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 .
This application is in response to the reply and amendments filed 10/13/2025.
Claims 19-34, 36-37 and 38-46(new) are pending.
Previous rejections of the claims under 35 USC 103 and non-statutory double patenting rejections are maintained and recited below.
Allowable Subject Matter
Claims 40, 43, and 46 contain allowable subject matter.
The following is a statement of reasons for the indication of allowable subject matter: art fails to teach or suggest the sequence of steps for fractionating pyrolysis oil wherein an anti-solvent is added prior to extraction solvent and in an amount of the anti-solvent from about 1 % to about 20 % mass ratio of the pyrolysis oil.
Claims 40, 43, and 46 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Response to Arguments
Applicant's arguments filed 10/13/2026 have been fully considered but they are not persuasive.
Applicant argues modifying the process of Moore by removing carbon from the wastewater raffinate of Moore is improper because there is no articulated identity of the carbons in the stream, how they could be used or why one would further process the stream.
Applicant’s arguments have been considered but are not persuasive. In response, Moore teaches wherein the “undesirable carbon containing compounds” include, but are not limited to, aldehydes and carboxylic acids. Par. (0006). Moore also teaches extracting into the extract, all of the compounds B and leaving in the raffinate substantially all of compounds A. Par. (0026). Compounds A include i) aldehydes, ii) ketones, iii) carboxylic acids, and iv) combinations thereof; and compounds B including C4+ compounds free of (i), (ii), and (iii). Par. (0026). Further, Moore teaches wherein the raffinate contains undesirable carbons and is referred to as waste water. Moore, par. (0027; 0006). It is common knowledge to reduce contaminants in wastewater prior to disposal to meet environmental regulations, including toxic carbon compounds like aldehydes.
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.
5. Claim(s) 19-23, 28-34, 37-39, 41-42, and 44-45 is/are rejected under 35 U.S.C. 103 as being unpatentable over Moore (US 2013/0306557) in view of Gajjela (GB2539685).
With respect to claims 19-20, Moore teaches a process comprising:
providing a pyrolysis oil first mixture comprising organic and aqueous phases;
contacting the oil with the diluent such as LCO naphtha, toluene, methyl isobutyl ketone, reformate, a bio-oil fraction, hydrotreated bio-oil fraction (0040) to modify the specific gravity and yield a second mixture, including adding 5wt%, 10wt%, and 20wt% LCO (0075; Table 1);
contacting the mixture with an extraction solvent such as methyl isobutyl ketone, cyclopentyl-methyl-ether, or combination (0060), and, having a water solubility of less than 2.5g/mL (0060);
separating the second mixture into an organic phase comprising the extractant, oil phase (0019-0020), and an aqueous phase comprising the raffinate (0007-0032), wherein the extractant oil phase comprises substantially all of group B carbons and the raffinate water phase comprises substantially all of the undesirable group A carbons. Compounds A include i) aldehydes, ii) ketones having 3-4 carbons, iii) carboxylic acids having 3-4 carbons, and iv) combinations thereof; and compounds B including C4+ compounds free of (i), (ii), and (iii). Par. (0026).
Moore teaches wherein the aqueous phase comprises aldehydes, ketones having 3-4 carbons, and carboxylic acids having 3-4 carbon, but is silent regarding wherein the aqueous phase is further subject to distillation to separate pyrolytic sugars and phenolic monomers.
Gajjela also falls in the art of separation of pyrolysis oil into organic and aqueous phases using an extraction process comprising a series of extraction stages. Page 4, line 24+. After the extraction and separation into aqueous and organic phases, Gajjela teaches that the aqueous stream may be subject to distillation to further separate remaining hydrocarbons from the water. While the specific extraction steps are different, both arts teach treating pyrolysis oil using a series of steps to extract valuable hydrocarbons in an organic HAF, leaving an aqueous biproduct containing smaller amounts of hydrocarbons. It would have been obvious to one of ordinary skill in the art at the time of filing to subject the aqueous raffinate of Moore to distillation to remove remaining hydrocarbon components to allow further use, sale or disposal of the water or separated compounds.
