DETAILED ACTION
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 .
Response to Amendment
The rejection of claim 2 under 35 USC § 102(b) anticipated by FR-2134763 A5 is withdrawn by the examiner in view of the amendment filed on 8/3/2026.
A new Non-Final Office Action follows.
Claim Rejections - 35 USC § 102
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 the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1, 3 and 5 are rejected under 35 U.S.C. 102(b) as being anticipated by FR-2134763 A5.
The FR reference discloses a process for producing aromatic compounds from a gasoline feedstock from a catalytic cracking unit by charging the feedstock to a first hydrogenation zone operated in the present of hydrogen and a first catalyst to hydrogenate diolefins contained in the feedstock to produce a selective hydrogenation effluent (page 7, lines 15-24). The effluent is then passed into a fractionation zone to produce at least one C5- fraction containing compounds with 5 carbon atoms or few and a C6+ fraction containing compounds with at least 6 carbon atoms (page 7, lines 25-26). The C6+ fraction is hydrogenated olefins contained in the C6+ fraction in a second hydrogenation zone operated the presence of hydrogen and a second catalyst to produce a second hydrogenation effluent (page 7, lines 26-32). The second effluent is then passed into an extraction zone to produce an extracted stream concentrated in aromatics compounds and a raffinate stream concentrated in non-aromatic compounds (page 7, lines 33-35; page 2, lines 1-3). The first hydrogenation is operated at a temperature of 140o C, at a pressure of 28kg/cm2 (2.7 Mpa), at a hourly volumetric flow rate: 2 volumes per volume of catalyst (LHSV 2h-1) and at molar ratio of hydrogen to hydrocarbon is about 0.5 (it is estimate that the ratio is within the claimed ranges 2-100 Sm3/m3 ) . The first catalyst comprises a support and a metal of Group VIII (Examples 1 and 2). The second hydrogenation zone is operated at a temperature of 340o C, at a pressure of 40 Kg/cm2 (3.9 Mpa), a hourly feed volumetric flow rate: 4 volumes per volume of catalyst (LHSV 4 h-1). The second catalyst comprises a support and metal of Group VIII. (examples 1 and 2).
With respect to the amended limitation that the second cut is withdrawn at the bottom of a fractionation column, the fractionation step disclosed in the FR reference inherently involves a distillation operation in which lighter hydrocarbons (C5-) are removed overhead and heavier hydrocarbons are withdrawn as a bottoms stream. Accordingly, the claimed “second cut withdrawn at the bottom” is inherently disclosed.
With respect to the amended boiling range of the gasoline feedstock extending from C2/C3 hydrocarbons up to about 260°C, such range corresponds to conventional gasoline or pyrolysis gasoline feedstocks, as taught by the FR reference.
With respect to the amended limitation that the second cut, hydrogenation effluent, and aromatic stream comprise aromatic compounds containing 6 to 11 carbon atoms, gasoline-range aromatics inherently consist of C6-C11 compounds. Accordingly, this limitation merely describes the inherent composition of the streams disclosed in the FR reference.
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.
Claims 4, 17 and 18 are rejected under 35 U.S.C. 103 as being unpatentable over FR-2134763 A5.
The process of the FR reference is as discussed above.
Regarding claim 4, the FR reference does not teach that the C6+ fraction exhibiting a content of less than or equal to 5000 ppm of compounds having boiling point of greater than 217o C.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to have modified the process of FR reference by producing a C6+ fraction exhibiting a content of less than or equal to 5000 ppm of compounds having boiling point of greater than 217o C because the FR reference intended to producing a C6+ fraction comprising compounds having at least 6 carbon atoms. As control of the end-point boiling range and exclusion of heavier hydrocarbons from gasoline fractions was a routine optimization well within the level of ordinary skill in the art. The intent of the FR reference to produce a gasoline-range C6+ fraction comprising compounds having at least six carbon atoms would have motivated such routine fractionation control.
Regarding claims 17-18, FR does not expressly disclose that the hydrogenation effluent contains aromatic compounds containing 10 carbon atoms in an amount of about 7.22 wt.%, as recited in claim 17, or that the aromatic stream contains compounds containing 10 carbon atoms in an amount of about 6.4 wt.%, as recited in claim 18.
