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 .
Claim Status
Claims 1, 8, 12, and 18 are amended. Claim 3 is cancelled.
Claims 1, 2, and 4-20 are pending for examination below.
Response to Arguments
Applicant's arguments filed 12 June 2026 have been fully considered but they are not persuasive.
Applicant argues on pages 2-3 of the Remarks that Novak teaches away from selectively retaining residual oxygenates within the claimed range, because Novak teaches removing as much oxygen as possible in a substantial deoxygenation step and that the most preferred range in Novak is outside the claimed range.
In response, the Examiner respectfully notes that references are not limited to the most preferred options, but are instead used for all they teach. Novak teaches the broader ranges of 0.1 wt% or less, 0.05 wt% or less, and 0.01 wt% or less (paragraph [0024]), each of which overlaps the claimed range of 50 ppm to 0.4 wt%, rendering the claimed range prima facie obvious. Further, the term “substantial deoxygenation” does not exclude the claimed amounts, as indicated by the teachings of Novak of the broader ranges. As such, the fact that Novak recites substantial deoxygenation is not a teaching away from some amount of oxygen remaining in the stream, as claimed and as taught by Novak in paragraph [0024].
Applicant argues on page 3 of the Remarks that one of ordinary skill would not control the conditions of Novak to obtain the claimed range because the argument would require the skilled artisan to disregard Novak’s teaching that lower oxygen is better.
In response, the Examiner respectfully disagrees. Novak does teach substantial deoxygenation, but this does not inherently mean that Novak wishes to remove all oxygen, but merely means that deoxygenation is a goal of the hydrotreatment (paragraph [0024]). This is the case in Applicant’s process as well, where one of the purposes of the hydrotreatment is to remove oxygen (paragraph [0062]). As such the deoxygenation during the hydrotreatment of Novak does not teach away from the claimed deoxygenation due to the overlapping ranges of Novak and the claimed process, and one of ordinary skill in the art would continue to understand that the process of Novak is controlled to obtain the overlapping oxygen content.
Applicant argues on pages 3-4 of the Remarks that the instant specification demonstrates evidence of unexpected results regarding the claimed range.
In response, the Examiner respectfully disagrees. While the instant application contains an Example having an oxygen content in the claimed range, it is not compared to any other process. There is a single example at 0.39 wt% oxygen content, and no comparison to lower or higher oxygen contents. Thus, the assertion that the deep dewaxing severity in the Example would be expected to result in substantial yield loss is unsupported by the Example. Further, the instant specification focuses on the zeolite ZSM-48 as being important to the invention (paragraph [0052]) as much as the oxygen content. As such, there is no evidence of unexpected results, due to the oxygen content or the zeolite, and the process remains obvious.
Applicant argues on pages 4-5 of the Remarks that Novak doesn’t teach the diesel yield, that the Examiner’s position in the Office Action is not a proper position of inherency.
In response, the Examiner notes that the Office is unable to test the claimed processes or the processes in the prior art. As such, the Examiner must take the reasonable position that any results of the claimed process, if said process is taught by the reference, would be expected to occur, absent evidence to the contrary. Novak teaches the same process with the same catalysts and overlapping conditions (see Office Action below for specifics). As such, one of ordinary skill in the art would continue to expect similar results, including a diesel yield of 80 wt% or higher, absent any evidence to the contrary.
Applicant argues on page 5 of the Remarks that the claimed yield is achieved due to the oxygen content, and that the Examples of Novak do not achieve the claimed results at all conditions.
In response, as noted above, there is no evidence that the oxygen content is what provides the yield in the Example in the instant specification. Further, the teachings of Novak are not limited to the Examples, and the Example at 670°F is acknowledged as having increased cracking (paragraph [0047]). As such, one of ordinary skill in the art which desires to minimize cracking as preferred by Novak would be able to determine that the Example at 670°F was undesirable, and as such the Example does not teach away from the rest of the process and conditions of Novak which are desired to reduce cracking (paragraph [0046]). Thus, the process of Novak continues to render obvious the claimed process and results.
Applicant argues on page 6 of the Remarks that the same Example at 670°F in Novak also means that the product does not simultaneously comprise the claimed cloud point, cetane rating, and yield, that Novak does not teach a single Example where all the properties are shown, and it is improper to rely on different examples to establish different claim limitations.
In response, as explained above, a single Example in Novak does not teach away from the remaining teachings, especially because Novak acknowledges that the amount of cracking at 670°F is undesirable (paragraph [0047]). Further, the Examiner has not relied on different Examples for different claim limitations. The Examiner has referred to Table 2 to establish the range of possible results for each limitation, not selecting a single Example for one limitation and a different Example for a different limitation. There is nothing improper in using a range of teachings in Novak to render obvious a claimed range, as Novak is not limited to a single example but is used for all the teachings, and Novak teaches ranges of cetane number and other properties in Table 2. As such, Novak continues to render the process obvious.
