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Biobased Aldehydes from Fatty Epoxides through Thermal Cleavage of β‐Hydroxy Hydroperoxides**
ChemSusChem ( IF 7.5 ) Pub Date : 2020-10-30 , DOI: 10.1002/cssc.202002364 Thomas De Dios Miguel 1 , Nam Duc Vu 1 , Marc Lemaire 1 , Nicolas Duguet 1
ChemSusChem ( IF 7.5 ) Pub Date : 2020-10-30 , DOI: 10.1002/cssc.202002364 Thomas De Dios Miguel 1 , Nam Duc Vu 1 , Marc Lemaire 1 , Nicolas Duguet 1
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The ring‐opening of epoxidized methyl oleate by aqueous H2O2 has been studied using tungsten and molybdenum catalysts to form the corresponding fatty β‐hydroxy hydroperoxides. It was found that tungstic acid and phosphotungstic acid gave the highest selectivities (92–93 %) towards the formation of the desired products, thus limiting the formation of the corresponding fatty 1,2‐diols. The optimized conditions were applied to a range of fatty epoxides to give the corresponding fatty β‐hydroxy hydroperoxides with 30–80 % isolated yields (8 examples). These species were fully characterized by 1H and 13C NMR spectroscopy and HPLC‐HRMS, and their stability was studied by differential scanning calorimetry. The thermal cleavage of the β‐hydroxy hydroperoxide derived from methyl oleate was studied both in batch and flow conditions. It was found that the thermal cleavage in flow conditions gave the highest selectivity towards the formation of aldehydes with limited amounts of byproducts. The aldehydes were both formed with 68 % GC yield, and nonanal and methyl 9‐oxononanoate were isolated with 57 and 55 % yield, respectively. Advantageously, the overall process does not require large excess of H2O2 and only generates water as a byproduct.
中文翻译：
通过热裂解β-羟基氢过氧化物，从脂肪氧化物中提取生物基醛**
已经使用钨和钼催化剂研究了H 2 O 2水溶液对环氧油酸甲酯的开环反应，形成了相应的脂肪β-羟基氢过氧化物。发现钨酸和磷钨酸对所需产物的形成具有最高的选择性（92-93％），从而限制了相应的脂肪族1,2-二醇的形成。将优化的条件应用于一系列脂肪环氧化物，得到相应的脂肪β-羟基氢过氧化物，分离产率为30-80％（8个例子）。这些物种的特征是1 H和13用差示扫描量热法研究了13 C NMR光谱和HPLC-HRMS及其稳定性。在分批和流动条件下都研究了油酸甲酯衍生的β-羟基氢过氧化物的热裂解。发现在流动条件下的热裂解对具有有限量的副产物的醛的形成提供了最高的选择性。生成的醛均以68％的GC收率分离出壬醛和9-氧代壬酸甲酯，收率分别为57％和55％。有利地，整个过程不需要大量过量的H 2 O 2，而仅产生水作为副产物。
更新日期：2021-01-08
中文翻译：
通过热裂解β-羟基氢过氧化物，从脂肪氧化物中提取生物基醛**
已经使用钨和钼催化剂研究了H 2 O 2水溶液对环氧油酸甲酯的开环反应，形成了相应的脂肪β-羟基氢过氧化物。发现钨酸和磷钨酸对所需产物的形成具有最高的选择性（92-93％），从而限制了相应的脂肪族1,2-二醇的形成。将优化的条件应用于一系列脂肪环氧化物，得到相应的脂肪β-羟基氢过氧化物，分离产率为30-80％（8个例子）。这些物种的特征是1 H和13用差示扫描量热法研究了13 C NMR光谱和HPLC-HRMS及其稳定性。在分批和流动条件下都研究了油酸甲酯衍生的β-羟基氢过氧化物的热裂解。发现在流动条件下的热裂解对具有有限量的副产物的醛的形成提供了最高的选择性。生成的醛均以68％的GC收率分离出壬醛和9-氧代壬酸甲酯，收率分别为57％和55％。有利地，整个过程不需要大量过量的H 2 O 2，而仅产生水作为副产物。
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