Cresol

Last updated
Isomers of Cresol [1] [2] [3] [4]
Skeletal formula
O-Kresol.svg
M-Kresol.svg
P-Kresol.svg
Ball-and-stick model Ortho-cresol-3D-balls.png Meta-cresol-3D-balls.png Para-cresol-3D-balls.png
General
Common name o-cresol m-cresol p-cresol
Preferred IUPAC name 2-methylphenol3-methylphenol4-methylphenol
Systematic name 2-methylbenzenol3-methylbenzenol4-methylbenzenol
Other namesortho-cresol
2-hydroxytoluene
meta-cresol
3-hydroxytoluene
para-cresol
4-hydroxytoluene
Molecular formula C7H8O
SMILES oc1c(C)cccc1oc1cc(C)ccc1oc1ccc(C)cc1
Molar mass 108.14 g/mol
Appearance at room
temperature and pressure
colorless crystalsthicker liquidgreasy-looking solid
CAS number [95-48-7][108-39-4][106-44-5]
mixture of cresols (tricresol): [1319-77-3]
Properties
Density and phase 1.05 g/cm3, solid1.03 g/cm3, liquid1.02 g/cm3, liquid
Solubility in pure water
at 20−25 °C
2.5 g/100 ml2.4 g/100 ml1.9 g/100 ml
soluble in strongly alkaline water
Melting point 29.8 °C (303.0 K)11.8 °C (285.0 K)35.5 °C (309.7 K)
Boiling point 191.0 °C (464.2 K)202.0 °C (475.2 K)201.9 °C (475.1 K)
Acidity (pKa)10.28710.0910.26
Viscosity solid at 25 °C ? cP at 25 °Csolid at 25 °C
Structure
Dipole moment 1.35 D 1.61 D 1.58 D
Hazards
SDS
Main hazards flammable, ingestion and inhalation toxicity hazard
Flash point 81 °C c.c.86 °C86 °C c.c.
GHS pictograms GHS-pictogram-acid.svg GHS-pictogram-skull.svg
RTECS numberGO6300000GO6125000GO6475000
Related compounds
Related phenols xylenols
Related compounds bromocresol green, cresol red
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Infobox disclaimer and references

Cresols (also known as hydroxytoluene, toluenol, benzol 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 methyl phenols . Cresols commonly occur as either solids or liquids because their melting points are generally close to room temperature. Like other types of phenols, they are slowly oxidized by exposure to air, and the resulting impurities often give the samples a yellow to brownish red tint. Cresols have an odor characteristic to that of other simple phenols, reminiscent to some of a "coal tar" smell. The name "cresol" is an adduct of phenol and their traditional source, creosote.

Contents

Structure and production

In its chemical structure, a molecule of cresol has a methyl group substituted onto the ring of phenol. There are three forms (isomers) of cresol: ortho-cresol (o-cresol), meta-cresol (m-cresol), and para-cresol (p-cresol). These forms occur separately or as a mixture, which can also be called cresol or more specifically, tricresol.[ citation needed ] About half of the world's supply of cresols are extracted from coal tar. The rest is produced by hydrolysis of chlorotoluenes or the related sulfonates. Another method entails methylation of phenol with methanol over a solid acid catalyst, often comprising magnesium oxide or alumina. Temperatures above 300 °C are typical. Anisole converts to cresols under these conditions. [5] [6]

Another isomer of cresol is called Benzyl alcohol, or alpha-cresol (α-cresol). Benzyl alcohol has a hydroxy group inside a methyl group on the benzene ring.

Applications

Cresols are precursors or synthetic intermediates to other compounds and materials, including plastics, pesticides, pharmaceuticals, and dyes. [6]

For cresol bactericides or disinfectants the mechanism of action is due to the destruction of bacterial cell membranes. [7] [8]

Most recently, cresols have been used to create a breakthrough in manufacturing carbon nanotubes at scale that are separated and not twisted, without additional chemicals that change the surface properties of the nanotubes. [9] [10]

Commercial examples

Derivatives

Derivatives of p-cresol include:

Derivatives of o-cresol include:

Derivatives of m-cresol include:

Health effects

When cresols are inhaled, ingested, or applied to the skin, they can be very harmful. Effects observed in people include irritation and burning of skin, eyes, mouth, and throat; abdominal pain and vomiting; heart damage; anemia; liver and kidney damage; facial paralysis; coma; and death.

Breathing high levels of cresols for a short time results in irritation of the nose and throat. Aside from these effects, very little is known about the effects of breathing cresols, for example, at lower levels over longer times.

Ingesting high levels results in kidney problems, mouth and throat burns, abdominal pain, vomiting, and effects on the blood and nervous system.

Skin contact with high levels of cresols can burn the skin and damage the kidneys, liver, blood, brain, and lungs.

Short-term and long-term studies with animals have shown similar effects from exposure to cresols. No human or animal studies have shown harmful effects from cresols on reproduction.

It is not known what the effects are from long-term ingestion or skin contact with low levels of cresols.

The Occupational Safety and Health Administration has set a permissible exposure limit at 5 ppm (22 mg/m3) over an eight-hour time-weighted average, while the National Institute for Occupational Safety and Health recommends a limit of 2.3 ppm (10 mg/m3). [12]

See also

Related Research Articles

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<span class="mw-page-title-main">Phenol</span> Organic compound (C6H5OH)

Phenol, or Benzenol, is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group bonded to a hydroxy group. Mildly acidic, it requires careful handling because it can cause chemical burns.

