MadSci Network: Chemistry

Re: Under what conditions could naphthenic oil form a naphthalene?

Date: Tue Apr 17 14:09:31 2001
Posted By: Tony Gaglierd, Faculty, Natural Science and Engineering Technology, Point Park College
Area of science: Chemistry
ID: 986316659.Ch

Stacy from Ohio does not indicate wether chloronapthalenes were actually 
found in the spent fluids or wether there presence was inferred.

Chlornapthalenes present

Napthenic oil (as opposed to napthalenic oil)is a misnomer because that 
type of fluid contains little or no naphthalene. Rather it is a petroleum-
based fluid that contains a high percentage of alicyclic or closed-ringed 
aliphatic compounds. For naphthalene to form, a 10-carbon bicyclic compound
(decalin) would have to dehydrogenate under high temperatures. Traces of a
contaminant such as iron particles could then react with chlorine 
containing compounds to form ferric chloride. The ferric chloride could 
catalyze the chlorination of naphthalene.

Alternate Explanation

A more likely scenario is that the fluoroelastemers were degraded by 
oxidants such as peroxides. Lubricating oils like tires contain many 
additives. Those used in lubricating oils include
antioxidants, antiwear additives, and corrosion inhibitors. Peroxide 
formation is accelerated by heat light and catalysts. Oxidation inhibitors 
function in one of three ways: (1) by combining with and modifying 
peroxides, (2)by decomposing the peroxide, or (3) by rendering the
oxidation catalysts inert. Water, acids or other contaminants present in 
the lubricating oils could deactivated the anti oxidants and provide an 
avenue for peroxides to degrade the elastomers.     

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