Nonene

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Nonene is an alkene with the molecular formula C9H18. Many structural isomers are possible, depending on the location of the C=C double bond and the branching of the other parts of the molecule. Industrially, the most important nonenes are trimers of propene: Tripropylene. This mixture of branched nonenes is used in the alkylation of phenol to produce nonylphenol, a precursor to detergents, which are also controversial pollutants. [1]

Linear nonenes

Linear Nonene
Name 1-Nonene 2-Nonene 3-Nonene 4-Nonene
Systematic nameNon-1-eneNon-2-eneNon-3-eneNon-4-ene
Structure Non-1-ene 200.svg Cis-Non-2-ene structure.svg
Trans-Non-2-ene structure.svg
Cis-Non-3-ene structure.svg
Trans-Non-3-ene structure.svg
Cis-Non-4-ene structure.svg
Trans-Non-4-ene structure.svg
CAS Number 124-11-8
  • 2216-38-8
  • 6434-77-1 (cis)
  • 6434-78-2 (trans)
  • 125146-82-9
  • 20237-46-1 (cis)
  • 20063-77-8 (trans)
  • 2198-23-4
  • 10405-84-2 (cis)
  • 10405-85-3 (trans)
27215-95-8 (all isomers)
PubChem CID 31285 from PubChem CID 33744 from PubChem CID 88350 from PubChem CID 94226 from PubChem
Chemical formula C9H18
Molecular weight 126.24 g·mol−1
Melting point −81 °C [2]
Boiling point 147 °C [2] 144–145 °C [3] 147 °C [4]
Density 0,73 g·cm−3 (20 °C) [2] 0,734 g·cm−3 (25 °C) [3] 0,734 g·cm−3 (25 °C) [5] 0,73 g·cm−3 [4]
GHS hazard pictograms GHS-pictogram-flamme.svg GHS-pictogram-silhouette.svg GHS-pictogram-exclam.svg [2] GHS-pictogram-flamme.svg [3] GHS-pictogram-flamme.svg [5] GHS-pictogram-flamme.svg GHS-pictogram-silhouette.svg [4]
GHS hazard statements H226, H304, H315, H319, H335H226H226H226, H304
P261, P301+P310, P305+P351+P338, P331P210, P233, P240, P241, P242, P243, P280, P301, P310
P303+P361+P353, P331, P370+P378, P403+P235, P405, P501

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6
H
5
OH
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<span class="mw-page-title-main">Resveratrol</span> Polyphenol with a stilbene skeleton

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

Nonylphenols are a family of closely related organic compounds composed of phenol bearing a 9 carbon-tail. Nonylphenols can come in numerous structures, all of which may be considered alkylphenols. They are used in manufacturing antioxidants, lubricating oil additives, laundry and dish detergents, emulsifiers, and solubilizers. They are used extensively in epoxy formulation in North America but its use has been phased out in Europe. These compounds are also precursors to the commercially important non-ionic surfactants alkylphenol ethoxylates and nonylphenol ethoxylates, which are used in detergents, paints, pesticides, personal care products, and plastics. Nonylphenol has attracted attention due to its prevalence in the environment and its potential role as an endocrine disruptor and xenoestrogen, due to its ability to act with estrogen-like activity. The estrogenicity and biodegradation heavily depends on the branching of the nonyl sidechain. Nonylphenol has been found to act as an agonist of the GPER (GPR30).

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Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oily liquid has a sweet odor reminiscent of benzaldehyde. Over time, samples of cyclohexanone assume a pale yellow color. Cyclohexanone is slightly soluble in water and miscible with common organic solvents. Millions of tonnes are produced annually, mainly as a precursor to nylon.

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H
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<span class="mw-page-title-main">Gold(III) bromide</span> Chemical compound

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<span class="mw-page-title-main">Asterric acid</span> Chemical compound

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

Mesitol (2,4,6-trimethylphenol) is an organic compound with the formula (CH3)3C6H2OH. It is one of several isomers of trimethylphenol. The name and structure of mesitol derives from the combination of mesitylene and phenol.

<span class="mw-page-title-main">Aluminium phenolate</span> Chemical compound

Aluminium phenolate is the metalloorganic compound with the formula [Al(OC6H5)3]n. It is a white solid. 27Al NMR studies suggest that aluminium phenolate exists in benzene solution as a mixture of dimer and trimer. The compound is can be prepared by the reaction of elemental aluminium with phenol:

<span class="mw-page-title-main">2-Iodophenol</span> Chemical compound

2-Iodophenol (o-iodophenol) is an aromatic organic compound with the formula IC6H4OH. It is a pale yellow solid that melts near room temperature. It undergoes a variety of coupling reactions in which the iodine substituent is replaced by a new carbon group ortho to the hydroxy group of the phenol, which can be followed by cyclization to form heterocycles.

References

  1. Fiege, H.; Voges, H. W.; Hamamoto, T.; Umemura, S.; Iwata, T.; Miki, H.; Fujita, Y.; Buysch, H. J.; Garbe, D. (2000-06-15). Phenol Derivatives. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA. pp. a19_313. doi:10.1002/14356007.a19_313. ISBN   978-3-527-30673-2. OCLC   46878292 . Retrieved 2022-06-08.{{cite book}}: |work= ignored (help)
  2. 1 2 3 4 Record of 1-Nonen in the GESTIS Substance Database of the Institute for Occupational Safety and Health , accessed on 1 February 2016.
  3. 1 2 3 Sigma-Aldrich Co. , trans-2-Nonen, 99% . Retrieved on 2 June 2017.
  4. 1 2 3 Entry from 4-Nonene (cis- and trans-mixture) from TCI Europe, retrieved on 2 June 2017
  5. 1 2 Sigma-Aldrich Co. , trans-3-Nonene, 99% . Retrieved on 2 June 2017.