A fraction of naphthenic acids isolated from the lubricating oil portion of a Gulf Coast crude petroleum has been investigated in detail. The fraction had an average molecular weight of 317 and an average molecular formula of C20.7H35.2O2.1. The corresponding naphthene hydrocarbons were prepared from these acids by way of the ethyl esters, alcohols, and iodides. These naphthene hydrocarbons were found to have higher viscosity indices than those of a typical naphthene-base oil.Evidence was obtained to indicate that the acids were monobasic compounds containing on the average about 2.6 rings per molecule. No more than about 5 per cent by weight of aromatic material was present.

Vol. 58 yielded 14 g. of /S-chloroethanesulfonyl chloride. Hydrolysis yielded ß-chloroethanesulfonic acid.10 Ammonium /3-Chloroethanesulfonate.-The viscous ßchloroethanesulfonic acid was treated with coned, ammonium hydroxide and the solution evaporated to dryness under reduced pressure. The residue was crystallized from alcohol.

It has been well established that natural petroleum oils consist mainly of a mixture of aliphatic, naphthenic and aromatic hydrocarbons or chemical combinations of these types in various proportions. Relative to the naphthenic or saturated ring portion, the average number of rings per molecule can be determined by known methods of ring analysis.2 For lubricating oils the values generally range from one to five or more rings per molecule.With respect to the size of the rings present, some evidence has caused several investigators to assume that six-carbon membered (cyclohexane) rings predominate in the naphthenic portion.2 However, more recent indications are that five-carbon membered (cyclopentane) rings may be present and may even, in many cases, be in the majority.3 This latter theory is also supported by the fact that cyclopentane rings have generally been found in the naphthenic acids occurring in petroleum.4Attempts to solve this problem have been hindered by the absence of physical data on pure multicyclic compounds containing cyclopentane rings. Only bicyclopentyl itself has been investigated to any great extent.5 Important additions to the field of dicyclopentyl and bicyclopentyl derivatives have been made recently by several investigators6a,b,c but practically noth-(1) Presented before the Division of Petroleum Chemistry of the

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