DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 29 December 2025 has been entered.
Claims 1-3 and 5-21 are pending, with claims 16-21 withdrawn from consideration.
The previous rejections have been maintained. The rejections follow.
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 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.
Claims 1-3, 5-9, and 13-14 are rejected under 35 U.S.C. 103 as being unpatentable over Myers (US 2,911,360) in view of Duncum (WO 02/18519) and McFarlane (US 2012/0152807).
Regarding claims 1-3, 5-6, and 14, Myers teaches dosing a crude with caustic based on the desired removal of naphthenic acids (column 1, line 15-column 2, line 22). Myers teaches adding the caustic to a static hydrocarbon crude oil with an alcohol solvent such as methanol or ethanol (column 2, line 66-column 3, line 20). Myers teaches extracting the naphthenate salts from the crude oil (column 3, lines 25-35), decanting the alcohol solvent mixture, and subjecting to solvent recovery so the alcohol solvent can be recycled to the extraction step (column 6, lines 14-75). Examiner considers Myers to disclose a “defined period” of reaction time, since Myers teaches reaction of the crude and solvent in order to separate alcoholic soap from the crude.
Myers teaches determining caustic dosage based on removal of naphthenic acids
Myers does not explicitly disclose (1) measuring total acid number and determining dosage from TAN (2) the newly amended limitations regarding stopping circulation and allowing the contents to become sedentary to create a static environment within the bulk tankage (3) a single solvent mixture is formed by dosing solvent feed with caustic (4) the solvent feed comprises at least 20% water, one or more alcohols, and glycerol and the glycerol in part preventing emulsion from forming.
Regarding (1) and (3), Duncum teaches a similar process for removing naphthenic acids from crude oil and crude oil distillates using caustic and alcohols. Duncum teaches measure TAN to determine the dosage (page 1, lines 1-10) and page 4, lines 8-30). Duncum teaches that the crude oil may be contacted with a solution of metal hydroxide in polar solvent (page 4, liens 25-30), which Examiner considers to read on the claimed “single solvent mixture”.
Therefore, it would have been obvious to the person having ordinary skill in the art to have used TAN to determine caustic dosage and metal hydroxide polar solvent solution/single solvent mixture, as disclosed by Duncum, for the benefit of determining the appropriate caustic dosage as required by Myers. It is not seen where such a selection would result in any new or unexpected results. It is further expected that the same naphthenates, asphaltenes, salts, metals, chlorides, sulfides, mercaptans, phenols, and polycyclics will be recovered, since the prior art teaches treating of the same hydrocarbon crude oil with the same caustic and alcohol materials as applied to the instant specification. It is not seen where such a selection would result in any new or unexpected results.
Regarding (2), it appears that the claimed process is drawn to batch processing, while Myers is run continuously. However, Examiner notes that both batch and continuous processing are well-known in the art, and may be utilized depending upon available equipment. Examiner additionally notes that the person having ordinary skill in the art may select to run a batch process, if performing a lab scale test, to determine suitability. Examiner additionally notes MPEP 2144.04, V, E: noting that batch and continuous processing are well known in the art.
Therefore, it would have been an obvious modification to run the Myers process in a batch process, depending on equipment availability or to perform a lab scale test. It is not seen where such a modification would result in any new or unexpected results.
Regarding (4), McFarlane teaches a similar process for removing acidic compounds from hydrocarbons using sodium hydroxide and alcohols, including methanol, ethanol, and glycerol [0056-0059].
Therefore, it would have been obvious to the person having ordinary skill in the art to have used glycerol in combination with the methanol and ethanol of the previous combination, since McFarlane teaches it is suitable for the same purpose of removing acidic components from hydrocarbons.
McFarlane teaches that alcohol water mixtures are used, and that the amount of water is selected to be lower than the level of the active agent [0056]. McFarlane teaches ethanol, propanol, glycerol, and a combination thereof [0056]. McFarlane teaches that the ratio of water is adjusted in order to tailor the chemical properties of the active agent to the properties of the particular acidic hydrocarbon feed to be treated (to modulate degree of solubility of the active agent in the acidic hydrocarbon feed and the desired efficiency for reducing the content of the acidic constituent in the acidic hydrocarbon feed) [0056]. McFarlene teaches using 99.9 wt% to 50 % active agent (alcohol) with water as a modifier [0011]. Therefore, it would have been obvious to the person having ordinary skill in the art to have appropriately selected amounts of water and alcohols, in order to achieve the desired total acid number reduction.
Further, it would have been obvious to the person having ordinary skill in the art to have appropriately selected the amounts of glycerol and ethanol based off of availability, economics, and performance. It is not seen where such a selection would result in any new or unexpected results. It is further expected that the same prevention of emulsion would occur from the McFarlene process, since the same glycerol component is used.
Regarding claim 7, Myers teaches appropriately selecting the amount of alcohol, and caustic in order to obtain the desired extraction (column 3, lines 1-20).
Therefore, it would have been obvious to the person having ordinary skill in the to select an appropriate mass ratio, such as claimed, for the benefit of obtaining the desired removal of naphthenic acids. It is not seen where such a selection would result in any new or unexpected results.
