throbber
Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`UNITED STATES PATENT AND TRADEMARK OFFICE
`_______________
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`_____________
`
`DAICEL CORPORATION
`Petitioner
`v.
`
`CELANESE INTERNATIONAL CORPORATION
`Patent Owner
`
`Patent No. 8,076,507
`Issue Date: Dec 13, 2011
`Title: REMOVAL OF PERMANGANATE REDUCING COMPOUNDS FROM
`METHANOL CARBONYLATION PROCESS STREAM
`
`Inter Partes Review No. 2015-00171
`____________________________________________________________
`
`FIRST DECLARATION OF WILLIAM C. JONES
`
`(cid:44)(cid:51)(cid:53)(cid:3)(cid:49)(cid:82)(cid:17)(cid:3)(cid:21)(cid:19)(cid:20)(cid:24)(cid:16)(cid:19)(cid:19)(cid:20)(cid:26)(cid:20)
`(cid:40)(cid:91)(cid:75)(cid:76)(cid:69)(cid:76)(cid:87)(cid:3)(cid:20)(cid:19)(cid:22)(cid:28)
`
`000001
`
`

`
`Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`I, William C. Jones, hereby declare and say that:
`
`I. Introduction
`
`1.
`
`I am a chemical engineer, currently retired from Eastman Chemical
`
`Company.
`
`2.
`
`I have more than 40 years of experience in industrial-scale chemical
`
`processing, including the industrial-scale production of acetic acid and acetic
`
`anhydride. A copy of my curriculum vitae is attached as Exhibit 1038.
`
`3.
`
`I am very familiar with the subject matter of industrial-scale distillations and
`
`separations, in general. Most of my career at Eastman Chemical was involved
`
`in R&D and operations management for production of acetic acid and acetyl
`
`derivatives. This included pilot plant operation for production of acetic acid
`
`via methyl acetate carbonylation, and the design, construction,
`
`commissioning, and operation of acetic acid plants for Eastman and later for
`
`SIPCHEM (Saudi International Petrochemical Company). I also led process
`
`improvement and development efforts for the acetyl processes at Eastman and
`
`SIPCHEM. I was the Technology Director for the development of a nickel
`
`catalyzed methanol carbonylation technology. The last 5 years of my career
`
`at Eastman were spent in Eastman’s licensing group as Director of
`
`2
`000002
`
`

`
`Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`Technology. During this time, the licensing of acetic acid technology was a
`
`major focus of my work. My evaluation of projects included the technical
`
`aspects, as well as economic, financial and business evaluations comparing
`
`Eastman technology with other acetic acid technologies.
`
`4.
`
`I am named inventor on two patents/patent applications, both involving the
`
`process of methanol carbonylation. A listing of my patents and patent
`
`applications is included with my CV. These are relevant because they relate
`
`to and partially describe my experience and expertise in the field of the
`
`production and purification of acetic acid and acetic anhydride.
`
`5.
`
`I have been retained by the law firm of Foley & Lardner LLP, counsel for
`
`Daicel Corporation, to consult with legal counsel, to prepare this and
`
`potentially other declarations, and to be available to testify in this matter. In
`
`providing expert consulting services in this matter, I am being paid at a rate of
`
`$175/hour for time spent on this matter, and I am being reimbursed for actual
`
`expenses. My compensation in no way depends upon the outcome of this
`
`inter partes reexamination proceeding, or any other proceeding before the US
`
`Patent and Trademark Office, or matter in litigation.
`
`6.
`
`I have considered the following documents in forming my opinions:
`
`3
`000003
`
`

