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 .
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 (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.
Claims 1, 6, 7, and 10–13 is/are rejected under 35 U.S.C. §103 as unpatentable over CN101941890A in view of CN101774893A, CN101885479A, and Wammes and Westerterp (“WAMMES”).
CN101941890A discloses a continuous system and process for producing m-cresol, including continuous salt formation, tubular diazotization, continuous hydrolysis, phase separation, rectification, spent-acid concentration, and recycle. See ¶¶30–36 and 42.
CN101941890A does not expressly use an in-situ-generated N₂O₃ gas stream or a gas-liquid trickle-bed diazotization reactor. CN101774893A supplies the same claimed chemical conversion: m-toluidine is converted to m-toluidine sulfate, diazotized with nitrogen oxides, hydrolyzed in aqueous sulfuric acid and aromatic solvent, phase-separated, rectified, and the acid recovered and reused. CN101774893A ’s Example 1 uses equimolar NO and NO₂, i.e., the stoichiometric gas composition associated with N₂O₃. See CN101774893A ¶¶32–34, 42, 46, 52, and 61.
CN101885479A teaches generating the required N₂O₃-forming gas on demand by mixing NO and O₂. In its example, 80 mL/min NO and 20 mL/min O₂ pass first through the oxidation reactor and then through a fully mixed equilibrium reactor, yielding approximately equimolar NO and NO₂, described as the N₂O₃-equivalent composition, while avoiding N₂O₄. See CN101885479A ¶¶37, 41, 57, and 92–98.
WAMMES establishes that a packed trickle-bed reactor was a conventional gas-liquid contacting configuration and identifies interfacial area, liquid holdup, pressure drop, and maintenance of trickle flow as known design considerations.
A person of ordinary skill would have had reason to implement CN101774893A ’s established NOx-based m-cresol chemistry in CN101941890A’s continuous equipment arrangement, generate CN101774893A ’s required equimolar NO/NO₂ reagent immediately before use through CN101885479A’s staged NO/O₂ mixer, and employ WAMMES’s packed trickle-bed configuration to obtain controlled gas-liquid contact and heat and mass transfer. There would have been a reasonable expectation of success because CN101774893A already consumes the same gas composition produced by CN101885479A, and CN101941890A and CN101774893A use the same starting material, acid system, diazotization/hydrolysis sequence, and product.
If “a set of packed columns” is construed as necessarily requiring more than one column, duplicating the known packed contactor in series or parallel for additional residence time, capacity, or staged temperature control would have been a predictable duplication of a known gas-liquid contacting unit rather than a new functional relationship.
For the additional limitations:
Claim 6: CN101885479A discloses a packed tower 25 mm in diameter and 1000 mm high, giving a diameter-to-height ratio of 1:40, within the claimed 1:60–1:20 range.
Claim 7: CN101885479A expressly mixes NO and O₂ to prepare the N₂O₃-forming gas.
Claim 10: CN101941890A and CN101774893A both disclose rectification/distillation of the cresol-containing organic layer.
Claim 11: The references disclose the corresponding process steps. CN101774893A adds aqueous sulfuric acid and aromatic solvent, including toluene, together before receiving the diazonium stream, satisfying the claimed aqueous/toluene hydrolysis premix under its broadest reasonable interpretation.
Claim 12: CN101885479A discloses gas-generation temperatures of 20–80°C and contact times of 2–18 seconds. Those ranges overlap the claimed 5–25°C and 0.1–15 minutes, because 0.1 minute is six seconds.
Claim 13: CN101885479A’s 80:20 NO:O₂ example is O₂:NO = 1:4, expressly meeting an endpoint of the claimed 1:10–1:4 range.
Overlapping ranges establish a prima facie case where the same variable serves the same purpose and the record contains no showing of criticality or unexpected results. MPEP §2144.05. (uspto.gov)
Claim 2
Claim 2 is/are rejected under §103 over the combination applied to claim 1 further in view of CN110508231A.
CN101774893A expressly cools the m-toluidine sulfate stream to approximately −3 to 5°C before or during diazotization. CN110508231A teaches a jacketed spiral-coil reactor connected to the diazotization feed arrangement. The jacket rapidly removes heat through the coil wall, provides uniform temperature control, and limits diazonium decomposition; its preferred 0–12°C interval overlaps the claimed 5–20°C interval.
