KR101196114B1 - Novel Pairs of Working Substances for Absorption Heat Pumps, Absorption Refrigeration Machines and Heat Transformers - Google Patents

Abstract

The present invention relates to a pair of materials comprising a working substance and an ionic liquid, the use of such materials in absorption heat pumps, absorption refrigerators and heat converters, and corresponding devices.

Working material pair, absorption heat pump, absorption chiller, heat converter

Description

Novel Pairs of Working Substances for Absorption Heat Pumps, Absorption Refrigeration Machines and Heat Transformers}

The present invention relates to novel working material pairs for absorption heat pumps, absorption chillers and heat converters.

The absorption circuit only requires a minimal influx of advanced electrical energy for the operation of the liquid pump, which in principle provides an excellent opportunity for rational energy utilization for heating and cooling, and heat recovery.

Particularly practical and future-oriented uses of this technology are in the sectors of air conditioning buildings with renewable energy, such as solar or geothermal energy, and in the use or recovery of waste heat from many industrial processes.

Two variations of the circuit can be distinguished:

1. Absorption Heat Pump (AHP) and Absorption Chiller (ARM)

In this process variant, heat is supplied to the cycle process at relatively high temperature levels (driving heat), heat is released at intermediate temperature levels (heating heat), and heat is absorbed from the environment at low temperature levels (environmental cooling).

AHP and ARM differ only at different temperature levels at which heat is absorbed from the environment so that cooling occurs in the environment, ie, "cold" occurs.

2. Absorption Heat Transducer (AHT)

In this process variant, the heat obtained at the intermediate temperature level is introduced in a cycle process, a portion of which is converted to a higher temperature level and released as useful heat. The other part of the heat supplied is released to the environment at low temperature levels.

Typical temperature levels for the absorption process are as follows:

Upper temperature: 80 to 150 ° C

Medium temperature: 50-80 ° C.

Sub-temperature: -20 to 20 ° C (temperature below 0 ° C only for AHP)

Absorption processes for heat conversion have been known and have been industrially carried out for over 100 years (eg US 3,638,452, US 3,626,716, DE 101 003 95). Nevertheless, while there is an increasing search for practical ways to use energy reasonably within the growing framework of discussion of energy and climate issues, the technology has not been widely used to date.

The main reason for this is the lack of technically efficient, harmless and functionally reliable functional substance pairs (volatile functional substances-absorbent media) for this type of processes.

In many investigational studies, pairs of novelty agonists have been investigated over time and process modeled and simulated using the resulting mixture data (D. Seher, Forschungsberichte des Deutschen Kaelte und Klimatechnischen Vereins, No. 16, 1985; R Hengerer, Dissertation Universitaet Stuttgart, 1991; AO Genssle, Fortschritt-Berichte VDI, Series 19, No. 130, VDI Verlag 2001; AD Lucas et al., Int. Journal of Refrigeration 27 (2004) 324-330).

Criteria for optimal working material pairs for absorption heat pumps, absorption chillers and heat converters may be formulated according to the above references as follows:

-Non-toxic and non-explosive

-Chemical resistance below 150 ℃

High vaporization enthalpy of the working medium, such as water

High solubility of the working medium in the absorbing medium

Significant vapor pressure decay of the working medium upon dissolution in the absorbent medium

Low vapor pressure damping of the absorbing medium

Very complete miscibility of working and absorbing media

Good thermal conductivity of the working and absorbing media

Low viscosity of the absorbent medium and the mixture of working and absorbent media

Both the working medium and the absorbing medium cannot be corrosive;

Finally, only two systems (pair of agonists), namely lithium bromide / water and ammonia / water, have been achieved for the actual operation of the absorption plant so far, of which ammonia / water is used predominantly in ARM. All material pairs containing organic components investigated so far have been rejected for technical, ecological or safety reasons.

However, the two commonly used systems have serious drawbacks.

Thus, in the case of system ammonia / water, a rectifier is required in the absorption circuit to achieve substantially complete separation of the two materials due to the volatility of the absorption medium water, which reduces the overall efficiency of the process. In addition, the pressure required to condense ammonia is relatively high, so the plant must be designed to withstand the proper pressure.

The functional group of lithium bromide / water has a significant miscibility gap, like all systems containing inorganic salts. If the low temperature level is too low, salts may precipitate from the solution into the crystals and damage the plant by plugging lines, valves and pumps. To avoid this, only a small amount of water is taken from the solution so that the concentration of lithium bromide does not increase too high. As a result, the outgassing range is reduced, which in turn reduces the efficiency of the plant. Apart from this effect, the performance of the device is additionally reduced by the relatively large amount of water that must be transported and cooled in the solvent for the absorption medium between the stripper and the absorber. In addition, concentrated aqueous solutions of lithium bromide are very corrosive at elevated temperatures, which forces the use of special constituent materials. Therefore, A. D. Lucas et al. (Int. Journal of Refrigeration 27 (2004) 324-330) propose to use a salt mixture of lithium bromide and potassium formate to reduce these problems. However, the problem can only be alleviated in this way within narrow limits. This system is also not industrially established.

The drawbacks of the agent pairs investigated so far are essentially poor absorption of the agent in the absorbent medium, incomplete miscibility of the agent with the absorbent medium, and volatilization of the absorbent medium. In addition, a severe corrosion phenomenon on the constituent material occurs in many cases, which makes the use of the agent pair more difficult.

One object of the present invention was to find a pair of working materials which are suitable for use in absorption heat pumps, absorption chillers and / or heat converters and which do not have these drawbacks.

Another object is to have a vapor pressure low enough to avoid problems in the separation of the substance, to be stable at the expected temperature, to have a non-limiting miscibility with the working substance such as water or ammonia, and to absorb it in a suitable manner. Was to find an absorbent medium. It is also advantageous to find an absorption medium that is liquid over the entire temperature range contemplated to avoid crystallization problems and to allow all of the functional substances present in the absorption medium, such as water or ammonia, to be taken out and used.

Ionic liquids have been known since the late 1940s. These are salt melts which are preferably liquid at room temperature and below room temperature and represent a new class of solvents having non-molecular ionic properties. A common definition of ionic liquids to distinguish them from known salt melts is the melting point below 80 ° C. Other references suggest melting points below room temperature for this purpose. For the purposes of the present application, ionic liquids are salts having a melting point of less than 80 ° C., preferably less than room temperature, in the pure state.

Typical cation / anion combinations to obtain ionic liquids are, for example, dialkylimidazolium, pyridinium, ammonium and phosphonium, tetrafluoroborate, methylsulfate with halides. Many additional combinations of cations and anions are also conceivable which result in low melting salts.

This class of materials has the following properties:

Good solvent capacity for many materials

Substantially no vapor pressure (thus no azeotrope formation)

-Non-combustible

Wide liquid range from -60 ° C to 400 ° C

An overview of ionic liquids, their preparation, properties and uses can be found in, for example, Ionic Liquids in Synthesis, P. Wasserscheid, T. Welton, Wiley; Green Industrial Applications on Ionic Liquids (NATO Science Series. I. Mathematics, Physics and Chemistry, 92); Ionic Liquids "Industrial Applications for Green Chemistry" (ACS Symposium Series, 818), Robin D. Rogers (ed.).

It has only been found in the present invention that a pair of functional substances comprising a functional substance and an ionic liquid has been found. It has also been found that ionic liquids can be used as absorption media in absorption heat pumps, absorption chillers and heat converters. Likewise, the present invention relates to absorption heat pumps, absorption freezers and heat converters comprising a working material and an ionic liquid as the working material pair.

Agonist pairs,

A) agonist; And

B) ionic liquid

It includes.

For the purposes of the present invention, the ionic liquid is preferably a salt of formula (I), (II) or (III), or mixtures thereof, having a melting point of ≦ 180 ° C .:

B1) [A] _n ⁺ [Y] ^n- (I)

(Wherein n is 1, 2, 3 or 4, [A] ⁺ is a quaternary ammonium cation, oxonium cation, sulfonium cation or phosphonium cation, [Y] ^n- is monovalent, divalent, Trivalent or tetravalent anion);

B2) Mixed Salts of Formula (II)

In which [A ¹ ] ⁺ , [A ² ] ⁺ , [A ³ ] ⁺ , and [A ⁴ ] ⁺ are defined as B1 above, as mentioned above for [A] ⁺ and [Y] ^n- Independently selected from the groups mentioned); or

B3) Mixed Salts of Formula (III):

Wherein [A ¹ ] ⁺ , [A ² ] ⁺ , and [A ³ ] ⁺ are independently selected from the groups mentioned above for [A] ⁺ and [Y] ⁿ⁻ as defined under B1 [M ¹ ] ⁺ , [M ² ] ⁺ and [M ³ ] ⁺ are monovalent metal cations, [M ⁴ ] ²⁺ is a divalent metal cation, and [M ⁵ ] ³⁺ is a trivalent metal cation being).

For the present invention, the agonists are organic or inorganic liquids, preferably water, ammonia, methanol or chlorofluorocarbons such as freons, prigens with a enthalpy of vaporization of ≧ 400 KJ / kg. Preferred here are water, methanol or ammonia, in particular working substances such as ammonia.

The ionic liquid preferably has ≦ 150 ° C .; In particular, it has a melting point of ≤ 80 ° C.

In another preferred embodiment, the ionic liquid has a melting point in the range of -50 ° C to 150 ° C, in particular in the range of -20 ° C to 120 ° C.

In another preferred embodiment, the ionic liquid has a melting point of ≦ 80 ° C., in particular ≦ room temperature. Preference is given to ionic liquids in which the cation [A] ⁺ is a quaternary ammonium cation, preferably comprising 1 to 5, preferably 1 to 3, particularly preferably 1 or 2 nitrogen atoms.

