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
Filing Receipt and Priority
The filing receipt mailed 12/07/2023 states that the instant application is a continuation of PCT/CN2021/097009 filed 05/28/2021.
A certified copy of the PCT document has not been submitted with this disclosure. Support for the instant claims in the PCT document cannot be verified. The effective filing date is therefore 11/24/2023.
Information Disclosure Statement
The information disclosure statement submitted 05/09/2024 has been considered. The following NPL submissions have not been considered for the following reasons.
NPL entry 2 to a Duan et al. has not been considered because of an incorrect date.
NPL entry 3 to a Ma, has not been considered because the document is illegible. Examiner requests a legible copy.
Rejections
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.
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.
Claim 2-3, 5, and 6-9 is 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 2 states “SO42-/MxOy”. The claim only states that “M represents a metal atom”. “x” and “y” are not defined by the claim or the specification.
Additionally, the use of the virgule (“/”, forward slash) is typically reserved to denote a ratio of one component to another. Currently, “SO42-/MxOy” is not defined by the specification and the broadest reasonable interpretation would include a ratio of “SO42-“ to “MxOy”. While the art describes superacidic metal oxide catalysts (discussion below), the instant specification and claim does not make this distinction clear and the current claim language includes possible compositions of sulfate “SO42-“ ions to metal oxides “MxOy” that are not defined by the instant specification. Therefore, one of ordinary skill in the art would not know the metes and bounds of the claims.
For similar reasons, claim 3 is also rejected.
Claims 6-8 state “more preferably” (claim 6) and “preferably” (claims 7 and 8) after claiming a broader range. A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
Claim 5 states “the mass concentration of ethanol in the ethanol aqueous solution is 30-65%”. There is insufficient antecedent basis for “the mass concentration” within the claims. However, applicant may amend the claim to state “wherein ethanol in the ethanol aqueous solution is 30%-65% based on a mass concentration.”
Claims 7-8 also state “the molar ratio” (claims 7-8). There is insufficient antecedent basis for this within the claims. Regarding claim 7, Applicant may amend the claim to state “wherein the amount of the sulfamic acid to the amount of the sulfuric trioxide is 4-8:1 molar ratio”. Similar language can be used in claim 8.
Claim 9 states “the reactor”. There is insufficient antecedent basis for this limitation in the claims.
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.
KSR Rationales
The MPEP in section 2143, subsection I gives examples of Rationales for supporting a conclusion of obvious. These rationales are non-exhaustive and include (A) Combining prior art elements according to known methods to yield predictable results; (B) Simple substitution of one known element for another to obtain predictable results; (C) Use of known technique to improve similar devices (methods, or products) in the same way; (D) Applying a known technique to a known device (method, or product) ready for improvement to yield predictable results; (E) “Obvious to try” – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success; (F) Known work in one field of endeavor may prompt variations of it for use in either the same field or a different one based on design incentives or other market forces if the variations are predictable to one of ordinary skill in the art; (G) Some teaching, suggestion, or motivation in the prior art that would have led one of ordinary skill to modify the prior art reference or to combine prior art reference teachings to arrive at the claimed invention.
Claim(s) 1-10 is/are rejected under 35 U.S.C. 103 as being unpatentable over Jiu (CN111377882, effective filing date 2018-12-30, machine translation provided, citations made to machine translation) in view of Arata (Green Chem., 2009, 11, 1719-1728), and Bender (The Kinetics of Simultaneous Hydrolysis and Alcoholysis of Esters and Aqueous Alcohol Solutions, 10/11/1958).
Claim 1 is drawn to a process for preparing acesulfame potassium involving i) an intermediate preparation step, ii) a sulfonation cyclization step, iii) a hydrolysis step, and v) a salt forming step. The intermediate step involves adding triethylamine to a sulfamic acid solution and carrying out an amination reaction to produce an ammonium sulfamate solution, adding diketene, and then carrying out an acylation reaction under the addition of a solid superacid catalyst to obtain said intermediate solution. The sulfonization step involves dissolving sulfur trioxide in a solvent to form a cyclizing agent solution and then adding the sulfonization solution to the intermediate solution. The hydrolysis step involves adding a hydrolysis agent to cyclized product solution. The salt forming step involves adding potassium hydroxide to obtain acesulfame potassium.
