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 .
Claim Status
Claims 1-21 were filed on 8/10/2023 and claim 22 was newly added in the response filed 2/11/2026. Claims 1-22 are pending.
Priority
The instant application was filed on 8/10/2023 and claims the benefit of priority to:
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See filing receipt dated 1/2/2024. Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Specification/Drawings
The amendment filed 2/11/2026 is objected to under 35 U.S.C. 132(a) because it introduces new matter into the disclosure. 35 U.S.C. 132(a) states that no amendment shall introduce new matter into the disclosure of the invention. The added material which is not supported by the original disclosure is as follows:
Structure (IIIB) in Fig. 2:
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and
Structure (Vb) in Fig. 5.
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Applicant is required to cancel the new matter in the reply to this Office Action.
The disclosure is objected to because of the following informalities: Tables 1 and 2 on p.12-13 are illegible.
The drawings are objected to as failing to comply with 37 CFR 1.84(p)(5) because they do not include the following reference sign(s) mentioned in the description: structure VII, which is mentioned with respect to Fig 4 in [0021] of the specification as filed.
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. 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.
Appropriate correction is required.
Claim Objections
Claims 3-6, 9, 14, 17-19, 21, and 22 are objected to because of the following informalities:
Claims 3-6 are objected to because the structures are blurry and difficult to read.
Claim 6 is objected to because the carbene ligand structure should immediately follow the phrase “R1 is”. For example, the first option in the claim should be changed from: “R1 is and R2
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is hydrogen” to
“R1 is
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and R2 is hydrogen”.
In line 2 of claim 9, the word “reactor” should be amended to recite “reactor:” to indicate the list of alternative options which follow.
In line 3 of claim 9, the indefinite article “a” should be inserted before “temperature”
In line 3 of claim 9, the phrase “with a” should be inserted before “space velocity”.
In line 4 of claim 9, the phrase “with a” should be inserted before the word “stirring”.
In line 1 of claim 14, the definite article “the” should be inserted before the word “hydrogenation”.
In line 1 of claim 17, the definite article “the” should be inserted before the word “metathesis”.
In line 4 of claim 17, the word “and” should be inserted before the word “stirring”.
Claim 18 is objected to because the preamble differs from all of the other claims. Consistent language should be used throughout the claim set.
In line 1 of claim 19, the definite article “the” should be inserted before the word “metathesis”.
In line 2 of claim 21, the word “preferred” should be deleted.
In line 3 of claim 21, the word “and” should be inserted before the word “stirring”.
In line 3 of claim 21, the word “of” should be inserted before “0.5 h”.
Claim 22 is objected to because it is missing a period “.” at the end of the claim. See MPEP 608.01(m).
Appropriate correction is required.
In step b) of claim 1, the Examiner further suggests replacing the word “lysing” with “breaking” as described in [0024] of the specification as filed.
Claim Rejections - 35 USC § 112(a)
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claim 22 is rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
The claimed structure, also present in newly amended Fig. 2 and 4, was not explicitly depicted in the disclosure as filed. At the top of p. 7 of the response filed 2/11/2026, the Applicant indicates that [0021] of the specification provides support for the amendment. However, there does not appear to be evidence to support the claimed structure in that paragraph. Therefore, the ligand appears to be new matter.
Claim Rejections - 35 USC § 112(b)
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 1-22 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.
Step c) of claim 1 recites “separating esters and olefins from the C10 to C13 chain by fractional distillation”. The preamble of the claim recites that the process produces “olefins and C10 to C13 esters” from methyl fatty acid esters (C16-18, see [0002] of the specification as filed).
Therefore, though there is antecedent basis for C10 to C13 esters, it is not clear what the “C10 to C13 chain” that is separated from “esters” and “olefins” by fractional distillation refers to. There are several possible interpretations. Referring to Applicant’s Fig. 5 for the purposes of discussion, wherein compound 1 is butene (a C4 olefin); the two C18 methyl ester reactants are the “methyl esters of the hydrogenated mixture” which undergo butenolysis to produce the olefins and ester metathesis products 2-9.
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The first interpretation is that the C10 to C13 chain is attached to an ester and corresponds to the “C10 to C13 ester” product (compounds 3, 5, and 9 of Fig. 5), which is removed from other esters not having the desired chain length (compound 7 of Fig. 5) and olefins (compounds 2, 4, 6, and 8 of Fig. 5).
