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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 6/9/2026 has been entered.
Claim Status
Claim 49 was newly added in the response filed 6/9/2026. Claims 1, 3-16, 18-20, and 49 are pending.
Maintained Claim Rejections - 35 USC § 103
The rejection of record is on p. 2-12 of the OA dated 1/8/2026 and is maintained.
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claim(s) 1 and 3-12 is/are rejected under 35 U.S.C. 103 as being unpatentable over Hu (US 2015/0183731, published on 7/2/2015, of record) as evidenced by Carbon Dioxide (“5.5 Dissolved Gases: Carbon Dioxide, pH, and Ocean Acidification”, downloaded from https://rwu.pressbooks.pub/webboceanography/chapter/5-5-dissolved-gases-carbon-dioxide-ph-and-ocean-acidification/ on 6/25/2025, of record) and Climate Change (“Climate change: atmospheric carbon dioxide”, downloaded from https://www.climate.gov/news-features/understanding-climate/climate-change-atmospheric-carbon-dioxide on p=6/25/2025, of record).
Applicant Claims
A process for producing taurine comprising:
mixing aminoethanol sulfate ester (AES) with a carbonate or bicarbonate, or combination thereof, thus producing a reaction mixture; and
heating the reaction mixture in the presence of a sulfite or a bisulfite, or combination thereof, such that taurine is formed;
wherein a molar ratio of the carbonate or bicarbonate, or combination thereof to the AES in the reaction mixture is equal to or greater than 0.1 and less than 1.0.
Determining the Scope and Content of the Prior Art (MPEP §2141.01)
Hu discloses a cyclic process for the production of taurine from monoethanolamine (MEA). See abstract. Hu teaches that the process follows the following Scheme in [0008]:
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. In the first step (1) monoethanolamine (MEA) is treated with sulfuric acid (H2SO4) to produce 2-aminoethyl hydrogen sulfate ester (AES). In the second step (2), AES is reacted with a sulfite (M2SO3) to produce taurine and a sulfate (M2SO4) in a sulfonation step. Both reactions are carried out under aqueous conditions. See examples.
Hu further teaches that hydrolysis is a competing mechanism in the second step (2):
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. See [0027]. Hu teaches that one of the options to mitigate the undesirable hydrolysis reaction is to control the pH of the sulfonation by continuously dosing the reaction solution with a base or employing a buffering system. Hu teaches that the bases include sodium and potassium hydroxide (claims 3-5), ammonium hydroxide (claims 3 and 4) and ammonium carbonate (claim 1). See [0030-0032]. Hu also teaches that the sulfonation reaction requires heat and that the reaction temperature falls within the range of 90 to 150°C. See [0026]. In examples 4-8 in [0051-0053], Hu teaches that the base (ammonium hydroxide) is added to the mother liquor containing ammonium sulfite. Hu then teaches “AES is then charged and pH rechecked and if necessary readjusted to 7.2 with ammonium hydroxide or dilute sulfuric acid”. This indicates that the base can be present at the beginning of the reaction, in addition to being continuously added. Therefore the examples of Hu teach that the base is present before heating (claims 7 and 12), and if the base is also continuously dosed, then it is also added during the step of heating (claim 12).
Ascertainment of the Difference Between Scope of the Prior Art and the Claims (MPEP §2141.02-03)
Regarding claims 1, 2, 7, and 12, Hu does not explicitly teach an example wherein the base in the sulfonation step is ammonium carbonate.
Regarding claims 3-6, Hu does not explicitly teach that a mixture of bases is present in the reaction. Nor does Hu comment on the presence of carbon dioxide in the reaction mixture.
Finding of Prima Facie Obviousness Rationale and Motivation (MPEP §2142-2143)
It would have been prima facie obvious to one of ordinary skill in the art to arrive at the instantly claimed process based on the teachings of Hu, as evidenced by Carbon Dioxide and Climate Change, with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill in the art would have been motivated to use ammonium carbonate as a base in the sulfonation (step 2) reaction of Hu because Hu explicitly suggests as much, indicating that ammonium carbonate is a preferred base because ammonium cations are already present in the system.