It would have been obvious to connect that known jacketed coil to the outlet of the salt-forming reactor and use it to cool and maintain the salt feed entering the packed diazotization contactor. This is the same temperature-control function taught by CN110508231A and addresses the cooling expressly required by CN101774893A .
Claim 3
Claim 3 is/are rejected under §103 over the combination applied to claim 1 further in view of US4845638.
CN101774893A already removes excess nitrous acid using urea. US4845638 teaches a separate continuous removal vessel downstream of a diazotization reactor and controlled addition of sulfamic acid or urea to destroy excess nitrite/nitrous acid in a diazotization solution.
It would have been obvious to implement CN101774893A ’s excess-nitrosating-agent removal as US4845638’s separate continuously controlled removal unit to improve endpoint control and prevent excess nitrosating species from entering hydrolysis.
This ground applies under the reasonable construction that “excess NOx from the diazotization salt” encompasses residual nitrite, nitrous acid, and dissolved reactive nitrogen oxides.
Claim 4
Claim 4 is/are rejected under §103 over the combination applied to claim 1 further in view of Sharma et al.
Sharma continuously feeds a diazonium stream to a CSTR for acidic hydrolysis and explains that the CSTR provides rapid mixing, an independently controllable residence time, gas release, and avoidance of pressure accumulation associated with diazonium decomposition.
A skilled person would have used Sharma’s CSTR as the hydrolysis reactor in the continuous m-cresol train to obtain those expressly identified mixing, residence-time, and gas-handling benefits. The substitution is between known continuous hydrolysis reactors performing the same operation.
Claims 5 and 15
Claims 5 and 15 are rejected under §103 over the combination applied to claims 1 and 11 further in view of US5649322.
US5649322 teaches continuous gas-liquid scrubber columns containing packings of all types and expressly identifies arranged or structured packing. CN101885479A discloses different packing types and specifically uses porcelain Raschig rings, a conventional random packing.
It would have been obvious to select structured or random packing for the respective packed contacting sections based on known pressure-drop, wetting, interfacial-area, and fouling considerations. The claimed selection produces the expected contacting function of those known packing classes.
Claim 8
Claim 8 is/are rejected under §103 over the combination applied to claim 3 further in view of US5649322.
For examination only, claim 8 is provisionally construed consistently with claim 13 and the specification as encompassing an O₂:NO ratio from approximately 0.10 to 0.25—i.e., from 0.6:6 to 1:4.
US5649322 teaches approximately 0.15–0.30 mole O₂ per mole of excess NO, overlapping that provisional range. CN101885479A’s 20:80 O₂:NO example is exactly 0.25 or 1:4. The O₂:NO ratio is taught as controlling oxidation of NO, the NO:NO₂ equilibrium, N₂O₃ production, and unwanted N₂O₄ formation. Selection within the overlapping range therefore would have been routine optimization of an expressly result-effective variable.
Claim 9
Claim 9 is/are rejected under §103 over the combination applied to claim 1 further in view of US20160318853A1.
CN101941890A and CN101774893A already recover and recycle sulfuric acid. US20160318853A1 reports seven successive diazotization/hydrolysis cycles using recovered sulfuric acid while maintaining commercially useful yield and purity. See ¶¶404–415.
It would have been obvious to configure and operate the known acid-recovery unit for at least six cycles because the reference expressly demonstrates that seven cycles are practicable and reduce fresh-acid consumption and waste without unacceptable loss of process performance.
Claim 14
Claim 14 is/are rejected under §103 over the combination applied to claim 11 further in view of Yu et al. and US4717514.
CN101774893A establishes formation of the required m-toluidine sulfate salt. US4717514 teaches contacting/dissolving toluidine in 1.5–10 moles of sulfuric acid per mole of toluidine, encompassing three to six moles; sulfuric acid containing up to 8% water, encompassing 98%; and a 10–55°C range, preferably beginning at 15°C, overlapping 15–20°C. Yu expressly uses one mole of toluidine with three moles of 98% sulfuric acid and operates the resulting sulfate-containing process stream at 20°C.
