Carbonated estolides and methods of making and using the same

A method of making an estolide containing a cyclic carbonate, said method comprising

• (a) forming epoxidized estolide by reacting formic acid and H2O2 with at least one estolide compound of the Formula
• wherein x and y are each equal to 1 or greater than 1 and x is independent from each occurrence and y is independent from each occurrence,
• wherein n is 0-9,
• R1 is H, or an linear alkyl chain or a branched alkyl chain or
• wherein R9 and R10 are independently selected from hydrogen and C-1 to C-36 hydrocarbon which may be saturated or unsaturated, branched or straight chain, or substituted or unsubstituted,
• and R2-R7 are independently selected from —CH2—, —C═C—, or
• (b) reacting said epoxidized estolide with an alkylammonium salt and pressurized CO2 to form an estolide containing a cyclic carbonate having the Formula
• wherein x and y are each equal to 1 or greater than land x is independently from each occurrence and y is independently from each occurrence,
• wherein n is 0-9,
• R1 is H, or an linear alkyl chain or a branched alkyl chain or
• wherein R9 and R10 are independently selected from hydrogen and C-1 to C-36 hydrocarbon which may be saturated or unsaturated, branched or straight chain, or substituted or unsubstituted,
• and R2-R7 are independently selected from —CH2—, —C═C—, or
• wherein residual epoxide or unsaturated groups may still be present.

A urethane containing estolide having the Formula

• wherein x and y are each equal to 1 or greater than 1 and x is independent from each occurrence and y is independent from each occurrence,
• wherein n is 0-9,
• R1 is H, or an linear alkyl chain or a branched alkyl chain or
• wherein R9 and R10 are independently selected from hydrogen and C-1 to C-36 hydrocarbon which may be saturated or unsaturated, branched or straight chain, or substituted or unsubstituted,
• and R2-R7 are independently selected from —CH2—, —C═C—, or
• R11 and R12 are independently selected from H, any alkyl chain [C1-C14], any branched alkyl chain [C1-C14], any alkyl chain containing an amine or hydroxyl group [C1-C14].

A method to making a urethane containing estolide, said method comprising

• (a) forming epoxidized estolide by reacting formic acid and H2O2 with at least one estolide compound of the Formula
• wherein x and y are each equal to 1 or greater than land x is independently from each occurrence and y is independently from each occurrence,
• wherein n is 0-9,
• R1 is H, or an linear alkyl chain or a branched alkyl chain or
• wherein R9 and R10 are independently selected from hydrogen and C-1 to C-36 hydrocarbon which may be saturated or unsaturated, branched or straight chain, or substituted or unsubstituted,
• and R2-R7 are independently selected from —CH2—, —C═C—, or
• (b) reacting said epoxidized estolide with an alkylammonium salt and pressurized CO2 to form an estolide containing a cyclic carbonate having the Formula
• wherein x and y are each equal to 1 or greater than land x is independently from each occurrence and y is independently from each occurrence,
• wherein n is 0-9,
• R1 is H, or an linear alkyl chain or a branched alkyl chain or
• wherein R9 and R10 are independently selected from hydrogen and C-1 to C-36 hydrocarbon which may be saturated or unsaturated, branched or straight chain, or substituted or unsubstituted,
• and R2-R7 are independently selected from —CH2—, —C═C—, or
• (c) and reacting said estolide containing a cyclic carbonate with an amine or diamine to form a urethane containing estolide having the Formula
• R11 and R12 are independently selected from H, any alkyl chain [C1-C14], any branched alkyl chain [C1-C14], any alkyl chain containing an amine or hydroxyl group [C1-C14].