<span class="mw-page-title-main">Creosote</span> Tar distillation byproduct used as wood preservative

Creosote is a category of carbonaceous chemicals formed by the distillation of various tars and pyrolysis of plant-derived material, such as wood, or fossil fuel. They are typically used as preservatives or antiseptics.

<span class="mw-page-title-main">Butylated hydroxytoluene</span> Chemical compound

Butylated hydroxytoluene (BHT), also known as dibutylhydroxytoluene, is a lipophilic organic compound, chemically a derivative of phenol, that is useful for its antioxidant properties. BHT is widely used to prevent free radical-mediated oxidation in fluids and other materials, and the regulations overseen by the U.S. F.D.A.—which considers BHT to be "generally recognized as safe"—allow small amounts to be added to foods. Despite this, and the earlier determination by the National Cancer Institute that BHT was noncarcinogenic in an animal model, societal concerns over its broad use have been expressed. BHT has also been postulated as an antiviral drug, but as of December 2022, use of BHT as a drug is not supported by the scientific literature and it has not been approved by any drug regulatory agency for use as an antiviral.

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<i>p</i>-Xylene Chemical compound

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Lysol is a brand of American cleaning and disinfecting products distributed by Reckitt, which markets the similar Dettol or Sagrotan in other markets. The line includes liquid solutions for hard and soft surfaces, air treatment, and hand washing. The active ingredient in many Lysol products is benzalkonium chloride, but the active ingredient in the Lysol "Power and Free" line is hydrogen peroxide. Lysol has been used since its invention in the late 19th century as a household and industrial cleaning agent, and previously as a medical disinfectant.

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p-Chlorocresol, or 4-chloro-3-methylphenol (ClC6H3CH3OH), also known as p-chloro-m-cresol, is a potent disinfectant and antiseptic. It appears as a pinkish white crystalline solid and has a melting point of 64-66°C. It is also used as a preservative in cosmetics and medicinal products for both humans and animals. It is used as an active ingredient in some preparations of veterinary medicines for tropical, oral and parenteral use. Normally, the concentration of p-Chlorocresol in oral and parenteral veterinary products are 0.1-0.2%. Concentrations are higher (~0.5%) in tropical veterinary products. p-Chlorocresol contains microbial activity against both gram positive and gram negative bacteria and fungi.

ortho-Cresol (IUPAC name: 2-methylphenol, also known as 2-hydroxytoluene or ortho-Toluenol) is an organic compound with the formula CH3C6H4(OH). It is a colourless solid that is widely used intermediate in the production of other chemicals. It is a derivative of phenol and is an isomer of p-cresol and m-cresol.

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3-Methylphenethylamine (3MPEA) is an organic compound with the chemical formula of C9H13N. 3MPEA is a human trace amine associated receptor 1 (TAAR1) agonist, a property which it shares with its monomethylated phenethylamine isomers, such as amphetamine (α-methylphenethylamine), β-methylphenethylamine, and N-methylphenethylamine.

Creolin is a generic name for disinfectants whose composition varies according to origin. One of its uses is as a disinfectant. It is extracted from the dry distillation of wood. The residue remaining in the autoclave vessel is a dark, syrupy mass called creosote, which is composed mainly of phenolic acid and cresylic acid. The original composition of creolin was this creosote tar oil, caustic soda, soaps, and very little water. It is of low technology and a very powerful disinfectant.

References

  1. o-CRESOL (ICSC)
  2. m-CRESOL (ICSC)
  3. p-CRESOL (ICSC)
  4. Pubchem. "o-cresol". pubchem.ncbi.nlm.nih.gov. Retrieved 2018-01-16.
  5. W. W. Hartman (1923). "p-Cresol". Organic Syntheses. 3: 37. doi:10.15227/orgsyn.003.0037.
  6. 1 2 Helmut Fiegein "Cresols and Xylenols" in Ullmann's Encyclopedia of Industrial Chemistry" 2007; Wiley-VCH, Weinheim. doi : 10.1002/14356007.a08_025
  7. Judis, Joseph (1962). "Studies on the Mechanism of Action of Phenolic Disinfectants I". Journal of Pharmaceutical Sciences. 51 (3): 261–265. doi:10.1002/jps.2600510317. PMID   14452711.
  8. "IDENTIFICATION Name Cresol". DrugBank Online. 12 June 2020.
  9. "Making carbon nanotubes as usable as common plastics: Researchers discover that cresols disperse carbon nanotubes at unprecedentedly high concentrations". ScienceDaily, Northwestern University. 15 May 2018. Archived from the original on 2018-05-16.
  10. Chiou, Kevin; Byun, Segi; Kim, Jaemyung; Huang, Jiaxing (29 May 2018). "Additive-free carbon nanotube dispersions, pastes, gels, and doughs in cresols". Proceedings of the National Academy of Sciences. 115 (22): 5703–5708. Bibcode:2018PNAS..115.5703C. doi: 10.1073/pnas.1800298115 . PMC   5984515 . PMID   29760075. Open Access logo PLoS transparent.svg
  11. SIMMONS, W.H. (1908). THE HANDBOOK OF SOAP MANUFACTURE no. SCOTT, GREENWOOD & SON.
  12. Documentation for Immediately Dangerous To Life or Health Concentrations (IDLHs) - Cresol (o, m, p isomers)