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 .
This communication is in response to the amendment and reply filed 7/14/2026.
Claims 1-19 and 20 are pending.
Response to Arguments
Applicant's arguments filed 7/14/2026 have been fully considered but they are not persuasive. Applicant argues the art fails to teach solvent assisted visbreaking as claimed. However, the art teaches mixing the heavy hydrocarbon feed with an aromatic solvent upstream of the visbreaking. This is interpreted as solvent assisted visbreaking. Alternatively, in view of the claimed amendments, EP 0133774 discloses “visbreaking heavy petroleum resids in the presence of certain hydrogen-donor solvents, visbreaking severity can be greatly increased without significant coke or sediment formation.” Page 2.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim(s) 1-3 and 7-15 is/are rejected under 35 U.S.C. 102(a) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over Tsuchitani (US 5,182,011).
Alternatively, Claim(s) 1-3 and 6-15 is/are rejected under 35 U.S.C. 103 as obvious over Tsuchitani (US 5,182,011) in view of Choi (EP 0133774).
With respect to claim 1, Tsuchitani teaches a process for preparing pitches (abstract), comprising a four-step treatment of (1) heat-treatment, (2) distillation, (3) extraction of soluble from insoluble, and (4) distillation (abstract).
Tsuchitani teaches mixing a heavy hydrocarbon feedstock with an aromatic oil and soluble oil (containing aromatic hydrocarbons) and subjecting the mixture to heat treating in a heat treatment unit to produce a first effluent comprising a heat-treated product (col. 12, lines 60-68). The hydrocarbon is subjected to visbreaking conditions in the presence of an aromatic solvent and therefore is interpreted as solvent assisted visbreaking. The effluent is distilled or flashed in a first separation unit to produce a distillate fraction and a thermally cracked heavy component (i.e. a second effluent) (col. 13, lines 4-8). “The thermal-cracked heavy component which is the bottom fraction of the distillation column 17 is sent to the insoluble component separator.” Col. 35, lines 55+; col. 13, lines 9+. A solvent is mixed with the bottoms and fed to a separator where the mixture is separated into an insoluble component to obtain high molecular weight bituminous material (i.e. product (ii)) (col. 13, lines 9-15) and a component substantially soluble in the aromatic solvent containing solvent and heavy cracked components (26 in figure 2). This is interpreted as deasphalting with a solvent. Tsuchitani teaches hydrogenating the pitch, distilling to remove solvent, and further heat treating the pitch in a subsequent heat treatment step to produce mesophase pitch (col. 36, lines 10-21). Tsuchitani teaches the same process of heat treatment, distillation, and deasphalting the bottoms product, it is inherent or else obvious to one of ordinary skill at the time of filing that the soluble and insoluble fractions will each contain a portion of the pitch and solvent, and that the soluble fraction and insoluble fraction would each contain soluble and insoluble components of the effluent, respectively.
Tsuchitani discloses subjecting the feed to visbreaking conditions in the presence of an aromatic solvent and therefore is interpreted as solvent assisted visbreaking. Alternatively, Choi (EP 0133774) discloses a process for visbreaking heavy oil. The visbreaking includes subjecting heavy oil to an elevated temperature for a period of time corresponding to an equivalent reaction time in the presence a hydro-aromatic solvent. Page 2. “[B]y visbreaking heavy petroleum resids in the presence of certain hydrogen-donor solvents, visbreaking severity can be greatly increased without significant coke or sediment formation.” Page 2. Aromatic solvents useful in improving visbreaking while minimizing coke and sediment formation include, for example, highly aromatic petroleum refinery streams, fluidized catalytic cracker cycle oil or bottoms fractions, polycyclic aromatic hydrocarbon constituents such as naphthalene, dimethylnaphthalene, anthracene, etc., aromatic extract, coal tar, hydrocracking fractions, among others. Pages 2-7. Therefore, before the filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to conduct the heat treating of Tsuchitani in a solvent assisted visbreaking process as shown in Choi because Tsuchitani itself teaches an embodiment wherein aromatic hydrocarbons are blended with the feed before treating and Choi discloses that visbreaking in the presence of an aromatic solvent allows the severity of visbreaking to be increased without significant coke or sediment formation.
