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 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 1-20 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.
The term “fast gas chromatograph” in claims 1, 14 and 20 is a relative term which renders the claims indefinite. The term “fast gas chromatograph” is not defined by the claims, the specification does not provide a standard for ascertaining the requisite degree, and one of ordinary skill in the art would not be reasonably apprised of the scope of the invention. Applicant should consider reciting a cycle time associated with the ”fast gas chromatograph” to clearly and distinctly recite the subject matter which applicant seeks to protect. For examination purposes, a gas chromatograph of any speed will be considered to read on the claims.
Claims 2-13 and 15-19 are rejected as depending from a rejected base claim.
Claim Rejections - 35 USC § 102
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.
Claims 1, 8, 9, 11, 14, 16 and 18 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Wiegand et al. (US 5,589,630).
Per claim 1, Wiegand et al. teach a method comprising:
distilling a hydrocarbon feed (401; Fig. 5) to provide a plurality of distillation fractions (coming off the top of distillation column 402) using a distillation column (402);
obtaining a draw stream (from top of column 402, in fluid communication with valve 406) from one or more of the plurality of distillation fractions; and
analyzing the draw stream with a fast gas chromatograph (403) to directly determine a carbon number distribution of the draw stream (col. 16, lines 40-42, A homogeneous, representative, single phase sample was obtained from the column and feed stream and sent to the fast GC in a timely manner.), the fast gas chromatograph having a cycle time that is less than a residence time of a specified component of the draw stream within the distillation column (Table 2, col. 15, lines 8-15, As is readily apparent from the above example, the retention times using the Process GC and the Conventional Capillary GC were much longer than the fast GC methods shown in columns 1-4 of Table 2. In employing the isothermal 5 meter column fast GC method, the column temperature of 110.degree. C. was selected so as to separate the C6 fraction (1-hexene, trans-2-hexene, etc.) in the column in less than 30 seconds.), and the fast gas chromatograph being in-line with or in parallel with the draw stream (Fig. 5).
Per claim 8, wherein a hydrocarbon product within the draw stream has a density of about 600 kg/m³ to about 880 kg/m³ (Table 2, at least one of the hexene compounds listed).
Per claim 9, wherein the draw stream comprises an alkane, an alkene, or any combination thereof (Table 2).
Per claim 11, Wiegand et al. disclose wherein the draw stream comprises one or more hydrocarbons having a carbon number of C24 or less (Table 2).
Per claim 14, Wiegand et al. teach a system comprising:
a distillation column (402) comprising a feed inlet (401) and a draw line (in fluid communication with valve 406), wherein the draw line is configured to provide a draw stream comprising a distillation fraction separated within the distillation column (col. 16, lines 40-42, A homogeneous, representative, single phase sample was obtained from the column and feed stream and sent to the fast GC in a timely manner.); and
a fast gas chromatograph (403) in fluid communication with the draw line, the fast gas chromatograph being configured to directly determine a carbon number distribution of the draw stream (FIGS. 4a-f are gas chromatograms for a gas sample containing various moieties having 1-6 carbon atoms.) and having a cycle time that is less than a residence time of a specified component of the draw stream within the distillation column (Table 2, col. 15, lines 8-15, As is readily apparent from the above example, the retention times using the Process GC and the Conventional Capillary GC were much longer than the fast GC methods shown in columns 1-4 of Table 2. In employing the isothermal 5 meter column fast GC method, the column temperature of 110.degree. C. was selected so as to separate the C6 fraction (1-hexene, trans-2-hexene, etc.) in the column in less than 30 seconds.), and wherein the fast gas chromatograph is in-line with or in parallel with the draw stream (Fig. 5).
Per claim 16, Wiegand discloses wherein the distillation column is a tray distillation column, a packed distillation column, a divided wall distillation column, or any combination thereof. (col. 13, lines 1-6, Applications for fast GC include but are not limited to analysis of feed streams, streams removed from a single unit operation (for example a distillation tray or the middle of a plug flow reactor), internal process streams, recycle streams, blow off gases, vent gases, purge gases, catalyst concentrations in various streams and the like.; EXAMPLE 3, Fast gas chromatography was employed to rapidly determine the composition profile, i.e., the concentration of components at various locations (heights or trays) within a distillation column which separates ethane from ethylene). The fast GC was employed to measure methane, ethane, ethylene, acetylene, propane, and propylene concentrations in the reflux stream as well as several points located along the distillation column.).
