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 1-10 are pending in the application. Claims 1-9 are rejected. Claim 10 is withdrawn from further consideration.
Election/Restrictions
Applicant’s election without traverse of Group I, claims 1-9, in the reply filed on December 30th, 2025 is acknowledged.
Claim 10 is withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on December 30th, 2025.
Priority
This application claims priority under 35 U.S.C. 119(a-d) to CN202211475554.8, filed November 23rd, 2022.
Receipt is acknowledged of papers submitted under 35 U.S.C. 119(a)-(d), which papers have been placed of record in the file.
Information Disclosure Statement
The Examiner has considered the Information Disclosure Statement(s) filed on July 18th, 2023.
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.
Claims 4 and 6 are 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 4 is rejected as indefinite based on the limitation “an amount of the catalyst added is 0.3%~3%”. The instant claims do not specify what type of percentage is being used. For instance, it could be a molar percentage based on one or both of the reactants, a weight/volume percentage in the sulfur trioxide solution, a weight/weight percentage in the sulfur trioxide solution, a weight/volume percentage based on the volume upon mixing the two solutions or a weight/weight percentage based on the weight upon mixing the two solutions. The instant specification does not clarify the issue especially since Figure 1 depicts the catalyst as not being part of the sulfur trioxide solution and the various examples separately refer to catalyst solutions.
Claim 4 is further rejected as indefinite based on the limitation “the sulfur trioxide solution and the mixed solution C are cooled to -20°C to 20°C after the pre-cooling process.” The pre-cooling process of parent claim 1 involves pre-cooling the ethylene oxide solution and the mixed solution C. Mixed solution C is formed from the sulfur trioxide solution, i.e. the sulfur trioxide solution is no longer a distinct entity separate from the mixed solution C. It is unclear if claim 4 was intended to define the pre-cooling of the mixed solution C and the ethylene oxide solution or if claim 4 is attempting to define an embodiment where the sulfur trioxide solution is subjected to its own pre-cooling process prior to forming mixed solution C.
Claim 6 is rejected as indefinite based on the limitation “and a pre-cooling temperature after mixing is controlled to be -20°C to 40°C.” It is unclear when this temperature range applies in the overall process. Claim 1, from which claim 6 depends, recites a step of “pre-cooling the ethylene oxide solution and the mixed solution C”. It is possible the limitation is referring to (1) the temperature obtained after the actual “pre-cooling” step of claim 1 or (2) the temperature prior to the pre-cooling step, i.e. the temperature before cooling.
Claim Rejections - 35 USC § 112(d)
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 2 is 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 2 recites that solution B is one or a mixture of two options selected from a closed list. Claim 2 further recites a lower limit of the solvent mass fraction for solution B as zero, which would entail having no solvent present. Claim 1, however, requires the presence of some amount of solution B since it is mixed with ethylene oxide. 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. The zero endpoint of claim 2 could be excluded by, for instance, reciting “a solvent in the ethylene oxide solution is up to 80% of a mass fraction of the solution.”
Claim 6 is 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 6 is rejected as indefinite; however, one interpretation is that the temperature range of claim 6 is referring to the actual pre-cooling temperature of claim 1. An upper limit of 40°C for a non-reactive mixing step relative to ambient temperature, however, would not necessarily entail cooling. 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.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim(s) 1-9 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by CN 115745951 A by Ren et al., which was published March 7th, 2023, herein referred to as CN ‘951. A machine translation is appended to the reference and will be referred to herein.
Applicant cannot rely upon the certified copy of the foreign priority application to overcome this rejection because a translation of said application has not been made of record in accordance with 37 CFR 1.55. When an English language translation of a non-English language foreign application is required, the translation must be that of the certified copy (of the foreign application as filed) submitted together with a statement that the translation of the certified copy is accurate. See MPEP §§ 215 and 216.
CN ‘951 teaches a method (page 2 of the machine translation and where paragraph [0011] of the original document discloses the reaction scheme to yield what would be commonly named as ethylene sulfate): “which uses a solution A to dissolve sulfur trioxide to prepare a sulfur trioxide solution, uses a solution B and ethylene oxide to mix and prepare an ethylene oxide solution, adds a catalyst to the sulfur trioxide solution and uniformly mixes the catalyst to obtain a mixed solution C, pre-cools the ethylene oxide solution and the mixed solution C, and then enters a group of microchannel reactors for real-time reaction to obtain a mixed solution containing a crude vinyl sulfate product, and then passes through a post-treatment process to obtain a crude vinyl sulfate product.” The process teaches solutions A and solutions B to prepare sulfur trioxide and ethylene oxide solutions, respectively, where the sulfur trioxide solution further contains a catalyst. The process further includes precooling the sulfur trioxide/catalyst and ethylene oxide solutions and introducing them into a set of microchannel reactors followed by post-treatments to obtain ethylene sulfate.
