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 .
Claim Status
Claims 1-21 were filed in a preliminary amendment on 12/19/2023. Claims 1-20 have been amended and claim 21 has been cancelled.
Claims 1-20 are currently pending and under examination.
Priority
The instant application is a national stage application of PCT/KR2022/019067 filed on 11/29/2022, which claims foreign priority to Korean application no. 10-2021-0166974 filed on 11/29/2021, Korean application no. 10-2021-0166975 filed on 11/29/2021, Korean application no. 10-2021-0167306 filed on 11/29/2021, Korean application no. 10-2021-0167409 filed on 11/29/2021, Korean application no. 10-2021-0167455 filed on 11/29/2021, Korean application no. 10-2021-0167456 filed on 11/29/2021, Korean application no. 10-2021-0167457 filed on 11/29/2021, Korean application no. 10-2022-0161897 filed on 11/28/2022.
Should applicant desire to obtain the benefit of foreign priority under 35 U.S.C. 119(a)-(d) prior to declaration of an interference, a certified English translation of the foreign application must be submitted in reply to this action. 37 CFR 41.154(b) and 41.202(e).
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 12/19/2023 is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement has been considered by the examiner.
Objections to the Specification
The use of the term “ASTM”, which is a trade name or a mark used in commerce, has been noted in the third paragraph of page 26 and the second paragraph of page 27 in the instant specification. The term should be accompanied by the generic terminology; furthermore, the term should be capitalized wherever it appears or, where appropriate, include a proper symbol indicating use in commerce such as ™, SM , or ® following the term.
Although the use of trade names and marks used in commerce (i.e., trademarks, service marks, certification marks, and collective marks) are permissible in patent applications, the proprietary nature of the marks should be respected and every effort made to prevent their use in any manner which might adversely affect their validity as commercial marks.
In the instant case, the term “ASTM” is capitalized but does not include the proper symbol indicating use in commerce. Applicant is advised to include the proper symbol with the term.
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 20 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 20 contains the trademark/trade name “ASTM”. Where a trademark or trade name is used in a claim as a limitation to identify or describe a particular material or product, the claim does not comply with the requirements of 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph. See Ex parte Simpson, 218 USPQ 1020 (Bd. App. 1982). The claim scope is uncertain since the trademark or trade name cannot be used properly to identify any particular material or product. A trademark or trade name is used to identify a source of goods, and not the goods themselves. Thus, a trademark or trade name does not identify or describe the goods associated with the trademark or trade name. In the present case, the trademark/trade name is used to identify/describe a standardized method to measure the biobased and biogenic carbon content of a sample using radiocarbon analysis and, accordingly, the identification/description is indefinite.
For purposes of applying prior art, the limitation in instant claim 20 of “ASTM D6866-21” which be interpreted as the standardized method of measuring biocarbon as defined by the published method of ASTM D6866-21.
Claim Interpretation
Regarding the instant limitation “alkali metal” recited in claims 1-20, the term “alkali metal” is used typically to refer to a metal in group 1 of the periodic table. However, the instant specification discloses the term “alkali metal” includes both alkali metal and alkali earth metal. Therefore, the term “alkali metal” is being interpreted to include metals in both groups 1 and 2 of the periodic table.
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.
Claims 1-2, 11-12, and 15-18, and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Abraham et al. (WO2014/144400 A1, published 09/18/2014, PTO-892) in view of Purac et al. (CN104093691B, published 10/08/2014, PTO-892, both translation and original included).
Abraham et al. teaches a method of recovery of 3-hydroxypropionic acid (3-HP) (see title). 3-HP broth produced by fermentation from glucose in yeast is used as the starting material for the processing steps. After completion of the fermentation, various ionic species are present that are desirable to remove. The removal of certain ions is facilitated in the acidification step through the formation of insoluble and/or easily isolatable compounds. For example, undesired calcium present in the fermentation broth is removed by lowering the pH through the addition of H2S04 or other acidic compounds that will form insoluble and/or easily isolatable compounds with calcium (see 0019). The fermentation broth contains 37g/L 3-HP in addition to other fermentation by-products including unfermented sugars, other organic acids such as lactic, pyruvic, succinic, and salts (see 0047). Cell removal and evaporation are typically carried out before the acidulation. It is believed that the concentration of the 3HP and/or salts thereof in the fermentation broth and absence of cells allows for more efficient acidulation and processing after acidulation, such as gypsum removal (see 0086). Referring to step 2 of FIG. 1 (shown below), the fermentation broth is obtained and is fed into several centrifuges. The centrifuges each have a disc stack configuration where the cell free fermentation broth containing 3 HP and/or salts thereof pass through to the product discharge. To improve the recovery of 3HP from the overall recovery process, additional water (2-3 times the volume of the cell concentrate stream) is mixed with the concentrate stream. Referring to FIG. 1 , step 3, the cell free 3HP containing combined broth is evaporated to raise the concentration of 3 HP (and/or salts thereof). The broth feeds into a mechanical vapor recompression (MVR) evaporator to remove water from the broth. The concentrated broth exits the evaporator at 240 g/L 3 HP equivalents. Referring to FIG. 1 , step 4, sulfuric acid is added to evaporated concentrated 3 HP containing broth to lower the pH and convert most of the calcium salts of 3 HP to the free acid form. The CaSO4, formed (also known as gypsum) precipitates out of solution. Referring to FIG. 1, step 5, the acidulated 3HP broth containing gypsum particles is next clarified to remove gypsum. Typically, the evaporation step before the acidulation step is carried out in a
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manner that provides a broth concentrated in 3 HP equivalents, wherein the 3 HP equivalent concentration is below 350 g/L, preferably below 330 g/L. Referring to FIG. 1 , step 6, the clarified 3HP broth is next treated to reduce the total sulfate ions and phosphate ions present in the broth to produce a reduced ion aqueous solution. The broth is passed through a cation exchange column first to remove residual calcium as well as other cations such as potassium and manganese. The 3 HP effluent out of the
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cation column is then fed into an anion column where anions are removed, in particular phosphate and sulfate anions. The properties of the reduced ion aqueous solution comprising 3HP that is obtainable from the above-described demineralization described above are indicated in Table 10-2 (see 0082-0095).