Per claim 18, Wiegand et al. disclose wherein the distillation column is in fluid communication with a hydrocarbon processing operation (Fig. 5 shows the fractions are routed through piping and passed through a heat exchanger for cooling/heating to prior to extraction or recycling).
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.
Claims 2-4, 6-7, 12, 15 and 19 are rejected under 35 U.S.C. 103 as being unpatentable over Wiegand et al. (‘630).
Per claim 2, Wiegand et al. disclose that a cycle time for hydrocarbons is less than 400 seconds (Table 2, col. 15, lines 8-15, As is readily apparent from the above example, the retention times using the Process GC and the Conventional Capillary GC were much longer than the fast GC methods shown in columns 1-4 of Table 2. In employing the isothermal 5 meter column fast GC method, the column temperature of 110.degree. C. was selected so as to separate the C6 fraction (1-hexene, trans-2-hexene, etc.) in the column in less than 30 seconds.). Wiegand et al. do not explicitly disclose wherein the cycle time for C₂₄ hydrocarbons is about 400 seconds or less.
It is submitted that it would have been a routine matter of process design to modify the method of Wiegand et al. such that it comprises wherein the cycle time for C₂₄ hydrocarbons is about 400 seconds or less in order to, for example, reduce the time taken to analyze the fractions of a draw stream and reduce potential system dead time while waiting for results, absent a proper showing (e.g., comparative test data) of any new and unexpected result.
Per claim 3, Wiegand et al. disclose adjusting one or more operational parameters of the distillation column (col. 3, lines 40-43, Additional timer and temperature controllers, programmers and heat transfer fluids may also be provided to the temperature control/column apparatus to modify the temperature of the column and its contents.). Tirmizi et al. do not explicitly disclose that the adjustment is based on the carbon number distribution of the draw stream.
It would have been well within the purview of the skilled artisan to modify the method of Tirmizi et al. such that it includes the adjustment is based on the carbon number distribution of the draw stream in order to, for example, fine tune the distillation column based on desired results.
Per claim 4, Wiegand et al. disclose wherein the one or more operational parameters comprises at least one of: a temperature of a zone in the distillation column; an operating pressure of the distillation column; a draw rate of the draw stream; a feed rate of the hydrocarbon feed; a presence, an absence, or a flow rate of a reflux flow to the distillation column; a presence, an absence, or a flow rate of a return stream flow to the distillation column; a draw rate of an overheads distillation fraction; and an amount of heat added to a distillation column reboiler (col. 3, lines 40-43, Additional timer and temperature controllers, programmers and heat transfer fluids may also be provided to the temperature control/column apparatus to modify the temperature of the column and its contents.).
Per claim 6, Wiegand et al. do not explicitly disclose the method further comprising further comprising:
determining a range of retention times for one or more known hydrocarbon samples having a specified carbon number (Cₙ), wherein n is a number of carbon atoms.
It is submitted that it would have been a routine matter of design choice to have the method determining a range of retention times for one or more known hydrocarbon samples having a specified carbon number (Cₙ), wherein n is a number of carbon atoms, depending on the types of hydrocarbons anticipated to be present in the gas and the results desired.
Per claim 7, Wiegand et al. do not disclose wherein a peak obtained from the fast gas chromatograph having a retention time within the range of retention times is classified as comprising Cₙ hydrocarbons, a peak obtained from the fast gas chromatograph with a retention time below the range of retention times for Cₙ is classified as comprising Cₙ₋₂ hydrocarbons, and a peak obtained from the fast gas chromatograph with a retention time above the range of retention times for Cₙ is classified as comprising Cₙ₊₂ hydrocarbons.
It is submitted that it would have been readily obvious to modify the method of Wiegand et al. such that it comprises wherein a peak obtained from the fast gas chromatograph having a retention time within the range of retention times is classified as comprising Cₙ hydrocarbons, a peak obtained from the fast gas chromatograph with a retention time below the range of retention times for Cₙ is classified as comprising Cₙ₋₂ hydrocarbons, and a peak obtained from the fast gas chromatograph with a retention time above the range of retention times for Cₙ is classified as comprising Cₙ₊₂ hydrocarbons given the fact that higher carbon chain compounds typically have higher boiling points and lower carbon chain compounds typically have lower boiling points.
