Liquids

• US 8,992,798 B2
• Filed: 06/28/2011
• Issued: 03/31/2015
• Est. Priority Date: 04/07/2004
• Status: Active Grant

• Current Assignee: Worn Again Technologies Ltd.
• Original Assignee: Innovia Films Limited (Innovia Films)
• Inventors: Walker, Adam John
• Primary Examiner(s): MC GINTY, DOUGLAS J
• Application Number:
  US13/170,686
• Publication Number:
  US 20110257433A1
• Time in Patent Office: 1,372 Days
• Field of Search: 252/364, 562/579, 564/159
• US Class Current: 252/364
• CPC Class Codes: B01J 31/003 containing enzymes
• CPC Class Codes: B01J 31/0278 containing nitrogen as cationic centre
• CPC Class Codes: C07C 215/08 with only one hydroxy group and one amino group bound to the carbon skeleton
• CPC Class Codes: C07C 215/12 the nitrogen atom of the amino group being further bound to hydrocarbon groups substituted by hydroxy groups
• CPC Class Codes: C07C 215/40 with quaternised nitrogen atoms bound to carbon atoms of the carbon skeleton
• CPC Class Codes: C07C 217/30 having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C08K 5/19 Quaternary ammonium compounds
• CPC Class Codes: C08K 5/3415 Five-membered rings
• CPC Class Codes: C10N 2020/077 Ionic Liquids
• CPC Class Codes: Y02P 20/54 using solvents, e.g. supercritical solvents or ionic liquids

Abstract

The present invention relates to an ionic liquid comprising an anion and a cation, wherein the cation is a primary, secondary or tertiary ammonium ion containing a protonated nitrogen atom.

Claims

1. A process for dissolving an organic, inorganic, or biological material, the process comprising contacting the organic, inorganic, or biological material with an ionic liquid, the ionic liquid comprising an anion and a cation characterised in that the cation is a tertiary nitrogen-containing cation of the formula (I)

N⁺HRR′

R″

 

 

(I)

wherein;

R is a hydrocarbyl group optionally interrupted by one or more ether or thioether linkages, and substituted with one or more substituents selected from nitrogen-containing functional groups, alkenyl, alkoxy, carbonyl and carboxyl groups;

or from thiol, alkythio, sulphonyl, thiocyanate, isothiocyanate, azido, hydrazino, halogen, boronate and silyl groups;

R′ and

R″

, which may be the same or different, each represent H or a hydrocarbyl group optionally interrupted by one or more ether or thioether linkages, and optionally substituted with one or more substituents selected from nitrogen-containing functional groups, alkyl, alkenyl, alkoxy, hydroxy, carbonyl and carboxyl groups;

or from thiol, alkythio, sulphonyl, thiocyanate, isothiocyanate, azido, hydrazino, halogen, boronate and silyl groups; and

any two or three of R, R′ and

R″

may be joined together with the N to form a cyclic group.

2. The process of claim 1, wherein at least one of R, R′

or R″

is substituted with a nitrogen-containing functional group, and wherein one or more such nitrogen-containing functional group is a basic nitrogen-containing functional group.

3. The process of claim 1, wherein at least one of R, R′

or R″

is substituted with a nitrogen-containing functional group, and wherein one or more such nitrogen-containing functional group is selected from nitrile, nitro, amino and substituted amino.

4. The process of claim 3, wherein one or more substituted amino group is selected from mono- or di-alkylamino and alkyamido.

5. The process of claim 4, wherein one or more dialkylamino group is a dimethylamino group.

6. The process of claim 1, wherein one or more of R, R′

or R″

is substituted with an alkoxy group.

7. The process of claim 6, wherein one or more alkoxy group is a methoxy group.

8. The process of claim 6, wherein one or more of R, R′

or R″

is interrupted by an ether linkage.

9. The process of claim 1, wherein one or both of R′

or R″

is an unsubstituted hydrocarbyl group.

10. The process of claim 1, wherein the anion is selected from the group consisting of halogenated inorganic anions, nitrates, sulphates, phosphates, carbonates, sulphonates, alkylsulphonates, carboxylates, and alkylcarboxylates.

11. The process of claim 10, wherein the alkyl substituent of the alkylsulphonates or the alkylcarboxylates is substituted at any position with alkenyl, alkoxy, alkeneoxy, aryl, arylalkyl, aryloxy, amino, aminoalkyl, thio, thioalkyl, hydroxyl, hydroxyalkyl, carbonyl, oxoalkyl, carboxyl, carboxyalkyl or halide.

12. The process of claim 10, wherein the anion is chosen from bis(trifluoromethylsulphonyl)imide, carbonate, hydrogen carbonate, sulphate, hydrogen sulphate, silicate, phosphate, hydrogen phosphate, dihydrogen phosphate, metaphosphate, methanesulphonate, trifluoromethanesulphonate, ethylenediaminetetraacetate, chloride, bromide, iodide, hexafluorophosphate, tetrafluoroborate, trifluoroacetate, pentafluoropropanoate, heptafluorobutanoate, oxalate, formate, acetate, propanoate, butanoate, pentanoate, hexanoate, heptanoate, octanoate, nonanoate, decanoate, benzoate, benezenedicarboxylate, benzenetricarboxylate, benzenetetracarboxylate, chlorobenzoate, fluorobenzoate, pentachlorobenzoate, pentafluorobenzoate, salicylate, glycolate, lactate, pantothenate, tartrate, hydrogen tartrate, mandelate, crotonate, malate, pyruvate, succinate, citrate, fumarate, phenylacetate, and an organic carboxylate.