`
`Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`1013
`
`1014
`
`1015
`1016
`1017
`
`Exhibit No. Document
`1002
`U.S. Patent No. 8,076,507 (“the ’507 Patent”)
`First Declaration of Jeremy Cooper
`1003
`Curriculum Vitae for Jeremy Cooper
`1004
`1005
`Declaration of Mr. Hiroyuki Miura (“the Miura Decl.”)
`1006
`Résumé of Mr. Hiroyuki Miura.
`1007
`U.S. Patent Appl. 10/708,420 (“the ’420 Application”)
`1008
`U.S. Patent Appl. 11/788,455 (“the ’455 Application”)
`1009
`Applicant’s Response of January 6, 2011 in the ’455 Application
`1010
`U.S. Patent No. 5,625,095 (“the ’095 Patent”)
`1011
`U.S. Patent No. 6,339,171 (“the ’171 Patent”)
`Akinori, S. “Acetic Acid Synthesis From Methanol” J. Japan
`1012
`Petroleum Institute 20(5); 379-462 (1977)
`Certified English Translation of Akinori, S. “Acetic Acid
`Synthesis From Methanol” J. Japan Petroleum Institute 20(5);
`379-462 (1977) (“Akinori Translation”)
`European Patent Application Publication No. 1720821 (“EP
`’821”)
`Annex 3 as submitted in EP’821 (“Annex 3”)
`European Patent No. 0687662 A2
`Perry’s Chemical Engineers’ Handbook, Sixth Edition, 1984,
`pages 3-25 to 3-63.
`Oxford English Dictionary, second edition, 2002.
`Japanese Patent Application No. 2000-72712 (“JP 2000-72712”)
`Certified English Translation of JP 2000-72712 (“JP ’712”)
`Copy of http://www.rb-e.com/s/iodine-industry.asp as obtained
`on September 3, 2014.
`Interlocutory decision rendered by the Opposition Board in
`European Patent Application No. 05723599.6
`European Patent Application No. 05723599.6
`U.S. Patent No. 7,223,833
`Experiment results “D6” submitted by Daicel in opposition
`proceedings in European Patent Application No. 05723599.6
`Experiment results “D7” submitted by Daicel in opposition
`proceedings in European Patent Application No. 05723599.6
`Celanese Response as filed in the ’455 Application on July 7,
`2011
`Morello et al. “Commercial Extraction Equipment” Absorption
`
`1018
`1019
`1020
`1021
`
`1022
`
`1023
`1024
`1025
`
`1026
`
`1027
`
`1028
`
`4
`000004
`
`

`
`Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`and Extraction Sixteenth Annual Chemical Engineering
`Symposium 42(6); 1021-1035 (1950).
`
`1029
`1030
`
`Sander, S. et al. Chem. Eng. Res. and Design. 85(1): 149-154.
`Diep, B.T. et al. J. Chem. Eng. Data. 32(3); 330-333 (1987).
`
`
`
`I have also reviewed the following documents, which I understand were
`
`previously prepared and served on the opposing party in this proceeding: (i)
`
`the Supplemental Declaration of Jeremy Cooper; (ii) an excerpt from the
`
`Minerals Yearbook 2000; (iii) an excerpt from Fundamentals of Chemistry,
`
`Third Edition; (iv) a printout of the webpage at
`
`http://www.chemguide.co.uk/physical/equilibria/kc.html; and (v) an excerpt
`
`from Perry’s Chemical Engineers’ Handbook, Sixth Edition.
`
`Testimony Relevant To The Claims Of The ’507 Patent
`
`7.
`
`I am informed that Celanese International Corporation filed U.S. Patent
`
`Application No. 10/708,420 (Ex 1007; “the ’420 Application”) on March 2,
`
`2004, on April 20, 2007 U.S. Patent Application No. 11/788,455 (Ex 1008;
`
`“the ’455 Application”) was filed as a continuing application, and that on
`
`December 13, 2011 U.S. Patent No. 8,076,507 (Ex 1002; “the ‘507 Patent”)
`
`issued therefrom. I understand that the named inventors of the ’507 Patent are
`
`Mark O. Scates, David A. Trueba, and Raymond J. Zinobile. I will refer
`
`5
`000005
`
`

