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 .
Detailed Action
This office action is in response to applicant’s communication filed on 7/15/24.
Claims 25-44 are pending in this application and are being examined in this Office Action.
Election/Restrictions
Restriction is required under 35 U.S.C. 121 and 372.
This application contains the following inventions or groups of inventions which are not so linked as to form a single general inventive concept under PCT Rule 13.1.
In accordance with 37 CFR 1.499, applicant is required, in reply to this action, to elect a single invention to which the claims must be restricted.
Group 1, claim(s) 25-40, drawn to a method for large scale conversion of a fatty alcohol to a fatty aldehyde.
Group 2, claim(s) 41-42, drawn to a method of purifying the fatty aldehyde.
Group 3, claim(s) 43-44, drawn to a composition of more than 93% by weight of fatty aldehyde.
Claim 1 link(s) inventions 1-2. The restriction requirement among the linked inventions is subject to the nonallowance of the linking claim(s): claim 25. Upon the indication of allowability of the linking claim(s), the restriction requirement as to the linked inventions shall be withdrawn and any claim(s) depending from or otherwise requiring all the limitations of the allowable linking claim(s) will be rejoined and fully examined for patentability in accordance with 37 CFR 1.104. Claims that require all the limitations of an allowable linking claim will be entered as a matter of right if the amendment is presented prior to final rejection or allowance, whichever is earlier. Amendments submitted after final rejection are governed by 37 CFR 1.116; amendments submitted after allowance are governed by 37 CFR 1.312.
Applicant(s) are advised that if any claim presented in a continuation or divisional application is anticipated by, or includes all the limitations of, the allowable linking claim, such claim may be subject to provisional statutory and/or nonstatutory double patenting rejections over the claims of the instant application. Where a restriction requirement is withdrawn, the provisions of 35 U.S.C. 121 are no longer applicable. In re Ziegler, 443 F.2d 1211, 1215, 170 USPQ 129, 131-32 (CCPA 1971). See also MPEP § 804.01.
The groups of inventions listed above do not relate to a single general inventive concept under PCT Rule 13.1 because, under PCT Rule 13.2, they lack the same or corresponding special technical features for the following reasons:
The method of Group 1 clearly lacks a special technical feature being obvious over Guerret et al. (US 2024/0254067 A1, pub date Aug. 1, 2024, filed May 27, 2022, claiming priority to FR 2105616 filed May 28, 2021), in view of Greene et al. (“Continuous-Flow Aerobic Oxidation of Primary Alcohols with a Copper(I)/TEMPO Catalyst,” Org. Process Res. Dev. 2013, 17, 1247-1251), and further in view of Ley et al. (“Tetrapropylammonium Perruthenate, Pr4N+RuO4-, TPAP: A Catalytic Oxidant for Organic Synthesis,” Synthesis, 1994, 639-666). (Please see the 103 rejections below)
The election of an invention or species may be made with or without traverse. To preserve a right to petition, the election must be made with traverse. If the reply does not distinctly and specifically point out supposed errors in the restriction requirement, the election shall be treated as an election without traverse. Traversal must be presented at the time of election in order to be considered timely. Failure to timely traverse the requirement will result in the loss of right to petition under 37 CFR 1.144. If claims are added after the election, applicant must indicate which of these claims are readable on the elected invention or species.
Should applicant traverse on the ground that the inventions have unity of invention (37 CFR 1.475(a)), applicant must provide reasons in support thereof. Applicant may submit evidence or identify such evidence now of record showing the inventions to be obvious variants or clearly admit on the record that this is the case. Where such evidence or admission is provided by applicant, if the examiner finds one of the inventions unpatentable over the prior art, the evidence or admission may be used in a rejection under 35 U.S.C. 103 or pre-AIA 35 U.S.C. 103(a) of the other invention.
In the event of rejoinder, the requirement for restriction between the product claims and the rejoined process claims will be withdrawn, and the rejoined process claims will be fully examined for patentability in accordance with 37 CFR 1.104. Thus, to be allowable, the rejoined claims must meet all criteria for patentability including the requirements of 35 U.S.C. 101, 102, 103 and 112. Until all claims to the elected product are found allowable, an otherwise proper restriction requirement between product claims and process claims may be maintained. Withdrawn process claims that are not commensurate in scope with an allowable product claim will not be rejoined. See MPEP § 821.04(b). Additionally, in order to retain the right to rejoinder in accordance with the above policy, applicant is advised that the process claims should be amended during prosecution to require the limitations of the product claims. Failure to do so may result in a loss of the right to rejoinder. Further, note that the prohibition against double patenting rejections of 35 U.S.C. 121 does not apply where the restriction requirement is withdrawn by the examiner before the patent issues. See MPEP § 804.01.
