Nonene

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 name	Non-1-ene	Non-2-ene	Non-3-ene	Non-4-ene
Structure
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)
CAS Number	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	^[2]	^[3]	^[5]	^[4]
GHS hazard statements	H226, H304, H315, H319, H335	H226	H226	H226, H304
	P261, P301+310, P305+351+338, P331			P210, P233, P240, P241, P242, P243, P280, P301, P310 P331, P303+361+353, P370+378, P403+235, P405, P501

References

↑ Fiege, H.; Voges, H. W.; Hamamoto, T.; Umemura, S.; Iwata, T.; Miki, H.; Fujita, Y.; Buysch, H. J. et al. (2000-06-15) (in en). 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. https://onlinelibrary.wiley.com/doi/10.1002/14356007.a19_313. Retrieved 2022-06-08.
↑ ^2.0 ^2.1 ^2.2 ^2.3 Record of 1-Nonen in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 1 February 2016.
↑ ^3.0 ^3.1 ^3.2 Sigma-Aldrich Co., trans-2-Nonen, 99%. Retrieved on 2 June 2017.
↑ ^4.0 ^4.1 ^4.2 Entry from 4-Nonene (cis- and trans-mixture) from TCI Europe, retrieved on 2 June 2017
↑ ^5.0 ^5.1 Sigma-Aldrich Co., trans-3-Nonene, 99%. Retrieved on 2 June 2017.

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[1] Fiege, H.; Voges, H. W.; Hamamoto, T.; Umemura, S.; Iwata, T.; Miki, H.; Fujita, Y.; Buysch, H. J. et al. (2000-06-15) (in en). 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. https://onlinelibrary.wiley.com/doi/10.1002/14356007.a19_313. Retrieved 2022-06-08.

[GESTIS-2] 2.0 ^2.1 ^2.2 ^2.3 Record of 1-Nonen in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 1 February 2016.

[Sigma-3] 3.0 ^3.1 ^3.2 Sigma-Aldrich Co., trans-2-Nonen, 99%. Retrieved on 2 June 2017.

[TCI-4] 4.0 ^4.1 ^4.2 Entry from 4-Nonene (cis- and trans-mixture) from TCI Europe, retrieved on 2 June 2017

[Sigma3-5] 5.0 ^5.1 Sigma-Aldrich Co., trans-3-Nonene, 99%. Retrieved on 2 June 2017.

v t e Alkenes
Alkenes	Ethene ( C₂H₄ ) Propene ( C₃H₆ ) Butene ( C₄H₈ ) Pentene ( C₅H₁₀ ) Hexene ( C₆H₁₂ ) Heptene ( C₇H₁₄ ) Octene ( C₈H₁₆ ) Nonene ( C₉H₁₈ ) Decene ( C₁₀H₂₀ )
Preparations	Dehydrohalogenation from haloalkane Dehydration reaction from alcohol Semihydrogenation from alkyne Bamford–Stevens reaction Barton–Kellogg reaction Boord olefin synthesis Chugaev elimination Cope reaction Corey–Winter olefin synthesis Grieco elimination Hofmann elimination Horner–Wadsworth–Emmons reaction Hydrazone iodination Julia olefination Kauffmann olefination McMurry reaction Peterson olefination Ramberg–Bäcklund reaction Shapiro reaction Takai olefination Wittig reaction Olefin metathesis Ene reaction Cope rearrangement
Reactions	Hydrogenation Halogenation Hydration Electrophilic addition Oxymercuration reaction Hydroboration Cyclopropanation Epoxidation Dihydroxylation Ozonolysis Hydrohalogenation Polymerization Diels–Alder reaction Wacker process Dehydrogenation Ene reaction Friedel-Crafts Alkylation