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 .
This communication is in response to the amendment and reply filed 7/7/2026.
Claims 11-19 and 20-23 (new) are pending.
Response to Arguments
Previous rejections of the claims under 35 USC 112 are withdrawn in view of the amendments to the claims.
Previous rejections of the claims under 35 USC 103 are maintained.
Applicant's arguments filed 7/7/2026 have been fully considered but they are not persuasive. Applicant characterizes the art and argues the art fails to teach or suggest conversion of oxygenated compounds to alcohols, as required by the present claims.
In response, the art teaches reaction in a slurry processing operating under conditions which overlap the claimed conditions with a slurry catalyst as claimed for partial conversion of the oxygen-containing compounds in the first reactor. Given the same process is conducted on the same feed, it is expected that the same carbonyl and carboxyl conversion to alcohol occurs.
Alternatively, such conversion of carbonyl and carboxyl compounds to alcohols under hydrotreating conditions is known in the art. For example, US 2024/0124787 discloses wherein “liquid oil, e.g. pyrolysis oil is stabilized at low temperatures by the conversion of at least the most reactive compounds in the pyrolysis oil, such as furfural, furans, aldehydes, ketones and acids, into alcohols, for instance by efficiently converting carbonyls into alcohols. The alcohols can further be converted to saturated organic compounds during the stabilization, and/or in a subsequent hydroprocessing stage such as HDO.” Par. [0012]. The process occurs in the presence of a hydrogenation catalyst and hydrogen at overlapping conditions to the cited art. Therefore, it is expected that the same conversion to alcohols would occur.
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.
Claim(s) 1-13 and 17-19 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kalnes (CA 2879323).
Alternatively, Claim(s) 1-13 and 17-19 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kalnes (CA 2879323) in view of Stummann (US 2024/0124787).
With respect to claim 11, Kalnes (CA 2879323) teaches a method for producing a stabilized biomass oil, comprising:
providing a biomass oil selected from a biomass pyrolysis oil with oxygen having up to 30% or greater (0019), which is within the range of 8 to 55% by mass oxygen; he biomass-derived pyrolysis oil include carboxylic acids, phenols, cresols, alcohols, aldehydes, etc, and is chemically and thermally unstable (0020);
providing a catalyst at least one metal selected from the metals in groups 3 to 14 (0025) which may be known catalyst (0025) and may be in a slurry reactor (0024), thus the catalyst would be unsupported;
hydroconversion and hydrotreating the biomass oil in the presence of hydrogen (0021) and catalyst in a slurry reactor (0024), occurring at a reaction temperature for hydroconversion may range from 100-350 C under a pressure of 3.5-15 MPa for an LHSV of 0.1-1/hr (0026), which overlaps the claimed ranges;
the effluent contains improved stability (0007). Kalnes teaches conversion of oxygen in the effluent to 0-10 %, which is an oxygen conversion greater than 20%, and given substantially the same feed may be reacted in the same hydroconversion reactor and metal catalyst with the same reaction conditions, a carbonyl conversion in the range claimed is also expected.
A prima facie case of obviousness is established when a prior art range encompasses, overlaps, touches or lies inside a claimed range. MPEP 2144.05
Kalnes does not expressly teach the stabilized biomass oil containing alcohols resulting from the conversion of sugars, ketones, aldehydes and carboxylic acids into alcohols. However, Kalnes teaches reaction in a slurry processing operating under conditions which overlap the claimed conditions with a slurry catalyst as claimed for partial conversion of the oxygen-containing compounds in the first reactor. Given the same process is conducted on the same feed, it is expected that the same carbonyl and carboxyl conversion to alcohol occurs.
Alternatively, with respect to the conversion of carbonyls and carboxyls to alcohols in the hydroconversion reaction, Stummann (US 2024/0124787) stabilizing pyrolysis or HTL oils through hydrotreating in the presence of hydrogen and a catalyst results under overlapping conditions to Kalnes results in such conversion. Stummann discloses “pyrolysis oil is stabilized at low temperatures by the conversion of at least the most reactive compounds in the pyrolysis oil, such as furfural, furans, aldehydes, ketones and acids, into alcohols, for instance by efficiently converting carbonyls into alcohols.” Par. [0012]. “Ni—Mo based catalyst is capable of effectively stabilizing liquid oils such as pyrolysis oils or HTL oils at low temperatures, i.e. in the range 20-240° C.” Par. [0011] Similar to Kalnes, “[t]he alcohols can further be converted to saturated organic compounds during the stabilization, and/or in a subsequent hydroprocessing stage such as HDO.” Par. [0012]. Hydrotreating process operates in a fixed bed at the following operating conditions: inlet temperature of 20-240° C, a pressure of 100-200 barg, a liquid hourly space velocity (LHSV) of 0.1-1.1 h−1, and a hydrogen to liquid oil ratio of 1000-6000 NL/L. Par. [0013]. The stabilization reactor enables stabilization at these operating conditions by “converting carbonyls to alcohols and thereby increase[s] operation time before plugging issues—if any—arise, while at the same time suppressing coking of the catalyst and attendant catalyst deactivation, as well as avoiding hydrogen starvation.” Par. [0014]. While the specific stabilization reaction occurs in a fixed bed in Stummann, par. [0013], the same reactions are expected to occur where operating at the same conditions on the same feedstream. Therefore, before the filing date of the claimed invention, it would have been expected that conversion of oxygen compounds to alcohol would occur given substantially the same process is conducted at overlapping conditions, or would have been obvious to one of ordinary skill in the art to convert carbonyls to alcohols in the first reaction stage of Kalnes for stabilization as taught in Stummann for the benefit of increasing operation time before plugging issues—if any—arise, while at the same time suppressing coking of the catalyst and attendant catalyst deactivation, as well as avoiding hydrogen starvation.
