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 1-18 and 21-24 are pending. Claims 1-18 and 21-24 are under examination. Claims 1-18 and 21-24 are rejected. No claims allowed.
Filing Receipt
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Claim Interpretation
The phrase “utilized acetylation fluid” is a fluid recovered from any wood acetylation process (See the current specification page 6 lines 16-17). The specification goes on to recite on page 1, “Generally, the utilized acetylation fluid will comprise by-products from wood acetylation, extracted components from wood, such as terpenes and/or terpenoids, and excess acetylation fluid. Typically, when including acetic anhydride in the acetylation fluid, a byproduct is acetic acid”. The above generalization is not a definition but rather an example. Alterations to the “utilized acetylation fluid” prior to the cooling step in claim 1 are acceptable. See current claim 10.
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.
Claims 1-18 and 21-24 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 1 and all dependent claims are directed to formation of crystals. However, the identity of the composition of the crystals needs clarity. For example, solidification (freezing) and/or melting temperatures of pure and impure substances are different. See page 10 of the current specification. Thus, any substance in the “utilized acetylation fluid” may be forming a crystal and not the acetic acid. Cooling below the melting point of pure acetic acid may or may not be crystalizing acetic acid from an impure acetic acid solution. Clarification is needed.
Additionally, claim 1 may be referring to the melting temperature/point of glacial acetic acid or another temperature presumably the melting point of an impure acetic acid or any temperature that causes any acetic acid to melt in any impure or pure form.
Additionally, clarity is needed as to what entity is being purified. The utilized
acetylation fluid or the acetic acid. See argument for claim 2 immediately below.
Claim 2 is directed towards removing impurities. However, the substance from where the impurities are removed is not understood. It is not understood if the impurities are removed from the “utilized acetylation fluid” or removed from acetic acid when the acetic acid is presumably crystalized. Claim 2 could be referring to removing impurities from a utilized acetylation fluid wherein acetic acid has been removed by crystallization. Moreover, claim 2 could be removing the impurities from the utilized acetylation fluid prior at any crystallization taking place. Additionally, the impurities could be crystalized out in claim 1, due to the crystals of claim 1 not being identified nor the temperatures being utilized.
Claim 2 utilizes the phrase “such as”. MPEP 2173.05(d): Description of examples or preferences is properly set forth in the specification rather than the claims. If stated in the claims, examples and preferences may lead to confusion over the intended scope of a claim.
Claims 4, 7, 12, and 15 have preferable phrases. MPEP 2173.05(d): Description of examples or preferences is properly set forth in the specification rather than the claims. If stated in the claims, examples and preferences may lead to confusion over the intended scope of a claim. Dependent claim 22 is also rejected due to being dependent on rejected claim 7.
Claim 6, step (c) is directed to recirculating said acetic acid melt. Clarity as to the definition of recirculating is needed. The acetic acid melt may be recirculated to step (a). However step (a) lacks antecedent basis for an acetic acid melt. Moreover, if the acetic acid melt is recirculated to step (a), the question becomes how the melt that is in step (a) is subjected to cooling in step (d). rejection is being applied to claim 15 which also requires a recirculation.
Recirculating is redundant in claim 6. Removing step (c) does not appear to alter the scope of the claim. The question becomes why recirculating is being utilized. Without understanding why the word recirculating is being used, recirculating may therefore be imparting unknown limitations into the claims.
Additionally, regarding claim 15, clarification of recirculated is needed. Claim 15 can be written without the word recirculated. For example the fluid remaining can be subjected to the steps of cooling and crystallization. Additionally, claim 15 appears to be in need of a melt so additional crystallizations can occur. See claim 14, wherein plurality of subsequent melting and re-crystallization steps occur.
Regarding claim 10, the phrase "such as" renders the claim indefinite because it is unclear whether the limitations following the phrase are part of the claimed invention. See MPEP § 2173.05(d).
