DETAILED ACTION
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114 was filed in this application after a decision by the Patent Trial and Appeal Board, but before the filing of a Notice of Appeal to the Court of Appeals for the Federal Circuit or the commencement of a civil action. 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examination under 37 CFR 1.114 and the fee set forth in 37 CFR 1.17(e) has been timely paid, the appeal has been withdrawn pursuant to 37 CFR 1.114 and prosecution in this application has been reopened pursuant to 37 CFR 1.114. Applicant’s submission filed on 02/27/2026 has been entered.
Status of claim rejections
The rejection of record under 35 USC 103 is maintained and modified in view of Applicant’s amendments in the response filed 02/27/2026.
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 1, 3-7, 10-13 and 16-30 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.
Claims 1, and 21-26 recite the limitation “at least about”. The term “at least about” in the claims is indefinite because the recitation of “at least” sets a lower limit but “about” does not set a lower limit. Thus, the claims are indefinite. Please note that the dependent claims are also indefinite due to dependency on indefinite claim 1.
Claim 30 recites the “about 900 to about 300”. The term “about” in the claim is indefinite because the recitation of “about” does not set a lower limit to what the temperature may be (does the claim encompass temperatures of 87 degrees C? or 303 degrees?). Thus, the claim is indefinite.
Claim Interpretation
Claim 1 recites “wherein the method results in ethanolamine having a purity equal to or greater than 60% and a yield . . . equal to or greater than 60% . . .” The examiner is interpreting this limitation as an intended result of the method steps (i.e., the steps of adding a base, precipitating, sterilizing, and removing ethanolamine) as the wherein clause in a method claim is “not given weight when it simply expresses the intended result of a process step positively recited.’" Id. (quoting Minton v. Nat’l Ass’n of Securities Dealers, Inc., 336 F.3d 1373, 1381, 67 USPQ2d 1614, 1620 (Fed. Cir. 2003)) (see MPEP 2111.04).
Regarding claims 1 and 21-26, the examiner is interpreting the deprotonation of ethanolamine molecules to occur as a result of the step of addition of a base (e.g., such as a strong base).
Modified 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.
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.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
First rejection
Claims 1, 3-7, 9-13, and 17-27 are rejected under 35 U.S.C. 103 as being unpatentable over Soucaille et al (WO 2007/144346, IDS-FOR, hereinafter “Soucaille”) in view of McNabb (US 6,077,976, IDS-US), JP 2004529626 (prior art of record, translation cited below, hereinafter “JP626”), van Grinsven et al (WO 99/21821, IDS-FOR, hereinafter “van Grinsven”) and as evidenced by Fruchey et al (EP2305766 B1 published 04/06/2011).
Soucaille teaches a method for biological production of ethanolamine from a fermentable carbon source (Abstract). Soucaille teaches recombinant E. coli is combined with modified minimal medium in a 300 ml fermentor for ethanolamine production (Example 6). Soucaille further teaches base, i.e., NH4OH, is added to the resulting fermentation composition comprising ethanolamine to maintain a pH between 6.5 and 8 (Example 6) during fermentation. As such, Soucaille teaches adding base to the fermentation composition when the pH is below the 6.5 to 8 range, i.e., “less than 8.” Soucaille also teaches recovering ethanolamine from the fermentation composition (page 5, lines 12-15).
Soucaille does not explicitly teach increasing the pH of the fermentation composition to equal to or greater than pH 9 or removing ethanolamine from the fermentation composition by distillation. However, McNabb teaches that ethanolamine can be recovered from aqueous streams containing inorganic salts, which would include, e.g., the inorganic salts in the medium by Soucaille (McNabb, Abstract; Soucaille, Table 2). McNabb teaches the aqueous stream is mixed with strong base, e.g., NaOH or KOH, to raise the pH to 9-13.5 (column 1, lines 50-54). McNabb further teaches the aqueous stream (water) is then extracted (exchanged) with an alkylphenol solvent (column 1, lines 53-55). In specific examples, McNabb teaches the alkylphenol solvents are butylphenol and octylphenol (Examples 1 and 2). McNabb further teaches the solvents have higher boiling points than ethanolamine, which allows for recovery of ethanolamine by distillation (Examples 1 and 2).
One of ordinary skill in the art would have been motivated combine the teachings of Soucaille and McNabb in order to advantageously remove ethanolamine from the fermentation composition taught by Soucaille using art-recognized extraction and distillation techniques with a reasonable expectation of success. Further, as McNabb teaches adding strong base to ethanolamine fermentation to increase pH to 9-13.5, absent evidence to the contrary, addition of the base would also result in deprotonation of the ethanolamine molecules
None of the references explicitly teach deprotonation of ethanolamine molecules or precipitation of impurities.
