7_0 Phenol_cell_0_7_1
ChEBIPhenol_cell_0_8_0 Phenol_cell_0_8_1
ChEMBLPhenol_cell_0_9_0 Phenol_cell_0_9_1
ChemSpiderPhenol_cell_0_10_0 Phenol_cell_0_10_1
DrugBankPhenol_cell_0_11_0 Phenol_cell_0_11_1
ECHA InfoCardPhenol_cell_0_12_0 Q130336#P2566Phenol_cell_0_12_1
KEGGPhenol_cell_0_13_0 Phenol_cell_0_13_1
PubChem CIDPhenol_cell_0_14_0 Phenol_cell_0_14_1
RTECS numberPhenol_cell_0_15_0 Phenol_cell_0_15_1
UNIIPhenol_cell_0_16_0 Phenol_cell_0_16_1
CompTox Dashboard (EPA)Phenol_cell_0_17_0 Phenol_cell_0_17_1
PropertiesPhenol_header_cell_0_18_0
Chemical formulaPhenol_cell_0_19_0 C6H6OPhenol_cell_0_19_1
Molar massPhenol_cell_0_20_0 94.113 g·molPhenol_cell_0_20_1
AppearancePhenol_cell_0_21_0 Transparent crystalline solidPhenol_cell_0_21_1
OdorPhenol_cell_0_22_0 Sweet and tarryPhenol_cell_0_22_1
DensityPhenol_cell_0_23_0 1.07 g/cmPhenol_cell_0_23_1
Melting pointPhenol_cell_0_24_0 40.5 °C (104.9 °F; 313.6 K)Phenol_cell_0_24_1
Boiling pointPhenol_cell_0_25_0 181.7 °C (359.1 °F; 454.8 K)Phenol_cell_0_25_1
Solubility in waterPhenol_cell_0_26_0 8.3 g/100 mL (20 °C)Phenol_cell_0_26_1
log PPhenol_cell_0_27_0 1.48Phenol_cell_0_27_1
Vapor pressurePhenol_cell_0_28_0 0.4 mmHg (20 °C)Phenol_cell_0_28_1
Acidity (pKa)Phenol_cell_0_29_0 9.95 (in water),

18.0 (in DMSO),

29.1 (in acetonitrile)Phenol_cell_0_29_1

Conjugate basePhenol_cell_0_30_0 PhenoxidePhenol_cell_0_30_1
UV-vis (λmax)Phenol_cell_0_31_0 270.75 nmPhenol_cell_0_31_1
Dipole momentPhenol_cell_0_32_0 1.224 DPhenol_cell_0_32_1
PharmacologyPhenol_header_cell_0_33_0
ATC codePhenol_cell_0_34_0 C05BB05 () D08AE03 (), N01BX03 (), R02AA19 ()Phenol_cell_0_34_1
HazardsPhenol_header_cell_0_35_0
Safety data sheetPhenol_cell_0_36_0 Phenol_cell_0_36_1
GHS pictogramsPhenol_cell_0_37_0 Phenol_cell_0_37_1
GHS hazard statementsPhenol_cell_0_38_0 H301, H311, H314, H331, H341, H373Phenol_cell_0_38_1
GHS precautionary statementsPhenol_cell_0_39_0 P261, P280, P301+310, P305+351+338, P310Phenol_cell_0_39_1
NFPA 704 (fire diamond)Phenol_cell_0_40_0 2

3 0Phenol_cell_0_40_1

Flash pointPhenol_cell_0_41_0 79 °C (174 °F; 352 K)Phenol_cell_0_41_1
Explosive limitsPhenol_cell_0_42_0 1.8–8.6%Phenol_cell_0_42_1
LD50 (median dose)Phenol_cell_0_43_0 317 mg/kg (rat, oral)

270 mg/kg (mouse, oral)Phenol_cell_0_43_1

LDLo (lowest published)Phenol_cell_0_44_0 420 mg/kg (rabbit, oral)

