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
Claim Status
Claims 1-23 are pending. Claims 1-23 are under examination. Claims 2 and 19 are objected to. Claims 1, 4-18 and 20-23 are rejected. No claims allowed.
Filing Receipt
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Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 3 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 3 recites the limitation "in the intermediate step, an acetaldehyde included in the reaction solution after the first step is hydrogenated" in lines 2-3. There is insufficient antecedent basis for this limitation in the claim.
Claim 2, from where claim 3 depends requires the intermediate step of reducing an unreacted vinyl acetate. The intermediate step in claim 2 does not require or suggest hydrogenating an acetaldehyde.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries 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.
Claim(s) 1, 4-6 and 9-10 is/are rejected under 35 U.S.C. 103 as being unpatentable over Eastham et al. (USPGPub 2006/0128985, Published 06-2006).
Scope of the Prior Art
Eastham et al. teach the following reaction of vinyl acetate, carbon monoxide (CO) and Methanol (MeOH), in the presence of Pd2(dba)3 1,2-bis(di-tert-butylphosphinomethyl)benzene (first catalyst) and methane sulphonic acid (alkyl sulfonic acid, (claim 10) to prepare methyl-2-acetoxy propanoate (MAP) (page 12-13, par. 160-166, Tables 1-3). MAP is shown immediately below. MAP Is the first ester
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compound represented by General Formula (2). Variable R1 is methyl.
Concerning the lactic acid ester of General Formula (3), Eastham et al. teach “both the linear and branched products were produced (methyl-2-acetoxy propanoate and methyl-3-acetoxy propanoate), which can be used as precursors to the industrially favorable methyl lactate and 1,3 propanediol… . Instead of a high selectivity to the linear product based on the steric bulk of the ligands, the reaction favored, the branched metal-alkyl intermediate which is the precursor to the hydrolysis/transesterification product methyl lactate” (p. 12, par. 162).
To sum up and in general, Eastham et al. teach the transesterification reaction is utilized to transesterify the acetoxy product of the carbonylation reaction to prepare the hydroxy ester (par. 18-20). The hydroxy ester being the methyl lactate.
The immediately above transesterification reaction is the current second step. Eastham et al. goes on to teach the transesterification is carried out by any suitable technique known to those skilled in the art (par. 29).
Eastham et al. teach the alcohol and second catalyst in the current second step
as follows (par. 29).
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When methanol is utilized in the above transesterification, so as to not alter the hydroxy alkyl alkanoate, the acetic acid ester of General Formula (4) is formed due to the cleavage of the acetoxy group in the current compound of General Formula (2).
Concerning claim 4, Eastham et al. teach the carbonylation of vinyl acetate in the presence of a hydroxyl group containing compound such as methanol, ethanol, propanol, etc. (par. 84-85).
Concerning claims 5-6 the Pd2(dba)3 1,2-bis(di-tert-butylphosphinomethyl) benzene is the first catalyst including Pd from Group 10 elements and an organic phosphine ligand.
Ascertain the Differences
The prior art teach the individual steps of the claimed process in various locations within Eastham et al. and not in a centralized location.
Obviousness
However, it would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have transesterified MAP arrived at by the ordinary artisan when practicing the teachings of Eastham et al. with methanol in the presence of the second catalyst to prepare methyl lactate with a reasonable expectation of success. In doing so, the ordinary artisan would have also generated the methyl acetate of current compound of General Formula (4) and would have therefore arrived at the current the current invention of claim 1.
Methyl acetate would have been produced because the methods of the prior art are substantially similar to the methods of the current invention. Both the prior art teach the claimed first step and the transesterification of the first ester compound represented by the General Formula (2).
Substantially identical methods yield substantially identical products. See MPEP 2112.01 I. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977). “When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not.” In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990).
Concerning claim 4, the ordinary artisan would have substituted one alcohol for another to obtain predictable results. See MPEP 2141 III (B).