However, van Grinsven teaches that aqueous alkanolamines, such as ethanolamine, can be purified via a two-step distillation utilizing film-type evaporators with wiped-film evaporators yielding better results than falling-film evaporators (Abstract; page 5, lines 20-30; page 7, lines 9-15). Van Grinsven teaches raising pH of the solution to 12 and explains that raising the pH to 12 allows for increased alkanolamine recovery (i.e., increased yields) by decreasing the amount of heat stable salts in the form of strong acids bound to the amine (see pg. 8, lines 4 to pg 10, line 4). van Grinsven further teaches that the first distillation step carried out at 130 to 180°C at 40 to 90 kPa, and the second distillation step is carried out at 120 to 200°C at 2 to 10 kPa (page 6, lines 17-20; page 7, lines 12-15). In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); see also MPEP § 2144.05(I).
Fruchey evidences that addition of strong bases such as KOH can be used to adjust pH of fermentation broths to higher pH (such as up to 13) and to precipitate impurities (such as color body impurities) from the broth (see paragraphs 0031-35).
One of ordinary skill in the art would have been motivated to advantageously utilize art-recognized distillation techniques and parameters, such as those taught by van Grinsven, for use in the method taught by Soucaille, McNabb, and JP626 with a reasonable expectation of successfully distilling the alkanolamines, as well as increased alkanolamine recovery by decreasing the amount of heat stable salts in the form of strong acids bound to the amine and to precipitate impurities.
Moreover, it would have been a matter of routine experimentation utilizing standard laboratory techniques available at the time of filing to determine the optimal operational parameters in the method taught by Soucaille and McNabb to maximize ethanolamine yield (> 60%), purity (> 60%), the amount of base to include in the fermentation composition to deprotonate 40-95% of the molecules with a reasonable expectation of success (see MPEP 2144.05), as van Grinsven teaches that increasing the pH of the fermentation broth increases alkanolamine recovery by decreasing the amount of heat stable strong acid salts (i.e., deprotonate the alkanolamine solutions as instantly claimed).
The references do not explicitly teach sterilizing or separating biomass from the fermentation composition prior to removing ethanolamine by distillation.
However, it would have been prima facie obvious at the time of filing to sterilize the fermentation composition taught by Soucaille and McNabb and separate biomass from the fermentation composition prior to removing ethanolamine by distillation because JP626 teaches sterilization of a fermentation composition after separation from the biomass by filtration (Abstract; ¶ 0091, see also ¶¶ 0127-0128).
One of ordinary skill in the art would have been motivated to modify Soucaille and McNabb in view of JP626 in order to advantageously kill/remove any residual microbes in the fermentation composition to avoid downstream contamination issues with a reasonable expectation of success. Moreover, one of ordinary skill in the art would have been free to sterilize/filter the fermentation composition taught by Soucaille and McNabb before and/or after the addition of base with a reasonable expectation of success. See In re Burhans, 154 F.2d 690, 69 USPQ 330 (CCPA 1946) (selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results).
Accordingly, the claimed invention was prima facie obvious to one of ordinary skill in the art at the time of filing especially in the absence of evidence to the contrary.
Second rejection
Claims 28-29 are rejected under 35 U.S.C. 103 as being unpatentable over Soucaille, McNabb, JP626, and van Grinsven as applied to claims 1, 3-7, 9-13, and 17-27 above, and further in view of Ollivier (US 20100261240 A1).
As discussed above, claims 1, 3-7, 9-13, and 17-27 were rendered prima facie obvious by Soucaill, McNabb, and JP626. The references do not explicitly teach the solvent is glycerol, ethylene glycol, etc. or that the amount of solvent added is suitable to maintain a liquid composition.
However, Ollivier teaches a method for purifying an alcohol from a fermentation broth, comprising at least the following steps: filtering the fermentation broth in order to obtain an aqueous solution containing the alcohol, adding glycerol to the aqueous solution, purifying and recovering the alcohol (see claim 1 and claim 8). Ollivier also teaches that the addition of glycerol avoids the precipitation of salts during the purification of alcohol from the fermentation broth, and the glycerol solubilizes salts in order to retain them in the liquid phase until the end of the purification process (see paragraph 11).
One of ordinary skill would have been motivated to modify the method of Soucaille, McNabb, and J626 by using glycerol as taught by Ollivier to arrive at the claimed invention with a reasonable expectation of success. One of ordinary skill would have been motivated to make the modification because Ollivier teaches that glycerol advantageously avoids the precipitation of salts during the purification of alcohol from the fermentation broth, and solubilizes salts in order to retain them in the liquid phase until the end of the purification process.
Accordingly, the claimed invention was prima facie obvious to one of ordinary skill in the art at the time of filing especially in the absence of evidence to the contrary.
Third rejection
Claim 30 is rejected under 35 U.S.C. 103 as being unpatentable over Soucaille, McNabb, JP626 and van Grinsven as applied to claims 1, 3-7, 9-13, and 17-27 above, and further in view of Watanabe et al (US 5633408 A).