500 mg/kg (dog, oral) 80 mg/kg (cat, oral)Phenol_cell_0_44_1

LC50 (median concentration)Phenol_cell_0_45_0 19 ppm (mammal)

81 ppm (rat) 69 ppm (mouse)Phenol_cell_0_45_1

PEL (Permissible)Phenol_cell_0_46_0 TWA 5 ppm (19 mg/m) [skin]Phenol_cell_0_46_1
REL (Recommended)Phenol_cell_0_47_0 TWA 5 ppm (19 mg/m) C 15.6 ppm (60 mg/m) [15-minute] [skin]Phenol_cell_0_47_1
IDLH (Immediate danger)Phenol_cell_0_48_0 250 ppmPhenol_cell_0_48_1
Related compoundsPhenol_header_cell_0_49_0
Related compoundsPhenol_cell_0_50_0 Thiophenol

Sodium phenoxidePhenol_cell_0_50_1

Phenol_cell_0_51_0 Phenol_cell_0_51_1

Phenol is an aromatic organic compound with the molecular formula C6H5OH. Phenol_sentence_4

It is a white crystalline solid that is volatile. Phenol_sentence_5

The molecule consists of a phenyl group (−C6H5) bonded to a hydroxy group (−OH). Phenol_sentence_6

Mildly acidic, it requires careful handling because it can cause chemical burns. Phenol_sentence_7

Phenol was first extracted from coal tar, but today is produced on a large scale (about 7 billion kg/year) from petroleum-derived feedstocks. Phenol_sentence_8

It is an important industrial commodity as a precursor to many materials and useful compounds. Phenol_sentence_9

It is primarily used to synthesize plastics and related materials. Phenol_sentence_10

Phenol and its chemical derivatives are essential for production of polycarbonates, epoxies, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous pharmaceutical drugs. Phenol_sentence_11

Properties Phenol_section_0

Phenol is an organic compound appreciably soluble in water, with about 84.2 g dissolving in 1000 mL (0.895 M). Phenol_sentence_12

Homogeneous mixtures of phenol and water at phenol to water mass ratios of ~2.6 and higher are possible. Phenol_sentence_13

The sodium salt of phenol, sodium phenoxide, is far more water-soluble. Phenol_sentence_14

Acidity Phenol_section_1

Phenol is a weak acid. Phenol_sentence_15

In aqueous solution in the pH range ca. 8 - 12 it is in equilibrium with the phenolate anion C6H5O (also called phenoxide): Phenol_sentence_16

Phenol_description_list_0

  • C6H5OH ⇌ C6H5O + HPhenol_item_0_0

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. Phenol_sentence_17

In this way, the negative charge on oxygen is delocalized on to the ortho and para carbon atoms through the pi system. Phenol_sentence_18

An alternative explanation involves the sigma framework, postulating that the dominant effect is the induction from the more electronegative sp hybridised carbons; the comparatively more powerful inductive withdrawal of electron density that is provided by the sp system compared to an sp system allows for great stabilization of the oxyanion. Phenol_sentence_19

In support of the second explanation, the pKa of the enol of acetone in water is 10.9, making it only slightly less acidic than phenol (pKa 10.0). Phenol_sentence_20

Thus, the greater number of resonance structures available to phenoxide compared to acetone enolate seems to contribute very little to its stabilization. Phenol_sentence_21

However, the situation changes when solvation effects are excluded. Phenol_sentence_22

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 ​⁄3 of the increased acidity of phenol is attributable to inductive effects, with resonance accounting for the remaining difference. Phenol_sentence_23

Hydrogen bonding Phenol_section_2

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_sentence_24

The enthalpies of adduct formation and the –OH IR frequency shifts accompanying adduct formation have been studied. Phenol_sentence_25

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. Phenol_sentence_26

The relative acceptor strength of phenol toward a series of bases, versus other Lewis acids, can be illustrated by C-B plots. Phenol_sentence_27

