An alternative route to the conventional one for fatty alcohol synthesis was investigated. It was possible to synthesize lauryl alcohol from methyl laurate via reduction by transfer of hydrogen and hydride in liquid phase, in noncatalytic reactions and without the supply of H₂ gaseous. Pure NaBH₄ or alumina‐supported NaBH₄ and methanol were used as co‐reactants and 100% fatty alcohol selectivities were achieved. The aim of supporting the metal hydride was to increase its stability and achieve the full recovery of the solid at the end of reaction. When alumina‐supported NaBH₄ was used, a final fatty alcohol yield of 93% was achieved. The use of methanol and NaBH₄ in amounts higher than stoichiometric is important to generate alkoxyborohydride anions which act as better reducing species than NaBH₄. The reaction conditions effect was investigated and the role of short carbon chain alcohol structure was elucidated. The effect of fatty acid methyl ester structure was also studied. Fatty acid methyl esters with shorter carbon chain length and without unsaturation (methyl laurate, methyl myristate) were easily reduced using NaBH₄/Al₂O₃ and methanol reaching high conversions and fatty alcohol selectivities. Unsaturated fatty acid methyl ester with longer carbon chain (methyl oleate) introduced steric hindrance which disfavoured interaction between ester and reducing solid surface and fatty acid methyl ester conversion was noticeably lower. A reaction mechanism based on alkoxyborohydride anions as the actual reducing species was proposed. This mechanism fully interprets results obtained during fatty acid methyl ester reduction using short carbon chain alcohols and metal hydride.

中文翻译：

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在不提供气态H2的情况下将植物油衍生的脂肪酸甲酯还原为脂肪醇

研究了用于脂肪醇合成的常规途径的替代途径。在非催化反应中且不供应气态H _2的情况下，可以通过在液相中转移氢和氢化物通过还原从月桂酸甲酯合成月桂醇。纯NaBH ₄或氧化铝负载的NaBH ₄和甲醇用作共反应物，脂肪醇的选择性达到100％。负载金属氢化物的目的是增加其稳定性并在反应结束时实现固体的完全回收。当使用氧化铝负载的NaBH ₄时，最终的脂肪醇收率达到93％。使用甲醇和NaBH ₄高于化学计量的量对于生成烷氧基硼氢化物阴离子比NaBH ₄具有更好的还原性非常重要。研究了反应条件的影响，阐明了短碳链醇结构的作用。还研究了脂肪酸甲酯结构的影响。使用NaBH ₄ / Al ₂ O ₃可以轻松还原具有较短碳链长度且不饱和的脂肪酸甲酯（月桂酸甲酯，肉豆蔻酸甲酯）和甲醇达到高转化率和脂肪醇选择性。具有较长碳链的不饱和脂肪酸甲酯（油酸甲酯）引入了位阻，不利于酯之间的相互作用并降低了固体表面，脂肪酸甲酯的转化率明显降低。提出了以烷氧基硼氢化物阴离子为实际还原物种的反应机理。该机理充分解释了使用短碳链醇和金属氢化物还原脂肪酸甲酯期间获得的结果。