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
Claims 48, 49, 52, 54, 56-62, and 66-69 of D. Slivensky et al., US 17/597,817 (Jul. 29, 2020) are pending and under examination. Claims 48, 49, 52, 54, 56-62, and 66-69 are rejected.
Claim Interpretation
Examination requires claim terms first be construed in terms in the broadest reasonable manner during prosecution as is reasonably allowed in an effort to establish a clear record of what applicant intends to claim. See, MPEP § 2111; MPEP § 2106(II). Under a broadest reasonable interpretation, words of the claim must be given their plain meaning, unless such meaning is inconsistent with the specification. See MPEP § 2111.01. Claim interpretation is updated from the previous Office action in view of Applicant’s amendments.
The Invention of Independent Claim 48
Claim 48 recites:
48. A method of making recycle (C4)alkanoic acid (r-(C4)alkanoic acid), said method comprising the steps
(i) pyrolizing a waste plastic stream to provide recycle content pyoil (r-pyoil), and
(ii) steam cracking a feed stream comprising (a) r-pyoil, wherein the r-pyoil is not hydroprocessed prior to the steam cracking and (b) a C2-C4 hydrocarbon composition,
thereby providing an olefin stream comprising a recycle propylene composition(r-propylene), and
(iii) carboxylating said r-propylene to thereby produce a carboxylation effluent comprising (C4)alkanoic acid.
The specification provides alternative definitions of "(C4)alkanoic acid" as follows:
[0047] As used herein, "(C4)alkanoic acid" means a composition comprising butyric acid, isobutyric acid, or combinations, whether or not the butyric acid or isobutyric acid has recycle content.
[0048] As used herein, "(C4)alkanoic acid" means a composition comprising butyric acid, isobutyric acid, or combinations, which has recycle content.
Specification at page 12, [0047]-[0048]. The working examples exemplify handing and cracking of pyoil, but no working example is presented regarding the claim 48 process. Specification at pages 158-216.
The specification provides the following general disclosure regarding the claim 48 process:
[0338] . . . This method for making r-(C4)alkanoic acid includes contacting propylene with water, CO and a catalyst or CO2 and a catalyst in a reaction zone under temperatures and pressures for a sufficient period of time to permit the propylene, water and CO, or propylene and CO2 to form (C4)alkanoic acid, and can be carried out by methods known in the art.
Specification at page 124, [0338]. In view of the foregoing specification discussion, the invention of claim 48 can be schematically summarized as follows:
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The Invention of Independent Claim 49
Independent claim 49 recites as follows.
49. A method of making recycle (C4)alkanoic acid (r-(C4)alkanoic acid), said method comprising the steps
(i) pyrolizing a waste plastic stream to provide recycle content pyoil (r-pyoil), and
(ii) steam cracking a feed stream comprising r-pyoil and a C2-C4 hydrocarbon composition,
thereby providing an olefin stream comprising a recycle propylene composition (r-propylene), and
(iii) hydroformylating said r-propylene at a pressure of at least 1000 psi to thereby provide a recycle content (C4)alkanal (r(C4)alkanal), and
(iv) oxidizing said r(C4) alkanal to thereby produce an oxidation effluent comprising (C4)alkanoic acid.
The meaning of “(C4)alkanoic acid (r-(C4)alkanoic acid)” was discussed above. The specification provides alternative meanings of "(C4)alkanal" as follows:
[0045] As used herein, "(C4)alkanal" means a composition comprising butyraldehyde, isobutyraldehyde, or combinations, whether or not the butyraldehyde or isobutyraldehyde has recycle content.
[0046] As used herein, "r-(C4)alkanal" means a composition comprising butyraldehyde, isobutyraldehyde, or combinations, which has recycle content.
Similar to claim 48 (as discussed above) the specification does not disclose any working examples regarding the claim 49 process.
The specification provides the following general disclosure regarding the claim 49 process.
[0339] Another example of a method of making r-(C4)alkanoic acid includes an oxidation method in which r-(C4)alkanal (as discussed herein) is fed to a reaction vessel and reacted to produce an oxidation effluent that includes r-(C4)alkanoic acid. This method for making r-(C4)alkanoic acid includes contacting (C4)alkanal with oxygen and a catalyst in a reaction zone under temperatures and pressures for a sufficient period of time to permit the (C4)alkanal and oxygen to form (C4)alkanoic acid, and can be carried out by methods known in the art.
