Guerbet Alcohols: From Processes under Harsh Conditions to Synthesis at Room Temperature under Ambient Pressure,ChemCatChem

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Guerbet Alcohols: From Processes under Harsh Conditions to Synthesis at Room Temperature under Ambient Pressure
ChemCatChem ( IF 3.8 ) Pub Date : 2016-01-26 , DOI: 10.1002/cctc.201501241
Marc Biermann ₁ , Hendrik Gruß ₁ , Werner Hummel ₁ , Harald Gröger ₁

Affiliation

A novel synthetic approach towards Guerbet alcohols, which are important intermediates in the production of plasticizers, lubricants, and surfactants, was developed. In contrast to the harsh reaction conditions of Guerbet alcohols produced today, which include high temperatures, the new developed process runs at room temperature. The key feature of this alternative process is the combination of organocatalytic and enzymatic steps towards a chemoenzymatic synthesis. In detail, the piperidinyloxyl‐catalyzed oxidation of 1‐hexanol by using hypochlorite and the lysine‐catalyzed homoaldol condensation of the resulting aldehyde were combined with two subsequent enzymatic reductions of the C=C and C=O bonds of the in situ formed 2‐branched α,β‐unsaturated aldehyde by means of an ene reductase from Gluconobacter oxydans and an alcohol dehydrogenase from Rhodococcus sp. under in situ cofactor regeneration. The desired 2‐branched aliphatic primary alcohol was obtained with high conversion and selectivity and without the need for intermediate purifications.

中文翻译：

格尔伯特醇：从严酷条件下的过程到室温常压下的合成

开发了一种新型的Guerbet醇合成方法，Guerbet醇是增塑剂，润滑剂和表面活性剂生产中的重要中间体。与当今生产的Guerbet醇苛刻的反应条件（包括高温）相反，新开发的工艺在室温下运行。该替代方法的关键特征是有机催化步骤与酶促步骤的结合，以实现化学酶促合成。详细地讲，使用次氯酸盐的哌啶子基氧基催化的1-己醇氧化和赖氨酸催化的醛缩合的醛缩醛缩合反应，以及随后的两个酶促还原原位形成的2-羟基的C = C和C = O键的过程。氧化葡糖杆菌中的烯还原酶使α，β-不饱和醛支化和来自红球菌属（Rhodococcus sp。）的醇脱氢酶。在原位辅因子再生下。所需的2支脂肪族伯醇具有较高的转化率和选择性，无需中间纯化即可获得。

更新日期：2016-01-26

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