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 .
Status of the Application
Receipt of the Response and Amendment after Non-Final Office Action filed April 24, 2026 is acknowledged.
The status of the claims upon entry of the present amendments stands as follows:
Pending claims:
1-3, 6-15, 18-28, 30-45
Withdrawn claims:
30-42
Previously canceled claims:
4-5, 16-17, 29
Newly canceled claims:
None
Amended claims:
1, 21
New claims:
45
Claims currently under consideration:
1-3, 6-15, 18-28, 43-45
Currently rejected claims:
1-3, 6-15, 18-28, 43-45
Allowed claims:
None
The Examiner notes that claim 29 was previously cancelled and thus remains canceled in the present action. The Examiner notes that claim 45 has been designated as “(Previously Presented)”. However, claim 45 is new and was not present in the previous claim set.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1, 11-15, 18, 19, 22, and 43-45 are rejected under 35 U.S.C. 103 as being unpatentable over Stern 1 (DE 69808029 T2) in view of Stern 2 (US 5,908,946).
Regarding claims 1, Stern 1 teaches of an esterification reaction of monoglycerides into diglycerides in the presence of a catalyst including zinc or tin compositions ([0021]-[0022]). Stern also teaches that the oils of the present invention can include used frying oils ([0024]). Stern 1 also teaches that the esterification is carried out at a preferred temperature of 180 to 200[Symbol font/0xB0]C ([0037]), which falls within the claimed range of “about 120[Symbol font/0xB0]C to about 200[Symbol font/0xB0]C”.
Stern 1 does not teach that the catalyst is selected from the group consisting of zinc metal, chloride salts of zinc or tin, oxide salts of zinc or tin, sulfate salts of zinc or tin, and a combination thereof.
However, in the same field of endeavor by the same inventor, Stern 2 teaches of an esterification process using catalysts selected from zinc oxide and zinc aluminates (Abstract).
It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to substitute the zinc oxide of Stern 2 for the zinc compounds of Stern 1 and yield predictable results of a zinc catalyzed esterification. The claim would have been obvious because one of ordinary skill in the art would have been able to make this simple substitution of one known element for another and yield predictable results to one of ordinary skill in the art, see MPEP §2143(B).
Regarding claim 11, Stern 1 teaches that the esterification is carried out with monoglycerides, fatty acids, and the heterogenous catalyst ([0015]; [0022]). Thus, there are no exogenous reactants included in the process.
Regarding claim 12, Stern 1 teaches the re-esterification process as lasting for 3 hours (Table 1), which falls within the claimed range of “at least 3 hours”.
Regarding claim 13, Stern 1 teaches that after 2 hours of the esterification reaction, no monoglyceride remains in the ester ([0052]), which falls within the claimed range of “no more than about 18 wt% of monoglycerides”.
Regarding claim 14, Stern 1 teaches that the amount of monoglycerides at time = 0 (i.e., the beginning of the treatment) was 3.3% and fell during the process (Table 1). Thus, the frying oil contained less than 18 wt% of monoglycerides throughout the predetermined period.
Regarding claim 15, although the cited prior art does not teach that the catalytic reaction prevents or decreases the rate of an autooxidation reaction, this is an inherent result of performing the method as claimed as evidenced by the instant specification. The instant specification discloses that catalytic subsystems are responsible for reducing the rate of autooxidation reactions (p. 15, l. 8-12).
Regarding claim 18, Stern 1 also teaches that the esterification is carried out at a preferred temperature of 180 to 200[Symbol font/0xB0]C ([0037]), which overlaps with the claimed range of “from about 150[Symbol font/0xB0]C to about 190[Symbol font/0xB0]C”.
With respect to the overlapping ranges, MPEP §2144.05 teaches that it would have been obvious to one of ordinary skill in the art before the effective filing date of the invention to have selected the overlapping portion of the ranges disclosed by the reference because selection of overlapping portion of ranges has been held to be a prima facie case of obviousness.
Regarding claim 19, Stern 1 does not teach wherein the temperature is about 170[Symbol font/0xB0]C.
However, in the same field of endeavor, Stern 2 teaches an esterification process where the reaction temperature is between 170[Symbol font/0xB0]C and 250[Symbol font/0xB0]C (col. 4, l. 61-62), which contains the claimed value of “about 170[Symbol font/0xB0]C”.
