Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claim Interpretation
The following claim interpretation is herein presented to clarify on the record these limitations recited in each of the noted claims:
In claim 1, recitation of “heavies” in parts a) and b) is interpreted as concerning “heavy byproducts formed from aldehyde compounds due to aldol condensation reactions as described at page 1, lines 11-20 of the instant Specification.
Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
Claims 1-9 are rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention.
In claim 1, in part b), it is unclear whether “a final OSN separation membrane refers back to one of the “at least one…nanofiltration (OSN) separation membrane”.
In claim 2, it is unclear whether “one OSN separation membrane” refers back to the “at least one…nanofiltration (OSN) separation membrane” introduced in claim 1.
In claim 3, it is unclear whether “two OSN separation membrane” refers back to the “at least one…nanofiltration (OSN) separation membrane” introduced in claim 1.
In claim 4, each of “the first OSN separation membrane” and “the second separation membrane” lacks antecedent basis, since claim 3 doesn’t restrict the “two OSN separation membranes” to be in series such that a permeate or retentate stream from a first of the membranes is provided to a second of the membranes.
In claim 5, recitation of the incinerating being within, or ‘up to 10 miles of the product-catalyst separation or reaction zone is inconsistent and contradictory with recitation in independent claim 1 of the incinerating being on-site.
In claim 7, it is unclear whether “at least one OSN separation membrane” and “a first OSM separation membrane” respectively refer back to the at least one of and a first of “at least one…nanofiltration (OSN) separation membrane” introduced in claim 1.
In claim 9, it is unclear whether “prior to incineration” refers back to the “incinerating” introduced in step c) of claim 1.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-9 are rejected under 35 U.S.C. 103 as being unpatentable over Wiese et al PGPUBS Document US 2008/0251456 (Wiese) in view of the Escapenet English translation of Document ES 2561653 (‘653), Geilen et al PGPUBS Document US 2016/0236150 (Geilen) and Brown et al PGPUBS Document US 2004/0102658 (Brown).
Referenced paragraph numbers of the Descriptions of the applied PGPUBS Documents and the Escapenet translation document are identified with “[ ]” symbols, for the Escapenet translation the “[ ]” symbol referring to the paragraph immediately preceding the symbol.
For claim 1, Wiese discloses a process for recovering rhodium from a hydroformylation process [0001, 0002, 0013, 0035 and 0083 regarding recovery of rhodium which is recycled to the hydroformylation process] that comprises producing at least one aldehyde in a reaction zone (Abstract and [0026-0027, 0034] concerning a hydroformylation reaction which contains or results in an aldehyde product] and [0079 re the hydroformylation being carried out in a stirred vessel, or in a jet nozzle, tube or loop reactor and carried out in one or more stages]),
the reaction zone comprising a C₆ to C₂₂ olefin, hydrogen and carbon monoxide in the presence of a catalyst ([0020 and 0022 regarding receiving a hydroformylation reaction mixture in a downstream membrane separation step which comprises C6 to C12 olefins, catalyst, carbon monoxide and [0018 concerning presence of hydrogen]) ,
wherein the catalyst comprises rhodium and an organophosphorus ligand ([0024 re presence of free organophosphorus ligand in the catalyst], [0035 re presence of inactive catalyst including recoverable rhodium metal] and [0069 re catalyst metals including rhodium compounds]), the process comprising:
(a) receiving a tails stream from a product-catalyst separation zone, wherein the tails stream comprises aldehydes, heavies, rhodium, and an organophosphorous ligand ([0035 re [0081] or [0083] re reactor recycle stream 6 or stream 14 received containing a hydroformylation product mixture 3’ separated from reaction zone vessel 4’ and containing rhodium and catalyst material and inherently also containing reaction mixture of aldehydes, organophosphorus ligand, rhodium and heavies in the form of C12 olefins, per discussion of [0018, 0020, 0022, 0024, 0036 and 0069 above]);
(b) providing at least a portion of the tails stream to at least one nanofiltration separation membrane, wherein a final permeate stream exits a final
c) heat-treating the final permeate stream [0035 and 0036 re “subsequent thermal separation stages”].
Claim 1, and claims dependent therefrom, firstly differ by requiring that the nanofiltration step or steps constitute providing at least one organic solvent nanofiltration (OSN) separation medium.