Suitable cations are, for example, cations of formulas (IVa) to (IVw), and oligomers comprising these structures:

Another suitable cation is a phosphonium cation of formula (IVx), and an oligomer comprising these structures:

In the above formulas (IVa) to (IVx),

Radicals R are organic, saturated or unsaturated, bicyclic or cyclic, aliphatic, containing 1 to 20 carbon atoms, which are unsubstituted or which may be interrupted or substituted by 1 to 5 heteroatoms or functional groups; Aromatic or aliphatic radicals;

Radicals R ¹ to R ⁹ are each independently of one another hydrogen, sulfo groups, or carbon-containing organic, saturated, unsubstituted or interrupted or substituted by 1 to 5 heteroatoms or functional groups; Or an unsaturated, bicyclic or cyclic, aliphatic, aromatic or aliphatic radical (wherein radicals R ¹ to R ⁹ bonded to a carbon atom in the formula (IV) above (but not to a hetero atom) are additionally Halogen or functional group); or

Two adjacent radicals selected from the group consisting of R ¹ to R ⁹ are also together containing a divalent carbon containing 1 to 30 carbon atoms, which may be unsubstituted or interrupted or substituted by 1 to 5 heteroatoms or functional groups. It may form organic, saturated or unsaturated, bicyclic or cyclic, aliphatic, aromatic or aliphatic radicals.

In the definitions of the radicals R and R ¹ to R ⁹ , possible heteroatoms are in principle all heteroatoms which can formally substitute a -CH ₂ -group, -CH = group, -C≡, or = C = group. When the carbon containing radical contains heteroatoms, oxygen, nitrogen, sulfur, phosphorus and silicon are preferred. Preferred groups are especially -O-, -S-, -SO-, -SO _2- , -NR'-, -N =, -PR'-, -POR'- and -SiR ' _2- , wherein the radical R 'Is the remainder of the carbon containing radicals. When the radicals R ¹ to R ⁹ are bonded to a carbon atom (not a heteroatom) in the above formula (IV), they may also be bonded directly via a heteroatom.

Suitable functional groups are in principle all functional groups which can be attached to carbon atoms or heteroatoms. Suitable examples are -OH (hydroxy), = O (particularly as carbonyl group), -NH ₂ (amino), = NH (imino), -COOH (carboxy), -CONH ₂ (carboxamide), -SO ₃ H (sulfo) and -CN (cyano). Functional groups and heteroatoms may also be directly adjacent, such that a combination of a plurality of adjacent atoms may be, for example, -O- (ether), -S- (thioether), -COO- (ester), -CONH- (secondary) amide) or -CONR '- (3 tertiary amide), for example di - (C ₁ -C ₄ - alkyl) amino, C ₁ -C ₄ - alkyloxycarbonyl, or C ₁ -C ₄ - alkyloxy is also Included.

Examples of the halogen include fluorine, chlorine, bromine and iodine.

Radical R is preferably

Unbranched or branched C ₁ -C ₁₈ which may be unsubstituted or substituted with one or more hydroxy, halogen, phenyl, cyano, C ₁ -C ₆ -alkoxycarbonyl and / or sulfonic acid groups, and having 1 to 20 carbon atoms Alkyl such as methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl- 1-propyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3- Methyl-2-pentyl, 4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl, 2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, 1-heptyl, 1-octyl, 1-nonyl, 1-decyl, 1-undecyl, 1-dodecyl, 1-tetradecyl, 1-hexadecyl, 1-octadecyl, 2-hydroxyethyl, benzyl, 3-phenylpropyl, 2 Cyanoethyl, 2- (methoxycarbonyl) ethyl, 2- (ethoxycarbonyl) ethyl, 2- (n-butoxycarbonyl) ethyl, trifluoromethyl, difluoromethyl, fluoromethyl Pentafluoroethyl, heptafluoropropyl, heptafluoroisopropyl, nonafluorobutyl, nonafluoroisobutyl, undecylfluoropentyl, undecylfluoroisopentyl, 6-hydroxyhexyl and propylsulfonic acid;

Glycols, butylene glycols and oligomers thereof, having from 1 to 100 units and having hydrogen or C ₁ -C ₈ -alkyl as end groups, and for example R ^A O— (CHR ^B —CH ₂ —O ) _p -CHR ^B -CH ₂ -or R ^A O- (CH ₂ CH ₂ CH ₂ CH ₂ O) _p -CH ₂ CH ₂ CH ₂ CH ₂ O- (wherein R ^A and R ^B are each preferably Hydrogen, methyl or ethyl and p is preferably 0, 1, 2 or 3), in particular 3-oxabutyl, 3-oxapentyl, 3,6-dioxaheptyl, 3,6-dioxaoctyl, 3, 6,9-trioxadedecyl, 3,6,9-trioxoundecyl, 3,6,9,12-tetraoxatridecyl and 3,6,9,12-tetraoxatetradecyl;

- vinyl; And

N, N-di-C ₁ -C ₆ -alkylamino such as N, N-dimethylamino and N, N-diethylamino.

The radicals R are particularly preferably unbranched and unsubstituted C ₁ -C ₁₈ -alkyl such as methyl, ethyl, 1-propyl, 1-butyl, 1-pentyl, 1-hexyl, 1-heptyl, 1-octyl, 1- Decyl, 1-dodecyl, 1-tetradecyl, 1-hexadecyl, 1-octadecyl, in particular methyl, ethyl, 1-butyl and 1-octyl, or CH ₃ O- (CH ₂ CH ₂ O) _p -CH ₂ CH ₂ — and CH ₃ CH ₂ O— (CH ₂ CH ₂ O) _p —CH ₂ CH ₂ —, where p is 0, 1, 2 or 3.

Radicals R ¹ to R ⁹ are each independently of the other

- Hydrogen;

Halogen;

Functional groups;

Optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and / or heterocycles, and / or one or more oxygen and / or sulfur atoms and / or one or more substituted or unsubstituted imino groups C ₁ -C ₁₈ -alkyl which may be interrupted by;

Optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and / or heterocycles, and / or one or more oxygen and / or sulfur atoms and / or one or more substituted or unsubstituted imino groups C ₂ -C ₁₈ -alkenyl, which may be interrupted by;

C ₆ -C ₁₂ -aryl optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and / or heterocycles;

C ₅ -C ₁₂ -cycloalkyl which may optionally be substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and / or heterocycles;

C ₅ -C ₁₂ -cycloalkenyl which may be optionally substituted by functional group, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatom and / or heterocycle; or

A 5- or 6-membered oxygen-, nitrogen- and / or sulfur-containing heterocycle, optionally substituted by functional group, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatom and / or heterocycle ;

Two adjacent radicals together

Optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and / or heterocycles, and / or one or more oxygen and / or sulfur atoms and / or one or more substituted or unsubstituted imino groups It is preferred to form unsaturated, saturated or aromatic rings which can be interrupted by.

C ₁ -C ₁₈ -alkyl, which may optionally be substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and / or heterocycles, preferably is methyl, ethyl, 1-propyl, 2-propyl , 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl- 1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2- Methyl-3-pentyl, 3-methyl-3-pentyl, 2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1- Butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, heptyl, octyl, 2-ethylhexyl, 2,4,4-trimethylpentyl, 1,1,3,3-tetramethyl Butyl, 1-nonyl, 1-decyl, 1-undecyl, 1-dodecyl, 1-tridecyl, 1-tetradecyl, 1-pentadecyl, 1-hexadecyl, 1-heptadecyl, 1-octadec Yarn, cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl, cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl, benzyl (phenylmethyl), diphenylmethyl (benzhydryl), tri Phenylmethyl, 1-phenylethyl, 2-phenylethyl, 3-phenylpropyl, α, α-dimethylbenzyl, p-tolylmethyl, 1- (p-butylphenyl) ethyl, p-chlorobenzyl, 2,4-dichloro Benzyl, p-methoxybenzyl, m-ethoxybenzyl, 2-cyanoethyl, 2-cyanopropyl, 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, 2-butoxycarbonylpropyl, 1,2-di- (methoxycarbonyl) ethyl, methoxy, ethoxy, formyl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 2-methyl-1 , 3-dioxolan-2-yl, 4-methyl-1,3-dioxolan-2-yl, 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 4-hydroxybutyl, 6 -Hydroxyhexyl, 2-aminoethyl, 2-aminopropyl, 3-aminopropyl, 4-aminobutyl, 6-aminohexyl, 2-methylaminoethyl, 2-methyl Aminopropyl, 3-methylaminopropyl, 4-methylaminobutyl, 6-methylaminohexyl, 2-dimethylaminoethyl, 2-dimethylaminopropyl, 3-dimethylaminopropyl, 4-dimethylaminobutyl, 6-dimethylaminohexyl , 2-hydroxy-2,2-dimethylethyl, 2-phenoxyethyl, 2-phenoxypropyl, 3-phenoxypropyl, 4-phenoxybutyl, 6-phenoxyhexyl, 2-methoxyethyl, 2 -Methoxypropyl, 3-methoxypropyl, 4-methoxybutyl, 6-methoxyhexyl, 2-ethoxyethyl, 2-ethoxypropyl, 3-ethoxypropyl, 4-ethoxybutyl, 6-e Oxyhexyl, acetyl, C _q F _{2 (qa) + (1-b)} H _{2a + b} (where q is 1 to 30, 0 ≦ a ≦ q, and b = 0 or 1) (eg CF ₃ , C ₂ F ₅ , CH ₂ CH ₂ -C _(q-2) F _{2 (q-2) +1} , C ₆ F ₁₃ , C ₈ F ₁₇ , C ₁₀ F ₂₁ , C ₁₂ F ₂₅ ), Chloromethyl, 2-chloroethyl, trichloromethyl, 1,1-dimethyl-2-chloroethyl, methoxymethyl, 2-butoxyethyl, diethoxymethyl, diethoxyethyl, 2-isopropoxyethyl, 2- Methoxypropyl, 2-octyloxyethyl, 2-methoxyisopropyl, 2- (methoxycarbonyl) ethyl, 2- (ethoxycarbonyl) ethyl, 2- (n-butoxycarbonyl) ethyl, butylthio Methyl, 2-dodecylthioethyl, 2-phenylthioethyl, 5-hydroxy-3-oxapentyl, 8-hydroxy-3,6-dioxaoctyl, 11-hydroxy-3,6,9-tri Oxoundecyl, 7-hydroxy-4-oxaheptyl, 11-hydroxy-4,8-dioxoundecyl, 15-hydroxy-4,8,12-trioxapentadecyl, 9-hydroxy-5 Oxanonyl, 14-hydroxy-5,10-dioxatetradecyl, 5-methoxy-3-oxapentyl, 8-methoxy-3,6-dioxaoctyl, 11-methoxy-3,6, 9-trioxoundecyl, 7-methoxy-4-oxaheptyl, 11-methoxy-4,8-dioxoundecyl, 15-methoxy-4,8,12-trioxapentadecyl, 9-meth Oxy-5-oxanonyl, 14-methoxy-5,10-dioxatetradecyl, 5-ethoxy-3-oxapentyl, 8-ethoxy-3,6-dioxaoctyl, 11-ethoxy-3 , 6,9-trioxoundecyl, 7-ethoxy-4-oxaheptyl, 11-ethoxy-4,8-dioxoundecyl, 15-ethoxy-4,8,12-trioxapentadecyl, 9-ethoxy-5-oxanonyl or 14-ethoxy-5,10-oxatetradecyl.

Optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and / or heterocycles, and / or one or more oxygen and / or sulfur atoms and / or one or more substituted or unsubstituted imino groups C ₂ -C ₁₈ -alkenyl, which may be interrupted by, is preferably vinyl, 2-propenyl, 3-butenyl, cis-2-butenyl, trans-2-butenyl or C _q F _{2 (qa)- (1-b)} H _{2a -b} (wherein q ≦ 30, 0 ≦ a ≦ q, and b = 0 or 1).

C ₆ -C ₁₂ -aryl, which may optionally be substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and / or heterocycles, preferably is phenyl, tolyl, xylyl, α-naphthyl , β-naphthyl, 4-diphenylyl, chlorophenyl, dichlorophenyl, trichlorophenyl, difluorophenyl, methylphenyl, dimethylphenyl, trimethylphenyl, ethylphenyl, diethylphenyl, iso-propylphenyl, tert-butyl Phenyl, dodecylphenyl, methoxyphenyl, dimethoxyphenyl, ethoxyphenyl, hexyloxyphenyl, methylnaphthyl, isopropylnaphthyl, chloronaphthyl, ethoxynaphthyl, 2,6-dimethylphenyl, 2,4 , 6-trimethylphenyl, 2,6-dimethoxyphenyl, 2,6-dichlorophenyl, 4-bromophenyl, 2-nitrophenyl, 4-nitrophenyl, 2,4-dinitrophenyl, 2,6-di Nitrophenyl, 4-dimethylaminophenyl, 4-acetylphenyl, methoxyethylphenyl, ethoxymethylphenyl, methylthiophenyl, isopropylthiophenyl or tert-butyl tea (In the formula, 0≤a≤5 Im) phenyl, or _{C 6 F (a-5)} H a a.

C ₅ -C ₁₂ -cycloalkyl, which may optionally be substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and / or heterocycles, preferably is cyclopentyl, cyclohexyl, cyclooctyl, cyclo Dodecyl, methylcyclopentyl, dimethylcyclopentyl, methylcyclohexyl, dimethylcyclohexyl, diethylcyclohexyl, butylcyclohexyl, methoxycyclohexyl, dimethoxycyclohexyl, diethoxycyclohexyl, butylthiocyclohexyl, chlorocyclo Hexyl, dichlorocyclohexyl, dichlorocyclopentyl, C _q F _{2 (qa)-(1-b)} H _{2a -b} , wherein q ≦ 30, 0 ≦ a ≦ q, and b = 0 or 1, Or saturated or unsaturated bicyclic systems such as norbornyl or norbornenyl.

C ₅ -C ₁₂ -cycloalkenyl, which may optionally be substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and / or heterocycles, is preferably 3-cyclopentenyl, 2-cyclo Hexenyl, 3-cyclohexenyl, 2,5-cyclohexadienyl or C _q F _{2 (qa) -3 (1-b)} H _2a-3b (where q ≦ 30, 0 ≦ a ≦ q, And b = 0 or 1).

5- or 6-membered oxygen-, nitrogen- and / or sulfur-containing heterocycles which may be optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and / or heterocycles are preferred. Halyfuryl, thiophenyl, pyryl, pyridyl, indolyl, benzoxazolyl, dioxolyl, dioxyl, benzimidazolyl, benzthiazolyl, dimethylpyridyl, methylquinolyl, dimethylpyryl, methoxyfuryl, dimethoxy Pyridyl or difluoropyridyl.

Two adjacent radicals together are optionally substituted by a functional group, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatom and / or heterocycle, optionally one or more oxygen and / or sulfur atoms and / or one or more When forming unsaturated, saturated or aromatic rings which can be interrupted by substituted or unsubstituted imino groups, they are preferably 1,3-propylene, 1,4-butylene, 1,5-pentylene, 2-oxa -1,3-propylene, 1-oxa-1,3-propylene, 2-oxa-1,3-propylene, 1-oxa-1,3-propenylene, 3-oxa-1,5-pentylene, 1-aza-1,3-propenylene, 1-C ₁ -C ₄ -alkyl-1-aza-1,3-propenylene, 1,4-buta-1,3-dienylene, 1-aza -1,4-buta-1,3-dienylene or 2-aza-1,4-buta-1,3-dienylene.

When the radical contains oxygen and / or sulfur atoms and / or substituted or unsubstituted imino groups, the number of oxygen and / or sulfur atoms and / or imino groups is not limited at all. In general, there will be up to 5, preferably up to 4, very particularly preferably up to 3 in the radicals.

If the radical contains heteroatoms, there is at least one carbon atom, preferably at least two carbon atoms, between any heteroatoms.

Radicals R ¹ to R ⁹ are each independently of the other

- Hydrogen;

Unbranched or branched C ₁ -C, which may be unsubstituted or substituted by one or more hydroxy, halogen, phenyl, cyano, C ₁ -C ₆ -alkylcarbonyl and / or sulfonic acid groups ₁₈ -alkyl, for example methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl), 2-methyl-2-propyl (tert-butyl ), 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 2,2- Dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl, 2,2-dimethyl-1-butyl, 2,3-dimethyl-1- Butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, 1-heptyl, 1-octyl, 1- Nonyl, 1-decyl, 1-undecyl, 1-dodecyl, 1-tetradecyl, 1-hexadecyl, 1-octadecyl, 2-hydroxyethyl, benzyl, 3-phenylprop , 2-cyanoethyl, 2- (methoxycarbonyl) ethyl, 2- (ethoxycarbonyl) ethyl, 2- (n-butoxycarbonyl) ethyl, trifluoromethyl, difluoromethyl, fluorine Rhomethyl, pentafluoroethyl, heptafluoropropyl, heptafluoroisopropyl, nonafluorobutyl, nonafluoroisobutyl, undecylfluoropentyl, undecylfluoroisopentyl, 6-hydroxyhexyl and propyl Sulfonic acid;

Glycols, butylene glycols and oligomers having from 1 to 100 units and hydrogen or C ₁ -C ₈ -alkyl as end groups, for example R ^A O— (CHR ^B —CH ₂ —O) _p —CHR ^B -CH ₂ -or R ^A O- (CH ₂ CH ₂ CH ₂ CH ₂ O) _p -CH ₂ CH ₂ CH ₂ CH ₂ O- (wherein R ^A and R ^B are each preferably hydrogen, methyl or ethyl And p is preferably 0, 1, 2 or 3), in particular 3-oxabutyl, 3-oxapentyl, 3,6-dioxaheptyl, 3,6-dioxaoctyl, 3,6,9- Trioxadedecyl, 3,6,9-trioxoundecyl, 3,6,9,12-tetraoxatridecyl and 3,6,9,12-tetraoxatetradecyl;

- vinyl; And

Particular preference is given to N, N-di-C ₁ -C ₆ -alkylamino such as N, N-dimethylamino and N, N-diethylamino.

The radicals R ¹ to R ⁹ are each independently of each other hydrogen or C ₁ -C ₁₈ -alkyl, such as methyl, ethyl, 1-butyl, 1-pentyl, 1-hexyl, 1-heptyl, 1-octyl, phenyl, 2- Hydroxyethyl, 2-cyanoethyl, 2- (methoxycarbonyl) ethyl, 2- (ethoxycarbonyl) ethyl, 2- (n-butoxycarbonyl) ethyl, N, N-dimethylamino, N , N-diethyl-amino, chlorine or CH ₃ O- (CH ₂ CH ₂ O) _p -CH ₂ CH ₂ -and CH ₃ CH ₂ O- (CH ₂ CH ₂ O) _p -CH ₂ CH _2- ( In the formula, it is very particularly preferred that p is 0, 1, 2 or 3.

Cation [A] ⁺ two

^{One of the} radicals R ¹ to R ⁵ is methyl, ethyl or chlorine and the remaining radicals R ¹ to R ⁵ are each hydrogen;

R ³ is dimethylamino and the remaining radicals R ¹ , R ² , R ⁴ and R ⁵ are each hydrogen;

All radicals R ¹ to R ⁵ are hydrogen;

R ² is carboxy or carboxamide and the remaining radicals R ¹ , R ² , R ⁴ and R ⁵ are each hydrogen;

R ¹ and R ² , or R ² and R ³ together are 1,4-buta-1,3-dienylene and the remaining radicals R ¹ , R ² , R ⁴ and R ⁵ are each hydrogen, pyridinium ions ( IVa);

Especially

R ¹ to R ⁵ are each hydrogen;

Very particular preference is given to ionic liquids in which one of the radicals R ¹ to R ⁵ is methyl or ethyl and the remaining radicals R ¹ to R ⁵ are each hydrogen pyridinium ions (IVa).