As discussed above, claims 1, 3-7, 9-13, and 17-27 were rendered prima facie obvious by Soucaill, McNabb, JP626 and van Grinsven. The references do not explicitly teach the distillation occurs at a bottoms temperature of 90-300 degrees C.
However, Watanabe teaches various processes for the production and purification of alkanolamines including ethanolamine (see claim 1, 5, and 6 and abstract). Watanabe teaches that during the distillation of the alkanolamine, impurities can be remarkably reduced, if distillation is carried out at a certain column bottom temperature or less of a distillation column in heating and distilling the crude alkanolamine solution to obtain a monoalkanolamine (see col 3, lines 55-60). Watanabe further teaches proper distillation bottom temperatures of 100° to 200° C or more (including 160° to 220° C; see claim 3, see col 6; see claim 8). Note that Watanabe’s range of 100° to 200° C or more lies within the claimed range of 90-300 ° C. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. 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).
One of ordinary skill would have been motivated to modify the method of Soucaille, McNabb, J626, and van Grisen by using the bottoms temperatures as taught by Watanabe to arrive at the claimed invention. One of ordinary skill would have been motivated to make the modification because Watanabe teaches that temperatures of 100° to 200° C or more is capable of advantageously reduce impurities and aid in distilling ethanolamines.
Accordingly, the claimed invention was prima facie obvious to one of ordinary skill in the art at the time of filing especially in the absence of evidence to the contrary.
Response to Arguments
Applicant's arguments filed 02/27/2026 have been fully considered but they are not persuasive.
On pg. 7-8 of the remarks, Applicant argues that none of the references teach precipitating impurities from the fermentation broth, the % deprotonation of ethanolamine molecules, the & purity, or % yield of ethanolamine. Applicant argues that McNabb teaches away from precipitating salt impurities from the wastewater stream, and that the wastewater streams of Examples 1 and 2 contain sodium sulfate impurities. Applicant argues that the addition of caustic does not result in precipitation of sodium sulfate salts because it forms a stable mixture of dissolved ions because they are highly water soluble. Applicant also argues that the sterilizing step of JP626 does not cure the deficiencies of the combined teachings of McNabb and Soucaille and argues the same in regards to the rejection of claims 5-7.
In response, the examiner disagrees. First, while neither Soucaille or McNabb explicitly teach precipitating impurities from the fermentation composition, Fruchey evidences that addition of strong bases such as KOH (i.e., the base contemplated by McNabb) can be used to adjust pH of fermentation broths to higher pH (such as up to 13) and to precipitate impurities (such as color body impurities) from the broth (see paragraphs 0031-35). Van Grinsven further teaches that increased pH (i.e., at least a pH of 12) increases alkanolamine recovery by decreasing the amount of heat stable salts in the form of strong acids bound to the amine. Thus, the combined teachings of the references provide one of ordinary skill the necessary teaching, suggestion, and motivation to perform the steps as instantly claimed to arrive at the claimed invention. Applicant’s arguments fail to take the totality of the teachings of the references into consideration, especially as all of the references teach known methods of ethanolamine recovery that yield no more than predictable results.
Second, the specification does not define the term “amount sufficient” as it relates to how much base to add to deprotonate ethanolamine nor does it provide any guidance, other than reciting that “the precise amount of base required may vary depending on the strength of the base”. Thus, it would have been a matter of routine experimentation utilizing standard laboratory techniques available at the time of filing to determine the optimal operational parameters in the method taught by Soucaille and McNabb to, e.g., maximize ethanolamine yield (> 60%), purity (> 60%), and the amount of base to include in the fermentation composition to deprotonate 40-95% of the molecules with a reasonable expectation of success (see MPEP 2144.05) as van Grinsven teaches that increasing the pH of the fermentation broth increases alkanolamine recovery by decreasing the amount of heat stable strong acid salts (i.e., deprotonate the alkanolamine solutions as instantly claimed).
Third, regarding Applicant’s arguments regarding McNabb teaching away from precipitating salt impurities, the examiner notes that an obviousness rejection under 35 U.S.C 103 requires one of ordinary skill to balance each individual teaching of the prior art references with the totality of the references in combination. The claim as written requires precipitation of impurities in the fermentation broth generally after addition of the base. Soucaille and McNabb teach using strong bases like KOH during ethanolamine purification, and Fruchey evidences that KOH is capable of precipitating impurities (such as color body impurities) from the broth (see paragraphs 0031-35). As such, when looking at the totality of the teachings of the references, one of ordinary skill would have been motivated to follow the method steps of Soucaille, McNabb, van Grinsven, and JP626 to arrive at the claimed invention and advantageously precipitate impurities from the fermentation broth using a strong base. As such, the rejections of record are maintained as set forth above.
Conclusion
NO CLAIMS ALLOWED.
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/G.C.R./Examiner, Art Unit 1651
/THOMAS J. VISONE/Supervisory Patent Examiner, Art Unit 1672