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 .
Current Status of 18/063,841
This Office action is responsive to the Applicant remarks and amended claims of 11/20/2025. Claims 1-21 are pending and have been examined on the merits.
Priority
The instant application claims priority to U.S. Provisional Application No. 63/288,451, filed 12/10/2021.
Response to Amendment
Applicants assert that Scavuzzo does not teach or suggest use of a glycerol solution for the nitration reaction. In support, Applicants rely on the affidavit of Dr. Brisbane, which alleges that addition of water would significantly reduce the nitrating power of nitric acid in the synthesis of DNG. Applicants further contend that the secondary references cited in the rejection do not teach or suggest reacting and aqueous glycerol solution with nitric acid in a microfluidic reactor to ultimately produce glycidyl nitrate. These arguments have been fully considered but are not persuasive.
Applicants argue that Liu does not describe reaction methods and therefore fails to teach the glycerol solution of the instant claims. While Liu does not disclose nitration chemistry, it was not cited for that purpose. Rather, Liu was cited for its teaching that mixing of viscous fluids in microfluidic systems presents a known challenge due to laminar flow conditions associated with low Reynolds numbers (see Stroock, Abraham D., et al. "Chaotic mixer for microchannels." Science 295.5555 (2002): 647-651.; Wang, Shasha, Xiaoyang Huang, and Chun Yang. "Mixing enhancement for high viscous fluids in a microfluidic chamber." Lab on a Chip 11.12 (2011): 2081-2087.; and Lee, Chia-Yen et al. “Microfluidic mixing: a review.” International journal of molecular sciences vol. 12,5 (2011): 3263-87. doi:10.3390/ijms12053263 for reference). As recognized in the art, viscous liquids such as glycerol are particularly difficult to mix efficiently in microreactors because mixing is dominated by molecular diffusion under laminar flow. Liu teaches that dilution of glycerol with water reduces viscosity and measurably improves mixing performance. Thus, Liu provides an express solution to a well-recognized problem in microfluidic chemistry, inadequate mixing of viscous reagents. Applying this known mixing strategy to a microfluidic nitration reaction comprising glycerol would have been an obvious design choice to improve reaction performance.
Applicants also argue that Braune teaches formation of a mononitrate ester from a glycol and does not teach production of glycidyl nitrate, and therefore would not have motivated the artisan to employ aqueous nitration conditions for glycidyl nitrate synthesis. This argument is not persuasive because it conflates the nitration step with the subsequent cyclization step. [0016], [0033], [0041], and [0046] of the instant specification make clear that nitration of glycerol is a discrete step that precedes base-mediated cyclization to form the epoxide. The structural characteristics of glycidyl nitrate are therefore irrelevant to whether the initial nitration of a glycol can proceed in the presence of water. Braune teaches that nitration of glycol under aqueous conditions is feasible. Accordingly, Braune directly rebuts the assertion that the artisan would have expected aqueous conditions to render nitration inoperable.
Scavuzzo already teaches performing the same two-step reaction in a microfluidic reaction but does not disclose predilution of glycerol with water. Liu teaches that dilution of viscous glycerol with water improves mixing in microfluidic systems, addressing a known limitation of such reactors. Braune teaches that glycol nitration remains operable under aqueous conditions. In view of these teachings, pre-diluting glycerol with water prior to nitration represents the predictable application of known techniques to a known process, yielding no more than expected results. The combination therefore amounts to the use of known elements according to their established functions to solve a recognized problem, which supports the conclusions of obviousness.
The other arguments presented by the Applicants take the same position that the combination of the references above do not teach the glycerol solution. These arguments are unpersuasive for the reasons discussed above.
Claim Rejections - 35 USC § 103 (Maintained)
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.