Per claim 12, Wiegand et al. do not disclose wherein the hydrocarbon feed comprises up to about 5 wt% hydrocarbons having a carbon number of C₂₄ or greater.
It is submitted that it would have been a routine matter of process design to modify the method of Wiegand et al. such that it comprises wherein the hydrocarbon feed comprises up to about 5 wt% hydrocarbons having a carbon number of C₂₄ or greater in order to, for example, create products suitable for an intended use, depending on the result desired.
Per claim 15, Wiegand et al. disclose that a cycle time for hydrocarbons is less than 400 seconds (Table 2, col. 15, lines 8-15, As is readily apparent from the above example, the retention times using the Process GC and the Conventional Capillary GC were much longer than the fast GC methods shown in columns 1-4 of Table 2. In employing the isothermal 5 meter column fast GC method, the column temperature of 110.degree. C. was selected so as to separate the C6 fraction (1-hexene, trans-2-hexene, etc.) in the column in less than 30 seconds.). Wiegand et al. do not explicitly disclose wherein the cycle time for C₂₄ hydrocarbons is about 400 seconds or less.
It is submitted that it would have been a routine matter of process design to modify the method of Wiegand et al. such that it comprises wherein the cycle time for C₂₄ hydrocarbons is about 400 seconds or less in order to, for example, reduce the time taken to analyze the fractions of a draw stream and reduce potential system dead time while waiting for results, absent a proper showing (e.g., comparative test data) of any new and unexpected result.
Per claim 19, Wiegand et al. disclose the method comprising:
a controller capable of receiving data from the fast gas chromatograph (col. 12, lines 43-56, The fast gas chromatographic technology is readily employed to rapidly determine the compositions of process streams and these compositions can be used for process control. As used herein, process variables are defined as any variable in the system that are uncontrolled variables (such as uncontrolled flows, compositions, temperatures in the process that are used by personnel for monitoring the operation of the process equipment), manipulated variables are defined as the variable in the process that is directly manipulated to produce a process control (such as a valve position or a set point on a control loop), and control variables are the variables that the manipulated variables are trying to control at a specific value (such as a composition, temperature, or pressure at a location, a flow rate, reflux ratio or the like).) and sending instructions regarding one or more operational parameters to the distillation column and associated hardware (col. 12, lines 60-67, For example, a person skilled in the art would know how to design a control systems for a distillation column in which set points for reflux ratio, feed rate, bottoms flow, reboiler duty, and the like are manipulated to control distillate compositions. Similarly a person skilled in the art would know how to design a control system for a polyolefins polymerization reactor in which gas composition is manipulated to control polymer properties.; col. 16, lines 42-47, The compositional analysis provided by the fast GC is used to control the reflux ratio (defined as 406 divided by 404) of the column. The set point on the internal fast GC control loop is reset by a slower, outer control loop whose set point is controlled by a conventional chromatographic analysis.).
Claims 5 and 17 are rejected under 35 U.S.C. 103 as being unpatentable over Wiegand et al. (‘630) in view of Rounbehler et al. (US 5,092,155).
Per claim 5, Wiegand et al. do not disclose wherein the fast gas chromatograph comprises a resistively heated, micro-packed column.
Rounbehler et al., also directed to a method (Abstract, A highly selective, sensitive, fast detection system and method are disclosed for detecting vapors of specific compounds in air.), disclose wherein a fast gas chromatograph comprises a resistively heated (col. 2, lines 40-44, In a preferred embodiment of the invention, a low temperature pyrolyzer receives the output of a first temperature-programmed gas chromatograph containing a glass capillary tube extending through a resistively heatable metal tube.), micro-packed column (50, 54; col. Tubes 50 having an inner diameter of about 0.53 mm, an outer diameter of about 0.8 mm and a length of about 19 mm have been found to be suitable, with flow and mass transfer calculations showing that at a sample flow rate of about 130 cm.sup.3 per minute through a collector containing 400 such tubes, at least about forty percent of the gas molecules in the sample will contact the inner wall, and thus the GC material 52, of such tubes.) in order to, for example, rapidly detect a compound in a gas.