Very particularly preferred pyridinium ions (IVa) include 1-methylpyridinium, 1-ethylpyridinium, 1- (1-butyl) pyridinium, 1- (1-hexyl) pyridinium, 1- (1-octyl Pyridinium, 1- (1-hexyl) pyridinium, 1- (1-octyl) pyridinium, 1- (1-dodecyl) pyridinium, 1- (1-tetradecyl) pyridinium, 1- (1 -Hexadecyl) pyridinium, 1,2-dimethylpyridinium, 1-ethyl-2-methylpyridinium, 1- (1-butyl) -2-methylpyridinium, 1- (1-hexyl) -2-methyl Pyridinium, 1- (1-octyl) -2-methylpyridinium, 1- (1-dodecyl) -2-methylpyridinium, 1- (1-tetradecyl) -2-methylpyridinium, 1- ( 1-hexadecyl) -2-methylpyridinium, 1-methyl-2-ethylpyridinium, 1,2-diethylpyridinium, 1- (1-butyl) -2-ethylpyridinium, 1- (1- Hexyl) -2-ethylpyridinium, 1- (1-octyl) -2-ethylpyridinium, 1- (1-dodecyl) -2-ethylpyridinium, 1- (1-tetradecyl) -2-ethyl Pyridinium, 1- (1-hexadecyl) -2-ethylpyridinium, 1,2-dimethyl-5-ethylpyridinium, 1,5-diethyl-2-methylpyridinium, 1- (1-butyl) -2-methyl-3- Ethylpyridinium, 1- (1-hexyl) -2-methyl-3-ethylpyridinium and 1- (1-octyl) -2-methyl-3-ethylpyridinium, 1- (1-dodecyl) -2 -Methyl-3-ethylpyridinium, 1- (1-tetradecyl) -2-methyl-3-ethylpyridinium and 1- (1-hexadecyl) -2-methyl-3-ethylpyridinium. .

Cation [A] ⁺ two

R ¹ to R ⁴ are each hydrogen;

Very particular preference is given to ionic liquids in which one of R ¹ to R ⁴ is methyl or ethyl and the remaining radicals R ¹ to R ⁴ are each hydrogen pyridazinium ion (IVb).

Cation [A] ⁺ two

R ¹ is hydrogen, methyl or ethyl and R ² to R ⁴ are each independently hydrogen or methyl;

Very particular preference is given to ionic liquids which are pyrimidinium ions (IVc) in which R ¹ is hydrogen, methyl or ethyl, R ² and R ⁴ are each methyl and R ³ is hydrogen.

Cation [A] ⁺ two

R ¹ is hydrogen, methyl or ethyl and R ² to R ⁴ are each independently hydrogen or methyl;

R ¹ is hydrogen, methyl or ethyl, R ² and R ⁴ are each methyl and R ³ is hydrogen;

R ¹ to R ⁴ are each methyl;

Very particular preference is given to ionic liquids in which pyrazinium ions (IVd) are each R ¹ to R ⁴ methyl or hydrogen.

Cation [A] ⁺ two

R ¹ is hydrogen, methyl, ethyl, 1-propyl, 1-butyl, 1-pentyl, 1-hexyl, 1-octyl, 2-hydroxyethyl or 2-cyanoethyl, R ² to R ⁴ are each Very particular preference is given to ionic liquids which are imidazolium ions (IVe) which are independently of each other hydrogen, methyl or ethyl.

Very particularly preferred imidazolium ions (IVe) include 1-methylimidazolium, 1-ethylimidazolium, 1- (1-butyl) imidazolium, 1- (1-octyl) imidazolium, 1 -(1-dodecyl) imidazolium, 1- (1-tetradecyl) imidazolium, 1- (1-hexadecyl) imidazolium, 1,3-dimethylimidazolium, 1-ethyl-3- Methylimidazolium, 1- (1-butyl) -3-methylimidazolium, 1- (1-butyl) -3-ethylimidazolium, 1- (1-hexyl) -3-methylimidazolium, 1- (1-hexyl) -3-ethylimidazolium, 1- (1-hexyl) -3-butylimidazolium, 1- (1-octyl) -3-methylimidazolium, 1- (1- Octyl) -3-ethylimidazolium, 1- (1-octyl) -3-butylimidazolium, 1- (1-dodecyl) -3-methylimidazolium, 1- (1-dodecyl)- 3-ethylimidazolium. 1- (1-dodecyl) -3-butylimidazolium, 1- (1-dodecyl) -3-octylimidazolium. 1- (1-tetradecyl) -3-methylimidazolium, 1- (1-tetradecyl) -3-ethylimidazolium, 1- (1-tetradecyl) -3-butylimidazolium, 1- (1-tetradecyl) -3-octylimidazolium, 1- (1-hexadecyl) -3-methylimidazolium, 1- (1-hexadecyl) -3-ethylimidazolium, 1- (1 Hexadecyl) -3-butylimidazolium, 1- (1-hexadecyl) -3-octylimidazolium, 1,2-dimethylimidazolium, 1,2,3-trimethylimidazolium. 1-ethyl-2,3-dimethylimidazolium, 1- (1-butyl) -2,3-dimethylimidazolium, 1- (1-hexyl) -2,3-dimethylimidazolium, 1- ( 1-octyl) -2,3-dimethylimidazolium, 1,4-dimethylimidazolium, 1,3,4-trimethylimidazolium, 1,4-dimethyl-3-ethylimidazolium, 3-butyl Imidazolium, 1,4-dimethyl-3-octylimidazolium, 1,4,5-trimethylimidazolium, 1,3,4,5-tetramethylimidazolium, 1,4,5-trimethyl- 3-ethyl imidazolium, 1,4,5-trimethyl-3-butylimidazolium and 1,4,5-trimethyl-3-octylimidazolium are mentioned.

Cation [A] ⁺ two

Very particular preference is given to ionic liquids which are pyrazolium ions (IVf), (IVg) or (IVg '), wherein R ¹ is hydrogen, methyl or ethyl and R ² to R ⁴ are each independently hydrogen or methyl.

Cation [A] ⁺ two

Very particular preference is given to ionic liquids which are pyrazolium ions (IVh), wherein R ¹ to R ⁴ are each independently hydrogen or methyl.

Cation [A] ⁺ two

Very particular preference is given to ionic liquids in which 1-pyrazolium ions (IVi) in which R ¹ to R ⁶ are each independently hydrogen or methyl.

Cation [A] ⁺ two

Very particular preference is given to ionic liquids in which 2-pyrazolinium ions (IVj ') wherein R ¹ is hydrogen, methyl, ethyl or phenyl and R ² to R ⁶ are each independently hydrogen or methyl.

Cation [A] ⁺ two

R ¹ and R ² are each independently hydrogen, methyl, ethyl or phenyl, and R ³ to R ⁶ are each independently a pyrizolinium ion (IVk) or (IVk ') which is hydrogen or methyl Very particular preference is given to liquid liquids.

Cation [A] ⁺ two

R ¹ and R ² are each independently hydrogen, methyl, ethyl, 1-butyl or phenyl, R ³ and R ⁴ are each independently hydrogen, methyl or ethyl, and R ⁵ and R ⁶ are each independently Very particular preference is given to ionic liquids which are imidazolinium ions (IVl) which are hydrogen or methyl.

Cation [A] ⁺ two

R ¹ and R ² are each independently of each other hydrogen, methyl or ethyl, and each of ionic liquids is imidazolinium ion (IVm) or (IVm ') wherein R ³ to R ⁶ are each independently hydrogen or methyl. Very particularly preferred.

Cation [A] ⁺ two

- R ¹ to R ³ is each hydrogen, methyl or ethyl independently of each other, R ⁴ to R ⁶ are independently of each other as already is hydrogen or methyl, each Jolly hydronium ions (IVn), or (IVn ') of the ionic liquid is Very particularly preferred.

Cation [A] ⁺ two

Ionic liquids are thiazolium ions (IVo) or (IVo ') or oxazolium ions (IVp), wherein R ¹ is hydrogen, methyl, ethyl or phenyl and R ² and R ³ are each independently hydrogen or methyl Very particularly preferred.

Cation [A] ⁺ two

R ¹ and R ² are each independently hydrogen, methyl, ethyl or phenyl and R ³ is hydrogen, methyl or phenyl 1,2,4-triazolium ion (IVq), (IVq ') or (IVq " Very particular preference is given to ionic liquids.

Cation [A] ⁺ two

^1,2 , wherein R ¹ is hydrogen, methyl or ethyl, R ² and R ³ are each independently hydrogen or methyl, or R ² and R ³ together are 1,4-buta-1,3-dienylene; Very particular preference is given to ionic liquids which are 3-triazolium ions (IVr), (IVr ') or (IVr ").

Cation [A] ⁺ two

Very particular preference is given to ionic liquids in which R ¹ is hydrogen, methyl, ethyl or phenyl and pyrrolidinium ions (IVs) wherein R ² to R ⁹ are each independently hydrogen or methyl.

Cation [A] ⁺ two

R ¹ and R ⁴ are each independently hydrogen, methyl, ethyl or phenyl, and R ² and R ³ , and R ⁵ to R ⁸ are each independently hydrogen, methyl imidazolidinium ion (IVt) Very particular preference is given to ionic liquids.

Cation [A] ⁺ two

R ¹ to R ³ are each independently of the other C ₁ -C ₁₈ -alkyl;

R ¹ to R ³ are each independently of each other hydrogen or C ₁ -C ₁₈ -alkyl, and R ⁴ is 2-hydroxyethyl;

R ¹ and R ² together are 1,5-pentylene or 3-oxa-1,5-pentylene and R ³ is C ₁ -C ₁₈ -alkyl, 2-hydroxyethyl or 2-cyanoethyl Very particular preference is given to ionic liquids which are ammonium ions (IVu).