Further regarding claim 1, Hu does not explicitly teach a molar ratio of base to AES. However, Hu teaches that the pH of the reaction is kept in the desired region of 6.0 to 8.0. See [0032] and [0051-0053]. As evidenced by Table 1-2 in [45-46] of the specification as filed, this is the same range as the inventive examples. Therefore, the molar ratio of the base : AES will overlap with that claimed. Further, it would be prima facie obvious to monitor and adjust the concentration of base in the mixture to keep the reaction mixture within the disclosed pH range. Also see MPEP 2144.05.
Further regarding claims 3-6, a person of ordinary skill in the art would have been motivated to use a mixture of ammonium carbonate and another acceptable base, including ammonium hydroxide and sodium hydroxide [0031] because using combinations of known acceptable reactants is prima facie obvious. If a mixture of bases is used in the process of Hu, the process will still predictably produce taurine from AES under pH control. Further regarding claim 6, though Hu is silent regarding the presence of carbon dioxide in the reaction mixture, the reaction conditions of Hu are expected to include carbon dioxide. As evidenced by Carbon Dioxide, carbon dioxide is soluble in water and engages in a reversible reaction to form carbonic acid, which can then be converted to bicarbonate and carbonate depending on the pH of the mixture. See Fig. 5.5.2:
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. Therefore, if the reaction comprises ammonium carbonate, then the mixture comprises dissolved carbon dioxide. Likewise, the skilled artisan would be motivated to bubble CO2 into the reaction mixture in order to generate more carbonate using the well-known acid base reactions above. Alternatively, Hu appears to teach that the reaction mixture is exposed to the atmosphere before heating in the autoclave in the examples. As evidenced by Climate Change (see whole document), carbon dioxide is also present in air/the atmosphere. Thus, carbon dioxide is also being introduced into the reaction mixture from this source.
Regarding claims 8-11, Hu teaches that the molar ratio of the sulfite to AES is from 1:1 to 5:1. See [0026]. This range overlaps with all of those claimed. See MPEP 2144.05.
Claim(s) 13-16, 18-20, and 49 is/are rejected under 35 U.S.C. 103 as being unpatentable over Hu (US 2015/0183731, published on 7/2/2015, of record), as evidenced by Carbon Dioxide and Climate Change as applied to claims 1 and 3-12, and further in view of Yamamoto (US 4657704, published on 4/14/1987, of record) and Plutschack (“The Hitchhiker’s Guide to Flow Chemistry” Chemical Reviews, 2017, p. 111796, of record).
Applicant Claims
Applicant claims the process of claim 1, wherein the heating is carried out in the presence of an inert gas and each of the AES, base, and sulfite are fed to a sulfonation vessel in separate lines and mixed in the vessel or are heated in a sealed sulfonation vessel under an inert gas pressure greater than autogenous pressure.
Applicant claims the process of claim 14 having one of the claimed residence times and the sulfonation vessel of claim 16.
Determining the Scope and Content of the Prior Art (MPEP §2141.01)
The examples of Hu appear to teach that the sulfite and base are mixed first, and then that the AES is added to the combined mixture before heating. The examples also appear to teach that the reaction mixture is exposed to the atmosphere before the sulfonation vessel, an autoclave, is closed and heated. See [0051-0053].
The examples of Hu all appear to be carried out batchwise in a sealed autoclave. See [0045-0055]. Hu also teaches that the reactions are carried out at elevated temperatures and at autogenous to greater than autogenous pressures. See [0026]. Hu teaches that reactions which employ a buffer in place of a base are stirred for a residence time of 24 or 40 hours. See examples 1-3. When a base is added to the system in the cyclic examples 4-8, then the reaction time is decreased to 18 hours.
Yamamoto teaches an analogous process to that of Hu for producing aminoalkylsulfonic acids. Yamamoto teaches that the process comprises reacting a halide of the following formula (wherein X is a halogen):
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with a sulfite to produce an aminoalkylsulfonic acid of the following formula:
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. See abstract and claims. When n is 2 and R1, R2, and R3 are H, the product compound corresponds to taurine. Therefore, Yamamoto teaches a process wherein the sulfate ester leaving group of Hu is replaced by a halogen leaving group. Yamamoto further teaches that the reaction is heated, preferably in stages. See abstract. Yamamoto teaches that the reaction can be carried out under a nitrogen (N2) atmosphere (claims 13, 14, 19, 20, and 49). See examples and claim 1. Yamamoto also appears to teach batch reactions in the examples.