The teachings of Abraham et al. differ from that of the instantly claimed invention in that Abraham et al. does not teach crystallizing the 3-hydroxypropionic acid salt formed in the fermentation process, as required by instant claim 1.
Purac et al. teaches a method of carboxylate acidification (see title). The fermentation process is carried out in a fermentation reactor (1)(see below) to produce a carboxylic acid. Magnesium base is added during the fermentation (not shown) so that magnesium carboxylate is formed. A liquid feed comprising magnesium carboxylate is supplied to the acidification reactor (3) where it is contacted with a gas stream (4) derived from the thermal decomposition step (9). In the acidification reactor (3), magnesium carboxylate is converted to a carboxylic acid and magnesium chloride by reaction with gaseous HCl. A stream comprising an inert gas and usually also gaseous H2O is withdrawn via line (12). The stream (5) comprising the carboxylic acid and magnesium chloride is subjected to a separation step (6). In the figure, this is shown as being carried out in a separate reactor, but depending on the separation method, this can also be carried out in an acidification reactor. The separation step (6) produces a stream (7) comprising a carboxylic acid and a stream (8) as an aqueous liquid comprising magnesium chloride. The stream (8) is supplied to a thermal decomposition unit (9) where magnesium chloride is converted to HCl and MgO and an inert gas is added via line (10). The HCl containing gas stream (4) is supplied to the acidification reactor (3). If desired, the MgO taken out through the line (11) can be reacted with water to form a solution containing magnesium hydroxide, which is recycled to the fermentation reactor (1).
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Figure 2 (shown above) shows a variation of the process of Figure 1 in which the concentration step (13) is inserted between the fermentation step (1) and the acidification step (3). The product stream (21) comprising magnesium carboxylate is withdrawn from the fermentation reactor (1) and supplied to a concentrator (13). Excess water is removed through line (14) and concentrated product stream (22) is provided to acidification step (3). As mentioned before, an attractive embodiment of the process according to the invention is a concentration step in which a concentrated liquid having a temperature of at least 60 ° C, in particular at least 75 ° C, more particularly 80-120 ° C, is produced, as this will have higher selectivity for HCl in the adsorbed liquid feed is obtained compared to adsorbing water from the gas feed (see paragraphs 74-75 of translated document). The concentration of magnesium carboxylate in the liquid feed is not critical, typically 50-750 g/L (see paragraph 22 of translated document). Purac et al. teaches the carboxylate is a mono-, di- or tricarboxylic acid salt comprising at least 2-8 carbon atoms (C2-C8 carboxylate). The C2-C8 carboxylate may be selected from the group consisting of lactate, succinate, propionate, 3-hydroxypropionate, hydroxybutyrate, citrate, fumarate, itaconate, adipic acid salts, acrylates, levulinates, maleates, terephthalates and 2,5-furandicarboxylates (see paragraph 24 of translated document). Purac et al. teaches the fermentation process can include a purification step in which the magnesium carboxylate is crystallized from the fermented nutrient base, which can then be dissolved in water to form an aqueous solution, which typically has a higher concentration of carboxylate than the fermented nutrient base. This purification step may have the advantage of being able to achieve higher yields in the first precipitation step due to the higher concentration of magnesium carboxylate (see paragraph 114 of translated document).
It would have been obvious before the effective filing date of the claimed invention to combine the teachings of Abraham et al. with the teachings of Purac et al. by crystallizing 3-hydroxypropionate using magnesium hydroxide as a neutralizing base, as taught by Purac et al., to arrive at the instantly claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to crystallize the magnesium 3-hydroxyprionate because, as taught by Purac et al., has the advantage of being able to achieve higher yields in the first precipitation step due to the higher concentration of magnesium carboxylate. One of ordinary skill in the art would have a reasonable expectation of success because purification of starting materials (i.e. crystallizing the magnesium carboxylate) is routine method optimization.