Geilen teaches the separation of homogenous catalysts from reaction mixtures with the help of organophilic nanofiltration (Abstract, [0002]), the catalysts used being organometallic complex compounds having rhodium or another metal as a central atom [0018 and 0019], the nanofiltration employing solvent-based nanofiltration [0021 re organic solvent nanofiltration (OSN) processes, generally] and [0048 re treatment of the catalyst-containing stream with organophilic nanofiltration, in which a reaction mixture comprising a liquid organic solvent comprised of mixture of dissolved feed materials, and target products and by-products are passed through a membrane to yield a permeate and retentate stream, with one of the streams being relatively enriched in catalyst].
Geilen also teaches at [0034, 0044 and 0048-0049] that such OSN nanofiltration results in relatively high membrane performance as measured by a membrane performance indicator of up to more than an index value of more than 0.35 or more than 0.75, thus resulting in a more economical and profitable recovery of the catalyst metal.
Thus, it would have been obvious to one of ordinary skill in the art of conducting hydroformylation reactions to have modified the Wiese method by utilizing organic solvent nanofiltration (OSN) for the disclosed nanofiltration method step, as cumulatively taught by Geilen, in order to enable providing of a relatively high membrane performance as measured by a membrane performance indicator, thus resulting in a more economical and profitable recovery of the rhodium catalyst metal.
Claim 1, and claims dependent therefrom, also differ by requiring the (c) heat-treating to comprise incinerating the final permeate stream on-site, to create a rhodium- containing ash.
Publication ‘653 teaches nanofiltration of a hydroformylation product mixture, including rhodium catalysts, accompanied or followed by incineration or other thermal treatment [0037 re use of rhodium as a hydroformylation catalyst], [0041, 0042 re recovery of rhodium by nanofiltration], and [0104 such nanofiltration being accompanied or followed by treating the product mixture by a thermal separation step or specifically incineration re an incineration step to recover adsorbed metal]).
Brown also teaches recovering rhodium catalyst values from hydroformylation product mixtures [0001, 0023, 0024], followed by incinerating a reaction product stream in the form of ion-exchange treated resin by incineration to form an ash,
which can advantageously be treated to separate the rhodium catalyst from other metal oxides and other materials to form an homogenous catalyst, effective to successfully return more than 90% of the rhodium to the hydroformylation for reuse as catalyst [0024, 0027 and 0036-0039] .
Brown suggests such incineration being on-site [0048 re the incineration to ash being conducted in a same chamber, as initially used for ion exchange resin separation of rhodium present, followed by washing the resin with methanol, thus the incineration to ash necessarily being conducted in the same chamber as previous method steps employed for recovering the rhodium catalyst].
Brown suggests motivation for such on-site or nearby location of incineration zone relative to other method step locations regarding such on-site location of all operations for recovering the rhodium in [0005] which states an objective of economically operating the process, in part met by reducing any requirement to transport rhodium-catalyst containing streams long distance to an incineration zone by locating the zone for performing incineration on site or nearby location(s) where other method steps are conducted.
Thus, it would have been obvious to one of ordinary skill in the art of conducting hydroformylation reactions to have modified the Wiese method by incinerating the final permeate stream, and by conducting such incineration on-site, to create a rhodium- containing ash, as cumulatively taught by ‘653 and Brown, in order to effectively separate the rhodium catalyst from other metal oxides and other materials to form an homogenous catalyst, effective to successfully return more than 90% of the rhodium to the hydroformylation for reuse as catalyst; and to conduct such method step economically by performing the incineration to ash on site and in or adjacent the same equipment utilized for performing other method steps.
For claims 2 and 3, Wiese also discloses wherein the process uses one nanofiltration separation membrane [0022, 0035 and 0083-0084 concerning membrane unit M1, and optional use of a 2nd membrane unit M2, the membrane(s) being nanofiltration membrane(s)]. Geilen also teaches utilization of a first and 2nd membrane separation unit 20 [0113-0120].
For claim 3, it would have been further obvious to have employed plural membrane units, as cumulatively taught by Wiese and Geilen, to inherently enable more complete separation of rhodium catalyst materials from other materials resulting from the hydroformylation.
For claim 4, Wiese also discloses wherein all of the permeate stream from the first separation membrane is provided to the second separation membrane (figure 3 re permeate stream 8’ from 1st membrane M1 being directed through intermediate vessels 9, 19 and D to 2nd membrane M2 and see [0083 regarding separation processes in intermediate vessels 9 and 19 being performed only optionally.