With respect to claim 2, Tsuchitani teaches wherein a portion of the mother liquid (deasphalted oil separated in 24) is mixed with the feedstream prior to heat treating. This stream includes components boiling at a temperature below 350C, which overlaps the claimed streams of naphtha through gas oil range.
With respect to claim 3, Tsuchitani teaches wherein the first solvent is a monocyclic aromatic hydrocarbon or solvent having similar solubility (col 13). Exemplified solvents include benzene, toluene, xylene (col. 21, lines 36+) as well as mixed solvents of hexane, heptane, acetone, MEK, methanol, ethanol, kerosene, gas oil, naphtha, with quinoline, pyridine, coal tar gas oil, wash oil, carbonyl oil, anthracene oil, aromatic low boiling oil (col. 21, lines 50+).
With respect to claims 7 and 8, Tsuchitani teaches a “method can be employed for separating the insoluble materials” including filtration. Therefore, it would have been obvious to one of ordinary skill in the art at the time of fling to remove fines and other particles from the thermal cracked effluent 16 or portion thereof such as 19 before further treatment using means well known in the art to achieve predictable results.
With respect to claim 9, Tsuchitani teaches recycling solvent from the first distillation unit for use in the heat treatment unit (col. 35, line 52+).
With respect to claim 10, Tsuchitani teaches wherein heat treating the heavy hydrocarbon feedstock in a heat treatment unit occurs at least at a temperature ranging of 400-600°C (col. 26, line 5), which overlaps the claimed range of from 350 to 550°C; and a residence time of 30-1,000 seconds (col. 26, line 6), which overlaps the claimed range of about 5 minutes or greater.
With respect to claim 11, Tsuchitani teaches wherein the hydrocarbon feed contains a number of impurities such as It would have been obvious to one of ordinary skill in the art at the time of filing to subject the feed to hydrotreating to remove contaminants in a known way prior to producing isotropic or mesophase pitch.
With respect to claim 12, Tsuchitani teaches hydrotreating the bottoms product, which would result in at least partially removing a mixture of gas and heteroatoms contaminants, oxygenates, and metals (col. 33).
With respect to claim 13, Tsuchitani teaches heat treating the first pitch product and/or the isotropic pitch product to produce a mesophase pitch (col. 35, line 1+).
With respect to claim 14, Tsuchitani teaches optionally sparging a gas through the first pitch product and/or the isotropic pitch product to produce a mesophase pitch (col. 35, line 11).
With respect to claim 15, Tsuchitani teaches producing a high-performance fiber such as carbon or graphitized fiber from the mesophase pitch product (abstract).
Claim(s) 4, 6 and 16-19 is/are rejected under 35 U.S.C. 103 as obvious over Tsuchitani (US 5,182,011) as applied to claims 1-3 and 6-15, further in view of Choi (US 2022/0235283).
Alternatively, Claim(s) 4, 6 and 16-19 is/are rejected under 35 U.S.C. 103 as obvious over Tsuchitani (US 5,182,011) in view of Choi (EP 0133774) as applied to claims 1-3 and 6-15, further in view of Choi (US 2022/0235283).
With respect to claim 4, Tsuchitani teaches the limitations of claims 1-3 as discussed above. Tsuchitani is silent regarding deasphalting the soluble product fraction in a second deasphalting unit as claimed in claim 4.
Choi ‘283 is directed to deasphalting residual oil (abstract). Choi teaches using a two-step process to minimize the production of pitch while maintaining the DAO quality by utilizing a two-stage process (0004-0005). Choi teaches deasphalting the residual fraction in a first unit producing a pitch and first soluble product; deasphalting the first soluble product in a second deasphalting unit to produce a deasphalted oil and a second insoluble comprising resin (0029; 0043). The first solvent may be e.g. propane, butane, pentane, or combinations thereof (0035) and the second solvent may be any number of solvents, including those propane, butane, pentane (0046).
Before the filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to use two stage deasphalting of Choi as the deasphalting step of Tsuchitani because both are directed to methods for deasphalting residual oils, Choi teaches benefit of improved separation of components using two stage, and each is known in the art and the combination of such would do not more than obtain predictable results.
Before the filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to select two known deasphalting solvents in the process of Tsuchitani as suggested by Tsuchitani to achieve the desired separation of insoluble components from soluble components. It would have been obvious to select a higher solubility solvent for the first deasphalting stage where the desired product fractions include maximized soluble product and heaviest portion of insoluble compared to the resin.
