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 Status
Claims 1-14 are amended.
Claims 1-14 are pending for examination below.
Claim Interpretation
Claim 4 recites “separating the dearomatization effluent…and directing at least an amount of the high boiling fraction to a material catalytically active in hydrocracking…” However, claims 5 and 6 are dependent on claim 4, but discuss separation of the deoxygenation effluent instead of the dearomatization effluent recited in claim 4. This dependency was present in the original claims and is repeated in the specification, where there is separation of the deoxygenation effluent, a portion is passed to dearomatization, and there is also separation of the dearomatization effluent and a portion is passed to hydrocracking (see PGPub paragraphs [0014] and [0021]). As such, the claims will be interpreted as written, which is that claim 4 recites separation of the dearomatization effluent but claims 5 and 6 refer back to the deoxygenation separation of instant claim 1.
Response to Arguments
Applicant’s arguments and amendments, see Remarks, filed 26 May 2026, with respect to the rejection(s) of claim(s) 1-14 under USC 102 and 103 have been fully considered and are persuasive. The combination of Nousiainen and Iversen does not teach the process of claim 1 as amended to require sending the dearomatization intermediate to the hydrocracking step. Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of newly cited prior art and 112(a), (b), and (c) issues resulting from the amendments.
Claim Objections
Claim 13 is objected to because of the following informalities:
Claim 13 recites “the stream directed to contact the material catalytically active in hydrodearomatization”. For antecedent basis purposes, this should be “the amount of the deoxygenated distillate fraction” rather than “the stream”.
Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 1-14 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
Claim 1 recites separation of a hydrodeoxygenated intermediate into at least a “deoxygenated distillate fraction”, passing at least an amount of the deoxygenated distillate fraction to hydrodearomatization to obtain a dearomatized intermediate, and “directing the dearomatized intermediate” to hydrocracking to obtain a hydrocracked intermediate. Upon review of the specification, the Examiner has determined that there is no support for performing the steps in the claimed order, and the claim is thus new matter. There are 3 embodiments supported by the specification as filed, as shown in Fig. 2, 3, and 4. Figure 2 includes separation of a hydrodeoxygenated intermediate to obtain a distillate fraction and a heavy fraction, passing the distillate fraction to the hydrodearomatization, and passing the heavy fraction to the hydrocracking. Figure 3 includes separation of a hydrodeoxygenated intermediate to obtain a distillate fraction and a heavy fraction, and sending the heavy fraction to a combined hydrodearomatization/hydrocracking reactor. Figure 4 includes deoxygenation followed by hydrodearomatization, then followed by separation of a distillate and heavy fraction and sending the heavy fraction to the hydrocracking. There is no teaching in the specification that the embodiments can be combined, and no general teaching which indicates that the order can be separation, and then hydrodearomatization and hydrocracking in separate reactors of the same fraction.
Claim 3 recites “directing at least an amount of the deoxygenated intermediate to contacting a material catalytically active in hydrocracking…”. However, there is no support in the specification for passing two different feeds, the portion of deoxygenated intermediate of claim 3 and the dearomatized effluent of claim 1, to hydrocracking. The embodiments in the Figures pass either a portion of the dearomatized effluent or a portion of the deoxygenated effluent to the hydrocracking, but there are no embodiments which hydrocrack both kinds of feeds.
Claim 14 recites that the “hydrodearomatization inlet is in fluid communication with the fractionation section outlet” and that the “hydrocracking section inlet is in fluid communication with the hydrodearomatization section outlet.” Upon review of the specification, the Examiner has determined there is no support for arranging the reactors in the claimed manner, as no embodiments show the claimed arrangement and there is no further description of the apparatus. In Figure 2, the hydrodearomatization and hydrocracking are parallel reactors that are not connected at all. In Figure 3, the hydrodearomatization and hydrocracking are combined in a single reactor, and there is no outlet or inlet described or shown within the reactor. In Figure 4, hydrodearomatization outlet is in fluid communication with the separation step inlet, which is reverse order of the claimed steps.
Claims 2 and 5-13 are rejected as being dependent on a rejected base claim.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 4 and 9 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Claim 4 recites “further comprising the step of separating the dearomatized intermediate into at least a high boiling fraction boiling above 300°C and a vapor fraction and directing at least an amount of the high boiling fraction to contact a material catalytically active in hydrocracking…” However, claim 1 already recites “directing the dearomatized intermediate to contact a material catalytically active in hydrocracking…” As such, claim 4 does not incorporate all the limitations of claim 1.
For purposes of examination, the Examiner will consider that claim 1 is open to separation of the dearomatized intermediate before hydrocracking, as in Figure 4. However, as claimed, this is a combination of embodiments and remains new matter as discussed above.
Claim 9 recites “directing an amount or a combination of amounts of…dearomatized intermediate to an upstream process step.” However, claim 1 again already recites “directing the dearomatized intermediate to contact a material catalytically active in hydrocracking…” As such, claim 9 does not incorporate all the limitations of claim 1.
