Selective Electrochemical Hydrogenation of Alkynes to Alkenes

Abstract

Various embodiments include a method for the partial electrochemical hydrogenation of alkynes of the chemical formula (I) to alkenes, wherein R and R′ are selected from inorganic and/or organic radicals, the method comprising: hydrogenating the compound of the chemical formula (I) on a copper-containing electrode.

What is claimed is: 
     
         1 . A method for the partial electrochemical hydrogenation of alkynes of the chemical formula (I) to alkenes, 
       
         
           
           
               
               
           
         
         wherein R and R′ each comprise at least one inorganic or organic radicals, the method comprising: 
         hydrogenating the compound of the chemical formula (I) on a copper-containing electrode. 
       
     
     
         2 . The method as claimed in  claim 1 , wherein the inorganic and organic radicals comprise at least one compound selected from the group consisting of: —H, -D, alkyl, alkenyl, alkynyl and/or aryl radicals, —OH, —OR*, —SH, —SR*, —NH 2 , —NR*R*, —COOH, —COOR*, —CHO, —COR*, —PH 2 , —PR*R*, —F, —Cl, —Br, —I, —NO, and —NO 2 , where R* and R* are organic and/or inorganic radicals. 
     
     
         3 . The method as claimed in  claim 1 , wherein neither R nor R′ are —H or -D. 
     
     
         4 . The method as claimed in  claim 1 , wherein the alkyne of the chemical formula (I) comprises no electron-withdrawing radicals. 
     
     
         5 . The method as claimed in  claim 4 , wherein the electron-withdrawing radicals comprise a compound selected from the group consisting of: —COOH, —COOR*, and fluorinated alkyl or aryl radicals. 
     
     
         6 . The method as claimed in  claim 1 , wherein the alkyne of the chemical formula (I) comprises no further reducible functional groups apart from the triple bond. 
     
     
         7 . The method as claimed in  claim 1 , wherein the hydrogenation is carried out with a proton donor selected from water and alcohols having 1 to 20 carbon atoms. 
     
     
         8 . The method as claimed in  claim 1 , wherein:
 the copper-containing electrode is configured as comprises a gas diffusion electrode; and   the alkyne of the chemical formula (I) is gaseous.   
     
     
         9 . (canceled) 
     
     
         10 . A device for the partial electrochemical hydrogenation of alkynes of the chemical formula (I) to alkenes, 
       
         
           
           
               
               
           
         
         wherein R and R′ are selected from inorganic and/or organic radicals, the device comprising: 
         an electrolysis cell with a copper-containing electrode configured to reduce the alkyne of the chemical formula (I) to an alkene; 
         a source of the alkyne of the chemical formula (I); and 
         a first feeding device configured to feed the alkyne of the chemical formula (I) from the source of the alkyne of the chemical formula (I) to the electrolysis cell. 
       
     
     
         11 . The device as claimed in  claim 10 , wherein:
 the copper-containing electrode comprises a gas diffusion electrode; and   the first feeding device for the alkyne of the chemical formula (I) feeds the alkyne of the chemical formula (I) to the gas diffusion electrode.