Claims 1-3 and 21 are rejected under 35 U.S.C. 103 as being unpatentable over Scavuzzo (US 10,562,873, found in IDS filed 12/09/2022) in view of Braune (US 8,536,366 B2, found in IDS filed 12/09/2022) and Liu (Liu, Ying Zheng, Byoung Jae Kim, and Hyung Jin Sung. "Two-fluid mixing in a microchannel." International journal of heat and fluid flow 25.6 (2004): 986-995.).
Determining the scope of the prior art:
Scavuzzo teaches:
A method of producing glycidyl nitrate. The method comprises reacting glycerol and nitric acid in a microfluidic reactor to form a nitrated glycerol compound (Col 1, lines 47-48)
Reacting the nitrated glycerol compound with a base in the microfluidic reactor to form glycidyl nitrate (claim 1)
Braune teaches:
•The reaction of monohydric and polyhydric alcohols with nitrating agents such as nitric acid or nitrating acid gives the corresponding nitrate esters, e.g. glyceryl trinitrate from glycerin (Col 1, lines 12-15)
• The reactive alcohols are compounds of Formula (I) (Col 2, lines 40-41)
• The compound of Formula (I) is preferably 1,3-propanediol or 1,4-butanediol. The reaction of the compound of formula (I) with nitric acid occurs in a first solvent. The first solvent is typically hydrophilic, and is preferably water. (Col 5, lines 37-41), reading on instant claims 1 and 2
Liu teaches:
The mixing of pure water with a solution of glycerol in water was investigated for three different mass fractions of glycerol (φ= 0, 0.2, 0.4). These fluids were chosen to test the mixing behavior of fluids with different properties and a large concentration gradient. At Re=1, the mixing performance of both mixers varied inversely with the mass fraction of glycerol due to the dominance of molecular diffusion. (Conclusion, pg. 994), provides motivation for claims 1-3 and 21
Ascertaining the differences between the prior art and the claims at issue:
Scavuzzo does not teach a glycerol solution, including an aqueous glycerol solution nor does the reference specify a specific viscosity at a given temperature of for a glycerol solution. The reference does not teach a range of aqueous glycerol solutions comprising from about 30% by weight glycerol to about 90% by weight glycerol.
Braune does not teach a glycerol solution, an aqueous glycerol solution, nor does it teach a specific viscosity of glycerol solutions or provide information regarding the percentage by weight of glycerol in said solutions.
Liu does not teach the claimed reaction process.
Resolving the level of ordinary skill in the pertinent art:
Those of relevant skill in the art are those with the level of skill of the inventors of the references cited to support the Examiner’s positions.
Considering objective evidence present in the application indicating obviousness or nonobviousness:
The artisan would have been motivated to modify the process of Scavuzzo by pre-diluting the glycerol with water to a specified viscosity before contact with nitric acid. Braune teaches that nitrate-ester formation in microreactors is feasible in the presence of water, alleviating the concern that water would quench the nitration agent in a microfluidic reactor. The artisan would expect that dilution of glycerol with water (reducing viscosity) would predictably improve the mixing of the two components and improve the reaction yield. Selecting a specific viscosity at about 20°C is therefore a results-effective set-point obtainable through routine optimization. Applicants have provided no evidence of criticality for the claimed viscosity or temperature, rendering the choice an optimization of known variables.
Claims 1 and 4-7 are rejected under 35 U.S.C. 103 as being unpatentable over Scavuzzo, Braune, Liu in view of Raston (Britton, Joshua, and Colin L. Raston. "Multi-step continuous-flow synthesis." Chemical Society Reviews 46.5 (2017): 1250-1271.).
Determining the scope of the prior art:
The teachings of Scavuzzo, Braune, and Liu are discussed above and are incorporated by reference into this rejection. These references teach the limitations of instant claim 1.
