DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
This communication is in response to the application filed 1/31/2025.
Claims 1-20 are pending.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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.
Claim(s) 1, 3-5, 7-8, 13-15, and 17-19 is/are rejected under 35 U.S.C. 103 as being unpatentable over Takeshita (US 20110272268) in view of Ramamurthy (WO 2018127817).
With respect to claims 1, 13-14, and 19, Takeshita (US 20110272268) discloses a process for producing DCPD resin from cracked gas. Abstract. A cracked gasoline having C5-C9 hydrocarbons is recovered from an ethylene cracking unit (i.e. pyrolysis gasoline from a steam cracking facility). Par. [0012]; [0034]-[0035]. The effluent is subject to a dimerization reaction and the dimerization reaction subject to separation such as distillation to recover C5, BTX, and a residual stream comprising crude DCPD (i.e. resin production facility). Par. [0037]-[0038].
Takeshita is silent regarding producing the cracked gasoline is derived from a recycled hydrocarbon and processing a portion of the BTX having recycle material in an aromatic complex to produce r-paraxylene having at least 85 weight percent.
Ramamurthy (WO 2018127817) teaches a process for the production of hydrocarbons from waste plastics. Abstract; par. [0079]. The process includes pyrolysis and hydroprocessing of waste plastics to produce a hydrocarbon product and feeding the liquid hydrocarbon (a pyrolysis naphtha) to upgrading, which may be steam cracking unit. Abstract; par. [0099], [0101]. The steam cracked effluent, less gases, is sent to further processing for production of cumene and para-xylene, par. [0079]-[0080]; [0091], both well known for use in the production of resins. The cracked product is subject to separation to produce an aromatics rich stream and the aromatics rich stream is further separated into a benzene product, xylene product, and C7, C9, and/or C10 aromatics. The C7, C9, and/or C10 aromatics are converted in a disproportionation & transalkylation unit to yield additional benzene and xylenes. Abstract; par. [0074]-[0078]. The benzene, along with propylene, is passed to an alkylation unit for the production of cumene. Par. [0086]-[0090].
Therefore, before the filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to modify Takeshita in view of Ramamurthy by sending the pyrolysis gasoline obtained from waste plastics of Ramamurthy to DCPD resin production unit of Takeshita and sending the recovered BTX back to the aromatics separation and treatment unit of Ramamurthy for the benefit of production of DCPD resin in addition to cumene and paraxylene using recycled materials. Both teach production of resin and aromatics from steam cracked gasoline and Ramamurthy teaches wherein high-quality aromatics may be produced using hydrocarbon derived from waste plastics. The integration would provide the benefit of producing a final resin product or chemicals for resin production from a recycle waste materials, and the integration of the two would do nothing more than combine known processes in a known way to perform their intended functions.
With respect to the concentration of the paraxylene stream, Ramamurthy teaches production of para-xylene, further conversion of o- and m-xylenes to para-xylenes, par. [0071]-[0072], and the xylene stream may be separated into individual fractions via e.g. extractive distillation, crystallization, adsorption, or combinations, par. [0079]. Ramamurthy does not explicitly state the para-xylene fraction includes at least 85 weight percent paraxylene, however, it would have been within the skill and obvious to one of ordinary skill at the time of filing to design the conversion and separation of xylene fractions for maximum isolation of individual fractions to improve purity for use downstream.
With respect to claims 3 and 15, the hydrocarbon feed to the steam cracking unit, r-hydrocarbon, includes pyrolysis oil derived from the pyrolysis of waste plastic, as well as recycled saturates from downstream separation. Ramamurthy at par. [0100]-[0101].
With respect to claim 4, the hydrocarbon stream is a stream from pyrolysis effluent separated by any suitable gas-liquid separator, including distillation columns. Par. [0027].
With respect to claim 5, the pygas from the naphtha cracker would be rich in aromatics and sent to further separation of BTX+EB. Par. [0106]. The steam cracking unit is operated to maximize aromatics, which are recovered. The saturates may be returned. The effluent includes e.g. 35-37% gasoline range stream. Par. [0102]. The steam cracking effluent includes methane, ethylene and propylene, saturates, and gasoline and diesel. See table at par. [0104]. While the PONA content of the steam cracked product fraction is not disclosed, same or similar feed is treated using steam cracking for production of BTX-EB. It is expected that the production of aromatics produced by treating the same or overlapping feed in the same steam cracking reaction for the production of aromatics would result in an aromatics content within the broad range claimed of at least 20 and/or not more than 85 weight percent content of benzene, toluene, and xylenes (BTX).
With respect to claims 7 and 8, Takeshita discloses treatment to remove impurities, dimerization (polymerization unit), and separation of BTX, unreacted C5 for recycle and DCPD. Par. [0003]; [0034]-[0038]. Before the filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to return the unreacted C5 to the dimerization reactor to increase production of DCPD as recycle of unreacted and isolated feed is well known.
With respect to claim 16, Takeshita is silent regarding the specific composition of the aromatics stream, however, given a BTX stream is recovered from the effluent comprising heavier cyclic hydrocarbons (DCPD and similar) using distillation, it is expected that the BTX would contain a majority of benzene, toluene, xylene and hydrocarbons within the same boiling range, along with some hydrocarbons in the abutting fractions, including C9 to C12 aromatics. With respect to the specific amounts, before the filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to modify the conditions for separation step or series of separation steps to achieve the desired stream for downstream processing considering at least cost of separation unit or units and the optimum product split.