During a telephone conversation with Joe Ta on 6/19/26 a provisional election was made without traverse to prosecute the invention of Group I, claims 25-40. Affirmation of this election must be made by applicant in replying to this Office action. Claims 41-44 are withdrawn from further consideration by the examiner, 37 CFR 1.142(b), as being drawn to a non-elected invention.
As a result, claims 25-40 are being examined in this Office Action.
Priority
The applicant claims benefit as follows:
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Objections
Claim 25 is objected to because of the following informalities:
Claim 25 is objected to because of informal wording. Claim 25 recites the phrase “in the reaction mixture to the reaction mixture” in step b). The phrase is unclear and appears to contain a typographical error. Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
Claim 39 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112, second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention.
Claim 39 is indefinite because the claim recites that “the amount of water absorbing or adsorbing material added is at least 10 g per mmol of fatty alcohol present in the reaction medium prior to oxidation.”
However, it is unclear whether applicant intended “g per mmol” or “mg per mmol.” None of the working examples in applicant’s specification which use molecular sieves appear to fall within the claimed amount.
For example, Example 5 uses 20 g of 4 Å molecular sieves with 252 g of fatty alcohol mixture. Example 6 uses about 64-65 g of molecular sieves with about 800 g of fatty alcohol mixture. Also, Examples 16, 17 and 19 similarly fall outside of applicant’s claimed range. These examples appear to correspond to amounts far below 10 g/mmol, and instead appear closer to about 0.02 g/mmol in these examples.
Thus, the claim language appears inconsistent with the disclosed working examples and the metes and bounds of claim 39 are unclear. 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 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 of this title, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 25-36 and 40 are rejected under 35 U.S.C. 103 as being unpatentable over Guerret et al. (US 2024/0254067 A1, pub date Aug. 1, 2024, filed May 27, 2022, claiming priority to FR 2105616 filed May 28, 2021), in view of Greene et al. (“Continuous-Flow Aerobic Oxidation of Primary Alcohols with a Copper(I)/TEMPO Catalyst,” Org. Process Res. Dev. 2013, 17, 1247-1251), and further in view of Ley et al. (“Tetrapropylammonium Perruthenate, Pr4N+RuO4-, TPAP: A Catalytic Oxidant for Organic Synthesis,” Synthesis, 1994, 639-666).
Determination of the Scope and Content of the Prior Art
(MPEP §2141.01)
Guerret et al. teaches a method for synthesizing aldehyde-terminated pheromones from corresponding alcohols (see “Chem 1” reaction below), wherein R is a linear aliphatic chain having at least 9 carbon atoms and 1 to 4 unsaturations. Guerret et al. teaches that the method is carried out continuously in the presence of a copper-based catalytic system under air pressure of more than 1 bar and at a temperature of between 30 and 200 degree C. Guerret et al. further teaches that the method offers high productivity and high selectivity of the reaction. (Guerret et al., Abstract; paragraphs [0001]-[0002])
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Guerret et al. teaches that insect pheromones require a precise mixture, and specifically discusses the sex pheromone of Cydalima perspectalis as a mixture of Z and E-11 hexadecenal in the precise ratio of 80/20. Guerret et al. further teaches that traces of Z/E-11-hexadecenol completely neutralize the effect of the pheromone, thereby teaching the importance of converting the alcohol precursor to the aldehyde product and controlling residual alcohol impurity. (Guerret et al., paragraphs [0003]-[0005])
