CA3074850A1 - Ionic liquids for upgrading of bitumen - Google Patents

Ionic liquids for upgrading of bitumen Download PDF

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Publication number
CA3074850A1
CA3074850A1 CA3074850A CA3074850A CA3074850A1 CA 3074850 A1 CA3074850 A1 CA 3074850A1 CA 3074850 A CA3074850 A CA 3074850A CA 3074850 A CA3074850 A CA 3074850A CA 3074850 A1 CA3074850 A1 CA 3074850A1
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Prior art keywords
ionic liquid
bitumen
diluent
feedstock
mixture
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CA3074850A
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French (fr)
Inventor
Carrie Fanai
Todd Pugsley
Ying QI
Karolina Matuszek
Douglas Robert Macfarlane
Alan Loyd Chaffee
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Suncor Energy Inc
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Suncor Energy Inc
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Priority to CA3074850A priority Critical patent/CA3074850A1/en
Priority to CA3172921A priority patent/CA3172921A1/en
Priority to CA3172912A priority patent/CA3172912A1/en
Priority to CA3172913A priority patent/CA3172913A1/en
Priority to CA3111226A priority patent/CA3111226A1/en
Priority to US17/192,704 priority patent/US20210277315A1/en
Priority to CA3172927A priority patent/CA3172927A1/en
Publication of CA3074850A1 publication Critical patent/CA3074850A1/en
Pending legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G55/00Treatment of hydrocarbon oils, in the absence of hydrogen, by at least one refining process and at least one cracking process
    • C10G55/02Treatment of hydrocarbon oils, in the absence of hydrogen, by at least one refining process and at least one cracking process plural serial stages only
    • C10G55/06Treatment of hydrocarbon oils, in the absence of hydrogen, by at least one refining process and at least one cracking process plural serial stages only including at least one catalytic cracking step
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G1/00Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
    • C10G1/002Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal in combination with oil conversion- or refining processes
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G1/00Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
    • C10G1/04Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal by extraction
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G11/00Catalytic cracking, in the absence of hydrogen, of hydrocarbon oils
    • C10G11/02Catalytic cracking, in the absence of hydrogen, of hydrocarbon oils characterised by the catalyst used
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10Feedstock materials
    • C10G2300/1077Vacuum residues
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20Characteristics of the feedstock or the products
    • C10G2300/201Impurities
    • C10G2300/202Heteroatoms content, i.e. S, N, O, P
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20Characteristics of the feedstock or the products
    • C10G2300/30Physical properties of feedstocks or products
    • C10G2300/302Viscosity

Abstract

Processes for upgrading a bitumen feedstock in presence of an ionic liquid are described, and can improve bitumen properties such as viscosity and composition, and reduced contaminant content, such as a reduced Total Acid Number (TAN) and a reduced heavy metal content. Processes for upgrading bitumen in presence of an ionic liquid can include a catalytic cracking treatment carried out under catalytic cracking conditions, and/or a non-catalytic treatment, as well as various separation steps to separate the ionic liquid or a diluent if present in the bitumen feedstock.
The ionic liquids that can be used in the context of the processes described herein include ionic liquids that are feed-miscible or feed-immiscible.

Description

IONIC LIQUIDS FOR UPGRADING OF BITUMEN
TECHNICAL FIELD
[1] The technical field generally relates to the treatment of bitumen, and more particularly to the upgrading of bitumen using ionic liquids.
BACKGROUND
[2] Bitumen generally has a high viscosity, irrespective of whether it has been recovered by mining operations or by in situ recovery processes. This high viscosity can make the pipeline transportation of bitumen difficult. Various methods exist to decrease bitumen viscosity and increase suitability for pipeline transportation, although such methods have various drawbacks. Bitumen generally also include undesirable components, such as sulphur, naphthenic acids and heavy metals.
[3] Bitumen upgrader facilities of various designs can upgrade the bitumen to produce less viscous products and to remove undesirable components. However, conventional upgrader facilities have high associated capital and operating costs. In addition, in some conventional upgrading methods such as severe thermal cracking, hydrogen originally present in the bitumen is lost to the gas phase such that, in the absence of added hydrogen, significant yet undesirable olefin production can occur.
[4] Another option to improve bitumen viscosity is to dilute the bitumen, for example with naphtha or natural gas condensate as a diluent. Diluted bitumen is often referred to as "dilbit". While bitumen dilution does not have the same capital cost penalty as a bitumen upgrader facility, it still has high associated operating costs.
For example, since dilbit includes a significant volume of diluent (e.g., one third diluent and two thirds bitumen per barrel of diluted bitumen), significant pipeline capacity is therefore taken up by the diluent for pipelining of the dilbit as well as the return pipelining of separated diluent to be reused in bitumen dilution.
[5] Various challenges still exist with regard to bitumen upgrading processes and there is a need for enhanced technologies.

SUMMARY
[6] In accordance with an aspect, there is provided a process for treating a bitumen feedstock. The process comprises contacting an acidic ionic liquid catalyst with the bitumen feedstock to obtain an ionic liquid-bitumen mixture; subjecting the ionic liquid-bitumen mixture to a catalytic cracking treatment, the catalytic cracking treatment comprising heating the ionic liquid-bitumen mixture under catalytic cracking conditions to obtain an ionic liquid-cracked bitumen mixture; and separating the acidic ionic liquid catalyst from the ionic liquid-cracked bitumen mixture to obtain a cracked bitumen product and a recovered acidic ionic liquid catalyst.
[7] In some implementations, the bitumen feedstock comprises a diluent-depleted bitumen stream from a distillation unit, a diluent stripping unit or a diluent recovery unit.
[8] In some implementations, the bitumen feedstock comprises a diluent-depleted bitumen stream that is obtained from a bitumen froth treatment operation.
[9] In some implementations, the bitumen feedstock comprises a diluent-depleted bitumen stream that has not been subjected to fractionation or distillation prior to being contacted with the acidic ionic liquid catalyst.
[10] In some implementations, the bitumen feedstock comprises a residuum stream from a distillation tower that has been operated to remove light hydrocarbon components.
[11] In some implementations, the bitumen feedstock comprises a bitumen stream that is obtained from an in situ recovery operation or from surface mining operations.
[12] In some implementations, the process further comprises subjecting the bitumen feedstock to a pre-treatment prior to the contacting of the bitumen feedstock with the acidic ionic liquid catalyst.
[13] In some implementations, the pre-treatment comprises heating the bitumen feedstock at a pre-treatment temperature.

, ,
[14] In some implementations, the pre-treatment temperature is sufficient to reduce viscosity of the bitumen feedstock.
[15] In some implementations, the pre-treatment comprises adding a diluent to the bitumen feedstock.
[16] In some implementations, the diluent comprises at least one of a naphthenic solvent, an aromatic hydrocarbon, and a non-deasphalting organic solvent.
[17] In some implementations, the diluent comprises toluene.
[18] In some implementations, the bitumen feedstock comprises bitumen and a diluent.
[19] In some implementations, the process further comprises recovering the diluent to obtain a recovered diluent.
[20] In some implementations, recovering the diluent is performed after the catalytic cracking treatment of the ionic liquid-bitumen mixture under catalytic cracking conditions and before separating the acidic ionic liquid catalyst from the ionic liquid-cracked bitumen mixture.
[21] In some implementations, recovering the diluent is performed after separating the acidic ionic liquid catalyst from the ionic liquid-cracked bitumen mixture.
[22] In some implementations, recovering the diluent comprises evaporating the diluent from the ionic liquid-cracked bitumen mixture or the cracked bitumen product.
[23] In some implementations, the process further comprises contacting at least a portion of the recovered diluent with the bitumen feedstock.
[24] In some implementations, the recovered acidic ionic liquid catalyst is reused as part of the acidic ionic liquid catalyst that contacts the bitumen feedstock.
[25] In some implementations, separating the acidic ionic liquid catalyst from the ionic liquid-cracked bitumen mixture comprises a liquid-liquid extraction of the ionic liquid-cracked bitumen mixture.
[26] In some implementations, the liquid-liquid extraction of the ionic liquid-cracked bitumen mixture comprises washing the ionic liquid-cracked bitumen mixture with water.
[27] In some implementations, the acidic ionic liquid catalyst is a Lewis acidic ionic liquid catalyst comprising a Lewis acidic anion and a cation selected from the group consisting of 1,3-dialkylimidazolium cations, tetraalkylphosphonium cations, tetraalkylammonium cations, trialkylammonium cations and combinations thereof.
[28] In some implementations, the Lewis acidic ionic liquid catalyst comprises a Lewis acidic anion and a 1-alkyl-3-methylimidazolium cation.
[29] In some implementations, the 1-alkyl-3-methylimidazolium cation is selected from the group consisting of 1-ethyl-3-methylimidazolium (EMIM) and 1-n-buty1-3-methylimidazolium (BMIM).
[30] In some implementations, the Lewis acidic ionic liquid catalyst comprises a Lewis acidic anion and a trialkylammonium cation.
[31] In some implementations, the trialkylammonium cation comprises triethylammonium.
[32] In some implementations, the Lewis acidic anion is a chlorometallate anion.
[33] In some implementations, the chlorometallate anion is selected from the group consisting of AlC14-, Al2C17-, FeCI4- and Fe2C17-.
[34] In some implementations, the Lewis acidic ionic liquid is selected from the group consisting of [EMIM][AICI4], [BMIM][AICI4], [EMIK[FeC14], [BM1M][FeC14].
[35] In some implementations, the Lewis acidic ionic liquid is [EMIM][AICI4].
[36] In some implementations, the Lewis acidic ionic liquid comprises a metal ion-modified ionic liquid.
[37] In some implementations, the metal ion-modified ionic liquid is selected from the group consisting of [Et3NH][AIC14]-Ni2+, [EMIM][AIC14]-Ni2+, [BM IM1[AICI4]-Ni2+, [Et3NH][AIC141-Fe2+, [EMIM][AICI4]-Fe2+, [BM IMHAICI4j-Fe2+ and combinations thereof.

,
[38] In some implementations, the acidic ionic liquid catalyst is a Bronsted acidic ionic liquid catalyst.
[39] In some implementations, the heating is performed at a temperature between about 50 C and about 250 C.
[40] In some implementations, the concentration of the acidic ionic liquid catalyst in the ionic liquid-bitumen mixture is between about 5 wt% and about 50 wt%.
[41] In accordance with another aspect, there is provided a process for upgrading a bitumen feedstock. The process comprises contacting the bitumen feedstock with a feed-miscible ionic liquid to obtain an ionic liquid-bitumen mixture; and subjecting the ionic liquid-bitumen mixture to a non-catalytic treatment, the non-catalytic treatment comprising mixing the ionic liquid-bitumen mixture at a mixing temperature below an asphaltene aggregation temperature of the ionic liquid-bitumen mixture to obtain a treated ionic liquid-bitumen mixture; wherein at least one of a Total Acid Number (TAN) of the treated ionic liquid-bitumen mixture, a viscosity of the treated ionic liquid-bitumen mixture and an asphaltene content of the treated ionic liquid-bitumen mixture is reduced compared to the bitumen feedstock.
[42] In some implementations, the bitumen feedstock comprises diluent-depleted bitumen stream from a distillation unit, a diluent stripping unit or a diluent recovery unit.
[43] In some implementations, the bitumen feedstock comprises a diluent-depleted bitumen stream that is obtained from a bitumen froth treatment operation.
[44] In some implementations, the bitumen feedstock comprises a diluent-depleted bitumen stream that has not been subjected to fractionation or distillation prior to being contacted with the feed-miscible ionic liquid.
[45] In some implementations, the bitumen feedstock comprises a residuum stream from a distillation tower that has been operated to remove light hydrocarbon components.
[46] In some implementations, the bitumen feedstock comprises a bitumen stream that is obtained from an in situ recovery operation or from surface mining operations.
[47] In some implementations, the process further comprises subjecting the bitumen feedstock to a pre-treatment prior to the contacting of the bitumen feedstock with the feed-miscible ionic liquid.
[48] In some implementations, the pre-treatment comprises heating the bitumen feedstock at a pre-treatment temperature.
[49] In some implementations, the pre-treatment temperature is sufficient to reduce viscosity of the bitumen feedstock.
[50] In some implementations, the pre-treatment comprises adding a diluent to the bitumen feedstock.
[51] In some implementations, the diluent comprises at least one of a naphthenic solvent, an aromatic hydrocarbon, and a non-deasphalting organic solvent.
[52] In some implementations, the diluent comprises toluene.
[53] In some implementations, the bitumen feedstock comprises bitumen and a diluent.
[54] In some implementations, the process further comprises recovering the diluent to obtain a recovered diluent.
[55] In some implementations, the process further comprises separating the feed-miscible ionic liquid from the treated ionic liquid-bitumen mixture to obtain a recovered feed-miscible ionic liquid and a treated bitumen product.
[56] In some implementations, recovering the diluent is performed after the non-catalytic treatment of the ionic liquid-bitumen mixture and before separating the feed-miscible ionic liquid from the treated ionic liquid-bitumen mixture.
[57] In some implementations, recovering the diluent is performed after separating the feed-miscible ionic liquid from the treated ionic liquid-bitumen mixture.
[58] In some implementations, recovering the diluent comprises evaporating the diluent from the treated ionic liquid-bitumen mixture or from the treated bitumen product.

