B - Operations – Transporting – 01 – J
Patent
B - Operations, Transporting
01
J
B01J 31/02 (2006.01) C07C 17/38 (2006.01) C07C 33/14 (2006.01) C07C 45/34 (2006.01) C07C 45/50 (2006.01) C07C 47/02 (2006.01) C07C 49/543 (2006.01) C07C 315/02 (2006.01) C07C 317/14 (2006.01) C07D 303/32 (2006.01) C07D 333/76 (2006.01) C07F 9/09 (2006.01) C07F 9/141 (2006.01) C07F 9/50 (2006.01)
Patent
CA 2126778
ABSTRACT OF THE DISCLOSURE Stoichiometric and catalytic chemical transformations may be carried out in solution using novel fluorous multiphase systems (FMS). The term "fluorous" is defined as a carbon-fluorine bond rich organic molecule which is generated by replacing hydrogen atoms bonded to carbon atoms with fluorine. The FMS consists of a fluorous phase containing a fluorous solvent, typically a fluorocarbon or a fluorohydrocarbon, either of the foregoing with or without substituent groups, and a reagent or a catalyst containing a sufficient number of fluorous moieties to render it preferentially soluble in the fluorous solvent and located at the interface of the fluorous and nonfluorous phases. The nonfluorous i.e. the second solvent, may be any known organic or nonorganic solvent(s) with limited or no solubility in the fluorous solvent that is effective for dissolving the reactants and/or separating the reaction products. Typically a nonfluorous solvent having a Hildebrand solubility parameter of at least about 18.0 MPa? is suitable. The reaction can occur simultaneously in the fluorous phase and at the interface of the phases. The FMS reagents and FMS catalysts in the present invention contain sufficient number of fluorous moieties to render them preferentially soluble into the fluorous phase and at the interface without impairing the ability of the catalyst or reagent to be effective or participate in the reaction and while maintaining the reaction in a liquid or fluid phase. The most appropriate fluorous moieties are linear, branched and carbocyclic fluorocarbon alkyl chains with high carbon numbers that are effective to enable the catalyst or reagent to remain fluorous phase compatible. The fluorous moieties, optionally, may also contain O, S, N, P, As and Si, that assist in rendering the catalysts and reagents fluorous phase compatible. The FMS reagents and catalysts can be prepared by (1) fluorination (i.e., replacement of C-H bonds with fluorine); (2) fluorofunctionalization, e.g., the attachment of fluorous moieties to the reagents or catalysts; or (3) by total synthesis. The fluorous multiphase systems have utility for facilitating the separation of the FMS catalyst or spent FMS reagent. The possibility of separating the catalyst or the spent reagent from the products has utility in the design and synthesis of catalysts and reagents with high product selectivity, resulting in especially environmentally friendly processes.
Horvath Istvan Tamas
Rabai Jozsef
Borden Ladner Gervais Llp
Exxon Research And Engineering Company
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