Specification at page 125, [0339]. In view of the specification, claim 49 is schematically summarized as follows
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Interpretation of “hydroprocessed”
Applicant has amended claim 48 to recite “wherein the r-pyoil is not hydroprocessed prior to the steam cracking”. This amendment (a negative limitation) is supported by the specification at pages 54-55, [0151]. Here, the specification teaches that hydroprocessing is an alternative embodiment. MPEP § 2173.05(i) (If alternative elements are positively recited in the specification, they may be explicitly excluded in the claims, citing, In re Johnson, 558 F.2d 1008, 1019, 194 USPQ 187, 196 (CCPA 1977)).
The term “hydroprocessing” is broadly and reasonably interpreted based on its plain meaning, the art and the specification as reduction employing hydrogen and, typically, a hydrogenation catalyst. MPEP § 2111. This is consistent with the specification. Specification at pages 54-55, [0151]. This interpretation is also consistent with the art. See e.g., S. Bezergianni et al., 68 Progress in Energy and Combustion Science, 29-64 (2018).
Hydroprocessing is a catalytic process that enables targeted catalytic reactions with the addition of hydrogen. The aim of hydroprocessing is to increase the hydrogen-to-carbon ratio and to almost completely remove undesirable heteroatoms such as sulfur, nitrogen, oxygen and some metals. Furthermore, in some cases, hydroprocessing also targets to the reduction of olefin and the aromatic content of the feedstock. The key reactions involved in hydroprocessing include hydrodesulphurization (HDS), hydrodenitrogenation (HDN), hydrodemetallization (HDM), hydrogenation (HYD) and hydrodeoxygenation (HDO). HDS and HDN enable sulfur and nitrogen removal respectively [100], both of which are environmentally driven, aiming to mitigate SOX and NOX emissions of fuel combustion.
Bezergianni at page 37 col. 1
Withdrawal Rejections 35 U.S.C. 112(b)
Rejection of claims 48, 56-62, and 66-68 under 35 U.S.C. 112(b) as indefinite is withdrawn in view of Applicant’s amendment cancelling limitation at issue.
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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied for establishing a background for determining obviousness under AIA 35 U.S.C. 103(a) 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.
Claims 48, 49, 52, 54, 56-62 and 66-69 are rejected under 35 U.S.C. 103 as obvious over K. Ramamurthy et al., WO 2018/127813 (2018) (“Ramamurthy”) and A. Angyal et al., 91 Fuel Processing Technology, 1717-1724 (2010) (“Angyal”) in combination with S. Besecke et al., US 4,452,999 (1984) (“Besecke”); G. Phillips et al., US 4,755,624 (1988) (“Phillips”); H. Yu et al., 56 Angewandte Chemie, International Edition, 3867-3871 (2017) (“Yu”); and/or J. Huang et al., Preparative Biochemistry and Biotechnology, 427-434 (2018) (“Huang”).
K. Ramamurthy et al., WO 2018/127813 (2018) (“Ramamurthy”)
Ramamurthy teaches the production of high value products, such as olefins and aromatic hydrocarbons from mixed plastics via processes which include pyrolysis, hydroprocessing, steam cracking, alkylation, and olefin metathesis, wherein cumene and propylene are the preferred products. Ramamurthy at page 1, [0001].
In Example 1, Ramamurthy teaches pyrolyzing mixed waste plastic having an 82% olefinic feed (e.g., high-density polyethylene (HDPE), low-density polyethylene (LDPE), linear low-density polyethylene (LLDPE), and polypropylene (PP)); 11 % polystyrene (PS); and the remaining 7% was polyethylene terephthalate (PET)) in a continuous catalytic cracking in circulating fluidized bed at 390 to 560 °C cup mix temperature of feed and catalyst. Ramamurthy at page 22, [0096].
Ramamurthy teaches that in the case of a single stage pyrolysis process, the pyrolysis product (which corresponds to the instant claim 48 and 49 r-pyoil) had the composition shown in Table 1 (reproduced below), where the propylene content of the pyrolysis effluent was 23.7%, the overall yield of light gas olefins was about 43 wt.%, and the liquid product boiling below 240 °C had an aromatic concentration of 87.5 wt.%. Ramamurthy at page 22, [0096].
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Ramamurthy at page 23, Table 1.
Ramamurthy Example 1 further teaches that the above pyrolysis product of Table 1 (which corresponds to the instant claim 48 and 49 r-pyoil) was processed according Figures 1A and 1B (i.e., hydroprocessing, steam cracking, metathesis) where yields at various stages were calculated and summarized in the Table reproduced below. Ramamurthy at page 23, [0097].