Claim(s) 7, and 11-12 is/are rejected under 35 U.S.C. 103 as being unpatentable over Eastham et al. (USPGPub 2006/0128985, Published 06-2006) as applied to claims 1, 4-6 and 9-10 in the above 103 rejection and in further view of Chaudhari et al. (USPGPub 2005/0143600, Published 06-2005).
Scope of the Prior Art
The teachings of Eastham et al. are in the above 103 rejection and are incorporated by reference. Additional teachings are as follows. Eastham et al. teach conversions as high as 83% (page 12-13, par. 160-166, Tables 1-3) and is mute with regards to selectivity other than a “significantly higher selectivity” (par. 123) and the favoring of the MAP product (par. 162).
Ascertain the Differences
Eastham et al. does not teach a monodentate phosphine ligand nor pyridine as the nitrogen atom-containing heterocyclic compound included in the first catalyst.
Secondary References
Chaudhari et al. teach the use of Pd triphenylphosphine (PPh3), a monodentate organic phosphine ligand and pyridine in a carbonylation reaction of vinyl acetate with CO, CH3OH, and p-toluenesulphonic acid yielding 99% conversion of vinyl acetate and a selectivity of 76.45% to methyl-2-acetoxy propionate (MAP) (p. 3, par. 41-42).
Chaudhari et al. teach overcoming the drawbacks of low activity, catalyst stability, use of toxic chemicals, and severe operating conditions (par. 11).
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have performed the carbonylation of vinyl acetate with an alcohol, CO, Pd PPH3, a sulfonic acid and pyridine with a reasonable expectation of success. The ordinary artisan would have done so to achieve the conversions and selectivity taught by Chaudhari et al.
Claim(s) 8, 16-18 and 20-23 is/are rejected under 35 U.S.C. 103 as being unpatentable over Eastham et al. (USPGPub 2006/0128985, Published 06-2006) and Chaudhari et al. (USPGPub 2005/0143600, Published 06-2005) as applied to claims 1, 4-7 and 9-12 in the above 103 rejection and in further view of Wahl et al. (A General and Efficient Method for the Alkoxycarbonylation of alfa-Chloro Ketones, Adv.Synth.Catal., 354, pp. 3105-3114, Published, 2012).
Scope of the Prior Art
The teachings both individual and combined of Eastham et al. and Chaudhari et al. are in the above 103 rejections and are incorporated by reference. Eastham et al. teach screening of ligands for the catalytic activity of the ligand characterized by conversion and yield (p. 12-13 and Tables 1-3).
The limitations of 17-18 and 20-23 were addressed in the above 103 rejections when addressing current claims 4, 6 and 9-12 respectively.
Ascertain the Differences
Neither Eastham et al. and/or Chaudhari et al. teach the organic phosphine ligand represented by General Formula (5) of claim 8.
Secondary References
Wahl et al. teach the currently claimed organic phosphine ligand as seen below on the following page. Wherein variable R3 and R4 are phenyl (C6 aryl or cycloalkyl group), R5 is a dimethyl amine (dialkyl amino group having two C1 alkyl groups) and
R6-R9 are hydrogen (p. 3106, 6a and 6b respectively).
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Wahl et al. teach overlapping ligands taught by Chaudhari et al. See triphenylphosphine compound 1a taught by Wahl et al. (p. 3106).
Wahl et al. teach the screening of the aforementioned ligands and other monophosphines for conversion and yield in the alkoxycarbonylation of α-chloro ketones in the presence of CO, CH3-OH and a palladium catalyst. With above ligand 6b having 100% conversion and 93 yield. Which is comparable to the PPh3 ligand 1a having 98% conversion and 97% yield (Wahl et al., p. 3106, Table 1.).
Although the current claims are directed to the reaction of CO and CH3-OH with vinyl acetate, both the current reaction and the reactions taught by Wahl et al., Eastham et al. and Chaudhari et al. are alkoxycarbonylation reactions conducted in the presence of a Pd metal catalyst, organic phosphine ligands, CO and CH3-OH.
