DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claim Objections
Claims 1-7 and 10 are objected to because of the following informalities:
With regard to claim 1, the claim recites “a feedstock containing at least 5 wt% originating from…” The term “aromatics” was inadvertently removed in the preliminary amendment, and should be restored so the preamble recites “at least 5 wt% aromatics”.
Also with regard to claim 1, the claim recites in steps a and c “in the presence of dihydrogen”. This lacks antecedent basis and common terminology, and should be amended to recite “in presence of H2” or “in presence of hydrogen gas” for clarity. The Examiner notes that claims 3, 4, 6, and 7 also recite “the presence of dihydrogen” and should be amended in the same way.
With regard to claim 2, the claim recites “directing a unstabilized” in line 1. This should be corrected to “an unstabilized” for grammatical clarity.
Also with regard to claim 2, the claim recites “said composition originating from thermal decomposition of solids” in the last line. This should be “said feedstock” for antecedent basis purposes.
With regard to claim 4, line 2 recites “separating the dearomatized intermediate, in at least a high boiling fraction…” This should be “separating the dearomatized intermediate into at least…” for grammatical clarity.
With regard to claim 5, the claim recites in lines 2-3 “with a stripping medium, at a temperature above 150°C and a difference from the hydrodeoxygenation conditions being less than 10 bar.” For clarity and correctness, the claim should recite “with a stripping medium at a temperature above 150°C and with a pressure difference from the hydrodeoxygenation conditions of less than 10 bar.”
With regard to claim 6, the claim recites in line 2 “a heavy fraction boiling above a boiling point limit being 320°C…” This is unnecessarily wordy and for consistency with other claims and within claim 6 should be amended to recite “heavy fraction boiling above 320°C…”
With regard to claim 7, the claim recites “A process according to claim 6 wherein…” This should be “claim 6, wherein” with the comma for consistency within the claims.
With regard to claim 10, the claim recites in lines 1-2 “where hydrodearomatization conditions…” This should be “said hydrodearomatization conditions” for antecedent basis purposes.
Also with regard to claim 10, the claim recites in lines 2-3 “the interval” multiple times. This should be “an interval” or “a range” for antecedent basis purposes in each case.
Appropriate correction is required.
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 4-9 and 11 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.
With regard to claim 4, the claim recites in line 4 “the material catalytically active in hydrocracking”. However, claim 4 is dependent on claims 1 and 2, none of which recite the hydrocracking catalyst, which is only present in claim 3. Thus, the recitation of “the material catalytically active in hydrocracking” lacks antecedent basis and is indefinite.
For purposes of examination, the Examiner will consider that the catalyst of claim 4 is in a reactor which is used for hydrocracking of the dearomatized effluent. The embodiments in the Figures do not show sending both the heavy from the deoxygenation and heavy from the dearomatization to the same hydrocracking unit, only showing one or the other. Thus, the catalyst of claim 4 is not the same catalyst as the catalyst in claim 3, and claim 4 should be amended to recite “a material catalytically active in hydrocracking”.
With regard to claim 6, the claim recites “A process according to claim 4, wherein separating the intermediate…” However, there are two different intermediates which have been separated in claims 1 and 4, claim 1 separates the deoxygenated intermediate and claim 4 separates the dearomatized intermediate. Thus, the phase “separating the intermediate” lacks antecedent basis.
For purposes of examination, the remainder of claim 6 refers to “the deoxygenated intermediate”. Thus, the separation in lines 1-2 will be considered to be performed on the deoxygenated intermediate. Appropriate correction is respectfully requested.
With regard to claim 8, the claim recites “The process according to claim 6, wherein the mass of the heavy fraction is less than 15 wt% of the feedstock.” While claim 6 does separate a heavy fraction, it is not separated from the feedstock, but is separated from the deoxygenated intermediate. Thus, it is unclear how the heavy fraction can be less than 15 wt% of the feedstock, when the heavy fraction has not previously been recited as part of the feedstock.
For purposes of examination, the specification discusses the heavy fraction being less than 15% of the feedstock immediately after discussing passing the heavy fraction optionally to the thermal decomposition to obtain a decomposed heavy product as part of said feedstock (paragraph bridging pages 4-5). Thus, it appears that claim 8 should actually be dependent on claim 7, which recites passing the heavy fraction to the thermal decomposition to obtain a decomposed heavy product as part of said feedstock, but also that claim 8 should recite “the decomposed heavy product” instead of “the heavy fraction” if this is the case. Appropriate clarification and amendment are respectfully requested.