Guerret et al. teaches a continuous method comprising feeding a continuous reactor under oxygen pressure between 1 and 30 bar with an alcohol of general formula (I) (see formula below) in an apolar organic liquid phase and a copper-based catalyst, with a copper ligand of formula “Chem 6” (see formula below), in a polar liquid phase, wherein the alcohol is oxidized to the corresponding aldehyde. Guerret et al. further teaches recovering the aldehyde by liquid/liquid separation. Guerret et al. teaches that the copper-based catalyst may further comprise TEMPO or a derivative thereof, a base such as NMI, DBU, DBN, or an acetate salt, and bipyridine. Guerret et al. also teaches an apolar organic phase such as a C5-C8 alkane, particularly hexane, and a polar phase selected from acetonitrile, DMSO, sulfolane, imidazolium salts, and mixtures thereof. (Guerret et al., paragraphs [0021]-[0035])
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Guerret et al. exemplifies large-scale production of Z11-hexadecenal from Z11-hexadecenol. In Example 4, Guerret et al. teaches preparing 5.6 L of Z11-hexadecenol in 14 L of hexane, preparing a catalyst solution containing copper iodide, bipyridine, N-methyl imidazole and TEMPO, pumping the two solutions by HPLC pumps into the H.E.R. reactor, introducing oxygen at 12 bars at a flow rate of 2 L/min, and recovering Z11-hexadecenal. Thus, Guerret et al. teaches the same general large-scale fatty/pheromone alcohol to fatty/pheromone aldehyde oxidation process as presently claimed. (Guerret et al., paragraphs [0128]-[0135])
Ascertainment of the Difference Between Scope the Prior Art and the Claims
(MPEP §2141.012)
Guerret et al. teaches the large-scale fatty/pheromone alcohol oxidation process using a copper-based catalyst system, oxygen pressure, solvent, and aldehyde recovery. However, Guerret et al. is deficient in the sense that, while Guerret et al. teaches oxygen pressure and oxygen feed in a continuous pheromone aldehyde process, Guerret et al. does not expressly recite the claimed O2 dissolving rates in the exact manner claimed in claims 25-28.
Greene et al. cures this deficiency. Greene et al. teaches controlled oxygen delivery in a scalable continuous-flow Cu(I)/TEMPO alcohol oxidation process, including 9% oxygen in nitrogen, gas delivery by mass flow controller, gas/liquid mixing, visible slug flow, pressure control by back-pressure regulator, and pumped delivery of alcohol and catalyst solutions. Therefore, Greene et al. teaches that oxygen concentration, oxygen delivery, gas/liquid contacting, pressure, and residence time are process variables for scalable Cu(I)/TEMPO aerobic oxidation of alcohols to aldehydes. (Greene et al., pages 1247-1248, Figures 1-2)
In particular, Greene et al. teaches a scalable, continuous-flow process for aerobic oxidation of primary alcohols to aldehydes using a homogeneous Cu(I)/TEMPO catalyst system. Greene et al. teaches use of a dilute oxygen source, 9% oxygen in nitrogen, to avoid flammable oxygen/organic mixtures, and teaches that the method was demonstrated with nine different alcohols, including one up to 100 g scale. Greene et al. further teaches that the flow-based catalytic method provides advantages for aerobic oxidation of alcohols, including substantially shorter residence times and broader substrate scope. (Greene et al., abstract, page 1247)
Greene et al. further teaches a flow reactor having components for storage and delivery of substrate and catalyst, a heated reaction zone, and a liquid/vapor separation unit. Greene et al. teaches that gas is delivered as premixed 9% O2 in N2 by a mass flow controller and is combined with liquid solutions, wherein the catalyst and alcohol solutions are delivered by pumps. Greene et al. teaches that the two-phase mixture flows into the tube reactor and that a slug flow pattern with alternating gas and liquid regions is visible in the PTFE tubing. Greene et al. further teaches that the overall pressure is adjusted with a back-pressure regulator. (Greene et al., page 1248, Figure 1 and Figure 2)
Greene et al. teaches that the catalytic reaction system includes Cu(OTf), bpy, TEMPO, NMI, and alcohol substrate in acetonitrile solution. Greene et al. further teaches that the Cu(I)/TEMPO catalyst is highly selective for conversion of primary alcohols to aldehydes, including aliphatic substrates, and teaches development of a scalable continuous-flow process for this reaction. (Greene et al., pages 1247-1248)
Guerret et al. is further deficient in the sense that it does not expressly teach adding the claimed water absorbing or adsorbing material to the reaction mixture of claim 25.
