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 5, 8, and 10 are amended. Claims 4 and 17 are cancelled. Claim 14 is withdrawn due to an earlier restriction requirement.
The amendments to claims 5, 8, and 10 and the cancellation of claim 17 overcome the previous 112(a) and (b) rejections and claim objections.
Claims 1-3, 5-13, 15, 16, and 18-20 are pending for examination below.
Response to Arguments
Applicant's arguments filed 30 June 2026 have been fully considered but they are not persuasive.
Applicant argues on page 9 of the Remarks that Thompson does not teach the claimed sulfided decarboxylation catalyst because paragraph [0039] broadly discusses optional catalyst pretreatments including reduction and in separate embodiments sulfidation and paragraph [0047] teaches that decarboxylation is achieved using a high nickel catalyst excluding molybdenum, but does not disclose sulfidation.
In response, the Examiner respectfully disagrees. The combination of separately listed embodiments is not improper unless the reference excludes the combination of embodiments, and Thompson does not state that embodiments cannot be used together. Thus, there is no teaching away from combining embodiments from different paragraphs within Thompson in order to obtain the claimed catalyst, as one of ordinary skill in the art would be motivated to select any catalyst options taught by Thompson in order to form a desired catalyst. Further, as noted by Applicant in the Remarks, Thompson explicitly provides a motivation for using the sulfiding step, which is that sulfiding may be desirable for the long term activity of the catalyst (paragraph [0037]). Therefore, one of ordinary skill in the art would find it obvious to use the sulfiding step for the reasons of Thompson when performing any reaction with any catalyst of Thompson, as Thompson does not restrict the usefulness of the sulfiding to only certain catalysts or reactions in paragraph [0039]. As such, it remains obvious to select the catalyst of Thompson which comprises only nickel for decarboxylation and sulfide the nickel catalyst, in order to help the catalyst activity as taught by Thompson in paragraph [0037].
Applicant argues in the paragraphs bridging pages 9-10 of the Remarks that decarboxylation is disclosed in paragraph [0060] of Thompson, but this paragraph does not describe a sulfided catalyst, only mentioning reduction and tying the reduction to the desired odd to even ratio. Thus, Thompson does not disclose the claimed sulfided high nickel catalyst with the desired decarboxylation reaction, and the omission is significant because claim 1 requires a sulfided catalyst.
In response, the Examiner respectfully disagrees. As explained above, Thompson clearly renders obvious decarboxylation using a combination of a nickel catalyst which has been sulfided, as taught in paragraphs [0039] and [0047]). Thompson is not required to provide the explicit motivation for the sulfidation within the same paragraph as the teaching of the decarboxylation. While Thompson does not explicitly teach that the sulfidation is used for decarboxylation, Thompson also does not teach away from using sulfidation for the decarboxylation catalyst, instead teaching sulfidation as a pretreatment option for any catalyst for the reactions disclosed in Thompson (paragraph [0039]). Because Thompson is not limited to a single embodiment but is instead used for all its teachings, one of ordinary skill in the art would find it obvious to use a sulfided high nickel catalyst for decarboxylation in order to retain high catalyst activity, as both ideas are explicitly disclosed in Thompson, absent any evidence of criticality or unexpected results. It is known in the art that sulfided nickel catalysts are selective for decarboxylation whereas sulfided NiMo or Mo catalysts are selective for hydrodeoxygenation (see attached NPL to Kubicka page 200, last paragraph before section 2, and also pages 205-206, section 3.5). As such, it remains obvious from the teachings of Thompson to select the option for sulfiding, for the reasons of catalyst activity as explicitly taught by Thompson, when also selecting the nickel catalyst for decarboxylation explicitly taught by Thompson.
Applicant argues on pages 10-11 of the Remarks that Thompson does not teach the claimed aviation fuel because Thompson does not demonstrate compliance with the ASTM D86 standards, and that the Examiner’s position of a reasonable expectation of the resulting aviation fuel having the claimed properties lacks evidentiary support.