Regarding instant claims 1, the evaporated concentrated 3 HP containing broth, as taught by Abraham et al., corresponds to the instant concentrate containing 3-hydroxypropionic acid which is combined with using magnesium hydroxide, corresponding to the instant alkali metal salt, as a neutralizing base to crystallize 3-hydroxyprionate, as taught by Purac et al., corresponding to the instant 3-hydroxypropionic acid crystal. Abraham et al. further teaches sulfuric acid is added to 3 HP containing broth to lower the pH and convert most of the calcium salts of 3 HP to the free acid form. The CaS04, formed (also known as gypsum) precipitates out of solution, corresponding to the instant alkali metal salt hydrate. The acidulation step corresponds to the instant step of adding an acid to the aqueous solution containing 3-HP acid salt crystal to form alkali metal salt hydrate and 3-hp acid. Regarding the step of forming an aqueous solution containing the 3-HP acid salt crystal, Purac et al. teaches the crystals can be separated from the fermentation broth and put into an aqueous solution, corresponding to the instant step of forming an aqueous solution containing the 3-HP acid salt crystal. Abraham et al. further teaches the acidulated 3HP broth containing gypsum particles is next clarified to remove gypsum, corresponding to the instant step of separating the alkali metal salt hydrate and the 3-
HP acid.
Regarding instant claim 2 and 17, Abraham et al. teaches the solution of 3-HP equivalents can be concentrated to 240 g/L, as shown in Table 10-2 above, corresponding to the instant aqueous solution containing at least 100 g/L of the 3-HP acid salt crystal as required by instant claim 2. Furthermore, the solution of 3-HP equivalents having a concentration of 240 g/L corresponds to the instant concentration of 100 g/L or more and 800 g/L or less as required by instant claim 17.
Regarding instant claim 11, Abraham et al. teaches after the acidulation and clarification steps,
corresponding to the instant step of adding an acid and separating the alkali metal salt hydrate, the
clarified 3HP broth is next treated to reduce the total sulfate ions and phosphate ions present in the
broth to produce a reduced ion aqueous solution. The broth is passed through a cation exchange
column which produced a 3-HP effluent, corresponding to the instant step of contacting a solution
containing 3-HP acid formed after separating the alkali metal salt hydrate with a cation exchange resin
column and recovering the 3-HP acid.
Regarding instant claim 12, Purac et al. teaches a concentrated liquid, corresponding to the instant aqueous solution, having a temperature of at least 60 °C, corresponding to the instant temperature of the aqueous solution of 0 °C or more and 90 °C or less. 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 MPEP 2144.05).
Regarding instant claims 15-16, one of ordinary skill in the art would understand the concentration of 3-HP is optimizable by known methods. Furthermore, Purac et al. teaches the concentration of magnesium carboxylate in the liquid feed is not critical, typically 50-750 g/L. Likewise, one of ordinary skill in the art would understand that the amount of magnesium carboxylate necessarily flows from the amount of carboxylic acid in the liquid feed. Therefore, the amount of carboxylic acid in the liquid feed prior to forming the magnesium carboxylate would be 50-750 g/L as well, corresponding to the instant concentrate containing at least 300 g/L of 3-HP, as required by instant claim 15, and 350 g/L-900 g/L of 3-hydroxyprionic acid, as required by instant claim 16. 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 MPEP 2144.05).
Regarding instant claim 18, Purac et al. teaches the base used is Mg(OH)2, corresponding to the instant alkali metal salt being Mg(OH)2.
Regarding instant claim 20, the limitation of the 3-hydroxypropionic acid salt crystal has a particle size distribution D50 of 20 μm or more and 90 μm or less, and (D90-D10)/D50 of 1.00 or more and 3.00 or less and have a radioactive isotope content of 20 pMC (percent modern carbon) or more and a biocarbon content of 20 wt% or more as measured by ASTM D6866-21 standard are all functions of the crystal produced that would necessarily flow from the method used to make the crystal. Therefore, since the method to produce 3-HP crystal is obvious over Purac et al., the crystals produced and therefore, their functions are also obvious.
Claim 3 is rejected under 35 U.S.C. 103 as being unpatentable over Abraham et al. (WO2014/144400 A1, published 09/18/2014, PTO-892) in view of Purac et al. (CN104093691B, published 10/08/2014, PTO-892), as applied to claim 1 above, and further in view of Huang et al. (NPL, published 11/25/2006, PTO-892).
The combined teachings of Abraham et al. and Purac et al. were discussed above.
The combined teachings of Abraham et al. and Purac et al. differ from that of the instantly claimed invention in that Abraham et al. and Purac et al. does not teach electrodialyzing the acid-added solution from which the alkali metal salt hydrate has been separated.
Huang et al. teaches conventional electrodialysis (CED) for demineralizing or concentrating organic acids or organic salts. When it comes to organic acid production, CED has been used to demineralize or concentrate organic acids or organic salts. In the case of demineralization, it is better to acidify the feed so that most of organic anions can exist in the form of acid molecules and stay in the feed, and more inorganic anions can migrate into the adjacent compartment (see section 3.1).