With regard to claim 9, the claim recites “A process according to claim 1…directing an amount or a combination of amounts of middle distillate, dearomatized middle distillate, hydrocracked product, heavy fraction, hydrocracked intermediate, dearomatized intermediate, or product stream to an upstream process step…” However, only the “dearomatized intermediate” is recited in claim 1. Thus, the remaining fractions recited lack nexus with claim 1, as it is unclear if they are produced in the claimed process, or obtained from outside the process. Thus, the claim is indefinite.
For purposes of examination, the Examiner will consider all fractions produced in all the dependent claims, which include most of the listed fractions, can be recycled in claim 9. However, appropriate amendment needs to be made to clarify where the fractions are produced or to change the dependency so that the fractions have nexus and antecedent basis.
With regard to claim 11, the claim recites “an active metal taken from the group comprising platinum….and molybdenum…” This is improper Markush wording. “A Markush grouping is a closed group of alternatives, i.e., the selection is made from a group "consisting of" (rather than "comprising" or "including") the alternative members. Abbott Labs., 334 F.3d at 1280, 67 USPQ2d at 1196. If a Markush grouping requires a material selected from an open list of alternatives (e.g., selected from the group "comprising" or "consisting essentially of" the recited alternatives), the claim should generally be rejected under 35 U.S.C. 112(b) as indefinite because it is unclear what other alternatives are intended to be encompassed by the claim." MPEP 2173.05(h)I;
For purposes of examination, the Examiner will consider that the claim is intended to be a Markush group. The language should be amended to recite “an active metal selected from the group consisting of” to be proper Markush language.
With regard to claims 5 and 7, the claims are rejected as being dependent on a rejected base claim.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1, 9-11, 13, and 14 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Nousiainen et al. (WO 2015/004329, cited on IDS of 04/24/2024).
With regard to claim 1, Nousiainen teaches a method for producing hydrocarbons (Abstract) comprising the following steps (Figure 2 and corresponding description pages 27-28):
a) providing a feedstock of biological origin 4 with hydrogen gas 5 to a hydrodeoxygenation reactor 30 comprising an HDO catalyst to produce a product (deoxygenated intermediate) (page 27, lines 18-24), where the feedstock is a pyrolysis oil from lignin derived compounds (originating from thermal decomposition of solids) (page 5, line 29) which comprises 25-40 wt% aromatic compounds (page 7, line 25). This is within the range of at least 5 wt% of instant claim 1.
b) separating the product (deoxygenated intermediate) in fractionator 50 to obtain a diesel stream 11 (page 27, lines 34-36) where the diesel stream has a boiling point range of 160-380°C (page 22, line 20) which is within the range of above 150°C of instant claim 1.
c) passing the diesel fraction 11 with hydrogen gas 5 to a hydrodearomatization reactor 60 comprising a HDA catalyst to provide a liquid hydrocarbon product 13 comprising low aromatics content (dearomatized intermediate) (page 27, line 39-page 28, line 6).
With regard to claim 9, Nousiainen teaches recycling a heavy fraction 12 back to the hydrodeoxygenation reactor 30 (upstream) (page 27, lines 37-38 and Figure 2). This forms a liquid recycling loop as claimed.
With regard to claim 10, Nousiainen teaches the hydrodearomatization conditions include a temperature of 300°C, a pressure of 90 bar, and an LHSV of 1 h-1 (page 28, Example 1, lines 25-26). These are within the ranges of 200-350°C, 30-200 bar, and 0.5 to 8 h-1 of instant claim 10.
With regard to claim 11, Nousiainen teaches the catalyst is NiMo on a silica-alumina (refractory) support.
With regard to claim 13, Nousiainen teaches cooling the hydrodeoxygenation product (deoxygenated intermediate) before separating and passing the diesel fraction to hydrodearomatization (page 23, lines 18-22).
With regard to claim 14, Nousiainen teaches an apparatus for hydroprocessing a pyrolysis product as a feedstock comprising 25-40 wt% aromatics (page 7, line 25), within the range of at least 5 wt% of instant claim 14, comprising the following (Figure 2 and corresponding description pages 27-28):
a) a hydrodeoxygenation section 30 having an inlet for feed stream 4 and an outlet for stream 7 and
b) a hydrodearomatization section 60 having an inlet for stream 11 and an outlet for stream 13, where the outlet of the hydrodeoxygenation section 30 is in fluid communication through the separator 40 with the inlet of the hydrodearomatization section 60, as claimed.