In response, the Examiner respectfully disagrees. Thompson discloses that the product can be used as jet fuel (claimed aviation fuel) and as explained above teaches the same process of decarboxylation of a similar feedstock at similar conditions and over a similar catalyst. The Examiner is unable to run the tests themselves, and thus must rely on the assumption that a similar process produces a similar result, including the claimed ASTM D86 properties, absent any evidence of unexpected results or criticality to the differences between the claimed process and the process in the prior art. If Applicant has any such evidence, such as evidence that reduced catalysts perform differently than sulfided catalysts for decarboxylation, this would be taken into account. The Examples in the instant specification compare an entirely different catalyst to a sulfided catalyst, and thus are not evidence comparing the closest prior art of Thompson with the claimed process. Absent such evidence of unexpected results or criticality, the Examiner’s position is maintained. The Examiner is not required to have evidentiary support for an obviousness rejection, but merely is required to lay forth a reasonable position with clear articulation of the reasons that the results are obvious, which is included within the rejection below and repeated in the response herein. After this articulation, the burden of proof of non-obviousness shifts to the Applicant (MPEP 2142). Therefore, Thompson continues to render obvious the claimed catalyst and, as such, the claimed process and results of the process, absent any evidence to the contrary, which has not been provided.
Applicant argues on pages 11-12 of the Remarks that the Examiner has used Applicant’s claim as a template, first assuming the sulfidation can be combined with the decarboxylation catalyst and second assuming the process necessarily produces an aviation fuel having the claimed ASTM end-boiling point despite Thompsons’ silence, where the assumptions are interdependent and Thompson establishes neither the catalyst nor the resulting product.
In response to applicant's argument that the examiner's conclusion of obviousness is based upon using Applicant’s disclosure as a template (improper hindsight reasoning), it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971). As addressed in detail above, Thompson does render obvious the claimed catalyst and process, where Thompson provides explicit motivation to sulfide the catalyst generally and to specifically use a nickel oxide in the decarboxylation (paragraphs [0037] and [0047]). Thus, Thompson does in fact teach both requirements of the catalyst and reaction, because Thompson is not limited to a single embodiment but is used for all the teachings within. As such, the Examiner has come to the reasonable conclusion that the boiling point of the resulting aviation fuel is a resulting property of the process of Thompson. Having established the prima facie case of obviousness, the burden shifts to the Applicant to provide evidence that this is not the case (MPEP 2142). No evidence has been provided, and the rejection is maintained.
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 1-3, 5, 10, 11,15, 16, 18, and 19 are rejected under 35 U.S.C. 103 as being unpatentable over Thompson et al. (US 2016/0060186).
With regard to claims 1, 3, 10, 18, and 19, Thompson teaches a method for conversion of oxygen containing compounds to hydrocarbon products (paragraph [0001]) comprising reacting a feedstock of over 50 wt% C18 based polyester (fatty acid ester) compounds by decarboxylation (paragraph 0060]) over a catalyst to obtain a product (decarboxylation mixture) (paragraphs [0050]-[0053]) and where the product includes jet fuel (paragraph [0006]), which is a specific type of aviation fuel. The C18 portion is a chain residue (side chain) (paragraph [0084] and Formula II). The range of over 50 wt% C18-based compounds is within the range of at least 40 wt% C18 side chains of instant claim 1, and overlaps the range of at least 60 wt% C18 side chains of instant claim 3, rendering the range prima facie obvious. This range of over 50 wt% C18-based polyester (fatty acid ester) compounds in the feedstock is also within the range of at least 50 wt% fatty acid esters of instant claim 10.
Thompson further teaches that the reaction is selective toward decarboxylation (paragraph [0060]) and that for decarboxylation the catalyst comprises at least 40 wt% nickel and excludes the presence of Mo (paragraphs [0047] and [0050]). This is within the range of more than 5 wt% Ni of instant claim 1. Thompson does not explicitly teach that the catalyst also excludes the presence of Co and W, however, Thompson teaches a monometallic catalyst is selected in certain embodiments (paragraph [0038]). In the case a monometallic nickel catalyst is selected as taught by Thompson in paragraphs [0050] and [0038], the amounts of Mo, Co, and W are expected to be 0 wt% each, which is within the range of less than 1 wt% each of instant claim 1. Thompson additionally teaches the catalyst is sulfided (paragraph [0039]).
