Amines as effective ligands in iridium-catalyzed decarbonylative dehydration of biosourced substrates†,Catalysis Science & Technology

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Amines as effective ligands in iridium-catalyzed decarbonylative dehydration of biosourced substrates†
Catalysis Science & Technology ( IF 4.4 ) Pub Date : 2018-07-10 00:00:00 , DOI: 10.1039/c8cy00621k
Jérémy Ternel _{1,

2,

3,

4,

5} , Bastien Léger _{1,

2,

3,

4,

5} , Eric Monflier _{1,

2,

3,

4,

5} , Frédéric Hapiot _{1,

2,

3,

4,

5}

Affiliation

Linear α-olefins (LAOs) and linear internal olefins (LIOs) are essential intermediates in the synthesis of surfactants, lubricants, and polymers. Concurrently with petroleum-based industrial processes, the production of LAOs and LIOs from renewable feedstocks has gained increasing interest in recent years. Organometallic catalysts have been developed designedly, especially Pd, Fe and Ir catalysts. However, such catalysts are mostly stabilized by phosphanes, ligands sometimes difficult to handle especially on large scales. Alternatives to phosphanes would thus be highly desirable. In the present study, we demonstrate that Ir catalysts coordinated by amines are suitable to decarbonylate a wide range of biosourced substrates under mild conditions. The resulting LAOs and LIOs are obtained with good conversion provided that the nature and the quantity of the amines are controlled accurately. The LAO/LIO selectivity can also be tuned by a judicious choice of experimental conditions. Interestingly, the Ir-based catalytic system is applicable to the decarbonylative dehydration of saturated, unsaturated and polyunsaturated fatty acids.

中文翻译：

胺作为铱催化生物来源底物进行脱羰脱水的有效配体†

线性α-烯烃（LAOs）和线性内部烯烃（LIOs）是表面活性剂，润滑剂和聚合物合成中必不可少的中间体。与基于石油的工业过程同时进行的是，近年来，由可再生原料生产LAO和LIO的兴趣日益增加。已经设计开发了有机金属催化剂，特别是Pd，Fe和Ir催化剂。然而，此类催化剂大部分被膦稳定，配体有时难以处理，尤其是大规模处理。因此，非常需要膦的替代物。在本研究中，我们证明了由胺配位的Ir催化剂适合在温和条件下使各种生物来源的底物脱羰。只要精确控制胺的性质和数量，就可以得到具有良好转化率的所得LAO和LIO。还可以通过明智地选择实验条件来调整LAO / LIO的选择性。有趣的是，基于Ir的催化体系适用于饱和，不饱和和多不饱和脂肪酸的脱羰脱水。

更新日期：2018-07-10

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