It would have been obvious before the effective filing date of the claimed invention to combine the teachings of Abraham et al. and Purac et al. with the teachings of Huang et al. by producing 3-HP crystals and acidifying the resultant 3-HP crystals, as taught by Abraham et al. and Purac et al., and electrodialyzing an acidified solution of organic acid, as taught by Huang et al., to arrive at the instantly claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to electrodialyze the acidified solution because, as taught by Huang et al., electrodialysis of an acidified solution of organic acid will demineralize the solution. Therefore, this will increase the purity of the organic acid produced. One of ordinary skill in the art would have a reasonable expectation of success because Huang et al. teaches CED can demineralize organic acids and furthermore, acidified solutions keep more of the organic acid in the feed which would increase yield.
Claim 4 is rejected under 35 U.S.C. 103 as being unpatentable over Abraham et al. (WO2014/144400 A1, published 09/18/2014, PTO-892) in view of Purac et al. (CN104093691B, published 10/08/2014, PTO-892) in view of Huang et al. (NPL, published 11/25/2006, PTO-892), as applied to claim 3 above, and further in view of Merkel et al. (NPL, published 11/21/2020, PTO-892).
The combined teachings of Abraham et al., Purac et al., and Huang et al. were discussed above.
The combined teachings of Abraham et al., Purac et al., and Huang et al. differ from that of the instantly claimed invention in that they do not teach wherein the electrodialyzing is carried out until the time point when electrical conductivity in a desalination tank for recovering a desalting product formed by the electrodialyzing is reduced to 50% or less of an initial electrical conductivity in the desalination tank.
Merkel et al. teaches an electrodialytic desalination on acid whey stream (see title). The nanofiltrated acid whey (NFAW) was obtained in curd produced and provided by Madeta a.s. milk factory (Jindřichův Hradec, Czech Republic), which produces milk-based desserts, yoghurts, fermented milk products, as well as curd and yoghurt desserts using acidification by ferments. The NFAW before and after ED was characterized in terms of conductivity (see section 2.1). The conductivity of the solutions was recorded every 5 min. The starting conductivity of the solution is 8.4 mS⋅cm−1 (see Table 1). After ∼60 min, the electrodialysis of salt was interrupted when the conductivity of diluate was below 1 mS⋅cm−1 (see section 2.2.1).
It would have been obvious before the effective filing date of the claimed invention to combine the teachings of Abraham et al., Purac et al., and Huang et al. with the teachings of Merkel et al. by electrodialyzing an acidified solution of organic acid, as taught by Abraham et al., Purac et al., and Huang et al., and stopping the electrodialysis based on a predetermined decrease in conductivity. It would have been prima facie obvious for one of ordinary skill in the art to stop the electrodialysis based on conductivity measurements because Merkel et al. teaches stopping electrodialysis of NFAW based on a predetermined conductivity measurement. One of ordinary skill in the art would have a reasonable expectation of success because measuring conductivity levels to determine desalination efficiency is routine optimization of electrodialysis.
Regarding instant claim 4, Merkel et al. teaches a starting conductivity of 8.4 mS⋅cm−1 and stops the electrodialysis when the conductivity in the diluate, corresponding to the instant desalination tank, is below 1 mS⋅cm−1 which is calculated to 11.9% of the original conductivity, corresponding to the instant electrical conductivity being reduced to 50% or less of the initial value.
Claims 5-9 are rejected under 35 U.S.C. 103 as being unpatentable over Abraham et al. (WO2014/144400 A1, published 09/18/2014, PTO-892) in view of Purac et al. (CN104093691B, published 10/08/2014, PTO-892), as applied to claim 1 above, and further in view of Hanchar et al. (EP2681182B1, published 12/27/2017, PTO-892)
The combined teachings of Abraham et al. and Purac et al. were discussed above. Purac et al. further teaches Mg(OH)2 can be used as a neutralizing agent in a fermentation process. Alternatively, Mg(OH)2 is first converted to magnesium carbonate (MgCO3), which is then used as a neutralizing agent in the fermentation process (see paragraph 62 of translated document).
The combined teachings of Abraham et al. and Purac et al. differ from that of the instantly claimed invention in that Abraham et al. and Purac et al. does not teach reacting the alkali metal salt hydrate with ammonia water or a hydroxide ion containing solution to form an alkali metal hydroxide.
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Hanchar et al. teaches a process flow diagram showing a process of producing an organic acid using a magnesium salt, recycling at least a portion of the magnesium salt, and separating ammonium sulfate that is also produced in the process (see Fig. 2 below and 0012).
Regarding instant claims 5-8, it would have been obvious before the effective filing date of the claimed invention to combine the teachings of Abraham et al. and Purac et al. with the teachings of Hanchar et al. by separating the magnesium sulfate, as taught by Abraham et al. and Purac et al., and reacting the magnesium sulfate with ammonium hydroxide, as taught by Hanchar et al., to arrive at the instantly claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to react the magnesium sulfate with ammonium hydroxide because, as taught by Hanchar et al., this enables the recycling of the salt to fermentation processes which reduces waste. One of ordinary skill in the art would have a reasonable expectation of success because reacting magnesium sulfate with ammonium hydroxide to precipitate magnesium hydroxide and form ammonium sulfate is a routine, well-characterized chemical reaction that follows predictable solubility and thermodynamic principles.
