198b University Geological Survey of Kansas. 
during the course of time may bring about another phase—the polymeri- 
zation and addition of unsaturated residues—producing high molecular 
products, such as lubricating oils. 
“The changes occurring during these phases may overlap. Some sub- 
stances may be converted into end-products while others are still in 
transition; for example, the ethylenes. Others again may not yet have 
begun to change; for example, the wax esters. Petroleum deposits may, 
therefore, be looked upon as continually undergoing transformation. 
“The different groups of hydrocarbons may have originated somewhat. 
as follows: 
“First. The methane series (homologues of marsh-gas) are formed 
directly from bitumen; that is, from the intermediate products formed in 
part from fatty radicals by loss of carbon dioxide (high molecular hydro- 
carbons with radicals of free fatty acids and their esters). 
“Second. The ethylene series (olefines). In so far as the lower mem- 
bers occur, they must have been formed directly. On account of their 
unsaturated nature and their tendency to unite and to polymerize, they 
in time disappear, but to some extent are re-formed during the distilla- 
tion of petroleum, especially in the high-boiling portions; for example, 
in the cracking process. 
“Third. The naphthene series. The relatively larger quantities of 
naphthenes are probably rather indirectly formed than directly by the 
decomposition of hydroaromatic olefines by heat and pressure, according 
to Kraemer and Aschan. Experiments of the speaker, together with 
Eberle, confirm the results of Aschan. Hexylene (methyl-propyl- 
ethylene) of density of 0.6870 and melting-point 67° to 68°, after heating 
in a sealed tube for fourteen days at 360° to 365°, shows a density equal 
to 0.7282° and melting-point 67° to 240°, and a lessened bromine absorp- 
tion. According to Rogowski, propylene heated to from 400° to 405° is 
more than half converted into a gas containing tri-methylene which no 
longer absorbs bromine. The remaining unsaturated hydrocarbons can 
polymerize to lubricating oils. 
“Fourth. The lubricating oils (difficultly separable mixtures of satu- 
rated and unsaturated hydrocarbons of the methane, naphthene, ethylene 
and acetylene series, etc.) may originate by direct decomposition of fatty 
esters through rapid or slow change or through self-polymerization and 
addition of unsaturated hydrocarbons which were formed through the 
breaking up of organic residues with or without catalyzers,* or by syn- 
thesis from unsaturated components, such as styrol and allyl alcohol. 
Benzene and its homologues may have been formed at moderately high 
temperatures by the decomposition of fats or from the substituted fatty 
acids derived from albuminous substances; or also by ring formation 
from aliphatic compounds. 
“There is very strong evidence in favor of ferment action only in the 
first and not in the last stages of transformation, and, on the other hand, 
of violent action in the closing processes of formation of the proto- 
petroleums. : 
* Ethylene hydrocarbons such as amylene and hexylene were found by Rosenquist to go 
over into high boiling viscous oils when warmed under pressure, even without the use of 
aluminum chloride. 
