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 of Group I, claims 1-2, 4-23 and 25-30 in the reply filed on 10/30/2025 is acknowledged. Because applicant did not distinctly and specifically point out the supposed errors in the restriction requirement, the election has been treated as an election without traverse (MPEP § 818.01(a)).
Claim 24 has been withdrawn by the examiner from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Claim Rejections - 35 USC § 112
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 7, 19, 21 and 23 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.
A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claims 7 and 23 recite the broad recitation before “preferably”, and the claim also recites the narrower statement of the range/limitation after “preferably”. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
Regarding claim 19, the preamble indicates the dependency on claim 1, whereas the body of the claim recites the dependency of L1 on claim 18 “L1 is a tridentate ligand as defined in claim 18”, rendering the scope of the claim vague and indefinite.
Regarding claim 21, the limitation "(e.g. -Cl, -Br, -I)" renders the claim indefinite because it is unclear whether the parenthetical limitation is part of the claimed invention. See MPEP § 2173.05(d).
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 25 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. The claim is drawn to a method of making a compound using the process of claim 1, however, since claim 1 is drawn to a hydrogenation of glycerol ester, it is implicitly understood that a compound is prepared by the process. As such, claim 25 fails to further limit the subject matter of claim 25. Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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.
Claims 1-2, 4-21 and 25-30 are rejected under 35 U.S.C. 103 as being unpatentable over patent number CN109956970A (CN’970; cited in IDS 03/01/2023 and machine translation attached herewith).
Regarding claims 1-2, 4-5, 15-17 and 26-29, CN’970 teaches a hydrogenation process of glyceryl trilaurate or glyceryl tristearate, comprising treating a composition that comprises the aforementioned glycerol ester with a base and a biphenyl tridentate ligand ruthenium complex catalyst in the presence of molecular hydrogen. The reference exemplifies that 3 mmol of the esters (III-u and III-v), 3 μL of the catalyst 8, and 0.3 mmol of NaOMe (base) has been used (Table 2). Furthermore, the nonexemplified embodiment of CN’970 teaches the biphenyl tridentate ligand ruthenium complex is complexed with 0.001-0.1 mol% of the amount of the ester compound. These amounts are converted to weight percent as follows:
Examples
mmol
mol.wt.
wt.
wt.%
ester III-u
3
639
1917
99.07
NaOMe
0.3
54.03
16.209
0.84
catalyst 8
0.003
610.04
1.83012
0.09
total
1935.039
mmol
mol.wt.
wt.
wt.%
ester III-v
3
891.48
2674.44
99.33
NaOMe
0.3
54.03
16.209
0.60
catalyst 8
0.003
610.04
1.83012
0.07
total
2692.479
Non-exemplified embodiment
0.001mol% cat and 1mol% base
mol
mol.wt.
wt.
wt.%
ester III-u
10
639
6390
99.915
NaOMe
0.1
54.03
5.403
0.084
catalyst 8
0.0001
610.04
0.061004
0.001
total
6395.464
0.1mol% cat and 10mol% base
mol
mol.wt.
wt.
wt.%
ester III-u
10
639
6390
99.068
NaOMe
1
54.03
54.03
0.838
catalyst 8
0.01
610.04
6.1004
0.095
total
6450.13
0.001mol% cat and 1mol% base
mol
mol.wt.
wt.
wt.%
ester III-u
10
639
6390
99.161
NaOMe
1
54.03
54.03
0.838
catalyst 8
0.0001
610.04
0.061004
0.001
total
6444.091
From the above, while the amount of the catalyst in the non-exemplified embodiments of CN’970 overlaps with that of the claimed invention, the weight percent range of the base in the composition is lower than the claimed at least of 7 wt%. However, difference in concentration will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. See MPEP § 2144.05. In this instance, the disclosure fails to provide the criticality or unexpected results of using such a high amount of the base. The instant specification discusses under Example 1 (page 32), that “when the amount of base is increased, the C18:1 conversion for the hydrogenation reaction increases significantly despite the catalyst loading remaining very low”. Similarly, CN’970 achieves an optimal conversion rate of greater than 99% for glyceryl esters III-u and III-v (Table 2). The same conversion rate is expected to be obtained when the hydrogenation process is conducted using the weight percent of the catalyst and the base of the non-exemplified embodiment. Accordingly, absent any showing of unexpected results or criticality, the instantly claimed process for hydrogenation of a glycerol ester is prima facie obvious over the teachings of CN’970.
Regarding claims 4-5, CN’970 teaches that non-limiting examples of bases used in the catalytic hydrogenation are sodium methoxide, sodium ethoxide, sodium isopropoxide, sodium tert-butoxide, potassium methoxide, potassium ethoxide, potassium isopropoxide, and potassium tert-butoxide ([0040]).
Regarding claims 6-7, 9-10 and 30, the catalytic hydrogenation of ester compounds can be carried out under solvent-free conditions or in the presence of solvent/s such as one or a mixture of several organic solvents such as tetrahydrofuran, toluene, methanol, and 1,4-dioxane ([0039]).