It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to modify the process of Stern 1 with the use of the process temperatures of Stern 2. The claim would have been obvious because all claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective function, and the combination yielded nothing more than predictable results to one of ordinary skill in the art, see MPEP §2143(A).
Regarding claim 22, Stern 1 does not teach wherein the catalyst is selected from the group consisting of zinc metal, zinc chloride (ZnCl2), zinc oxide (ZnO), zinc sulfate heptahydrate (ZnSO4 7 H2O), tin(II) chloride dihydrate (SnCl2 2 H2O), tin(IV) chloride pentahydrate (SnCl4- 5 H2O), and combinations thereof.
However, in the same field of endeavor, Stern 2 teaches of an esterification process using catalysts selected from zinc oxide and zinc aluminates (Abstract).
It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to substitute the zinc oxide of Stern 2 for the zinc compounds of Stern 1 and yield predictable results of a zinc catalyzed esterification. The claim would have been obvious because one of ordinary skill in the art would have been able to make this simple substitution of one known element for another and yield predictable results to one of ordinary skill in the art, see MPEP §2143(B).
Regarding claim 43, Stern 1 teaches that frying oils are able to be used as a starting material ([0004]) and that esterification is carried out in a 1 L glass vessel ([0051]). Thus, it logically follows that the frying oil was moved from a fryer to the glass vessel. Regarding the limitation “an adjacent or nearby vessel”, having the secondary reaction vessel in close proximity for a subsequent processing step would be obvious in order to optimize the process.
Regarding claim 44, Stern 1 does not teach adding at least one exogenous reactant to the vessel in which step (a) is carried out.
However, in the same field of endeavor, Stern 2 teaches an esterification process with monoalcohols (i.e., an exogenous reactant; Abstract).
It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to modify the process of Stern 1 with the addition of monoalcohol as taught by Stern 2 as an exogenous reactant for esterification. The claim would have been obvious because all claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective function, and the combination yielded nothing more than predictable results to one of ordinary skill in the art, see MPEP §2143(A).
Regarding claim 45, Stern 1 does not teach adding glycerol.
However, in the same field of endeavor, Stern 2 teaches glycerin (i.e., glycerol) as a reactant in esterification (col. 1, l. 21-22, 26-30).
It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to modify the process of Stern 1 to also include glycerin as taught by Stern 2. The claim would have been obvious because all claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective function, and the combination yielded nothing more than predictable results to one of ordinary skill in the art, see MPEP §2143(A).
Claims 2, 3, 6-10 are rejected under 35 U.S.C. 103 as being unpatentable over Stern 1 (DE 69808029 T2) in view of Stern 2 (US 5,908,946) as applied to claim 1 above, and further in view of Seybold (US 5391385 A).
Regarding claim 2, Stern 1 and Stern 2 do not teach contacting the frying oil with an adsorbent selected from the group consisting of a functionalized silica gel, an unfunctionalized silica gel, and combinations thereof.
However, in the same field of endeavor, Seybold teaches of the treatment of cooking oil with amorphous silica (Abstract).
It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to modify the process of Stern 1 with the addition of a silica treatment step as taught by Seybold. One of ordinary skill would have been motivated to make this modification because Seybold teaches that silica reduces contaminants known to degrade oil (Abstract).
Regarding claim 3, Stern 1 and Stern 2 do not teach the temperature for treating the frying oil with silica.
However, in the same field of endeavor, Seybold teaches that the temperature for treating with silica gel is 180[Symbol font/0xB0]F to 400[Symbol font/0xB0]F (equivalent to 82[Symbol font/0xB0]C to 204[Symbol font/0xB0]C; col. 5, l. 27-30), which overlaps with the claimed range of “about 50[Symbol font/0xB0]C to about 150[Symbol font/0xB0]C”.
It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to modify the process of Stern 1 with the use of a silica treatment step at the temperature taught by Seybold. One of ordinary skill would have been motivated to make this modification because Seybold teaches that silica reduces contaminants known to degrade oil (Abstract).
With respect to the overlapping ranges, MPEP §2144.05 teaches that it would have been obvious to one of ordinary skill in the art before the effective filing date of the invention to have selected the overlapping portion of the ranges disclosed by the reference because selection of overlapping portion of ranges has been held to be a prima facie case of obviousness.