A person of ordinary skill would have applied those known acid-strength, stoichiometric, and temperature conditions to CN101774893A ’s m-toluidine salt preparation to control acid-base heat release, viscosity, salt dissolution, and suitability of the feed for low-temperature diazotization. CN101774893A supplies the meta isomer; Yu and US4717514 are relied upon for the process conditions rather than for substitution of the para isomer.
Claim 16
As written, claim 16 is rejected under §103 over the combination applied to claim 9 further in view of CN1515531A and EP0653236A1.
CN1515531A discloses the same m-toluidine-to-m-cresol chemistry and removes excess nitrite from the low-temperature diazonium stream with sulfamic acid. EP0653236A1 teaches a one- or multistage countercurrent reaction column and a combined embodiment in which NOx-containing gas is treated with aqueous sulfamic acid after oxygen addition. It permits operation from 0–100°C, overlapping the claimed 0–5°C interval, and identifies diazotization exhaust as a suitable source.
CN101774893A carries out diazotization and excess-reagent removal at −3 to 5°C, providing the claimed 0–5°C operating interval. CN101885479A teaches that excess NO₂ establishes N₂O₄ and that controlling the NO/NO₂ equilibrium reduces or eliminates N₂O₄.
It would have been obvious to replace CN101774893A ’s urea treatment with the known sulfamic-acid treatment, to use EP0653236A1’s gas-liquid removal column for gaseous excess NOx, and retain the low temperature already used for the diazonium stream. Removing excess NO₂/nitrous species reduces the concentration available for NO₂ dimerization and would predictably suppress N₂O₄ formation. Thus, the “thereby suppressing” limitation is supported by an articulated equilibrium-based expectation, not solely by an unsupported inherency assertion.
Claim Rejections - 35 USC § 112
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.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 8 and 16 rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 8
The limitation “a ratio of flow rate of NO with oxygen is 0.6–1:4–6” does not define the ratio with reasonable certainty. It fails to identify:
Which numerical interval corresponds to NO and which corresponds to oxygen;
Whether the endpoints are paired as 0.6:4 and 1:6, or as 0.6:6 and 1:4;
Whether the intended ratio is NO:O₂ or O₂:NO; and
Whether “flow rate” means molar, mass, or volumetric flow and, if volumetric, whether the gases are measured under common temperature and pressure conditions.
The specification does not cure the ambiguity. It variously describes NO:oxygen as 7:1–4:1 with a preferred 6:1 ratio, O₂:NO as 1:10–1:4, and repeats the ambiguous “0.6–1:4–6” notation.
Accordingly, a person of ordinary skill cannot determine the metes and bounds of claim 8 with reasonable certainty.
Claim 16
Claim 16 begins “[t]he process … as claimed in claim 9,” but claim 9 is directed to a system. It is therefore unclear whether claim 16 covers:
A process using the system of claim 9;
A system configured to perform the stated process; or
A process intended to depend from process claim 11.
In addition, claim 16 recites “the excess NOx removal unit (105)” without antecedent basis. Claim 9 depends from claim 1, and neither claim 1 nor claim 9 introduces that unit. The unit appears in claim 3, which claim 16 does not incorporate.
The phrase “incorporating sulfamic acid to the excess NOx removal unit” also fails to state clearly whether sulfamic acid is fed into the unit, added to the diazonium stream within the unit, or incorporated structurally into the unit. These defects prevent a skilled reader from determining the statutory category and boundaries of the claim with reasonable certainty.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 16 rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Claim 16 refers to claim 9 but does not specify a further limitation of the subject matter of claim 9. Claim 9 is a system claim. Claim 16 instead identifies itself as “the process” and recites process steps without stating that the steps constitute a method of making or using the system of claim 9 and without clearly incorporating all limitations of that system.
A claim in a different statutory class can sometimes properly refer to another claim—for example, “a method of operating the system of claim 9”—if it incorporates all limitations and then adds a further limitation. The present claim lacks that relationship.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DEBORAH D CARR whose telephone number is (571)272-0637. The examiner can normally be reached Monday-Friday (10:30 am -6:30 pm).
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Renee Claytor can be reached at 572-272-8394. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/DEBORAH D CARR/ Primary Examiner, Art Unit 1691