. Phenol_sentence_28

Phenoxide anion Phenol_section_3

The phenoxide anion is a strong nucleophile with a nucleophilicity comparable to the one of carbanions or tertiary amines. Phenol_sentence_29

It can react at both its oxygen or carbon sites as an ambident nucleophile (see HSAB theory). Phenol_sentence_30

Generally, oxygen attack of phenoxide anions is kinetically favored, while carbon-attack is thermodynamically preferred (see Thermodynamic versus kinetic reaction control). Phenol_sentence_31

Mixed oxygen/carbon attack and by this a loss of selectivity is usually observed if the reaction rate reaches diffusion control. Phenol_sentence_32

Tautomerism Phenol_section_4

Phenol exhibits keto-enol tautomerism with its unstable keto tautomer cyclohexadienone, but only a tiny fraction of phenol exists as the keto form. Phenol_sentence_33

The equilibrium constant for enolisation is approximately 10, which means only one in every ten trillion molecules is in the keto form at any moment. Phenol_sentence_34

The small amount of stabilisation gained by exchanging a C=C bond for a C=O bond is more than offset by the large destabilisation resulting from the loss of aromaticity. Phenol_sentence_35

Phenol therefore exists essentially entirely in the enol form. Phenol_sentence_36

Phenoxides are enolates stabilised by aromaticity. Phenol_sentence_37

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". Phenol_sentence_38

Reactions Phenol_section_5

Phenol is highly reactive toward electrophilic aromatic substitution as the oxygen atom's pi electrons donate electron density into the ring. Phenol_sentence_39

By this general approach, many groups can be appended to the ring, via halogenation, acylation, sulfonation, and other processes. Phenol_sentence_40

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. Phenol_sentence_41

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. Phenol_sentence_42

Aqueous solutions of phenol are weakly acidic and turn blue litmus slightly to red. Phenol_sentence_43

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. Phenol_sentence_44

Phenol_description_list_1

  • C6H5OH + NaOH → C6H5ONa + H2OPhenol_item_1_1

When a mixture of phenol and benzoyl chloride are shaken in presence of dilute sodium hydroxide solution, phenyl benzoate is formed. Phenol_sentence_45

This is an example of the Schotten–Baumann reaction: Phenol_sentence_46

Phenol_description_list_2

  • C6H5OH + C6H5COCl → C6H5OCOC6H5 + HClPhenol_item_2_2

Phenol is reduced to benzene when it is distilled with zinc dust or when its vapour is passed over granules of zinc at 400 °C: Phenol_sentence_47

Phenol_description_list_3

  • C6H5OH + Zn → C6H6 + ZnOPhenol_item_3_3

When phenol is reacted with diazomethane in the presence of boron trifluoride (BF3), anisole is obtained as the main product and nitrogen gas as a byproduct. Phenol_sentence_48

Phenol_description_list_4

  • C6H5OH + CH2N2 → C6H5OCH3 + N2Phenol_item_4_4

When phenol reacts with iron(III) chloride solution, an intense violet-purple solution is formed. Phenol_sentence_49

Production Phenol_section_6

Because of phenol's commercial importance, many methods have been developed for its production, but only the cumene process is the dominant technology. Phenol_sentence_50

Cumene process Phenol_section_7

Accounting for 95% of production (2003) is the cumene process, also called Hock process. Phenol_sentence_51

It involves the partial oxidation of cumene (isopropylbenzene) via the Hock rearrangement: Compared to most other processes, the cumene process uses relatively mild conditions and relatively inexpensive raw materials. Phenol_sentence_52

For the process to be economical, both phenol and the acetone by-product must be in demand. Phenol_sentence_53

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. Phenol_sentence_54

A route analogous to the cumene process begins with cyclohexylbenzene. Phenol_sentence_55

It is oxidized to a hydroperoxide, akin to the production of cumene hydroperoxide. Phenol_sentence_56

Via the Hock rearrangement, cyclohexylbenzene hydroperoxide cleaves to give phenol and cyclohexanone. Phenol_sentence_57

