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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on December 10, 2025 has been entered.
Detailed Action
This office action is a response to applicant’s communication submitted December 10, 2025 wherein claim 2 is amended. This application is a national stage application of PCT/US2020/059292, filed November 6, 2020, which claims benefit of provisional application 62/932038, filed November 7, 2019.
Claims 2 and 58-62 are pending in this application.
Claims 2 and 58-62 as amended are examined on the merits herein.
Withdrawn Rejections
Applicant’s amendment and arguments, submitted December 10, 2025, with respect to the rejection of claims 2 and 58-61 under 35 USC 103 for being obvious over Buchanan et al. in view of Ward et al. in view of Akah et al. in view of Angyal et al. in view of Dwidar et al., have been fully considered and found to be persuasive to remove the rejection as the process described by Ward et al. involves an intermediate hydrocracking step such that the material supplied to the steam cracking step is a gas fraction that is not necessarily considered to be a pyrolysis oil. Therefore the rejection is withdrawn.
The following new grounds of rejection are introduced:
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.
Claims 2, 58, and 60 are rejected under 35 U.S.C. 103 as being unpatentable over Buchanan et al. (US pre-grant publication 2012/0238742, of record in previous action) in view of Van Zijl et al. (PCT international publication WO2020/152317, Reference included with PTO-1449 submitted August 24, 2022) in view of Dwidar et al. (Reference of record in previous action)
Independent claim 2 claims a process for making a cellulose ester composition comprising steps of pyrolyzing a plastic waste, feeding the resulting pyrolysis oil into a steam cracker in combination with a non-recycle hydrocarbon, processing the olefin effluent by one of several further reactions to produce butyric acid or butyric anhydride, and reacting said reactant with cellulose to produce a cellulose ester. Dependent claim 58 further specifies that the cellulose ester is cellulose acetate butyrate.
Buchanan et al. discloses a process for producing a cellulose ester comprising dissolving cellulose in an ionic liquid, and then esterifying the cellulose in the ionic liquid. (p. 1 paragraph 9) The process further comprises adding a carboxylate donor to the ionic liquid, which can include a C2-C4 straight chain carboxylic acid, from which one skilled in the art would at once envisage butyric acid, or an anhydride such as butyric anhydride. (p. 5 paragraphs 55-56, p. 7 paragraph 77) The cellulose ester can be a mixed ester, containing ester groups selected from a list including acetate and butyrate. (p. 10 paragraph 92) In particular, cellulose acetate butyrate is described as one of the mixed esters that can be produced by this process. (p. 12 paragraphs 107 and 108) Buchanan et al. does not specifically describe the source of the butyric acid or butyric anhydride.
Van Zijl et al. discloses a process for treating waste plastic feedstocks comprising providing a hydrocarbon stream obtained by treatment of a waste plastic feedstock, providing a hydrocarbon stream B, combining the two streams, and processing the combined stream in a steam cracker. (p. 3 paragraph 12) The waste plastic stream A can be obtained by pyrolysis of waste plastic, in which case it is reasonably considered to be a pyrolysis oil. (p. 7 paragraphs 34 and 35) The hydrocarbon stream B consists of various nonrecycle content hydrocarbons. (p. 10 paragraph 51 – p. 11 paragraph 50) The combined stream C preferably contains between 1 and 10% of stream A, which falls within the scope of present claim 60, with the remainder being stream B. (p. 13 paragraph 67) The resulting cracked product comprises lower olefins such as ethylene and propylene as predominant products. (p. 14 paragraph 73)
Dwidar et al. discloses that butyric acid can be produced by transformation of propylene into butyraldehyde, which is then transformed into butyric acid. (p. 2 section 2)
It would therefore have been obvious to one of ordinary skill in the at the time of the invention to use pyrolysis of waste plastic and subsequent steam cracking of the resulting pyrolysis oil to produce propylene, which could then be subject to chemical conversion to butanoic acid to produce butanoic acid for use in the process described by Buchanan et al. One of ordinary skill in the art would have been motivated by Buchanan et al. to look for sources of butyric acid to use in the disclosed process, since this compound is described as a useful reactant. Note that while Van Zijl et al. describes propylene as a feedstock for the production of polypropylene, nothing about the disclosure would suggest that propylene produced by this process would necessarily have to be used for this specific purpose and could not be utilized to make other products, such as butyric acid, for which propylene is a known precursor.
