A Two‐Step Oxidative Cleavage of 1,2‐Diol Fatty Esters into Acids or Nitriles by a Dehydrogenation–Oxidative Cleavage Sequence,ChemSusChem

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A Two‐Step Oxidative Cleavage of 1,2‐Diol Fatty Esters into Acids or Nitriles by a Dehydrogenation–Oxidative Cleavage Sequence
ChemSusChem ( IF 7.5 ) Pub Date : 2018-08-23 , DOI: 10.1002/cssc.201801640
Boris Guicheret ₁ , Yann Bertholo ₁ , Philippe Blach ₂ , Yann Raoul ₂ , Estelle Métay ₁ , Marc Lemaire ₁

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Dehydrogenative oxidation of vicinal alcohols catalyzed by a commercially 64 wt.% Ni/SiO₂ catalyst leads to the formation of α‐hydroxyketone. This first step was developed without additional solvent according to two protocols: “under vacuum” or “with an olefin scavenger”. The synthesis of ketols was carried out with good conversions and selectivities. The recyclability of the supported nickel was also studied. Acyloin was then cleaved with oxidative reagent “formic acid/hydrogen peroxide”, which is cheap and can be used on a large scale for industrial oxidation processes. The global yield of this sequential system was up to 80 % to pelargonic acid and azelaic acid monomethyl ester without intermediate purification. By treating the acyloin intermediate with hydroxylamine, nitriles were obtained with a good selectivity.

中文翻译：

通过脱氢氧化裂解序列将1,2-二元醇脂肪酯进行两步氧化裂解为酸或腈

工业上64重量％的Ni / SiO ₂催化邻位醇的脱氢氧化催化剂导致形成α-羟基酮。根据两个协议：“在真空下”或“使用烯烃清除剂”开发了第一步，无需额外的溶剂。酮醇的合成以良好的转化率和选择性进行。还研究了负载型镍的可回收性。然后用廉价的氧化剂“甲酸/过氧化氢”裂解乙酰胆碱，该氧化剂价格便宜，可大规模用于工业氧化过程。无需中间纯化，该连续系统的总收率高达壬二酸和壬二酸单甲酯的80％。通过用羟胺处理酰化甘油中间体，以良好的选择性获得了腈。

更新日期：2018-08-23

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