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Higher alkane

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Higher alkane

Higher alkanes are alkanes with a high number of carbon atoms. It is common jargon. One definition says higher alkanes are alkanes having nine or more carbon atoms. Thus, according to this definition, nonane is the lightest higher alkane. As pure substances, higher alkanes are rarely significant, but they are major components of useful lubricants and fuels.

The preparation of specific long-chain hydrocarbons typically involves manipulations of long chain precursors or the coupling of two medium-chain components. For the first case, fatty acids can be a source of higher alkanes via decarboxylation reaction. Such processes have been investigated as a route to biodiesel.

Fatty acid esters and fatty acid nitriles react with long chain Grignard reagents to give, after suitable workup, long-chain ketones. The Wolff-Kishner Reaction provides a way to remove the ketone functionality, giving long-chain hydrocarbons.

Even-numbered, long-chain hydrocarbons can also be synthesized through electrolysis and the Wurtz reactions of alkyl bromides.

Higher alkanes can also be isolated and purified from natural or synthetic mixtures. Coal tar is a traditional source of mixtures of long-chain hydrocarbons. Careful fractionation, first using urea clathrates to remove branched hydrocarbons, and then distillation, produces pure n-hydrocarbons from petroleum.

Regarding synthetic sources, the Fischer-Tropsch process (or FT process) produces a mixture of hydrocarbons by the hydrogenation of carbon monoxide. The products obtained are liquid hydrocarbons and waxy solids, mostly n-paraffins. The liquid fraction ranges from C6 to C20, while the solid fraction consists of hydrocarbons above C21.

Some branched higher alkanes are insect pheromones. 9- and 7-methyltricosanes are active for ladybird beetles (Adalia bipunctata). The emerald ash borer (Agrilus planipennis Fairmaire) responds to 9-methylpentacosane. Female Asian long-horned beetles Anoplophora glabripennis, which are very damaging, secrete 2-methyldocosane.

Higher alkanes in general are relatively inert, just like low molecular weight alkanes they can react with oxygen and start a combustion reaction. They can undergo cracking in the presence of alumina or silica catalysts, forming lower alkanes and alkenes.

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