Ley et al. cures this deficiency with respect to the known use and function of molecular sieves in alcohol oxidation reactions. Ley et al. teaches that water formed during catalytic alcohol oxidation can be removed by activated finely powdered 4 Å or 3 Å molecular sieves, and that removal of water favors aldehyde formation over carboxylic acid formation because an aldehyde hydrate is necessary for aldehyde oxidation to carboxylic acid. (Ley et al., page 640)
In other words, Ley et al. teaches that during catalytic oxidations it is necessary to remove water formed during the reaction to achieve high catalytic turnovers, and that this is best achieved by adding activated finely powdered 4 Å or 3 Å molecular sieves. Ley et al. further teaches that primary alcohol oxidations give aldehydes rather than carboxylic acids in nonaqueous solution due to efficient removal of water by molecular sieves, because an aldehyde hydrate is necessary for oxidation of aldehydes to carboxylic acids. Ley et al. is relied upon for this water-removal and aldehyde-selectivity teaching, not for replacing the Guerret et al. copper/TEMPO catalyst system with TPAP/NMO. (NMO is N-methylmorpholine N-oxide) (Ley et al., page 640)
Ley et al. further teaches typical alcohol oxidation procedures using powdered 4 Å molecular sieves at 500 mg/mmol of alcohol. Ley et al. teaches that the reaction mixture includes alcohol and powdered 4 Å molecular sieves in solvent, including procedures using acetonitrile as solvent or an acetonitrile/dichloromethane mixture. Thus, Ley et al. teaches adding molecular sieves directly to alcohol oxidation reaction mixtures to remove water and favor aldehyde formation. (Ley et al., page 641, Methods A-D)
Finding of Prima Facie Obviousness Rationale and Motivation
(MPEP §2142-2143)
Therefore, it would be prima facie obvious to one of ordinary skill in the art at the time of the invention to modify the Guerret et al. large-scale fatty/pheromone alcohol oxidation process with the controlled oxygen delivery, gas/liquid flow, pressure, and process optimization teachings of Greene et al., because both references are directed to aerobic oxidation of primary alcohols to aldehydes using copper/TEMPO catalyst systems and oxygen. Since Greene et al. teaches oxygen concentration, oxygen pressure, gas/liquid flow, and residence time as useful process variables in scalable Cu(I)/TEMPO aerobic alcohol oxidation, the claimed oxygen dissolving or oxygen feed rate would have been an obvious result effective variable to optimize for the oxidation of fatty alcohol to fatty aldehyde.
Additionally, it would be prima facie obvious to one of ordinary skill in the art at the time of the invention to include a water absorbing or adsorbing material, such as molecular sieves, in the Guerret et al. copper-catalyzed fatty alcohol oxidation reaction mixture, because Ley et al. teaches the predictable benefit of removing water formed during alcohol oxidation to improve aldehyde formation and reduce acid formation. The proposed modification does not require adding NMO or changing Guerret et al.’s copper/TEMPO oxidation catalyst system. Rather, the modification is the addition of a known water-removing solid to a known alcohol-to-aldehyde oxidation reaction for the expected purpose of improving aldehyde selectivity and reducing carboxylic acid formation.
With regard to claim 29, Guerret et al. teaches that the pheromone aldehyde process is carried out under air/oxygen pressure of more than 1 bar, and Greene et al. teaches aerobic alcohol oxidation using an oxygen-containing gas mixture of 9% O2 in N2. Therefore, utilizing air or an oxygen-containing gas as the O2 source would have been obvious to one of ordinary skill in the art.
With regard to claim 30, Guerret et al. teaches feeding a continuous reactor under oxygen pressure. Greene et al. further teaches gas delivery by mass flow controller and combining gas and liquid feeds in a flow reactor to form a gas/liquid mixture. Thus, pumping or feeding the oxygen-containing gas through the reaction mixture would have been obvious in view of the oxygen-fed aerobic oxidation processes of Guerret et al. and Greene et al.
With regard to claim 31, Guerret et al. teaches a copper-based catalyst system. To the extent that Guerret et al. does not expressly rely on the same copper(I) salt language recited in the claim, Greene et al. cures this deficiency by teaching a Cu(I)/TEMPO catalyst system including Cu(OTf), bpy, TEMPO, and NMI in acetonitrile solution for aerobic oxidation of alcohols to aldehydes. Therefore, the claimed copper(I) salt would have been obvious in the copper/TEMPO alcohol oxidation process.