Very particularly preferred ammonium ions (IVu) are methyltri (1-butyl) ammonium, 2-hydroxyethylammonium, N, N-dimethylpiperidinium and N, N-dimethylmorpholinium.

Cation [A] ⁺ two

Very particular preference is given to ionic liquids of guanidinium ions (IVv) in which R ¹ to R ⁵ are each methyl.

Very particularly preferred guanidinium ions (IVv) are N, N, N ', N', N ", N" -hexamethylguanidinium.

Cation [A] ⁺ two

R ¹ and R ² are each independently of each other methyl, ethyl, 1-butyl or 1-octyl, and R ³ is hydrogen, methyl, ethyl, acetyl, —SO ₂ OH or —PO (OH) ₂ ;

R ¹ is methyl, ethyl, 1-butyl or 1-octyl, R ² is a -CH ₂ -CH ₂ -OR ⁴ group, and R ³ and R ⁴ are each independently hydrogen, methyl, ethyl, acetyl, -SO ₂ OH or -PO (OH) ₂ ;

R ¹ is —CH ₂ —CH ₂ —OR ⁴ , R ² is —CH ₂ —CH ₂ —OR ⁵ , and R ³ to R ⁵ are each independently hydrogen, methyl, ethyl, acetyl, Very particular preference is given to ionic liquids which are collinium ions (IVw) which are SO ₂ OH or —PO (OH) ₂ .

Cation [A] ⁺ two

Very particular preference is given to ionic liquids wherein R ¹ to R ³ are each independently of one another C ₁ -C ₁₈ -alkyl, in particular phosphonium ions (IVx) being butyl, isobutyl, 1-hexyl or 1-octyl.

Among these cations, pyridinium ion (IVa), imidazolium ion (IVe) and ammonium ion (IVu), in particular 1-methylpyridinium, 1-ethylpyridinium, 1- (1-butyl) pyridinium, 1 -(1-hexyl) pyridinium, 1- (1-octyl) pyridinium, 1- (1-hexyl) pyridinium, 1- (1-octyl) pyridinium, 1- (1-dodecyl) pyridinium, 1- (1-tetradecyl) pyridinium, 1- (1-hexadecyl) pyridinium, 1,2-dimethylpyridinium, 1-ethyl-2-methylpyridinium, 1- (1-butyl) -2- Methylpyridinium, 1- (1-hexyl) -2-methylpyridinium, 1- (1-octyl) -2-methylpyridinium, 1- (1-dodecyl) -2-methylpyridinium, 1- ( 1-tetradecyl) -2-methylpyridinium, 1- (1-hexadecyl) -2-methylpyridinium, 1-methyl-2-ethylpyridinium, 1,2-diethylpyridinium, 1- (1 -Butyl) -2-ethylpyridinium, 1- (1-hexyl) -2-ethylpyridinium, 1- (1-octyl) -2-ethylpyridinium, 1- (1-dodecyl) -2-ethyl Pyridinium, 1- (1-tetradecyl) -2-ethylpyridinium, 1- (1-hexadecyl) -2-ethylpyridinium, 1,2-dimethyl-5-ethylpyridinium, 1,5-di Tyl-2-methylpyridinium, 1- (1-butyl) -2-methyl-3-ethylpyridinium, 1- (1-hexyl) -2-methyl-3-ethylpyridinium, 1- (1-octyl ) -2-methyl-3-ethylpyridinium, 1- (1-dodecyl) -2-methyl-3-ethylpyridinium, 1- (1-tetradecyl) -2-methyl-3-ethylpyridinium, 1- (1-hexadecyl) -2-methyl-3-ethylpyridinium, 1-methylimidazolium, 1-ethylimidazolium, 1- (1-butyl) imidazolium, 1- (1-octyl ) Imidazolium, 1- (1-dodecyl) imidazolium, 1- (1-tetradecyl) imidazolium, 1- (1-hexadecyl) imidazolium, 1,3-dimethylimidazolium, 1-ethyl-3-methylimidazolium, 1- (1-butyl) -3-methylimidazolium, 1- (1-hexyl) -3-methylimidazolium, 1- (1-octyl) -3 -Methylimidazolium, 1- (1-dodecyl) -3-methylimidazolium, 1- (1-tetradecyl) -3-methylimidazolium, 1- (1-hexadecyl) -3-methyl Imidazolium, 1,2-dimethylimidazolium, 1,2,3-trimethylimidazolium, 1-ethyl-2,3-dimethylimidazolium, 1- (1-butyl) -2,3-dimethyl Imidazolium, 1- (1-hexyl) -2,3-di Thilimidazolium and 1- (1-octyl) -2,3-dimethylimidazolium, 1,4-dimethylimidazolium, 1,3,4-trimethylimidazolium, 1,4-dimethyl-3- Ethylimidazolium, 3-butylimidazolium, 1,4-dimethyl-3-octylimidazolium, 1,4,5-trimethylimidazolium, 1,3,4,5-tetramethylimidazolium, 1,4,5-trimethyl-3-ethylimidazolium, 1,4,5-trimethyl-3-butylimidazolium and 1,4,5-trimethyl-3-octylimidazolium and 2-hydroxyethyl Ammonium is preferred.

The metal cations [M ¹ ] ⁺ , [M ² ] ⁺ , [M ³ ] ⁺ , [M ⁴ ] ²⁺ , and [M ⁵ ] ³⁺ mentioned in formulas (IIIa) to (IIIj) are generally of the periodic table Group 1, 2, 6, 7, 8, 9, 10, 11, 12 and 13 metal cations. Suitable metal cations are, for example, Li ⁺ , Na ⁺ , K ⁺ , Cs ⁺ , Mg ²⁺ , Ca ²⁺ , Ba ²⁺ , C ³⁺ , Fe ²⁺ , Fe ³⁺ , CO ²⁺ , Ni ^{2 +} , Cu ²⁺ , Ag ⁺ , Zn ²⁺ and A1 ³⁺ .

As anions, it is possible in principle to use all anions which, in combination with cations, give an ionic liquid.

The anion [Y] ^n- of the ionic liquid is for example selected from:

Groups of halides and halogen containing compounds of the formula:

^{F -, Cl -, Br -} , I -, BF 4 -, PF 6 -, AlCl 4 -, Al 2 C1 7 -, Al 3 Cl 10 -, AlBr 4 -, FeCl 4 -, BCi 4 -, SbF 6 _{^{-, AsF 6 -, ZnCl 3}} -, SnCl 3 -, CuCl 2 -, CF 3 SO 3 -, (CF 3 SO 3) 2 N -, CF 3 CO 2 -, CCl 3 CO 2 -, CN -, SCN ^{-, OCN -, NO 2 -} , NO 3 -, N (CN) -;

Groups of sulfates, sulfites and sulfonates of the formula:

_{^{SO 4 2 -, HSO 4 -}} , SO 3 2 -, HSO 3 -, R a OSO 3 -, R a SO 3 -;

Group of phosphates of the formula

_{^{PO 4 3 -, HPO 4 2}} -, H 2 PO 4 -, R a PO 4 2 -, HR a PO 4 -, R a R b PO 4 -;

Group of phosphonates and phosphinates of the formula:

_{^{R a HPO 3 -, R a}} R b PO 2 -, R a R b PO 3 -;

A group of phosphites of the formula:

_{^{PO 3 3 -, HPO 3 2}} -, H 2 PO 3 -, R a PO 3 2 -, R a HPO 3 -, R a R b PO 3 -;

A group of phosphonites and phosphinites of the formula:

_{^{R a R b PO 2 -,}} R a HPO 2 -, R a R b PO -, R a HPO -;

A group of carboxylates of the formula:

R ^a COO ^-;

-Group of borate of the formula:

_{^{BO 3 3 -, HBO 3 2}} -, H 2 BOR 3 -, R a R b BO 3 -, R a HBO 3 -, R a BO 3 2 -, B (OR a) (OR b) (OR c) (OR ^d ) ^- , B (HSO ₄ ) ^- , B (R ^a SO ₄ ) ^- ;

A group of boronates of the formula:

_{^{RaBO 2 2 -, R a R}} b BO -;

Groups of carbonates and carboxylic acid esters of the formula:

_{^{HCO 3 -, CO 3 2 -}} , R a CO 3 -;

Groups of silicates and silicate esters of the formula:

_{^{SiO 4 4 -, HSiO 4 3}} -, H 2 SiO 4 2 -, H 3 SiO 4 -, R a SiO 4 3 -, R a R b SiO 4 2 -, R a R b R c SiO 4 -, HR _{^{a SiO 4 2-, H 2 R}} a SiO 4 -, HR a R b SiO 4 -;

Group of alkylsilane and arylsilane salts of the formula:

_{^{R a SiO 3 3 -, R}} a R b SiO 2 2 -, R a R b R c SiO -, R a R b R c SiO 3 -, R a R b R c SiO 2 -, R a R b SiO _^32;

Group of carboxyamide, bis (sulfonyl) imide and sulfonylimide of the formula:

A group of methides of the formula:

A group of alkoxides and aryloxides of the formula:

R ^a O ^-;

A group of halomethlates of the formula:

[M _r Hal _t ] ^s- ;

(Wherein M is a metal, Hal is fluorine, chlorine, bromine or iodine, r and t are positive integers indicating the stoichiometry of the complex and s is a positive integer and represents the charge of the complex);

Group of sulfides, hydrosulfides, polysulfides, hydropolysulfides and thiolates of the formula:

^{S 2 -, HS -, [} S v] 2-, [HS v] -, [R a S] -

Wherein v is a positive integer from 2 to 10;

^{_{- Fe (CN) 6 3-,}} Fe (CN) 6 4-, MnO 4 -, Fe (CO) 4 - group of complex metal ions such as.

