A New, Simple and Efficient Method of Steglich Esterification of Juglonewith Long-Chain Fatty Acids: Synthesis of a New Class of Non-Polymeric Wax DepositionInhibitors for Crude Oil

Journal of the Brazilian Chemical Society

Vitor Gilles¹  Mariana A. Vieira¹  Valdemar Lacerda Jr.¹  Eustáquio V. R. Castro¹  Reginaldo B. Santos¹  Ednilson Orestes¹  José W. M. Carneiro¹  Sandro J. Greco¹ 

关键词: juglone;    Steglich esterification;    fatty acid;    wax deposition inhibitor;   

DOI  :  10.5935/0103-5053.20140216

来源: SciELO

【 摘 要 】

Direct esterification on naphthoquinone presented itself as a hard task. Usualmethodologies apply acyl chloride in pyridine or anhydrides but with long-chainesters this procedure proved to be ineffective because of the low yields obtained. Wepresent a new synthesis of long-chain esters of juglone based on Steglichesterification using a cheap Lewis acid as cocatalyst. Yields obtained areconsiderably better than those found previously. Computational chemistry was used toevaluate the effects of CeCl3 as cocatalyst. Prepared compounds weretested as wax deposition inhibitors in crude oil. Palmitic ester of juglone was ableto lower 4 ºC on the wax appearance temperature (WAT) of the studied oil,representing a reduction of precipitated normal paraffin of 1.5% m/m.

【 授权许可】

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