With regard to claim 32, Guerret et al. and Greene et al. teach the use of ligand, aminoxyl radical compound, and base in the catalyst system. Guerret et al. teaches TEMPO derivative, base, and bipyridine, and Greene et al. teaches Cu(I), bipyridine, TEMPO, and NMI. Thus the claimed catalyst components would have been obvious to one of ordinary skill in the art.
With regard to claims 33-34, Guerret et al. teaches non-halogenated solvents including an apolar organic phase such as hexane and polar phases including acetonitrile, DMSO, sulfolane, or ionic liquids. Greene et al. further teaches acetonitrile as the solvent for Cu(I)/TEMPO aerobic alcohol oxidation. Ley et al. also teaches oxidation reactions using acetonitrile. Therefore, the claimed non-halogenated solvents and listed solvents would have been obvious as known solvents for the alcohol oxidation process.
With regard to claims 35-36, Guerret et al. teaches selective production of aldehyde-terminated pheromones and high productivity/high selectivity in the oxidation. To the extent Guerret et al. does not expressly recite the exact acid/aldehyde ratio or conversion language of the claims, Greene et al. cures this deficiency by teaching high-yield oxidation of primary alcohols to aldehydes, including aliphatic alcohols, with little formation of carboxylic acid byproducts. Ley et al. further teaches that removing water with molecular sieves favors aldehyde formation over carboxylic acid formation because aldehyde hydrate is necessary for further oxidation to carboxylic acid. Thus, the claimed conversion to aldehyde and reduced conversion to acid would have been obvious in view of the combined teachings of Guerret et al., Greene et al., and Ley et al.
With regard to claim 40, Guerret et al. teaches pheromone aldehyde products having linear aliphatic chains of at least 9 carbons and 1 to 4 unsaturations, including Z/E-11-hexadecenal pheromone aldehydes. Thus, the claimed fatty aldehyde species, including hexadecenal species, are taught or rendered obvious by Guerret et al.
Note that an express suggestion to substitute one equivalent component or process for another is not necessary to render such substitution obvious. In re Fout, 675 F.2d 297, 213 USPQ 532 (CCPA 1982). The use of controlled oxygen feed/pressure/flow and the addition of a known water adsorbing material such as molecular sieves represent predictable process modifications of known alcohol-to-aldehyde oxidation reactions.
Claims 37-38 are rejected under 35 U.S.C. 103 as being unpatentable over Guerret et al. (US 2024/0254067 A1, pub date Aug. 1, 2024, filed May 27, 2022, claiming priority to FR 2105616 filed May 28, 2021), in view of Greene et al. (“Continuous-Flow Aerobic Oxidation of Primary Alcohols with a Copper(I)/TEMPO Catalyst,” Org. Process Res. Dev. 2013, 17, 1247-1251), further in view of Ley et al. (“Tetrapropylammonium Perruthenate, Pr4N+RuO4-, TPAP: A Catalytic Oxidant for Organic Synthesis,” Synthesis, 1994, 639-666), and further in view of Luzzio et al. (“A Facile Oxidation of Alcohols Using Pyridinium Chlorochromate/Silica Gel,” J. Chem. Educ. 1999, 76, 974-975).
Determination of the Scope and Content of the Prior Art
(MPEP §2141.01)
As discussed above, Guerret et al. teaches the large-scale pheromone/fatty alcohol to pheromone/fatty aldehyde oxidation process using a copper-based catalyst system, oxygen pressure, solvent, and aldehyde recovery. Greene et al. teaches scalable Cu(I)/TEMPO aerobic oxidation of primary alcohols to aldehydes using oxygen gas mixtures, gas/liquid flow, pressure, acetonitrile, Cu(I), bipyridine, TEMPO, and NMI. Ley et al. teaches adding activated powdered 4 Å or 3 Å molecular sieves to alcohol oxidation reaction mixtures to remove water formed during oxidation and teaches use of powdered 4 Å molecular sieves at 500 mg/mmol of alcohol.