`
`Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`herein to the applicant of, and the named inventors in, the ’507 Patent
`
`collectively as “Celanese.”
`
`8.
`
`I am informed that only claims 42-44, 47-51, 53 and 55-57 of the ’507 Patent
`
`are involved in this proceeding. Where appropriate, I will refer to these
`
`claims as either “the claims,” or the “Celanese claims.”
`
`9.
`
`Generally speaking, claims 42-44, 47-51, 53 and 55-57 are directed to a
`
`process for separating a mixture comprising water, acetic acid, methyl iodide,
`
`methyl acetate, methanol, and at least one permanganate reducing compound
`
`(PRC), where the process includes 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 (“DME”);
`
`and (b) extracting the PRC enriched overhead stream with water to produce an
`
`aqueous stream comprising said at least one PRC, and a raffinate stream
`
`comprising methyl iodide. The distilling step separates the mixture
`
`comprising water, acetic acid, methyl iodide, methyl acetate, methanol, and at
`
`least one PRC into a “PRC enriched overhead stream” that contains DME and
`
`a PRC. See the ’507 Patent, claim 42. This PRC enriched overhead stream is
`
`then extracted with water to create an aqueous stream comprising at least one
`
`PRC and a raffinate. Id. The extracting step also must include at least one of
`
`6
`000006
`
`

`
`Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`three “wherein” clauses in claim 42. The first two “wherein” clauses each
`
`require that at least two consecutive extraction steps be performed; the
`
`difference being the first requires a fresh water stream to be used in each
`
`discrete extraction stage and the second requires a single water stream to pass
`
`through each of the discrete extraction stages in series. Id. The third
`
`“wherein” clause requires use of a continuous contacting extractor rather than
`
`two consecutive extraction steps. Id.
`
`10.
`
`I have reviewed claims 42-44, 47-51, 53, 55, and 56 of the ’507 Patent and it
`
`is my opinion that all of the elements of these claims are disclosed, or at least
`
`taught or suggested, by U.S. Patent No. 5,626,095 (“the ’095 Patent;” Ex.
`
`1010). My opinion is further solidified when one considers as evidence, the
`
`experimental results set forth in the Declaration of Mr. Hiroyuki Miura (Ex.
`
`1005; “the Miura Decl.”).
`
`11.
`
`I have reviewed claims 42-44, 47-51, 53, 55, and 56 of the ’507 Patent and it
`
`is my opinion that all of the elements of these claims are taught or suggested
`
`by U.S. Patent No. 6,339,171 (“the ’171 Patent;” Ex. 1011).
`
`12.
`
`It is also my opinion that all of the elements of claims 42-44, 47-51, 53, 55,
`
`and 56 of the ’507 Patent are taught or suggested by U.S. Patent No.
`
`7
`000007
`
`

`
`Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`6,339,171 (Ex. 1011; “the ’171 Patent”), alone, or in the alternative, in
`
`combination with the ’095 Patent and Akinori (Ex. 1012/1013).
`
`13.
`
`It is also my opinion that all of the elements of claims 42-44, 47-51, 53, and
`
`55-57 of the ’507 Patent are taught or suggested by the ’171 Patent in
`
`combination with the ’095 Patent and Akinori and Japanese Patent
`
`Application No. 2000-72712 (“JP 2000-72712”). An English Translation of
`
`JP 2000-72712 (“JP ’712”) is referenced in the following discussion.
`
`14. The Miura Declaration provides further information, as described below.
`
`Level of Skill in the Art
`
`15.
`
`I am informed that the ’507 Patent has a priority date of March 2, 2004, which
`
`is the filing date of the ’420 Application. I recognize that when considering
`
`the understanding of a skilled scientist – as it relates to the ’507 Patent – I
`
`should consider the skilled scientist as of this priority date. For simplicity
`
`herein, I use “in March 2004,” and the like, to mean as of March 2, 2004, the
`
`effective filing date of the ’507 Patent.
`
`16.
`
`In March 2004, one of ordinary skill in the art would have generally
`
`understood acetic acid production on an industrial scale including the
`
`distillation processes and extraction processes that are used in acetic acid or
`
`8
`000008
`
`