Regarding instant claims 2-9 the prior art recites analogous limitations on page 2 of the machine translation including the following:
the mass ratio of sulfur trioxide and ethylene oxide is 1: 0.5-1.5; The solution A is at least one or more of dichloromethane, dichloroethane, trichloromethane, and carbon tetrachloride; the solvent in the sulfur trioxide solution is 10-60% of the mass fraction of the solution; the solution B is at least one or two of trichloromethane and carbon tetrachloride; and the solvent in the ethylene oxide solution is 0-80% of the mass fraction of the solution. (corresponding to instant claim 2)
As an improvement of the above technical solution, the reaction residence time in each microchannel reactor in the set of microchannel reactors is 5-20 s, and the reaction pressure is 200-1000 Kpa. (corresponding to instant claim 3)
As an improvement of the above technical solution, the catalyst is at least one of anhydrous pyridine, triethylamine or N, N-dimethylformamide, and the addition amount of the catalyst is 0.3-3%; and the temperature of the sulfur trioxide solution and the mixed solution C decreases to − 20°C to 20°C after the pre-cooling process. (corresponding to instant claim 4)
As an improvement of the above technical solution, the solution A is used to dissolve sulfur trioxide to prepare a sulfur trioxide solution, and a process of preparing an ethylene oxide solution by mixing solution B and ethylene oxide to prepare an ethylene oxide solution is performed by using a mixer. (corresponding to instant claim 5)
As an improvement of the above technical solution, the mixer is selected from a tube-type online mixer or a microchannel online mixer, wherein the online mixer is preferably a static mixer, and the pre-cooling temperature after mixing is controlled between − 20°C and 40° C. (corresponding to instant claim 6)
As an improvement of the above technical solution, the material of the reaction module of the tubular reactor is silicon carbide, glass, stainless steel or ceramic, and the continuous feeding is driven by a diaphragm pump. (corresponding to instant claim 7)
As an improvement of the above technical solution, the post-treatment process includes centrifugation, distillation, extraction, crystallization and filtration. (corresponding to instant claim 8)
As an improvement of the above technical solution, the post-treatment process includes centrifugation, distillation, extraction, crystallization and filtration; wherein the solvent used for extraction is one or more of ethanol, methanol, water, dioxane, dichloromethane, dichloroethane, diethyl ether, dimethyl carbonate, diethyl carbonate, and dioxolane, or a combination of multiple solvents for extraction. (corresponding to instant claim 9)
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 USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The 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/process/file/efs/guidance/eTD-info-I.jsp.
Claims 1-7 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-10 of copending Application No. 18/353,903. The claims of the copending case recite analogous preparation and reaction of a solution of sulfur trioxide and ethylene oxide, pre-cooling and introducing into a set of microchannel reactors. Claim 1 of the copending case, however, does not recite adding a catalyst into the sulfur trioxide solution. Dependent claim 7 of the copending case recites “a catalyst is added while preparing the sulfur trioxide solution by dissolving sulfur trioxide with the solution A”. At least since the copending case does not specify to where the catalyst is added and only explicitly refers to the catalyst addition occurring while preparing the sulfur trioxide solution, a person having ordinary skill in the art would have been motivated to add the catalyst to the sulfur trioxide solution. The catalyst limitations of claim 7 of the copending case are recited in instant claim 4. Regarding instant claims 2, 3, 4 and 7, claims 2, 4, 4 and 6, respectively, of the copending case recite analogous limitations. Regarding instant claims 5 and 6, the instantly claimed limitations are recited in claims 4 and 5 of the copending case.
This is a provisional nonstatutory double patenting rejection.