Regarding instant claim 9, it would have been obvious before the effective filing date of the claimed invention to combine the teachings of Abraham et al. and Purac et al. with the teachings of Hanchar et al. by separating the magnesium sulfate, as taught by Abraham et al. and Purac et al., and reacting the magnesium sulfate with ammonium hydroxide, as taught by Hanchar et al., and further converting the formed magnesium hydroxide to magnesium carbonate, as taught by Purac et al., to arrive at the instantly claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to form magnesium carbonate from magnesium sulfate because, as taught by Hanchar et al., this enables the recycling of the salt to fermentation processes which reduces waste. Furthermore, Purac et al. teaches magnesium carbonate can be substituted for magnesium hydroxide as the neutralizing agent in the fermentation process. One of ordinary skill in the art would have a reasonable expectation of success because reacting magnesium sulfate with ammonium hydroxide to precipitate magnesium hydroxide and further convert this to magnesium carbonate is a routine, well-characterized chemical reaction that follows predictable solubility and thermodynamic principles.
Claim 10 is rejected under 35 U.S.C. 103 as being unpatentable over Abraham et al. (WO2014/144400 A1, published 09/18/2014, PTO-892) in view of Purac et al. (CN104093691B, published 10/08/2014, PTO-892), as applied to claim 1 above, and further in view of Tengler et al. (WO2013192450A1, published 12/27/2013, PTO-892).
The combined teachings of Abraham et al. and Purac et al. were discussed above.
The combined teachings of Abraham et al. and Purac et al. differ from that of the instantly claimed invention in that Abrahm et al. and Purac et al. do not teach wherein the acid is phosphoric acid, and the alkali metal salt hydrate is phosphoric acid salt.
Tengler et al. teaches purification of 3-hydroxypropionic acid from crude cell broth. The process includes (a) providing a fermentation broth comprising 3-HP, or salt thereof; (b) removing a substantial amount of water from said fermentation broth to give a concentrated fermentation broth; (c) extracting said 3-HP from said concentrated fermentation broth with an organic solvent, wherein said organic solvent has a boiling point of less than 170 °C; and (d) distilling the extract from step (c) to give said high purity 3-HP and/or its ester (see claim 1). The process further includes adjusting pH of said concentrated
fermentation broth with an acid after step (b) (see claim 17). Tengler et al. further teaches the pH is adjusted with an inorganic acid. The inorganic acid is sulfuric acid or phosphoric acid. During the pH adjusting process, solids may precipitate out of the concentrated acidic broth. The solids can be separated from the rest of the material, for example, by filtration (see 0008).
It would have been obvious before the effective filing date of the claimed invention to substitute the teachings of Abraham et al. and Purac et al. with the teachings of Tengler et al. by substituting the sulfuric acid, as taught by Abraham et al., with phosphoric acid, as taught by Tengler et al., to arrive at the instantly claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to substitute sulfuric acid with phosphoric acid because, as taught by Tengler et al., both phosphoric acid and sulfuric acid are capable of acidifying 3-HP from fermentation broth. One of ordinary skill in the art would have a reasonable expectation of success because Tengler et al. teaches that both of these acids perform the same functional role.
Claims 19 are rejected under 35 U.S.C. 103 as being unpatentable over Abraham et al. (WO2014/144400 A1, published 09/18/2014, PTO-892) in view of Purac et al. (CN104093691B, published 10/08/2014, PTO-892), as applied to claim 1 above, and further in view of McDonald et al. (NPL, published 2021, IDS dated 12/19/2023).
The combined teachings of Abraham et al. and Purac et al. were discussed above.
The combined teachings of Abraham et al. and Purac et al. differ from that of the instantly claimed invention in that Abraham et al. and Purac et al. does not teach the alkali metal salt is Ca(OH)2 or the 3-HP acid salt crystal including 3-HP acid calcium salt.
McDonald et al. teaches addition of a neutralizing base such as one of the calcium compounds Ca(OH)2, CaO, or CaCO3 stabilizes pH and causes many carboxylic acids to crystallize as calcium salts, which may further benefit the fermentation by sequestering inhibitory products.154 Magnesium compounds are also used, but to a lesser extent (see page 376, first paragraph).
It would have been obvious before the effective filing date of the claimed invention to substitute the teachings of Abraham et al. and Purac et al. with the teachings of McDonald et al. by substituting the magnesium hydroxide, as taught by Purac et al., with calcium hydroxide, as taught by McDonald et al. to arrive at the instantly claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to substitute the magnesium hydroxide for calcium hydroxide because, as taught by McDonald et al., both calcium and magnesium hydroxide can be used as bases in the fermentation process to produce carboxylic acids. One of ordinary skill in the art would have a reasonable expectation of success because McDonald et al. teaches both bases function to neutralize the pH in the fermenter and crystallize the produced carboxylate.
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.
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Claims 1, 18, and 20 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 3, 6, and 10 of copending Application No. 18/010033 (‘033) in view of Purac et al. (CN104093691B, published 10/08/2014, PTO-892).