Applicant argues on pages 6-7 of the Remarks that the secondary references Shih and Rockwell do not cure the deficiencies of Novak.
In response, as acknowledged in the Remarks, the Examiner is merely using the secondary references for other limitations, and as explained above, Novak continues to render obvious the oxygen content and resulting diesel properties. As such, the rejections are maintained.
Applicant argues on page 8 of the Remarks that adding the cracking catalyst of MFI to the process as taught by Rockwell is at odds with the high yield requirements and that the Examiner has not identified any teaching suggesting this combination.
In response, the Examiner notes that Rockwell is cited as explicitly teaching the same cloud point adjustment using the stacking catalysts. Applicant has not provided any evidence that the alleged increased cracking activity of the ZSM-5 would negatively affect the yield of diesel when performing the process at the claimed conditions. Thus, as Rockwell teaches a similar cloud point adjustment using the claimed catalyst combination, Rockwell provides motivation to use the stacked catalyst, absent evidence to the contrary.
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.
Claims 1, 2, 4-9, 12, and 15-20 are rejected under 35 U.S.C. 103 as being unpatentable over Novak et al. (US 2011/0219672) in view of Shih et al. (WO 2015/065679, cited on IDS of 08/08/2023).
With regard to claims 1, 2, 4, 6, 8, 9, 12, 16, 18, and 20, Novak teaches a method for hydroprocessing fuel feedstocks from biocomponent sources (paragraph [0001]) comprising the following steps:
a) contacting a feed comprising palm oil (bio-derived feedstock) with a catalyst and hydrogen treat gas (instant claims 4 and 12) (paragraph [0028]) in a reactor under hydrotreatment conditions of a temperature of 635°F (335°C), pressure of 380 psig, treat gas rate of 780 scf/bbl, and a LHSV of 0.6 h-1 (paragraph [0039]). These are within the ranges of 260-400°C, 200-5000 psig, 200-10,000 scf/bbl, and 0.1 to 10 hr-1 of instant claims 6 and 20. Novak further teaches that the resulting liquid product from the hydrotreating comprises 0.1 wt% or less oxygenates (paragraph [0024]), which overlaps the ranges of 50 ppm to 0.4 wt% of instant claims 1 and 12 and 0.1 to 0.4 wt% of instant claims 8 and 18, rendering the ranges prima facie obvious.
Novak does not explicitly teach that the conditions are controlled to selectively retain residual oxygenates and obtain the overlapping oxygenate content. However, Novak teaches the same hydrotreating conditions and an overlapping range of oxygen content resulting from the hydrotreating. Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention that the hydrotreating conditions in Novak are controlled to obtain the overlapping oxygen content, as claimed.
b) separating the hydrotreating product into a gas product and a liquid product (paragraph [0029]).
c) contacting the liquid product with a hydrogen treat gas (instant claim 4) (paragraph [0033]) and ZSM-48 in a separate dewaxing reactor (instant claim 2) to obtain a product stream (paragraph [0033]). Novak further teaches that the isomerization/dewaxing reduces the cloud point by at least about 50°C (paragraph [0027]), which is the same as the claimed range of 50°C or more of instant claims 1 and 12.
Novak further teaches that the product includes a winter diesel (arctic diesel) (paragraph [0027]) having a cetane value of 89.8, 90.1, 90.3, or 104 (page 5, Table 2), which values are within the ranges of at least 75 of instant claims 1 and 12 and 85 or above of instant claims 9 and 16. Novak further teaches the cloud point is -30, 043.9, -46.9, or -49.7 (page 5, Table 2), which values are within the range of a cloud point of -20°C or less of instant claims 1 and 12. Novak additionally teaches that the dewaxed product includes the diesel and also naphtha range hydrocarbons (page 5, Table 3).
Novak teaches embodiments where there is liquid recycle to the hydrotreating reactor, but also embodiments where there is no liquid recycle to the hydrotreating reactor (Figures 1 and 2 and paragraphs [0031]-[0032]). Thus, Novak teaches that the product having the claimed properties can be obtained from a single pass through the hydrotreatment and isomerization/dewaxing reactors, as claimed in instant claim 1.
Novak does not specifically teach i) separating the dewaxed product into liquid products and gas products; ii) fractionating the liquid products to obtain the naphtha range product and the diesel product, or iii) the yield of the diesel product.