Accordingly, it would have been readily obvious for the skilled artisan to modify the fast gas chromatograph of Wiegand et al. such that it comprises wherein the fast gas chromatograph comprises a resistively heated, micro-packed column in order to, for example, rapidly detect a compound in a gas.
Per claim 17, Wiegand et al. do not disclose wherein the fast gas chromatograph comprises a resistively heated, micro-packed column.
Rounbehler et al., also directed to a method (Abstract, A highly selective, sensitive, fast detection system and method are disclosed for detecting vapors of specific compounds in air.), disclose wherein a fast gas chromatograph comprises a resistively heated (col. 2, lines 40-44, In a preferred embodiment of the invention, a low temperature pyrolyzer receives the output of a first temperature-programmed gas chromatograph containing a glass capillary tube extending through a resistively heatable metal tube.), micro-packed column (50, 54; col. Tubes 50 having an inner diameter of about 0.53 mm, an outer diameter of about 0.8 mm and a length of about 19 mm have been found to be suitable, with flow and mass transfer calculations showing that at a sample flow rate of about 130 cm.sup.3 per minute through a collector containing 400 such tubes, at least about forty percent of the gas molecules in the sample will contact the inner wall, and thus the GC material 52, of such tubes.) in order to, for example, rapidly detect a compound in a gas.
Accordingly, it would have been readily obvious for the skilled artisan to modify the fast gas chromatograph of Wiegand et al. such that it comprises wherein the fast gas chromatograph comprises a resistively heated, micro-packed column in order to, for example, rapidly detect a compound in a gas.
Claims 10 and 13 are rejected under 35 U.S.C. 103 as being unpatentable over Wiegand et al. (‘630) in view of Tirmizi et al. (US 2018/0119033).
Per claim 10, Wiegand et al. do not disclose wherein the alkane and/or the alkene are obtained from (a) an ethylene oligomerization process or (b) hydrogenation of a reaction product obtained from an ethylene oligomerization process.
Tirmizi et al., also directed to a method (Abstract, The present invention is directed to methods and apparatus for conducting gas chromatography more rapidly than previously disclosed.), disclose wherein an alkane and/or the alkene are obtained from (a) an ethylene oligomerization process (Abstract, Processes are provided for producing hydrocarbon base oils from alcohols, including by converting one or more alcohols into linear alpha olefins, and then forming branched oligomers with one or more olefin feedstock(s) which are subsequently hydrogenated and fractionated.; [0016] For example, in one embodiment, ethanol is dehydrated to ethylene and included in the olefin mixture.; [0070] The ethyl alcohol derived olefins are made by dehydration of ethyl alcohol to ethylene, followed by a catalytic oligomerization to form a linear alpha-olefin product as disclosed in the prior art, for example, the Ineos (Ethyl) process “Ethylene chain growth process,”; [0092] Following purification 3, the ethylene is subjected to oligomerization 4, phase separation 5, and distillation 6 to provide product LAOs.) or (b) hydrogenation of a reaction product obtained from an ethylene oligomerization process (Abstract, Processes are provided for producing hydrocarbon base oils from alcohols, including by converting one or more alcohols into linear alpha olefins, and then forming branched oligomers with one or more olefin feedstock(s) which are subsequently hydrogenated and fractionated.) in order to, for example, produce hydrocarbon base oils (Abstract, Processes are provided for producing hydrocarbon base oils from alcohols, including by converting one or more alcohols into linear alpha olefins, and then forming branched oligomers with one or more olefin feedstock(s) which are subsequently hydrogenated and fractionated.).
Accordingly, it would have been readily obvious for the skilled artisan to modify the method of Wiegand et al. such that it comprises wherein the alkane and/or the alkene are obtained from (a) an ethylene oligomerization process or (b) hydrogenation of a reaction product obtained from an ethylene oligomerization process in order to, for example, produce hydrocarbon base oils.
Per claim 13, Wiegand et al. do not disclose wherein the hydrocarbon feed is a product of an olefin oligomerization process.
Tirmizi et al. disclose wherein a hydrocarbon feed is a product of an olefin oligomerization process ([0029] According to one embodiment, oligomer product is passed to a distillation column to remove and/or recycle the unreacted olefin monomer (D1) and the bottoms (R1) are passed to a 2.sup.nd, 3.sup.rd, and 4.sup.th distillation stage which can each be a fractional distillation column or alternatively a short-path evaporator.) in order to, for example, remove and/or recycle unreacted monomer. .