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Although the claims at issue are not identical, they are not patentably distinct from each other because ‘033 recites
1. A process of recovering 3-hydroxypropionic acid, comprising the steps of: forming a concentrate containing the 3-hydroxypropionic acid in an amount of 350 g/L or more to 900 g/L or less by concentrating the purified fermented solution; forming crystals of 3-hydroxypropionate in the concentrate by stirring in the presence of a metal salt comprising at least one cation selected from the group consisting of Na+, Mg2+; separating the crystals of 3-hydroxypropionate from the concentrate, and converting the crystals into 3-hydroxypropionic acid.
3. The process of claim 1 wherein the metal salt is Ca(OH)2, Mg(OH)2, or a mixture thereof.
6. The process of claim 1 wherein the crystals of 3-hydroxypropionate have a particle size distribution D50 of 20 μm or more and 90 μm or less, and (D90-D10)/D50 of 1.00 or more and 3.00 or less.
10. The process of claim 1 wherein the crystals of 3-hydroxypropionate have a radioactive isotope content of 20 pMC (percent modern carbon) or more and a biocarbon content of 20 wt% or more as measured by ASTM D6866-21 standard.
The claims of ‘033 differs from that of the instantly claimed invention in that ‘033 does not exemplify the step of adding an acid to the aqueous solution to form and separate the alkali metal salt hydrate and 3-HP acid.
The teachings of Purac et al. were discussed above.
It would have been obvious before the effective filing date of the claimed invention to combine ‘033 with the teachings of Purac et al. by producing crystals of 3-hydroxypropionate, as recited by ‘033, and recovering 3-HP from the crystals, as taught by Purac et al., to arrive at the instantly claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to recover 3-HP from the crystals of 3-hydroxypropionate because the acidification, as taught by Purac et al., is used to convert the crystals of 3-HP to the free acid form. One of ordinary skill in the art would have a reasonable expectation of success because acidifying carboxylate salts to produce the free acid is a well-established reaction.
Regarding instant claim 18, ‘033 recites wherein the metal salt is Ca(OH)2, Mg(OH)2, or a mixture thereof, corresponding to the instant alkali metal salt being Ca(OH)2, Mg(OH)2 or a mixture thereof.
Regarding instant claim 20, ‘033 recites wherein the crystals of 3-hydroxypropionate have a particle size distribution D50 of 20 μm or more and 90 μm or less, and (D90-D10)/D50 of 1.00 or more and 3.00 or less and have a radioactive isotope content of 20 pMC (percent modern carbon) or more and a biocarbon content of 20 wt% or more as measured by ASTM D6866-21 standard, corresponding to the instant 3-hydroxypropionic acid salt crystal having a particle size distribution D50 of 20 μm or more and 300 μm or less, and a (D90-D10)/D50 of 1.00 or more and 3.00 or less, and the 3-hydroxypropionic acid salt crystal has a radioactive carbon isotope content of at least 20 pMC (percent modern carbon), and a biocarbon content of at least 20 wt.%, as measured according to the standard of ASTM D6866-21.
Claims 1-2, 13, and 15-17 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 6-8, and 10 of copending Application No. 18/570596 (‘596).
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Although the claims at issue are not identical, they are not patentably distinct from each other because ‘596 recites:
1. A process of recovering an alkali metal sulfate, comprising: forming an organic acid fermentation liquid containing an alkali metal salt of an organic acid; and adding sulfuric acid to the organic acid fermentation liquid to form and recover an alkali metal sulfate.
6. The process of recovering an alkali metal sulfate according to claim 1, wherein: the alkali metal sulfate is recovered as a crystal of the alkali metal sulfate having a particle size of 0.5 μm to 100 μm.
7. The process of recovering an alkali metal sulfate according to claim 1, wherein: the adding sulfuric acid to the organic acid fermentation liquid to form and recover an alkali metal sulfate further comprises, forming and separating an alkali metal salt crystal of organic acid in the organic acid fermentation liquid in the presence of an alkali metal salt; preparing a solution containing the alkali metal salt crystal of organic acid; and adding sulfuric acid to the solution containing the alkali metal salt crystal of organic acid to form and recover the alkali metal sulfate.
8. The process of recovering an alkali metal sulfate according to claim 1 or 7, wherein: the organic acid fermentation liquid or the solution containing the alkali metal salt crystal of organic acid contains 10 g/L to 600 g/L of an alkali metal salt of organic acid or an organic acid.
10. The process of recovering an alkali metal sulfate according to claim 1, further comprising: recovering an organic acid formed when adding sulfuric acid to an organic acid fermentation liquid containing the alkali metal salt of organic acid.
The claims of ‘596 differs from that of the instantly claimed invention in that ‘596 does not recite that the formed solution of the 3-HP crystal is aqueous, as required by instant claim 1, wherein the aqueous solution contains at least 100 g/L of the 3-hydroxypropionic acid salt crystal, as required by instant claim 2, wherein the concentrate contains at least 300 g/L of the 3-hydroxypropionic acid as required by instant claim 15, and wherein the aqueous solution contains the 3-hydroxypropionic acid salt crystal at a concentration of 100 g/L or more and 800 g/L or less as required by instant claim 17.
