Reação de condensação do glicerol com compostos carbonílicos : síntese, caracterização e aplicação em cristais líquidos
Autor(a) principal: | |
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Data de Publicação: | 2015 |
Outros Autores: | , , , |
Tipo de documento: | Artigo |
Idioma: | por |
Título da fonte: | Repositório Institucional da UFRGS |
Texto Completo: | http://hdl.handle.net/10183/131116 |
Resumo: | Condensation reactions of glycerol with aldehydes and ketones were performed under thermal heating and microwave irradiation regimes. Homogeneous and heterogeneous catalysts were tested in both conditions. A silica sulfated (SiO2–SO3H) heterogeneous catalyst demonstrated the best performance relative to a selectivity of >95% in favor of 5-membered ketals. For acetals, preference in favor of 5-membered or 6-membered functional groups depends on the nature of the catalyst. Homogenous catalysts favor the more stable 6-membered acetals, whereas heterogeneous catalysts favor the less stable 5-membered acetals. However, the isomer ratios in the acetalization reaction are too low, and hence the reaction cannot be used in a synthetic plan for functional materials. Ketalization processes mediated by SiO2–SO3H show a high selectivity in favor of a 5-membered ring (1,3-dioxolane). The scope of condensation was tested with different ketones. A mechanism for heterogeneous catalysis related to the selectivity in the cyclization process is presented herein. Solketal, a commercial product, was also obtained by a condensation reaction of glycerol and propanone, and showed a high selectivity in favor of 1,3-dioxolane. It was transformed to potential allylic and chiral intermediates. A mesogenic core was connected to the organic framework of glycerol to produce a monomer liquid crystal material with a stable smectic-C mesophase. |
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Kautz, JacquelineFeltrin, Carlos WillianSales, Eric SouzaEifler-Lima, Vera LuciaMerlo, Aloir Antonio2015-12-15T02:37:47Z20150100-4042http://hdl.handle.net/10183/131116000980570Condensation reactions of glycerol with aldehydes and ketones were performed under thermal heating and microwave irradiation regimes. Homogeneous and heterogeneous catalysts were tested in both conditions. A silica sulfated (SiO2–SO3H) heterogeneous catalyst demonstrated the best performance relative to a selectivity of >95% in favor of 5-membered ketals. For acetals, preference in favor of 5-membered or 6-membered functional groups depends on the nature of the catalyst. Homogenous catalysts favor the more stable 6-membered acetals, whereas heterogeneous catalysts favor the less stable 5-membered acetals. However, the isomer ratios in the acetalization reaction are too low, and hence the reaction cannot be used in a synthetic plan for functional materials. Ketalization processes mediated by SiO2–SO3H show a high selectivity in favor of a 5-membered ring (1,3-dioxolane). The scope of condensation was tested with different ketones. A mechanism for heterogeneous catalysis related to the selectivity in the cyclization process is presented herein. Solketal, a commercial product, was also obtained by a condensation reaction of glycerol and propanone, and showed a high selectivity in favor of 1,3-dioxolane. It was transformed to potential allylic and chiral intermediates. A mesogenic core was connected to the organic framework of glycerol to produce a monomer liquid crystal material with a stable smectic-C mesophase.application/pdfporQuímica nova. São Paulo. Vol. 38, n. 8 (set. 2015), p. 1053-1062GlicerolCondensaçãoCompostos carbonílicosCristais líquidosGlycerol derivativesCondensation reactionHeterogeneous catalystLiquid crystalsSolketal transformationReação de condensação do glicerol com compostos carbonílicos : síntese, caracterização e aplicação em cristais líquidosCondensation reaction of glycerol and carbonyl compounds : synthesis, characterization, and derivatization for liquid crystalsinfo:eu-repo/semantics/articleinfo:eu-repo/semantics/otherinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFRGSinstname:Universidade Federal do Rio Grande do Sul (UFRGS)instacron:UFRGSORIGINAL000980570.pdf000980570.pdfTexto completoapplication/pdf1676195http://www.lume.ufrgs.br/bitstream/10183/131116/1/000980570.pdfa3b44ac067d1829d3c2439caf609ac75MD51TEXT000980570.pdf.txt000980570.pdf.txtExtracted Texttext/plain47888http://www.lume.ufrgs.br/bitstream/10183/131116/2/000980570.pdf.txte02018e11538b9181978cc445f686788MD52THUMBNAIL000980570.pdf.jpg000980570.pdf.jpgGenerated Thumbnailimage/jpeg1931http://www.lume.ufrgs.br/bitstream/10183/131116/3/000980570.pdf.jpg9672ac556ffdbe9de2ab74aa453308ffMD5310183/1311162018-10-25 09:49:08.721oai:www.lume.ufrgs.br:10183/131116Repositório de PublicaçõesPUBhttps://lume.ufrgs.br/oai/requestopendoar:2018-10-25T12:49:08Repositório Institucional da UFRGS - Universidade Federal do Rio Grande do Sul (UFRGS)false |
