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 1,3 and 9-10, 16-23 of S. Zhang, et al., US 17/286,666 (04/19/2021) are pending, under examination on merits and are rejected.
Withdrawal of Office Action Finality
A request for continued examination of US 17/286,666 under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 10/22/2025 has been entered. The supplemental amendment filed by Applicant on 11/06/2025 has been entered.
Election/Restrictions
Pursuant to the restriction requirement, Applicant elected Group I ( now claims 1,3 and 9-10, 16-23), with traverse, in the reply filed on 03/18/2024. Claims 5, 11-12 drawn to non-elected Group (II) are canceled. The Restriction Requirement is maintained as FINAL.
Pursuant to the election of species requirement, Applicant elected, without traverse, copper-based loaded catalyst as the species of hydrogenation catalyst, nitrobenzene as the species of nitro compound and aniline as the species of amino compound respectively in the reply filed on 03/18/2024 for prosecution on the merits to which the claims shall be restricted if no generic claim is finally held to be allowable.
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Now claims 1,3 and 9-10, 16-23of the elected invention read on the elected species. The elected species was searched and determined to be unpatentable as discussed in the 103 rejections below. The provisional species requirement is in effect. No claim is withdrawn as not read on the elected species.
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.
Pursuant to 35 U.S.C. 112(b), the claim must apprise one of ordinary skill in the art of its scope so as to provide clear warning to others as to what constitutes infringement. MPEP 2173.02(II); Solomon v. Kimberly-Clark Corp., 216 F.3d 1372, 1379, 55 USPQ2d 1279, 1283 (Fed. Cir. 2000). The meaning of every term used in a claim should be apparent from the prior art or from the specification and drawings at the time the application is filed. Claim language may not be ambiguous, vague, incoherent, opaque, or otherwise unclear in describing and defining the claimed invention. MPEP § 2173.05(a).
Insufficient Antecedent Basis
Claims 1,3 and 9-10, 16-23 are rejected under 35 U.S.C. 112(b) as indefinite because the claim 1 recites the limitation "wherein the fluidized bed reactor comprises a dense phase reaction zone . . . .". Given there are at least three fluidized bed reactors ( for hydrogenation, regeneration and activation respectively) in the claimed method, one ordinary skilled artisan does not know which fluidized bed reactor has the structural limitation of "wherein the fluidized bed reactor comprises a dense phase reaction zone . . . .".
Claim 3 is further rejected under 35 U.S.C. 112(b) as indefinite because there is insufficient antecedent basis for the recited limitation of “A1 to A3, A6 and B1 to B3” in the claim.
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.
Claims 1,3 and 9-10, 16-23 and the elected species are rejected under 35 U.S.C. 103 as being unpatentable over K. Sommer, et al, US20100280271A1 (2010) (“Sommer”) in view of S. Diao, et al. 286 Applied Catalysis A: General 30-35 (2005)(“Diao”); X.L. Jiang 45 Chlor-Alkali Industry 30-34 (2009) (“Jiang”) and C.K. Olin et al. US 2,891094 (1959) (“Olin”).
K. Sommer, et al, US20100280271A1 (2010) (“Sommer”)
Sommer teaches a process for the hydrogenation of nitroaromatics to aromatic amines in the gas phase with hydrogen using a catalyst arranged in stationary or virtually stationary beds in a reactor and at least a portion of the catalyst in the reactor is replaced continuously or at periodic intervals with at least 10% of the catalyst being replaced within 20 days. Sommer at page 1, [0001], emphasis added. Sommer teaches that nitrobenzene is particularly preferred as the nitroaromatic. Sommer at page 4, [0063].
Sommer teaches that the hydrogenation process can therefore be operated completely continuously. Sommer at page 5, [0075], line 19-10.
Sommer teaches that the nitroaromatic can be metered into the reactor through atomization of the liquid nitroaromatic into the fresh hydrogen or circulating gas/hydrogen stream by means of one-component or two-component nozzles. Sommer at page 5, [0065].
Sommer teaches that the gas mixture entering into the reactor has a preferred entry temperature of from 150° C to 400° C and the hydrogenation is preferably carried out under an absolute pressure of from 1 bar to 50 bar. Sommer at page 6, [0097]-[0098].
Sommer teaches that catalysts which can be employed are in principle any of the contacts described hitherto for the gas phase hydrogenation of nitro compounds. Sommer at page 7, [0105], line 1-3, emphasis added. Sommer teaches that copper catalyst is useful for the gas phase hydrogenation of nitroaromatics. Sommer at page 1, [00145], line 1-3, emphasis added.
