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 .
DETAILED ACTION
Claims 1-10 of Y. Kim, et al, US 18/257,322 (06/14/2023) are pending. Claims 8-10 are withdrawn as drawn to non-elected Group (II). Claim 1-7 are under examiner on merits and rejected.
Priority
Acknowledgment is made of applicant's claim for foreign priority based on an application filed in KR on 12/14/2020. It is noted, however, that applicant has not filed a certified copy of the KR10-2020-0174054 application as required by 37 CFR 1.55.
Election/Restrictions
Pursuant to the Restriction/Election requirement, Applicant elected Group (I), (claims 1-7), without traverse, in the Reply filed on 01/05/2026. Claims 8-10 drawn to non-elected Groups (II) are withdrawn from consideration pursuant to 37 CFR 1.142(b).
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
35 USC § 102 Rejection Over Joseph
Claims 1 and 3-7 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by T. Joseph, et al. 206, Journal of molecular catalysis A: Chemical, 13-21(2003)(“Joseph”).
Joseph teaches a process for preparing hydrido chlorocarbonyl tris-(triphenylphosphine) ruthenium(II) complex—[RuHCl(CO)(PPh3)3] as follows:
A solution of RuCl3·3H2O (2.61 g, 10 mmol) in 2-methoxyethanol (200 ml) and aqueous formaldehyde (200 ml; 40%, w/v) were added rapidly and successively to a vigorously stirred boiling solution of TPP (15.8 g, 60 mmol) in the same solvent (300 ml). The mixture was refluxed for 10 min, allowed to cool, filtered, washed with ethanol and hexane successively and dried in vacuum to obtain a light brown colored solid in good yield. The purity and structure of the complex was confirmed by melting point, elemental analysis and FTIR.
Joseph at page 14, right col. 2.2.4. Synthesis of hydrido chlorocarbonyl tris-(triphenylphosphine) ruthenium(II) complex—[RuHCl(CO)(PPh3)3], emphasis added.
It should be noted that once ruthenium chloride is mixed with formaldehyde at a temperature of 124-125ºC that is the boiling point of 2-methoxyethanol, a ruthenium complex comprising a CO ligand and ruthenium would be formed1 through reacting of ruthenium chloride with formaldehyde as the instant specification teaches that ruthenium chloride (RuCl3) reacts with formaldehyde (CH2O) resulting a the ruthenium complex comprising a CO ligand and ruthenium and the temperature of the reaction is not limited. See specification at page 9, [36]-[37]. It is appropriate to look to the instant specification for evidence that a claimed feature is inherent in the prior art. See, MPEP § 2112.02(I).
Thus, the Joseph process comprises:
(i). preparing a ruthenium complex by reacting ruthenium chloride with formaldehyde; and
(ii) adding triphenylphosphine to the ruthenium complex and then allowing a reaction to proceed to form the product of RuHCl(CO)(PPh3)3 .
Which meets each and every active steps limitation of claims 1, 4 and 7, therefore, claims 1, 4 and 7 are anticipated. With regards the claim preamble of “a catalyst for selective hydrogenation of cyclododecatriene”, it is merely interpreted as intended using rather claim limitations because it dose not limit the structure of the claimed invention. MPEP 2111.02.
Claim 3 is anticipated because in the Joseph process, the mole ratio of ruthenium chloride to formaldehyde is 10 mmol to 2660 mmol [(200 ×0.40)÷30 =2.66 mol] that is 1:266.
Claim 5 is anticipated because reaction of triphenylphosphine with the ruthenium complex in the Joseph process is conducted at a temperature of 124-125ºC or higher at which formaldehyde is vaporized.
Claim 6 is anticipated because in the Joseph process, the mole ratio of ruthenium chloride to triphenylphosphine is 1:6.
35 USC § 102 Rejection Over Kim
Claim 1 and 3-7 are rejected under 35 U.S.C. 102(a)(1)(a)(2) as being anticipated by Y. Kim, et al. WO2020130280A1 (published on 06/25/2020) (“Kim”). Kim is published in Korean, its US granted patent US11571687B2 (Kim-US) is used as English translation.
Kim names another inventor and published on 06/25/2020 that is less than one year than the filling date of the KR10-2020-0174054 (12/14/2020), Applicant may file a certified copy of the KR10-2020-0174054 and consider an exception under 35 U.S.C. 102(b) to remove Kim as prior art.
Kim teaches method for recovering a selective homogeneous hydrogenation catalyst includes: a step of synthesizing cyclododecene by selectively hydrogenating a first reaction solution containing cyclododecatriene, triphenylphosphine, formaldehyde, and ruthenium chloride, the cyclododecene being synthesized by preparation of a selective homogeneous hydrogenation catalyst from the triphenylphosphine, the formaldehyde, and the ruthenium chloride during the selective hydrogenation; and a step of distilling and separating unreacted cyclododecatriene and cyclododecadiene, and the cyclododecene that is a product from a second reaction solution in which the cyclododecene synthesis is completed, and recovering the selective homogeneous hydrogenation catalyst. Kim-US at col. 2, line 20-33, emphasis added.