Claim 11 needs clarity as to why the temperature of cooling is reiterated to be below the melting point of acetic acid as is directed in claim 1 from where claims 10 and 11 depend. Perhaps the cooling step in claim 11 is not the cooling step in claim 1.
However, claim 10 from where claim 11 depends recites “said cooling” presumably referring to the “cooling” in claim 1. Clarity is needed.
Claim 14 comprises a plurality of subsequent melting and re-crystallizing steps. As to what is being melted and as to what is being re-crystallized is unknown at this time. Clarity is needed. In interest of compact prosecution, claim 14 is being interpreted as further comprising at least once, melting the separated acetic acid crystals of claim 1 and re-crystallizing the melt.
Claim 17 and 18 are directed to obtaining acetic acid via the process of claim 1.
However, claim 1 from where claim 17 and 18 depend is directed to formation of crystals of an unknown composition. The question becomes how acetic acid is obtained in claim 17 and 18. Clarity is needed.
Claims 8 and 21-22 are directed to adding seed crystals. The identity of the seed crystals are unknown. Note: claim 5 is not being rejected for the immediately above reason due to the seeds being acetic acid seed crystals. Claim 8, although depending from claim 5, is held indefinite because seed crystals in claim 8 is not referring to the seed crystals in claim 5. The definite article “the” does not precede seed crystals in claim 8. In general, any seed crystal of any substance that can be found in utilized acetylation fluid can be added at this point. This is because the identity of the crystal material in claim 1 is unknown.
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, 9, 13 and 16 is/are rejected under 35 U.S.C. 103 as being unpatentable over Nasheri et al. (WO2005/077626, Published 08-2005) and Muller et al. (US Patent 1,941,951, Patent date 01-1934).
Scope of the Prior Art
Nasheri et al. teach the acetylation of wood using acetic anhydride and the reuse of the remaining liquids. See page 11 and claims of Nasheri et al.
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Page 11
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Concerning claim 3, see claim 20 of Nasheri et al.
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Nasheri et al. goes on to teach isolation of acetic acid for dehydrating to acetic anhydride for reuse. See Nasheri et al. page 9.
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Note: the acetylation fluid post acetylation contains acetic acid and acetic acid anhydride (see pages 2 and 9).
Ascertain the Differences
Nasheri et al. does not teach subjecting the recovered acetylation fluid to cooling below the melting point of acetic acid under the formation of crystals, and separating the crystals from the fluid.
Secondary References
Muller et al. teach separation of acetic acid from acetic anhydride and water (column 1, lines 1-6). Muller et al. teach the separation is performed readily and efficiently by cooling (column 1, lines 34-40).
Muller et al. goes on to teach rate of cooling dictates crystallization of water and/or acetic acid (column 2, lines 51-78). Muller et al. teach the fractions achieved by the act of cooling are also influenced not only by the conditions of the operation but also by the composition of the starting material (column2, lines 75-80).
Muller et al. exemplifies the separation of acetic acid from acetic anhydride by crystallizing the acetic acid at -70C. (page 2, Example 1). Example 3 of Muller et al. solidifies acetic acid and water from acetic anhydride at temperatures -30 and -40C.
Muller et al. teach filtration for separating the crystals (page 2, Example 1).
Muller et al. teach modifications/changes to the claims and specification may be made (page 2, column 2, lines 90-105).
Muller et al. teach the recovered acetic anhydride to be utilized for purposes of acetylation (column 2, lines 51-65).
Concerning claim 13, Muller et al. teach washing (page 2, first column Example 5).
The above teachings of the secondary reference overlap with the teachings of
the primary reference and render the secondary reference analogous art to the
invention. The prior art is analogous due to the prior art teaching the crystallization of acetic acid from solutions containing the anhydride. The overlapping subject matter being the separation a acetic acid from mixtures containing acetic acid and anhydride.
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 Nasheri et al. and Muller et al. to arrive at the current invention with a reasonable expectation of success.