Regarding claims 8 and 11-12, the volume percent of the solvent/s as instantly claimed are not taught by CN’970, however, determining the amount of solvent in a given reaction process would be within the purview of one of ordinary skilled in the art. The skilled artisan would determine the optimal workable amount of solvent by routine experimentation and thus the volume% as claimed is not inventive.
Regarding claims 13-14, the reaction hydrogen pressure is 3 to 10 MPa (30 to 100 bar) and temperature in CN’970 is 60 to 100 °C ([0038]).
Regarding claims 18-21, CN’970 exemplifies biphenyl tridentate ligand ruthenium complex catalysts as follows:
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188
564
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180
609
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Regarding claim 25, the hydrogenation process of trilaurate III-u and glyceryl tristearate III-v produces alcohols IV-a-u and IV-a-v, respectively (Table 2).
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to process for hydrogenation of a glycerol ester, comprising treating a composition which comprises a glycerol ester with a base and a transition metal catalyst in the presence of molecular hydrogen, wherein the base is present in at least 7 wt % based upon the total weight of said composition and wherein the catalyst is present in less than or equal to 0.05 wt % based upon the total weight of said composition in view of the teachings of CN’970.
Claims 22 and 23 are rejected under 35 U.S.C. 103 as being unpatentable over patent number CN109956970A (CN’970) as applied to claims 1-2, 4-21 and 25-30 above, and further in view of patent application publication number US2014/0328748A1 (US’748).
The teachings of CN’970 have been set forth above.
Regarding claims 22-23, the reference fails to teach or suggest the catalysts of claim 22 and the hydrogenation process of natural oil.
The deficiencies however are cured by US’748.
Similar to the teachings of CN’970, US’748 is also drawn to a hydrogenation process of ester, by treating a composition comprising an ester, a catalyst complex and a base in the presence of molecular hydrogen ([0067]):
[T]he process of catalytic reduction of esters implies the usage of at least one of the metal complexes 1 or 2, hydrogen pressure, and optionally a base and a solvent. The base may be necessary in those cases when the metal catalyst 1 contains one or more halogen atoms bonded to the metal. The treatment with base can be done prior to the reduction or in situ by adding base to the reaction mixture during hydrogenation.
The esters hydrogenated by the process of US’748 are compounds of the following formulae ([0063]), the last one being a glycerol ester:
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183
308
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Regarding claim 22, one of the exemplified catalysts in US’748 is the same as instantly claimed ([0047]):
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123
128
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Greyscale
Regarding claim 23, US’748 teaches the catalyst complexes of Formulae II and III, have been found to show high selectivity toward reduction of the ester groups in the presence of C═C double bonds and as such it provides a useful way of deriving unsaturated alcohols from natural products such as, but not limited to, olive or canola oils, under mild reduction conditions ([0062]).
In accordance to MPEP § 2143, the Supreme Court in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) identified a number of rationales to support a conclusion of obviousness which are consistent with the proper “functional approach” to the determination of obviousness as laid down in Graham and discussed circumstances in which a patent might be determined to be obvious. In this case, at least prong (B) simple substitution of one known element for another to obtain predictable results applies. CN’970 uses a different catalyst and glycerol ester than those of claims 22-23 in the hydrogenation process. US’748 teaches the catalyst as claim 22 and natural oil glycerol ester as in claim 23 to perform the same hydrogenation process. Thus, a simple substitution of CN’970’s catalyst or glycerol ester with that of US’748 would yield nothing more than the predictable hydrogenated product.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to process for hydrogenation of a glycerol ester, comprising treating a composition which comprises a glycerol ester with a base and a transition metal catalyst in the presence of molecular hydrogen, wherein the base is present in at least 7 wt % based upon the total weight of said composition and wherein the catalyst is present in less than or equal to 0.05 wt % based upon the total weight of said composition, wherein the transition metal catalyst is
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268
602
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and wherein the composition which comprises a glycerol ester(s) is a natural oil, preferably a natural oil selected from almond oil, avocado oil, behen oil, brazil nut oil, cashew nut oil, castor oil, chia seed oil, cocoa butter oil, coconut oil, corn oil, cottonseed oil, linseed oil, grape seed, hemp seed, macadamia nut oil, mustard oil, olive oil, palm oil, palm kernel oil, peanut oil, pecan nut oil, perilla oil, poppyseed oil, pracaxi oil, rice bran oil, safflower oil, sea buckthorn oil, sesame oil, soybean oil, sunflower oil, vigna mungo oil, and walnut oil, more preferably a natural oil selected from linseed oil, olive oil, palm oil, palm kernel oil, rapeseed oil, and sunflower oil in view of the teachings of CN’970 and US’748.
Citation of Relevant Prior Art
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Spasyuk, D. et al. “Replacing Phosphorus with Sulfur for the Efficient Hydrogenation of Esters” Angew. Chem. Int. Ed. 2013, 52, 2538 –2542, https://doi.org/10.1002/anie.201209218Digital teaches hydrogenation of esters using the catalyst of claim 22 (Fig. 1):
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120
120
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Conclusion
Claims 1-2, 4-23 and 25-30 are rejected and no claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MEDHANIT W BAHTA whose telephone number is (571)270-7658. The examiner can normally be reached Monday-Friday 8am-5pm.
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/MEDHANIT W BAHTA/Primary Examiner, Art Unit 1692