Regarding claim 58, as mentioned previously, Buchanan et al. specifically describes making cellulose acetate butyrate.
Therefore the invention taken as a whole is prima facie obvious.
Claims 2 and 58-61 are rejected under 35 U.S.C. 103 as being unpatentable over Buchanan et al. (US pre-grant publication 2012/0238742, of record in previous action) in view of Stabel et al. (US patent 5731483, cited in PTO-1449 submitted August 24, 2022) in view of Akah et al. (Reference of record on previous action) in view of Angyal et al. (Reference of record in previous action) Dwidar et al. (Reference of record in previous action)
Independent claim 2 claims a process for making a cellulose ester composition comprising steps of pyrolyzing a plastic waste, feeding the resulting pyrolysis oil into a steam cracker in combination with a non-recycle hydrocarbon, processing the olefin effluent by one of several further reactions to produce butyric acid or butyric anhydride, and reacting said reactant with cellulose to produce a cellulose ester. Dependent claim 58 further specifies that the cellulose ester is cellulose acetate butyrate.
Buchanan et al. discloses a process for producing a cellulose ester comprising dissolving cellulose in an ionic liquid, and then esterifying the cellulose in the ionic liquid. (p. 1 paragraph 9) The process further comprises adding a carboxylate donor to the ionic liquid, which can include a C2-C4 straight chain carboxylic acid, from which one skilled in the art would at once envisage butyric acid, or an anhydride such as butyric anhydride. (p. 5 paragraphs 55-56, p. 7 paragraph 77) The cellulose ester can be a mixed ester, containing ester groups selected from a list including acetate and butyrate. (p. 10 paragraph 92) In particular, cellulose acetate butyrate is described as one of the mixed esters that can be produced by this process. (p. 12 paragraphs 107 and 108) Buchanan et al. does not specifically describe the source of the butyric acid or butyric anhydride.
Stabel et al. discloses a method for converting waste plastic to feed materials for steam cracking. (column 1 lines 9-25) The plastic waste is melted and fed into a reactor at high temperature, in a process that is reasonably considered to be pyrolysis and to result in pyrolysis oil. (column 2 lines 28-50) The products of this steam cracking process include propylene. (column 2 lines 25-27, column 7 example 1)
Akah et al. discloses that propylene is typically obtained as a byproduct of steam cracking of feedstocks, including feed alkanes such as ethane and propane. (p. 266 left column second paragraph, also table 1) Angyal et al. discloses that steam cracking feedstocks can be derived by mild cracking (pyrolysis) of various plastic wastes. (p. 1718 left column second paragraph) Results of the initial pyrolysis included gas, distillate, and oil. (p. 1718 left column second paragraph) The products of steam cracking included propylene. (p. 1722 table 3) Dwidar et al. discloses that butyric acid can be produced by transformation of propylene into butyraldehyde, which is then transformed into butyric acid. (p. 2 section 2)
It would therefore have been obvious to one of ordinary skill in the at the time of the invention to use pyrolysis of waste plastic and subsequent steam cracking of the resulting pyrolysis oil to produce propylene, which could then be subject to chemical conversion to butanoic acid to produce butanoic acid for use in the process described by Buchanan et al. One of ordinary skill in the art would have been motivated by Buchanan et al. to look for sources of butyric acid to use in the disclosed process, since this compound is described as a useful reactant. Note that while Stabel et al. describes propylene as a feedstock for the production of polypropylene, nothing about the disclosure would suggest that propylene produced by this process would necessarily have to be used for this specific purpose and could not be utilized to make other products, such as butyric acid, for which propylene is a known precursor.
Furthermore regarding the limitation requiring a step of co-feeding the recycled pyoil into the steam cracker along with a non-recycled hydrocarbon stream, It would have been obvious to one of ordinary skill in the art at the time of the invention to carry out steam cracking of multiple different feedstocks, including both recycled pyoil and nonrecycled hydrocarbons such as natural gas. One of ordinary skill in the art would have found this to be obvious because both types of feedstocks are described as being useful for steam cracking to produce light olefins in the cited art, suggesting using both feedstocks as sources of light olefins (e.g. propylene) in steam cracking.