For claim 5, Brown further teaches wherein the incinerator in which the final permeate stream is incinerated to create the rhodium-containing ash is located within a ten mile radius of the product-catalyst separation zone ([0043 and 0046 re rhodium values being extracted, i.e. “separated” from an aldehyde hydroformylation column, i.e. “product-catalyst separation zone” using ion exchange resin] and [0048 re the incineration to ash being conducted in a same chamber, as initially used for ion exchange resin separation of rhodium present, followed by washing the resin with methanol, thus the incineration to ash necessarily being conducted in the same chamber as previous method steps employed for recovering the rhodium catalyst].
Brown suggests motivation for such on-site or nearby location of incineration zone relative to other method step locations regarding such on-site location of all operations for recovering the rhodium in [0005] which states an objective of economically operating the process, in part met by reducing any expenses and operational structure otherwise necessary to transport rhodium-catalyst containing streams long distance to an incineration zone by locating the zone for performing incineration on-site or nearby location(s) where other method steps are conducted.
Thus, it would have been further obvious to one of ordinary skill in the art of conducting hydroformylation reactions to have modified the Wiese method by incinerating the rhodium-containing ash within a ten mile radius of the product-catalyst separation zone, to more economically operate the process, in part met by reducing any expenses and operational structure otherwise necessary to transport rhodium-catalyst containing streams long distance to an incineration zone by locating the zone for performing incineration on-site.
For claim 6, Brown specifically teaches the method as further comprising recovering rhodium from the rhodium-containing ash [0024, 0027 and 0036-0039 re effective to successfully return more than 90% of the rhodium to the hydroformylation for reuse as catalyst].
For claim 7, Wiese further discloses passing at least a portion of retentate from at least one separation membrane through the first separation membrane (figure 3 and [0083] re retentate stream 7/14 being recirculated so as to pass again through the 1st separation membrane) .
For claim 8, Brown also suggests wherein the final permeate stream is incinerated within 90 days of the tails stream leaving the product-catalyst separation zone by teaching the incineration being conducted on-site from a final permeate stream of the nanofiltration ([0043 and 0046 re rhodium values being extracted, i.e. “separated” from an aldehyde hydroformylation column, i.e. “product-catalyst separation zone” using ion exchange resin], and
[0048 re the incineration to ash being conducted in a same chamber, as initially used for ion exchange resin separation of rhodium present, followed by washing the resin with methanol, thus the incineration to ash necessarily being conducted in the same chamber as previous method steps employed for recovering the rhodium catalyst, thus the incineration being conducted almost immediately after the separation of product from rhodium catalyst, rather than after a waiting or transportation period of any given number of days]).
Brown suggests motivation for such on-site or nearby location of incineration zone relative to other method step locations, and corresponding short time duration between separation of rhodium catalyst from product and incineration in [0005] which states an objective of economically operating the process, in part met by reducing any expenses and operational structure otherwise necessary to transport rhodium-catalyst containing streams long distance to requirement to transport rhodium-catalyst containing streams long distance to an incineration zone by locating the zone for performing incineration on site or nearby where other method steps are conducted, thus conducted immediately following the performance of other method steps, instead of after a waiting period of a given number of days.
Thus, it would have been further obvious to one of ordinary skill in the art of conducting hydroformylation reactions to have modified the Wiese method by incinerating the rhodium-containing ash immediately after performing other of the method steps instead of after a waiting period of a given number of days, to more economically operate the process, in part met by reducing any expenses and operational structure otherwise necessary to transport rhodium-catalyst containing streams long distance to an incineration zone by locating the zone for performing incineration on-site, with attendant incinerating of the rhodium-containing ash immediately after performing other of the method steps instead of after a waiting period of a given number of days.
For claim 9, Brown also teaches the further method step of treating the final permeate stream to be incinerated, prior to incineration, to recover residual aldehyde product [0036 regarding pre-treating resin containing the rhodium-catalyst containing stream by drying and pre-heating, so as to prevent the uncontrolled release of particulates from the process].
It would have been further obvious to the skilled artisan to have performed such pre-treating and drying of the stream to be incinerated, so as to prevent the uncontrolled release of particulates from the process.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Primary Examiner Joseph Drodge at his direct government formal facsimile phone number telephone number of 571-272-1140. The examiner can normally be reached on Monday-Friday from approximately 8:00 AM to 1:00PM and 2:30 PM to 5:30 PM.
If attempts to reach the examiner are unsuccessful, the examiner' s supervisor, Benjamin Lebron, of Technology Center Unit 1773, can reached at 571-272-0475.
The telephone number, for official, formal communications, for the examining group where this application is assigned is 571-273-8300.
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JWD
07/10/2026
/JOSEPH W DRODGE/Primary Examiner, Art Unit 1773
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