Synthetic esters derived from high stability oleic acid

Abstract

The present invention is directed to a composition comprising a synthetic ester having a fatty acid mixture including: oleic acid in amount of at least about 85 wt % of the fatty acid mixture; linoleic acid in an amount of about 3 wt % of the fatty acid mixture or less; and linolenic acid in an amount of about 0.5 wt % of the fatty acid mixture or less.

1 .- 14 . (canceled) 
     
     
         15 . A method of preparing a synthetic ester, the method comprising reacting a fatty acid mixture with an alcohol, wherein the fatty acid mixture comprises:
 a. oleic acid in amount of at least about 85 wt % of the fatty acid mixture;   b. linoleic acid in an amount of about 3 wt % of the fatty acid mixture or less; and   c. linolenic acid in an amount of about 0.5 wt % of the fatty acid mixture or less.   
     
     
         16 . The method of  claim 15 , wherein the oleic acid is a high stability oleic acid. 
     
     
         17 . The method of  claim 15 , wherein the alcohol is selected from the group consisting of: trimethylol propane (TMP), neopentyl glycol (NPG), pentaerythritol (PE), 2-butyl-2-ethyl-1,3-propanediol (BEPD), 2,2,4-trimethyl-1,3-propanediol (TMPD), polyglycerol, 2,2-diethyl-1,3-propanediol, 1,3,-propanediol, 1,2-propanediol, 1,4-butanediol, 1,4-butenediol, 1,4-butynediol, 1,6-hexanediol, 1,2-cyclohexanediol, 1,4-cyclohexanediol, 1,2-, 1,3-, 1,4-, 1,8-, 2,4-, 2,7-, and 4,5-octanediol, tricyclodecane dimethanol (TCD), 1,4-cyclohexanedimethanol, 1,12-dodecanediol, 2-methyl-2,4-pentanediol, 2-methyl-1,3-propanediol (MPD), 2-methyl-1,2-propanediol, 2-hydroxyethoxy-ethan-2-ol, dipropylene glycol (3 isomer mixture), di-pentaerythritol, tri-pentaerythritol, di-trimethylolpropane (di-TMP), triethylene glycol, tri-propylene glycol, tetraethylene glycol, tetrapropylene glycol, polyethylene glycol (PEG, 1\4W 200-1.000.000 g/mol), polypropylene glycol (PPG, MW 200-10.000 g/mol), ethylene glycol, 1,2,-, 1,3-, 2,3-butanediol, 1,1-, 1,3-, 1,4-, 2,3-, 2,4-pentanediol, 2-butene-1,2-diol, 2-butene-1,4-diol, 2-methyl-1,5-pentanediol, 2,4-dimethyl-2,4-pentanediol, 2,2-diethyl-1,4-butanediol, 2-pentene-1,5-diol, 2-propyl-1,3-butanediol, 1,4-hexanediol, 1,6-hexanediol, 5-methyl-1,2-hexanediol, 1-phenyl-1,2-ethanediol, 2-phenyl-1,2-propanediol, 1,6-diphenyl-1,6-hexanediol, 1,2-diphenyl-1,2-ethanediol, tris(2-hydroxyethyl)isocyanurate (THEIC), poly-tetrahyfrofuran (poly-THF, MW 250, 650, 1000, 1400, 1800 and 2000 g/mol), 2-ethyl-1,3-hexanediol (EHD), EO-PO block copolymers, EO-PO-EO block copolymers, PO-EO block copolymers, PO-EO-PO block copolymers, 1,2-pentanediol, 4-methyl-1,4-hexanediol, 3,3-dimethyl-1,6-hexanediol, 2,4-dimethyl-3-hexene-2,5-diol, 2,3-, 2,4-, 2,5-, 3,4-hexanediol, 1,2,3,6-hexanetetrol, 2-heptene-1,6-diol, 5-ethyl-3-methyl-2,4-heptanediol, 2-methyl-2-octene-1,4-diol, 2,4,4,5,5,7-hexamethyl-3,6-octanediol, 2,7-dimethyl-4-octane-2,7-diol, 2-butyl-4-ethyl-3-methyl-1,3-octanediol, 1,9-nonanediol, 1,2-, 1,10-decanediol, 5-decyne-4,7-diol, 5,8-diethyl-6,7-dodecanediol, 9-octadecene-1,12-diol, 9,10,1,12-octadecanediol, 1,9-, 1,11-undecanediol, 1,13-tridecanediol, 1,2-tetradecanediol, 1,2-, 1,16-hexadecanediol, 1,2-, 1,12-octadecanediol, 2-isobutyl-1,3-propanediol, 2-ethyl-1,3-propanediol, 2-ethyl-1,3-butanediol, 2,2-diethyl-1,4-butanediol, 2,2,3,3,-tetramethyl-1,4-butanediol, bisphenol A, hydrogenated bisphenol A, ortho,meta, para-xylene-alpha, alpha diols, 3,6-dimethyl-ortho-xylene-alpha,alpha-diol, alpha,alpha-dimethyl-para-xylene-alpha,alpha diol, 1,6-diphenyl-1,6-hexanediol; 2-ethyl-2-(hydroxymethyl)-1,3-propanediol ethoxylates (TMP-EOx where x ranges from 1 to 100 moles of EO), 2-ethyl-2-(hydroxymethyl)-1,3-propanediol propoxylates (TMP-POx, where x ranges from 1-100 moles of PO), 2-ethyl-2-(hydroxymethyl)-1,3-propanediol (random) alkoxylates (TMP-EOx-POy, TMP-EOx-POy-EOx, TMP-POx-EOy, TMP-POx-EOy-POx, where x and y range from 1-100 moles both for E0 and PO), 2-ethyl-2-(hydroxymethyl)-1,3-propanediol butoxylate (TMP-BuOx, where x ranges from 1-25 moles of BuO (butyleneoxide)), 2,2-dimethyl-1,3-propanediol ethoxylates (NPG-EOx, where x ranges from 1 to 100 moles of EO), 2,2-dimethyl-1,3-propanediol propoxylates (NPG-PDx, where x ranges from 1 to 100 moles of PO), 2,2-dimethyl-1,3-propanediol (random) alkoxylates (NPG-EOx-POy, NPG-POx-EOy, NPG-EOx-POy-EOx, NPG-POx-EOy-POx where x and y range from 1 to 100 moles for both EO and PO), 2,2-dimethyl-1,3-propanediol butoxylate (NPG-BuOx, where x ranges from 1 to 25 moles of BuO), 2,2-bis(hydroxymethyl)-1,3-propanediol ethoxylates (penta EOx, where x ranges from 1-100 moles of EO), 2,2-bis(hydroxymethyl)-1,3-propanediol propoxylates (penta POx, where x ranges from 1-100 moles of propyleneoxide (PO)), 2,2-bis(hydroxymethyl)-1,3-propanediol (random) alkoxylates (penta EOx-POy where x and y range from 1-100 moles of EO and PO), 2,2-bis(hydroxymethyl)-1,3-propanediol EOx-POy-EOx (penta EOx-POy-EOx, where x and y range from 1-100 moles of EO and PO), 2,2-bis(hydroxymethyl)-1,3-propanediol butoxylates (penta BuOx, where x ranges from 1-25 moles of butyleneoxide), 2-butyl-2-ethyl-1,3-propanediol (BEPD) ethoxylates (BEPD-EOx, where x ranges from 1-100 moles of EO), 2-butyl-2-ethyl-1,3-propanediol propoxylates (BEPD-POx, where x ranges from 1-100 moles of PO), 2-butyl-2-ethyl-1,3-propanediol (random) alkoxylates (BEPD-EOx-POy, BEPD-EOx-POy-EOx, BEPD-POx-EOy-POx, where x ranges from 1-100 moles of E0 and PO), and 2-butyl-2-ethyl-1,3-propanediol butoxylates (BEPD-BuOx, where x ranges from 1-25 moles of butyleneoxide). 
     
