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One-pot synthesis of alcohols from olefins catalyzed by rhodium and ruthenium complexes

Paper ID Volume ID Publish Year Pages File Format Full-Text
42154 45912 2010 12 PDF Available
Title
One-pot synthesis of alcohols from olefins catalyzed by rhodium and ruthenium complexes
Abstract

The one-pot synthesis of butanol and heptanol from propene and 1-hexene, respectively, was performed using Ru3(PPh3)Cl2 and Rh(CO)2(acac) in the presence of triphenylphosphene. The effects of various reaction parameters, including catalyst concentration, gas partial pressures, and temperature, were investigated. Two methods for performing the one-pot synthesis were developed and are discussed. In the first method, stoichiometric quantities of CO and propene or 1-hexene were fed to the autoclave. It was found that residual carbon monoxide necessary for the hydroformylation poisoned the Ru catalyst used for the hydrogenation. Venting the hydroformylation gases was therefore necessary for hydrogenation of the aldehyde to proceed. In the second method, sub-stoichiometric quantities of CO relative to olefin were fed to the autoclave, and CO conversion was driven to nearly 100%. In this case, the low residual CO concentration allowed the hydrogenation to proceed readily. The optimal temperatures and gas pressures for the hydroformylation were not the optimal temperatures and pressures for the hydrogenation. A strategy is described for maximizing the performance of both steps. Under optimal conditions, 100% conversion of propene to butanol could be achieved with 97% selectivity, and 99% conversion of 1-hexene to hepatanol could be achieved with 98% selectivity. The only byproduct observed in the latter case was a small amount of 2-hexene, which did not undergo hydroformylation. A possible reaction mechanism is proposed for both the hydroformylation of the olefin and the hydrogenation of aldehyde based on spectroscopic evidence.

Graphical abstractThe one-pot synthesis of butanol and heptanol from propene and 1-hexene, respectively, was performed using Ru(PPh3)Cl2 and Rh(CO)2(acac) in the presence of triphenylphosphene. Two methods for performing the one-pot synthesis were developed and are discussed.Figure optionsDownload full-size imageDownload high-quality image (20 K)Download as PowerPoint slide

Keywords
Olefin; Alcohol; Aldehyde hydrogenation; Hydroformylation; One-pot synthesis
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One-pot synthesis of alcohols from olefins catalyzed by rhodium and ruthenium complexes
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 374, Issues 1–2, 1 February 2010, Pages 201–212
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
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Full-text PDF Download
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