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Reduction of Alkenes: Catalytic Hydrogenation02:13

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Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
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Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
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Introduction
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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Wolff–Kishner reduction involves converting aldehydes and ketones to alkanes using hydrazine and a base. The reaction converts a carbonyl group to a methylene group. The method was independently discovered by N. Kishner in 1911 and L. Wolff in 1912. The reduction is carried out in high-boiling solvents such as ethylene glycol and diethylene glycol because heat is required to deprotonate the N–H proton in one of the reaction steps.                                       ...
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Integrated electrochemical CO2 reduction and hydroformylation.

Brandon J Jolly1, Michael J Pung1, Chong Liu1,2

  • 1Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, USA. chongliu@chem.ucla.edu.

Dalton Transactions (Cambridge, England : 2003)
|May 3, 2024
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Summary

This study integrates electrochemical carbon dioxide reduction (CO2RR) with hydroformylation to produce aldehydes from CO2. It cleverly uses hydrogen evolution from CO2RR to supply necessary gases for aldehyde synthesis in a single pass.

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Area of Science:

  • Catalysis
  • Electrochemistry
  • Green Chemistry

Background:

  • Integrated multi-catalyst processes are crucial for converting feedstocks and pollutants into valuable chemicals efficiently.
  • Carbon dioxide (CO2) is an abundant C1 source and a significant environmental pollutant, making its chemical transformation highly desirable.

Purpose of the Study:

  • To develop a novel process for synthesizing aldehydes directly from CO2.
  • To integrate electrochemical CO2 reduction (CO2RR) with hydroformylation in a one-pot, one-pass system.
  • To utilize the hydrogen evolution reaction (HER) byproduct from CO2RR as a reactant for hydroformylation.

Main Methods:

  • A vial-in-vial reactor was employed to spatially segregate CO2RR and hydroformylation catalyst systems.
  • Electrochemical reduction of CO2 was coupled with hydroformylation of styrene.
  • Transport of CO and H2 generated during CO2RR to the hydroformylation site was enabled.

Main Results:

  • High aldehyde yields were achieved from CO2RR and styrene using a homogeneous rhodium catalyst (97% yield).
  • A heterogenized rhodium catalyst on mesoporous silica also produced aldehydes from CO2, yielding 43%.
  • The process successfully repurposed hydrogen evolution from CO2RR and eliminated the need for external H2 addition.

Conclusions:

  • This work demonstrates a viable method for aldehyde synthesis from CO2 by integrating CO2RR and hydroformylation.
  • The developed system efficiently utilizes CO2 as a feedstock and repurposes HER, contributing to sustainable chemical synthesis.
  • This approach expands the scope of one-pass catalytic processes for transforming feedstocks into commodity chemicals.