Plasticizer alcohols have been synthesised from renewable reagents through a borane-free oxidation/reduction sequence.
Bis(2-ethyl-hexyl) phthalate (DEHP) is one of the most important and widely used industrial plasticizers and is generated from 2-ethyl-1-hexanol (2EH) and phthalic anhydride. In the process of converting bio-butanol to jet fuels, a significant amount of 2-ethyl-1-hexene is produced as a by-product, and is an attractive feedstock to generate 2EH. 
In this work, Benjamin Harvey and colleagues from the United States Navy-Naval Air Systems Command (NAVAIR) demonstrate an efficient method for formal anti-Markovnikov hydration of 1,1-disubstituted alkenes. Their approach generates the plasticizer alcohols by the oxidation/hydration/hydrogenation of branched chain alkenes under mild, borane-free conditions. This process was successfully applied to the production of 2EH from 2-ethyl-1-hexene, and presents an alternative to hydroboration for a challenging subset of hindered olefins.
This article is free to access until the 29th August 2012! Click on the link below to find out more…
Synthesis of renewable plasticizer alcohols by formal anti-Markovnikov hydration of terminal branched chain alkenes viaa borane-free oxidation/reduction sequence, Benjamin G. Harvey, Heather A. Meylemans and Roxanne L. Quintana, Green Chem., 2012, DOI: 10.1039/C2GC35595G
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