Additional Prior Art
The closest prior art besides CN 115745951 A appears to be CN 109456303 A by Zhou et al. Zhou et al. teach the following general microchannel reaction (page 2 of the machine translation):
A process for the continuous production of vinyl sulfate and 4-methyl vinyl sulfate in microchannel reactor chemical technology, in the presence of a catalyst, continuously passes diluted liquid sulfur trioxide and diluted ethylene oxide or propylene oxide through a microchannel reactor system, and reacts continuously in a microchannel reactor system at an equimolar ratio to produce vinyl sulfate and 4-methylvinyl sulfate.
The prior art further teaches that the microchannel reactor contains a heat-exchange system as follows (page 2 of the machine translation):
The micro-channel reactor set micro-reaction is integrated with micro-heat exchange, and the micro-reaction refers to mixing the diluted ethylene oxide or propylene oxide and the diluted liquid sulfur trioxide in a micro-channel reactor for micro-mixing and reacting; the micro-heat exchange refers to the thermal effect generated by the micro-reaction, and also comprises in-situ heat exchange of the material in the micro-channel reactor of ethylene oxide or propylene oxide; and the material conveying uses a corrosion-resistant digital display pump.
The instant claims require “pre-cooling” each of the sulfur trioxide and ethylene oxide solutions. As an example of pre-cooling, CN 114591288 A by Yue et al. discloses a different reaction to yield ethylene sulfate including the following steps on page 16 of the machine translation:
At room temperature, 6.2068kg (100mol) of ethylene glycol, 31.034kg of dimethyl carbonate and 0.0310kg of N,N'-dicyclohexylcarbodiimide (the mass ratio of the three is 1:5:0.005, ethyl acetate The mass percentage of glycol is 19.98%), passed into heat exchanger 1 and fully mixed and pre-cooled to 5 °C to obtain ethylene glycol mixed solution (water content (50ppm), in addition in heat exchanger 1 and microchannel A filter (filter accuracy of 0.1 µm) was installed between the reactors. At the same time, 14.8467kg (110mol) of sulfonyl chloride was passed into heat exchanger 2 and pre-cooled to 5°C;
The example above uses ethylene glycol and sulfonyl chloride instead of ethylene oxide and sulfur trioxide. While it may be the case that a person having ordinary skill in the art would have been motivated to combine Chao et al. and Yue et al. to incorporate pre-cooling, Zhao et al. teach the following on page 3 of the machine translation:
Process and operation: A pre-formulated sulfur trioxide and ethylene oxide or ethylene oxide solution (prepared by a solution) is used as a raw material (containing a composite catalyst in a solution of ethylene oxide or propylene oxide), which is conveyed through a digital pump (a corrosion-resistant delivery pump), […]
The section above (and each example of Zhao et al.) incorporates the catalyst with the ethylene oxide reactant. The instant claims, however, require incorporation of the catalyst with sulfur trioxide. The Examiner finds insufficient guidance or motivation regarding this additional change needed to arrive at the instant claims since it is possible that Zhao et al. chose their arrangement to avoid any pre-reactor interactions between their catalyst and sulfur trioxide. Regardless, the absence of guidance on why a particular choice was made in the prior art does not imply that the choice is irrelevant or that it can be modified with a reasonable expectation of success.
The Examiner has further considered a potential rejection under 35 USC 103 over CN 115724822 A by Ren et al. (alone), which discloses an analogous sulfur trioxide and ethylene oxide reaction in a microchannel reactor using pre-cooled solutions. Ren et al. further teach the use of a catalyst on page 3 of the machine translation:
As an improvement of the above-mentioned technical scheme, in the process of using solution A to dissolve sulfur trioxide to prepare sulfur trioxide solution, a catalyst is added at the same time, and the catalyst is anhydrous pyridine, trimethylamine, triethylamine or N,N-dimethyl At least one of the base amides, the addition amount of the catalyst is 0.3-3%.
The language above does not clearly indicate where the catalyst “is added”. The drawings, however, clarify that three separate components are introduced into the microchannel system where one is a separately cooled catalyst at the arrowed position:
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For at least this reason, the Examiner finds that CN ‘822 on its own does not reasonably teach or suggest the instantly claimed approach where the catalyst is added to the sulfur trioxide solution. The instant claims are, however, subject to a double patenting rejection over copending application No. 18/353,903 that appears to be in the same patent family. Since the double patenting rejection is only made over the claims of the copending case (where the disclosure, including the drawings, is not considered as part of the double patenting analysis), the same rationale does not apply to the double patenting rejection above.
Conclusion
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/MATTHEW P COUGHLIN/Primary Examiner, Art Unit 1626
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