Accordingly, it would have been readily obvious for the skilled artisan to modify the method of Wiegand et al. such that it comprises wherein a hydrocarbon feed is a product of an olefin oligomerization process in order to, for example, remove and/or recycle unreacted monomer.
Claim 20 is rejected under 35 U.S.C. 103 as being unpatentable over Tirmizi et al. (US 2018/0119033) in view of Wiegand et al. (US 5,589,630).
Per claim 20, Tirmizi et al. disclose a method comprising:
forming a product stream comprising one or more linear alpha olefins by an olefin
oligomerization process (Abstract, Processes are provided for producing hydrocarbon base oils from alcohols, including by converting one or more alcohols into linear alpha olefins, and then forming branched oligomers with one or more olefin feedstock(s) which are subsequently hydrogenated and fractionated.);
optionally hydrogenating the product stream (Abstract, Processes are provided for producing hydrocarbon base oils from alcohols, including by converting one or more alcohols into linear alpha olefins, and then forming branched oligomers with one or more olefin feedstock(s) which are subsequently hydrogenated and fractionated.);
distilling at least a portion of the product stream to provide a plurality of distillation
fractions using a distillation column ([0029] According to one embodiment, oligomer product is passed to a distillation column to remove and/or recycle the unreacted olefin monomer (D1) and the bottoms (R1) are passed to a 2.sup.nd, 3.sup.rd, and 4.sup.th distillation stage which can each be a fractional distillation column or alternatively a short-path evaporator.);
obtaining a draw stream from one or more of the plurality of distillation fractions ([0103] FIG. 12 shows an embodiment of a C8-C16 distillation related to the inventive subject matter disclosed herein. According to one embodiment, oligomer product is passed to a distillation column to remove and/or recycle the unreacted olefin monomer (D1) and the bottoms (R1) are passed to a 2.sup.nd, 3.sup.rd, and 4.sup.th distillation stage which can each be a fractional distillation column or alternatively a short-path evaporator.; Fig. 12). Tirmizi et al. do not disclose analyzing the draw stream with a fast gas chromatograph to directly determine a carbon number distribution of the draw stream, the fast gas chromatograph having a cycle time that is less than a residence time of a specified component of the draw stream within the distillation column, and the fast gas chromatograph being in-line with or in parallel with the draw stream.
Wiegand et al. disclose a method comprising analyzing a draw stream with a fast gas chromatograph (403) to directly determine a carbon number distribution of the draw stream (FIGS. 4a-f are gas chromatograms for a gas sample containing various moieties having 1-6 carbon atoms.), the fast gas chromatograph having a cycle time that is less than a residence time of a specified component of the draw stream within a distillation column (Table 2, col. 15, lines 8-15, As is readily apparent from the above example, the retention times using the Process GC and the Conventional Capillary GC were much longer than the fast GC methods shown in columns 1-4 of Table 2. In employing the isothermal 5 meter column fast GC method, the column temperature of 110.degree. C. was selected so as to separate the C6 fraction (1-hexene, trans-2-hexene, etc.) in the column in less than 30 seconds.), and wherein the fast gas chromatograph is in-line with or in parallel with the draw stream (Fig. 5) in order to, for example, reduce the time taken to analyze the fractions of a draw stream and reduce system dead time while waiting for results (col. 2, lines 22-25, The methods and apparatus of the invention reduce the time necessary to perform gas chromatography by minimizing system dead volume along with sample and component bandwidths.).
Accordingly, it would have been readily obvious for the skilled artisan to modify the method of Tirmizi et al. such that it comprises analyzing the draw stream with a fast gas chromatograph to directly determine a carbon number distribution of the draw stream, the fast gas chromatograph having a cycle time that is less than a residence time of a specified component of the draw stream within the distillation column, and the fast gas chromatograph being in-line with or in parallel with the draw stream in order to, for example, reduce the time taken to analyze the fractions of a draw stream and reduce system dead time while waiting for results.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to FRED PRINCE whose telephone number is (571)272-1165. The examiner can normally be reached M-F: 0900-1730.
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/FRED PRINCE/
Primary Examiner
Art Unit 1779