Cyclohexanone is an important precursor to some nylons. Phenol_sentence_58

Oxidation of benzene and toluene Phenol_section_8

The direct oxidation of benzene to phenol is theoretically possible and of great interest, but it has not been commercialized: Phenol_sentence_59

Phenol_description_list_5

  • C6H6 + O → C6H5OHPhenol_item_5_5

Nitrous oxide is a potentially "green" oxidant that is a more potent oxidant than O2. Phenol_sentence_60

Routes for the generatation of nitrous oxide however remain uncompetitive. Phenol_sentence_61

An electrosynthesis employing alternating current gives phenol from benzene. Phenol_sentence_62

The oxidation of toluene, as developed by Dow Chemical, involves copper-catalyzed reaction of molten sodium benzoate with air: Phenol_sentence_63

Phenol_description_list_6

  • C6H5CH3 + 2 O2 → C6H5OH + CO2 + H2OPhenol_item_6_6

The reaction is proposed to proceed via formation of benzyoylsalicylate. Phenol_sentence_64

Older methods Phenol_section_9

Early methods relied on extraction of phenol from coal derivatives or the hydrolysis of benzene derivatives. Phenol_sentence_65

Hydrolysis of benzenesulfonate Phenol_section_10

An early commercial route, developed by Bayer and Monsanto in the early 1900s, begins with the reaction of a strong base with benzenesulfonate. Phenol_sentence_66

The conversion is represented by this idealized equation: Phenol_sentence_67

Phenol_description_list_7

  • C6H5SO3H + 2 NaOH → C6H5OH + Na2SO3 + H2OPhenol_item_7_7

Hydrolysis of chlorobenzene Phenol_section_11

Chlorobenzene can be hydrolyzed to phenol using base (Dow process) or steam (Raschig–Hooker process): Phenol_sentence_68

Phenol_description_list_8

  • C6H5Cl + NaOH → C6H5OH + NaClPhenol_item_8_8
  • C6H5Cl + H2O → C6H5OH + HClPhenol_item_8_9

These methods suffer from the cost of the chlorobenzene and the need to dispose of the chloride by product. Phenol_sentence_69

Coal pyrolysis Phenol_section_12

Phenol is also a recoverable byproduct of coal pyrolysis. Phenol_sentence_70

In the Lummus Process, the oxidation of toluene to benzoic acid is conducted separately. Phenol_sentence_71

Miscellaneous methods Phenol_section_13

Phenyldiazonium salts hydrolyze to phenol. Phenol_sentence_72

The method is of no commercial interest since the precursor is expensive. Phenol_sentence_73

Phenol_description_list_9

  • C6H5NH2 + HCl/NaNO2 → C6H5OH + N2 + H2O + NaClPhenol_item_9_10

Salicylic acid decarboxylates to phenol. Phenol_sentence_74

Uses Phenol_section_14

The major uses of phenol, consuming two thirds of its production, involve its conversion to precursors for plastics. Phenol_sentence_75

Condensation with acetone gives bisphenol-A, a key precursor to polycarbonates and epoxide resins. Phenol_sentence_76

Condensation of phenol, alkylphenols, or diphenols with formaldehyde gives phenolic resins, a famous example of which is Bakelite. Phenol_sentence_77

Partial hydrogenation of phenol gives cyclohexanone, a precursor to nylon. Phenol_sentence_78

Nonionic detergents are produced by alkylation of phenol to give the alkylphenols, e.g., nonylphenol, which are then subjected to ethoxylation. Phenol_sentence_79

Phenol is also a versatile precursor to a large collection of drugs, most notably aspirin but also many herbicides and pharmaceutical drugs. Phenol_sentence_80

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. Phenol_sentence_81

Depending on the pH of the solution either DNA or RNA can be extracted. Phenol_sentence_82

Medical Phenol_section_15

Phenol was once widely used as an antiseptic, its use pioneered by Joseph Lister (see History section). Phenol_sentence_83

From the early 1900s to the 1970s it was used in the production of carbolic soap. Phenol_sentence_84