Sommer teaches:
[0144] A suitable conveying gas for the catalyst is, for example, hydrogen or mixtures of hydrogen and inert gases or inert gases. The preferred inert gas is nitrogen.
[0145] The gas preferably flows through with speeds of from 0.1 m/s to 20 m/s, preferably 0.5 m/s to 10 m/s and most preferably at 1 m/s to 3 m/s. The gas speed is in general not constant because of the change in cross-section of the curved, circular catalyst layer and because of the change in the temperature and composition of the gas in the reaction zone.
[0146] The catalyst removed (catalyst discharge) preferably passes through a stripping stage in which the reaction gas is removed from the wedges and the catalyst support particles. Stripping is carried out by means of an inert gas, preferably nitrogen, flowing through.
Sommer at page 8, [0144]-[0146], emphasis added.
Sommer teaches that:
[0149] Before feeding back into the reactor, the recycled portion can be regenerated completely or partly by treatment with oxygen-containing gas mixtures, preferably air or air/ nitrogen mixtures, at elevated temperature, and in particular at temperatures of from 100° C. to 400° C., preferably at temperatures of from 200° C. to 300° C. This regeneration can be carried out completely (no longer a significant residual carbon content) or also incompletely ( e.g., for a shorter time and/or at a lower temperature than in the case of the complete regeneration).
[0150] The catalyst mixture obtained in this way is preferably stripped again before feeding it back into the process in order to remove the oxygen from the wedges and the catalyst support particles. This stripping may be done by flowing an inert gas, preferably nitrogen, through the catalyst.
[0151] The catalyst mixture obtained in this way then passes through an activation with an activating gas, preferably hydrogen. The activation is carried out at temperatures of from 100° C. to 400° C., preferably from 200° C. to 300° C.
[0152] The catalyst mixture obtained in this way is optionally brought together and mixed with the catalyst recycled without regeneration. These components can also be brought together before the activation, as described above. The catalyst mixture is then fed back into the process.
Sommer at page 8, [0149]-[0152], emphasis added. Sommer teaches that the process can be conducted as shown in the Fig. 2 flow diagram as indicated below.
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Sommer at page 9, [0156]-[0168].
Thus, Sommer teaches a process for the hydrogenation of nitrobenzene and the process comprises:
(i). a hydrogenation step,
Wherein, nitroaromatics is contacted with hydrogen gas and a hydrogenation catalyst in a hydrogenation reactor (1) to obtain the product (aniline) and a spent catalyst
(ii). a regeneration step,
wherein, the spent catalyst is regenerated in a regeneration reactor (13) to obtain a regenerated catalyst;
(iii). an activation step,
wherein, the regenerated catalyst is activated in an activation reactor (10) to obtain an activated catalyst;
(iv). a recycling step,
wherein, the regenerated catalyst and the activated catalyst are recycled to the hydrogenation step;
The Sommer process further comprises:
at least one step of degassing the spent catalyst(11) between the hydrogenation step and the regeneration step,
at least one step of degassing the regenerated catalyst(9) between the regeneration step and the activation step, and
a catalyst supplemental step (3d) introducing a supplement hydrogenation catalyst to the activation step.
Difference between Sommer and the Claims
Sommer differs from the independent claim 1 in that:
(i). Sommer does not teach that the hydrogenation step, the regeneration step and the activation step are each conducted in a fluidized bed reactor;
(ii). Sommer does not specify the catalyst for the hydrogenation of nitrobenzene is copper-based loaded catalyst,
(iii). Sommer further does not teach the specifics of the particle volume fractions in the transportation pipelines for the catalyst transportation. That is, Sommer does not specifically teach the following claim 1 limitations:
Claim 1 . . . wherein the particle volume fraction in the unit of % in the transportation pipeline of the spent catalyst . . . .
. . . .
and wherein C1, C2, C3, C4, and C6 and D1, D2, D3, and D4 are in the range of 0.5-5%.
(iv). Sommer does not teach the claimed condition to initiate the catalyst supplement that is:
the catalyst supplement step is initiated when the standard deviation of the instantaneous pressure fluctuation is greater than 600 Pa, or when the catalyst particles having a particle diameter of less than 100 um account for greater than 3 wt% by mass percent of all catalyst particles in the dense phase reaction zone.
S. Diao, et al. 286 Applied Catalysis A: General 30-35 (2005)(“Diao”)
Diao teaches that :
Gaseous hydrogenation of nitrobenzene (NB) over a catalyst is an important way to prepare aniline (AN), an important raw material for synthetic dyes, rubber chemicals, amino resins, and polyurethane (via diphenylmethane-4, 40-diisocyanate (MDI)). This highly exothermic reaction is normally conducted in a fluidized bed reactor, with the convenience of heat exchange.
