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US 7,252,791 B2Granted
Ionic liquids
OwnerPeter Wasserscheid, Andreas Bösmann +1inventors
InventorsPeter Wasserscheid, Andreas Bösmann, Roy Van Hal
Life of this patent
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Abstract
Low melting ionic compounds of the general formula (cation) (R′SO4) in which R′ is a branched or linear, saturated or unsaturated, aliphatic or alicyclic functionalized or non-functionalized hydrocarbon chain with 3-36 carbon atoms are provided. These compounds can serve as ionic liquids, e.g. as solvents or solvent additives in chemical reactions, as extraction agents or as heat carriers. The compounds comprise a cation and anionic sulfate ester.
Claims21
A process for employing the compound of Formula 1,
- (cation)(R′SO4) Formula 1
- comprising the step of:
- employing the compound as a solvent, or solvent additive in a chemical process;
- employing the compound as an extraction solvent for a material separation;
- or employing the compound as a heat carrier, or heat carrier additive in a heat exchange unit, wherein:
- R′ is selected from the group consisting of a linear or branched, saturated or unsaturated, aliphatic or alicyclic, functionalized or non-functionalized alkyl radical with 3-36 carbon atoms, wherein R′ is optionally functionalized with one or more X groups;
- X is selected from the group consisting of an —OH, —OR″, —COOH, —COOR″, —NH2, —SO4, —F, —Cl, —Br, —I or —CN;
- and R″ is selected from the group consisting of a branched or linear hydrocarbon chain with 1-12 carbon atoms;
- the compound has a melting point of less than 100° C.;
- and
- the cation is a nitrogen-containing cation selected from the group consisting of a quaternary ammonium cation with the general formula (NR1R2R3R)+, an imidazolium cation, a pyridinium cation, a pyrazolium cation, a phosphonium and a triazolium cation, wherein
- a) the radicals R1, R2, R3 are selected independently at each occurrence from the group consisting of:
- i) linear or branched, saturated or unsaturated, aliphatic or alicyclic alkyl groups with 1 to 20 carbon atoms;
- ii) 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 is optionally substituted with at least one group selected from C1-C6 alkyl groups and/or halogen atoms;
- iii) aryl, aryl-C1-C6 alkyl groups with 5 to 12 carbon atoms in the aryl radical, which is optionally substituted with at least one C1-C6 alkyl group and/or a halogen atom;
- and
- b) the radical R is selected from the group consisting of:
- i) linear or branched, saturated or unsaturated, aliphatic or alicyclic alkyl groups with 1 to 20 carbon atoms;
- ii) 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 is optionally substituted with at least one C1-C6 alkyl group and/or halogen atom;
- and
- iii) aryl-C1-C6 alkyl groups with 5 to 12 carbon atoms in the aryl radical, which is optionally substituted with at least one C1-C6 alkyl group and/or halogen atom.
18 more elements
A process for employing the compound of Formula 1
- (cation)(R′SO4) Formula 1
- comprising the step of:
- employing the compound as a solvent, or solvent additive in a chemical process;
- employing the compound as an extraction solvent for a material separation;
- or employing the compound as a heat carrier, or heat carrier additive in a heat exchange unit, wherein:
- R′ is selected from the group consisting of a linear or branched, saturated or unsaturated, aliphatic or alicyclic, functionalized or non-functionalized alkyl radical with 3-36 carbon atoms, wherein R′ is optionally functionalized with one or more X groups;
- X is selected from the group consisting of an —OH, —OR″, —COOH, —COOR″, —NH2, —SO4, —F, —Cl, —Br, —I or —CN;
- and R″ is selected from the group consisting of a branched or linear hydrocarbon chain with 1-12 carbon atoms;
- the compound has a melting point of less than 100° C.;
- the cation is a nitrogen-containing cation selected from the group consisting of a quaternary ammonium cation with the general formula (NR1R2R3R)+, an imidazolium cation, a pyridinium cation, a pyrazolium cation, a phosphonium and a triazolium cation;
- the compound of the Formula 1 is substantially hydrolytically stable in neutral aqueous solution (pH=7) up to 80° C., and
- a) the radicals R1, R2, R3 are selected independently at each occurrence from the group consisting of:
- i) linear or branched, saturated or unsaturated, aliphatic or alicyclic alkyl groups with 1 to 20 carbon atoms;
- ii) 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 is optionally substituted with at least one group selected from C1-C6 alkyl groups and/or halogen atoms;
- iii) aryl, aryl-C1-C6 alkyl groups with 5 to 12 carbon atoms in the aryl radical, which is optionally substituted with at least one C1-C6 alkyl group and/or a halogen atom;
- and
- b) the radical R is selected from the group consisting of:
- i) linear or branched, saturated or unsaturated, aliphatic or alicyclic alkyl groups with 1 to 20 carbon atoms;
- ii) 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 is optionally substituted with at least one C1-C6 alkyl group and/or halogen atom;
- and
- iii) aryl-C1-C6 alkyl groups with 5 to 12 carbon atoms in the aryl radical, which is optionally substituted with at least one C1-C6 alkyl group and/or halogen atom.
18 more elements
A process for employing the compound of Formula 1
- (cation)(R′SO4) Formula 1
- comprising the step of:
- employing the compound as a solvent, or solvent additive in a chemical process;
- employing the compound as an extraction solvent for a material separation;
- or employing the compound as a heat carrier, or heat carrier additive in a heat exchange unit, wherein:
- a) (R′SO4) is an alkyl sulfate ester, wherein the alkyl moiety is selected from the group consisting of butyl, octyl, 2-ethylhexyl, and dodecyl;
- b) the cation is a nitrogen containing cation selected from the group consisting of 1-ethyl-3-methylimidazolium, 1-butyl-3-methylimidazolium butyl, 1-hexyl-3-methylimidazolium, 1-octyl-3-methylimidazolium, 1-decyl-3-methylimidazolium, 1-dodecyl-3-methylimidazolium, 1-butyl-pyridinium, trimethyldecylammonium, trioctylmethylammonium, trimethyldecylammonium, and trihexyltetradecylphosphonium;
- c) the compound has a melting point of less than 100° C.;
- and
- d) the compound of the Formula 1 is substantially hydrolytically stable in neutral aqueous solution (pH=7) up to 80° C.
7 more elements
Dependencies are inferred from the claim text.