Wherein R ^a , R ^b , R ^c and R ^d are each independently of the other

- Hydrogen;

-C ₁ -C ₃₀ -alkyl, or aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, -O-, -CO-,- CO-O- or -CO-N <-substituted derivatives, for example methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methyl-1-propyl (isobutyl), 2 -Methyl-2-propyl (tert-butyl), 1-pentyl, 2-pentyl, 3-pentyl, 2-methyl-1-butyl, 3-methyl-1-butyl, 2-methyl-2-butyl, 3- Methyl-2-butyl, 2,2-dimethyl-1-propyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1- Pentyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2-methyl-3-pentyl, 3-methyl-3-pentyl, 2,2-dimethyl-1- Butyl, 2,3-dimethyl-1-butyl, 3,3-dimethyl-1-butyl, 2-ethyl-1-butyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl, Heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, ecosil, henicosil, docosyl, trico Yarn, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacyl, phenylmethyl (benzyl), diphenylmethyl, triphenylmethyl, 2-phenylethyl, 3-phenylpropyl, Cyclopentylmethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl, cyclohexylmethyl, 2-cyclohexylethyl, 3-cyclohexylpropyl, methoxy, ethoxy, formyl, acetyl or C _q F _{2 (qa) + (1-b)} H _{2a + b} , wherein q ≦ 30, 0 ≦ a ≦ q, and b = 0 or 1 (eg CF ₃ , C ₂ F ₅ , CH ₂ CH ₂ -C _{(q -2)} F _{2 (q-2) +1} , C ₆ F ₁₃ , C ₈ F ₁₇ , C ₁₀ F ₂₁ , C ₁₂ F ₂₅ );

C ₃ -C ₁₂ -cycloalkyl, or aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, -O-, -CO- or -CO-O-substituted derivatives such as cyclopentyl, 2-methyl-1-cyclopentyl, 3-methyl-1-cyclopentyl, cyclohexyl, 2-methyl-1-cyclohexyl, 3-methyl-1- Cyclohexyl, 4-methyl-1-cyclohexyl or C _q F _{2 (qa)-(1-b)} H _{2a -b} , wherein q ≦ 30, 0 ≦ a ≦ q, and b = 0 or 1 );

C ₂ -C ₃₀ -alkenyl, or aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, -O-, -CO- or -CO-O-substituted derivatives such as 2-propenyl, 3-butenyl, cis-2-butenyl, trans-2-butenyl, or C _q F _{2 (qa)-(1-b)} H _2a-b , wherein q ≦ 30, 0 ≦ a ≦ q, and b = 0 or 1;

C ₃ -C ₁₂ -cycloalkenyl, or aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, -O-, -CO- Or -CO-O-substituted derivatives such as 3-cyclopentenyl, 2-cyclohexenyl. 3-cyclohexenyl, 2,5-cyclohexadienyl, or C _q F _{2 (qa) -3 (1-b)} H _2a-3b (where q ≦ 30, 0 ≦ a ≦ q, and b = 0 or 1);

Aryl or heteroaryl of 2 to 30 carbon atoms, or alkyl-, aryl-, heteroaryl-, cycloalkyl-, halogen-, hydroxy-, amino-, carboxy-, formyl-, -O-, -CO- or -CO-O-substituted derivatives such as phenyl, 2-methylphenyl (2-tolyl), 3-methylphenyl (3-tolyl), 4-methylphenyl, 2-ethylphenyl, 3-ethylphenyl, 4 -Ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 4-phenylphenyl , 1-naphthyl, 2-naphthyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, or C ₆ F _(5-a) H _a , where 0 ≦ a ≦ 5;

The two radicals together are optionally substituted by functional groups, aryl, alkyl, aryloxy, alkyloxy, halogen, heteroatoms and / or heterocycles, and / or optionally one or more oxygen and / or sulfur atoms and / or It forms an unsaturated, saturated or aromatic ring that can be interrupted by one or more substituted or unsubstituted imino groups.

Very particularly preferred anions are chloride; Bromide; Iodide; Thioisocyanate; Hexafluorophosphate; Trifluoromethanesulfonate; Methanesulfonate; Formate; acetate; Mandelate; Nitrates; Nitrite; Trifluoroacetate; Sulfate; Hydrosulfate; Methylsulfate; Ethyl sulfate; 1-propylsulfate; 1-butylsulfate; 1-hexylsulfate; 1-octyl sulfate; Phosphate; Dihydrophosphate; Hydrophosphate; C ₁ -C ₄ -dialkylphosphate: propionate; Tetrachloroaluminate; Al ₂ C1 ₇ ^-; Chlorozincate; Chloroperate; Bis (trifluoromethylsulfonyl) imide; Bis (pentafluoroethylsulfonyl) imide; Bis (methylsulfonyl) imide; Bis (p-tolylsulfonyl) imide; Tris (trifluoromethylsulfonyl) methide; Bis (pentafluoroethylsulfonyl) methide; p-tolylsulfonate; Tetracarbonyl cobaltate; Dimethylene glycol monomethyl ether sulfate; Oleate; Stearate; Acrylates; Methacrylate; Maleate; Hydrocitrate; Vinyl phosphonates; Bis (pentafluoroethyl) phosphinate; Borate, such as bis [salicylate (2-)] borate, bis [oxalato (2-)] borate, bis [1,2-benzenediolato (2-)-O, O '] borate, tetracyano Borate, tetrafluoroborate; Dicyanamide; Tris (pentafluoroethyl) trifluorophosphate; Tris (heptafluoropropyl) trifluorophosphate, cyclic arylphosphates such as catecholphosphate (C ₆ H ₄ O ₂ ) P (O) O ^- and chlorocobaltate.

Very particularly preferred anions are chloride, bromide, hydrosulfate, tetrachloroaluminate, thioisocyanate, methylsulfate, ethylsulfate, methanesulfonate, formate, acetate, dimethylphosphate, diethylphosphate, p-tolylsulfonate , Tetrafluoroborate and hexafluorophosphate.

As a cation,

Methyltri- (1-butyl) ammonium, 2-hydroxyethylammonium, 1-methylimidazolium, 1-ethylimidazolium, 1- (1-butyl) imidazolium, 1- (1-octyl) imide Dazolium, 1- (1-dodecyl) imidazolium, 1- (1-tetradecyl) imidazolium, 1- (1-hexadecyl) imidazolium, 1,3-dimethylimidazolium, 1- Ethyl-3-methylimidazolium, 1- (1-butyl) -3-methylimidazolium, 1- (1-butyl) -3-ethylimidazolium, 1- (1-hexyl) -3-methyl Imidazolium, 1- (1-hexyl) -3-ethylimidazolium, 1- (1-hexyl) -3-butylimidazolium, 1- (1-octyl) -3-methylimidazolium, 1 -(1-octyl) -3-ethylimidazolium, 1- (1-octyl) -3-butylimidazolium, 1- (1-dodecyl) -3-methylimidazolium, 1- (1- Dodecyl) -3-ethylimidazolium, 1- (1-dodecyl) -3-butylimidazolium, 1- (1-dodecyl) -3-octylimidazolium, 1- (1-tetradecyl ) -3-methylimidazolium, 1- (1-tetradecyl) -3-ethylimidazolium, 1- (1-tetradecyl) -3-butylimidazolium, 1- (1-tetradecyl)- 3-octylimidazolium, 1- (1-hexadecyl) -3-methylimidazolium, 1- (1-hexadecyl) -3-ethylimidazolium, 1- (1-hexadecyl) -3-butylimidazolium, 1- (1 -Hexadecyl) -3-octylimidazolium, 1,2-dimethylimidazolium, 1,2,3-trimethylimidazolium, 1-ethyl-2,3-dimethylimidazolium, 1- (1- Butyl) -2,3-dimethylimidazolium, 1- (1-hexyl) -2,3-dimethylimidazolium, 1- (1-octyl) -2,3-dimethylimidazolium, 1,4- Dimethylimidazolium, 1,3,4-trimethylimidazolium, 1,4-dimethyl-3-ethylimidazolium, 3-butylimidazolium, 1,4-dimethyl-3-octylimidazolium, 1 , 4,5-trimethylimidazolium, 1,3,4,5-tetramethylimidazolium, 1,4,5-trimethyl-3-ethylimidazolium, 1,4,5-trimethyl-3-butyl Imidazolium or 1,4,5-trimethyl-3-octylimidazolium,

As an anion,

Chloride, bromide, hydrosulfate, tetrachloroaluminate, thioisocyanate, methylsulfate, ethylsulfate, methanesulfonate, formate, acetate, dimethylphosphate, diethylphosphate, p-tolylsulfonate, tetrafluoroborate Or ionic liquids comprising hexafluorophosphate are particularly preferred:

Also particularly preferred are the following ionic liquids:

1,3-dimethylimidazolium methyl sulfate, 1,3-dimethylimidazolium hydrosulfate, 1,3-dimethylimidazolium dimethyl phosphate, 1-ethyl-3-methylimidazolium methyl sulfate, 1 -Ethyl-3-methylimidazolium hydrosulfate, 1-ethyl-3-methylimidazolium thiocyanate, 1-ethyl-3-methylimidazolium acetate, 1-ethyl-3-methylimidazolium methane Sulfonate, 1-ethyl-3-methylimidazolium diethylphosphate, 1- (1-butyl) -3-methylimidazolium methylsulfate, 1- (1-butyl) -3-methylimidazolium hydro Sulfate, 1- (1-butyl) -3-methylimidazolium thioisocyanate, 1- (1-butyl) -3-methylimidazolium acetate, 1- (1-butyl) -3-methylimidazolium Methanesulfonate, 1- (1-dodecyl) -3-methylimidazolium methylsulfate, 1- (1-dodecyl) -3-methylimidazolium hydrosulfate, 1- (1-tetradecyl) 3-methylimidazolium methylsulfate, 1- (1-tetradecyl) -3-meth Imidazolium hydrosulfate, 1- (1-hexadecyl) -3-methylimidazolium methylsulfate or 1- (1-hexadecyl) -3-methylimidazolium hydrosulfate or 2-hydroxyethyl Ammonium formate.