Diao at page 30, left col. line 1-7, emphasis added.
Diao teaches a two-stage fluidized bed (TSFB) reactor for the gaseous hydrogenation of nitrobenzene to aniline as indicated below.
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Diao concludes that the two-stage fluidized bed (TSFB) reactor makes both the selectivity of nitrobenzene to aniline and the stable life-time of the catalyst to be increased. Diao also concludes that the two-stage fluidized bed (TSFB) reactor makes the cycle for the production of high purity aniline products can be significantly prolonged and the regeneration method for the catalyst becomes relatively simple and flexible; which are all favorable for the large-scale production of aniline product in high purity and at low cost. Diao at page 35, left col. Conclusion
Diao also teaches the hydrogenation condition for gaseous hydrogenation of nitrobenzene to aniline in the two-stage fluidized bed (TSFB) reactor:
Cu-SiO2 as the catalyst,
at a temperature of 240-280 ºC (513-553k),
at a pressure of 0.1013 MPa (atmospheric pressure),
and the molar ratio of hydrogen to nitrobenzene is 11(See Diao Abstract and Experimental Section).
Thus, Diao motivates one ordinary skill to modify the Sommer method by replacing the Sommer reactor with the Diao two-stage fluidized bed (TSFB) reactor for gaseous hydrogenation of nitrobenzene (NB) over catalyst Cu-SiO2 (See Diao abstract) to aniline.
X.L. Jiang 45 Chlor-Alkali Industry 30-34 (2009) (“Jiang”)
Jiang teaches that the specific surface area of Cu-SiO2 catalyst must be controlled within a certain range. If the particles are too fine, they will be easily taken out of the fluidized bed by the gas. The catalyst should also have a certain strength and not be easily damaged when boiling in the fluidized bed. The average particle size of industrial Cu-SiO₂ catalyst is 290 μm, the apparent density is 650kg/m3, and the Cu mass fraction is 16%-20%. Jiang at page 8/16, paragraph 2, line 3-8.
Jiang teaches that there are many factors that affect the activity of the catalyst such as raw material purity, fluidization quality, hydrogen-to-oil ratio, and raw material input, bed temperature, reaction temperature, regeneration temperature, activation temperature, emergency shutdown and abnormal factors in the production process also have a great impact on the catalyst activity. Jiang at page 8/16, 3 Factors affecting Cu-SiO₂ catalyst during production to page 9/16.
Regarding to hydrogen-to-oil ratio, Jiang teaches that:
the hydrogen-to-oil ratio refers to the mass ratio of hydrogen and nitrobenzene entering the fluidized bed. If the hydrogen-to-oil ratio is too high, the catalyst will suffer wear and serious loss, and it will easily produce large bubbles and surges, which will lead to deterioration of fluidization quality and affect the activity of the catalyst; if the hydrogen-to-oil ratio is too low, the superficial velocity of the tower will be reduced, and the distribution plate will be damaged. The appropriate hydrogen-to-oil ratio is an important factor in ensuring product yield and raw material conversion rate, but it must also be adjusted accordingly according to the catalyst service life and production load.
Jiang at page 9/16, 3.3 Hydrogen to oil ratio.
With regards to fluidization quality, Jiang teaches that:
In a normally operating fluidized bed reactor, the particle flow state can be divided into two parts, namely the dense phase section (a certain area away from the distribution plate) and the dilute phase section (the area located above the average surface of the bed). The main factor affecting fluidization is the superficial velocity of gas passing through the fluidized bed. If the gas superficial velocity is too small, the catalyst in the fluidized bed cannot be completely suspended, and the reaction materials and the catalyst cannot be fully contacted, which may easily cause a local overheating reaction; if the superficial velocity is too large, the reaction in the dilute phase section will be too violent , the heat cannot be removed in time, which can easily cause the carbonization reaction between nitrobenzene and aniline, deactivating the catalyst, and the catalyst can easily be taken out of the bed. If the load of the catalyst is too large (the amount of raw material processed by a unit amount of catalyst in a unit time), the activity of the catalyst will also decrease.
Jiang at page 10/16, 3.4 Fluidization quality.
With regards to the temperature in the hydrogenation step, Jiang teaches that:
If the reaction temperature is too high, in addition to the decrease in catalytic activity due to surface carbon, it will also cause side reactions, affect the selectivity of the hydrogenation reaction, and increase the difficulty of product separation. When the reaction temperature exceeds 280°C, the catalyst will become resinous; when the temperature exceeds 285°C, side reaction will occurs. If the reaction temperature is too low and nitrobenzene is not easy to completely vaporize. The liquid droplets condensed from some raw materials and finished product gases immerse into the catalyst surface, which not only accelerates the carbon deposition process, but also causes particle breakage and pulverization due to changes in thermal stress, resulting in catalyst banding. Output increases.