Plutschack is a review of flow chemistry. Plutschack teaches that flow chemistry involves the use of channels or tubing to conduct a reaction in a continuous stream rather than in a flask. Flow equipment provides chemists with unique control over reaction parameters enhancing reactivity or in some cases enabling new reactions. See abstract. Plutschack teaches that commonly reported benefits of continuous processes include better mixing, more efficient heat transfer, and easy-scale up. See first paragraph in introduction section 1 on p. 11797. Plutschack teaches that these benefits lead to reduced energy input, which is particularly attractive from an industrial perspective. See second paragraph in introduction section 1 on p. 11797. Plutschack teaches that flow reactors are suitable for multiphasic reactions and can accommodate many different flow regimes. See section 2.1 on p. 11797-11799. Plutschack also teaches that flow chemistry is a modular technique that can be modified to suit the unique needs of the reaction under consideration. See section 3 on p. 11805 to 11806. Plutschack teaches a simple example of the different zones that can be included in the continuous flow reactor in Fig. 11 on p. 11806:
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. Also see discussion thereof in section 3 on p. 11805-11806. Plutschack teaches that each reactant may have its own line, and that mixing units can be inserted at any point to connect one or more reagent lines to each other before being introduced into the reactor (claims 16).
Plutschack teaches that the systems can contain delivery lines for liquid and gaseous reactants. Plutschack teaches that residence time in the reactors is regulated by precise control over the movement of fluids in the reactor. See sections 3.2 on p. 11806-11807. Plutschack teaches the most common reactor types for flow reaction in Fig. 16 on p. 11809:
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. Also see section 3.4 on p. 11809-11811.
Sections 5 to 6 of Plutschack are dedicated to working examples of flow chemistry processes, which encompass a wide variety of reactions. Thus, Plutschack teaches the broad applicability of flow chemistry.
Ascertainment of the Difference Between Scope of the Prior Art and the Claims (MPEP §2141.02-03)
Hu does not explicitly teach that the heating is carried out in the presence of an inert gas and that each of the AES, base, and sulfite are fed to a sulfonation vessel in separate lines and mixed in the sulfonation vessel. Hu does not explicitly teach a sulfonation apparatus having at least two parts (claim 16). Nor does Hu explicitly teach the residence times of claims 17 and 18.
Finding of Prima Facie Obviousness Rationale and Motivation (MPEP §2142-2143)
It would have been prima facie obvious to combine the teachings of Hu, Yamamoto, and Plutschack to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to carry out the heating step of Hu under an inert, nitrogen atmosphere, because Yamamoto teaches that this is a known modification for analogous reactions. Therefore, if the reactions of Hu were carried out under a nitrogen atmosphere, the process would still predictably produce taurine. Also see MPEP 2143(I)(B).
A person of ordinary skill in the art would have been further motivated to modify the order of addition of the reactants in the process of Hu to arrive at that claimed because the selection of any order of performing steps and/or mixing ingredients is prima facie obvious. Also see MPEP 2144.04(IV)(C). As Hu teaches that the sulfonation reaction requires heat, the skilled artisan would not expect the order of addition prior to heating to affect the outcome of the reaction.
A person of ordinary skill would have been motivated to carry out the reaction of Hu and Yamamoto continuously because continuous operation is obvious in view of batch processes. See MPEP 2144.04(V)(E). Plutschack is cited to teach modular and adjustable systems for continuous flow operation which would accommodate all of instant steps (a), (b), and (c). Therefore, Plutschack provides support that the combined reaction of Hu and Yamamoto can be predictably facilitated in a continuous fashion. Also see MPEP 2143(B). Further regarding claims 16, as discussed in the preceding section, the selection of any order of performing steps and/or mixing ingredients is prima facie obvious. Also see MPEP 2144.04(IV)(C).
Regarding claim 15, see discussion of claims 8-11 in previous rejection.