Concentrated phenol liquids are commonly used for permanent treatment of ingrown toe and finger nails, a procedure known as a chemical matrixectomy. Phenol_sentence_85

The procedure was first described by Otto Boll in 1945. Phenol_sentence_86

Since that time it has become the chemical of choice for chemical matrixectomies performed by podiatrists. Phenol_sentence_87

Phenol in medicinal formulation is also used as a preservative in some vaccines. Phenol_sentence_88

Phenol spray, usually at 1.4% phenol as an active ingredient, is used medically to help sore throat. Phenol_sentence_89

It is the active ingredient in some oral analgesics such as Chloraseptic spray, TCP and Carmex, commonly used to temporarily treat pharyngitis. Phenol_sentence_90

Niche uses Phenol_section_16

Phenol is so inexpensive that it attracts many small-scale uses. Phenol_sentence_91

It is a component of industrial paint strippers used in the aviation industry for the removal of epoxy, polyurethane and other chemically resistant coatings. Phenol_sentence_92

Phenol derivatives have been used in the preparation of cosmetics including sunscreens, hair colorings, skin lightening preparations, as well as in skin toners/exfoliators. Phenol_sentence_93

However, due to safety concerns, phenol is banned from use in cosmetic products in the European Union and Canada. Phenol_sentence_94

History Phenol_section_17

Phenol was discovered in 1834 by Friedlieb Ferdinand Runge, who extracted it (in impure form) from coal tar. Phenol_sentence_95

Runge called phenol "Karbolsäure" (coal-oil-acid, carbolic acid). Phenol_sentence_96

Coal tar remained the primary source until the development of the petrochemical industry. Phenol_sentence_97

In 1841, the French chemist Auguste Laurent obtained phenol in pure form. Phenol_sentence_98

In 1836, Auguste Laurent coined the name "phène" for benzene; this is the root of the word "phenol" and "phenyl". Phenol_sentence_99

In 1843, French chemist Charles Gerhardt coined the name "phénol". Phenol_sentence_100

The antiseptic properties of phenol were used by Sir Joseph Lister (1827–1912) in his pioneering technique of antiseptic surgery. Phenol_sentence_101

Lister decided that the wounds themselves had to be thoroughly cleaned. Phenol_sentence_102

He then covered the wounds with a piece of rag or lint covered in phenol, or carbolic acid as he called it. Phenol_sentence_103

The skin irritation caused by continual exposure to phenol eventually led to the introduction of aseptic (germ-free) techniques in surgery. Phenol_sentence_104

Joseph Lister was a student at University College London under Robert Liston, later rising to the rank of Surgeon at Glasgow Royal Infirmary. Phenol_sentence_105

Lister experimented with cloths covered in carbolic acid after studying the works and experiments of his contemporary, Louis Pasteur in sterilizing various biological media. Phenol_sentence_106

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. Phenol_sentence_107

In examining Pasteur's research, Lister began to piece together his theory: that patients were being killed by germs. Phenol_sentence_108

He theorized that if germs could be killed or prevented, no infection would occur. Phenol_sentence_109

Lister reasoned that a chemical could be used to destroy the micro-organisms that cause infection. Phenol_sentence_110

Meanwhile, in Carlisle, England, officials were experimenting with a sewage treatment, using carbolic acid to reduce the smell of sewage cess pools. Phenol_sentence_111

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. Phenol_sentence_112

He had his first chance on August 12, 1865, when he received a patient: an eleven-year-old boy with a tibia bone fracture which pierced the skin of his lower leg. Phenol_sentence_113

Ordinarily, amputation would be the only solution. Phenol_sentence_114

However, Lister decided to try carbolic acid. Phenol_sentence_115

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. Phenol_sentence_116

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. Phenol_sentence_117

Reapplying fresh bandages with diluted carbolic acid, the boy was able to walk home after about six weeks of treatment. Phenol_sentence_118