Braune additionally teaches:
The extraction of a nitrate ester from acidic esterification conditions with high selectivity and high yield (Col 7, lines 45-53)
Extraction of the nitrated ester from the acidic esterification conditions comprises a two-phase solvent system with the first solvent being a hydrophilic solvent, preferably water (Col. 5, lines 39-41) and the second solvent being typically a hydrophobic solvent. Suitable second solvents are organic solvents in which the nitrated ester has high solubility and which is inert under reaction conditions. Preferred second solvents are halogenated hydrocarbons such as dichloromethane and tetrachloroethane (Col. 5, lines 45-53), reading on instant claims 4-7.
Raston teaches:
The purification of intermediate compound of multi-step transformations in continuous-flow synthesis is vital to increase reaction yields and efficiencies (Key learning points, pg. 1), reading on instant claims 4-7.
Ascertaining the differences between the prior art and the claims at issue:
Scavuzzo and Liu do not teach the extraction of excess nitric acid from the dinitroglycerol solution, recovering the dinitroglycerol solution into and organic solvent before reacting the dinitroglycerol with the base, and extracting the dinitroglycerol into dichloromethane before reacting the dinitroglycerol with the base.
Raston does not teach the claimed chemical reaction.
Braune does not teach a glycerol solution, an aqueous glycerol solution, nor does it teach a specific viscosity of glycerol solutions or provide information regarding the percentage by weight of glycerol in said solutions.
Resolving the level of ordinary skill in the pertinent art:
Those of relevant skill in the art are those with the level of skill of the inventors of the references cited to support the Examiner’s positions.
Considering objective evidence present in the application indicating obviousness or nonobviousness:
The artisan would have been motivated to separate the nitrated ester intermediate from the acidic esterification conditions before the subsequent base-mediated step to avoid acid carryover that would consume and dilute the effective base concentration and potentially promote side-reactions or decomposition under the mixed acid base conditions. This addresses base neutralization and mixed acid/base side-reactions, known causes of yield loss and instability. The references discussed above are in the same technical field and address the same process problem, acid carryover into a subsequent base-mediated step, in the same technical context, nitrate-ester formation under acidic conditions followed by a downstream base mediated transformation. They address the same purpose in the same field, supporting combination under Deere. Raston provides the motivation for why the artisan would purify reaction intermediates in continuous-flow processes. The artisan would expect that purification/separation of reaction intermediates would improve the yield and efficiency of the reaction. Braune teaches a ready, field-tested solution tailored to nitrate ester formation under acidic conditions. The solution comprises a two-phase extraction that selectively partitions the nitrate ester into an immiscible, acid-stable organic phase, enabling removal of the acidic aqueous phase. The artisan would combine Raston’s sequencing rationale with Braune’s extraction protocol to remove residual acid before base addition, with a reasonable expectation of success and a predictable improvement in outcomes. The artisan would expect that this process would provide improvements to yield and efficiency of the process.
Claims 1 and 8 are rejected under 35 U.S.C. 103 as being unpatentable over Scavuzzo, Braune, and Liu in view of Highsmith ‘311 (U.S. 6,362,311, found in IDS filed 12/09/2022).
Determining the scope of the prior art:
The teachings of Scavuzzo, Braune, and Liu are discussed above and are incorporated by reference into this rejection. These references teach the limitations of instant claim 1.
Highsmith ‘311 teaches:
The cyclization of dinitroglycerin into glycidyl nitrate is performed in the presence of an inorganic hydroxide, including alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, and lithium hydroxide (Col 3, lines 48-51)
Ascertaining the differences between the prior art and the claims at issue:
Scavuzzo, Braune, and Liu do not explicitly teach the use of potassium hydroxide (KOH).
Highsmith ‘311 does not teach all elements of the claimed chemical reactions.
Resolving the level of ordinary skill in the pertinent art:
Those of relevant skill in the art are those with the level of skill of the inventors of the references cited to support the Examiner’s positions.