     
         18 . The method of  claim 15 , wherein the alcohol is selected from the group consisting of neo pentyl glycol (NPG), trimethylol propane (TMP), penta-erythritol (PE), di-TMP, di-PE, 2-ethyl hexanol, butyl ethyl propane diol (BEPD), trimethyl propanediol (TMPD), propylene glycol, and combinations thereof. 
     
     
         19 . The method of  claim 15 , wherein the alcohol is selected from the group consisting of neo pentyl glycol, trimethylol propane, and penta-erythritol. 
     
     
         20 . The method of  claim 15 , wherein the alcohol is trimethylol propane. 
     
     
         21 . The method of  claim 15 , wherein the linolenic acid is present in an amount of about 0.2 wt % of the fatty acid mixture or less. 
     
     
         22 . The method of  claim 15 , wherein a composition comprising the synthetic ester meets standards for fire resistance according to Factory Mutual Approvals Class Number 6930, April 2009. 
     
     
         23 . The method of  claim 15 , wherein a composition comprising the synthetic ester maintains oxidative stability for about 2,500 hours or greater according to ASTM D943. 
     
     
         24 . The method of  claim 15 , wherein a composition comprising the synthetic ester exhibits a pour point temperature of about −10° C. or less. 
     
     
         25 . The method of  claim 15 , wherein the fatty acid mixture is derived from cleaving of a high stability algal oil sourced from genetically modified algae.