Obviousness
Therefore, it would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have screened/tried the ligands 6a and 6b of Wahl et al. in the arrived at carbonylation of vinyl acetate with a reasonable expectation of success. The ordinary artisan would have done so to characterize the conversion and yield of ligands 6a and 6b.
The ordinary artisan would have had a reasonable expectation of success due to both Wahl et al. and Chaudhari et al. teaching overlapping ligands used in alkoxycarbonylation reactions. The ordinary artisan would have looked to Wahl et al. because Wahl et al., Eastham et al. and Chaudhari et al. teach alkoxycarbonylation reactions conducted in the presence of a Pd metal catalyst, organic phosphine ligands, CO and CH3-OH.
Additionally, due to Wahl et al. and Eastham et al. teaching the screening of ligands in alkoxycarbonylation reactions and that each ligand performs differently, this establishes ligands as a result effective variable. The ordinary artisan would have arrived at the currently claimed ligands via routine experimental screening of known alkoxycarbonylation ligands that can be used in alkoxycarbonylation reactions.
MPEP 2144.05 II. A. and B. “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).
Claim(s) 13 is/are rejected under 35 U.S.C. 103 as being unpatentable over Eastham et al. (USPGPub 2006/0128985, Published 06-2006) as applied to claims 1, 4-6 and 9-10 in the above 103 rejection and in further view of Mixan (US Patent 4,487,933, Patent date 12-1984).
Scope of the Prior Art
The teachings of Eastham et al. are in the above 103 rejection and are
incorporated by reference. As a reminder Eastham et al. teach the second catalyst as follows. “The transesterification takes place in the presence of a suitable catalyst such as for example methane sulphonic acid or p-toluene sulphonic acid (par. 29). Eastham et al. teach the transesterification reaction is utilized to transesterify the acetoxy product of the carbonylation reaction to prepare the hydroxy ester (par. 18-20).
Ascertain the Differences
Eastham et al. does not teach the second catalyst being one of the bases in claim 13.
Secondary References
Mixan teaches the acid transesterification catalysts of Eastham et al. and the currently claimed transesterification catalysts as conventional acid and base transesterification catalysts. For example, Mixan teaches “conventional acid and base transesterification catalysts, e.g., toluene sulfonic acid, ion exchange resins, sodium methoxide, sodium carbonate and potassium carbonate” (column 1, lines 25-40).
The above teachings render the prior art overlapping in nature to previous teachings and analogous art to the invention.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have substituted one known conventional acid transesterification catalyst toluene sulfonic acid taught by Eastham et al. for a conventional base transesterification catalyst sodium methoxide taught by Mixan. Upon doing so the ordinary artisan would have arrived at the current invention.
The ordinary artisan would have done so with a reasonable expectation of
success because Mixan teach the claimed catalysts and the catalyst taught by Eastham
et al. are conventional transesterification catalysts. The ordinary artisan would have looked to Mixan because of overlapping transesterification catalysts taught by Eastham et al..
Claim(s) 14-15 is/are rejected under 35 U.S.C. 103 as being unpatentable over Eastham et al. (USPGPub 2006/0128985, Published 06-2006) as applied to claims 1, 4-6 and 9-10 in the above 103 rejection and in further view of Fahmy et al. (Biomass pyrolysis: past, present, and future, 22, p. 17-32, 2020, However, Published online 16 June 2018. See first page of Fahmy et al.)
Scope of the Prior Art
The teachings of Eastham et al. are in the above 103 rejection and are incorporated by reference. As a reminder Eastham et al. teach the use of CO and ethanol in the reaction with vinyl acetate (page 12-13, par. 160-166, Tables 1-3 and par. 84-85).
In the process according to the present invention, the carbon monoxide may be used in pure form or diluted with an inert gas such as nitrogen, carbon dioxide or a noble gas such as argon. Small amounts of hydrogen, typically less than 5% by volume, may also be present (par. 88).