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Ramamurthy at page 23, [0097] (circling added). As can be seen from the above Table, the hydroprocessing did not affect the yield of propylene but markedly increased the yield of benzene. Applicant has amended claim 48 to recite “wherein the r-pyoil is not hydroprocessed prior to the steam cracking”.1 In this regard, Ramamurthy teaches that the purpose of “hydrotreating” (which is synonymous with “hydroprocessing”) is to maximize benzene production:
To maximize benzene production, the liquid obtained from low severity and/or high severity pyrolysis can be further hydrocracked and/or hydrotreated to reduce a boiling point of the heavies (e.g., heavies can be cracked to mostly C10-hydrocarbons), and to also saturate liquid olefins. Benzene can be further alkylated with propylene to form cumene.
Ramamurthy at page 3, lines 9-13 (emphasis added). One purpose of Ramamurthy is the production of propylene as well as benzene for their subsequent reaction with each other to form cumene. Ramamurthy at page 1, [0002]. Thus, Ramamurthy seeks to optimize both benzene and propylene production, where the Example 1 “hydrotreatment” is directed to benzene optimization. Ramamurthy at page 3, lines 3-12.
The pyrolysis can be configured to maximize propylene and/or aromatics, with high yields of BTX and EB. Maximizing propylene yields can also be achieved by employing a metathesis reaction to convert ethylene and butylenes streams to propylene, and further by employing a steam cracker to further crack a liquid stream from pyrolysis, thereby converting a portion of the liquid stream to light gas olefins. To maximize benzene production, the liquid obtained from low severity and/or high severity pyrolysis can be further hydrocracked and/or hydrotreated to reduce a boiling point of the heavies (e.g., heavies can be cracked to mostly C10-hydrocarbons), and to also saturate liquid olefins. Benzene can be further alkylated with propylene to form cumene.
Ramamurthy at page 3, lines 3-12. In summary, one of ordinary skill seeking only propylene (and not benzene) would be motivated to modify the process of Ramamurthy to (per claim 48) omit the hydroprocessing/hydrotreating step, where the propylene-containing pyrolysis oil is directly steam cracked to further increase propylene amount.
Ramamurthy directly teaches this in the following further paragraph of Example 1:
[0099] A pyrolysis oil recovered from the pyrolysis could be further fed to a hydrocracker. Gases would be cracked in gas steam crackers and liquids would be cracked in liquid steam crackers. The products would be separated. Ethylene and butylenes would then be subjected to metathesis to produce propylene. Propylene and benzene would then be reacted to produce a cumene product.
Ramamurthy at page 25, [0099] (emphasis added). Here Ramamurthy is teaching one of ordinary skill that the pyrolysis oil can be fed directly to steam cracking, without hydroprocessing, so as to produce propylene.
Finally, Ramamurthy’s above steam cracking teaches the claim 48 and 49 limitation of steam cracking a pyrolysis oil composition comprising “a C2-C4 hydrocarbon composition”:
Claims 48 and 49 (ii) steam cracking a feed stream comprising (a) r-pyoil and (b) a C2-C4 hydrocarbon composition,
thereby providing an olefin stream comprising a recycle propylene composition(r-propylene)
because the pyrolysis effluent comprises C2-C4 hydrocarbons (i.e., propane, butadiene, butane, etc.).
Differences between Ramamurthy and Claims 48 and 49
Ramamurthy differs from claims 48 and claims 49 in that this reference does not teach the following claim limitations:
48. (iii) carboxylating said r-propylene to thereby produce a carboxylation effluent comprising (C4)alkanoic acid.
49. (iii) hydroformylating said r-propylene to thereby provide a recycle content (C4)alkanal (r(C4)alkanal), and
(iv) oxidizing said r(C4) alkanal to thereby produce an oxidation effluent comprising (C4)alkanoic acid.
Ramamurthy further differs from claim 48 to the extent that it does not teach a working example where, per claim 48, “the r-pyoil is not hydroprocessed prior to the steam cracking”.
A. Angyal et al., 91 Fuel Processing Technology, 1717-1724 (2010) (“Angyal”)
Angyal is cited here for teaching the two-step pyrolysis/steam cracking of plastic waste, to form propylene where no hydroprocessing step is performed. Angyal is cited here as further motivation for one of ordinary skill to modify Ramamurthy to (per claim 48) omit the hydroprocessing/hydrotreating step, where the propylene-containing pyrolysis oil is directly steam cracked.
Angyal teaches that largest parts the enormous plastic volume are polyethylene, polypropylene and polystyrene, on the other hand the efficient recycling of polymer wastes is still unsolved, because of the unstable market of reusable plastic wastes. Angyal at page 1717, col. 1
Angyal teaches cracking of polyethylene (PE), polyethylene–polypropylene (PEPP) and polyethylenepolystyrene (PEPS) in a pilot scale tubular reactor with the temperature of 530 °C and the residence time of 15 min. Angyal at Abstract. Angyal teaches that the produced hydrocarbon fractions as light- and middle distillates were then tested by using a laboratory steam cracking unit. Angyal at Abstract.