`
`Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`acetic anhydride production. The person of ordinary skill in the art would
`
`have understood chemical reactions in general, and, particularly, the primary
`
`reactions and the side-reactions associated with acetic acid production. While
`
`the person of ordinary skill in the art may have an advanced degree (M.S. or
`
`Ph.D.) in chemistry or chemical engineering, such is not necessarily required.
`
`A chemist or chemical engineer with a BSc honours degree and
`
`approximately five years of time in an industrial setting producing acetic acid,
`
`acetic anhydride, or related chemicals, would also have the requisite training
`
`and understanding of the nuances of large scale chemical production to be a
`
`person of ordinary skill in the art in this context
`
`17. Thus, there is no particular degree requirement. The person of ordinary skill
`
`in the art may be a qualified chemist or chemical engineer, however
`
`separations experience, an understanding of industrial-scale processes, and
`
`experience in the production of acetic acid, acetic anhydride, or related
`
`chemicals, is required.
`
`The Claims of the ’507 Patent
`
`18. The Claims of the ’507 Patent recite:
`
`9
`000009
`
`

`
`Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`42. 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 raffinate stream comprising methyl
`iodide,
`
`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 therefrom said aqueous stream
`comprising said at least one PRC and said raffinate 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 therefrom said aqueous stream
`comprising said at least one PRC and said raffinate stream
`
`10
`000010
`
`

`
`Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`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.
`
`43. The method of claim 42, wherein said PRC enriched
`overhead stream comprises an amount of dimethyl 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.
`
`44. The process of claim 42, wherein said at least one PRC
`comprises acetaldehyde.
`
`47. The process of claim 42, further comprising the steps
`of:
`
`performing a liquid-vapor phase separation on an effluent
`of a 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
`
`11
`000011
`
`

`
`Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`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 raffinate stream is
`recycled directly or indirectly back into said methanol
`carbonylation reactor.
`
`48. The process of claim 47 wherein said at least one PRC
`comprises acetaldehyde
`
`49. The method of claim 48, wherein sufficient
`acetaldehyde
`is removed from said PRC enriched
`overhead stream to maintain a concentration of propionic
`acid of less than about 400 parts per million by weight in
`said liquid product stream.
`
`50. The method of claim 48, 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.
`
`51. The method of claim 42, 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 of the mixture during said
`distillation step (a).
`
`12
`000012
`
`

`
`Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`53. The method of claim 42, wherein said distillation step
`(a) comprises distillation using a single distillation
`column.
`
`55. The method of claim 42, 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 1.8 wt %.
`
`56. The method of claim 42, wherein said dimethyl ether
`is present in said PRC enriched overhead stream at a
`concentration sufficient to produce said aqueous stream
`comprising said at least one PRC having a methyl iodide
`concentration between about 1.8 wt % and 0.5 wt %.
`
`57. The method of claim 42, 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 or equal to
`about 0.5 wt %.
`
`19. As I will describe below, it is my opinion that the person of ordinary skill in
`
`the art would have found that prior to March 2004, and at least as of the
`
`publication dates of the ’095 and ’171 Patent, the methods of claims 42-44,
`
`13
`000013
`
`

