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`CE Ex. 2021
`Daicel v. Celanese
`|PR2O15_00173
`
` 1
`
`

`
`LISTING OF THE CLAIMS:
`
`This listing ofclaims will replace all prior versions and listings ofclaims in the
`
`application:
`
`I. (Original) An improved method for reduction and/or removal of permanganate-
`
`reducing compounds (PRC's), CH carboxylic acids and C342 alkyl iodide compounds formed in
`
`the carbonylation ofa carbonylatable reactant selected from the group consisting of methanol,
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`methyl acetate, methyl formate and dimethyl ether and mixtures thereof to an acetic acid product,
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`the products ofsaid earbonylation including a volatile ‘phase that is distilled to yield a purified
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`acetic _acid product and a first overhead comprising methyl iodide, water andat least one PRC,
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`wherein the improvement comprises the steps of: (a) distilling at least a portion ofthe tirst
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`overhead to produce a second overhead stream comprising methyl iodide, dirnethyl ether, and
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`said at least one PRC; (b) extracting the second overhead stream with water to form a first
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`raftinate and a first aqueous extract stream containing said at least one PRC; and (c) extracting
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`the tirst rattinate with water to form a second rafiinate and a second aqueous extract stream
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`containing said at least one PRC.
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`2. (Original) The method of claim I, wherein said at least one PRC comprises
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`acetaldchyde.
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`3. (Original)
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`'The method of claim 2, wherein sufiicient aeetaldehyde is removed from
`
`said volatile phase to maintain in said purified product a concentration of propionic acid less than
`
`about 400 parts per million by weight.
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`4. (Original) The method of claim 2, wherein sufficient acetaldehyde is removed from
`
`said volatile phase to maintain in said purified product a concentration of propionic acid less than
`
`about 250 parts per million by weight.
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`5. (Canceled)
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` 2
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`6. (Original) The method ofclaim 1, wherein extraction steps (b) and (c) are performed
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`in separate vessels.
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`7. (Original) The method of claim 1, wherein extraction steps (b) and (c) are performed
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`in at least one packed-bed extractor.
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`8. (Original) The method of claim l, wherein extraction steps (b) and (e) are performed
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`on trays within a single extraction vessel.
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`9. (Canceled)
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`l0. (Original) The method of claim ‘I, further comprising at least one further step of
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`.
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`extracting the second rafiinate with water to provide a third aqueous extract and a third rafiinate.
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`l 1. (Original) The method of claim l 0, wherein water for the at least one further
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`extraction step comprises at least a portion of one or more ofsaid first, second and third aqueous
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`CXll’élCl streams.
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`12. (Original) The method ofclaim 1, wherein said first overhead comprises dimethyl
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`ether.
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`13. (Canceled)
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`l4. (Original) The method ofelaim 1, wherein said distillation step (a) further comprises
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`the step of forming dimethyl ether during the distillation.
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`l5. (Original) The method ofclaim 1, wherein said distillation step (a) comprises at least
`
`two sequential distillation steps.
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`16. (Original) The method ofclaim I, wherein said second overhead comprises an _
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`amount of dimethyl ether in excess of any dimethyl ether present in the first overhead.
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` 3
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`

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`l7. (Original) A process for producing acetic acid, comprising the steps ofi
`
`(a) carbonylating at least one reactant selected from the group consisting of methanol,
`
`methyl acetate, methyl formate and dimethyl ether in a reactor containing a suitable reaction
`
`medium comprising an organic iodide;
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`(b) separating the products of said carbonylation into a volatile product ‘phase comprising
`
`acetic acid, and a less volatile phase:
`
`(c) distilling said volatile product phase to yield a purified acetic acid product and a first
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`overhead comprising said organic iodide and at least one permanganate reducing compound
`
`(PRC):
`
`(d) distilling at least a portion of the lirst overhead to produce a PRC-enriched second
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`overhead, said second overhead further comprising dimethyl ether; and
`
`(e) extracting the second overhead with water, wherein step (e) comprises at least two
`
`consecutive extraction steps, each extraction step comprising contacting the second overhead
`
`with water and separating therefrom an aqueous stream comprising said at least one PRC.
`
`18. (Original) The method of claim 17, wherein said at least one PRC comprises
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`acetaldehyde.
