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 .
Non-Final Rejection
The Status of Claims:
Claims 9-19 are pending.
Claim 18 is objected.
Claims 9-19 are rejected.
DETAILED ACTION
1. Claims 9-19 are under consideration in this Office Action.
Priority
2. It is noted that this application is a 371 of PCT/FI2022/050025 01/14/2022, which ha a foreign priority document, FINLAND FI20215049 01/15/2021.
Drawings
3. The drawing filed on 7/14/23 was accepted by the examiner.
IDS
4. The IDS filed on 10/13/2023 are reviewed by the examiner.
Claim Objections
Claim 18 is objected to because of the following informalities:
In claim 18, the claim recites “according to claim 1”. This is improper because the claim 18 depends on the canceled claim 1. Appropriate correction is required.
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 12 and 19 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 pre-AIA the applicant regardn as the invention.
In claim 12 and 19, the term “ Tosic acid ” is recited. This expression can be vague because the claim does not define what is meant by the term “Tosic acid ”.
The examiner recommends to put the corresponding chemical name.
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 9-10, 13-18 are rejected under 35 U.S.C. 112, first paragraph, because the specification, while being enabling for a silica- supported sulfonic acid and Si-Tosic acid as a catalyst does not reasonably provide enablement for all kinds of catalysts known in the art. The specification does not enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to include all kinds of catalysts unrelated to the claimed invention commensurate in scope with these claims.
Furthermore, the instant specification fails to provide information that would allow the skilled artisan to practice the instant invention without undue experimentation.
Attention is directed to In re Wands, 8 USPQ2d 1400 (CAFC 1988) at 1404 where the court set forth the eight factors to consider when assessing if a disclosure would have required undue experimentation, citing Ex Parte Forman, 230 USPQ 546 (BdApls 1986) at 547 the court recited eight factors:
1) the quantity of experimentation necessary,
2) the amount of direction or guidance provided,
3) the presence or absence of working examples,
4) the nature of the invention,
5) the state of the prior art,
6) the relative skill of those in the art,
7) the predictability of the art, and
8) the breath of the claims.
The Nature of the Invention
The nature of the invention in claim 9 is as follows:
9. (New) A method for producing furandicarboxylic acid (FDCA) and furandicarboxylic acid esters (FDCAE) from aldaric acid esters, the method comprising:- adding an aldaric acid ester and a catalyst into a pressure reactor, - adding a non-alcoholic solvent to the pressure reactor, - pressurizing the pressure reactor with an inert gas, - increasing the temperature inside the pressure reactor to a temperature of up to 2400C and mixing the contents of the pressure reactor, - cooling the pressure reactor to a temperature of 20 to 25
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- filtering the catalyst and removing the solvent by evaporation, and - collecting the formed product.
The State of the Prior Art
The states of the prior art are described as followed:
Asikainen et al (WO 2016/166421 A1) discloses a method of producing furan carboxylates from aldaric acids or their esters in the presence of a solid heterogeneous catalyst such as from solid sulfonic acids on different polymer, silica, alumina or zirconia carriers.
GATTINGER et al (US 20170144982 A1) teaches a method for forming 2,5-furan dicarboxylic acid (FDCA), the method comprising: providing a reaction medium comprising a 6-carbon aldaric acid, an acid catalyst, and an ionic liquid; the ionic liquid comprises a counter anion chosen from sulfate, hydrogen sulfate, nitrate, fluoride, chloride, bromide, iodide, methyl sulfonate, and fluoroborate anion. The acid catalyst comprises an acid corresponding to the counter anion of the ionic liquid. The acid catalyst is sulfuric acid, nitric acid, hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, liquid phase organic sulfonic acid, methyl sulfonic acid and/or fluoroboric acid.
Thomas et al (WO 2015/189481 A1) teaches a method for producing muconic acid from aldaric acid, characterized in that the method is also capable of producing furan chemicals, the method comprising selective catalytic dehydroxylation of the aldaric acid by heating the aldaric acid with a solvent and a reductant in a pressurized container to temperatures between 90 to 300 °C in the presence of a transition metal catalyst for a pre-determined reaction time and purifying the resulting product(s).
As the prior art have been discussed in the above, there is no conclusive data that all the kinds of catalysts would work to produce the final desired product in the process except for using the specific catalyst.
The predictability or lack thereof in the art
In the instant case, the instant claimed invention is highly unpredictable since one skilled in the art would recognize that any catalyst would not work on the claimed process in the same way as those catalysts such as a silica- supported sulfonic acid and Si-Tosic acid disclosed in the specification.