Angyal teaches that polyethylene, polypropylene and polystyrene wastes were treated in the cracking experiments. Angyal at page 1718 (“2.1. Materials”).
Angyal teaches the following thermal cracking (pyrolysis) of plastic wastes.
2.2.1. Cracking procedure of plastic wastes
Cracking of polyethylene, polyethylene–polypropylene and polyethylene– polystyrene wastes was carried out in a pilot scale tubular reactor having a yearly capacity of 75 t. The reaction parameters were determined after the consideration of earlier experimental results: reaction temperature was 530 °C, while the residence time was 15 min. The schematic diagram of the tubular reactor is illustrated in Fig. 1. Plastic wastes and catalyst2 were previously mixed and then driven into the reactor tube by an extruder. The reactor was heated with controlled gas heaters, and directly connected to the distillation column, which separated the cracking products. Four products were separated: gas, light-, middle distillate, and heavy oil.
Angyal at page 1718 (“2.2.1. Cracking procedure of plastic wastes”). Angyal teaches that the light distillate fractions consisted of hydrocarbons in the rage of C5–C11; the composition of middle distillates contained hydrocarbons from C9 to C26. Angyal at page 1720, col. 1 (referencing Figs. 4 and 5).
In a second step, Angyal teaches steam cracking of the above obtained light and middle distillates from the above pyrolysis (which corresponds to the instantly claimed “pyrolysis oil”). Angyal at page 1722 (last four lines of col. 1).
Angyal teaches the following steam cracking procedure.
2.2.2. Steam cracking of mild cracking products
The construction and operation of steam cracking apparatus (Fig. 2) was presented in previous paper. Two pumps fed the feedstock and water into the preheater furnace. The main pyrolysis reactor was connected directly to the preheater and equipped with a three sector furnace and three individual temperature controllers. The cooling system was attached to the outlet of the reactor. After the cooling system the gases were lead into a wet gas meter to measure the volume of the produced gases. The steam cracking parameters were optimised earlier and were as follows; in case of light distillate; temperature: 860 °C, residence time: 0.3 s, steam/raw material: 0.54 wt.%; middle distillate; temperature: 830 °C, residence time: 0.3 s, steam/raw material: 0.85 wt.%.
Angyal at page 1718 (“2.2.2. Steam cracking of mild cracking products”). Angyal teaches that in all cases methane, ethylene and propylene were the main components of the pyrogas. Angyal at page 1722 (“3.3. Steam cracking of cracking products”). Angyal teaches that in case of the steam cracking of the middle distillate, the propylene concentration in the pyrogas was higher than that obtained by steam cracking the reference material (i.e., naphtha). Angyal at page 1722, col. 2, lines 6-9.
In Figs. 8 and 9, Angyal summarizes that the yields of propylene from steam cracking of waste polyethylene (PE), and polyethylene–polypropylene (PPE) of the light and middle distillates ranged from 7% to 19%. Angyal at page 1723.
It is important to note here that Angyal’s pyoil, which was steam cracked, cannot be confirmed one way or the other to meet the claim 48 and 49 limitation of comprising “a C2-C4 hydrocarbon composition”, as indicated by strikeout text below.
Claims 48 and 49 . . . (ii) steam cracking a feed stream comprising (a) r-pyoil, wherein the r-pyoil is not hydroprocessed prior to the steam cracking
In summary, Angyal teaches a two-step pyrolysis/steam cracking of plastic waste, to form propylene where no hydroprocessing step is performed. Angyal provides further motivation for one of ordinary skill to modify Ramamurthy to (per claim 48) omit the hydroprocessing/hydrotreating step, where the propylene-containing pyrolysis oil is directly steam cracked.
S. Besecke et al., US 4,452,999 (1984) (“Besecke”)
Besecke is cited here for teaching the claim 48 limitation of:
48. (iii) carboxylating said r-propylene to thereby produce a carboxylation effluent comprising (C4)alkanoic acid.
Besecke teaches conditions which permit a large-scale method for the preparation of isobutyric acid or its esters from propylene, carbon monoxide, and water or an alcohol. Besecke at col. 2, lines 56-64. In Example 1, Besecke exemplifies the disclosed process, summarized as follows:
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Besecke teaches that isobutyric acid or its lower alkyl esters can be converted by dehydrogenation into methacrylic acid or its lower alkyl esters,which latter materials are in turn starting materials for valuable synthetic resins. Besecke at col. 1, lines 5-10.