Considering objective evidence present in the application indicating obviousness or nonobviousness:
The artisan would have been motivated to use potassium hydroxide (KOH) as the base in Scavuzzo’s base mediated cyclization step because both Scavuzzo and Highsmith ‘311 address the same purpose in the same field, conversion of nitrated glycerol intermediates to glycidyl nitrate, and Highsmith ‘311 explicitly identifies inorganic hydroxides (including KOH) as suitable for the same cyclization. Substituting KOH into Scavuzzo’s process is a known substitution of one base for another to perform the same function, with predictable results and a reasonable expectation of success. The artisan would reasonably expect that the substitution of a generic base for KOH would result in the formation of the desired glycidyl nitrate.
Claims 1 and 9-10 are rejected under 35 U.S.C. 103 as being unpatentable over Scavuzzo, Braune, and Liu.
Determining the scope of the prior art:
The teachings of Scavuzzo, Braune, and Liu are discussed above and are incorporated by reference into this rejection. These references teach the limitations of instant claim 1.
Scavuzzo additionally teaches:
‘reaction solution’ means and includes a combination of reagents (e.g., the glycerol and nitrating agent, the nitrated glycerol compound and base) in an optional solvent (Col 3, lines 48-51), reading on instant claims 9 and 10.
The nitric acid used as a nitrating agent may be concentrated nitric acid (98%) or a nitric acid solution. The nitric acid solution includes the nitric acid and a solvent, such as dichloromethane. A ratio of the solvent to the nitric acid (solvent:nitric acid may range from about 0.1:1 to about 1:1 (Col 5, lines 11-16), reading on instant claims 9 and 10.
Ascertaining the differences between the prior art and the claims at issue:
The combined teachings of the references listed above in section 1 teach all the limitations of instant claim 1. The teachings of Scavuzzo discussed above regarding the allowed ratios of solvent to nitric acid ratios are identical to those claimed in the instant application.
Resolving the level of ordinary skill in the pertinent art:
Those of relevant skill in the art are those with the level of skill of the inventors of the references cited to support the Examiner’s positions.
Considering objective evidence present in the application indicating obviousness or nonobviousness:
Scavuzzo teaches a nitric acid solution comprising nitric acid and a solvent comprising water or DCM and discloses solvent:nitric acid ratios that encompasses/overlaps the claimed range; accordingly, a prima facie case of obviousness is established. 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). Note MPEP 2144.05.
Claims 11-14 are rejected under 35 U.S.C. 103 as being unpatentable over Scavuzzo, Braune, Liu and Highsmith ‘311.
Determining the scope of the prior art:
The combined teachings of Scavuzzo, Braune, and Liu are discussed above and teach the method of producing glycidyl nitrate comprising reacting a glycerol solution and nitric acid in a microfluidic reactor and reacting the dinitroglycerol solution with a base in the microfluidic reactor to form glycidyl nitrate. The teachings of Highsmith ‘311 are also discussed above and teach KOH as the base used in the cyclization reaction. These teachings are incorporated by reference into this rejection.
Scavuzzo teaches:
Glycerol and nitric acid may be reacted at a temperature ranging from about 15°C to about 30°C (Col 5, lines 55-56), reading on instant claim 11
The dinitroglycerol compound and base may be reacted in the microfluidic reactor at a temperature of from about 10°C to about 35 °C, reading on instant claim 11
The base may include, but is not limited to, sodium hydroxide, and a concentration of the sodium hydroxide may range from about 3.0M to about 10.0 M (Col 6, lines 59-67)
Sodium hydroxide may be an aqueous solution of sodium hydroxide. In some embodiments, the concentration of sodium hydroxide in the aqueous solution of sodium hydroxide is about 7.2 M (Col 6, line 63-67), reading on instant claim 12
Controlling the temperature of the nitration reaction, the DNG compound may be produced at a higher purity by deacresing the side reactions that produce the MNG compound of NG (Col 5, lines 60-67).