With respect to claim 6, Choi taches the first soluble stream may have a metals content, such as 1-50 wt. ppm. Par. [0041]. The second insoluble stream may have a metals content of 10 to 70 % of the initial feed, such as 0.1-25 ppm. Par. [0057]. Thus, the metals removal overlaps the range of at least 20 to 25%.
With respect to claim 16, Tsuchitani in view of Choi teaches the limitations of claims 1-4, 6-10, and 12-15 above and applied here, including additional hydrotreating.
With respect to claim 17, it would have been obvious to select a higher solubility solvent for the first deasphalting stage where the desired product fractions include maximized soluble product and heaviest portion of insoluble compared to the resin.
With respect to claim 18, Tsuchitani teaches wherein the first solvent is a monocyclic aromatic hydrocarbon or solvent having similar solubility (col 13). Exemplified solvents include benzene, toluene, xylene (col. 21, lines 36+) as well as mixed solvents of hexane, heptane, acetone, MEK, methanol, ethanol, kerosene, gas oil, naphtha, with quinoline, pyridine, coal tar gas oil, wash oil, carbonyl oil, anthracene oil, aromatic low boiling oil (col. 21, lines 50+).
With respect to claim 19, Tsuchitani teaches a “method can be employed for separating the insoluble materials” including filtration. Therefore, it would have been obvious to one of ordinary skill in the art at the time of fling to remove fines and other particles from the thermal cracked effluent 16 or deasphalted oil before further treatment using means well known in the art to achieve predictable results.
Claim(s) 5 and 20 is/are rejected under 35 U.S.C. 103 as obvious over Tsuchitani (US 5,182,011) as applied to claims 1-3 and 6-15, further in view of Govindhakannan (US 2019/0093025).
Alternatively, Claim(s) 5 and 20 is/are rejected under 35 U.S.C. 103 as obvious over Tsuchitani (US 5,182,011) in view of Choi (EP 0133774) as applied to claims 1-3 and 6-15, further in view of Govindhakannan (US 2019/0093025).
With respect to claim 5, Tsuchitani teaches the limitations of claims 1-3 as discussed above. Tsuchitani is silent regarding deasphalting the insoluble product fraction (stream 28 in Tsuchitani) in a second deasphalting unit as claimed in claim 5.
Govindhakannan teaches solvent deasphalting of residue hydrocarbons in series (abstract). Govindhakannan teaches that “SDA typically recovers no more than about 40 wt. % product. Hence, further recovery is very desirable in SDA to make it worthwhile” (0004). The art teaches solvent extracting the feed 20 in a first unit 24 to separate a deasphalted oil 30 and a first pitch 32; stripping solvent from the first pitch in 50; and deasphalting the first pitch in second deasphalting unit 84 to obtain a second DAO 90 and a second pitch 92 (0027; Figure). The solvent in the downstream unit is higher than the solubility of the first, specifically, the “second solvent . . . is heavier than the first solvent, solubilizes the aliphatic and lighter hydrocarbon material in the first pitch stream that is heavier than the first pitch stream in the first pitch line” (0027). The art teaches that “SDA typically recovers no more than about 40 wt. % product. Hence, further recovery is very desirable in SDA to make it worthwhile” (0005).
Before the filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to use two stage deasphalting of Govindhakannan as the deasphalting step of Tsuchitani because both are directed to methods for deasphalting residual oils, Govindhakannan teaches benefit of improved separation and recovery of desirable product using two stage deasphalting over one stage, and each is known in the art and the combination of such would do not more than obtain predictable results.
With respect to claim 20, Tsuchitani discloses “[t]he process can be suitably applied to the preparation of pitches for HP carbon fiber production, in which the presence of even a slight amount of light fractions or the presence of solid materials such as cokes generally cause significant problems.” Col. 20, lines 30+. The pitch may be carbonized or graphitized. E.g. Table 7.
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 Brandi Doyle whose telephone number is (571)270-1141. The examiner can normally be reached Monday-Friday, 8:00 AM - 3:00 PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Prem Singh can be reached at (571)272-6381. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/BRANDI M DOYLE/Examiner, Art Unit 1771
/PREM C SINGH/Supervisory Patent Examiner, Art Unit 1771
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