Chiral Ionic Liquid Solvents for Asymmetric Synthesis

DESCRIPTION (provided by applicant): This Small Business Innovation Research Phase I project will investigate newly discovered ionic liquids (IL's) that are based on asymmetric organic anions for use as environmentally friendly, VOC-free "green" solvents including four new room-temperature ionic liquids (RTIL's). These new solvents have been demonstrated for use in organic synthesis, and for oxidations in particular. The solvents may provide more environmentally benign pathways for synthesis of asymmetric drugs and intermediates by reducing harmful emissions and regulatory costs. The racemic forms of the solvents have already been isolated and are anticipated to have use for asymmetric oxidation reactions. Additional advantage in asymmetric synthesis may arise via the use of enantiomerically pure versions of the ionic liquid solvents. With liquid ranges as great as -50 xC to 250 xC, the solvents are anticipated to have use under a wide range of reaction conditions. nGimat proposes to investigate the properties of the new ionic liquids and develop more environmentally benign versions of asymmetric organic oxidations. This work will provide a scientific underpinning to the commercialization effort for these materials for applications in cooperation with our commercialization partner, a Fortune 500 manufacturer of organic solvents and performance chemicals. To date, we have discovered four room temperature ionic liquids (RTILs), and in Phase I, we will execute a search for additional members of the series that may also be ionic liquids. The recent trend towards environmentally friendly products has caused an increase in the use of green solvents in product formulations and industrial processes. Regulations governing the use of solvents classified as Hazardous Air Pollutants (HAP) or as Volatile Organic Compounds (VOC) are forcing companies to look for alternatives to solvents presently in use. Volatile organic solvents are a source of VOC emissions and hazardous air pollution and are implicated in ozone depletion and global warming, therefore, there is an opportunity for the introduction of products that are designed to eliminate VOC emissions from industrial processes. nGimat's goal is to release new ionic liquid solvents that meet these needs within 3-4 years. nGimat will license materials developed under Phase II to companies that manufacture pharmaceuticals, intermediates, performance chemicals, organic solvents or related products. Organic solvents play a major role in the synthesis of asymmetric drugs and intermediates, but many organic solvents are volatile and are harmful to the environment and to human health. Ionic liquid solvents offer a non-volatile alternative to replace volatile solvents in asymmetric drug synthesis. A new family of ionic liquid solvents will be investigated for their use in asymmetric synthesis.