Process for modifying unsaturated triacylglycerol oils; resulting products and uses thereof

Abstract

A process for modifying an unsaturated triacylglycerol oil, such as an vegetable oil stock, to enhance its fluidity and/or oxidative stability is provided. Lubricants containing a modified an unsaturated triacylglycerol oil and methods for their production and use are also provided.

What is claimed is:  
     
         1 . A process for modifying an unsaturated triacylglycerol oil comprising: 
 reacting the unsaturated triacylglycerol oil with an olefinic hydrocarbon to form a cycloaddition product comprising triacylglycerols which have at least one unsaturated fatty acyl chain modified to include a cycloaddition adduct; and    at least partially hydrogenating the cycloaddition product to form a hydrogenated cycloaddition product.    
     
     
         2 . The process of  claim 1  wherein the at least partially hydrogenating step comprises hydrogenating the cycloaddition product to form a hydrogenated cycloaddition product having an Iodine Value reduced by at least about 10% with respect to that of the cycloaddition product.  
     
     
         3 . The process of  claim 1  wherein the at least partially hydrogenating step comprises hydrogenating the cycloaddition product to form a hydrogenated cycloaddition product having an active methylene content reduced by at least about 0.5 with respect to that of the cycloaddition product.  
     
     
         4 . The process of  claim 1  wherein the reacting step comprises reacting the unsaturated triacylglycerol oil with an olefinic hydrocarbon including a diene.  
     
     
         5 . The process of  claim 4  wherein the reacting step comprises reacting the unsaturated triacylglycerol oil with an olefinic hydrocarbon including a diene selected from the group consisting of cyclopentadiene, alkyl substituted cyclopentadienes, butadiene, alkyl substituted butadienes, and mixtures thereof.  
     
     
         6 . The process of  claim 4  wherein the reacting step comprises reacting the unsaturated triacylglycerol oil with a diene comprising cyclopentadiene.  
     
     
         7 . The process of  claim 6  wherein the reacting step comprises reacting the unsaturated triacyiglycerol oil with a diene further comprising 1-methylcyclo-pentadiene and 2 -methyl cyclopentadiene.  
     
     
         8 . The process of  claim 1  wherein the reacting step comprises reacting the unsaturated triacylglycerol oil with sufficient olefinic hydrocarbon to form a cycloaddition product having an average cycloaddition content of at least about 0.25 adducts per triacyiglycerol molecule.  
     
     
         9 . The process of  claim 1  wherein the unsaturated triacylglycerol oil has an Iodine Value of no more than about 150.  
     
     
         10 . The process of  claim 1  wherein the reacting step comprises reacting the olefinic hydrocarbon with an unsaturated triacylglycerol oil selected from the group consisting of soybean oil, rapeseed oil, olive oil, sunflower oil, safflower oil, peanut oil, cottonseed oil, crambe oil, mustard oil, meadowfarm oil, herring oil, menhaden oil and mixtures thereof.  
     
     
         11 . The process of  claim 10  wherein the sunflower oil comprises a high oleic sunflower oil.  
     
     
         12 . The process of  claim 10  wherein the rapeseed oil comprises a high oleic canola oil.  
     
     
         13 . The process of  claim 1  wherein the reacting step comprises reacting an olefinic hydrocarbon including a diene with an unsaturated triacylglycerol oil including soybean oil.  
     
     
         14 . The process of  claim 1  wherein the reacting step comprises forming a cycloaddition product having an AOM value at least about 50% higher than that of the unsaturated triacylglycerol oil.  
     
     
         15 . The process of  claim 1  wherein the at least partially hydrogenating step comprises forming a hydrogenated cycloaddition product having an AOM value at least about 50% higher than that of the cycloaddition product.  
     
     
         16 . The process of  claim 1  wherein the reacting step comprises reacting the unsaturated triacylglycerol oil with an olefinic hydrocarbon including a monoolefinic hydrocarbon.  
     
     
         17 . A modified unsaturated triacylglycerol oil comprising triacylglycerols which include at least one unsaturated fatty acyl chain modified to include a cycloaddition adduct; wherein said modified vegetable oil stock has a viscosity at 40° C. of no more than about 200 cP.  
     
     
         18 . The modified unsaturated triacylglycerol oil of  claim 17  having an AOM value of at least about 50 hours.  
     
     
         19 . The modified unsaturated triacylglycerol oil of  claim 17  having an Iodine Value of no more than about 130.  
     
     
         20 . The modified unsaturated triacylglycerol oil of  claim 17  having an active methylene content of no more than about 1.5.  
     
     
         21 . A method for producing a lubricant comprising: 
 reacting an unsaturated triacylglycerol oil with an olefinic hydrocarbon to form a cycloaddition product including at least one triacylglycerol cycloaddition adduct.    
     
     
         22 . The method of  claim 21  wherein the unsaturated triacylglycerol oil has an Iodine Value of no more than about 140.  
     
     
         23 . The method of  claim 21  further comprising hydrogenating the cycloaddition product to form a hydrogenated cycloaddition product having an Iodine Value reduced by at least about 10 Iodine Value units with respect to that of the cycloaddition product.  
     
     
         24 . The method of  claim 21  further comprising blending the hydrogenated cycloaddition product with a petroleum based lubricant base stock.  
     
     
         25 . A lubricant comprising unsaturated triacylglycerols modified to have at least one fatty acyl chain including a cycloaddition adduct.  
     
     
         26 . A process for producing a lubricant base stock comprising: 
 reacting an unsaturated triacylglycerol oil having an Iodine Value of about 50 to about 150 with an olefinic hydrocarbon to form a cycloaddition product comprising triacylglycerols which have at least one unsaturated fatty acyl chain modified to include a cycloaddition adduct.    
     
     
         27 . The process of  claim 26  wherein the cycloaddition product has an AOM value at least about 50% higher than that of the unsaturated triacylglycerol oil.  
     
     
         28 . The process of  claim 26  wherein the cycloaddition product has an active methylene content at least about 10% lower than that of the unsaturated triacylglycerol oil.  
     
     
         29 . The process of  claim 26  comprising hydrogenating the cycloaddition product to produce a hydrogenated cycloaddition product having an Iodine Value at least about 10% lower than that of the cycloaddition product.  
     
     
         30 . The process of  claim 29  further comprising fractionating the hydrogenated cycloaddition product to produce a fractionating cycloaddition product having an Iodine Value at least about 10% higher than that of the hydrogenated cycloaddition product.  
     
     
         31 . A lubricant formed by a process comprising: 
 reacting an olefinic hydrocarbon with an unsaturated triacylglycerol to form a cycloaddition product comprising a triacylglycerol having at least one unsaturated fatty acyl chain modified to include a cycloaddition adduct.    
     
     
         32 . The lubricant of  claim 31  wherein the process further comprises at least partially hydrogenating the a cycloaddition product to form a hydrogenated a cycloaddition product.  
     
     
         33 . A method of reducing friction between moving parts comprising applying a lubricant to at least one of said moving parts, wherein the lubricant comprises at least one unsaturated triacylglycerol oil modified to comprise at least one fatty acyl chain including a cycloaddition adduct.  
     
     
         34 . A method of disposing of a used lubricant comprising biodegrading the used lubricant; 
 wherein the used lubricant is derived from a lubricant comprising an unsaturated triacylglycerol modified to have at least one fatty acyl chain including a cycloaddition adduct.