With respect to claims 17 and 18, in Ramamurthy the separation of aromatics may include “selective adsorption, selective absorption, extractive distillation, solvent extraction followed by distillation, and the like, or combinations thereof.” Par. [0057]; [0065]; [0070]. Toluene may be subject to tansalkylation/disproprionation to xylenes. Par. [0074]-[0078]. Mixed xylenes may be separated to recover p-xylenes. Par. [0079]. With respect to the specific solvent for solvent extraction or extractive distillation, claimed solvents are common in the art and selection of a desired solvent would have bene obvious to and within the skill of one in the art at the time of filing.
Claim(s) 2, 6, 9 and 12 is/are rejected under 35 U.S.C. 103 as being unpatentable over Takeshita (US 20110272268) in view of Ramamurthy (WO 2018127817) as applied to claims 1, 3-5, 7-8, 13-15, and 17-19 above, further in view of Bitting (US 20210130699).
With respect to claim 2, the feed to the steam cracking reactor is a pyrolysis oil, typically a pygas or naphtha range oil produced from recycled waste plastics, i.e. r-hydrocarbon. Ramamurthy at par. [0100]. Ramamurthy is silent regarding wherein recovery of the recycled gasoline from the steam cracking facility of step (a) includes cooling and separating at least a portion of the r-cracked effluent stream to provide the r-pyrolysis gasoline stream. However, quenching of steam cracked effluent to stop the reaction and prevent downstream polymerization and fouling is well known in the art.
Alternatively, in the analogous art of production of recycled hydrocarbons from waste plastic pyrolysis and steam cracking, Bitting discloses quenching and separating the r-cracked effluent. A recycled waste plastic is passed to pyrolysis reactor for conversion to r-pygas and r-pyoil. The r-pyoil is passed to a cracker and the effluent subject to separation to produce light olefins, hydrogen, and pyrolysis gasoline. Figure 1. The cracker for pyoil may be a gas cracker in the presence of steam for steam cracking. Par. [0403]-[0404]. The effluent is subject to cooling in a transfer line exchanger and/or with direct quench. Par. [0418]; Figure 5. Cooling in the transfer line exchanger and/or by other means is to “prevent production of large amounts of undesirable by-products and to minimize fouling in downstream equipment, and also to generate steam.” Par. [0547]. The cooled effluent is separated into r-product streams and r-pyrolysis gasoline. Figure 1, 4.
Therefore, before the filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to modify the steam cracking of Ramamurthy and Takeshita to include cooling or quenching between the cracking furnace and downstream effluent separation as taught in Bitting because all are directed to steam cracking, Bitting and Ramamurthy are directed to cracking recycled pyoil in gas crackers, and quenching effluent out of the furnace is standard in the art of cracking for the benefit of preventing “production of large amounts of undesirable by-products and to minimize fouling in downstream equipment, and also to generate steam”.
With respect to claim 6, Bitting discloses steam cracking the r-pyoil alone or in the presence of non-recycle feed. Par. [0360]; [0406].
With respect to claim 9, Ramamurthy teaches the production of paraxylene from the aromatics contained in cracked gasoline. Bitting teaches wherein the feed may include non-recycled content, resulting in a paraxylene stream comprising r-paraxylene and non-recycled paraxylene.
With respect to claim 12, Ramamurthy and Takeshita are silent regarding the relative location of the waste treatment and downstream processing including wherein at least two of the steam cracking facility, the hydrocarbon resin production facility, and the aromatics complex are co- located. Bitting discloses “large-scale production of one or more materials having recycle content” via pyrolysis of recycled waste, followed by downstream treatment. Bitting at par. []. The “pyrolysis unit producing recycle content pyrolysis oil (r-pyoil) and/or recycle content pyrolysis gas (r-pygas) can be co-located with the production facility[ or] can be sourced from a remote pyrolysis unit and transported to the production facility.” Bitting at par. [0006], [0266], [0360].
Claim(s) 10, 11 and 20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Takeshita (US 20110272268) in view of Ramamurthy (WO 2018127817) as applied to claims 1, 3-5, 7-8, 13-15, and 17-19 above, further in view of Linck (US 2021/0348063).
With respect to claims 10, 11, and 20, Takeshita and Ramamurthy teach the limitations discussed above. Ramamurthy teaches production of high-value chemicals including r-paraxylene. The art is silent regarding downstream use of para-xylene, including oxidizing at the r-paraxylene stream in a terephthalic acid production facility to form recycled content terephthalic acid (r-TPA) and reacting at least a portion of the r-TPA with ethylene glycol (EG) in a polyethylene terephthalate (PET) production facility to provide recycled content PET (r-PET).
Linck (US 2021/0348063) discloses a process for effective recycling of waste polymer into the same or different polymer. Par. [0075]. “[H]ydrodeoxygenation of PET can be used to recover para-xylene, which may, in turn, be conveniently processed to upgraded PET according to known methods involving oxidation of para-xylene to its dicarboxylic acid derivative, namely terephthalic acid (TPA), optionally followed by esterification or possibly transesterification of an esterified intermediate, and then copolymerization with ethylene glycol.” Par. [0075].
Therefore, before the filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to modify the integrated process to include downstream use of para-xylene produced in Ramamurthy by oxidation to TPA and conversion to PET resin because both are directed to the use of waste plastics to produce additional high value chemicals, the integration allows production of a PET product from the intermediate chemical. Ramamurthy teaches production of para-xylene and Link teaches the production of para-xylene along with the downstream use of para-xylene to produce TPA and then PET resin; thus, the claimed elements were known in the prior art and could have been combined as claimed by known methods with no change in their respective functions, and the combination yielded nothing more than predictable results to one of ordinary skill in the art.
Double Patenting
A double patenting rejection is not necessitated at this time. While a number of related applications which claim similar processes exist, at this time they fail to integrate the resin facility in the manner presently claimed.
Conclusion
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/BRANDI M DOYLE/Examiner, Art Unit 1771
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