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
Examiner acknowledges Applicant’s response filed 30 March 2026 containing remarks and amendments to the claims.
Claims 1, 5-6, 9, 12-14, and 16-26 are pending.
The previous rejections have been maintained. The rejections follow.
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 1, 5-6, 9, and 12-14 are rejected under 35 U.S.C. 103 as being unpatentable over Gleim (US 3,165,463) in view of Soled (US 6,162,350) and Dysard (WO 2005/056728).
Regarding claims 1 and 12, Gleim teaches mixing a distillate hydrocarbon feed with an activated organometallic compound to obtain a combined feed (column 1, lines 1-45 and column 2, lines 45-column 3, lines 75); mixing the combined feed with gaseous hydrogen to hydroprocess the combined feed under hydrogen atmosphere at a temperature in the range of 225-500°C and a pressure range of 500-5000 psig to decompose the organometallic catalyst (column 3, lines 1-75). Gleim teaches separating the first gaseous phase from a hydrocarbon liquid phase free from catalyst and a catalyst containing sludge (column 3, lines 50-75). Gleim teaches the hydrocarbon liquid is separated from the catalyst sludge by centrifugal separation (column 8, lines 1-40), reading on the claimed “metal capture unit being a centrifuge”.
Gleim teaches 0.1-10% activated catalyst (column 4, lines 30-70). Gleim teaches the organo metallic compound is selected from iron, and molybdenum (column 4, lines 1-65).
Gleim teaches hydrofining various sulfur/nitrogen containing feedstocks including heavy hydrocarbons, crude oil, and distillates obtained therefrom (column 1, lines 20-45).
Gleim does not explicitly disclose (1) which distillates are used as feedstocks (2) further fractionation of the products (3) adsorption as the metal removal step.
Regarding (1), Soled teaches a similar hydrofining process in which various distillates are treated to remove sulfur and nitrogen therefrom, including naphtha and diesel (column 23, line 59-column 24, line 30). Examiner considers diesel feeds to be treated to remove sulfur to read on the claimed “sour diesel or partially hydrotreated diesel”, as they have sulfur to be removed.
Therefore, it would have been obvious to the person having ordinary skill in the art to have selected an appropriate sulfur/nitrogen containing distillate feed in the process of Gleim, such as the naphtha and diesel disclosed by Soled, since Soled teaches that naphtha and diesel feeds contain nitrogen and sulfur compounds that may be removed by hydroprocessing.
Regarding (2), Examiner notes that fractionation of hydrotreated effluent is well known in the art in order to recover various product fractions.
Therefore, it would have been obvious to the person having ordinary skill in the art to have performed well known fractionation to the effluent, in order to recover desired product fractions. It is not seen where such fractionation would result in any new or unexpected results.
Regarding (3), Dysard teaches a method for treating diesel to remove sulfur and nitrogen (abstract). Dysard teaches that after hydrotreatment stage, the effluent is fed to an adsorbent stage to further remove contaminants [0014]. Dysard teaches various sorbents including silica, alumina, activated carbon, sieves, or clay [0014].
Therefore, it would have been obvious to the person having ordinary skill in the art to have performed the Dysard adsorption step in combination with the hydrotreatment of the previous combination, for the benefit of obtaining further purification. It is expected that the same metal capture would occur as claimed, since Dysard teaches the same contact with the same adsorbents as claimed. It is not seen where Applicant has distinguished the process steps in this regard.
Regarding claim 5, Gleim does not explicitly disclose residence time.
However, Examiner notes that residence time is a well-known process variable for hydrotreatment. Soled teaches selection of appropriate reaction times including 1 min to 24 hours (column 11, lines 14-17).
Therefore, it would have been obvious to the person having ordinary skill in the art to have selected an appropriate residence time, such as that disclosed by Soled, for the benefit of obtaining the desired sulfur and nitrogen removal.
Regarding claim 6, Gleim teaches slurry reactor (column 2, lines 60-65).
Regarding claim 9, Gleim teaches recycling the recovered catalyst in elemental or combined form (column 6, lines 1-50). The instant claims appear to contain an additional metal recovery step. Examiner considers this to be mere duplication of steps. Alternatively, the person having ordinary skill in the art may combine two or more of the Gleim catalyst recovery steps, such as centrifuge, in order to recover the desired catalytic metal.
Regarding claims 13-14, Dysard teaches that the adsorbents may be desorbed by an elution solvent such as diesel, so that the adsorbents can be reused in the process [0014]. Examiner notes that the instant specification teaches the same treatment with diesel to perform desorption of metal [0032]. In this regard, it is not clear where Applicant has distinguished the Dysard diesel wash desorption step from the claimed diesel desorption step to recover metal.
Claims 16-20 and 22-26 are rejected under 35 U.S.C. 103 as being unpatentable over Gleim (US 3,165,463) in view of Soled (US 6,162,350) and Dysard (WO 2005/056728) as applied to claim 1 above, and further in view of Aldridge (US 4,066,530).
Regarding claims 16-20 and 22-24, the previous combination teaches the limitations of claim 1, as discussed above. The further claims contain a slightly different order of separation. Examiner notes that order of performing process steps is prima facie obvious in the absence of new or unexpected results (see MPEP 2144.04, IV, C).
Further, Aldridge teaches a similar process for hydroconversion with organometallic catalyst followed by separation steps. Aldridge teaches multiple separation steps, in different orders, in order to obtain the same recovery of catalytic materially and liquid products (see figure, column 5, line 35-column 6, line 40).
Therefore, it would have been obvious to the person having ordinary skill in the art to have modified the order of fractions, such as disclosed by Aldridge, since the order of steps does not appear to impact the result. Each of the prior art results in the same separation of solids, liquid products, and gas products.