Jiang at page 10/16-11/16, 3.6 Reaction temperature. With regards to the temperature in the regeneration step, Jiang teaches that:
During the regeneration process, if the temperature exceeds 500°C, the catalyst activity will drop significantly and cannot be restored. Poor temperature control may also result in insufficient carbon burning and partial blockage of the catalyst micropores, as well as incomplete oxidation of Cu to generate Cu₂O). Every time it is regenerated, the pore structure and crystal lattice of the catalyst will be affected, and the activity will be reduced by 5% to 10%.
Jiang at page 11/16, 3.7 Regeneration temperature. Jiang also teaches the steps for regeneration of Cu-SiO2 catalyst as follows:
①The system performs high-temperature blowing for 4~5 hours.
②Replace the system with nitrogen until it is qualified.
③Control the center temperature of the fluidized bed to about 180 C.
④Slowly open the compressed air valve to vent air to the system, open the exhaust gas vent valve, slightly close the circulating hydrogen valve, control the temperature rise rate to ≤50 ℃/h, adjust the amount of air inlet, so that the core temperature is 370~400℃, and maintain 4 ~5h, maintain the pressure in the bed at 0.10~0.15 MPa.
⑤ When the pressure in the bed begins to rise, open the exhaust valve until it is fully open. If the pressure still rises, close the air inlet valve.
Jiang at page 14/16, 4.1.1 Regeneration steps.
Thus, Jiang teaches a method for catalyst regeneration in a fluidized bed reactor.
With regards the activation of Cu-SiO2 catalyst Jiang teaches that
For Cu-SiO₂ catalysts, activation refers to the process of reducing the inactive CuO distributed on the surface of silica gel in newly prepared or regenerated catalysts to active elemental Cu with H₂.
Jiang at page 11/16, 3.8 Activation temperature.
Therefore, one ordinary skill would be appraised that H2O steam would be formed during the step of activation due to the reaction between CuO and H2.
Jiang also teaches the steps for activation of Cu-SiO2 catalyst as follows:
①Replace the system with nitrogen until it is qualified.
②Open the high-pressure steam valve to heat the fluidized bed.
③When the center temperature of the fluidized bed is ≥180°C, open the hydrogen inlet valve and pass hydrogen into the system for activation. Adjust the incoming hydrogen flow and control the temperature rise rate to ≤50°C/h.
④Control activation temperature ≤260℃. When the core temperature begins to drop, the hydrogen inlet valve can be opened appropriately and the vent valve can be used to control the system pressure.
⑤ Activation ends when the temperature continues to drop.
Jiang at page 15/16, 4.1.2 Activation steps.
Thus, Jiang teaches a method for catalyst activation in a fluidized bed reactor.
To summarize, Jiang teaches one ordinary skilled artisan how to regenerate and activate Cu-SiO2 catalyst a fluidized bed reactor respectively.
C.K. Olin et al. US2,891094 (1959) (“Olin”)
Olin teaches a new catalyst for the reduction of nitrobenzene to aniline. Olin at col. 1, line 15-19. Olin teaches that the catalyst prepared by this process is a homogeneous dispersion of copper distributed through the silica carrier, with the copper well bonded to the carrier, so that it is not separable therefrom mechanically or by washing after impregnation. Olin at col. 2, line 8-13 (emphasis added). Thus, Olin catalyst is a Cu-SiO2 as Jiang teaches.
Olin also teaches to utilize the Cu-SiO2 catalyst to reduce nitrobenzene as follows:
A mixture of nitrobenzene from the vaporizer and an excess of hydrogen gas enter the reactor 2 together. The reacting gases which enter the reactor 2 can conveniently consist of approximately 10–20 mole percent nitrobenzene and 80-90 mole percent hydrogen.
The mixture of nitrobenzene vapor and hydrogen pass upward through a porous distributor plate into the reaction chamber, the catalyst powder being carried upward through the chamber by the flow of gases. The grid at the base of the reaction chamber is perforated with holes of such size and number as to provide a pressure drop of about 1 pound per square inch. This serves to distribute the gases across the catalyst bed and to provide jets of gas in the bed for gas-catalyst mixing. The holes in the grid must be large enough to prevent plugging by catalyst particles. The gases at reacting conditions (e.g. 20 pounds per square inch and 270 °C.) have a density of about 60 percent that of air at standard conditions. The vapor velocity within the reactor 2 is approximately 1 foot per second.