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 and 3 are rejected under 35 U.S.C. 103 as being unpatentable over Nousiainen et al. (WO 2015/004329, cited on IDS of 04/24/2024) as applied to claim 1 above, and further in view of Iversen et al. (US 2021/0062098).
With regard to claim 2, Nousiainen teaches the process above, where the pyrolysis oil feedstock can be purified prior to hydroprocessing (page 9, lines 9-10).
Nousiainen does not specifically teach a step of contacting an unstabilized pyrolysis oil feedstock with hydrogen at hydrotreating conditions to produce the pyrolysis oil feedstock.
Iversen teaches a process for upgrading a renewable oil (paragraph [0025]) from solid biomass (paragraph [0055]). Iversen further teaches the method comprises passing the crude renewable feed to a stabilization unit in the presence of hydrogen at a temperature and pressure (paragraphs [0110]-[0111]) before passing the stabilized liquid to the hydroprocessing steps include hydrodeoxygenation and hydrodearomatization (paragraphs [0398] and [0417]). Iversen further teaches the stabilization zone purifies the oil by reducing aromatics and metals and thus reduces down time of the process and extends catalyst lifetime of the hydroprocessing catalysts (paragraph [0110]).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to add the step of stabilization of Iversen to the process of Nousiainen, because Nousiainen and Iversen each teach hydroprocessing an oil from solid biomass in hydrodeoxygenation and dehydroaromatization zones, Nousiainen teaches purification of the pyrolysis oil before the hydroprocessing, and Iversen teaches that the stabilization purifies the oil and reduces down time of the process and extends catalyst lifetime of the hydroprocessing catalysts (paragraph [0110]).
With regard to claim 3, Nousiainen teaches the process above. Nousiainen further teaches separating a heavy fraction 12 from the product in fractionator 50 (deoxygenated intermediate).
Nousiainen does not explicitly teach at least a portion of the heavy fraction 12 can be sent to a hydrocracking step.
Iversen teaches a process for upgrading a renewable oil (paragraph [0025]) from solid biomass (paragraph [0055]). Iversen further teaches the method comprises (see Figure 6) passing the feed through hydrodeoxygenation zones I and II, fractionating the feed into a low boiling fraction comprising a boiling point up to 350°C (paragraph [0413]) and a high boiling fraction, sending the low boiling component to hydrodearomatization, and sending the high boiling fraction to hydrocracking with a hydrocracking catalyst (paragraphs [0415]-[0417] and [0426]). Iversen further teaches that adding the step of hydrocracking the high boiling fraction significantly reduces the amount of residue and density of the high boiling fraction, maximizing middle distillate range fuel products (paragraph [0426]).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to add the step of hydrocracking the heavy (high boiling) fraction to the process of Nousiainen, because Nousiainen and Iversen each teach hydroprocessing oil from thermal treatment of solid biomass including hydrodeoxygenation and fractionation into a fraction comprising diesel and a heavy (high boiling) fraction, and Iversen teaches that sending the high boiling fraction to hydrocracking significantly reduces the amount of residue and density of the high boiling fraction, maximizing middle distillate range fuel products (paragraph [0426]).
Claims 4 and 6-8 are rejected under 35 U.S.C. 103 as being unpatentable over Nousiainen et al. (WO 2015/004329, cited on IDS of 04/24/2024) in view of Iversen et al. (US 2021/0062098) as applied to claim 2 above, and further in view of Quignard et al. (US 2011/0167713).
With regard to claim 4, Nousiainen teaches the process above.
Nousiainen fails to teach i) separating the dearomatized product (dearomatized intermediate) to obtain a heavy fraction and vapor fraction or ii) sending the heavy fraction to hydrocracking.