`
`I9. (Original) The method ofclaim 18, wherein sufficient acetaldehyde is removed from
`
`said volatile phase to maintain in said purified product a concentration of propionic acid less than
`
`about 400 parts per million by weight.
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`20. (Original) The method of claim ‘I8, wherein sufficient acetaldehyde is removed From
`
`said volatile phase to maintain in said purified product a concentration ofpropionic acid less than
`
`about 250 parts per millionby weight.
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`21 . (canceled)
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`22. (Original) The process ofclaim I7, wherein the at least two extraction steps are
`
`performed in separate vessels.
`
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`23. (Original) The process of claim I7, wherein extraction steps (b) and (c) are
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`performed on trays within a single extraction vessel.
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`24. (Original) The process of claim 17, wherein the at least two extraction steps are
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`performed in at least one packed-bed extractor.
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`25. (Original) The process ofclaim 17, wherein water for at least one of the at least two
`
`extraction steps comprises at least a portion ofone of the aqueous extract streams.
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`26. (Original) The method of claim I7, wherein said second overhead comprises an
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`amount of dimethyl ether in excess ofany dimethyl ether present in the first overhead.
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`27. (Original) The process ofclaim l7, wherein said First overhead comprises dimethyl
`
`ether.
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`28. (Canceled)
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`29. (Original) The process ofclaim I7, wherein said distillation step (d) further
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`comprises the step of forming dimethyl ether during the distillation.
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`30. (Previously Presented)
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`A process for separating a mixture comprising water, acetic
`
`acid. methyl iodide. methyl acetate, methanol, and at least one permanganate reducing compound
`
`(PRC), said process comprising the steps of: (a) distilling the mixture to separate the mixture into
`
`a plurality of streams, at least one of said streams being a PRC enriched overhead stream
`
`comprising dimethyl ether; and (b) extracting the PRC enriched overhead stream with water to
`
`produce an aqueous stream comprising said at least one PRC, and a rattinate stream comprising
`
`methyl iodide.
`
`3 l. (Previously Presented)
`
`The method of claim 30, wherein said PRC enriched
`
`overhead stream comprises an amount of dimethyl ether in excess ofany dimethyl ether present
`
` 5
`
`

`
`in the mixture comprising water, acetic acid, methyl iodide, methyl acetate, methanol, and at
`
`least one PRC.
`
`32. (Canceled)
`
`33. (Original) The process of claim 30, wherein said at least one PRC comprises
`
`acetaldehyde.
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`34. (Original) The method ofclaim 30, wherein said distillation step (a) further
`
`comprises the step of forming dimethyl ether during the distillation.
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`35. (Original) The process ofclaim 30. further comprising the step ofproviding said
`
`mixture by separating a liquid composition into a light phase and a heavy phase, said liquid
`
`composition comprising water, acetic acid, methyl iodide, methyl acetate, methanol, and said at
`
`least one PRC. wherein the light phase comprises said mixture and the heavy phase comprises
`
`methyl iodide.
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`36. (Previously Presented)
`
`The process ofclaim 35, wherein said at least one PRC
`
`comprises acetaldehyde.
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`37. (Previously Presented)
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`The process of claim 30. further comprising the steps of:
`
`performing a liquid-vapor phase separation on an effluent ofa methanol carbonylation reactor to
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`flirm a vapor phase and a liquid phase; distilling the vapor phase to form a first overhead and a
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`liquid product stream comprising acetic acid; and condensing at least a portion of the first
`
`overhead to provide said mixture comprising water, acetic acid, methyl iodide, methyl acetate,
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`methanol, and at least one PRC, and wherein at least a portion of said raffinate stream is recycled
`directly or indirectly back into said methanol carbonylation reactor.
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`38. (Canceled)
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` 6
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`

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`39. (Previously Presented)
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`The process of claim 37, wherein said at least one PRC
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`com rises acetaldch dc.
`P
`Y
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`40. (Previously Presented)
`
`The method ofclaim 39, wherein sufficient aeetaldehyde is
`
`removed from said PRC enriched overhead stream_to maintain a concentration ofpropionic acid
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`of less than about 400 parts per million by weight in said liquid product stream.