The second is that the C10 to C13 chain refers to a C10-C13 olefin (compounds 2 and 4), which is removed from esters (compounds 3, 5, 7, and 9) and olefins (compounds 6 and 9) not having the desired chain length.
The third is that the C10 to C13 chain is intended to encompass the product esters and olefins (compounds 2-5 and 9 of fig. 5), which are removed from other esters (compound 7 of Fig. 5) and olefins (compounds 6 and 8 of Fig. 5) not having the desired chain length.
The fourth is that the C10 to C13 chain is some sort of by-product that is separated from the product “esters” (C10-C13) and “olefins”.
The specification does not appear to elaborate or provide any examples regarding the fractional distillation. As indicated above, Tables 1 and 2, summarizing examples 1 and 2 are illegible. As the desired product of the process is methyl esters having C10-C13 carbon chains, it is likely that the first interpretation is correct; however, this is not clear from the present claim language. None of the dependent claims cure this deficiency.
Claim 3 is indefinite because the variable “R” on the catalyst is not defined.
Claim 5 is indefinite because the variables “R1 and “R2” are undefined.
Claim 18 is rejected for being indefinite because it is not clear if the organic solvent and inert gas are optional. The claim recites “characterized in that the metathesis reaction of olefins can be conducted in organic solvent and with inert gas”. The indefinite phrase “can be” is used instead of “is” (if both the solvent and gas are required) or “is optionally” (if the solvent and gas are optional).
Claim 19 is rejected because there is a lack of antecedent basis for “the organic solvent”. Claim 19 depends from claim 17 and an organic solvent is not introduced until claim 18.
Claim 20 is rejected because there is a lack of antecedent basis for “the inert gas”. Claim 20 depends from claim 17 and an inert gas is not introduced until claim 18.
Claim Rejections - 35 USC § 112(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 12 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.
Claim 11 from which claim 12 depends, recites that the catalyst is composed of 0.05 to 5.0% (mass/mass, m/m) Pd and 0.01 to 1% m/m Ag deposited on gamma-alumina. While claim 12 does further limit the concentration of the Pd, the claim also indicates that it is deposited on active carbon. This appears to be an improper broadening of claim 11, which requires gamma-alumina as a support. The specification as filed appears to consider active carbon and gamma-alumina (Al2O3) to be alternatives to one another.
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.
Claim(s) 1-5, 7-10, and 17-22 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kaido (US2010/0094034, published on 4/15/2010) in view of Cohen (US2013/0035502, published on 2/7/2013).
The Applicant claims a method for producing olefins and C10 to C13 esters from methyl fatty acid esters (FAME), the process comprising:
Catalytically hydrogenating FAME with di- and tri-unsaturated chains;
Lysing (breaking) the carbonic chains of methyl esters of the hydrogenated mixture by the cross-metathesis reaction with olefins of carbonic chains in the range of C2 to C6; and
Separating esters and olefins by fractional distillation.
Kaido teaches an improved method for conducting metathesis comprising:
Providing a polyunsaturated fatty acid composition;
Providing a hydrogenation catalyst;
Hydrogenating at least a portion of the polyunsaturated fatty acid composition in the presence of the hydrogenation catalyst to form a partially hydrogenated composition;
Providing a metathesis catalyst comprising a transition metal; and
Metathesizing at least a portion of the partially hydrogenated composition in the presence of the metathesis catalyst to form a composition comprising a mixture of metathesis products. See claims.
Steps a) to c) of Kaido correspond to the instantly claimed hydrogenation step a) and steps d) to e) of Kaido correspond to the instantly claimed metathesis step b).
Kaido teaches that the polyunsaturated fatty acid composition subjected to hydrogenation includes polyunsaturated fatty esters comprising di- and tri-unsaturation. See [0020] and [0030], including Table A, and [0075-0076], including Table B. Kaido exemplifies methyl fatty acid esters, including methyl linoleate, and FAMEs derived from vegetable oils (claim 2). Kaido teaches that the polyunsaturated FAME is partially hydrogenated to produce a composition comprising a relatively higher number of monounsaturated FAMEs. See abstract and [0109-0131]. Kaido teaches that the partially hydrogenated composition can comprise 85 wt% or more of the monounsaturated FAME and 1 wt% or less of the polyunsaturated FAME. See [0100 and 0129].
