Radical generating catalyst, method for producing radical, method for producing oxidation reaction product, drug, and drug for agriculture and livestock

Abstract

An object of a first aspect of the present invention is to provide a radical generating catalyst that can generate (produce) radicals under mild conditions. In order to achieve the above object, a first radical generating catalyst according to the first aspect of the present invention is characterized in that it includes ammonium and/or a salt thereof. A second radical generating catalyst according to the first aspect of the present invention is characterized in that it includes an organic compound having Lewis acidic properties and/or Brønsted acidic properties.

1 - 70 . (canceled) 
     
     
         71 . A radical generating catalyst comprising:
 an ammonium salt represented by the following chemical formula (XI) (excluding peroxodisulfate) and having a Lewis acidity of 0.4 eV or more, wherein
 the radical generating catalyst catalyzes radical generation from a radical source in a liquid that is not acidic, and 
 the radical source is at least one selected from the group consisting of halogenous acids, halite ions, and halites: 
   
       
         
           
           
               
               
           
         
       
       where in the chemical formula (XI),
 R 11 , R 21 , R 31 , and R 41  are each a hydrogen atom or an alkyl group and may each comprise an ether bond, a carbonyl group, an ester bond, or an amide bond, or an aromatic ring, 
 and R 11 , R 21 , R 31 , and R 41  may be the same or different from each other, and 
 X −  is an anion (excluding a peroxodisulfate ion). 
 
     
     
         72 . The radical generating catalyst according to  claim 71 , wherein
 in the ammonium salt represented by the chemical formula (XI),   R 11 , R 21 , R 31 , and R 41  are each a hydrogen atom or an alkyl group, and   R 11 , R 21 , R 31 , and R 41  may be the same or different from each other.   
     
     
         73 . The radical generating catalyst according to  claim 71 , wherein
 the ammonium salt represented by the chemical formula (XI) is an ammonium salt represented by the following chemical formula (XII):   
       
         
           
           
               
               
           
         
       
       where in the chemical formula (XII),
 R 111  is an alkyl group having 5 to 40 carbon atoms and may comprise an ether bond, a carbonyl group, an ester bond, or an amide bond, or an aromatic ring, and 
 R 21  and X −  are the same as those in the chemical formula (XI). 
 
     
     
         74 . The radical generating catalyst according to  claim 71 , wherein
 the ammonium salt represented by the chemical formula (XI) is at least one selected from the group consisting of benzethonium chloride, benzalkonium chloride, hexadecyltrimethylammonium chloride, tetramethylammonium chloride, ammonium chloride, tetrabutylammonium chloride, cetylpyridinium chloride, hexadecyltrimethylammonium bromide, dequalinium chloride, edrophonium, didecyldimethylammonium chloride, benzyltriethylammonium chloride, oxytropium, carbachol, glycopyrronium, safranin, sinapine, tetraethylammonium bromide, hexadecyltrimethylammonium bromide, suxamethonium, sphingomyelin, denatonium, trigonelline, neostigmine, paraquat, pyridostigmine, phellodendrine, pralidoxime methiodide, betaine, betanin, bethanechol, lecithin, and cholines.   
     
     
         75 . The radical generating catalyst according to  claim 71 , wherein
 the ammonium salt represented by the chemical formula (XI) is an ammonium salt represented by the following chemical formula (XIII):   
       
         
           
           
               
               
           
         
       
       where in the chemical formula (XIII),
 R 111  is an alkyl group having 5 to 40 carbon atoms, and 
 X −  is the same as that in the chemical formula (XI). 
 
     
     
         76 . The radical generating catalyst according to  claim 71 , wherein
 the ammonium salt is a salt of NH 4   + .   
     
     
         77 . The radical generating catalyst according to  claim 76 , wherein
 the ammonium salt is NH 4 Cl.   
     
     
         78 . The radical generating catalyst according to  claim 71 , wherein
 the ammonium salt is a hexafluorophosphate of the ammonium.   
     
