New methods for disproportionation quenching of ozonides

Abstract

The present disclosure provides improved methods of performing ozonolysis on alkenes comprising non-reductive quenching of ozonide intermediates using Bronsted bases to yield aldehyde, ketone and/or carboxylic acid products.

1 . A method of non-reductive quenching of ozonides using Bronsted bases to yield aldehyde and carboxylic acid, or ketone and carboxylic acid products, wherein the method comprises (a) reacting an alkene with ozone to generate a secondary ozonide intermediate, and (b) quenching the ozonide by adding an alkali metal or alkaline earth metal hydroxide, carbonate, bicarbonate, sulfate, or phosphate, to the ozonide in a C 8 -C 26  fatty acid solvent with water co-solvent to form the corresponding alkali metal or alkaline earth metal C 8 -C 26  fatty acid carboxylate salt Bronsted base in-situ, to yield the aldehyde and carboxylic acid, or the ketone and carboxylic acid products; and
 wherein step (b) does not comprise a reducing agent and/or an oxidizing agent.   
     
     
         2 . (canceled) 
     
     
         3 . (canceled) 
     
     
         4 . (canceled) 
     
     
         5 . (canceled) 
     
     
         6 . The method of  claim 1 , wherein the inorganic Bronsted base is an alkali metal fatty acid carboxylate. 
     
     
         7 . The method of  claim 1 , wherein the fatty acid carboxylate is a a C 8 , C 10 , C 12 , C 14 , C 16 , C 18 , C 20 , C 22 , C 24  or C 26  fatty acid carboxylate. 
     
     
         8 . The method of  claim 1 , wherein the fatty acid carboxylate is a saturated fatty acid carboxylate. 
     
     
         9 . The method of  claim 1 , wherein the fatty acid carboxylate is an unsaturated fatty acid carboxylate. 
     
     
         10 . The method of  claim 1 , wherein the alkali metal or alkaline earth metal hydroxide, carbonate, bicarbonate, sulfate or phosphate added in step (b) is an alkali metal or alkaline earth metal hydroxide. 
     
     
         11 . (canceled) 
     
     
         12 . The method of  claim 1 , wherein the carboxylic acid is an unsaturated fatty acid and the unsaturated fatty acid is the alkene precursor to the ozonide. 
     
     
         13 . The method of  claim 10 , wherein the alkali metal or alkaline earth metal hydroxide is selected from the group consisting of sodium hydroxide, potassium hydroxide, calcium hydroxide, magnesium hydroxide. 
     
     
         14 . (canceled) 
     
     
         15 . The method of  claim 1 , wherein step (b) occurs at a temperature from 30 to 100° C., optionally, wherein said temperature is between 50 and 90° C. or between 50 and 80° C. 
     
     
         16 . The method of  claim 1 , wherein the method further comprises isolating or purifying an aldehyde product and a carboxylic acid product, or a ketone product and a carboxylic acid product, from the quenching step (b). 
     
     
         17 . The method of  claim 1 , wherein the alkene is a monounsaturated fatty acid or ester. 
     
     
         18 . The method of  claim 1 , wherein the alkene is a terpene. 
     
     
         19 . The method of  claim 18 , wherein the terpene is selected from pinenes, camphenes, citronellol, citronellal, isopulegol, longifolene, isothujone and thujone. 
     
     
         20 . The method of  claim 1 , wherein the alkene is oleic acid, ricinoleic acid, erucic acid, or any esters thereof. 
     
     
         21 . The method of  claim 1 , wherein the secondary ozonide is a monosubstituted, disubstituted, or trisubstituted ozonide, and the products comprise aldehyde or ketone product and carboxylic acid product. 
     
     
         22 . The method of  claim 8 , wherein the fatty acid carboxylate is selected from a caprylate, caprate, laurate, myristate, palmitate, stearate, arachidate, behenate, lignocerate or ceroate. 
     
     
         23 . The method of  claim 9 , wherein the fatty acid carboxylate is selected from a myristoleate, pamitoleate, sapienate, oleate, elaidate, gadolaeate, eicosenoate, erucate, eicosadienoate, docosadienoate, linoleate, linolenate, stearidonate, or arachidonate. 
     
     
         24 . The method of  claim 17 , wherein the alkene is a C 8 -C 26  monounsaturated fatty acid or ester.