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 .
Claim Objections
Claim 20 is objected to because of the following informalities: “an isobutene containing a C4- hydrocarbon mixture” is awkward syntax. The office recommends –a C4-hydrocarbon mixture containing isobutene—.
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 12-18 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.
Regarding claim 12, it is unclear what is intended to be encompassed by recitation of “selected from the group of polar nitrogen containing compounds and mixtures thereof.” A Markush group is a list of alternatives; however, no alternatives are recited by the single recitation of “polar nitrogen containing compounds.” It is therefore unclear what species are encompassed by the Markush group and, correspondingly, what mixtures of species.
Claim 19 is not included in this rejection because, although it depends from claim 11, it remedies the deficiencies thereof by reciting a clear list of alternatives encompassed by the Markush group.
Claim 15 recites the limitation "the bottom stream" in lines 1-2. There is insufficient antecedent basis for this limitation in the claim.
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.
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 12-19 are rejected under 35 U.S.C. 103 as being unpatentable over Arganbright et al (US 5,446,231) in view of Godsmark et al (US 2011/0282092) and Peters et al (US 2006/0122444).
Regarding claims 12 and 18, Arganbright discloses a process for purifying a raw C4-hydrocarbon mixture to remove nitrile contaminants (catalyst deactivator) comprising (see col. 1, lines 7-11; col. 2, lines 3-6, isobutylene feed mixture):
(a) contacting the raw C4-hydrocarbon mixture in countercurrent flow with an aqueous stream in an extraction unit yielding an intermediate C4-hydrocarbon mixture (see col. 2, lines 45-61); and
(b) withdrawing at least part of the intermediate C4-hydrocarbon mixture from the extraction unit (see col. 2, lines 59-61).
The resulting C4-hydrocarbon mixture contains less than 1 ppm of catalyst deactivator (poisons) (see col. 2, lines 48-49).
Arganbright does not explicitly disclose: (1) the concentrations of isobutene, other butenes, butadiene, C3- and C5+ hydrocarbons, and catalyst deactivator in the raw C4-hydrocarbon mixture; and (2) a step for dewatering the withdrawn intermediate C4-hydrocarbon mixture (claim step (c)).
With respect to (1), the office notes that the concentrations of the components in the mixture depend on its source. In this regard, Arganbright discloses the source being from a fluidized catalytic cracking (FCC) process (see col. 2, lines 29-37). With respect to nitriles, the concentration must be at least 1 ppm, given the purification results in a concentration of less than 1 ppm, as discussed above, and is, therefore, at the very least overlapping the claimed range.
With respect to the C4 components, reference is drawn to Godsmark, which similarly discloses treatment of a C4-hydrocarbon mixture obtained from FCC (see [0044]). The mixture comprises isobutene in concentrations of at least 15 wt.% and may additionally contain other butenes, and less than 7000 ppm butadiene (see [0025]; [0046]-[0047]), thus teaching concentrations overlapping the claimed ranges. The selection of a suitable starting material, including one having the claimed composition, amounts to nothing more than routine experimentation for a person of ordinary skill in the art and would be associated with a reasonable expectation of success. The claimed concentrations of components in the starting mixture are not considered to patentably distinguish the instant claims over the cited prior art.
With respect to (2), Arganbright discloses its process being a pretreatment prior to downstream etherification (see col. 1, lines 8-11).
Peters discloses that water present in an isobutenic mixture stemming from water washing can be removed by drying. Drying is advantageous in order to reduce formation of alcohols (i.e., tert-butyl alcohol) in the etherification process and avoidance of technical problems associated with separation of water at low temperature (for example intermediate storage) (see [0051]-[0052]).
It would have been obvious to a person of ordinary skill in the art at the time of filing the instant claimed invention to modify the process of Arganbright by including a dewatering step, as suggested by Peters, in order to prevent problems downstream (i.e., in etherification reaction and storage) associated with the presence of water.
Regarding claim 13, Arganbright discloses wherein the extraction unit comprises an extraction column 22, wherein the raw C4-hydrocarbon mixture 10 is fed to the lower part and the aqueous stream (solvent 18) is fed to the upper part thereof (see Fig. 1).
Regarding claim 14, Arganbright does not explicitly disclose the claimed pressure (4 to 7 bar) and temperature (30 to 60°C) for operating the extraction column. However, a person of ordinary skill in the art would determine, by routine experimentation, the optimum operating conditions to carry out the extraction which is associated with maximum removal of the nitrile contaminants. Absent a showing of criticality or unexpected results, the claimed temperature and pressure are not considered to patentably distinguish the instant claims over the cited prior art.
Regarding claim 15, Arganbright discloses recycling the solvent stream (i.e. bottom stream withdrawn from the bottom of the extraction column) to the extraction column, including up to 80% (see col. 6, lines 1-2).
Regarding claim 16, Arganbright discloses that when the feed mixture is a C4-mixture, water is sufficient for removal of the acetonitrile contaminants (see col. 2, lines 59-62). Godsmark provides further evidence that water is a preferred extraction solvent (see [0020]-[0021]). Thus, for a C4-hydrocarbon mixture feed, use of 100% by weight of water would be obvious to a person of ordinary skill in the art and associated with a reasonable expectation of success.
Regarding claim 17, Peters discloses a phase separator for step (c) (see [0051], distillative removal is considered equivalent to a phase separator).
Regarding claim 19, Arganbright discloses wherein the catalyst deactivator is acetonitrile (see col. 2, line 62).
Claims 20 and 22 are rejected under 35 U.S.C. 103 as being unpatentable over Brunner et al (US 4,287,379) in view of Arganbright and Peters.
