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 .
Status of Claims
Claims 1-20 are pending. This is the first Office Action on the merits.
Claim Interpretation
The term “sacrificial metal alkyl compound” is interpreted to mean any metal alkyl compound capable of reacting with a catalyst deactivation compound, thereby producing a nonreactive solid product (Spec., [0014]-[0016]).
Claim Objections
Claim 15 is objected to because of the following informalities. Appropriate correction is required.
It is noted that the inclusion of a material or article worked upon by a structure being claimed does not impart patentability to the claim. MPEP 2115. Additionally, the limitation “a liquid phase hydrogenation reactor,” as currently recited, is not configured to receive “the purified aromatic hydrocarbon stream” from the “reboiler.”
For clarity, Applicant is suggested to amend claim 15 as follows:
15. A system for liquid phase hydrogenation of an aromatic compound, the system comprising:
a source of a crude aromatic mixture comprising the aromatic compound, a catalyst deactivation compound, and water;
a distillation column operable to separate [[a]] the crude aromatic mixture
a reboiler operable to heat the bottoms stream to form a recycle stream and a purified aromatic hydrocarbon stream;
a source of a sacrificial metal alkyl stream comprising a metal alkyl compound connected to the reboiler, to the recycle stream, to the purified aromatic hydrocarbon stream, or a combination thereof;
a liquid phase hydrogenation reactor operable to react the aromatic compound in the purified aromatic hydrocarbon stream with hydrogen in a presence of a homogeneous hydrogenation catalyst to form a cycloalkane compound; and
a liquid cooling loop operable to receive a portion of a liquid reaction medium comprising liquid phase reaction components and solid particulates and to cool the portion of the liquid reaction medium prior to recycling the cooled liquid reaction medium to the liquid phase hydrogenation reactor.
Claim Rejections - 35 USC § 102 / § 103
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
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 and 10-14 are rejected under 35 U.S.C. 102(a)(1) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over Snell et al. (US 10,669,217 B2, cited in IDS dated 09/11/2024).
Regarding claim 1, Snell discloses a process comprising:
introducing a sacrificial metal alkyl compound (“a component that will react with reactive species”; Fig. 4, 406) to a stream or equipment (405) comprising an aromatic compound and a catalyst deactivation compound (“oxygen-containing species”), wherein a location of the stream or equipment is upstream of a liquid phase hydrogenation reactor (420), wherein the location is not in a liquid cooling loop of the liquid phase hydrogenation reactor (col. 17, line 19 – col. 18, line 21; see also Fig. 4); and
reacting the sacrificial metal alkyl compound with the catalyst deactivation compound in the stream or equipment (col. 17, lines 38-42: “A component that will quickly react with species that undesirably encourage plating out of catalyst metal (e.g., nickel) and/or catalyst decomposition product(s) on the surfaces within heat exchanger 440, is added from a component source 406 into hydrocarbon feed line 405).
Snell does not explicitly disclose the reaction of the metal alkyl compound with the catalyst deactivation compound forms “a nonreactive solid product.”
However, Snell discloses that suitable materials for the sacrificial metal alkyl compound include aluminum alkyls, e.g., having the formula (R3)3Al where (R3) is an aliphatic group having from 1 to about 6 carbon atoms, and also discloses that the oxygen-containing species may include oxygen and water (col. 11, lines 2-7; col. 17, line 67- col. 18, line 3). One skilled in the art would expect the reaction of such aluminum alkyls with oxygen and water to produce aluminum alkoxides and/or aluminum oxide and aluminum hydroxide, respectively, which are considered nonreactive solid products.
Regarding claim 10, Snell discloses:
introducing the aromatic compound (Fig. 4, 405) and hydrogen (415) into the liquid phase hydrogenation reactor (420) (col. 17, lines 35-38);
reacting the aromatic compound with the hydrogen in a presence of a homogeneous hydrogenation catalyst in the liquid phase hydrogenation reactor to form a cycloalkane compound (455) (col. 11, line 52 – col. 12, line 13; see Fig. 4);
withdrawing a portion of a liquid reaction medium (425) comprising liquid phase reaction components and solid particulates from the liquid phase hydrogenation reactor (col. 18, lines 28-31 and 58-63);
flowing the portion of the liquid reaction medium that is withdrawn from the liquid phase hydrogenation reactor through the liquid cooling loop (col. 18, lines 28-38);
removing part of the portion from the liquid cooling loop; (col. 16, lines 3-7);
filtering the part to produce a permeate (395) comprising a portion of the liquid phase reaction components and a retentate (380) comprising the solid particulates (col. 8, lines 58-61; col. 16, lines 7-10 and 35-39); and
recycling the permeate to the liquid cooling loop or directly to the liquid phase hydrogenation reactor (col 16, lines 35-48).