Regarding claims 6 and 7, Stern 1 and Stern 2 do not teach wherein step (c) is carried out for a predetermined period, and wherein, at the end of the predetermined period, the frying oil comprises no more than about 25 wt% polar compounds (claim 6) or wherein the frying oil comprises no more than about 25 wt% polar compounds at all times during the predetermined period (claim 7).
However, in the same field of endeavor, Seybold teaches that all of the oils used comprise 20 wt% or less of polar compounds (p. 4, Table 3), which falls within the claimed range of “no more than 25%”. Seybold also teaches a contact time of 1 minute to 20 minutes (i.e., a predetermined period; col. 5, l. 31-35). Because the untreated oils have polar compounds less than 20 wt%, it logically follows that the oil would comprise less than 20 wt% polar compounds for the entire treatment period.
It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to modify the process of Stern 1 with the polar compound composition and treatment of Seybold. One of ordinary skill would have been motivated to make this modification because Seybold teaches that polar compounds can contribute to off flavors (col. 1, l. 63-64).
Regarding claim 8, Stern 1 and Stern 2 do not teach wherein the contact with silica is carried out with food not frying in the frying oil.
However, in the same field of endeavor, Seybold teaches that the process may be used with fryer oil (claim 8). Although claim 11 of Seybold states that the silica composition is maintained in the frying oil during the food frying process, this is not a requirement of claim 8. Thus, one of ordinary skill would recognize that the process of claim 8 can be carried out without food in the vessel used for the silica treatment.
It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to modify the process of Stern 1 with the use of the silica treatment taught by Seybold. One of ordinary skill would have been motivated to make this modification because Seybold teaches that silica reduces contaminants known to degrade oil (Abstract).
Regarding claims 9 and 10, although Stern 1 and Seybold do not teach the order of step (a) and step (c) as claimed, MPEP §2144.04(C) states “selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results”, In re Burhans, 154 F.2d 690, 69 USPQ 330 (CCPA 1946). Therefore, it would have been obvious to perform the silica treatment at any of the claimed times.
Claims 20, 21, and 25 are rejected under 35 U.S.C. 103 as being unpatentable over Stern 1 (DE 69808029 T2) in view of Stern 2 (US 5,908,946) as applied to claim 1 above, and further in view of Cooper 2 (US 4,983,329).
Regarding claims 20 and 21, Stern 1 and Stern 2 do not teach wherein the process is carried out at an ambient pressure of no more than about 1 atm (claim 20) or from about 0.89 atm to about 1 atm (claim 21).
However, in the same field of endeavor, Cooper 2 teaches an esterification process carried out at reduced pressures of from about 0.01 mm to atmospheric pressure (equivalent to 1.31579e-5 atm to 1 atm; col. 2, l. 52-54), which falls within the claimed range of “no more than 1 atm” (claim 20) and overlaps with the claimed range of “from about 0.89 atm to about 1 atm” (claim 21).
It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to modify the process of Stern 1 with the use of the pressures taught by Cooper 2. The claim would have been obvious because all claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective function, and the combination yielded nothing more than predictable results to one of ordinary skill in the art, see MPEP §2143(A).
With respect to the overlapping ranges, MPEP §2144.05 teaches that it would have been obvious to one of ordinary skill in the art before the effective filing date of the invention to have selected the overlapping portion of the ranges disclosed by the reference because selection of overlapping portion of ranges has been held to be a prima facie case of obviousness.
Regarding claim 25, Stern 1 does not teach wherein the catalyst is present in an amount from about 0.05 wt% to about 1.5 wt% of a total weight of the frying oil.
However, in the same field of endeavor, Cooper 2 teaches a concentration of catalyst of 0.6 to 0.68 wt% (col. 6, Table 4), which falls within the claimed range of “from about 0.05 wt% to about 1.5 wt%”.
It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to modify the process of Stern 1 with the use of the amount of catalyst as taught by Cooper 2. The claim would have been obvious because all claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective function, and the combination yielded nothing more than predictable results to one of ordinary skill in the art, see MPEP §2143(A).