Thompson also teaches the ratio of odd-numbered to even-numbered hydrocarbons in the decarboxylation product is at least 5:1 (paragraph [0060]), which is within the ranges of at least 1.5:1 of instant claim 1, at least 2:1 of instant claim 18, and at least 3:1 of instant claim 19.
Thompson does not explicitly teach the boiling range end point of the jet fuel is below 300°C according to ASTM D86. However, Thompson teaches overlapping conditions to the conditions in instant claim 2, including a temperature of 200-500°C (page 13, claim 108), pressure of greater than 1 atm (1.01 bar) (page 13, claim 109), space velocity of 1 to 5 h-1 (paragraph [0066]), and that the catalyst comprises a support (carrier) which is alumina (refractory oxide) (paragraph [0042]). Thus, because Thompson teaches the similar process with similar feed, conditions, catalyst, and decarboxylation selectivity to produce a product comprising a similar jet fuel (aviation fuel) as described above, one of ordinary skill in the art would reasonably find it obvious to expect the jet fuel of Thompson to also have an end point of below 300°C according to ASTM D86, as claimed, absent any evidence to the contrary.
With regard to claims 2, 15, and 16, Thompson further teaches a temperature of 200-500°C (page 13, claim 108), pressure of greater than 1 atm (1.01 bar) (page 13, claim 109), space velocity of 1 to 5 h-1 (paragraph [0066]), and the catalyst comprises a support (carrier) which is alumina (refractory oxide which is inert and substantially free of zeolites instant claims 2, 15, and 16) (paragraph [0042]). These overlap the ranges of 250-400°C, 30-150 bar, and 0.1-2 h-1 of instant claim 2, rendering the ranges prima facie obvious.
With regard to claim 5, Thompson teaches that the polyesters are saturated or unsaturated (paragraphs [0118]-[0120]). Thus, it would have been obvious to one of ordinary skill in the art at the time of the invention to select polyesters that are 100% saturated, which is a feedstock comprising less than 10 wt% olefinic oxygenates as claimed.
With regard to claim 11, Thompson teaches the process further comprises hydrocracking the product (deoxygenated hydrocarbon mixture) over a catalyst (paragraph [0054]).
Claims 6, 8, 12, and 13 are rejected under 35 U.S.C. 103 as being unpatentable over Thompson et al. (US 2016/0060186) as applied to claims 1 and 11 above, and further in view of Ratnasamy et al. (US 2015/0080623).
With regard to claim 6, Thompson teaches that the oxygenated feedstock can include saturated or unsaturated components (paragraphs [0118]-[0120]). Thompson does not specifically teach the amount of unsaturated components in the feedstock. However, it would have been obvious to one of ordinary skill in the art at the time of the invention to select a feedstock comprising at least 10 wt% unsaturated compounds, as claimed, because Thompson teaches that the components can be saturated or unsaturated and selecting a feedstock comprising at least 10 wt% unsaturated compounds would be obvious to try without undue experimentation and with a reasonable expectation of success, because Thompson teaches that unsaturated components are known to be used in the process.
Thompson does not specifically teach saturating the feedstock comprising unsaturated oxygenates to produce the saturated oxygenated feedstock.
Ratnasamy teaches a process for conversion of carboxylic acid based feedstocks by decarboxylation (paragraph [0002]) to jet fuels (paragraph [0037]). Ratnasamy further teaches that saturated carboxylic acids can be produced by selective hydrogenation of unsaturated carboxylic acids, and that saturated carboxylic acids are more favorable for the decarboxylation process (paragraph [0029]).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use the hydrogenation process of Ratnasamy in the process of Thompson, because each of Thompson and Ratnasamy teach conversion of oxygenated feedstocks based on carboxylic acids by decarboxylation to jet fuels, and Ratnasamy teaches that saturated carboxylic acid based oxygenates can be produced by hydrogenation and that saturation is desirable for the decarboxylation reaction (paragraph [0029]).
With regard to claim 8, Thompson teaches the process above, where the product comprises a jet fuel.
Thompson does not explicitly teach i) the boiling range of the jet fuel includes a T10 point below 205°C and a final boiling point below 300°C according to ASTM D86 or ii) separating the jet fuel.
