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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 06 November 2025 has been entered.
Claims 1-3, 5-7, and 9-14 are amended. Claims 15-19 are new. Claim 3 is cancelled. Claim 14 is withdrawn due to an earlier restriction requirement.
Claims 1-3, 5-13, and 15-19 are pending for examination below.
Response to Arguments
Applicant’s arguments and amendments, see Remarks, filed 06 November 2025, with respect to the rejection(s) of claim(s) 1-3 and 5-13 under USC 103 over Ratnasamy have been fully considered and are persuasive. Ratnasamy does not teach a sulfided catalyst. Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of newly discovered prior art in view of the amendment.
Claim Objections
Claims 8 and 10 are objected to because of the following informalities:
With regard to claim 8, the claim recites “separating the deoxygenated hydrocarbon mixture…to provide a hydrocracked intermediate fuel…” However, claim 1 does not recite a hydrocracking step, thus the intermediate fuel from the product of claim 1 is not hydrocracked. As such, the term “hydrocracked” is a typographical error and should be deleted from claim 8.
With regard to claim 10, the claim recites “or fatty acids”. This should be “fatty acid esters” for antecedent basis purposes.
Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claim 17 is rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
With regard to claim 17, the claim recites “wherein the reaction comprises decarboxylation and hydrodeoxygenation without substantial hydrocracking.” Applicant has generally recited that the amended claims find support in paragraphs [0023], [0034], [0038], [0041], [0043], and [0046], where the Examiner assumes the paragraphs refer to the published application as there are no paragraph numbers in the instant specification as filed. The Examiner is unable to find the support for this recitation in the cited paragraphs or in the specification as a whole. Paragraph [0042] discuss the nature of the hydrocracking catalyst for the selectivity of the hydrocracking, but this is referring to the separate hydrocracking step as claimed in claims 11 and 12. Paragraph [0043] discusses that the decarboxylation reaction favors producing the desired aviation range hydrocarbons, but makes no mention of hydrocracking explicitly, and if referring back to the previous paragraph, is discussing the separate hydrocracking step which is claimed. Paragraph [0046] states that when the reaction comprises “a high selectivity towards decarboxylation over hydrodeoxygenation, stable production of hydrocarbons boiling in the aviation fuel range is possible…compared to hydrodeoxygenation in combination with hydrocracking”. However, this is comparing decarboxylation versus hydrodeoxygenation, as opposed to claim 17 which recites that both take place. Further, it is not clear that the “hydrodeoxygenation in combination with hydrocracking” of paragraph [0046] means that the hydrodeoxygenation and hydrocracking are occurring simultaneously, as the phrase “combination” can mean two separate steps used in the same process, which aligns with the process of claims 11 and 12.
Thus, there is no support for the recitations that i) the claimed reaction comprises both decarboxylation and hydrodeoxygenation or ii) that the reactions take place without substantial hydrocracking, and the claim is new matter.
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 5-7 and 17 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
With regard to claim 5, the claim recites “wherein the feedstock is a saturated decarboxylation feedstock, comprising less than 10 wt% oxygenates.” Claim 1 recites that the feedstock “comprises fatty acid esters and/or triglycerides”. It is unclear whether the saturated decarboxylation feedstock of claim 5 is a further limitation stating that the fatty acid esters and/or triglycerides are saturated, or instead is a separate decarboxylation feedstock comprising different saturated oxygenates which is used with the feedstock of claim 1, which would not further limit the independent claim. Thus, the claim is indefinite.
For purposes of examination, the Examiner will consider that the intent of claim 5 is to specify that the feedstock of claim 1 is a feedstock comprising saturated oxygenates, where the oxygenates are specifically the fatty acid esters and/or triglycerides as in claim 1 (see instant specification page 7, lines 27-28 and page 12, lines 19-20). The Examiner suggests “wherein said feedstock comprises saturated fatty acid esters and/or triglycerides and comprising less than 10 wt% olefinic oxygenates.”
With regard to claim 17, the claim recites “substantial hydrocracking.” The term “substantial” is a relative term which renders the claim indefinite. The term “substantial” is not defined by the claim, the specification does not provide a standard for ascertaining the requisite degree, and one of ordinary skill in the art would not be reasonably apprised of the scope of the invention.
For purposes of examination, there is no definition of substantial in the specification and, as discussed above, no support for the claimed concept. Thus, the Examiner will give “substantial” the broadest reasonable interpretation, which is that the reaction comprises mainly the decarboxylation, where the hydrocracking is a non-preferred side reaction that takes place in small amounts, if at all.
With regard to claims 6 and 7, the claims are rejected as being dependent on a rejected base claim.
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, 10, 11, and 15-19 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 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]).
With regard to claim 17, Thompson teaches that the reaction when using the nickel catalyst and compounds having C18 side chains favors decarboxylation rather than hydrodeoxygenation (paragraphs [0047] and [0060]). Further, 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. Thus, it is expected that the decarboxylation of Thompson also occurs without substantial hydrocracking, as claimed, absent any evidence to the contrary.
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
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.
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/Alyssa L Cepluch/Examiner, Art Unit 1772
/IN SUK C BULLOCK/Supervisory Patent Examiner, Art Unit 1772