Bio-based base oils from fatty acids and biomass

Abstract

Disclosed herein are lubricant compositions containing 75-99% by weight of a base oil that includes one or more branched aliphatic compounds having the following formula: R 1 R 2 HC—CH 2 —CHR 3 R 4 (I) wherein R 1 and R 3 are independently selected from alkyl groups having 8 to 26 carbon atoms, and R 2 and R 4 are independently selected from the group consisting of H and alkyl groups having 5 to 7 carbon atoms, with a proviso that at least one of R 2 and R 4 is not hydrogen. The alkyl groups are substituted or unsubstituted, or branched or unbranched; R 1 and R 3 may be the same or different; and the total carbon content of the branched aliphatic compound of formula (I) is in the range of 26 to 66. The lubricant compositions also include an effective amount of one or more additives. Also, disclosed herein are processes for making such compositions and their uses in pharmaceutical and personal care products.

1 . A lubricant composition comprising:
 a. 75-99% by weight of a base oil comprising one or more branched aliphatic compounds having the following formula:
   R 1 R 2 HC—CH 2 —CHR 3 R 4   (I)
 
   wherein:
 (i) R 1  and R 3  are independently selected from alkyl groups having 8 to 26 carbon atoms, 
 (ii) R 2  and R 4  are independently selected from the group consisting of H and alkyl groups having 5 to 7 carbon atoms, with a proviso that at least one of R 2  and R 4  is not hydrogen, 
   wherein the alkyl groups are substituted or unsubstituted, or branched or unbranched,   wherein R 1  and R 3  may be the same or different, and   wherein the total carbon content of the branched aliphatic compound of formula (I) is in the range of 26 to 66; and   b. an effective amount of one or more additives.   
     
     
         2 . The lubricant composition according to  claim 1 , wherein at least one of the one or more branched aliphatic compounds has a bio-based content in the range of 20 to 100%, according to ASTM-D6866. 
     
     
         3 . The lubricant composition according to  claim 1 , wherein at least one of the one or more branched aliphatic compounds has one of the following structures: 
       
         
           
           
               
               
           
         
       
     
     
         4 . The lubricant composition according to  claim 1 , wherein the base oil further comprises a minor amount of one or more alkanes having a carbon content in the range of 1 to 25. 
     
     
         5 . The lubricant composition according to  claim 1 , wherein the one or more additives are selected from the group consisting of antioxidants, stabilizers, detergents, dispersants, demulsifiers, antioxidants, anti-wear additives, pour point depressants, viscosity index modifiers, friction modifiers, anti-foam additives, defoaming agents, corrosion inhibitors, wetting agents, rust inhibitors, copper passivators, metal deactivators, extreme pressure additives, and combinations thereof. 
     
     
         6 . The lubricant composition according to  claim 1 , further comprising one or more co-base oils selected from the group consisting of API Group I base oil, Group II base oil, Group III base oil, Group IV base oil, Group V base oil, gas-to-liquid (GTL) base oil, and combinations thereof. 
     
     
         7 . The lubricant composition according to  claim 1 , wherein at least one of the one or more branched aliphatic compounds of formula (I) has a kinematic viscosity at 100° C. in the range of 2 to 100 cSt, as measured by ASTM D445. 
     
     
         8 . The lubricant composition according to  claim 1 , wherein at least one of the one or more branched aliphatic compounds of formula (I) has a kinematic viscosity at 40° C. in the range of 6 to 100 cSt, as measured by ASTM D445. 
     
     
         9 . The lubricant composition according to  claim 1 , wherein at least one of the one or more branched aliphatic compounds of formula (I) has a viscosity index, calculated from kinetic viscosity at 100° C. and 40° C., in the range of 100 to 200, as measured by ASTM D2270. 
     
     
         10 . The lubricant composition according to  claim 1 , wherein at least one of the one or more branched aliphatic compounds of formula (I) has a pour point in the range of 2° C. to −160° C., as measured by ASTM D97. 
     
     
         11 . The lubricant composition according to  claim 1 , wherein at least one of the one or more branched aliphatic compounds of formula (I) has an oxidation stability in the range of 150° C. to 300° C., as measured by ASTM D6375. 
     
     
         12 . The lubricant composition according to  claim 1 , wherein the base oil has a kinematic viscosity of at least 3 cSt, as measured by ASTM D445. 
     
     
         13 . The lubricant composition according to  claim 1 , wherein the base oil has a bio-based content in the range of 30 to 100%, according to ASTM-D6866. 
     
