Prosecution Insights
Last updated: April 18, 2026
Application No. 18/250,277

Process And Catalyst For The Catalytic Hydrogenation Of Organic Carbonyl Compounds

Final Rejection §103
Filed
Apr 24, 2023
Examiner
CHU, YONG LIANG
Art Unit
1731
Tech Center
1700 — Chemical & Materials Engineering
Assignee
Topsoe A/S
OA Round
2 (Final)
75%
Grant Probability
Favorable
3-4
OA Rounds
2y 6m
To Grant
78%
With Interview

Examiner Intelligence

Grants 75% — above average
75%
Career Allow Rate
1057 granted / 1414 resolved
+9.8% vs TC avg
Minimal +3% lift
Without
With
+3.4%
Interview Lift
resolved cases with interview
Typical timeline
2y 6m
Avg Prosecution
44 currently pending
Career history
1458
Total Applications
across all art units

Statute-Specific Performance

§101
1.0%
-39.0% vs TC avg
§103
33.8%
-6.2% vs TC avg
§102
20.6%
-19.4% vs TC avg
§112
29.0%
-11.0% vs TC avg
Black line = Tech Center average estimate • Based on career data from 1414 resolved cases

Office Action

§103
DETAILED ACTION The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA . Claims 13, and 24-25 have been amended. Claim 27 is cancelled. New claims 28-31 are added. Claims 1-26 and 28-31 are pending in the instant application. Claims 13-26 remain withdrawn. Claims 1-12, and 28-31 are under examination on the merits. Response to Amendment The Amendment by Applicants’ representative Mr. Travis D. Boone on 03/05/2026 has been entered. Information Disclosure Statements Applicants’ Information Disclosure Statements, filed on 02/18/2026 and 03/06/2026, have been considered. Please refer to Applicant’s copies of the PTO-1449 submitted herewith. Response to Arguments/Amendments Claim rejection under 35 U.S.C.§112(b) Applicant’s argument on the ground that claim 1 does not introduce or refer to "active ingredients," nor does it suggest that the percentages are calculated on any basis other than the total weight of the catalyst composition. Accordingly, a person of ordinary skill in the art would understand the recited percentages to be based on the total weight of the catalyst composition. Applicant’s argument is found persuasive. The rejection is hereby withdrawn. Claim rejection under 35 U.S.C.§102(a)(1) Applicant’s argument is on the ground that Claim 1 requires at least 50 wt% spinel in the oxidized form as determined by XRD, while Gao is silent as to any quantitative spinel fraction. Therefore, Gao fails to teach express structural limitation of at least 50 wt% spinel in the oxidized form as determined by XRD. Applicant’s argument is found persuasive. The rejection over Gao is hereby withdrawn. In terms of the 102-rejection over Shi et al., Applicant argued that Shi reports that CuAI2O4 spinel appears at elevated calcination temperatures. However, Shi does not quantify the spinel fraction, does not state that spinel becomes a majority phase, and does not disclose >50 wt% spinel by XRD. Detection of spinel peaks is not equivalent to disclosure of at least 50 wt% spinel. Accordingly, Shi does not anticipate claim 1. Applicant’s argument is found persuasive. The rejection over Gao is hereby withdrawn. Claim rejection under 35 U.S.C.§103(a) Applicant’s argument is on the ground that neither reference of Shi et al. nor Gao et al. quantifies spinel content nor teaches increasing spinel to >50 wt%. There is no disclosure or suggestion that a skilled artisan would (or could) deliberately modify the art processes to obtain a catalyst in which spinel constitutes at least half of the oxidized composition. Applicant’s argument has been fully considered, but not sufficient to overcome the rejection because Shi et al. discloses the XRD patterns of the catalysts calcined at different temperatures are shown in Fig. 11, wherein after the catalyst CZA-d-2-t was calcined at 550 °C, the CuAl2O4 spinel phase was formed; and the higher the calcination temperature is, the higher the crystallization degree of CuAl2O4 (spinel phase) was produced (see right column at p.1139 to left column at p.1140). Furthermore, Shi et al. discloses the CuZn0.3AlOx (CZA) catalysts were prepared by fractional co-precipitation of the method (d) (see right column at p.1133). It can be found that a substantially identical co-precipitation method was also disclosed in Example 1 of Applicant’s Specification [0020-0026, and 0093] (“a. Coprecipitating” and “Example 1. Preparation of Catalyst A”). Specifically, Shi et al. discloses the Cu/ZnO/Al2O3 catalyst (CZA-d-2-450) prepared by fractional co-precipitation with aging at 70 °C for 2 h and calcination at 450 °C for 4 hour shows the highest activity for L-phenylalanine methyl ester hydrogenation to L- phenylalanol (see “5. Conclusions” at p.1135); and