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 1-20 are pending. Claims 1-7 are under examination. Claims 8-20 are withdrawn. Claims 1-7 are rejected. No claims allowed.
Election/Restrictions
Claims 8-20 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 08/24/2025.
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 6 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 6 ends with the phrase “methods for the rectification concentration comprise one or more of ordinary distillation, atmospheric rectification, vacuum rectification, and molecular rectification in series”. This phrase broadens the “vacuum rectification” in line 4 of claim 6 and renders the claim indefinite.
Additionally, claim 6 requires an absolute pressure of 0.29 MPa and a broader range of pressures 0-10 MPa. These pressures contradict each other. Clarity as to which pressure/s are being claimed is needed. Moreover, pressures above and/or at 1 atm are indefinite due to a “vacuum rectification” being required. Note: 1 atm is 0.101 MPa. Any pressure at or above 0.101 MPa is not a vacuum as required by claim 6.
The limitation of vacuum rectification will be met when the claimed concentration percent, column and column bottom and feed temperatures, pressures, plate number, reflux ratio and absolute pressure are met.
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) 1-2, 4-5 and 7 is/are rejected under 35 U.S.C. 103 as being unpatentable over Jianhua et al. (CN102153461, Published 08-2011. Machine translation attached.), Zhang et al. (US Patent 7,960,594, Patent date 06-2011), and Nianjun et al. (CN103508878, Published 01-2014. Machine translation attached.) as evidence by Chemistry (3 pages, Published 11-2020), Reddit (7 pages, Published 6 years ago or 2019), and Rddennehy (3 pages, Published 08/23/2021).
Interpretation of the Claims
The term “high-purity glycolic acid” in claim 1 is interpreted to be about 91.5-
99.1% glycolic acid. See current specification paragraph 32.
Rectification and the technology including the column in the current claims are interpreted to include distillation, distillation technology and distillation column respectively and the techniques included in current claim 6. This interpretation is based on the current specification on page 3, wherein paragraph 19 recites the following. “In one example, methods for the rectification concentration in step II may include one or more of ordinary distillation, atmospheric rectification, vacuum rectification, and molecular rectification in series”.
Rectification technology is contemplated and/or exemplified in paragraphs 14 and 42, but is not defined. Usually, rectification technology is interpreted to mean just that, rectification technology. However due to the loose definition of rectification comprising distillation, rectification and/or rectification technology, rectification technology is interpreted to mean distillation technology and the techniques in claim 6.
The claimed concentration of the glycolic acid via rectification is accomplished by
rectifying/distilling water and/or solvent away from the glycolic acid and not the rectification/distilling of the glycolic acid. Glycolic acid is not being vaporized and condensed.
Scope of the Prior Art
Jianhua et al. teach a method for preparing glycolic acid from ethylene glycol (page 1/1, first line). Concerning separating and purifying the obtained crude glycolic acid, Jianhua et al. teach evaporating water in the reaction product to concentrate the glycolic acid in the product to 70-80 wt% (page 1/1, claim 2). Jianhua et al. goes on to teach crystallizing the glycolic acid into crystals (page 1/1, claim 3). The 70-80 wt% overlaps the wt% in current claims 2 and 6.
Jianhua et al. teach the evaporation can be accomplished by conventional methods in the area, such as reduced pressure evaporation (par. 12).
Jianhua et al. teach the use of the vacuum distillation method to evaporate the water (p. 4/5, par. 40).
Concerning claim 2 and the supported catalyst utilized in transforming the ethylene glycol to synthesize the crude glycolic acid, Jianhua et al. teach V2O3 possessing the catalytic function and the presence of Al2O3. (p. 2/5, par. 20) The Al2O3 is interpreted as the support.
Concerning claim 2 and step III, Jianhua et al. teach crystallization method can be a conventional method (p. 2/5, par. 12). Jianhua et al. goes on to teach cooling the concentrated product to 8-15C (p. 2/5, par. 12). Concerning the current crystallization kettle, Jianhua et al. teach the use of “flasks” (p. 5/5, top). Jianhua et al. teach the glycolic acid crystals are filtered and vacuum dried (p. 2/5, par. 9). The filtration and drying is the currently claimed filtering and separating. Concerning the high purity glycolic acid, Jianhua et al. teach 99.5 wt% purity (p. 5/5, par. 45).
Concerning claim 7 and the crystallization temperature, Jianhua et al. teach
cooling to 8-11C (p. 1/1, claim 9 of Jianhua et al.). The temperature range overlaps the current range of -20 to 40C.