For purposes of examination, the Examiner will consider that claim 1 is open to separation of the dearomatized intermediate such that a portion can be recycled as in claim 9.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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 1, 2, 4, and 6-14 are rejected under 35 U.S.C. 103 as being unpatentable over Iversen (WO 2019/138002).
With regard to claims 1, 4, 6, and 7, Iversen teaches a process for upgrading oxygen containing renewable oil (Abstract), where the oxygen containing renewable oil is produced by hydrothermal liquefaction of biomass (page 11, lines 1-10) and comprises at least 20 wt% aromatics and an oxygen content of 3 to 20 wt% (page 11, lines 15-23). These ranges are within the range of at least 5 wt% aromatics and overlapping the range of 5-50 wt% oxygen of instant claim 1, rendering the range prima facie obvious. The hydrothermal liquefaction is a thermal decomposition of solids process as described in the instant specification page 11, lines 19-26. Iversen further teaches that the process comprises the following steps:
a) passing the oxygen containing renewable oil to a first reaction zone comprising a catalyst and conditions for substantially reducing the oxygen content in the presence of hydrogen (claimed hydrodeoxygenation catalyst and conditions) to produce a partially upgraded oil (claimed deoxygenated intermediate) (page 75, lines 5-20).
b) passing the partially upgraded oil (deoxygenated intermediate) to a second reaction zone comprising hydrogen gas and conditions and a catalyst to perform dearomatization by saturation of aromatics (claimed hydrodearomatization under hydrodearomatization conditions) to produce a second partially upgraded oil (claimed dearomatized intermediate) (page 77, lines 19-22).
c) separating the second partially upgraded oil into at least one partially upgraded low boiling oil fraction and at least one partially upgraded high boiling oil fraction (claimed heavy fraction instant claim 7) (page 80, lines 1-10) where the high boiling oil has a boiling point of greater than 320°C (page 8, lines 14-16), which is within the ranges of boiling above 150°C of instant claim 1, boiling above 300°C of instant claim 4, and boiling above 320°C of instant claim 6. Iversen teaches that the low boiling fraction comprises a fraction boiling up to 320°C (claimed middle distillate fraction) (page 80, lines 15-16), which overlaps the range of about 150°C to 320°C of instant claim 6 and renders the range prima facie obvious. Iversen further teaches the low boiling fraction is further passed to an additional dearomatization step (hydrodearomatization of instant claim 6) (page 81, lines 5-10).
d) passing the partially upgraded high boiling oil (heavy fraction instant claim 7) to a reaction zone comprising hydrogen, a hydrocracking catalyst and conditions to obtain a hydrocracking product (page 82, lines 24-29).
Iversen fails to teach that the separation of product takes place after the first (hydrodeoxygenation) reactor rather than after the second (hydrodearomatization) reactor. However, this is merely a selection of the order of steps. The selection of the order of steps is prima facie obvious absent any evidence of criticality (see MPEP 2144.04(IV)C). Also, the instant specification obtains good results with a process which comprises hydrodeoxygenation, hydrodearomatization, then hydrocracking of a heavy fraction obtained from the hydrodearomatization effluent (Figure 4, Table 3) and a process which fractionates and then does a combined hydrodearomatization/hydrocracking of the heavy fraction (Table 3 and Figure 3). As such, it would have been obvious to one of ordinary skill in the art at the time of the invention to perform the steps of separation, hydrodearomatization, and hydrocracking of Iversen in the claimed order with a reasonable expectation of success and without undue experimentation, absent any evidence to the contrary.
With regard to claim 2, Iversen teaches contacting the oxygen containing renewable oil with a catalyst in a stabilization zone of the first reactor prior to contacting the oil with catalysts in the first and second reaction zone (page 20, lines 16-17 and page 22, lines 23-25) where the stabilization is a hydrotreatment step in the presence of hydrogen gas (page 21, lines 29-30).
With regard to claim 8, Iversen does not specifically teach the portion of the product that is in the heavy fraction. However, Iversen teaches the hydrodeoxygenation step having a catalyst of a. Ni and/or Mo, and b. Co (page 72, lines 29-31) on an alumina (refractory) support (page 73, lines 1-2) and conditions including 260-350°C (page 70, line 24), 80-150 bar (page 70, line 3). 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, Iversen 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 heavy fraction, and thus the heavy fraction of Iversen is expected to be present in an amount which is similar to the claimed amount of less than 15 wt% of the feedstock, as claimed, absent any evidence to the contrary.
With regard to claim 9, Iversen teaches separating a part of the partially upgraded oil product (dearomatized intermediate) and recycling upstream before the deoxygenation (Figure 6 and page 80, lines 21-24)
With regard to claim 10, Iversen teaches the second reaction zone (dearomatization) comprises a temperature of 350-420°C (page 78, line 4), a pressure of below 200 bar (page 78, line 30), and a LHSV of 0.1 to 1.5 h-1 (page 78, line 12). These overlap the ranges of 200-350°C, 30 to 200 bar, and 0.5 to 8 h-1 of instant claim 9, rendering the ranges prima facie obvious.