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`41. (Previously Presented)
`
`The method ofclaim 39, wherein sufficient acetaldehyde is
`
`removed from said PRC enriched overhead stream to maintain a concentration of propionic acid
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`of less than about 250 parts per million by weight in said liquid product stream.
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`42. (Previously Presented)
`
`The method of Claim 34, wherein said distillation step (a)
`
`further comprises the step of adding water to distillation step (a) in an amount sufficient to
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`produce dimethyl ether from a portion ofthe mixture during the distillation step (a).
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`43. (Previously Presented)
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`The method ofClaim 30, wherein the dimethyl ether is
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`produced from the mixture during said distillation step (a), wherein the dimethyl ether is added
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`to the mixture prior to distillation step (a), wherein the dimethyl ether is added to at least one of
`
`the plurality of streams produced by distillation step (a), or a combination thereof.
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`44.
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`(Previously Presented)
`
`The method of Claim 30, wherein said distillation
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`step (a) comprises distillation using a single distillation column.
`
`The method of Claim 30, wherein said distillation
`(Previously Presented) ‘
`45.
`step (21) comprises distillation using at least two distillation columns.
`
`I
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`46.
`
`(Previously Presented)
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`The method ofClaim 30, wherein said dimethyl
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`ether is present in said PRC enriched overhead stream at a concentration sufiicient to produce
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`said aqueous stream comprising said at least one PRC having a methyl iodide concentration of
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`less than 1.8 \VI°/0.
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`47.
`
`(Previously Presented)
`
`The method of Claim 30, wherein said dimethyl
`
`ether is present in said PRC enriched overhead stream at a concentration sutiieieiit to produce
`
`said aqueous stream comprising said at least one PRC having a methyl iodide concentration
`between about l.8 wt% and 0.5 wt%.
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`48.
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`(Previously Presented)
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`The method of Claim 30, wherein said dimethyl
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`ether is present in said PRC enriched overhead stream at a concentration su flicient to produce
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`said aqueous stream comprising said at least one "PRC having a methyl iodide concentration of
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`less than or equal to about 0.5 wt%.
`
`49. (Previously Presented)
`
`A process for separating a mixture comprising water, acetic
`
`acid, methyl iodide, methyl acetate, methanol, and at least one permanganate reducing compound
`
`(PRC), said process comprising the steps of:
`
`(a) distilling the mixture to separate the mixture into a plurality of streams, at least one of
`
`said streams being a PRC. enriched overhead stream comprising dimethyl ether; and
`
`(b) extracting the PRC enriched overhead stream with water to produce an aqueous
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`stream comprising said at least one PRC. and a raftinate stream comprising methyl iodide,
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`wherein step (b) comprises at least two consecutive extraction steps, each extraction step
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`comprising contacting the PRC enriched overhead stream with a water stream and separating
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`therefrom said aqueous stream comprising’ said at least one PRC and said rafiinate stream
`
`comprising methyl iodide, wherein a fresh water stream is used in each discrete extraction
`
`stage;or
`
`wherein step (b) comprises at least two consecutive extraction steps, each extraction step
`
`comprising contacting the PRC enriched overhead stream with a water stream and separating
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`tliereironi said aqueous stream comprising said at least one PRC and said ramnate stream
`
`comprising methyl iodide. wherein a single water stream passes through each of said discrete
`
`extraction stages in series: or
`
`wherein step (b) comprises contacting the PRC enriched overhead stream with a water
`
`stream and separating therefrom said aqueous stream comprising said at least one PRC and said
`
`raffinate stream comprising methyl iodide using a continuous contacting extractor; or a
`
`combination thereof.
`
` 8
`
`

`
`50. (Previously Presented)
`
`The method ofelaim 49, wherein said PRC enriched
`
`overhead stream comprises an amount ofdimethyl ether in excess of any dimethyl ether present
`
`in the mixture comprising water, acetic acid, methyl iodide, methyl acetate, methanol, and at
`
`least one PRC.
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`51. (Previously Presented)
`
`The process ofclaim 49, wherein said at least one PRC
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`comprises acetaldehyde.
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`52. (Previously Presented)
`
`The process of claim 49, further comprising the step of
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`providing said mixture by separating a liquid composition into a light phase and a heavy phase,
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`said liquid composition comprising water, acetic acid, methyl iodide. methyl acetate. methanol,
`
`and said at least one PRC, wherein the light phase comprises said mixture and the heavy phase
`
`comprises methyl iodide.