Olin at col. 4, line 6-25 (emphasis added).
It should be noted that the hydrogenation condition of Olin (such as catalyst, temperature, pressure and molar ration of hydrogen to nitrobenzene) is similar to the condition taught by Diao.
To summarize, Olin teaches the conditions of hydrogenation of nitrobenzene with Cu-SiO2 as: the vapor velocity is 1 foot per second (0.3 m/s), the molar ratio of hydrogen gas to the nitrobenzene is 4.5-8, the reaction temperature is 270°C, the reaction pressure is 20 pound per square inch (0.138 MPa).
Obviousness of the Claims
It would have been prima facie obvious for one skilled artisan to arrive at the instantly claimed inventions based on the teachings from Sommer, Diao, Jiang and Olin with a reasonable expectation of success before the effective filing date of the claimed invention.
Claim 1 is obvious because one ordinary skilled artisan in the art is motivated to modify Sommer method of hydrogenation of nitrobenzene by replacing the Sommer reactor with the Diao two-stage fluidized bed (TSFB) reactor with Cu-SiO2 as the hydrogen catalyst (which is an elected species of hydrogenation catalyst) in view of the teaching from Diao. Given the Diao two-stage reactor is a fluidized bed reactor wherein the catalyst particles are held suspended by the fluid stream of the reaction raw material, therefore, the claim 1 limitations of:
wherein the hydrogenation reactor is a fluidized bed reactor, the hydrogenation catalyst is a copper-based catalyst, and a full inventory of the cooper- based catalyst in the hydrogenation reactor is in contact with the reaction raw material.
are met by the arts.
The Diao two-stage fluidized bed (TSFB) reactor comprise a dense phase reaction zone, given Diao teaches that the hydrogenation condition for gaseous hydrogenation of nitrobenzene to aniline in the two-stage fluidized bed (TSFB) reactor is at a pressure of 0.1013 MPa, thus one ordinary skill in the art is further motivated include one dynamic pressure measuring point mounted on the side wall of the dense phase reaction zone so that can measure the instantaneous pressure fluctuation in the dense phase reaction zone because Jiang teaches that fluctuations in system pressure can cause fluidization changes in parameters such as the height of the movable bed and the pressure difference on the distribution plate may cause Cu-SiO2 catalyst to stick to the distribution plate or even deactivates of Cu-SiO2 catalyst (See Jiang at page 13/16, 3.10.3 System pressure fluctuations); which meets the claim 1 limitation of:
wherein the fluidized bed reactor comprises a dense phase reaction zone, at least one dynamic pressure measuring point is mounted on the side wall of the dense phase reaction zone to measure the instantaneous pressure fluctuation in the dense phase reaction zone.
With regards to the limitation of :
the catalyst supplement step is initiated when the standard deviation of the instantaneous pressure fluctuation is greater than 600 Pa, or when the catalyst particles having a particle diameter of less than 100 um account for greater than 3 wt% by mass percent of all catalyst particles in the dense phase reaction zone.
"[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. MPEP § 2144.05(II) (citing In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). Herein, Applicant does not provide any evidence the claimed condition is critical to the claimed process; rather as mentioned above that one ordinary skilled artisan has a motivation to optimize catalyst supplement based on the fluctuations in system pressure into the claimed ranges because Jiang teaches that fluctuations in system pressure may deactivates of Cu-SiO2 catalyst.
One ordinary skill in the art is further motivated to conduct each of the step of catalyst ( Cu-SiO2) regeneration and the step of catalyst (Cu-SiO2) activation in a fluidized bed reactor with a reasonable expectation of success because Jiang teaches the specific steps for regeneration and activation of catalyst Cu-SiO2 in a fluidized bed reactor respectively.
With regard to claim limitation:
Claim 1 . . . wherein the particle volume fraction in the unit of % in the transportation pipeline of the spent catalyst . . . .
. . . .
and wherein C1, C2, C3, C4, and C6 and D1, D2, D3, and D4 are in the range of 0.5-5%.
Jiang teaches that” load of the catalyst” through the system is an optimizable parameter:
If the load of the catalyst is too large (the amount of raw material processed by a unit amount of catalyst in a unit time), the activity of the catalyst will also decrease.
Jiang at page 10/16, 3.4 Fluidization quality.
Therefore, one ordinary skill is motivated to optimize the particle volume fractions in the pipeline for the transportation of the catalyst into the claimed range so that can maintain the catalytic activities of the catalyst and make sure the process can be conducted continuously. "[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. MPEP § 2144.05(II) (citing In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). The specification provides no evidence that this parameter is critical . MPEP § 2144.05(II).