Thus, it would have been obvious for the ordinary artisan to have acetylated wood as in current claim 16 and purified the utilized acetylation fluid for reuse with a reasonable expectation of success. The ordinary artisan would have done so because Nasheri et al. teach acetylation of wood and separation/purification of the by-products for reuse (p. 9, 11).
Next, the ordinary artisan being taught by Nasheri et al. that reaction by-products
may optionally be separated, purified and recycled by methods known in the art, would have looked to the art and would have found and practiced the teachings of Muller et al. to crystalize acetic acid from solutions containing acetic anhydride. In doing so, the ordinary artisan would have arrived at the current invention with a reasonable expectation of success. The success from knowing acetic acid compositions crystalize from liquid compositions of acetic acid and acetic acid anhydride when undergoing cooling as taught by Muller at al.
The ordinary artisan would have looked to Muller et al. and would have combined
the teachings therein with Nasheri et al. due to the overlapping subject matter and because Muller et al. being analogous art the invention.
Concerning claim 2, upon crystallization of the acetic acid, the claimed impurities would have been removed. 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).
Both the methods of the claimed invention and the prior art require cooling a utilized acetylation fluid below the melting point of acetic acid under the formation of crystals and separating the crystals from the fluid. Thus, the removal of the claimed impurities from the product purified utilized acetylation fluid/acetic acid would have occurred.
Claim(s) 1-5, 8, 10-13 and 16 is/are rejected under 35 U.S.C. 103 as being unpatentable over Nasheri et al. (WO2005/077626, Published 08-2005), Choi et al. (Separation of Acetic Acid from Acetic Acid-Water Mixture by Crystallization, Separation Science and Technology, 48: 1056–1061, Published 2013).
Scope of the Prior Art
The individual and combinational teachings of Nasheri et al. are written in the above rejection and are incorporated by reference. As a reminder, Nasheri et al. teach the removal of the acetic anhydride from the acetic acid and purification of the acetic acid by methods known in the art (bottom of page 9).
Ascertain the Differences
Nasheri et al. does not teach purifying the recovered acetic acid via crystallization.
Secondary References
Choi et al. teach in general that crystallization is used to purify chemicals (page 1056).
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Choi et al. goes on to teach methods of melt crystallization for purification of acetic acid (p. 1056-1057). Concerning a temperature below the melting temperature of acetic acid, Choi et al. teach -10C (p. 1056). Concerning the separation of the fluid, Choi et al. teach upon formation of the ice layer, the residual solution was drained (p. 1057).
Concerning claim 5 and 8 and addition of seed crystals, Choi et al. teach the following (p. 1056).
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Concerning claim 12, the cooling temperature was a parameter that was investigated (p. 1056).
Concerning claim 13, Choi et al. teach that washing was found to be effective in removing the impurity on the surface (p. 1056).
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have purified the recovered acetic acid from the utilized wood acetylation processes taught by Nasheri et al. with a reasonable expectation of success.
The ordinary artisan would have done so because Nasheri et al. teach the removal of the acetic anhydride from the acetic acid (current claim 10) and purification of the acetic acid by methods known in the art (bottom of page 9).
The ordinary artisan would have looked to the art for purification methods and would have chosen the melt crystallization methods taught by Choi et al. over other conventional purification methods that require big energy consumption and additional chemicals (Choi et al., p. 1056).
The ordinary artisan would have had a reasonable expectation of success in purifying acetic acid via melt crystallization because Choi et al. teach “crystallization of organic materials from the melt is also a separation technique to enable the purification of chemicals” (Choi et al., p. 1056). In doing so the ordinary artisan would have arrived at the current invention.
Concerning claim 2, upon crystallization of the acetic acid, the claimed impurities
would have been removed. 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).
