Method of preparing a hydroxy functional vegetable oil

Abstract

A simple, economical preparative method for the provision of hydroxyl functional materials that are derived by converting the alkene groups of the unsaturated molecules found in vegetable oils, into hydroxyl groups.

1 . A method of preparing a hydroxy functional vegetable oil, the process comprising contacting a raw vegetable oil with hydrogen peroxide and an organic acid in the presence of water for a sufficient period of time, a sufficient temperature, and a sufficient pressure to form alcohols from unsaturated moieties in the vegetable oil, and thereafter separating any volatiles from the hydroxylated functional vegetable oil, wherein the organic acid has from 1 to 20 carbon atoms selected from the group consisting of saturated moities and unsaturated moities.  
     
     
         2 . A method of preparing a hydroxy functional vegetable oil as claimed in  claim 1  wherein the vegetable oil is selected from the group consisting of corn oil, palm oil, soybean oil, cottonseed oil, peanut oil, rapeseed oil, safflower oil, canola, fish oils, beef tallow, lard, olive oil, and sunflower oil.  
     
     
         3 . A method of preparing a hydroxy functional vegetable oil as claimed in  claim 1  wherein the raw vegetable oil is contacted with a combination of the peroxide and organic acid essentially simultaneously.  
     
     
         4 . A method of preparing a hydroxy functional vegetable oil as claimed in  claim 1  wherein the raw vegetable oil is contacted with the organic acid first, and then contacted with the peroxide.  
     
     
         5 . A method of preparing a hydroxy functional vegetable oil as claimed in  claim 1  wherein the raw vegetable oil is contacted with the peroxide first and then is contacted with the organic acid.  
     
     
         6 . A method of preparing a hydroxy functional vegetable oil as claimed in  claim 1  wherein the time of reaction if from 1 to 24 hours.  
     
     
         7 . A method of preparing a hydroxy functional vegetable oil as claimed in  claim 1  wherein the temperature ranges from about 25° C. to about 125° C.  
     
     
         8 . A method of preparing a hydroxy functional vegetable oil as claimed in  claim 1  wherein the amount of organic acid that is used ranges from about 0.4 molar equivalents in volume to about 2.0 molar equivalents in volume based on the amount of raw vegetable oil.  
     
     
         8 . A method of preparing a hydroxy functional vegetable oil as claimed in  claim 1  wherein the organic acid that is used is a mixture of two or more organic acids.  
     
     
         10 . A method of preparing a hydroxy functional vegetable oil as claimed in  claim 1  wherein the amount of peroxide that is used ranges from about 0.7 to about 6.0 equivalents based on the amount of unsaturation in the raw vegetable oil.  
     
     
         11 . A hydroxy functional vegetable oil when prepared by the method of  claim 1 .  
     
     
         12 . A method of preparing a hydroxy functional vegetable oil as claimed in  claim 1  wherein there is additionally present a solvent.  
     
     
         13 . A method of preparing hydroxy functional vegetable oil as claimed in  claim 1  wherein the hydroxy functional vegetable oil that is obtained is extracted from the reaction mass using a solvent selected from the group consisting of toluene, methylene chloride, tetrahydrofuran, methanol, ethanol, and ethyl acetate.  
     
     
         14 . A method as claimed in  claim 13  wherein following extraction, the solvent is removed and the hydroxy functional vegetable residue is subjected to distillation.  
     
     
         15 . A method as claimed in  claim 13  wherein following extraction, the solvent is removed and the hydroxy functional vegetable residue is subjected to an evaporation step.  
     
     
         16 . In a polyurethane article, the incipient ingredients being a hydroxy functional vegetable oil of  claim 11  and a urethane system reactive with the hydroxy functional vegetable oil.  
     
     
         17 . A method of preparing a cured polyurethane, the method comprising reacting a hydroxy functional vegetable oil as claimed in  claim 11  with a reactive urethane system and allowing the polyurethane to cure.  
     
     
         18 . A polyurethane article prepared by the method of  claim 17 .  
     
     
         19 . A polyurethane article as claimed in  claim 18  that is a foamed material.  
     
     
         20 . The foamed material as claimed in  claim 19  that is a flexible foam.  
     
     
         21 . The foamed material as claimed in  claim 19  that is a rigid foam.  
     
     
         22 . The foamed material as claimed in  claim 19  that is a semi-rigid foam.  
     
     
         23 . The foamed material as claimed in  claim 21  that is a construction foam.  
     
     
         24 . The foamed material as claimed in  claim 23  that is used as insulation in construction.  
     
     
         25 . The foamed material as claimed in  claim 23  that is an ornamental foam.  
     
     
         26 . A cured polyurethane article as claimed in  claim 18  that is an elastomer material.  
     
     
         27 . A cured polyurethane article as claimed in  claim 18  that is a castable material.  
     
     
         28 . A cured polyurethane article as claimed in  claim 18  that is a carpet backing.  
     
     
         29 . The method as claimed in  claim 17  that is a reaction injectable molding method.  
     
     
         30 . The method as claimed in  claim 17  that is a castable molding method.  
     
     
         31 . The method as claimed in  claim 17  that is a slab stock method.  
     
     
         32 . The method as claimed in  claim 17  that is an extrusion method.