A New, Simple and Efficient Method of Steglich Esterification of Juglone with Long-Chain Fatty Acids: Synthesis of a New Class of Non-Polymeric Wax Deposition Inhibitors for Crude Oil
Direct esterification on naphthoquinone presented itself as a hard task. Usual methodologies apply acyl chloride in pyridine or anhydrides but with long-chain esters this procedure proved to be ineffective because of the low yields obtained. We present a new synthesis of long-chain esters of juglone based on Steglich esterification using a cheap Lewis acid as cocatalyst. Yields obtained are considerably better than those found previously. Computational chemistry was used to evaluate the effects of CeCl3 as cocatalyst. Prepared compounds were tested as wax deposition inhibitors in crude oil. Palmitic ester of juglone was able to 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.
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Sociedade Brasileira de Química
2015
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oai:scielo:S0103-505320150001000742015-02-03A New, Simple and Efficient Method of Steglich Esterification of Juglone with Long-Chain Fatty Acids: Synthesis of a New Class of Non-Polymeric Wax Deposition Inhibitors for Crude OilGilles,VitorVieira,Mariana A.Lacerda Jr.,ValdemarCastro,Eustáquio V. R.Santos,Reginaldo B.Orestes,EdnilsonCarneiro,José W. M.Greco,Sandro J. juglone Steglich esterification fatty acid wax deposition inhibitor Direct esterification on naphthoquinone presented itself as a hard task. Usual methodologies apply acyl chloride in pyridine or anhydrides but with long-chain esters this procedure proved to be ineffective because of the low yields obtained. We present a new synthesis of long-chain esters of juglone based on Steglich esterification using a cheap Lewis acid as cocatalyst. Yields obtained are considerably better than those found previously. Computational chemistry was used to evaluate the effects of CeCl3 as cocatalyst. Prepared compounds were tested as wax deposition inhibitors in crude oil. Palmitic ester of juglone was able to 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.info:eu-repo/semantics/openAccessSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society v.26 n.1 20152015-01-01info:eu-repo/semantics/articletext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532015000100074en10.5935/0103-5053.20140216 |
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Gilles,Vitor Vieira,Mariana A. Lacerda Jr.,Valdemar Castro,Eustáquio V. R. Santos,Reginaldo B. Orestes,Ednilson Carneiro,José W. M. Greco,Sandro J. |
| spellingShingle |
Gilles,Vitor Vieira,Mariana A. Lacerda Jr.,Valdemar Castro,Eustáquio V. R. Santos,Reginaldo B. Orestes,Ednilson Carneiro,José W. M. Greco,Sandro J. A New, Simple and Efficient Method of Steglich Esterification of Juglone with Long-Chain Fatty Acids: Synthesis of a New Class of Non-Polymeric Wax Deposition Inhibitors for Crude Oil |
| author_facet |
Gilles,Vitor Vieira,Mariana A. Lacerda Jr.,Valdemar Castro,Eustáquio V. R. Santos,Reginaldo B. Orestes,Ednilson Carneiro,José W. M. Greco,Sandro J. |
| author_sort |
Gilles,Vitor |
| title |
A New, Simple and Efficient Method of Steglich Esterification of Juglone with Long-Chain Fatty Acids: Synthesis of a New Class of Non-Polymeric Wax Deposition Inhibitors for Crude Oil |
| title_short |
A New, Simple and Efficient Method of Steglich Esterification of Juglone with Long-Chain Fatty Acids: Synthesis of a New Class of Non-Polymeric Wax Deposition Inhibitors for Crude Oil |
| title_full |
A New, Simple and Efficient Method of Steglich Esterification of Juglone with Long-Chain Fatty Acids: Synthesis of a New Class of Non-Polymeric Wax Deposition Inhibitors for Crude Oil |
| title_fullStr |
A New, Simple and Efficient Method of Steglich Esterification of Juglone with Long-Chain Fatty Acids: Synthesis of a New Class of Non-Polymeric Wax Deposition Inhibitors for Crude Oil |
| title_full_unstemmed |
A New, Simple and Efficient Method of Steglich Esterification of Juglone with Long-Chain Fatty Acids: Synthesis of a New Class of Non-Polymeric Wax Deposition Inhibitors for Crude Oil |
| title_sort |
new, simple and efficient method of steglich esterification of juglone with long-chain fatty acids: synthesis of a new class of non-polymeric wax deposition inhibitors for crude oil |
| description |
Direct esterification on naphthoquinone presented itself as a hard task. Usual methodologies apply acyl chloride in pyridine or anhydrides but with long-chain esters this procedure proved to be ineffective because of the low yields obtained. We present a new synthesis of long-chain esters of juglone based on Steglich esterification using a cheap Lewis acid as cocatalyst. Yields obtained are considerably better than those found previously. Computational chemistry was used to evaluate the effects of CeCl3 as cocatalyst. Prepared compounds were tested as wax deposition inhibitors in crude oil. Palmitic ester of juglone was able to 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. |
| publisher |
Sociedade Brasileira de Química |
| publishDate |
2015 |
| url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532015000100074 |
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