Both the methods of the claimed invention and the prior art require cooling under the formation of crystals of a utilized acetylation fluid comprising acetic acid to below the melting point of acetic acid and separating the crystals from the fluid. Thus, the removal of the claimed impurities from the product purified utilized acetylation fluid/acetic acid would have occurred.
Concerning claim 12, the ordinary artisan instructed to investigate the cooling
temperature would have done so and arrived at the cooling temperatures of claim 12 via 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).
Claim(s) 17-18 and 23-24 is/are rejected under 35 U.S.C. 103 as being unpatentable over Nasheri et al. (WO2005/077626, Published 08-2005) and Muller et al. (US Patent 1,941,951, Patent date 01-1934) as applied to claims 1-4, 9, 13 and 16 in the above 103 rejections and in further view of Benstead et al. (WO2016/009060, Published 01-2016. Cited in the IDS filed 01/25/2023).
Scope of the Prior Art
The individual and combinational teachings of Nasheri et al. and Muller et al. are in the above 103 rejection and are incorporated by reference.
As a reminder, Nasheri et al. teach isolation and purification and use of the acetic acid (page 9).
Ascertain the Differences
Nasheri et al. and/or Muller et al. do not teach the dehydration of acetic acid to prepare ketene nor the reaction thereof with acetic acid to prepare acetic anhydride.
Secondary References
Benstead et al. teach preparing acetic anhydride via preparing ketene from acetic acid and then reacting the ketene with acetic acid to prepare acetic anhydride (p. 3). Benstead et al. teach preparing ketene from the dehydration of acetic acid (p. 1).
Benstead et al. teach wood acetylation and an outlet for the acetylation fluid (p. 3).
The above teachings of the secondary reference overlap with the teachings of the primary reference and render the secondary reference analogous art to the invention. The overlapping subject matter being a wood acetylation with acetylation fluid.
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 recovered acetic acid from the combinational teachings of Nasheri et al. and Muller et al. in the processes taught by Benstead et al. to prepare ketene and/or acetic anhydride with a reasonable expectation of success. The ordinary artisan would have done so to satisfy a source for acetic anhydride and due to the fact that Nasheri et al. teach to separate and utilize the fluid from the acetylation process. The ordinary artisan would have had a reasonable expectation of success due to Benstead et al. teaching acetic anhydride is prepared from acetic acid and ketene.
The ordinary artisan would have looked to Benstead et al. due to the overlapping teachings and due to Benstead et al. being analogous art to the invention.
Concerning claim 23, the optional language is optional. Additionally, the acetic acid from the combinational teachings of Nasheri et al. and Muller et al. would have necessarily been purified due to both the methods of the prior art and the current methods being substantially identical. Utilizing the purified acetic acid in subsequent processes as currently claimed to prepare ketene and then acetic anhydride would have been obvious. The reason being Nasheri et al. teach isolation and purification and use of the acetic acid (page 9).
Concerning claim 24, reuse of the prepared acetic anhydride from the combinational teachings of Nasheri et al., Muller et al. and Benstead et al. in the processes of acetylation of wood from the combinational teachings of Nasheri et al., Muller et al. and Benstead et al. would have been obvious. The reason being, Nasheri et al. prepared acetic anhydride as a source for the processes of Nasheri et al. (p. 9).
Claim(s) 1-8, 10-16 and 21-22 is/are rejected under 35 U.S.C. 103 as being unpatentable over Nasheri et al. (WO2005/077626, Published 08-2005), Jingsong et al. (CN106800605, Published 06-2017. Cited in IDS filed 01/25/2023. Translation attached) and Choi et al. (Separation of Acetic Acid from Acetic Acid-Water Mixture by Crystallization, Separation Science and Technology, 48: 1056–1061, Published 2013).
Scope of the Prior Art
The individual and combinational teachings of Nasheri et al. and Choi et al. are written in the above 103 rejections and are incorporated herein.