The nitrating agent may be concentrated nitric acid or a nitric acid solution. The nitric acid solution includes nitric acid and a solvent. The ration of the solvent to the nitric acid may range from 0.1:1 to 1:1 (solvent: nitric acid) (Col 5, lines 11-20)
Ascertaining the differences between the prior art and the claims at issue:
Scavuzzo does not explicitly disclose KOH as a suitable base for the cyclization reaction nor does it disclose the cyclization reaction temperature range of 50°C to 60°C.
Resolving the level of ordinary skill in the pertinent art:
Those of relevant skill in the art are those with the level of skill of the inventors of the references cited to support the Examiner’s positions.
Considering objective evidence present in the application indicating obviousness or nonobviousness:
It has been previously shown that the combined teachings of the references Scavuzzo, Braune, and Liu teach a method of producing glycidyl nitrate comprising reacting an aqueous glycerol solution in a microfluidic reactor and reacting the dinitroglycerol solution with a base in a microfluidic reactor to form glycidyl nitrate. It has been shown that the viscosity of the glycerol at a specific temperature is a result-effective variable obtainable through routine optimization. The references also teach the viscosity limitations imposed by instant claim 13. The temperature ranges of about 15°C to about 55°C for the initial reaction and about 20°C to about 60°C for the subsequent reaction of instant claim 11 are disclosed by Scavuzzo. The temperature ranges encompass/overlap with the claimed ranges of instant claim 11; accordingly, a prima facie case of obviousness is established. 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). Note MPEP 2144.05. This makes obvious the limitations of instant claims 11 and 13.
Highsmith ‘311 teaches that KOH is a suitable inorganic hydroxide in the cyclization reaction for the formation of glycidyl nitrate. Scavuzzo teaches that the range of concentrations of the aqueous solution of NaOH (an equivalent inorganic hydroxide) is from 3.0-10.0 M and specifically states that in some embodiments the concentration is 7.2 M. Highsmith ‘311 explicitly identifies KOH for the same cyclization; substituting KOH into Scavuzzo’s base step is a known substitution among inorganic hydroxides to perform the same function with predictable results. And because Scavuzzo teaches aqueous NaOH at the concentration range disclosed above, specifying a concentration of 7.2 M KOH is an analogous concentration choice. This makes obvious the limitations of instant claim 12.
All claim elements of instant claim 14 have been made obvious with the exception of the temperature range of about 50°C to about 60°C for the base mediated cyclization reaction. Temperature is an optimizable, results-effective variable. The art teaches controlling temperature to manage purity and side reactions in these microreactors. The artisan would routinely adjust temperature to achieve the desired balance. Selecting about 50-60°C, although outside Scavuzzo’s disclosed range, represents routine optimization of a results-effective variable from a closely adjacent range, with a predictable expectation of achieving the same transformation. See MPEP §2144.05. This makes obvious the limitations of instant claim 14.
Claims 15-20 are rejected under 35 U.S.C. 103 as being unpatentable over Scavuzzo, Braune, Liu, Raston, and Highsmith ‘311 in view of Highsmith ‘061 (U.S. 6,870,061 B2, found in IDS submitted 12/09/2022) and von Rohr (Assmann, Nora, Agnieszka Ładosz, and Philipp Rudolf von Rohr. "Continuous micro liquid‐liquid extraction." Chemical Engineering & Technology 36.6 (2013): 921-936.).
Determining the scope of the prior art:
The teachings of Scavuzzo, Braune, Liu, Raston, and Highsmith ‘311 are discussed above and are incorporated by reference into this rejection.
Scavuzzo additionally teaches:
The nitration reaction and the intramolecular ring closure reaction are conducted in a microfluidic reactor that includes pumps (col 8, lines 1-3).