However, it would have been obvious before the effective filing date of the claimed invention to modify the process as recited by ‘596 by using an aqueous solvent to form the solution of 3-HP crystal to arrive at the instantly claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to use an aqueous solution because an aqueous solution is required to dissociate the organic acid anion from the cation during the acidification step which allows for the free ions to react faster. One of ordinary skill in the art would have a reasonable expectation of success because organic acid salts are generally soluble in aqueous solutions and the choice of solvent is a routine step in process optimization.
Regarding instant claim 1, ‘596 recites forming and separating an alkali metal salt crystal of organic acid in the organic acid fermentation liquid in the presence of an alkali metal salt, corresponding to the instant step of forming and separating a 3-hydroxypropionic acid salt crystal from a concentrate containing 3-hydroxypropionic acid in the presence of an alkali metal salt. ‘596 further recites preparing a solution containing the alkali metal salt crystal of organic acid, corresponding to the instant step of forming an aqueous solution containing the 3-hydroxypropionic acid salt crystal. Lastly, ‘596 recites adding sulfuric acid to the solution containing the alkali metal salt crystal of organic acid to form and recover the alkali metal sulfate, corresponding to the instant step of adding an acid to the aqueous solution containing the 3-hydroxypropionic acid salt crystal to form and separate the alkali metal salt hydrate and the 3-hydroxypropionic acid.
Regarding instant claim 2, ‘596 recites the solution containing the alkali metal salt crystal of organic acid contains 10 g/L to 600 g/L of an alkali metal salt of organic acid, corresponding to the instant aqueous solution containing at least 100 g/L of the 3-hydroxypropionic acid salt crystal. 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 MPEP 2144.05).
Regarding instant claim 13, ‘596 recites the alkali metal sulfate is recovered as a crystal of the alkali metal sulfate having a particle size of 0.5 μm to 100 μm, corresponding to the instant precipitate having a particle size of 0.5 μm or more and 500 μm or less is formed during the adding of the acid to the aqueous solution containing the 3-hydroxypropionic acid salt crystal. 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 MPEP 2144.05).
Regarding instant claim 15, ‘596 recites the organic acid fermentation liquid contains 10 g/L to 600 g/L of an organic acid, corresponding to the instant concentrate containing 350 g/L or more and 900 g/L or less of the 3-hydroxypropionic acid. 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 MPEP 2144.05).
Regarding instant claim 16, ‘596 recites the organic acid fermentation liquid contains 10 g/L to 600 g/L of an organic acid, corresponding to the instant concentrate containing 350 g/L or more and 900 g/L or less of the 3-hydroxypropionic acid. 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 MPEP 2144.05).
Regarding instant claim 17, ‘596 recites the solution containing the alkali metal salt crystal of organic acid contains 10 g/L to 600 g/L of an alkali metal salt of organic acid, corresponding to the instant aqueous solution containing the 3-hydroxypropionic acid salt crystal at a concentration of 100 g/L or more and 800 g/L or less. 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 MPEP 2144.05).
Claims 1, 12-14, and 18 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 3, 15-16, and 18 of copending Application No. 18/570184 (‘184).
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Although the claims at issue are not identical, they are not patentably distinct from each other because ‘184 recites:
1. A process of recovering 3-hydroxypropionic acid, comprising: forming a 3-hydroxypropionate crystal in a concentrate containing 3-hydroxypropionic acid in the presence of an alkali metal salt; preparing a solution containing 3-hydroxypropionate crystal separated from the concentrate; stirring an acid and the solution containing 3-hydroxypropionate crystal to form a precipitate; and subjecting the precipitate to a first washing.
3. The process of recovering 3-hydroxypropionic acid according to claim 1, wherein: before the stirring an acid and the solution containing 3-hydroxypropionate crystal to form a precipitate, the process further comprises adding an acid to the solution containing 3-hydroxypropionate crystal at a temperature of 30 °C or more and 90 °C or less.
15. The process of recovering 3-hydroxypropionic acid according to claim 1, wherein: a particle size of the precipitate is at least 1.0 μm.
16. The process of recovering 3-hydroxypropionic acid according to claim 1, wherein: a moisture content of the precipitate is 150% or less.
18. The process of recovering 3-hydroxypropionic acid according to claim 1, wherein: the alkali metal salt is Ca(OH)2, Mg(OH)2, or a mixture thereof.
‘184 differs from that of the instantly claimed invention in that ‘184 does not recite that the formed solution of the 3-HP crystal is aqueous, as required by instant claim 1, wherein the acid is added to aqueous solution containing the 3-hydroxypropionic acid salt crystal at a temperature of the aqueous solution of 0 °C or more and 90 °C or less as required by instant claim 12, wherein a precipitate having a particle size of 0.5 μm or more and 500.0 μm or less is formed during the adding of the acid to the aqueous solution containing the 3-hydroxypropionic acid salt crystal as required by instant claim 13, and wherein a moisture content of the precipitate is 200% or less as required by instant claim 14.