Dependent claims 2 and 3 specify a solid superacid catalyst which are SO42-/MxOy (claim 2) and SO42-/Fe2O3 (claim 3).
Claim 4 specifies deionized water or aqueous ethanol as hydrolysis agents.
Claim 5 specifies aqueous ethanol as the hydrolysis agent.
Claim 6 specifies reaction conditions for the hydrolysis reaction which are a temperature of 0 to 20o C and a reaction time of 30-400 s.
Claim 7 specifies molar ratios of sulfamic acid to sulfur trioxide, 4-8:1, and a solvent which is dichloromethane.
Claim 8 specifies the molar ratio of sulfur trioxide to water content in the hydrolysis agent as 1: 1-4.
Claim 9 specifies steps to generate an intermediate solution. Shown below.
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Claim 10 specifies that the method is carried out in a continuous reactor.
Jiu describes a method of synthesizing acesulfame potassium in a continuous process via micro mixer (abstract). Jiu on p. 6, para. [0008] states “Aminosulfonic acid-sulfur trioxide method: aminosulfonic acid is used as raw material and reacted with diketene in the presence of triethylamine to generate triethylamine salt of acetyl acetamide sulfonate.” Jiu in para. [0009] continues “…Method (3) uses industrially available aminosulfonic acid, diketene, triethylamine, sulfur trioxide and glacial acetic acid as raw materials.” Not only does Jiu teach this method, but Jiu beginning on p. 8, para. [0010] teaches a method involving sulfamic acid, diketene, triethylamine. Jiu states “The purpose of this invention is to provide a continuous method for producing acesulfame potassium. The method involves using sulfamic acid as a raw material and reacting it with diketene in the presence of triethylamine to generate acetylacetamide sulfonate (DKA). Then the product undergoes continuous cyclization with sulfur trioxide, continuous hydrolysis, continuous extraction, continuous separation, and continuous crystallization to prepare AK sugar.” Reaction details are taught beginning in para. [0014] which states “Aminosulfonic acid and dichloromethane are continuously mixed and dissolved, and then continuously neutralized with triethylamine solution. The neutralized solution and diketene are fed into a continuous reactor, where an addition acylation reaction is carried out to obtain DKA reaction solution.”
Jiu in para. [0016] teaches dissolving sulfur trioxide in dichloromethane to generate a cyclization agent. This agent is then added to the DKA reaction solution (para. [0017]) and hydrolyzed to obtained a acesulfame potassium reaction solution. This acesulfame potassium solution is then fed into an extraction device (para. [0019]) where the organic phase is treated with potassium hydroxide to obtain the acesulfame product.
Jiu in para. [0031] teaches reactions conditions of the hydrolysis reaction which include reaction temperatures between 25o C and 100oC. The instant claims claim hydrolysis temperatures between 0oC and 20oC. These ranges are sufficiently close enough that one of ordinary skill in the art would find it obvious to reduce the temperature range in efforts to optimize the reaction yield.
Additionally, claims 7-8 claim ratios between different components of the reactions. Claim 7 states “the molar ratio of the sulfamic acid to the amount of the sulfur trioxide…”. The sulfamic acid is a component of the first intermediate solution. The sulfur trioxide is a component of the sulfonation cyclization step. Jiu discusses ratios for the specific solutions. An example is found in para. [0033] which states “The mass ratio of m(acesulfame potassium reaction solution):m (dichloromethane) is 1:0.5-15…”. While Jiu may not specifically contemplate ratios between components such as the sulfamic acid to sulfur trioxide, this would be well within the skillset of one of ordinary skill in the art to alter and optimize, similar to the temperature of the hydrolysis reaction.