Regarding claim 11, nonreactive solid products are expected to be generated from the reaction of the sacrificial metal alkyl compound (i.e. aluminum alkyls) with the catalyst deactivation compound (i.e. water and oxygen), as discussed above (col. 11, lines 2-7; col. 17, line 67- col. 18, line 3). Since the solids precipitate in the liquid phase, the solids particulates in the liquid reaction medium (Fig. 3, 325; Fig. 4, 425) are expected to comprise the nonreactive solid products.
Regarding claim 12, Snell discloses that the catalyst deactivation compound comprises oxygen-containing species, such as oxygen or water, that are reactive with catalyst metals (col. 17, lines 38-42; col. 17, line 67- col. 18, line 3).
Regarding claim 13, Snell discloses that suitable materials for the sacrificial metal alkyl compound include aluminum alkyls, e.g., having the formula (R3)3Al where (R3) is an aliphatic group having from 1 to about 6 carbon atoms (col. 11, lines 2-7)
Regarding claim 14, Snell discloses that the aromatic compound comprises benzene and/or toluene (col. 13, lines 37-38).
Claims 2-9 and 15-20 are rejected under 35 U.S.C. 102(a)(1) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over Snell et al. (US 10,669,217 B2, cited in IDS dated 09/11/2024), as applied to claim 1, and further in view of Lin et al. (US 2007/0299294 A1).
Regarding claim 2, Snell teaches the process of claim 1, as discussed above.
Snell does not teach:
prior to introducing the sacrificial metal alkyl compound, distilling a crude aromatic mixture comprising the aromatic compound, the catalyst deactivation compound, and water into an overhead product comprising the water and a bottoms product comprising the aromatic compound and the catalyst deactivation compound; and
reboiling, in a reboiler, the bottoms product to form a recycle stream and a purified aromatic hydrocarbon stream comprising the aromatic compound,
wherein aromatic compound is introduced to the liquid phase hydrogenation reactor via the purified aromatic hydrocarbon stream.
However, Lin, directed to a process for removing benzene from a reformate and converting benzene to cyclohexane ([0038]), teaches the step of distilling, in a benzene azeotropic column (Fig. 2, 12), a crude aromatic mixture (49) comprising benzene and water (which also corresponds to a catalyst deactivation compound) into an overhead product (50) comprising the water and a bottoms product (51) comprising benzene and residual water, wherein a portion of the bottom product is sent to a hydrogenation reactor (14) ([0044]). Although Snell is silent on operating a reboiler to reboil the bottoms product to form a recycle stream and a purified aromatic hydrocarbon stream, a distillation column is generally understood to require a reboiler at the bottom to form a reflux stream and a bottom product stream. Therefore, the claimed reboiling step is considered an obvious feature associated with the benzene azeotropic column.
Therefore, before the effecting filing date of the instant invention, it would have been obvious to one of ordinary skill in the art to modify Snell by obtaining a hydrogenation feedstock by distilling a crude aromatic mixture comprising benzene and water into an overhead product comprising the water and a bottoms product comprising benzene and residual water, wherein a portion of the bottom product, after recovered from a reboiler, is sent to the hydrogenation reactor, as taught by Lin, because Lin teaches a method of providing an aromatic compound stream that can be used as a feedstock to a hydrogenation process for producing a valuable product (e.g. cyclohexane) and this merely involves application of a known source to a known process to yield predictable results.
Regarding claim 3, Snell discloses that suitable materials for the sacrificial metal alkyl compound include aluminum alkyls, e.g., having the formula (R3)3Al where (R3) is an aliphatic group having from 1 to about 6 carbon atoms, and also discloses that the oxygen-containing species may include oxygen and water (col. 11, lines 2-7; col. 17, line 67- col. 18, line 3). One skilled in the art would expect the reaction of alkyl aluminum with water or oxygen to accelerate with increasing temperature. Therefore, one would have been motivated to optimize the amount of the sacrificial metal alkyl compound based on the temperature of process liquid in the reboiler of the benzene azeotropic column, since it has been held that, where the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation. MPEP 2144.05 II.
Regarding claim 4, Snell teaches adding the sacrificial metal alkyl compound (Fig. 4, 406) to the aromatic hydrocarbon stream (405) (col. 17, lines 38-42), which corresponds to a purified aromatic hydrocarbon in the modified process of Snell, in view of Lin (“Snell/Lin”).
Regarding claim 5, the aromatic hydrocarbon stream (Fig. 4, 405) of Snell, which corresponds to a purified aromatic hydrocarbon in the modified process of Snell, in view of Lin (“Snell/Lin”), is connected to the liquid phase hydrogenation reactor (420) (col. 17, lines 35-38; Fig. 4).
Regarding claim 6, Lin teaches that the water content in the bottoms product stream that is sent to the hydrogenation reactor is kept to a level of less than 200 ppm ([0044]). The claimed range of less than 20 ppmw falls within the range taught by Lin and is considered prima facie obvious. In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. MPEP 2144.05. I.