According to T.P.Hilditch, the author of the “Catalytic Processes in Applied Chemistry” (see pages Xiii-XV, 1929), there is a definitive reason for an unpredictable aspect of the catalysts in the art of organic chemistry. T.P.Hilditch expressly teaches that any catalyst would not work for any kind of the reaction process; for example, the specific catalysts such as mineral acids, acetic anhydride , sulfuric acid, calcium chloride, and etc can be used for the esterification; on the other hand, this same kind of catalyst will not apply to the other types of the reaction process in the followings: the chlorination of organic compounds, the oxidation of organic compounds, the process for rubber accelerators, the hydrogenation or the dehydrogenation processes, ammonia synthesis, ammonia oxidation , sulfuric acid manufacture, and etc. (see pages Xiii-XV).
Furthermore, the specification of the claimed invention does support the very idea of the unpredictable aspect of the catalysts by disclosing the following specific, workable catalyst for the process, not all kinds of the catalyst known in the art.
Moreover, chemical reactions are well-known to be unpredictable, In re Marzocchi, 169 USPQ 367, In re Fisher, 166 USPQ 18. Additionally, catalytic processes, such as are present here, are inherently unpredictable. The U.S. District Court District of Connecticut held in MOBIL OIL CORPORATION v. W.R. GRACE & COMPANY, 180 USPQ 418 that “there is an inherent mystery surrounding the unpredictability of the performance of catalysts; a mystery which is generally recognized and acknowledged by chemists in the cracking art. This is one more reason why the presumption of patent validity "should not be disregarded especially in a case of this sort where the intricate questions of [bio]chemistry involved are peculiarly within the particular competence of the experts of the Patent Office.” Merck & Co. v. Olin Mathieson Chemical Corp., 253 F.2d 156, 164, 116 USPQ 484, 490 (4th Cir. 1958)". "The catalytic action can not be forecast by its chemical composition, for such action is not understood and is not known except by actual test, Corona Cord Tire Co. v. Dovan Chemical Corp., 276 U.S. 358, 368-369 (1928). Also see, Application of Grant, 304 F.2d 676, 679, 134 USPQ 248, 250-251 (CCPA 1962); Rich Products Corp. v. Mitchell Foods, Inc., 357 F.2d 176, 181, 148 USPQ 522, 525-526 (2d Cir. 1966), cert. denied 385 U.S. 821, 151 USPQ 757 (1966); Ling-Temco-Vought, Inc. v. Kollsman Instrument Corp., 372 F.2d 263, 268, 152 USPQ 446, 450-451 (2d Cir. 1967); Georgia-Pacific Corp. v. United States Plywood Corp., 258 F.2d 124, 132-133, 118 USPQ 122, 128-129."
Therefore, from the above, it is clear that the use of a generic term “ a catalyst can not ensure to form the desired claimed product in a good yield.
The amount of direction or guidance present
The direction present in the instant specification is that not any catalyst can be led to the formation of the desired product. According to the specification, it is silent as to how any catalyst can be led to the formation of the desired product and fails to provide guidance as to whether any catalyst is sufficient enough to allow to form the desired product in sufficient quantities; the specification fails to provide a correlation between the claimed process of the invention and the functional language of any one catalyst layer.
The presence or absence of working examples
There are three examples of using Si-Tosic acid for producing the desired FDCA compound in the specification. This can not be the representatives for all the solid catalysts which would work for the claimed process. Thus, the specification fails to provide enough working examples as to how the other types of catalysts can be resulted in the claimed products, i.e. again, there is no correlation between the functional language of any catalyst and the desired final product.
The breadth of the claims
The breadth of the claims is that any catalyst would work on the claimed process in the same way as the disclosed catalyst without considering the affect or impact of the different catalysts on the starting compound , thereby affecting the yield of the desired final product.
The quantity of experimentation needed
The quantity of experimentation needed is undue experimentation. One of skill in the art would need to determine which one of the catalysts would be capable of forming the desired product and would furthermore then have to determine which one of the catalysts would not be resulted in the claimed desired compounds in a sufficient quantity.
Therefore, in view of the Wands factors and In re Fisher (CCPA 1970) discussed above, to practice the claimed invention herein, a person of skill in the art would have to engage in undue experimentation to test which solid catalyst can be employed to produce the desired claimed compound encompassed in the instant claims, with no assurance of success.