Therefore, the critical differences between Jiu and the instant claims are the use of a solid superacid catalyst and the use of aqueous ethanol within the hydrolysis reaction. This is addressed by the combination of Arata, further, the combination of Bender.
Arata is drawn to superacidic metal oxides used in organic synthesis (title). Arata on p. 1720, table 1 teaches a number of sulfonate metal oxide catalysts.
Arata, Table 1
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Arata on p. 1721, sec. 1. The Friedel’s-Crafts reactions teaches the use of the superacid catalysts above to perform alkylation and acylation reactions. Arata states “In the two main reactions, alkylation and acylation, the latter has been predominantly selected; it is less reactive than the former. In addition, the catalytic acylation of aromatics via the Friedel’s-Crafts reaction is attractive for organic synthesis and a prerequisite challenge to green technology. Traditional methods depend on the use of at least stoichiometric quantities of Lewis acids, such as aluminum trichloride and boron trifluoride, because the Lewis catalysts are consumed by coordination with the formed aromatic ketones.”
The instant claims are drawn to carrying out an acylation reaction under the presence of a superacid such as those taught in Arata. Arata teaches that the superacid catalysts not only function as effective acylation catalysts but that they also circumvent the use of stochiometric amounts of Lewis acids (less wasteful).
Bender is drawn to a study that examines the kinetics of simultaneous hydrolysis and alcoholysis of esters in aqueous alcohol solutions (title). Bender on p. 1592-1593, sec. Results teaches ethanol-water mixture as a solvent for the hydroxide ion-catalyzed hydrolysis of acetyl-L-phenylalanine methyl and ethyl esters. Bender on p. 1596 further teaches the hydrolysis of ethyl acetate in methanol-water and ethanol-water solutions. A range of concentrations were tested in Bender as Bender states “The experimental slopes of plots of ln koh vs 1/D gave reasonable linearity over the range of 15-80 volume percent methanol and 30-50 volume percent ethanol.”
Jiu in para. [0059]-[0060] already teaches the use of water as a hydrolysis agent where it states “The DKA reaction solution and cyclizing agent are continuously fed into the cyclization microreactor to generate the cyclization reaction solution, which is then continuously fed into the hydrolysis microreactor to obtain the acesulfame acid reaction solution. The feed volume ratio of the DKA reaction solution, cyclizing agent and water is 1:0.2-3:0.3-3…”. As Bender teaches that aqueous ethanol is capable of affording hydrolysis reactions, one of ordinary skill in the art would only need to use aqueous-ethanol in place of water in the hydrolysis step.
The instantly claimed method involves a number of steps that are well known within the art. The modification of the hydrolysis temperature and use of aqueous-ethanol are modifications within the skillset of one of ordinary skill. Not only is the use of aqueous-ethanol a simple solvent substitution, one of ordinary skill could make the modification with a reasonable assumption of success as Bender teaches hydrolysis reactions can be performed with aqueous-ethanol solvent. Similarly, the addition of a superacid catalyst that is well-known within the art would also be obvious as Arata teaches SO42-/Fe2O3 catalysts are effective in performing acylation reactions.
Therefore, it would have been prima facie obvious at the time of the effective filing date for one of ordinary skill in the art to have combined the teachings of Jiu, Arata, and Bender to arrive at the instant claims with a reasonable assumption of success. One of ordinary skill would be motivated to make the modifications as the art teaches that these modifications are effective for their purposes (catalyzing an acylation reaction and performing a hydrolysis reaction) and would be predictably successful.
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 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-4 and 6-10 of copending Application No. 18/519,151.
The reference claims are drawn to a method of preparing acesulfame potassium (claims shown below).
This is a provisional nonstatutory double patenting rejection.
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Where the reference claims are different is in the temperature of the hydrolysis step which is -10oC - -20oC. This change would be obvious to one of ordinary skill as it is well within their skillset.
Conclusion
No claims allowed.
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/L.G./Examiner, Art Unit 1624
/SUSANNA MOORE/Primary Examiner, Art Unit 1624