Also derived from dimers of ionic liquids [A] _n ⁺ [Y] ⁿ⁻ , wherein n = 1 or 2, and [A] _n ⁺ , wherein n = 1 or 2, Corresponding salts are preferred, wherein the cation [A] ⁺ is of formula (IVa), (IVe), (IVf), (IVg), (IVg '), (IVh), (IVm), where NR ¹ Is replaced by oxygen), (IVq), (IVq "), (IVr '), (IVv), (IVu), (Ivx), in particular

[In the formula,

R is hydrogen;

Linear or branched C ₁ -C ₂₀ -alkyl which may have one or more groups selected from halogen, hydroxyl, cyano, amino and mercapto; or

-(R ^x -X) _w -R ^y (wherein w = 1-10, R ^x is linear or branched C ₁ -C ₂₀ -alkyl, R ^y is hydrogen, or linear or branched C ₁₎ -C ₁₀ -alkyl, X is an ether, thioether, ester, siloxane or amide group;

R ¹ , R ² , R ³ , R ⁴ and R ⁵ are each independently hydrogen;

Halides, hydroxy,

Linear or branched C ₁ -C ₂₀ -alkyl which may have one or more groups selected from halogen, hydroxyl, cyano, amino and mercapto; or

-(R ^x -X) _w -R ^y (wherein w = 1-10, R ^x is linear or branched C ₁ -C ₂₀ -alkyl, R ^y is hydrogen, or linear or branched C ₁₎ -C ₁₀ -alkyl, X is an ether, thioether, ester, siloxane or amide group;

[In the formula,

R and R ¹ are each independently hydrogen;

Linear or branched C ₁ -C ₂₀ -alkyl which may have one or more groups selected from halogen, hydroxyl, cyano, amino and mercapto; or

-(R ^x -X) _w -R ^y (wherein w = 1-10, R ^x is linear or branched C ₁ -C ₂₀ -alkyl, R ^y is hydrogen, or linear or branched C ₁₎ -C ₁₀ -alkyl, X is an ether, thioether, ester, siloxane or amide group;

R ² , R ³ and R ⁴ are each independently hydrogen;

Halides, hydroxy,

Linear or branched C ₁ -C ₂₀ -alkyl which may have one or more groups selected from halogen, hydroxyl, cyano, amino and mercapto; or

-(R ^x -X) _w -R ^y (wherein w = 1-10, R ^x is linear or branched C ₁ -C ₂₀ -alkyl, R ^y is hydrogen, or linear or branched C ₁₎ -C ₁₀ -alkyl, X is an ether, thioether, ester, siloxane or amide group;

(In the formula,

R and R ¹ are each independently hydrogen;

Linear or branched C ₁ -C ₂₀ -alkyl which may have one or more groups selected from halogen, hydroxyl, cyano, amino and mercapto; or

-(R ^x -X) _w -R ^y (wherein w = 1-10, R ^x is linear or branched C ₁ -C ₂₀ -alkyl, R ^y is hydrogen, or linear or branched C ₁₎ -C ₁₀ -alkyl, X is an ether, thioether, ester, siloxane or amide group;

R ² , R ³ and R ⁴ are each independently hydrogen;

Halides, hydroxy,

Linear or branched C ₁ -C ₂₀ -alkyl which may have one or more groups selected from halogen, hydroxyl, cyano, amino and mercapto; or

-(R ^x -X) _w -R ^y (wherein w = 1-10, R ^x is linear or branched C ₁ -C ₂₀ -alkyl, R ^y is hydrogen, or linear or branched C ₁₎ -C ₁₀ -alkyl, X is an ether, thioether, ester, siloxane or amide group;

[In the formula,

R is hydrogen;

Linear or branched C ₁ -C ₂₀ -alkyl which may have one or more groups selected from halogen, hydroxyl, cyano, amino and mercapto; or

-(R ^x -X) _w -R ^y (wherein w = 1-10, R ^x is linear or branched C ₁ -C ₂₀ -alkyl, R ^y is hydrogen, or linear or branched C ₁₎ -C ₁₀ -alkyl, X is an ether, thioether, ester, siloxane or amide group;

R ¹ , R ² , R ³ and R ⁴ are each independently hydrogen;

Halides, hydroxy,

Linear or branched C ₁ -C ₂₀ -alkyl which may have one or more groups selected from halogen, hydroxyl, cyano, amino and mercapto; or

-(R ^x -X) _w -R ^y (wherein w = 1-10, R ^x is linear or branched C ₁ -C ₂₀ -alkyl, R ^y is hydrogen, or linear or branched C ₁₎ -C ₁₀ -alkyl, X is an ether, thioether, ester, siloxane or amide group;

[In the formula,

R is hydrogen;

Linear or branched C ₁ -C ₂₀ -alkyl which may have one or more groups selected from halogen, hydroxyl, cyano, amino and mercapto; or

-(R ^x -X) _w -R ^y (wherein w = 1-10, R ^x is linear or branched C ₁ -C ₂₀ -alkyl, R ^y is hydrogen, or linear or branched C ₁₎ -C ₁₀ -alkyl, X is an ether, thioether, ester, siloxane or amide group;

R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are each independently hydrogen;

Halides, hydroxy,

Linear or branched C ₁ -C ₂₀ -alkyl which may have one or more groups selected from halogen, hydroxyl, cyano, amino and mercapto; or

-(R ^x -X) _w -R ^y (wherein w = 1-10, R ^x is linear or branched C ₁ -C ₂₀ -alkyl, R ^y is hydrogen, or linear or branched C ₁₎ -C ₁₀ -alkyl, X is an ether, thioether, ester, siloxane or amide group;

NR ¹ is replaced by oxygen;

[In the formula,

R and R ³ are each independently of the other hydrogen;

Linear or branched C ₁ -C ₂₀ -alkyl which may have one or more groups selected from halogen, hydroxyl, cyano, amino and mercapto; or

-(R ^x -X) _w -R ^y (wherein w = 1-10, R ^x is linear or branched C ₁ -C ₂₀ -alkyl, R ^y is hydrogen, or linear or branched C ₁₎ -C ₁₀ -alkyl, X is an ether, thioether, ester, siloxane or amide group;

R ¹ and R ² are each independently hydrogen;

Halides, hydroxy,

Linear or branched C ₁ -C ₂₀ -alkyl which may have one or more groups selected from halogen, hydroxyl, cyano, amino and mercapto; or

-(R ^x -X) _w -R ^y (wherein w = 1-10, R ^x is linear or branched C ₁ -C ₂₀ -alkyl, R ^y is hydrogen, or linear or branched C ₁₎ -C ₁₀ -alkyl, X is an ether, thioether, ester, siloxane or amide group;

[In the formula,

R and R ¹ are each independently hydrogen;

Linear or branched C ₁ -C ₂₀ -alkyl which may have one or more groups selected from halogen, hydroxyl, cyano, amino and mercapto; or

-(R ^x -X) _w -R ^y (wherein w = 1-10, R ^x is linear or branched C ₁ -C ₂₀ -alkyl, R ^y is hydrogen, or linear or branched C ₁₎ -C ₁₀ -alkyl, X is an ether, thioether, ester, siloxane or amide group;

R ² and R ³ are each independently hydrogen;

Halides, hydroxy,

Linear or branched C ₁ -C ₂₀ -alkyl which may have one or more groups selected from halogen, hydroxyl, cyano, amino and mercapto; or

-(R ^x -X) _w -R ^y (wherein w = 1-10, R ^x is linear or branched C ₁ -C ₂₀ -alkyl, R ^y is hydrogen, or linear or branched C ₁₎ -C ₁₀ -alkyl, X is an ether, thioether, ester, siloxane or amide group;

[In the formula,

R, R ¹ , R ² and R ³ are each independently hydrogen;

Linear or branched C ₁ -C ₂₀ -alkyl which may have one or more groups selected from halogen, hydroxyl, cyano, amino and mercapto; or

-(R ^x -X) _w -R ^y (wherein w = 1-10, R ^x is linear or branched C ₁ -C ₂₀ -alkyl, R ^y is hydrogen, or linear or branched C ₁₎ -C ₁₀ -alkyl, X is an ether, thioether, ester, siloxane or amide group;

R and R ¹ are each independently of the other hydrogen;

Linear or branched C ₁ -C ₂₀ -alkyl which may have one or more groups selected from halogen, hydroxyl, cyano, amino and mercapto; or

-(R ^x -X) _w -R ^y (wherein w = 1-10, R ^x is linear or branched C ₁ -C ₂₀ -alkyl, R ^y is hydrogen, or linear or branched C ₁₎ -C ₁₀ -alkyl, X is an ether, thioether, ester, siloxane or amide group;

R ² and R ³ together form a 3-oxa-1,5-pentylene radical, which in turn

Halogen, hydroxyl;

Linear or branched C ₁ -C ₂₀ -alkyl which may have one or more groups selected from halogen, hydroxyl, cyano, amino and mercapto; or

-(R ^x -X) _w -R ^y (wherein w = 1-10, R ^x is linear or branched C ₁ -C ₂₀ -alkyl, R ^y is hydrogen, or linear or branched C ₁₎ -C ₁₀ -alkyl, X can be substituted by ether, thioether, ester, siloxane or amide group;

R and R ¹ are each independently of the other hydrogen;

Linear or branched C ₁ -C ₂₀ -alkyl which may have one or more groups selected from halogen, hydroxyl, cyano, amino and mercapto; or

-(R ^x -X) _w -R ^y (wherein w = 1-10, R ^x is linear or branched C ₁ -C ₂₀ -alkyl, R ^y is hydrogen, or linear or branched C ₁₎ -C ₁₀ -alkyl, X is an ether, thioether, ester, siloxane or amide group;

R ² and R ³ together form a 1,4-buta-1,3-dienylene radical, which in turn

Halogen, hydroxyl;

Linear or branched C ₁ -C ₂₀ -alkyl which may have one or more groups selected from halogen, hydroxyl, cyano, amino and mercapto; or

-(R ^x -X) _w -R ^y (wherein w = 1-10, R ^x is linear or branched C ₁ -C ₂₀ -alkyl, R ^y is hydrogen, or linear or branched C ₁₎ -C ₁₀ -alkyl, X may be substituted by ether, thioether, ester, siloxane or amide group;

[In the formula,

R, R ¹ , R ² , R ³ , R ⁴ and R ⁵ are each independently hydrogen;

Linear or branched C ₁ -C ₂₀ -alkyl which may have one or more groups selected from halogen, hydroxyl, cyano, amino and mercapto; or

-(R ^x -X) _w -R ^y (wherein w = 1-10, R ^x is linear or branched C ₁ -C ₂₀ -alkyl, R ^y is hydrogen, or linear or branched C ₁₎ -C ₁₀ -alkyl, X is an ether, thioether, ester, siloxane or amide group;

[In the formula,

R, R ¹ , R ² and R ³ are each independently hydrogen;

Linear or branched C ₁ -C ₂₀ -alkyl which may have one or more groups selected from halogen, hydroxyl, cyano, amino and mercapto; or

-(R ^x -X) _w -R ^y (wherein w = 1-10, R ^x is linear or branched C ₁ -C ₂₀ -alkyl, R ^y is hydrogen, or linear or branched C ₁₎ -C ₁₀ -alkyl, X is an ether, thioether, ester, siloxane or amide group.