Luzzio et al. teaches that adsorbents in alcohol oxidations, including Celite, molecular sieves, alumina, or silica gel, have been used with PCC to facilitate removal of byproducts or to provide anhydrous conditions that would otherwise lead to unwanted side reactions and decreased yields. Luzzio et al. further teaches that oxidation of primary alcohols to aldehydes can be compromised by side reactions resulting in formation of carboxylic acids, and that anhydrous PCC/silica gel oxidation conditions minimize formation of carboxylic acids as products of aldehyde hydrate oxidation. (Luzzio et al., page 974)
Ascertainment of the Difference Between Scope the Prior Art and the Claims
(MPEP §2141.012)
Guerret et al., Greene et al., and Ley et al. teach or suggest adding molecular sieves to alcohol oxidation reaction mixtures. However, these references are deficient to the extent that they do not expressly recite all of the water absorbing or adsorbing material species listed in claim 37, such as silica gels and aluminas, and do not expressly recite the final water content of 2 wt% or less as recited in claim 38.
Luzzio et al. cures this deficiency. Luzzio et al. teaches that adsorbents in alcohol oxidations, including Celite, molecular sieves, alumina, or silica gel, have been used to provide anhydrous conditions that would otherwise lead to unwanted side reactions and decreased yields. Luzzio et al. also teaches that anhydrous PCC/silica gel oxidation conditions minimize formation of carboxylic acids as products of aldehyde hydrate oxidation. Thus, Luzzio et al. teaches the use of the same type of adsorbent materials recited in claim 37 and the same reason for using anhydrous/water-removing conditions, namely reducing unwanted side reactions and carboxylic acid formation. (Luzzio et al., page 974)
Finding of Prima Facie Obviousness Rationale and Motivation
(MPEP §2142-2143)
Therefore, it would be prima facie obvious to one of ordinary skill in the art at the time of the invention to use molecular sieves, silica gel, alumina, or other conventional adsorbent materials in the Guerret et al./Greene et al. alcohol oxidation reaction mixture, because Ley et al. teaches the use of molecular sieves in alcohol oxidation reaction mixtures and Luzzio et al. teaches that adsorbents such as molecular sieves, alumina, or silica gel are used in alcohol oxidations to provide anhydrous conditions that avoid unwanted side reactions and decreased yields. Thus, the claimed materials of claim 37 would have been obvious known water absorbing or adsorbing materials for alcohol oxidation reactions.
With regard to claim 38, Guerret et al., Greene et al., Ley et al., and Luzzio et al. do not expressly recite the final water content of 2 wt% or less. However, Ley et al. and Luzzio et al. cure the deficiency by teaching the use of molecular sieves, silica gel, alumina, or other adsorbents to provide anhydrous conditions in alcohol oxidation reactions. It would have been prima facie obvious to one of ordinary skill in the art at the time of the invention to use an amount of water absorbing or adsorbing material sufficient to reduce the water content of the oxidation reaction mixture, because Ley et al. teaches the use of molecular sieves in the oxidation reaction mixture and Luzzio et al. teaches that anhydrous conditions minimize unwanted side reactions and carboxylic acid formation from aldehyde hydrate oxidation. Once the prior art teaches adding water absorbing or adsorbing materials to improve alcohol-to-aldehyde oxidation and reduce acid formation, the amount sufficient to achieve a desired low water content would have been a result effective variable that one of ordinary skill in the art would have optimized through routine experimentation.
Furthermore, applicant’s own specification acknowledges that removal of water formed during the reaction improves yield and that water is involved in formation of carboxylic acids. Thus, the art-recognized reason to use anhydrous conditions and water adsorbents in alcohol oxidation is directed to the same result desired by applicant, namely improved aldehyde yield and reduced acid formation.
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. See 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.2d438, 164 USPQ 619 (CCPA 1970); and 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) may be used to overcome an actual or provisional rejection based on a nonstatutory double patenting ground provided the conflicting application or patent is shown to be commonly owned with this application. See 37 CFR 1.130(b).
Effective January 1, 1994, a registered attorney or agent of record may sign a terminal disclaimer. A terminal disclaimer signed by the assignee must fully comply with 37 CFR 3.73(b).
The USPTO internet Web site contains terminal disclaimer forms which may be used. Please visit http://www.uspto.gov/forms/. The filing date of the application will determine what form 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 http://www.uspto.gov/patents/process/file/efs/guidance/eTD-info-I.jsp.
Claims 25-38 and 40 are provisionally rejected on the ground of nonstatutory obviousness-type double patenting as being unpatentable over claims 1-20 of copending Application No. 18564580, in view of Greene et al. (“Continuous-Flow Aerobic Oxidation of Primary Alcohols with a Copper(I)/TEMPO Catalyst,” Org. Process Res. Dev. 2013, 17, 1247-1251), further in view of Ley et al. (“Tetrapropylammonium Perruthenate, Pr4N+RuO4-, TPAP: A Catalytic Oxidant for Organic Synthesis,” Synthesis, 1994, 639-666).