the Cu/ZnO/Al2O3 catalyst (CZA-d-5-450) has a largest BET surface area of 159 m2/g (see Table 1 at p.1135) and best selectivity to L-p-ol on the L-phenylalanine methyl ester hydrogenation for both 10 minutes and 5 hours (see Fig. 1 at p.1135). Applicant’s invention would have been obvious over Shi et al. because the claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977). "When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). Therefore, the 103(a) rejection is maintained. The following rejection is necessitated by the amendment filed 03/05/2026: 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 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 of this title, 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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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. Claims 1-12 and 28-31 are rejected under 35 U.S.C. 103 as being unpatentable over Shi et al. in view of Gao et al. Determination of the scope and content of the prior art (MPEP §2141.01) Shi et al. discloses a catalyst composition for catalytic hydrogenation of L-phenylalanine methyl ester to L- phenylalaninol, and a method of preparing the catalyst Cu/ZnO/Al2O3 having the optimal mole ratio of Cu:Zn:Al= 1:0.3:1 (see “2.1. Catalyst preparation” at p.1133) according to the disclosed by the reference [30] Gao et al. Gao et al. discloses a catalyst composition (C5) for catalytic hydrogenation of L-phenylalanine methyl ester to L- phenylalaninol, wherein the mole ratio of Cu:Zn:Al= 1.07:0.55:1, and the Cu amount (wt%) in the catalyst is 37.6 wt% (see Table 1 at p.1057). Accordingly, the Zn amount (wt%) in the catalyst is calculated to be 19.9 wt%; and the amount of Al (wt%) in the catalyst is calculated to be 14.9 wt%, which reads on the limitation of Applicant’s claim 1. In addition, Shi et al. discloses the XRD patterns of the catalysts calcined at different temperatures are shown in Fig. 11, wherein after the catalyst CZA-d-2-t was calcined at 550 °C, the CuAl2O4 spinel phase was formed; and the higher the calcination temperature is, the higher the crystallization degree of CuAl2O4 (spinel phase) was produced (see right column at p.1139 to left column at p.1140, and “5. Conclusions” at p.1142). Gao et al. discloses a catalyst composition (C5) for catalytic hydrogenation of L-phenylalanine methyl ester to L- phenylalaninol, wherein the mole ratio of Cu:Zn:Al= 1.07:0.55:1, and the Cu amount (wt%) in the catalyst is 37.6 wt% (see Table 1 at p.1057). Accordingly, the Zn amount (wt%) in the catalyst is calculated to be 19.9 wt% (36x37.6/68, wherein “36” is based on 65.37x0.55, “37.6” is based on the amount of Cu in the catalyst is 37.6 wt%, and “68” is based on the 63.54x1.07); and the amount of Al (wt%) in the catalyst is calculated to be 14.9 wt% (27x37.6/68). In addition, Gao et al. teaches that the Cu/ZnO/Al2O3 catalyst with a Cu/Zn/Al molar ratio of 1.0:0.3:1.0 shows the highest activity and ee selectivity (see 4. Conclusions at p.1061). Ascertainment of the difference between the prior art and the claims (MPEP §2141.02) The difference between Applicant’s claims 1-2 and Shi et al is that the prior art is silent on the catalyst composition Cu/ZnO/Al2O3 comprising in its oxidized form 12-38% by weight of Cu, 13-35% by weight of Zn, and 12-30% by weight of Al. In addition, Shi et al. does not teach the composition comprising in its oxidized form at least 50% by weight of a spinel structure as determined by X-ray diffraction (XRD). Finding of prima facie obviousness--rational and motivation (MPEP §2142-2413) However, Shi et al. discloses the catalyst Cu/ZnO/Al2O3 having the optimal mole ratio of Cu:Zn:Al= 1:0.3:1 (see “2.1. Catalyst preparation” at p.1133) according to the disclosed by the reference [30] Gao et al., wherein Gao et al. discloses the catalyst composition (C5) having the Cu is 37.6 wt%, the Zn is 19.9 wt%, and the Al is 14.9 wt%. Therefore, the difference of the catalyst composition Cu/ZnO/Al2O3 comprising in its oxidized form 12-38% by weight of Cu, 13-35% by weight of Zn, and 12-30% by weight of Al is further taught and/or suggested by Gao et al. Furthermore, the secondary reference of Gao et al. was specifically referred by Shi et al. as the reference [30] for preparing the catalyst composition of Cu/ZnO/Al2O3. More importantly, Shi et al. discloses the CuZn0.3AlOx (CZA) catalysts were prepared by different precipitation methods a)-d), and their physicochemical properties are greatly affected by the preparation method and conditions, and the uniform size distribution of CuO species can be obtained by fractional co-precipitation of method d) (see right column at