In view of the foregoing, the cited reference combination teaches each and every limitation of claim 1, which is therefore obvious over the cited arts.
Claim 31 and claim 19 are obvious because one ordinary skill is motivated to optimize the average mass flowrate into the claimed range because Jiang teaches that the “average mass flowrate” of catalyst through the system is an optimizable parameter. (See Jiang at page 10/16, 3.4 Fluidization quality). Generally, the average mass flowrate (in analogy to concentration or temperature) will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such range is critical. "[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. MPEP § 2144.05(II) (citing In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). The specification provides no evidence that the claimed parameters in claim 3 and 19 are critical . MPEP § 2144.05(II).
Claim 9 and 17 is obvious because Olin Cu-SiO2 catalyst is a copper-based loaded catalyst and Olin teaches that the prefer size of the catalyst is 20-150 microns in diameter. Olin at col. 3, line 24-26. With regarding the size difference between 20-150 µM and the claimed 5-150 µM or 20-70µM, in the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. MPEP 2144.05.I. Herein, the claimed range of 20-70 lies inside of the prior art range 20-150; the claimed range of 5-150 overlaps with the prior art range 20-150; therefore, a prima facie case of obviousness exists.
Claim 10 is obvious because Jiang teaches the apparent density of Cu-SiO2 catalyst is 650kg/m3 which anticipates the claimed 300-1200 kg/m3. Note that claim 10 is parsed by “and/or”, so the prior art need only teach one claimed alternative.
Claim 16 is obvious because one ordinary skill in the art is motivated to initiate a catalyst supplement step when there is an significant pressure fluctuations in the reactor system because Jiang teaches that fluctuations in system pressure can cause fluidization changes in parameters such as the height of the movable bed and the pressure difference on the distribution plate may cause Cu-SiO2 catalyst to stick to the distribution plate or even deactivates of Cu-SiO2 catalyst. Jiang at page 13/16, 3.10.3 System pressure fluctuations. With regards to the claimed standard deviation of the instantaneous pressure in claim 16, again "[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." MPEP 2144.05. II. Herein, neither prior art nor the specification provides evidence the claimed ranges are critical to the claimed process, therefore, claim 16 is obvious.
Claim 18 is obvious because Jiang teaches that the average particle size of industrial Cu-SiO₂ catalyst is 290 μm. Note that claim 18 is parsed by “and/or”, so the prior art need only teach one claimed alternative.
Claim 20 is obvious because one ordinary skill in the art is further motivated to set up the hydrogenation reaction step at the condition as taught by Olin (the vapor velocity is 0.3 m/s, the molar ratio of hydrogen gas to the nitrobenzene is 4.5-8, the reaction temperature is 270°C, the reaction pressure is 0.138 MPa). These conditions all anticipates the claimed ranges by the instant claim 20. Note that claim 20 is parsed by “and/or”, so the prior art need only teach one claimed alternative.
Claim 21 is obvious because one ordinary skilled artisan is motivated to modify the size of the hydrogenation reactor, the regeneration reactor and/or activation reactor based on his real condition.
Claims 22-23 are obvious because one of ordinary skill in the art is motivate to optimize average flow rate of the supplemental hydrogenation catalyst based the amount of the catalyst in the hydrogenation reactor into the claimed ranges because Sommer teaches that at least a portion of the catalyst in the reactor is replaced continuously or at periodic intervals with at least 10% of the catalyst being replaced within 20 days. Sommer at page 1, [0001], line 4-7. Again "[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. MPEP § 2144.05(II) (citing In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).
Applicant’s Argument
Applicant first argues on the ground that the Jiang does not specific teach the limitation of:
Claim 1. . . . the catalyst supplement step is initiated when the standard deviation of the instantaneous pressure fluctuation is greater than 600 Pa, or when the catalyst particles having a particle diameter of less than 100 um account for greater than 3 wt% by mass percent of all catalyst particles in the dense phase reaction zone.
Claim 16.The hydrogenation reaction process according to claim 1, wherein the catalyst supplement step is initiated when a response frequency of at least one dynamic pressure measuring point is not less than 100 Hz, and/or when the standard deviation of the instantaneous pressure fluctuation is greater than 1500 Pa, the catalyst supplement step is initiated, and/or when the catalyst particles having a particle diameter of less than 100 m comprise greater than 5wt% by mass percent of all catalyst particles in the dense phase reaction zone.
See II. Rejections Under 35 U.S.C.§ 103 at page 11/14-12/14 of the Remarks submitted on 11/06/2025.