, 7
[59] In some implementations, the process further comprises contacting at least a portion of the recovered diluent with the bitumen feedstock.
[60] In some implementations, the recovered feed-miscible ionic liquid is reused as part of the feed-miscible ionic liquid that contacts the bitumen feedstock.
[61] In some implementations, the feed-miscible ionic liquid comprises a carbamate ionic liquid, a phosphonium ionic liquid, and combinations thereof.
[62] In some implementations, the carbamate ionic liquid comprises N, N'-dipropylammonium, N, N'-dipropyl carbamate (DPCARB) or N, N'-dibenzylammonium, N, N'-dibenzyl carbamate (DBCARB), and combinations thereof.
[63] In some implementations, the phosphonium ionic liquid comprises trihexyl-tetradecylphosphonium dicyanamide.
[64] In some implementations, the non-catalytic treatment further comprises heating the ionic liquid-bitumen mixture at a heating temperature below the mixing temperature.
[65] In some implementations, the heating temperature is between about 20 C
and about 120 C.
[66] In some implementations, the heating is performed near atmospheric pressure.
[67] In some implementations, the concentration of the feed-miscible ionic liquid in the ionic liquid-bitumen mixture is between about 5 wt% and about 50 wt%.
[68] In accordance with another aspect, there is provided a process for upgrading a bitumen feedstock comprising bitumen and a diluent. The process comprises contacting the bitumen feedstock with a feed-immiscible ionic liquid to obtain an ionic liquid-bitumen mixture; and subjecting the ionic liquid-bitumen mixture to a non-catalytic treatment, the non-catalytic treatment comprising mixing the ionic liquid-bitumen mixture to obtain a treated ionic liquid-bitumen mixture; wherein at least one of a Total Acid Number (TAN) of the treated ionic liquid-bitumen mixture and a heavy metal content of the treated ionic liquid-bitumen mixture is reduced compared to the bitumen feedstock.

, ,
[69] In some implementations, the bitumen feedstock comprises a residuum stream from a distillation tower that has been operated to remove light hydrocarbon components.
[70] In some implementations, the bitumen feedstock comprises a bitumen stream that is obtained from an in situ recovery operation or from surface mining operations.
[71] In some implementations, the diluent is selected from the group consisting of a naphthenic diluent, toluene and a mixture thereof.
[72] In some implementations, the process further comprises subjecting the treated ionic liquid-bitumen mixture to a liquid-liquid separation to obtain a first phase comprising the bitumen and the diluent and a second phase comprising a recovered feed-immiscible ionic liquid.
[73] In some implementations, the process further comprises separating the first phase to recover the diluent as a recovered diluent, and to obtain a treated bitumen product.
[74] In some implementations, recovering the diluent comprises evaporating the diluent to obtain the treated bitumen product.
[75] In some implementations, the process further comprises contacting at least a portion of the recovered diluent with the bitumen feedstock.
[76] In some implementations, the recovered feed-immiscible ionic liquid is reused as part of the feed-immiscible ionic liquid that contacts the bitumen feedstock.
[77] In some implementations, the feed-immiscible ionic liquid comprises an amino acid based ionic liquid, an imidazolium ionic liquid, a phosphonium ionic liquid, a carbamate ionic liquid, and combinations thereof.
[78] In some implementations, the amino acid ionic liquid comprises tetraethylammonium P-alaninate, 1-ethyl-3-methylimidazolium glycinate, and combinations thereof.

, ,
[79] In some implementations, the imidazolium ionic liquid comprises 1-ethy1-3-methylimidazolium ethyl sulphate, 1-butyl-3-methylimidazolium tetrafluoroborate, 1-ethyl-3-methylimidazolium tetrafluoroborate, and combinations thereof.
[80] In some implementations, the phosphonium ionic liquid comprises tributyl-methylphosphonium methyl sulphate.
[81] In some implementations, the carbamate ionic liquid comprises N, N'-dimethylammonium, N, N'-dimethylcarbamate (DMCARB).
[82] In some implementations, the non-catalytic treatment further comprises heating the ionic liquid-bitumen mixture at a heating temperature.
[83] In some implementations, the heating temperature is between about 40 C
and about 70 C.
[84] In some implementations, the concentration of the feed-immiscible ionic liquid in the ionic liquid-bitumen mixture is between about 5 wt% and about 50 wt%.
[85] In some implementations, the proportion of the bitumen relative to the feed-immiscible ionic liquid is between about 1:2 w/w and about 1:1 w/w.
[86] In some implementations, the heavy metal content comprises at least one of a nickel content, an iron content and a vanadium content.
[87] In accordance with another aspect, there is provided a process for upgrading a bitumen feedstock comprising bitumen and a diluent. The process comprises contacting the bitumen feedstock with an ionic liquid to obtain an ionic liquid-bitumen mixture;
mixing the ionic liquid-bitumen mixture at a mixing temperature; and separating the ionic liquid-bitumen mixture to obtain a first phase comprising treated bitumen and the diluent from a second phase comprising a recovered ionic liquid; wherein the treated bitumen has a reduced heavy metal content compared to the bitumen feedstock.
[88] In some implementations, the bitumen feedstock comprises a residuum stream from a distillation tower that has been operated to remove light hydrocarbon components.

, 10
[89] In some implementations, the bitumen feedstock comprises a bitumen stream that is obtained from an in situ recovery operation or from surface mining operations.
[90] In some implementations, the diluent is selected from the group consisting of a naphthenic diluent, toluene and a mixture thereof.
[91] In some implementations, the ionic liquid is a feed-immiscible ionic liquid, and wherein the first phase and the second phase are obtained by subjecting the ionic liquid-bitumen mixture to a liquid-liquid separation.
[92] In some implementations, the process further comprises separating the first phase to recover the diluent as a recovered diluent, and to obtain a treated bitumen product.
[93] In some implementations, recovering the diluent comprises evaporating the diluent to obtain the treated bitumen product.
[94] In some implementations, the process further comprises contacting at least a portion of the recovered diluent with the bitumen feedstock.
[95] In some implementations, the recovered ionic liquid is reused as part of the ionic liquid that contacts the bitumen feedstock.
[96] In some implementations, the ionic liquid comprises an amino acid based ionic liquid, an imidazolium ionic liquid, a phosphonium ionic liquid, a carbamate ionic liquid, and combinations thereof.
[97] In some implementations, the amino acid ionic liquid comprises tetraethylammonium 13-alaninate, 1-ethy1-3-methylimidazolium glycinate, and combinations thereof.
[98] In some implementations, the imidazolium ionic liquid comprises 1-ethy1-3-methylimidazolium ethyl sulphate, 1-butyl-3-methylimidazolium tetrafluoroborate, 1-ethyl-3-methylimidazolium tetrafluoroborate, and combinations thereof.
[99] In some implementations, the phosphonium ionic liquid comprises tributyl-methylphosphonium methyl sulphate.
[100] In some implementations, the carbamate ionic liquid comprises N, N'-dimethylammonium, N, N'-dimethylcarbamate (DMCARB).
[101] In some implementations, the process further comprises heating the ionic liquid-bitumen mixture at a heating temperature.
[102] In some implementations, the heating temperature is between about 40 C
and about 70 C.
[103] In some implementations, the concentration of the ionic liquid in the ionic liquid-bitumen mixture is between about 5 wt% and about 50 wt%.
[104] In some implementations, the proportion of the bitumen relative to the ionic liquid is between about 1:2 w/w and about 1:1 w/w.
[105] In some implementations, the heavy metal content comprises at least one of a nickel content, an iron content, and a vanadium content.
[106] In accordance with another aspect, there is provided a process for upgrading a bitumen feedstock comprising bitumen and a diluent. The process comprises contacting the bitumen feedstock with an amino acid ionic liquid to obtain an ionic liquid-bitumen mixture; mixing the ionic liquid-bitumen mixture at a mixing temperature; and separating the ionic liquid-bitumen mixture to obtain a first phase comprising treated bitumen and the diluent from a second phase comprising a recovered amino acid ionic liquid; wherein the Total Acid Number (TAN) of the treated bitumen is reduced compared to the TAN of the bitumen feedstock.
[107] In some implementations, the bitumen feedstock comprises a residuum stream from a distillation tower that has been operated to remove light hydrocarbon components.
[108] In some implementations, the bitumen feedstock comprises a bitumen stream that is obtained from an in situ recovery operation or from surface mining operations.
[109] In some implementations, the diluent is selected from the group consisting of a naphthenic diluent, toluene and a mixture thereof.
[110] In some implementations, the first phase and the second phase are obtained by subjecting the ionic liquid-bitumen mixture to a liquid-liquid separation.
[111] In some implementations, the process further comprises separating the first phase to recover the diluent as a recovered diluent, and to obtain a treated bitumen product.
[112] In some implementations, recovering the diluent comprises evaporating the diluent to obtain the treated bitumen product.
[113] In some implementations, the process further comprises contacting at least a portion of the recovered diluent with the bitumen feedstock.
[114] In some implementations, the recovered amino acid ionic liquid is reused as part of the amino acid ionic liquid that contacts the bitumen feedstock.
[115] In some implementations, the amino acid ionic liquid comprises tetraethylammonium 13-alaninate, 1-ethyl-3-methylimidazolium glycinate, and combinations thereof.
[116] In some implementations, the process further comprises heating the ionic liquid-bitumen mixture at a heating temperature.
[117] In some implementations, the heating temperature is between about 40 C
and about 70 C.
[118] In some implementations, the concentration of the amino acid ionic liquid in the ionic liquid-bitumen mixture is between about 5 wt% and about 50 wt%.
[119] In some implementations, the proportion of the bitumen relative to the amino acid ionic liquid is between about 1:2 w/w and about 1:1 w/w.
[120] In accordance with another aspect, there is provided a process for upgrading a bitumen feedstock. The process comprises contacting a first ionic liquid catalyst with the bitumen feedstock to obtain a first ionic liquid-bitumen mixture; subjecting the first ionic liquid-bitumen mixture to a catalytic cracking treatment, the catalytic cracking treatment comprising heating the first ionic liquid-bitumen mixture under catalytic cracking , , conditions to obtain an ionic liquid-cracked bitumen mixture; contacting the ionic liquid-cracked bitumen mixture with a second ionic liquid to obtain a second ionic liquid-bitumen mixture; and subjecting the second ionic liquid-bitumen mixture to a non-catalytic treatment, the non-catalytic treatment comprising mixing the second ionic liquid-bitumen mixture to obtain a treated ionic liquid-bitumen mixture.
[121] In some implementations, the process further comprises separating the first ionic liquid catalyst from the ionic liquid-cracked bitumen mixture to obtain a recovered first ionic liquid catalyst.
[122] In some implementations, the recovered first ionic liquid is reused as part of the first ionic liquid that contacts the bitumen feedstock.
[123] In some implementations, the process further comprises separating the second ionic liquid from the treated ionic liquid-bitumen mixture to obtain a recovered second ionic liquid.
[124] In some implementations, the recovered second ionic liquid is reused as part of the second ionic liquid that contacts the ionic liquid-cracked bitumen mixture.
[125] In some implementations, the process further comprises adding a diluent to the bitumen feedstock or to the second ionic liquid-bitumen mixture.
[126] In some implementations, the process further comprises subjecting the bitumen feedstock to a pre-treatment prior to the contacting of the bitumen feedstock with the first ionic liquid catalyst.
[127] In some implementations, the pre-treatment comprises heating the bitumen feedstock at a pre-treatment temperature.
[128] In some implementations, the pre-treatment temperature is sufficient to reduce viscosity of the bitumen feedstock.
[129] In some implementations, the pre-treatment comprises adding a diluent to the bitumen feedstock.