Kaido teaches that the partial hydrogenation is carried out in a stirred reactor with a catalyst, including those comprising palladium (Pd) and Pd/C with a silver (Ag) promoter. See [0080-0092]. Kaido teaches that the partial hydrogenation is carried out at a temperature within the range of 50-350°C, which overlaps with the range of claim 9 and encompasses the 50°C of claim 10. Kaido teaches that the pressure of the reaction ranges from about 15 to 3000 psig (about 1 to 207 bar), which encompasses the range of claim 9. See [0093]. Kaido teaches that the temperature and pressure of the reaction can vary with the catalyst. See [0102]. Example 2 in [0169-0189] teaches an exemplary partial hydrogenation procedure, wherein soybean oil is contacted with hydrogen gas in the presence a copper catalyst (Cu-0202P) in a Parr pressure reactor with an agitation (stirring) rate of 300 rpm or 500 rpm and stirred for a total of 6 hours. The rpm and stirring time values of Kaido fall within the range of claim 9, and 500 rpm is identical to that of claim 10. The temperatures, pressures, and catalyst load were varied according to Table 3 and Fig.3. Though Kaido does not explicitly teach a stirring time of 0.5 h (claim 10), Kaido teaches that the identity of the catalysts, as well as catalyst load, and reaction temperatures and pressures will all affect the reaction selectivity and yield. Therefore, the claimed stirring time is within the range of routine optimization and is expected to vary depending on all the variables recited above. Also see Example 4 in [0191-0194] including Table 5. MPEP 2144.05.
Kaido teaches that the monounsaturated FAME obtained from the partial hydrogenation is subjected to either a self-metathesis reaction (see Fig. 1) or a cross-metathesis (see Fig. 2). Also see [0138-0147]. The cross-metathesis reaction corresponds to instant step b). Fig. 2 exemplifies the following reaction:
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, wherein (28) are the reactants, (30) are the ester products having terminal olefins, and (32) are the terminal olefin products. The cross-metathesis partner is ethylene (claim 7), a C2 olefin, and [0146] teaches that the olefin partner also includes C3-C6 olefins (“small olefin”), including 1-butene (claims 7 and 8). The ester products of Fig. 2 are shown to contain a C5-C17 carbon chain and preferably the carbon chain lengths fall within the range C8 to C13. See [0147].
Kaido discusses metathesis catalysts in [0148-0152]. Catalysts 12, 14, 22, 24, 26 correspond to catalysts of formula (I) of claim 3, wherein R is PCy3 or a N-heterocyclic carbene (NHC) ligand. Catalyst 12 corresponds to the catalyst of claim 4, wherein R is PCy3 (II) and catalyst 14 corresponds to the catalyst of claim 22 having the NHC ligand. See [0149]. Catalyst 20 corresponds to a catalyst of formula (IV) of claim 5, wherein R1 is PCy3 and R2 is H. See [0150].
Kaido teaches that the metathesis reaction conditions, including stoichiometry, atmosphere, solvent, temperature and pressure, are not particularly limited as long as the conditions are sufficient to produce a desired product. See [0153]. Kaido teaches that the temperature may be greater than -40°C and less than 150°C, preferably from about 20-120°C, which encompasses or overlaps the range of claim 17 and the 50°C of claim 21. See [0157]. Kaido teaches that the pressure can be greater than 10kPa and less than 7000kPa (about 0.1 to 70 bar), preferably 100-3000 kPa (1 to 30 bar), which encompasses or overlaps with the range of claim 17 and the 5 bar of claim 21. See [0158]. In example 1, Kaido teaches a stirring time of 4 hours at a temperature of 50°C in a stirred reaction vessel (Fisher-Porter). See [0168]. Example 5 teaches a stirring time of 15-480 min at a temperature of 70°C in a stirred reaction vessel. See [0195-0197]. Therefore, the examples of Kaido teach stirring times which encompass those claimed (17 and 21). Kaido does not explicitly teach a stirring speed in rpm for the metathesis reaction; however, Kaido teaches that the hydrogenation reaction is stirred at an rpm of 300 or 500 rpm, which falls within the range of claim 17 and includes the 500 rpm of claim 21. Therefore, the skilled artisan would also expect this rpm to be suitable for the metathesis reaction. Additionally, as Kaido teaches that the metathesis reaction conditions are not particularly limited, then the claimed reaction parameters are can be reasonably obtained through routine optimization. Also see MPEP 2144.05.
Regarding claims 18-20, Kaido teaches that the metathesis may be carried out in an inert gas, including nitrogen and argon and in a solvent, including toluene. See [0153-0154]. Kaido does not explicitly teach the purity of the inert gas, however, it would be prima facie obvious to use pure (>99.9%) gas in order to avoid by-product formation.
