DETAILED ACTION
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 .
Election/Restrictions
Applicant's election with traverse of Group I, claims 1 and 10 in the reply filed on 11/20/25 is acknowledged. The traversal is on the ground(s) that Groups I and II should be examined together as they have a common inventive concept. Applicants state that the claims are all drawn to a unified inventive concept of the conversion of cellulose to polyols by employing a specific Al-Ni-W catalyst supported on zeolite and that these catalytic systems achieves 100% complete cellulose conversion into polyols with a high degree of ethylene glycol selectivity and this catalytic system represent the core inventive concept linking the process and catalyst claims. Applicants then point to the features claimed in claims 2-9 and note they are entirely within the scope and inventive concept of claim 1. Applicants then state the process of claim 1 cannot be carried out without the catalyst of claims 2-9 and the catalysts utility is defined only within the context of the claimed cellulose conversion process. Applicants then argue the catalyst is reusable and allows for scalability.
This is not found persuasive because the catalyst of claim 2 is not coextensive with that of claim 1. The catalysts in claim 1 require specific zeolites/supports used in the preparation of the catalysts claimed. These catalysts do not include Y zeolite, beta zeolite, gamma zeolite, alumina zeolite, or boehmite zeolite, which are all embraced by the present claim 2. As such, present claim 2 embraces catalysts outside the scope of claim 1. So while claim 1 may embrace catalysts of claim 2; various catalysts of claim 2 would not be embraced by the catalysts in claim 1. Further, the intended use of the catalysts in claim 2 “for 100% conversion of cellulose in polyol” (note this should read conversion of cellulose into polyol) would not impart novelty to the same. That is – the catalysts meeting the structural limitations of the claim could be present in the literature without being used for conversion of cellulose into polyols and still read on the catalyst claims. As such, the search would be required beyond the methods of claim 1 to determine if the broader catalysts are indeed present for various uses. The supposed advantageous features of being reusable and afford a scalable process are not relevant to the restriction.
The requirement is still deemed proper and is therefore made FINAL.
Drawings
The drawings are objected to because they are blurry. Specifically, the HPLC chromatogram in Figure 1 and Figure 11. Corrected drawing sheets in compliance with 37 CFR 1.121(d) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. The figure or figure number of an amended drawing should not be labeled as “amended.” If a drawing figure is to be canceled, the appropriate figure must be removed from the replacement sheet, and where necessary, the remaining figures must be renumbered and appropriate changes made to the brief description of the several views of the drawings for consistency. Additional replacement sheets may be necessary to show the renumbering of the remaining figures. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance.
Specification
The disclosure is objected to because of the following informalities: on page 1, line 20, the phrase “forone-pot” should read “for one-pot”.
On page 6, line 25, the phrase “mild reaction conditions.Suitable” should read “mild reaction conditions. Suitable”
Appropriate correction is required.
Claim Objections
Claim 1 is objected to because of the following informalities: there should be a comma after Al-Ni-W/NaY at the end of the 9th line of the claim. Appropriate correction is required.
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 and 10 are rejected under 35 U.S.C. 103 as being unpatentable over Hamdy et al. (New Catalyst with multiple active sites for selective hydrogenolysis of cellulose to ethylene glycol, Green Chemistry, 2017, vol. 19, pp 5144-5151) in view of Gu et al. (Scientific Reports, 2019, 9:11938, 10 pages – NPL reference C3 from applicant’s IDS filed 5/9/23).
.
The claims of the instant application are drawn to methods of converting cellulose into polyols comprising reacting cellulose with a catalyst in a ratio of from 1:0.3 to 1:1 in the batch reactor with a solvent (water as in claim 10) at a temperature of 200-230°C and a pH in the range of 4.5-2 while stirring in the range of 700-1000rpm and a pressure in the range of 40-70 bars of Hydrogen for 1.5-12 hours to obtain polyol with 100% conversion of the cellulose into polyols; wherein the polyols are ethylene glycol, 1,2-propane diol, glucose, sorbitol, xylitol, erythritol, and glycerol; and the catalyst is selected from Al-Ni-W/HY, Al-Ni-W/NaY, Al-Ni-W/HZSM-5 and Al-Ni-W/Na-ZSM-5 wherein the ratio of Ni is in the range of 3-12%; Al is 5-15%; and W is 5-30%.