The amounts of C10 aromatic compounds in the hydrogenation effluent and recovered aromatic stream are dependent upon the composition of the gasoline feedstock, the fractionation conditions used to produce the second cut, and the subsequent hydrogenation and aromatic separation conditions.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to have operated the process of FR using a gasoline feedstock and process conditions that provide about 7.22 wt.% C10 aromatic compounds in the hydrogenation effluent and about 6.4 wt.% C10 compounds in the recovered aromatic stream because the relative concentrations of individual gasoline-range aromatic compounds in these streams are dependent upon known process variables, including the feedstock composition and fractionation and separation conditions, and adjustment of such variables to obtain a desired distribution of C6–C11 aromatic compounds would have been within the ordinary skill in the art.
Claim 2 is rejected under 35 U.S.C. § 103 as being unpatentable over FR-2134763 A5 in view of Feugnet et al. (US 9,249,364 B2).
FR discloses the process of claim 1 as discussed above, but does not expressly disclose that the gasoline feedstock comprises a gasoline cut resulting from a catalytic cracking unit.
Feugnet teaches a process employing a catalytic cracking unit (FCC) producing a gasoline cut, followed by selective hydrogenation of the gasoline obtained from the FCC unit. Feugnet specifically teaches that selective hydrogenation converts diolefins contained in the FCC gasoline into olefins and that the selectively hydrogenated gasoline is thereafter separated by distillation into light and heavy gasoline cuts. Feugnet further teaches FCC gasoline having an endpoint of about 150°C to 220°C. (See abstract; col. 3, lines 1-5, col. 3, line 63 through col. 5, line 54)
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to have used a gasoline cut resulting from a catalytic cracking unit, as taught by Feugnet, as the gasoline feedstock in the process of FR because Feugnet teaches that FCC gasoline is suitably subjected to selective hydrogenation to convert diolefins to olefins before fractionation into gasoline cuts. Such a modification would have constituted the use of a known unsaturated gasoline feedstock in FR's process for the same purpose of selectively hydrogenating diolefins prior to downstream fractionation and treatment.
Claims 6-10 are rejected under 35 U.S.C. 103 as being unpatentable over FR-2134763 A5 in view of Lee et al. (US 2013/0225838 A1).
The process of the FR reference is as discussed above.
The FR reference does not teach an extracting step as claimed.
Lee discloses a liquid-liquid extraction process for producing aromatic compounds. In this process, a hydrocarbon mixture is fed into a liquid-liquid extractor (Figure 3(340)) with a solvent stream (Figure 3(130)). This action separates the mixture into a raffinate (Figure 3(104)) and an extract (Figure 3(105)) that is concentrated in aromatic compounds. The extract is then stripped in a stripping section (Figure 3(346)), which separates it into a gas stream (Figure 3(108)) of non-aromatic compounds and a purified extract (Figure 3(112)). Following this, the aromatics are separated from the purified extract and the solvent using an aromatics recovery tower (Figure 3(341)). This yields a solvent stream (Figure 3(118)) and overhead vapors that form the aromatic stream (Figure 3(116)). The gas stream from the stripping section (Figure 3(108)) is condensed and separated in a condenser-settler (Figure 3(347)) to obtain a raffinate recycle stream (Figure 3(109)) and an aqueous phase (Figure 3(110)). The raffinate from the extractor (Figure 3(104)) is washed with water in a water wash tower (Figure 3(244)), which is fed by a water stream (Figure 3(134)). This washing step produces a non-aromatic stream (Figure 3(135)) and wash water (Figure 3(133)). The solvent used in the process included sulfolane (paragraph 0046).
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to have modified the process of the FR reference by utilizing the separation steps as suggested by Lee because such techniques were known to be effective for separating gasoline-range aromatic compounds and represent the predictable use of prior-art extraction technology in a known aromatic recovery process.
Claim 16 is rejected under 35 U.S.C. § 103 as being unpatentable over FR-2134763 A5 in view of Feugnet et al. (US 9,249,364 B2), and further in view of Bafna et al. (WO 2017/205083 A1).