Response to Arguments on p. 6-8 of the Response filed on 6/9/2026:
Applicant argues:
“In Hu, the carbonate is simply added to control the pH of an ongoing reaction. In
contrast, the present application contemplates the reaction of the AES with the carbonate, to produce intermediates. Thus, the present claims recite the creation of a reaction mixture including the AES and the carbonate or bicarbonate and then heating this mixture. It is this premixing that allows the molar ratios recited in the claims to be achieved. By establishing the claimed molar ratio of 0.1 to less than 1.0 in a cool reaction mixture prior to heating, Applicants prevent the localized over-alkalization and subsequent alkaline hydrolysis of the AES ester bond that naturally occurs when dropping a basic carbonate directly into a hot, ongoing reaction mixture as done in Hu. This cool pre-mixing step creates a distinct, significantly more stable reaction pathway that maximizes taurine yield-an operational advantage that cannot be achieved or replicated by Hu's real-time, high-temperature pH control mechanism.
In addition, when carbonate is added to a heated ongoing reaction between AES and sulfite, the carbonate reacts with the acidic products to produce carbon dioxide.
R-O-SO3H + (NH4)2CO3 -> R-O-SO3 NH + NH4 + H20 + CO2 T
This continuous production of carbon dioxide from the continuous addition of the carbonate does lower the pH (through the neutralization of the acids), but never builds up to the claimed molar ratio as it is turned into CO2 gas. As evidenced by Carbon Dioxide, the CO2 can interact with water to form carbonic acid. The conversion of carbonic acid into bicarbonate requires a sufficiently acidic environment - which is precisely what the continuous addition of ammonium carbonate taught by Hu is attempting to avoid. Thus, the amount of carbonate added continuously to control the pH of the reaction mixture of Hu will never build up enough to achieve the claimed molar ratios as the carbonate will be converted to CO2 gas and carbonic acid.
In view of the above, the combination of the references fails on two counts: 1) the references do not teach the creation of a reaction mixture comprising AES and carbonate or bicarbonate prior heating; and 2) the molar ratio of greater than 0.1 and less than 1.0 is never achieved in Hu as the carbonate is continually converted to CO2 gas and carbonic acid. The remainder of the references do not overcome this deficiency in the teachings of Hu.”
The Applicant’s arguments have been fully considered but are not persuasive. Paragraphs [0031-0032] of Hu teach controlling the pH of the sulfonation step is critical because at too acidic of a pH side reactions, including hydrolysis, become prominent. Hu teaches that the pH can be controlled by a buffer or “continuously dosing the reaction solution with base”. In examples 4-8 in [0051-0053], Hu teaches that the base (ammonium hydroxide) is added to the mother liquor containing ammonium sulfite. Hu then teaches “AES is then charged and pH rechecked and if necessary readjusted to 7.2 with ammonium hydroxide or dilute sulfuric acid”. This indicates that the base can be present at the beginning of the reaction, in addition to being continuously added. Hu further teaches that the sulfonation takes place at 120°C in an autoclave (sealed reactor). The other examples in [0043-0049] teach the use of an ammonium buffer system that is in place at the beginning of the reaction, wherein the sulfonation is heated at 110°C in an autoclave under autogenous pressure. Therefore, the Examiner respectfully disagrees that Hu “does not teach or suggest that the carbonate can be present in the reaction mixture prior to heating”.
Though the Applicant argues that the carbonate is “simply added to control the pH of an ongoing reaction” in Hu, this appears to be the same utility for the carbonate in the inventive examples as evidenced by Table 2 of the specification as filed. Both the basic carbonate and the NaOH are varied in Table 2 to control the pH of the feed. Regarding a reaction of AES with carbonates to produce “intermediates” in the inventive process, there is no evidence to show that this step occurs or is critical to the claimed process. The only place it is discussed in the specification is in [33] and [43], which recites “without being bound by theory, AES may also react with carbonate and/or bicarbonate to form one or more intermediates”. The examples in the specification as filed teach that the sulfonation is carried out at a temperature of 130-150°C and at a pressure of 100-200 psi N2, which is under harsher conditions than what is taught in the examples of Hu. However, there is no objective evidence that “this cool pre-mixing step creates a distinct, significantly more stable reaction pathway that maximizes taurine yield—an operational advantage that cannot be achieved or replicated by Hu’s real-time high-temperature pH control mechanism”. See MPEP 2145.