L. Slaugh et al., US 3,239,566 (1966) (“Slaugh”)
Slaugh is cited here for teaching the claim 49 limitation of:
Claim 49 . . . (iii) hydroformylating said r-propylene at a pressure of at least 1000 psi to thereby provide a recycle content (C4)alkanal (r(C4)alkanal) . . .
Slaugh teaches hydroformylation olefinically unsaturated compounds to produce aldehydes. Slaugh at col. 1, lines 10-15. Slaugh teaches the following general reaction
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Slaugh at col. 1, lines 35-40. Slaugh teaches that propylene is a suitable hydrocarbon. Slaugh at col. 6, line 15. Slaugh teaches that pressures in the broad range from atmospheric up to about 2000 psig and higher may be employed. Slaugh at col. 4, lines 63-65.
H. Yu et al., 56 Angewandte Chemie, International Edition, 3867-3871 (2017) (“Yu”)
Yu is cited here for teaching the claim 49 limitation of:
Claim 49 . . . (iv) oxidizing said r(C4) alkanal to thereby produce an oxidation effluent comprising (C4)alkanoic acid.
Yu teaches heterogeneous iron(III)-catalyzed aerobic oxidation of aldehydes in water under mild conditions. Yu at Abstract.
Yu teaches the following oxidation of aldehydes to carboxylic acids gives high yields.
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Yu at page 3869, Table 2. Yu teaches 99% yield in the conversion of butyraldehyde to butyric acid (24). Yu at page 3869, Table 2. Yu teaches that the oxidation of aldehydes to carboxylic acids is one of the most well-known and most frequently used methodologies. Yu at page 3867, col. 1.
J. Huang et al., Preparative Biochemistry and Biotechnology, 427-434 (2018) (“Huang”)
Huang teaches butyric acid is a commercially useful product with a global market of 80,000 tons per year. Huang at page 427, col. 1.
Obviousness Rationale
Claims 48 and 49 are obvious for the following reasons. The claim 48 and 49 pyrolysis and steam cracking steps (i) and (ii) are obvious because one of ordinary skill is motivated to practice the pyrolysis/steam cracking of waste plastic as taught by Ramamurthy Example 1, (per claim 48) “wherein the r-pyoil is not hydroprocessed prior to the steam cracking” so as to arrive at a propylene stream. Ramamurthy at page 22, [0096] (Example 1).
One of ordinary skill thereby meets the claim 48 steps of:
48. A method of making recycle (C4)alkanoic acid (r-(C4)alkanoic acid), said method comprising the steps
(i) pyrolizing a waste plastic stream to provide recycle content pyoil (r-pyoil), and
(ii) steam cracking a feed stream comprising (a) r-pyoil, wherein the r-pyoil is not hydroprocessed prior to the steam cracking and (b) a C2-C4 hydrocarbon composition,
thereby providing an olefin stream comprising a recycle propylene composition(r-propylene) . . .
as well as the same steps in claim 49 that differ from claim 48 only in that they do not recite the claim 48 limitation of “wherein the r-pyoil is not hydroprocessed prior to the steam cracking”.
One of ordinary skill is so motivated because plastic waste represents an economical feed stream. For example, Ramamurthy teaches that the plastic waste can be pyrolyzed to produce high yields of light gas olefins (i.e., ethylene, propylene, butylenes). Ramamurthy at page 3, lines 3-4.
One of ordinary skill is motivated to practice Ramamurthy, where (per claim 48) “the r-pyoil is not hydroprocessed prior to the steam cracking” because as can be seen from Ramamurthy Table, the hydroprocessing did not affect the yield of propylene. Ramamurthy Table at page 23, [0097]. Rather, as discussed in detail above, the purpose of Ramamurthy’s hydroprocessing is to increase the yield of benzene. See above discussion citing Ramamurthy at page 3, lines 3-12. Here, one of ordinary skill seeking only propylene is motivated to omit this step in the interest of reaction efficiency. One of ordinary skill is further motivated because Angyal teaches a two-step pyrolysis/steam cracking of plastic waste, to form propylene where no hydroprocessing step is performed.
One of ordinary skill is further motivated to prepare isobutyric acid from Ramamurthy’s propylene stream according to the method of Besecke, thereby meeting the final claim 48 limitation:
48 . . . (iii) carboxylating said r-propylene to thereby produce a carboxylation effluent comprising (C4)alkanoic acid.
in view of the utility of isobutryic acid taught by Besecke. One of ordinary skill thereby meets each and every limitation of claim 48.