Additional teachings of Choi et al. are as follows. Choi et al. teach a partial melt of the crystals (p. 1057 left column). Choi et al. teach impure inclusions occluded on the outside of the layer are easily drained away at the beginning of the sweeting operation (p. 1058).
Ascertain the Differences
Nasheri et al. does not teach the purification of acetic acid via the steps of cooling the recovered acetylation fluid to below the melting point of acetic acid under formation of crystals, subjecting a first portion of the crystals to melting so as to obtain an acetic acid melt, thereby retaining a second portion of the crystals, recirculating said acetic acid melt, subjecting said melt to cooling to below the melting point of acetic acid in the presence of at least part of the retained crystals, nor the plurality of subsequent melting and re-crystallizing steps in claim 14.
Secondary References
Jingsong et al. teach the repeated freezing and heating of acetic acid to prepare edible acetic acid as follows (par. 17).
“Edible acetic acid can be recovered from the recycled hydrolysate using a freezing method. i.e., the acetic acid is cooled to 0-10C to crystallize. The liquid is separated. The crystals are repeatedly heated and melted, and after repeated freezing and heating, it can be concentrated into an edible acetic acid solution of a suitable concentration. The recovered edible acetic acid can be recycled”. The above temperatures overlap the temperatures being claimed.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have purified the recovered acetic acid in the wood acetylation processes taught by Nasheri et al. with a reasonable expectation of success.
The ordinary artisan would have done so because Nasheri et al. teach the removal of the acetic anhydride from the acetic acid and purification of the acetic acid by methods known in the art (bottom of page 9).
The ordinary artisan would have looked to the art for purification methods and would have chosen the repeated melt freeze crystallization methods taught by Jingsong et al. with a reasonable expectation of success. The reasonable expectation of success from Choi et al. teaching “crystallization of organic materials from the melt is also a separation technique to enable the purification of chemicals” (Choi et al., p. 1056).
Concerning subjecting a first portion of the crystals to melting and retaining a second portion of the crystals, this is obvious because Choi et al. teach upon formation of the ice layer, the residual solution was drained (p. 1057).
Concerning the claimed recirculating said acetic acid melt, the teaching of repeated heated and melted, and repeated freezing by Jingsong et al. reads on this limitation.
Concerning the claimed cooling of the melt to below the melting point of acetic acid in the presence of at least part of the retained crystals, this is obvious due to Jingsong et al. teaching repeated heated and melted, and repeated freezing. A repeated heating and melting and refreezing does not necessarily require separation of the melt from the crystals when crystallizing is occurring.
Concerning claim 7, and the first portion, Choi et al. teach a partial melt of the crystals. Thus, a portion of the crystals are melted. Concerning the percent in claim 7, Nasheri et al. teach acetic acid is to be purified and Choi et al. teach the sweating/melt is utilized to drain away impurities. Thus, the amount of melting which is dependent on the impurities in/on the crystals would be 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).
Concerning claim 12, 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 14, Choi et al. teach repeated heating and melting and freezing and heating on the acetic acid. This teaching reads on claim 14.
Concerning claim 15, it would have been obvious to have utilized any fluids containing acetic acid in the purification steps of the combinational teachings of Nasheri et al., Jingsong et al., and Choi et al. This is because Nasheri et al. teach the purification of by-products that include acetic acid for reuse (p. 9).
The ordinary artisan knowing crystallization is utilized to purify compounds (Choi et al. p. 1056), would have utilized crystallization on any fluids that contain acetic acid. This includes the fluid remaining after the separation of the crystals in claim 15. Concerning the number of recirculations, this is interpreted as the number of melting and freezing. Jingsong et al. teach repeated melting and freezing. Thus, the ordinary artisan would have repeated the freezing and melting as currently claimed until the purification for the acetic acid taught by Nasheri et al. was accomplished.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to BLAINE G DOLETSKI whose telephone number is (571)272-2766. The examiner can normally be reached M-F 7-4 EST.
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/B.G.D/Examiner, Art Unit 1692 /Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625