The anion [Y] ^n- is a halide, tetrafluoroborate, sulfate, phosphate, R ^U R ^V PO ₂ ^-, DC hold imide, carboxylate R ^U -COO ^-, sulfonate -SO ₃ R ^{U -,} benzene sulfonate, toluene sulfonate, organic sulfates R ^U -O-SO ₃ ^-, bis (sulfone) imide _{^{[R U -SO 2 -N-SO}} 2 -R V] -, the structure [R ^U -CO-N -CO-R ^{V] -} and _{^{[R U -SO 2 -N-CO}} -R V] - is selected from imide, and the group consisting of formate, in which

R ^U and R ^V are each independently of each other linear or branched, aliphatic or cycloaliphatic C ₁ -C ₂₀ -alkyl, C ₅ -C ₁₅ -aryl, C ₅ -C ₁₅ -aryl-C ₁ -C ₆ -alkyl Or C ₁ -C ₆ -alkyl-C ₅ -C ₁₅ -aryl,

The radicals may be substituted with one or more radicals selected from the group consisting of halogen and hydroxyl.

Particular preference is given to working material pairs which comprise water, methanol or ammonia, in particular water or ammonia, as component A) and which comprise an ionic liquid according to one of the above specific embodiments as component B). Very preferred are functional substance pairs comprising water as component A). Particular preference is likewise given to functional substance pairs comprising ammonia as component A).

Particular preference is likewise given to the functional substance pairs which comprise at least 10% by weight, preferably at least 20% by weight, in particular at least 30% by weight, of the functional substances as component A).

Particular preference is likewise given to component B) as component B) comprising up to 90% by weight, preferably up to 80% by weight, in particular up to 70% by weight, of ionic liquids relative to the total weight of the working material pair.

In addition, particular preference is given to a pair of working materials which are compatible with the working material and the ionic liquid in the temperature range of -20 to 200 ° C, particularly preferably -5 to 150 ° C.

Particular preference is given to a pair of functional substances in which the functional substance is water.

In addition, particular preference is given to a pair of working materials which are compatible with the working material and the ionic liquid in the temperature range of -60 to 100 ° C, particularly preferably -40 to 50 ° C. Here, a pair of functional substances in which the functional substance is ammonia is preferred.

In another embodiment, the ionic liquid can be applied to a suitable solid support.

The present invention also provides the use of ionic liquids as absorbent media in absorption heat pumps, absorption chillers and heat converters. In preferred embodiments, the above preferred embodiments apply similarly.

The present invention relates to an absorption heat pump, an absorption chiller and a heat converter, comprising a liquefier, an expansion engine, a boiler and an absorber and comprising an ionic liquid as the absorption medium. In preferred embodiments, the above preferred embodiments for ionic liquids apply similarly.

The invention likewise relates to an absorption heat pump, an absorption freezer and a heat converter, comprising a liquefier, an expansion engine, a stripper and an absorber, and comprising a working material pair comprising a working material and an ionic liquid. In preferred embodiments, the above preferred embodiments for the agonist pair apply similarly.

The invention is illustrated by the following examples.

The ionic liquids used according to the invention have a slightly small vapor pressure; Working material pairs according to the invention comprising ionic liquids and working materials are particularly useful, ie separation problems as for example in the case of ammonia / water working material pairs are avoided.

The ionic liquids used according to the invention are liquids in the operating range of the temperature range; The working material pairs according to the invention comprising ionic liquids and working materials are therefore particularly useful because no salt crystallization problem arises. The total amount of working substance, such as water, can therefore be taken from the absorbent medium and used for cooling (the degassing range is wide). In addition, only the absorbent medium itself, i.e. the ionic liquid, must be cooled during the transport of the absorbent medium between the stripper and the absorber, ie the ionic liquid must be cooled, but as in the case of the material pairs of lithium bromide and water, By way of example, the working material does not need to be cooled.

Compatibility of the ionic liquid with the working substance is assured; Thus, the ionic liquid ethylmethylimidazolium triflate can be mixed with water.

Furthermore, the heat resistance of the ionic liquid is excellent; [Blake et al., Proceedings of the 11 ^th Solar PACES International Symposium, 2002] estimate that temperatures above 300 ° C. can be achieved. Thus, the pair of working materials of the present invention also has good stability and heat resistance.

In addition, the toxicity of the ionic liquids tested so far has been classified as low (eg LD ₅₀ > 1000 mg / kg); Since its vapor pressure is substantially unmeasurable, it does not form a potentially ignitable mixture and thus does not exhibit both explosion hazard and toxicity problems.

It has also been found that the vapor pressure of water can be reduced by 1/4 upon dissolution in ionic liquids such as 2-hydroxyethylammonium formate.

For this purpose, the partial pressure of water with respect to the aqueous 2-hydroxyethylammonium formate solution was obtained (by FTIR spectroscopy on gas) at normal phase equilibrium temperature. At 30.5 ° C., the partial pressure of water for a solution comprising 84% by weight of 2-hydroxyethylammonium formate and 16% by weight of water was found to be about 10 mbar, but the partial pressure of water relative to water itself is about 40 mbar. . At a temperature of 34 ° C., the partial pressure of water for the solution comprising 87% by weight of 2-hydroxyethylammonium formate and 13% by weight of water was found to be about 12 mbar, but it was found that The partial pressure is about 50 mbar.

For conventional absorption chillers operated so far using a lithium bromide / water working material pair, the working material pair is likewise a system ionic liquid / water, for example N-ethyl-N-methylimidazolium tetrafluoroborate It can be replaced with / water and there is no need to change the configuration of the machine to allow operation with fresh absorption media.

In one preferred embodiment, an absorption heat pump conventionally operated using an agonist pair of water / ammonia can be operated using an agonist pair of ionic liquids / ammonia. In this case, since the separation of ammonia from the ionic liquid by evaporation of ammonia is complete, the conventional rectification of the other manner of the water / ammonia mixture is unnecessary.

Claims (15)

A) a functional substance selected from the group consisting of water, ammonia, and methanol; And B) Ionic liquids, salt melts with melting points below 80 ° C An apparatus selected from the group consisting of an absorption heat pump, an absorption chiller, and an absorption system heat converter, comprising a pair of working materials of: The device of claim 1 wherein the ionic liquid is a salt of formula I, II or III, or a mixture thereof: B1) [A] _n ⁺ [Y] ^n- (I) (Wherein n is 1, 2, 3 or 4, [A] ⁺ is a quaternary ammonium cation, oxonium cation, sulfonium cation or phosphonium cation, [Y] ^n- is monovalent, divalent, Trivalent or tetravalent anion); B2) Mixed Salts of Formula (II)

Wherein [A ¹ ] ⁺ , [A ² ] ⁺ , [A ³ ] ⁺ and [A ⁴ ] ⁺ are B1) as defined above for [A] ⁺ and [Y] ⁿ⁻ as defined under Independently selected from the groups); or B3) Mixed Salts of Formula (III):

Wherein [A ¹ ] ⁺ , [A ² ] ⁺ and [A ³ ] ⁺ are independently selected from the groups mentioned above for [A] ⁺ and [Y] ^n- as defined under B1; , [M ¹ ] ⁺ , [M ² ] ⁺ and [M ³ ] ⁺ are monovalent metal cations, [M ⁴ ] ²⁺ is a divalent metal cation, and [M ⁵ ] ³⁺ is a trivalent metal cation ). A device according to claim 1 or 2 comprising component B as component B comprising one ionic liquid of formula (I), (II) or (III). A device according to claim 1 or 2, comprising component B as component B comprising at least one ionic liquid of formula (I), (II) or (III). The device of claim 1, wherein the ionic liquid is a liquid in a temperature range of −20 ° C. to 200 ° C. 4. The device of claim 1 or 2, wherein the working substance and the ionic liquid are miscible in the temperature range of −20 ° C. to 200 ° C. 4. The device according to claim 1 or 2, wherein the agonist is water. The device of claim 1 or 2, wherein the working substance and the ionic liquid are miscible in the temperature range of −60 ° C. to 100 ° C. 4. The device of claim 1 or 2, wherein the agonist is ammonia. delete delete The device of claim 1 or 2, wherein the ionic liquid is an absorption medium and further comprises a liquefier, an expansion engine, a boiler, and an absorber. The device of claim 2, wherein the working material is absorbed in the ionic liquid and the device is an absorption heat pump. The device of claim 2, wherein the working substance is absorbed in the ionic liquid and the device is an absorption refrigerator. The device of claim 2, wherein the working material is absorbed in the ionic liquid and the device is an absorption-based heat transducer.