Respecting the further limitations of claim 49, one of ordinary skill is motivated to first convert the propylene stream (obtained as above) to butyraldehyde according to the hydroformylation method of Slaugh (“at a pressure of at least 1000 psi) and then convert the obtained butyraldehyde to butyric acid according to the oxidation method of Yu (in view of the utility of isobutryic acid taught by Besecke) thereby meeting the final claim 49 limitations of:
49 . . . (iii) hydroformylating said r-propylene at a pressure of at least 1000 psi to thereby provide a recycle content (C4)alkanal (r(C4)alkanal), and
(iv) oxidizing said r(C4) alkanal to thereby produce an oxidation effluent comprising (C4)alkanoic acid.
One of ordinary skill is motivated to hydroformylate “said r-propylene at a pressure of at least 1000 psi” because Slaugh teaches that propylene is a suitable hydrocarbon. Slaugh at col. 6, line 15. And Slaugh teaches that pressures in the broad range from atmospheric up to about 2000 psig and higher may be employed. Slaugh at col. 4, lines 63-65. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. MPEP § 2144.05(I). Each and every limitation of claim 49 is therefore met by the cited art.
Claim 52 recites a “gas furnace” as follows:
52. The method of claim 49, wherein the r-propylene is derived from cracking r-pyoil in a gas furnace.
The specification defines the claim 52 term “gas furnace” as follows:
A gas furnace is a furnace having at least one coil which receives (or operated to receive), at the inlet of the coil at the entrance to the convection zone, a predominately vapor-phase feed (more than 50% of the weight of the feed is vapor) ("gas coil").
Specification at pages 78-79, [0220] (emphasis added). The specification does not define the term “coil”. The plain meaning of coil is a length of something wound or arranged in a spiral. The broadest reasonable interpretation of claim 52’s “gas furnace”, consistent with the specification, is where the furnace’s reaction zone is in the shape of coiled tube.
As discussed above, both Angyal and Ramamurthy teach steam cracking of a r-pyoil stream in a furnace. Ramamurthy does not specifically teach the dimensions of the pyrolysis unit. With respect to the furnace/pyrolysis unit, Ramamurthy teaches:
Mixed plastics (e.g., waste plastics) can be either placed in the pyrolysis unit 100 or fed to the pyrolysis unit 100 via waste plastic stream 110. In the pyrolysis unit 100, the waste plastic stream 110 is converted via pyrolysis to a pyrolysis product, wherein the pyrolysis product comprises a gas phase (e.g., pyrolysis gases, such as C1 to C4 gases, hydrogen (H2), carbon monoxide (CO), carbon dioxide (CO2), hydrochloric acid (HCl) gas, etc.) and a liquid phase (e.g., pyrolysis liquid).
Ramamurthy at page 4, [0017].
Ramamurthy further teaches:
[0019] The pyrolysis unit 100 may be any suitable vessel configured to convert waste plastics into gas phase and liquid phase products (e.g., simultaneously). The vessel may be configured for gas phase, liquid phase, vapor-liquid phase, gas-solid phase, liquid-solid phase, or slurry phase operation. The vessel may contain one or more beds of inert material or pyrolysis catalyst comprising sand, zeolite, alumina, a catalytic cracking catalyst, or combinations thereof. Generally, the pyrolysis catalyst is capable of transferring heat to the components subjected to the pyrolysis process in the pyrolysis unit 100. Alternatively, the pyrolysis unit 100 can be operated without any catalyst (e.g., pure thermal pyrolysis). The pyrolysis unit 100 may be operated adiabatically, isothermally, nonadiabatically, non-isothermally, or combinations thereof. The pyrolysis reactions of this disclosure may be carried out in a single stage or in multiple stages. For example, the pyrolysis unit 100 can be two reactor vessels fluidly connected in series.
Ramamurthy at pages 4-5, [0019] (emphasis added). Here claim 52, requiring that “the r-propylene is derived from cracking r-pyoil in a gas furnace” is obvious because it relates merely to design choice regarding the furnace shape (i.e. the shape of the pyrolysis unit or steam cracker taught by Ramamurthy). See MPEP § 2144.04 (IV)(B) (citing In re Dailey, 357 F.2d 669, 149 USPQ 47 (CCPA 1966), where the court held that the configuration of the claimed disposable plastic nursing container was a matter of choice which a person of ordinary skill in the art would have found obvious absent persuasive evidence that the particular configuration of the claimed container was significant). Here the specification fails to set forth any reasons why the differences between the claimed coil-shape furnace and the prior art tubular-shaped furnace would result in a different function or give unexpected results.3
Claim 54 recites as follows:
54. The method of claim 49, wherein a cracker facility in which the r-propylene made is in fluid communication, continuously or intermittently, with an (C4)alkanal formation facility.