Regarding claim 58, as mentioned previously, Buchanan et al. specifically describes making cellulose acetate butyrate. Regarding claims 59 and 61, one of ordinary skill in the art would have found it to be obvious to use natural gas comprising for example propane as part of the feedstock, in view of the disclosure by Akah et al. that these gasses are a typical feedstock for production of propylene.
Regarding claim 60, it would furthermore have been obvious to one of ordinary skill in the art at the time of the invention to determine the appropriate amount of each feedstock to use in the steam cracking process, based on factors such as their relative cost and availability, and the desired product distribution.
Therefore the invention taken as a whole is prima facie obvious.
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. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); 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.2d 438, 164 USPQ 619 (CCPA 1970); 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) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) 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 www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 2 and 59-61 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-3, 7, and 17 of U.S. Patent No. 12397467 (Cited in PTO-892, herein referred to as ‘467) in view of Van Zijl et al. (PCT international publication WO2020/152317, Reference included with PTO-1449 submitted August 24, 2022) in view of Dwidar et al. (Reference of record in previous action)
Claim 1 is directed to a process for producing a cellulose ester comprising obtaining recycle content ethylene, converting the ethylene into a reactant for preparing a cellulose ester, and reacting said reactant with cellulose to produce the cellulose ester. Claim 3 further describes steps wherein the ethylene is converted to propionic acid which is converted to propionic anhydride. Claim 2 further describes the cellulose ester as being a cellulose propionate, which can additionally be a cellulose propionate butyrate. Dependent claim 7 further describes steps of making said ethylene by pyrolyzing waste plastic, followed by cracking the pyoil to produce ethylene. Dependent claim 17 further describes an embodiment wherein the pyoil is between 1-40% of a combined feed stream subjected to cracking, wherein the remainder is a non-recycle feedstock including C2-C4 hydrocarbons, which one of ordinary skill in the art would have seen as including ethane and propane. The claims of ‘467 do not specifically describe an embodiment also comprising steps of producing propylene from pyrolysis oil, converting the propylene into butyric acid, and butyric anhydride, and using this as an additional reactant to produce cellulose acetate butyrate.
Van Zijl et al. discloses a process for treating waste plastic feedstocks comprising providing a hydrocarbon stream obtained by treatment of a waste plastic feedstock, providing a hydrocarbon stream B, combining the two streams, and processing the combined stream in a steam cracker. (p. 3 paragraph 12) The waste plastic stream A can be obtained by pyrolysis of waste plastic, in which case it is reasonably considered to be a pyrolysis oil. (p. 7 paragraphs 34 and 35) The hydrocarbon stream B consists of various nonrecycle content hydrocarbons. (p. 10 paragraph 51 – p. 11 paragraph 50) The combined stream C preferably contains between 1 and 10% of stream A, which falls within the scope of present claim 60, with the remainder being stream B. (p. 13 paragraph 67) The resulting cracked product comprises lower olefins such as ethylene and propylene as predominant products. (p. 14 paragraph 73)
Dwidar et al. discloses that butyric acid can be produced by transformation of propylene into butyraldehyde, which is then transformed into butyric acid. (p. 2 section 2)
It would therefore have been obvious to one of ordinary skill in the at the time of the invention to use pyrolysis of waste plastic and subsequent steam cracking of the resulting pyrolysis oil to produce propylene, which could then be subject to chemical conversion to butanoic acid to produce butanoic anhydride to use in the process described by the claims of ‘467 for producing cellulose propionate butyrate. One of ordinary skill in the art would have been motivated by the reference to cellulose propionate butyrate in the claims of ‘467 to look for sources of butyric anhydride to use to introduce butyrate esters analogously to the use of propionic anhydride to introduce the propionate esters.. Note that while Van Zijl et al. describes propylene as a feedstock for the production of polypropylene, nothing about the disclosure would suggest that propylene produced by this process would necessarily have to be used for this specific purpose and could not be utilized to make other products, such as butyric acid, for which propylene is a known precursor.
Claims 2 and 58-61 are rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1 of U.S. Patent No. 12371625 (Cited in PTO-892, herein referred to as ‘625) in view of over Buchanan et al. (US pre-grant publication 2012/0238742, of record in previous action) in view of Dwidar et al. (Reference of record in previous action)
Claim 1 of ‘625 claim a process comprising steam cracking a pyoil that has not been hydrotreated, to produce a product stream containing propylene. Claim 1 of ‘625 further specifies that the pyoil is 1-25% of the feed stream, and the remainder is non-recycled propane. The presently claimed process differs from that of ‘625 in that it does not include further steps of converting the propylene to butyric acid or butyric anhydride, and reacting the butyric anhydride with cellulose to make cellulose butyrate.