With regard to claim 11, Iversen teaches that the second reaction zone (dearomatization) comprises a catalyst comprising Co, Ni, W, or Mo on an alumina (refractory) support (page 72, line 29-page 73, line 5).
With regard to claim 12, Iversen teaches that the catalysts in the first and second reaction zones have different activities (page 18, lines 20-22). Iversen does not specifically teach that the activity of the second reaction zone catalyst (hydrodearomatization catalyst) has a higher activity than the first reaction zone (hydrodeoxygenation) catalyst. However, this is merely selection from a finite list of two options, which is obvious to try (see MPEP . Further, because Iversen teaches the catalysts have different activities and the hydrodeoxygenation and hydrodearomatization steps, one of ordinary skill could select the hydrodearomatization catalyst to have the higher activity with a reasonable expectation of success and without undue experimentation.
With regard to claim 13, Iversen teaches heating the feed to the hydrodeoxygenation by recovering the heat from another part of the process (page 71, lines 13-15). Iversen further teaches the first reaction zone is very exothermic (page 21, line 22). Therefore, while Iversen does not explicitly teach cooling the first reaction effluent before hydrodearomatization, it would have been obvious to one of ordinary skill in the art at the time of the invention to cool the first reaction effluent, as claimed, because Iversen teaches heating the feed by recovering heat from another part of the process and that the first hydrodeoxygenation zone produces a lot of heat because the reaction is very exothermic (page 21, line 22).
With regard to claim 14, Iversen teaches an apparatus for upgrading oxygen containing renewable oil (Abstract), where the oxygen containing renewable oil is produced by hydrothermal liquefaction of biomass (page 11, lines 1-10) and comprises at least 20 wt% aromatics and an oxygen content of 3 to 20 wt% (page 11, lines 15-23). These ranges are within the range of at least 5 wt% aromatics and overlapping the range of 5-50 wt% oxygen of instant claim 14, rendering the range prima facie obvious. The hydrothermal liquefaction is a thermal decomposition of solids process as described in the instant specification page 11, lines 19-26.
Iversen further teaches that the apparatus comprises the following components (see Figure 6):
a) a first reaction zone I comprising an inlet, an outlet, and a first catalyst (page 72, lines 4-7 and Figure 6).
b) a second reaction zone II comprising a catalyst, an inlet in fluid communication with the outlet of reaction zone I, and an outlet (page 77, lines 19-22).
c) a separation having an inlet in fluid communication with the second reaction zone II and an outlet for a partially upgraded high boiling oil fraction where the high boiling oil has a boiling point of greater than 320°C (page 8, lines 14-16), which is within the range of boiling above 150°C of instant claim 14.
d) a fourth reaction zone IV having an inlet in fluid communication with the separation unit and an outlet.
Iversen fails to teach that the separation unit is located in fluid communication with the first reactor rather than in fluid communication with the second (hydrodearomatization) reactor. However, this is merely a change in the sequence of the units. A change in sequence is prima facie obvious absent any evidence of criticality (see MPEP 2144.04(IV)C). Also, the instant specification obtains good results with an apparatus which comprises hydrodeoxygenation, hydrodearomatization, separation, then hydrocracking of a heavy fraction obtained from the hydrodearomatization effluent (Figure 4, Table 3) and an apparatus which has hydrodeoxygenation, fractionation, and a combined hydrodearomatization/hydrocracking reactor (Table 3 and Figure 3). As such, it would have been obvious to one of ordinary skill in the art at the time of the invention to place the apparatus of hydrodeoxygenation, separation, hydrodearomatization, and hydrocracking of Iversen in the claimed order with a reasonable expectation of success and without undue experimentation, absent any evidence to the contrary.
Claim 5 is rejected under 35 U.S.C. 103 as being unpatentable over Iversen (WO 2019/138002) as applied to claim 4 above, and further in view of Joseck et al. (US 2012/0261307).
With regard to claim 5, Iversen teaches that the separating comprises multiple separation steps (page 80, lines 1-12).
Iversen fails to teach a stripping step at the claimed temperature and pressure.
Joseck teaches a process for hydroprocessing hydrocarbon feedstocks. Joseck teaches performing separation between the reaction 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 includes a stripper and that the temperature for the stripper is the same as the preceding hydroprocessing zone (paragraph [0032]) and Iversen teaches the hydrodeoxygenation conditions include a temperature of 350-420°C (page 78, line 4). Thus, according to Iversen in view of Joseck, the temperature of the stripper is 350-420°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 Iversen, because Iversen teaches the multiple separation steps and Joseck teaches that using a high pressure high temperature stripper as part of the separation step provides decreased capital cost, decreased need for hydrogen gas, and decreased operating costs (paragraph [0040]).
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
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
/Renee Robinson/Primary Examiner, Art Unit 1772
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