,
[130] In some implementations, the diluent comprises at least one of a naphthenic solvent, an aromatic hydrocarbon, and a non-deasphalting organic solvent.
[131] In some implementations, the diluent comprises toluene.
[132] In some implementations, the bitumen feedstock comprises bitumen and a diluent.
[133] In some implementations, the process further comprises recovering the diluent following the non-catalytic treatment to obtain a recovered diluent.
[134] In some implementations, the process further comprises contacting at least a portion of the recovered diluent with the bitumen feedstock or the second ionic liquid-bitumen mixture.
[135] In some implementations, the first ionic liquid catalyst comprises an acidic ionic liquid catalyst.
[136] In some implementations, the acidic ionic liquid catalyst is a Lewis acidic ionic liquid comprising a Lewis acidic anion and a cation selected from the group consisting of 1,3-dialkylimidazolium cations, tetraalkylphosphonium cations, tetraalkylammonium cations, trialkylammonium cations and combinations thereof.
[137] In some implementations, the Lewis acidic ionic liquid catalyst comprises a Lewis acidic anion and a 1-alkyl-3-methylimidazolium cation.
[138] In some implementations, the 1-alkyl-3-methylimidazolium cation is selected from the group consisting of 1-ethyl-3-methylimidazolium (EMIM) and 1-n-buty1-3-methylimidazolium (BMIM).
[139] In some implementations, the Lewis acidic ionic liquid catalyst comprises a Lewis acidic anion and a trialkylammonium cation.
[140] In some implementations, the trialkylammonium cation comprises triethylam mon ium.
[141] In some implementations, the Lewis acidic anion is a chlorometallate anion.

, ,
[142] In some implementations, the chlorometallate anion is selected from the group consisting of AlC14-, Al2C17-, FeCI4- and Fe2C17-.
[143] In some implementations, the Lewis acidic ionic liquid is selected from the group consisting of [EMIMMIC14], [BMIM][AICI4], [EMINI][FeC14], [BMIK[FeCI4].
[144] In some implementations, the Lewis acidic ionic liquid is [EMIM][AIC14].
[145] In some implementations, the Lewis acidic ionic liquid comprises a metal ion-modified ionic liquid.
[146] In some implementations, the metal ion-modified ionic liquid is selected from the group consisting of [Et3NH][AICI4]-Ni2+, [EMIM][AIC14]-Ni2+, [BMIM][AICI4J-Ni2+, [Et3NFI][AlC14]-Fe2+, [EMIM][AICI4]-Fe2+, [BMIM][AIC14-Fe2+ and combinations thereof.
[147] In some implementations, the second ionic liquid is a feed-miscible ionic liquid.
[148] In some implementations, the feed-miscible ionic liquid comprises a carbamate ionic liquid, a phosphonium ionic liquid, and combinations thereof.
[149] In some implementations, the carbamate ionic liquid comprises N, N'-dipropylammonium, N, N'-dipropyl carbamate (DPCARB) or N, N'-dibenzylammonium, N, N'-dibenzyl carbamate (DBCARB), and combinations thereof.
[150] In some implementations, the phosphonium ionic liquid comprises trihexyl-tetradecylphosphonium dicyanamide.
[151] In some implementations, the second ionic liquid is a feed-immiscible ionic liquid.
[152] In some implementations, the feed-immiscible ionic liquid comprises an amino acid based ionic liquid, an imidazolium ionic liquid, a phosphonium ionic liquid, a carbamate ionic liquid, and combinations thereof.
[153] In some implementations, the amino acid ionic liquid comprises tetraethylammonium 13-alaninate, 1-ethyl-3-methylimidazolium glycinate, and combinations thereof.

, ,
[154] In some implementations, the imidazolium ionic liquid comprises 1-ethy1-methylimidazolium ethyl sulphate, 1-butyl-3-methylimidazolium tetrafluoroborate, 1-ethyl-3-methylimidazolium tetrafluoroborate, and corn binations thereof.
[155] In some implementations, the phosphonium ionic liquid comprises tributyl-methylphosphonium methyl sulphate.
[156] In some implementations, the carbamate ionic liquid comprises N, N'-dimethylammonium, N, N'-dimethylcarbamate (DMCARB).
[157] In some implementations, at least one of a Total Acid Number (TAN), a viscosity, a heavy metal content, and an asphaltene content of the treated ionic liquid-bitumen mixture is reduced compared to the bitumen feedstock.
[158] In some implementations, the heavy metal content comprises at least one of a nickel content, an iron content, and a vanadium content.
BRIEF DESCRIPTION OF THE DRAWINGS
[159] Figure 1 is a flowchart of a general flow diagram for treating a bitumen feedstock including a catalytic cracking treatment followed by an ionic liquid separation, wherein various bitumen recovery processes are shown.
[160] Figure 2 is a flowchart of a general flow diagram for treating a bitumen feedstock including a non-catalytic treatment followed by an ionic liquid separation, wherein various bitumen recovery processes are shown.
[161] Figure 3 is a flowchart of a process for treating a bitumen feedstock, including a catalytic cracking treatment, in accordance with an implementation.
[162] Figure 4 is a flowchart of a process for treating a bitumen feedstock, including a blending/mixing step, a catalytic cracking treatment, and a separation step to separate a diluent and an ionic liquid from an ionic liquid-cracked bitumen mixture, in accordance with an implementation.

, ,
[163] Figure 5 is a flowchart of a process for treating a bitumen feedstock, including a blending/mixing step, a catalytic cracking treatment, and a separation step to separate a diluent and an ionic liquid from an ionic liquid-cracked bitumen mixture, in accordance with another implementation.
[164] Figure 6 is a flowchart of a process for treating a bitumen feedstock, including a blending/mixing step, a catalytic cracking treatment, and a separation step to separate a diluent and an ionic liquid from an ionic liquid-cracked bitumen mixture, in accordance with yet another implementation.
[165] Figure 7 is a flowchart of a process for treating a bitumen feedstock, including a catalytic cracking treatment, and a separation step to separate a diluent and an ionic liquid from an ionic liquid-cracked bitumen mixture, in accordance with an implementation.
[166] Figure 8 is a flowchart of a process for treating a bitumen feedstock, including a non-catalytic treatment, and a separation step to separate an ionic liquid from a treated ionic liquid-bitumen mixture, in accordance with an implementation.
[167] Figure 9 is a flowchart of a process for treating a bitumen feedstock, including a non-catalytic treatment, and a separation step to separate a diluent and an ionic liquid from a treated ionic liquid-bitumen mixture, in accordance with an implementation.
[168] Figure 10 is a flowchart of a process for treating a bitumen feedstock, including a catalytic treatment followed by a non-catalytic treatment, in accordance with an implementation.
DETAILED DESCRIPTION
[169] Techniques described herein relate to the treatment of a bitumen feedstock, and can also be referred to as "upgrading" or "partial upgrading". The upgrading, or partial upgrading, of the bitumen feedstock can include subjecting the bitumen feedstock to a catalytic cracking treatment in the presence of an ionic liquid or subjecting the bitumen feedstock to a non-catalytic treatment in the presence of an ionic liquid at a given temperature, each performed as a standalone step. The upgrading, or partial upgrading, of the bitumen feedstock can also include a combination of the catalytic cracking treatment in presence of a first ionic liquid and the non-catalytic treatment in presence of a second ionic liquid performed according to a given sequence. The upgrading techniques described herein can facilitate viscosity and/or density reduction of the bitumen feedstock, and improve its chemical composition for instance by reducing asphaltene content and/or removing impurities such as sulphur and heavy metals. The viscosity and/or density reduction can, in turn, help reduce or eliminate diluent requirements for the bitumen product to be pipelinable. The upgrading techniques can also facilitate avoiding the need for the addition of an external source of hydrogen (i.e., hydroprocessing steps) in order to produce a higher quality bitumen product, the higher quality bitumen product having for instance a reduced sulphur content, a reduced metal content, a reduced total acid number, and/or a reduced viscosity compared to an untreated bitumen feedstock. It should be understood that as used herein, the expression "a method/process/system for upgrading a bitumen feedstock" may refer to an upgrading of the bitumen feedstock (e.g., a treatment of the bitumen feedstock that makes the bitumen feedstock pipelinable) or to a partial upgrading of the bitumen feedstock (e.g., a treatment of the bitumen feedstock that takes the bitumen feedstock closer to being pipelinable). In some implementations, the bitumen feedstock can be subjected to a pre-treatment step prior to the addition of the ionic liquid for the subsequent catalytic cracking treatment or non-catalytic treatment. For instance, the pre-treatment can include the addition of a diluent and/or a heating step. The pre-treatment can contribute to achieve desired properties of the bitumen feedstock, for instance with regard to its viscosity, to facilitate the subsequent interaction with the ionic liquid.
Bitumen feedstock and viscosity characteristics and overview of general process
[170]
As mentioned above, techniques are described herein to facilitate the reduction in viscosity of bitumen feedstocks and/or improve its chemical composition of the bitumen feedstocks. The term "bitumen" as used herein refers to hydrocarbon material extracted from bituminous formations, such as oil sands formations, the density of which is typically around 1000 kg/m3, and the viscosity of which is typically between about 1 million cP to about 100 million cP when measured at 20 C. The bitumen feedstock can include bitumen that was extracted from oil sands ore using a surface mining process, or using an in situ recovery process (e.g., a thermal energy-based recovery method such as steam assisted gravity drainage (SAGD) or cyclic steam stimulation (CSS), a solvent-based recovery method such as in situ solvent or solvent-steam extraction, an in situ combustion recovery method, a cold production process, an electromagnetic energy assisted process, or a concurrent or sequential combination thereof). The bitumen included in the bitumen feedstock can also come from any other suitable source, such as bitumen obtained from a non-aqueous extraction process or bitumen obtained from a paraffinic froth treatment.
[171] The bitumen feedstock refers to the bitumen material that is subjected to the upgrading techniques in presence of an ionic liquid. In some implementations, the bitumen feedstock includes both heavy and light hydrocarbon fractions and has very low or substantially zero water content and mineral solids content (e.g., below 2.5% water, or below 0.5% water and below 1.0% solids). The bitumen feedstock can include various non-hydrocarbon compounds (e.g., sulfur, heavy metals, etc.) that are often found in bitumen and may be associated with certain fractions or solubility classes of bitumen, such as asphaltenes.
[172] It should also be noted that the bitumen feedstock can in some cases be a blend of different hydrocarbon streams, e.g., one or more heavy hydrocarbon streams can be blended with one or more light hydrocarbon streams to form a blended bitumen feedstock that has desired properties to be subjected to upgrading techniques in the presence of an ionic liquid as described herein.
[173] Referring to Figures 1 and 2, the bitumen feedstock can include bitumen extracted using surface mining operations. In such operations, the oil sands ore 34 is extracted through mining, followed by breaking down and crushing of the ore 36, which produces a looser material that can be mixed with warm or hot water to obtain a slurry preparation suitable for hydrotransport 38. At this stage, the slurry can also be subjected to various forms of conditioning to improve its properties. The hydrotransport 38 provides a pipeline connection between mining operations 36 and primary extraction operations 40. The primary extraction 40 is performed to separate the hydrotransported slurry into bitumen froth 42 and tailings 44. The bitumen froth 42 is then subjected to secondary extraction 46, or froth treatment, to separate the bitumen 32 from froth treatment tailings , 20 48 using a solvent or diluent 50, thereby producing a bitumen feedstock 70.
Optionally, the bitumen feedstock 32 can be further processed in a diluent recovery unit that has received the diluted bitumen feedstock from the secondary extraction 46 to recover the solvent or diluent 50. The bitumen feedstock 70 can thus also be a diluent-depleted bitumen produced by a diluent recovery unit that recovers paraffinic solvent from a solvent diluted bitumen overflow stream that is part of a paraffinic froth treatment operation.
[174] Still referring to Figuresl and 2, the bitumen feedstock can also include bitumen 52 extracted using in situ recovery operations. In situ recovery operations comprise injecting a pre-heated mobilizing fluid 54 via an injection well 56 overlying a production well 58. A produced fluid 60 is extracted from the production well 58 and subjected to at-surface processing 62 to separate a stream of recycled mobilizing fluid 64 from a bitumen feedstock 70 suitable for the upgrading techniques described herein.
In implementations where the mobilizing fluid 64 comprises a solvent or a diluent, the bitumen feedstock 70 can optionally be further processed in a diluent recovery unit that has received the bitumen feedstock from an in situ recovery facility to recover the solvent or diluent.
[175] It is to be understood that as used herein, the expression "bitumen feedstock"
can thus refer to either one of a diluted bitumen feedstock, i.e., a bitumen feedstock that still includes a solvent or a diluent, or to a bitumen feedstock from which solvent or diluent has been removed therefrom, in both cases when the bitumen feedstock has been obtained from surface mining operations or when the bitumen feedstock is obtained from in situ recovery operations.
[176] In some implementations, the bitumen feedstock is a diluent-depleted bitumen stream that has not been subjected to certain conventional separation steps, such as fractionation or distillation, prior to the upgrading, and therefore still has many if not substantially all of the heavy and light hydrocarbon components of the native bitumen. In other implementations, the bitumen feedstock can be a residuum stream from a distillation tower (e.g., vacuum distillation tower) that has been operated to remove light hydrocarbon components (e.g., gas oils and other hydrocarbons that boil below about 525 C).
[177] In some implementations, the bitumen feedstock subjected to upgrading in the presence of an ionic liquid can include bitumen extracted from various sources, and can be combined in a blending step 66 prior to being subjected to the upgrading. A