The specification does not define the term “facility”. Under a broadest reasonable interpretation, consistent with its plain meaning, the term “facility” encompasses merely the place where the reaction apparatus exists. MPEP § 2111. With respect to the meaning of “fluid communication”, the specification teaches that:
[0417] The fluid communication can be gaseous or liquid. The fluid communication need not be continuous and can be interrupted by storage tanks, valves, or other purification or treatment facilities, so long as the r-propylene can be transported from the manufacturing facility to the (C4)alkanal facility through an interconnecting pipe network and without the use of truck, train, ship, or airplane.
Specification at page 154, [0417]. Claim 54 is obvious because one of ordinary skill is motivated to prepare the propylene from plastic waste according to Ramamurthy at one location and is further motivated to convert the propylene stream to butyraldehyde according to the hydroformylation method of Phillips at a second location thereby the limitations of claim 54.
Claim 56 recites:
56. The process method of claim 48, wherein the r-pyoil is a liquid at 25°C and 1 atm., and predominantly comprises C5 to C25 hydrocarbons.
The specification defines “predominantly” means more than 50 percent by weight. Specification at page 14, [0049]. Claim 56 is obvious because Ramamurthy teaches that hydrocarbon liquid stream 130 may comprise heavy hydrocarbon molecules in an amount of from 10 wt.% to 90 wt.%, based on the total weight of the hydrocarbon liquid stream 130. Ramamurthy at page 8, [0032]. Ramamurthy teaches that the heavy hydrocarbon molecules may include paraffins, i-paraffins, olefins, naphthenes, aromatic hydrocarbons, or combinations thereof. Ramamurthy at page 8, [0032]. Ramamurthy teaches that these molecules are in the range of C1-C22. Ramamurthy at page 8, [0033]-[0034]. And in Ramamurthy’s Example 2, it is taught that a hydrotreated pyrolysis liquid can typically comprise 35-45% paraffins, 35-45% iso-paraffins, 15-20% naphthenes, and 5-10% aromatics, wherein the hydrotreated pyrolysis liquid boils below 400 °C. Ramamurthy at page 25, [00100]. These Example 2 hydrotreated products are r-pyoil liquids and are all hydrocarbons because the starting waste plastic was a hydrocarbon. In sum, Ramamurthy’s range of 10 wt.% to 90 wt.% hydrocarbons (where the hydrocarbons are C1-C22) substantially overlaps with the claimed range of more than 50 percent by weight C5 to C25 hydrocarbons. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. MPEP § 2144.05. In any case, the specific concentration of C5 to C25 hydrocarbons in Ramamurthy’s hydrocarbon liquid stream 130 will be broken down to smaller hydrocarbons (including propene) upon Ramamurthy’s steam cracking (which is the same concept of the instant claims). Thus, the claim 56 concentration limitation of “predominantly comprises C5 to C25 hydrocarbons” in this context is an obvious concentration limitation. Generally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. MPEP § 2144.04(II)(A) (citing In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955) ("[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”)). Therefore claim 56 is obvious.
Claim 57 is obvious at least because Ramamurthy teaches that the olefins can be present in the hydrocarbon liquid stream 130 in an amount of 5 wt.%, 10 wt.%, 20 wt.%, 30 wt.%, 40 wt.%, or more based on the total weight of the hydrocarbon liquid stream 130. Ramamurthy at page 8, [0034]. This overlaps with the claim 57 alternative of “(6) olefins present in an amount ranging from 40-85 as wt.% based on the weight of the r-pyoil”. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. MPEP § 2144.05.
Claim 58 is obvious at least because in Ramamurthy’s Example 2, it is taught that a hydrotreated pyrolysis liquid can typically comprise 35-45% paraffins, 35-45% iso-paraffins, 15-20% naphthenes, and 5-10% aromatics, wherein the hydrotreated pyrolysis liquid boils below 400 °C. Ramamurthy at page 25, [00100]. These Example 2 hydrotreated products are r-pyoil liquids and are all hydrocarbons (having no oxygen, nitrogen or sulfur) because the starting waste plastic was a hydrocarbon. Ramamurthy’s Example 2 r-pyoil thus meets the wt% limitations of claim 58 (1), (2) and (3).
Claim 59 is obvious because the specification teaches that the solubility of water in the r-pyoil at 1 atm and 25°C is less than 2 wt.%. Specification at page 71 [0202]. Since the Ramamurthy r-pyoil are the same as those claimed, derived from the same waste plastic, and therefor expected to have the same low water solubility. Once a reference teaching product appearing to be substantially identical is made the basis of a rejection, and the examiner presents evidence or reasoning to show inherency, the burden of production shifts to the applicant. MPEP § 2112(V) (citing In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433-34 (CCPA 1977).