Regarding claim 20, Brunner discloses a process for obtaining isobutene from an isobutene-containing C4-hydrocarbon mixture in a plant comprising an etherification unit 4, a first distillation unit 6, an ether cleavage unit 11, and a second distillation unit 13 (see Abstract; Figure). The process comprises:
(i) contacting the C4-hydrocarbon mixture 1 with a primary alcohol 2 and reacting the mixture with the primary alcohol in the presence of an acidic catalyst (acid condensing agent, ion exchanger in its acid form) to form a first reaction mixture 5 comprising an alkyl tert-butyl ether in the etherification unit 4 (see col. 2, lines 30-40; col. 7, lines 11-21);
(ii) distilling the first reaction mixture from the etherification unit in the first distillation unit 6, a C4-hydrocarbon raffinate being withdrawn as a first overhead product 7, the alkyl tert-butyl ether being withdrawn as a first liquid or vaporous bottom product 8, and vaporizing 9 the bottom product if it is withdrawn as a liquid (see col. 7, lines 20-28);
(iii) reacting the vaporous bottom product in the presence of an acidic catalyst obtaining a second reaction mixture 12 in the ether cleavage (decomposing) unit 11, the second reaction mixture comprising isobutene and the primary alcohol (see col. 7, lines 23-30); and
(iv) distilling the second reaction mixture from the ether cleavage unit in the second distillation unit 13, isobutene being withdrawn as a second overhead product 14, the primary alcohol being withdrawn as a second bottom product 15 and being recycled to the etherification unit (see col. 7, lines 30-36).
Brunner does not disclose the C4-hydrocarbon mixture being obtained from a pre-treating process as claimed. It is noted, however, that Brunner discloses the feed being sourced from a catalytic cracking process (see col. 3, lines 39-45).
Arganbright discloses that acidic ion exchange resins used in etherification processes (as is the case in Brunner) suffer from poisoning by basic compounds, such as nitriles, which are found in C4 mixture streams obtained from catalytic cracking processes (see col. 2, lines 1-44). Arganbright discloses a process for removing these nitrile contaminants (catalyst deactivator) comprising (see col. 1, lines 7-11; col. 2, lines 3-6, isobutylene feed mixture):
(a) contacting the raw C4-hydrocarbon mixture in countercurrent flow with an aqueous stream in an extraction unit yielding an intermediate C4-hydrocarbon mixture (see col. 2, lines 45-61); and
(b) withdrawing at least part of the intermediate C4-hydrocarbon mixture from the extraction unit (see col. 2, lines 59-61).
The resulting C4-hydrocarbon mixture contains less than 1 ppm of catalyst deactivator (poisons), wherein the catalyst deactivator is acetonitrile (see col. 2, lines 48-49 and 62).
Arganbright does not disclose a step for dewatering the withdrawn intermediate C4-hydrocarbon mixture (claim step (c)).
In this regard, Arganbright discloses its process being a pretreatment prior to downstream etherification (see col. 1, lines 8-11), as noted above.
Peters discloses that water present in an isobutenic mixture stemming from water washing can be removed by drying. Drying is advantageous in order to reduce formation of alcohols (i.e., tert-butyl alcohol) in the etherification process and avoidance of technical problems associated with separation of water at low temperature (for example intermediate storage) (see [0051]-[0052]).
It would have been obvious to a person of ordinary skill in the art at the time of filing the instant claimed invention to apply the pre-treatment steps as disclosed in Arganbright and Peters to the process of Brunner, in order to remove nitrile contaminants which act as catalyst poison to the ion exchange catalyst used in etherification, as shown in Arganbright, and to remove water in order to prevent problems downstream (i.e., in etherification reaction and storage) associated with the presence of water, as shown in Peters.
Regarding claim 22, Brunner discloses wherein the primary alcohol is isobutanol and the alkyl tert-butyl ether is isobutyl tert-butyl ether (see col. 3, lines 67-68; col. 8, lines 13-17).
Claim 21 is rejected under 35 U.S.C. 103 as being unpatentable over Brunner in view of Arganbright and Peters, as applied to claim 20, in further view of Godsmark.
Regarding claim 22, neither Brunner nor Arganbright explicitly discloses the concentrations of isobutene, other butenes, butadiene, and catalyst deactivator in the raw C4-hydrocarbon mixture.
However, in this regard, the office notes that the concentrations of the components in the mixture depend on its source. Arganbright discloses the source being from a fluidized catalytic cracking (FCC) process (see col. 2, lines 29-37). With respect to nitriles, the concentration must be at least 1 ppm, given the purification results in a concentration of less than 1 ppm, as discussed above, and is therefore at the very least overlapping the claimed range.
With respect to the C4 components, reference is drawn to Godsmark, which similarly discloses treatment of a C4-hydrocarbon mixture obtained from FCC (see [0044]). The mixture comprises isobutene in concentrations of at least 15 wt.% and may additionally contain other butenes, and less than 7000 ppm butadiene (see [0025]; [0046]-[0047]), thus teaching concentrations overlapping the claimed ranges. The selection of a suitable starting material, including one having the claimed composition, amounts to nothing more than routine experimentation for a person of ordinary skill in the art and would be associated with a reasonable expectation of success. The claimed concentrations of components in the starting mixture are not considered to patentably distinguish the instant claims over the cited prior art.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RENEE ROBINSON whose telephone number is (571)270-7371. The examiner can normally be reached Monday - Thursday 8:00a-5:00p and Friday 8:00a-2:00p.
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/Renee Robinson/Primary Examiner, Art Unit 1772
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