Kaido teaches that the disclosed process is an improvement over prior art metathesis reactions because including a hydrogenation step prior to a metathesis step can provide several benefits, including reduction of catalyst demand and simplification of metathesis products. When a polyunsaturated FAME is subjected directly to a metathesis reaction, each instance of a double-bond can be a site of reaction, which increases the load on the catalyst and the complexity of the metathesis product mixture. Kaido teaches that the hydrogenation can also avoid unwanted by-products, including volatile organic compounds (VOCs), which also simplifies purification requirements. See abstract, [0004-0005, 0010, 0137, 00144-0145] and example 5 in [0195-0197].
Kaido does not explicitly teach a fractional distillation separation step following the metathesis, corresponding to instant step c.
Cohen teaches an analogous process to that of Kaido, wherein a natural oil feedstock is metathesized with a low or medium molecular weight olefin in the presence of a catalyst to produce a metathesized product comprising olefins and esters, and separating the olefins from the esters. See abstract and claims. Cohen teaches that the low or medium molecular weight olefin includes C2-C6 olefins. See claims 2-4. Cohen teaches that the natural oil feedstock includes fatty acid methyl esters [0023-0026] and that the process produces C10-C12 methyl esters and various olefins. See claim 15, [0093], and examples. Cohen also teaches that the feedstock may be partially hydrogenated prior to the metathesis reaction. See [0060]. Cohen teaches that the metathesis takes place in reactor (20) and the esters and olefins obtained at the end of the reaction (22) are fed to a separation unit (30), which can separate the olefins (32) from the esters (34). See Fig. 1, [0065 and 0090-0091]. The separation unit (30) can be a distillation column and produces two fractions. See [0072, 0090].
It would have been prima facie obvious to combine the teachings of Kaido and Cohen to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to separate the metathesized mixture of Kaido by distillation because Cohen teaches that such a distillation is known and predictable to separate the olefins from the esters. Cohen further teaches that the olefins and esters have different uses, thereby providing further motivation to separate them. See [0036-0038, 0072, 0093, and 0114-0121]. Also see MPEP 2143(I)(A).
Claim(s) 6 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kaido (US2010/0094034, published on 4/15/2010) in view of Cohen (US2013/0035502, published on 2/7/2013), as applied to claims 1-5, 7-10, and 17-22 above, and further in view of Caijo (“Screening of a selection of commercially available homogeneous Ru-catalysts in valuable olefin metathesis transformations” Catal. Sci. Technol. 2013, p. 429).
Kaido discusses metathesis catalysts in [0148-0152], and including preferred homogeneous ruthenium NHC containing catalysts 12, 14, 20, 22, 24, and 26 (corresponding to catalysts in instant claims 3-5 and 22 as discussed above). Cohen also teaches the use of various homogeneous ruthenium NHC containing catalysts in the examples. Though Kaido teaches a catalyst having the core of claim 5 (20), Kaido does not explicitly teach any of the specific substituent combinations required in claim 6. Nor does Cohen.
Caijo is directed toward screening commercially available homogeneous Ru-catalysts in several metathesis reactions. See abstract. Caijo teaches a commercially available fast-initiation pre-catalyst of formula M73SIPr:
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. See Fig. 1 and discussion thereof on p. 429-430. This catalyst corresponds to the third option of claim 6, wherein R1 is the NHC ligand shown in the claim and R2 is NHCO2iBu. Caijo teaches that M73SIPr exhibited good yield in all reactions it was tested in. See Tables 1 and 3-4 on p. 430-433.
It would have been prima facie obvious to combine the teachings of Kaido, Cohen, and Caijo to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to substitute the metathesis catalyst of Caijo for one of those disclosed in the combined process of Kaido and Cohen, because replacing one known homogeneous ruthenium NHC containing metathesis catalyst with another is obvious and predictable. Further, Caijo teaches that the claimed catalyst is commercially available and can facilitate all of the reactions it was tested in to produce the products in good to high yield, thus underscoring its suitability as a convenient and effective catalyst in the combined process of Kaido and Cohen. Also see MPEP 2143(I)(B).
Claim(s) 11-16 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kaido (US2010/0094034, published on 4/15/2010) in view of Cohen (US2013/0035502, published on 2/7/2013), as applied to claims 1-5, 7-10, and 17-22 above, and further in view of Tacke (US 5734070, published on 3/31/1998); Petro (US 4021374, published on 5/3/1977); and Gadja (US 7453016, published on 11/18/2008).