These arguments have been fully considered but not persuasive. As mentioned in the 103 rejection above that while Jiang does not specifies the claimed pressure fluctuation to initiate catalyst supplement, however, Jiang does teaches that fluctuations in system pressure may deactivaty of Cu-SiO2 catalyst (See Jiang at page 13/16, 3.10.3 System pressure fluctuations), therefore, one ordinary skill in the art is motivated to optimize the condition to initiate catalyst supplement based on the pressure fluctuation in the system. Generally, with respect to optimization of result-effective variables (herein is the pressure fluctuation to initiate catalyst supplement), changes to the prior art involving degree is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions. MPEP § 2144.05(II)(A) (citing In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955); In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929).
Applicant’s Argument Regarding the Criticality of the I) “all of C1 to C3, C6 and D1 to D3 are 0.5-5%" and II) "the catalyst supplement step is initiated when the standard deviation of the instantaneous pressure fluctuation is greater than 600 Pa, or when the catalyst particles having a particle diameter of less than 100 m account for greater than 3 wt% by mass percent of all catalyst particles in the dense phase reaction zone.
Applicant further argues on the ground that:
Applicant demonstrated the criticality of the i) “all of C1 to C3, C6 and D1 to D3 are 0.5-5%" ("the particle volume fraction") and II) "the catalyst supplement step is initiated when the standard deviation of the instantaneous pressure fluctuation is greater than 600 Pa, or when the catalyst particles having a particle diameter of less than 100 m account for greater than 3 wt% by mass percent of all catalyst particles in the dense phase reaction zone."
. . . .
In contrast, according to Comparative Example 1, C1 to C6 and D1 to D5 is out of the value range of 0.5-5% defined in claimed invention, i.e., in Comparative Example 1, C6 is 0.3%, and no the supplement of the fine particle catalyst was carried out, the expansion coefficient of the dense phase reaction zone was 1.46, the maximum temperature difference at any part in the reaction zone was 13.8° C, the fluidization quality of Comparative Example 1 is significantly inferior to Examples 1-18. One skilled artisan would have readily appreciated that, although Comparative Example 1 can be operated continuously, due to the lack of adding fine catalyst particles during the process and the lower particle volume fraction (C6), compared to Examples
See II. Rejections Under 35 U.S.C.§ 103 at page 13/14 of the Remarks submitted on 11/06/2025. Emphasis added.
These arguments are not persuasive because the parameters of the Comparative
Example 1 described in the specification as follows:
The average mass flowrates for the transportation in the pipelines (Al-A6 and B1-B5) were all 7 kg/h, and for the particle volume fractions for the pipelines (C1-C6 and D1-D5), C1-C5 were 0.83%, C6 was 0.55%, D1-D5 were 1.06%.
Specification at page 42/60, line 18-20, emphasis added. Clearly, each of the C1 to C6 and D1 to D5 in the range of 0.5%-5% rather out of the value range of 0.5-5% as argued.
Relevant Sections of the MPEP
A greater than expected result and evidence of unobvious or unexpected advantageous properties are evidentiary factors pertinent to the legal conclusion of obviousness of the claims at issue. MPEP § 716.02(a)(I)/(II). However, the burden is on Applicant to establish that the evidence relied upon demonstrates that the differences in results are in fact unexpected and unobvious and of both statistical and practical significance. MPEP § 716.02(b). Evidence of unexpected properties may be in the form of a direct or indirect comparison of the claimed invention with the closest prior art which is commensurate in scope with the claims. MPEP § 716.02(b)(III).
Furthermore, whether the unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support; that is, the showing of unexpected results must be reviewed to see if the results occur over the entire claimed range. MPEP § 716.02(d). The nonobviousness of a broader claimed range can be supported by evidence based on unexpected results from testing a narrower range if one of ordinary skill in the art would be able to determine a trend in the exemplified data which would allow the artisan to reasonably extend the probative value thereof. MPEP § 716.02(d)(I).
Further, an affidavit or declaration under 37 CFR 1.132 also must compare the claimed subject matter with the closest prior art to be effective to rebut a prima facie case of obviousness. MPEP § 716.02(e).