Regarding the Applicant’s arguments that all of the carbonate will be turned into CO2 gas and carbonic acid in the reaction mixture such that the reaction mixture of Hu will never build up enough to achieve the claimed molar ratios as the carbonate will be converted to CO2 gas and carbonic acid, this argument is not persuasive. The Applicant fails to account for the reversible nature of the acid/base neutralization reaction, especially as the reaction of Hu is carried out in a sealed autoclave such that CO2 gas that is generated cannot escape and is available to be redissolved in the reaction mixture, especially if the pressure reaches too high in the autoclave. Further, Hu explicitly teaches that enough of the base should be added to control the pH of the reaction. As argued in the rejection, if Hu teaches the same pH as the instant inventive reactions and explicitly teaches that the concentration of base in the mixture controls the pH, then the skilled artisan would arrive at the instantly claimed molar ratios based on the teachings of Hu. Arguments presented by applicant cannot take the place of evidence in the record. See In re De Blauwe, 736 F.2d 699, 705, 222 USPQ 191, 196 (Fed. Cir. 1984); In re Schulze, 346 F.2d 600, 602, 145 USPQ 716, 718 (CCPA 1965); In re Geisler, 116 F.3d 1465, 43 USPQ2d 1362 (Fed. Cir. 1997). See MPEP 2145.
Therefore, the rejection of record is maintained.
Double Patenting
The rejections of record on p. 14-16 of the OA dated 1/8/2026 and reiterated herein.
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, 3-16, 18-20, and 49 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 2, 5-8, 12, 15, 17, 18, 22, 26, 27, and 31-38 of co-pending Application No. 18/002329 (‘329, reference application, claims indicated as being allowable in NOA dated 5/21/2026).
Although the claims at issue are not identical, they are not patentably distinct from each other because claim 1 of ‘329 is a species of the process of instant claim 1 and 49, which further comprises a step for producing AES from MEA and sulfuric acid. Regarding claims 3-6, see claims 1 and 2 of ‘329 and MPEP 2144.07; regarding claims 7 and 12, see claims 5-7 of ‘329; regarding claims 8-11 and 15, see claim 8 of ‘329; regarding claims 13, 19, 20, and 49 see claims 12 and 15 of ‘329; regarding claims 14, 16, and 49, see claim 26 of ‘329 and MPEP 2144.04(IV)(C). Regarding claims 17-18 though the claims of ‘329 do not explicitly teach or suggest these limitations, they are routinely optimizable variables in continuous processes. See MPEP 2144.05. This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 1, 3-16, 18-20, and 49 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-20 of co-pending Application No. 17/907151 (‘151, reference application), as evidenced by Carbon Dioxide (“5.5 Dissolved Gases: Carbon Dioxide, pH, and Ocean Acidification”, downloaded from https://rwu.pressbooks.pub/webboceanography/chapter/5-5-dissolved-gases-carbon-dioxide-ph-and-ocean-acidification/ on 6/25/2025). *151 was abandoned on 4/23/2026, however a petition for revival of an application for patent abandoned unintentionally under 37 CFR 1.137(a) filed 6/29/2026 is under review.
Although the claims at issue are not identical, they are not patentably distinct from each other because claim 1 of ‘151 is an obvious variant of the process of instant claims 1, 2, and 49, wherein the bicarbonate or carbonate is formed in situ from carbon dioxide and the base of claim 3 of ‘151. See Fig. 5.5.2 in the evidentiary reference. Regarding claims 3-6, see claims 3-5 of ‘151; regarding claims 7 and 12, see claims 6-7 of ‘151; regarding claims 8-11 and 15, see claims 8-11 of ‘151; regarding claims 13, 19, 20, and 49, see claims 13, 14, 19, and 20 of ‘151; regarding claims 14, 16, and 49 see claims 14 and 16 of ‘151 and MPEP 2144.04(IV)(C); regarding claims 17 and 18, see claims 17 and 18 of ‘151.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
The Office acknowledges the Applicant’s request to have the provisional non-statutory double patenting rejections held in abeyance on p. 8-9 of the response filed 6/9/2026.
Conclusion
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/AMY C BONAPARTE/Primary Examiner, Art Unit 1692
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