With regard to separating i), Iversen teaches a process for upgrading a renewable oil (paragraph [0025]) from solid biomass (paragraph [0055]). Iversen further teaches the method comprises hydrodeoxygenation, separating the product to obtain a fraction comprising diesel range hydrocarbons (paragraph [0413]), dearomatization of the diesel range hydrocarbons, and then separating the dearomatization product to obtain a gas fraction (vapor) and a gas oil (heavy) product (Figure 6). Thus, Iversen teaches that the product from dearomatization also comprises a heavy gas oil product and vapor which can be separated (Figure 6). Iversen teaches dearomatization at below 380°C, 0.1 to 1.5 h-1 LHSV, and at least 20 bar (paragraphs [0418]-[0422]). Nousiainen teaches temperature of 300°C, a pressure of 90 bar, and an LHSV of 1 h-1 (page 28, Example 1, lines 25-26). Thus, because Iversen and Nousiainen teach the same hydrodearomatization of the same diesel fraction at similar conditions, one of ordinary skill in the art would reasonably conclude that the hydrodearomatization product of Nousiainen also contains a heavy fraction and vapor, as claimed.
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to separate the product of the dearomatization of Nousiainen to obtain the heavy fraction, because Nousiainen and Iversen each teach hydrodeoxygenation, separation into a diesel fraction, and dearomatization to obtain a diesel product at similar conditions, Nousiainen is silent regarding the presence of other heavy fractions, and Iversen teaches that the product of the diesel fraction from hydrodearomatization comprises a gas oil (heavy) fraction and vapor which can be separated.
With regard to the hydrocracking heavy fraction ii), Quignard teaches a method for thermal conversion of solid biomass (paragraph [0001]). Quignard further teaches the product can be separated to obtain a gas oil fraction (paragraph [0124]), which can be hydrocracked in order to obtain products having good specifications (paragraph [0128]).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to pass the heavy fraction of Nousiainen in view of Iversen to a hydrocracking step as taught by Quignard, because each of Nousiainen in view of Iversen and Quignard teaches conversion of biomass to oils and separating a gas oil fraction, and Quignard teaches that passing the gas oil fraction to hydrocracking produces products meeting desired specifications (paragraph [0128]).
With regard to claim 6, Nousiainen teaches the method above, where the separation of the deoxygenated effluent provides a heavy residue 12 and a diesel fraction 11 (page 27, lines 35-36) and where as noted above the diesel fraction is contacted with the dearomatization catalyst in unit 60 (page 27, lines 39-40). As above, the diesel fraction is boiling from 160-380°C (page 22, line 20), which is within the range of above 150°C of instant claim 6.
Nousiainen does not specifically teach the boiling point of the heavy residue. However, as the diesel fraction has a boiling end point of 380°C and one of ordinary skill in the art understands that the heavy fraction is heavier than the diesel fraction, one of ordinary skill in the art would reasonably conclude that the initial boiling point of the heavy fraction is similar to or above the end point of the diesel fraction. Thus, the initial boiling point of the heavy fraction is reasonably expected to be about 380°C or higher, which is within the range of above 320°C of instant claim 6.
With regard to claim 7, Nousiainen teaches that a portion of the heavy residue 12 is recycled, and a portion is removed from the process (page 27, lines 37-39 and Figure 2). Thus the heavy residue is withdrawn as heavy product, as claimed.
With regard to claim 8, Nousiainen does not specifically teach the portion of the product that is in the heavy fraction. However, Nousiainen teaches the hydrodeoxygenation step having a catalyst of Ni, Mo, and/or Co on an oxide (refractory) support (page 18, line 38-page 19, line 6) and conditions including 280-450°C (page 24, line 40), 50-180 bar (page 25, line 11), and LHSV of 0.1-5 h-1 (page 25, line 16). The instant specification teaches hydrodeoxygenation at temperatures of 250-400°C, pressure 30-150 bar, and LHSV of 0.1-2 h-1, with a catalyst comprising Mo, W, Ni, and/or Co on a refractory oxide support (page 15).
Thus, Nousiainen teaches the same feedstock passed to the same hydrodeoxygenation step at similar conditions and with the same catalyst to produce the same product which is fractionated to produce a diesel product and a heavy fraction, and thus the heavy fraction of Nousiainen is expected to be less than 15 wt% of the feedstock, as claimed, absent any evidence to the contrary.
Claim 5 is rejected under 35 U.S.C. 103 as being unpatentable over Nousiainen et al. (WO 2015/004329, cited on IDS of 04/24/2024) in view of Iversen et al. (US 2021/0062098) and Quignard et al. (US 2011/0167713) as applied to claim 4 above, and further in view of Joseck et al. (US 2012/0261307).