Claims 23 and 24 are rejected under 35 U.S.C. 103 as being unpatentable over Stern 1 (DE 69808029 T2) in view of Stern 2 (US 5,908,946) as applied to claim 1 above, and further in view of Klingelhoefer (US 2021/0380900 A1).
Regarding claims 23 and 24, Stern 1 does not teach wherein at the outset of the reaction step, a molar ratio of glycerol to free fatty acids in the oil is between about 0.5 and about 2.0 (claim 23) or is about 1.0 (claim 24).
However, in the same field of endeavor, Klingelhoefer teaches a method of treating oil with a catalyst (Abstract), where the treated oil may be spent cooking oil (i.e., frying oil; [0033]), and where the oil preferably has an initial molar ratio of glycerol to free fatty acid from 1:2 to 1:1 ([0050]), which falls in the claimed range of “between about 0.5 and about 2.0” (claim 23) and overlaps with the claimed range of “about 1.0” (claim 24).
It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to modify the process of Stern 1 with the molar ratio of glycerol to free fatty acid as taught by Klingelhoefer. The claim would have been obvious because all claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective function, and the combination yielded nothing more than predictable results to one of ordinary skill in the art, see MPEP §2143(A).
Claim 26 is rejected under 35 U.S.C. 103 as being unpatentable over Stern 1 (DE 69808029 T2) in view of Stern 2 (US 5,908,946) as applied to claim 1 above, as evidenced by Wang (Wang, Longxia, et al. “Ionic liquid-functionalized ZnO nanomaterial: Multifunctional additives enhangin tribological performance and corrosion resistance in ester oil”, Triboligy International, Vol. 202, 110320, published October 12, 2024 [accessed online June 24, 2026]).
Regarding claim 26, although Stern 1 and Stern 2 do not teach wherein the catalyst is insoluble or poorly soluble in frying oil, this is an inherent property of zinc oxide as evidenced by Wang. Wang discloses that ZnO (zinc oxide) has poor oil solubility (p. 2, col. 1, ¶ 3).
Claims 27 and 28 are rejected under 35 U.S.C. 103 as being unpatentable over Stern 1 (DE 69808029 T2) in view of Stern 2 (US 5,908,946) as applied to claim 1 above, and further in view of Cooper 1 (US 5,288,884).
Regarding claims 27 and 28, Stern 1 does not teach wherein at least part of the catalyst is provided on a surface of at least one supporting structure or substrate (claim 27) or wherein the at least one supporting structure or substrate comprises at least one of an alumina support, a zirconia support, a silica support, a titania support, a ceramic support, a glass surface, a nanoscale porous ceramic fiber, a wire mesh, a rod, a honeycomb structure, a structure having many pores or channels with round or polygonal cross-sections, a sphere, a plate, a tube, and a random geometric structure, and a porous zeolite bead.
However, in the same field of endeavor, Cooper 1 teaches that a catalyst may be supported on a material such as alumina or silica (col. 8, lines 54-58).
It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to modify the process of Stern 1 to use a catalyst support as taught by Cooper 1. One of ordinary skill would have been motivated to make this modification because Cooper 1 teaches that supporting catalysts on a porous inert refractory material is advantageous (col. 8, l. 54-57).
Response to Arguments
Claim Objections: Applicant has overcome the objections to the claims based on amendments in the Claims. Accordingly, the objections have been withdrawn.
Claim Rejections – 35 U.S.C. §102 of claims 1, 2, 8-11, 15, 18, 22, 26-28, and 44 over Cooper 1: Applicant’s arguments with respect to claim(s) 1, 2, 8-11, 15, 18, 22, 26-28, and 44 have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Claim Rejections – 35 U.S.C. §103 of claims 3, 12, 19-21, and 25 over Cooper 1; claims 6, 7, 13, 14, and 43 over Cooper 1 and Seybold; and claims 23 and 24 over Cooper 1 and Klingelhoefer: Applicant’s arguments with respect to claim(s) 3, 6, 7 12-14, 19-21, 23-25, and 43 have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
The rejections of claims 1-3, 6-15, 18-28, 43-45 have been maintained herein.
Conclusion
THIS ACTION IS MADE FINAL. 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.
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/A.S.H./Examiner, Art Unit 1793
/EMILY M LE/Supervisory Patent Examiner, Art Unit 1793
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