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 .
Priority
This application is a 371 of PCT/EP2021/062450 filed 05/11/2021. Applicant’s claim for the benefit of a prior-filed application under 35 U.S.C. 119(e) or under 35 U.S.C. 120, 121, 365(c), or 386(c) is acknowledged.
Acknowledgment is made of applicant’s claim for foreign priority under 35 U.S.C. 119 (a)-(d) based on EPO 20175376.1 filed 05/19/2020. Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Status of the Claims
Claims 1-22 are pending. Claims 1, 3, 5, 10, 13 and 22 are amended. Claim 20 was withdrawn.
Claims 1-19, 21 and 22 (claim set filed 08/08/2025) are examined on the merits herein.
Withdrawal of Rejections
The response and amendment filed on 08/08/2025 are acknowledged. All of the amendment and arguments have been thoroughly reviewed and considered.
For the purposes of clarity of the record, the reasons for the Examiner's withdrawal and/or maintaining if applicable, of the substantive or essential claim rejections are detailed directly below and/or in the Examiner's response to arguments section.
The previous claims 1, 3 and 22 objections have been withdrawn necessitated by amendment of claims 1, 3 and 22.
The previous claims 5, 10 and 13 rejections under 35 U.S.C. 112(b) have been withdrawn necessitated by amendment of claims 5, 10 and 13.
The previous claims 1-11 and 21 double patenting rejection over application 17/292,857 has been withdrawn necessitated by abandonment of application 17/292,857.
The previous claims 1, 6 and 10 double patenting rejection over application 16/969,853 has been withdrawn necessitated by abandonment of application 16/969,853.
Maintained Rejections
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1-6, 10, 11-13, 18, 19, 21 and 22 are rejected under 35 U.S.C. 103 as being unpatentable over Gildemyn (Gildemyn et al. Biotechnol. Biofuels, 2017, 10, 83, 1-15) in view of Lee (Lee et al. Applied Catalysis A: General, 2015, 506, 288-293 on record in IDS), Alonzo (Alonzo et al. Tetrahedron, 2008, 64, 1847-1852 on record in IDS), Taco-Vasquez (Taco-Vasquez and Holtzappe AIChE Journal, 2016, 62, 1707- 1715) and Morris (US 4158668 A on record in IDS) and as evidenced by PubChem (PubChem CID 8892, Caproic acid [retrieved on 07/17/2025]. Retrieved from the Internet: <https://pubchem.ncbi.nlm.nih.gov/compound/Caproic-Acid>) and Ahmadvand (Ahmadvand et al. Int. J. Envir. Sci. & Technol., 2020, 17, 3541-3548).
Regarding claim 1, Gildemyn teaches Clostridium kluyveri culture that converts ethanol/acetic acid mixtures to medium-chain carboxylic acids (Abstract). Gildemyn describes production of n-butyric acid comprising 4 carbon atoms and n-caproic acid comprising 6 carbon atoms (p. 8, left column, 2nd paragraph). Gildemyn mentions the high rate of n-caproic acid production: “Increasing the organic loading rates resulted in proportionally higher production rates of n-caproic acid, which were up to 40 mM day−1 (4.64 g L−1 day−1) at carbon conversion efficiencies of 90% or higher.” (Abstract and Figure 4). N-caproic acid is the hexanoic acid as evidenced by PubChem. Gildemyn discloses in-line extraction of produced alkanoic acids in the bioreactor (Abstract). The extraction is performed in a solvent consisting of mineral oil containing tri-n-octylphosphine oxide (TOPO) (p. 5, left column).
Thus, Gildemyn teaches steps (a) and (b) of the method of producing linear fatty acids.
Gildemyn does not teach steps (c)-(f), i.e. steps of ketonization, hydrogenation, dehydration and hydroxy or alkoxy carbonylation.
Lee teaches ketonization of hexanoic acid to ketone, 6-undecanone, (Abstract) to produce “high-energy- density C11 ketone from biologically produced hexanoic acid (p. 288, right column, last paragraph). Ketonization was performed with several metal oxide catalysts, including zirconia oxide (ZrO2) (p. 289, right column, 3rd paragraph, Table 1). Zirconia oxide exhibited excellent stability and negligible leaching in contrast to MgO and MnOx (p. 292, left column, 1st paragraph). Zirconia oxide was used in the form of aerogel providing high surface area: “A high-surface-area zirconia aerogel was prepared, which successfully ketonized hexanoic acid to 6-undecanone with high conversion, 72.3%, and high selectivity, 92.6%.” (Abstract). Lee concluded that: “High-surface-area zirconia aerogels exhibited high stability and excellent catalytic activity under a flow of a hexanoic acid reactant, which must be appropriate for a continuous process.” (p. 292, right column, last paragraph). Thus, Lee teaches step (c) of the method of producing linear fatty acids.
Alonso teaches reduction of variety of ketones and aldehydes by transfer hydrogenation in the presence of nickel nanoparticles (Abstract). Alonso mentions that while several noble metal catalysts were used for hydrogenation, such as ruthenium or platinum, nickel appears to be alternative to the expensive transition metal complexes (p. 1847, right column). Alonzo describes that nickel nanoparticles could be re-utilized several times and maintain high activity in a very simple reaction medium (p. 1851, right column, 2nd paragraph). Alonso teaches hydrogenation of aromatic and aliphatic ketones. For aliphatic ketones Alonzo discloses that the hydrogenation of 6-undecanone to 6-undecanol provides good yields and required short reaction time (p. 1849, right column, 2nd paragraph, Table 3). Thus, Alonzo teaches step (d) of the method of producing linear fatty acids.
Taco-Vasquez teaches conversion of mixed alcohols to hydrocarbons using HZSM-5 (SiO2/Al2O3 =280 mol/mol) (Abstract). The mixed alcohols comprise alkanols with 3-13 carbon atoms including 6- undercanol (p. 1709, Table 2). Taco-Vasquez describes that mixed alcohols dehydrate to produce olefins and depending on the reaction temperature, olefins oligomerize to hydrocarbons ranging from C3 to C12 (p. 1707, right column, 2nd paragraph). Figures 14 and 15 demonstrate that linear olefins undergo mostly dehydration (p. 1713). Taco-Vasquez mentions that at low weight hourly space velocity (WHSV) and low temperature only dehydration reaction occurs (p. 1713, right column, last paragraph and p. 1714, left column, 1st paragraph). HZSM-5 is a heterogeneous catalyst since it is solid mineral, i.e. aluminosilicate SiO2/Al2O3 (Abstract). Besides HZSM-5 Taco-Vasquez mentions ZSM-5 zeolite (p. 1707, left column, 2nd paragraph). Both HZSM-5 and ZSM-5 are acidic catalysts as evidenced by Ahmadvand teaching that HZSM-5 and ZSM-5 have acidic properties (p. 3544, Table 1) with HZSM-5 having higher acidity (Abstract). Thus, Taco-Vasquez teaches step (e) of the method of producing linear fatty acids.
Morris teaches preparation of carboxylic acids with greater than 50% of carboxylate groups at the terminal position from olefins greater than 50% of which has unsaturation at other than terminal position. Reaction is performed in the presence of water, carbon monoxide, cobalt catalyst and pyridine-type promoter (Abstract). Morris mentions that the process is preferably carried out in the presence of saturated carboxylic acids such as acetic acid (column 3, lines 32-34). Morris describes that olefins include linear olefins such as undecene, dodecene or octadecene containing more than 10 carbon atoms (column 2, lines 43-46). Morris discloses production of fatty acids by the described method containing linear fatty acids comprising up-to 38 carbon atoms (column, 4, lines 39-50). Morris provides examples of carboxylation of C10, C11 and C12 olefins which were more than 90% internal olefins with 80% conversion to corresponding C11, C12 and C13 fatty acids which were more than 65% linear (column 5, lines 35-43). Thus, Morris teaches step (f) of the method of producing linear fatty acids.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to add ketonization of hexanoic acid produced by biological fermentation and extraction as described by Gildemyn and perform ketonization as described in Lee teaching for ketonization of hexanoic acid to 6-undercanone. One would have been motivated to make this combination since Lee teaches production of high-energy-density ketone from biologically produced hexanoic acid and provides efficient catalyst, zirconia aerogel. A skilled artisan would have reasonably expected success in this combination because Gildemyn describes synthesis of hexanoic acid by microbial fermentation and extraction and Lee provides method of chemical ketonization of hexanoic acid.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to add hydrogenation of alkenone, such as 6-undecanone, as described by Alonzo, to 6-undecanone, obtained by biological fermentation described by Gildemyn and ketonization described by Lee teaching. One would have been motivated to make this combination since Alonzo teaches hydrogenation of aliphatic ketones with high efficiency, in a simple reaction and with inexpensive catalyst. A skilled artisan would have reasonably expected success in this combination because Gildemyn, Lee and Alonzo describes manipulation of aliphatic compounds, i.e. Gildemyn describes synthesis of hexanoic acid by microbial fermentation and extraction, Lee provides method of chemical ketonization of hexanoic acid to 6-undecanone and Alonzo teaches hydrogenation of 6- undercanone to 6-undercanol.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to add dehydration of alkanol, such as 6-undercanol, as described by Taco- Vasquez, to alkanol obtained based on Gildemyn, Lee and Alonzo teachings as described above. One would have been motivated to make this combination since Taco-Vasquez teaches dehydration of various alkanols with HZSM-5 catalyst and effect of various reaction conditions. A skilled artisan would have reasonably expected success in this combination because Gildemyn, Lee, Alonzo and Taco-Vasquez describes manipulation of aliphatic hydrocarbons, i.e. Gildemyn describes synthesis of hexanoic acid by microbial fermentation and extraction, Lee provides method of chemical ketonization of hexanoic acid to 6-undecanone, Alonzo teaches hydrogenation of 6-undercanone to 6-undercanol and Taco-Vasquez describes dehydration of 6-undercanol.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to add carbonylation step to produce fatty acid from alkene as described by Morris to alkene obtained by biological fermentation and extraction described by Gildemyn, ketonization described by Lee, hydrogenation described by Alonzo and dehydration described by Taco- Vasquez. One would have been motivated to make this combination since Morris teaches carboxylation of olefins with various length and structure and describes various reaction conditions. The produced fatty acids can be used as bio-fuel or in consumer products such as detergent. A skilled artisan would have reasonably expected success in this combination because Gildemyn, Lee, Alonzo, Taco-Vasquez and Morris describes consecutive reactions of manipulation of aliphatic hydrocarbons which are independent on each other and can be combined to arrive at the claimed final product of liner fatty acids comprising 7-28 carbon atoms. In particular, Gildemyn describes synthesis of hexanoic acid by microbial fermentation and extraction, Lee provides method of chemical ketonization of hexanoic acid to 6-undecanone, Alonzo teaches hydrogenation of 6-undercanone to 6-undercanol, Taco-Vasquez describes dehydration of 6-undercanol to 5-undecene and Morris teaches carbonylation of olefins including alkenes, such as 5-undecene, to fatty acids of up-to 39 carbon atoms.
Thus, teachings of Gildemyn, Lee, Alonzo, Taco-Vasquez and Morris as evidenced by PubChem and Ahmadvand render claim 1 obvious.
Regarding claims 2-5, Lee teaches metal oxide catalysts, zirconia catalyst and zirconia aerogel catalyst (Abstract, p. 289, right column, 3rd paragraph, Table 1) as described above. Lee discloses ketonization performed at 360°C (p. 289, right column, last paragraph) which is close to claimed range of 150°C-350°C.
Pursuant to MPEP 2144.05(I), a prima facie case of obviousness exists where the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have the same properties. In the instant case, the temperature for ketonization of 360°C is very close to the upper range of claimed temperature, i.e. 350°C, and is expected to provide ketonization of alkanoic acid.
Thus, Lee teaching in combination with Gildemyn, Alonzo, Taco-Vasquez and Morris teachings and as evidenced by PubChem and Ahmadvand renders claims 2-5 obvious.
Regarding claim 6, Gildemyn teaches Clostridium kluyveri as microorganism producing linear alkanoic acids from ethanol/acetic acid (Abstract). Thus, Gildemyn teaching in combination with Lee, Alonzo, Taco-Vasquez and Morris teachings and as evidenced by PubChem and Ahmadvand renders claim 6 obvious.
Regarding claim 10, Gildemyn teaches that decrease of pH from 7.0 to 5.5 results in quick extraction of n-caproic acid (p. 11, left column, 1st paragraph). Thus, Gildemyn teaching in combination with Lee, Alonzo, Taco-Vasquez and Morris teachings and as evidenced by PubChem and Ahmadvand renders claim 10 obvious.
Regarding claim 11, Alonzo teaches nickel as transition metal catalyst during hydrogenation (Abstract) as described above. Thus Alonzo teaching in combination with Gildemyn, Lee, Taco-Vasquez and Morris teachings and as evidenced by PubChem and Ahmadvand renders claim 11 obvious.
Regarding claims 12 and 13, Taco-Vasquez teaches aluminosilicate zeolite, HZSM-5 (Abstract) as heterogeneous catalyst which is acidic as evidenced by Ahmadvand (Abstract). Besides HZSM-5 Taco- Vasquez mentions ZSM-5 zeolite used for dehydration (p. left column, 2nd paragraph). Both HZSM-5 and ZSM-5 are aluminosilicate zeolites with HZSM-5 having higher acidity as evidenced by Ahmadvand (Abstract).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to try using ZSM-5 for dehydration of alkanol as described by Taco-Vasquez. One would have been motivated to make do that with reasonably expected success since HZSM-5 and ZSM-5 are aluminosilicate zeolites with difference in acidic properties with HZSM-5, protonated form of ZSM-5, being more acidic as evidenced by Ahmadvand and ZSM-5 can provide increased dehydration efficiency depending on alkanol used. Thus, Taco-Vasquez teaching in combination with Gildemyn, Lee, Alonzo and Morris teachings and as evidenced by PubChem and Ahmadvand renders claims 12 and 13 obvious.
Regarding claim 19, Morris teaches carbonylation in the presence of saturated carboxylic acids such as acetic acid (column 3, lines 32-34) as described above. Thus, Morris teaching in combination with Gildemyn, Lee, Alonzo and Taco-Vasquez teachings and as evidenced by PubChem and Ahmadvand renders claim 19 obvious.
Regarding claim 21, Gildemyn teaches production of n-caproic acid from ethanol and acetic acid and mentions that increase in ratio of acetic acid enables faster and more efficient n-caproic acid production (Abstract). N-caproic acid is the hexanoic acid as evidenced by PubChem. Thus, Gildemyn teaching in combination with Lee, Alonzo, Taco-Vasquez and Morris teachings and as evidenced by PubChem and Ahmadvand renders claim 21 obvious.
Regarding claim 22, Lee teaches ketonization of hexanoic acid to 6-undercanone (Abstract), Alonzo teaches hydrogenation of 6-undecanone to 6-undecanol (p. 1849, right column, 2nd paragraph, Table 3). Taco-Vasquez teaches dehydration of 6-undecanol (p. 1709, Table 2). Morris teaches carbonylation of undecene and describes conversion of olefin with 11 carbon atoms to produce linear fatty acid with 12 carbon atoms (column 5, lines 35-43), which is dodecanoic fatty acid. Thus, Gildemyn, Lee, Alonzo, Taco-Vasquez and Morris teachings and as evidenced by PubChem and Ahmadvand render claim 22 obvious.
Claims 7-9 are rejected under 35 U.S.C. 103 as being unpatentable over Gildemyn (Gildemyn et al. Biotechnol. Biofuels, 2017, 10, 83, 1-15) in view of Lee (Lee et al. Applied Catalysis A: General, 2015, 506, 288-293 on record in IDS), Alonzo (Alonzo et al. Tetrahedron, 2008, 64, 1847-1852 on record in IDS), Taco-Vasquez (Taco-Vasquez and Holtzappe AIChE Journal, 2016, 62, 1707-1715) and Morris (US 4158668 A on record in IDS) and as evidenced by PubChem (PubChem CID 8892, Caproic acid [retrieved on 07/17/2025]. Retrieved from the Internet: <https://pubchem.ncbi.nlm.nih.gov/compound/Caproic- Acid>) and Ahmadvand (Ahmadvand et al. Int. J. Envir. Sci. & Technol., 2020, 17, 3541-3548) as applied to claim 1 above, and further in view of Gorak (WO 2019002240 A1).
Teachings of Gildemyn, Lee, Alonzo, Taco-Vasquez and Morris have been set forth above.
Gildemyn, Lee, Alonzo, Taco-Vasquez and Morris do not teach tetradecane during extraction of linear alkanoic acid.
Regarding claims 7-9, Gorak teaches recovering of acetic acid from aqueous stream (Abstract). Gorak provides examples of different extraction mixtures including extractants and diluents (p. 9, Table 2). Gorak discloses that combination of TOPO (extractant) with n-tetradecane, 2-undecanone and phenyldodecane (diluents) achieved good distribution coefficients for high extractant concentrations (p. 10, lines 27-30). Gorak describes that extractant to diluent concentration varied from 15-50% for extractant and 85-50% for diluent (p. 10, lines 3-5) that corresponds to ratio of TOPO to tetradecane of 1:6 to 1:1. The ratio of 1:6 in Gorak teaching is close to the claimed ratio of 1:10.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to add tetradecane from Gorak teaching to TOPO used for extraction of linear alkanoic acids in Gildemyn teaching. One would have been motivated to make this combination since Gorak showed high efficiency of extraction of alkanoic acid, acetic acid, by combination of TOPO and tetradecane. A skilled artisan would have reasonably expected success in this combination because Gildemyn and Gopak teach extraction of linear alkanoic acids.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention that the ratio of extraction components is a result effective variable. One would have been motivated to optimize the ratio of TOPO to tetradecane to achieve the highest efficiency depending on alkanoic acid used. A skilled artisan would have reasonably expected success in this optimization because selection of components ratio is routine and conventional.
Thus, Gildemyn, Lee, Alonzo, Taco-Vasquez, Morris and Gopak teachings and as evidenced by PubChem and Ahmadvand render claims 7-9 obvious.
Claims 14 and 15 are rejected under 35 U.S.C. 103 as being unpatentable over Gildemyn (Gildemyn et al. Biotechnol. Biofuels, 2017, 10, 83, 1-15) in view of Lee (Lee et al. Applied Catalysis A: General, 2015, 506, 288-293 on record in IDS), Alonzo (Alonzo et al. Tetrahedron, 2008, 64, 1847-1852 on record in IDS), Taco-Vasquez (Taco-Vasquez and Holtzappe AIChE Journal, 2016, 62, 1707-1715) and Morris (US 4158668 A on record in IDS) and as evidenced by PubChem (PubChem CID 8892, Caproic acid [retrieved on 07/17/2025]. Retrieved from the Internet: <https://pubchem.ncbi.nlm.nih.gov/compound/Caproic-Acid>) and Ahmadvand (Ahmadvand et al. Int. J. Envir. Sci. & Technol., 2020, 17, 3541-3548) as applied to claim 1 above, and further in view of Han (Han et al. Applied Catalysis A: General, 2011, 396, 8-13).
Teachings of Gildemyn, Lee, Alonzo, Taco-Vasquez and Morris have been set forth above.
Gildemyn, Lee, Alonzo, Taco-Vasquez and Morris do not teach transition metal and molybdenum as transition metal in dehydration step.
Han teaches modification of HZSM-5 catalyst with molybdenum oxide and its application to dehydration of ethanol to ethylene (Abstract). Han described that Mo/HZSM-5 catalyst exhibited much better catalytic performance in ethanol dehydration compared with HZSM-5 (Abstract).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to add molybdenum as transition metal and modify HZSM-5 of Taco-Vasquez teaching to Mo/HZSM-5 as described in Han teaching and apply it to dehydration of alkanol such as 6- undecanol obtained based on Gildemyn, Lee and Alonzo teachings. One would have been motivated to make this modification since Han showed increase in catalytic performance of Mo/HZSM-5 compared with HZSM-5. A skilled artisan would have reasonably expected success in this combination because Gildemyn, Lee, Alonzo, Taco-Vasquez and Han teach manipulation of aliphatic compounds. Thus, Gildemyn, Lee, Alonzo, Taco-Vasquez, Morris and Han teachings and as evidenced by PubChem and Ahmadvand render claims 14 and 15 obvious.
Claims 16 and 18 are rejected under 35 U.S.C. 103 as being unpatentable over Gildemyn (Gildemyn et al. Biotechnol. Biofuels, 2017, 10, 83, 1-15) in view of Lee (Lee et al. Applied Catalysis A: General, 2015, 506, 288-293 on record in IDS), Alonzo (Alonzo et al. Tetrahedron, 2008, 64, 1847-1852 on record in IDS), Taco-Vasquez (Taco-Vasquez and Holtzappe AIChE Journal, 2016, 62, 1707-1715) and Morris (US 4158668 A on record in IDS) and as evidenced by PubChem (PubChem CID 8892, Caproic acid [retrieved on 07/17/2025]. Retrieved from the Internet: <https://pubchem.ncbi.nlm.nih.gov/compound/Caproic-Acid>) and Ahmadvand (Ahmadvand et al. Int. J. Envir. Sci. & Technol., 2020, 17, 3541-3548) as applied to claim 1 above, and further in view of Fenton (Fenton J. Org. Chem., 1973, 38, 3192-3198).
Teachings of Gildemyn, Lee, Alonzo, Taco-Vasquez and Morris have been set forth above.
Gildemyn, Lee, Alonzo, Taco-Vasquez and Morris do not teach transition metal in carbonylation step to comprise phosphine ligand and transition metal to be palladium.
Fenton teaches hydratocarbonylation of olefins with carbon monoxide to produce saturated acids, i.e. fatty acids (Abstract). Acetic acid is used as a solvent (p. 3194, right column, 1st paragraph). Reaction is performed in the presence of catalyst which is palladium-phosphine complex (Abstract). Fenton describes carbonylation of 1-octene chosen to represent olefins for fatty acid synthesis (p. 3193, left column, 1st paragraph) and reports up-to 80% conversion rate (p. 3193, Table 1). Fenton describes effect of different reaction conditions, different phosphine ligands and mechanism of catalysis by palladium-phosphine system (Abstract, Table VI, p. 3196-3198 – Proposed General Mechanism).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to substitute cobalt catalyst in Morris teaching with palladium-phosphine complex described in Fenton teaching and use it for the same purpose of production of fatty acids from olefins obtained based on Gildemyn, Lee, Alonzo and Taco-Vasquez teachings. One would have been motivated to make this modification since Fenton teaches the same product of the reaction, fatty acids, and the same components of the reaction, i.e. carbon monoxide and acetic acid, and different catalyst providing the high conversion rate and Fenton describes the mechanism of reaction. A skilled artisan would have reasonably expected success in this combination because Gildemyn, Lee, Alonzo, Taco-Vasquez, Morris and Fenton teach manipulation of aliphatic compounds. Thus, Gildemyn, Lee, Alonzo, Taco-Vasquez, Morris and Fenton teachings and as evidenced by PubChem and Ahmadvand render claims 16 and 18 obvious.
Claim 17 is rejected under 35 U.S.C. 103 as being unpatentable over Gildemyn (Gildemyn et al. Biotechnol. Biofuels, 2017, 10, 83, 1-15) in view of Lee (Lee et al. Applied Catalysis A: General, 2015, 506, 288-293 on record in IDS), Alonzo (Alonzo et al. Tetrahedron, 2008, 64, 1847-1852 on record in IDS), Taco-Vasquez (Taco-Vasquez and Holtzappe AIChE Journal, 2016, 62, 1707-1715), Morris (US 4158668 A on record in IDS) and Fenton (Fenton J. Org. Chem., 1973, 38, 3192-3198) as evidenced by PubChem (PubChem CID 8892, Caproic acid [retrieved on 07/17/2025]. Retrieved from the Internet: <https://pubchem.ncbi.nlm.nih.gov/compound/Caproic-Acid>) and Ahmadvand (Ahmadvand et al. Int. J. Envir. Sci. & Technol., 2020, 17, 3541-3548) as applied to claims 1 and 16 above, and further in view of Dong (Dong et al. Nature Commun., 2017, 8, 14117, 1-7) as evidenced by Neumann (Neumann and Jackstell, Encyclopedia of Reagents for Organic Synthesis, 2022, Pyridine, 2,2′-[1,2-phenylenebis [methylene[(1,1-dimethylethyl) phosphinidene]]]bis, pp. 1-4).
Teachings of Gildemyn, Lee, Alonzo, Taco-Vasquez, Morris and Fenton have been set forth above.
Gildemyn, Lee, Alonzo, Taco-Vasquez, Morris and Fenton do not teach phosphine ligand to be 2,2′-[1,2-phenylenebis[methylene[(1,1-dimethylethyl)phosphinidene]]]bis[pyridine].
Dong teaches alkoxycarbonylation of alkenes in the presence of carbon monoxide and methanol and with a palladium catalyst based on a new phosphine ligand, i.e. 1,2-bis((tert-butyl(pyridin-2-yl)phosphanyl)methyl)benzene L3 (pytbpx) (Abstract, p. 3, Figure 2)). 1,2-bis((tert-butyl(pyridin-2- yl)phosphanyl)methyl)benzene is an alternate name for 2,2′-[1,2-phenylenebis[methylene[(1,1- dimethylethyl)phosphinidene]]]bis[pyridine] as evidenced by Neumann (p. 1, left column). The chemical formulas are the same as can be seen from formula for 2,2′-[1,2-phenylenebis[methylene[(1,1- dimethylethyl)phosphinidene]]]bis[pyridine in Neumann teaching (p. 1) and formula for L3 pytbpx in Dong teaching (p. 4, Figure 3). Dong describes that application of the novel catalyst to different olefins provides excellent yield and that it can be used for: “transformation of nearly any alkene into a versatile ester product” (Abstract). Therefore the novel catalyst can be used for alkoxy carbonylation of linear alkenes for production of linear fatty acid esters as claimed in step (f) of claim 1.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to substitute phosphine ligand in Fenton teaching with 2,2′-[1,2- phenylenebis[methylene[(1,1-dimethylethyl)phosphinidene]]]bis[pyridine] described in Dong teaching and use it for production of fatty acid esters from olefins obtained based on Gildemyn, Lee, Alonzo and Taco-Vasquez teachings. One would have been motivated to make this modification since Dong teaches that the novel catalyst provides excellent product yield and can be applied to any alkene. A skilled artisan would have reasonably expected success in this combination because Gildemyn, Lee, Alonzo, Taco-Vasquez, Morris, Fenton and Dong teach manipulation of aliphatic compounds. Thus, Gildemyn, Lee, Alonzo, Taco-Vasquez, Morris, Fenton and Dong teachings and as evidenced by PubChem, Ahmadvand and Neumann render claim 17 obvious.
Response to Arguments
Applicant's arguments filed 08/08/2025 have been fully considered but they are not persuasive.
Applicant argues (addressing pages 7-10 of the Remarks) that: “None of the claimed method steps are connected in the cited prior art and claims are not being considered "as a whole" … the current rejection has failed to take account that the claims are directed to a method with steps that are performed in a sequence where the ending materials of one step are the starting materials of the next.” Applicant further argues that Gildemyn and Morris do not mention anything about long-chained carboxylic acid and Lee and Alonzo do no use ethanol and/or linear alkanoic acid as starting material. Applicant emphasizes that: “"[T]o have a reasonable expectation of success, one must be motivated to do more than merely to vary all parameters or try each of numerous possible choices until one possibly arrived at a successful result." Applicant reminds to avoid improper hindsight and argues that: the cited prior art provides no guidance whatsoever that would lead one skilled in the art on path through the teachings of the six cited prior art reference and arrive at the claims of the current application.” These arguments are not persuasive because:
In response to applicant's arguments against the references individually, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986). In instant case, the rejection is based on combination of prior art of Gildemyn, Lee, Alonzo, Taco-Vasquez and Morris making obvious method of producing linear fatty acid comprising steps of claim 1 that are performed in a sequence where the ending materials of one step are the starting materials of the next as follows: Gildemyn describes synthesis of hexanoic acid by microbial fermentation of ethanol (Abstract), Lee provides method of chemical ketonization of hexanoic acid to 6-undecanone (Abstract), Alonzo teaches hydrogenation of 6-undercanone to 6-undercanol (p. 1849, right column, 2nd paragraph, Table 3), Taco-Vasquez describes dehydration of 6-undercanol to 5-undecene (p. 1709, Table 2) and Morris teaches carbonylation of 5-undecene to fatty acids of up-to 39 carbon atoms (column 2, lines 43-46; column 4, lines 39-50).
In response to applicant's argument that the examiner's conclusion of obviousness is based upon improper hindsight reasoning, it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971).
In response to applicant’s argument that there is no teaching, suggestion, or motivation to combine the references, the examiner recognizes that obviousness may be established by combining or modifying the teachings of the prior art to produce the claimed invention where there is some teaching, suggestion, or motivation to do so found either in the references themselves or in the knowledge generally available to one of ordinary skill in the art. See In re Fine, 837 F.2d 1071, 5 USPQ2d 1596 (Fed. Cir. 1988), In re Jones, 958 F.2d 347, 21 USPQ2d 1941 (Fed. Cir. 1992), and KSR International Co. v. Teleflex, Inc., 550 U.S. 398, 82 USPQ2d 1385 (2007). In this case, the prior art of Gildemyn, Lee, Alonzo, Taco-Vasquez and Morris is in the similar field of endeavor, teaching the consecutive reactions of manipulation of aliphatic hydrocarbons, wherein each of the references teach the manipulation step (fermentation, extraction, ketonization, hydrogenation, dehydration, hydrocarboxylation) with the same predictable function in the combination as they are independently providing a reasonable expectation of success in combination of prior art and motivation to combine them. Additionally motivation for combination comes from the benefits described by the prior art, e.g. Gildemyn teaches high rate of production of hexanoic acid from ethanol, the product of syngas fermentation (Abstract); Lee teaches higher-energy-density C11 ketone, 6-undercanone, production from biologically produced hexanoic acid (p. 288, right column, last paragraph) and describes catalyst, zirconia aerogel, with high stability and catalytic activity (p. 292, right column, last paragraph); Alonzo teach hydrogenation of 6-undecanone to 6-undecanol with good yields and within short reaction time (p. 1849, right column, 2nd paragraph, Table 3) with nickel nanoparticles as cost-efficient and highly active catalyst (p. 1851, right column, 2nd paragraph); Taco-Vasquez describes aluminosilicate zeolites, HZSM-5 and ZSM-5 as heterogeneous catalyst for dehydration of alkanols including 6-undercanol (Abstract) and Morris teaches production of carboxylic acids, synthetic fatty acids, by carboxylation of olefins that can supplement or replace the natural products (column 1, lines 26-29) and which can be used as bio-fuel or in consumer products such as detergent.
Applicant argues that MPEP § 2143.01 explains that a proposed modification cannot render the prior art unsatisfactory for its intended purpose or change the principle of operation of a reference. Applicant provides an example: “One skilled in the art would having no reason to deviate from the combined teaching of Gildemyn or Morris AND Lee AND Alonso and instead dehydrate the secondary alcohol to higher alkenes in order to provide the starting material of Taco-Vasquez. There is no basis anywhere in the cited prior art to do this. Further, dehydrate the secondary alcohol is contrary to the purposes of the teachings of Gildemyn or Morris AND Lee AND Alonso and violates at least MPEP § 2143.01.” These arguments are not persuasive because: prior art teaches consecutive reactions reaching the intended purpose of production of linear fatty acids as described above and combination of references does not change the principle of the reactions taught. Regarding the provided example, Taco-Vasquez teaches dehydration of the secondary alcohols to alkenes (Abstract, Table 2). Morris describes that in order to obtain carboxylic acids with carboxylate group at the terminal position, it is necessary to use alpha olefin which can be obtained only through special processing and is generally more expensive (column 1, lines 54-59). The advantage of Morris method is to prepare carboxylic acids with more than 50% carboxylate groups at the terminal position from olefins containing less than 10% of more expensive alpha-olefins (column 1, lines 60-67). Morris provides examples of carboxylation of C10, C11 and C12 olefins which were more than 90% internal olefins with 80% conversion to corresponding C11, C12 and C13 fatty acids which were more than 65% linear (column 5, lines 35-43). Therefore, Morris method needs alkenes produced as described by Taco-Vasquez from secondary alcohols obtained by method described by Alonzo (Abstract) which in their turn are obtained from alkanone, such as 6-undecanone, by ketonization of hexanoic acid, produced by fermentation of ethanol as taught by Gildemyn (Abstract), as described by Lee (Abstract). Thus, combination of the prior art results in the production of the claimed product.
Applicant argues that the advantages of the current application, i.e. starting from a cheap and readily available raw material for production of higher linear fatty acids, preferably lauric acid; production of the raw material using a means that does not kill any animal or plant; using the biotechnological step for producing high and pure yield of hexanoic acid that can be then readily used for the production of higher alkanones, preferably 6-undecanone, and further to higher linear fatty acids, preferably lauric acid, using a chemical step, are not mentioned in the cited prior art. These arguments are nor persuasive because the combination of prior art provides the mentioned advantages., i.e. Gildemyn teaches production of hexanoic acid from ethanol, which is cheap and available raw material, by microorganism without killing animal or plant, with high production rates, which were up to 40 mM day−1 (4.64 g L−1 day−1) at carbon conversion efficiencies of 90% or higher (Abstract) and lauric acid is produced by combination of chemical steps based on prior art of Lee, Alonzo, Taco-Vasquez and Morris as described above.
Therefore the 35 U.S.C. 103 rejection is maintained.
Maintained Rejections
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.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-3, 5-7, 10-15 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-3, 5-7 and 9-14 of copending Application No. 18/285,196 (reference application) in view of Morris (US 4158668 A on record in IDS).
Claim 1 is directed to a method of producing linear fatty acids comprising steps of (a) contacting ethanol and/or linear alkanoic acid comprising 2-5 carbon atoms with at least one microorganism to produce a linear alkanoic acid comprising 4-7 carbon atoms; (b) extracting the intermediate; (c) contacting the intermediate with ketonization catalyst to produce linear alkanone comprising 7-28 carbon atoms; (d) hydrogenation of linear alkanone to linear alkanol; (e) dehydration of linear alkanol to form linear alkene and (f) hydroxy or alkoxy carbonylation of the linear alkene to produce linear fatty acid or an ester thereof.
Regarding claim 1, reference claim 1 teaches steps (a)-(e) corresponding to instant steps (a)–(e) and including all instant claim 1 limitations.
The reference claim 1 does not teach hydroxy or alkoxy carbonylation of linear alkene to produce linear fatty acid or an ester.
Morris teaches preparation of carboxylic acids with greater than 50% of carboxylate groups at the terminal position from olefins in the presence of water, carbon monoxide, cobalt catalyst and pyridine-type promoter (Abstract). Morris mentions that the process is preferably carried out in the presence of saturated carboxylic acids such as acetic acid (column 3, lines 32-34). Morris describes that olefins include linear olefins such as undecene, dodecene or octadecene containing more than 10 carbon atoms (column 2, lines 43-46). Morris discloses production of fatty acids by the described method containing linear fatty acids containing up-to 38 carbon atoms (column, 4, lines 39-50). Morris provides examples of carboxylation of C10, C11 and C12 olefins which were more than 90% internal olefins with 80% conversion to corresponding C11, C12 and C13 fatty acids which were more than 65% linear (column 5, lines 35-43).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to add carbonylation step to produce fatty acid from alkene as described by Morris to alkene obtained by method described in reference application. One would have been motivated to make this combination since Morris teaches carboxylation of olefins with various length and structure and describe various reaction conditions and addition of carbonylation step will produce fatty acids used as bio-fuel or consumer products. A skilled artisan would have reasonably expected success in this combination because reference application teaches production of linear alkenes and Morris provides carbonylation of alkenes to fatty acids.
Thus, claim 1 of reference application and Morris teaching render claim 1 obvious.
Claim 2 of instant application is drawn to a metal oxide catalyst as ketonization catalyst. That corresponds to claim 2 of reference application.
Claim 3 of instant application is drawn to a group of metal oxide catalysts. That corresponds to claim 3 of reference application.
Claim 5 of instant application is drawn to a reaction temperature of step (c) of 150°C-350°C. That corresponds to claim 5 of reference application.
Claim 6 of instant application is drawn to a group of microorganisms for step (a). That corresponds to claim 6 of reference application.
Claim 7 of instant application is drawn to a group of alkyl-phosphine oxides. That corresponds to claim 7 of reference application.
Claim 10 of instant application is drawn to pH in (b) of 5.5-8. That corresponds to claim 9 of reference application.
Claim 11 of instant application is drawn to a group of hydrogenation metal catalysts. That corresponds to claim 10 of reference application.
Claim 12 of instant application is drawn to an aluminosilicate zeolite catalyst. That corresponds to claim 11 of reference application.
Claim 13 of instant application is drawn to the catalyst comprising ZSM-5. That corresponds to claim 12 of reference application.
Claim 14 of instant application is drawn to the catalyst in step (e) comprising transition metal. That corresponds to claim 13 of reference application.
Claim 15 of instant application is drawn to the transition metal being molybdenum. That corresponds to claim 14 of reference application.
Therefore, since instant claims 1-3, 5-7 and 10-15 encompass the subject matter of the reference claims 1-3, 5-7 and 9-14, they are rejected under obviousness double patenting.
This is a provisional nonstatutory double patenting rejection.
Conclusion
No claims are allowed.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to LIOUBOV G KOROTCHKINA whose telephone number is (571)270-0911. The examiner can normally be reached Monday-Friday: 8:00-5:30.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Sharmila G Landau can be reached at (571)272-0614. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/L.G.K./Examiner, Art Unit 1653
/SHARMILA G LANDAU/Supervisory Patent Examiner, Art Unit 1653