hydrocarbon co-feed 68 can also be added to the blending step 66.
[178] Referring to Figure 1, an ionic liquid is then added 72 to the bitumen feedstock 70 to obtain an ionic liquid-bitumen mixture 74, which is then subjected to a catalytic cracking treatment 76 under conditions to produce an ionic liquid-cracked bitumen mixture 78. Further details regarding the expression "catalytic cracking treatment" as used herein and the conditions at which the catalytic cracking treatment is performed are provided below. The ionic liquid-cracked bitumen mixture 78 can optionally be separated 80 to recover at least a portion of the ionic liquid as a recovered ionic liquid 96. A
cracked bitumen product 82 is then obtained. In some implementations, the cracked bitumen product 82 can be a partially upgraded product that can be subjected to further upgrading treatment(s) if deemed necessary. In other implementations, the cracked bitumen product 82 can be sufficiently upgraded such that pipeline specifications are met, or further processed if needed.
[179] Referring to Figure 2, an ionic liquid is added 72 to the bitumen feedstock 70 to obtain an ionic liquid-bitumen mixture 74, which is then subjected to a non-catalytic treatment 84 to produce a treated ionic liquid-bitumen mixture 86. The treated ionic liquid-bitumen mixture 86 can optionally be separated 88 to recover at least a portion of the ionic liquid as a recovered ionic liquid. A bitumen product 90 is then obtained.
Similarly to what is mentioned above regarding the cracked bitumen product 82, the bitumen product 90 can be a partially upgraded product that can be subjected to further upgrading treatment(s) if deemed necessary, or the bitumen product 90 can be sufficiently upgraded such that pipeline specifications are met, for instance.
[180] In some implementations, the bitumen feedstock 70 can be subjected to a pre-treatment prior to the addition of the ionic liquid to the bitumen feedstock 70 for the subsequent catalytic cracking treatment 76 or non-catalytic treatment 84. The pre-treatment can include various steps depending on the results that are desired to be achieved, and depending on the characteristics of the bitumen feedstock 70.
The pre-treatment can include adding a diluent, or additive agent, to the bitumen feedstock. The = , addition of the diluent to the bitumen feedstock 70 can contribute to dilute the bitumen feedstock 70 and reduce its viscosity. In some scenarios, the reduced viscosity of the bitumen feedstock 70 can facilitate the blending of the mixture of bitumen feedstock/diluent with the ionic liquid. Examples of suitable diluents can include for instance aromatic hydrocarbons, non-deasphalting organic solvents, and the like. In some scenarios, the diluent can be for instance toluene or xylene.
Furthermore, in some implementations, the pre-treatment can include a heating step, whether or not a diluent has been added to the bitumen feedstock 70 during the pre-treatment step, and if a diluent has been added, prior to or after the addition of the diluent. The heating step can be performed prior to or during the addition of the ionic liquid to the bitumen feedstock 70. In some implementations, the heating step can be performed at a temperature sufficient to decrease the viscosity of the bitumen feedstock 70, which can facilitate the subsequent blending of the bitumen feedstock 70 with the ionic liquid. In some implementations and as will be discussed in further detail below, the addition of the diluent, or additive agent, can also be performed simultaneously with the addition of the ionic liquid, in a blending/mixing step. It is to be noted that while Figures 4-6 and 9 illustrate a mixing/blending step where the bitumen feedstock 70 is blended/mixed with the ionic liquid and optionally a diluent, the addition of the diluent can be done prior to the addition of the ionic liquid, i.e., not necessarily simultaneously.
[181] The upgrading techniques in presence of an ionic liquid, including the catalytic cracking treatment 76 and the non-catalytic treatment 84, will now be described in further detail.
Catalytic cracking using ionic liquids for upgrading bitumen
[182] Conventional upgrading techniques can include cracking treatments such as thermal cracking and catalytic cracking to convert heavy hydrocarbon fractions, such as bitumen, to lighter fractions that are considered more valuable, such as gasoline and distillate, by breaking the chemical bonds of long-chain hydrocarbons into smaller-chain hydrocarbons. These conventional upgrading techniques generally involve treating heavy hydrocarbons at high temperature and/or high pressure, and can lead to the formation of coke as an undesirable by-product. In the case of catalytic cracking, coke can in turn deactivate the catalyst when depositing thereon, and so can heavy metals, , nitrogen and sulfur. In the context of the present description and in contrast with conventional cracking techniques, the expression "catalytic cracking treatment" in the presence of an ionic liquid and the conditions at which the catalytic cracking treatment is performed (which can also be referred to as "catalytic cracking conditions" in the context of the present description) refer to a treatment operated at a temperature and/or a pressure that is lower compared to the temperature and pressure conditions at which are conducted conventional cracking processes, as will be described in more detail below.
[183] With reference to Figure 3, an implementation of a bitumen feedstock 70 that is subjected to a catalytic cracking treatment 76 in presence of an ionic liquid used as a catalyst is shown. In some implementations, the conditions at which the catalytic cracking treatment is performed can include operating the catalytic cracking treatment 76 at temperatures between about 50 C and about 250 C. In some scenarios and without being limiting, the conditions at which the catalytic cracking treatment is performed can include operating the catalytic cracking treatment 76 near atmospheric pressure.
[184] In some implementations, the ionic liquid catalyst is a Lewis acidic ionic liquid catalyst and comprises a complex anion (e.g., AlC14- formed from complexation between Lewis acid A1C13 and anion CI-) and a cation (e.g., an imidazolium cation or an ammonium cation). Lewis acids have the ability to act as an electron pair acceptor.
Lewis acids are formed by reacting a metal halide with an organic halide salt, at various molar ratios. Several factors can contribute to make Lewis acidic ionic liquids advantageous for catalytic application. In some implementations, the ionic liquid catalyst is a Bronsted acidic ionic liquid catalyst. Bronsted acidic ionic liquids can catalyse reactions due to a labile proton which is present in their structure (in the cation or in the anion). For example, Bronsted acidic ionic liquids can include acidic functional groups such as SO3H or COOH, attached to the cation, or can include an acidic hydrogen on a nitrogen or oxygen atom in the cation. Bronsted acidic ionic liquids can be prepared by proton transfer between a Bronsted acid and a Bronsted base. The most common Bronsted acidic ionic liquids include a protonated imidazolium cation, a protonated pyridinium cation, a guanidinium cation, a protonated ammonium cation, a COOH-bearing imidazolium cation or a SO3H-bearing imidazolium cation. For instance, their acidity can be modulated to provide the opportunity to design materials that are tailor made for certain applications, their ability to dissolve a wide range of materials can eliminate the need to add solvent, and they can act as both catalyst and solvent at the same time. In what follows and unless otherwise specified, the term "acidic ionic liquid catalyst" is meant to refer to a Bronsted acidic ionic liquid catalyst, a Lewis acidic ionic liquid catalyst, or a combination thereof.
Examples of Bronsted acidic ionic liquid cations:
R.._ NH+
N+
\_/