Kim teaches working examples such as Example 1 as follows:
Example 1
Cyclododecatriene (CDT), ruthenium chloride (RuCl3), triphenylphosphine (TPP), and formaldehyde were added in a molar ratio of 7,500:1:110:220, a reaction solution was stirred under a condition of 6 bar of hydrogen, and selective hydrogenation was performed under a condition of 160° C. and 20 bar were maintained for 2 hours. In this case, the reaction was performed in a stirred-tank reactor provided with a gas induction hollow stirrer.
The selective hydrogenation was performed for 2 hours, the temperature was cooled to 30° C. or lower under a nitrogen condition to recover the reaction solution, and the reaction solution was distilled in a distillation apparatus at 0.1 bar or less and 110° C.
After the distillation was completed, the temperature was cooled to 30° C. or lower under a nitrogen condition to recover a selective homogeneous hydrogenation catalyst.
Kim-US at col. 9, Example 1. Line 45-60.
It should be noted that once ruthenium chloride is mixed with formaldehyde at 160ºC, a ruthenium complex comprising a CO ligand and ruthenium would be formed for the same reason as given above. Thus, the Kim Example 1 process comprises:
(i). preparing a ruthenium complex by reacting ruthenium chloride with formaldehyde; and
(ii) adding triphenylphosphine to the ruthenium complex and then allowing a reaction to proceed to form a catalyst product.
which meets each and every active steps limitation of claims 1, 4 and 7, therefore, claims 1, 4 and 7 are anticipated. The claim preamble of “a catalyst for selective hydrogenation of cyclododecatriene” is merely interpreted as intended use rather claim limitations because it does not limit the structure of the claimed invention. MPEP 2111.02.
Claim 3 is anticipated because in the Kim Example 1, the mole ratio of ruthenium chloride to formaldehyde is 1:220.
Claim 5 is anticipated because reaction of triphenylphosphine with the ruthenium complex in the Kim process is conducted at a temperature of 160ºC at which formaldehyde is vaporized.
Claim 6 is anticipated because in the Joseph process, the mole ratio of ruthenium chloride to triphenylphosphine is 1:110.
Claim Rejections - 35 USC § 103
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.
Claim 2 is rejected under 35 U.S.C. 103 as being unpatentable over T. Joseph, et al. 206, Journal of molecular catalysis A: Chemical, 13-21 (2003)(“Joseph”) as applied above for the rejection of claim 1.
T. Joseph, et al. 206, Journal of molecular catalysis A: Chemical, 13-21 (2003)(“Joseph”)
The Joseph process has been discussed above for the 102 rejection.
Joseph also teaches that the synthesized RuHCl(CO)(PPh3)3 can be immobilization on a support to be used as catalyst for hydrogenation of olefins. Joseph at page 19, left col. 3.2. Catalytic activity and Table 2.
Difference between Joseph and Claim 2
The Joseph process differs from the instant claim 2 only in that the reaction between ruthenium chloride and formaldehyde in the Joseph process is not conducted at a temperature of 40°C to 80°C.
Obviousness Rationale of Claim 2
One ordinary skill seeking RuHCl(CO)(PPh3)3 as a supported catalyst is motivated to modify the Joseph process by :
(i). first forming a mixture comprising ruthenium chloride and formaldehyde; and then
(ii). adding triphenylphosphine to the mentioned mixture and then allowing a reaction to proceed to form the product of RuHCl(CO)(PPh3)3 .
thus arrive at a method meeting each and every limitation of claim 1, and claim 1 is obvious. Note that any order of performing process steps is prima facie obvious. See MPE 2144.04 (C).
Claim 2 is obvious because one ordinary skill seeking high yield of production is further motivated to optimize the reaction conditions of the proposed process including the temperature of mixing the ruthenium chloride and the formaldehyde into the claimed ranges. Generally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. MPEP § 2144.04(II)(A) (citing In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955) ("[w]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation”)). Herein, neither the prior art or the instant application provides evidence to show the claimed ranges are critical. Rather the specification discloses that:
[37] The temperature in the step (S1) is not limited as long as it is in a range in which ruthenium chloride reacts with formaldehyde, . . . ..
Specification at page 9, [37], line 10-12, emphasis added.
Double Patenting
Nonstatutory double patenting rejection over US11571687B2 has been considered but not applied because they have different inventive concepts.
Conclusion
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/FRANK S. HOU/Examiner, Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
1 Once a reference teaching product appearing to be substantially identical is made the basis of a rejection, and the examiner presents evidence or reasoning to show inherency, the burden of production shifts to the applicant. MPEP § 2112(V) (citing In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433-34 (CCPA 1977). This is a procedural burden shifting. The requirement that the prior art necessarily teaches the alleged inherent (functional) element still remains. MPEP § 2112(IV). However, the burden is shifted to Applicant to demonstrate the alleged inherent element is not necessarily present in the cited prior art. Stated differently, when the examiner "has reason to believe" that the prior art reference inherently teaches the functional limitation, the burden shifts to the patent applicant to show that the functional limitation cannot be met by the prior art reference. MPEP 2112(V), see also, In re Schreiber, 128 F.3d 1473, 1478 (Fed. Cir. 1997); In re Chudik, 674 F. App'x 1011, 1012 (Fed. Cir. 2017) (both citing In re Swinehart, 439 F.2d 210, 212, 58 C.C.P.A. 1027 (C.C.P.A. 1971)).