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 .
Office Action Summary
This is the office action summary for application 18/256088 filed 06/06/2023.
Claims 16-33 are currently pending and have been fully considered.
Claims 1-15 have been cancelled.
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.
Claim(s) 16-33 is/are rejected under 35 U.S.C. 103 as being unpatentable over de OLIVEIRA FILHO et al. (US 2020/0157439).
Regarding claims 16, 26, 27 and 29, de OLIVEIRA FILHO et al. teach in paragraphs 1 and 155 a process for scavenging hydrogen sulphide and/or mercaptans from a hydrocarbon stream with a composition.
The composition comprises compounds of Group III and compounds of Group IV.
Compounds of Group III is taught from paragraphs 89-98 to include a bisoxazolidine.
Compounds of Group IV is taught from paragraphs 101-117 to include amines such as monoethanolamine and 2-(2-aminoethoxy)ethanol.
Monoethanolamine would meet the claimed limitations of formula (I) with R1 being divalent linear and having 2 carbon atoms and n being 1 and R2 being H and R3 being H.
The amount of compounds of Group III is taught in paragraph 143 to comprise 0.1 to 20 wt% of the total content of active components.
The amount of Group IV is taught in paragraph 144 to comprise 0.1 to 15 wt% of the total content of active components.
Using more compounds of Group III such as bisoxazolidine than compounds of Group IV such as amines would be well within one of ordinary skill in the art since it has been established that where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
Regarding claims 28 and 33, the hydrocarbons that may be treated are taught in paragraph 12 to include crude oil and natural gas.
Regarding claim 17, the amount of compounds of Group III is taught in paragraph 143 to comprise 0.1 to 20 wt% of the total content of active components.
The amount of compounds of Group IV is taught in paragraph 144 to comprise 0.1 to 15 wt% of the total content of active components.
Using a ratio of more than 1 to 20 of compounds of Group III such as bisoxazolidine to compounds of Group IV such as amines would be well within one of ordinary skill in the art since it has been established that where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
Regarding claim 18, the formula of the bisoxazolidine is taught in paragraphs 95-97 to be
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338
620
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wherein R is H or methyl, and n is 1 or 2.
One particular example is 3,3'-methylenebis-5-methyl-oxazolidine ( MBO )
Regarding claim 19, compounds of Group IV are taught in paragraphs 101-117 to include 2-(2-aminoethoxy)ethanol.
2-(2-aminoethoxy)ethanol has the following formula.
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160
574
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2-(2-aminoethoxy)ethanol meets the present limitations wherein n is 2, R1 is a divalent linear alkyl group having 2 carbon atoms, R2 is H and R3 is also H.
Regarding claims 21, and 30, aside from the examples taught in paragraph 116, compounds of Group IV include tertiary amines with 3 hydroxy groups. A tertiary amine version of 2-(2-aminoethoxy)ethanol would comprise R2 being CH2CH2OCH2CH2OH and R3 being CH2CH2OCH2CH2OH.
A tertiary amine version of 2-(2-aminoethoxy)ethanol would meet the present limitations wherein n is 2, R1 is a divalent linear alkyl group having 2 carbon atoms, R2 and R3 are both –(R4-O)m-H wherein m is 2 and R4 is a divalent linear alkyl group having 2 carbon atoms
Regarding claim 20, monoethanolamine has a molecular weight of about 61 g/mol.
Regarding claims 22 and 31, monoethanolamine is taught in paragraphs 101-117.
Regarding claim 23, the composition is taught in paragraphs 151-152 and 154 to comprise a solvent.
Regarding claim 32, the solvent is taught in paragraph to be present from a concentration from 1 to 90 wt%.
Where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
Regarding claims 24 and 25, the amount of compounds of Group III is taught in paragraph 143 to comprise 0.1 to 20 wt% of the total content of active components.
The amount of compounds of Group IV is taught in paragraph 144 to comprise 0.1 to 15 wt% of the total content of active components.
The solvent is taught in paragraph to be present from a concentration from 1 to 90 wt%.
Where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
Therefore, the invention as a whole would have been prima facie obvious to one of ordinary skill in the art at the time of the invention.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
DE OLIVEIRA FILHO et al. (US 2020/0109329) also teach a process for scavenging hydrogen sulphide and/or mercaptans from a hydrocarbon stream with a composition that comprise oxazolidines and amines.
RIVERS (US 6117310) teaches bisoxazolidines for scavenging sulfhydryl compounds such as hydrogen sulphide. The bisoxazolidines are produced from reactions with an alkanolamine. RIVERS teaches that a cosolvent may be added.
MENENDEZ et al. (USPGPUB 2013/0004393) teach scavenging a sulfur-containing compound comprise hydrogen sulfide and/or mercaptan with a nitrogen containg scavenger. The nitrogen containing scavenger includes alkanolamines and bisoxazolidines.
DILLON (US 4978512) teach use of bisoxazolidines in compositions for reducing hydrogen sulfides and sulfides from gaseous and/or liquid hydrocarbon streams.
FISCHER (US 2776870) teach the use of alkanolamines for treating gases for removal of acidic constituents such as hydrogen sulfide.
MARCYMOB (RU2008150509A) teach a hydrogen sulfide neutralizer comprising oxazolidine and amines.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MING CHEUNG PO whose telephone number is (571)270-5552. The examiner can normally be reached M-F 10-6.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, PREM SINGH can be reached at 5712726381. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/MING CHEUNG PO/Examiner, Art Unit 1771
/ELLEN M MCAVOY/Primary Examiner, Art Unit 1771