N+ SO3H
N+HR
[185] In some implementations, the cation can include for instance 1,3-dialkylimidazolium cations, tetraalkylphosphonium cations, tetraalkylammonium cations, trialkylammonium cations, and combinations thereof. In some implementations, the Lewis acidic ionic liquid catalyst comprises a complex anion formed from complexation between a Lewis acid and Lewis base anion, and a 1-alkyl-3-methylimidazolium cation.
In some scenarios, the 1-alkyl-3-methylimidazolium cation can be for instance 1-ethy1-3-methylimidazolium (EMIM) or 1-n-butyl-3-methylimidazolium (BMIM). When the Lewis acidic ionic liquid catalyst comprises a complex anion and a trialkylammonium cation, the trialkylammonium cation can be for instance triethylammonium. In some implementations, the complex anion is a chlorometallate anion, and can be for instance AlC14-, Al2C17-, FeC14- and Fe2CI7-. In some implementations, the Lewis acidic ionic liquid catalyst can be for instance [EMIM][AICI4], [BMIM][AIC14], [EMIM][FeCI4], [BMIM][FeCI4].
In yet other implementations, Lewis acidic ionic liquid catalyst can include a metal ion-modified ionic liquid, which can be for instance [Et3NH][AICI4]-Ni2+, [EMIM][AIC14]-Ni2+, [BMIM][AIC14]-Ni2+, [Et3NH][AIC14]-Fe2+, [EMIM][AICI4]-Fe2+, [BM IM][AIC14]-Fe2+, and combinations thereof. It should be understood that as used herein, the term "complex anion" can be referred to as a "Lewis acidic anion".
[186] In some implementations, the concentration of the acidic ionic liquid catalyst in the ionic liquid-bitumen mixture can be between about 5 wt% and about 50 wt%.
In other implementations, the concentration of the acidic ionic liquid catalyst in the bitumen/diluent mixture 210 can be below 5 wt%, or above 50 wt%. The concentration of the acidic ionic liquid catalyst in the ionic liquid-bitumen mixture can depend for instance of the characteristics of the bitumen feedstock, and/or the characteristics of the acidic ionic liquid catalyst.
[187]
The catalytic cracking treatment 76 can be performed in any suitable vessel, or reactor, that can be operated at conditions as described herein and that enables the obtention of an ionic liquid-cracked bitumen mixture 78. In some implementations, the vessel can be a vessel designed such that the ionic liquid-cracked bitumen mixture 78 can be retrieved as an overflow stream and an undesirable products stream such as coke can be retrieved as an underflow stream. In other implementations, the ionic liquid-cracked bitumen mixture 78 can be retrieved from the vessel as a single stream that includes all of the hydrocarbon components but that has improved physical and/or chemical properties. As mentioned above, the conditions enabling the catalytic cracking of the ionic liquid-bitumen mixture 74 generally include a temperature and a pressure at which the catalytic cracking treatment 76 is conducted, for a given duration.
The conditions at which the catalytic cracking treatment is performed can vary depending on the characteristics of the bitumen feedstock 70. For instance, for a bitumen feedstock 70 having a high proportion of heavy hydrocarbon, the severity of the catalytic cracking can be increased, while for a bitumen feedstock having a low proportion of heavy hydrocarbon, the severity of the catalytic cracking can be decreased.
"Severity" as used herein refers to the severity of the conditions of temperature and residence time at which the bitumen feedstock is treated. The severity can be expressed in terms of an equivalent reaction time (ERT) in seconds of residence time when a reactor is operating at 427 C (800 F). The ERT corresponds to the residence time that would achieve the same conversion of heavy material at a given temperature as if the reaction was conducted at 427 C (800 F).
[188] Still referring to Figure 3, optionally, the ionic liquid-cracked bitumen mixture 78 can be subjected to a separation step 92 to separate the acidic ionic liquid catalyst 98 and/or to separate diluent 94 that was initially part of the bitumen feedstock, if applicable, from the ionic liquid-cracked bitumen mixture 78. A cracked bitumen product 90 is then obtained. The cracked bitumen product 90 can be subjected to separation to be separated into various streams according to their boiling points, for instance in a fractionator or distillation column.
[189] Referring to Figures 4 to 6, a bitumen feedstock 70 and an acidic ionic liquid catalyst are blended or mixed 100 together to obtain an ionic liquid-bitumen mixture 74.
Optionally, a diluent 102 can also be added to the ionic liquid-bitumen mixture 74 during the mixing step 100, for instance to improve characteristic(s) of the ionic liquid-bitumen mixture 74 or to facilitate the obtention of an at least partially homogenized ionic liquid-bitumen mixture 74 by further reducing its viscosity. As mentioned above, in some scenarios, the bitumen feedstock 70 can already include a diluent, such that it may not be advantageous to add additional diluent during the mixing step 100. In other scenarios, even if bitumen feedstock 70 already includes a diluent, there may still advantages to add additional diluent during the mixing step 100, for instance to obtain given characteristics of the ionic liquid-bitumen mixture 74. Examples of suitable diluents that can be used include natural gas condensates, hexane or cyclohexane, naphthenic diluent, or any other suitable diluent.
[190] Still with reference to Figures 4 to 6, the ionic liquid-bitumen mixture 74 is then subjected to the catalytic cracking treatment 76 to produce the ionic liquid-cracked bitumen mixture 78. The ionic liquid-cracked bitumen mixture 78 is then subjected to one or two separation steps, to recover at least a portion of diluent 102 if present, and at least a portion of the acidic ionic liquid catalyst 72. The ionic liquid-cracked bitumen mixture 78 can be subjected to a single separation step 104 configured to separate the diluent 102 and the acidic ionic liquid catalyst 72 from the ionic liquid-cracked bitumen mixture 78 in a single step, as shown in Figure 4. In some implementations, the acidic ionic liquid catalyst 72 and the diluent 102 can be separated from the cracked bitumen product 90 as a single stream, and optionally separated from each other thereafter.
When the ionic liquid-cracked bitumen mixture 78 is subjected to two separation steps 106,108, the two separation steps 106,108 can be performed in one sequence or the other. In some implementations, the separation step 104, 106, 108 can be performed for instance in a gravity settler, a diluent recovery unit, or a solvent recovery unit. Figure 5 illustrates an implementation where the ionic liquid-cracked bitumen mixture 78 is , , subjected to a first separation step 106 to recover a recovered diluent 94 and produce a diluent-depleted cracked bitumen mixture 110, which is then subjected to a second separation step 108 to recover a recovered acidic ionic liquid catalyst 98 and produce the cracked bitumen product 90. Figure 6 illustrates another implementation where the ionic liquid-cracked bitumen mixture 78 is subjected to a first separation step 108 to recover a recovered acidic ionic liquid catalyst 98 and produce an ionic liquid-depleted cracked bitumen mixture 112 which is then subjected to a second separation step 106 to recover a recovered diluent 94 and produce the cracked bitumen product 90.
[191] The separation step 106 is configured to recover the diluent 102 from the ionic liquid-cracked bitumen mixture 78 or from the ionic liquid-depleted cracked bitumen mixture 112. In some implementations, the separation step 106 can include evaporating the diluent 102 from the liquid-cracked bitumen mixture 78 or from the ionic liquid-depleted cracked bitumen mixture 112 to obtain the recovered diluent 94. At least a portion of the recovered diluent 94 can be recycled to be used as the diluent 102 that can be optionally added to the bitumen feedstock 70 and the acidic ionic liquid catalyst 72 for the mixing step 100.
[192] The separation step 108 is configured to recover the acidic ionic liquid catalyst 98 from the ionic liquid-cracked bitumen mixture 78 or the diluent-depleted cracked bitumen mixture 110. In some implementations, the separation step 108 includes a liquid-liquid extraction of the ionic liquid-cracked bitumen mixture 78 or the diluent-depleted cracked bitumen mixture 110. In implementations where the acidic ionic liquid catalyst is water soluble, the liquid-liquid extraction of the ionic liquid-cracked bitumen mixture 78 or the diluent-depleted cracked bitumen mixture 110 can include washing the ionic liquid-cracked bitumen mixture 78 or the diluent-depleted cracked bitumen mixture 110 with water. At least a portion of the recovered acidic ionic liquid catalyst 98 can be recycled to be reused as the acidic ionic liquid catalyst 72 to be combined with the bitumen feedstock 70.
[193] Referring now to Figure 7, an embodiment of the implementations described above is presented. In the embodiment shown, a bitumen feedstock 200 is blended/mixed 208 with a diluent 206 to obtain a bitumen/diluent mixture 210.
The diluent 206 can be chosen for instance to arrive at certain characteristics of the , , bitumen/diluent mixture 210, for example in terms of viscosity. The diluent 206 can include for instance natural gas condensates, hexane or cyclohexane, naphthenic diluent, or any other suitable diluent. In some implementations, the blending/mixing step 208 can include heating the bitumen feedstock 200 for a given period of time.
The bitumen/diluent mixture 210 is then subjected to catalytic cracking 212 in presence of an acidic ionic liquid catalyst 214, the bitumen/diluent mixture 210 and the acidic ionic liquid catalyst 214 forming an ionic liquid-bitumen mixture. In some implementations, the concentration of the acidic ionic liquid catalyst in the ionic liquid-bitumen mixture can be between about 5 wt% and about 50 wt%. In other implementations, the concentration of the acidic ionic liquid catalyst in the ionic liquid-bitumen mixture can be below 5 wt%, or above 50 wt%. The catalytic cracking 212 is performed under conditions that can include for instance heating the ionic liquid-bitumen mixture at temperatures between 50 C and 250 C. In some scenarios and without being !imitative, the catalytic cracking can be performed at pressures near normal atmospheric pressure. It is to be understood that other conditions can be implemented for the catalytic cracking treatment, and can be determined or adjusted depending on the bitumen/diluent mixture 210 physical and chemical properties, among other factors. Following the catalytic cracking 212, a cracked reaction mixture 216 is subjected to diluent removal 218 to recover at least a portion of the diluent as recovered diluent 220 and obtain a diluent-depleted cracked bitumen mixture 222. The diluent removal 218 step can be done by evaporation of the diluent 206. In some implementations, a system including a diluent recovery unit, a solvent recovery unit or a flash drum can be used to recover the diluent 206.
Optionally, the recovered diluent 220 can be recycled to be reused to blend/mix with the bitumen feedstock 200. The diluent-depleted cracked bitumen mixture 222 is then subjected to another separation step 224 to separate at least a portion of the acidic ionic liquid catalyst 214 from the diluent-depleted cracked bitumen mixture 222 as a recovered acidic ionic liquid catalyst 226 and to produce a cracked bitumen product 228.
In some scenarios, when the acidic ionic liquid catalyst 214 is water soluble, the second separation step 224 can be performed as a water washing step. Although Figure shows the diluent separation step 218 performed prior to the acidic ionic liquid catalyst separation step 224, it is to be understood that the order of these steps can be interchanged such that the acidic ionic liquid catalyst separation step 224 can be performed prior to the diluent separation step 218. In some implementations and as mentioned above, the sequence of the separation steps 218, 224 can be determined according to the characteristics of the diluent 206 and the acidic ionic liquid catalyst 214 and the corresponding separation techniques that have to be put in place to recover each of them.
Non-catalytic treatment using ionic liquids for upgrading bitumen
[194] As mentioned above, reducing the viscosity of a bitumen feedstock can be advantageous to improve its pipelinability. There can also be advantages in reducing the total acid number (TAN) of the bitumen feedstock, which can in turn contribute to reduce corrosive properties of the bitumen feedstock. It can be also advantageous to remove certain contaminants such as sulphur and heavy metals, and/or to decrease the asphaltene content of the bitumen feedstock. The techniques described below are aimed at improving such characteristics of the bitumen feedstock by subjecting the bitumen feedstock to a non-catalytic treatment in presence of an ionic liquid.
[195] With reference to Figure 8, in an implementation of a non-catalytic treatment, a bitumen feedstock 300 is combined with an ionic liquid 304 in a blending/mixing step 306 to form an ionic liquid-bitumen mixture 308. The bitumen feedstock 300 can be of various sources and have various characteristics as previously described above. The bitumen feedstock 300 can optionally include a diluent. If the bitumen feedstock 300 incudes a diluent, the diluent can be separated from the bitumen feedstock 300 prior to the non-catalytic treatment, or the bitumen feedstock 300 can remain as a mixture of bitumen and diluent. In some implementations, the ionic liquid 304 can be added to the bitumen feedstock 300 to reach a concentration of the ionic liquid 304 ranging from about 5 wt% to about 50 wt%. In other implementations, the concentration of the acidic ionic liquid catalyst in the ionic liquid-bitumen mixture can be below 5 wt%, or above 50 wt%.
[196] The ionic liquid-bitumen mixture 308 is then subjected to a non-catalytic treatment 310 in a suitable vessel. In the context of the present description, the non-catalytic treatment 310 is performed under non-catalytic cracking conditions, and could thus be considered as a mild thermal treatment that is performed at low severity conditions. In some implementations, the non-catalytic cracking conditions include performing the non-catalytic treatment 310 at a temperature at which asphaltene aggregation within the ionic liquid-bitumen mixture 308 is avoided. For instance, in some embodiments, the temperature at which is conducted the non-catalytic treatment can be between about 20 C and about 120 C. In some implementations, the temperature at which is conducted the non-catalytic treatment 310 can be a temperature that enables proper mixing of the bitumen feedstock 300 with the ionic liquid 304 during the blending/mixing step 306, i.e., a temperature at which the respective viscosity of the bitumen feedstock 300 and the ionic liquid 304 is low enough to allow sufficient contact between the bitumen feedstock 300 and the ionic liquid 304. In some implementations, the non-catalytic treatment 310 can be performed at room temperature. The temperature at which the non-catalytic treatment 310 is conducted and the duration of the non-catalytic treatment 310 can depend on the endpoint that is desired to be achieved, on the initial viscosity of the bitumen feedstock 300 or of the ionic liquid 304, and/or on the properties of the ionic liquid used, for example.
[197] In the implementation shown in Figure 8, the ionic liquid 304 that is combined with the bitumen feedstock 300 for the non-catalytic treatment 310 includes ionic liquids that are miscible in bitumen or a mixture of bitumen and diluent, L e., that are feed-miscible. Examples of ionic liquids that are miscible in a mixture of bitumen and toluene can include for instance some carbamate ionic liquids such as N, N'-dipropylammonium, N, N'-dipropyl carbamate (DPCARB) and N, N'-dibenzylammonium, N, N'-dibenzyl carbamate (DBCARB), phosphonium ionic liquids such as Trihexyl-tetradecylphosphonium dicyanamide (Cyphos IL 105), among others. In some implementations, the ionic liquid 304 used for the non-catalytic treatment 310 can be chosen according to its likelihood to not have cracking functionality, although the solvent properties of anionic liquid used for catalytic cracking may still favor its use under non-catalytic conditions.
[198] Following the non-catalytic treatment 310, a treated ionic liquid-bitumen mixture 312 is obtained, which then may optionally be subjected to a separation step 314 to separate the ionic liquid 304 from the treated ionic liquid-bitumen mixture 312 and produce a recovered ionic liquid 316 and a treated bitumen product 318. When no separation step is performed, the treated ionic liquid-bitumen mixture 312 can be considered to correspond to the treated bitumen product 318. In some implementations, such a non-catalytic treatment 310 of the ionic liquid-bitumen mixture 306 can contribute to improve physical properties of the bitumen feedstock 300 such as viscosity reduction and asphaltene content reduction, as well as TAN reduction. In some implementations, the alkalinity of the ionic liquid 304 can be correlated with the TAN
reduction that is achieved: the stronger the alkalinity of the ionic liquid 304, the greater the TAN reduction in the treated ionic liquid-bitumen mixture 312 or the treated bitumen product 90. In some implementations, subjecting the ionic liquid-bitumen mixture 308 to the non-catalytic treatment 310 as described herein can facilitate achieving viscosity reduction ranging from 40% to 90% and/or TAN reduction ranging from 15% to 55%, when ionic liquids such as DPCARB, DBCARB and Cyphos IL 105 are used.
[199] Referring now to Figure 9, in another implementation of a non-catalytic treatment, a bitumen feedstock 300, a diluent 302 and an ionic liquid 304 are combined in a blending/mixing step 306 to produce an ionic liquid-bitumen mixture 308. The diluent 302 can be for instance a naphthenic diluent. In implementations where the bitumen feedstock 300 already includes a diluent, the diluent 302 addition can be omitted.
[200] In the implementation shown in Figure 9, the ionic liquid 304 that is combined with the bitumen feedstock 300 for the non-catalytic treatment 311 include ionic liquids that are immiscible in a mixture of bitumen and toluene, e., that are feed-immiscible.
Ionic liquids that are immiscible in a bitumen and toluene mixture can include for instance amino acid based ionic liquids such as tetraethylammonium 6-alaninate and 1-ethy1-3-methylimidazolium glycinate, imidazolium ionic liquids such as 1-ethy1-methylimidazolium ethyl sulphate and 1-butyl-3-methylimidazolium tetrafluoroborate, phosphonium ionic liquids such as Tributyl-methylphosphonium methyl sulphate, and carbamate ionic liquids such as N, N'-dimethylammonium, N, N'-dimethylcarbamate (DMCARB).
[201] In some implementations, the ionic liquid 304 can be added to the bitumen feedstock 300 to reach a concentration of the ionic liquid 304 ranging from about 5 wt%
to about 50 wt%. In some implementations, the proportion of the bitumen relative to the feed-immiscible ionic liquid is between about 1:2 w/w and about 1:1 w/w.
[202] The ionic liquid-bitumen mixture 309 is then subjected to the non-catalytic treatment 311 to produce a treated ionic liquid-bitumen mixture 312. The non-catalytic treatment 311 shown in Figure 9 can include heating the ionic liquid-bitumen mixture 309, for instance at temperatures ranging from about 40 C to 70 C, which can facilitate efficient mixing of the three components of the ionic liquid-bitumen mixture 309. The non-catalytic treatment 311 can also include mixing, which can facilitate the transfer of at least a portion of contaminants contained in the bitumen feedstock 300 from the bitumen feedstock 300 to the mixture of diluent 302 and ionic liquid 304. In some implementations, the non-catalytic treatment 311 can include heating the ionic liquid-bitumen mixture 308 at a first temperature for a first duration as part of a first thermal treatment, and then heating the ionic liquid-bitumen mixture 309 at a second temperature for a second duration as part of a second thermal treatment and so on, to ensure that proper mixing and contact between the bitumen feedstock 300 and the ionic liquid 304 can be achieved.
[203] The treated ionic liquid-bitumen mixture 312 is then subjected to a liquid-liquid extraction 320, during which a first phase 324 that includes the bitumen feedstock 300 and the diluent 302 (or the bitumen feedstock 300 if the bitumen feedstock 300 already includes a diluent) is separated from a second phase that includes the ionic liquid 304.
The liquid-liquid extraction 320 can facilitate at least partial removal of undesirable components from the bitumen feedstock 300, such as sulphur, naphthenic acids and heavy metals, by enabling transfer of the undesirable components to the ionic liquid 304.
The liquid-liquid extraction 320 can be performed in any suitable vessel, which can be for instance a liquid-liquid separation unit or a decanter. The first phase that includes the bitumen and the diluent can be withdrawn as a bitumen-diluent mixture stream 324. In some implementations, the bitumen-diluent mixture stream 324 can be subjected to additional separation step(s) 326 to separate the diluent from the bitumen and obtain a recovered diluent 330, which can optionally be recycled for reuse in the blending/mixing step 306, and a treated bitumen product 328. In other implementations, it can also be advantageous to keep the diluent and the bitumen combined together, for instance such that the viscosity of the diluent-bitumen mixture is within a given range. The second phase that includes the ionic liquid 304 can be withdrawn as a recovered ionic liquid stream 322, which can optionally be recycled for reuse in the blending/mixing step 306.