With respect to claim 12, Kalnes teaches the reaction temperature for hydroconversion may range from 100-350 C (0026), which overlaps the claimed ranges.
With respect to claim 13, Kalnes teaches the reaction Pressure for hydroconversion may range of 3.5-15 MPa (0026), which overlaps the claimed ranges.
With respect to claim 17, Kalnes teaches recovering and returning effluent to the reactor (0034).
With respect to claim 18, Kalnes teaches fractionating the effluent (0034) which produces light and heavy fraction of biooil.
With respect to claim 19, Kalnes teaches at least part of the effluent may be used as a high energy density fuel (0007; 0003, 0004).
Claim(s) 14-16 and 20-23 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kalnes (CA 2879323) as applied to claims 11-13 and 17-19, further in view of Lamminpas (CA 3160348).
Alternatively, Claim(s) 14-16 and 20-23 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kalnes (CA 2879323) in view of Stummann (US 2024/0124787) as applied to claims 11-13 and 17-19, further in view of Lamminpas (CA 3160348)..
With respect to claim 14-16 and 20, Kalnes teaches a number of metals in the claimed range, including Mo, W, Co, Pd, among others (0026) and teaches using slurry catalyst (0025).
Kalnes does not explicitly teach wherein the precursor of the unsupported hydrotreatment catalyst is a metal compound selected from ammonium salts, sulfates, nitrates, chlorides, naphthenates, oxyhydroxides, carbamates, dithioates, oxides, octoates, metallocenes, or any other organometallic compound.
Lamminpas is directed to the design of “[a] process for hydrotreating recycled or renewable feedstocks with a catalytic microparticle slurry, and a process for manufacturing the catalytic microparticle slurry” (abstract). Lamminpas teaches “particles disperse readily in hydrocarbons and in liquid carbonaceous feedstocks, and have a large accessible surface area which makes them effective when used as a catalyst in hydrotreating of oxygen-containing feedstocks”. The catalyst may be, for example, Molybdenum sulphide formed from a molybdenum salt (page 10-11). The particles are dispersed in the liquid medium and may be separated from the effluent using known techniques such as filters, settling, magnetic separation or cyclones (page 9).
Therefore, before the filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to modify the metal catalyst in slurry reactor of Kalnes by selecting the disclosed metal slurry catalyst of Lamminpas because both are directed to hydrotreating for deoxygenation of biomass derived oil containing overlapping ranges of oxygen using a slurry reactor, and Lamminpas discloses specific slurry catalyst which may be used and because it is obvious to combine known elements from the art to do no more than obtain predictable results.
With respect to claims 21-23, Kalnes teaches at least part of the effluent may be used as a high energy density fuel (0007; 0003, 0004).
Additional Art Made of Record
US 2025/0084316 discloses a first stabilization of biooil prior to second deoxygenation processing. “[T]he stabilization step is conducted at a temperature of 20-240° C., a pressure of 100-200 barg and a liquid hourly space velocity (LHSV) of 0.1-1.1 h.sup.−1, and a hydrogen to liquid oil ratio is 1000-6000 NL/L, such as 2000-5000 NL/L, suitably in any of: a fixed bed reactor, a slurry bed reactor, trickle bed reactor, and a fluidized bed reactor.” Par. [0065]. In stabilization carbonyl compounds are converted to alcohols at low temperature to prevent polymerization in later high temperature reactions. Par. [0003].
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 Brandi Doyle whose telephone number is (571)270-1141. The examiner can normally be reached Monday-Friday, 8:00 AM - 3:00 PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Prem 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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/BRANDI M DOYLE/ Examiner, Art Unit 1771
/PREM C SINGH/ Supervisory Patent Examiner, Art Unit 1771
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