     
         79 . The radical generating catalyst according to  claim 71 , wherein
 the radical source is a chlorite ion.   
     
     
         80 . A radical generating catalyst comprising:
 an ammonium salt represented by the following chemical formula (XI) and having a Lewis acidity of 0.4 eV or more, wherein
 the radical generating catalyst catalyzes radical generation from a radical source in the presence of an oxidizing agent, 
 the oxidizing agent is O 2 , and 
 the radical source is at least one selected from the group consisting of: nitrogen-containing aromatic cation derivatives represented by the following formulae (A-1) to (A-8); 9-substituted acridinium ions represented by the following formula (A-9); quinolinium ion derivatives represented by the following formula (I); stereoisomers and tautomers thereof, and salts thereof: 
   
       
         
           
           
               
               
           
         
       
       where in the chemical formula (XI),
 R 11 , R 21 , R 31 , and R 41  are each a hydrogen atom or an alkyl group and may each comprise an ether bond, a carbonyl group, an ester bond, or an amide bond, or an aromatic ring, and R 11 , R 21 , R 31 , and R 41  may be the same or different from each other, and 
 X −  is an anion, 
 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       where in the formulae (A-1) to (A-8) and (A-9),
 R is a hydrogen atom or any substituent, 
 Ar is an electron donor group, and the number of Ars may be one or more, and when a plurality of Ars are present, they may be the same or different from each other, 
 a nitrogen-containing aromatic ring that forms a nitrogen-containing aromatic cation may or may not have at least one substituent other than R and Ar, and 
 in the formula (I), 
 R 1  is a hydrogen atom or any substituent, 
 Ar 1  to Ar 3  are each a hydrogen atom or the electron donor group and may be the same or different from each other, and at least one of Ar 1  to Ar 3  is the electron donor group. 
 
     
     
         81 . A method for producing a radical, the method comprising:
 mixing a Lewis acid having a Lewis acidity of 0.4 eV or more, O 2 , and a radical source together; and   reacting the Lewis acid, the O 2 , and the radical source with each other in a liquid, wherein   the Lewis acid is the radical generating catalyst according to  claim 80 , and   the radical source is at least one selected from the group consisting of: nitrogen-containing aromatic cation derivatives represented by the formulae (A-1) to (A-8); 9-substituted acridinium ions represented by the formula (A-9); quinolinium ion derivatives represented by the formula (I); stereoisomers and tautomers thereof; and salts thereof.   
     
     
         82 . A method for producing a radical, the method comprising:
 mixing a Lewis acid having a Lewis acidity of 0.4 eV or more (excluding peroxodisulfate) with a radical source; and   reacting the Lewis acid with the radical source in a liquid, wherein   the Lewis acid having a Lewis acidity of 0.4 eV or more comprises an inorganic substance, and   the radical source is at least one selected from the group consisting of halogenous acids, halite ions, and halites.   
     
     
         83 . The method according to  claim 82 , wherein
 the inorganic substance comprises a metal ion.   
     
     
         84 . The method according to  claim 83 , wherein
 the inorganic substance is at least one selected from the group consisting of alkaline-earth metal ions, rare-earth ions, Mg 2+ , Sc 3+ , Li + , Fe 2+ , Fe 3+ , A13+, silicate ions, and borate ions.   
     
     
         85 . A method for producing an oxidation reaction product by oxidizing a substance to be oxidized, the method comprising:
 a radical production step of producing a radical by a method comprising:
 mixing a Lewis acid having a Lewis acidity of 0.4 eV or more (excluding peroxodisulfate) with a radical source; and 
 reacting the Lewis acid with the radical source in a liquid that is not acidic, wherein 
 the radical source is at least one selected from the group consisting of halogenous acids, halite ions, and halites; and 
 reacting the substance to be oxidized with an oxidizing agent by action of the radical, thereby generating the oxidation reaction product. 
   
     
     
         86 . The method according to  claim 85 , wherein
 the radical also serves as the oxidizing agent.