The pumps 10 are configured to introduce the reagents into the microfluidic reactor 5 at a desired flow rate, such as at a constant flow rate. Pumps 10 of varying sizes may be used to achieve the desired flow rate and reagent feed ratio. The glycerol and nitric acid are introduced into the microfluidic reactor 5 through inlets (not shown) and combined with mixing in the first reaction channel 20. The sodium hydroxide is introduced into the microfluidic reactor 5 through an inlet (not shown) and combined with the DNG compound in the second reaction channel 20. The reaction of the glycerol and nitric acid and the DNG compound and sodium hydroxide is based on the flow rate of the reagents through the microfluidic reactor 5 and the length of the first and second reaction channels 20. The flow rate of each of the reagents may be the same or may be different. Alternatively, the desired reagent feed ratio of each of the reagents may be achieved by dilution. Depending on the amount of GLYN to be produced, the pumps 10 may be syringe pumps or other conventional pumps (Col 8, lines 33-51)
The microfluidic reactor may include one or more reaction channels configured to react the reagents (e.g., glycerol and nitric acid, DNG compound and base) to form the GLYN (Col 9, lines 4-6)
The reaction volume of the microfluidic reactor comprising less than about 20 mL and an inner diameter of a reaction channel of the microfluidic reactor of less than or equal to about 1000 um (Col 15, lines 53-57), reading on instant claim 20
Highsmith ‘061 teaches:
A second product stream 107 leaving the second reaction vessel 125 is optionally combined with a second solvent stream 108 of DCM to form product stream 109, which is fed to the separation apparatus 130 for separating glycidyl nitrate from the second product stream 107 (Col 6, lines 65-68, Col 7, lines 1-2)
Von Rohr teaches:
The use of liquid:liquid phase extraction in microfluidics for chemical reactions during screening of a reaction or even during production (Introduction)
A stationary organic extractant phase is contacted with a usually aqueous moving sample (Introduction).
Ascertaining the differences between the prior art and the claims at issue:
Scavuzzo does not teach:
Inlets configured to introduce diluted glycerol, KOH, and DCM
The use of liquid:liquid phase separators for the removal of nitric acid from the dinitroglycerol solution and the recovery of glycidyl nitrate
The use of potassium hydroxide and the separate introduction of DCM
Resolving the level of ordinary skill in the pertinent art:
Those of relevant skill in the art are those with the level of skill of the inventors of the references cited to support the Examiner’s positions.
Considering objective evidence present in the application indicating obviousness or nonobviousness:
It would have been obvious to the artisan to configure the microfluidic system of Scavuzzo to include one or more dedicated inlets for each reactant, meter those reactants with separate pumps, incorporate one or more liquid-liquid phase separators to continuously remove intermediate and final product streams, route the two process steps through separate microchannels, and select a reactor volume with the same reactor volume and inner diameter of the reaction channel. Scavuzzo teaches dedicated inlets and independent pumps for controlled addition; applying the same protocol to all required reagents is a routine use of a known element for its known function (stoichiometry and residence-time control). Highsmith ‘061 teaches conducting the cyclization in the presence of DCM to enable organic/aqueous phase separation of glycidyl nitrate from basic aqueous media; implementing Highsmith ‘061’s protocol in a continuous flow variant would have motivated the artisan to incorporate liquid:liquid separator modules and separate channels to isolate the acidic first step from the basic second step and prevent back mixing. Selecting the same inner diameter and a reactor volume overlapping in range with Scavuzzo’s disclosure reflects optimization of results-effective variable (e.g., Reynolds number, interfacial area, heat/mass-transfer coefficients, etc.) to obtain the same performance, absent evidence of criticality. Matching Scavuzzo’s dimensions is a design choice that predictably preserves the disclosed regimes. Combining these well-known modules according to their established functions yields no more than predictable benefits of continuous processing, such as stable metering of reactant/reagents, tunable residence times, and efficient phase management, with a reasonable expectation of success.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-10 and 21 are rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1 of U.S. Patent No. 10,562,873 in view of Scavuzzo, Braune, Liu, Raston, and Highsmith ‘311.
