Process for removing polar impurities from hydrocarbons and mixtures of hydrocarbons

A process for the purification of a hydrocarbon, or mixture of hydrocarbons, comprising one or more impurities that are extractable with an organic ionic liquid, the process comprising the steps of:

• a) providing a hydrocarbon, or mixture of hydrocarbons, comprising one or more impurities that are extractable with an organic ionic liquid;
• b) exposing the hydrocarbon, or mixture thereof, to one or more organic ionic liquids while agitating for a period of time sufficient and at a temperature sufficient for the organic ionic liquid to extract at least a portion of the one or more impurities from the hydrocarbon and to form an at least biphasic mixture with the hydrocarbon, or mixture thereof;
• and
• c) separating the organic ionic liquid from the hydrocarbon, or mixture thereof, whereby the amount of one or more impurities in the hydrocarbon, or mixture thereof, is reduced;
• wherein
• d) the organic ionic liquid comprises one or more organic anions and one or more organic cations, and the identity of the organic anion and organic cation is independently selected at each occurrence;
• e) the one or more impurities is selected from the group consisting of nitrogen-containing impurities;
• halogen-containing impurities;
• oxygen-containing impurities, said oxygen-containing impurities being selected from the group consisting of aldehydes, ketones, carboxylic acids and peroxides;
• and a mixture of two or more thereof;
• f) the organic anion is selected from the group consisting of alkylsulfonate, arylsulfonate, arylalkylsulfonate, alkoxysulfonate, alkylarylsulfonate, alkylcarboxylate, arylcarboxylate, arylalkylcarboxylate, alkoxycarboxylate, alkylarylcarboxylate, acetate, benzoate and any member of the group optionally substituted with one or more halogen atoms;
• and
• g) the organic cation is selected from the group consisting of quaternary ammonium cation, phosphonium cation, imidazolium cation, pyrdinium cation, pyrazolium cation, and triazolium cation.

A process for the purification of a hydrocarbon, or mixture of hydrocarbons, comprising one or more impurities that are extractable with an organic ionic liquid, the process consisting essentially of:

• a) providing a hydrocarbon, or mixture of hydrocarbons, comprising one or more impurities that are extractable with an organic ionic liquid;
• b) exposing the hydrocarbon, or mixture thereof, to one or more organic ionic liquids while agitating for a period of time sufficient and at a temperature sufficient for the organic ionic liquid to extract at least a portion of the one or more impurities from the hydrocarbon and to form an at least biphasic mixture with the hydrocarbon, or mixture thereof;
• and
• c) separating the organic ionic liquid from the hydrocarbon, or mixture thereof, whereby the amount of one or more impurities in the hydrocarbon, or mixture thereof, is reduced;
• wherein
• d) the organic ionic liquid comprises one or more organic anions and one or more organic cations, and the identity of the organic anion and organic cation is independently selected at each occurrence;
• and
• e) the one or more impurities is one or more sulfur-containing impurities selected from the group consisting of organic aliphatic or aromatic sulfur compounds, mercaptane, thiophene, methylthiophene, or dibenzolthiophene;
• wherein the ionic liquid is a compound, or a mixture of compounds, of the Formula 1
• (A)n+(Y)n−, Formula 1
• wherein:
• n=1 or 2;
• the anion (Y)n− is selected from the group consisting of alkylsulfonate, arylsulfonate, arylalkylsulfonate, alkoxysulfonate, alkylarylsulfonate, alkylcarboxylate, arylcarboxylate, arylalkylcarboxylate, alkoxycarboxylate, alkylarylcarboxylate, acetate, benzoate and any member of the group optionally substituted with one or more halogen atoms;
• the cation (A)+ is selected from the group consisting of
• quaternary ammonium cations of general formula
• (NR1R2R3R)+,
• phosphonium cations of general formula
• (PR1R2R3R)+,
• imidazolium cations of general formula
• wherein the imidazole nucleus may be substituted with at least one group selected from C1-C6 alkyl, C1-C6 alkoxy, C1-C6 aminoalkyl, C5-C16 aryl or C5-C16-aryl-C1-C6-alkyl groups;
• pyridinium cations of general formula
• wherein the pyridine nucleus may be substituted with at least one group selected from C1-C6 alkyl, C1-C6 alkoxy, C1-C6 aminoalkyl, C5-C16 aryl or C5-C16-aryl-C1-C6-alkyl groups;
• pyrazolium cations of general formula
• wherein the pyrazole nucleus may be substituted with at least one group selected from C1-C6 alkyl, C1-C6 alkoxy, C1-C6 aminoalkyl, C5-C16 aryl or C5-C16-aryl-C1-C6-alkyl groups;
• and
• triazolium cations of general formula
• wherein the triazole nucleus may be substituted with at least one group selected from C1-C6 alkyl, C1-C6 alkoxy, C1-C6 aminoalkyl, C5-C16 aryl or C5-C16-aryl-C1-C6-alkyl groups;
• the residues R1, R2, R3 are independently selected at each occurrence from the group consisting of:
• hydrogen;
• linear or branched, saturated or unsaturated, aliphatic or alicyclic alkyl groups having from 1 to 20 carbon atoms;
• heteroaryl, heteroaryl-C1-C6-alkyl groups having from 3 to 8 carbon atoms in the heteroaryl residue 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;
• and
• aryl, aryl-C1-C6-alkyl groups having from 5 to 16 carbon atoms in the aryl residue which may be optionally substituted with at least one C1-C6 alkyl group and/or halogen atom;
• and
• the residue R is independently selected at each occurrence from the group consisting of:
• linear or branched, saturated or unsaturated, aliphatic or alicyclic alkyl groups having from 1 to 20 carbon atoms;
• heteroaryl, heteroaryl-C1-C6-alkyl groups having from 3 to 8 carbon atoms in the heteroaryl residue 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 having from 5 to 16 carbon atoms in the aryl residue which may be optionally substituted with at least one C1-C6 alkyl group and/or halogen atom.