Hamdy discloses the catalytic conversion of cellulose to polyols using a catalyst having 3Al-15W-3Ni with a TUD-1 support. The Al-W-Ni catalyst was shown to allow for 100% conversion of cellulose (see table 3) compared to those lacking Al, W, or Ni all having 87% or less conversion. The polyols were glycerol, 1,2-propylene glycol, ethylene glycol, etc. – see table 3. The reaction was performed at 1.0:0.25 cellulose:catalyst ratio; used water as a solvent, performed at 503K (equivalent to 230 °C), and initial pressure of 4MPa (40 bars H); and for 1.5h. The catalysts were also shown to be recyclable (see figure 8).
What is not taught is the specific ranges of Ni-Al-W claimed herein (where the only difference is the art used 3% Al and the present claims are drawn to 5-15%), the pH of the reaction, and the HY, NaY, HZSM-5 or Na-ZSM-5 zeolites. Hamdy teaches that Al facilitates the hydrolysis of cellulose; then the formed products was converted over tungsten (W) to form glycoaldehydes, wherein these compounds are finally reduced to ethylene glycol (and polyols) over the Ni (see left column on page 5150), thus showing the importance of having all three in their Al-Ni-W catalyst.
Gu teaches methods of generating C2/C3 glycols (ethylene and propylene glycols) from cellulose using a β-zeolite and Na-ZSM-5 as the support (see figure 1). The ratio of cellulose to catalyst is 1:0.3 (0.5g cellulose and 0.15g catalyst) where the solvent is water, the temperature is 245°C and a pressure of 6MPa (60 bars of H) for 30min.
Thus, it would have been obvious to one of skill in the art at the time of the invention to modify the process conditions such as concentration and pH with these reference before them as these are normal process modifications undertaken in optimization. Likewise, it would have been obvious to modify the zeolite with a varying one such as those used in Gu et al. in determining the optimal catalyst as Gu. Teaches these are acceptable when used in correlative methods set forth herein.
Claim(s) 1 and 10 are rejected under 35 U.S.C. 103 as being unpatentable over Gu et al. (Scientific Reports, 2019, 9:11938, 10 pages – NPL reference C3 from applicant’s IDS filed 5/9/23).
The claims of the present application are set forth above.
Gu discloses methods of generating C2/C3 glycols (ethylene and propylene glycols) from cellulose using a β-zeolite and Na-ZSM-5 as the support (see figure 1). The ratio of cellulose to catalyst is 1:0.3 (0.5g cellulose and 0.15g catalyst) where the solvent is water, the temperature is 245°C and a pressure of 6MPa (60 bars of H) for 30min. Gu notes that Ni and W provide synergistic results when used together in producing glycols, especially in the hydrolysis of cellulose. Gu used various percentages of Ni and W (see page 4) with 5-25wt% of W and 1-15wt% of Ni. Likewise, Table 1 shows various co-catalysts including those containing Al (see entry 6 of table 1 for example) which provided 100% conversion of cellulose. Gu also notes that various products such as ethylene glycol, propylene glycol, sorbitol, mannitol as well as other products such as propanediol, glycerol, and erythritol to name a few (see figure 1). What is not specifically exemplified is the exact process conditions claimed herein, nor the specific Ni-W-Al catalysts claimed herein.
It would have been obvious to one of skill in the art to modify the reaction conditions such as temperature and time as these are normal process modifications undertaken in optimization. Likewise, it would have been obvious to add Al to the Ni-W catalysts of Gu as they use their synergistically disclosed Ni-W catalysts with an Al-containing co catalyst and show excellent results (see Table 1).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to TRAVISS C MCINTOSH III whose telephone number is (571)272-0657. The examiner can normally be reached Monday-Friday 9AM-5:30PM 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, Scarlett Goon can be reached at 571-270-5241. 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.
/TRAVISS C MCINTOSH III/ Primary Examiner, Art Unit 1693