Concerning claim 7 and the seed crystals added to that of the glycolic acid in concentrated solution, Jianhua et al. teach overlapping wt% of 1 to 5 (p. 2/5, par. 12). Moreover, Jianhua et al. teach the addition of seeds to be a result effective variable. For example, Jianhua et al. teach the addition of seeds and the amount thereof changes the time of crystallization “too long too little, and too much then can cause the reduction of production efficiency” (p. 2/5, par. 12). Jianhua et al. goes on to teach “The selection of crystal seed and the definiteness of add-on all belong to the common sense of this area…” (p. 2/5, par. 12).
Concerning claim 7 and the stirring rate, stirring rate is a result effective variable as evidence by Chemistry (p. 2 of 3, middle of page).
Concerning claim 7 and the cooling rate, cooling rate is a result effective variable as evidence by Reddit (p. 2 of 7).
Concerning claim 7 and the seed concentration, increasing seeding in crystallization to be a result effective variable as evidence by Rddennehy (p. 3 of 3). For example, the effect of adding increasing amounts of seed crystals should be studied.
Additionally, Rddennehy strengthens the argument that stirring to be a result effective variable due to Rddennehy teaching the impact on agitation should be assessed (p. 3 of 3). Moreover, Rddennehy reinforces agitation/stirring and cooling rate are result effective variables because Rddennehy teach “Seed crystals need to be introduced into as homogeneous environment as possible and carefully grown, avoiding excessive build-up of supersaturation in the bulk. This is addressed partially by appropriate cooling and suspension conditions, but how the seeds are introduced is also important. The seed crystals should be well dispersed at the point of addition and slurrying the seeds in a solvent is an ideal method to do this. Slurrying may alter the seed physical properties so this step should also be studied” (p. 3 of 3).
Ascertain the Differences
Jianhua et al. does not teach the raw material ethylene glycol being a bio-based platform compound. Jianhua et al. does not teach the coupling of the rectification column upstream from and in series to the crystallization kettle.
Secondary References
Zhang et al. teach preparing the claimed bio-based platform compound ethylene glycol from cellulose (column 1, lines 1-15). Zhang et al. goes on to teach benefits of using renewable sources of ethylene glycol. For example, Zhang et al. teach “reduce the dependence on the petroleum, so as to build an eco friendly manufacturing process” (column 1, lines 20-45).
The above teachings render the prior art overlapping in nature to the teachings of Jianhua et al. and analogous art to the invention. Overlapping because both references teach ethylene glycol.
Concerning the rectification-crystallization coupling and the crystallization kettle coupled in series with the rectification column, Nianjun et al. teach an evaporation/distillation column apparatus connected in series to a crystallization kettle for concentrating and crystallizing a hydrolysate comprising glycolic acid and water to
prepare high-purity glycolic acid crystals (Figure 1, par. 22). See item 4 in Figure 1 below as the coupling.
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Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have combined the teachings of the prior art to arrive at the invention with a reasonable expectation of success.
For example, the ordinary artisan in need of a source of ethylene glycol would have sourced the ethylene glycol from cellulose as taught by Zhang et al. (current claim 4). The ordinary artisan would have done so to “reduce the dependence on the petroleum, so as to build an eco friendly manufacturing process”.
After generating glycolic acid from the ethylene glycol taught by Zhang et al. and the supported catalyst taught by Jianhua et al.(current claim 5), the ordinary artisan would have then concentrated the glycolic acid solution with the distillation taught by Jianhua et al. to greater than or equal to 70 wt.%. Distillation methods taught by Jianhua et al. can necessarily incorporate distillation columns as evidence by Nianjun et al. (Figure 1, par. 22).
Concerning the current crystallization, the ordinary artisan would have arrived at the high purity filtered and separated crystalline glycolic acid with a reasonable expectation of success because Jianhua et al. teaches to do so.
Concerning the coupling of the vacuum distillation method taught by Jianhua et al. to the crystallization kettle in series, Nianjun et al. teach evaporator/distillation column apparatus in fluid communication to a crystallizer (item 4 in Figure 1 of Nianjun et al.). The ordinary artisan would have utilized the fluid or at least coupled setup item 4 taught by Nianjun et al. to couple in series the vacuum distillation method taught by Jianhua et al. to the crystallization flask taught by Jianhua et al. The ordinary artisan would have done so with an expectation of success to aid in the placement of the
glycolic acid concentrate to the crystallizer and because coupling of distillation and crystallizers are known in the prior art..
Concerning claim 7 and the crystallization temperature, MPEP 2144.05 I.: “In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976).”
