Nova Patents
CA2973971C

Separations with ionic liquid solvents

Abstract

Disclosed are systems and methods which provide a process stream comprising a gaseous component, capture the gaseous component from the process stream by an ionic liquid solvent of a separator, and recover a captured gaseous component from the ionic liquid solvent in a regenerator. A second gaseous component from the process stream may be captured by the ionic liquid solvent of the separator, and the second gaseous component may be recovered from the ionic liquid solvent in the regenerator. Alternatively, the second gaseous component from the process stream may be uncaptured by the ionic liquid solvent, and the uncaptured second gaseous component may be recovered from a membrane unit.

CA2973971C, drawing sheet 1
Sheet 1 of 3

Term

8.3 yearsleft in the term

Expires 15 January 2035.

  1. Priority and filed
  2. Granted
  3. Today
  4. Expires

23 claims: 13 independent, 10 dependent

  1. 1
    CLAIMS:1. A method comprising: providing a polymerization process stream comprising an olefin and an alkane, wherein the olefin is propylene and the alkane is propane;capturing at least a portion of the olefin from the process stream by an ionic liquid solvent;and recovering at least a portion of a captured olefin from the ionic liquid solvent, wherein the ionic liquid comprises butylethylimidazolium tetrafluoroborate ([beim][BF4]), butylethylimidazolium hexafluorophosphate ([beim][[PF6]), butylethylimidazolium trifluoromethanesulfonate ([beim][TfO]), butylethylimidazolium nitrate ([beim][NO3]), butylmethylimidazolium trifluoroacetate ([bmim][TFA]), diethylimidazolium trifluoroacetate ([eeim][TFA]), diethylimidazolium trifluoromethanesulfonate ([eeim][TfO]), diethylimidazolium nitrate ([eeim][NO 3 ]), dimethylimidazolium nitrate ([mmim][N0 3 ]), ethyl-2,4-dimethylimidazolium trifluoroacetate ([e-2,4-mmim][TFA]), ethyl-2,4-dimethylimidazolium trifluoromethanesulfonate ([e-2,4-mmim][TfO]), ethyl-2,4-dimethylimidazolium nitrate ([e-2,4-mmim][NO 3 ]), ethyldimethylimidazolium tetrafluoroborate ([emmim][BF4]), ethyldimethylimidazolium trifluoroacetate ([emmim][TFA]), ethyldimethylimidazolium trifluoromethanesulfonate ([emmim][TfO]), ethylmethylimidazolium trifluoroacetate ([emim][TFA]), ethylmethylimidazolium nitrate ([emim][N0 3 ]), ethylpropylimidazolium tetrafluoroborate ([eprim][BF4]), ethylpropylimidazolium hexafluorophosphate ([eprim] [PF«]), ethylpropylimidazolium trifluoroacetate ([eprim] [TF A]), ethylpropylimidazolium trifluoromethanesulfonate ([eprim] [TfO]), ethylpropylimidazolium nitrate ([eprim] [NOs]), ethoxyethylmethylimidazolium tetrafluoroborate ([etO-emim][BF4]), ethoxyethylmethylimidazolium hexafluorophosphate ([etO-emim][PF6]), ethoxyethylmethylimidazolium trifluoroacetate ([etO-emim][TFA]), ethoxyethylmethylimidazolium trifluoromethanesulfonate ([etO-emim][TfO]), ethoxyethylmethylimidazolium nitrate ([etO-emim][NO 3 ]), ethoxydimethylimidazolium methanesulfonate ([etO-mmim][CH 3 SO 3 ]), ethoxydimethylimidazolium trifluoroacetate ([etO-mmim][TFA]), heptylmethylimidazolium tetrafluoroborate ([hpmim][BF4]), hexylethylimidazolium tetrafluoroborate ([hxeim][BF4]), hexylmethylimidazolium Date Reçue/Date Received 2021-08-17 84031127 tetrafluoroborate ([hxmim][BF4]), hexylmethylimidazolium hexafluorophosphate ([hxmim][PFe]), hexylmethylimidazolium nitrate ([hxmim][N03]), hexyldimethylimidazolium tetrafluoroborate ([hxmmim][BF4]), methoxy ethylmethylimidazolium tetrafluoroborate ([meO-emim] [BF4]), methoxyethylmethylimidazolium hexafluorophosphate ([meO-emim] [PFô]), methoxy ethylmethylimidazolium trifluoroacetate ([meO-emim][TFA]), methoxyethylmethylimidazolium trifluoromethanesulfonate ([meO-emim] [TfO]), methoxyethylmethylimidazolium nitrate ([me0-emim][N03]), methoxypropylmethylimidazolium tetrafluoroborate ([meO-prmim][BF4]), methoxypropylmethylimidazolium hexafluorophosphate ([meO-prmim][PF6]), methoxypropylmethylimidazolium trifluoroacetate ([meO-prmim][TFA]), methoxypropylmethylimidazolium trifluoromethanesulfonate ([meO-prmim][TfO]), methylpropylimidazolium methanesulfonate ([mprim][CH3SO3]), methylpropylimidazolium trifluoroacetate ([mprim][TFA]), methylpropylimidazolium nitrate ([mprim][N03]), hydroxy lethylmethylimidazolium methanesulfonate ([OHemim][CH3SO3]), hydroxyloctylmethylimidazolium tetrafluoroborate ([OH-omim][BF4]), hydroxyloctylmethylimidazolium hexafluorophosphate ([OH-omim][PF6]), hydroxyloctylmethylimidazolium nitrate ([OH-omim][NO3]), hydroxylpropylmethylimidazolium methanesulfonate ([OH-prmim][CH3SO3]), octylmethylimidazolium tetrafluoroborate ([omim][BF4]), phenylethylmethylimidazolium methanesulfonate ([ph-emim][CH3SO3]), phenylethylmethylimidazolium hexafluorophosphate ([ph-emim][PF6]), phenylethylmethylimidazolium trifluoroacetate ([ph-emim][TFA]), phenylethylmethylimidazolium trifluoromethanesulfonate ([phemim][TfO]), phenylethylmethylimidazolium nitrate ([ph-emim][N03]), phenylmethylimidazolium methanesulfonate ([ph-mim][CH3SO3]), phenylmethylimidazolium trifluoroacetate ([ph-mim][TFA]), phenylmethylimidazolium trifluoromethanesulfonate ([ph-mim][TfO]), phenylmethylimidazolium nitrate ([phmim][N03]), phenyldimethylimidazolium methanesulfonate ([ph-mmimHCHsSCh]), phenyldimethylimidazolium phenyldimethylimidazolium phenyldimethylimidazolium phenyldimethylimidazolium hexafluorophosphate trifluoroacetate trifluoromethanesulfonate nitrate ([ph-mmim][N03]), ([ph-mmim] [PFô]), ([ph-mmim] [TFA]), ([ph-mmim][TfO]), pentylmethylimidazolium Date Reçue/Date Received 2021-08-17 84031127 tetrafluoroborate ([pnmim][BF4]), pentylmethylimidazolium hexafluorophosphate ([pnmim][PF6]), pentylmethylimidazolium trifluoroacetate ([pnmim][TFA]), pentylmethylimidazolium trifluoromethanesulfonate ([pnmim][TfO]), pentylmethylimidazolium nitrate ([pnmim][N03]), propylmethylimidazolium trifluoroacetate ([prmim][TFA]), propylmethylimidazolium trifluoromethansulfonate ([prmim][TfO]), propylmethylimidazolium nitrate ([prmim][N03]), l-butyl-2methylpyridinium tetrafluoroborate ([l-b-2-mpy][BF4]), l-butyl-2-methylpyridinium hexafluorophosphate ([l-b-2-mpy][PF6]), l-butyl-2-methylpyridinium trifluoromethanesulfonate ([l-b-2-mpy][TfO]), l-butyl-3-methylpyridinium tetrafluoroborate ([l-b-3-mpy][BF4]), l-butyl-3-methylpyridinium hexafluorophosphate ([l-b-3-mpy][PFô]), l-butyl-4-methylpyridinium tetrafluoroborate ([l-b-4-mpy][BF4]), 1butyl-4-methylpyridinium hexafluorophosphate ([l-b-4-mpy][PFe]), l-ethyl-2methylpyridinium tetrafluoroborate ([l-e-2-mpy][BF4]), l-ethyl-2-methylpyridinium trifluoroacetate ([l-e-2-mpy][TFA]), l-ethyl-2-methylpyridinium trifluoromethanesulfonate ([l-e-2-mpy][TfO]), l-ethyl-3-methylpyridinium tetrafluoroborate ([l-e-3-mpy][BF4]), l-ethyl-3-methylpyridinium trifluoroacetate ([l-e-3mpy][TFA]), l-ethyl-3-methylpyridinium trifluoromethanesulfonate ([l-e-3-mpy][rfO]), l-ethyl-4-dimethylacetylpyridinium tetrafluoroborate ([l-e-4-DMApy][BF4]), l-ethyl-4dimethylacetylpyridinium hexafluorophosphate ([l-e-4-DMApy][PFe]), l-ethyl-4methylpyridinium tetrafluoroborate ([l-e-4-mpy][BF4]), l-ethyl-4-methylpyridinium trifluoroacetate ([l-e-4-mpy][TFA]), l-ethyl-4-methylpyridinium trifluoromethanesulfonate ([l-e-4-mpy][TfO]), l-ethyl-4-methylpyridinium nitrate ([l-e-4mpy][NO 3 ]), l-hexyl-4-methylpyridinium tetrafluoroborate ([l-hx-4-mpy][BF4]), 1-propyl3-methylpyridinium tetrafluoroborate ([l-pr-3-mpy][BF4]), l-propyl-3-methylpyridinium hexafluorophosphate ([l-pr-3-mpy][PFô]), l-propyl-3-methylpyridinium trifluoroacetate ([l-pr-3-mpy][TFA]), l-propyl-3-methylpyridinium trifluoromethanesulfonate ([l-pr-3mpy][TfO]), l-propyl-4-methylpyridinium tetrafluoroborate ([l-pr-4-mpy][BF4]), 1propyl-4-methylpyridinium hexafluorophosphate ([l-pr-3-mpy][PF6]), l-propyl-4methylpyridinium trifluoroacetate ([l-pr-4-mpy][TFA]), l-propyl-4-methylpyridinium trifluoromethanesulfonate ([l-pr-4-mpy][TfO]), l-propyl-4-methylpyridinium nitrate ([1pr-4-mpy][NO3]), butylpyridinium hexafluorophosphate ([bpy][PFô]), butylpyridinium trifluoroacetate ([bpy][TFA]), butylpyridinium trifluoromethanesulfonate ([bpy][TfO]), Date Reçue/Date Received 2021-08-17 84031127 butylpyridinium nitrate ([bpy][NO 3 ]), ethylpyridinium nitrate ([epy][NO 3 ]), heptylpyridinium tetrafluoroborate ([hppy][BF4]), heptylpyridinium hexafluorophosphate ([hppyHPFe]), heptylpyridinium nitrate ([hppy][NO 3 ]), hexylpyridinium tetrafluoroborate ([hxpy][BF4]), hexylpyridinium hexalfuorophosphate ([hxpy][PF6]), hexylpyridinium trifluoromethansulfonate ([hxpy][TfO]), hexylpyridinium nitrate ([hxpy][NO 3 ]), hydroxypropylpyridinium methanesulfonate ([OH-prpy][CH 3 SO 3 ]), octylpyridinium tetrafluoroborate ([opy][BF 4 ]), pentylpyridinium tetrafluoroborate ([pnpy][BF 4 ]), pentylpyridinium hexafluorophosphate ([pnpy][PFe]), pentylpyridinium trifluoroacetate ([pnpy][TFA]). pentylpyridinium trifluoromethanesulfonate ([p»py][TfO]), pentylpyridinium nitrate ([pnpy][NO3]), propylpyridinium trifluoroacetate ([prpy][TFA]), propylpyridinium trifluoromethanesulfonate ([prpy][TfO]), propylpyridinium nitrate ([prpy][NO 3 ]), butylmethylpyrrolidinium tetrafluoroborate ([bmpyr][BF 4 ]), butylmethylpyrrolidinium hexafluorophosphate ([bmpyr][PFô]), butylmethylpyrrolidinium trifluoromethanesulfonate ([bmpyr][TfO]), butylpyrrolidinium acetate ([bpyr][CH 3 CÛ2]), hexylmethylpyrrolidinium tetrafluoroborate ([hxmpyr][BF 4 ]), hexylmethylpyrrolidinium hexafluorophosphate ([hxmpyr][PF6]), hexylpyrrolidinium acetate ([hxpyr][CH 3 CO2]), hexylpyrrolidinium trifluoroacetate ([hxpyr][TFA]), octylpyrrolidinium tetrafluoroborate ([opyr][BF 4 ]), octylpyrrolidinium methanesulfonate ([opyr][CH 3 SO 3 ]), octylpyrrolidinium hexafluorophosphate ([opyr][PF6]), octylpyrrolidinium nitrate ([opyr][NO 3 ]), propylmethylpyrrolidinium tetrafluoroborate ([prmpyr][BF 4 ]), propylmethylpyrrolidinium hexafluorophosphate ([prmpyr][PF6]), propylmethylpyrrolidinium trifluoroacetate ([prmpyr][TFA]), propylmethylpyrrolidinium trifluoromethanesulfonate ([prmpyr][TfO]), butylethyldimethylammonium butylethyldimethylammonium butylethyldimethylammonium butylethyldimethylammonium tetrafluoroborate hexafluorophosphate trifluoroacetate trifluoromethanesulfonate ([bemm-N] [BF 4 ]), ([bemm-N][PF 6 ]), ([bemm-N] [TFA]), ( [bemm-N] [TfO]), butyltrimethylammonium trifluoroacetate ([bmmm-N][TFA]), butyltrimethylammonium trifluoromethanesulfonate ([bmmm-N][TfO]), butyltrimethylammonium nitrate ([bmmmN][N0 3 ]), Ν,Ν,Ν-trimethylethanolammonium methanesulfonate ([choline][CH 3 SO 3 ]), Ν,Ν,Ν-trimethylethanolammonium nitrate ([choline] [NO 3 ]), ethylammonium hexafluorophosphate ([e-N][PFô]), tetraethylammonium tetrafluoroborate ([eeee-N][BF 4 ]), tetraethylammonium hexafluorophosphate ([eeee-N][PF6]), tetraethylammonium Date Reçue/Date Received 2021-08-17 84031127 trifluoromethanesulfonate ([eeee-N][TfO]), butyldimethylethanolammonium trifluoroacetate ([OHe-bmm-N][TFA]), butyldimethylethanolammonium trifluoromethanesulfonate ([OHe-bmm-N][TfO]), butyldimethylethanolammonium nitrate ([0He-bmm-N][N03]), ethyldimethylethanolammonium nitrate ([0He-emm-N][ NO3]), or combinations thereof.
  2. 4
    The method of any one of claims 1 to 3, wherein a total selectivity of the ionic liquid solvent to the olefin over propane is from 8 to 300.
  3. 5
    The method of any one of claims 1 to 4, wherein the ionic liquid solvent comprises a Ag(I) salt a Cu(I) salt or combinations thereof.
  4. 8
    The method of any one of claims 1 to 7, wherein said capturing is performed at a liquid-to-gas mass flow ratio from 1 to 350.
  5. 10
    The method of any one of claims 1 to 9, wherein a total solubility of the alkane in the ionic liquid solvent is 0.01 to 10 mol/L.
  6. 11
    The method of any one of claims 1 to 10, wherein said capturing is performed at a liquid-to-gas mass flow ratio such that at least a portion of the alkane is captured by the ionic liquid solvent in addition to the capture of at least a portion of the olefin.
  7. 14
    The method of any one of claims 11 to 13, further comprising:recovering at least a portion of a captured alkane from the ionic liquid solvent.
  8. 16
    The method of any one of claims 1 to 15, wherein said capturing is performed at a liquid-to-gas mass flow ratio such that at least a portion of the alkane from the process stream is not captured by the ionic liquid solvent.
  9. 19
    The method of any one of claims 1 to 18, wherein the ionic liquid solvent has a total selectivity to the olefin over the alkane greater than the total selectivity of [emim][Tf2N]-Ag to the olefin over the alkane.
  10. 20
    The method of any one of claims 1 to 19, wherein the olefin is captured by the ionic liquid solvent at a temperature from 20 °C to 40 °C.
  11. 21
    The method of any one of claims 1 to 20, wherein the olefin is captured by the ionic liquid solvent at a pressure from 100 psia (689.48 kPa) to 250 psia (1723.69 kPa). Date Reçue/Date Received 2021-08-17 84031127
  12. 22
    The method of any one of claims 1 to 21, wherein the ionic liquid solvent comprises a cation, an anion, and a Ag(I) salt, wherein the Ag(I) salt comprises an anion, wherein the anion of the Ag(I) salt matches the anion of the ionic liquid solvent.
  13. 23
    The method of any one of claims 1 to 22, wherein the ionic liquid solvent comprises a cation, an anion, and a Cu(I) salt, wherein the Cu(I) salt comprises an anion, wherein the anion of the Cu(I) salt matches the anion of the ionic liquid solvent. Date Reçue/Date Received 2021-08-17 CA 02973971 2017-07-14 (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT)