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 .
Election/Restrictions
Applicant's election with traverse of Group I, species (i), claims 1, 3-5, 7-15 and 17, in the reply filed on January 14, 2026 is acknowledged. The traversal is on the ground(s) that examining all claims in this application would not be a serious burden and the scopes of claims 5 and 17 overlap.
This is not found persuasive because any differences in scope requires a different analysis which can lead to a different field of search and application of prior art.
The requirement is still deemed proper and is therefore made FINAL.
Accordingly, claims 2 (method), 6 (species) and 16 (method) are withdrawn from consideration as being directed to a non-elected invention.
Drawings
The drawings were received on August 14, 2024. These drawings are acceptable.
Claim Objections
Claims 3 and 9-10 are objected to because of the following informalities:
Claim 3
line 1, please insert the word -- the -- before the word “carbon”.
This is an instance where the article should be added to ensure proper antecedent basis for the claim terminology.
Claim 9
line 3, please insert the word -- the -- before the word “carbon”.
This is an instance where the article should be added to ensure proper antecedent basis for the claim terminology.
line 4, please insert the word -- the -- before the word “carbon”.
This is an instance where the article should be added to ensure proper antecedent basis for the claim terminology.
line 6, please insert the word -- the -- before the word “methanol”.
This is an instance where the article should be added to ensure proper antecedent basis for the claim terminology.
line 9, please insert the word -- the -- before the word “formaldehyde”.
This is an instance where the article should be added to ensure proper antecedent basis
for the claim terminology.
line 9, please insert the word -- the -- before the word “methanol”.
This is an instance where the article should be added to ensure proper antecedent basis for the claim terminology.
Claim 10
line 1, please insert the word -- the -- before the word “oxymethylene”.
This is an instance where the article should be added to ensure proper antecedent basis for the claim terminology.
Claim Rejections - 35 USC § 112
Claims 9 and 13 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 9
line 8, “said compartments” lack antecedent basis.
Antecedent basis must be laid for each recited element in a claim, typically, by introducing each element with the indefinite article (“a” or “an”). See Slimfold Mfg. Co. v. Kincaid Properties, Inc., 626 F. Supp 493, 495 (N.D. Ga. 1985), aff'd, 810 F.2d 1113 (Fed. Cir. 1987) (citing P. Rosenberg, 2 Patent Law Fundamentals § 14.06 (2d. Ed. 1984)). Subsequent mention of an element is to be modified by the definite article “the”, “said” or “the said,” thereby making the latter mention(s)
of the element unequivocally referable to its earlier recitation.
Claim 13
line 1, recites “reacting”.
It is unclear from the claim language what the relationship is between the cathodic reaction recited in claim 1, lines 6-7; the anodic reaction recited in claim 1, line 8; and the reacting.
Claim 14
line 1, recites “the reaction”.
It is unclear from the claim language which reaction this limitation is further limiting. Is it the cathodic reaction recited in claim 1, lines 6-7; the anodic reaction recited in claim 1, line 8; or the reaction recited in claim 13, lines 1-2.
Appropriate correction is required.
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.
I. Claim(s) 1, 3-5, 8, 10-12, 15 and 17 is/are rejected under 35 U.S.C. 103 as being
unpatentable over Teamey et al. (US Patent Application Publication No. 2013/0140187 A1) in view of Ouda et al. (“Poly (Oxymethylene) Dimethyl Ether Synthesis - A Combined Chemical Equilibrium Investigation Towards an Increasingly Efficient and Potentially Sustainable Synthetic Route,” Reaction Chemistry & Engineering (2017), Vol. 2, No. 1, pp. 50-59).
Regarding claim 1, Teamey teaches a method of producing oxymethylene dimethyl ether1, comprising:
• preparing via paired electrosynthesis, paired electrosynthesis meaning that both anodic and cathodic reactions (= electrochemical reduction of carbon dioxide with co-oxidation of an alcohol) [page 1, [0004]] form one or more selected from the group consisting of oxymethylene dimethyl ether and at least one intermediate compound to formation of oxymethylene dimethyl ether (= formaldehyde 212) [page 3, [0030]; and Fig. 2],
wherein the paired electrosynthesis comprises:
- a cathodic reaction of electrochemically reducing one or more selected from the group consisting of carbon monoxide and carbon dioxide (= electrochemical reduction of carbon
dioxide) [page 1, [0004]]; and
- an anodic reaction of electrochemically oxidising methanol (= co-oxidation of an alcohol) [page 1, [0004]; and page 3, [0030]]; and
wherein the at least one intermediate compound comprises formaldehyde (=
formaldehyde 212) [page 3, [0030]; and Fig. 2].
Teamey does not explicitly teach wherein oxymethylene dimethyl ether is prepared.
Teamey teaches that:
Electrochemical cell 102 is generally operational to reduce carbon dioxide in the first region 116 to a first product 113 recoverable from the first region 116 while producing a second product 115 recoverable from the second region 118. Cathode 122 may reduce the carbon dioxide into a first product 113 that may include one or more compounds. Examples of the first product 113 recoverable from the first region 116 by first product extractor 110 may include carbon monoxide, formic acid, formaldehyde, methanol, oxalate, oxalic acid, glyoxylic acid, glycolic acid, glyoxal, glycolaldehyde, ethylene glycol, acetic acid, acetaldehyde, ethanol, ethylene, methane, ethane, lactic acid, propanoic acid, acetone, isopropanol, 1-propanol, 1,2-propylene glycol, propane, 1-butanol, and 2-butanol (page 2, [0022]).
Ouda teaches that:
There have been a number of recent reports describing the conversion CO2 typically with H2 (e.g. via thermo- or electrochemical routes), followed by upgrading if necessary, to produce high purity “clean” fuels and platform chemicals.3–7 These products, typically oxygenates including methanol, dimethyl ether and more recently members of the poly(oxymethylene) dimethyl ether family (denoted hereon as MeOH, DME and OME respectively) are characterised by interesting intrinsic combustion properties (e.g. significantly reduced soot and particulate matter production), when employed in pure form or blended with conventional fuels.8–10 (page 50, right column, lines 7-18).
Synthetic routes to polyoxymethylene dimethyl ethers (OME) based on the synthesis of
CH3OH from recycled CO2 and sustainable H2 via aqueous or anhydrous routes are shown in Fig. 1:
PNG
media_image1.png
408
582
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Greyscale
(page 51).
It would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to modify the method taught by Teamey with wherein oxymethylene dimethyl ether is prepared. The person with ordinary skill in the art
would have been motivated to make this modification because Teamey teaches that the cathode reduces carbon dioxide into formaldehyde in [0022] where formaldehyde is an intermediate compound to the formation of OME (oxymethylene dimethyl ether) as shown by Ouda in Fig. 1, which is a “clean” fuel and platform chemical as taught by Ouda on page 50, right column, lines 7-13, and which is used as a substitute for diesel as by Ouda on page 50, abstract.
Regarding claim 3, Teamey teaches electrochemically reducing carbon dioxide (=
electrochemical reduction of carbon dioxide) [page 1, [0004]]; and wherein the at least one
intermediate compound further comprises formic acid (= formic acid) [page 2, [0022]].
Regarding claim 4, Teamey teaches wherein
- the paired electrosynthesis is carried out in an electrolyte (= catholyte electrolytes (page 5, [0059]); and alkaline or hydroxide electrolytes (page 6, [0065])) or
- the electrochemically reducing one or more selected from the group consisting of carbon monoxide and carbon dioxide is carried out in a catholyte (= a catholyte) [page 2, [0021]]; or
- the electrochemically oxidising methanol is carried out in an anolyte (= an anolyte) [page 2, [0021]].
Regarding claim 5, Teamey teaches wherein
- the electrolyte comprises methanol; or
- the catholyte comprises methanol; or
- the anolyte comprises methanol (= a preferred embodiment of the present disclosure is the use of a methanol feed to both the anode and the cathode) [page 3, [0030]].
Regarding claim 8, Teamey teaches that the method is performed in an electrochemical reactor (= electrochemical cell 102) [page 2, [0021]], wherein
- the one or more selected from the group consisting of carbon monoxide and carbon dioxide is electrochemically reduced in a compartment, comprising a cathode (= first region 116 may include a cathode 122) [page 2, [0021]], said cathode comprising one or more selected from the group of the groups consisting of metals, carbon-doped materials, and carbon-based materials (page 5, [0058]); or
- the methanol is electrochemically oxidised in a compartment, comprising an anode (=
second region 118 may include an anode 124) [page 2, [0021]], said anode comprising one or
more metals (page 3, [0042]).
Regarding claim 10, Teamey does not explicitly teach wherein oxymethylene dimethyl ether is formed in one or more selected from the group consisting of the compartment comprising the anode and the compartment comprising the cathode.
The subject matter would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention because Teamey teaches formaldehyde in the first region 116 (page 2, [0022]) and formaldehyde in the second region (page 3, [0031]) where oxymethylene dimethyl ether is synthesized from formaldehyde as taught by Ouda (page 51, Fig. 1).
Regarding claim 11, Teamey does not explicitly teach wherein said compartments are
the same compartment.
Teamey teaches that electrochemical cell 102 may be implemented as a divided cell (page 2, [0021]).
It would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to modify the said compartments taught by Teamey with wherein said compartments are the same compartment. The person with ordinary skill in the art would have been motivated to make this modification because Teamey teaches that the electrochemical cell may be implemented as a divided cell on page 2, [0021]. Hence, an undivided cell would have been suitable to use.
The disclosure of reference must be considered for what it fairly teaches one of ordinary skill in the art, pertinence of non-preferred disclosure must be reviewed in such light. In re
Meinhardt 157 USPQ 270; and MPEP § 2123 and § 2141.02(VI).
Regarding claim 12, Teamey teaches wherein the paired electrosynthesis is carried out
at:
- atmospheric pressure or higher (= for example, the electrochemical cell may operate at higher pressures, such as pressures above atmospheric pressure) [page 4, [0053]]; or
- a temperature of 0 °C or higher (= the anolyte operating temperatures may be in the same ranges as the ranges for the catholyte, and may be in a range of 0o C. to 95o C) [page 5, [0063]].
Regarding claim 15, Ouda teaches wherein the oxymethylene dimethyl ether comprises one or more compounds represented by general formula CH3O(CH2O)nCH3, wherein “n” is an
integer of 1 or more (=
PNG
media_image2.png
180
162
media_image2.png
Greyscale
) [page 51, Fig. 1].
Regarding claim 17, Teamey teaches wherein
- the electrolyte comprises 10 % or less of water, based on total weight of the electrolyte; or
- the anolyte comprises 10 % or less of water, based on total weight of the anolyte; or
- the catholyte comprises 10 % or less of water, based on total weight of the catholyte (=
an aqueous solvent comprises at least 5% water. A non-aqueous solvent comprises less than 5%
water) [page 6, [0067]].
II. Claim(s) 7, 9 and 13-14 is/are rejected under 35 U.S.C. 103 as being unpatentable over Teamey et al. (US Patent Application Publication No. 2013/0140187 A1) in view of Ouda et al. (“Poly (Oxymethylene) Dimethyl Ether Synthesis - A Combined Chemical Equilibrium
Investigation Towards an Increasingly Efficient and Potentially Sustainable Synthetic Route,” Reaction Chemistry & Engineering (2017), Vol. 2, No. 1, pp. 50-59) as applied to claims 1, 3-5, 8, 10-12, 15 and 17 above, and further in view of Flanders et al. (US Patent Application Publication No. 2022/0136119 A1).
Regarding claim 7, Teamey in view of Ouda teaches the method of at least claims 1, 3-5, 8, 10-12, 15 and 17 as applied above. The references do not explicitly teach wherein one or more selected from the group consisting of at least part of the carbon monoxide and at least part of the carbon dioxide originates from one or more selected from the group consisting of a pre-combustion process, a combustion process, a natural gas stream, a biogas stream, synthesis gas, water, and air.
Teamey teaches a carbon dioxide source 106 (page 2, [0020]).
Flanders teaches that:
A system may optionally include an upstream source of carbon dioxide input, connected to an input of a carbon dioxide reactor of the disclosure, including one or more of: a biogas production system; an ethanol fermentation system such as corn ethanol production system, a beer production system, a wine production system; a natural gas processing system; a cement production system; a blast furnace system, for example a steel blast furnace system, capable of producing blast furnace gas; a coke gas production system; power plant systems, such as petroleum power plant systems, natural gas power plant systems, coal power plant systems; petroleum refinery systems; ethylene production systems; ammonia production systems;
hydrogen production systems, such as water-gas shift systems; natural gas processing plants (e.g., Benfield processing); ethylene oxide production systems; aluminum smelting systems; liquified natural gas (LNG) production systems; solid feedstock gasifiers (e.g., municipal solid waste, biomass, or coal feedstocks); reformers (e.g., steam methane reformers, autothermal reformers); systems performing Boudouard reactions; direct air capture (DAC) of carbon dioxide process; atmospheres of planets or moons (e.g., the Martian atmosphere), soil of moons (e.g., the soil of the earth's moon), and/or any other system capable of producing carbon dioxide. An upstream source of carbon dioxide may be connected directly to an input of a carbon dioxide reactor of the disclosure (e.g., serves as the input, such as connected to the reduction catalyst via the cathode flow field and/or gas diffusion layer, etc.) or alternatively the upstream source may be connected to a purification system; a gas compression system; or both a purification system and a gas compression system, in either order; which then connect to an input of a carbon dioxide system of the disclosure. Multiple purification and/or gas compression systems (e.g., scrubbers, etc.) may be employed (page 4, [0070]).
It would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to modify at least part of the carbon monoxide and at least part of the carbon dioxide taught by Teamey with wherein one or more selected from the group consisting of at least part of the carbon monoxide and at least part of the carbon
dioxide originates from one or more selected from the group consisting of a pre-combustion process, a combustion process, a natural gas stream, a biogas stream, synthesis gas, water, and air. The person with ordinary skill in the art would have been motivated to make this modification because Teamey teaches a carbon dioxide source broadly where using a natural gas stream, a biogas stream and air would have provided a carbon dioxide source.
MPEP § 2143(I)(A) states that “combining prior art elements according to known methods to yield predictable results” may be obvious. The claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination would yield nothing
more than predictable results. Furthermore, MPEP § 2144.07 states that “The selection of a known material based on its suitability for its intended use supported a prima facie obviousness
determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 US 327, 65 USPQ 297 (1945).”
Regarding claim 9, Teamey teaches:
- feeding a non-aqueous mixture (= a catholyte may comprise a non-aqueous solvent) [page 6, [0067]] comprising one or more selected from the group consisting of carbon monoxide, carbon dioxide, and methanol to the compartment (= the use of a methanol feed to the cathode) [page 3, [0030]],
- feeding a non-aqueous mixture (= a anolyte may comprise a non-aqueous solvent) [page 6, [0067]] comprising methanol to the compartment (= the use of a methanol feed to the anode) [page 3, [0030]], wherein the anode comprises platinum (= examples of catalysts may include the metal and metal oxides of transition metals and their alloys and mixtures, including those of W, Mo, V, Fe, Ru, Ir, Au, and Pt) [page 3, [0042]].
Teamey in view of Ouda teaches the method of at least claims 1, 3-5, 8, 10-12, 15 and
17 as applied above. The references do not explicitly teach the following:
a. Wherein the cathode comprises boron doped diamond (BDD).
Teamey teaches that:
The cathode may comprise a number of high surface area materials to include copper, stainless steels, carbon, and silicon, which may be further coated with a layer of material which may be a conductive metal or semiconductor. A very thin plastic screen may be incorporated against the cathode side of the membrane to prevent the membrane from touching the high surface area cathode structure. The high surface area cathode structure may be mechanically pressed against the cathode current distributor backplate, which may be composed of material that has the same surface composition as the high surface area cathode. For electrochemical reductions, the cathode electrode may be a suitable conductive electrode, such as Al, Au, Ag, Bi, C, Cd, Co,
Cr, Cu, Cu alloys (e.g., brass and bronze), Ga, Hg, In, Mo, Nb, Ni, NiCo2O4, Ni alloys (e.g., Ni 625, NiHX), Ni-Fe alloys, Pb, Pd alloys (e.g., PdAg), Pt, Pt alloys (e.g., PtRh), Rh, Sn, Sn alloys (e.g., SnAg, SnPb, SnSb), Ti, V, W, Zn, stainless steel (SS) (e.g., SS 2205, SS 304, SS 316, SS 321), austenitic steel, ferritic steel, duplex steel, martensitic steel, Nichrome (e.g., NiCr 60:16 (with
Fe)), elgiloy (e.g., Co-Ni-Cr), degenerately doped n-Si, degenerately doped n-Si:As, degenerately doped n-Si:B, degenerately doped n-Si, degenerately doped n-Si:As, and degenerately doped n-Si:B. Other conductive electrodes may be implemented to meet the criteria of a particular application. For photoelectrochemical reductions, the electrode may be a p-type semiconductor, such as p-GaAs, p-GaP, p-InN, p-InP, p-CdTe, p-GalnP2 and p-Si, or an n-type semiconductor, such as n-GaAs, n-GaP, n-InN, n-InP, n-CdTe, n-GalnP2 and n-Si. Other semiconductor electrodes may be implemented to meet the criteria of a particular application including, but not limited to, CoS, MoS2, TiB, WS2, SnS, Ag2S, CoP2, Fe3P, Mn3P2, MoP, Ni2Si, MoSi2, WSi2, CoSi2, Ti4O7, SnO2, GaAs, GaSb, Ge, and CdSe (page 5, [0058]).
Flanders teaches that:
Characteristics of the catalysts (e.g., particle size, catalyst species, etc.) can additionally or alternatively be used to affect CCP and/or H2 production. For example, larger catalyst particles can result in poor carbon dioxide transport, thereby inhibiting CCP production and reducing the CCP:H2 ratio, whereas smaller catalyst particles can favor CCP production, thereby increasing the ratio. The relative number of active sites with high turnover frequency for hydrogen evolution (“hydrogen sites”) and those with high turnover frequency for carbon dioxide reduction (“carbon dioxide sites”) can additionally or alternatively be dependent on catalyst particle size: larger catalyst particles typically have a higher ratio of hydrogen sites to carbon dioxide sites, favoring H2 production, whereas smaller catalyst particles typically have a lower ratio, favoring CO production. The catalyst type (e.g., catalyst species) can additionally or
alternatively be used to control the reactor output, such as by employing a mixture of one or more catalyst materials, wherein a first set of catalyst materials (e.g., gold) favor carbon dioxide
reduction and a second set of catalyst materials (e.g., platinum) favor water reduction. In examples, a substantially pure gold catalyst can be used to achieve high CCP:H2 ratios, a substantially pure platinum catalyst can be used to achieve low CCP:H2 ratios, and gold-platinum mixtures (e.g., alloyed particles, mixtures of gold particles and platinum particles, etc.) of varying composition can be used to achieve various intermediate ratios (e.g., more gold for higher ratios, more platinum for lower ratios). The catalyst can additionally or alternatively include V, Cr, Mn, Fe, Co, Ni, Cu, Sn, Zr, Nb, Mo, Ru, Rh, Pd, Ag, Cd, Hf, Ta, W, Re, Ir, Hg, Al, Si, In, Ga, Tl, Pb, Bi, Sb, Te, Sm, Tb, Ce, Nd, and/or combinations thereof. The catalyst can additionally or alternatively be associated with (e.g., attached to, supported by, embedded in, adjacent, in contact with, etc.) one or more support structures (e.g., support particles, support matrix, etc.), which may be conductive support structures such as carbon, boron-doped diamond, and/or fluorine-doped tin oxide. However, the catalyst can additionally or alternatively include any other suitable materials (pages 8-9, [0103]).
It would have been obvious to a person having ordinary skill in the art before the effective filing date of the claimed invention to modify the cathode taught by Teamey with
wherein the cathode comprises boron doped diamond (BDD). The person with ordinary skill in the art would have been motivated to make this modification because the substitution of art recognized equivalents as shown by Flanders in [0103] is within the level of ordinary skill in the art. In addition the substitution of one cathode for another is likely to be obvious when it does
nothing more than yield predictable results.
b. Combining the mixtures of said compartments into one reaction mixture, wherein the reaction mixture comprises formaldehyde and methanol.
Teamey teaches that the first product 113 recoverable from the first region 116 by first product extractor 110 may include formaldehyde and methanol (page 2, [0022]). For example, the second product may include a methanol/formaldehyde mixture (page 4, [0054]).
It would have been obvious to a person having ordinary skill in the art before the
effective filing date of the claimed invention to modify the method taught by Teamey by combining the mixtures of said compartments into one reaction mixture. The person with ordinary skill in the art would have been motivated to make this modification because Teamey teaches that electrochemical cell may be implemented as a divided cell on page 2, [0021]. Hence, an undivided cell would have been suitable to use, and the catholyte and anolyte would have been combined.
Regarding claim 13, Ouda teaches reacting the reaction mixture to form oxymethylene dimethyl ether (= CO2 → Methanol → Formaldehyde → OME) [page 51, Fig. 1].
Regarding claim 14, Teamey teaches wherein the reaction is carried out at:
- atmospheric pressure or higher (= for example, the electrochemical cell may operate at
higher pressures, such as pressures above atmospheric pressure) [page 4, [0053]]; or
- a temperature of 0 °C or higher (= the anolyte operating temperatures may be in the same ranges as the ranges for the catholyte, and may be in a range of 0o C. to 95o C) [page 5, [0063]].
Any inquiry concerning this communication or earlier communications from the examiner should be directed to EDNA WONG whose telephone number is (571) 272-1349. The examiner can normally be reached Monday-Friday, 7:00 AM- 3:30 PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Luan Van can be reached at (571) 272-8521. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/EDNA WONG/Primary Examiner, Art Unit 1795
1 A preamble is not necessarily accorded any patentable weight where it merely recites the purpose of a process or the intended use of a structure, and where the body of the claim does not depend on the preamble for completeness but, instead, the process steps or structural limitations are able to stand alone. See MPEP § 2111.02(II).