p.1133), and the Cu/ZnO/Al2O3 catalyst (CZA-d-2-450), prepared by fractional co-precipitation with aging at 70 °C for 2 h and calcination at 450 °C for 4 hour, shows the highest activity for L-phenylalanine methyl ester hydrogenation to L- phenylalanol (see “5. Conclusions” at p.1135); and the Cu/ZnO/Al2O3 catalyst (CZA-d-5-450) has a largest BET surface area of 159 m2/g (see Table 1 at p.1135) and best selectivity to L-p-ol on the L-phenylalanine methyl ester hydrogenation for both 10 minutes and 5 hours (see Fig. 1 at p.1135). A substantially identical co-precipitation method is also disclosed in Example 1 of Applicant’s Specification [0020-0026, and 0093] (“a. Coprecipitating” and “Example 1. Preparation of Catalyst A”). The claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977). "When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). Therefore, Shi et al. in view of Gao et al. would have rendered claims 1-2 obvious. In terms of claim 3 wherein the composition comprises in its oxidized form at least 60% by weight of a spinel structure as determined by X-ray diffraction, Shi et al. discloses the formation of spinel oxide are closely related to the calcination temperature, resulting in the variation of SBET, Scu, Dcu and dcuo. Shi et al. discloses the XRD patterns of the catalysts calcined at different temperatures are shown in Fig. 11, wherein after the catalyst CZA-d-2-t was calcined at above 650 °C and below 750 °C, the CuAl2O4 spinel phase was formed as a major crystal product CuAl2O4 (spinel phase) (see right column at p.1139 to left column at p.1140), which reads on the composition comprises in its oxidized form at least 60% by weight of a spinel structure as determined by X-ray diffraction. In terms of claim 4 wherein the catalyst composition comprises in its oxidized form 15-38% by weight of Cu, Shi et al. discloses the XRD patterns of the catalysts calcined at different temperatures are shown in Fig. 11, wherein after the catalyst CZA-d-2-t was calcined at above 650 °C and below 750 °C, the CuAl2O4 spinel phase was formed as a major crystal product CuAl2O4 (spinel phase), wherein Cu is in its oxidized form. In terms of claim 5 wherein having in its oxidized form an olive-green color corresponding to approximately Red:100 Green:100 Blue:50, the limitation is considered to be inherited property of the catalysts calcined at different temperatures are shown in Fig. 11, wherein after the catalyst CZA-d-2-t was calcined at above 650 °C and below 750 °C, the CuAl2O4 spinel phase was formed as a major crystal product CuAl2O4 (spinel phase), wherein Cu is in its oxidized form. In terms of claim 6 wherein the catalyst composition comprises in its oxidized form 13-24% by weight of Zn, Gao et al. discloses the catalyst composition (C5) having the Cu is 37.6 wt%, the Zn is 19.9 wt%, and the Al is 14.9 wt%. In terms of claim 7 wherein the catalyst composition comprises in its oxidized form 17-24% by weight of Al, Shi et al. discloses the catalyst CZA-d-2-450, wherein the catalysts have the Al is 23.87 wt% [(26.98x0.98)/(63.54x1.03+65.37x0.29+26.98x0.98)x100%=23.87 wt%], see Table 4 at p.1139. In terms of claim 8 wherein the catalyst composition in its oxidized form comprises less than 0.01 wt% Ni and/or less than 0.01 wt% Cr, both Shi et al. and Gao et al. disclose the catalysts without mentioning Ni and Cr. Therefore, the catalysts comprise less than 0.01 wt% Ni and/or less than 0.01 wt% Cr. In terms of claims 9-10, neither Shi et al. nor Gao et al. teaches the catalyst composition having in its oxidized form a radial crush strength, SCS, of between 25 and 150 kp/cm or between 10 and 75 kp/cm, and/or a density in the range of from 1.45-2.35 g/cm3. However, Gao et al. discloses a substantially same method for preparing the catalyst composition (see “2.1 Catalyst preparation”) as the preparing method of presently claimed catalyst composition (see “Example 1. Preparation of Catalyst A” of the present specification at p.15). Even though Gao et al. is silent on the limitation of the catalyst composition having in its oxidized form a radial crush strength, SCS, of between 25 and 150 kp/cm or between 10 and 75 kp/cm, and/or a density in the range of from 1.45-2.35 g/cm3, the said physical property is considered to be the inherited physical property of the catalyst composition. Because the presently claimed catalyst composition and the catalyst composition of Gao et al. were prepared by the substantially same preparation methods, the claimed physical properties of the catalyst compositions in claims 9 and 10 would have been either inherited or obvious over the catalyst composition disclosed by Gao et al. It has