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US 8,075,777 B2Granted
Process for the separation of diastereomers
AssigneeE. I. Du Pont de Nemours and Company
InventorsMark Brandon Shiflett, Akimichi Yokozeki
Life of this patent
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Abstract
A process for separating the diastereomers of a compound such as dihydrodecafluoropentane by using an ionic liquid to increase separation efficiency. The process may involve separation of the threo and erythro diastereomers of HFC-4310mee by liquid-liquid extraction wherein at least one ionic liquid is used as the extractant.
Claims17
A process for separating one diastereomer of dihydrodecafluoropentane from a mixture comprising at least one pair of diastereomers of dihydrodecafluoropentane, comprising contacting the mixture with a solvent consisting essentially of at least one ionic liquid in which one of the diastereomers is soluble to a greater extent than the other diastereomer, and separating the lower-solubility diastereomer from the mixture;
- wherein an ionic liquid comprises a cation selected from the group consisting of the following eleven cations:
- wherein R1, R2, R3, R4, R5, R6 are independently selected from the group consisting of:
- (i) H;
- (ii) halogen;
- (iii) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene, optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH;
- (iv) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene comprising one to three heteroatoms selected from the group consisting of O, N, Si and S, and optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH;
- (v) C6 to C20 unsubstituted aryl, or C3 to C25 unsubstituted heteroaryl having one to three heteroatoms independently selected from the group consisting of O, N, Si and S;
- and
- (vi) C6 to C25 substituted aryl, or C3 to C25 substituted heteroaryl having one to three heteroatoms independently selected from the group consisting of O, N, Si and S;
- and wherein said substituted aryl or substituted heteroaryl has one to three substituents independently selected from the group consisting of:
- (1) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene, optionally substituted with at least one member selected from the group consisting of Cl, Br, F I, OH, NH2 and SH,
- (2) OH,
- (3) NH2, and
- (4) SH;
- R7, R8, R9 and R10 are independently selected from the group consisting of:
- (vii) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene, optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH;
- (viii) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene comprising one to three heteroatoms selected from the group consisting of O, N, Si and S, and optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH;
- (ix) C6 to C25 unsubstituted aryl, or C3 to C25 unsubstituted heteroaryl having one to three heteroatoms independently selected from the group consisting of O, N, Si and S;
- and
- (x) C6 to C25 substituted aryl, or C3 to C25 substituted heteroaryl having one to three heteroatoms independently selected from the group consisting of O, N, Si and S;
- and wherein said substituted aryl or substituted heteroaryl has one to three substituents independently selected from the group consisting of:
- (1) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene, optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH,
- (2) OH,
- (3) NH2, and
- (4) SH;
- and
- wherein, optionally, at least two of R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 together form a cyclic or bicyclic alkanyl or alkenyl group;
- and
- an anion selected from the group consisting of [CH3CO2]—, [HSO4]—, [CH3OSO3]—, [C2H5OSO3]—, [AlCl4]—, [CO3]2—, [HCO3]—, [NO2]—, [NO3]—, [SO4]2—, [PO4]3—, [HPO4]2—, [H2PO4]—, [HSO3]—, [CuCl2]—, Cl—, Br—, I—, SCN—, and any fluorinated anion.
26 more elements
A process for performing an industrial operation selected from the group consisting of a calibration operation, a cleaning operation, a rinsing operation, a drying operation, a particulate removal operation, a solvent operation, a dispersion operation, a heat transfer operation, and an insulating operation, comprising
- (a) contacting a mixture comprising a pair of diastereomers of dihydrodecafluoropentane with a solvent that consists essentially of at least one ionic liquid in which one of the diastereomers is soluble to a greater extent than the other diastereomer,
- (b) separating the lower-solubility diastereomer from the mixture, and
- (c) employing the separated diastereomer in the operation;
- wherein an ionic liquid comprises a cation selected from the group consisting of the following eleven cations:
- wherein R1, R2, R3, R4, R5 and R6 are independently selected from the group consisting of:
- (i) H;
- (ii) halogen;
- (iii) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene, optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH;
- (iv) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene comprising one to three heteroatoms selected from the group consisting of O, N, Si and S, and optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH;
- (v) C6 to C20 unsubstituted aryl, or C3 to C25 unsubstituted heteroaryl having one to three heteroatoms independently selected from the group consisting of O, N, Si and S;
- and
- (vi) C6 to C25 substituted aryl, or C3 to C25 substituted heteroaryl having one to three heteroatoms independently selected from the group consisting of O, N, Si and S;
- and wherein said substituted aryl or substituted heteroaryl has one to three substituents independently selected from the group consisting of:
- (1) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene, optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH,
- (2) OH,
- (3) NH2, and
- (4) SH;
- R7, R8, R9 and R10 are independently selected from the group consisting of:
- (vii) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene, optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH;
- (viii) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene comprising one to three heteroatoms selected from the group consisting of O, N, Si and S, and optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH;
- (ix) C6 to C25 unsubstituted aryl, or C3 to C25 unsubstituted heteroaryl having one to three heteroatoms independently selected from the group consisting of O, N, Si and S;
- and
- (x) C6 to C25 substituted ary, or C3 to C25 substituted heteroaryl having one to three heteroatoms independently selected from the group consisting of O, N, Si and S;
- and wherein said substituted aryl or substituted heteroaryl has one to three substituents independently selected from the group consisting of:
- (1) —CH3, —C2H5, or C3 to C25 straight-chain, branched or cyclic alkane or alkene, optionally substituted with at least one member selected from the group consisting of Cl, Br, F, I, OH, NH2 and SH,
- (2) OH,
- (3) NH2, and
- (4) SH;
- and
- wherein, optionally, at least two of R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 together to form a cyclic or bicyclic alkanyl or alkenyl group;
- and
- an anion selected from the group consisting of [CH3CO2]—, [HSO4]—, [CH3OSO3]—, [C2H5OSO3]—, [AlCl4]—, [CO3]2—, [HCO3]—, [NO2]—, [NO3]—, [SO4]2—, [PO4]3—, [HPO4]2—, [H2PO4]—, [HSO3]—, [CuCl2]—, Cl—, Br—, I—, SCN—, and any fluorinated anion
29 more elements
Dependencies are inferred from the claim text.