With regard to claim 5, Nousiainen teaches the method above, where the hydrodeoxygenation product is separated in a separator 40 and a separator 50 (page 27, lines 28-36).
Nousiainen does not specifically teach i) the separators comprise a stripper or ii) the stripping conditions.
With regard to the stripper i), Iversen teaches a process for upgrading a renewable oil (paragraph [0025]) from solid biomass (paragraph [0055]). Iversen further teaches the method comprises separating the product from hydrodeoxygenation in a recovery unit comprising at least one stripper (paragraph [0345]). Thus, Iversen teaches it is known and suitable to include a stripper in the separation of the hydrodeoxygenation effluent.
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use a stripper in the separation steps of Nousiainen, because Nousiainen teaches separation but is silent regarding the means, and Iversen teaches it is known and suitable to use a stripper for the separation.
With regard to stripping conditions ii), Joseck teaches a process for hydroprocessing hydrocarbon feedstocks. Joseck teaches performing separation between the separation zones using separators conducted with less than 100 psi (6.9 bar) pressure drop from the hydroprocessing zones (paragraph [0031]). This is within the range of less than 10 bar of instant claim 5. Joseck further teaches the separator is a stripper and that the temperature for the stripper is the same as the preceding hydroprocessing zone (paragraph [0032]), while Nousiainen teaches the hydrodeoxygenation conditions include a temperature of 280-450°C (page 24, line 40). Thus, according to Nousiainen in view of Joseck, the temperature of the stripper is 280-450°C, which is within the range of above 150°C of instant claim 5. Joseck additionally teaches that a process which uses the high pressure and temperature strippers does not require the typical disengaging steps, thus providing decreased capital cost, decreased need for hydrogen gas, and decreased operating costs (paragraph [0040]).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use the high pressure stripper and conditions of Joseck in the process of Nousiainen in view of Iversen, because Nousiainen in view of Iversen teaches the presence of a stripper but is silent regarding the conditions, and Joseck teaches that using a high pressure high temperature stripper provides decreased capital cost, decreased need for hydrogen gas, and decreased operating costs (paragraph [0040]).
Claim 12 is rejected under 35 U.S.C. 103 as being unpatentable over Nousiainen et al. (WO 2015/004329, cited on IDS of 04/24/2024) as applied to claim 1 above, and further in view of Urade et al. (US 2017/0009143).
With regard to claim 12, Nousiainen teaches the process above, where the catalyst for the hydrodearomatization comprises Pt or Pd on an oxide (refractory) support (page 20, lines 31-33 and 37).
Nousiainen fails to explicitly teach the catalyst has higher hydrogenation activity than the material catalytically active in hydrodeoxygenation. However, the instant specification recites that this higher hydrogenation activity is obtained by using a catalyst “comprising an elevated amount of active metals, such as from at least 0.1 wt%, at least 0.5 wt% or at least 1 wt%, to 3 wt% Pt or Pd noble metal” (page 7, lines 19-25). Thus, one of ordinary skill in the art would consider that any catalyst meeting these metal amounts has the claimed higher hydrogenation activity.
Nousiainen is silent regarding the amount of the metals in the hydrodearomatization catalyst.
Urade teaches a process for hydroprocessing renewable feeds to upgrade a diesel fraction (paragraph [0055]). Urade further teaches the catalyst for the process is a catalyst comprising 0.05 to 3 wt% platinum or palladium on an oxide (refractory) support, and that this catalyst is useful when a large amount of aromatics saturation (dearomatization) is required without converting much of the diesel product to gasoline (paragraph [0062]).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use the amounts of Urade for the catalyst of Nousiainen, because each of Nousiainen and Urade teaches hydrodearomatization of a diesel product from a renewable feed over a catalyst comprising Pt or Pd on an oxide support, Nousiainen is silent regarding the amounts, and Urade teaches the amounts are suitable for large amounts of aromatics saturation (dearomatization) without conversion of diesel to gasoline (paragraph [0062]). Using these amounts is expected to give the catalyst having a higher hydrogenation activity than the hydrodeoxygenation catalyst, as claimed.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ALYSSA L CEPLUCH whose telephone number is (571)270-5752. The examiner can normally be reached M-F, 8:30 am-5 pm, EST.
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/Alyssa L Cepluch/Examiner, Art Unit 1772
/IN SUK C BULLOCK/Supervisory Patent Examiner, Art Unit 1772