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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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.
5. Claims 9-19 are rejected under 35 U.S.C. 103 as being unpatentable over Asikainen et al (WO 2016/166421 A1) in view of Thomas et al (WO 2015/189481 A1) and Silicycle ( SiliaBond® Tosic Acid, Silicyclem Inc, 2015, p.1-2) and Wikipedia (Methyl acetate ,December 2019, p.1-6).
Determination of the scope and content of the prior art
Asikainen et al discloses a method of producing furan carboxylates from aldaric acids or their esters in the presence of a solid heterogeneous catalyst and a solvent with short reaction time. The feedstock for the production is a stable compound, which allows industrial scaling of the process.
Furthermore, it includes the steps of: charging an aldaric acid, a non-toxic heterogeneous solid acid catalyst and an organic solvent into a pressure reaction vessel to form a reaction mixture, heating the reaction mixture to a temperature of 130 to 250 °C as in claim 15 in said reaction vessel, maintaining the temperature in the reaction vessel for a pre-determined reaction time, cooling the reaction down to room temperature between 20 and 25 °C, collecting the reaction mixture, recovering the desired furan ester(s) and/or acid(s) from the reaction mixture process (see page 4, a paragraph#0024) as in claim 9 in the following example:
To a pressure reactor equipped with magnetic stirring bar and Teflon liner were charged the solvent (20 ml), galactaric acid (2.0 g) and solid catalyst (1.0 g). The reactor was closed and heated in an oil bath to the reaction temperature for indicated time. The reaction could be performed under air or inert gases as in claim 14. After the indicated reaction time, the solid and liquid phases were separated, and organic compounds from the solid phase were extracted with hot solvent. The fractions were analysed with GC-FID for quantitative analysis of each furan compound (see page 10 , lines 5-11).
In addition, it is preferred to use a solvent vapor pressure of 5 to 50 bars as in claim 17 , preferably 15 to 30 bars in the reaction vessel(see page 5 ,a paragraph#0027)
The general method was repeated using a commercial catalyst, phenyl sulfonic acid ethyl sulfide silica, and 1-butanol as solvent. The conditions and the obtained reaction products are given in Table 2 (see page 11 , example 2, table 2) as shown below:
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as in claim 16 , Another suitable raw material or feedstock for furan carboxylate production according to another embodiment is glucaric acid ester having formula XII: glucaric acid ester having formula XII:
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(see page 5 ,a paragrah#0031)
The aldaric acid used as raw material or feedstock is either galactaric acid or glucaric acid in either free acid or ester form.(see page 6, a paragraph#0032)
According to one embodiment, the catalyst is selected from solid sulfonic acids on different polymer, silica, alumina or zirconia carriers. More precisely, the catalyst is selected from perfuorosulfonic acid polymers as in claim 11(such as Nafion NR50), phenyl sulfonic acid ethyl sulfide silica, sulfonated alumina catalyst and sulfonated zirconia catalyst (see page 6, a paragraph#0033).
At least some embodiments of the present invention find industrial application in generating a full value chain from the forest industry, agriculture, or food industry side streams to platform chemicals and end applications. In principle, this chain comprises production of aldaric acids from aldoses and side-stream carbohydrates, converting the aldaric acids to dicarboxylic acids, which in turn are used as platform chemicals for various bio-based applications, as in claim 18 such as bio-based polyesters and nylon. According to one example, the present method produces 2,5-Furandicarboxylic acid for use in the production of polyethylene furanoate (see page 8, aparagraph#0045).
The current invention, however, differs from the prior art in that the aldaric acid ester being mucic acid methyl ester and the catalyst being Si-Tosic acid and the solvent being acetic acid ester (methyl acetate) are unspecified in the prior art.
Thomas et al teaches the purification of mucic acid methyl ester as in claim 10 and its application of for producing FDCA and FDDCAME in the following:
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(see page 9, example 4)
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(see Fig. 1 ).
Also, Silicycle discloses that silia bond tosic acid as in claim 12 can be used as an acid catalyst for organic reactions (see page 1 , the first paragraph).
In addition, Wikipedia teaches that methyl acetate as in claim 13 is occasionally used as a solvent, being weakly polar and lipophilic, but its close relative ethyl acetate is a more common solvent being less toxic and less soluble in water. Methyl acetate has a solubility of 25% in water at room temperature. At elevated temperature its solubility in water is much higher (see page 5, a section of uses).
