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在金属盐存在下，离子液体中甲基亚油酸酯与丙烯的烷基化反应。

Alkylation of Methyl Linoleate with Propene in Ionic Liquids in the Presence of Metal Salts.

作者信息

Pomelli Christian Silvio, Ghilardi Tiziana, Chiappe Cinzia, de Angelis Alberto Renato, Calemma Vincenzo

机构信息

Dipartimento di Farmacia, Università di Pisa, via Bonanno 33, Pisa 56126, Italy.

ENI Downstream R & D, Development Operations and Technology, S. Donato Milanese (Mi) 20097, Italy.

出版信息

Molecules. 2015 Dec 7;20(12):21840-53. doi: 10.3390/molecules201219805.

DOI:10.3390/molecules201219805
PMID:26690107
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6332105/
Abstract

Vegetable oils and fatty acid esters are suitable precursor molecules for the production of a variety of bio-based products and materials, such as paints and coatings, plastics, soaps, lubricants, cosmetics, pharmaceuticals, printing inks, surfactants, and biofuels. Here, we report the possibility of using Lewis acidic ionic liquids (ILs) to obtain polyunsaturated ester dimerization-oligomerization and/or, in the presence of another terminal alkene (propene), co-polymerization. In particular, we have tested the Lewis acidic mixtures arising from the addition of a proper amount of GaCl₃ (Χ > 0.5) to two chloride-based (1-butyl-3-methylimidazolium chloride, [bmim]Cl, and 1-butylisoquinolium chloride, [BuIsoq]Cl) or by dissolution of a smaller amount of Al(Tf₂N)₃ (Χ = 0.1) in 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, [bmim][Tf₂N]. On the basis of product distribution studies, [bmim][Tf₂N]/Al(Tf₂N)₃ appears the most suitable medium in which methyl linoleate alkylation with propene can compete with methyl linoleate or propene oligomerization.

摘要

植物油和脂肪酸酯是生产各种生物基产品和材料的合适前体分子，如油漆和涂料、塑料、肥皂、润滑剂、化妆品、药品、印刷油墨、表面活性剂和生物燃料。在此，我们报告了使用路易斯酸性离子液体（ILs）实现多不饱和酯二聚化-低聚化和/或在另一种末端烯烃（丙烯）存在下进行共聚的可能性。具体而言，我们测试了通过向两种氯化物基离子液体（1-丁基-3-甲基咪唑鎓氯化物，[bmim]Cl，和1-丁基异喹啉鎓氯化物，[BuIsoq]Cl）中添加适量的GaCl₃（Χ > 0.5）或在1-丁基-3-甲基咪唑鎓双（三氟甲基磺酰）亚胺，[bmim][Tf₂N]中溶解少量的Al(Tf₂N)₃（Χ = 0.1）而产生的路易斯酸性混合物。基于产物分布研究，[bmim][Tf₂N]/Al(Tf₂N)₃似乎是最适合亚油酸甲酯与丙烯烷基化反应与亚油酸甲酯或丙烯低聚化反应竞争的介质。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/376d/6332105/3812cd958b55/molecules-20-19805-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/376d/6332105/cc332bbcb9d4/molecules-20-19805-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/376d/6332105/dd806b41e63e/molecules-20-19805-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/376d/6332105/1b126f242ee4/molecules-20-19805-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/376d/6332105/12d90080eacf/molecules-20-19805-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/376d/6332105/0c638be59879/molecules-20-19805-g001a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/376d/6332105/383f77577c69/molecules-20-19805-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/376d/6332105/085b1d863488/molecules-20-19805-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/376d/6332105/fc079295ed74/molecules-20-19805-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/376d/6332105/80078316ff0d/molecules-20-19805-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/376d/6332105/3812cd958b55/molecules-20-19805-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/376d/6332105/cc332bbcb9d4/molecules-20-19805-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/376d/6332105/dd806b41e63e/molecules-20-19805-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/376d/6332105/1b126f242ee4/molecules-20-19805-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/376d/6332105/12d90080eacf/molecules-20-19805-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/376d/6332105/0c638be59879/molecules-20-19805-g001a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/376d/6332105/383f77577c69/molecules-20-19805-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/376d/6332105/085b1d863488/molecules-20-19805-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/376d/6332105/fc079295ed74/molecules-20-19805-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/376d/6332105/80078316ff0d/molecules-20-19805-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/376d/6332105/3812cd958b55/molecules-20-19805-g006.jpg

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