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 .
Claims Status
Claims 1-5, 7 and 8 are pending. Claim 1 has been amended. Claim 6 has been canceled.
Applicant’s arguments, filed 06/03/2026, with respect to the rejection(s) of claim(s) 1-8 under 35 USC 35 have been fully considered and are persuasive. Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of Beck et al. (US 3616320 A).
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claim Rejections - 35 USC § 103
Claim(s) 1-5, 7 and 8 is/are rejected under 35 U.S.C. 103(a) as being unpatentable over Liu et al. (CN 116555788 A, machine translation) in view of Beck et al. (US 3616320 A).
Considering claim 1, Liu discloses a method for electrolytic reduction of acrylonitrile to produce adiponitrile, comprising following steps: mixing the acrylonitrile with an electrolyte solution and then performing the electrolytic reduction to obtain the adiponitrile; wherein components of the electrolyte solution comprise: a supporting electrolyte, an electrode protector, a complexing agent, a quaternary ammonium salt (page 2, 5th paragraph); a material of an anode used for the electrolytic reduction comprises any one of carbon steel, stainless steel (page 5, Example 1); and a distance between a cathode and the anode during the electrolytic reduction is 3 millimeters (mm) (page 4, last paragraph).
Liu does not disclose and hexanetricarbonitrile.
Liu discloses that conversion of acrylonitrile comprises other organics, and Liu focuses on selectivity towards adiponitrile (pate 4, last paragraph).
Liu discloses temperature for the electrolytic reduction is 30-70°C (page 3, 2nd paragraph), which overlaps the claimed range of 20-50 degrees Celsius (°C), a current density is 200-5000 A/m2 (page 3, 2nd paragraph), which overlaps the claimed range of 500-5000 amperes per square meter (A/m2).
Liu further teaches that reaction time is calculated according to formula: Reaction time = (2 x acrylonitrile mass x Faraday constant)/(acrylonitrile molar mass x current). Therefore, the Faraday per mole can be calculated and is dependent on reaction time and current applied, as well as number of moles of acrylonitrile.
Liu is silent as to the electric charge is 0.5-0.9 Faraday per mole (F/mol).
Liu does not disclose the easily oxidizable substance selected from the claimed group.
However, Beck teaches it is advantageous to add to the electrolysis mixture a small amount of a substance which is more easily oxidized anodically than the electrolyte salt, acrylonitrile or adiponitrile. Anodic oxidation of the starting material or reaction product which occurs as a secondary reaction and results in loss of yield is suppressed by such an addition. Examples of suitable substances are lower alcohols, particularly methanol, and lower aldehydes (col. 2, lines 29-42).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have the electric charge in the range of 0.5-0.9 Faraday per mol in the method of Liu as modified by Beck, because Liu teaches Faraday per mole can be calculated and is dependent on reaction time and current applied, as well as number of moles of acrylonitrile, Liu however, does not disclose reaction time, necessary for calculating this value, and one of ordinary skill would have known to optimize the reaction time in order to achieve the most complete reaction without significant time penalty. Furthermore, Liu meets the claimed limitations of current density, temperature, concentration and linear velocity, therefore one would expect the value of the electric charge would be also substantially similar.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention that the organic matter in Liu will have hexanetricarbonitrile, because Liu meets all the method steps and compositions of the instant claims, therefore the products would be expected to be the same or inherently be the same. Furthermore, the instant specification discloses that currently, the electrolytic preparation of adiponitrile from acrylonitrile is widely adopted. While producing adiponitrile, this method may also yield hexanetricarbonitrile (instant specification [0005]). Therefore, one would have expected that hexanetricarbonitrile is present in the organic matter other than adiponitrile in Liu.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to add to the electrolysis mixture a small amount of a substance which is more easily oxidized anodically than the electrolyte salt, acrylonitrile or adiponitrile, because Beck teaches anodic oxidation of the starting material or reaction product which occurs as a secondary reaction and results in loss of yield is suppressed by such an addition. Examples of suitable substances are lower alcohols, particularly methanol, and lower aldehydes.
Considering claim 2, Liu discloses a concentration of the supporting electrolyte (phosphate) in the electrolyte solution is 1-20 wt% (page 4, 3rd paragraph), which overlaps the claimed range of 7.5-12.5 percent by weight (wt.%), and the supporting electrolyte comprises a phosphate; a concentration of the electrode protector (borax) in the electrolyte solution is 0.01 to 5 wt% (page 4, 3rd paragraph), which overlaps the claimed range of 1-4 wt.%; a concentration of the complexing agent (EDTA) in the electrolyte solution is 0.1-10 wt%, which overlaps the claimed range of 0.5-1.5 wt.%, and the complexing agent comprises ethylene diamine tetraacetic acid (EDTA) (page 4, 3rd paragraph); and a concentration of the quaternary ammonium salt in the electrolyte solution is 2 wt% (page 4, 3rd paragraph), which is within the claimed range of 0.5-2.5 wt.%.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have the recited range because a prima facie case of obviousness exists in the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art”. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990). Furthermore, "[ A ] prior art reference that discloses a range encompassing a somewhat narrower claimed range is sufficient to establish a prima facie case of obviousness." In re Peterson, 315 F.3d 1325, 1330, 65 USPQ2d 1379, 1382-83 (Fed. Cir. 2003). See MPEP 2144.05.
Considering claim 3, Liu discloses the phosphate comprises sodium dihydrogen phosphate (page 5, Example 1); and the quaternary ammonium salt comprises tetrabutylammonium hydroxide (page 5, Example 1).
Considering claim 4, Liu discloses the concentration of the acrylonitrile in the electrolyte solution is 7 wt% (page 5, Example 1), which is very close to the claimed range of 7.5-15 wt%.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to use slightly more acrylonitrile in the method of Liu, because one would expect similar results, while optimizing the reaction process with the expectation of producing larger quantity of product in a single batch.
Considering claim 5, Liu discloses the concentration of the easily oxidizable (ethylene glycol) substance in the electrolyte solution is 0.1-10 wt% (62 g/mol, d=1g/mL), which corresponds to 0.016-1.6 mol/L, which overlaps the claimed range of 0.1-5.0 moles per liter (mol/L).
Considering claim 7, Liu discloses the cathode is Cd (page 5, Example 1).
Considering claim 8, Liu discloses the linear velocity of the solution is 1.2 m/s (page 5, Example 1).
Response to Arguments
Applicant’s arguments with respect to claim(s) 1-8 have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Conclusion
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 nonprovisional extension fee (37 CFR 1.17(a)) 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 mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Wojciech Haske whose telephone number is (571)272-5666. The examiner can normally be reached M-F: 9:30 am - 6:00 pm.
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/WOJCIECH HASKE/Examiner, Art Unit 1794
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