`
`Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`47-51, 53, and 55-57 were known in the art and to those of ordinary skill in the
`
`art.
`
`Acetic Acid Production
`
`20. As I understand the technology presented in the ’507 Patent, it is directed to
`
`the production of acetic acid. Specifically, the process is a variation on the
`
`Monsanto process. Both Celanese and Daicel licensed their original process
`
`from Monsanto. The Monsanto process was developed for the production of
`
`acetic acid by the rhodium-catalyzed carbonylation of methanol. (see
`
`Akinori, English translation, page 7). The ’507 Patent describes the
`
`production of acetic acid at col. 1, lines 13-21 as:
`
`This invention relates to an improved process for the
`removal of permanganate reducing compounds and alkyl
`iodides formed by the carbonylation of methanol in the
`presence of a Group VIII metal carbonylation catalyst.
`More specifically, this invention relates to an improved
`process for reducing and/or removing precursors of
`permanganate reducing compounds and alkyl iodides
`from intermediate streams during the formation of acetic
`acid by said carbonylation processes.
`
`14
`000014
`
`

`
`Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`21. Specifically, the ’507 Patent provides for a process for the purification of
`
`acetic acid, after its production, by the removal of permanganate reducing
`
`compound and alkyl iodides. Refer to ’507, col. 2, lines 30-36 and 45-49.
`
`Permanganate reducing compounds, or PRC’s include materials such as
`
`acetaldehyde, acetone, methyl ethyl ketone, butyraldehyde, crotonaldehyde,
`
`2-ethyl crotonaldehyde, and 2-ethyl butyraldehyde and the like, and the aldol
`
`condensation products thereof. Refer to ’507, col. 2, lines 30-36 and 45-49.
`
`22. At col. 4 lines 12 to 26, the ’507 Patent describes a process for producing
`
`acetic acid that includes the following steps: (a) reacting methanol,… with
`
`carbon monoxide…. (b) separating the products of the reaction into a volatile
`
`product phase that contains acetic acid, methyl iodide, water, and
`
`permanganate reducing compounds (PRC’s), and a less volatile phase
`
`containing the catalyst and acetic acid; (c) distilling the volatile product phase
`
`to yield a purified product and a first overhead that contains organic iodide,
`
`water, acetic acid, and unreacted methanol; (d) distilling at least a portion of
`
`the first overhead to produce a second overhead containing methyl iodide,
`
`water, C2-12 alkyl iodides, PRC’s and DME. Claim 42 focuses on a process for
`
`separating a mixture comprising water, acetic acid, methyl iodide, methyl
`
`acetate, methanol, and at least one permanganate reducing compound (PRC).
`
`15
`000015
`
`

`
`Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`The methanol is unreacted methanol from the Step (a) described above (i.e.,
`
`(a) reacting methanol,…). See ’507 Patent col. 4, l. 23.
`
`23. Apart from the claims this is the only place where the first overhead is
`
`mentioned. From this context “first overhead” clearly refers to the stream
`
`labelled 28 emanating from the top of column 14 in Figure 1 and 2.
`
`24. At col. 8, lines 1-24, the ’507 Patent provides a more detailed explanation as:
`
`The present invention may broadly be considered as an
`improved process
`for distilling PRC’s, primarily
`aldehydes and alkyl iodides, from a vapor phase acetic
`acid stream, such as the overhead from a light ends
`distillation column or a combined light-ends/drying
`column. The vapor phase stream is distilled and then
`twice extracted to remove PRC’s. An especially preferred
`method of removing aldehydes and alkyl iodides from a
`first vapor phase acetic acid stream, and reducing levels of
`propionic acid in the product, includes the following steps:
`a) condensing the first vapor phase acetic acid stream in a
`first condenser and biphasically separating it to form a
`first heavy liquid phase product and a first light liquid
`phase product; b) distilling the first light liquid phase
`product in a first distillation column to form a second
`vapor phase acetic acid product stream which is enriched
`with aldehydes and alkyl iodides with respect to said first
`
`16
`000016
`
`