However, it would have been obvious before the effective filing date of the claimed invention to modify the process as recited by ‘184 by using an aqueous solvent to form the solution of 3-HP crystal to arrive at the instantly claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to use an aqueous solution because an aqueous solution is required to dissociate the organic acid anion from the cation during the acidification step which allows for the free ions to react faster. One of ordinary skill in the art would have a reasonable expectation of success because organic acid salts are generally soluble in aqueous solutions and the choice of solvent is a routine step in process optimization.
Regarding instant claim 1, ‘184 recites forming a 3-hydroxypropionate crystal in a concentrate containing 3-hydroxypropionic acid in the presence of an alkali metal salt, corresponding to the instant step of forming a 3-HP acid salt crystal from a concentrate containing 3-hydroxypropionic acid in the presence of an alkali metal salt. ‘184 further recites preparing a solution containing 3-hydroxypropionate crystal separated from the concentrate, corresponding to the instant step of separating the crystal from the concentrate. ‘184 further teaches stirring an acid and the solution containing 3-hydroxypropionate crystal to form a precipitate and subjecting the precipitate, corresponding to the instant alkali metal salt hydrate to a first washing, which naturally flows into the instant step of separating the alkali metal salt hydrate and the 3-HP.
Regarding instant claim 12, ‘184 recites adding an acid to the solution containing 3-hydroxypropionate crystal at a temperature of 30 °C or more and 90 °C or less, corresponding to the instant step of the acid is added to aqueous solution containing the 3-hydroxypropionic acid salt crystal at a temperature of the aqueous solution of 0 °C or more and 90 °C or less. 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 MPEP 2144.05).
Regarding instant claim 13, ‘184 recites a particle size of the precipitate is at least 1.0 μm, corresponding to the instant precipitate having a particle size of 0.5 μm or more and 500.0 μm or less formed during the adding of the acid to the aqueous solution containing the 3-hydroxypropionic acid salt crystal. 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 MPEP 2144.05).
Regarding instant claim 14, ‘184 recites wherein a moisture content of the precipitate is 150% or less, corresponding to the instant moisture content of the precipitate being 200% or less. 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 MPEP 2144.05).
Regarding instant claim 18, ‘184 recites the alkali metal salt is Ca(OH)2, Mg(OH)2, or a mixture thereof, corresponding to the instant alkali metal salt being Ca(OH)2, Mg(OH)2 or a mixture thereof.
Allowable Subject Matter
Claims 13-14 would be allowable if amended to overcome the Double Patenting rejection above.
Regarding the instant limitations of a precipitate having a particle size of 0.5-500.0 μm and a moisture content of 200% or less is formed during the adding of the acid to the aqueous solution containing the 3-hydroxypropionic acid salt crystal, based on the structural information of the reaction and precipitate recited in the claims as well as description given in the specification (see page 4, third paragraph), one of ordinary skill in the art would understand the precipitate to be a chemical derivative of the reaction between the claimed acid and the claimed alkali metal salt hydrate and not a 3-HP precipitate. Therefore, the closest prior art is Zurz et al. (NPL, published 03/08/2005). Zurz et al. teaches studying the possibilities to obtain α-hemihydrate from flue gas gypsum, a waste product produced in large volumes in the generation of electricity from coal. The experiments were performed using both various salt and sulfuric acid solutions. Also included in our work was the study of the effect of a series of agents added to the system, to modify the morphology of the formed α-hemihydrate crystals and thus to improve the quality of the produced binder. Zurz et al. also teaches using varying conditions to include heat, addition of sulfuric acid, and addition of an organic acid additive to produce precipitates of gypsum in differing hydrate states with various crystal morphologies (see Introduction section). Table IV shows the reaction product formed and the crystal morphology of different flue gas gypsum products treated in sulfuric acid solutions of different concentration and heated to different temperatures. It appears that the outcome of the treatment at equal experimental conditions depended also on the quality of the starting flue gas gypsum used. A dehydration of the dihydrate got under way only if a threshold concentration of the acid and a threshold temperature were exceeded. At too high acid concentrations, calcium sulfate anhydrite, rather than hemihydrate, was formed as the reaction product. A simultaneous presence of a-hemihydrate and anhydrite in the produced material was common (see Morphology-Sulfuric Acid Solutions section).
While Zurz et al. teaches the morphology and moisture content of gypsum precipitates produced from electrolyte solutions can be influenced by the addition of organic acids, sulfuric acid, and heat, one of ordinary skill in the art would not have a reason to combine this with the process with the teachings of Purac et al. (cited above) because Zurz et al. focuses on gypsum produced from the electrical production industry and not gypsum produced from fermentation waste. Furthermore, this results in gypsum precipitates used for binders in industry and not for use in fermentation processes. Furthermore, no prior art discusses the control of morphology of gypsum crystals produced from fermentation processes. Therefore, there is no motivation to combine the teachings of Purac et al. with Zurz et al. and claims 13-14 are free of prior art.
Conclusion
No claim is found allowable.
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/KRISTEN W BRADY/ Examiner, Art Unit 1692
/AMY C BONAPARTE/ Primary Examiner, Art Unit 1692
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