The non-catalytic treatment 311 thus produces the bitumen-diluent mixture stream 324, or the treated bitumen product 328, if diluent has been separated therefrom.
[204] As mentioned above, different ionic liquids that are immiscible in a mixture of bitumen and toluene can be used, or ionic liquids that are feed-immiscible, the choice of which can depend for instance of the characteristic(s) of the bitumen feedstock that is desired to be improved. For instance, subjecting the ionic liquid-bitumen mixture 309 to the non-catalytic treatment 311 as described herein in the presence of amino acid based ionic liquids can facilitate TAN reduction, which in some implementations, can be up to 100%. Similarly to the non-catalytic treatment 310 in presence of an ionic liquid that is miscible in a mixture of bitumen and toluene, the alkalinity of the ionic liquid 304 that is immiscible in a mixture of bitumen and toluene can be correlated with the TAN
reduction achieved when the non-catalytic treatment 311 is performed. In some implementations, the concentration of metals such as nickel and vanadium can also be reduced when the ionic liquid-bitumen mixture 309 is subjected to the non-catalytic treatment 311. For instance, the reduction of nickel can be up to about 60%, and the reduction in vanadium can be up to 30%, depending on the ionic liquid used.
Catalytic cracking treatment and non-catalytic treatment in sequence
[205] The techniques described herein to upgrade a bitumen feedstock in presence of an ionic liquid can also include a combination of a catalytic cracking treatment and a non-catalytic treatment performed sequentially to take advantage of the respective improvements on the bitumen properties that can be achieved by performing each of these two treatments. The choice of the ionic liquid used for the catalytic cracking treatment and the non-catalytic treatment and the sequence of the treatments, L e., which ones of the catalytic cracking treatment and a non-catalytic treatment is performed first, can depend for instance on the characteristics of the bitumen feedstock, on the desired characteristics of the resulting partially upgraded bitumen product and/or on the overall process configuration and design.
[206] Referring to Figure 10, an implementation of an upgrading technique that includes a catalytic cracking treatment of a mixture of bitumen and an ionic liquid followed by a non-catalytic treatment of the resulting cracked mixture of bitumen and an , ionic liquid is shown. In this implementation, a bitumen feedstock 400 and a first ionic liquid 402 are combined in a first blending/mixing step 406 to produce a first ionic liquid-bitumen mixture 408. In certain embodiments, the first ionic liquid 402 comprises an acidic ionic liquid catalyst as described above. The first ionic liquid-bitumen mixture 408 is then subjected to a catalytic cracking treatment 410 under conditions as detailed above, to convert heavy hydrocarbons to lighter hydrocarbons. The catalytic cracking treatment 410 produces an ionic liquid-cracked bitumen mixture 412. In some implementations, the ionic liquid-cracked bitumen mixture 412 can be separated to remove the diluent, if present in the bitumen feedstock 400, and/or the ionic liquid 402, to obtain a cracked bitumen product 416. The separation step 414 can thus be configured to separate a recovered ionic liquid 418 and optionally a recovered diluent 420. Various separation methods can be implemented to separate the first ionic liquid 402 from the ionic liquid-cracked bitumen mixture 412, depending on the properties of the first ionic liquid 402. For instance, in some implementations, the first ionic liquid 402 can be miscible in water and thus can be removed by a water washing step. Each one of the recovered ionic liquid 418 and the recovered diluent 420 can be recycled to be reused in other parts of the process.
[207] Following the separation step 414, the cracked bitumen product 416 is then combined with a second ionic liquid 422 in a second blending/mixing step 424.
The blending/mixing step 424 can also include the addition of a diluent, for instance if the bitumen feedstock 400 does not initially include such diluent and depending on the choice of the second ionic liquid 422 and the choice of non-catalytic treatment that follows. For instance, when the second ionic liquid 422 is an ionic liquid that is miscible in a mixture of bitumen and toluene as described above, the presence of a diluent can be optional. When the second ionic liquid 422 is an ionic liquid that is immiscible in a mixture of bitumen and toluene as described above, it can be advantageous to add a diluent if the bitumen feedstock 400 does not initially include such diluent.
[208] Following the second blending/mixing step 424, a second ionic liquid-bitumen mixture 426 is obtained. The second ionic liquid-bitumen mixture 426 is subjected to a non-catalytic treatment 428 to obtain a treated ionic liquid-bitumen mixture 430. The configuration of the non-catalytic treatment 428 can be chosen according to the , 35 endpoint(s) that are desired to be achieved, which in turn can contribute to determine the type of ionic liquid that is used as the second ionic liquid 422.
[209] In some implementations, when a reduction in viscosity or a reduction of TAN in the cracked bitumen product 416 is desired, the second ionic liquid 422 can be chosen to be an ionic liquid that is miscible in a mixture of bitumen and diluent, and the non-catalytic treatment 428 generally includes mixing the second ionic liquid-bitumen mixture 426 at a given temperature for a given duration. Examples of suitable second ionic liquids 422 in such implementations include carbamate ionic liquids such as DPCARB, DBCARB, and phosphonium ionic liquids such as Cyphos IL 105. In some implementations, the temperature at which is performed the non-catalytic treatment 428 can range for instance from room temperature to about 100 C. In some implementations, the duration of the non-catalytic treatment 428 can be for instance from 24 hours to 96 hours. It is to be understood that the temperature and the duration of the non-catalytic treatment 428 can vary according to numerous factors including the characteristics of the cracked bitumen product 416 and the second ionic liquid chosen. Optionally, the second ionic liquid 422 can be separated 432 from the treated ionic liquid-bitumen mixture 430 to obtain a treated bitumen product 434.
[210] In other implementations, when a reduction in contaminants such as sulphur and heavy metals, a TAN reduction, and/or a decrease the asphaltene content of the cracked bitumen product 416 is desired, the second ionic liquid 422 can be chosen to be an ionic liquid that is immiscible in a mixture of bitumen and diluent. Examples of suitable second ionic liquids 422 in such implementations include amino acid based ionic liquids, phosphonium ionic liquids and carbamate ionic liquids such as DMCARB. In these implementations, the non-catalytic treatment 428 can include mixing the second ionic liquid-bitumen mixture 426 at a given temperature for a given duration, and can be followed by a separation 432 that can be a liquid-liquid separation. As mentioned above, the mixing of the second ionic liquid-bitumen mixture 426 can facilitate the transfer of at least a portion of contaminants from the bitumen to the mixture of diluent and the second ionic liquid 422. The liquid-liquid extraction can then be performed to separate a first phase that includes bitumen and diluent of the second ionic liquid-bitumen mixture 426 from a second phase that includes the second ionic liquid 422. The first phase can be considered to correspond to the treated bitumen product 434, or if the diluent can then , , be separated from the first phase, the resulting bitumen can correspond to the treated bitumen product 434.
[211] It should to be understood that although Figure 10 illustrates an implementation that includes a catalytic cracking treatment followed by a non-catalytic treatment, in other implementations, the process for upgrading a bitumen feedstock can be in the reverse sequence and include the non-catalytic treatment followed by the catalytic cracking treatment.

Claims (153)

37
1. A process for treating a bitumen feedstock, the process comprising:
contacting an acidic ionic liquid catalyst with the bitumen feedstock to obtain an ionic liquid-bitumen mixture;
subjecting the ionic liquid-bitumen mixture to a catalytic cracking treatment, the catalytic cracking treatment comprising heating the ionic liquid-bitumen mixture under catalytic cracking conditions to obtain an ionic liquid-cracked bitumen mixture; and separating the acidic ionic liquid catalyst from the ionic liquid-cracked bitumen mixture to obtain a cracked bitumen product and a recovered acidic ionic liquid catalyst.
2. The process of claim 1, wherein the bitumen feedstock comprises a diluent-depleted bitumen stream from a distillation unit, a diluent stripping unit or a diluent recovery unit.
3. The process of claim 1, wherein the bitumen feedstock comprises a diluent-depleted bitumen stream that is obtained from a bitumen froth treatment operation.
4. The process of claim 1, wherein the bitumen feedstock comprises a diluent-depleted bitumen stream that has not been subjected to fractionation or distillation prior to being contacted with the acidic ionic liquid catalyst.
5. The process of claim 1, wherein the bitumen feedstock comprises a residuum stream from a distillation tower that has been operated to remove light hydrocarbon components.
6. The process of claim 1, wherein the bitumen feedstock comprises a bitumen stream that is obtained from an in situ recovery operation or from surface mining operations.
7. The process of any one of claims 1 to 6, further comprising subjecting the bitumen feedstock to a pre-treatment prior to the contacting of the bitumen feedstock with the acidic ionic liquid catalyst.
8. The process of claim 7, wherein the pre-treatment comprises heating the bitumen feedstock at a pre-treatment temperature.
9. The process of claim 8, wherein the pre-treatment temperature is sufficient to reduce viscosity of the bitumen feedstock.
10. The process of any one of claims 7 to 9, wherein the pre-treatment comprises adding a diluent to the bitumen feedstock.
11. The process of claim 10, wherein the diluent comprises at least one of a naphthenic solvent, an aromatic hydrocarbon, and a non-deasphalting organic solvent.
12. The process of claim 10 or 11, wherein the diluent comprises toluene.
13. The process of claim 6, wherein the bitumen feedstock comprises bitumen and a diluent.
14. The process of any one of claims 10 to 13, further comprising recovering the diluent to obtain a recovered diluent.
15. The process of claim 14, wherein recovering the diluent is performed after the catalytic cracking treatment of the ionic liquid-bitumen mixture under catalytic cracking conditions and before separating the acidic ionic liquid catalyst from the ionic liquid-cracked bitumen mixture.
16. The process of claim 14, wherein recovering the diluent is performed after separating the acidic ionic liquid catalyst from the ionic liquid-cracked bitumen mixture.
17. The process of any one of claims 14 to 16, wherein recovering the diluent comprises evaporating the diluent from the ionic liquid-cracked bitumen mixture or the cracked bitumen product.
18. The process of any one of claims 14 to 17, further comprising contacting at least a portion of the recovered diluent with the bitumen feedstock.
19. The process of any one of claims 1 to 18, wherein the recovered acidic ionic liquid catalyst is reused as part of the acidic ionic liquid catalyst that contacts the bitumen feedstock.
20. The process of any one of claims 1 to 19, wherein separating the acidic ionic liquid catalyst from the ionic liquid-cracked bitumen mixture comprises a liquid-liquid extraction of the ionic liquid-cracked bitumen mixture.
21. The process of claim 14, wherein the liquid-liquid extraction of the ionic liquid-cracked bitumen mixture comprises washing the ionic liquid-cracked bitumen mixture with water.
22. The process of any one of claims 1 to 21, wherein the acidic ionic liquid catalyst is a Lewis acidic ionic liquid catalyst comprising a Lewis acidic anion and a cation selected from the group consisting of 1,3-dialkylimidazolium cations, tetraalkylphosphonium cations, tetraalkylammonium cations, trialkylammonium cations and combinations thereof.
23. The process of claim 22, wherein the Lewis acidic ionic liquid catalyst comprises a Lewis acidic anion and a 1-alky1-3-methylimidazolium cation.
24. The process of claim 23, wherein the 1-alky1-3-methylimidazolium cation is selected from the group consisting of 1-ethy1-3-methylimidazolium (EMIM) and 1-n-buty1-methylimidazolium (BMIM).
25. The process of claim 22, wherein the Lewis acidic ionic liquid catalyst comprises a Lewis acidic anion and a trialkylammonium cation.
26. The process of claim 25, wherein the trialkylammonium cation comprises triethylam m on ium.
27. The process of any one of claims 22 to 26, wherein the Lewis acidic anion is a chlorometallate anion.
28. The process of claim 27, wherein the chlorometallate anion is selected from the group consisting of AlC14-, Al2C17-, FeC14- and Fe2C17-.