Claim 39 is not included in this provisional obviousness-type double patenting rejection because claim 39 is separately rejected under 35 U.S.C. 112(b) as being indefinite.
The teachings of Greene et al. and Ley et al. have been discussed previously within this office action.
The instant claims are directed to a method of converting fatty alcohol to fatty aldehyde using a copper source catalyst, solvent, oxygen feed/dissolution, and water absorbing or adsorbing material, wherein more than 50 wt% fatty alcohol is converted to fatty aldehyde and less than 50 wt% is converted to fatty acid.
Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of copending Application No. 18564580 are directed to a continuous method for preparing an aldehyde from a corresponding, wherein the alcohol is oxidized to the aldehyde under oxygen pressure using a copper-based catalyst system.
Thus, the instant claims and the claims of copending Application No. 18564580 are directed to the same basic invention, namely copper-catalyzed aerobic oxidation of long-chain/fatty/pheromone alcohols to corresponding aldehydes and are therefore an obvious variation.
As a result, the differences between instant claim 25 and the claims of copending Application No. 18564580 are not patentably distinct. To the extent instant claim 25 recites kilogram-scale fatty alcohol and solvent, such scale would have been an obvious matter of routine process scale-up and throughput in view of the continuous aldehyde production process claimed in copending Application No. 18564580.
To the extent instant claim 25 and dependent claims 26-30 recite specific O2 feed/dissolution rates, air or oxygen-containing gas, and pumping or bubbling, such limitations would have been obvious process optimizations because the claims of copending Application No. 18564580 already recite oxidation under oxygen pressure, and Greene et al. teaches controlled oxygen delivery in continuous-flow Cu(I)/TEMPO alcohol oxidation, including 9% O2 in N2, gas delivery by mass flow controller, gas/liquid mixing, slug flow, and back-pressure regulation. (Guerret et al., claims 1 and 12-16; Greene et al., pages 1247-1248, Figures 1-2)
The catalyst and solvent limitations of instant claims 31-34 are also not patentably distinct. The claims of copending Application No. 18564580 already recite a copper-based catalyst system, copper salts, TEMPO or derivative thereof, base, bipyridine, an alkane apolar phase such as hexane, and polar solvents including acetonitrile. Greene et al. further teaches Cu(I)/TEMPO catalyst systems including Cu(OTf), [Cu(CH3CN)4]OTf, bipyridine, TEMPO, NMI, and acetonitrile for aerobic oxidation of alcohols to aldehydes. Thus, the claimed copper source, ligand, aminoxyl radical, base, and solvent selections would have been obvious variations of the same copper/TEMPO alcohol oxidation chemistry. (Guerret et al., claims 1-6, 9-10, and 19-20; Greene et al., pages 1247-1250)
The conversion, acid-reduction, water-removal, and fatty aldehyde limitations of instant claims 35-38 and 40 are likewise not patentably distinct. The claims of copending Application No. 18564580 recite oxidation of the long-chain alcohol to the corresponding aldehyde, and the specification teaches high productivity and high selectivity. Greene et al. teaches high-yield oxidation of primary alcohols to aldehydes with little formation of carboxylic acid byproducts. Ley et al. teaches adding activated powdered 4 Å or 3 Å molecular sieves to alcohol oxidation reaction mixtures to remove water formed during oxidation, improve catalytic turnover, and favor aldehyde formation over carboxylic acid formation. Therefore, the claimed aldehyde conversion, reduced acid formation, water absorbing or adsorbing material, final water content, and fatty aldehyde species would have been obvious results of routine optimization of the same alcohol-to-aldehyde oxidation process. (Guerret et al., claims 1-20; Greene et al., pages 1249-1250; Ley et al., pages 640-641)
Accordingly, instant claims 25-38 and 40 are not patentably distinct from claims 1-20 of copending Application No. 18564580 when viewed in light of Greene et al. and Ley et al.
This is a provisional obviousness-type double patenting rejection, because the conflicting claims have not in fact been patented.
Conclusion
No claim is allowed.
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Jennifer Cho Sawyer
Patent Examiner
Art Unit: 1691
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691
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