Buchanan et al. discloses a process for producing a cellulose ester comprising dissolving cellulose in an ionic liquid, and then esterifying the cellulose in the ionic liquid. (p. 1 paragraph 9) The process further comprises adding a carboxylate donor to the ionic liquid, which can include a C2-C4 straight chain carboxylic acid, from which one skilled in the art would at once envisage butyric acid, or an anhydride such as butyric anhydride. (p. 5 paragraphs 55-56, p. 7 paragraph 77) The cellulose ester can be a mixed ester, containing ester groups selected from a list including acetate and butyrate. (p. 10 paragraph 92) In particular, cellulose acetate butyrate is described as one of the mixed esters that can be produced by this process. (p. 12 paragraphs 107 and 108) Buchanan et al. does not specifically describe the source of the butyric acid or butyric anhydride.
Dwidar et al. discloses that butyric acid can be produced by transformation of propylene into butyraldehyde, which is then transformed into butyric acid. (p. 2 section 2)
It would therefore have been obvious to one of ordinary skill in the at the time of the invention to use pyrolysis of waste plastic and subsequent steam cracking of the resulting pyrolysis oil to produce propylene, which could then be subject to chemical conversion to butanoic acid to produce butanoic acid for use in the process described by Buchanan et al. One of ordinary skill in the art would have been motivated by Buchanan et al. to look for sources of butyric acid to use in the disclosed process, since this compound is described as a useful reactant.
Regarding claim 58, as mentioned previously, Buchanan et al. specifically describes making cellulose acetate butyrate.
Claims 2 and 58-62 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 3, 4, 7, 8, and 17 of U.S. Patent No. 12338211 (Cited in PTO-892, herein referred to as ‘211) in view of over Buchanan et al. (US pre-grant publication 2012/0238742, of record in previous action) in view of Dwidar et al. (Reference of record in previous action)
Claims 3 and 4 of ‘211 claim a process comprising steam cracking a pyoil that in a thermal steam furnace, and then converting the propylene to a C4 alkanal. Claims 7 and 8 of ‘211 further describe the pyoil as containing recycle content, of example waste plastic. Claim 17 of ‘211 further specifies that the pyoil feed stream contains an additional C2-C4 hydrocarbon feed stream, which one of ordinary skill in the art would see as including ethane or propane. The presently claimed process differs from that of ‘211 in that it does not include further steps of converting the C4 alkanal to butyric acid or butyric anhydride, and reacting the butyric anhydride with cellulose to make cellulose butyrate.
Buchanan et al. discloses a process for producing a cellulose ester comprising dissolving cellulose in an ionic liquid, and then esterifying the cellulose in the ionic liquid. (p. 1 paragraph 9) The process further comprises adding a carboxylate donor to the ionic liquid, which can include a C2-C4 straight chain carboxylic acid, from which one skilled in the art would at once envisage butyric acid, or an anhydride such as butyric anhydride. (p. 5 paragraphs 55-56, p. 7 paragraph 77) The cellulose ester can be a mixed ester, containing ester groups selected from a list including acetate and butyrate. (p. 10 paragraph 92) In particular, cellulose acetate butyrate is described as one of the mixed esters that can be produced by this process. (p. 12 paragraphs 107 and 108) Buchanan et al. does not specifically describe the source of the butyric acid or butyric anhydride.
Dwidar et al. discloses that butyric acid can be produced by transformation of propylene into butyraldehyde, which is then transformed into butyric acid. (p. 2 section 2)
It would therefore have been obvious to one of ordinary skill in the at the time of the invention to use pyrolysis of waste plastic and subsequent steam cracking of the resulting pyrolysis oil to produce propylene, which could then be subject to chemical conversion to butanoic acid to produce butanoic acid for use in the process described by Buchanan et al. One of ordinary skill in the art would have been motivated by Buchanan et al. to look for sources of butyric acid to use in the disclosed process, since this compound is described as a useful reactant.
Regarding claim 58, as mentioned previously, Buchanan et al. specifically describes making cellulose acetate butyrate.