,
29. The process of any one of claims 22 to 28, wherein the Lewis acidic ionic liquid is selected from the group consisting of [EMIM][AIC14], [BMIM][AIC14], [EMIM][FeCl4], [BMIM][FeCl4].
30. The process of claim 29, wherein the Lewis acidic ionic liquid is [EMIM][AlCl4].
31. The process of claim 22, wherein the Lewis acidic ionic liquid comprises a metal ion-modified ionic liquid.
32. The process of claim 31, wherein the metal ion-modified ionic liquid is selected from the group consisting of [Et3NFI][AlCl4]-Ni2+, [EMlM][AlCla]-Ni2+, [BMIM][AlCl4]-Ni2+, [Et3NH][AlCl4]-Fe2+, [EMlIV1][Alad-Fe2+, [BM lfvl][AlCl4]-Fe2+ and combinations thereof.
33. The process of any one of claims 1 to 21, wherein the acidic ionic liquid catalyst is a Bronsted acidic ionic liquid catalyst.
34. The process of any one of claims 1 to 33, wherein the heating is performed at a temperature between about 50 C and about 250 C.
35. The process of any one of claims 1 to 34, wherein the concentration of the acidic ionic liquid catalyst in the ionic liquid-bitumen mixture is between about 5 wt% and about 50 wt%.
36. A process for upgrading a bitumen feedstock, comprising:
contacting the bitumen feedstock with a feed-miscible ionic liquid to obtain an ionic liquid-bitumen mixture; and subjecting the ionic liquid-bitumen mixture to a non-catalytic treatment, the non-catalytic treatment comprising mixing the ionic liquid-bitumen mixture at a mixing temperature below an asphaltene aggregation temperature of the ionic liquid-bitumen mixture to obtain a treated ionic liquid-bitumen mixture;
wherein at least one of a Total Acid Number (TAN) of the treated ionic liquid-bitumen mixture, a viscosity of the treated ionic liquid-bitumen mixture and an asphaltene content of the treated ionic liquid-bitumen mixture is reduced compared to the bitumen feedstock.
37. The process of claim 36, wherein the bitumen feedstock comprises diluent-depleted bitumen stream from a distillation unit, a diluent stripping unit or a diluent recovery unit.
38. The process of claim 36, wherein the bitumen feedstock comprises a diluent-depleted bitumen stream that is obtained from a bitumen froth treatment operation.
39. The process of claim 36, wherein the bitumen feedstock comprises a diluent-depleted bitumen stream that has not been subjected to fractionation or distillation prior to being contacted with the feed-miscible ionic liquid.
40. The process of claim 36, wherein the bitumen feedstock comprises a residuum stream from a distillation tower that has been operated to remove light hydrocarbon components.
41. The process of claim 36, wherein the bitumen feedstock comprises a bitumen stream that is obtained from an in situ recovery operation or from surface mining operations.
42. The process of any one of claims 36 to 41, further comprising subjecting the bitumen feedstock to a pre-treatment prior to the contacting of the bitumen feedstock with the feed-miscible ionic liquid.
43. The process of claim 42, wherein the pre-treatment comprises heating the bitumen feedstock at a pre-treatment temperature.
44. The process of claim 43, wherein the pre-treatment temperature is sufficient to reduce viscosity of the bitumen feedstock.
45. The process of any one of claims 42 to 44, wherein the pre-treatment comprises adding a diluent to the bitumen feedstock.
46. The process of claim 45, wherein the diluent comprises at least one of a naphthenic solvent, an aromatic hydrocarbon, and a non-deasphalting organic solvent.
47. The process of claim 45 or 46, wherein the diluent comprises toluene.
48. The process of claim 41, wherein the bitumen feedstock comprises bitumen and a diluent.
49. The process of any one of claims 45 to 48, further comprising recovering the diluent to obtain a recovered diluent.
50. The process of any one of claims 36 to 49, further comprising separating the feed-miscible ionic liquid from the treated ionic liquid-bitumen mixture to obtain a recovered feed-miscible ionic liquid and a treated bitumen product.
51. The process of claim 50, wherein recovering the diluent is performed after the non-catalytic treatment of the ionic liquid-bitumen mixture and before separating the feed-miscible ionic liquid from the treated ionic liquid-bitumen mixture.
52. The process of claim 50, wherein recovering the diluent is performed after separating the feed-miscible ionic liquid from the treated ionic liquid-bitumen mixture.
53. The process of any one of claims 49 to 52, wherein recovering the diluent comprises evaporating the diluent from the treated ionic liquid-bitumen mixture or from the treated bitumen product.
54. The process of any one of claims 49 to 53, further comprising contacting at least a portion of the recovered diluent with the bitumen feedstock.
55. The process of any one of claims 50 to 54, wherein the recovered feed-miscible ionic liquid is reused as part of the feed-miscible ionic liquid that contacts the bitumen feedstock.
56. The process of any one of claims 36 to 55, wherein the feed-miscible ionic liquid comprises a carbamate ionic liquid, a phosphonium ionic liquid, and combinations thereof.
57. The process of claim 56, wherein the carbamate ionic liquid comprises N, N'-dipropylammonium, N, N'-dipropyl carbamate (DPCARB) or N, N'-dibenzylammonium, N, N'-dibenzyl carbamate (DBCARB), and combinations thereof.
58. The process of claim 56, wherein the phosphonium ionic liquid comprises trihexyl-tetradecylphosphonium dicyanamide.
59. The process of any one of claims 36 to 58, wherein the non-catalytic treatment further comprises heating the ionic liquid-bitumen mixture at a heating temperature below the mixing temperature.
60. The process of claim 59, wherein the heating temperature is between about and about 120 C.
61. The process of claim 59 or 60, wherein the heating is performed near atmospheric pressure.
62. The process of any one of claims 36 to 61, wherein the concentration of the feed-miscible ionic liquid in the ionic liquid-bitumen mixture is between about 5 wt% and about 50 wt%.
63. A process for upgrading a bitumen feedstock comprising bitumen and a diluent, comprising:
contacting the bitumen feedstock with a feed-immiscible ionic liquid to obtain an ionic liquid-bitumen mixture; and subjecting the ionic liquid-bitumen mixture to a non-catalytic treatment, the non-catalytic treatment comprising mixing the ionic liquid-bitumen mixture to obtain a treated ionic liquid-bitumen mixture;
wherein at least one of a Total Acid Number (TAN) of the treated ionic liquid-bitumen mixture and a heavy metal content of the treated ionic liquid-bitumen mixture is reduced compared to the bitumen feedstock.
64. The process of claim 63, wherein the bitumen feedstock comprises a residuum stream from a distillation tower that has been operated to remove light hydrocarbon components.
65. The process of claim 63, wherein the bitumen feedstock comprises a bitumen stream that is obtained from an in situ recovery operation or from surface mining operations.
66. The process of any one of claims 63 to 65, wherein the diluent is selected from the group consisting of a naphthenic diluent, toluene and a mixture thereof.
67. The process of any one of claims 63 to 56, further comprising subjecting the treated ionic liquid-bitumen mixture to a liquid-liquid separation to obtain a first phase comprising the bitumen and the diluent and a second phase comprising a recovered feed-immiscible ionic liquid.
68. The process of claim 67, further comprising separating the first phase to recover the diluent as a recovered diluent, and to obtain a treated bitumen product.
69. The process of claim 68, wherein recovering the diluent comprises evaporating the diluent to obtain the treated bitumen product.
70. The process of claim 68 or 69, further comprising contacting at least a portion of the recovered diluent with the bitumen feedstock.
71. The process of any one of claims 67 to 70, wherein the recovered feed-immiscible ionic liquid is reused as part of the feed-immiscible ionic liquid that contacts the bitumen feedstock.
72. The process of any one of claims 63 to 71, wherein the feed-immiscible ionic liquid comprises an amino acid based ionic liquid, an imidazolium ionic liquid, a phosphonium ionic liquid, a carbamate ionic liquid, and combinations thereof.
73. The process of claim 72, wherein the amino acid ionic liquid comprises tetraethylammonium 8-alaninate, 1-ethy1-3-methylimidazolium glycinate, and combinations thereof.
74. The process of claim 72, wherein the imidazolium ionic liquid comprises 1-ethy1-3-methylimidazolium ethyl sulphate, 1-buty1-3-methylimidazolium tetrafluoroborate, 1-ethy1-3-methylimidazolium tetrafluoroborate, and combinations thereof.

,
75. The process of claim 72, wherein the phosphonium ionic liquid comprises tributyl-methylphosphonium methyl sulphate.
76. The process of claim 72, wherein the carbamate ionic liquid comprises N, N'-dimethylammonium, N, N'-dimethylcarbamate (DMCARB).
77. The process of any one of claims 63 to 76, wherein the non-catalytic treatment further comprises heating the ionic liquid-bitumen mixture at a heating temperature.
78. The process of claim 77, wherein the heating temperature is between about and about 70 C.
79. The process of any one of claims 63 to 78, wherein the concentration of the feed-immiscible ionic liquid in the ionic liquid-bitumen mixture is between about 5 wt%
and about 50 wt%.
80. The process of any one of claims 63 to 78, wherein the proportion of the bitumen relative to the feed-immiscible ionic liquid is between about 1:2 w/w and about 1:1 w/w.
81. The process of any one of claims 63 to 80, wherein the heavy metal content comprises at least one of a nickel content, an iron content and a vanadium content.
82. A process for upgrading a bitumen feedstock comprising bitumen and a diluent, comprising:
contacting the bitumen feedstock with an ionic liquid to obtain an ionic liquid-bitumen mixture;
mixing the ionic liquid-bitumen mixture at a mixing temperature; and separating the ionic liquid-bitumen mixture to obtain a first phase comprising treated bitumen and the diluent from a second phase comprising a recovered ionic liquid;
wherein the treated bitumen has a reduced heavy metal content compared to the bitumen feedstock.