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`53. (Previously Presented)
`
`The process o‘l’claim 52, wherein said at least one PRC
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`comprises acetaldehyde.
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`54. (Previously Presented)
`
`The process of claim 49, further comprising the steps of:
`
`performing a liquid-vapor phase separation on an effluent of a methanol carbonylation reactor to
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`'l’orm a vapor phase and a liquid phase; distilling the vapor phase to form a first overhead and a
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`liquid product stream comprising acetic acid; and condensing at least a portion of the first
`
`overhead to provide said mixture comprising waterdacetie acid, methyl iodide, methyl acetate,
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`methanol, and at least one PRC, and wherein at least a portion of said raffinate stream is recycled
`
`directly or indirectly back into said methanol carbonylation reactor.
`
`55. (Previously Presented)
`
`The process of claim 54 wherein said at least one PRC
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`comprises acetaldehyde.
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`
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`56. (Previously Presented)
`
`The method ofelaim 55, wherein sufficient acetaldehyde is
`
`removed from said PRC enriched overhead stream to maintain a concentration ofpropionic acid
`
`of less than about 400 parts per million by weight in said liquid product stream.
`
`57. (Previously Presented)
`
`The method of claim 55, wherein sufficient acetaldehyde is
`
`removed from said PRC enriched overhead stream to maintain a concentration of propionic acid
`
`ofless than about 250 parts per million by weight in said liquid product stream.
`
`58. (Previously Presented)
`
`The method ofClaim 49, wherein said distillation step (a)
`
`further comprises the step of adding water to distillation step (a) in an amount sufficient to
`
`produce dimethyl ether from a portion ofthe mixture during said distillation step (a).
`
`59. (Previously Presented)
`
`The method of Claim 49, wherein the dimethyl ether is
`
`produced from the mixture during said distillation step (a), wherein the dimethyl ether is added
`
`to the mixture prior to distillation step (a), wherein the dimethyl ether is added to at least one of
`
`the plurality of streams produced by distillation step (a), or a combination thereof.
`
`60.
`
`(Previously Presented)
`
`The method of Claim 49, wherein said distillation
`
`step (a) comprises distillation using a single distillation column.
`
`6].
`
`(Previously Presented)
`
`The method of Claim 49, wherein said distillation
`
`step (21) comprises distillation using at least two distillation columns.
`
`62.
`
`(Previously Presented)
`
`The method of Claim 49, wherein said dimethyl
`
`ether is present in said PRC enriched overhead stream at a concentration sufficient to produce
`
`each of said aqueous streams comprising said at least one PRC, wherein each have a methyl
`
`iodide concentration of less than l .8 wt%.
`
`63.
`
`(Previously Presented)
`
`The method ofClaim 49, wherein said dimethyl
`
`ether is present in said PRC enriched overhead stream at a concentration sufileient to produce
`
`IO
`
`10
`
`
`10
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`

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`said aqueous stream comprising said at least one PRC having a methyl iodide concentration
`
`between about 1.8 wt% and 0.5 wt%.
`
`64.
`
`(Previously Presented)
`
`The method of Claim 49, wherein said dimethyl
`
`ether is present in said PRC enriched overhead stream at a concentration suflieient to produce
`
`each of said aqueous streams comprising said at least one PRC, wherein each have a methyl
`
`iodide concentration oflessthan or equal to about 0.5 wt%.
`
`65. (Previously Presented)
`
`A process for separating a mixture comprising water, acetic
`
`acid, methyl iodide, methyl acetate, methanol, and at least one permanganate reducing compound
`
`g
`
`(PRC), said process comprising, the steps of
`
`(a) distilling the mixture to separate the mixture into a plurality of streams, at least one of
`
`said streams being a PRC enriched overhead stream comprising dimethyl ether; and
`
`(b) extracting the PRC enriched overhead stream with water to form a first ratlinate and a
`first aqueous extract stream comprising said at least one PRC; followed by extracting the first
`raffinate with water to form a second raflinatc and a second aqueous extract stream comprising
`
`said at least one ‘PRC.