Claims 2, 58, and 60 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-8 of U.S. Patent No. 12312540 (Cited in PTO-1449, herein referred to as ‘540) in view of over Buchanan et al. (US pre-grant publication 2012/0238742, of record in previous action) in view of Van Zijl et al. (PCT international publication WO2020/152317, Reference included with PTO-1449 submitted August 24, 2022) in view of Dwidar et al. (Reference of record in previous action)
Claim 1 ‘540 claim a process comprising introducing a pyrolysis feed into a furnace to produce a pyrolysis oil, and then steam cracking the pyrolysis oil to produce ethylene and propylene. Claims 2-8 of ‘211 further describe the pyrolysis feed as including waste plastic. The presently claimed process differs from that of ‘211 in that it does not include further steps of converting the C4 alkanal to butyric acid or butyric anhydride, and reacting the butyric anhydride with cellulose to make cellulose butyrate.
Buchanan et al. discloses a process for producing a cellulose ester comprising dissolving cellulose in an ionic liquid, and then esterifying the cellulose in the ionic liquid. (p. 1 paragraph 9) The process further comprises adding a carboxylate donor to the ionic liquid, which can include a C2-C4 straight chain carboxylic acid, from which one skilled in the art would at once envisage butyric acid, or an anhydride such as butyric anhydride. (p. 5 paragraphs 55-56, p. 7 paragraph 77) The cellulose ester can be a mixed ester, containing ester groups selected from a list including acetate and butyrate. (p. 10 paragraph 92) In particular, cellulose acetate butyrate is described as one of the mixed esters that can be produced by this process. (p. 12 paragraphs 107 and 108) Buchanan et al. does not specifically describe the source of the butyric acid or butyric anhydride.
Dwidar et al. discloses that butyric acid can be produced by transformation of propylene into butyraldehyde, which is then transformed into butyric acid. (p. 2 section 2)
It would therefore have been obvious to one of ordinary skill in the at the time of the invention to use pyrolysis of waste plastic and subsequent steam cracking of the resulting pyrolysis oil to produce propylene, which could then be subject to chemical conversion to butanoic acid to produce butanoic acid for use in the process described by Buchanan et al. One of ordinary skill in the art would have been motivated by Buchanan et al. to look for sources of butyric acid to use in the disclosed process, since this compound is described as a useful reactant.
The present claims also differ from the claims of ‘540 in that they do not describe adding a non-recycle component to the pyrolysis oil. However, Van Zijl et al. discloses a process for treating waste plastic feedstocks comprising providing a hydrocarbon stream obtained by treatment of a waste plastic feedstock, providing a hydrocarbon stream B, combining the two streams, and processing the combined stream in a steam cracker. (p. 3 paragraph 12) The waste plastic stream A can be obtained by pyrolysis of waste plastic, in which case it is reasonably considered to be a pyrolysis oil. (p. 7 paragraphs 34 and 35) The hydrocarbon stream B consists of various nonrecycle content hydrocarbons. (p. 10 paragraph 51 – p. 11 paragraph 50) The combined stream C preferably contains between 1 and 10% of stream A, which falls within the scope of present claim 60, with the remainder being stream B. (p. 13 paragraph 67) The resulting cracked product comprises lower olefins such as ethylene and propylene as predominant products. (p. 14 paragraph 73)
Therefore it would have been obvious to one of ordinary skill in the art at the time of the invention to combine the pyrolysis oil used in the method of ‘540 with an additional non-recycle hydrocarbon feedstock, in view of the suggestion of Van Zijl to do so.
Regarding claim 58, as mentioned previously, Buchanan et al. specifically describes making cellulose acetate butyrate.
Claims 2 and 58-62 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 4, and 11 of copending Application No. 16/881030 (US pre-grant publication 2020/0369965, cited in PTO-1449, herein referred to as ‘030) in view of Buchanan et al. (US pre-grant publication 2012/0238742, of record in previous action) in view of Dwidar et al. (Reference of record in previous action)
Claim 1 of ‘030 claims a method for making olefins comprising steam cracking a combination of a non-recycle feed comprising ethane, propane and/or butane and a recycle content pyrolysis oil comprising waste plastic, wherein the waste plastic pyoil is present in an amount of 1-30% by weight. Dependent claim 11 of ‘030 further describes the nonrecycle feed as being ethane and/or propane. Dependent claim 4 descries the product stream as including propylene. The presently claimed process differs from that of ‘030 in that it does not include further steps of converting the propylene to butyric acid or butyric anhydride, and reacting the butyric anhydride with cellulose to make cellulose butyrate.