`
`Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`vapor phase acetic acid stream; c) condensing the second
`vapor phase stream in a second condenser to form a
`second liquid phase product; d) distilling the second liquid
`phase product in a second distillation column to form a
`third vapor phase stream; e) condensing the third vapor
`phase stream and extracting the condensed stream with
`water to remove residual acetaldehyde therefrom; and f)
`extracting the extracted condensed stream with water to
`remove additional residual acetaldehyde therefrom.
`
`25. The specification further points out that while the light phase of the first
`
`overhead is preferred, the heavy or light phase may be used, as provided at
`
`col. 8, lines 34-39:
`
`Either phase of the light ends overhead may be
`subsequently distilled to remove the PRC’s and primarily
`the acetaldehyde component of the stream, although it is
`preferred to remove PRC’s from the light phase (30)
`because it has been found that the concentration of
`acetaldehyde is somewhat greater in that phase.
`
`26. Although the concentration of acetaldehyde in the light aqueous phase is
`
`likely to be greater than in the heavy methyl iodide phase the quantity of
`
`acetaldehyde available in the light phase may be insufficient, perhaps only
`
`one sixth of that in the heavy phase. Celanese recognized this issue in the
`
`17
`000017
`
`

`
`Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`’171 Patent and the ’507 Patent and recycled large amounts of water from
`
`stream 46 to compensate. Refer the ’507 Patent col. 9, lines 24-30.
`
`27. Figure 1 of the ’507 Patent is indicated as depicting the method of the prior
`
`art, while Figure 2 is indicated as depicting the claimed methods. The only
`
`difference between Figures 1 and 2 of the ’507 Patent is the incorporation of
`
`an additional extractor (25) and streams flowing to and from the additional
`
`extractor (25). Further, step (a) of claim 42 of the ’507 Patent should be
`
`considered to be admitted prior art as well, because it is merely describing a
`
`distillation that is done according to Figure 1 of the ’171 Patent.
`
`
`
`18
`000018
`
`

`
`Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`
`
`28. Acetic acid is produced in a reactor at a temperature of between 150 and 250
`
`ºC. (’507 Patent, col. 7, lines. 4 and 5). A liquid product having dissolved
`
`gases from the reactor is directed to a flasher (not depicted) that removes the
`
`catalyst as a base stream. (’507 Patent, col. 7, lines 46-59). The dissolved
`
`gases, consisting of carbon monoxide, methane, hydrogen, and carbon
`
`dioxide leave the flasher as an overhead stream which is directed to the “light
`
`ends” or “splitter column” 14 (pictured). Id. Exiting light ends column 14 is
`
`stream 28 which is directed to decanter 16. (’507, col. 7, lines 64-65). The
`
`light ends phase (or light phase) 30 is then further distilled. (’507, col. 7, lines
`
`65-67, and col. 8, lines 42-50).
`
`19
`000019
`
`

`
`Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`29. With regard to claim 42 and the description that the “PRC enriched overhead
`
`stream,” the ’507 Patent mentions “stream 28, containing PRC’s,” “light
`
`phase (30) is directed to column 18, which serves to form a second vapor
`
`phase (36) enriched in aldehydes…” and “stream 52 containing PRC's” as a
`
`distillation product from column 22. Thus, a broadest reasonable
`
`interpretation of “PRC enriched overhead stream” would include “a stream
`
`containing PRC’s.
`
`30. Claim 42 recites the term “raffinate stream.” As set forth in the claim, the
`
`“raffinate stream” is formed by extracting the PRC enriched overhead stream
`
`with water to produce an aqueous stream comprising said at least one PRC,
`
`and a raffinate stream comprising methyl iodide. The term “raffinate” is not
`
`defined in the specification of the ’507 Patent. Instead, the person of ordinary
`
`skill in the art must rely on industry standard definitions, which would
`
`indicate that the term is related to the phase that does not contain the extracted
`
`component of an extraction.
`
`31.
`
`In terms of Figure 2 of the ’507 Patent, there are two extractors described by
`
`reference numbers 27 (“the first extractor”) and 25 (“the second extractor”).
`
`See col. 10, line 56 to col. 11, line 2. The second raffinate is designated in
`
`Figure 2 by reference number 72. The second raffinate, 72 (“raffinate
`
`20
`000020
`
`

