Carbonated estolides and methods of making and using the same
Inventors
Doll, Kenneth M. • Isbell, Terry • Cermak, Steven C. • Kenar, James A.
Assignees
US Department of Agriculture USDA
Publication Number
US-9850222-B2
Publication Date
2017-12-26
Expiration Date
2036-08-01
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Abstract
Disclosed herein are the conversion of estolide compounds having unsaturated fatty acid groups into estolides containing cyclic carbonate moieties and methods of making and using the same. The estolides containing a cyclic carbonate may be used to produce urethane containing estolides.
Core Innovation
The invention relates to the conversion of estolide compounds having unsaturated fatty acid groups into estolides containing cyclic carbonate moieties and methods of making and using the same. Specifically, the invention discloses estolides containing a cyclic carbonate group and processes to form them via epoxidized estolide intermediates. The estolides containing the cyclic carbonate may be further reacted to produce urethane containing estolides.
The problem being solved arises from the limitations of biobased lubricants produced from natural products, which, while attractive for their biodegradability and lubricity, suffer from poor cold temperature attributes and poor oxidative and hydrolytic stabilities. Chemical modification of vegetable oils, such as the formation of estolides, improves these properties. However, the ability to introduce cyclic carbonate moieties onto more complex biobased materials possessing unsaturation such as estolides has not been previously investigated, representing an opportunity to enhance the functionality and utility of estolides.
Claims Coverage
The patent contains three main independent claims covering novel estolide compounds and methods for making cyclic carbonate containing estolides and urethane containing estolides. Below are the main inventive features extracted from these independent claims.
Estolide containing a cyclic carbonate
An estolide compound containing a 5-membered cyclic carbonate moiety with a defined formula where x and y represent the lengths of hydrocarbon chains and R groups represent various hydrogen or hydrocarbon substituents covering linear or branched alkyl chains, saturated or unsaturated, and substituted or unsubstituted hydrocarbons.
Method of making estolides containing cyclic carbonates
A method comprising (a) reacting formic acid and hydrogen peroxide with an estolide compound having unsaturated fatty acid groups to form an epoxidized estolide intermediate and (b) reacting the epoxidized estolide with an alkylammonium salt under supercritical carbon dioxide to form an estolide containing a 5-membered cyclic carbonate.
Method of making urethane containing estolides
A method comprising reacting estolides containing a cyclic carbonate moiety with an amine or diamine to produce urethane containing estolides having specified structural formulas, where R groups and chain lengths vary similarly to the cyclic carbonate estolides.
The claims comprehensively cover (1) novel estolide compounds containing cyclic carbonate groups, (2) methods for synthesizing these compounds via epoxidation and carbonation under specific conditions including use of supercritical carbon dioxide and alkylammonium salts, and (3) methods for making urethane containing estolides by ring-opening the cyclic carbonate with amines, thus describing compositions and methods for functionalized biobased estolide materials.
Stated Advantages
Estolides containing cyclic carbonates have unexpectedly high viscosities compared to starting estolides, which broadens their utility as lubricants or functional fluids.
The cyclic carbonate group introduces potential chemical functionality that allows further chemical modification, including formation of urethane linkages.
The urethane containing estolides produced can be used to prepare polyurethane coatings without toxic isocyanates, offering a safer alternative.
Documented Applications
Use of carbonated estolides as lubricants, hydraulic fluids, or gear oils due to improved viscosity and stability properties.
Preparation of polyurethane coatings via ring-opening reactions of carbonated estolides with amines, enabling isocyanate-free polyurethane materials.
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