Ascertainment of the difference between the prior art and the claims
1. The difference between the current application and the applied Asikainen et al art is that the Asikainen et al does not expressly teach the aldaric acid ester being mucic acid methyl ester and the catalyst being Si-Tosic acid and the solvent being acetic acid ester(methyl acetate). The deficiencies of the Asikainen et al are partially cured by Thomas et al , Silicycle and Wikipedia.
2. The difference between the current application and the applied Thomas art is that the Thomas does not expressly teach the catalyst being Si-Tosic acid and the solvent being acetic acid ester(methyl acetate). The deficiencies of the Thomas et al are partially cured by Silicycle and Wikipedia.
3. The difference between the current application and the applied Thomas art is that the Thomas does not expressly teach the catalyst being Si-Tosic acid and the solvent being acetic acid ester(methyl acetate). The deficiencies of the Thomas et al are cured by Silicycle and Wikipedia.
4. The difference between the current application and the applied Silicycle art is that the Silicycle does not expressly teach the method for producing FDCA and FDCAE and the solvent being acetic acid ester(methyl acetate). The deficiencies of the Silicycle are cured by Asikainen et al, Thomas et al and Wikipedia.
5. The difference between the current application and the applied Wikipedia Thomas art is that the Thomas does not expressly teach the method for producing FDCA and FDCAE, the catalyst being Si-Tosic acid. The deficiencies of the Thomas et al are cured partially by Asikainen et al, Thomas et al and Silicycle.
Resolving the level of ordinary skill in the pertinent art.
Regarding the Claim 19 with respect to the lack of disclosing the solvent being acetic acid ester(methyl acetate, Wikipedia does teach that methyl acetate is used as a pleasant smell of a solvent and has a solubility of 25% in water at room temperature. Asikainen et al teaches the use of alcohol instead of methyl acetate as a solvent in the method of producing furan carboxylates from aldaric acids or their esters in the presence of the solid heterogeneous catalyst, Wikipedia does mention that methyl acetate is used as a solvent and has a solubility of 25% in water at room temperature.
So, if the skilled artisan in the art had desired to use methyl acetate as an alternative to the alcohol solvent in the method of producing furan carboxylates from aldaric acids or their esters , it would have been obvious to the skilled artisan in the art to be motivated to do so because of the high solubility in water and its pleasant smell.
Considering objective evidence present in the application indicating obviousness or nonobviousness.
Asikainen et al expressly discloses the method of producing furan carboxylates from aldaric acids or their esters in the steps of: charging the aldaric acid, phenyl sulfonic acid ethyl sulfide silica and the organic alcohol solvent into a pressure reaction vessel to form a reaction mixture, heating the reaction mixture to a temperature of 130 to 250 °C in the reaction vessel, maintaining the temperature in the reaction vessel for a pre-determined reaction time, cooling the reaction down to room temperature between 20 and 25 °C, collecting the reaction mixture, recovering the desired furan ester(s) and/or acid(s) from the reaction mixture process.
Whereas Thomas et al teaches the purification of mucic acid methyl ester and its application of for producing FDCA and FDDCAME. Also, Silicycle discloses that silia bond Tosic acid can be used as an acid catalyst for organic reactions (see page 1 , the first paragraph). In addition, Wikipedia does teach that methyl acetate is used as a solvent, being weakly polar and lipophilic has a solubility of 25% in water at room temperature.
Both of Asikainen et al and Thomas are closely related to the method of producing furan carboxylates from aldaric acids or their esters and its intermediate mucic acid methyl ester compound, whereas Silicycle and Wikipedia teach either the availability of Si-Tosic acid as the acid catalyst or methyl acetate as the solvent in the organic synthesis.
So, if the skilled artisan had desired to perform the method of producing furan carboxylates from aldaric acids or their esters by using mucic acid methyl ester as a starting material in the presence of Si-Tosic acid as the acid catalyst and methyl acetate as the alternative to the alcohol solvent, it would have been obvious to the skilled artisan in the art before the effective filing date of the claimed invention to be motivated to incorporate the teachings of Thomas’s mucic acid methyl ester and Silicycle’s Si-Tosic acid and Wikipedia’s methyl acetate into Asikainen et al method.
This is because the skilled artisan in the chemical art would expect such combined methods to be feasible and successful as guidance shown in the prior art.
Conclusion
Claims 9-19 are rejected.
Claim 18 is objected.
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/TAYLOR V OH/ Primary Examiner, Art Unit 1625 10/15/2025