With regard to the boiling point range i), Thompson teaches a similar process with similar feed, conditions, catalyst, and decarboxylation selectivity to produce a product comprising a similar jet fuel (aviation fuel) as described above, one of ordinary skill in the art would reasonably expect the jet fuel of Thompson to also have an end point of below 300°C, as claimed, absent any evidence to the contrary.
With regard to the separation ii), Ratnasamy teaches that it is known to separate the reaction products of decarboxylation to obtain jet fuel (paragraph [0009]). Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to add the step of separating the jet fuel from the product of Thompson, because each of Thompson and Ratnasamy teaches decarboxylation to produce a product comprising jet fuel, and Ratnasamy teaches separation of the jet fuel from the decarboxylation product is known (paragraph [0009]).
With regard to claim 12, Thompson teaches the process of claim 11 above, where there is an additional hydrocracking step (paragraph [0054]).
Thompson is silent regarding the conditions and catalyst for the hydrocracking, thus one of ordinary skill in the art would look to related art to find suitable conditions and catalyst for the hydrocracking.
Ratnasamy teaches a process for conversion of carboxylic acid based feedstocks by decarboxylation (paragraph [0002]) to jet fuels (paragraph [0037]). Ratnasamy further teaches the decarboxylated paraffins undergo further transformation through hydrocracking (paragraph [0002]) and that the catalyst for cracking comprises an acidic oxide component which is an aluminosilicate zeolite which can increase cracking (molecular sieve showing high cracking activity) (paragraph [0028]) and a metal which is nickel (paragraph [0019]). Ratnasamy also teaches a temperature of 200 to 450°C and a pressure of 1 to 60 bar (paragraph [0031]), which overlap the ranges of 300-450°C and 30-150 bar of instant claim 12, rendering the ranges prima facie obvious.
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use the hydrocracking conditions and catalyst of Ratnasamy in the process of Thompson, because each of Thompson and Ratnasamy teach decarboxylation of carboxylic acid based oxygenates followed by hydrocracking, Thompson is silent regarding the conditions and catalyst, and Ratnasamy teaches the claimed conditions and catalyst are suitable for hydrocracking (paragraphs [0028] and [0031]).
Thompson and Ratnasamy are silent with regard to the LHSV. However, the space velocity of the reaction is a process parameter which is known to affect the conversion of the reactants, and thus can be optimized. It would have been obvious to one having ordinary skill in the art to have determined the optimum value of an LHSV of between 0.5-8 h-1 as claimed, through routine experimentation in the absence of a showing of criticality. See MPEP 2144.05(II).
With regard to claim 13, Thompson teaches the process further comprises isomerization of the decarboxylation product (paragraph [0054]).
Thompson is silent regarding the conditions and catalyst for the isomerization, thus one of ordinary skill in the art would look to related art to find suitable conditions and catalyst for the hydrocracking.
Ratnasamy teaches a process for conversion of carboxylic acid based feedstocks by decarboxylation (paragraph [0002]) to jet fuels (paragraph [0037]). Ratnasamy further teaches that the decarboxylated paraffins undergo further transformation through isomerization (paragraph [0002]). Ratnasamy also teaches that the catalyst for isomerization comprises an acidic oxide component which is an aluminosilicate zeolite which can increase isomerization (molecular sieve showing high isomerization activity) (paragraph [0028]) and a metal which is nickel (paragraph [0019]). Ratnasamy further teaches a temperature of 200 to 450°C and a pressure of 1 to 60 bar (paragraph [0031]), which overlap the ranges of 250-350°C and 30-150 bar of instant claim 13, rendering the ranges prima facie obvious.
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use the isomerization conditions and catalyst of Ratnasamy in the process of Thompson, because each of Thompson and Ratnasamy teach decarboxylation of carboxylic acid based oxygenates followed by isomerization, Thompson is silent regarding the conditions and catalyst, and Ratnasamy teaches the claimed conditions and catalyst are suitable for isomerization (paragraphs [0028] and [0031]).
Thompson and Ratnasamy are silent with regard to the LHSV. However, the space velocity of the reaction is a process parameter which is known to affect the conversion of the reactants, and thus can be optimized. It would have been obvious to one having ordinary skill in the art to have determined the optimum value of an LHSV of between 0.5-8 h-1 as claimed, through routine experimentation in the absence of a showing of criticality. See MPEP 2144.05(II).