Concerning claim 7 and the stirring rate and the cooling rate and seed concentration, these parameters are determined to be result effective variables. Thus adjusting these parameters during routine experimentation to arrive at the claimed ranges would have been obvious. 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) 6 is/are rejected under 35 U.S.C. 103 as being unpatentable over Jianhua et al. (CN102153461, Published 08-2011. Machine translation attached.), Zhang et al. (US Patent 7,960,594, Patent date 06-2011), and Nianjun et al. (CN103508878, Published 01-2014. Machine translation attached.) as evidence by Chemistry (3 pages, Published 11-2020), Reddit (7 pages, Published 6 years ago or 2019), and Rddennehy (3 pages, Published 08/23/2021) as applied to claims 1-2, 4-5 and 7 and in further view of Stichlmair (Distillation and Rectification, 98 pages, Published 2005) and as evidence by McCabe (Appendix II-H. McCabe-Thiele Analysis, 15 pages, Published 11-2002), AMACS (AMACS Process Tower Internals, 3 pages, Published 09/20/2018).
Scope of the Prior Art
The teachings of Jianhua et al., Zhang et al., and Nianjun et al. as evidence by Chemistry, Reddit, and Rddennehy are in the above 103 rejection and are incorporated by reference.
As a reminder Jianhua et al. teach the use of vacuum distillation methods when evaporating the water from the crude glycolic acid solution (p. 4/5, par. 40). The taught vacuum distillation reads on the claimed vacuum rectification.
Jianhua et al. teach overlapping temperatures and pressures compared to the claimed 20 to 250C, 60C, 0-10 MPa and 0.29 MPa. For example, Jianhua et al. teach 60-120C and 10-30 kPa or (0.01 to 0.03 MPa) (p. 5/5). Additionally, Jianhua et al. teach overlapping crude glycolic acid concentrations in wt% as currently claimed. For example, Jianhua et al. teach evaporating water in the reaction product to concentrate the glycolic acid in the product to 70-80 wt% (page 1/1, claim 2). Concerning the starting concentration of the crude glycolic acid solution with a mass fraction of 35 wt.%,
Jianhua et al. teach the content of the glycolic acid is about 35wt% or so (page 4/5, par.
40).
Ascertain the Differences
Jianhua et al., Zhang et al., and Nianjun et al. do not teach the feed temperature, the use of plates or the number thereof, nor the reflux ratio.
Secondary References
Stichlmair teach motivation to utilize plate columns when vacuums are employed. For example, Stichlmair teach plate columns can also be operated efficiently at very low liquid loads, e.g., in vacuum operation”, “heat to be added or removed easily” and “plate columns are also relatively insensitive to impurities in the liquid” (bridging pages 75-76).
The above teachings render the prior art overlapping in nature to the teachings of Jianhua et al. and analogous art to the invention. The reason being the prior art teach the use of a vacuum.
Concerning the reflux ratio, this is a result effective variable as evidence by McCabe. For example, McCabe teach the operation of a distillation column requires an idea of the operating conditions to use the achieve the desired separation. A crucial piece of information to have is the minimum reflux ratio. The minimum reflux ratio is a theoretical minimum that would require an infinite number of stages (page II-H-11). Thus, the reflux ratio has an impact on the number of stages. McCabe teach when designing a distillation column it is useful to know the ideal number of stages (page II-H-1).
Concerning the feed temperature, this is considered a result effective variable as
evidence by McCabe, For example, McCabe teach the state of the feed to the distillation tower is an important parameter for the engineer to know (page II-H-5). McCabe teach variations of the feed including cold, vaporized and superheated (page II-H-5). This teaching is interpreted to imply temperature of the feed. For example, cold feed implies a cold temperature.
Plates are trays and stages and are a result effective variable as evidence by AMACS. For example, AMACS teach “Trays are separation devices used in process plants, most often in distillation towers. The tray column is one the most widely used types of distillation columns. It is also at times referred to as a plate column. The number of trays and stages in the column is designed for the desired purity and difficulty of the separation process. Height of the column also determines the number of stages” (p. 2 of 3).
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have utilized the plate column taught by Stichlmair as the vacuum distillation taught by Jianhua et al. The ordinary artisan would have done so with a reasonable expectation of success because Stichlmair teach the use of plate columns being run efficiently when utilizing a vacuum. Moreover, additional benefits to motivate the ordinary artisan in using a plate column are “heat to be added or removed easily” and “plate columns are also relatively insensitive to impurities in the liquid”.
