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

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논문

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

학술지

ChemCatChem

저자명

Biermann, Marc; Gruß, Hendrik; Hummel, Werner; Grö ger, Harald

초록

<P><B>Abstract</B></P><P>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&#8208;catalyzed oxidation of 1&#8208;hexanol by using hypochlorite and the lysine&#8208;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&#8208;branched &alpha;,&beta;&#8208;unsaturated aldehyde by means of an ene reductase from <I>Gluconobacter oxydans</I> and an alcohol dehydrogenase from <I>Rhodococcus</I> sp. under in situ cofactor regeneration. The desired 2&#8208;branched aliphatic primary alcohol was obtained with high conversion and selectivity and without the need for intermediate purifications.</P>

발행연도

2016

ISSN

1867-3880

ISSN

1867-3899

8

5

페이지

pp.895-899

주제어

biocatalysis; chemoenzymatic synthesis; domino reactions; Guerbet alcohols; organocatalysis

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논문; 2016-01-26

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