With regard to i) and ii), Shih teaches a process for hydroprocessing distillate feeds to form low cloud point fuels (paragraph [0002]) where the feed is a biocomponent feed (paragraph [0020]). Shih teaches that the process comprises passing the feed to hydrotreating, fractionation, dewaxing, and then separation of the dewaxed product into a light ends (gas product), naphtha fraction, and at least one distillate fraction (paragraph [0043]) where the distillate fraction is an arctic diesel product (paragraph [0030]). Thus, Shih teaches that it is known to separate gas products, naphtha products, and arctic diesel products from a similar dewaxed product formed from hydrotreating and dewaxing a similar bicomponent feed.
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to separate a gas product, a naphtha product, and an arctic diesel product from the dewaxed product of Novak, because each of Novak and Shih teaches taking a biocomponent feed and performing hydrotreating and dewaxing with the same ZSM-48 catalyst at similar conditions, Novak teaches that the product is produced by dewaxing under a hydrogen atmosphere and that the product comprises gas phase (paragraph [0043]), naphtha (page 5, Table 3), and winter diesel (artic diesel) products (paragraph [0027]), and Shih teaches it is known to separate the gas product, naphtha product, and at least one distillate product which is arctic diesel from the dewaxed effluent (paragraph [0043]).
With regard to iii), Novak teaches the process comprises dewaxing over the same ZSM-48 catalyst and at conditions of 600 psig, 2000 scf/bbl, 2.14 h-1, and 620-650°F (327-343°C) (paragraph [0042] and Table 2), which are within the ranges of 260-400°C, 200-5000 psig, 200-10000 scf/bbl and 0.1 to 10 hr-1 of instant claims 6 and 20. Therefore, Novak teaches a similar bio-based feed which is hydrotreated at the same conditions to obtain a product having overlapping oxygen content and then is dewaxed at the same conditions over the same catalyst to obtain the same winter (arctic) diesel product having the same cetane index and cloud point. Therefore, one of ordinary skill in the art would reasonably expect that the process of Novak also produces a yield of the diesel product of 80 wt% or more, as claimed, absent any evidence to the contrary.
With regard to claims 5 and 15, Novak teaches recycling at least a portion of the gas phase products from the hydrotreating to the first reactor as the recycled hydrogen treat gas stream (combining with the first portion of hydrogen-rich treat gas stream) (paragraph [0028]).
With regard to claims 7 and 17, Novak teaches the dewaxing pressure of 600 psig (paragraph [0042]) which is within the claimed range of 200-5000 psig, the same ZSM-48 catalyst, and the claimed cloud point reduction of at least 50°C (paragraph [0027]). Thus, one of ordinary skill in the art would reasonably conclude that the pressure of Novak is an effective pressure which balances higher isomerization activity at lower pressures with lower catalyst deactivation rate at higher pressures, as claimed..
With regard to claim 19, Novak teaches pretreating the palm oil to remove impurities (contaminants) such as metals and gums (paragraph [0039]).
Claims 10, 11, 13, and 14 are rejected under 35 U.S.C. 103 as being unpatentable over Novak et al. (US 2011/0219672) in view of Shih et al. (WO 2015/065679, cited on IDS of 08/08/2023) as applied to claims 1 and 12 above, and further in view of Rockwell et al. (US 2019/0185771).
With regard to claims 10, 11, 13, and 14, Novak teaches the method above, where the dewaxing catalyst comprises ZSM-48 (paragraph [0026]).
Novak does not specifically teach stacking the ZSM-48 with a selective cracking catalyst.
Rockwell teaches a process for dewaxing bioderived diesel (paragraph [0002]) where the catalyst can comprise a combination of isomerization and cracking dewaxing catalysts, including ZSM-48 as an isomerization dewaxing catalyst and ZSM-5 as a cracking catalyst (paragraph [0017]) and where the dewaxing adjusts the cloud point downward, possibly from 10 to -50°C (ΔCP of 60°C). Thus, Rockwell teaches that it is known to use mixtures of isomerization and cracking catalysts for dewaxing (instant claims 10 and 13) and to change the cloud point by the desired at least 50°C, as claimed in instant claims 11 and 14.
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to stack the ZSM-48 and the ZSM-5 of Rockwell in order to produce the desired cloud point reduction by the combination of isomerization and cracking, as claimed, because each of Novak and Rockwell teaches dewaxing over zeolite catalysts comprising ZSM-48, and Rockwell teaches that combining ZSM-5 as a selective cracking catalyst with ZSM-48 produces a dewaxed bioderived diesel having the desirable cloud point (paragraph [0017]).
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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 ALYSSA L CEPLUCH whose telephone number is (571)270-5752. The examiner can normally be reached M-F, 8:30 am-5 pm, EST.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, In Suk Bullock can be reached at 571-272-5954. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/Alyssa L Cepluch/Examiner, Art Unit 1772
/Renee Robinson/Primary Examiner, Art Unit 1772
Prosecution Insights