     
         14 . A method comprising providing the lubricant composition according to  claim 1 , and using it for lubricating industrial machinery, an automobile, aviation machinery, a refrigeration compressor, agricultural equipment, a marine vessel, agriculture equipment, medical equipment, hydropower production machinery, and food processing equipment. 
     
     
         15 . A composition comprising:
 one or more branched aliphatic compounds having the following formula:
   R 1 R 2 HC—CH 2 —CHR 3 R 4   (I)
 
   wherein:   R 1  and R 3  are independently selected from alkyl groups having 8 to 26 carbon atoms,   R 2  and R 4  are independently selected from the group consisting of H and alkyl groups having 5 to 7 carbon atoms, with a proviso that at least one of R 2  and R 4  is not hydrogen,   wherein the alkyl groups are substituted or unsubstituted, or branched or unbranched,   wherein R 1  and R 3  may be the same or different, and   wherein the total carbon content of the branched aliphatic compound of formula (I) is in the range of 26 to 66; and   wherein the composition has a bio-based content in the range of 30 to 100%, according to ASTM-D6866.   
     
     
         16 . A method of making the composition of  claim 15 , the method comprising the steps of:
 a) providing a first component comprising one or more of a furfural or its derivative and a second component comprising a ketone having the formula R 1 R 3 CO, wherein each R 1  and R 3  is independently selected from the group consisting of alkyl groups having 8 to 26 carbon atoms,   wherein at least one of the first component and the second component is bio-derived from a renewable source;   b) condensing the first component with the second component in the presence of a basic catalyst to form at least one condensed furan compound (CF) selected from the group consisting of:   
       
         
           
           
               
               
           
         
         where R 5  is hydrogen, methyl, ethyl, or hydroxymethyl; and 
         c) hydrodeoxygenating the at least one condensed furan compound (CF) in the presence of a hydrodeoxygenation catalyst to obtain one or more branched aliphatic compounds of formula (I). 
       
     
     
         17 . The method according to  claim 16 , wherein the step of providing a second component comprising a ketone comprises ketonic decarboxylyzing one or more fatty acids from one or more natural oils or waste cooking oils. 
     
     
         18 . The method according to  claim 16 , wherein the basic catalyst is selected from the group consisting of liquid bases (including inorganic liquid bases and organic liquid bases) and solid bases. 
     
     
         19 . The method according to  claim 16 , wherein the hydrodeoxygenation catalyst is a solid acid supported metal based catalyst, a physical mixture of a metal based catalyst, or a metal/metal oxide catalyst and preferably Pd/C, Pd/SiO 2  or Pt/C, with a solid acid. 
     
     
         20 . The method according to  claim 19 , wherein the hydrodeoxygenation catalyst is a solid acid supported metal based catalyst selected from Ni/ZSM-5, Pd/ZSM-5, Pd/BEA, or a physical mixture of a metal based catalyst with a solid acid, including Pd/C+ZSM-5, Pd/C+BEA, Pt/C+BEA, and preferably a supported metal-metal oxide catalyst such as Ir—ReO x /SiO 2 , Ir—MoO x /SiO 2  or  1 M 2 MO/SiO 2 , wherein  1 M=Ir, Ru, Ni, Co, Pd, Pt, or Rh and  2 M=Re, Mo, W, Nb, Mn, V, Ce, Cr, Zn, Co, Y, or Al. 
     
     
         21 . A method comprising preparing the composition according to  claim 16 , and using it as a base oil in a pharmaceutical or personal care product. 
     
     
         22 . A personal care composition comprising:
 a base oil comprising the composition of  claim 15 ; and   an effective amount of one or more additives selected from the group consisting of pigments, fragrances, emulsifiers, wetting agents, thickeners, emollients, rheology modifiers, viscosity modifiers, gelling agents, antiperspirant agents, deodorant actives, fatty acid salts, film formers, anti-oxidants, humectants, opacifiers, monohydric alcohols, polyhydric alcohols, fatty alcohols, preservatives, pH modifiers, moisturizers, skin conditioners, stabilizing agents, proteins, skin lightening agents, topical exfoliants, antioxidants, retinoids, refractive index enhancers, photo-stability enhancers, SPF improvers, UV blockers, and water.   
     
     
         23 . The personal care composition of  claim 22 , further comprising an active ingredient selected from the group consisting of antibiotics, antiseptics, antifungals, corticosteroids, and anti-acne agents. 
     
     
         24 . A pharmaceutical composition comprising:
 a base oil comprising the composition of  claim 15 ;   an effective amount of one or more pharmaceutically active ingredients; and   optionally, one or more pharmaceutically acceptable excipients.