FR in view of Feugnet teaches the process of claim 2 as discussed above, including treating a gasoline feedstock comprising a gasoline cut resulting from a catalytic cracking unit. FR further teaches fractionation of the selectively hydrogenated gasoline followed by hydrogenation of the heavier aromatic-containing fraction.
FR in view of Feugnet does not expressly teach additionally sending a pyrolysis gasoline into the fractionation unit B and/or hydrogenation unit C.
Bafna teaches co-processing catalytic-cracking naphtha and pyrolysis gasoline. Specifically, Bafna teaches producing a full-range cracked naphtha stream (109) in catalytic cracking unit 101 and a pyrolysis gasoline stream (108) in steam cracking unit 102, combining at least a portion of the full-range cracked naphtha stream with at least a portion of the pyrolysis gasoline stream to form combined stream 110, and subjecting the combined stream to hydrogen treatment in hydroprocessing unit 103, followed by fractionation of the hydroprocessed stream in splitter 104 to produce a light C5/C6 stream 112 and an aromatic-rich heavier stream 114 (Figs. 1 and 3; claim 1). Bafna further teaches that the hydroprocessing includes hydrogenation of diolefins and saturation of mono-olefins (claim 2).
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to have additionally introduced pyrolysis gasoline into the hydrogenation treatment of the heavier gasoline fraction in the process of FR as modified by Feugnet, as suggested by Bafna, because Bafna teaches that FCC naphtha and pyrolysis gasoline are compatible unsaturated gasoline feedstocks that can be combined and subjected to common hydrogen treatment. Such modification would have predictably permitted the pyrolysis gasoline and catalytic-cracking gasoline fractions to be treated together in common hydrogenation equipment rather than requiring separate hydrogenation treatment.
Response to Arguments
Applicant's arguments have been fully considered but are not persuasive except to the extent specifically noted below.
Applicant argues that FR-2134763 A5 (“FR”) does not disclose the claimed aromatic compounds containing 6 to 11 carbon atoms because FR is directed primarily to production of benzene, toluene, and xylenes, and because the examples do not show C9 or C10 aromatic compounds. Applicant further argues that the Office cannot rely upon inherency because the presence of C9–C11 aromatic compounds is not necessarily established by FR.
The Examiner agrees that the cited examples of FR do not establish that C9, C10, or C11 aromatic compounds are necessarily present. Accordingly, the rejection is not maintained on the basis that C9–C11 aromatic compounds are inherently present. Applicant's arguments and cited authorities concerning the requirements for establishing inherency therefore do not alter the rejection.
Claim 1, however, does not require the presence of aromatic compounds at each carbon number from C6 through C11, nor does claim 1 separately require the presence of C9, C10, or C11 aromatic compounds. Rather, claim 1 recites a second cut “containing aromatic compounds containing 6 to 11 carbon atoms,” a hydrogenation effluent containing such aromatic compounds, and an aromatic stream concentrated in such aromatic compounds. FR expressly discloses benzene (C6), toluene (C7), xylenes (C8), and ethylbenzene (C8) in the relevant process streams. Each of these is an aromatic compound having a carbon number falling within the recited range of 6 to 11 carbon atoms. Thus, FR expressly, rather than inherently, satisfies the claimed C6–C11 aromatic limitation. The absence of C9 or C10 compounds from the examples therefore does not distinguish claim 1.
Applicant also argues that FR teaches away because it separates hydrocarbons higher than C8 and subjects a C6-C8 cut to hydrogenation/hydrodesulfurization. This argument is not persuasive. The expressly disclosed C6-C8 aromatic compounds fall within the broader claimed range of C6-C11 aromatic compounds. Moreover, with respect to the anticipation rejection, FR's preference for processing a C6-C8 fraction and recovering benzene, toluene, and xylenes does not negate its express disclosure of aromatic compounds falling within the claimed range. Accordingly, the rejection of claim 1 does not require modification of FR to include C9–C11 aromatic compounds.
Applicant further argues that FR does not disclose the claimed fractionation, hydrogenation, and extraction stages. This argument is not persuasive. As set forth in the rejection, FR discloses selective hydrogenation of the unsaturated gasoline, subsequent fractionation to remove lighter C5 hydrocarbons and obtain the heavier aromatic-containing fraction, hydrogenation/hydrodesulfurization of that fraction, and subsequent separation of aromatic compounds from non-aromatic compounds. Accordingly, the process sequence recited in claim 1 is disclosed by FR.