Claims 1-10 and 21 of the instant application are not patentably distinct from claim 1 of ‘873. Claim 1 of ‘873 discloses the same two-step microfluidic process; the instant claims merely add (1) use of a glycerol solution, (2) extracting the nitrate-ester intermediate from the acidic solution before the subsequent base step, (3) substituting KOH for NaOH, and (4) specifying a dilution range for the nitric acid solution. Each of these differences is an obvious variant in the same field and for the same purpose: (1) selecting an aqueous glycerol solution to achieve a desired viscosity in flow chemistry is routine optimization of a results-effective variable (per the teachings of Braune and Liu, see above); (2) separating residual acid from the nitrated ester prior to base addition is a conventional step that predictably reduces base neutralization and side reactions (per the teachings of Raston), (3) replacing NaOH with KOH is a known substitution among inorganic hydroxides to perform the same cyclization with predictable results and a reasonable expectation of success (see Highsmith ‘311), and (4) choosing a nitric acid dilution range is merely selection/optimization of concentration, and approaching/overlapping range on a results-effective parameter (see Scavuzzo) that would be routinely adjusted in microreactors. These rationale are consistent with the teachings and motivations described in the 103 rejections above and are incorporated by reference into this rejection for completeness.
Claims 11-14 are rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1 of U.S. Patent No. 10,562,873 in view of Scavuzzo, Braune, Liu and Highsmith ‘311.
Claims 11-14 of the instant application are not patentably distinct from claim 1 of ‘873. Claim 1 of ‘873 recites the same two-step microfluidic process. The additional limitations in the instant claims are as follows: (1) specifying nitration temperatures and cyclization temperatures, (2) substituting KOH for the base used in the cyclization reaction, (3) specifying the concentration of the base solution used in the reaction, and (4) specifying a viscosity and a specified temperature for the glycerol solution. These additional limitations are not sufficient to distinguish the instant application’s claims from ‘873. Temperature, viscosity, and base concentrations are results-effective process variables that the artisan routinely optimizes in microreactors to balance heat removal, and mixing. Selecting overlapping or closely adjacent temperature ranges is a predictable optimization with a reasonable expectation of success. Similarly, replacing NaOH or an unspecified base with KOH is a known substitution among inorganic hydroxides to perform the same cyclization reaction with predictable results. These rationale are consistent with the teachings and motivations described in the 103 rejections above and are incorporated by reference into this rejection for completeness.
Claims 15-20 are rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1 of U.S. Patent No. 10,562,873 in view of Scavuzzo, Braune, Liu, Raston, Highsmith ‘311, Highsmith ‘061, and von Rohr.
Claims 15-20 of the instant application are not patentably distinct from claim 1 of ‘873. ‘873 claim 1 already claims the same two-step microfluidic process. Instant claims 15-20 merely recited a system configures to carry out that method, specifying: (1) a microreactor with separate inlets for an aqueous glycerol feed, nitric acid, a base, and an organic solvent, (2) liquid-liquid phase separators to remove residual acid and recover glycidyl nitration, (3) pumps for reagent/solvent streams, (4) explicit first and second reaction channels corresponding to the nitration and cyclization steps, and (5) microreactor geometry. Each of these is a conventional, predictable engineering implementation of the same process: providing dedicated inlets and pumps, channelizing sequential steps, and adding in line liquid:liquid separators are known to address recognized issues with a reasonable expectation of success. Selection of channel inner diameter and volumes reflet routine choice from a finite predictable set. The difference in the statutory of the instant claims relative to the reference claim does not render the claims patentably distinct as the apparatus is merely an obvious apparatus to practice the same method. These rationale are consistent with the teachings and motivations described in the 103 rejections above and are incorporated by reference into this rejection for completeness.
Conclusion
No claims are allowed.
THIS ACTION IS MADE FINAL. 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 CONNOR KENNEDY ENGLISH whose telephone number is (571)270-0813. The examiner can normally be reached Monday Friday, 8 a.m. 5 p.m. ET..
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/C.K.E./Examiner, Art Unit 1625 /Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625