`
`Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`stream”), is then split and recycled to the reactor (72) and to a distillation
`
`column 22, as stream 68. See Fig. 2. It is noteworthy that stream 68 is not
`
`discussed or disclosed in the specification of the ’507 Patent, other than
`
`appearing in Figure 2.
`
`32. Because the first and second aqueous extract streams are only produced upon
`
`extraction, i.e. by an extractor, the first aqueous extract stream is designated
`
`by reference number 64 (“aqueous extract stream”) (Ex. 1002, col. 10, l. 58),
`
`and the second aqueous extract stream is designated by referenced number 70
`
`(“aqueous extract stream”). (Ex. 1002, col. 11, l. 4).
`
`33.
`
`It should also be noted that a raffinate is the extraction phase that contains less
`
`of the extracted component after an extraction. For example, the Oxford
`
`Dictionary defines raffinate as “[t]he refined fraction which results after
`
`removal of impurities by solvent extraction, spec. in oil refining.” Such a
`
`definition comports well with the examples used in the ’507 Patent. For
`
`example, at col. 10, ll. 58-62, the ’507 Patent states:
`
`The aqueous extract stream 64 leaves the extractor 27
`from the top thereof. This PRC-rich, and in particular,
`acetaldehyde-rich aqueous phase is directed to waste
`treatment. Also exiting the extractor is raffinate stream 66
`containing methyl iodide.
`
`21
`000021
`
`

`
`Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`34. Accordingly, it is clear that a raffinate is the fraction of the extraction that
`
`contains methyl iodide. However, claim 42 recites, in the first two of the three
`
`“wherein” clauses, that the extraction comprises at least two consecutive
`
`extraction steps, and each extraction step 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.” My interpretation of this language is that the
`
`extractors are operated in series with respect to the extract feed. The feed to
`
`the first extractor is the PRC enriched overhead stream and the feed to the
`
`second extractor is the raffinate stream from the first extractor. The raffinate
`
`from these two extractors is the liquid phase consisting primarily of methyl
`
`iodide which contains less of the PRC than the original extract feed.
`
`35. Claim 42 also recites the term “aqueous stream comprising said at least one
`
`PRC.” As set forth in the claim, the “aqueous stream comprising said at least
`
`one PRC” is formed along with a raffinate stream. Again, claim 42 recites, in
`
`the first two of the three “wherein” clauses, that the extraction comprises at
`
`least two consecutive extraction steps, and each extraction step comprises
`
`“contacting the PRC enriched overhead stream with a water stream and
`
`separating therefrom said aqueous stream comprising said at least one PRC
`
`22
`000022
`
`

`
`Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`and said raffinate stream comprising methyl iodide.” In terms of Figure 2 of
`
`the ’507 Patent, there are two extractors described by reference numbers 27
`
`(“the first extractor”) and 25 (“the second extractor”). (Ex. 1002, col. 10, ll.
`
`50-51 and 64). Because the first aqueous extract stream is only produced
`
`upon extraction, i.e. by an extractor, the first aqueous extract stream is
`
`designated by reference number 64 (“aqueous extract stream”) and the second
`
`aqueous extract stream is only produced upon extraction, i.e. by an extractor,
`
`the second aqueous extract stream is designated in Figure 2 by reference
`
`number 70 (“aqueous extract stream”). See col. 10, l. 58; col. 11, l. 4 and (Ex.
`
`1003, ¶ 21). The term “aqueous stream comprising said at least one PRC”
`
`includes both the first and second aqueous extract streams.
`
`36. Claim 47 recites “at least a portion of said raffinate stream is directly or
`
`indirectly recycled back into said methanol carbonylation reactor.” As noted
`
`above, the raffinate stream is not limited to a first or second raffinate stream.
`
`Furthermore, the recycling may be indirect or direct. Therefore, under a
`
`broadest reasonable interpretation, this term should be interpreted as the
`
`liquid stream coming from the extractor which contains the lower water and
`
`higher methyl iodide concentration (i.e., the stream that is not the aqueous
`
`23
`000023
`
`