The Results Proffered in the Specification
First of all, Applicant does not provide any proffered compared results to show the claim “all of C1 to C3, C6 and D1 to D3 are 0.5-5%" is critical. See Examples 1-comparative Example 2. Regarding the claimed pressure fluctuation, Examiner summarizes the proffered comparative results between Examples 16-18 and comparative Example 1 as indicated in the Table below:
Example 16
Example 17
Example 18
Comparative 1
Average mass flowrate
(A1-A6 and B1-B5),
kg/h
All 13
All 13
All 13
All 7
Particle volume
fractions for the
pipelines (C1-C6 and D1-D5)
C1-C5 were 0.9%, C6 was 0.6%, D1-D5 were 1.2%
C1-C5 were 0.9%, C6 was 0.6%, D1-D5 were 1.2%
C1-C5 were 0.9%, C6 was 0.6%, D1-D5 were 1.2%
C1-C5 were 0.83%, C6 was 0.55%, D1-D5 were 1.06%
Ratio of the average
mass flowrate of the
supplement hydrogenation catalyst
hydrogenation catalyst
inventory in the
hydrogenation reactor,
h-1
0.00005
0.00005
0.00005
0.00005
Dimensionless particle
diameter in the
fluidized bed reactor
10
10
10
10
dimensionless gas
velocity in the fluidized bed reactor
0.1
0.1
0.1
0.1
Dimensionless particle
diameter in the
regenerator
8
8
8
8
Dimensionless gas
velocity in the regenerator
0.15
0.15
0.15
0.15
Dimensionless particle
diameter in the activator
8
8
8
8
Dimensionless gas
velocity in the activator
0.15
0.15
0.15
0.15
Standard deviation value of the pressure pulsation at any point of the bed layer of the dense phase reaction zone maintained by supplementing fine catalyst particles, Pa
500
500
500
No control, without the supplement of the fine particle catalyst
solid particle inventory
of hydrogenation reactor: solid particle inventory of
regeneration reactor: solid particle inventory of activation reactor
30: 1: 1
40:3:3
40:3:3
40:3:3
Height of the hydrogenation reactor:height of the
Regeneration reactor:height of the
activation reactor
5:1:1
2:1:1
5:1:1
5:1:1
Diameter of the
hydrogenation
reactor:diameter of the
regeneration
reactor:diameter of the
activation reactor
4: 1: 1
4: 1: 1
6: 1: 1
4: 1: 1
Expansion coefficient of the dense phase reaction zone
1.62
1.64
1.66
1.46
Maximum temperature
difference in the reaction zone, °C
7.2
7.2
7.0
13.8
Carbon deposition content when the reaction time was 90 minutes under the high space velocity,%
could be controlled at no greater than 0.7%
Could be controlled at no greater than 0.7%
could be controlled at no greater than 0.73%
could be controlled at no greater than 0.7%
The Proffered Results Do Not Overcome the § 103 Rejection Because Applicant Has Not Met Its Burden of Demonstrating that the Proffered Result Is Unexpected
Given the average mass flowrate (A1-A6 and B1-B5) of the comparative Example 1 only is the 54% (7/13) of Examples 16-18 AND there is no catalyst supplement in the comparative Example 1 while Examples 16-18 has catalyst supplement, there is no unexpected that the maximum temperature difference in the reaction zone of the comparative Example 1 is higher (51%) than those of Examples 16-18. Applicant has provided no explanation of why the claimed parameters are critical. Applicant has therefore not met its burden. MPEP § 716.02(b). The burden is on Applicant to establish that the evidence relied upon demonstrates that the differences in results are in fact unexpected and unobvious and of both statistical and practical significance. MPEP § 716.02(b).
The Proffered Results Do Not Overcome the § 103 Rejection Because the Proffered Results are Not Commensurate in Scope with the Claims
Whether the unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support; that is, the showing of unexpected results must be reviewed to see if the results occur over the entire claimed range. MPEP § 716.02(d). Herein, one the Cu-SiO2 catalyst is compared which is clearly not commensurate in scope with the large genera of copper-based catalyst claimed by the claim 1.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to FRANK S. HOU whose telephone number is (571)272-1802. The examiner can normally be reached 6:30 am-2:30 pm Eastern on Monday to Friday. Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached on (571)2705241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/FRANK S. HOU/Examiner, Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
1 Based on the claim set submitted on 06/05/2025 and claim 19 as well consistent with the specification, A1 is interpreted as the average mass flowrate in of the spent catalyst being transported from the hydrogenation step to the hydrogenation degassing step; B1 is interpreted as the average mass flowrate of the spent catalyst being transported from the hydrogenation degassing step to the regeneration step, A2 is interpreted as the average mass flowrate of the regenerated catalyst being transported from the regeneration step to the first regeneration degassing step, B2 is interpreted as the average mass flowrate of the regenerated catalyst being transported from the first regeneration degassing step to the activation step, A3 is interpreted as the average mass flowrate in of the activated catalyst being transported from the activation step to the activation degassing step, B3 is interpreted as the average mass flowrate of the activated catalyst being transported from the activation degassing step to the recycling step, A6 is interpreted as the average mass flowrate of the regenerated catalyst or the activated catalyst being transported from the recycling step to the hydrogenation step.