Adamantane Essay Research Paper The unique nature

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Adamantane Essay, Research Paper The unique nature of diamond is heavily dependent upon its composition, crystal structure, and mechanical, thermal, and electromagnetic properties.1 Of those dependencies, composition exacts the most influence over the characteristics. Crystal structure is the repeating pattern of diamond?s composition, and each of the properties are the result of molecular interaction which is determined by composition. Therefore, composition is paramount in the determination of the qualities of diamond. Before its discovery, adamantane was known as decaterpene, the name applied by Decker to his tricyclic hydrocarbon. Decker believed that his decaterpene was similar in structure as the diamond lattice. Decaterpene, as in diamond, was proposed by Decker to be

highly structured and strain free.2 Decker proposed decaterpene in 1924, but that was all it was until 1933 when the structure was proven to exist. Isolated in the petroleum of Hodinin, Czechoslovakia by Landa and Machachaeck, decaterpene became incarnate.3 However, the fact that they found the structure Decker predicted did not mean that his nomenclature would be used to identify the compound. That honor was bestowed upon its discoverers Landa and Machcahcaeck who used the Greek translation of diamond, adamantane, to identify the compound.2 Crude petroleum is separated into its component compounds by fractional distillation. The procedure involves a sample of the petroleum to be heated until the sample is vaporized leaving behind any solid impurities. The resulting steam enters

a fractional distillation column in which a temperature gradient had been instilled. The temperature of the column decreases as the steam rises through the column. The idea is that, as the temperature of the column decreases, the vapor temperature will decrease. When the boiling point of a compound is passed, the compound will condense on the sides of the column and be collected in the fraction well at that point. Thus the mixture is separated into fractions of compounds with similar boiling points in a mixture.4 Adamantane?s high boiling point caused it to be one of the initial compounds to condense with the kerosene fraction in the 190o C cut.5 The only problem with the fractional distillation method is that adamantane cannot be extracted in large quantities because it exists

in only a small quantity in petrol. The presence of adamantane was found to be only 0.0004% of the composition of petroleum by the fractional distillation method.2 Adamantane is not alone in the petroleum distillate in which it is present. Alkylated adamantane derivatives also show up in adamantane containing distillate. (II, III, IV) The output of adamantane is capable of being increased if the thiourea adduct method is employed on the petroleum. Landa and Hale were able to isolate complexes of adamantane from crude petroleum that had bonded to thiourea.5 Now that the natural product has been discovered, the next logical step would be to formulate the natural process in which the compound was made. As of 1964, the natural method that creates the adamantane compound had not been

found. The natural process that was attempted was to bombard adamantane-free petroleum with catalysts in an attempt to initiate the formation of adamantane. The resulting mixture was fractioned and analyzed to see if any extra adamantane was created. In most cases, the catalyst failed to produce any adamantane. However, many of the catalysts produced derivatives that had the ring structure but with extra components attached.5 The only catalyst shown to make a significant amount was AlCl3, but not enough was created for the catalyst to be considered for mass production of adamantane. Catalysts that failed were: oil-bearing stone from Hodin with and without HF, aluminum silicate, aluminum oxide, concentrated sulfuric acid, zinc chloride, iron(III) chloride, tin(IV) chloride,