`
`Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`extract) and that this stream is recycled back to the methanol carbonylation
`
`reactor either directly or via other equipment or process steps (i.e., indirectly).
`
`37. Referring back to FIG. 2 of the ’507 Patent, slip stream 68 is shown recycling
`
`the methyl iodide-rich raffinate phase from the second stage aqueous
`
`extraction 25 to the distillation column 22, but there is no mention of stream
`
`68 in the description.
`
`38.
`
`It is readily apparent from Figures 1 and 2 of the ’507 Patent, that the only
`
`difference between “prior art” Figure 1 and “inventive” Figure 2 is the
`
`existence of the second extractor 25, as well as connectors thereto, 66, 70, and
`
`72. This difference is depicted as one additional extraction step in the bottom
`
`right corner of Figure 2.
`
`39. Thus, the sole differences between Figure 1 and Figure 2 may be realized by
`
`simply focusing on the bottom right corner of the two figures. As shown in
`
`Figure 2, slipstream 68 recycles part of the second raffinate 72 back into the
`
`second distillation column 22. Indeed the description of Figure 1 and Figure 2
`
`merge into each other. There is no mention of the additional extraction step
`
`with regard to Figure 2, but in the description of Figure 1 (the prior art) the
`
`additional water extraction step is included. For example:
`
`24
`000024
`
`

`
`Patent No. 8,076,507
`First Declaration of Mr. William C. Jones
`
`…e) condensing the third vapor phase stream and
`extracting the condensed stream with water to remove
`residual acetaldehyde therefrom; and f) extracting the
`extracted condensed stream with water to remove
`additional residual acetaldehyde therefrom.
`
`Refer to ’507 Patent Col. 8, lines 20 to 23). The ’507 Patent also describes
`
`raffinate stream 66 as being extracted with additional water in a second
`
`extractor 25. Refer to ’507 Patent Col. 10 line

This document is available on Docket Alarm but you must sign up to view it.


Or .

Accessing this document will incur an additional charge of $.

After purchase, you can access this document again without charge.

Accept $ Charge
throbber

Still Working On It

This document is taking longer than usual to download. This can happen if we need to contact the court directly to obtain the document and their servers are running slowly.

Give it another minute or two to complete, and then try the refresh button.

throbber

A few More Minutes ... Still Working

It can take up to 5 minutes for us to download a document if the court servers are running slowly.

Thank you for your continued patience.

This document could not be displayed.

We could not find this document within its docket. Please go back to the docket page and check the link. If that does not work, go back to the docket and refresh it to pull the newest information.

Your account does not support viewing this document.

You need a Paid Account to view this document. Click here to change your account type.

Your account does not support viewing this document.

Set your membership status to view this document.

With a Docket Alarm membership, you'll get a whole lot more, including:

  • Up-to-date information for this case.
  • Email alerts whenever there is an update.
  • Full text search for other cases.
  • Get email alerts whenever a new case matches your search.

Become a Member

One Moment Please

The filing “” is large (MB) and is being downloaded.

Please refresh this page in a few minutes to see if the filing has been downloaded. The filing will also be emailed to you when the download completes.

Your document is on its way!

If you do not receive the document in five minutes, contact support at support@docketalarm.com.

Sealed Document

We are unable to display this document, it may be under a court ordered seal.

If you have proper credentials to access the file, you may proceed directly to the court's system using your government issued username and password.


Access Government Site

We are redirecting you
to a mobile optimized page.





Document Unreadable or Corrupt

Refresh this Document
Go to the Docket

We are unable to display this document.

Refresh this Document
Go to the Docket