''meta''-Cresol, also 3-methylphenol, is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon- hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...

with the formula CH₃C₆H₄(OH). It is a colourless, viscous liquid that is used as an intermediate in the production of other chemicals. It is a derivative of

phenol Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it ...

and is an isomer of ''p''-cresol and ''o''-cresol.

Production

Together with many other compounds, ''m''-cresol is traditionally extracted from

coal tar Coal tar is a thick dark liquid which is a by-product of the production of coke and coal gas from coal. It is a type of creosote. It has both medical and industrial uses. Medicinally it is a topical medication applied to skin to treat psoria ...

, the volatile materials obtained in the production of coke from (bituminous) coal. This residue contains a few percent by weight of

and isomeric

cresol Cresols (also hydroxytoluene or cresylic acid) are a group of aromatic organic compounds. They are widely-occurring phenols (sometimes called ''phenolics'') which may be either natural or manufactured. They are also categorized as methylphenols. ...

s. In the cymene–cresol process,

toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon. It is a colorless, water-insoluble liquid with the smell associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) ...

is alkylated with

propylene Propylene, also known as propene, is an unsaturated organic compound with the chemical formula CH3CH=CH2. It has one double bond, and is the second simplest member of the alkene class of hydrocarbons. It is a colorless gas with a faint petrole ...

to give isomers of

cymene ''p''-Cymene is a naturally occurring aromatic organic compound. It is classified as an alkylbenzene related to a monoterpene. Its structure consists of a benzene ring ''para''-substituted with a methyl group and an isopropyl group. ''p''-C ...

, which can be oxidatively dealkylated analogous to the

cumene process The cumene process (cumene-phenol process, Hock process) is an industrial process for synthesizing phenol and acetone from benzene and propylene. The term stems from cumene (isopropyl benzene), the intermediate material during the process. It was ...

. Another method, involves

carbonylation Carbonylation refers to reactions that introduce carbon monoxide into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry. The term carbo ...

of a mixture of

methallyl chloride Methallyl chloride is the organic compound with the formula CH2=C(CH3)CH2Cl. It is a colorless liquid and a lacrymator. Its properties are similar to those of allyl chloride. It is a strong alkylating agent used to install isobutenyl groups. ...

and

acetylene Acetylene ( systematic name: ethyne) is the chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in its pur ...

in the presence of

nickel carbonyl Nickel carbonyl (IUPAC name: tetracarbonylnickel) is a nickel(0) organometallic compound with the formula Ni(CO)4. This colorless liquid is the principal carbonyl of nickel. It is an intermediate in the Mond process for producing very high-pu ...

Applications

''m''-Cresol is a precursor to numerous compounds. Important applications include: * pesticides such as fenitrothion and

fenthion Fenthion is an organothiophosphate insecticide, avicide, and acaricide. Like most other organophosphates, its mode of action is via cholinesterase inhibition. Due to its relatively low toxicity towards humans and mammals, fenthion is listed as ...

* synthetic

vitamin E Vitamin E is a group of eight fat soluble compounds that include four tocopherols and four tocotrienols. Vitamin E deficiency, which is rare and usually due to an underlying problem with digesting dietary fat rather than from a diet low in vitami ...

methylation In the chemical sciences, methylation denotes the addition of a methyl group on a substrate, or the substitution of an atom (or group) by a methyl group. Methylation is a form of alkylation, with a methyl group replacing a hydrogen atom. These t ...

to give 2,3,6-trimethylphenol *

antiseptic An antiseptic (from Greek ἀντί ''anti'', "against" and σηπτικός ''sēptikos'', "putrefactive") is an antimicrobial substance or compound that is applied to living tissue/skin to reduce the possibility of infection, sepsis, or putre ...

s, such as

amylmetacresol Amylmetacresol (AMC) is an antiseptic used to treat infections of the mouth and throat. It is used as an active pharmaceutical ingredient in Strepsils, Cēpacol, Gorpils and Lorsept throat lozenges, typically in combination with dichloroben ...

* a

solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...

for

polymer A polymer (; Greek ''poly-'', "many" + '' -mer'', "part") is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic and ...

s. For example,

polyaniline Polyaniline (PANI) is a conducting polymer and organic semiconductor of the semi-flexible rod polymer family. The compound has been of interest since the 1980s because of its electrical conductivity and mechanical properties. Polyaniline is one ...

is cast from a solution of ''m''-cresol to form a polyaniline film with a superior conductivity than polyaniline alone. This phenomenon is known as secondary doping. *preservatives in some

insulin Insulin (, from Latin ''insula'', 'island') is a peptide hormone produced by beta cells of the pancreatic islets encoded in humans by the ''INS'' gene. It is considered to be the main anabolic hormone of the body. It regulates the metabol ...

preparations *the starting point in the

total synthesis Total synthesis is the complete chemical synthesis of a complex molecule, often a natural product, from simple, commercially-available precursors. It usually refers to a process not involving the aid of biological processes, which distinguishes i ...

thymol Thymol (also known as 2-isopropyl-5-methylphenol, IPMP), , is a natural monoterpenoid phenol derivative of ''p''-Cymene, isomeric with carvacrol, found in oil of thyme, and extracted from '' Thymus vulgaris'' (common thyme), ajwain, and va ...

, an important synthetic chemical for regions lacking natural sources of the flavor compound: :: C₇H₈O + C₃H₆ C₁₀H₁₄O *synthesis of dicresulene and policresulen *synthesis of toliprolol, tolamolol & cresatin

Natural occurrences

''m''-Cresol is a component found in temporal glands secretions during

musth Musth or must (from Persian, )''The Oxford Dictionary and Thesaurus: American edition'', published 1996 by Oxford University Press; p. 984 is a periodic condition in bull (male) elephants characterized by aggressive behavior and accompanied by ...

in male African elephants (''Loxodonta africana''). ''m''-Cresol is a constituent of

tobacco smoke Tobacco smoke is a sooty aerosol produced by the incomplete combustion of tobacco during the smoking of cigarettes and other tobacco products. Temperatures in burning cigarettes range from about 400 °C between puffs to about 900 °C d ...

. ''m''-Cresol is a component found in secretions from the ant ''

Colobopsis saundersi ''Colobopsis saundersi'', synonym ''Camponotus saundersi'', is a species of ant found in Malaysia and Brunei, belonging to the genus ''Colobopsis''. A worker can explode suicidally and aggressively as an ultimate act of defense, an ability it ha ...

'' during

Autothysis Autothysis (from the Greek roots ''autos-'' "self" and ''thysia'' "sacrifice") or suicidal altruism is the process where an animal destroys itself via an internal rupturing or explosion of an organ which ruptures the skin. The term was proposed by ...

References

External links

NIOSH Pocket Guide to Chemical Hazards
cdc.gov

chemicalbook.com {{DEFAULTSORT:Cresol, m- Cresols

Production

Applications

Natural occurrences

See also

References

External links