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. Phenol_sentence_119

Second World War Phenol_section_18

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. Phenol_sentence_120

Injections of phenol were used as a means of individual execution by Nazi Germany during the Second World War. Phenol_sentence_121

It was originally used by the Nazis in 1939 as part of the Aktion T4 euthanasia program. Phenol_sentence_122

The Germans learned that extermination of smaller groups was more economical by injection of each victim with phenol. Phenol_sentence_123

Phenol injections were given to thousands of people. Phenol_sentence_124

Maximilian Kolbe was also killed with a phenol injection after surviving two weeks of dehydration and starvation in Auschwitz when he volunteered to die in place of a stranger. Phenol_sentence_125

Approximately one gram is sufficient to cause death. Phenol_sentence_126

Occurrences Phenol_section_19

Phenol is a normal metabolic product, excreted in quantities up to 40 mg/L in human urine. Phenol_sentence_127

The temporal gland secretion of male elephants showed the presence of phenol and 4-methylphenol during musth. Phenol_sentence_128

It is also one of the chemical compounds found in castoreum. Phenol_sentence_129

This compound is ingested from the plants the beaver eats. Phenol_sentence_130

Occurrence in whisky Phenol_section_20

Phenol is a measurable component in the aroma and taste of the distinctive Islay scotch whisky, generally ~30 ppm, but it can be over 160ppm in the malted barley used to produce whisky. Phenol_sentence_131

This amount is different from and presumably higher than the amount in the distillate. Phenol_sentence_132

Biodegradation Phenol_section_21

Cryptanaerobacter phenolicus is a bacterium species that produces benzoate from phenol via 4-hydroxybenzoate. Phenol_sentence_133

Rhodococcus phenolicus is a bacterium species able to degrade phenol as sole carbon sources. Phenol_sentence_134

Toxicity Phenol_section_22

Phenol and its vapors are corrosive to the eyes, the skin, and the respiratory tract. Phenol_sentence_135

Its corrosive effect on skin and mucous membranes is due to a protein-degenerating effect. Phenol_sentence_136

Repeated or prolonged skin contact with phenol may cause dermatitis, or even second and third-degree burns. Phenol_sentence_137

Inhalation of phenol vapor may cause lung edema. Phenol_sentence_138

The substance may cause harmful effects on the central nervous system and heart, resulting in dysrhythmia, seizures, and coma. Phenol_sentence_139

The kidneys may be affected as well. Phenol_sentence_140

Long-term or repeated exposure of the substance may have harmful effects on the liver and kidneys. Phenol_sentence_141

There is no evidence that phenol causes cancer in humans. Phenol_sentence_142

Besides its hydrophobic effects, another mechanism for the toxicity of phenol may be the formation of phenoxyl radicals. Phenol_sentence_143

Since phenol is absorbed through the skin relatively quickly, systemic poisoning can occur in addition to the local caustic burns. Phenol_sentence_144

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. Phenol_sentence_145

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_sentence_146

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. Phenol_sentence_147

Chemical burns from skin exposures can be decontaminated by washing with polyethylene glycol, isopropyl alcohol, or perhaps even copious amounts of water. Phenol_sentence_148

Removal of contaminated clothing is required, as well as immediate hospital treatment for large splashes. Phenol_sentence_149

This is particularly important if the phenol is mixed with chloroform (a commonly used mixture in molecular biology for DNA and RNA purification). Phenol_sentence_150

Phenol is also a reproductive toxin causing increased risk of abortion and low birth weight indicating retarded development in utero. Phenol_sentence_151

Phenols Phenol_section_23

Main article: Phenols Phenol_sentence_152

The word phenol is also used to refer to any compound that contains a six-membered aromatic ring, bonded directly to a hydroxyl group (-OH). Phenol_sentence_153

Thus, phenols are a class of organic compounds of which the phenol discussed in this article is the simplest member. Phenol_sentence_154

See also Phenol_section_24

Phenol_unordered_list_10


Credits to the contents of this page go to the authors of the corresponding Wikipedia page: en.wikipedia.org/wiki/Phenol.