Buchanan et al. discloses a process for producing a cellulose ester comprising dissolving cellulose in an ionic liquid, and then esterifying the cellulose in the ionic liquid. (p. 1 paragraph 9) The process further comprises adding a carboxylate donor to the ionic liquid, which can include a C2-C4 straight chain carboxylic acid, from which one skilled in the art would at once envisage butyric acid, or an anhydride such as butyric anhydride. (p. 5 paragraphs 55-56, p. 7 paragraph 77) The cellulose ester can be a mixed ester, containing ester groups selected from a list including acetate and butyrate. (p. 10 paragraph 92) In particular, cellulose acetate butyrate is described as one of the mixed esters that can be produced by this process. (p. 12 paragraphs 107 and 108) Buchanan et al. does not specifically describe the source of the butyric acid or butyric anhydride.
Dwidar et al. discloses that butyric acid can be produced by transformation of propylene into butyraldehyde, which is then transformed into butyric acid. (p. 2 section 2)
It would therefore have been obvious to one of ordinary skill in the at the time of the invention to use pyrolysis of waste plastic and subsequent steam cracking of the resulting pyrolysis oil to produce propylene, which could then be subject to chemical conversion to butanoic acid to produce butanoic acid for use in the process described by Buchanan et al. One of ordinary skill in the art would have been motivated by Buchanan et al. to look for sources of butyric acid to use in the disclosed process, since this compound is described as a useful reactant.
Regarding claim 58, as mentioned previously, Buchanan et al. specifically describes making cellulose acetate butyrate.
This is a provisional nonstatutory double patenting rejection.
Claims 2 and 58-62 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 18 and 21 of copending Application No. 16/881032 (US pre-grant publication 2020/0369966, cited in PTO-892, herein referred to as ‘032) in view of Buchanan et al. (US pre-grant publication 2012/0238742, of record in previous action) in view of Angyal et al. (Reference included with PTO-1449) in view of Dwidar et al. (Reference of record in previous action)
Claim 18 of ‘032 claims a method for making olefins comprising steam cracking a combination of a non-recycle feed comprising C2-C4 hydrocarbons and a recycle content pyrolysis oil comprising waste plastic. Dependent claim 21 of ‘032 further describes the nonrecycle feed as comprising at least 60% ethane and/or propane. The presently claimed process differs from that of ‘032 in that it does not describe the olefins as including propylene, or include further steps of converting the propylene to butyric acid or butyric anhydride, and reacting the butyric anhydride with cellulose to make cellulose butyrate.
Buchanan et al. discloses a process for producing a cellulose ester comprising dissolving cellulose in an ionic liquid, and then esterifying the cellulose in the ionic liquid. (p. 1 paragraph 9) The process further comprises adding a carboxylate donor to the ionic liquid, which can include a C2-C4 straight chain carboxylic acid, from which one skilled in the art would at once envisage butyric acid, or an anhydride such as butyric anhydride. (p. 5 paragraphs 55-56, p. 7 paragraph 77) The cellulose ester can be a mixed ester, containing ester groups selected from a list including acetate and butyrate. (p. 10 paragraph 92) In particular, cellulose acetate butyrate is described as one of the mixed esters that can be produced by this process. (p. 12 paragraphs 107 and 108) Buchanan et al. does not specifically describe the source of the butyric acid or butyric anhydride.
Angyal et al. discloses that steam cracking feedstocks can be derived by mild cracking (pyrolysis) of various plastic wastes. (p. 1718 left column second paragraph) Results of the initial pyrolysis included gas, distillate, and oil. (p. 1718 left column second paragraph) The products of steam cracking included propylene. (p. 1722 table 3)
Dwidar et al. discloses that butyric acid can be produced by transformation of propylene into butyraldehyde, which is then transformed into butyric acid. (p. 2 section 2)
It would therefore have been obvious to one of ordinary skill in the at the time of the invention to use pyrolysis of waste plastic and subsequent steam cracking of the resulting pyrolysis oil to produce propylene, which could then be subject to chemical conversion to butanoic acid to produce butanoic acid for use in the process described by Buchanan et al. One of ordinary skill in the art would have been motivated by Buchanan et al. to look for sources of butyric acid to use in the disclosed process, since this compound is described as a useful reactant.