Claim 7 is rejected under 35 U.S.C. 103 as being unpatentable over Thompson et al. (US 2016/0060186) in view of Ratnasamy et al. (US 2015/0080623) as applied to claim 6 above, and further in view of Ellig et al. (US 2015/0057477) and Hirano et al. (US 4,789,654).
With regard to claim 7, Thompson in view of Ratnasamy teaches the hydrogenation to produce saturated oxygenates above.
Thompson in view of Ratnasamy is silent with regard to the conditions and catalyst for the pre-hydrogenation. Thus, one of ordinary skill in the art would look to related art to find suitable conditions and catalyst.
Ellig teaches hydrogenation of olefins in renewable feeds including glycerides and free fatty acids to produce fuels (paragraphs [0021], [0016]). Ellig teaches that the hydrogenation conditions include a catalyst comprising nickel/molybdenum on a refractory oxide support (paragraph [0022]), a temperature of 200 to 300°C, a pressure of 200 to 1000 psi (13.8 to 68.9 bar) (paragraph [0022]), and a LHSV of about 1 to about 4 (paragraph [0023]). These ranges overlap the ranges of 150 to 280°C, 30-150 bar, and 0.1 to 2 LHSV of instant claim 7, rendering the ranges prima facie obvious.
Ellig is silent with regard to the amount of nickel and molybdenum. However, Ellig teaches that the catalyst comprising nickel and molybdenum is well known in the art (paragraph [0022]).
Hirano teaches a catalyst for hydrotreating to produce fuels (Abstract). Hirano teaches that the catalyst comprises Group VIA and Group VIII metal on an alumina support (Abstract) where the Group VIA metal can be molybdenum and the Group VIII metal can be nickel (column 3, lines 53-57). Hirano further teaches that the amount of Group VIA metal is 5 to 20 wt% and the amount of Group VIII metal is 1 to 10 wt% (column 3, lines 58-62), which are within the range of 5 to 20 wt% molybdenum and overlaps the range of 1 to 5 wt% nickel, rendering the range prima facie obvious.
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use the amounts of nickel and molybdenum of Hirano in the catalyst of Ellig, because Ellig and Hirano each teach a hydrogenation catalyst for producing fuels, Ellig is silent regarding the amounts but says the catalysts are well known, and Hirano teaches a hydrogenation catalyst having the claimed amounts is known.
It would have been obvious to one of ordinary skill in the art at the time of the invention to use the conditions and catalyst of Ellig in view of Hirano in the method of Ratnasamy, because Ratnasamy and Ellig each teach hydrogenation of renewable feeds comprising glycerides and fatty acids to saturate olefins, Ratnasamy is silent regarding the conditions and catalyst, and Ellig teaches that the claimed hydrogenation conditions are suitable for hydrogenation of a similar feed.
Claim 9 is rejected under 35 U.S.C. 103 as being unpatentable over Thompson et al. (US 2016/0060186) as applied to claim 1 above, and further in view of Ellig et al. (US 2015/0057477).
With regard to claim 9, Thompson teaches the process above, where the catalyst is sulfided by contacting with a sulfur containing compound in the hydrogen flow (paragraph [0039]).
Thompson fails to explicitly teach the sulfiding is done in situ during the reacting or the amount of the sulfur compound in the hydrogen feed.
Ellig teaches a process for deoxygenation of renewable feeds (Abstract) to produce jet fuels (paragraph [0014]). Ellig further teaches that the feed to the deoxygenation comprises a sulfiding agent to maintain the sulfided state of the deoxygenation catalyst (paragraph [0022]), where the sulfiding agent is added in an amount of less than 2000 ppm (paragraph [0018]), which overlaps the range of at least 50 ppmv of instant claim 9, rendering the range prima facie obvious.
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use the sulfiding step of Thompson during the deoxygenation reaction, as claimed, because Thompson and Ellig each teach deoxygenation of renewable feeds to produce jet fuel, using a sulfided catalyst, and Ellig teaches that sulfiding during the reaction is known and is used to maintain the sulfided state (paragraph [0022]).
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
/IN SUK C BULLOCK/Supervisory Patent Examiner, Art Unit 1772