Kaido discusses metathesis catalysts in [0080-0092], specifically mentioning palladium on carbon (active carbon-claims 12 and 15) with silver as a promoter in [0083]. Kaido further teaches that partial hydrogenation can alter the fatty acid composition through positional and/or geometrical isomerization, specifically mentioning that the cis bonds originally present in naturally occurring soybean oil are converted in part to the trans form. See [0081 and 0111]. Cohen also teaches the use of various hydrogenation catalysts in [0084-0088], including palladium catalysts. Neither Kaido nor Cohen teach a catalyst comprising the claimed concentrations of palladium (Pd) and silver (Ag) on a gamma-alumina support.
Tacke teaches a process for continuously hydrogenating unsaturated fats, fatty acids, or fatty acid esters on a shaped catalyst in a solid bed. See abstract. Tacke teaches that “use can be made for the method according to the invention of all known hydrogenation catalysts”, including those containing promoters. Tacke specifically teaches that silver is a known promoter for nickel and palladium catalysts that reduces the formation of undesired trans-isomers. See col. 3, lines 23-33; col. 1, lines 24-36; and claim 18. Tacke further teaches examples of Pd supported on carbon (0.5-2 wt% Pd/C-claims 12 and 15) or alumina (0.5 wt% Pd/Al2O3). See Tables 2-3 in col. 7-10.
Petro is directed toward selective hydrogenating catalysts comprising at least one platinum group component and at least one of a group IB or group IIB component. See abstract. Petro teaches that the catalyst comprises Pd in 0.5 to 10 wt% and the Group IB or IIB metal, including silver, in 0.05-10 wt%. These ranges overlap with, encompass, or include the concentrations in claims 11-16. See claim 3 and col. 2, lines 36-41. Petro teaches that “the invention is based on the recognition that by varying the amount of metal belonging to groups IB and/or IIB of the Periodic System the selectivity can be controlled over a wide range, permitting the catalysts to be used in stereospecific hydrogenation processes as well.” See col. 1, lines 55-68. Therefore, Petro teaches that the ratio of Pd to Group IB or IIB metal (Ag) is a results effective variable that can be modified to affect the selectivity of the catalyst. Also see MPEP 2144.05.
Gadja teaches a selective hydrogenation process for the selective hydrogenation of diolefins having from about 8 to about 19 carbon atoms per molecule to monoolefins in the presence of a layered catalyst comprising at least one Group 10 metal and at least one Group 11 metal deposited on a second refractory inorganic component. See abstract and claims. Gadja teaches that the Group 10 metal is platinum or palladium and that the Group 11 metal is copper or silver. See claims 6-8. Gadja further teaches the use of gamma-alumina (claims 11, 13, and 16) as the second refractory inorganic component. See claim 5 and col. 5, lines 17-40. Gadja teaches an example wherein the catalyst comprises 0.02 wt% Pd and 0.065 wt% Ag deposited on alumina. See example 4 and Table 3 in col.13.
It would have been prima facie obvious to combine the teachings of Kaido, Cohen, Tacke, Petro, and Gadja to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to use a hydrogenation catalyst comprising 0.05 to 5.0 wt% palladium and 0.01 to 1.0 wt% silver deposited on gamma-alumina or active carbon in the hydrogenation step of the combined process of Kaido and Cohen because replacing one known selective hydrogenation catalyst with another is obvious and predictable. Kaido explicitly suggests the combination of a Pd/Ag hydrogenation catalyst; Tacke teaches that said catalysts, which can be deposited on active carbon; are known to reduce the formation of less desirable trans-isomers in the claimed process; Petro teaches ranges of Pd and Ag that overlap with those claimed and that the ratio between the two is a results effective variable that can be routinely optimized to arrive at a catalyst suitable for the desired reaction; and Gadja teaches that gamma-alumina is also an exemplary support. Based on the teachings of all the references as a whole, the skilled artisan would select the claimed catalyst because it would be predictably selective towards the hydrogenation of polyunsaturated compounds to monounsaturated compounds without significant isomerization. Also see MPEP 2143(I)(B).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AMY C BONAPARTE whose telephone number is (571)272-7307. The examiner can normally be reached 11-7.
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/AMY C BONAPARTE/ Primary Examiner, Art Unit 1692