Regarding claim 58, as mentioned previously, Buchanan et al. specifically describes making cellulose acetate butyrate.
This is a provisional nonstatutory double patenting rejection.
Claims 2 and 58-62 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 33 of copending Application No. 17/595510 (US pre-grant publication 2022/0186124, cited in PTO-892, herein referred to as ‘510) in view of Buchanan et al. (US pre-grant publication 2012/0238742, of record in previous action) in view of Angyal et al. (Reference of record in previous action) in view of Dwidar et al. (Reference of record in previous action)
Claim 33 of ‘510 claims a method for making olefins comprising steam cracking a combination of a non-recycle feed comprising C2-C4 hydrocarbons and a recycle content pyrolysis oil comprising waste plastic. The presently claimed process differs from that of ‘510 in that it does not describe the olefins as including propylene, or include further steps of converting the propylene to butyric acid or butyric anhydride, and reacting the butyric anhydride with cellulose to make cellulose butyrate.
Buchanan et al. discloses a process for producing a cellulose ester comprising dissolving cellulose in an ionic liquid, and then esterifying the cellulose in the ionic liquid. (p. 1 paragraph 9) The process further comprises adding a carboxylate donor to the ionic liquid, which can include a C2-C4 straight chain carboxylic acid, from which one skilled in the art would at once envisage butyric acid, or an anhydride such as butyric anhydride. (p. 5 paragraphs 55-56, p. 7 paragraph 77) The cellulose ester can be a mixed ester, containing ester groups selected from a list including acetate and butyrate. (p. 10 paragraph 92) In particular, cellulose acetate butyrate is described as one of the mixed esters that can be produced by this process. (p. 12 paragraphs 107 and 108) Buchanan et al. does not specifically describe the source of the butyric acid or butyric anhydride.
Angyal et al. discloses that steam cracking feedstocks can be derived by mild cracking (pyrolysis) of various plastic wastes. (p. 1718 left column second paragraph) Results of the initial pyrolysis included gas, distillate, and oil. (p. 1718 left column second paragraph) The products of steam cracking included propylene. (p. 1722 table 3)
Dwidar et al. discloses that butyric acid can be produced by transformation of propylene into butyraldehyde, which is then transformed into butyric acid. (p. 2 section 2)
It would therefore have been obvious to one of ordinary skill in the at the time of the invention to use pyrolysis of waste plastic and subsequent steam cracking of the resulting pyrolysis oil to produce propylene, which could then be subject to chemical conversion to butanoic acid to produce butanoic acid for use in the process described by Buchanan et al. One of ordinary skill in the art would have been motivated by Buchanan et al. to look for sources of butyric acid to use in the disclosed process, since this compound is described as a useful reactant.
Regarding claim 58, as mentioned previously, Buchanan et al. specifically describes making cellulose acetate butyrate.
This is a provisional nonstatutory double patenting rejection.
Claims 2 and 58-62 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 48 of copending Application No. 17/597817 (US pre-grant publication 2022/0281796, cited in PTO-892, herein referred to as ‘817) in view of Buchanan et al. (US pre-grant publication 2012/0238742, of record in previous action)
Claim 48 of ‘817 claims a method for making butyric acid comprising steam cracking a combination of a non-recycle feed comprising C2-C4 hydrocarbons and a recycle content pyrolysis oil comprising waste plastic. The presently claimed process differs from that of ‘817 in that it does not describe reacting the butyric acid with cellulose to make cellulose butyrate.
Buchanan et al. discloses a process for producing a cellulose ester comprising dissolving cellulose in an ionic liquid, and then esterifying the cellulose in the ionic liquid. (p. 1 paragraph 9) The process further comprises adding a carboxylate donor to the ionic liquid, which can include a C2-C4 straight chain carboxylic acid, from which one skilled in the art would at once envisage butyric acid, or an anhydride such as butyric anhydride. (p. 5 paragraphs 55-56, p. 7 paragraph 77) The cellulose ester can be a mixed ester, containing ester groups selected from a list including acetate and butyrate. (p. 10 paragraph 92) In particular, cellulose acetate butyrate is described as one of the mixed esters that can be produced by this process. (p. 12 paragraphs 107 and 108) Buchanan et al. does not specifically describe the source of the butyric acid or butyric anhydride.
It would therefore have been obvious to one of ordinary skill in the at the time of the invention to use pyrolysis of waste plastic and subsequent steam cracking of the resulting pyrolysis oil to produce butanoic acid for use in the process described by Buchanan et al. One of ordinary skill in the art would have been motivated by Buchanan et al. to look for sources of butyric acid to use in the disclosed process, since this compound is described as a useful reactant.
Regarding claim 58, as mentioned previously, Buchanan et al. specifically describes making cellulose acetate butyrate.
This is a provisional nonstatutory double patenting rejection.
Claims 2, 58, and 60 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 2, 29, and 30 of copending Application No. 19/211476 (US pre-grant publication 2025/0276949, cited in PTO-892, herein referred to as ‘476) in view of over Buchanan et al. (US pre-grant publication 2012/0238742, of record in previous action) in view of Van Zijl et al. (PCT international publication WO2020/152317, Reference included with PTO-1449 submitted August 24, 2022)
Claim 1 of ‘476 claims a process for making a C4 alkanal comprising hydroformylating a propylene composition. Claim 2 of ‘476 further describes the pyoil as containing recycle content. Claims 29 and 30 further define the alkanal as isobutyraldehyde. The presently claimed process differs from that of ‘211 in that it does not include further steps of converting the C4 alkanal to butyric acid, and reacting the butyric acid with cellulose to make cellulose butyrate.
Buchanan et al. discloses a process for producing a cellulose ester comprising dissolving cellulose in an ionic liquid, and then esterifying the cellulose in the ionic liquid. (p. 1 paragraph 9) The process further comprises adding a carboxylate donor to the ionic liquid, which can include a C2-C4 straight chain carboxylic acid, from which one skilled in the art would at once envisage butyric acid, or an anhydride such as butyric anhydride. (p. 5 paragraphs 55-56, p. 7 paragraph 77) The cellulose ester can be a mixed ester, containing ester groups selected from a list including acetate and butyrate. (p. 10 paragraph 92) In particular, cellulose acetate butyrate is described as one of the mixed esters that can be produced by this process. (p. 12 paragraphs 107 and 108) Buchanan et al. does not specifically describe the source of the butyric acid or butyric anhydride.
Van Zijl et al. discloses a process for treating waste plastic feedstocks comprising providing a hydrocarbon stream obtained by treatment of a waste plastic feedstock, providing a hydrocarbon stream B, combining the two streams, and processing the combined stream in a steam cracker. (p. 3 paragraph 12) The waste plastic stream A can be obtained by pyrolysis of waste plastic, in which case it is reasonably considered to be a pyrolysis oil. (p. 7 paragraphs 34 and 35) The hydrocarbon stream B consists of various nonrecycle content hydrocarbons. (p. 10 paragraph 51 – p. 11 paragraph 50) The combined stream C preferably contains between 1 and 10% of stream A, which falls within the scope of present claim 60, with the remainder being stream B. (p. 13 paragraph 67) The resulting cracked product comprises lower olefins such as ethylene and propylene as predominant products. (p. 14 paragraph 73)
It would therefore have been obvious to one of ordinary skill in the at the time of the invention to use pyrolysis of waste plastic and subsequent steam cracking of the resulting pyrolysis oil to produce propylene, which could then be subject to chemical conversion to butanoic acid to produce butanoic acid for use in the process described by Buchanan et al. One of ordinary skill in the art would have been motivated by Buchanan et al. to look for sources of butyric acid to use in the disclosed process, since this compound is described as a useful reactant. Furthermore, in view of the disclosure of Van Zijl et al., one of ordinary skill in the art would have found it to be obvious to further perform the steam cracking of the pyoil on a mixed feed comprising both recycle waste plastic pyoil and nonrecycle hydrocarbons. One of ordinary skill in the art would have seen this to be obvious in view of the suggestion of Van Zijl to use such a mixed feed in steam cracking to produce olefins including propylene.
Regarding claim 58, as mentioned previously, Buchanan et al. specifically describes making cellulose acetate butyrate.
Conclusion
No claims are allowed in this action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ANDREA OLSON whose telephone number is (571)272-9051. The examiner can normally be reached M-F 6am-3:00pm.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Y Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/ANDREA OLSON/ Primary Examiner, Art Unit 1693 1/15/2026