Regarding claim 7, the modified process of Snell, in view of Lin, teaches:
separating the nonreactive solid product (residual water) from the aromatic compound in a guard unit (Lin: [0046])
after separating, introducing the aromatic compound and hydrogen into the liquid phase hydrogenation reactor (Lin: [0046]; Snell: col. 17, lines 35-38); and
reacting the aromatic compound with the hydrogen in a presence of a homogeneous hydrogenation catalyst in the liquid phase hydrogenation reactor to form a cycloalkane compound (Snell: col. 11, line 52 – col. 12, line 13).
Regarding claims 8 and 9, the modified process of Snell, in view of Lin, teaches:
flowing the purified aromatic hydrocarbon stream through a guard unit containing an adsorbent, which can be considered a filter, to produce a hydrogenation reactor feed stream comprising the aromatic compound (Lin: [0046]),
wherein the hydrogenation reactor feed stream is connected to the liquid phase hydrogenation reactor (Lin: [0046]; Snell: col. 17, lines 35-38).
Regarding claim 15, Snell discloses a system for liquid phase hydrogenation of an aromatic compound, the system comprising (see Figs 3 and 4):
a sacrificial metal alkyl stream (Fig. 4, 406) comprising a metal alkyl compound connected to the aromatic hydrocarbon stream (405) (col. 17, lines 35-42);
a liquid phase hydrogenation reactor (Fig. 4, 420) operable to react the aromatic compound with hydrogen in a presence of a homogeneous hydrogenation catalyst to form a cycloalkane compound (col. 11, line 52 – col. 12, line 13; col. 17, lines 35-42); and
a liquid cooling loop (Fig. 3, 330, 340) operable to receive a portion (335) of a liquid reaction medium (325) comprising liquid phase reaction components and solid particulates and to cool the portion of the liquid reaction medium prior to recycling the cooled liquid reaction medium to the liquid phase hydrogenation reactor (col. 16, lines 3-48).
Snell does not teach:
a distillation column operable to separate a crude aromatic mixture comprising the aromatic compound, a catalyst deactivation compound, and water into an overhead stream comprising water and a bottoms stream comprising the aromatic compound and the catalyst deactivation compound; and
a reboiler operable to heat the bottoms stream to form recycle stream and a purified aromatic hydrocarbon stream.
However, Lin, directed to a process for removing benzene from a reformate and converting benzene to cyclohexane ([0038]), teaches the step of distilling, in a benzene azeotropic column (Fig. 2, 12), a crude aromatic mixture (49) comprising benzene and water (which also corresponds to a catalyst deactivation compound) into an overhead product (50) comprising the water and a bottoms product (51) comprising benzene and residual water, wherein a portion of the bottom product is sent to a hydrogenation reactor (14) ([0044]). Although Snell is silent on operating a reboiler to reboil the bottoms product to form a recycle stream and a purified aromatic hydrocarbon stream, a distillation column is generally understood to require a reboiler at the bottom to form a reflux stream and a bottom product stream. Therefore, the claimed reboiler is considered an obvious feature associated with the benzene azeotropic column.
Therefore, before the effecting filing date of the instant invention, it would have been obvious to one of ordinary skill in the art to modify Snell by including a distillation column operable to separate a crude aromatic mixture comprising benzene and water into an overhead product comprising the water and a bottoms product comprising benzene and residual water and a reboiler to properly operate the distillation column, as taught by Lin, because Lin teaches a method and apparatus for providing an aromatic compound stream that can be used as a feedstock to a hydrogenation process for producing a valuable product (e.g. cyclohexane) and this merely involves application of known prior art elements for obtaining a feedstock to a known process to yield predictable results.
Regarding claim 16, Snell, in view of Lin, teaches separator (guard unit 13 in Lin) having an inlet connected to the purified aromatic hydrocarbon stream (from benzene azeotropic column 12) and an outlet connected to an inlet of the liquid phase hydrogenation reactor, wherein the separator is operable to separate a nonreactive solid product from the aromatic compound (Lin: [0046]).
Regarding claims 17 and 18, Lin teaches a guard unit 13 containing an adsorbent bed ([0046]). Additionally, such an adsorbent can be considered a filter.
Regarding claim 19, Snell teaches:
a slip stream (Fig. 3, 325) connected to the liquid cooling loop and operable to receive part of the portion of the liquid reaction medium (col. 16, lines 3-48);
a filter (370) having an inlet fluidly coupled to the slip stream and operable to separate the slip stream into a permeate (395) comprising a portion of the liquid phase reaction components and a retentate (380) comprising the solid particulates (col. 16, lines 3-48); and
a permeate stream connected to the filter and to the liquid cooling loop, and operable to flow the permeate from the filter to the liquid cooling loop (col. 16, lines 3-48).
Regarding claim 20, Snell, in view of Lin, teaches a hydrogen feed line (Fig. 4, 415) connected to the purified aromatic hydrocarbon stream (405), wherein the sacrificial metal alkyl stream (406) is connected to the hydrogen feed line (col. 17, lines 46-53).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JASON Y CHONG whose telephone number is (571)431-0694. The examiner can normally be reached Monday-Friday 9:00am-5:30pm.
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/JASON Y CHONG/Examiner, Art Unit 1772
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