Ascertain the Differences
Eastham et al. does not teach the source of CO being from pyrolyzing plastic or a biomaterial and ethanol being bioethanol derived from a plant.
Secondary References
Fahmy et al. teach pyrolysis of organic substances produces gaseous products carbon monoxide and hydrogen (syngas) (p. 18).
Fahmy et al. teach converting biomass chemically—by hydrolysis—to sugars, which may be fermented to give bioethanol (p. 18).
Fahmy et al. teach organic matter used for charring may include synthetic polymers, wood, or biological tissues (p. 20). Herein organic material can be the claimed plastic or biomaterial.
The above teachings render the prior art as analogous art to the invention.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have satisfied a source of the CO and ethanol needed by the ordinary artisan from the teachings of Fahmy et al.
The expectation of success from the teaching that CO may be pure or have hydrogen.
Upon doing so the ordinary artisan would have arrived at the current invention.
Claim Objections
Claims 2 and 19 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
The closest prior art to the invention of claim 2 is Eastham et al. (USPGPub 2006/0128985, Published 06-2006).
Eastham et al. teach the following reaction of vinyl acetate, carbon monoxide (CO) and Methanol (MeOH), in the presence of Pd2(dba)3 1,2-bis(di-tert-butylphosphinomethyl)benzene (first catalyst) and methane sulphonic acid (alkyl sulfonic acid, claim 10) to prepare methyl-2-acetoxy propanoate (MAP) (page 12-13, par. 160-166, Tables 1-3). MAP is shown immediately below. MAP Is the first ester
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compound represented by General Formula (2). Variable R1 is methyl.
Concerning the lactic acid ester of General Formula (3), Eastham et al. teach “both the linear and branched products were produced (methyl-2-acetoxy propanoate and methyl-3-acetoxy propanoate), which can be used as precursors to the industrially favorable methyl lactate and 1,3 propanediol… . Instead of a high selectivity to the linear product based on the steric bulk of the ligands, the reaction favored, the branched metal-alkyl intermediate which is the precursor to the hydrolysis/transesterification product methyl lactate” (p. 12, par. 162).
Eastham et al. teach the other components which contain the catalyst system which may be recycled and/or reused in further reactions with minimal supplementation of fresh catalyst (par. 123). This teaching is interpreted to suggest any products/reactants may be recycled in the processes taught by Eastham et al. This would include any unreacted vinyl acetate.
However, Eastham et al. does not teach reducing unreacted vinyl acetate to prepare an acetic acid ester.
It would not have been obvious to have modified the prior art to arrive at the current invention. There being no motivation to do so.
The closest prior art to the invention of claim 19 is Wahl et al. (A General and Efficient Method for the Alkoxycarbonylation of alfa-Chloro Ketones, Adv.Synth.Catal., 354, pp. 3105-3114, Published, 2012).
Wahl et al. teach an organic phosphine ligand as seen below. Wherein variable R3 and R4 are phenyl (C6 aryl or cycloalkyl group), R5 is a dimethyl amine (dialkyl amino group having two C1 alkyl groups) and R6-R9 are hydrogen (p. 3106, 6a and 6b respectively).
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Wahl et al. teach the screening of ligands for conversion and yield in the alkoxycarbonylation of α-chloro ketones in the presence of CO, CH3-OH and a palladium catalyst. With above ligand 6b having 100% conversion and 93 yield. Which is comparable to the PPh3 ligand 1a having 98% conversion and 97% yield (Wahl et al., p. 3106, Table 1).
However, Wahl et al. does not teach the ligand of claim 19 wherein R5 and R9 are methoxy groups and R6-R8 are hydrogen.
It would not have been obvious to have modified the prior art to arrive at the current invention. There being no motivation to do so.
Conclusion
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/B.G.D/Examiner, Art Unit 1692 /Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625