Claims 60-62 are obvious for the following reasons. Note that claims 60 and 61 recites “can have” which implies possibility. For example, claim 60 recites:
60. (Previously Presented) The method of claim 59, wherein the r-pyoil can have the following compositional content:
a. carbon atom content of at least 75 wt.%;
b. hydrogen atom content of at least 10 wt%,
c. an oxygen atom content not to exceed 10 wt.%,
in each case based on the weight of the r-pyoil
The limitations of claim 60-62 are met by the proposed obviousness rational because the Ramamurthy r-pyoil are the same as those claimed, derived from the same waste plastic, they are expected to have the same composition content and physical properties. Once a reference teaching product appearing to be substantially identical is made the basis of a rejection, and the examiner presents evidence or reasoning to show inherency, the burden of production shifts to the applicant. MPEP § 2112(V) (citing In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433-34 (CCPA 1977).
Claims 66-68 are obvious for the same reasons as claim 52.
New claim 69 further recites “wherein the pyrolyzing is performed in an extruder”. The specification mentions “extruder” only once and does not define this term. Specification at page 48, [0133]. Claim 69 is obvious because Ramamurthy teaches that an extruder is suitable for conducting the pyrolysis as a well as “any other suitable equipment offering a heated surface to assist in cracking”. Ramamurthy at page 5, [0021]. Claim 69 relates merely to design choice regarding the furnace. See MPEP § 2144.04 (IV)(B) (citing In re Dailey, 357 F.2d 669, 149 USPQ 47 (CCPA 1966).
Applicant’s Argument
Respecting claim 48, Applicant argues that Ramamurthy teaches the use of a hydroprocessing unit between the pyrolysis unit and the steam cracking unit. Reply at pages 7-8 (citing Ramamurthy, paragraphs [0013]-[0014], [0039]; [0042], and [0046]). Applicant argues that the hydroprocessing conditions will have an impact on the composition of the r-pyoil and be different from the r-pyoil obtained from the claimed method prior to steam cracking.
This argument is not persuasive because Applicant cites no evidence regarding how hydroprocessing conditions will have an impact on the composition. Arguments presented by applicant cannot take the place of evidence in the record. MPEP § 2145(I). This argument is further not persuasive because, as discussed in detail above, one of ordinary skill would understand that Ramamurthy seeks to optimize both benzene and propylene production, where the Ramamurthy’s Example 1 hydrotreatment or hydroprocessing is directed to benzene optimization. Ramamurthy at page 3, lines 3-12. Here, one of ordinary skill seeking only propylene is motivated to omit hydroprocessing in the interest of reaction efficiency. One of ordinary skill is further motivated because Angyal teaches a two-step pyrolysis/steam cracking of plastic waste, to form propylene where no hydroprocessing step is performed.
Respecting claim 49, Applicant argues that the amendment of "hydroformylating said r-propylene at a pressure of at least 1000 psig" overcomes this rejection because previously cited G. Phillips et al., US 4,755,624 (1988) (“Phillips”) teaches a low pressure hydroformylation process from about 15 psig to about 800 psig.
This argument is not persuasive because the above rejection replaces Philips with Slaugh. One of ordinary skill is motivated to hydroformylate “said r-propylene at a pressure of at least 1000 psi” because Slaugh teaches that propylene is a suitable hydrocarbon. Slaugh at col. 6, line 15. And Slaugh teaches that pressures in the broad range from atmospheric up to about 2000 psig and higher may be employed. Slaugh at col. 4, lines 63-65. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. MPEP § 2144.05(I). Each and every limitation of claim 49 is therefore met by the cited art.
Conclusion
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ALEXANDER R. PAGANO
Examiner
Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
1 Note that, per Claim Interpretation above, the term “hydroprocessed” is broadly and reasonably interpreted as reduction employing hydrogen and, typically, a hydrogenation catalyst.
2 Angyal teaches the typical properties of the catalyst were as follows; zeolite type: clinoptilolite, crystal structure: monoclinic, Si/Al ratio: 6.4, average grain size: 35.9 μm, BET surface area: 46.1 m2/g, micropore area: 30.3 m2/g, pore area: 9.8 m2/g, pore volume: 0.027 cm3/g, micropore volume: 0.014 cm3/g. Angyal at page 1718 (“2.1. Materials”).
3 See also, In re Rice, 341 F.2d 309, 314 (CCPA 1965) ("Appellants have failed to show that the [differences in the claimed invention], as compared to [ the reference], result in a difference in function or give unexpected results"); In re Kuhle, 526 F.2d 553, 555 (CCPA 1975) ("Use of such a means of electrical connection in lieu of those used in the references solves no stated problem and would be an obvious matter of design choice within the skill of the art."); In re Chu, 66 F.3d 292, 298-99 (Fed. Cir. 1995).