`
`66. (Previously Presented)
`
`The method ofelaim 65, wherein said PRC enriched
`
`overhead stream comprises an amount ofdimethyl ether in excess of any dimethyl ether present
`
`in the mixture comprising water, acetic acid, methyl iodide, methyl acetate, methanol, and at
`
`least one PRC.
`
`67. (Previously Presented)
`
`The process of claim 65, wherein said at least one PRC
`
`comprises acetaldehyde.
`
`68. (Previously Presented)
`
`The process ofclaim 65, further comprising the step of
`
`providing said mixture by separating a liquid composition into a light phase and a heavy phase,
`
`said liquid composition comprising water, acetic acid, methyl iodide, methyl acetate, methanol,
`
`and said at least one PRC. wherein the light phase comprises said mixture and the heavy phase
`
`comprises methyl iodide.
`
`ll
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`11
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`11
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`

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`69. (Previously Presented)
`
`The process of claim 68, wherein said at least one PRC
`
`comprises acetaldehyde.
`
`70. (Previously Presented)
`
`The process of claim 69, further comprising the steps of:
`
`performing a liquid—vapor phase separation on an ettluent ofa methanol carbonylation reactor to
`
`form a vapor phase and a liquid phase; distilling the vapor phase to form a first overhead and a _
`
`liquid product stream comprising acetic acid; and condensing at least a portion of the first
`
`overhead to provide said mixture comprising water, acetic acid, methyl iodide, methyl acetate,
`
`methanol. and at least one PRC, and wherein at least a portion of said second rafiinate is
`
`recycled directly or indirectly back into said methanol carbonylation reactor.
`
`71. (Previously Presented)
`
`The process of claim 70 wherein said at least one PRC
`
`comprises acetaldehyde.
`
`72. (Previously Presented)
`
`The method of claim 7], wherein sufficient acetaldehyde is
`
`removed from said PRC enriched overhead stream to maintain a concentration ofpropionic acid
`
`of less than about 400 parts per million by weight in said liquid product stream.
`
`73. (Previously Presented)
`
`The method ofclaim 7l, wherein sufficient acetaldehyde is
`
`removed from said PRC enriched overhead stream to maintain a concentration of propionic acid
`
`of less than about 250 parts per million by weight in said liquid product stream.
`
`74. (_Prcviously Presented)
`
`The method ofClaim 65, wherein said distillation step (a)
`
`further comprises the step of adding water to distillation step (a) in an amount sufficient to
`
`produce an amount ofdimcthyl ether lrom a portion of the mixture during said distillation step
`
`(ii) '
`
`75. (Previously Presented)
`
`The method ofClaim 65, wherein the dimethyl ether is
`
`produced from the mixture during said distillation step (21), wherein the dimethyl ether is added
`
`I2
`
`12
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`to the mixture prior to distillation step (a), wherein the dimethyl ether is added to at least one of
`
`the plurality ofstreams produced by distillation step (a), or a combination thereof.
`
`76.
`
`(Previously Presented)
`
`The method ofClaim 65, wherein said distillation
`
`step (21) comprises distillation using a single distillation column.
`
`77.
`
`(Previously Presented)
`
`The method of Claim 65. wherein said distillation
`
`step (a) comprises distillation using at least two distillation columns.
`
`78.
`
`(Previously Presented)
`
`The method of Claim 65, wherein said dimethyl
`
`ether is present in said PRC enriched overhead stream at a concentration sufficient to produce
`
`said first aqueous extract stream comprising said at least one PRC and said second aqueous
`
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`
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`
`79.
`
`(Previously Presented)
`
`The method ofClaim 65, wherein said dimethyl
`
`ether is present in said PRC enriched overhead stream at a concentration sufiicient to produce
`
`said aqueous stream comprising said at least one "PRC having a methyl iodide concentration
`)
`
`between about L8 wt% and 0.5 wt”/o.
`
`80.
`
`(Previously Presented)
`
`' The method ofClaim 65, wherein said dimethyl
`
`ether is present in said PRC enriched overhead stream at a concentration sufiicient to produce
`
`said first aqueous extract stream comprising said at least one PRC and said second aqueous
`
`extract stream comprising said at least one'PRC, wherein each of said aqueous extract streams
`
`have a methyl iodide concentration of less than or equal to about 0.5 wt%.
`
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