Regarding claims 8-9, the previous combination does not explicitly disclose residence time.
However, McFarlane teaches selecting appropriate contact times in order to achieve the desired removal of acidic compounds.
Therefore, it would have been obvious to the person having ordinary skill in the art to have appropriately selected the contact time, in order to achieve the desired removal of acidic compounds.
Regarding claim 13, Myers teaches temperatures of 50-200°F (column 3, lines 22-25), which overlaps with the claimed range.
Claims 10-12 are rejected under 35 U.S.C. 103 as being unpatentable over Myers (US 2,911,360) in view of Duncum (WO 02/18519) and McFarlane (US 2012/0152807) as applied to claim 1 above, and further in view of Chen (US 5,182,024).
Regarding claims 10-12, the previous combination teaches the limitations of claim 1, as discussed above. The previous combination teaches decanting the spent solvent and subjecting to treatment to remove impurities so the solvent may be recycled. Mond teaches using thermal desorption to recover steam (page 2, lines 33-65).
The previous combination does not explicitly disclose reverse osmosis.
However, Chen teaches it is common to use reverse osmosis to purify various solvents such as ethanol (column 1, lines 1-14 and column 2, lines 55-64).
Therefore, it would have been obvious to the person having ordinary skill in the art to have used the reverse osmosis of Chen, in order to obtain the desired purified solvent stream of the previous combination, so it may be recycled to save raw material costs.
Claims 15 is rejected under 35 U.S.C. 103 as being unpatentable over Myers (US 2,911,360) in view of Duncum (WO 02/18519) and McFarlane (US 2012/0152807) as applied to claim 1 above, and further in view of Merrill (US 43,325).
Regarding claim 15, the previous combination teaches the limitations of claim 1, as discussed above.
The previous combination does not explicitly disclose adding acid to contact the hydrocarbons.
However, Merrill teaches that it is well known in the art to contact acidic hydrocarbons with sulfuric acid to remove undesirable compounds, in combination with caustic treatment (page 1, column 1, paragraph 2).
Therefore, it would have been obvious to the person having ordinary skill in the art to have performed the Merrill acid treatment in combination with the process of the previous combination, for obtaining further removal of undesirable compounds.
Response to Arguments
Applicant's arguments filed 29 December 2025 have been fully considered but they are not persuasive.
Examiner considers Applicant’s arguments to be:
The prior art does not disclose the mixture of water, alcohol, and glycerol, wherein emulsion is prevented from forming. McFarlane excludes water.
The office action has not addressed “stopping of circulation creating a static environment”. Switching between batch and continuous would destroy the prior art.
Regarding Applicant’s first argument, McFarlene explicitly discloses the presence of alcohols in combination with water and sodium hydroxide [0011]. McFarlane teaches that alcohol water mixtures are used, and that the amount of water is selected to be lower than the level of the active agent [0056]. McFarlane teaches ethanol, propanol, glycerol, and a combination thereof [0056]. McFarlane teaches that the ratio of water is adjusted in order to tailor the chemical properties of the active agent to the properties of the particular acidic hydrocarbon feed to be treated (to modulate degree of solubility of the active agent in the acidic hydrocarbon feed and the desired efficiency for reducing the content of the acidic constituent in the acidic hydrocarbon feed) [0056]. McFarlene teaches using 99.9 wt% to 50 % active agent (alcohol) with water as a modifier [0011]. Therefore, it would have been obvious to the person having ordinary skill in the art to have appropriately selected amounts of water and alcohols, in order to achieve the desired total acid number reduction.
Regarding Applicant’s second argument, it is not seen where Applicant has described how such a modification would destroy the prior art processes.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
US 17725393 – related application covering similar subject matter. ‘393 differs in that the claims are drawn to an apparatus system, which would differ in scope from the instant method claims.
Mond (GB 556,606) – previously cited, teaches liquid liquid extraction for removing acidic compounds from hydrocarbon using glycerol, ethanol, water, and sodium hydroxide (page 1, lines 12-17, 70-80 and page 4, lines 66-123).
Poirier (US 5,199,978) – teaches removing acidic compounds from hydrocarbons using ethanol and NaOH.
Thompson (US 4,510,047) – teaches using reverse osmosis to recover solvents.
Babcock (US 4,673,484) – teaches reverse osmosis to recover alcohol solvents.
Woods (US 2008/0209799) –teaches reverse osmosis to purify glycerol.
Fuqua (US 2,424,158) – teaches removing naphthenic acids from hydrocarbon using ethanol and glycerin solvents.
Pierotti (US 2,360,861) – teaches solvent extraction with ethanol and glycerol.
Varadaraj (US 5,961,821) – teaches reduction of TAN in hydrocarbon oils.
Grosso (US 2008/0314758) – teaches solvent recovery.
Al-Hajji (US 2013/0037448) – teaches reducing total acid number in refinery feedstocks using caustic.
THIS ACTION IS MADE FINAL. 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 MICHELLE STEIN whose telephone number is (571)270-1680. The examiner can normally be reached Monday-Friday 8:30 AM-5:00 PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Prem C 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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/MICHELLE STEIN/Primary Examiner, Art Unit 1771