Given Moore teaches treating the same or similar feed, with the same solvents as claimed, to produce a water phase having aldehydes and ketones, which includes sugar compounds, it is expected that the same or overlapping range of compounds would be present in the organic and aqueous streams after separation.
With respect to claim 21, Moore teaches using e.g. ethyl acetate and MIBK. Each have a density of less than 1000 kg/m3. Moore also teaches using a solvent having a density less than 1 (0031).
With respect to claim 22 and 23, Moore teaches using e.g. MIBK or ethyl acetate (0060), which falls within the selected solvents and forms an azeotrope with water when distilled.
With respect to claims 28 and 30, Moore teaches mixing the solvent and pyrolysis oil before separating. In one example solvent and biooil are vigorously mixed for 30 seconds (0073). In another example, the solvent and biooil are stirred for one hour (0082).
With respect to claims 31 and 32, Moore teaches mixing and stirring of the two fluids. It would have been obvious to one of ordinary skill in the art at the time of filing to select any known means for mixing and stirring, including continuous or batch reactors, to achieve the desired contact between the solvent and biooil.
With respect to claim 29, Moore is silent regarding the required contact temperature. However, the process operates to mix two liquid streams liquid at room temperature. It would have been obvious to one of ordinary skill in the art at the time of the invention to contact the two reactants at room temperature to ensure the streams remain in liquid state and to minimize costs.
With respect to claim 33, Moore teaches wherein separating the mixture comprises allowing the mixture to settle in a settling vessel (0019-0020; 0047).
With respect to claim 34, Moore teaches allowing the mixture to settle. It is known that the amount of time allowed to settle will affect the composition of each phase. It would have been obvious to one of ordinary skill in the art at the time of filing to optimize the settling time to achieve an acceptable quality in the aqueous and oil phases.
With respect to claims 38-39, 41-42, 44-45, Moore teaches combining the pyrolysis oil with an aqueous solution of water-soluble compound (0043-44; see also 0045-0047). The aqueous solution is an anti-solvent. See a as claimed.
Claim(s) 24-27 and 36 is/are rejected under 35 U.S.C. 103 as being unpatentable over Moore and Gajjela as applied to claims 19-23, 28-34 and 37 as applied above, further in view of Tseng (US 2013/0172451).
With respect to claims 24-27 and 36, Moore teaches using a solvent such as MIBK, but fails to explicitly teach isobutyl acetate or n-butyl acetate.
Tseng teaches a method for separating aqueous and oil phases from a pyrolysis oil using an extractant/diluent. “In an embodiment, the extractant may comprise a solvent such as ethyl acetate, propyl acetate, butyl acetate, methyl isopropyl ketone (MIPK), methyl isobutyl ketone (MIBK), methyl i-amyl ketone (MIAK), ethyl ethyl ketone (EEK) or toluene. The solvent and the biomass pyrolysis oil have a weight ratio of about 0.1:1-1:1.” (0024). The solvent compounds and amounts taught in Tseng overlaps those of Moore. It is prima facie obvious to combine two compositions each of which is taught by the prior art to be useful for the same purpose, in order to form a third composition to be used for the very same purpose... [T]he idea of combining them flows logically from their having been individually taught in the prior art." In re Kerkhoven, 626 F.2d 846, 850, 205 USPQ 1069, 1072 (CCPA 1980).
It would have been obvious to one of ordinary skill in the art at the time of the invention to use isobutyl acetate or n-butyl acetate in combination with or in place of MIBK because both are known for extraction and separation of pyrolysis oil, including in overlapping solvent:oil ratios.
Double Patenting
Previous nonstatutory double patent rejection over U.S. Patent No. 11,466,220 is withdrawn because US 11,466,220 fails to claim the final distillation step.
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