The Synthesis of Multicyclopentyls¹

Abstract

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

Synthesis of high density aviation fuel with cyclopentanol derived from lignocellulose

“…Over the 30 wt.% Ni-SiO 2 -DP catalyst, evidently higher carbon yields to bi(cyclopentane) (41.4%) and tri(cyclopentane) (12.8%) were achieved by the HDO of Guerbet products of cyclopentanol at 503 K and 6 MPa. These alkanes have high densities (bi(cyclopentane): 0.86 g mL −1 ; tri(cyclopentane) 0.91 g mL −1 )30. In real application, they can be used as high-density aviation fuels or additives to increase the volumetric heating value of bio-jet fuel or bio-diesel.…”

The Chemistry and Utilization of Cyclopentadiene.

“…to -40°C. ), added with the production of cyclopentenyl chloride (95,140,170). This compound decomposed on standing, with resinification and evolution of The halogenated derivatives of cyclopentadiene are interesting starting points for the synthesis of a large number of organic derivatives, including amines, alcohols, and thiocyanates.…”

“…chloride. It should be stored in the dark at low temperatures or, better, used at once(95, 140,165,170).…”

High-potential Working Fluids for Next Generation Binary Cycle Geothermal Power Plants

“…Reported boiling points are 185-186°C (760 mm) for the dimer, 140-141°C (10 mm) for the trimer, and 183-185°C (3 mm) for the fully saturated tetramer. [19] An isomeric trimer had a boiling point of 300-301°C (760 mm). Obviously, these will accumulate somewhere on the hot surfaces and probably eventually form coke.…”