20667-04-3Relevant academic research and scientific papers
Development of an Enzymatic Process for the Production of (R)-2-Butyl-2-ethyloxirane
Roiban, Gheorghe-Doru,Sutton, Peter W.,Splain, Rebecca,Morgan, Christopher,Fosberry, Andrew,Honicker, Katherine,Homes, Paul,Boudet, Cyril,Dann, Alison,Guo, Jiasheng,Brown, Kristin K.,Ihnken, Leigh Anne F.,Fuerst, Douglas
, p. 1302 - 1310 (2017)
An epoxide resolution process was rapidly developed that allowed access to multigram scale quantities of (R)-2-butyl-2-ethyloxirane 2 at greater than 300 g/L reaction concentration using an easy-to-handle and store lyophilized powder of epoxide hydrolase from Agromyces mediolanus. The enzyme was successfully fermented on a 35 L scale and stability increased by downstream processing. Halohydrin dehalogenases also gave highly enantioselective resolution but were shown to favor hydrolysis of the (R)-2 epoxide, whereas epoxide hydrolase from Aspergillus Niger instead provided (R)-7 via an unoptimized, enantioconvergent process.
Renewable plasticizer alcohols from olefin oligomers and methods for making the same
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Page/Page column 6, (2018/04/20)
An efficient, low-temperature process to convert well-defined olefin oligomers, particularly butene oligomers to branched chain alcohols suitable for use as precursors to plasticizers commonly used in industry, and more specifically, the olefin feedstocks can be conveniently and renewably produced from short chain alcohols.
Palladium on Charcoal Catalyzed 3,4-Hydroperoxidation of α-Substituted Enals with Triethylsilane and Water
Tuokko, Sakari,Pihko, Petri M.
supporting information, p. 1649 - 1652 (2016/07/06)
Aldehyde α-hydroperoxides can be accessed from α-substituted acroleins with triethylsilane and water under Pd/C catalysis and aerobic conditions. The reaction is composed of a Pd/C-catalyzed conjugate reduction step and a hydroperoxidation step. The hydroperoxidation takes place via autoxidation of sufficiently stable enols formed in situ by transfer hydrogenation. Upon reduction, 2,2-disubstituted 1,2-diols are obtained directly from aldehydes.
Synthesis of renewable plasticizer alcohols by formal anti-Markovnikov hydration of terminal branched chain alkenes via a borane-free oxidation/reduction sequence
Harvey, Benjamin G.,Meylemans, Heather A.,Quintana, Roxanne L.
, p. 2450 - 2456 (2013/02/23)
An efficient method for the formal anti-Markovnikov hydration of 1,1-disubstituted alkenes has been developed. The utility of the process has been demonstrated by conversion of bio-derived butene oligomers into primary alcohols through initial oxidation to vicinal acetoxy-alcohols, diols, or diacetates, followed by selective dehydration/tautomerization of the diols, and hydrogenation of the intermediary aldehydes. This approach allows for the isolation of important industrial plasticizer alcohols from a renewable source. In a broader context, this pathway, which can be conducted with sustainable, conventional reagents under mild conditions, represents a unique alternative to hydroboration for a challenging subset of hindered olefins.
Oxidative Cleavage of Olefins into Carboxylic Acids with Hydrogen Peroxide by Tungstic Acid
Oguchi, Takahito,Ura, Toshikazu,Ishii, Yasutaka,Ogawa, Masaya
, p. 857 - 860 (2007/10/02)
A facile conversion of olefins into carboxylic acids could be achieved by using aqueous hydrogen peroxide (35percent-H2O2) in the presence of catalytic amounts of tungstic acid (5 wtpercent).The oxidation was markedly influenced by the acidity of the reaction medium, and it was found to proceed favorably under a weak acidic condition (pH 4-5).