With respect to claim 2, Applicant correctly points out that FR principally identifies pyrolysis/steam-cracking gasoline rather than a gasoline cut resulting from a catalytic-cracking unit. Accordingly, FR alone is not relied upon for this limitation. Feugnet et al. (US 9,249,364 B2) teaches a gasoline cut obtained from a catalytic cracking unit, selective hydrogenation of diolefins contained in the FCC gasoline, and subsequent fractionation of the selectively hydrogenated gasoline into gasoline cuts. Thus, Feugnet establishes that FCC gasoline was a known unsaturated gasoline feed suitably subjected to the same type of selective diolefin hydrogenation and subsequent fractionation employed by FR.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to have used a gasoline cut resulting from a catalytic cracking unit, as taught by Feugnet, as the gasoline feedstock in the process of FR because Feugnet teaches that FCC gasoline contains diolefins and is suitably subjected to selective hydrogenation of the diolefins before subsequent fractionation. Such use constitutes application of a known unsaturated gasoline feedstock to a known process for selectively hydrogenating diolefins and subsequently processing the resulting gasoline fraction.
With respect to claim 4, Applicant argues that the limitation requiring no more than 5000 ppm by weight of compounds boiling above 217°C represents a deliberate process-control feature rather than an arbitrary distillation endpoint. The argument has been considered but is not persuasive. FR already employs fractionation to control the composition and boiling range of the fraction subjected to downstream hydrogenation and aromatic recovery. The amount of higher-boiling material retained in such a fraction is dependent upon known fractionation variables, including the selected cut point and operating conditions. Controlling the heavy-end content of the fraction therefore constitutes optimization of a known fractionation operation. Applicant has not established that the particular limit of 5000 ppm above 217°C is critical or produces an unexpected result relative to other heavy-end concentrations obtainable through operation of the known fractionation process.
With respect to claims 6-10, Applicant argues that Lee does not cure the alleged deficiencies of FR. This argument is not persuasive because Lee is not relied upon to remedy the C6-C11 aromatic limitation or the basic process sequence of claim 1. FR supplies those limitations for the reasons discussed above. Lee is relied upon for the particular aromatic extraction and solvent-handling features recited in claims 6-10, including liquid-liquid extraction, extract stripping, aromatic recovery, solvent recovery and recycle, raffinate washing, phase separation, and the use of sulfolane. It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to have employed Lee's known aromatic-extraction arrangement in the aromatic-separation stage of FR because Lee teaches such equipment and solvent systems for their established purpose of separating aromatic hydrocarbons from mixtures containing aromatic and non-aromatic hydrocarbons.
With respect to new claim 16, Applicant argues that FR treats pyrolysis/steam-cracking gasoline as the starting gasoline and therefore does not disclose separately sending pyrolysis gasoline into fractionation unit B and/or hydrogenation unit C of a process treating catalytic-cracking gasoline. FR and Feugnet do not expressly disclose this additional limitation. However, Bafna teaches co-processing catalytic-cracking naphtha and pyrolysis gasoline. Bafna teaches producing full-range cracked naphtha in a catalytic cracking unit and pyrolysis gasoline in a steam cracking unit, combining at least portions of the FCC naphtha and pyrolysis gasoline, subjecting the combined gasoline stream to hydrogen treatment, and thereafter fractionating the treated stream into a light C5/C6 stream and an aromatic-rich heavier stream (see Figs. 1 and 3; claims 1–2).
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to have additionally processed pyrolysis gasoline with the catalytic-cracking gasoline in the process of FR as modified by Feugnet, as taught by Bafna, because Bafna teaches that FCC naphtha and pyrolysis gasoline are compatible unsaturated gasoline feeds that can be combined and subjected to common hydrogen treatment and subsequent fractionation, thereby permitting the gasoline streams to be processed using common treatment equipment.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to TAM M NGUYEN whose telephone number is (571)272-1452. The examiner can normally be reached Mon - Frid.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Prem C Singh can be reached at 571-273-6381. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/TAM M NGUYEN/Primary Examiner, Art Unit 1771
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