dc.title.pt_BR.fl_str_mv |
Reação de condensação do glicerol com compostos carbonílicos : síntese, caracterização e aplicação em cristais líquidos |
dc.title.alternative.en.fl_str_mv |
Condensation reaction of glycerol and carbonyl compounds : synthesis, characterization, and derivatization for liquid crystals |
title |
Reação de condensação do glicerol com compostos carbonílicos : síntese, caracterização e aplicação em cristais líquidos |
spellingShingle |
Reação de condensação do glicerol com compostos carbonílicos : síntese, caracterização e aplicação em cristais líquidos Kautz, Jacqueline Glicerol Condensação Compostos carbonílicos Cristais líquidos Glycerol derivatives Condensation reaction Heterogeneous catalyst Liquid crystals Solketal transformation |
title_short |
Reação de condensação do glicerol com compostos carbonílicos : síntese, caracterização e aplicação em cristais líquidos |
title_full |
Reação de condensação do glicerol com compostos carbonílicos : síntese, caracterização e aplicação em cristais líquidos |
title_fullStr |
Reação de condensação do glicerol com compostos carbonílicos : síntese, caracterização e aplicação em cristais líquidos |
title_full_unstemmed |
Reação de condensação do glicerol com compostos carbonílicos : síntese, caracterização e aplicação em cristais líquidos |
title_sort |
Reação de condensação do glicerol com compostos carbonílicos : síntese, caracterização e aplicação em cristais líquidos |
author |
Kautz, Jacqueline |
author_facet |
Kautz, Jacqueline Feltrin, Carlos Willian Sales, Eric Souza Eifler-Lima, Vera Lucia Merlo, Aloir Antonio |
author_role |
author |
author2 |
Feltrin, Carlos Willian Sales, Eric Souza Eifler-Lima, Vera Lucia Merlo, Aloir Antonio |
author2_role |
author author author author |
dc.contributor.author.fl_str_mv |
Kautz, Jacqueline Feltrin, Carlos Willian Sales, Eric Souza Eifler-Lima, Vera Lucia Merlo, Aloir Antonio |
dc.subject.por.fl_str_mv |
Glicerol Condensação Compostos carbonílicos Cristais líquidos |
topic |
Glicerol Condensação Compostos carbonílicos Cristais líquidos Glycerol derivatives Condensation reaction Heterogeneous catalyst Liquid crystals Solketal transformation |
dc.subject.eng.fl_str_mv |
Glycerol derivatives Condensation reaction Heterogeneous catalyst Liquid crystals Solketal transformation |
description |
Condensation reactions of glycerol with aldehydes and ketones were performed under thermal heating and microwave irradiation regimes. Homogeneous and heterogeneous catalysts were tested in both conditions. A silica sulfated (SiO2–SO3H) heterogeneous catalyst demonstrated the best performance relative to a selectivity of >95% in favor of 5-membered ketals. For acetals, preference in favor of 5-membered or 6-membered functional groups depends on the nature of the catalyst. Homogenous catalysts favor the more stable 6-membered acetals, whereas heterogeneous catalysts favor the less stable 5-membered acetals. However, the isomer ratios in the acetalization reaction are too low, and hence the reaction cannot be used in a synthetic plan for functional materials. Ketalization processes mediated by SiO2–SO3H show a high selectivity in favor of a 5-membered ring (1,3-dioxolane). The scope of condensation was tested with different ketones. A mechanism for heterogeneous catalysis related to the selectivity in the cyclization process is presented herein. Solketal, a commercial product, was also obtained by a condensation reaction of glycerol and propanone, and showed a high selectivity in favor of 1,3-dioxolane. It was transformed to potential allylic and chiral intermediates. A mesogenic core was connected to the organic framework of glycerol to produce a monomer liquid crystal material with a stable smectic-C mesophase. |
publishDate |
2015 |
dc.date.accessioned.fl_str_mv |
2015-12-15T02:37:47Z |
dc.date.issued.fl_str_mv |
2015 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article info:eu-repo/semantics/other |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10183/131116 |
dc.identifier.issn.pt_BR.fl_str_mv |
0100-4042 |
dc.identifier.nrb.pt_BR.fl_str_mv |
000980570 |
identifier_str_mv |
0100-4042 000980570 |
url |
http://hdl.handle.net/10183/131116 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.ispartof.pt_BR.fl_str_mv |
Química nova. São Paulo. Vol. 38, n. 8 (set. 2015), p. 1053-1062 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
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