, ,
83. The process of claim 82, wherein the bitumen feedstock comprises a residuum stream from a distillation tower that has been operated to remove light hydrocarbon components.
84. The process of claim 82, wherein the bitumen feedstock comprises a bitumen stream that is obtained from an in situ recovery operation or from surface mining operations.
85. The process of any one of claims 82 to 84, wherein the diluent is selected from the group consisting of a naphthenic diluent, toluene and a mixture thereof.
86. The process of any one of claims 82 to 85, wherein the ionic liquid is a feed-immiscible ionic liquid, and wherein the first phase and the second phase are obtained by subjecting the ionic liquid-bitumen mixture to a liquid-liquid separation.
87. The process of any one of claims 82 to 86, further comprising separating the first phase to recover the diluent as a recovered diluent, and to obtain a treated bitumen product.
88. The process of claim 87, wherein recovering the diluent comprises evaporating the diluent to obtain the treated bitumen product.
89. The process of claim 87 or 88, further comprising contacting at least a portion of the recovered diluent with the bitumen feedstock.
90. The process of any one of claims 82 to 89, wherein the recovered ionic liquid is reused as part of the ionic liquid that contacts the bitumen feedstock.
91. The process of any one of claims 82 to 90, wherein the ionic liquid comprises an amino acid based ionic liquid, an imidazolium ionic liquid, a phosphonium ionic liquid, a carbamate ionic liquid, and combinations thereof.
92. The process of claim 91, wherein the amino acid ionic liquid comprises tetraethylammonium P-alaninate, 1-ethy1-3-methylimidazolium glycinate, and combinations thereof.

, .
93. The process of claim 91, wherein the imidazolium ionic liquid comprises 1-ethy1-3-methylimidazolium ethyl sulphate, 1-buty1-3-methylimidazolium tetrafluoroborate, 1-ethy1-3-methylimidazolium tetrafluoroborate, and combinations thereof.
94. The process of claim 91, wherein the phosphonium ionic liquid comprises tributyl-methylphosphonium methyl sulphate.
95. The process of claim 91, wherein the carbamate ionic liquid comprises N, N'-dimethylammonium, N, N'-dimethylcarbamate (DMCARB).
96. The process of any one of claims 82 to 95, further comprising heating the ionic liquid-bitumen mixture at a heating temperature.
97. The process of claim 96, wherein the heating temperature is between about and about 70 C.
98. The process of any one of claims 82 to 97, wherein the concentration of the ionic liquid in the ionic liquid-bitumen mixture is between about 5 wt% and about 50 wt%.
99. The process of any one of claims 82 to 97, wherein the proportion of the bitumen relative to the ionic liquid is between about 1:2 w/w and about 1:1 w/w.
100. The process of any one of claims 82 to 99, wherein the heavy metal content comprises at least one of a nickel content, an iron content, and a vanadium content.
101. A process for upgrading a bitumen feedstock comprising bitumen and a diluent, comprising:
contacting the bitumen feedstock with an amino acid ionic liquid to obtain an ionic liquid-bitumen mixture;
mixing the ionic liquid-bitumen mixture at a mixing temperature; and separating the ionic liquid-bitumen mixture to obtain a first phase comprising treated bitumen and the diluent from a second phase comprising a recovered amino acid ionic liquid;

, , wherein the Total Acid Number (TAN) of the treated bitumen is reduced compared to the TAN of the bitumen feedstock.
102. The process of claim 101, wherein the bitumen feedstock comprises a residuum stream from a distillation tower that has been operated to remove light hydrocarbon components.
103. The process of claim 101, wherein the bitumen feedstock comprises a bitumen stream that is obtained from an in situ recovery operation or from surface mining operations.
104. The process of any one of claims 101 to 103, wherein the diluent is selected from the group consisting of a naphthenic diluent, toluene and a mixture thereof.
105. The process of any one of claims 101 to 104, wherein the first phase and the second phase are obtained by subjecting the ionic liquid-bitumen mixture to a liquid-liquid separation.
106. The process of any one of claims 101 to 105, further comprising separating the first phase to recover the diluent as a recovered diluent, and to obtain a treated bitumen product.
107. The process of claim 106, wherein recovering the diluent comprises evaporating the diluent to obtain the treated bitumen product.
108. The process of claim 106 or 107, further comprising contacting at least a portion of the recovered diluent with the bitumen feedstock.
109. The process of any one of claims 101 to 108, wherein the recovered amino acid ionic liquid is reused as part of the amino acid ionic liquid that contacts the bitumen feedstock.
110. The process of any one of claims 101 to 109, wherein the amino acid ionic liquid comprises tetraethylammonium [3-alaninate, 1-ethy1-3-methylimidazolium glycinate, and combinations thereof.
111. The process of any one of claims 101 to 110, further comprising heating the ionic liquid-bitumen mixture at a heating temperature.
112. The process of claim 111, wherein the heating temperature is between about 40 C and about 70 C.
113. The process of any one of claims 101 to 112, wherein the concentration of the amino acid ionic liquid in the ionic liquid-bitumen mixture is between about 5 wt%
and about 50 wt%.
114. The process of any one of claims 101 to 112, wherein the proportion of the bitumen relative to the amino acid ionic liquid is between about 1:2 w/w and about 1:1 w/w.
115. A process for upgrading a bitumen feedstock, comprising:
contacting a first ionic liquid catalyst with the bitumen feedstock to obtain a first ionic liquid-bitumen mixture;
subjecting the first ionic liquid-bitumen mixture to a catalytic cracking treatment, the catalytic cracking treatment comprising heating the first ionic liquid-bitumen mixture under catalytic cracking conditions to obtain an ionic liquid-cracked bitumen mixture;
contacting the ionic liquid-cracked bitumen mixture with a second ionic liquid to obtain a second ionic liquid-bitumen mixture; and subjecting the second ionic liquid-bitumen mixture to a non-catalytic treatment, the non-catalytic treatment comprising mixing the second ionic liquid-bitumen mixture to obtain a treated ionic liquid-bitumen mixture.
116. The process of claim 115, further comprising separating the first ionic liquid catalyst from the ionic liquid-cracked bitumen mixture to obtain a recovered first ionic liquid catalyst.
117. The process of claim 116, wherein the recovered first ionic liquid is reused as part of the first ionic liquid that contacts the bitumen feedstock.
118. The process of any one of claims 115 to 117, further comprising separating the second ionic liquid from the treated ionic liquid-bitumen mixture to obtain a recovered second ionic liquid.
119. The process of claim 118, wherein the recovered second ionic liquid is reused as part of the second ionic liquid that contacts the ionic liquid-cracked bitumen mixture.
120. The process of any one of claims 115 to 119, further comprising adding a diluent to the bitumen feedstock or to the second ionic liquid-bitumen mixture.
121. The process of any one of claims 115 to 120, further comprising subjecting the bitumen feedstock to a pre-treatment prior to the contacting of the bitumen feedstock with the first ionic liquid catalyst.
122. The process of claim 121, wherein the pre-treatment comprises heating the bitumen feedstock at a pre-treatment temperature.
123. The process of claim 122, wherein the pre-treatment temperature is sufficient to reduce viscosity of the bitumen feedstock.
124. The process of any one of claims 121 to 123, wherein the pre-treatment comprises adding a diluent to the bitumen feedstock.
125. The process of claim 124, wherein the diluent comprises at least one of a naphthenic solvent, an aromatic hydrocarbon, and a non-deasphalting organic solvent.
126. The process of claim 124 or 125, wherein the diluent comprises toluene.
127. The process of claim 115, wherein the bitumen feedstock comprises bitumen and a diluent.
128. The process of any one of claims 124 to 127, further comprising recovering the diluent following the non-catalytic treatment to obtain a recovered diluent.
129. The process of claim 128, further comprising contacting at least a portion of the recovered diluent with the bitumen feedstock or the second ionic liquid-bitumen mixture.
130. The process of any one of claims 115 to 129, wherein the first ionic liquid catalyst comprises an acidic ionic liquid catalyst.
131. The process of claim 130, wherein the acidic ionic liquid catalyst is a Lewis acidic ionic liquid comprising a Lewis acidic anion and a cation selected from the group consisting of 1,3-dialkylimidazolium cations, tetraalkylphosphonium cations, tetraalkylammonium cations, trialkylammonium cations and combinations thereof.
132. The process of claim 131, wherein the Lewis acidic ionic liquid catalyst comprises a Lewis acidic anion and a 1-alky1-3-methylimidazolium cation.
133. The process of claim 132, wherein the 1-alky1-3-methylimidazolium cation is selected from the group consisting of 1-ethy1-3-methylimidazolium (EMIM) and 1-n-buty1-3-methylimidazolium (BMIM).
134. The process of claim 131, wherein the Lewis acidic ionic liquid catalyst comprises a Lewis acidic anion and a trialkylammonium cation.
135. The process of claim 134, wherein the trialkylammonium cation comprises triethylammonium.
136. The process of any one of claims 131 to 135, wherein the Lewis acidic anion is a chlorometallate anion.
137. The process of claim 136, wherein the chlorometallate anion is selected from the group consisting of A1C14-, Al2C17-, FeC14- and Fe2C17-.
138. The process of any one of claims 131 to 137, wherein the Lewis acidic ionic liquid is selected from the group consisting of [EMIM][AIC14], [BMIM][AIC14], [EMIM][FeCI4], [BMIM][FeC14].
139. The process of claim 138, wherein the Lewis acidic ionic liquid is [EMIM][A1C14].

, ,
140. The process of claim 131, wherein the Lewis acidic ionic liquid comprises a metal ion-modified ionic liquid.
141. The process of claim 140, wherein the metal ion-modified ionic liquid is selected from the group consisting of [Et3NH][A1C14]-Ni2+, [EM1M][A1C14]-Ni2+, [BMIM][A1C14]-Ni2+, [Et3NH][A1C14]-Fe2+, [EM1M][A1C14]-Fe2+, [BM1M][A1C14]-Fe2+ and combinations thereof.
142. The process of any one of claims 115 to 141, wherein the second ionic liquid is a feed-miscible ionic liquid.
143. The process of claim 142, wherein the feed-miscible ionic liquid comprises a carbamate ionic liquid, a phosphonium ionic liquid, and combinations thereof.
144. The process of claim 143, wherein the carbamate ionic liquid comprises N, N'-dipropylammonium, N, N'-dipropyl carbamate (DPCARB) or N, N'-dibenzylammonium, N, N'-dibenzyl carbamate (DBCARB), and combinations thereof.
145. The process of claim 143, wherein the phosphonium ionic liquid comprises trihexyl-tetradecylphosphonium dicyanamide.
146. The process of any one of claims 115 to 141, wherein the second ionic liquid is a feed-immiscible ionic liquid.
147. The process of claim 146, wherein the feed-immiscible ionic liquid comprises an amino acid based ionic liquid, an imidazolium ionic liquid, a phosphonium ionic liquid, a carbamate ionic liquid, and combinations thereof.
148. The process of claim 147, wherein the amino acid ionic liquid comprises tetraethylammonium 8-alaninate, 1-ethy1-3-methylimidazolium glycinate, and combinations thereof.
149. The process of claim 147, wherein the imidazolium ionic liquid comprises 1-ethyl-3-methylimidazolium ethyl sulphate, 1-buty1-3-methylimidazolium tetrafluoroborate, 1-ethy1-3-methylimidazolium tetrafluoroborate, and combinations thereof.
150. The process of claim 147, wherein the phosphonium ionic liquid comprises tributyl-methylphosphonium methyl sulphate.
151. The process of claim 147, wherein the carbamate ionic liquid comprises N, N'-dimethylammonium, N, N'-dimethylcarbamate (DMCARB).
152. The process of any one of claims 115 to 151, wherein at least one of a Total Acid Number (TAN), a viscosity, a heavy metal content, and an asphaltene content of the treated ionic liquid-bitumen mixture is reduced compared to the bitumen feedstock.
153. The process of claim 152, wherein the heavy metal content comprises at least one of a nickel content, an iron content, and a vanadium content.
CA3074850A 2020-03-05 2020-03-05 Ionic liquids for upgrading of bitumen Pending CA3074850A1 (en)

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CA3172912A CA3172912A1 (en) 2020-03-05 2021-03-04 Upgrading of heavy oil or heavy oil-derived feedstock by contact with a feed-miscible ionic liquid
CA3172913A CA3172913A1 (en) 2020-03-05 2021-03-04 Upgrading of a feedstock including heavy oil or heavy oil-derived product and a diluent by contact with an ionic liquid
CA3111226A CA3111226A1 (en) 2020-03-05 2021-03-04 Upgrading of heavy oil or heavy oil-derived product with ionic liquids
US17/192,704 US20210277315A1 (en) 2020-03-05 2021-03-04 Upgrading of heavy oil or heavy oil-derived product with ionic liquids
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