Regarding claims 25-26, Dysard teaches various sorbents including silica, alumina, activated carbon, sieves, or clay [0014].
Claim 21 is rejected under 35 U.S.C. 103 as being unpatentable over Gleim (US 3,165,463) in view of Soled (US 6,162,350) and Dysard (WO 2005/056728) as applied to claim 11 above, and further in view of Aldridge (US 4,066,530).
Regarding claim 21, the previous combination teaches the limitations of claim 11, as discussed above. The further claims contain a slightly different order of separation. Examiner notes that order of performing process steps is prima facie obvious in the absence of new or unexpected results (see MPEP 2144.04, IV, C).
Further, Aldridge teaches a similar process for hydroconversion with organometallic catalyst followed by separation steps. Aldridge teaches multiple separation steps, in different orders, in order to obtain the same recovery of catalytic materially and liquid products (see figure, column 5, line 35-column 6, line 40).
Therefore, it would have been obvious to the person having ordinary skill in the art to have modified the order of fractions, such as disclosed by Aldridge, since the order of steps does not appear to impact the result. Each of the prior art results in the same separation of solids, liquid products, and gas products.
Response to Arguments
Applicant’s arguments filed 30 March 2026 have been fully considered but they are not persuasive.
Examiner considers Applicant’s arguments to be:
Gleim teaches away from the claimed method. Gleim teaches temperatures below 310˚C and in the absence of hydrogen (column 5, lines 32-39).
The process results in unexpected results.
Regarding Applicant’s first argument, Examiner acknowledges that the referenced portion of Gleim teaches steps for preparing the organometallic material in the hydrocarbon feed. Subsequently to the preparation step, Gleim positively recites reaction of the colloidally dispersed catalyst with the hydrocarbon feed in the presence of hydrogen at temperatures of 225-500˚C (column 5, lines 51-55 and column3, lines 37-50), thus meeting the claim limitations.
Regarding Applicant’s second argument, it is not clear how the examples in the specification show evidence of new or unexpected results in comparison with the Gleim reference. Gleim teaches the claimed iron/molybdenum organometallic catalyst in a slurry reactor operated at conditions encompassing the claimed ranges (columns 3-4). The examples in the instant specification are more limited, and require SOSCAT-9 molybdenum in an amount of 10000 ppm and with 0.5 g dimethyl disulfide and 50 grams of sour diesel, using specific conditions, in order to obtain the sulfur reduction discussed. In contrast, the instant claims are simply drawn to “organometallic compound”, and do not require the amounts of reactants or sulfur reduction as discussed in the instant specification example. In this regard, Applicant’s argument is not commensurate in scope with the claim language.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Gatsis (US 4,943,548) – previously relied upon teaches i. mixing a hydrocarbon feed and an organometallic catalyst to obtain a combined feed (column 2, lines 48-67); mixing the combined feed with gaseous hydrogen to hydroprocess the combine feed (column 2, lines 48-67) at temperatures of 343-538°C and pressure of 500-5000 psig (34.48-344 bar) (column 4, lines 55-65), which overlaps with the claimed ranges. Gatsis teaches the hydroconverted product is separated from the catalyst by centrifuge (column 4, line 55-column 5, line 5).
Derouane (US 4,578,181) – previously relied upon teaches a similar process for hydroconversion of hydrocarbon feeds with organometallic catalysts. Derouane teaches similar centrifuge steps to recover recycle catalyst material 43 as well as gas and further distillable liquids 46 (see figure, column 5, line45-column 6, line14).
Kramer (US 5,298,152) - Kramer shows two separators followed by two distillation units (see figure). Kramer teaches an atmospheric distillation column (see figure 24).
Havlik (US 2014/0138283) – previously relied upon, Havlik teaches a similar method for recovering catalytic metal using adsorption in addition or alternative to centrifugal separation [0010], [0021], [0024], [0025]. Havlik teaches using clay sorbent [0025].
Prajapati (US 2016/0288101) – previously relied upon teaches hydroprocessing followed by solvent extraction to recover metals from the product stream [0033-0048].
Reynolds (US 2008/0135450) – previously relied upon teaches centrifuging and metals recovery steps [0016-0022]. Reynolds teaches fractionating liquid products prior to metals recovery steps.
Natori (US 5,792,824) – previously relied upon teaches adsorption separation and filtration are well known in the art to separate organometallic hydrogenation catalyst from hydrotreated hydrocarbons (column 44, lines 30-37 and column 42, lines 26-50).
Kalnes (US 5,028,313) – teaches multiple separation and distillation steps after hydrotreatment (see figure).
Bauer (US 2010/0122939) – teaches filtration and product fractionation after slurry processing (see figure).
Biswas (US 2009/0008290) – teaches recovery of catalyst slurry by solvent deasphalting, followed by product separation (See figure).
Chabot (US 2010/0065472) – teaches methods for recovery recycle slurry catalyst in hydroprocessing systems (see figure).
Lott (US 2005/0241991) – teaches catalyst withdrawal followed by fractionation steps (see figure 2c).
Doubrava (US 2003/0209106) – teaches filter steps to recover catalytic metals (abstract).
Odueyungbo (US 2012/0198718) – teaches filtration to recover hydroprocessing catalyst (abstract).
Gotteland (US 2013/0150232) – teaches recovery of slurry catalyst (see figure).
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MICHELLE STEIN whose telephone number is (571)270-1680. The examiner can normally be reached Monday-Friday 8:30 AM-5:00 PM.
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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 571-272-6381. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/MICHELLE STEIN/Primary Examiner, Art Unit 1771
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