long been recognized that a product is inseparable from its properties. The claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977). "When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). Therefore, the prima facie case can be rebutted by evidence showing that the prior art products do not necessarily possess the characteristics of the claimed product. In re Best, 562 F.2d at 1255,195 USPQ at 433. In addition, optimization of the physical properties of a radial crush strength, SCS and or density of a catalyst composition through the same preparation method disclosed in the prior art is a routine optimization. In the absence of unexpected results, one of ordinary skill in the art at the time of the invention would have been motivated to optimize the process to prepare the desired oxygen carriers. Therefore, Shi et al. in view of Gao et al. would have rendered claims 9-10 obvious. In terms of claim 11 having in its reduced form a copper metal surface area above 10 m2/g Cu, Shi et al. discloses the catalysts CZA-d-y-450 having a copper metal surface area (Scu) 12.4 m2/g, 16.6 m2/g, 14.9 m2/g, 13.5 m2/g, and 11.5 m2/g, which are above 10 m2/g Cu, see Table 3 at p.1137. In terms of claim 12 comprising in its oxidized form less than 15% by weight of ZnO, Shi et al. discloses the catalyst Cu/ZnO/Al2O3 with different Zn amounts C0-C7 (see Table 1 at p.1057). The C1 catalyst has its oxidized form less than 15% by weight of ZnO. In terms of claims 28-30, Shi et al. discloses the CuZn0.3AlOx (CZA) catalysts were prepared by fractional co-precipitation of method d) (see right column at p.1133), and the Cu/ZnO/Al2O3 catalyst (CZA-d-2-450), prepared by fractional co-precipitation with aging at 70 °C for 2 h and calcination at 450 °C for 4 hour, shows the highest activity for L-phenylalanine methyl ester hydrogenation to L- phenylalanol (see “5. Conclusions” at p.1135); and the Cu/ZnO/Al2O3 catalyst (CZA-d-5-450) has a largest BET surface area of 159 m2/g (see Table 1 at p.1135) and best selectivity to L-p-ol on the L-phenylalanine methyl ester hydrogenation for both 10 minutes and 5 hours (see Fig. 1 at p.1135). A substantially identical co-precipitation method is also disclosed in Example 1 of Applicant’s Specification [0020-0026, and 0093] (“a. Coprecipitating” and “Example 1. Preparation of Catalyst A”). The claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977). "When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). Therefore, Shi et al. in view of Gao et al. would have rendered claims 28-30 obvious. In terms of claim 31 wherein the catalyst composition is obtained by calcining a catalyst precursor composition, wherein the catalyst precursor composition is formed from an alkaline aluminate solution, Shi et al. (right column at p.1133) discloses the method d) for preparing the catalyst composition by co-precipitated the Al3+ solution and 0.5 M Na+ solution at pH=7.5, wherein the 0.5 M Na+ solution is a Na2CO3 solution (i.e., an alkaline aluminate solution), and the reaction precursor was calcinated at 450 °C. Conclusions Claims 1-12 and 28-31 are rejected. Claims 13-26 remain withdrawn. Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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 extension fee 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 date of this final action. Telephone Inquiry Any inquiry concerning this communication or earlier communications from the examiner should be directed to Yong L. Chu, whose telephone number is (571)272-5759. The examiner can normally be reached on M-F 8:30am-5:00pm. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Amber R. Orlando can be reached on 571-270-3149. The fax phone number for the organization where this application or proceeding is assigned is (571) 273-8300. Status Information regarding the status of an application may be obtained from the Patent Application Information Retrieval (PAIR) system. Status information for published applications may be obtained from either Private PAIR or Public PAIR. Status information for unpublished applications is available through Private PAIR only. For more information about the PAIR system, see http://pair-direct.uspto.gov. Should you have questions on access to the Private PAIR system, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). /YONG L CHU/Primary Examiner, Art Unit 1731
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Prosecution Timeline

Apr 24, 2023
Application Filed
Apr 24, 2023
Response after Non-Final Action
Feb 03, 2026
Non-Final Rejection — §103
Mar 05, 2026
Response Filed
Apr 08, 2026
Final Rejection — §103 (current)

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