Concerning the temperatures, pressures and wt.%’s of claim 6,MPEP 2144.05 I.:
“In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976).”
Concerning the feed temperature, number of plates and reflux ratio, these are
argued above to be result effective variables. Thus arriving at the claimed values for the result effective variables would have been arrived at by routine experimentation. 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).
Additionally, temperatures and pressures of the plate column are obvious. Evaporation of water, which has a boiling point property, would necessarily be effected by pressures and temperatures. A temperature approaching the boiling point of water would necessarily increase evaporation. Pressure is directly related to temperature. Finding the workable absolute pressures and bottom temperatures of the vacuum rectification column through routine experimentation would have been obvious.
Claim(s) 3 is/are rejected under 35 U.S.C. 103 as being unpatentable over Jianhua et al. (CN102153461, Published 08-2011. Machine translation attached.), Zhang et al. (US Patent 7,960,594, Patent date 06-2011), and Nianjun et al. (CN103508878, Published 01-2014. Machine translation attached.) as evidence by Chemistry (3 pages, Published 11-2020), Reddit (7 pages, Published 6 years ago or 2019), and Rddennehy (3 pages, Published 08/23/2021) as applied to claims 1-2, 4-5 and 7 and in further view of Saito et al. (JP1978046916, published 04-1978.
machine translation attached).
Scope of the Prior Art
The teachings of Jianhua et al., Zhang et al., and Nianjun et al. as evidence by
Chemistry, Reddit, and Rddennehy are in the above 103 rejection and are incorporated by reference.
Ascertain the Differences
Jianhua et al., Zhang et al., and Nianjun et al. do not teach the use pf a Pt/C catalysts to prepare the crude glycolic acid via the use of a bio-based ethylene glycol at 80C for 10 hours.
Secondary References
Saito et al. teach the catalytic conversion of ethylene glycol in the presence of water, and a Pt/C catalyst at 45-55C for 24 hours with a conversion of 99.5% and a yield of glycolic acid at 84.5% (p. 97-98, Examples 1-2).
Saito et al. teach temperatures of 20 to 80C which overlaps the current temp. of 80C (p. 97, right column). Saito et al. teach the reaction time is dependent on the ethylene glycol concentration (p. 97, right column). Saito et al. teach the reaction time varies depending on the reaction conditions such as the amount of catalyst used, but is approximately 5 to 30 hours (p. 97, left column). This time overlaps the claim time of 10 h.
Saito et al. teach overlapping methods to isolate the glycolic acid as compared to the teachings of Jianhua et al. and of those being claimed. For example, Saito et al. teach concentrating the glycolic acid product under reduced pressure at 45C, drying to obtain glycolic acid crystals (p. 97, right column).
Saito et al. teach motivation to use the Pt/C catalytic method. For example, Saito
et al. teach “The reaction solution obtained by the method of the present invention is colorless and transparent, and after concentration to a predetermined concentration. the purity of the active ingredient, hydroxyacetic acid, is 98% or more, and high-quality hydroxyacetic acid can be obtained without any purification steps.
Even more surprisingly, the platinum-carbon catalyst used in the method of the present invention can be used repeatedly more than 50 times without losing any of its activity even after 50 uses, and furthermore, the catalyst can be used as is without any operation to maintain its activity during repeated use. Therefore, despite the use of an
expensive metal catalyst, the cost of the catalyst can be kept very low, making the present invention advantageous for industrial production (p. 97, left column).
The above teachings render the prior art overlapping in nature to the teachings of Jianhua et al. and analogous art to the invention. The reason the prior art teach production of glycolic acid. .
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have utilized the ethylene glycol from cellulose as taught by Zhang et al. in the process to convert ethylene glycol to glycolic acid taught by Saito et al. with a reasonable expectation of success. The ordinary artisan would have done so to “reduce the dependence on the petroleum, so as to build
an eco friendly manufacturing process”.
Next the ordinary artisan would have utilized the arrived at concentrating vacuum distillation methods by the ordinary artisan in the previous 103 rejections to achieve the claimed separating and purifying the obtained crude glycolic acid using the rectification/crystallization coupling process to obtain high-purity glycolic acid. The ordinary artisan would have done so with a reasonable expectation of success to satisfy a need for the evaporative/crystallization taught by Saito et al.
The ordinary artisan would have looked to the prior art from the vantage point of Saito et al. because Saito et al. teach overlapping subject matter in relation to the prior art and was determined to be analogous art to the invention.
Conclusion
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/B.G.D/Examiner, Art Unit 1692 /Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625