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US 8,492,538 B1Granted
Cyclodextrin derivative salts
OwnerJose R. Matosinventor
Life of this patent
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Abstract
Chiral salts comprising anionic cyclodextrin derivatives with particular types of non-metal cations are provided. The anionic CD derivative salts can serve as ionic liquids and can possess substantial advantages over currently commercially available ionic liquids particularly for use as chiral phase transfer catalyst, chiral reaction medium, chiral extraction medium, and/or as chiral additive to a chemical process. Methods of preparing the same are provided.
Claims21
A cyclodextrin derivative salt comprising:
- one or more anionic cyclodextrin derivatives;
- and one or more cations independently selected at each occurrence from a phosphonium cation or a quaternary nitrogen-containing cation, wherein the quaternary nitrogen-containing cation excludes tetraalkylammonium cation, and wherein each cation is independently substituted or unsubstituted upon each occurrence, provided that when the quaternary nitrogen-containing cation is quaternary ammonium cation, it is of the general formula (NR1R2R3R)+, wherein the radicals R1, R2, and R3 are selected independently at each occurrence from the group consisting of:
- substituted linear or branched, saturated or unsaturated, aliphatic or alicyclic alkyl groups with 1 to 20 carbon atoms;
- heteroaryl groups, heteroaryl-C1-C6 alkyl groups with 3 to 8 carbon atoms in the heteroaryl radical and at least one heteroatom selected from N, O and S which may be substituted with at least one group selected from C1-C6 alkyl groups and/or halogen atoms;
- aryl, aryl-C1-C6 alkyl groups with 5 to 12 carbon atoms in the aryl radical, substituted with at least one C1-C6 alkyl group and/or a halogen atom;
- and
- the radical R is selected from the group consisting of:
- substituted linear or branched, saturated or unsaturated, aliphatic or alicyclic alkyl groups with 1 to 20 carbon atoms;
- heteroaryl-C1-C6 alkyl groups with 3 to 8 carbon atoms in the aryl radical and at least one heteroatom selected from N, O and S, which may be substituted with at least one C1-C6 alkyl group and/or halogen atom;
- aryl-C1-C6 alkyl groups with 5 to 12 carbon atoms in the aryl radical, substituted with at least one C1-C6 alkyl group and/or halogen atom;
- and
- wherein any two of R, R1, R2, R3 can join together to form a 4- to 8-membered heterocycle including the heteroatom to which each is attached.
9 more elements
A cyclodextrin derivative salt comprising a compound, or mixture of compounds, of the Formula 1,
- wherein:
- p is 4, 5 or 6;
- Q is independently selected at each occurrence from —OH, -sulfoalkyl ether-T, -sulfated alkyl ether-T, -sulfonate-T, -sulfate-T, -carboxyalkyl ether-T, succinylate-T, -sulfoalkylthio ether-T, -carboxylate-T, -phosphoalkyl ether-T, -phosphate-T, and -phosphonate-T, wherein at least one Q is not —OH, and optionally wherein at least one Q is selected from the group consisting of -alkyl ether and -hydroxyalkyl ether;
- and
- T is a cation independently selected at each occurrence from the group consisting of one or more cations independently selected at each occurrence from a phosphonium cation or a quaternary nitrogen-containing cation, wherein the quaternary nitrogen-containing cation excludes tetraalkylammonium cation, and wherein each of the above is independently substituted or unsubstituted upon each occurrence, provided that when the quaternary nitrogen-containing cation is quaternary ammonium cation, it is of the general formula (NR1R2R3R)+, wherein the radicals R1, R2, and R3 are selected independently at each occurrence from the group consisting of:
- substituted linear or branched, saturated or unsaturated, aliphatic or alicyclic alkyl groups with 1 to 20 carbon atoms;
- heteroaryl groups, heteroaryl-C1-C6 alkyl groups with 3 to 8 carbon atoms in the heteroaryl radical and at least one heteroatom selected from N, O and S which may be substituted with at least one group selected from C1-C6 alkyl groups and/or halogen atoms;
- aryl, aryl-C1-C6 alkyl groups with 5 to 12 carbon atoms in the aryl radical, substituted with at least one C1-C6 alkyl group and/or a halogen atom;
- and
- the radical R is selected from the group consisting of:
- substituted linear or branched, saturated or unsaturated, aliphatic or alicyclic alkyl groups with 1 to 20 carbon atoms;
- heteroaryl-C1-C6 alkyl groups with 3 to 8 carbon atoms in the aryl radical and at least one heteroatom selected from N, O and S, which may be substituted with at least one C1-C6 alkyl group and/or halogen atom;
- aryl-C1-C6 alkyl groups with 5 to 12 carbon atoms in the aryl radical, substituted with at least one
- C1-C6 alkyl group and/or halogen atom;
- and
- wherein any two of R, R1, R2, R3 can join together to form a 4- to 8-membered heterocycle including the heteroatom to which each is attached.
13 more elements
Dependencies are inferred from the claim text.