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Valorization of Unconventional Lipids from Microalgae or Tall Oil via a Selective Dual Catalysis One-Pot Approach
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2017-09-15 , DOI: 10.1021/jacs.7b06957 Sandra K. Hess 1 , Natalie S. Schunck 1 , Verena Goldbach 1 , Daniela Ewe 1 , Peter G. Kroth 1 , Stefan Mecking 1
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2017-09-15 , DOI: 10.1021/jacs.7b06957 Sandra K. Hess 1 , Natalie S. Schunck 1 , Verena Goldbach 1 , Daniela Ewe 1 , Peter G. Kroth 1 , Stefan Mecking 1
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A dual catalysis approach enables selective functionalization of unconventional feedstocks composed of complex fatty acid mixtures with highly unsaturated portions like eicosapentaenoate (20:5) along with monounsaturated compounds. The degree of unsaturation is unified by selective heterogeneous hydrogenation on Pd/γ-Al2O3, complemented by effective activation to a homogeneous carbonylation catalyst [(dtbpx)PdH(L)]+ by addition of diprotonated diphosphine (dtbpxH2)(OTf)2. By this one-pot approach, neat 20:5 as a model substrate is hydrogenated to up to 80% to the monounsaturated analogue (20:1), this is functionalized to the desired C21 α,ω-diester building block with a linear selectivity of over 90%. This catalytic approach is demonstrated to be suitable for crude microalgae oil from Phaeodactylum tricornutum genetically engineered for this purpose, as well as tall oil, an abundant waste material. Both substrates were fully converted with an overall selectivity to the linear α,ω-diester of up to 75%.
中文翻译：
通过选择性双催化一锅法对来自微藻或妥尔油的非常规脂质进行增值
双催化方法能够对由具有高度不饱和部分（如二十碳五烯酸 (20:5)）和单不饱和化合物的复杂脂肪酸混合物组成的非常规原料进行选择性功能化。不饱和度通过 Pd/γ-Al2O3 上的选择性多相氢化来统一，并通过添加双质子化二膦 (dtbpxH2)(OTf)2 有效活化均相羰基化催化剂 [(dtbpx)PdH(L)]+ 来补充。通过这种一锅法，纯 20:5 作为模型底物被氢化到高达 80% 的单不饱和类似物 (20:1)，这被功能化为具有线性选择性的所需 C21 α,ω-二酯结构单元超过 90%。这种催化方法被证明适用于为此目的进行基因工程改造的三角褐指藻粗微藻油，以及妥尔油，一种丰富的废料。两种底物都完全转化为线性 α,ω-二酯的总选择性高达 75%。
更新日期：2017-09-15
中文翻译：
通过选择性双催化一锅法对来自微藻或妥尔油的非常规脂质进行增值
双催化方法能够对由具有高度不饱和部分（如二十碳五烯酸 (20:5)）和单不饱和化合物的复杂脂肪酸混合物组成的非常规原料进行选择性功能化。不饱和度通过 Pd/γ-Al2O3 上的选择性多相氢化来统一，并通过添加双质子化二膦 (dtbpxH2)(OTf)2 有效活化均相羰基化催化剂 [(dtbpx)PdH(L)]+ 来补充。通过这种一锅法，纯 20:5 作为模型底物被氢化到高达 80% 的单不饱和类似物 (20:1)，这被功能化为具有线性选择性的所需 C21 α,ω-二酯结构单元超过 90%。这种催化方法被证明适用于为此目的进行基因工程改造的三角褐指藻粗微藻油，以及妥尔油，一种丰富的废料。两种底物都完全转化为线性 α,ω-二酯的总选择性高达 75%。
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